##############################################################################
### CIF submission form for Rietveld refinements (IUCr journals) ###
### Version 20 January 2005 ###
##############################################################################
# This is an electronic "form" for submitting the results of a Rietveld
# refinement of a model against powder diffraction measurements to an
# IUCr journal as a Crystallographic Information File (CIF). Full details
# of the CIF format are given in the paper "The Crystallographic Information
# File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall,
# F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].
#
# The current version of the powder CIF dictionary, which contains definitions
# of the terms staring _pd_, may be obtained from
# http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in
# the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html.
#
# Note that all fields should be numeric or character type EXCEPT those which
# are flagged as 'text' - free-form text of any length may be included in
# these latter fields provided the text block begins and ends with a semicolon
# as the first character of a new line. Note also that the query marks
# '?' are significant as placeholders, and should not be deleted where a data
# item is not given, UNLESS the accompanying data name is also deleted.
# Lines should not exceed 80 characters in length. The comments following
# the number sign '#' may be deleted if wished.
#=============================================================================
data_global
_audit_update_record
;
2012-05-28 # Formatted by publCIF
;
_publ_requested_journal 'Acta Crystallographica Section C'
#==============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name 'Lemmerer, Andreas'
_publ_contact_author_address
;
School of Chemistry
University of the Witwatersrand
Private Bag 3
P.O. Wits
2050
South Africa
;
_publ_contact_author_email andreas.lemmerer@wits.ac.za
_publ_contact_author_phone 27(11)7176711
_publ_contact_author_fax 27(11)7176749
loop_
_publ_author_name
_publ_author_address
'Lapidus, Saul H.'
;Department of Physics & Astronomy
Stony Brook University
Stony Brook
NY 11794-3800
USA
;
'Lemmerer, Andreas'
;Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand, Johannesburg
PO Wits 2050
South Africa
;
'Bernstein, Joel'
;Faculty of Science
NYU Abu Dhabi
P.O. Box 129188
Abu Dhabi
UAE
;
'Stephens, Peter W. '
;Department of Physics & Astronomy
Stony Brook University
Stony Brook
NY 11794-3800
USA
;
_publ_requested_category CO
_publ_requested_coeditor_name ?
_publ_contact_letter # Include date of submission
;
Date of submission 29 May 2012
The Editor
Acta Crystallographica Section C
Dear Sir
Please consider this revised CIF submission for publication in Acta
Crystallographica C. All authors have seen and approved the submission.
The CIF has passed the Chester CHECKCIF routines and produces a
satisfactory PRINTCIF file.
When you reply by e-mail with my reference number I will send a signed
Copyright Transfer Form.
The Structure Factor Listing and artwork will be transferred to
Chester as instructed in Notes to Authors.
Yours sincerely
Andreas Lemmerer
;
#==============================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)
_journal_data_validation_number ?
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes ?
_journal_techeditor_code ?
_journal_techeditor_notes ?
_journal_coden_ASTM ?
_journal_name_full ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_paper_category ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
#==============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
'Rietveld refinement of the co-crystal
(N'-(propan-2-ylidene)nicotinohydrazide) (2,4-dihydroxybenzoic acid)'
;
_publ_section_title_footnote .
#==============================================================================
# 4. TEXT (For Acta Cryst. C and E, include the text of your paper in the CIF)
_publ_section_related_literature
;
For related literature, see:
Aaker\=oy et al., 2002;
Bernstein et al., 1995;
Lapidus et al., 2010;
Lemmerer et al., 2010;
Lemmerer et al., 2011a;
Lemmerer et al., 2011b.
;
_publ_section_abstract
;
In this work, we present an additional example of using a covalent reaction to
alter the supramolecular assembly by modification of the possible hydrogen
bonding. This concept was first presented in Lemmerer et al.
[CrystEngComm (2011a), 13, 55--59]. This structure consists of a
reacted niazid molecule, N'-(propan-2-ylidene)nicotinohydrazide, and
2,4-dihydroxybenzoic acid. The structure was solved from powder diffraction
data with the use of simulated annealing. This further demonstrates that using
powder diffraction as a relevant and useful analytical tool to study
co-crystals and their hydrogen bonded interactions.
;
_publ_section_comment
;
The two molecules, isonicotinic acid hydrazide (isoniazid) and nicotinic acid
hydrazide (niazid), are ideal supramolecular reagents that readily
co-crystallize with a number of carboxylic acid coformer molecules (Lemmerer
et al., 2010). Interest in these two molecules, especially the former
which is widely used as an anti-tuberculosis agent, comes about due to a
recently introduced strategy called covalent assistance to supramolecular
synthesis (Lemmerer et al., 2011a; 2011b). This approach
enables the crystal engineer to control the supramolecular assembly of either
molecule by altering their hydrogen bonding functionality through a covalent
reaction with a ketone molecule that transforms the amine functional group to
an alkylidene group in a Schiff-based condensation reaction. Specifically, the
use of 2-propanone (acetone) replaces the two H atoms with hydrogen bonding
inert methyl groups. Under this concept, the acetone molecule is termed a
"modifier".
This "modifying" reaction occurs in the crystallization vessel by
using acetone as a crystallization solvent in a solution containing niazid and
a molecule with carboxylic acid functionality, in this case niazid and
2,4-dihydroxybenzoic acid. However, the one-pot covalent and supramolecular
reaction to form a co-crystal occasionally results in a powder sample rather
than single crystals. In this case, crystal suitable for single-crystal
analysis were not obtained, so the structure was determined by powder
diffraction. The structure solution from X-ray (synchrotron) powder
diffraction data and Rietveld refinement (Fig. 1 and 2) is reported here.
The asymmetric unit consists of one reacted niazid molecule to form
N'-(propan-2-ylidene)nicotinohydrazide, p-niazid, and one
molecule of 2,4-dihydroxybenzoic acid, both on general positions. In terms of
forming a co-crystal, the essential feature are the hydrogen bonded
interactions between unlike but complimentary functional groups on either of
the two molecules. The hydrogen bond that is often observed in co-crystals
involving pyridine and carboxylic acid containing molecules is the carboxylic
acid...pyridine hydrogen bond, COO---H...N (Aaker\=oy et al., 2002); it
appears in the majority of co-crystals of unreacted and reacted niazid and
isoniazid. As the covalent reaction does not alter any of the latter two
functional groups, we expect it to be present in the title compound, as is
observed in the asymmetric unit (Fig. 1). In addition, the phenol group in the
para position also participates in a hydrogen bond to a lone-pair on a
N atom, O4---H4...N3\^i\^ [symmetry operator: (i) -x+2, -y+1, -z+1], in this
case on the now altered propanylidene functional group, providing a further
link between the two molecules in the co-crystal. The combination of these two
different O---H...N hydrogen bonds forms a four-molecule hydrogen bonded ring,
with graph set notation R^4^~4~(30) (Bernstein et al., 1995)
(Fig. 3). The second phenol group, in the 2-position, forms an intramolecular
S(6) hydrogen bond, in agreement with Etter's rules (Etter, 1990). The
p-niazid molecules themselves are hydrogen bonded to each other using
the unreacted present amide functional group, to form C(4) chains using
N1---H1...O1^ii^ [symmetry operator: (ii) x, -y+3/2, z+1/2] hydrogen bonds
along the crystallographic a-axis (Fig. 4). These chains connect the
rings to form a 2-D layer in the ab-plane.
The title compound now presents a third example where niazid has been reacted
with acetone to form a co-crystal with a suitable carboxylic acid co-fomer.
The previous two examples involved alkyldicarboxylic acids, namely adipic and
sebacic acid, and formed 1-D ribbons (Lemmerer et al., 2011a).
Nonetheless, the C(4) chain is observed in all three co-crystals, as
well as the carboxylic acid...pyridine hydrogen bond. The 2-D assembly of (I)
results from the para phenol group hydrogen bonding to the
p-niazid molecule in addition to the latter hydrogen bond, whereas the
first two co-crystals have both carboxylic acid functional groups hydrogen
bonding to two crystallographically related p-niazid molecules. This
paper further demonstrates that structure solution from powder diffraction
data is a relevant and useful analytical tool to study co-crystals and their
hydrogen bonded interactions (Lapidus et al., 2010).
;
_publ_section_exptl_prep
# Details of the preparation of the sample(s)
# should be given here.
;
(N'-(propan-2-ylidene)nicotinohydrazide)(2,4-dihydroxybenzoic acid) is
synthesized according to previous methods, where an acetone solution ( 10 ml)
of niazid (0.150 g, 1.09 mmol)
and 2,4-dihydroxybenzoic acid (0.169 g, 1.09 mmol) is heated for a few hours,
followed by cooling
and crystallization over a few days by slow evaporation.
High-resolution synchrotron X-ray powder diffraction data were collected at the
X16C beamline at the National Synchrotron Light Source at Brookhaven National
Laboratory. X-rays of wavelength 0.6999 Angstroms were selected using a Si(1 1
1) channel cut monochromator. After the sample, the diffracted beam was
analyzed with a Ge (1 1 1) crystal and detected by a NaI scintillation
counter. Wavelength and diffractometer zero were calibrated using a sample of
NIST Standard Reference Material 1976, a sintered plate of Al~2~O~3~.
The sample was loaded in a nominal 1.5 mm glass capillary and spun during data
collection to improve powder averaging.
;
_publ_section_exptl_refinement
;
Indexing of the powder pattern was performed in TOPAS Academic (Coelho, 2003).
This indexing revealed a monoclinic unit cell and from systematic absences a
tentative space group of P2~1~/c was assigned. From the volume
of the unit cell, the contents of the asymmetric unit were hypothesized to be
one of each molecule. These molecules were then defined as z-matrices
and simulated annealing was performed in TOPAS Academic (Coelho, 2007). This
structure solution was confirmed by a successful refinement, in which bond
lengths and angles of similar chemical character (e.g. aromatic, O---C
bonds, N---C bonds, etc.) were refined to a single joint value.
Aromatic rings were restricted to be regular planar hexagons. The
C9---C8---N3---N1 and C7---C8---N3---N1 torsion were restricted to planar as
the double bond between N3 and C8 would not allow a rotation about that bond.
This strategy of refining bond lengths has been shown to result in values
comparable to a single-crystal measurement (Lapidus et al., 2010). H
atoms were placed by idealized geometry in reference to the other atoms,
specifically hydrogen bonds were inferred from donor-acceptor distances.
Errors in atomic positions were estimated by the bootstrap method of error
determination (Efron et al., 1986) as implemented in TOPAS Academic
(Coelho, 2007). This error estimation is performed by modifying a fraction of
the data within its statistical uncertainty and observing the change in each
refined atomic position. This process is repeated many times and an
uncertainty in each atomic position is estimated from the overall motion of
each atom over these cycles.
;
_publ_section_references
;
Aaker\=oy, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Amer. Chem.
Soc. 124, 14425--14432.
Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew.
Chem. Int. Ed. Engl. 34, 1555--1573.
Brandenburg, K. (1999). DIAMOND. Version 2.1e. Crystal Impact GbR, Bonn,
Germany.
Coelho, A. A. (2003). J. Appl. Crystallogr. 36, 86--95.
Coelho, A. A. (2007). TOPAS-Academic: General profile and structure analysis
software for powder diffraction data.; TOPAS-Academic is available at
http://topas-academic.net.
