##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2007-05-11
_journal_date_accepted     2007-05-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o2911
_journal_page_last     o2911
_journal_paper_category     QO
_journal_coeditor_code     FJ2033
_publ_contact_author_name
;
A. Thiruvalluvar
;
_publ_contact_author_address
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur-613 005
Tamil Nadu
India
;
_publ_contact_author_email     athiru@vsnl.net
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '+91(4362)255490'
_publ_section_title
;\
3-(4-Chlorophenyl)-1-(4,6-dimethylpyrimidin-2-yl)-1H-pyrazole-4-\
carbaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'A. Thiruvalluvar'
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'M. Subramanyam'
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'Balakrishna Kalluraya'
;
Department of Studies in Chemistry
Mangalore University
Mangalagangothri 574 199
Karnataka
India
;
    'B. Lingappa'
;
Department of Studies in Chemistry
Mangalore University
Mangalagangothri 574 199
Karnataka
India
;
data_I
_chemical_name_systematic
;
3-(4-Chlorophenyl)-1-(4,6-dimethylpyrimidin-2-yl)-1H-pyrazole-4-carbaldehyde
;
_chemical_name_common     'pyrimidine derivative'
_chemical_formula_moiety     'C16 H13 Cl N4 O'
_chemical_formula_sum     'C16 H13 Cl N4 O'
_chemical_formula_structural     'C16 H13 Cl N4 O'
_chemical_formula_iupac     'C16 H13 Cl N4 O'
_chemical_formula_weight     312.75
_chemical_melting_point     442.0(10)
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     7.2458(2)
_cell_length_b     13.6704(4)
_cell_length_c     14.4757(3)
_cell_angle_alpha     90.718(2)
_cell_angle_beta     92.618(2)
_cell_angle_gamma     93.6230(10)
_cell_volume     1429.33(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     53782
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     160.0(10)
_cell_special_details
;
?
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.453
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     648
_exptl_absorpt_coefficient_mu     0.275
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.830
_exptl_absorpt_correction_T_max     0.948
_exptl_special_details
;
Solvent used: Ethyl acetate
Cooling Device: Oxford Cryosystems Cryostream 700
Crystal mount: glued on a glass fibre
Mosaicity (deg.): 1.077(2)
Frames collected: 374
Seconds exposure per frame: 72
Degrees rotation per frame: 1.8
Crystal-Detector distance (mm): 30.0
;
_diffrn_ambient_temperature     160.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Nonius FR590 sealed tube generator'
_diffrn_radiation_monochromator     'horizontally mounted graphite crystal'
_diffrn_measurement_device_type
                                  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method     'φ and ω scans with κ offsets'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     34357
_diffrn_reflns_av_R_equivalents     0.0596
_diffrn_reflns_av_sigmaI/netI     0.0333
_diffrn_reflns_theta_min     2.04
