#------------------------------------------------------------------------------
#$Date: 2020-10-13 02:13:06 +0300 (Tue, 13 Oct 2020) $
#$Revision: 258315 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038886.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_4038886
loop_
_publ_author_name
'Beesu, Mallesh'
'Mehta, Goverdhan'
_publ_section_title
;
 Orthogonal Strapping of o-Haloaryl Ynones with Pyrazolones: A One-Pot,
 Domino Process toward Spiropyrazolones
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02087
_journal_year                    2020
_chemical_formula_moiety         '2(C24 H17 N3 O2)'
_chemical_formula_sum            'C48 H34 N6 O4'
_chemical_formula_weight         758.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                95.554(4)
_cell_angle_beta                 95.804(4)
_cell_angle_gamma                96.061(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9652(7)
_cell_length_b                   8.0725(8)
_cell_length_c                   30.441(3)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      2.58
_cell_volume                     1925.0(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1784
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            83127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.552
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1492 before and 0.0765 after correction. The Ratio of minimum to maximum transmission is 0.8598. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0851
_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)+(0.0627P)²+1.9643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4615
_reflns_number_total             8872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c02087_si_002.cif
_cod_data_source_block           gm129a_0m_a
_cod_database_code               4038886
_shelx_shelxl_version_number     2018/3
_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   0.983
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C42(H42), C38(H38), C11(H11), C2(H2), C36(H36), C12(H12),
 C34(H34), C44(H44), C43(H43), C3(H3), C15(H15), C13(H13), C14(H14), C33(H33),
 C32(H32), C19(H19), C29(H29), C31(H31), C23(H23), C20(H20), C21(H21), C22(H22),
  C27(H27), C28(H28), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O -0.0642(3) 0.6448(3) 0.38533(8) 0.0470(6) Uani 1 1 d . . . . .
O2 O 0.2486(3) 0.5411(3) 0.11569(8) 0.0519(7) Uani 1 1 d . . . . .
N4 N 0.0941(3) 0.8971(3) 0.37912(9) 0.0357(6) Uani 1 1 d . . . . .
O1 O -0.1811(3) 0.8674(4) 0.01185(9) 0.0629(8) Uani 1 1 d . . . . .
N5 N 0.2606(3) 0.9755(3) 0.39286(9) 0.0386(7) Uani 1 1 d . . . . .
O4 O 0.3565(3) 0.3127(3) 0.48822(9) 0.0606(8) Uani 1 1 d . . . . .
N6 N 0.1215(4) 0.8286(4) 0.48521(10) 0.0448(7) Uani 1 1 d . . . . .
N3 N 0.3420(3) 0.6343(4) 0.01519(10) 0.0431(7) Uani 1 1 d . . . . .
N2 N 0.5722(3) 0.8573(4) 0.10670(9) 0.0440(7) Uani 1 1 d . . . . .
N1 N 0.5072(3) 0.7047(4) 0.12086(9) 0.0435(7) Uani 1 1 d . . . . .
C24 C 0.0649(4) 0.7418(4) 0.39281(10) 0.0337(7) Uani 1 1 d . . . . .
C9 C 0.2326(4) 0.7135(4) 0.41984(10) 0.0320(7) Uani 1 1 d . . . . .
C16 C 0.3384(4) 0.8771(4) 0.41577(10) 0.0340(7) Uani 1 1 d . . . . .
C35 C 0.1979(4) 0.9864(4) 0.14639(11) 0.0368(8) Uani 1 1 d . . . . .
C5 C 0.2377(4) 0.5681(4) 0.49028(10) 0.0352(8) Uani 1 1 d . . . . .
C8 C 0.3090(4) 0.5645(4) 0.39882(11) 0.0351(8) Uani 1 1 d . . . . .
C4 C 0.1969(4) 0.7006(4) 0.46771(11) 0.0361(8) Uani 1 1 d . . . . .
C41 C 0.2294(4) 0.7252(4) 0.03245(10) 0.0336(7) Uani 1 1 d . . . . .
C45 C 0.2843(4) 0.8027(4) 0.08015(10) 0.0317(7) Uani 1 1 d . . . . .
C47 C 0.4518(4) 0.9130(4) 0.08369(10) 0.0351(7) Uani 1 1 d . . . . .
C40 C 0.0742(4) 0.7460(4) 0.00999(11) 0.0354(8) Uani 1 1 d . . . . .
