#------------------------------------------------------------------------------
#$Date: 2023-03-23 12:09:24 +0200 (Thu, 23 Mar 2023) $
#$Revision: 282017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106966
loop_
_publ_author_name
'Pansuriya, Pramod B.'
'Patel, Chintan'
'Friedrich, Holger B.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 Crystal structure of
 N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4,
 C13H12N4O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              649
_journal_page_last               652
_journal_paper_doi               10.1515/ncrs-2015-0229
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C13 H12 N4 O2'
_chemical_formula_weight         256.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   16.2353(11)
_cell_length_b                   16.8474(12)
_cell_length_c                   36.028(2)
_cell_measurement_reflns_used    70312
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      1.13
_cell_volume                     9854.5(11)
_computing_cell_refinement
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_data_collection
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_data_reduction
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_molecular_graphics    'OLEX-2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II Diffractometer'
_diffrn_measurement_method       '0.5° φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            70312
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.973
_diffrn_reflns_theta_min         1.130
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (APEX2, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             4288
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.861
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.00098(17)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   2.578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         10680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.578
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8820
_reflns_number_total             11817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0229_suppl.cif
_cod_data_source_block           isourea
_cod_original_cell_volume        9854.5(12)
_cod_database_code               8106966
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.988
_exptl_absorpt_special_details   n/a
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.01718(14) 0.09019(13) 0.30136(6) 0.0334(6) Uani 1 1 d . . . . .
O2A O 0.09788(13) 0.19241(13) 0.22651(6) 0.0306(5) Uani 1 1 d . . . . .
N1A N -0.0088(2) 0.2697(2) 0.40905(9) 0.0539(9) Uani 1 1 d . . . . .
N2A N -0.03382(15) 0.19856(15) 0.27255(7) 0.0235(6) Uani 1 1 d . . . . .
H2A H -0.0495 0.2472 0.2743 0.028 Uiso 1 1 calc R U . . .
N3A N -0.03566(15) 0.16005(15) 0.23874(7) 0.0243(6) Uani 1 1 d . . . . .
H3A H -0.0810 0.1438 0.2291 0.029 Uiso 1 1 calc R U . . .
N4A N 0.03786(15) 0.08732(15) 0.19679(7) 0.0246(6) Uani 1 1 d . . . . .
H4A H -0.0022 0.0543 0.1991 0.030 Uiso 1 1 calc R U . . .
C1A C 0.0557(3) 0.2322(3) 0.39584(11) 0.0479(10) Uani 1 1 d . . . . .
H1A H 0.1027 0.2295 0.4106 0.058 Uiso 1 1 calc R U . . .
C2A C 0.0580(2) 0.1969(2) 0.36169(9) 0.0340(8) Uani 1 1 d . . . . .
H2AA H 0.1044 0.1687 0.3543 0.041 Uiso 1 1 calc R U . . .
C3A C -0.00867(19) 0.20332(18) 0.33840(9) 0.0262(7) Uani 1 1 d . . . . .
C4A C -0.0773(2) 0.2451(2) 0.35046(10) 0.0385(9) Uani 1 1 d . . . . .
H4AA H -0.1231 0.2524 0.3354 0.046 Uiso 1 1 calc R U . . .
C5A C -0.0737(3) 0.2758(2) 0.38688(12) 0.0524(11) Uani 1 1 d . . . . .
H5A H -0.1199 0.3020 0.3959 0.063 Uiso 1 1 calc R U . . .
C6A C -0.00751(18) 0.15949(18) 0.30228(9) 0.0232(7) Uani 1 1 d . . . . .
C7A C 0.03928(18) 0.14899(18) 0.22125(8) 0.0215(6) Uani 1 1 d . . . . .
C8A C 0.09456(18) 0.07144(19) 0.16811(8) 0.0244(7) Uani 1 1 d . . . . .
C9A C 0.16561(19) 0.1153(2) 0.16180(10) 0.0325(8) Uani 1 1 d . . . . .
H9A H 0.1793 0.1572 0.1775 0.039 Uiso 1 1 calc R U . . .
C10A C 0.2158(2) 0.0963(2) 0.13203(10) 0.0412(9) Uani 1 1 d . . . . .
H10A H 0.2630 0.1262 0.1277 0.049 Uiso 1 1 calc R U . . .
C11A C 0.1976(3) 0.0347(3) 0.10886(12) 0.0504(11) Uani 1 1 d . . . . .
H11A H 0.2321 0.0226 0.0891 0.061 Uiso 1 1 calc R U . . .
C12A C 0.1269(3) -0.0097(2) 0.11513(11) 0.0503(11) Uani 1 1 d . . . . .
