#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228353.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_2228353
loop_
_publ_author_name
'Ather, Abdul Qayyum'
'Tahir, M. Nawaz'
'Khan, Misbahul Ain'
'Mehmood, Karamat'
'Chaudhry, Faryal'
_publ_section_title
;
 1,3-Diphenyl-1H-pyrazole-4-carbaldehyde
;
_journal_coeditor_code           HB5729
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3170
_journal_paper_doi               10.1107/S1600536810045630
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 N2 O'
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_name_systematic
;
1,3-Diphenyl-1H-pyrazole-4-carbaldehyde
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.932(6)
_cell_angle_beta                 90.135(5)
_cell_angle_gamma                107.991(6)
_cell_formula_units_Z            8
_cell_length_a                   10.1367(9)
_cell_length_b                   15.5952(16)
_cell_length_c                   16.7550(15)
_cell_measurement_reflns_used    4643
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      1.22
_cell_volume                     2504.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34716
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.0043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         8912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0901
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0599P)²+5.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2589
_reflns_number_gt                4643
_reflns_number_total             8912
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5729.cif
_cod_data_source_block           I
_cod_database_code               2228353
_cod_database_fobs_code          2228353
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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
O O1 0.6324(5) 0.4151(3) 0.5760(3) 0.0706(16) Uani . . 1.000
N N1 0.8394(4) 0.2089(3) 0.4618(3) 0.0490(17) Uani . . 1.000
N N2 0.8812(4) 0.2918(3) 0.4319(2) 0.0428(14) Uani . . 1.000
C C1 0.6788(5) 0.1383(3) 0.5612(3) 0.0446(17) Uani . . 1.000
C C2 0.7562(6) 0.0892(3) 0.5903(3) 0.0493(17) Uani . . 1.000
C C3 0.6934(6) 0.0185(4) 0.6334(3) 0.061(2) Uani . . 1.000
C C4 0.5531(7) -0.0053(4) 0.6477(4) 0.065(2) Uani . . 1.000
C C5 0.4758(7) 0.0432(4) 0.6173(4) 0.076(3) Uani . . 1.000
C C6 0.5391(6) 0.1157(4) 0.5744(4) 0.062(2) Uani . . 1.000
C C7 0.7457(5) 0.2158(3) 0.5157(3) 0.0436(17) Uani . . 1.000
C C8 0.7289(5) 0.3034(3) 0.5215(3) 0.0429(17) Uani . . 1.000
C C9 0.6454(6) 0.3399(4) 0.5749(3) 0.053(2) Uani . . 1.000
C C10 0.8163(5) 0.3480(3) 0.4661(3) 0.0470(17) Uani . . 1.000
C C11 0.9833(5) 0.3067(3) 0.3719(3) 0.0437(17) Uani . . 1.000
C C12 1.0281(6) 0.3897(4) 0.3421(3) 0.055(2) Uani . . 1.000
C C13 1.1282(7) 0.4025(4) 0.2846(4) 0.068(2) Uani . . 1.000
C C14 1.1816(6) 0.3351(4) 0.2571(3) 0.061(2) Uani . . 1.000
C C15 1.1377(6) 0.2537(4) 0.2883(3) 0.061(2) Uani . . 1.000