Efron, B. & Tibshirani, R. (1986). Stat. Sci. 1, 54--77.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120--126.
Lapidus, S. H., Stephens, P. W., Arora, K. K., Shattock, T. R. & Zaworotko, M.
J. (2010). Cryst. Growth Des. 10, 4630--4637.
Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2010). CrystEngComm,
12, 2856--2864.
Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011a).
CrystEngComm, 13, 55--59.
Lemmerer, A., Bernstein, J. & Kahlenberg, V. (2011b).
CrystEngComm, 13, 5692--5708.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920--925.
;
_publ_section_figure_captions
;
Figure 1. Atom labelling scheme for co-crystal (I).
Figure 2. High-resolution synchrotron powder diffraction data (dots) and
Rietveld fit of the data. The lower trace is the difference, measured minus
calculated, plotted to the same vertical scale.
Figure 3. View of the R^4^~4~(30) rings in the structure.
Figure 4. View of the C(4) synthon formed by the N1---H1...O1 hydrogen
bond.
;
_publ_section_acknowledgements
;
Use of the National Synchrotron Light Source, Brookhaven National Laboratory,
was supported by the U.S. Department of Energy, Office of Science, Office of
Basic Energy Sciences, under Contract No. DE-AC02--98CH10886. Some of this
work was carried out while AL and JB were in the Department of Chemistry,
Ben-Gurion University of the Negev, with financial support in part by Grant
No. 2004118 from the United States-Israel Binational Science Foundation
(Jerusalem). A. L. thanks the South African National Research Foundation for a
postdoctoral scholarship (SFP2007070400002) and the Oppenheimer Memorial Trust
for financial support, and the Molecular Sciences Institute for infrasture.
;
#==============================================================================
# If more than one structure is reported, sections 5-10 should be completed
# per structure. For each data set, replace the '?' in the data_? line below
# by a unique identifier.
#==============================================================================
data_I
# 5. CHEMICAL DATA
_chemical_name_systematic
'(N'-(propan-2-ylidene)nicotinohydrazide) (2,4-dihydroxybenzoic acid)'
_chemical_name_common ?
_chemical_formula_moiety 'C9 H11 N3 O, C7 H6 O4'
_chemical_formula_structural ?
_chemical_formula_analytical ?
_chemical_formula_sum 'C16 H17 N3 O5 '
_chemical_formula_weight 331.33
_chemical_melting_point ?
_chemical_compound_source ? # for minerals and
# natural products
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# 6. POWDER SPECIMEN AND CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a 8.5813(3)
_cell_length_b 22.7241(7)
_cell_length_c 8.8506(3)
_cell_angle_alpha 90
_cell_angle_beta 95.760(3)
_cell_angle_gamma 90
_cell_volume 1717.16(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 295
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.282
_cell_special_details
?
# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.
_pd_spec_size_axial 8 # perpendicular to
# equatorial plane
_pd_spec_size_equat 1.5 # parallel to
# scattering vector
# in transmission
_pd_spec_size_thick ? # parallel to
# scattering vector
# in reflection
# The next five fields are character fields that describe the specimen.
_pd_spec_mounting # This field should be
# used to give details of the
# container.
;
capillary
;
_pd_spec_mount_mode transmission # options are 'reflection'
# or 'transmission'
_pd_spec_shape cylinder # options are 'cylinder'
# 'flat_sheet' or 'irregular'
_pd_char_particle_morphology ?
_pd_char_colour 'white' # use ICDD colour descriptions
# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min. The pressure at which the sample was
# prepared is in kPa. The temperature of preparation is in K.
_pd_prep_cool_rate ?
_pd_prep_pressure ?
_pd_prep_temperature ?
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_coefficient_mu .092 # include if applicable
_exptl_absorpt_correction_type ? # include if applicable
_exptl_absorpt_process_details ? # include if applicable
_exptl_absorpt_correction_T_min ? # include if applicable
_exptl_absorpt_correction_T_max ? # include if applicable
#==============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
?
# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.
_pd_instr_location
;
X16C, National Synchrotron Light Source, Brookhaven National Laboratory
;
_pd_calibration_special_details # description of the method used
# to calibrate the instrument
;
NIST standard reference material 1976(sintered plate of Al2O3)
Well-isolated 7 reflections were used to calibrate wavelength and detector zero.
;
_diffrn_ambient_temperature 295
_diffrn_source 'synchrotron'
_diffrn_source_target ?
_diffrn_source_type ?
_diffrn_radiation_type synchrotron
_diffrn_measurement_device_type 'Huber diffractometer'
_diffrn_detector 'NaI scintillation counter'
_diffrn_detector_type ? # make or model of detector
_pd_meas_scan_method step # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details
?
# The following six items are used for angular dispersive measurements only.
_diffrn_radiation_wavelength 0.6999
_diffrn_radiation_monochromator 'Si(111) channel cut'
# The following four items give details of the measured (not processed)
# powder pattern. Angles are in degrees.
_pd_meas_number_of_points 6401
_pd_meas_2theta_range_min 3.0
_pd_meas_2theta_range_max 35.0
_pd_meas_2theta_range_inc 0.005
# The following three items are used for time-of-flight measurements only.
_pd_instr_dist_src/spec ?
_pd_instr_dist_spec/detc ?
_pd_meas_2theta_fixed ?
#==============================================================================
# 8. REFINEMENT DATA
# Use the next field to give any special details about the fitting of the
# powder pattern.
_pd_proc_ls_special_details
;
Molecules are defined as rigid bodies using the z-matrix function
implemented in TOPAS-Academic. The same isotropic displacement parameters are
assigned to each molecule.
;
# The next three items are given as text.
_pd_proc_ls_profile_function
;
Simple_Axial_model function with Rp=9999,Rs=330 in TOPAS-Academic
;
_pd_proc_ls_background_function
;
2 Pearson-Voight peaks and Chebyshev polynomial with 8 coefficients
;
_pd_proc_ls_pref_orient_corr
;
none
;
_pd_proc_ls_prof_R_factor 0.03827 # 3.827(%)
_pd_proc_ls_prof_wR_factor 0.04495 # 4.495(%)
_pd_proc_ls_prof_wR_expected 0.03048 # 3.048(%)
_refine_ls_R_I_factor ?
_refine_ls_R_Fsqd_factor ?
_refine_ls_R_factor_all ?
_refine_special_details
?
_refine_ls_matrix_type ?
_refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's)
# or 'calc' (calculated weights)
_refine_ls_weighting_details '1/(sigma*sigma)'
_refine_ls_extinction_coef ?
_refine_ls_number_parameters 67
_refine_ls_number_restraints ?
_refine_ls_number_constraints ?
_refine_ls_hydrogen_treatment constr
# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all 1.475
_refine_ls_restrained_S_all ?
_refine_ls_shift/su_max ?
_refine_ls_shift/su_mean ?
# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.
_pd_proc_2theta_range_min 3.0
_pd_proc_2theta_range_max 35.0
_pd_proc_2theta_range_inc 0.005
_pd_proc_wavelength 0.6999
_pd_block_diffractogram_id NP254
# The id used for the block containing
# the powder pattern profile (section 11).
# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions ?
_pd_proc_info_data_reduction ?
# The following items are used to identify the programs used.
_computing_data_collection SPEC
_computing_cell_refinement 'TOPAS-Academic (Coelho, 2003)'
_computing_data_reduction 'TOPAS-Academic (Coelho, 2007)'
_computing_structure_solution 'TOPAS-Academic (Coelho, 2007)'
_computing_structure_refinement 'TOPAS-Academic (Coelho, 2007)'
_computing_molecular_graphics 'Diamond (Brandenburg, 1999)'
_computing_publication_material 'publCIF (Westrip, 2010)'
#==============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uiso 0.7415(5) 0.70461(17) 0.2383(7) 1.000 0.0536(7) . .
N1 N Uiso 0.7505(5) 0.78157(12) 0.4156(5) 1.000 0.0536(7) . .
N2 N Uiso 0.5864(5) 0.59285(12) 0.5666(3) 1.000 0.0536(7) . .
N3 N Uiso 0.8521(4) 0.8122(3) 0.3279(7) 1.000 0.0536(7) . .
C1 C Uiso 0.63152(5) 0.68879(7) 0.4629(18) 1.000 0.0536(7) . .
C2 C Uiso 0.6644(5) 0.62883(15) 0.4714(3) 1.000 0.0536(7) . .
C3 C Uiso 0.4755(4) 0.61686(16) 0.6534(3) 1.000 0.0536(7) . .
C4 C Uiso 0.4426(4) 0.67682(11) 0.6449(4) 1.000 0.0536(7) . .
C5 C Uiso 0.5206(3) 0.71278(7) 0.5498(5) 1.000 0.0536(7) . .
C6 C Uiso 0.7095(4) 0.72476(10) 0.3678(3) 1.000 0.0536(7) . .
C7 C Uiso 0.9891(6) 0.90319(19) 0.2737(6) 1.000 0.0536(7) . .
C8 C Uiso 0.8839(2) 0.8674(2) 0.3612(4) 1.000 0.0536(7) . .
C9 C Uiso 0.8169(7) 0.898(2) 0.4886(6) 1.000 0.0536(7) . .
O2 O Uiso 0.6892(5) 0.4881(3) 0.5974(5) 1.000 0.0645(5) . .
O3 O Uiso 0.5693(5) 0.4852(3) 0.8131(5) 1.000 0.0645(5) . .
O4 O Uiso 0.9391(4) 0.24385(11) 0.8496(4) 1.000 0.0645(5) . .
O5 O Uiso 0.6268(5) 0.39759(19) 0.997(2) 1.000 0.0645(5) . .
C10 C Uiso 0.7317(2) 0.40453(12) 0.7582(2) 1.000 0.0645(5) . .
C11 C Uiso 0.7114(3) 0.37562(13) 0.8935(3) 1.000 0.0645(5) . .
C12 C Uiso 0.7817(3) 0.32116(13) 0.9245(3) 1.000 0.0645(5) . .
C13 C Uiso 0.8723(3) 0.29561(13) 0.8202(3) 1.000 0.0645(5) . .
C14 C Uiso 0.8926(3) 0.32452(10) 0.6849(3) 1.000 0.0645(5) . .
C15 C Uiso 0.8223(2) 0.37898(8) 0.6539(3) 1.000 0.0645(5) . .
C16 C Uiso 0.6565(4) 0.4628(2) 0.725(3) 1.000 0.0645(5) . .
H1 H Uiso 0.7125 0.79669 0.4984 1.000 0.0536(7) . .
H2A H Uiso 0.7361 0.61332 0.4153 1.000 0.0536(7) . .
H3 H Uiso 0.4251 0.59361 0.7149 1.000 0.0536(7) . .
H4A H Uiso 0.371 0.69234 0.701 1.000 0.0536(7) . .
H5A H Uiso 0.4993 0.75155 0.5444 1.000 0.0536(7) . .
H7A H Uiso 0.941 0.9371 0.245 1.000 0.0536(7) . .
H7B H Uiso 1.078 0.9108 0.3331 1.000 0.0536(7) . .
H7C H Uiso 1.011 0.8828 0.191 1.000 0.0536(7) . .
H9A H Uiso 0.809 0.8722 0.565 1.000 0.0536(7) . .
H9B H Uiso 0.88 0.9279 0.521 1.000 0.0536(7) . .