H12A H 0.1136 -0.0514 0.0993 0.060 Uiso 1 1 calc R U . . .
C13A C 0.0762(2) 0.0081(2) 0.14493(10) 0.0341(8) Uani 1 1 d . . . . .
H13A H 0.0297 -0.0226 0.1494 0.041 Uiso 1 1 calc R U . . .
O1B O 0.38815(13) 0.35445(13) 0.22614(6) 0.0297(5) Uani 1 1 d . . . . .
O2B O 0.56436(13) 0.44633(13) 0.20838(6) 0.0275(5) Uani 1 1 d . . . . .
N1B N 0.18250(17) 0.57093(17) 0.24826(9) 0.0359(7) Uani 1 1 d . . . . .
N2B N 0.45656(15) 0.43647(16) 0.26515(7) 0.0252(6) Uani 1 1 d . . . . .
H2B H 0.4552 0.4780 0.2790 0.030 Uiso 1 1 calc R U . . .
N3B N 0.52688(15) 0.38998(16) 0.26331(7) 0.0273(6) Uani 1 1 d . . . . .
H3B H 0.5423 0.3611 0.2817 0.033 Uiso 1 1 calc R U . . .
N4B N 0.62343(15) 0.32982(15) 0.22731(7) 0.0258(6) Uani 1 1 d . . . . .
H4B H 0.6188 0.2915 0.2429 0.031 Uiso 1 1 calc R U . . .
C1B C 0.2392(2) 0.5730(2) 0.27468(11) 0.0392(9) Uani 1 1 d . . . . .
H1B H 0.2327 0.6096 0.2938 0.047 Uiso 1 1 calc R U . . .
C2B C 0.3073(2) 0.5241(2) 0.27544(10) 0.0327(8) Uani 1 1 d . . . . .
H2BA H 0.3450 0.5272 0.2948 0.039 Uiso 1 1 calc R U . . .
C3B C 0.31856(18) 0.47060(17) 0.24693(9) 0.0226(7) Uani 1 1 d . . . . .
C4B C 0.26016(19) 0.4682(2) 0.21911(10) 0.0331(8) Uani 1 1 d . . . . .
H4BA H 0.2654 0.4327 0.1995 0.040 Uiso 1 1 calc R U . . .
C5B C 0.1942(2) 0.5191(2) 0.22099(11) 0.0369(9) Uani 1 1 d . . . . .
H5B H 0.1553 0.5171 0.2020 0.044 Uiso 1 1 calc R U . . .
C6B C 0.39023(18) 0.41533(19) 0.24480(8) 0.0231(7) Uani 1 1 d . . . . .
C7B C 0.57092(17) 0.39207(18) 0.23075(9) 0.0228(7) Uani 1 1 d . . . . .
C8B C 0.68515(18) 0.32373(18) 0.19991(9) 0.0249(7) Uani 1 1 d . . . . .
C9B C 0.76093(19) 0.2919(2) 0.21013(10) 0.0310(8) Uani 1 1 d . . . . .
H9B H 0.7691 0.2742 0.2343 0.037 Uiso 1 1 calc R U . . .
C10B C 0.8237(2) 0.2864(2) 0.18472(11) 0.0391(9) Uani 1 1 d . . . . .
H10B H 0.8742 0.2653 0.1918 0.047 Uiso 1 1 calc R U . . .
C11B C 0.8121(2) 0.3120(2) 0.14903(11) 0.0419(9) Uani 1 1 d . . . . .
H11B H 0.8553 0.3096 0.1321 0.050 Uiso 1 1 calc R U . . .
C12B C 0.7369(2) 0.3410(2) 0.13825(10) 0.0400(9) Uani 1 1 d . . . . .
H12B H 0.7286 0.3568 0.1138 0.048 Uiso 1 1 calc R U . . .
C13B C 0.6731(2) 0.3469(2) 0.16371(10) 0.0341(8) Uani 1 1 d . . . . .
H13B H 0.6222 0.3665 0.1563 0.041 Uiso 1 1 calc R U . . .
O1C O 0.25677(14) 0.18445(15) 0.55918(7) 0.0397(6) Uani 1 1 d . . . . .
O2C O 0.14443(14) 0.14188(15) 0.47860(7) 0.0386(6) Uani 1 1 d . . . . .
N1C N 0.05019(17) 0.18702(18) 0.66175(8) 0.0366(7) Uani 1 1 d . . . . .
N2C N 0.15424(17) 0.25356(17) 0.53258(7) 0.0312(7) Uani 1 1 d . . . . .
