##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File 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 core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_audit_creation_method     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2007-07-09
_journal_date_accepted     2007-07-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o510
_journal_page_last     o513
_journal_paper_category     FO
_journal_coeditor_code     SK3149
_publ_contact_author_name
;
Dr Christopher Glidewell
;
_publ_contact_author_address
;
University of St Andrews,
Fife KY16 9ST, UK
;
_publ_contact_author_email     cg@st-andrews.ac.uk
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
Two isomeric reaction products: hydrogen-bonded sheets in methyl
4-(5-amino-3-phenyl-1H-pyrazol-1-yl)-3-nitrobenzoate and
hydrogen-bonded chains of edge-fused rings in methyl
3-nitro-4-[(5-phenyl-1H-pyrazol-3-yl)amino]benzoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Portilla, Jaime' .
;    Departamento de Química,
     Universidad de Valle, AA 25360 Cali, Colombia
;
    'Mata, Ernesto G.' .
;     CONICET -- Facultad de Ciencias Bioquímicas y Farmacéuticas,
      Universidad Nacional de Rosario,
      Suipacha 531, S2002LRK, Argentina
;
    'Cobo, Justo' .
;  Departamento de Química Inorgánica y Orgánica
   Universidad de Jaén
   23071 Jaén
   Spain
;
    'Low, John N.' .
;    Department of Chemistry, University of Aberdeen,
     Meston Walk, Old Aberdeen AB24 3UE, Scotland
;
    'Glidewell, Christopher' .
;    School of Chemistry, University of St Andrews,
     Fife KY16 9ST, Scotland
;
data_I
_chemical_name_systematic
;
methyl 4-(5-amino-3-phenyl-1H-pyrazol-1-yl)-3-nitrobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 N4 O4'
_chemical_formula_sum     'C17 H14 N4 O4'
_chemical_formula_iupac     'C17 H14 N4 O4'
_chemical_formula_weight     338.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     12.3516(8)
_cell_length_b     7.5202(4)
_cell_length_c     17.1564(13)
_cell_angle_alpha     90.00
_cell_angle_beta     100.699(5)
_cell_angle_gamma     90.00
_cell_volume     1565.90(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3597
_cell_measurement_theta_min     3.19
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.435
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.951
_exptl_absorpt_correction_T_max     0.980
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker--Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     37526
_diffrn_reflns_av_R_equivalents     0.0569
_diffrn_reflns_av_sigmaI/netI     0.0356
_diffrn_reflns_theta_min     3.19
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_decay_%     0
_reflns_number_total     3597
_reflns_number_gt     2266
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1030
_refine_ls_R_factor_gt     0.0564
_refine_ls_wR_factor_gt     0.1403
_refine_ls_wR_factor_ref     0.1775
_refine_ls_goodness_of_fit_ref     1.080
_refine_ls_restrained_S_all     1.080
_refine_ls_number_reflns     3597
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0883P)²+0.9526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.331
_refine_diff_density_min     -0.389
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution
               'SIR2004 (Burla et al.,  2005) and WinGX (Farrugia, 1999)'
_computing_structure_refinement
                         'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.70074(15) 0.6050(3) 0.23515(10) 0.0254(4) Uani d . 1 . .
    C C11 0.72777(18) 0.5683(3) 0.31736(13) 0.0238(5) Uani d . 1 . .
    C C12 0.65260(17) 0.4875(3) 0.35802(13) 0.0242(5) Uani d . 1 . .
    N N12 0.54487(16) 0.4217(3) 0.31786(12) 0.0298(5) Uani d . 1 . .
    O O121 0.53573(13) 0.3643(2) 0.24990(10) 0.0343(4) Uani d . 1 . .
    O O122 0.46921(14) 0.4242(3) 0.35533(11) 0.0457(5) Uani d . 1 . .
    C C13 0.67791(19) 0.4603(3) 0.43961(13) 0.0265(5) Uani d . 1 . .
    C C141 0.81336(19) 0.4758(3) 0.56763(13) 0.0268(5) Uani d . 1 . .
    O O141 0.90419(14) 0.5090(2) 0.60530(9) 0.0362(4) Uani d . 1 . .
    O O142 0.73193(14) 0.4072(2) 0.59859(9) 0.0337(4) Uani d . 1 . .
    C C142 0.7569(2) 0.3743(4) 0.68303(14) 0.0403(6) Uani d . 1 . .