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     6537
_reflns_number_gt     5563
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0682
_refine_ls_R_factor_gt     0.0575
_refine_ls_wR_factor_gt     0.1576
_refine_ls_wR_factor_ref     0.1650
_refine_ls_goodness_of_fit_ref     1.166
_refine_ls_restrained_S_all     1.166
_refine_ls_number_reflns     6537
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0681P)²+1.7016P] 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     0.419
_refine_diff_density_min     -0.459
_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
    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'
    Cl Cl 0.1484 0.1585 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cl Cl1 0.51295(10) 0.68301(5) 0.01191(4) 0.0365(2) Uani . . 1.000
    O O41A 0.5611(3) 0.74111(14) 0.48792(13) 0.0342(6) Uani . . 1.000
    N N1A 0.7911(3) 0.43476(14) 0.48997(13) 0.0218(5) Uani . . 1.000
    N N2A 0.7564(3) 0.45038(14) 0.39789(13) 0.0221(5) Uani . . 1.000
    N N12A 0.9017(3) 0.28056(15) 0.46061(14) 0.0241(6) Uani . . 1.000
    N N16A 0.8668(3) 0.34137(15) 0.61465(14) 0.0224(6) Uani . . 1.000
    C C3A 0.6944(3) 0.54000(16) 0.39297(16) 0.0206(6) Uani . . 1.000
    C C4A 0.6906(3) 0.58290(17) 0.48430(16) 0.0219(6) Uani . . 1.000
    C C5A 0.7543(3) 0.51247(17) 0.54265(17) 0.0229(7) Uani . . 1.000
    C C11A 0.8575(3) 0.34531(17) 0.52289(16) 0.0216(6) Uani . . 1.000
    C C13A 0.9668(3) 0.19776(17) 0.49692(17) 0.0252(7) Uani . . 1.000
    C C14A 0.9818(3) 0.18455(18) 0.59144(18) 0.0267(7) Uani . . 1.000
    C C15A 0.9311(3) 0.25858(18) 0.64966(16) 0.0236(6) Uani . . 1.000
    C C31A 0.6484(3) 0.57771(17) 0.30050(16) 0.0213(6) Uani . . 1.000
    C C32A 0.6891(3) 0.52279(17) 0.22255(16) 0.0237(7) Uani . . 1.000
    C C33A 0.6465(4) 0.55425(18) 0.13403(17) 0.0271(7) Uani . . 1.000
    C C34A 0.5645(3) 0.64273(18) 0.12273(17) 0.0256(7) Uani . . 1.000
    C C35A 0.5241(3) 0.69938(18) 0.19835(18) 0.0259(7) Uani . . 1.000
    C C36A 0.5643(3) 0.66604(18) 0.28682(17) 0.0258(7) Uani . . 1.000
    C C41A 0.6371(4) 0.67460(18) 0.52475(17) 0.0267(7) Uani . . 1.000
    C C44A 1.0221(4) 0.1229(2) 0.42840(19) 0.0342(8) Uani . . 1.000
    C C46A 0.9439(4) 0.25196(19) 0.75273(17) 0.0278(7) Uani . . 1.000
    Cl Cl2 -0.16204(10) 0.51727(5) -0.18594(5) 0.0392(2) Uani . . 1.000
    O O41B 0.0848(3) 1.00278(14) -0.23689(13) 0.0395(7) Uani . . 1.000
    N N1B 0.2953(3) 1.00178(14) 0.06769(13) 0.0213(6) Uani . . 1.000
    N N2B 0.2305(3) 0.90661(14) 0.05160(14) 0.0221(6) Uani . . 1.000
    N N12B 0.3945(3) 0.96995(15) 0.22009(14) 0.0243(6) Uani . . 1.000
    N N16B 0.4076(3) 1.13192(15) 0.15907(14) 0.0237(6) Uani . . 1.000
    C C3B 0.1713(3) 0.90258(17) -0.03703(15) 0.0194(6) Uani . . 1.000
    C C4B 0.2013(3) 0.99737(17) -0.07844(16) 0.0217(6) Uani . . 1.000
    C C5B 0.2803(3) 1.05697(17) -0.00814(16) 0.0226(6) Uani . . 1.000
    C C11B 0.3705(3) 1.03589(17) 0.15578(16) 0.0216(6) Uani . . 1.000
    C C13B 0.4647(4) 1.00728(19) 0.30196(17) 0.0266(7) Uani . . 1.000