H2C H 0.1061 0.2746 0.5344 0.037 Uiso 1 1 calc R U . . .
N3C N 0.19934(18) 0.25911(17) 0.49961(7) 0.0334(7) Uani 1 1 d . . . . .
H3C H 0.2299 0.2996 0.4948 0.040 Uiso 1 1 calc R U . . .
N4C N 0.24947(17) 0.20211(17) 0.44789(7) 0.0325(7) Uani 1 1 d . . . . .
H4C H 0.2783 0.2450 0.4477 0.039 Uiso 1 1 calc R U . . .
C1C C 0.1148(2) 0.1436(3) 0.65347(10) 0.0467(10) Uani 1 1 d . . . . .
H1C H 0.1310 0.1053 0.6705 0.056 Uiso 1 1 calc R U . . .
C2C C 0.1603(2) 0.1507(3) 0.62130(10) 0.0437(10) Uani 1 1 d . . . . .
H2CA H 0.2058 0.1184 0.6171 0.052 Uiso 1 1 calc R U . . .
C3C C 0.13657(19) 0.2074(2) 0.59525(9) 0.0268(7) Uani 1 1 d . . . . .
C4C C 0.06918(19) 0.2531(2) 0.60387(9) 0.0281(7) Uani 1 1 d . . . . .
H4CA H 0.0512 0.2920 0.5874 0.034 Uiso 1 1 calc R U . . .
C5C C 0.0282(2) 0.2411(2) 0.63697(9) 0.0330(8) Uani 1 1 d . . . . .
H5C H -0.0173 0.2727 0.6422 0.040 Uiso 1 1 calc R U . . .
C6C C 0.1871(2) 0.2154(2) 0.56083(9) 0.0297(8) Uani 1 1 d . . . . .
C7C C 0.1924(2) 0.1958(2) 0.47485(9) 0.0300(8) Uani 1 1 d . . . . .
C8C C 0.26728(19) 0.14582(19) 0.41977(8) 0.0260(7) Uani 1 1 d . . . . .
C9C C 0.3445(2) 0.1517(2) 0.40354(9) 0.0332(8) Uani 1 1 d . . . . .
H9C H 0.3813 0.1905 0.4114 0.040 Uiso 1 1 calc R U . . .
C10C C 0.3667(2) 0.0994(2) 0.37551(10) 0.0402(9) Uani 1 1 d . . . . .
H10C H 0.4181 0.1036 0.3643 0.048 Uiso 1 1 calc R U . . .
C11C C 0.3129(3) 0.0414(2) 0.36425(11) 0.0451(10) Uani 1 1 d . . . . .
H11C H 0.3279 0.0061 0.3456 0.054 Uiso 1 1 calc R U . . .
C12C C 0.2372(2) 0.0359(3) 0.38053(11) 0.0490(10) Uani 1 1 d . . . . .
H12C H 0.2007 -0.0031 0.3726 0.059 Uiso 1 1 calc R U . . .
C13C C 0.2137(2) 0.0871(2) 0.40854(10) 0.0401(9) Uani 1 1 d . . . . .
H13C H 0.1623 0.0820 0.4197 0.048 Uiso 1 1 calc R U . . .
O1D O 0.00267(14) 0.16073(15) 0.02567(7) 0.0396(6) Uani 1 1 d . . . . .
O2D O -0.11764(15) 0.31324(16) 0.04439(7) 0.0419(6) Uani 1 1 d . . . . .
N1D N -0.1753(2) -0.0818(2) 0.02407(10) 0.0530(9) Uani 1 1 d . . . . .
N2D N -0.10339(18) 0.20146(18) -0.00988(8) 0.0379(7) Uani 1 1 d . . . . .
H2D H -0.1502 0.1918 -0.0201 0.045 Uiso 1 1 calc R U . . .
N3D N -0.06712(19) 0.27529(17) -0.01266(8) 0.0381(7) Uani 1 1 d . . . . .
H3D H -0.0461 0.2922 -0.0331 0.046 Uiso 1 1 calc R U . . .
N4D N -0.00592(18) 0.37430(17) 0.02054(8) 0.0375(7) Uani 1 1 d . . . . .
H4D H 0.0276 0.3729 0.0021 0.045 Uiso 1 1 calc R U . . .
C1D C -0.1059(3) -0.0607(2) 0.04240(12) 0.0511(11) Uani 1 1 d . . . . .
H1D H -0.0825 -0.0966 0.0589 0.061 Uiso 1 1 calc R U . . .
C2D C -0.0680(2) 0.0135(2) 0.03734(10) 0.0390(9) Uani 1 1 d . . . . .