    C C14 0.78084(18) 0.5075(3) 0.48066(13) 0.0240(5) Uani d . 1 . .
    C C15 0.85666(18) 0.5852(3) 0.44046(13) 0.0262(5) Uani d . 1 . .
    C C16 0.83036(18) 0.6158(3) 0.35967(13) 0.0263(5) Uani d . 1 . .
    N N2 0.75934(15) 0.5266(2) 0.18323(11) 0.0260(4) Uani d . 1 . .
    C C3 0.70062(18) 0.5674(3) 0.11141(13) 0.0256(5) Uani d . 1 . .
    C C31 0.73660(19) 0.5066(3) 0.03907(13) 0.0262(5) Uani d . 1 . .
    C C32 0.8428(2) 0.4419(3) 0.04009(14) 0.0312(6) Uani d . 1 . .
    C C33 0.8727(2) 0.3790(4) -0.02855(14) 0.0355(6) Uani d . 1 . .
    C C34 0.7980(2) 0.3806(3) -0.09988(14) 0.0355(6) Uani d . 1 . .
    C C35 0.6933(2) 0.4464(3) -0.10232(14) 0.0334(6) Uani d . 1 . .
    C C36 0.6626(2) 0.5094(3) -0.03337(13) 0.0304(5) Uani d . 1 . .
    C C4 0.60744(18) 0.6703(3) 0.11715(13) 0.0264(5) Uani d . 1 . .
    C C5 0.61022(18) 0.6951(3) 0.19633(13) 0.0256(5) Uani d . 1 . .
    N N5 0.54292(16) 0.7858(3) 0.23935(11) 0.0306(5) Uani d . 1 . .
    H H13 0.6249 0.4098 0.4668 0.032 Uiso calc R 1 . .
    H H14A 0.8229 0.2996 0.6956 0.060 Uiso calc R 1 . .
    H H145 0.6947 0.3132 0.6993 0.060 Uiso calc R 1 . .
    H H1C 0.7702 0.4876 0.7114 0.060 Uiso calc R 1 . .
    H H15 0.9274 0.6177 0.4689 0.031 Uiso calc R 1 . .
    H H16 0.8829 0.6696 0.3331 0.032 Uiso calc R 1 . .
    H H32 0.8949 0.4410 0.0884 0.037 Uiso calc R 1 . .
    H H33 0.9450 0.3343 -0.0270 0.043 Uiso calc R 1 . .
    H H34 0.8190 0.3365 -0.1468 0.043 Uiso calc R 1 . .
    H H35 0.6422 0.4488 -0.1511 0.040 Uiso calc R 1 . .
    H H36 0.5903 0.5549 -0.0355 0.036 Uiso calc R 1 . .
    H H4 0.5535 0.7138 0.0746 0.032 Uiso calc R 1 . .
    H H5A 0.5834 0.8580 0.2721 0.037 Uiso d R 1 . .
    H H5B 0.4926 0.8438 0.2069 0.037 Uiso d R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C5 . 1.370(3) no
    N1 N2 . 1.380(3) no
    N1 C11 . 1.415(3) no
    C11 C16 . 1.385(3) no
    C11 C12 . 1.400(3) no
    C12 C13 . 1.392(3) no
    C12 N12 . 1.466(3) no
    N12 O121 . 1.228(2) no
    N12 O122 . 1.229(3) no
    C13 C14 . 1.381(3) no
    C13 H13 . 0.95 no
    C141 O141 . 1.212(3) no
    C141 O142 . 1.326(3) no
    C141 C14 . 1.490(3) no
    O142 C142 . 1.445(3) no
    C142 H14A . 0.98 no
    C142 H145 . 0.98 no
    C142 H1C . 0.98 no
    C14 C15 . 1.391(3) no
    C15 C16 . 1.383(3) no
    C15 H15 . 0.95 no
    C16 H16 . 0.95 no
    N2 C3 . 1.344(3) no
    C3 C4 . 1.406(3) no
    C3 C31 . 1.467(3) no
    C31 C32 . 1.396(3) no
    C31 C36 . 1.400(3) no
    C32 C33 . 1.381(3) no
    C32 H32 . 0.95 no
    C33 C34 . 1.389(4) no
    C33 H33 . 0.95 no
    C34 C35 . 1.378(4) no
    C34 H34 . 0.95 no
    C35 C36 . 1.391(3) no
    C35 H35 . 0.95 no
    C36 H36 . 0.95 no
    C4 C5 . 1.365(3) no
    C4 H4 . 0.95 no
    C5 N5 . 1.389(3) no
    N5 H5A . 0.87 no
    N5 H5B . 0.87 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 N1 N2 . . 112.09(17) no
    C5 N1 C11 . . 126.98(18) no
    N2 N1 C11 . . 120.33(17) no
    C16 C11 C12 . . 118.5(2) no
    C16 C11 N1 . . 119.7(2) no
    C12 C11 N1 . . 121.72(19) no
    C13 C12 C11 . . 121.3(2) no
    C13 C12 N12 . . 116.0(2) no
    C11 C12 N12 . . 122.72(19) no
    O121 N12 O122 . . 123.9(2) no
