#------------------------------------------------------------------------------
#$Date: 2022-10-21 11:53:52 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278698 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105931.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_8105931
loop_
_publ_author_name
'Yu, Xiang'
'Zhao, You-Fang'
'Qin, Yan'
'Yan, Jing'
'Chen, Ya-Fang'
_publ_section_title
;
 The crystal structure of
 N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide,
 C23H22N2O4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1039
_journal_page_last               1041
_journal_paper_doi               10.1515/ncrs-2019-0249
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C23 H22 N2 O4'
_chemical_formula_sum            'C23 H22 N2 O4'
_chemical_formula_weight         390.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 111.111(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7478(4)
_cell_length_b                   10.0041(2)
_cell_length_c                   24.4749(6)
_cell_measurement_reflns_used    28859
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.3680
_cell_measurement_theta_min      3.5340
_cell_volume                     4053.88(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1169
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -20.00  25.00   0.75   10.21    --  -13.80 -99.00-150.00   60
  2  ω    -81.00  12.00   0.75   10.21    --  -13.80 -77.00 -30.00  124
  3  ω    -41.00  53.50   0.75   10.21    --  -13.80  77.00  90.00  126
  4  ω    -39.00  15.00   0.75   10.21    --  -13.80 -83.00  79.00   72
  5  ω    -70.00  -5.50   0.75   10.21    --  -13.80 129.00 -69.66   86
  6  ω    -68.00  -3.50   0.75   10.21    --  -13.80 126.00 153.60   86
  7  ω     -4.00  83.00   0.75   10.21    --   14.82  38.00  90.00  116
  8  ω     -4.00  83.00   0.75   10.21    --   14.82  38.00-120.00  116
  9  ω    -54.00  84.00   0.75   10.21    --   14.82   0.00 -60.00  184
 10  ω    -54.00  33.00   0.75   10.21    --   14.82 -38.00 -90.00  116
 11  ω    -64.00   2.00   0.75   10.21    --  -13.80 119.00  60.75   88
 12  ω     -9.00  60.00   0.75   10.21    --   14.82-112.00 -61.23   92
 13  ω    -20.00  53.50   0.75   10.21    --   14.82 -99.00  60.00   98
 14  ω     35.00  86.00   0.75   10.21    --   14.82 178.00 -90.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0190755000
_diffrn_orient_matrix_UB_12      -0.0054867000
_diffrn_orient_matrix_UB_13      -0.0208746000
_diffrn_orient_matrix_UB_21      0.0263260000
_diffrn_orient_matrix_UB_22      -0.0494550000
_diffrn_orient_matrix_UB_23      0.0175262000
_diffrn_orient_matrix_UB_31      -0.0279016000
_diffrn_orient_matrix_UB_32      -0.0504826000
_diffrn_orient_matrix_UB_33      -0.0149204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            93062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.533
_diffrn_reflns_theta_min         3.330
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         9585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0614
_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)+(0.0680P)²+1.7686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6513
_reflns_number_total             9585
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0249_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105931
_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_max   0.977
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C12(H12), C14(H14), C18(H18),
 C20(H20), C21(H21), C22(H22), N4(H4), C25(H25), C26(H26), C28(H28), C29(H29),
 C35(H35), C37(H37), C41(H41), C43(H43), C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C33(H33A,H33B,
 H33C), C38(H38A,H38B,H38C), C46(H46A,H46B,H46C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.26905(9) 0.96583(15) 0.33980(6) 0.0499(4) Uani 1 1 d . . . . .
O2 O 0.24264(14) 1.1723(2) 0.30743(9) 0.0881(6) Uani 1 1 d . . . . .
O3 O 0.34233(11) 0.54040(16) 0.42024(8) 0.0645(5) Uani 1 1 d . . . . .
O4 O 0.16120(10) 1.24119(13) 0.61106(7) 0.0517(4) Uani 1 1 d . . . . .
N1 N 0.20741(10) 1.05625(16) 0.54586(7) 0.0422(4) Uani 1 1 d . . . . .
N2 N 0.15460(11) 1.03074(16) 0.57499(8) 0.0448(4) Uani 1 1 d . . . . .