    C C14B 0.5048(3) 1.10726(19) 0.31526(17) 0.0269(7) Uani . . 1.000
    C C15B 0.4774(3) 1.16840(18) 0.24049(17) 0.0243(7) Uani . . 1.000
    C C31B 0.0901(3) 0.80849(17) -0.07541(16) 0.0214(6) Uani . . 1.000
    C C32B 0.0442(4) 0.73270(19) -0.01571(18) 0.0310(8) Uani . . 1.000
    C C33B -0.0313(4) 0.6433(2) -0.0493(2) 0.0349(8) Uani . . 1.000
    C C34B -0.0604(3) 0.62868(18) -0.14341(19) 0.0269(7) Uani . . 1.000
    C C35B -0.0130(4) 0.7013(2) -0.20448(18) 0.0321(8) Uani . . 1.000
    C C36B 0.0617(4) 0.79150(19) -0.17014(18) 0.0294(7) Uani . . 1.000
    C C41B 0.1626(4) 1.04061(19) -0.16822(17) 0.0285(7) Uani . . 1.000
    C C44B 0.5025(5) 0.9345(2) 0.37569(19) 0.0394(9) Uani . . 1.000
    C C46B 0.5244(4) 1.27659(19) 0.24509(19) 0.0323(8) Uani . . 1.000
    H H5A 0.76945 0.51769 0.60810 0.0274 Uiso . . 1.000
    H H14A 1.02609 0.12587 0.61604 0.0320 Uiso . . 1.000
    H H32A 0.74699 0.46284 0.23056 0.0285 Uiso . . 1.000
    H H33A 0.67301 0.51584 0.08170 0.0325 Uiso . . 1.000
    H H35A 0.46969 0.76023 0.18981 0.0311 Uiso . . 1.000
    H H36A 0.53419 0.70385 0.33889 0.0309 Uiso . . 1.000
    H H41A 0.66616 0.68331 0.58911 0.0320 Uiso . . 1.000
    H H44A 0.91088 0.08764 0.40056 0.0513 Uiso . . 1.000
    H H44B 1.09989 0.07644 0.45998 0.0513 Uiso . . 1.000
    H H44C 1.09147 0.15590 0.37990 0.0513 Uiso . . 1.000
    H H46A 1.07426 0.25825 0.77451 0.0417 Uiso . . 1.000
    H H46B 0.88815 0.18848 0.77132 0.0417 Uiso . . 1.000
    H H46C 0.87780 0.30481 0.77992 0.0417 Uiso . . 1.000
    H H4A 0.38606 0.89951 0.39133 0.0591 Uiso . . 1.000
    H H4B 0.55884 0.96872 0.43085 0.0591 Uiso . . 1.000
    H H4C 0.58734 0.88742 0.35318 0.0591 Uiso . . 1.000
    H H5B 0.31737 1.12461 -0.01242 0.0271 Uiso . . 1.000
    H H6A 0.59384 1.29624 0.19111 0.0484 Uiso . . 1.000
    H H6B 0.59991 1.29309 0.30168 0.0484 Uiso . . 1.000
    H H6C 0.41009 1.31127 0.24549 0.0484 Uiso . . 1.000
    H H14B 0.54977 1.13317 0.37380 0.0323 Uiso . . 1.000
    H H32B 0.06511 0.74263 0.04909 0.0372 Uiso . . 1.000
    H H33B -0.06302 0.59224 -0.00784 0.0418 Uiso . . 1.000
    H H35B -0.03094 0.68996 -0.26925 0.0385 Uiso . . 1.000
    H H36B 0.09374 0.84217 -0.21193 0.0353 Uiso . . 1.000
    H H41B 0.20395 1.10753 -0.17374 0.0342 Uiso . . 1.000
_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_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C34A . . 1.735(3) no
    Cl2 C34B . . 1.742(3) no
    O41A C41A . . 1.210(3) no
    O41B C41B . . 1.213(3) no
    N1A N2A . . 1.367(3) no
    N1A C5A . . 1.347(3) no
    N1A C11A . . 1.422(3) no
    N2A C3A . . 1.333(3) no
    N12A C13A . . 1.356(3) no
    N12A C11A . . 1.320(3) no
    N16A C11A . . 1.329(3) no
    N16A C15A . . 1.347(3) no
    N1B C5B . . 1.344(3) no
    N1B C11B . . 1.425(3) no
    N1B N2B . . 1.368(3) no
    N2B C3B . . 1.333(3) no
    N12B C13B . . 1.349(3) no
    N12B C11B . . 1.317(3) no
    N16B C11B . . 1.323(3) no
    N16B C15B . . 1.339(3) no
    C3A C31A . . 1.472(3) no
    C3A C4A . . 1.442(3) no
    C4A C5A . . 1.376(3) no
    C4A C41A . . 1.459(3) no