C C16 1.03802(19) 0.23882(12) 0.34566(11) 0.0506(17) Uani . . 1.000
O O2 0.09209(19) 0.44158(12) 0.58037(11) 0.0644(16) Uani . . 1.000
N N3 0.33043(19) 0.24537(12) 0.48630(11) 0.0433(16) Uani . . 1.000
N N4 0.36575(19) 0.32530(12) 0.45286(11) 0.0405(14) Uani . . 1.000
C C17 0.17474(19) 0.17575(12) 0.58564(11) 0.0384(17) Uani . . 1.000
C C18 0.15852(19) 0.08767(12) 0.55248(11) 0.0502(19) Uani . . 1.000
C C19 0.1044(6) 0.0147(4) 0.5952(3) 0.055(2) Uani . . 1.000
C C20 0.0655(5) 0.0274(3) 0.6720(3) 0.0508(19) Uani . . 1.000
C C21 0.0812(6) 0.1139(4) 0.7069(3) 0.0531(19) Uani . . 1.000
C C22 0.1365(5) 0.1882(3) 0.6647(3) 0.0484(17) Uani . . 1.000
C C23 0.2357(5) 0.2514(3) 0.5386(3) 0.0396(17) Uani . . 1.000
C C24 0.2102(5) 0.3372(3) 0.5403(3) 0.0393(17) Uani . . 1.000
C C25 0.1049(5) 0.3669(4) 0.5811(3) 0.0469(17) Uani . . 1.000
C C26 0.2954(5) 0.3806(3) 0.4830(3) 0.0438(17) Uani . . 1.000
C C27 0.4626(5) 0.3384(3) 0.3899(3) 0.0402(17) Uani . . 1.000
C C28 0.4935(6) 0.2652(4) 0.3532(4) 0.061(2) Uani . . 1.000
C C29 0.5852(7) 0.2762(4) 0.2916(4) 0.069(3) Uani . . 1.000
C C30 0.6470(6) 0.3599(4) 0.2681(3) 0.060(2) Uani . . 1.000
C C31 0.6156(6) 0.4331(4) 0.3051(3) 0.056(2) Uani . . 1.000
C C32 0.5242(5) 0.4236(4) 0.3679(3) 0.0517(19) Uani . . 1.000
O O3 0.4419(4) 0.5710(3) -0.0773(3) 0.0691(16) Uani . . 1.000
N N5 0.8514(4) 0.7740(3) 0.0322(3) 0.0502(17) Uani . . 1.000
N N6 0.8115(4) 0.6927(3) 0.0632(2) 0.0444(14) Uani . . 1.000
C C33 0.7671(5) 0.8451(3) -0.0696(3) 0.0460(17) Uani . . 1.000
C C34 0.6511(6) 0.8609(4) -0.1006(3) 0.061(2) Uani . . 1.000
C C35 0.6656(7) 0.9337(4) -0.1449(4) 0.064(2) Uani . . 1.000
C C36 0.7956(7) 0.9910(4) -0.1562(4) 0.066(3) Uani . . 1.000
C C37 0.9105(7) 0.9786(4) -0.1242(4) 0.069(3) Uani . . 1.000
C C38 0.8963(6) 0.9042(4) -0.0818(3) 0.057(2) Uani . . 1.000
C C39 0.7537(5) 0.7677(3) -0.0235(3) 0.0455(17) Uani . . 1.000
C C40 0.6495(5) 0.6820(3) -0.0279(3) 0.0435(17) Uani . . 1.000
C C41 0.5301(6) 0.6432(4) -0.0824(3) 0.055(2) Uani . . 1.000
C C42 0.6925(5) 0.6367(4) 0.0296(3) 0.0494(17) Uani . . 1.000
C C43 0.9001(5) 0.6761(4) 0.1228(3) 0.0466(17) Uani . . 1.000
C C44 0.8628(6) 0.5944(4) 0.1538(3) 0.059(2) Uani . . 1.000
C C45 0.9511(7) 0.5794(5) 0.2108(4) 0.069(3) Uani . . 1.000
C C46 1.0713(7) 0.6456(5) 0.2354(3) 0.066(3) Uani . . 1.000
C C47 1.1076(6) 0.7277(4) 0.2040(4) 0.063(2) Uani . . 1.000
C C48 1.0217(6) 0.7430(4) 0.1472(3) 0.054(2) Uani . . 1.000
O O4 -0.0749(4) 0.5732(3) -0.0812(3) 0.0707(17) Uani . . 1.000
N N7 0.3455(4) 0.7707(3) 0.0177(3) 0.0483(17) Uani . . 1.000
N N8 0.3045(4) 0.6894(3) 0.0502(3) 0.0463(17) Uani . . 1.000
C C49 0.2593(5) 0.8414(3) -0.0837(3) 0.0439(17) Uani . . 1.000
C C50 0.2157(5) 0.8280(4) -0.1632(3) 0.0493(17) Uani . . 1.000
C C51 0.2342(6) 0.9014(4) -0.2059(3) 0.060(2) Uani . . 1.000
C C52 0.2942(6) 0.9890(4) -0.1697(4) 0.065(2) Uani . . 1.000
C C53 0.3354(7) 1.0013(4) -0.0901(4) 0.067(2) Uani . . 1.000
C C54 0.3184(6) 0.9292(4) -0.0465(3) 0.0577(19) Uani . . 1.000