C18 C -0.0169(4) 0.9807(4) 0.35160(11) 0.0390(8) Uani 1 1 d . . . . .
C10 C 0.3589(4) 0.5706(4) 0.35314(11) 0.0390(8) Uani 1 1 d . . . . .
C37 C 0.1511(4) 0.8967(4) 0.10108(11) 0.0350(7) Uani 1 1 d . . . . .
C7 C 0.3439(4) 0.4374(4) 0.42174(11) 0.0403(8) Uani 1 1 d . . . . .
H7 H 0.389864 0.346516 0.406908 0.048 Uiso 1 1 calc R . . . .
C1 C 0.1997(4) 0.5675(5) 0.53408(11) 0.0451(9) Uani 1 1 d . . . . .
H1 H 0.226662 0.478569 0.550822 0.054 Uiso 1 1 calc R . . . .
C6 C 0.3160(4) 0.4290(4) 0.46832(12) 0.0412(8) Uani 1 1 d . . . . .
C46 C 0.3381(4) 0.6622(4) 0.10764(11) 0.0378(8) Uani 1 1 d . . . . .
C42 C 0.0358(4) 0.6699(4) -0.03347(11) 0.0435(9) Uani 1 1 d . . . . .
H42 H -0.069063 0.681620 -0.050062 0.052 Uiso 1 1 calc R . . . .
C38 C 0.0021(4) 0.9112(4) 0.07810(11) 0.0402(8) Uani 1 1 d . . . . .
H38 H -0.077241 0.969630 0.092828 0.048 Uiso 1 1 calc R . . . .
C39 C -0.0463(4) 0.8428(4) 0.03170(12) 0.0400(8) Uani 1 1 d . . . . .
C11 C 0.2487(5) 0.6050(5) 0.31759(12) 0.0481(9) Uani 1 1 d . . . . .
H11 H 0.135317 0.623256 0.321886 0.058 Uiso 1 1 calc R . . . .
C48 C 0.4778(5) 1.0700(5) 0.06272(13) 0.0490(9) Uani 1 1 d . . . . .
H48A H 0.418513 1.155704 0.077679 0.073 Uiso 1 1 calc GR . . . .
H48B H 0.432687 1.049586 0.031267 0.073 Uiso 1 1 calc GR . . . .
H48C H 0.599562 1.108957 0.065309 0.073 Uiso 1 1 calc GR . . . .
C17 C 0.5167(4) 0.9222(5) 0.43636(13) 0.0515(10) Uani 1 1 d . . . . .
H17A H 0.588747 0.843257 0.423613 0.077 Uiso 1 1 calc GR . . . .
H17B H 0.521769 0.916896 0.468486 0.077 Uiso 1 1 calc GR . . . .
H17C H 0.557029 1.036061 0.430554 0.077 Uiso 1 1 calc GR . . . .
C30 C 0.6160(5) 0.6208(6) 0.14862(12) 0.0552(11) Uani 1 1 d . . . . .
C2 C 0.1231(5) 0.6971(5) 0.55244(12) 0.0508(10) Uani 1 1 d . . . . .
H2 H 0.095783 0.699821 0.582145 0.061 Uiso 1 1 calc R . . . .
C36 C 0.1805(5) 1.1558(5) 0.15286(12) 0.0537(10) Uani 1 1 d . . . . .
H36 H 0.136848 1.210278 0.128621 0.064 Uiso 1 1 calc R . . . .
C12 C 0.5226(5) 0.5443(5) 0.34531(12) 0.0508(10) Uani 1 1 d . . . . .
H12 H 0.599626 0.519140 0.368998 0.061 Uiso 1 1 calc R . . . .
C34 C 0.2616(5) 0.9115(5) 0.18285(12) 0.0550(10) Uani 1 1 d . . . . .
H34 H 0.274924 0.795580 0.179495 0.066 Uiso 1 1 calc R . . . .
C44 C 0.3000(5) 0.5633(5) -0.02674(12) 0.0494(9) Uani 1 1 d . . . . .
H44 H 0.378562 0.498418 -0.039791 0.059 Uiso 1 1 calc R . . . .
C43 C 0.1507(5) 0.5784(5) -0.05194(12) 0.0488(9) Uani 1 1 d . . . . .
H43 H 0.127644 0.526386 -0.081602 0.059 Uiso 1 1 calc R . . . .