    C13A C14A . . 1.383(4) no
    C13A C44A . . 1.501(4) no
    C14A C15A . . 1.387(3) no
    C15A C46A . . 1.495(3) no
    C31A C32A . . 1.400(3) no
    C31A C36A . . 1.399(3) no
    C32A C33A . . 1.384(3) no
    C33A C34A . . 1.389(4) no
    C34A C35A . . 1.386(4) no
    C35A C36A . . 1.389(4) no
    C5A H5A . . 0.9500 no
    C14A H14A . . 0.9500 no
    C32A H32A . . 0.9500 no
    C33A H33A . . 0.9500 no
    C35A H35A . . 0.9500 no
    C36A H36A . . 0.9500 no
    C41A H41A . . 0.9500 no
    C44A H44C . . 0.9800 no
    C44A H44B . . 0.9800 no
    C44A H44A . . 0.9800 no
    C46A H46A . . 0.9800 no
    C46A H46B . . 0.9800 no
    C46A H46C . . 0.9800 no
    C3B C4B . . 1.443(3) no
    C3B C31B . . 1.472(3) no
    C4B C5B . . 1.376(3) no
    C4B C41B . . 1.457(3) no
    C13B C14B . . 1.388(4) no
    C13B C44B . . 1.496(4) no
    C14B C15B . . 1.391(4) no
    C15B C46B . . 1.497(4) no
    C31B C32B . . 1.391(3) no
    C31B C36B . . 1.392(3) no
    C32B C33B . . 1.380(4) no
    C33B C34B . . 1.379(4) no
    C34B C35B . . 1.375(4) no
    C35B C36B . . 1.392(4) no
    C5B H5B . . 0.9500 no
    C14B H14B . . 0.9500 no
    C32B H32B . . 0.9500 no
    C33B H33B . . 0.9500 no
    C35B H35B . . 0.9500 no
    C36B H36B . . 0.9500 no
    C41B H41B . . 0.9500 no
    C44B H4A . . 0.9800 no
    C44B H4B . . 0.9800 no
    C44B H4C . . 0.9800 no
    C46B H6A . . 0.9800 no
    C46B H6B . . 0.9800 no
    C46B H6C . . 0.9800 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cl1 C32B 3.512(3) . . no
    Cl1 C33B 3.531(3) . 1_655 no
    Cl2 C32A 3.567(2) . 2_665 no
    Cl1 H6A 3.0300 . 2_675 no
    Cl1 H5B 2.8300 . 2_675 no
    Cl2 H32A 3.1000 . 2_665 no
    Cl2 H46C 2.9700 . 1_454 no
    Cl2 H5A 3.0000 . 1_454 no
    Cl2 H6C 3.1500 . 2_575 no
    O41A C44B 3.162(3) . . no
    O41A C36A 3.076(3) . . no
    O41A C11A 3.181(3) . 2_666 no
    O41B C36B 3.054(3) . . no
    O41B C44A 3.279(3) . 2_665 no
    O41A H36A 2.2100 . . no
    O41A H4A 2.9200 . . no
    O41A H4C 2.8200 . . no
    O41A H14B 2.8000 . 2_676 no
    O41B H36B 2.2300 . . no
    O41B H14A 2.7600 . 1_464 no
    O41B H44A 2.6600 . 2_665 no
    N1A C5A 3.383(3) . 2_766 no
    N1A C41A 3.354(4) . 2_666 no
    N1B C5B 3.374(3) . 2_675 no
    N2A N12A 2.756(3) . . no
    N2B N12B 2.768(3) . . no
    N12A C41A 3.356(4) . 2_766 no
    N12A N2A 2.756(3) . . no
    N12A C4A 3.449(3) . 2_766 no
    N12B N2B 2.768(3) . . no
    N12B C41B 3.341(4) . 2_675 no
    N2A H32A 2.4300 . . no
    N2A H6B 2.7100 . 1_545 no
    N2B H32B 2.4700 . . no
    N12B H46B 2.8900 . 2_666 no
    N16A H5A 2.5600 . . no
    N16B H5B 2.5400 . . no
    C3A C5A 3.457(3) . 2_666 no
    C3B C4B 3.574(3) . 2_575 no
    C3B C5B 3.443(3) . 2_575 no
    C4A C11A 3.365(3) . 2_766 no
    C4A C5A 3.404(3) . 2_666 no
    C4A C4A 3.510(3) . 2_666 no
    C4A N12A 3.449(3) . 2_766 no
    C4B C3B 3.574(3) . 2_575 no
    C4B C11B 3.401(3) . 2_675 no
    C5A C11A 3.492(3) . 2_766 no
    C5A C3A 3.457(3) . 2_666 no
    C5A C4A 3.404(3) . 2_666 no
    C5A N1A 3.383(3) . 2_766 no