H2DA H -0.0199 0.0269 0.0499 0.047 Uiso 1 1 calc R U . . .
C3D C -0.1047(2) 0.06567(19) 0.01311(9) 0.0290(7) Uani 1 1 d . . . . .
C4D C -0.1763(2) 0.0437(2) -0.00475(11) 0.0444(10) Uani 1 1 d . . . . .
H4DA H -0.2024 0.0785 -0.0209 0.053 Uiso 1 1 calc R U . . .
C5D C -0.2077(3) -0.0292(2) 0.00162(14) 0.0563(12) Uani 1 1 d . . . . .
H5D H -0.2557 -0.0431 -0.0108 0.068 Uiso 1 1 calc R U . . .
C6D C -0.0640(2) 0.1463(2) 0.00897(10) 0.0365(8) Uani 1 1 d . . . . .
C7D C -0.0666(2) 0.3215(2) 0.02007(10) 0.0355(8) Uani 1 1 d . . . . .
C8D C 0.0100(2) 0.43248(19) 0.04775(10) 0.0307(8) Uani 1 1 d . . . . .
C9D C -0.0295(2) 0.4387(2) 0.08184(10) 0.0390(9) Uani 1 1 d . . . . .
H9D H -0.0725 0.4044 0.0877 0.047 Uiso 1 1 calc R U . . .
C10D C -0.0054(2) 0.4953(3) 0.10677(12) 0.0499(11) Uani 1 1 d . . . . .
H10D H -0.0318 0.4986 0.1296 0.060 Uiso 1 1 calc R U . . .
C11D C 0.0570(2) 0.5470(2) 0.09859(12) 0.0495(11) Uani 1 1 d . . . . .
H11D H 0.0731 0.5850 0.1159 0.059 Uiso 1 1 calc R U . . .
C12D C 0.0950(2) 0.5427(2) 0.06546(12) 0.0456(10) Uani 1 1 d . . . . .
H12D H 0.1365 0.5788 0.0598 0.055 Uiso 1 1 calc R U . . .
C13D C 0.0731(2) 0.4851(2) 0.03955(11) 0.0386(9) Uani 1 1 d . . . . .
H13D H 0.1007 0.4819 0.0170 0.046 Uiso 1 1 calc R U . . .
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'
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_3
C1A N1A C5A 116.9(3) . .
C6A N2A N3A 119.1(3) . .
C6A N2A H2A 120.5 . .
N3A N2A H2A 120.5 . .
N2A N3A C7A 116.5(2) . .
N2A N3A H3A 121.7 . .
C7A N3A H3A 121.7 . .
C7A N4A C8A 127.4(3) . .
C7A N4A H4A 116.3 . .
C8A N4A H4A 116.3 . .
N1A C1A C2A 123.9(4) . .
N1A C1A H1A 118.0 . .
C2A C1A H1A 118.0 . .
C1A C2A C3A 119.6(4) . .
C1A C2A H2AA 120.2 . .
C3A C2A H2AA 120.2 . .
C2A C3A C4A 118.8(3) . .
C2A C3A C6A 118.8(3) . .
C4A C3A C6A 122.2(3) . .
C3A C4A C5A 116.4(4) . .
C3A C4A H4AA 121.8 . .
C5A C4A H4AA 121.8 . .
N1A C5A C4A 124.3(4) . .
N1A C5A H5A 117.8 . .
C4A C5A H5A 117.8 . .
O1A C6A N2A 123.5(3) . .
O1A C6A C3A 119.6(3) . .
N2A C6A C3A 116.9(3) . .
O2A C7A N4A 125.0(3) . .
O2A C7A N3A 122.5(3) . .
N4A C7A N3A 112.5(3) . .
C13A C8A C9A 119.3(3) . .
C13A C8A N4A 116.6(3) . .
C9A C8A N4A 124.1(3) . .
C10A C9A C8A 119.5(3) . .
C10A C9A H9A 120.2 . .
C8A C9A H9A 120.2 . .
C11A C10A C9A 121.4(3) . .
C11A C10A H10A 119.3 . .
C9A C10A H10A 119.3 . .
C10A C11A C12A 119.3(4) . .
C10A C11A H11A 120.3 . .
C12A C11A H11A 120.3 . .
C13A C12A C11A 120.0(4) . .
C13A C12A H12A 120.0 . .
C11A C12A H12A 120.0 . .
C12A C13A C8A 120.4(3) . .
C12A C13A H13A 119.8 . .
C8A C13A H13A 119.8 . .
C1B N1B C5B 116.7(3) . .
C6B N2B N3B 118.8(3) . .
C6B N2B H2B 120.6 . .