H2 H 0.1341 0.9522 0.5731 0.054 Uiso 1 1 calc R . . . .
C1 C 0.23379(15) 1.0559(3) 0.29467(11) 0.0613(6) Uani 1 1 d . . . . .
C2 C 0.19009(17) 1.0006(3) 0.23797(12) 0.0736(8) Uani 1 1 d . . . . .
H2A H 0.1672 1.0577 0.2063 0.088 Uiso 1 1 calc R . . . .
C3 C 0.18169(16) 0.8688(3) 0.22975(11) 0.0708(7) Uani 1 1 d . . . . .
H3 H 0.1515 0.8360 0.1928 0.085 Uiso 1 1 calc R . . . .
C4 C 0.21820(14) 0.7768(3) 0.27665(10) 0.0534(6) Uani 1 1 d . . . . .
C5 C 0.21527(16) 0.6387(3) 0.27125(12) 0.0653(7) Uani 1 1 d . . . . .
H5 H 0.1853 0.6008 0.2353 0.078 Uiso 1 1 calc R . . . .
C6 C 0.25518(16) 0.5564(3) 0.31733(12) 0.0626(7) Uani 1 1 d . . . . .
H6 H 0.2522 0.4641 0.3127 0.075 Uiso 1 1 calc R . . . .
C7 C 0.30073(14) 0.6131(2) 0.37172(10) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.30533(12) 0.7516(2) 0.37966(9) 0.0407(5) Uani 1 1 d . . . . .
C9 C 0.26371(12) 0.8292(2) 0.33160(9) 0.0429(5) Uani 1 1 d . . . . .
C10 C 0.3495(2) 0.3997(3) 0.41407(17) 0.0938(10) Uani 1 1 d . . . . .
H10A H 0.3751 0.3827 0.3862 0.141 Uiso 1 1 calc GR . . . .
H10B H 0.2968 0.3598 0.4006 0.141 Uiso 1 1 calc GR . . . .
H10C H 0.3815 0.3619 0.4513 0.141 Uiso 1 1 calc GR . . . .
C11 C 0.35239(12) 0.8148(2) 0.43816(9) 0.0415(4) Uani 1 1 d . . . . .
H11A H 0.3963 0.7561 0.4602 0.050 Uiso 1 1 calc R . . . .
H11B H 0.3755 0.8986 0.4319 0.050 Uiso 1 1 calc R . . . .
C12 C 0.29926(11) 0.84007(19) 0.47269(8) 0.0379(4) Uani 1 1 d . . . . .
H12 H 0.2756 0.7650 0.4822 0.045 Uiso 1 1 calc R . . . .
C13 C 0.28159(11) 0.95671(19) 0.49148(8) 0.0380(4) Uani 1 1 d . . . . .
C14 C 0.22740(12) 0.9522(2) 0.52403(9) 0.0402(4) Uani 1 1 d . . . . .
H14 H 0.2064 0.8700 0.5292 0.048 Uiso 1 1 calc R . . . .
C15 C 0.31369(16) 1.0894(2) 0.48191(12) 0.0609(6) Uani 1 1 d . . . . .
H15A H 0.3712 1.0912 0.5018 0.091 Uiso 1 1 calc GR . . . .
H15B H 0.2895 1.1589 0.4971 0.091 Uiso 1 1 calc GR . . . .
H15C H 0.3010 1.1031 0.4407 0.091 Uiso 1 1 calc GR . . . .
C16 C 0.13491(12) 1.12703(19) 0.60623(9) 0.0398(4) Uani 1 1 d . . . . .
C17 C 0.07825(13) 1.08329(19) 0.63543(9) 0.0439(5) Uani 1 1 d . . . . .
C18 C 0.09078(14) 1.1311(2) 0.69118(9) 0.0458(5) Uani 1 1 d . . . . .
H18 H 0.1341 1.1879 0.7094 0.055 Uiso 1 1 calc R . . . .
C19 C 0.03929(16) 1.0952(2) 0.72021(11) 0.0569(6) Uani 1 1 d . . . . .
C20 C -0.0245(2) 1.0119(3) 0.69171(15) 0.0821(10) Uani 1 1 d . . . . .