    C5B N1B 3.374(3) . 2_675 no
    C5B C3B 3.443(3) . 2_575 no
    C5B C31B 3.594(3) . 2_575 no
    C11A C5A 3.492(3) . 2_766 no
    C11A C4A 3.365(3) . 2_766 no
    C11A O41A 3.181(3) . 2_666 no
    C11B C4B 3.401(3) . 2_675 no
    C13A C41A 3.293(4) . 2_766 no
    C13B C41B 3.484(4) . 2_675 no
    C15B C36B 3.547(4) . 2_675 no
    C31B C5B 3.594(3) . 2_575 no
    C32A C46B 3.523(3) . 1_545 no
    C32A Cl2 3.567(2) . 2_665 no
    C32B Cl1 3.512(3) . . no
    C33B Cl1 3.531(3) . 1_455 no
    C35A C46A 3.597(4) . 2_666 no
    C36A C41A 3.460(3) . . no
    C36A O41A 3.076(3) . . no
    C36B C41B 3.437(4) . . no
    C36B O41B 3.054(3) . . no
    C36B C46B 3.415(4) . 2_675 no
    C36B C15B 3.547(4) . 2_675 no
    C41A C13A 3.293(4) . 2_766 no
    C41A N12A 3.356(4) . 2_766 no
    C41A C36A 3.460(3) . . no
    C41A N1A 3.354(4) . 2_666 no
    C41B N12B 3.341(4) . 2_675 no
    C41B C46A 3.559(4) . 1_464 no
    C41B C13B 3.484(4) . 2_675 no
    C41B C36B 3.437(4) . . no
    C44A O41B 3.279(3) . 2_665 no
    C44B O41A 3.162(3) . . no
    C46A C35A 3.597(4) . 2_666 no
    C46A C41B 3.559(4) . 1_646 no
    C46B C32A 3.523(3) . 1_565 no
    C46B C36B 3.415(4) . 2_675 no
    C4A H36A 2.9200 . . no
    C4B H36B 2.9000 . . no
    C14A H4A 2.8600 . 2_666 no
    C15A H4A 3.0900 . 2_666 no
    C33A H33B 3.0300 . 1_655 no
    C34B H6C 3.0400 . 2_575 no
    C34B H32A 2.9800 . 2_665 no
    C35A H46A 2.9400 . 2_766 no
    C35A H46C 2.9400 . 2_666 no
    C35B H6C 2.9100 . 2_575 no
    C35B H32A 3.0800 . 2_665 no
    C35B H6A 3.0300 . 2_675 no
    C36A H46A 2.9300 . 2_766 no
    C36B H6A 2.8600 . 2_675 no
    C41A H36A 2.8000 . . no
    C41B H46B 3.0300 . 1_464 no
    C41B H36B 2.7900 . . no
    C46A H41B 2.9900 . 1_646 no
    C46A H32B 2.8700 . 2_666 no
    C46B H41A 2.8900 . 2_676 no
    C46B H32A 2.9400 . 1_565 no
    H4A O41A 2.9200 . . no
    H4A C14A 2.8600 . 2_666 no
    H4A C15A 3.0900 . 2_666 no
    H4B H14B 2.4100 . . no
    H4B H4B 2.3800 . 2_676 no
    H4C H36A 2.5200 . . no
    H4C O41A 2.8200 . . no
    H5A N16A 2.5600 . . no
    H5A Cl2 3.0000 . 1_656 no
    H5A H41A 2.4400 . . no
    H5B Cl1 2.8300 . 2_675 no
    H5B N16B 2.5400 . . no
    H5B H41B 2.4400 . . no
    H6A H32A 2.5200 . 1_565 no
    H6A C36B 2.8600 . 2_675 no
    H6A Cl1 3.0300 . 2_675 no
    H6A C35B 3.0300 . 2_675 no
    H6B H41A 2.5800 . 2_676 no
    H6B H14B 2.4500 . . no
    H6B N2A 2.7100 . 1_565 no
    H6C C34B 3.0400 . 2_575 no
    H6C C35B 2.9100 . 2_575 no
    H6C Cl2 3.1500 . 2_575 no
    H6C H41A 2.4800 . 2_676 no
    H14A H44B 2.4400 . . no
    H14A O41B 2.7600 . 1_646 no
    H14B H6B 2.4500 . . no
    H14B H4B 2.4100 . . no
    H14B O41A 2.8000 . 2_676 no
    H32A N2A 2.4300 . . no
    H32A C35B 3.0800 . 2_665 no
    H32A H6A 2.5200 . 1_545 no
    H32A Cl2 3.1000 . 2_665 no
    H32A C46B 2.9400 . 1_545 no
    H32A C34B 2.9800 . 2_665 no
    H32B C46A 2.8700 . 2_666 no
    H32B H46C 2.5900 . 2_666 no
    H32B N2B 2.4700 . . no
    H33A H33B 2.5400 . 1_655 no
    H33B H33A 2.5400 . 1_455 no