C3 C 0.0863(5) 0.8233(5) 0.52703(13) 0.0537(10) Uani 1 1 d . . . . .
H3 H 0.032537 0.912394 0.540082 0.064 Uiso 1 1 calc R . . . .
C15 C 0.3038(6) 0.6127(5) 0.27557(12) 0.0555(10) Uani 1 1 d . . . . .
H15 H 0.227373 0.634674 0.251357 0.067 Uiso 1 1 calc R . . . .
C13 C 0.5764(5) 0.5537(6) 0.30389(14) 0.0631(11) Uani 1 1 d . . . . .
H13 H 0.689748 0.535882 0.299450 0.076 Uiso 1 1 calc R . . . .
C14 C 0.4681(6) 0.5885(5) 0.26924(13) 0.0603(11) Uani 1 1 d . . . . .
H14 H 0.506165 0.595929 0.240839 0.072 Uiso 1 1 calc R . . . .
C33 C 0.3053(6) 1.0022(6) 0.22339(13) 0.0704(13) Uani 1 1 d . . . . .
H33 H 0.349284 0.948408 0.247745 0.084 Uiso 1 1 calc R . . . .
C32 C 0.2256(6) 1.2467(5) 0.19397(14) 0.0723(13) Uani 1 1 d . . . . .
H32 H 0.213912 1.362989 0.197494 0.087 Uiso 1 1 calc R . . . .
C19 C -0.1874(5) 0.9352(6) 0.34700(17) 0.0762(14) Uani 1 1 d . . . . .
H19 H -0.233307 0.846877 0.362278 0.091 Uiso 1 1 calc R . . . .
C29 C 0.5856(6) 0.4533(6) 0.15064(14) 0.0739(14) Uani 1 1 d . . . . .
H29 H 0.490685 0.389319 0.133263 0.089 Uiso 1 1 calc R . . . .
C31 C 0.2866(6) 1.1715(6) 0.22959(14) 0.0695(12) Uani 1 1 d . . . . .
H31 H 0.315650 1.233697 0.257961 0.083 Uiso 1 1 calc R . . . .
C23 C 0.0466(6) 1.1143(6) 0.33256(17) 0.0827(16) Uani 1 1 d . . . . .
H23 H 0.164806 1.151558 0.337157 0.099 Uiso 1 1 calc R . . . .
C20 C -0.2948(6) 1.0172(7) 0.3201(2) 0.0962(19) Uani 1 1 d . . . . .
H20 H -0.413978 0.984974 0.316908 0.115 Uiso 1 1 calc R . . . .
C21 C -0.2292(7) 1.1438(7) 0.2983(2) 0.101(2) Uani 1 1 d . . . . .
H21 H -0.300276 1.194016 0.277716 0.122 Uiso 1 1 calc R . . . .
C22 C -0.0623(8) 1.1968(7) 0.3062(2) 0.113(2) Uani 1 1 d . . . . .
H22 H -0.017943 1.292832 0.293540 0.136 Uiso 1 1 calc R . . . .
C27 C 0.6957(9) 0.3763(9) 0.1786(2) 0.112(2) Uani 1 1 d . . . . .
H27 H 0.677336 0.258778 0.179874 0.134 Uiso 1 1 calc R . . . .
C28 C 0.7523(6) 0.7176(9) 0.17434(19) 0.110(2) Uani 1 1 d . . . . .
H28 H 0.771777 0.834823 0.172695 0.132 Uiso 1 1 calc R . . . .
C25 C 0.8325(8) 0.4718(13) 0.2045(3) 0.158(4) Uani 1 1 d . . . . .
H25 H 0.907229 0.419693 0.223676 0.190 Uiso 1 1 calc R . . . .
C26 C 0.8591(7) 0.6400(13) 0.2024(3) 0.170(4) Uani 1 1 d . . . . .
H26 H 0.952003 0.704898 0.220342 0.204 Uiso 1 1 calc R . . . .
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
_geom_angle_publ_flag
N5 N4 C18 118.5(2) . . ?
C24 N4 N5 113.2(2) . . ?
C24 N4 C18 128.3(3) . . ?
C16 N5 N4 107.8(3) . . ?
C3 N6 C4 116.4(3) . . ?
C41 N3 C44 116.5(3) . . ?
C47 N2 N1 108.0(3) . . ?
