#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:54:59 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567548.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_1567548
loop_
_publ_author_name
'Muraoka, Masanobu'
'Goto, Masahide'
'Minami, Masaki'
'Zhou, Dayang'
'Suzuki, Takeyuki'
'Yajima, Tatsuo'
'Hayashi, Jun'ichi'
'Sogawa, Hiromitsu'
'Sanda, Fumio'
_publ_section_title
;
 Ethynylene-linked multifunctional benzoxazines: the effect of the
 ethynylene group and packing on thermal behavior
;
_journal_issue                   39
_journal_name_full               'Polymer Chemistry'
_journal_page_first              5590
_journal_page_last               5596
_journal_paper_doi               10.1039/D2PY00840H
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.38
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2bpcv8
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                98.672(7)
_cell_angle_beta                 96.018(7)
_cell_angle_gamma                90.007(6)
_cell_formula_units_Z            4
_cell_length_a                   7.4998(13)
_cell_length_b                   11.4895(17)
_cell_length_c                   18.504(3)
_cell_measurement_reflns_used    11580
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      1.79
_cell_volume                     1567.3(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14826
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.793
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656.00
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0152P)²+6.3219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4935
_reflns_number_total             7140
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2py00840h5.cif
_cod_data_source_block           210421-2
_cod_depositor_comments          'Adding full bibliography for 1567548.cif.'
_cod_original_cell_volume        1567.4(4)
_cod_database_code               1567548
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
O1 O 1.1477(4) 0.2991(2) 0.72490(14) 0.0252(6) Uani 1 1 d . . . . .
O2 O 0.6481(4) 0.3106(2) 0.72492(14) 0.0257(6) Uani 1 1 d . . . . .
N1 N 0.9923(4) 0.4087(3) 0.64092(15) 0.0199(6) Uani 1 1 d . . . . .
N2 N 0.4921(4) 0.1603(3) 0.64154(16) 0.0206(6) Uani 1 1 d . . . . .
C1 C 0.5100(4) 0.3930(3) 0.16610(19) 0.0195(7) Uani 1 1 d . . . . .
H1 H 0.575645 0.464794 0.181163 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4384(5) 0.3635(4) 0.0940(2) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.456765 0.414896 0.059639 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3401(5) 0.2601(4) 0.0708(2) 0.0326(9) Uani 1 1 d . . . . .
H3 H 0.291516 0.240565 0.020923 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3136(5) 0.1862(3) 0.1204(2) 0.0301(9) Uani 1 1 d . . . . .
H4 H 0.245361 0.115571 0.104799 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3852(5) 0.2134(3) 0.1931(2) 0.0254(8) Uani 1 1 d . . . . .
H5 H 0.365946 0.161357 0.226902 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4866(4) 0.3181(3) 0.21706(19) 0.0187(7) Uani 1 1 d . . . . .
C7 C 0.5705(5) 0.3409(3) 0.2904(2) 0.0239(7) Uani 1 1 d . . . . .
C8 C 0.6465(5) 0.3570(3) 0.35128(19) 0.0214(7) Uani 1 1 d . . . . .
C9 C 0.7391(4) 0.3727(3) 0.42418(18) 0.0190(7) Uani 1 1 d . . . . .
C10 C 0.7110(4) 0.4703(3) 0.47523(19) 0.0199(7) Uani 1 1 d . . . . .
H6 H 0.632215 0.529542 0.461108 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7951(4) 0.4837(3) 0.54654(19) 0.0191(7) Uani 1 1 d . . . . .
H7 H 0.772334 0.551188 0.580597 0.023 Uiso 1 1 calc R U . . .
C12 C 0.9146(4) 0.3975(3) 0.56870(18) 0.0171(6) Uani 1 1 d . . . . .
C13 C 0.9452(4) 0.3003(3) 0.51658(18) 0.0186(7) Uani 1 1 d . . . . .
H8 H 1.026556 0.241882 0.529997 0.022 Uiso 1 1 calc R U . . .
C14 C 0.8602(5) 0.2875(3) 0.44632(19) 0.0203(7) Uani 1 1 d . . . . .