H9C H Uiso 0.721 0.912 0.4555 1.000 0.0536(7) . .
H2 H Uiso 0.6395 0.523 0.5858 1.000 0.0645(5) . .
H4 H Uiso 0.9935 0.23299 0.7724 1.000 0.0645(5) . .
H5 H Uiso 0.5868 0.43268 0.966 1.000 0.0645(5) . .
H12 H Uiso 0.7686 0.30246 1.0119 1.000 0.0645(5) . .
H14 H Uiso 0.9511 0.308 0.6174 1.000 0.0645(5) . .
H15 H Uiso 0.8354 0.39767 0.5664 1.000 0.0645(5) . .
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.289(6) . . yes
O2 C16 1.32(2) . . yes
O3 C16 1.243(17) . . yes
O4 C13 1.323(4) . . yes
O5 C11 1.323(13) . . yes
O2 H2 0.9000 . . no
O4 H4 0.9000 . . no
O5 H5 0.9000 . . no
N1 N3 1.408(7) . . yes
N1 C6 1.393(4) . . yes
N2 C2 1.393(5) . . yes
N2 C3 1.393(5) . . yes
N3 C8 1.311(8) . . yes
N1 H1 0.9000 . . no
C1 C6 1.392(10) . . no
C1 C2 1.392(4) . . no
C1 C5 1.393(9) . . no
C3 C4 1.392(4) . . no
C4 C5 1.392(4) . . no
C7 C8 1.489(6) . . no
C8 C9 1.49(2) . . no
C2 H2A 0.9000 . . no
C3 H3 0.9000 . . no
C4 H4A 0.9000 . . no
C5 H5A 0.9000 . . no
C7 H7B 0.9000 . . no
C7 H7A 0.9000 . . no
C7 H7C 0.9000 . . no
C9 H9C 0.9000 . . no
C9 H9A 0.9000 . . no
C9 H9B 0.9000 . . no
C10 C16 1.489(7) . . no
C10 C11 1.392(3) . . no
C10 C15 1.392(3) . . no
C11 C12 1.392(4) . . no
C12 C13 1.392(4) . . no
C13 C14 1.392(4) . . no
C14 C15 1.392(3) . . no
C12 H12 0.9000 . . no
C14 H14 0.9000 . . no
C15 H15 0.9000 . . no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 H2 110.00 . . . no
C13 O4 H4 110.00 . . . no
C11 O5 H5 110.00 . . . no
N3 N1 C6 116.3(4) . . . yes
C2 N2 C3 120.0(3) . . . yes
N1 N3 C8 118.4(5) . . . yes
C6 N1 H1 120.00 . . . no
N3 N1 H1 124.00 . . . no
C5 C1 C6 120.0(2) . . . no
C2 C1 C6 120.0(7) . . . no
C2 C1 C5 119.9(7) . . . no
N2 C2 C1 120.0(5) . . . yes
N2 C3 C4 120.0(3) . . . yes
C3 C4 C5 120.0(3) . . . no
C1 C5 C4 120.1(3) . . . no
N1 C6 C1 118.9(5) . . . yes
O1 C6 C1 119.2(5) . . . yes
O1 C6 N1 122.0(3) . . . yes
N3 C8 C7 122.0(4) . . . yes
C7 C8 C9 116.1(15) . . . no
N3 C8 C9 122.0(15) . . . yes
N2 C2 H2A 120.00 . . . no
C1 C2 H2A 120.00 . . . no
N2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C5 C4 H4A 120.00 . . . no
C3 C4 H4A 120.00 . . . no
C1 C5 H5A 120.00 . . . no
C4 C5 H5A 120.00 . . . no
C8 C7 H7B 109.00 . . . no
H7A C7 H7C 110.00 . . . no
C8 C7 H7C 109.00 . . . no
H7A C7 H7B 110.00 . . . no
C8 C7 H7A 109.00 . . . no
H7B C7 H7C 110.00 . . . no
C8 C9 H9C 109.00 . . . no
H9A C9 H9C 110.00 . . . no
H9B C9 H9C 110.00 . . . no
H9A C9 H9B 110.00 . . . no
C8 C9 H9A 109.00 . . . no
C8 C9 H9B 109.00 . . . no
C15 C10 C16 120.0(9) . . . no
C11 C10 C15 120.0(2) . . . no
C11 C10 C16 120.0(9) . . . no
O5 C11 C12 117.2(5) . . . yes
O5 C11 C10 122.9(5) . . . yes
C10 C11 C12 120.0(2) . . . no
C11 C12 C13 120.0(3) . . . no
O4 C13 C12 120.0(3) . . . yes
O4 C13 C14 120.0(3) . . . yes
C12 C13 C14 120.0(3) . . . no
C13 C14 C15 120.0(2) . . . no
C10 C15 C14 120.0(2) . . . no
O2 C16 O3 123.4(8) . . . yes
O2 C16 C10 115.5(11) . . . yes
O3 C16 C10 121.1(16) . . . yes
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C10 C15 H15 120.00 . . . no
C14 C15 H15 120.00 . . . no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N3 C8 174.6(4) . . . . no
N3 N1 C6 O1 -10.7(6) . . . . no
N3 N1 C6 C1 169.4(5) . . . . no
C3 N2 C2 C1 0.0(7) . . . . no
C2 N2 C3 C4 0.0(5) . . . . no
N1 N3 C8 C7 -179.5(4) . . . . no
N1 N3 C8 C9 0.4(9) . . . . no
C5 C1 C2 N2 0.0(12) . . . . no
C6 C1 C2 N2 180.0(6) . . . . no
C2 C1 C5 C4 -0.1(12) . . . . no
C6 C1 C5 C4 180.0(6) . . . . no
C2 C1 C6 O1 37.0(11) . . . . no
C2 C1 C6 N1 -143.0(7) . . . . no
C5 C1 C6 O1 -143.0(8) . . . . no
C5 C1 C6 N1 36.9(11) . . . . no
N2 C3 C4 C5 -0.1(5) . . . . no
C3 C4 C5 C1 0.1(8) . . . . no
C15 C10 C11 O5 180.0(5) . . . . no
C15 C10 C11 C12 0.0(4) . . . . no
C16 C10 C11 O5 0.0(8) . . . . no
C16 C10 C11 C12 -180.0(6) . . . . no
C11 C10 C15 C14 0.0(3) . . . . no
C16 C10 C15 C14 180.0(6) . . . . no
C11 C10 C16 O2 176.7(7) . . . . no
C11 C10 C16 O3 -3.4(14) . . . . no
C15 C10 C16 O2 -3.3(12) . . . . no
C15 C10 C16 O3 176.7(9) . . . . no
O5 C11 C12 C13 -180.0(5) . . . . no
C10 C11 C12 C13 0.0(4) . . . . no
C11 C12 C13 O4 -180.0(3) . . . . no
C11 C12 C13 C14 0.0(4) . . . . no
O4 C13 C14 C15 180.0(3) . . . . no
C12 C13 C14 C15 0.0(4) . . . . no
C13 C14 C15 C10 0.0(3) . . . . no
#==============================================================================
# 11. POWDER PROFILE
# Each refinement must be accompanied by a listing of the powder profile
# in CIF format. Each listing should be sent as a separate file consisting
# of one data block containing a single powder profile. The _pd_block_id
# is used to associate each refinement with its corresponding powder profile
# since it must match the field _pd_block_diffractogram_id in section 8.
data_profile
_pd_block_id NP254
loop_
_pd_proc_point_id
_pd_proc_2theta_corrected # one of
# _pd_proc_energy_incident # these
# _pd_proc_d_spacing # three
_pd_proc_intensity_net
_pd_calc_intensity_net
_pd_proc_ls_weight
1 3.000 439 429 0.00197531
2 3.005 404 429 0.00214335
3 3.010 424 428 0.00204746
4 3.015 447 427 0.00194065
5 3.020 409 427 0.00212364
6 3.025 432 426 0.0020109
7 3.030 406 425 0.00214335
8 3.035 418 425 0.00208503
9 3.040 372 424 0.00233378
10 3.045 413 423 0.0021042
11 3.050 398 422 0.0021836
12 3.055 426 422 0.00204746
13 3.060 435 421 0.00199298
14 3.065 425 420 0.00204746
15 3.070 386 420 0.00224613
16 3.075 397 419 0.0021836
17 3.080 405 419 0.00214335
18 3.085 408 418 0.00212364
19 3.090 393 417 0.00220415
20 3.095 400 417 0.00216333
21 3.100 425 416 0.00204746
22 3.105 458 415 0.00189036
23 3.110 392 415 0.00222499
24 3.115 397 414 0.0021836
25 3.120 411 413 0.0021042
26 3.125 374 413 0.00231139
27 3.130 452 412 0.00192367
28 3.135 446 412 0.00194065
29 3.140 426 411 0.00202906
30 3.145 406 411 0.00214335
31 3.150 392 410 0.00222499
32 3.155 403 410 0.00214335
33 3.160 444 410 0.00195787
34 3.165 409 409 0.00212364
35 3.170 404 409 0.00214335
36 3.175 415 409 0.00208503
37 3.180 452 409 0.00192367
38 3.185 391 409 0.00222499
39 3.190 409 410 0.00212364
40 3.195 451 410 0.00192367
41 3.200 445 412 0.00195787
42 3.205 456 414 0.0019069
43 3.210 446 420 0.00194065
44 3.215 460 436 0.00189036
45 3.220 478 458 0.00181077
46 3.225 473 481 0.00184199
47 3.230 542 506 0.0016
48 3.235 508 532 0.00170753
49 3.240 577 559 0.00150231
50 3.245 589 587 0.00146798
51 3.250 611 616 0.00142399
52 3.255 679 645 0.00127551
53 3.260 647 676 0.00134176
54 3.265 692 707 0.00125748
55 3.270 722 740 0.0011973
56 3.275 748 773 0.00115693
57 3.280 849 808 0.00102073
58 3.285 866 844 0.00100144
59 3.290 890 881 0.00097656
60 3.295 962 919 0.0009018
61 3.300 966 959 0.00089641
62 3.305 1032 1000 0.00084016
63 3.310 1016 1042 0.00085496
64 3.315 1069 1086 0.00081168
65 3.320 1154 1132 0.00075061
66 3.325 1225 1179 0.00070733
67 3.330 1302 1228 0.00066426
68 3.335 1294 1280 0.00067116
69 3.340 1418 1333 0.00061269
70 3.345 1490 1389 0.00058344
71 3.350 1449 1447 0.0005978
72 3.355 1542 1508 0.00056153
73 3.360 1623 1572 0.00053336
74 3.365 1734 1638 0.00050048
75 3.370 1762 1708 0.00049164
76 3.375 1933 1782 0.00044887
77 3.380 1893 1860 0.00045853
78 3.385 1889 1942 0.00045853
79 3.390 2106 2029 0.00041144
80 3.395 2164 2122 0.0004
81 3.400 2413 2220 0.0003587
82 3.405 2364 2326 0.00036699
83 3.410 2533 2439 0.00034167
84 3.415 2577 2562 0.00033667
85 3.420 2748 2703 0.00031549
86 3.425 2718 2846 0.00031888
87 3.430 2953 2993 0.00029321
88 3.435 3159 3151 0.00027411
89 3.440 3308 3324 0.00026183
90 3.445 3342 3513 0.00025931
91 3.450 3683 3720 0.00023524
92 3.455 3868 3950 0.0002241
93 3.460 3974 4206 0.00021818
94 3.465 4389 4495 0.00019726
95 3.470 4545 4822 0.00019078
96 3.475 5166 5197 0.00016779
97 3.480 5373 5635 0.00016105
98 3.485 5997 6154 0.00014446
99 3.490 6444 6781 0.00013427
100 3.495 7432 7561 0.00011662
101 3.500 8150 8567 0.00010628
102 3.505 9478 9929 9.14e-005
103 3.510 11417 11912 7.588e-005
104 3.515 14577 15124 5.935e-005
105 3.520 19870 20833 4.357e-005
106 3.525 16890 17848 5.124e-005
107 3.530 6007 5327 0.00014412
108 3.535 2143 2478 0.00040322
109 3.540 1446 1557 0.0005978
110 3.545 942 1142 0.00091827
111 3.550 778 917 0.00111111
112 3.555 645 780 0.00134176
113 3.560 634 689 0.00136164