H20 H -0.0594 0.9869 0.7106 0.099 Uiso 1 1 calc R . . . .
C21 C -0.0380(2) 0.9649(3) 0.63670(17) 0.0982(12) Uani 1 1 d . . . . .
H21 H -0.0819 0.9095 0.6184 0.118 Uiso 1 1 calc R . . . .
C22 C 0.01351(18) 0.9998(3) 0.60823(14) 0.0771(9) Uani 1 1 d . . . . .
H22 H 0.0047 0.9671 0.5709 0.093 Uiso 1 1 calc R . . . .
C23 C 0.0528(2) 1.1483(4) 0.78048(13) 0.0904(10) Uani 1 1 d . . . . .
H23A H 0.1056 1.1874 0.7966 0.136 Uiso 1 1 calc GR . . . .
H23B H 0.0486 1.0764 0.8052 0.136 Uiso 1 1 calc GR . . . .
H23C H 0.0128 1.2149 0.7781 0.136 Uiso 1 1 calc GR . . . .
O5 O 0.56386(10) 0.46774(18) 0.70392(8) 0.0614(4) Uani 1 1 d . . . . .
O6 O 0.59196(16) 0.6733(3) 0.73497(13) 0.1088(8) Uani 1 1 d . . . . .
O7 O 0.50174(11) 0.04222(18) 0.62100(9) 0.0744(5) Uani 1 1 d . . . . .
O8 O 0.11940(10) 0.74961(14) 0.56374(9) 0.0658(5) Uani 1 1 d . . . . .
N3 N 0.23454(9) 0.55897(16) 0.58128(7) 0.0373(4) Uani 1 1 d . . . . .
N4 N 0.15676(9) 0.53398(15) 0.57946(7) 0.0366(4) Uani 1 1 d . . . . .
H4 H 0.1431 0.4539 0.5847 0.044 Uiso 1 1 calc R . . . .
C24 C 0.60162(18) 0.5575(4) 0.74803(15) 0.0775(8) Uani 1 1 d . . . . .
C25 C 0.6489(2) 0.5020(4) 0.80416(15) 0.0917(10) Uani 1 1 d . . . . .
H25 H 0.6753 0.5593 0.8351 0.110 Uiso 1 1 calc R . . . .
C26 C 0.65588(19) 0.3688(4) 0.81295(13) 0.0879(10) Uani 1 1 d . . . . .
H26 H 0.6870 0.3360 0.8497 0.106 Uiso 1 1 calc R . . . .
C27 C 0.61669(14) 0.2782(3) 0.76716(11) 0.0656(7) Uani 1 1 d . . . . .
C28 C 0.62150(16) 0.1388(3) 0.77156(13) 0.0756(9) Uani 1 1 d . . . . .
H28 H 0.6511 0.1004 0.8075 0.091 Uiso 1 1 calc R . . . .
C29 C 0.58408(16) 0.0571(3) 0.72479(14) 0.0710(8) Uani 1 1 d . . . . .
H29 H 0.5879 -0.0353 0.7291 0.085 Uiso 1 1 calc R . . . .
C30 C 0.54028(13) 0.1141(3) 0.67072(12) 0.0570(6) Uani 1 1 d . . . . .
C31 C 0.53350(12) 0.2530(2) 0.66384(10) 0.0477(5) Uani 1 1 d . . . . .
C32 C 0.57150(13) 0.3314(3) 0.71235(11) 0.0531(6) Uani 1 1 d . . . . .
C33 C 0.5124(2) -0.0993(3) 0.62216(19) 0.1038(12) Uani 1 1 d . . . . .
H33A H 0.4833 -0.1354 0.5840 0.156 Uiso 1 1 calc GR . . . .
H33B H 0.4923 -0.1379 0.6501 0.156 Uiso 1 1 calc GR . . . .
H33C H 0.5688 -0.1196 0.6331 0.156 Uiso 1 1 calc GR . . . .
C34 C 0.48551(12) 0.3149(2) 0.60558(10) 0.0490(5) Uani 1 1 d . . . . .
H34A H 0.5104 0.3986 0.6013 0.059 Uiso 1 1 calc R . . . .
H34B H 0.4860 0.2556 0.5743 0.059 Uiso 1 1 calc R . . . .