N2 N1 C30 118.8(3) . . ?
C46 N1 N2 113.2(3) . . ?
C46 N1 C30 127.9(3) . . ?
O3 C24 N4 127.8(3) . . ?
O3 C24 C9 126.8(3) . . ?
N4 C24 C9 105.5(3) . . ?
C16 C9 C24 99.7(2) . . ?
C16 C9 C8 111.5(3) . . ?
C16 C9 C4 110.9(3) . . ?
C8 C9 C24 111.5(3) . . ?
C8 C9 C4 114.3(3) . . ?
C4 C9 C24 107.7(2) . . ?
N5 C16 C9 113.8(3) . . ?
N5 C16 C17 122.2(3) . . ?
C17 C16 C9 124.0(3) . . ?
C36 C35 C37 118.5(3) . . ?
C36 C35 C34 117.5(3) . . ?
C34 C35 C37 124.0(3) . . ?
C4 C5 C1 118.0(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C5 C6 121.2(3) . . ?
C10 C8 C9 118.3(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 C10 120.3(3) . . ?
N6 C4 C9 113.9(3) . . ?
N6 C4 C5 123.8(3) . . ?
C5 C4 C9 122.3(3) . . ?
N3 C41 C45 114.0(3) . . ?
N3 C41 C40 123.8(3) . . ?
C40 C41 C45 122.2(3) . . ?
C41 C45 C46 107.9(3) . . ?
C47 C45 C41 111.2(3) . . ?
C47 C45 C37 110.7(3) . . ?
C47 C45 C46 100.0(2) . . ?
C37 C45 C41 114.2(3) . . ?
C37 C45 C46 111.8(3) . . ?
N2 C47 C45 113.4(3) . . ?
N2 C47 C48 122.1(3) . . ?
C48 C47 C45 124.4(3) . . ?
C41 C40 C42 117.8(3) . . ?
C41 C40 C39 120.8(3) . . ?
C42 C40 C39 121.4(3) . . ?
C19 C18 N4 120.6(3) . . ?
C23 C18 N4 119.6(3) . . ?
C23 C18 C19 119.6(4) . . ?
C11 C10 C8 122.9(3) . . ?
C12 C10 C8 119.3(3) . . ?
C12 C10 C11 117.8(3) . . ?
C35 C37 C45 118.0(3) . . ?
C38 C37 C35 120.5(3) . . ?
C38 C37 C45 121.2(3) . . ?
C8 C7 H7 117.9 . . ?
C8 C7 C6 124.2(3) . . ?
C6 C7 H7 117.9 . . ?
C5 C1 H1 120.6 . . ?
C2 C1 C5 118.9(3) . . ?
C2 C1 H1 120.6 . . ?
O4 C6 C5 121.4(3) . . ?
O4 C6 C7 121.4(3) . . ?
C7 C6 C5 117.1(3) . . ?
O2 C46 N1 127.7(3) . . ?
O2 C46 C45 127.1(3) . . ?
N1 C46 C45 105.3(3) . . ?
C40 C42 H42 120.4 . . ?
C43 C42 C40 119.3(3) . . ?
C43 C42 H42 120.4 . . ?
C37 C38 H38 117.9 . . ?
C37 C38 C39 124.1(3) . . ?
C39 C38 H38 117.9 . . ?
O1 C39 C40 121.6(3) . . ?
O1 C39 C38 121.0(3) . . ?
C38 C39 C40 117.4(3) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C15 120.4(4) . . ?
C15 C11 H11 119.8 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C29 C30 N1 121.2(4) . . ?
C29 C30 C28 121.5(4) . . ?
C28 C30 N1 117.4(4) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(4) . . ?
C3 C2 H2 120.7 . . ?
C35 C36 H36 119.4 . . ?
C32 C36 C35 121.1(4) . . ?
C32 C36 H36 119.4 . . ?
C10 C12 H12 119.3 . . ?
C13 C12 C10 121.4(4) . . ?
C13 C12 H12 119.3 . . ?
C35 C34 H34 119.5 . . ?
C33 C34 C35 121.0(4) . . ?
C33 C34 H34 119.5 . . ?
N3 C44 H44 118.0 . . ?
N3 C44 C43 124.1(4) . . ?
C43 C44 H44 118.0 . . ?
C42 C43 C44 118.6(3) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
N6 C3 C2 124.1(4) . . ?