N3B N2B H2B 120.6 . .
C7B N3B N2B 117.1(2) . .
C7B N3B H3B 121.5 . .
N2B N3B H3B 121.5 . .
C7B N4B C8B 124.5(3) . .
C7B N4B H4B 117.8 . .
C8B N4B H4B 117.8 . .
N1B C1B C2B 123.8(3) . .
N1B C1B H1B 118.1 . .
C2B C1B H1B 118.1 . .
C1B C2B C3B 118.8(3) . .
C1B C2B H2BA 120.6 . .
C3B C2B H2BA 120.6 . .
C4B C3B C2B 118.0(3) . .
C4B C3B C6B 118.7(3) . .
C2B C3B C6B 123.3(3) . .
C5B C4B C3B 118.8(3) . .
C5B C4B H4BA 120.6 . .
C3B C4B H4BA 120.6 . .
N1B C5B C4B 123.9(3) . .
N1B C5B H5B 118.0 . .
C4B C5B H5B 118.0 . .
O1B C6B N2B 122.7(3) . .
O1B C6B C3B 121.9(3) . .
N2B C6B C3B 115.4(3) . .
O2B C7B N4B 124.9(3) . .
O2B C7B N3B 122.4(3) . .
N4B C7B N3B 112.6(3) . .
C13B C8B C9B 119.0(3) . .
C13B C8B N4B 122.9(3) . .
C9B C8B N4B 118.1(3) . .
C10B C9B C8B 120.4(3) . .
C10B C9B H9B 119.8 . .
C8B C9B H9B 119.8 . .
C11B C10B C9B 120.3(3) . .
C11B C10B H10B 119.9 . .
C9B C10B H10B 119.9 . .
C10B C11B C12B 120.0(3) . .
C10B C11B H11B 120.0 . .
C12B C11B H11B 120.0 . .
C11B C12B C13B 120.2(3) . .
C11B C12B H12B 119.9 . .
C13B C12B H12B 119.9 . .
C8B C13B C12B 120.1(3) . .
C8B C13B H13B 120.0 . .
C12B C13B H13B 120.0 . .
C1C N1C C5C 116.4(3) . .
C6C N2C N3C 118.5(3) . .
C6C N2C H2C 120.8 . .
N3C N2C H2C 120.8 . .
C7C N3C N2C 116.7(3) . .
C7C N3C H3C 121.6 . .
N2C N3C H3C 121.6 . .
C7C N4C C8C 127.1(3) . .
C7C N4C H4C 116.5 . .
C8C N4C H4C 116.5 . .
N1C C1C C2C 124.8(4) . .
N1C C1C H1C 117.6 . .
C2C C1C H1C 117.6 . .
C1C C2C C3C 118.5(3) . .
C1C C2C H2CA 120.8 . .
C3C C2C H2CA 120.8 . .
C4C C3C C2C 116.9(3) . .
C4C C3C C6C 125.1(3) . .
C2C C3C C6C 118.0(3) . .
C3C C4C C5C 119.8(3) . .
C3C C4C H4CA 120.1 . .
C5C C4C H4CA 120.1 . .
N1C C5C C4C 123.6(3) . .
N1C C5C H5C 118.2 . .
C4C C5C H5C 118.2 . .
O1C C6C N2C 122.3(3) . .
O1C C6C C3C 120.0(3) . .
N2C C6C C3C 117.6(3) . .
O2C C7C N4C 125.9(3) . .
O2C C7C N3C 123.9(3) . .
N4C C7C N3C 110.2(3) . .
C13C C8C C9C 119.9(3) . .
C13C C8C N4C 124.2(3) . .
C9C C8C N4C 116.0(3) . .
C8C C9C C10C 119.7(3) . .
C8C C9C H9C 120.1 . .
C10C C9C H9C 120.1 . .
C11C C10C C9C 120.1(3) . .
C11C C10C H10C 119.9 . .
C9C C10C H10C 119.9 . .
C12C C11C C10C 119.7(4) . .
C12C C11C H11C 120.2 . .
C10C C11C H11C 120.2 . .
C11C C12C C13C 121.4(4) . .
C11C C12C H12C 119.3 . .
C13C C12C H12C 119.3 . .
C8C C13C C12C 119.3(3) . .
C8C C13C H13C 120.4 . .
C12C C13C H13C 120.4 . .
C5D N1D C1D 117.2(3) . .
C6D N2D N3D 117.8(3) . .
C6D N2D H2D 121.1 . .
N3D N2D H2D 121.1 . .
N2D N3D C7D 116.0(3) . .
N2D N3D H3D 122.0 . .