    H33B C33A 3.0300 . 1_455 no
    H36A C4A 2.9200 . . no
    H36A O41A 2.2100 . . no
    H36A H4C 2.5200 . . no
    H36A C41A 2.8000 . . no
    H36B C4B 2.9000 . . no
    H36B C41B 2.7900 . . no
    H36B O41B 2.2300 . . no
    H41A H5A 2.4400 . . no
    H41A H6C 2.4800 . 2_676 no
    H41A H6B 2.5800 . 2_676 no
    H41A C46B 2.8900 . 2_676 no
    H41B H46A 2.4300 . 1_464 no
    H41B H5B 2.4400 . . no
    H41B C46A 2.9900 . 1_464 no
    H44A O41B 2.6600 . 2_665 no
    H44B H14A 2.4400 . . no
    H46A C36A 2.9300 . 2_766 no
    H46A H41B 2.4300 . 1_646 no
    H46A C35A 2.9400 . 2_766 no
    H46B N12B 2.8900 . 2_666 no
    H46B C41B 3.0300 . 1_646 no
    H46C H32B 2.5900 . 2_666 no
    H46C Cl2 2.9700 . 1_656 no
    H46C C35A 2.9400 . 2_666 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2A N1A C5A . . . 112.13(19) no
    N2A N1A C11A . . . 122.00(19) no
    C5A N1A C11A . . . 125.9(2) no
    N1A N2A C3A . . . 105.52(18) no
    C11A N12A C13A . . . 114.2(2) no
    C11A N16A C15A . . . 115.2(2) no
    C5B N1B C11B . . . 125.1(2) no
    N2B N1B C5B . . . 112.43(19) no
    N2B N1B C11B . . . 122.43(19) no
    N1B N2B C3B . . . 105.31(18) no
    C11B N12B C13B . . . 114.3(2) no
    C11B N16B C15B . . . 115.4(2) no
    N2A C3A C4A . . . 110.2(2) no
    N2A C3A C31A . . . 117.6(2) no
    C4A C3A C31A . . . 132.2(2) no
    C3A C4A C5A . . . 104.7(2) no
    C3A C4A C41A . . . 136.9(2) no
    C5A C4A C41A . . . 118.4(2) no
    N1A C5A C4A . . . 107.5(2) no
    N1A C11A N12A . . . 117.4(2) no
    N12A C11A N16A . . . 130.0(2) no
    N1A C11A N16A . . . 112.7(2) no
    N12A C13A C14A . . . 121.4(2) no
    C14A C13A C44A . . . 122.7(2) no
    N12A C13A C44A . . . 115.9(2) no
    C13A C14A C15A . . . 118.8(2) no
    N16A C15A C46A . . . 116.5(2) no
    N16A C15A C14A . . . 120.6(2) no
    C14A C15A C46A . . . 122.9(2) no
    C3A C31A C36A . . . 122.9(2) no
    C3A C31A C32A . . . 118.9(2) no
    C32A C31A C36A . . . 118.3(2) no
    C31A C32A C33A . . . 121.2(2) no
    C32A C33A C34A . . . 119.1(2) no
    Cl1 C34A C33A . . . 119.28(19) no
    Cl1 C34A C35A . . . 119.58(19) no
    C33A C34A C35A . . . 121.1(2) no
    C34A C35A C36A . . . 119.1(2) no
    C31A C36A C35A . . . 121.1(2) no
    O41A C41A C4A . . . 129.2(2) no
    N1A C5A H5A . . . 126.00 no
    C4A C5A H5A . . . 126.00 no
    C15A C14A H14A . . . 121.00 no
    C13A C14A H14A . . . 121.00 no
    C31A C32A H32A . . . 119.00 no
    C33A C32A H32A . . . 119.00 no
    C32A C33A H33A . . . 120.00 no
    C34A C33A H33A . . . 120.00 no
    C36A C35A H35A . . . 120.00 no
    C34A C35A H35A . . . 120.00 no
    C31A C36A H36A . . . 119.00 no
    C35A C36A H36A . . . 119.00 no
    O41A C41A H41A . . . 115.00 no
    C4A C41A H41A . . . 115.00 no
    H44A C44A H44B . . . 110.00 no
    H44A C44A H44C . . . 109.00 no
    C13A C44A H44A . . . 109.00 no
    C13A C44A H44B . . . 109.00 no
    C13A C44A H44C . . . 109.00 no
    H44B C44A H44C . . . 110.00 no
    H46B C46A H46C . . . 109.00 no
    C15A C46A H46A . . . 109.00 no