114 3.565 575 625 0.00150231
115 3.570 536 578 0.00161288
116 3.575 564 542 0.00153787
117 3.580 499 514 0.00173611
118 3.585 494 492 0.00175067
119 3.590 516 473 0.00167966
120 3.595 446 457 0.00194065
121 3.600 478 444 0.00181077
122 3.605 443 432 0.00195787
123 3.610 451 421 0.00192367
124 3.615 407 410 0.00212364
125 3.620 461 399 0.00187403
126 3.625 430 386 0.0020109
127 3.630 427 368 0.00202906
128 3.635 412 368 0.0021042
129 3.640 394 368 0.0021836
130 3.645 405 368 0.00214335
131 3.650 414 367 0.00208503
132 3.655 438 367 0.00197531
133 3.660 407 367 0.00212364
134 3.665 396 366 0.0021836
135 3.670 393 366 0.00220415
136 3.675 408 366 0.00212364
137 3.680 385 366 0.00224613
138 3.685 410 365 0.0021042
139 3.690 373 365 0.00231139
140 3.695 439 365 0.00197531
141 3.700 426 365 0.00202906
142 3.705 393 364 0.00220415
143 3.710 360 364 0.00240292
144 3.715 413 364 0.00208503
145 3.720 397 364 0.0021836
146 3.725 387 363 0.00224613
147 3.730 373 363 0.00231139
148 3.735 395 363 0.0021836
149 3.740 410 363 0.0021042
150 3.745 388 362 0.00222499
151 3.750 402 362 0.00214335
152 3.755 354 362 0.00245074
153 3.760 372 362 0.00233378
154 3.765 364 361 0.00237954
155 3.770 397 361 0.0021836
156 3.775 381 361 0.00226757
157 3.780 382 361 0.00226757
158 3.785 373 360 0.00231139
159 3.790 374 360 0.00231139
160 3.795 384 360 0.00224613
161 3.800 375 360 0.00231139
162 3.805 398 360 0.00216333
163 3.810 374 359 0.00231139
164 3.815 378 359 0.00228932
165 3.820 400 359 0.00216333
166 3.825 410 359 0.0021042
167 3.830 388 358 0.00222499
168 3.835 371 358 0.00233378
169 3.840 349 358 0.00247519
170 3.845 365 358 0.00235649
171 3.850 343 358 0.00252519
172 3.855 372 357 0.00231139
173 3.860 336 357 0.00257672
174 3.865 385 357 0.00224613
175 3.870 404 357 0.00214335
176 3.875 353 357 0.00245074
177 3.880 369 356 0.00233378
178 3.885 365 356 0.00235649
179 3.890 378 356 0.00228932
180 3.895 342 356 0.00252519
181 3.900 371 356 0.00233378
182 3.905 352 356 0.00245074
183 3.910 366 355 0.00235649
184 3.915 364 355 0.00237954
185 3.920 327 355 0.00262985
186 3.925 329 355 0.00262985
187 3.930 356 355 0.00242665
188 3.935 329 354 0.00262985
189 3.940 377 354 0.00228932
190 3.945 335 354 0.00257672
191 3.950 330 354 0.00260308
192 3.955 365 354 0.00235649
193 3.960 354 354 0.00245074
194 3.965 375 353 0.00231139
195 3.970 326 353 0.00265703
196 3.975 351 353 0.00245074
197 3.980 335 353 0.00257672
198 3.985 341 353 0.00252519
199 3.990 348 353 0.00247519
200 3.995 382 353 0.00226757
201 4.000 365 352 0.00235649
202 4.005 371 352 0.00233378
203 4.010 379 352 0.00226757
204 4.015 306 352 0.00282933
205 4.020 365 352 0.00235649
206 4.025 325 352 0.00265703
207 4.030 383 352 0.00224613
208 4.035 312 351 0.00277008
209 4.040 356 351 0.00242665
210 4.045 338 351 0.00255076
211 4.050 384 351 0.00224613
212 4.055 324 351 0.00265703
213 4.060 363 351 0.00237954
214 4.065 380 351 0.00226757
215 4.070 360 350 0.00240292
216 4.075 328 350 0.00262985
217 4.080 338 350 0.00255076
218 4.085 364 350 0.00235649
219 4.090 354 350 0.00242665
220 4.095 322 350 0.00268464
221 4.100 306 350 0.00279947
222 4.105 373 350 0.00231139
223 4.110 353 349 0.00245074
224 4.115 344 349 0.0025
225 4.120 338 349 0.00255076
226 4.125 305 349 0.00282933
227 4.130 327 349 0.00262985
228 4.135 353 349 0.00245074
229 4.140 320 349 0.00268464
230 4.145 313 349 0.00274115
231 4.150 329 349 0.00262985
232 4.155 332 349 0.00260308
233 4.160 341 348 0.00252519
234 4.165 348 348 0.00247519
235 4.170 372 348 0.00231139
236 4.175 344 348 0.0025
237 4.180 337 348 0.00255076
238 4.185 358 348 0.00240292
239 4.190 329 348 0.00262985
240 4.195 366 348 0.00235649
241 4.200 400 348 0.00216333
242 4.205 314 348 0.00274115
243 4.210 352 347 0.00245074
244 4.215 346 347 0.00247519
245 4.220 331 347 0.00260308
246 4.225 333 347 0.00257672
247 4.230 318 347 0.00271267
248 4.235 346 347 0.00247519
249 4.240 332 347 0.00257672
250 4.245 375 347 0.00228932
251 4.250 335 347 0.00257672
252 4.255 317 347 0.00271267
253 4.260 357 347 0.00240292
254 4.265 320 347 0.00268464
255 4.270 337 347 0.00255076
256 4.275 362 346 0.00237954
257 4.280 341 346 0.00252519
258 4.285 343 346 0.0025
259 4.290 342 346 0.00252519
260 4.295 369 346 0.00233378
261 4.300 322 346 0.00268464
262 4.305 371 346 0.00231139
263 4.310 358 346 0.00240292
264 4.315 328 346 0.00262985
265 4.320 340 346 0.00252519
266 4.325 321 346 0.00268464
267 4.330 327 346 0.00262985
268 4.335 369 346 0.00233378
269 4.340 358 346 0.00240292
270 4.345 369 346 0.00233378
271 4.350 318 346 0.00271267
272 4.355 334 346 0.00257672
273 4.360 328 346 0.00262985
274 4.365 335 346 0.00257672
275 4.370 288 346 0.00298606
276 4.375 343 346 0.0025
277 4.380 363 346 0.00237954
278 4.385 357 346 0.00240292
279 4.390 329 346 0.00260308
280 4.395 354 346 0.00242665
281 4.400 358 346 0.00240292
282 4.405 327 346 0.00262985
283 4.410 334 346 0.00257672
284 4.415 329 347 0.00260308
285 4.420 355 347 0.00242665
286 4.425 350 347 0.00245074
287 4.430 347 348 0.00247519
288 4.435 369 348 0.00233378
289 4.440 327 349 0.00262985
290 4.445 339 350 0.00252519
291 4.450 334 351 0.00257672
292 4.455 346 353 0.00247519
293 4.460 354 357 0.00242665
294 4.465 378 364 0.00226757
295 4.470 382 371 0.00224613
296 4.475 396 379 0.00216333
297 4.480 389 388 0.00220415
298 4.485 419 397 0.00204746
299 4.490 402 406 0.00214335
300 4.495 410 416 0.0021042
301 4.500 432 426 0.00199298
302 4.505 452 437 0.0019069
303 4.510 440 448 0.00195787
304 4.515 493 460 0.00175067
305 4.520 465 472 0.00184199
306 4.525 494 486 0.00173611
307 4.530 512 499 0.00167966
308 4.535 493 515 0.00175067
309 4.540 529 532 0.00162591
310 4.545 540 547 0.00158728
311 4.550 502 564 0.00170753
312 4.555 663 581 0.00129393
313 4.560 585 599 0.00146798
314 4.565 633 618 0.00136164
315 4.570 647 638 0.00133198
316 4.575 647 660 0.00133198
317 4.580 690 683 0.00124861
318 4.585 720 708 0.00118906
319 4.590 828 735 0.0010339
320 4.595 786 763 0.00108922
321 4.600 784 794 0.00109644
322 4.605 837 827 0.00102728
323 4.610 880 864 0.00097656
324 4.615 903 904 0.0009526
325 4.620 959 948 0.00089641
326 4.625 1070 997 0.00080251
327 4.630 1075 1051 0.00079798
328 4.635 1117 1113 0.00076734
329 4.640 1258 1183 0.00068171
330 4.645 1282 1264 0.00067116
331 4.650 1419 1358 0.00060666
332 4.655 1505 1471 0.0005696
333 4.660 1614 1608 0.00053336
334 4.665 1796 1779 0.00047881
335 4.670 2046 2001 0.00041991
336 4.675 2405 2303 0.00035735
337 4.680 2752 2739 0.00031215
338 4.685 3322 3395 0.00025848
339 4.690 3909 4005 0.00021948
340 4.695 2534 2574 0.00033916
341 4.700 1311 1266 0.0006541
342 4.705 810 819 0.00106102
343 4.710 612 635 0.00140274
344 4.715 544 543 0.0015747
345 4.720 456 490 0.00189036
346 4.725 453 456 0.00189036
347 4.730 398 433 0.00216333
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1493 10.460 769 777 0.00111111
1494 10.465 746 754 0.00114134
1495 10.470 689 744 0.00123983
1496 10.475 797 742 0.00106797
1497 10.480 689 738 0.00123983
1498 10.485 709 737 0.00120563
1499 10.490 736 736 0.00115693
1500 10.495 695 737 0.00123115
1501 10.500 742 739 0.0011491
1502 10.505 688 741 0.00123983
1503 10.510 692 744 0.00123115
1504 10.515 693 748 0.00123115
1505 10.520 728 752 0.00117283
1506 10.525 742 758 0.0011491
1507 10.530 747 764 0.00114134
1508 10.535 736 771 0.00115693
1509 10.540 740 780 0.00115693
1510 10.545 803 790 0.00106102
1511 10.550 781 803 0.00108922
1512 10.555 728 818 0.00117283
1513 10.560 833 839 0.00102728
1514 10.565 854 873 0.00100144
1515 10.570 846 925 0.00100781
1516 10.575 902 993 0.00094675
1517 10.580 970 1074 0.00088052
1518 10.585 1052 1167 0.00081168
1519 10.590 1121 1272 0.0007631
1520 10.595 1239 1379 0.00068889
1521 10.600 1435 1469 0.00059488
1522 10.605 1459 1567 0.00058627
1523 10.610 1676 1693 0.00050956
1524 10.615 1724 1848 0.00049603
1525 10.620 1977 2031 0.00043222
1526 10.625 2234 2246 0.00038147
1527 10.630 2506 2500 0.00034041
1528 10.635 2676 2804 0.00031888
1529 10.640 3035 3180 0.00028152
1530 10.645 3681 3665 0.00023167
1531 10.650 4075 4312 0.00020943
1532 10.655 4972 5209 0.00017177
1533 10.660 5893 6447 0.00014481
1534 10.665 7258 7521 0.00011764