C7D N3D H3D 122.0 . .
C7D N4D C8D 127.7(3) . .
C7D N4D H4D 116.2 . .
C8D N4D H4D 116.2 . .
N1D C1D C2D 122.3(4) . .
N1D C1D H1D 118.8 . .
C2D C1D H1D 118.8 . .
C3D C2D C1D 117.5(3) . .
C3D C2D H2DA 121.3 . .
C1D C2D H2DA 121.3 . .
C2D C3D C4D 119.3(3) . .
C2D C3D C6D 116.4(3) . .
C4D C3D C6D 124.2(3) . .
C5D C4D C3D 118.9(4) . .
C5D C4D H4DA 120.5 . .
C3D C4D H4DA 120.5 . .
N1D C5D C4D 124.7(4) . .
N1D C5D H5D 117.7 . .
C4D C5D H5D 117.7 . .
O1D C6D N2D 121.7(3) . .
O1D C6D C3D 120.0(3) . .
N2D C6D C3D 118.1(3) . .
O2D C7D N4D 125.0(3) . .
O2D C7D N3D 122.3(3) . .
N4D C7D N3D 112.6(3) . .
C13D C8D C9D 118.8(3) . .
C13D C8D N4D 115.6(3) . .
C9D C8D N4D 125.6(3) . .
C10D C9D C8D 120.1(4) . .
C10D C9D H9D 120.0 . .
C8D C9D H9D 120.0 . .
C9D C10D C11D 121.0(4) . .
C9D C10D H10D 119.5 . .
C11D C10D H10D 119.5 . .
C12D C11D C10D 119.7(4) . .
C12D C11D H11D 120.1 . .
C10D C11D H11D 120.1 . .
C11D C12D C13D 121.0(4) . .
C11D C12D H12D 119.5 . .
C13D C12D H12D 119.5 . .
C8D C13D C12D 119.4(4) . .
C8D C13D H13D 120.3 . .
C12D C13D H13D 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C6A 1.235(4) .
O2A C7A 1.215(3) .
N1A C1A 1.313(5) .
N1A C5A 1.327(5) .
N2A C6A 1.328(4) .
N2A N3A 1.380(3) .
N2A H2A 0.8600 .
N3A C7A 1.383(4) .
N3A H3A 0.8600 .
N4A C7A 1.362(4) .
N4A C8A 1.410(4) .
N4A H4A 0.8600 .
C1A C2A 1.367(5) .
C1A H1A 0.9300 .
C2A C3A 1.374(5) .
C2A H2AA 0.9300 .
C3A C4A 1.387(5) .
C3A C6A 1.497(4) .
C4A C5A 1.412(5) .
C4A H4AA 0.9300 .
C5A H5A 0.9300 .
C8A C13A 1.387(5) .
C8A C9A 1.389(4) .
C9A C10A 1.385(5) .
C9A H9A 0.9300 .
C10A C11A 1.365(5) .
C10A H10A 0.9300 .
C11A C12A 1.388(6) .
C11A H11A 0.9300 .
C12A C13A 1.386(5) .
C12A H12A 0.9300 .
C13A H13A 0.9300 .
O1B C6B 1.227(4) .
O2B C7B 1.223(4) .
N1B C1B 1.325(5) .
N1B C5B 1.328(5) .
N2B C6B 1.351(4) .
N2B N3B 1.386(3) .
N2B H2B 0.8600 .
N3B C7B 1.374(4) .
N3B H3B 0.8600 .
N4B C7B 1.357(4) .
N4B C8B 1.411(4) .
N4B H4B 0.8600 .
C1B C2B 1.379(5) .
C1B H1B 0.9300 .
C2B C3B 1.379(4) .
C2B H2BA 0.9300 .
C3B C4B 1.380(4) .
C3B C6B 1.492(4) .
C4B C5B 1.374(5) .
C4B H4BA 0.9300 .
C5B H5B 0.9300 .
C8B C13B 1.375(5) .
C8B C9B 1.392(4) .
C9B C10B 1.373(5) .
C9B H9B 0.9300 .
C10B C11B 1.369(5) .
C10B H10B 0.9300 .
C11B C12B 1.372(5) .
C11B H11B 0.9300 .
C12B C13B 1.387(5) .
C12B H12B 0.9300 .
C13B H13B 0.9300 .
O1C C6C 1.247(4) .
O2C C7C 1.204(4) .
N1C C1C 1.312(5) .
N1C C5C 1.325(4) .
N2C C6C 1.317(4) .
N2C N3C 1.399(4) .
N2C H2C 0.8600 .
N3C C7C 1.395(4) .