C C55 0.2457(5) 0.7637(3) -0.0361(3) 0.0435(17) Uani . . 1.000
C C56 0.1416(5) 0.6776(3) -0.0397(3) 0.0440(17) Uani . . 1.000
C C57 0.0096(6) 0.6466(4) -0.0828(3) 0.0523(19) Uani . . 1.000
C C58 0.1845(5) 0.6332(3) 0.0175(3) 0.0442(17) Uani . . 1.000
C C59 0.3854(5) 0.6767(4) 0.1152(3) 0.0456(17) Uani . . 1.000
C C60 0.3706(6) 0.5903(4) 0.1348(3) 0.0546(19) Uani . . 1.000
C C61 0.4465(6) 0.5811(4) 0.1997(3) 0.060(2) Uani . . 1.000
C C62 0.5361(6) 0.6533(4) 0.2435(4) 0.065(2) Uani . . 1.000
C C63 0.5492(7) 0.7385(4) 0.2227(4) 0.075(3) Uani . . 1.000
C C64 0.4736(6) 0.7498(4) 0.1583(4) 0.066(2) Uani . . 1.000
H H2 0.85051 0.10389 0.58087 0.0589 Uiso . . 1.000
H H3 0.74626 -0.01426 0.65353 0.0725 Uiso . . 1.000
H H4 0.51177 -0.05327 0.67733 0.0771 Uiso . . 1.000
H H5 0.38094 0.02736 0.62541 0.0908 Uiso . . 1.000
H H6 0.48683 0.14908 0.55469 0.0745 Uiso . . 1.000
H H9 0.59662 0.30309 0.61223 0.0640 Uiso . . 1.000
H H10 0.82820 0.40689 0.45441 0.0562 Uiso . . 1.000
H H12 0.99197 0.43596 0.36019 0.0659 Uiso . . 1.000
H H13 1.15977 0.45823 0.26427 0.0811 Uiso . . 1.000
H H14 1.24721 0.34440 0.21758 0.0732 Uiso . . 1.000
H H15 1.17538 0.20802 0.27071 0.0726 Uiso . . 1.000
H H16 1.00809 0.18326 0.36646 0.0602 Uiso . . 1.000
H H18 0.18484 0.07771 0.50008 0.0602 Uiso . . 1.000
H H19 0.09443 -0.04369 0.57147 0.0659 Uiso . . 1.000
H H20 0.02851 -0.02200 0.70070 0.0608 Uiso . . 1.000
H H21 0.05453 0.12268 0.75942 0.0637 Uiso . . 1.000
H H22 0.14805 0.24639 0.68924 0.0584 Uiso . . 1.000
H H25 0.04212 0.32593 0.61009 0.0562 Uiso . . 1.000
H H26 0.30279 0.43768 0.46808 0.0525 Uiso . . 1.000
H H28 0.45295 0.20797 0.36967 0.0730 Uiso . . 1.000
H H29 0.60499 0.22610 0.26589 0.0828 Uiso . . 1.000
H H30 0.71008 0.36723 0.22717 0.0725 Uiso . . 1.000
H H31 0.65575 0.49007 0.28813 0.0670 Uiso . . 1.000
H H32 0.50546 0.47378 0.39433 0.0623 Uiso . . 1.000
H H34 0.56304 0.82262 -0.09178 0.0732 Uiso . . 1.000
H H35 0.58768 0.94349 -0.16675 0.0761 Uiso . . 1.000
H H36 0.80514 1.03927 -0.18639 0.0786 Uiso . . 1.000
H H37 0.99777 1.01937 -0.13051 0.0830 Uiso . . 1.000
H H38 0.97502 0.89429 -0.06135 0.0687 Uiso . . 1.000
H H41 0.52026 0.67578 -0.12427 0.0654 Uiso . . 1.000
H H42 0.64684 0.57838 0.04222 0.0596 Uiso . . 1.000
H H44 0.78001 0.54974 0.13715 0.0712 Uiso . . 1.000
H H45 0.92784 0.52416 0.23215 0.0822 Uiso . . 1.000
H H46 1.12959 0.63530 0.27372 0.0791 Uiso . . 1.000
H H47 1.18989 0.77259 0.22111 0.0760 Uiso . . 1.000
H H48 1.04565 0.79806 0.12559 0.0653 Uiso . . 1.000
H H50 0.17392 0.76955 -0.18798 0.0593 Uiso . . 1.000
H H51 0.20603 0.89206 -0.25977 0.0727 Uiso . . 1.000
H H52 0.30642 1.03845 -0.19869 0.0782 Uiso . . 1.000
H H53 0.37566 1.05987 -0.06517 0.0802 Uiso . . 1.000
H H54 0.34615 0.93888 0.00746 0.0697 Uiso . . 1.000
H H57 -0.01206 0.68650 -0.11423 0.0629 Uiso . . 1.000
H H58 0.13851 0.57531 0.03084 0.0530 Uiso . . 1.000
H H60 0.31062 0.53966 0.10490 0.0657 Uiso . . 1.000