N6 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
C11 C15 H15 119.9 . . ?
C14 C15 C11 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.1 . . ?
C34 C33 H33 119.5 . . ?
C34 C33 C31 121.1(4) . . ?
C31 C33 H33 119.5 . . ?
C36 C32 H32 119.6 . . ?
C31 C32 C36 120.8(4) . . ?
C31 C32 H32 119.6 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(4) . . ?
C20 C19 H19 119.8 . . ?
C30 C29 H29 120.4 . . ?
C30 C29 C27 119.1(6) . . ?
C27 C29 H29 120.4 . . ?
C33 C31 H31 120.8 . . ?
C32 C31 C33 118.5(4) . . ?
C32 C31 H31 120.8 . . ?
C18 C23 H23 120.3 . . ?
C18 C23 C22 119.4(4) . . ?
C22 C23 H23 120.3 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(5) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(4) . . ?
C22 C21 H21 120.5 . . ?
C23 C22 H22 119.3 . . ?
C21 C22 C23 121.4(5) . . ?
C21 C22 H22 119.3 . . ?
C29 C27 H27 120.0 . . ?
C25 C27 C29 119.9(6) . . ?
C25 C27 H27 120.0 . . ?
C30 C28 H28 120.6 . . ?
C26 C28 C30 118.8(6) . . ?
C26 C28 H28 120.6 . . ?
C27 C25 H25 120.0 . . ?
C26 C25 C27 119.9(5) . . ?
C26 C25 H25 120.0 . . ?
C28 C26 H26 119.6 . . ?
C25 C26 C28 120.7(7) . . ?
C25 C26 H26 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C24 1.212(4) . ?
O2 C46 1.208(4) . ?
N4 N5 1.412(4) . ?
N4 C24 1.363(4) . ?
N4 C18 1.423(4) . ?
O1 C39 1.222(4) . ?
N5 C16 1.275(4) . ?
O4 C6 1.219(4) . ?
N6 C4 1.342(4) . ?
N6 C3 1.335(5) . ?
N3 C41 1.334(4) . ?
N3 C44 1.342(4) . ?
N2 N1 1.409(4) . ?
N2 C47 1.276(4) . ?
N1 C46 1.364(4) . ?
N1 C30 1.418(4) . ?
C24 C9 1.547(4) . ?
C9 C16 1.513(4) . ?
C9 C8 1.520(5) . ?
C9 C4 1.524(4) . ?
C16 C17 1.486(4) . ?
C35 C37 1.487(5) . ?
C35 C36 1.386(5) . ?
C35 C34 1.391(5) . ?
C5 C4 1.376(4) . ?
C5 C1 1.397(5) . ?
C5 C6 1.477(5) . ?
C8 C10 1.488(5) . ?
C8 C7 1.332(4) . ?
C41 C45 1.526(4) . ?
C41 C40 1.385(4) . ?
C45 C47 1.511(4) . ?
C45 C37 1.523(4) . ?
C45 C46 1.544(4) . ?
C47 C48 1.479(5) . ?
C40 C42 1.393(5) . ?
C40 C39 1.468(5) . ?
C18 C19 1.358(5) . ?
C18 C23 1.349(5) . ?
C10 C11 1.392(5) . ?
C10 C12 1.383(5) . ?
C37 C38 1.337(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.464(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.366(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.464(5) . ?
C11 H11 0.9500 . ?
C11 C15 1.398(5) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C30 C29 1.357(6) . ?
C30 C28 1.390(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(5) . ?
C36 H36 0.9500 . ?
C36 C32 1.382(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(5) . ?
C34 H34 0.9500 . ?
C34 C33 1.365(5) . ?
C44 H44 0.9500 . ?
C44 C43 1.372(5) . ?
C43 H43 0.9500 . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.373(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.364(6) . ?
C14 H14 0.9500 . ?
C33 H33 0.9500 . ?
C33 C31 1.388(6) . ?
C32 H32 0.9500 . ?
C32 C31 1.365(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(6) . ?
C29 H29 0.9500 . ?
C29 C27 1.394(6) . ?
C31 H31 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.387(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.359(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.343(7) . ?
C22 H22 0.9500 . ?
C27 H27 0.9500 . ?
C27 C25 1.391(11) . ?
C28 H28 0.9500 . ?
C28 C26 1.383(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.361(12) . ?
C26 H26 0.9500 . ?