N3C H3C 0.8600 .
N4C C7C 1.347(4) .
N4C C8C 1.418(4) .
N4C H4C 0.8600 .
C1C C2C 1.380(5) .
C1C H1C 0.9300 .
C2C C3C 1.394(5) .
C2C H2CA 0.9300 .
C3C C4C 1.373(4) .
C3C C6C 1.493(4) .
C4C C5C 1.380(5) .
C4C H4CA 0.9300 .
C5C H5C 0.9300 .
C8C C13C 1.378(5) .
C8C C9C 1.388(4) .
C9C C10C 1.388(5) .
C9C H9C 0.9300 .
C10C C11C 1.371(5) .
C10C H10C 0.9300 .
C11C C12C 1.365(5) .
C11C H11C 0.9300 .
C12C C13C 1.381(5) .
C12C H12C 0.9300 .
C13C H13C 0.9300 .
O1D C6D 1.262(4) .
O2D C7D 1.215(4) .
N1D C5D 1.310(5) .
N1D C1D 1.353(5) .
N2D C6D 1.318(4) .
N2D N3D 1.380(4) .
N2D H2D 0.8600 .
N3D C7D 1.413(4) .
N3D H3D 0.8600 .
N4D C7D 1.327(4) .
N4D C8D 1.410(4) .
N4D H4D 0.8600 .
C1D C2D 1.405(5) .
C1D H1D 0.9300 .
C2D C3D 1.374(5) .
C2D H2DA 0.9300 .
C3D C4D 1.379(5) .
C3D C6D 1.518(5) .
C4D C5D 1.350(5) .
C4D H4DA 0.9300 .
C5D H5D 0.9300 .
C8D C13D 1.386(5) .
C8D C9D 1.390(5) .
C9D C10D 1.367(5) .
C9D H9D 0.9300 .
C10D C11D 1.369(6) .
C10D H10D 0.9300 .
C11D C12D 1.345(6) .
C11D H11D 0.9300 .
C12D C13D 1.393(5) .
C12D H12D 0.9300 .
C13D H13D 0.9300 .
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
C6A N2A N3A C7A -75.2(3) . . . .
C5A N1A C1A C2A -2.9(6) . . . .
N1A C1A C2A C3A 3.4(6) . . . .
C1A C2A C3A C4A -0.7(5) . . . .
C1A C2A C3A C6A -175.7(3) . . . .
C2A C3A C4A C5A -2.1(5) . . . .
C6A C3A C4A C5A 172.7(3) . . . .
C1A N1A C5A C4A -0.3(6) . . . .
C3A C4A C5A N1A 2.7(6) . . . .
N3A N2A C6A O1A 1.4(4) . . . .
N3A N2A C6A C3A -178.5(2) . . . .
C2A C3A C6A O1A 43.5(4) . . . .
C4A C3A C6A O1A -131.3(3) . . . .
C2A C3A C6A N2A -136.5(3) . . . .
C4A C3A C6A N2A 48.7(4) . . . .
C8A N4A C7A O2A -14.1(5) . . . .
C8A N4A C7A N3A 163.0(3) . . . .
N2A N3A C7A O2A -26.2(4) . . . .
N2A N3A C7A N4A 156.6(2) . . . .
C7A N4A C8A C13A -175.1(3) . . . .
C7A N4A C8A C9A 4.3(5) . . . .
C13A C8A C9A C10A 1.5(5) . . . .
N4A C8A C9A C10A -177.8(3) . . . .
C8A C9A C10A C11A -0.7(5) . . . .
C9A C10A C11A C12A 0.3(6) . . . .
C10A C11A C12A C13A -0.7(6) . . . .
C11A C12A C13A C8A 1.5(6) . . . .
C9A C8A C13A C12A -1.9(5) . . . .
N4A C8A C13A C12A 177.4(3) . . . .
C6B N2B N3B C7B 70.5(4) . . . .
C5B N1B C1B C2B -1.1(5) . . . .
N1B C1B C2B C3B 1.1(5) . . . .
C1B C2B C3B C4B -0.7(5) . . . .
C1B C2B C3B C6B 179.6(3) . . . .
C2B C3B C4B C5B 0.3(5) . . . .
C6B C3B C4B C5B -179.9(3) . . . .
C1B N1B C5B C4B 0.7(5) . . . .
C3B C4B C5B N1B -0.3(5) . . . .
N3B N2B C6B O1B 3.7(4) . . . .
N3B N2B C6B C3B -177.2(3) . . . .
C4B C3B C6B O1B -21.1(4) . . . .
C2B C3B C6B O1B 158.7(3) . . . .