H H61 0.43586 0.52325 0.21380 0.0720 Uiso . . 1.000
H H62 0.58753 0.64559 0.28671 0.0772 Uiso . . 1.000
H H63 0.60979 0.78907 0.25241 0.0903 Uiso . . 1.000
H H64 0.48343 0.80769 0.14466 0.0791 Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C7 . . . 104.8(4) no
N1 N2 C10 . . . 111.8(4) no
N1 N2 C11 . . . 118.8(4) no
C10 N2 C11 . . . 129.4(4) no
N4 N3 C23 . . . 105.0(2) no
N3 N4 C26 . . . 112.5(3) no
N3 N4 C27 . . . 119.0(2) no
C26 N4 C27 . . . 128.5(3) no
N6 N5 C39 . . . 105.2(4) no
N5 N6 C43 . . . 118.9(4) no
N5 N6 C42 . . . 112.5(4) no
C42 N6 C43 . . . 128.6(5) no
N8 N7 C55 . . . 104.4(4) no
N7 N8 C58 . . . 112.6(4) no
C58 N8 C59 . . . 128.2(5) no
N7 N8 C59 . . . 119.0(4) no
C2 C1 C7 . . . 120.1(5) no
C2 C1 C6 . . . 120.1(5) no
C6 C1 C7 . . . 119.8(5) no
C1 C2 C3 . . . 119.5(6) no
C2 C3 C4 . . . 121.5(6) no
C3 C4 C5 . . . 118.8(6) no
C4 C5 C6 . . . 120.1(6) no
C1 C6 C5 . . . 120.1(6) no
N1 C7 C8 . . . 110.9(4) no
N1 C7 C1 . . . 119.7(4) no
C1 C7 C8 . . . 129.4(5) no
C9 C8 C10 . . . 126.7(5) no
C7 C8 C10 . . . 104.7(4) no
C7 C8 C9 . . . 128.6(5) no
O1 C9 C8 . . . 125.8(5) no
N2 C10 C8 . . . 107.9(4) no
N2 C11 C12 . . . 119.7(5) no
C12 C11 C16 . . . 120.7(4) no
N2 C11 C16 . . . 119.7(4) no
C11 C12 C13 . . . 118.4(5) no
C12 C13 C14 . . . 121.5(6) no
C13 C14 C15 . . . 119.4(6) no
C14 C15 C16 . . . 120.5(5) no
C11 C16 C15 . . . 119.6(3) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C5 C4 H4 . . . 121.00 no
C3 C4 H4 . . . 121.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
O1 C9 H9 . . . 117.00 no
C8 C9 H9 . . . 117.00 no
N2 C10 H10 . . . 126.00 no
C8 C10 H10 . . . 126.00 no
C11 C12 H12 . . . 121.00 no
C13 C12 H12 . . . 121.00 no
C12 C13 H13 . . . 119.00 no
C14 C13 H13 . . . 119.00 no
C13 C14 H14 . . . 120.00 no
C15 C14 H14 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C14 C15 H15 . . . 120.00 no
C15 C16 H16 . . . 120.00 no
C11 C16 H16 . . . 120.00 no
C18 C17 C22 . . . 117.6(2) no
C18 C17 C23 . . . 119.7(2) no
C22 C17 C23 . . . 122.7(3) no
C17 C18 C19 . . . 121.6(3) no
C18 C19 C20 . . . 120.4(5) no
C19 C20 C21 . . . 119.5(5) no
C20 C21 C22 . . . 120.8(5) no
C17 C22 C21 . . . 120.2(4) no
C17 C23 C24 . . . 129.6(4) no
N3 C23 C24 . . . 111.1(4) no
N3 C23 C17 . . . 119.3(4) no
C25 C24 C26 . . . 126.2(5) no
C23 C24 C26 . . . 104.1(4) no
C23 C24 C25 . . . 129.0(5) no
O2 C25 C24 . . . 124.7(5) no
N4 C26 C24 . . . 107.3(4) no
N4 C27 C28 . . . 118.9(4) no
C28 C27 C32 . . . 120.9(5) no
N4 C27 C32 . . . 120.2(4) no
C27 C28 C29 . . . 119.8(5) no
C28 C29 C30 . . . 120.5(6) no
C29 C30 C31 . . . 119.5(6) no
C30 C31 C32 . . . 120.9(5) no
C27 C32 C31 . . . 118.4(5) no
C17 C18 H18 . . . 119.00 no
C19 C18 H18 . . . 119.00 no
C20 C19 H19 . . . 120.00 no
C18 C19 H19 . . . 120.00 no
C19 C20 H20 . . . 120.00 no
C21 C20 H20 . . . 120.00 no
C22 C21 H21 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C17 C22 H22 . . . 120.00 no
C21 C22 H22 . . . 120.00 no
O2 C25 H25 . . . 118.00 no