    O121 N12 C12 . . 118.68(19) no
    O122 N12 C12 . . 117.45(19) no
    C14 C13 C12 . . 119.3(2) no
    C14 C13 H13 . . 120.4 no
    C12 C13 H13 . . 120.4 no
    O141 C141 O142 . . 124.2(2) no
    O141 C141 C14 . . 123.5(2) no
    O142 C141 C14 . . 112.31(19) no
    C141 O142 C142 . . 115.54(19) no
    O142 C142 H14A . . 109.5 no
    O142 C142 H145 . . 109.5 no
    H14A C142 H145 . . 109.5 no
    O142 C142 H1C . . 109.5 no
    H14A C142 H1C . . 109.5 no
    H145 C142 H1C . . 109.5 no
    C13 C14 C15 . . 119.7(2) no
    C13 C14 C141 . . 121.4(2) no
    C15 C14 C141 . . 118.8(2) no
    C16 C15 C14 . . 120.8(2) no
    C16 C15 H15 . . 119.6 no
    C14 C15 H15 . . 119.6 no
    C15 C16 C11 . . 120.3(2) no
    C15 C16 H16 . . 119.9 no
    C11 C16 H16 . . 119.9 no
    C3 N2 N1 . . 103.63(17) no
    N2 C3 C4 . . 111.8(2) no
    N2 C3 C31 . . 120.5(2) no
    C4 C3 C31 . . 127.7(2) no
    C32 C31 C36 . . 118.3(2) no
    C32 C31 C3 . . 122.0(2) no
    C36 C31 C3 . . 119.7(2) no
    C33 C32 C31 . . 120.5(2) no
    C33 C32 H32 . . 119.7 no
    C31 C32 H32 . . 119.7 no
    C32 C33 C34 . . 120.6(2) no
    C32 C33 H33 . . 119.7 no
    C34 C33 H33 . . 119.7 no
    C35 C34 C33 . . 119.7(2) no
    C35 C34 H34 . . 120.1 no
    C33 C34 H34 . . 120.1 no
    C34 C35 C36 . . 120.0(2) no
    C34 C35 H35 . . 120.0 no
    C36 C35 H35 . . 120.0 no
    C35 C36 C31 . . 120.9(2) no
    C35 C36 H36 . . 119.6 no
    C31 C36 H36 . . 119.6 no
    C5 C4 C3 . . 105.98(19) no
    C5 C4 H4 . . 127.0 no
    C3 C4 H4 . . 127.0 no
    C4 C5 N1 . . 106.48(19) no
    C4 C5 N5 . . 133.5(2) no
    N1 C5 N5 . . 119.97(19) no
    C5 N5 H5A . . 108.7 no
    C5 N5 H5B . . 109.4 no
    H5A N5 H5B . . 110.9 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C11 C16 . . . . -126.6(2) no
    N2 N1 C11 C16 . . . . 63.0(3) no
    C5 N1 C11 C12 . . . . 52.2(3) no
    N2 N1 C11 C12 . . . . -118.2(2) no
    C16 C11 C12 C13 . . . . 2.2(3) no
    N1 C11 C12 C13 . . . . -176.6(2) no
    C16 C11 C12 N12 . . . . -175.9(2) no
    N1 C11 C12 N12 . . . . 5.3(3) no
    C13 C12 N12 O121 . . . . -146.4(2) no
    C11 C12 N12 O121 . . . . 31.8(3) no
    C13 C12 N12 O122 . . . . 32.2(3) no
    C11 C12 N12 O122 . . . . -149.7(2) no
    C11 C12 C13 C14 . . . . -2.7(3) no
    N12 C12 C13 C14 . . . . 175.54(19) no
    O141 C141 O142 C142 . . . . 0.7(3) no
    C14 C141 O142 C142 . . . . -179.44(19) no
    C12 C13 C14 C15 . . . . 1.6(3) no
    C12 C13 C14 C141 . . . . -178.0(2) no
    O141 C141 C14 C13 . . . . 177.1(2) no
    O142 C141 C14 C13 . . . . -2.7(3) no
    O141 C141 C14 C15 . . . . -2.5(3) no
    O142 C141 C14 C15 . . . . 177.68(19) no
    C13 C14 C15 C16 . . . . -0.1(3) no
    C141 C14 C15 C16 . . . . 179.5(2) no
    C14 C15 C16 C11 . . . . -0.3(3) no
    C12 C11 C16 C15 . . . . -0.7(3) no
    N1 C11 C16 C15 . . . . 178.16(19) no
    C5 N1 N2 C3 . . . . -1.5(2) no
    C11 N1 N2 C3 . . . . 170.23(19) no
    N1 N2 C3 C4 . . . . 0.5(2) no
    N1 N2 C3 C31 . . . . -179.92(19) no
    N2 C3 C31 C32 . . . . -15.0(3) no
    C4 C3 C31 C32 . . . . 164.5(2) no
    N2 C3 C31 C36 . . . . 163.7(2) no
    C4 C3 C31 C36 . . . . -16.8(4) no