1535 10.670 5779 5748 0.00014764
1536 10.675 3108 3193 0.00027411
1537 10.680 2113 2070 0.00040322
1538 10.685 1583 1587 0.00053833
1539 10.690 1382 1355 0.0006188
1540 10.695 1289 1239 0.00066085
1541 10.700 1113 1188 0.00076734
1542 10.705 1184 1176 0.00072263
1543 10.710 1166 1191 0.00073046
1544 10.715 1124 1229 0.0007589
1545 10.720 1301 1289 0.00065746
1546 10.725 1288 1365 0.00066085
1547 10.730 1358 1458 0.00062814
1548 10.735 1475 1567 0.00057785
1549 10.740 1577 1695 0.00054083
1550 10.745 1702 1843 0.00050048
1551 10.750 1817 2016 0.00047054
1552 10.755 2152 2221 0.00039682
1553 10.760 2280 2466 0.00037413
1554 10.765 2584 2765 0.00033058
1555 10.770 2796 3137 0.00030564
1556 10.775 3114 3611 0.00027411
1557 10.780 3663 4226 0.00023309
1558 10.785 4408 4982 0.00019344
1559 10.790 4871 5541 0.00017497
1560 10.795 4351 4971 0.00019616
1561 10.800 3651 4034 0.0002338
1562 10.805 3528 3766 0.00024187
1563 10.810 3822 3867 0.00022343
1564 10.815 3092 3208 0.00027594
1565 10.820 2023 2066 0.00042164
1566 10.825 1429 1504 0.0005978
1567 10.830 1286 1244 0.00066426
1568 10.835 1078 1104 0.00079349
1569 10.840 983 1019 0.00087016
1570 10.845 897 962 0.0009526
1571 10.850 858 922 0.00099513
1572 10.855 857 892 0.00099513
1573 10.860 836 868 0.00102073
1574 10.865 858 848 0.00099513
1575 10.870 802 834 0.00106102
1576 10.875 809 824 0.00105414
1577 10.880 782 815 0.00108922
1578 10.885 774 808 0.00110374
1579 10.890 812 803 0.00105414
1580 10.895 785 798 0.00108922
1581 10.900 788 794 0.00108206
1582 10.905 826 791 0.0010339
1583 10.910 711 789 0.0011973
1584 10.915 747 787 0.00114134
1585 10.920 749 786 0.00114134
1586 10.925 826 785 0.0010339
1587 10.930 794 784 0.00107498
1588 10.935 737 784 0.00115693
1589 10.940 753 784 0.00113367
1590 10.945 813 785 0.00104733
1591 10.950 729 786 0.00117283
1592 10.955 807 788 0.00105414
1593 10.960 809 790 0.00105414
1594 10.965 779 794 0.00109644
1595 10.970 765 798 0.00111856
1596 10.975 792 804 0.00107498
1597 10.980 797 812 0.00106797
1598 10.985 802 823 0.00106102
1599 10.990 858 836 0.00099513
1600 10.995 916 840 0.00092951
1601 11.000 884 814 0.00096447
1602 11.005 792 790 0.00107498
1603 11.010 793 778 0.00107498
1604 11.015 814 773 0.00104733
1605 11.020 784 772 0.00108922
1606 11.025 752 771 0.00113367
1607 11.030 837 771 0.00102073
1608 11.035 771 772 0.00110374
1609 11.040 787 776 0.00108206
1610 11.045 811 780 0.00105414
1611 11.050 794 782 0.00107498
1612 11.055 827 784 0.0010339
1613 11.060 803 787 0.00106102
1614 11.065 814 790 0.00104733
1615 11.070 866 793 0.00098269
1616 11.075 823 798 0.0010339
1617 11.080 786 804 0.00108206
1618 11.085 919 812 0.00092951
1619 11.090 783 821 0.00108922
1620 11.095 821 831 0.00104058
1621 11.100 832 844 0.00102728
1622 11.105 893 859 0.0009526
1623 11.110 840 876 0.00101424
1624 11.115 912 896 0.0009352
1625 11.120 945 919 0.0009018
1626 11.125 945 946 0.0009018
1627 11.130 1021 980 0.00083531
1628 11.135 1018 1023 0.00084016
1629 11.140 1044 1083 0.00081633
1630 11.145 1205 1172 0.00070733
1631 11.150 1233 1295 0.00069252
1632 11.155 1440 1452 0.00059199
1633 11.160 1689 1656 0.00050499
1634 11.165 1861 1925 0.00045853
1635 11.170 1932 1955 0.00044135
1636 11.175 2148 2011 0.00039682
1637 11.180 2344 2225 0.0003642
1638 11.185 2615 2500 0.00032582
1639 11.190 2874 2704 0.00029624
1640 11.195 2899 2793 0.00029421
1641 11.200 3342 3015 0.00025518
1642 11.205 3669 3355 0.00023238
1643 11.210 4060 3801 0.00021004
1644 11.215 4714 4382 0.00018066
1645 11.220 5348 5149 0.00015942
1646 11.225 6552 6200 0.00013002
1647 11.230 7887 7664 0.00010806
1648 11.235 10081 9356 8.463e-005
1649 11.240 9477 8692 9.002e-005
1650 11.245 4761 5019 0.00017921
1651 11.250 3120 2969 0.00027321
1652 11.255 2224 2104 0.00038296
1653 11.260 1843 1693 0.00046248
1654 11.265 1567 1475 0.00054336
1655 11.270 1481 1351 0.00057508
1656 11.275 1383 1279 0.00061573
1657 11.280 1320 1240 0.00064418
1658 11.285 1257 1224 0.00067817
1659 11.290 1213 1224 0.00070359
1660 11.295 1292 1239 0.00066085
1661 11.300 1315 1268 0.00064746
1662 11.305 1306 1312 0.00065077
1663 11.310 1422 1376 0.00060073
1664 11.315 1481 1470 0.00057508
1665 11.320 1608 1614 0.00053091
1666 11.325 1771 1830 0.00048092
1667 11.330 2092 2115 0.00040812
1668 11.335 2342 2462 0.0003642
1669 11.340 2704 2835 0.00031549
1670 11.345 3071 3080 0.00027778
1671 11.350 3088 3166 0.00027594
1672 11.355 3498 3359 0.00024338
1673 11.360 3758 3695 0.00022681
1674 11.365 4235 4141 0.0002012
1675 11.370 4781 4688 0.00017825
1676 11.375 5638 5346 0.00015129
1677 11.380 6449 6144 0.00013212
1678 11.385 7500 7123 0.00011366
1679 11.390 8579 8354 9.92e-005
1680 11.395 10419 9948 8.175e-005
1681 11.400 12317 12079 6.921e-005
1682 11.405 15336 14976 5.553e-005
1683 11.410 18918 18425 4.504e-005
1684 11.415 20005 18612 4.261e-005
1685 11.420 12733 11657 6.686e-005
1686 11.425 6503 6413 0.00013091
1687 11.430 4266 4039 0.0001995
1688 11.435 2954 2892 0.00028825
1689 11.440 2293 2265 0.00037125
1690 11.445 1978 1899 0.00043043
1691 11.450 1776 1672 0.00047881
1692 11.455 1486 1528 0.00057233
1693 11.460 1534 1437 0.00055625
1694 11.465 1382 1381 0.00061573
1695 11.470 1381 1351 0.00061573
1696 11.475 1326 1341 0.00064092
1697 11.480 1358 1348 0.00062814
1698 11.485 1419 1371 0.00060073
1699 11.490 1444 1409 0.00058912
1700 11.495 1607 1462 0.00053091
1701 11.500 1570 1534 0.00054336
1702 11.505 1649 1629 0.00051653
1703 11.510 1926 1752 0.00044135
1704 11.515 2048 1914 0.00041649
1705 11.520 2222 2131 0.00038296
1706 11.525 2479 2424 0.00034294
1707 11.530 2792 2800 0.00030457
1708 11.535 3194 3064 0.00026699
1709 11.540 2870 2638 0.00029624
1710 11.545 2021 1898 0.00042164
1711 11.550 1478 1455 0.00057508
1712 11.555 1284 1241 0.00066426
1713 11.560 1101 1134 0.0007716
1714 11.565 1080 1079 0.00078904
1715 11.570 1060 1052 0.00080251
1716 11.575 1032 1045 0.00082574
1717 11.580 1093 1055 0.00078025
1718 11.585 1059 1081 0.00080251
1719 11.590 1117 1123 0.0007631
1720 11.595 1104 1139 0.0007716
1721 11.600 1031 1038 0.00082574
1722 11.605 911 926 0.0009352
1723 11.610 903 866 0.00094095
1724 11.615 830 834 0.00102728
1725 11.620 819 814 0.00104058
1726 11.625 838 798 0.00101424
1727 11.630 738 782 0.00115693
1728 11.635 857 769 0.00099513
1729 11.640 795 764 0.00106797
1730 11.645 762 761 0.00111856
1731 11.650 765 758 0.00111111
1732 11.655 797 756 0.00106797
1733 11.660 842 754 0.00100781
1734 11.665 798 752 0.00106797
1735 11.670 800 750 0.00106102
1736 11.675 750 749 0.00113367
1737 11.680 802 748 0.00106102
1738 11.685 824 748 0.0010339
1739 11.690 748 747 0.00114134
1740 11.695 765 747 0.00111111
1741 11.700 770 747 0.00110374
1742 11.705 743 748 0.00114134
1743 11.710 803 751 0.00106102
1744 11.715 749 751 0.00113367
1745 11.720 789 751 0.00107498
1746 11.725 708 752 0.00120563
1747 11.730 702 752 0.00121405
1748 11.735 739 753 0.0011491
1749 11.740 854 754 0.00099513
1750 11.745 726 755 0.00117283
1751 11.750 742 757 0.0011491
1752 11.755 747 760 0.00114134
1753 11.760 783 763 0.00108922
1754 11.765 737 763 0.00115693
1755 11.770 759 758 0.00111856
1756 11.775 787 756 0.00108206
1757 11.780 781 756 0.00108922
1758 11.785 801 757 0.00106102
1759 11.790 770 758 0.00110374
1760 11.795 745 761 0.00114134
1761 11.800 845 766 0.00100781
1762 11.805 772 771 0.00110374
1763 11.810 830 779 0.00102728
1764 11.815 809 789 0.00105414
1765 11.820 844 805 0.00100781
1766 11.825 853 831 0.00099513
1767 11.830 868 873 0.00098269
1768 11.835 935 928 0.00090724
1769 11.840 999 993 0.00084999
1770 11.845 1105 1067 0.00076734
1771 11.850 1090 1151 0.00078025
1772 11.855 1236 1246 0.00068889
1773 11.860 1420 1355 0.0005978
1774 11.865 1471 1480 0.00057785
1775 11.870 1643 1626 0.00051653
1776 11.875 1832 1802 0.00046448
1777 11.880 2058 2005 0.00041311
1778 11.885 2275 2248 0.00037413
1779 11.890 2579 2553 0.00032938
1780 11.895 2977 2945 0.00028534
1781 11.900 3495 3470 0.00024338
1782 11.905 4170 4191 0.00020408
1783 11.910 4988 5110 0.00017043
1784 11.915 5479 5421 0.00015508
1785 11.920 3515 3713 0.00024187
1786 11.925 2101 2247 0.00040484
1787 11.930 1667 1601 0.00050956
1788 11.935 1347 1301 0.0006313