C24 C25 H25 . . . 118.00 no
N4 C26 H26 . . . 126.00 no
C24 C26 H26 . . . 126.00 no
C29 C28 H28 . . . 120.00 no
C27 C28 H28 . . . 120.00 no
C28 C29 H29 . . . 120.00 no
C30 C29 H29 . . . 120.00 no
C29 C30 H30 . . . 120.00 no
C31 C30 H30 . . . 120.00 no
C32 C31 H31 . . . 119.00 no
C30 C31 H31 . . . 120.00 no
C27 C32 H32 . . . 121.00 no
C31 C32 H32 . . . 121.00 no
C34 C33 C38 . . . 118.7(5) no
C34 C33 C39 . . . 121.0(5) no
C38 C33 C39 . . . 120.3(5) no
C33 C34 C35 . . . 120.3(6) no
C34 C35 C36 . . . 119.5(6) no
C35 C36 C37 . . . 121.2(6) no
C36 C37 C38 . . . 119.3(6) no
C33 C38 C37 . . . 120.9(6) no
N5 C39 C33 . . . 118.9(4) no
N5 C39 C40 . . . 110.8(4) no
C33 C39 C40 . . . 130.3(5) no
C39 C40 C41 . . . 130.2(5) no
C39 C40 C42 . . . 104.4(5) no
C41 C40 C42 . . . 125.3(5) no
O3 C41 C40 . . . 124.5(5) no
N6 C42 C40 . . . 107.1(5) no
N6 C43 C44 . . . 119.8(5) no
C44 C43 C48 . . . 121.3(5) no
N6 C43 C48 . . . 118.9(5) no
C43 C44 C45 . . . 118.8(6) no
C44 C45 C46 . . . 120.1(6) no
C45 C46 C47 . . . 120.7(6) no
C46 C47 C48 . . . 119.8(6) no
C43 C48 C47 . . . 119.4(5) no
C33 C34 H34 . . . 120.00 no
C35 C34 H34 . . . 120.00 no
C34 C35 H35 . . . 120.00 no
C36 C35 H35 . . . 120.00 no
C35 C36 H36 . . . 119.00 no
C37 C36 H36 . . . 119.00 no
C38 C37 H37 . . . 120.00 no
C36 C37 H37 . . . 120.00 no
C33 C38 H38 . . . 120.00 no
C37 C38 H38 . . . 120.00 no
C40 C41 H41 . . . 118.00 no
O3 C41 H41 . . . 118.00 no
C40 C42 H42 . . . 127.00 no
N6 C42 H42 . . . 126.00 no
C45 C44 H44 . . . 121.00 no
C43 C44 H44 . . . 121.00 no
C44 C45 H45 . . . 120.00 no
C46 C45 H45 . . . 120.00 no
C45 C46 H46 . . . 120.00 no
C47 C46 H46 . . . 120.00 no
C48 C47 H47 . . . 120.00 no
C46 C47 H47 . . . 120.00 no
C43 C48 H48 . . . 120.00 no
C47 C48 H48 . . . 120.00 no
C50 C49 C54 . . . 119.8(5) no
C50 C49 C55 . . . 121.5(4) no
C54 C49 C55 . . . 118.8(4) no
C49 C50 C51 . . . 119.8(5) no
C50 C51 C52 . . . 120.9(5) no
C51 C52 C53 . . . 118.6(6) no
C52 C53 C54 . . . 121.5(6) no
C49 C54 C53 . . . 119.5(5) no
N7 C55 C49 . . . 118.2(4) no
N7 C55 C56 . . . 111.3(4) no
C49 C55 C56 . . . 130.5(5) no
C55 C56 C57 . . . 128.9(5) no
C55 C56 C58 . . . 104.7(4) no
C57 C56 C58 . . . 125.7(5) no
O4 C57 C56 . . . 125.1(5) no
N8 C58 C56 . . . 107.0(4) no
N8 C59 C60 . . . 120.2(5) no
N8 C59 C64 . . . 119.3(5) no
C60 C59 C64 . . . 120.5(5) no
C59 C60 C61 . . . 118.4(5) no
C60 C61 C62 . . . 122.1(6) no
C61 C62 C63 . . . 118.4(6) no
C62 C63 C64 . . . 120.8(6) no
C59 C64 C63 . . . 119.8(6) no
C49 C50 H50 . . . 120.00 no
C51 C50 H50 . . . 120.00 no
C50 C51 H51 . . . 120.00 no
C52 C51 H51 . . . 120.00 no
C51 C52 H52 . . . 121.00 no
C53 C52 H52 . . . 121.00 no
C52 C53 H53 . . . 119.00 no
C54 C53 H53 . . . 119.00 no
C49 C54 H54 . . . 120.00 no
C53 C54 H54 . . . 120.00 no
O4 C57 H57 . . . 118.00 no
C56 C57 H57 . . . 117.00 no
N8 C58 H58 . . . 127.00 no
C56 C58 H58 . . . 127.00 no
C59 C60 H60 . . . 121.00 no
C61 C60 H60 . . . 121.00 no