    C36 C31 C32 C33 . . . . -1.3(4) no
    C3 C31 C32 C33 . . . . 177.4(2) no
    C31 C32 C33 C34 . . . . 0.6(4) no
    C32 C33 C34 C35 . . . . 0.4(4) no
    C33 C34 C35 C36 . . . . -0.6(4) no
    C34 C35 C36 C31 . . . . -0.2(4) no
    C32 C31 C36 C35 . . . . 1.1(3) no
    C3 C31 C36 C35 . . . . -177.6(2) no
    N2 C3 C4 C5 . . . . 0.7(3) no
    C31 C3 C4 C5 . . . . -178.9(2) no
    C3 C4 C5 N1 . . . . -1.6(2) no
    C3 C4 C5 N5 . . . . 179.1(2) no
    N2 N1 C5 C4 . . . . 2.0(2) no
    C11 N1 C5 C4 . . . . -169.1(2) no
    N2 N1 C5 N5 . . . . -178.54(19) no
    C11 N1 C5 N5 . . . . 10.4(3) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N5 H5A N2 2_655 0.87 2.33 3.131(3) 154 y
    N5 H5B O141 4_464 0.87 2.18 3.024(3) 163 y
    C16 H16 O121 2_655 0.95 2.39 3.304(3) 161 y
data_II
_chemical_name_systematic
;
methyl 3-nitro-4-[(5-phenyl-1H-pyrazol-3-yl)amino]benzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 N4 O4'
_chemical_formula_sum     'C17 H14 N4 O4'
_chemical_formula_iupac     'C17 H14 N4 O4'
_chemical_formula_weight     338.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     31.0506(4)
_cell_length_b     5.4210(11)
_cell_length_c     20.7251(12)
_cell_angle_alpha     90.00
_cell_angle_beta     121.071(6)
_cell_angle_gamma     90.00
_cell_volume     2988.1(7)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3420
_cell_measurement_theta_min     3.06
_cell_measurement_theta_max     27.52
_cell_measurement_temperature     120(2)
_exptl_crystal_description     lath
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1408
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.947
_exptl_absorpt_correction_T_max     0.967
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker--Nonius KappaCCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     33526
_diffrn_reflns_av_R_equivalents     0.0443
_diffrn_reflns_av_sigmaI/netI     0.0265
_diffrn_reflns_theta_min     3.06
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -40
_diffrn_reflns_limit_h_max     40
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_decay_%     0
_reflns_number_total     3420
_reflns_number_gt     2488
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0762
_refine_ls_R_factor_gt     0.0479
_refine_ls_wR_factor_gt     0.1111
_refine_ls_wR_factor_ref     0.1336
_refine_ls_goodness_of_fit_ref     1.107
_refine_ls_restrained_S_all     1.107
_refine_ls_number_reflns     3420
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0578P)²+4.6327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.283
_refine_diff_density_min     -0.355
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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' 0.0000 0.0000
                         '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 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_reduction     'EVALCCD (Duisenberg et al.,  2003)'
_computing_structure_solution
               'SIR2004 (Burla et al.,  2005) and WinGX (Farrugia, 1999)'
_computing_structure_refinement
                         'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.59810(6) 0.7513(3) 0.60667(8) 0.0228(4) Uani d . 1 . .