H9 H 0.883237 0.220267 0.412108 0.024 Uiso 1 1 calc R U . . .
C15 C 0.9458(5) 0.5043(3) 0.69662(18) 0.0205(7) Uani 1 1 d . . . . .
H10 H 0.813687 0.510780 0.694018 0.025 Uiso 1 1 calc R U . . .
H11 H 0.995340 0.579465 0.686752 0.025 Uiso 1 1 calc R U . . .
C16 C 1.0194(4) 0.4830(3) 0.77324(18) 0.0160(6) Uani 1 1 d . . . . .
C17 C 0.9922(4) 0.5673(3) 0.83358(18) 0.0187(7) Uani 1 1 d . . . . .
H12 H 0.930552 0.637440 0.826170 0.022 Uiso 1 1 calc R U . . .
C18 C 1.0540(5) 0.5496(4) 0.9037(2) 0.0291(8) Uani 1 1 d . . . . .
H13 H 1.035756 0.607307 0.944610 0.035 Uiso 1 1 calc R U . . .
C19 C 1.1442(5) 0.4454(4) 0.9140(2) 0.0353(10) Uani 1 1 d . . . . .
H14 H 1.186369 0.432615 0.962401 0.042 Uiso 1 1 calc R U . . .
C20 C 1.1727(5) 0.3612(3) 0.8549(2) 0.0266(8) Uani 1 1 d . . . . .
H15 H 1.232953 0.290541 0.862226 0.032 Uiso 1 1 calc R U . . .
C21 C 1.1118(5) 0.3815(3) 0.7848(2) 0.0211(7) Uani 1 1 d . . . . .
C22 C 1.1587(5) 0.3533(3) 0.66106(19) 0.0224(7) Uani 1 1 d . . . . .
H16 H 1.186794 0.293156 0.619783 0.027 Uiso 1 1 calc R U . . .
H17 H 1.256822 0.413047 0.670780 0.027 Uiso 1 1 calc R U . . .
C23 C 0.0107(5) -0.0576(3) 0.16536(19) 0.0225(7) Uani 1 1 d . . . . .
H18 H 0.075004 -0.122178 0.181045 0.027 Uiso 1 1 calc R U . . .
C24 C -0.0602(5) -0.0623(3) 0.09265(19) 0.0215(7) Uani 1 1 d . . . . .
H19 H -0.041758 -0.129688 0.057781 0.026 Uiso 1 1 calc R U . . .
C25 C -0.1578(5) 0.0310(3) 0.0708(2) 0.0261(8) Uani 1 1 d . . . . .
H20 H -0.204929 0.027372 0.020769 0.031 Uiso 1 1 calc R U . . .
C26 C -0.1872(5) 0.1283(3) 0.1203(2) 0.0283(8) Uani 1 1 d . . . . .
H21 H -0.257505 0.190523 0.104734 0.034 Uiso 1 1 calc R U . . .
C27 C -0.1161(5) 0.1364(3) 0.1920(2) 0.0280(8) Uani 1 1 d . . . . .
H22 H -0.135770 0.204737 0.225861 0.034 Uiso 1 1 calc R U . . .
C28 C -0.0146(5) 0.0448(3) 0.2156(2) 0.0253(8) Uani 1 1 d . . . . .
C29 C 0.0697(5) 0.0584(3) 0.2900(2) 0.0237(7) Uani 1 1 d . . . . .
C30 C 0.1462(5) 0.0710(3) 0.35091(19) 0.0207(7) Uani 1 1 d . . . . .
C31 C 0.2391(4) 0.0902(3) 0.42389(18) 0.0187(7) Uani 1 1 d . . . . .
C32 C 0.2107(5) 0.0176(3) 0.47532(19) 0.0209(7) Uani 1 1 d . . . . .
H23 H 0.131445 -0.048383 0.461550 0.025 Uiso 1 1 calc R U . . .
C33 C 0.2962(4) 0.0396(3) 0.54675(19) 0.0194(7) Uani 1 1 d . . . . .
H24 H 0.273924 -0.011390 0.580847 0.023 Uiso 1 1 calc R U . . .