C60 C61 H61 . . . 119.00 no
C62 C61 H61 . . . 119.00 no
C61 C62 H62 . . . 121.00 no
C63 C62 H62 . . . 121.00 no
C62 C63 H63 . . . 120.00 no
C64 C63 H63 . . . 120.00 no
C59 C64 H64 . . . 120.00 no
C63 C64 H64 . . . 120.00 no
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
O1 C9 . . 1.218(8) no
O2 C25 . . 1.212(6) no
O3 C41 . . 1.214(8) no
O4 C57 . . 1.202(8) no
N1 N2 . . 1.378(6) no
N1 C7 . . 1.333(7) no
N2 C10 . . 1.336(7) no
N2 C11 . . 1.428(6) no
N3 C23 . . 1.320(6) no
N3 N4 . . 1.366(3) no
N4 C26 . . 1.341(5) no
N4 C27 . . 1.430(5) no
N5 C39 . . 1.333(7) no
N5 N6 . . 1.364(6) no
N6 C42 . . 1.334(7) no
N6 C43 . . 1.437(7) no
N7 N8 . . 1.377(6) no
N7 C55 . . 1.325(7) no
N8 C59 . . 1.428(7) no
N8 C58 . . 1.337(7) no
C1 C7 . . 1.479(7) no
C1 C6 . . 1.374(8) no
C1 C2 . . 1.373(7) no
C2 C3 . . 1.370(7) no
C3 C4 . . 1.383(10) no
C4 C5 . . 1.375(10) no
C5 C6 . . 1.389(9) no
C7 C8 . . 1.422(7) no
C8 C10 . . 1.374(7) no
C8 C9 . . 1.427(8) no
C11 C12 . . 1.379(7) no
C11 C16 . . 1.375(5) no
C12 C13 . . 1.385(9) no
C13 C14 . . 1.365(9) no
C14 C15 . . 1.368(8) no
C15 C16 . . 1.380(6) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
C17 C18 . . 1.387(3) no
C17 C22 . . 1.392(5) no
C17 C23 . . 1.463(5) no
C18 C19 . . 1.376(6) no
C19 C20 . . 1.360(7) no
C20 C21 . . 1.375(7) no
C21 C22 . . 1.388(7) no
C23 C24 . . 1.437(7) no
C24 C25 . . 1.437(7) no
C24 C26 . . 1.379(7) no
C27 C28 . . 1.362(8) no
C27 C32 . . 1.372(7) no
C28 C29 . . 1.379(10) no
C29 C30 . . 1.362(8) no
C30 C31 . . 1.367(8) no
C31 C32 . . 1.393(8) no
C18 H18 . . 0.9300 no
C19 H19 . . 0.9300 no
C20 H20 . . 0.9300 no
C21 H21 . . 0.9300 no
C22 H22 . . 0.9300 no
C25 H25 . . 0.9300 no
C26 H26 . . 0.9300 no
C28 H28 . . 0.9300 no
C29 H29 . . 0.9300 no
C30 H30 . . 0.9300 no
C31 H31 . . 0.9300 no
C32 H32 . . 0.9300 no
C33 C39 . . 1.471(7) no
C33 C38 . . 1.379(8) no
C33 C34 . . 1.384(8) no
C34 C35 . . 1.390(8) no
C35 C36 . . 1.371(10) no
C36 C37 . . 1.356(10) no
C37 C38 . . 1.393(8) no
C39 C40 . . 1.419(7) no
C40 C41 . . 1.447(8) no
C40 C42 . . 1.395(7) no
C43 C48 . . 1.375(8) no
C43 C44 . . 1.370(8) no
C44 C45 . . 1.393(9) no
C45 C46 . . 1.361(10) no
C46 C47 . . 1.379(9) no
C47 C48 . . 1.376(9) no
C34 H34 . . 0.9300 no
C35 H35 . . 0.9300 no
C36 H36 . . 0.9300 no
C37 H37 . . 0.9300 no
C38 H38 . . 0.9300 no
C41 H41 . . 0.9300 no
C42 H42 . . 0.9300 no
C44 H44 . . 0.9300 no
C45 H45 . . 0.9300 no
C46 H46 . . 0.9300 no
C47 H47 . . 0.9300 no
C48 H48 . . 0.9300 no
C49 C50 . . 1.377(7) no
C49 C54 . . 1.392(7) no
C49 C55 . . 1.490(7) no
C50 C51 . . 1.377(8) no
C51 C52 . . 1.385(8) no
C52 C53 . . 1.373(9) no
C53 C54 . . 1.371(8) no
C55 C56 . . 1.424(7) no
C56 C57 . . 1.439(8) no
C56 C58 . . 1.381(7) no
C59 C60 . . 1.383(8) no
C59 C64 . . 1.348(8) no
C60 C61 . . 1.375(8) no
C61 C62 . . 1.351(9) no
C62 C63 . . 1.375(9) no
C63 C64 . . 1.379(9) no
C50 H50 . . 0.9300 no
C51 H51 . . 0.9300 no
C52 H52 . . 0.9300 no
C53 H53 . . 0.9300 no
C54 H54 . . 0.9300 no