C35 C 0.40024(11) 0.3401(2) 0.60045(9) 0.0419(5) Uani 1 1 d . . . . .
H35 H 0.3710 0.2659 0.6044 0.050 Uiso 1 1 calc R . . . .
C36 C 0.36113(11) 0.45670(19) 0.59091(8) 0.0370(4) Uani 1 1 d . . . . .
C37 C 0.27756(11) 0.45395(19) 0.58787(8) 0.0370(4) Uani 1 1 d . . . . .
H37 H 0.2546 0.3720 0.5909 0.044 Uiso 1 1 calc R . . . .
C38 C 0.39748(13) 0.5875(2) 0.58287(11) 0.0551(6) Uani 1 1 d . . . . .
H38A H 0.4054 0.5870 0.5461 0.083 Uiso 1 1 calc GR . . . .
H38B H 0.4485 0.5998 0.6141 0.083 Uiso 1 1 calc GR . . . .
H38C H 0.3617 0.6592 0.5832 0.083 Uiso 1 1 calc GR . . . .
C39 C 0.10250(12) 0.63346(19) 0.56957(9) 0.0388(4) Uani 1 1 d . . . . .
C40 C 0.01956(11) 0.59498(19) 0.56642(8) 0.0365(4) Uani 1 1 d . . . . .
C41 C 0.00208(11) 0.4783(2) 0.58977(9) 0.0390(4) Uani 1 1 d . . . . .
H41 H 0.0433 0.4174 0.6074 0.047 Uiso 1 1 calc R . . . .
C42 C -0.07599(12) 0.4500(2) 0.58743(9) 0.0451(5) Uani 1 1 d . . . . .
C43 C -0.13603(12) 0.5427(2) 0.56054(10) 0.0497(5) Uani 1 1 d . . . . .
H43 H -0.1883 0.5264 0.5591 0.060 Uiso 1 1 calc R . . . .
C44 C -0.12031(13) 0.6574(2) 0.53608(10) 0.0515(6) Uani 1 1 d . . . . .
H44 H -0.1618 0.7173 0.5178 0.062 Uiso 1 1 calc R . . . .
C45 C -0.04303(12) 0.6843(2) 0.53851(9) 0.0456(5) Uani 1 1 d . . . . .
H45 H -0.0325 0.7619 0.5216 0.055 Uiso 1 1 calc R . . . .
C46 C -0.09364(15) 0.3244(3) 0.61374(14) 0.0766(8) Uani 1 1 d . . . . .
H46A H -0.0903 0.2492 0.5903 0.115 Uiso 1 1 calc GR . . . .
H46B H -0.1470 0.3292 0.6150 0.115 Uiso 1 1 calc GR . . . .
H46C H -0.0550 0.3140 0.6528 0.115 Uiso 1 1 calc GR . . . .
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
C9 O1 C1 122.68(18) . .
C7 O3 C10 118.4(2) . .
C14 N1 N2 113.89(16) . .
N1 N2 H2 119.4 . .
C16 N2 N1 121.24(16) . .
C16 N2 H2 119.4 . .
O1 C1 C2 116.8(2) . .
O2 C1 O1 116.3(2) . .
O2 C1 C2 126.9(3) . .
C1 C2 H2A 119.4 . .
C3 C2 C1 121.3(3) . .
C3 C2 H2A 119.4 . .
C2 C3 H3 119.3 . .
C2 C3 C4 121.4(2) . .
C4 C3 H3 119.3 . .
C5 C4 C3 125.0(2) . .
C5 C4 C9 117.0(2) . .
C9 C4 C3 117.9(2) . .
C4 C5 H5 119.0 . .
C6 C5 C4 122.0(2) . .
C6 C5 H5 119.0 . .
C5 C6 H6 120.4 . .
C5 C6 C7 119.2(2) . .
C7 C6 H6 120.4 . .
O3 C7 C6 123.9(2) . .
O3 C7 C8 115.0(2) . .
C8 C7 C6 121.1(2) . .
C7 C8 C11 122.1(2) . .
C9 C8 C7 116.9(2) . .
C9 C8 C11 120.99(18) . .