    C15A C46A H46B . . . 109.00 no
    C15A C46A H46C . . . 109.00 no
    H46A C46A H46B . . . 109.00 no
    H46A C46A H46C . . . 109.00 no
    N2B C3B C4B . . . 110.1(2) no
    N2B C3B C31B . . . 118.4(2) no
    C4B C3B C31B . . . 131.5(2) no
    C3B C4B C5B . . . 104.8(2) no
    C3B C4B C41B . . . 136.7(2) no
    C5B C4B C41B . . . 118.5(2) no
    N1B C5B C4B . . . 107.3(2) no
    N1B C11B N12B . . . 117.4(2) no
    N1B C11B N16B . . . 112.7(2) no
    N12B C11B N16B . . . 129.9(2) no
    N12B C13B C14B . . . 121.5(2) no
    N12B C13B C44B . . . 116.1(2) no
    C14B C13B C44B . . . 122.4(2) no
    C13B C14B C15B . . . 118.2(2) no
    N16B C15B C14B . . . 120.7(2) no
    N16B C15B C46B . . . 116.3(2) no
    C14B C15B C46B . . . 123.0(2) no
    C3B C31B C32B . . . 119.4(2) no
    C3B C31B C36B . . . 122.2(2) no
    C32B C31B C36B . . . 118.4(2) no
    C31B C32B C33B . . . 120.9(2) no
    C32B C33B C34B . . . 119.5(2) no
    Cl2 C34B C33B . . . 119.7(2) no
    Cl2 C34B C35B . . . 119.3(2) no
    C33B C34B C35B . . . 121.1(2) no
    C34B C35B C36B . . . 119.1(2) no
    C31B C36B C35B . . . 120.9(2) no
    O41B C41B C4B . . . 128.8(2) no
    N1B C5B H5B . . . 126.00 no
    C4B C5B H5B . . . 126.00 no
    C13B C14B H14B . . . 121.00 no
    C15B C14B H14B . . . 121.00 no
    C31B C32B H32B . . . 120.00 no
    C33B C32B H32B . . . 120.00 no
    C32B C33B H33B . . . 120.00 no
    C34B C33B H33B . . . 120.00 no
    C34B C35B H35B . . . 120.00 no
    C36B C35B H35B . . . 120.00 no
    C31B C36B H36B . . . 120.00 no
    C35B C36B H36B . . . 120.00 no
    O41B C41B H41B . . . 116.00 no
    C4B C41B H41B . . . 116.00 no
    C13B C44B H4A . . . 109.00 no
    C13B C44B H4B . . . 110.00 no
    C13B C44B H4C . . . 109.00 no
    H4A C44B H4B . . . 109.00 no
    H4A C44B H4C . . . 109.00 no
    H4B C44B H4C . . . 109.00 no
    C15B C46B H6A . . . 109.00 no
    C15B C46B H6B . . . 109.00 no
    C15B C46B H6C . . . 109.00 no
    H6A C46B H6B . . . 110.00 no
    H6A C46B H6C . . . 109.00 no
    H6B C46B H6C . . . 109.00 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5A N1A N2A C3A . . . . -0.6(3) no
    C11A N1A N2A C3A . . . . 179.1(2) no
    N2A N1A C5A C4A . . . . 0.6(3) no
    C11A N1A C5A C4A . . . . -179.1(2) no
    N2A N1A C11A N12A . . . . 6.3(3) no
    N2A N1A C11A N16A . . . . -174.4(2) no
    C5A N1A C11A N12A . . . . -174.0(2) no
    C5A N1A C11A N16A . . . . 5.3(3) no
    N1A N2A C3A C4A . . . . 0.4(3) no
    N1A N2A C3A C31A . . . . 178.90(19) no
    C13A N12A C11A N1A . . . . 179.0(2) no
    C13A N12A C11A N16A . . . . -0.2(4) no
    C11A N12A C13A C14A . . . . 0.6(3) no
    C11A N12A C13A C44A . . . . -178.9(2) no
    C15A N16A C11A N1A . . . . -179.2(2) no
    C15A N16A C11A N12A . . . . 0.0(4) no
    C11A N16A C15A C14A . . . . -0.2(3) no
    C11A N16A C15A C46A . . . . 179.8(2) no
    N2B N1B C11B N16B . . . . -173.6(2) no
    C5B N1B C11B N12B . . . . -172.5(2) no
    C5B N1B C11B N16B . . . . 6.9(3) no
    N2B N1B C5B C4B . . . . 0.4(3) no
    C5B N1B N2B C3B . . . . -0.7(3) no