C4B C3B C6B N2B 159.8(3) . . . .
C2B C3B C6B N2B -20.4(4) . . . .
C8B N4B C7B O2B 8.3(5) . . . .
C8B N4B C7B N3B -169.3(3) . . . .
N2B N3B C7B O2B 20.0(4) . . . .
N2B N3B C7B N4B -162.4(2) . . . .
C7B N4B C8B C13B -40.2(5) . . . .
C7B N4B C8B C9B 140.7(3) . . . .
C13B C8B C9B C10B 2.3(5) . . . .
N4B C8B C9B C10B -178.4(3) . . . .
C8B C9B C10B C11B -0.3(5) . . . .
C9B C10B C11B C12B -1.9(6) . . . .
C10B C11B C12B C13B 2.0(6) . . . .
C9B C8B C13B C12B -2.3(5) . . . .
N4B C8B C13B C12B 178.6(3) . . . .
C11B C12B C13B C8B 0.1(6) . . . .
C6C N2C N3C C7C 85.6(4) . . . .
C5C N1C C1C C2C 0.1(6) . . . .
N1C C1C C2C C3C -0.4(6) . . . .
C1C C2C C3C C4C 0.6(5) . . . .
C1C C2C C3C C6C 179.0(3) . . . .
C2C C3C C4C C5C -0.4(5) . . . .
C6C C3C C4C C5C -178.7(3) . . . .
C1C N1C C5C C4C 0.1(5) . . . .
C3C C4C C5C N1C 0.1(5) . . . .
N3C N2C C6C O1C 0.1(5) . . . .
N3C N2C C6C C3C -177.6(3) . . . .
C4C C3C C6C O1C 163.8(3) . . . .
C2C C3C C6C O1C -14.5(5) . . . .
C4C C3C C6C N2C -18.4(5) . . . .
C2C C3C C6C N2C 163.3(3) . . . .
C8C N4C C7C O2C -3.1(5) . . . .
C8C N4C C7C N3C 173.5(3) . . . .
N2C N3C C7C O2C 7.7(5) . . . .
N2C N3C C7C N4C -169.0(3) . . . .
C7C N4C C8C C13C 20.6(5) . . . .
C7C N4C C8C C9C -158.6(3) . . . .
C13C C8C C9C C10C 1.4(5) . . . .
N4C C8C C9C C10C -179.4(3) . . . .
C8C C9C C10C C11C -0.9(5) . . . .
C9C C10C C11C C12C 0.6(6) . . . .
C10C C11C C12C C13C -0.7(6) . . . .
C9C C8C C13C C12C -1.5(5) . . . .
N4C C8C C13C C12C 179.3(3) . . . .
C11C C12C C13C C8C 1.2(6) . . . .
C6D N2D N3D C7D -71.7(4) . . . .
C5D N1D C1D C2D -1.5(6) . . . .
N1D C1D C2D C3D 0.9(6) . . . .
C1D C2D C3D C4D 0.4(5) . . . .
C1D C2D C3D C6D 178.3(3) . . . .
C2D C3D C4D C5D -1.1(6) . . . .
C6D C3D C4D C5D -178.8(4) . . . .
C1D N1D C5D C4D 0.8(7) . . . .
C3D C4D C5D N1D 0.5(7) . . . .
N3D N2D C6D O1D 3.6(5) . . . .
N3D N2D C6D C3D 178.2(3) . . . .
C2D C3D C6D O1D 4.0(5) . . . .
C4D C3D C6D O1D -178.2(3) . . . .
C2D C3D C6D N2D -170.7(3) . . . .
C4D C3D C6D N2D 7.1(5) . . . .
C8D N4D C7D O2D -2.6(6) . . . .
C8D N4D C7D N3D 176.3(3) . . . .
N2D N3D C7D O2D -26.1(5) . . . .
N2D N3D C7D N4D 154.9(3) . . . .
C7D N4D C8D C13D -174.1(3) . . . .
C7D N4D C8D C9D 8.6(5) . . . .
C13D C8D C9D C10D -0.8(5) . . . .
N4D C8D C9D C10D 176.4(3) . . . .
C8D C9D C10D C11D 0.7(6) . . . .
C9D C10D C11D C12D 0.4(6) . . . .
C10D C11D C12D C13D -1.5(6) . . . .
C9D C8D C13D C12D -0.3(5) . . . .
N4D C8D C13D C12D -177.8(3) . . . .
C11D C12D C13D C8D 1.4(5) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{ad046b18-4039-4dc0-be40-beccb112686e} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{ad046b18-4039-4dc0-be40-beccb112686e} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