    N N2 0.63253(6) 0.7928(3) 0.68076(8) 0.0214(3) Uani d . 1 . .
    C C3 0.66832(6) 0.6152(3) 0.71231(9) 0.0184(4) Uani d . 1 . .
    C C31 0.70897(6) 0.6193(3) 0.79170(9) 0.0182(4) Uani d . 1 . .
    C C32 0.74389(7) 0.4276(4) 0.82041(10) 0.0219(4) Uani d . 1 . .
    C C33 0.78193(7) 0.4238(4) 0.89564(10) 0.0238(4) Uani d . 1 . .
    C C34 0.78548(7) 0.6121(4) 0.94348(10) 0.0238(4) Uani d . 1 . .
    C C35 0.75135(7) 0.8050(4) 0.91523(10) 0.0238(4) Uani d . 1 . .
    C C36 0.71360(7) 0.8107(4) 0.84023(10) 0.0216(4) Uani d . 1 . .
    C C4 0.65743(7) 0.4485(3) 0.65562(10) 0.0202(4) Uani d . 1 . .
    C C5 0.61378(6) 0.5413(3) 0.59205(9) 0.0195(4) Uani d . 1 . .
    C C51 0.54722(6) 0.4771(3) 0.45658(9) 0.0183(4) Uani d . 1 . .
    C C52 0.52986(6) 0.3312(3) 0.39047(9) 0.0178(4) Uani d . 1 . .
    N N5 0.59048(6) 0.4223(3) 0.52237(8) 0.0212(3) Uani d . 1 . .
    N N52 0.55736(5) 0.1186(3) 0.38848(8) 0.0200(3) Uani d . 1 . .
    O O521 0.59647(5) 0.0523(3) 0.44756(7) 0.0265(3) Uani d . 1 . .
    O O522 0.54173(5) 0.0068(2) 0.32903(7) 0.0259(3) Uani d . 1 . .
    C C53 0.48594(6) 0.3880(3) 0.32318(10) 0.0185(4) Uani d . 1 . .
    C C54 0.45787(6) 0.5917(3) 0.31831(9) 0.0188(4) Uani d . 1 . .
    C C541 0.41265(7) 0.6645(3) 0.24683(10) 0.0194(4) Uani d . 1 . .
    O O541 0.38721(5) 0.8454(3) 0.23954(7) 0.0258(3) Uani d . 1 . .
    O O542 0.40194(5) 0.5128(2) 0.18978(7) 0.0227(3) Uani d . 1 . .
    C C542 0.35970(7) 0.5849(4) 0.11720(10) 0.0251(4) Uani d . 1 . .
    C C55 0.47383(7) 0.7361(3) 0.38303(10) 0.0205(4) Uani d . 1 . .
    C C56 0.51666(7) 0.6817(3) 0.44995(10) 0.0203(4) Uani d . 1 . .
    H H2 0.6277 0.9160 0.7034 0.026 Uiso d R 1 . .
    H H32 0.7416 0.2977 0.7880 0.026 Uiso calc R 1 . .
    H H33 0.8055 0.2923 0.9144 0.029 Uiso calc R 1 . .
    H H34 0.8111 0.6088 0.9952 0.029 Uiso calc R 1 . .
    H H35 0.7539 0.9349 0.9478 0.029 Uiso calc R 1 . .
    H H36 0.6907 0.9451 0.8215 0.026 Uiso calc R 1 . .
    H H4 0.6754 0.3028 0.6588 0.024 Uiso calc R 1 . .
    H H5 0.6041 0.2833 0.5213 0.025 Uiso d R 1 . .
    H H53 0.4752 0.2856 0.2803 0.022 Uiso calc R 1 . .
    H H54A 0.3296 0.6018 0.1209 0.038 Uiso calc R 1 . .
    H H54B 0.3538 0.4586 0.0797 0.038 Uiso calc R 1 . .