    C11B N1B N2B C3B . . . . 179.7(2) no
    C11B N1B C5B C4B . . . . 180.0(2) no
    N2B N1B C11B N12B . . . . 7.1(3) no
    N1B N2B C3B C4B . . . . 0.7(3) no
    N1B N2B C3B C31B . . . . -179.19(19) no
    C13B N12B C11B N1B . . . . -179.5(2) no
    C13B N12B C11B N16B . . . . 1.3(4) no
    C11B N12B C13B C44B . . . . -177.3(2) no
    C11B N12B C13B C14B . . . . 0.7(4) no
    C15B N16B C11B N12B . . . . -1.3(4) no
    C15B N16B C11B N1B . . . . 179.5(2) no
    C11B N16B C15B C14B . . . . -0.8(3) no
    C11B N16B C15B C46B . . . . 178.7(2) no
    C31A C3A C4A C5A . . . . -178.3(2) no
    N2A C3A C4A C5A . . . . 0.0(3) no
    N2A C3A C4A C41A . . . . -179.0(3) no
    N2A C3A C31A C36A . . . . 173.2(2) no
    C4A C3A C31A C32A . . . . 171.7(2) no
    C4A C3A C31A C36A . . . . -8.7(4) no
    N2A C3A C31A C32A . . . . -6.4(3) no
    C31A C3A C4A C41A . . . . 2.8(5) no
    C41A C4A C5A N1A . . . . 178.9(2) no
    C3A C4A C5A N1A . . . . -0.4(2) no
    C5A C4A C41A O41A . . . . -171.7(3) no
    C3A C4A C41A O41A . . . . 7.2(5) no
    N12A C13A C14A C15A . . . . -0.9(3) no
    C44A C13A C14A C15A . . . . 178.6(2) no
    C13A C14A C15A C46A . . . . -179.4(2) no
    C13A C14A C15A N16A . . . . 0.6(3) no
    C3A C31A C32A C33A . . . . 179.1(2) no
    C36A C31A C32A C33A . . . . -0.4(3) no
    C3A C31A C36A C35A . . . . 179.6(2) no
    C32A C31A C36A C35A . . . . -0.8(3) no
    C31A C32A C33A C34A . . . . 1.0(4) no
    C32A C33A C34A C35A . . . . -0.3(4) no
    C32A C33A C34A Cl1 . . . . 179.38(19) no
    Cl1 C34A C35A C36A . . . . 179.39(17) no
    C33A C34A C35A C36A . . . . -0.9(3) no
    C34A C35A C36A C31A . . . . 1.5(3) no
    N2B C3B C4B C5B . . . . -0.5(3) no
    N2B C3B C4B C41B . . . . -177.3(3) no
    C31B C3B C4B C5B . . . . 179.4(2) no
    C31B C3B C4B C41B . . . . 2.5(5) no
    N2B C3B C31B C32B . . . . 12.4(3) no
    N2B C3B C31B C36B . . . . -165.9(2) no
    C4B C3B C31B C32B . . . . -167.4(2) no
    C4B C3B C31B C36B . . . . 14.3(4) no
    C3B C4B C5B N1B . . . . 0.1(2) no
    C41B C4B C5B N1B . . . . 177.6(2) no
    C3B C4B C41B O41B . . . . 1.2(5) no
    C5B C4B C41B O41B . . . . -175.4(3) no
    N12B C13B C14B C15B . . . . -2.5(4) no
    C44B C13B C14B C15B . . . . 175.3(3) no
    C13B C14B C15B N16B . . . . 2.5(3) no
    C13B C14B C15B C46B . . . . -176.9(2) no
    C3B C31B C32B C33B . . . . -179.7(2) no
    C36B C31B C32B C33B . . . . -1.3(4) no
    C3B C31B C36B C35B . . . . 179.1(2) no
    C32B C31B C36B C35B . . . . 0.8(4) no
    C31B C32B C33B C34B . . . . 0.5(4) no
    C32B C33B C34B Cl2 . . . . -178.1(2) no
    C32B C33B C34B C35B . . . . 0.9(4) no
    Cl2 C34B C35B C36B . . . . 177.6(2) no
    C33B C34B C35B C36B . . . . -1.4(4) no
    C34B C35B C36B C31B . . . . 0.5(4) 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
    C32A H32A N2A . 0.9500 2.4300 2.770(3) 101.00 yes
    C32B H32B N2B . 0.9500 2.4700 2.800(3) 100.00 yes
    C36A H36A O41A . 0.9500 2.2100 3.076(3) 152.00 yes
    C36B H36B O41B . 0.9500 2.2300 3.054(3) 144.00 yes