1789 11.940 1199 1144 0.00071111
1790 11.945 1200 1054 0.00070733
1791 11.950 1030 1000 0.00082574
1792 11.955 923 967 0.00092386
1793 11.960 961 948 0.00088577
1794 11.965 967 939 0.00088052
1795 11.970 961 939 0.00088577
1796 11.975 1007 947 0.00084505
1797 11.980 955 965 0.00089107
1798 11.985 1009 998 0.00084016
1799 11.990 1030 1055 0.00082574
1800 11.995 1204 1156 0.00070733
1801 12.000 1295 1306 0.00065746
1802 12.005 1508 1492 0.0005642
1803 12.010 1718 1708 0.00049383
1804 12.015 1935 1955 0.0004395
1805 12.020 2213 2237 0.00038447
1806 12.025 2587 2559 0.00032819
1807 12.030 2990 2928 0.00028437
1808 12.035 3546 3355 0.00023963
1809 12.040 4006 3856 0.00021188
1810 12.045 4607 4450 0.00018461
1811 12.050 5431 5170 0.00015664
1812 12.055 6454 6064 0.00013151
1813 12.060 7572 7205 0.00011222
1814 12.065 9132 8717 9.299e-005
1815 12.070 11190 10784 7.588e-005
1816 12.075 14375 13545 5.908e-005
1817 12.080 16280 15640 5.221e-005
1818 12.085 11246 11768 7.561e-005
1819 12.090 6130 6385 0.00013873
1820 12.095 3809 3881 0.00022277
1821 12.100 2824 2791 0.00030036
1822 12.105 2549 2306 0.000333
1823 12.110 2142 2012 0.00039682
1824 12.115 1569 1512 0.00054083
1825 12.120 1261 1274 0.00067465
1826 12.125 1136 1140 0.00074651
1827 12.130 1061 1053 0.00080251
1828 12.135 985 989 0.00086505
1829 12.140 939 941 0.00090724
1830 12.145 918 903 0.00092386
1831 12.150 855 872 0.00099513
1832 12.155 868 848 0.00097656
1833 12.160 851 827 0.00100144
1834 12.165 781 810 0.00108922
1835 12.170 789 795 0.00107498
1836 12.175 798 783 0.00106797
1837 12.180 755 772 0.00112608
1838 12.185 770 763 0.00110374
1839 12.190 749 755 0.00113367
1840 12.195 734 749 0.00115693
1841 12.200 710 743 0.0011973
1842 12.205 787 738 0.00108206
1843 12.210 707 734 0.0011973
1844 12.215 727 730 0.00116484
1845 12.220 657 727 0.00129393
1846 12.225 734 725 0.00115693
1847 12.230 721 723 0.0011809
1848 12.235 765 722 0.00111111
1849 12.240 716 722 0.00118906
1850 12.245 708 723 0.0011973
1851 12.250 685 725 0.00123983
1852 12.255 737 728 0.0011491
1853 12.260 744 734 0.00114134
1854 12.265 697 743 0.00122255
1855 12.270 721 750 0.0011809
1856 12.275 671 737 0.00126645
1857 12.280 706 707 0.00120563
1858 12.285 718 687 0.0011809
1859 12.290 712 670 0.00118906
1860 12.295 648 662 0.00131275
1861 12.300 678 659 0.00124861
1862 12.305 661 657 0.00128467
1863 12.310 639 656 0.00133198
1864 12.315 688 656 0.00123115
1865 12.320 671 655 0.00126645
1866 12.325 660 654 0.00128467
1867 12.330 635 653 0.00133198
1868 12.335 647 652 0.00131275
1869 12.340 650 652 0.00130329
1870 12.345 663 651 0.00128467
1871 12.350 657 651 0.00129393
1872 12.355 611 651 0.00139229
1873 12.360 658 651 0.00129393
1874 12.365 683 651 0.00123983
1875 12.370 630 652 0.00135164
1876 12.375 604 652 0.00140274
1877 12.380 658 653 0.00129393
1878 12.385 623 654 0.00136164
1879 12.390 661 655 0.00128467
1880 12.395 641 656 0.00132231
1881 12.400 678 658 0.00124861
1882 12.405 612 661 0.00138196
1883 12.410 633 665 0.00134176
1884 12.415 633 669 0.00134176
1885 12.420 621 675 0.00136164
1886 12.425 669 680 0.00126645
1887 12.430 627 676 0.00135164
1888 12.435 630 665 0.00135164
1889 12.440 665 658 0.00127551
1890 12.445 632 655 0.00134176
1891 12.450 623 655 0.00136164
1892 12.455 656 656 0.00129393
1893 12.460 668 659 0.00126645
1894 12.465 669 665 0.00126645
1895 12.470 646 675 0.00131275
1896 12.475 676 689 0.00125748
1897 12.480 701 706 0.00121405
1898 12.485 735 727 0.00115693
1899 12.490 755 751 0.00112608
1900 12.495 782 779 0.00108206
1901 12.500 798 811 0.00106102
1902 12.505 816 847 0.00104058
1903 12.510 906 890 0.0009352
1904 12.515 964 940 0.00088052
1905 12.520 1027 1001 0.00082574
1906 12.525 1128 1075 0.00075061
1907 12.530 1213 1169 0.00069987
1908 12.535 1303 1289 0.00065077
1909 12.540 1415 1447 0.0005978
1910 12.545 1683 1650 0.00050499
1911 12.550 1845 1845 0.0004605
1912 12.555 1754 1741 0.00048303
1913 12.560 1203 1308 0.00070359
1914 12.565 964 1010 0.00088052
1915 12.570 817 866 0.00104058
1916 12.575 744 794 0.00114134
1917 12.580 735 756 0.00115693
1918 12.585 714 736 0.00118906
1919 12.590 716 725 0.0011809
1920 12.595 746 722 0.00113367
1921 12.600 749 724 0.00113367
1922 12.605 743 730 0.00114134
1923 12.610 707 742 0.0011973
1924 12.615 761 760 0.00111111
1925 12.620 785 786 0.00108206
1926 12.625 859 822 0.00098888
1927 12.630 863 867 0.00098269
1928 12.635 870 890 0.00097656
1929 12.640 811 821 0.00104733
1930 12.645 700 735 0.00121405
1931 12.650 640 691 0.00132231
1932 12.655 632 671 0.00134176
1933 12.660 628 662 0.00135164
1934 12.665 655 658 0.00129393
1935 12.670 637 658 0.00133198
1936 12.675 629 661 0.00135164
1937 12.680 613 667 0.00138196
1938 12.685 611 677 0.00138196
1939 12.690 609 691 0.00139229
1940 12.695 637 707 0.00133198
1941 12.700 650 709 0.00130329
1942 12.705 589 675 0.0014348
1943 12.710 585 644 0.00144573
1944 12.715 559 630 0.00151403
1945 12.720 632 623 0.00134176
1946 12.725 596 622 0.00142399
1947 12.730 582 622 0.00145679
1948 12.735 605 625 0.00140274
1949 12.740 564 629 0.00150231
1950 12.745 646 633 0.00131275
1951 12.750 574 640 0.00147929
1952 12.755 654 647 0.00129393
1953 12.760 624 656 0.00136164
1954 12.765 676 667 0.00125748
1955 12.770 668 680 0.00126645
1956 12.775 698 697 0.00121405
1957 12.780 669 718 0.00126645
1958 12.785 745 746 0.00114134
1959 12.790 746 784 0.00113367
1960 12.795 765 835 0.00111111
1961 12.800 917 888 0.00092386
1962 12.805 851 862 0.00099513
1963 12.810 693 744 0.00122255
1964 12.815 590 670 0.0014348
1965 12.820 626 636 0.00135164
1966 12.825 602 619 0.00140274
1967 12.830 580 609 0.00146798
1968 12.835 578 604 0.00146798
1969 12.840 597 601 0.00142399
1970 12.845 543 600 0.00156228
1971 12.850 562 601 0.00151403
1972 12.855 591 603 0.0014348
1973 12.860 561 606 0.00151403
1974 12.865 601 611 0.00141331
1975 12.870 609 616 0.00139229
1976 12.875 668 622 0.00126645
1977 12.880 614 629 0.00138196
1978 12.885 687 639 0.00123115
1979 12.890 675 651 0.00125748
1980 12.895 685 665 0.00123983
1981 12.900 740 684 0.0011491
1982 12.905 809 708 0.00104733
1983 12.910 856 739 0.00098888
1984 12.915 884 780 0.00095851
1985 12.920 932 817 0.00090724
1986 12.925 835 789 0.00101424
1987 12.930 700 701 0.00121405
1988 12.935 656 647 0.00129393
1989 12.940 649 622 0.00130329
1990 12.945 596 611 0.00142399
1991 12.950 575 607 0.00147929
1992 12.955 548 607 0.00155
1993 12.960 522 601 0.00162591
1994 12.965 572 587 0.00147929
1995 12.970 558 579 0.00151403
1996 12.975 548 574 0.00155
1997 12.980 569 571 0.00149074
1998 12.985 581 569 0.00145679
1999 12.990 559 567 0.00151403
2000 12.995 537 566 0.0015747
2001 13.000 562 565 0.00151403
2002 13.005 517 564 0.0016391
2003 13.010 583 563 0.00145679
2004 13.015 536 562 0.00158728
2005 13.020 543 561 0.00156228
2006 13.025 514 561 0.00165246
2007 13.030 570 560 0.00149074
2008 13.035 531 560 0.0016
2009 13.040 506 559 0.00167966
2010 13.045 561 559 0.00151403
2011 13.050 554 559 0.00152588
2012 13.055 550 559 0.00153787
2013 13.060 522 559 0.00162591
2014 13.065 544 559 0.00156228
2015 13.070 548 558 0.00155
2016 13.075 557 558 0.00152588
2017 13.080 513 558 0.00165246
2018 13.085 555 558 0.00152588
2019 13.090 551 558 0.00153787
2020 13.095 528 559 0.00161288
2021 13.100 530 559 0.0016
2022 13.105 530 560 0.0016
2023 13.110 619 561 0.00137174
2024 13.115 513 563 0.00165246
2025 13.120 521 565 0.00162591
2026 13.125 562 568 0.00151403
2027 13.130 585 572 0.00144573
2028 13.135 545 576 0.00155
2029 13.140 556 584 0.00152588
2030 13.145 576 596 0.00146798
2031 13.150 622 613 0.00136164
2032 13.155 621 635 0.00136164
2033 13.160 679 660 0.00124861
2034 13.165 691 691 0.00123115
2035 13.170 714 726 0.00118906
2036 13.175 687 769 0.00123115
2037 13.180 804 818 0.00105414
2038 13.185 841 870 0.00100781
2039 13.190 947 914 0.00089641
2040 13.195 977 956 0.00087016
2041 13.200 1036 1023 0.00081633
2042 13.205 1161 1124 0.00073046
2043 13.210 1297 1270 0.0006541
2044 13.215 1517 1486 0.00055888
2045 13.220 1774 1780 0.00047881
2046 13.225 1774 1783 0.00047881
2047 13.230 1253 1191 0.00067465
2048 13.235 945 884 0.00089641
2049 13.240 805 754 0.00105414