    H H54C 0.3671 0.7429 0.1020 0.038 Uiso calc R 1 . .
    H H55 0.4544 0.8754 0.3803 0.025 Uiso calc R 1 . .
    H H56 0.5261 0.7827 0.4927 0.024 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C5 . 1.333(2) no
    N1 N2 . 1.363(2) no
    N2 C3 . 1.356(2) no
    N2 H2 . 0.87 no
    C3 C4 . 1.379(2) no
    C3 C31 . 1.469(2) no
    C31 C32 . 1.394(3) no
    C31 C36 . 1.400(3) no
    C32 C33 . 1.388(2) no
    C32 H32 . 0.95 no
    C33 C34 . 1.387(3) no
    C33 H33 . 0.95 no
    C34 C35 . 1.385(3) no
    C34 H34 . 0.95 no
    C35 C36 . 1.382(3) no
    C35 H35 . 0.95 no
    C36 H36 . 0.95 no
    C4 C5 . 1.408(2) no
    C4 H4 . 0.95 no
    C5 N5 . 1.395(2) no
    C51 N5 . 1.364(2) y
    C51 C52 . 1.425(2) y
    C52 C53 . 1.391(2) y
    C53 C54 . 1.378(3) y
    C54 C55 . 1.404(2) y
    C55 C56 . 1.370(3) y
    C56 C51 . 1.419(3) y
    C52 N52 . 1.448(2) y
    N5 H5 . 0.87 no
    N52 O521 . 1.2522(19) y
    N52 O522 . 1.2262(19) y
    C53 H53 . 0.95 no
    C54 C541 . 1.475(2) no
    C541 O541 . 1.219(2) no
    C541 O542 . 1.334(2) no
    O542 C542 . 1.449(2) no
    C542 H54A . 0.98 no
    C542 H54B . 0.98 no
    C542 H54C . 0.98 no
    C55 H55 . 0.95 no
    C56 H56 . 0.95 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 N1 N2 . . 103.36(14) no
    C3 N2 N1 . . 113.40(15) no
    C3 N2 H2 . . 127.5 no
    N1 N2 H2 . . 118.7 no
    N2 C3 C4 . . 105.95(15) no
    N2 C3 C31 . . 123.09(16) no
    C4 C3 C31 . . 130.96(16) no
    C32 C31 C36 . . 118.49(16) no
    C32 C31 C3 . . 119.75(16) no
    C36 C31 C3 . . 121.76(16) no
    C33 C32 C31 . . 120.94(17) no
    C33 C32 H32 . . 119.5 no
    C31 C32 H32 . . 119.5 no
    C34 C33 C32 . . 119.98(17) no
    C34 C33 H33 . . 120.0 no
    C32 C33 H33 . . 120.0 no
    C35 C34 C33 . . 119.47(17) no
    C35 C34 H34 . . 120.3 no
    C33 C34 H34 . . 120.3 no
    C36 C35 C34 . . 120.81(18) no
    C36 C35 H35 . . 119.6 no
    C34 C35 H35 . . 119.6 no
    C35 C36 C31 . . 120.29(17) no
    C35 C36 H36 . . 119.9 no
    C31 C36 H36 . . 119.9 no
    C3 C4 C5 . . 104.91(16) no
    C3 C4 H4 . . 127.5 no
    C5 C4 H4 . . 127.5 no
    N1 C5 N5 . . 125.10(16) no
    N1 C5 C4 . . 112.37(16) no
    N5 C5 C4 . . 122.53(17) no
    N5 C51 C56 . . 122.09(16) no
    N5 C51 C52 . . 121.92(16) no
    C56 C51 C52 . . 116.00(16) no
    C53 C52 C51 . . 121.99(16) no
    C53 C52 N52 . . 115.77(15) no
    C51 C52 N52 . . 122.23(15) no
    C51 N5 C5 . . 130.60(16) no
    C51 N5 H5 . . 113.8 no
    C5 N5 H5 . . 115.3 no
    O522 N52 O521 . . 121.46(15) no
    O522 N52 C52 . . 119.26(14) no
    O521 N52 C52 . . 119.28(14) no
    C54 C53 C52 . . 120.40(16) no
    C54 C53 H53 . . 119.8 no
    C52 C53 H53 . . 119.8 no
    C53 C54 C55 . . 118.61(16) no
    C53 C54 C541 . . 121.75(16) no