C57 H57 . . 0.9300 no
C58 H58 . . 0.9300 no
C60 H60 . . 0.9300 no
C61 H61 . . 0.9300 no
C62 H62 . . 0.9300 no
C63 H63 . . 0.9300 no
C64 H64 . . 0.9300 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
C10 H10 O2 2_666 0.93 2.38 3.299(5) 168 yes
C12 H12 O2 2_666 0.93 2.45 3.373(6) 175 yes
C26 H26 O1 2_666 0.93 2.38 3.298(6) 169 yes
C32 H32 O1 2_666 0.93 2.55 3.423(7) 156 yes
C42 H42 O3 2_665 0.93 2.36 3.287(7) 173 yes
C44 H44 O3 2_665 0.93 2.57 3.495(8) 175 yes
C58 H58 O4 2_565 0.93 2.44 3.353(6) 165 yes
C60 H60 O4 2_565 0.93 2.49 3.330(8) 150 yes
C2 H2 Cg5 1_655 0.93 2.86 3.689(7) 149 yes
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
C7 N1 N2 C10 . . . . 0.2(5) no
C7 N1 N2 C11 . . . . 179.9(4) no
N2 N1 C7 C1 . . . . -179.3(4) no
N2 N1 C7 C8 . . . . -1.0(6) no
N1 N2 C10 C8 . . . . 0.7(6) no
C11 N2 C10 C8 . . . . -178.9(5) no
N1 N2 C11 C12 . . . . -179.0(5) no
N1 N2 C11 C16 . . . . -0.4(6) no
C10 N2 C11 C12 . . . . 0.6(8) no
C10 N2 C11 C16 . . . . 179.3(4) no
N4 N3 C23 C24 . . . . -0.9(4) no
N4 N3 C23 C17 . . . . 180.0(3) no
C23 N3 N4 C26 . . . . 0.0(4) no
C23 N3 N4 C27 . . . . -176.8(3) no
C27 N4 C26 C24 . . . . 177.4(4) no
C26 N4 C27 C28 . . . . -162.0(5) no
N3 N4 C27 C28 . . . . 14.2(6) no
N3 N4 C27 C32 . . . . -165.0(4) no
N3 N4 C26 C24 . . . . 1.0(5) no
C26 N4 C27 C32 . . . . 18.8(7) no
C39 N5 N6 C42 . . . . -0.6(6) no
N6 N5 C39 C40 . . . . 0.5(6) no
N6 N5 C39 C33 . . . . -179.3(4) no
C39 N5 N6 C43 . . . . 176.9(4) no
N5 N6 C43 C48 . . . . 0.6(7) no
N5 N6 C43 C44 . . . . -179.1(5) no
C42 N6 C43 C48 . . . . 177.7(5) no
C42 N6 C43 C44 . . . . -1.9(8) no
C43 N6 C42 C40 . . . . -176.8(5) no
N5 N6 C42 C40 . . . . 0.5(6) no
C55 N7 N8 C58 . . . . 0.7(6) no
C55 N7 N8 C59 . . . . -175.6(5) no
N8 N7 C55 C56 . . . . -1.1(6) no
N8 N7 C55 C49 . . . . -179.3(4) no
C58 N8 C59 C60 . . . . 21.8(8) no
N7 N8 C59 C60 . . . . -162.6(5) no
N7 N8 C59 C64 . . . . 19.0(8) no
N7 N8 C58 C56 . . . . 0.1(6) no
C58 N8 C59 C64 . . . . -156.6(6) no
C59 N8 C58 C56 . . . . 175.9(5) no
C6 C1 C7 C8 . . . . 43.6(8) no
C7 C1 C2 C3 . . . . 179.0(5) no
C2 C1 C7 C8 . . . . -136.3(6) no
C6 C1 C7 N1 . . . . -138.5(6) no
C6 C1 C2 C3 . . . . -0.9(8) no
C2 C1 C6 C5 . . . . 0.1(9) no
C2 C1 C7 N1 . . . . 41.7(7) no
C7 C1 C6 C5 . . . . -179.8(5) no
C1 C2 C3 C4 . . . . 0.7(8) no
C2 C3 C4 C5 . . . . 0.4(9) no
C3 C4 C5 C6 . . . . -1.2(10) no
C4 C5 C6 C1 . . . . 1.0(10) no
C1 C7 C8 C10 . . . . 179.5(5) no
N1 C7 C8 C9 . . . . -176.1(5) no
C1 C7 C8 C9 . . . . 2.1(9) no
N1 C7 C8 C10 . . . . 1.4(6) no
C10 C8 C9 O1 . . . . 4.9(10) no
C9 C8 C10 N2 . . . . 176.3(5) no
C7 C8 C9 O1 . . . . -178.2(6) no
C7 C8 C10 N2 . . . . -1.2(6) no
N2 C11 C12 C13 . . . . 179.3(5) no
C12 C11 C16 C15 . . . . -0.7(6) no
N2 C11 C16 C15 . . . . -179.3(4) no
C16 C11 C12 C13 . . . . 0.7(8) no
C11 C12 C13 C14 . . . . 0.4(9) no
C12 C13 C14 C15 . . . . -1.5(10) no
C13 C14 C15 C16 . . . . 1.5(8) no
C14 C15 C16 C11 . . . . -0.4(7) no
C23 C17 C18 C19 . . . . 178.6(4) no