2050 13.245 691 674 0.00123115
2051 13.250 633 627 0.00134176
2052 13.255 585 600 0.00144573
2053 13.260 588 583 0.00144573
2054 13.265 591 572 0.0014348
2055 13.270 536 564 0.00158728
2056 13.275 601 558 0.00141331
2057 13.280 565 554 0.00150231
2058 13.285 551 550 0.00153787
2059 13.290 563 548 0.00150231
2060 13.295 552 546 0.00153787
2061 13.300 524 544 0.00161288
2062 13.305 557 543 0.00152588
2063 13.310 512 543 0.00165246
2064 13.315 556 542 0.00152588
2065 13.320 511 543 0.00165246
2066 13.325 533 543 0.00158728
2067 13.330 513 544 0.00165246
2068 13.335 554 545 0.00152588
2069 13.340 556 546 0.00152588
2070 13.345 551 549 0.00153787
2071 13.350 529 552 0.0016
2072 13.355 531 556 0.0016
2073 13.360 563 562 0.00150231
2074 13.365 569 570 0.00149074
2075 13.370 559 579 0.00151403
2076 13.375 557 577 0.00152588
2077 13.380 563 557 0.00150231
2078 13.385 546 542 0.00155
2079 13.390 543 534 0.00156228
2080 13.395 548 530 0.00155
2081 13.400 483 527 0.00175067
2082 13.405 513 526 0.00165246
2083 13.410 522 525 0.00162591
2084 13.415 481 524 0.00176541
2085 13.420 539 524 0.0015747
2086 13.425 512 524 0.00165246
2087 13.430 504 524 0.00167966
2088 13.435 558 525 0.00151403
2089 13.440 504 527 0.00167966
2090 13.445 544 530 0.00156228
2091 13.450 545 534 0.00155
2092 13.455 540 539 0.0015747
2093 13.460 559 545 0.00151403
2094 13.465 539 552 0.0015747
2095 13.470 558 560 0.00151403
2096 13.475 586 569 0.00144573
2097 13.480 573 580 0.00147929
2098 13.485 609 593 0.00139229
2099 13.490 606 610 0.00140274
2100 13.495 639 632 0.00132231
2101 13.500 663 660 0.00127551
2102 13.505 709 699 0.0011973
2103 13.510 742 749 0.00114134
2104 13.515 806 787 0.00105414
2105 13.520 699 727 0.00121405
2106 13.525 599 626 0.00141331
2107 13.530 564 573 0.00150231
2108 13.535 557 548 0.00152588
2109 13.540 537 535 0.0015747
2110 13.545 565 527 0.00150231
2111 13.550 519 522 0.0016391
2112 13.555 511 519 0.00166597
2113 13.560 542 516 0.00156228
2114 13.565 532 514 0.0016
2115 13.570 504 513 0.00167966
2116 13.575 482 511 0.00176541
2117 13.580 512 510 0.00165246
2118 13.585 559 510 0.00151403
2119 13.590 456 509 0.00185791
2120 13.595 509 508 0.00166597
2121 13.600 457 508 0.00185791
2122 13.605 505 507 0.00167966
2123 13.610 518 507 0.0016391
2124 13.615 496 507 0.00170753
2125 13.620 553 506 0.00153787
2126 13.625 505 506 0.00167966
2127 13.630 480 506 0.00176541
2128 13.635 479 506 0.00176541
2129 13.640 470 507 0.00181077
2130 13.645 511 507 0.00166597
2131 13.650 518 508 0.0016391
2132 13.655 496 509 0.00170753
2133 13.660 477 509 0.00178034
2134 13.665 454 510 0.00187403
2135 13.670 542 512 0.00156228
2136 13.675 515 514 0.00165246
2137 13.680 488 518 0.00173611
2138 13.685 519 522 0.0016391
2139 13.690 535 528 0.00158728
2140 13.695 515 534 0.00165246
2141 13.700 487 541 0.00175067
2142 13.705 572 550 0.00147929
2143 13.710 548 560 0.00155
2144 13.715 467 573 0.00182628
2145 13.720 554 588 0.00153787
2146 13.725 561 607 0.00151403
2147 13.730 598 631 0.00142399
2148 13.735 651 663 0.00130329
2149 13.740 699 706 0.00121405
2150 13.745 680 761 0.00124861
2151 13.750 711 790 0.0011973
2152 13.755 664 707 0.00127551
2153 13.760 601 623 0.00141331
2154 13.765 580 588 0.00146798
2155 13.770 636 576 0.00133198
2156 13.775 575 576 0.00147929
2157 13.780 612 585 0.00139229
2158 13.785 592 601 0.0014348
2159 13.790 649 630 0.00130329
2160 13.795 666 670 0.00127551
2161 13.800 736 714 0.00115693
2162 13.805 753 745 0.00112608
2163 13.810 792 776 0.00107498
2164 13.815 893 825 0.0009526
2165 13.820 966 890 0.00088052
2166 13.825 1050 972 0.00080708
2167 13.830 1102 1072 0.0007716
2168 13.835 1283 1197 0.00066085
2169 13.840 1509 1354 0.00056153
2170 13.845 1688 1556 0.00050272
2171 13.850 2001 1808 0.00042512
2172 13.855 2230 2116 0.00038147
2173 13.860 2747 2469 0.00030887
2174 13.865 2767 2435 0.00030671
2175 13.870 1847 1669 0.0004605
2176 13.875 1176 1109 0.00072263
2177 13.880 944 852 0.0009018
2178 13.885 817 725 0.00104058
2179 13.890 687 656 0.00123983
2180 13.895 632 613 0.00134176
2181 13.900 643 586 0.00132231
2182 13.905 608 567 0.00139229
2183 13.910 553 554 0.00153787
2184 13.915 553 545 0.00153787
2185 13.920 534 540 0.00158728
2186 13.925 551 537 0.00153787
2187 13.930 586 536 0.00144573
2188 13.935 575 538 0.00147929
2189 13.940 551 542 0.00153787
2190 13.945 536 548 0.00158728
2191 13.950 577 555 0.00146798
2192 13.955 643 565 0.00132231
2193 13.960 607 577 0.00140274
2194 13.965 665 592 0.00127551
2195 13.970 660 611 0.00128467
2196 13.975 720 636 0.0011809
2197 13.980 667 667 0.00127551
2198 13.985 801 708 0.00106102
2199 13.990 841 752 0.00100781
2200 13.995 852 770 0.00099513
2201 14.000 857 747 0.00098888
2202 14.005 849 728 0.00100144
2203 14.010 682 668 0.00124861
2204 14.015 622 589 0.00136164
2205 14.020 596 549 0.00142399
2206 14.025 583 530 0.00145679
2207 14.030 498 520 0.00170753
2208 14.035 511 515 0.00166597
2209 14.040 518 512 0.0016391
2210 14.045 523 510 0.00162591
2211 14.050 551 510 0.00153787
2212 14.055 509 511 0.00166597
2213 14.060 580 514 0.00146798
2214 14.065 567 519 0.00150231
2215 14.070 506 525 0.00167966
2216 14.075 518 534 0.0016391
2217 14.080 556 545 0.00152588
2218 14.085 574 560 0.00147929
2219 14.090 591 581 0.0014348
2220 14.095 623 606 0.00136164
2221 14.100 689 636 0.00123115
2222 14.105 763 672 0.00111111
2223 14.110 733 715 0.00115693
2224 14.115 834 765 0.00102073
2225 14.120 891 824 0.0009526
2226 14.125 1065 897 0.00079798
2227 14.130 1122 997 0.0007589
2228 14.135 1263 1073 0.00067116
2229 14.140 1272 1077 0.00066769
2230 14.145 1322 1132 0.00064418
2231 14.150 1399 1188 0.00060666
2232 14.155 1508 1242 0.0005642
2233 14.160 1332 1235 0.00063769
2234 14.165 1143 1084 0.00074245
2235 14.170 992 948 0.00085496
2236 14.175 928 900 0.00091827
2237 14.180 815 904 0.00104058
2238 14.185 847 901 0.00100144
2239 14.190 830 872 0.00102073
2240 14.195 836 875 0.00101424
2241 14.200 842 904 0.00100781
2242 14.205 832 929 0.00102073
2243 14.210 892 972 0.0009526
2244 14.215 995 1040 0.00085496
2245 14.220 1031 1121 0.00082574
2246 14.225 1096 1183 0.00077591
2247 14.230 1132 1164 0.00075061
2248 14.235 924 1042 0.00091827
2249 14.240 827 896 0.00102728
2250 14.245 730 791 0.00116484
2251 14.250 703 729 0.00120563
2252 14.255 679 698 0.00124861
2253 14.260 696 687 0.00122255
2254 14.265 736 691 0.00115693
2255 14.270 706 706 0.00120563
2256 14.275 745 731 0.00114134
2257 14.280 823 769 0.0010339
2258 14.285 861 822 0.00098888
2259 14.290 898 894 0.00094675
2260 14.295 1006 996 0.00084505
2261 14.300 1142 1136 0.00074245
2262 14.305 1260 1275 0.00067465
2263 14.310 1239 1157 0.00068529
2264 14.315 759 841 0.00111856
2265 14.320 634 670 0.00134176
2266 14.325 579 592 0.00146798
2267 14.330 570 553 0.00149074
2268 14.335 533 530 0.0016
2269 14.340 517 515 0.0016391
2270 14.345 462 505 0.00184199
2271 14.350 432 498 0.00197531
2272 14.355 518 493 0.0016391
2273 14.360 494 489 0.00172173
2274 14.365 496 486 0.00172173
2275 14.370 434 484 0.00195787
2276 14.375 447 483 0.0019069
2277 14.380 515 482 0.00165246
2278 14.385 452 481 0.00187403
2279 14.390 486 482 0.00175067
2280 14.395 532 484 0.0016
2281 14.400 524 488 0.00162591
2282 14.405 504 494 0.00169351
2283 14.410 523 501 0.00162591
2284 14.415 480 510 0.00176541
2285 14.420 568 520 0.00149074
2286 14.425 533 532 0.0016
2287 14.430 613 547 0.00138196
2288 14.435 561 566 0.00151403
2289 14.440 620 589 0.00137174
2290 14.445 678 620 0.00125748
2291 14.450 721 662 0.0011809
2292 14.455 823 724 0.0010339
2293 14.460 853 818 0.00099513
2294 14.465 923 850 0.00092386
2295 14.470 807 742 0.00105414
2296 14.475 694 666 0.00122255
2297 14.480 610 584 0.00139229
2298 14.485 592 548 0.0014348
2299 14.490 544 536 0.00156228
2300 14.495 541 537 0.0015747
2301 14.500 568 544 0.00149074
2302 14.505 583 556 0.00145679
2303 14.510 604 570 0.00140274
2304 14.515 652 587 0.00130329
2305 14.520 666 609 0.00127551
2306 14.525 723 636 0.00117283
2307 14.530 660 670 0.00128467
2308 14.535 819 712 0.00104058
2309 14.540 831 763 0.00102073
2310 14.545 883 822 0.00096447
2311 14.550 964 882 0.00088052
2312 14.555 991 912 0.00085999