O1 C9 C4 119.8(2) . .
O1 C9 C8 116.46(18) . .
C8 C9 C4 123.7(2) . .
O3 C10 H10A 109.5 . .
O3 C10 H10B 109.5 . .
O3 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.4 . .
C8 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
C12 C11 C8 111.09(16) . .
C12 C11 H11A 109.4 . .
C12 C11 H11B 109.4 . .
C11 C12 H12 115.9 . .
C13 C12 C11 128.10(18) . .
C13 C12 H12 115.9 . .
C12 C13 C14 116.51(17) . .
C12 C13 C15 124.94(18) . .
C14 C13 C15 118.55(17) . .
N1 C14 C13 122.82(18) . .
N1 C14 H14 118.6 . .
C13 C14 H14 118.6 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O4 C16 N2 123.56(18) . .
O4 C16 C17 121.75(17) . .
N2 C16 C17 114.68(16) . .
C18 C17 C16 118.21(19) . .
C22 C17 C16 122.2(2) . .
C22 C17 C18 119.6(2) . .
C17 C18 H18 119.6 . .
C17 C18 C19 120.7(2) . .
C19 C18 H18 119.6 . .
C18 C19 C23 120.5(3) . .
C20 C19 C18 118.0(2) . .
C20 C19 C23 121.5(2) . .
C19 C20 H20 119.0 . .
C21 C20 C19 122.0(2) . .
C21 C20 H20 119.0 . .
C20 C21 H21 120.0 . .
C20 C21 C22 119.9(3) . .
C22 C21 H21 120.0 . .
C17 C22 H22 120.1 . .
C21 C22 C17 119.8(3) . .
C21 C22 H22 120.1 . .
C19 C23 H23A 109.5 . .
C19 C23 H23B 109.5 . .
C19 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C24 O5 C32 122.2(2) . .
C30 O7 C33 119.0(2) . .
C37 N3 N4 113.53(15) . .
N3 N4 H4 119.6 . .
C39 N4 N3 120.80(15) . .
C39 N4 H4 119.6 . .
O5 C24 C25 116.7(3) . .
O6 C24 O5 116.0(3) . .
O6 C24 C25 127.3(3) . .
C24 C25 H25 119.3 . .
C26 C25 C24 121.5(3) . .
C26 C25 H25 119.3 . .
C25 C26 H26 119.5 . .
C25 C26 C27 121.1(3) . .
C27 C26 H26 119.5 . .
C28 C27 C26 125.4(3) . .
C32 C27 C26 117.7(3) . .
C32 C27 C28 116.9(3) . .
C27 C28 H28 118.9 . .
C29 C28 C27 122.2(2) . .
C29 C28 H28 118.9 . .
C28 C29 H29 120.4 . .
C28 C29 C30 119.2(3) . .
C30 C29 H29 120.4 . .
O7 C30 C29 124.1(2) . .
O7 C30 C31 114.9(2) . .
C29 C30 C31 121.0(3) . .
C30 C31 C34 121.1(2) . .
C32 C31 C30 117.8(2) . .
C32 C31 C34 121.0(2) . .
O5 C32 C27 120.8(2) . .
O5 C32 C31 116.3(2) . .
C31 C32 C27 122.9(2) . .
O7 C33 H33A 109.5 . .
O7 C33 H33B 109.5 . .
O7 C33 H33C 109.5 . .
H33A C33 H33B 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C31 C34 H34A 109.4 . .
C31 C34 H34B 109.4 . .
H34A C34 H34B 108.0 . .
C35 C34 C31 111.07(17) . .
C35 C34 H34A 109.4 . .
C35 C34 H34B 109.4 . .
C34 C35 H35 116.2 . .
C36 C35 C34 127.58(19) . .
C36 C35 H35 116.2 . .
C35 C36 C37 116.61(17) . .
C35 C36 C38 124.29(17) . .
C37 C36 C38 119.10(17) . .
N3 C37 C36 122.88(17) . .
N3 C37 H37 118.6 . .
C36 C37 H37 118.6 . .
C36 C38 H38A 109.5 . .
C36 C38 H38B 109.5 . .
C36 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
O8 C39 N4 122.35(18) . .