C18 C17 C22 C21 . . . . -1.5(6) no
C22 C17 C18 C19 . . . . 1.1(5) no
C22 C17 C23 N3 . . . . 145.3(4) no
C22 C17 C23 C24 . . . . -33.7(7) no
C18 C17 C23 C24 . . . . 149.0(4) no
C23 C17 C22 C21 . . . . -178.9(5) no
C18 C17 C23 N3 . . . . -32.1(5) no
C17 C18 C19 C20 . . . . -0.2(7) no
C18 C19 C20 C21 . . . . -0.3(8) no
C19 C20 C21 C22 . . . . -0.2(9) no
C20 C21 C22 C17 . . . . 1.1(8) no
N3 C23 C24 C25 . . . . 171.9(5) no
C17 C23 C24 C25 . . . . -9.1(9) no
C17 C23 C24 C26 . . . . -179.5(5) no
N3 C23 C24 C26 . . . . 1.5(6) no
C26 C24 C25 O2 . . . . -12.8(8) no
C23 C24 C26 N4 . . . . -1.4(5) no
C23 C24 C25 O2 . . . . 178.7(5) no
C25 C24 C26 N4 . . . . -172.2(5) no
C28 C27 C32 C31 . . . . 2.2(8) no
N4 C27 C28 C29 . . . . 179.1(5) no
N4 C27 C32 C31 . . . . -178.6(4) no
C32 C27 C28 C29 . . . . -1.7(9) no
C27 C28 C29 C30 . . . . 1.2(10) no
C28 C29 C30 C31 . . . . -1.2(10) no
C29 C30 C31 C32 . . . . 1.8(9) no
C30 C31 C32 C27 . . . . -2.3(8) no
C38 C33 C34 C35 . . . . 1.7(8) no
C34 C33 C38 C37 . . . . 0.2(8) no
C39 C33 C38 C37 . . . . -179.0(5) no
C39 C33 C34 C35 . . . . -179.2(5) no
C38 C33 C39 C40 . . . . -152.4(5) no
C38 C33 C39 N5 . . . . 27.4(7) no
C34 C33 C39 N5 . . . . -151.8(5) no
C34 C33 C39 C40 . . . . 28.5(8) no
C33 C34 C35 C36 . . . . -1.4(9) no
C34 C35 C36 C37 . . . . -0.7(10) no
C35 C36 C37 C38 . . . . 2.6(10) no
C36 C37 C38 C33 . . . . -2.3(9) no
N5 C39 C40 C41 . . . . -175.4(5) no
C33 C39 C40 C42 . . . . 179.5(5) no
N5 C39 C40 C42 . . . . -0.2(6) no
C33 C39 C40 C41 . . . . 4.3(9) no
C39 C40 C41 O3 . . . . -174.8(6) no
C41 C40 C42 N6 . . . . 175.3(5) no
C42 C40 C41 O3 . . . . 10.9(9) no
C39 C40 C42 N6 . . . . -0.2(6) no
C44 C43 C48 C47 . . . . -0.1(9) no
N6 C43 C48 C47 . . . . -179.7(5) no
N6 C43 C44 C45 . . . . 179.2(5) no
C48 C43 C44 C45 . . . . -0.4(9) no
C43 C44 C45 C46 . . . . 0.7(9) no
C44 C45 C46 C47 . . . . -0.5(10) no
C45 C46 C47 C48 . . . . 0.0(10) no
C46 C47 C48 C43 . . . . 0.3(9) no
C54 C49 C50 C51 . . . . 1.7(8) no
C55 C49 C50 C51 . . . . -177.9(5) no
C50 C49 C54 C53 . . . . -1.5(9) no
C55 C49 C54 C53 . . . . 178.1(6) no
C50 C49 C55 N7 . . . . 143.5(5) no
C50 C49 C55 C56 . . . . -34.3(8) no
C54 C49 C55 N7 . . . . -36.1(7) no
C54 C49 C55 C56 . . . . 146.2(6) no
C49 C50 C51 C52 . . . . -1.1(9) no
C50 C51 C52 C53 . . . . 0.2(10) no
C51 C52 C53 C54 . . . . 0.1(10) no
C52 C53 C54 C49 . . . . 0.6(10) no
N7 C55 C56 C57 . . . . 172.2(5) no
N7 C55 C56 C58 . . . . 1.2(6) no
C49 C55 C56 C57 . . . . -10.0(9) no
C49 C55 C56 C58 . . . . 179.1(5) no
C55 C56 C57 O4 . . . . -177.9(6) no
C58 C56 C57 O4 . . . . -8.7(9) no
C55 C56 C58 N8 . . . . -0.7(6) no
C57 C56 C58 N8 . . . . -172.1(5) no
N8 C59 C60 C61 . . . . -177.6(5) no
C64 C59 C60 C61 . . . . 0.8(9) no
N8 C59 C64 C63 . . . . 178.1(6) no
C60 C59 C64 C63 . . . . -0.3(9) no
C59 C60 C61 C62 . . . . -1.2(9) no
C60 C61 C62 C63 . . . . 1.1(10) no
C61 C62 C63 C64 . . . . -0.6(10) no
C62 C63 C64 C59 . . . . 0.2(10) no