    C55 C54 C541 . . 119.61(16) no
    O541 C541 O542 . . 122.48(16) no
    O541 C541 C54 . . 124.05(16) no
    O542 C541 C54 . . 113.46(15) no
    C541 O542 C542 . . 115.60(14) no
    O542 C542 H54A . . 109.5 no
    O542 C542 H54B . . 109.5 no
    H54A C542 H54B . . 109.5 no
    O542 C542 H54C . . 109.5 no
    H54A C542 H54C . . 109.5 no
    H54B C542 H54C . . 109.5 no
    C56 C55 C54 . . 121.78(17) no
    C56 C55 H55 . . 119.1 no
    C54 C55 H55 . . 119.1 no
    C55 C56 C51 . . 121.18(17) no
    C55 C56 H56 . . 119.4 no
    C51 C56 H56 . . 119.4 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 N2 C3 . . . . -0.7(2) no
    N1 N2 C3 C4 . . . . 0.9(2) no
    N1 N2 C3 C31 . . . . -179.26(15) no
    N2 C3 C31 C32 . . . . 178.86(17) no
    C4 C3 C31 C32 . . . . -1.4(3) no
    N2 C3 C31 C36 . . . . -0.6(3) no
    C4 C3 C31 C36 . . . . 179.14(18) no
    C36 C31 C32 C33 . . . . 1.1(3) no
    C3 C31 C32 C33 . . . . -178.41(16) no
    C31 C32 C33 C34 . . . . 0.2(3) no
    C32 C33 C34 C35 . . . . -1.1(3) no
    C33 C34 C35 C36 . . . . 0.6(3) no
    C34 C35 C36 C31 . . . . 0.7(3) no
    C32 C31 C36 C35 . . . . -1.5(3) no
    C3 C31 C36 C35 . . . . 177.94(17) no
    N2 C3 C4 C5 . . . . -0.71(19) no
    C31 C3 C4 C5 . . . . 179.51(18) no
    N2 N1 C5 N5 . . . . -179.79(16) no
    N2 N1 C5 C4 . . . . 0.2(2) no
    C3 C4 C5 N1 . . . . 0.3(2) no
    C3 C4 C5 N5 . . . . -179.67(16) no
    N5 C51 C52 C53 . . . . -179.51(16) no
    C56 C51 C52 C53 . . . . 0.8(3) no
    N5 C51 C52 N52 . . . . -1.1(3) no
    C56 C51 C52 N52 . . . . 179.27(15) no
    C56 C51 N5 C5 . . . . -1.0(3) no
    C52 C51 N5 C5 . . . . 179.37(17) no
    N1 C5 N5 C51 . . . . -3.7(3) no
    C4 C5 N5 C51 . . . . 176.24(18) no
    C53 C52 N52 O522 . . . . 1.8(2) no
    C51 C52 N52 O522 . . . . -176.73(16) no
    C53 C52 N52 O521 . . . . -177.92(15) no
    C51 C52 N52 O521 . . . . 3.6(2) no
    C51 C52 C53 C54 . . . . 0.7(3) no
    N52 C52 C53 C54 . . . . -177.77(15) no
    C52 C53 C54 C55 . . . . -1.7(3) no
    C52 C53 C54 C541 . . . . 176.70(16) no
    C53 C54 C541 O541 . . . . -178.65(17) no
    C55 C54 C541 O541 . . . . -0.3(3) no
    C53 C54 C541 O542 . . . . 1.1(2) no
    C55 C54 C541 O542 . . . . 179.46(15) no
    O541 C541 O542 C542 . . . . 3.5(2) no
    C54 C541 O542 C542 . . . . -176.23(15) no
    C53 C54 C55 C56 . . . . 1.0(3) no
    C541 C54 C55 C56 . . . . -177.40(17) no
    C54 C55 C56 C51 . . . . 0.6(3) no
    N5 C51 C56 C55 . . . . 178.84(17) no
    C52 C51 C56 C55 . . . . -1.5(3) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N5 H5 O521 . 0.87 1.89 2.600(2) 137 y
    N2 H2 O541 3_676 0.87 1.96 2.828(2) 171 y
    C36 H36 O541 3_676 0.95 2.36 3.266(3) 159 y
    C53 H53 O522 2_655 0.95 2.54 3.487(2) 173 y