O8 C39 C40 121.15(18) . .
N4 C39 C40 116.50(16) . .
C41 C40 C39 123.96(17) . .
C41 C40 C45 118.97(18) . .
C45 C40 C39 117.06(18) . .
C40 C41 H41 119.3 . .
C40 C41 C42 121.45(18) . .
C42 C41 H41 119.3 . .
C41 C42 C46 120.79(19) . .
C43 C42 C41 117.8(2) . .
C43 C42 C46 121.4(2) . .
C42 C43 H43 119.2 . .
C44 C43 C42 121.7(2) . .
C44 C43 H43 119.2 . .
C43 C44 H44 120.0 . .
C43 C44 C45 120.1(2) . .
C45 C44 H44 120.0 . .
C40 C45 H45 120.0 . .
C44 C45 C40 120.0(2) . .
C44 C45 H45 120.0 . .
C42 C46 H46A 109.5 . .
C42 C46 H46B 109.5 . .
C42 C46 H46C 109.5 . .
H46A C46 H46B 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.388(3) .
O1 C9 1.380(2) .
O2 C1 1.201(3) .
O3 C7 1.361(3) .
O3 C10 1.426(3) .
O4 C16 1.223(2) .
N1 N2 1.390(2) .
N1 C14 1.277(2) .
N2 H2 0.8600 .
N2 C16 1.352(2) .
C1 C2 1.435(4) .
C2 H2A 0.9300 .
C2 C3 1.334(4) .
C3 H3 0.9300 .
C3 C4 1.431(4) .
C4 C5 1.387(4) .
C4 C9 1.398(3) .
C5 H5 0.9300 .
C5 C6 1.370(4) .
C6 H6 0.9300 .
C6 C7 1.404(3) .
C7 C8 1.397(3) .
C8 C9 1.381(3) .
C8 C11 1.512(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.497(3) .
C12 H12 0.9300 .
C12 C13 1.332(3) .
C13 C14 1.454(3) .
C13 C15 1.496(3) .
C14 H14 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.494(3) .
C17 C18 1.386(3) .
C17 C22 1.382(3) .
C18 H18 0.9300 .
C18 C19 1.392(3) .
C19 C20 1.376(4) .
C19 C23 1.504(4) .
C20 H20 0.9300 .
C20 C21 1.363(4) .
C21 H21 0.9300 .
C21 C22 1.379(4) .
C22 H22 0.9300 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
O5 C24 1.378(4) .
O5 C32 1.378(3) .
O6 C24 1.197(4) .
O7 C30 1.366(3) .
O7 C33 1.427(3) .
O8 C39 1.221(2) .
N3 N4 1.388(2) .
N3 C37 1.274(2) .
N4 H4 0.8600 .
N4 C39 1.345(2) .
C24 C25 1.438(5) .
C25 H25 0.9300 .
C25 C26 1.349(5) .
C26 H26 0.9300 .
C26 C27 1.414(4) .
C27 C28 1.399(4) .
C27 C32 1.397(3) .
C28 H28 0.9300 .
C28 C29 1.368(4) .
C29 H29 0.9300 .
C29 C30 1.393(4) .
C30 C31 1.400(3) .
C31 C32 1.380(3) .
C31 C34 1.506(3) .
C33 H33A 0.9600 .
C33 H33B 0.9600 .
C33 H33C 0.9600 .
C34 H34A 0.9700 .
C34 H34B 0.9700 .
C34 C35 1.494(3) .
C35 H35 0.9300 .
C35 C36 1.334(3) .
C36 C37 1.458(3) .
C36 C38 1.503(3) .
C37 H37 0.9300 .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
C39 C40 1.496(3) .
C40 C41 1.383(3) .
C40 C45 1.397(3) .
C41 H41 0.9300 .
C41 C42 1.395(3) .
C42 C43 1.387(3) .
C42 C46 1.496(3) .
C43 H43 0.9300 .
C43 C44 1.369(3) .
C44 H44 0.9300 .
C44 C45 1.378(3) .
C45 H45 0.9300 .
C46 H46A 0.9600 .
C46 H46B 0.9600 .
C46 H46C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O8 0.86 2.05 2.873(2) 161.0 .