2313 14.560 1030 873 0.00082574
2314 14.565 864 781 0.00098269
2315 14.570 770 698 0.00110374
2316 14.575 692 645 0.00123115
2317 14.580 656 618 0.00129393
2318 14.585 652 609 0.00130329
2319 14.590 627 612 0.00135164
2320 14.595 645 627 0.00132231
2321 14.600 718 654 0.0011809
2322 14.605 785 690 0.00108206
2323 14.610 684 694 0.00123983
2324 14.615 711 616 0.0011973
2325 14.620 577 546 0.00147929
2326 14.625 472 510 0.00179546
2327 14.630 537 492 0.00158728
2328 14.635 492 481 0.00172173
2329 14.640 465 475 0.00182628
2330 14.645 497 471 0.00170753
2331 14.650 440 468 0.00192367
2332 14.655 438 467 0.00194065
2333 14.660 440 466 0.00192367
2334 14.665 419 466 0.00202906
2335 14.670 478 467 0.00178034
2336 14.675 463 470 0.00184199
2337 14.680 484 473 0.00175067
2338 14.685 454 475 0.00187403
2339 14.690 459 473 0.00185791
2340 14.695 434 472 0.00195787
2341 14.700 453 474 0.00187403
2342 14.705 459 478 0.00185791
2343 14.710 481 483 0.00176541
2344 14.715 459 491 0.00185791
2345 14.720 501 500 0.00169351
2346 14.725 500 512 0.00169351
2347 14.730 507 529 0.00167966
2348 14.735 541 551 0.0015747
2349 14.740 560 578 0.00151403
2350 14.745 511 574 0.00166597
2351 14.750 504 522 0.00169351
2352 14.755 474 487 0.00179546
2353 14.760 463 471 0.00184199
2354 14.765 438 464 0.00194065
2355 14.770 451 460 0.00189036
2356 14.775 431 458 0.00197531
2357 14.780 476 457 0.00178034
2358 14.785 463 457 0.00184199
2359 14.790 420 458 0.00202906
2360 14.795 467 460 0.00182628
2361 14.800 446 463 0.0019069
2362 14.805 487 468 0.00173611
2363 14.810 496 473 0.00170753
2364 14.815 450 479 0.00189036
2365 14.820 469 487 0.00181077
2366 14.825 454 495 0.00187403
2367 14.830 497 504 0.00170753
2368 14.835 514 513 0.00165246
2369 14.840 529 526 0.00161288
2370 14.845 517 541 0.0016391
2371 14.850 570 562 0.00149074
2372 14.855 585 587 0.00145679
2373 14.860 560 616 0.00151403
2374 14.865 572 638 0.00147929
2375 14.870 634 625 0.00134176
2376 14.875 584 575 0.00145679
2377 14.880 548 531 0.00155
2378 14.885 506 505 0.00167966
2379 14.890 548 492 0.00155
2380 14.895 477 485 0.00178034
2381 14.900 511 483 0.00166597
2382 14.905 510 483 0.00166597
2383 14.910 523 484 0.00162591
2384 14.915 506 480 0.00167966
2385 14.920 482 472 0.00176541
2386 14.925 477 465 0.00178034
2387 14.930 480 462 0.00176541
2388 14.935 431 461 0.00197531
2389 14.940 509 460 0.00166597
2390 14.945 531 461 0.0016
2391 14.950 490 463 0.00173611
2392 14.955 464 466 0.00182628
2393 14.960 462 470 0.00184199
2394 14.965 479 476 0.00176541
2395 14.970 483 484 0.00176541
2396 14.975 477 493 0.00178034
2397 14.980 519 505 0.0016391
2398 14.985 503 519 0.00169351
2399 14.990 548 537 0.00155
2400 14.995 564 560 0.00150231
2401 15.000 593 586 0.00540657
2402 15.005 594 618 0.00400577
2403 15.010 639 660 0.00371802
2404 15.015 697 715 0.00338021
2405 15.020 729 779 0.00326531
2406 15.025 842 830 0.00279947
2407 15.030 796 830 0.00298606
2408 15.035 787 827 0.00301896
2409 15.040 830 862 0.00285968
2410 15.045 887 930 0.00268464
2411 15.050 966 1026 0.00245074
2412 15.055 1073 1139 0.00220415
2413 15.060 1153 1210 0.00204746
2414 15.065 1166 1186 0.00202906
2415 15.070 1162 1181 0.00204746
2416 15.075 1304 1240 0.00181077
2417 15.080 1435 1333 0.00165246
2418 15.085 1506 1394 0.0015747
2419 15.090 1487 1320 0.00158728
2420 15.095 1184 1110 0.00199298
2421 15.100 939 901 0.00252519
2422 15.105 772 759 0.00305241
2423 15.110 716 671 0.00330295
2424 15.115 641 617 0.00367309
2425 15.120 607 585 0.00390625
2426 15.125 565 567 0.00421656
2427 15.130 565 560 0.00421656
2428 15.135 557 562 0.00427186
2429 15.140 569 569 0.00416233
2430 15.145 618 583 0.00381039
2431 15.150 616 602 0.00385788
2432 15.155 621 627 0.00381039
2433 15.160 641 659 0.00367309
2434 15.165 721 701 0.00326531
2435 15.170 757 755 0.003121
2436 15.175 842 827 0.00279947
2437 15.180 900 926 0.00262985
2438 15.185 1055 1057 0.00224613
2439 15.190 1181 1177 0.0020109
2440 15.195 1103 1067 0.00214335
2441 15.200 840 803 0.00282933
2442 15.205 695 661 0.00341986
2443 15.210 613 603 0.00385788
2444 15.215 588 581 0.00400577
2445 15.220 624 577 0.00381039
2446 15.225 578 583 0.00410914
2447 15.230 608 599 0.00390625
2448 15.235 644 622 0.00367309
2449 15.240 692 654 0.00341986
2450 15.245 745 698 0.00319193
2451 15.250 777 758 0.00305241
2452 15.255 852 843 0.00277008
2453 15.260 950 955 0.0025
2454 15.265 1064 1023 0.00222499
2455 15.270 883 864 0.00268464
2456 15.275 705 713 0.00334124
2457 15.280 659 666 0.00358564
2458 15.285 646 667 0.00367309
2459 15.290 702 692 0.00338021
2460 15.295 748 733 0.00315617
2461 15.300 754 788 0.003121
2462 15.305 856 859 0.00277008
2463 15.310 910 949 0.00260308
2464 15.315 1063 1065 0.00222499
2465 15.320 1194 1214 0.00197531
2466 15.325 1364 1405 0.00173611
2467 15.330 1525 1627 0.00155
2468 15.335 1827 1773 0.00129393
2469 15.340 1596 1587 0.00147929
2470 15.345 1135 1216 0.00208503
2471 15.350 944 980 0.0025
2472 15.355 857 873 0.00277008
2473 15.360 821 837 0.00289051
2474 15.365 758 842 0.003121
2475 15.370 833 867 0.00282933
2476 15.375 834 883 0.00282933
2477 15.380 799 846 0.00295369
2478 15.385 754 761 0.003121
2479 15.390 669 670 0.00354308
2480 15.395 580 596 0.00405696
2481 15.400 551 550 0.00427186
2482 15.405 496 522 0.00475624
2483 15.410 487 505 0.00482253
2484 15.415 482 493 0.00489021
2485 15.420 455 482 0.00517572
2486 15.425 476 472 0.00495933
2487 15.430 461 465 0.00510204
2488 15.435 432 460 0.00548697
2489 15.440 446 458 0.00532793
2490 15.445 446 456 0.00532793
2491 15.450 452 456 0.005251
2492 15.455 410 456 0.00573921
2493 15.460 428 458 0.00548697
2494 15.465 421 462 0.00556917
2495 15.470 447 466 0.005251
2496 15.475 461 462 0.00510204
2497 15.480 464 449 0.00510204
2498 15.485 420 440 0.00565323
2499 15.490 446 436 0.00532793
2500 15.495 412 434 0.00573921
2501 15.500 427 433 0.00556917
2502 15.505 442 433 0.00532793
2503 15.510 434 433 0.00540657
2504 15.515 458 434 0.00517572
2505 15.520 443 435 0.00532793
2506 15.525 430 436 0.00548697
2507 15.530 429 438 0.00548697
2508 15.535 464 440 0.00510204
2509 15.540 441 444 0.00532793
2510 15.545 456 449 0.00517572
2511 15.550 446 455 0.00532793
2512 15.555 494 462 0.00475624
2513 15.560 454 463 0.00517572
2514 15.565 469 451 0.00502993
2515 15.570 427 440 0.00556917
2516 15.575 441 435 0.00532793
2517 15.580 434 432 0.00540657
2518 15.585 399 431 0.00591716
2519 15.590 420 430 0.00565323
2520 15.595 413 431 0.00573921
2521 15.600 429 431 0.00548697
2522 15.605 443 432 0.00532793
2523 15.610 417 433 0.00565323
2524 15.615 429 436 0.00548697
2525 15.620 428 439 0.00548697
2526 15.625 443 443 0.00532793
2527 15.630 440 449 0.00532793
2528 15.635 428 456 0.00548697
2529 15.640 470 465 0.00502993
2530 15.645 485 476 0.00489021
2531 15.650 517 492 0.00456538
2532 15.655 532 513 0.00444444
2533 15.660 602 540 0.00390625
2534 15.665 608 572 0.00385788
2535 15.670 674 611 0.00350128
2536 15.675 726 653 0.00322831
2537 15.680 782 687 0.00301896
2538 15.685 760 695 0.00308642
2539 15.690 769 693 0.00305241
2540 15.695 816 711 0.00289051
2541 15.700 819 759 0.00289051
2542 15.705 915 844 0.00257672
2543 15.710 1064 982 0.00222499
2544 15.715 1126 1101 0.00208503
2545 15.720 870 833 0.00271267
2546 15.725 678 627 0.00346021
2547 15.730 617 562 0.00381039
2548 15.735 568 541 0.00416233
2549 15.740 573 527 0.00410914
2550 15.745 519 510 0.00456538
2551 15.750 479 497 0.00495933
2552 15.755 493 493 0.00475624
2553 15.760 472 497 0.00495933
2554 15.765 477 506 0.00495933
2555 15.770 502 521 0.00469131
2556 15.775 497 541 0.00475624
2557 15.780 555 568 0.00427186
2558 15.785 561 602 0.00421656
2559 15.790 576 643 0.00410914
2560 15.795 620 689 0.00381039
2561 15.800 678 729 0.00346021
2562 15.805 716 748 0.00330295
2563 15.810 721 754 0.00326531
2564 15.815 746 776 0.00315617
2565 15.820 850 817 0.00277008
2566 15.825 847 836 0.00277008
2567 15.830 854 822 0.00277008
2568 15.835 868 836 0.00271267
2569 15.840 902 853 0.00260308
2570 15.845 831 786 0.00282933
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# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set.
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./