C34 C 0.4142(4) 0.1355(3) 0.56897(17) 0.0170(6) Uani 1 1 d . . . . .
C35 C 0.4456(4) 0.2076(3) 0.51658(18) 0.0190(7) Uani 1 1 d . . . . .
H25 H 0.527094 0.272449 0.530021 0.023 Uiso 1 1 calc R U . . .
C36 C 0.3604(5) 0.1860(3) 0.44578(19) 0.0200(7) Uani 1 1 d . . . . .
H26 H 0.383748 0.236286 0.411446 0.024 Uiso 1 1 calc R U . . .
C37 C 0.4463(5) 0.0907(3) 0.69605(18) 0.0205(7) Uani 1 1 d . . . . .
H27 H 0.496987 0.011061 0.685887 0.025 Uiso 1 1 calc R U . . .
H28 H 0.314328 0.082240 0.693484 0.025 Uiso 1 1 calc R U . . .
C38 C 0.5204(5) 0.1498(3) 0.7727(2) 0.0239(7) Uani 1 1 d . . . . .
C39 C 0.4917(5) 0.1008(3) 0.83435(19) 0.0228(7) Uani 1 1 d . . . . .
H29 H 0.426697 0.028374 0.827920 0.027 Uiso 1 1 calc R U . . .
C40 C 0.5538(5) 0.1527(3) 0.90547(19) 0.0206(7) Uani 1 1 d . . . . .
H30 H 0.534334 0.114712 0.946201 0.025 Uiso 1 1 calc R U . . .
C41 C 0.6442(5) 0.2604(3) 0.9164(2) 0.0261(8) Uani 1 1 d . . . . .
H31 H 0.686193 0.297173 0.964700 0.031 Uiso 1 1 calc R U . . .
C42 C 0.6729(5) 0.3143(3) 0.8551(2) 0.0288(8) Uani 1 1 d . . . . .
H32 H 0.732458 0.388680 0.861670 0.035 Uiso 1 1 calc R U . . .
C43 C 0.6125(5) 0.2569(3) 0.78383(19) 0.0229(7) Uani 1 1 d . . . . .
C44 C 0.6593(5) 0.2248(3) 0.66104(19) 0.0233(7) Uani 1 1 d . . . . .
H33 H 0.757083 0.169557 0.670880 0.028 Uiso 1 1 calc R U . . .
H34 H 0.687416 0.264423 0.619578 0.028 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(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
C21 O1 C22 111.2(3) . . ?
C43 O2 C44 110.5(3) . . ?
C12 N1 C22 122.3(3) . . ?
C12 N1 C15 121.6(3) . . ?
C22 N1 C15 113.4(3) . . ?
C34 N2 C44 122.0(3) . . ?
C34 N2 C37 120.7(3) . . ?
C44 N2 C37 114.0(3) . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 121.9(3) . . ?
C5 C6 C7 119.8(3) . . ?
C8 C7 C6 177.3(4) . . ?
C7 C8 C9 178.3(4) . . ?
C10 C9 C14 117.8(3) . . ?
C10 C9 C8 121.4(3) . . ?
C14 C9 C8 120.7(3) . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H6 119.2 . . ?
C11 C10 H6 119.2 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H7 119.9 . . ?
C12 C11 H7 119.9 . . ?
N1 C12 C13 122.0(3) . . ?
N1 C12 C11 120.1(3) . . ?
C13 C12 C11 117.9(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H8 119.3 . . ?
C12 C13 H8 119.3 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H9 119.5 . . ?
C9 C14 H9 119.5 . . ?
N1 C15 C16 111.0(3) . . ?
N1 C15 H10 109.4 . . ?
C16 C15 H10 109.4 . . ?
N1 C15 H11 109.4 . . ?
C16 C15 H11 109.4 . . ?
H10 C15 H11 108.0 . . ?
C21 C16 C17 119.1(3) . . ?
C21 C16 C15 121.8(3) . . ?
C17 C16 C15 119.1(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H12 119.7 . . ?
C16 C17 H12 119.7 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H13 120.4 . . ?
C19 C18 H13 120.4 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H14 119.6 . . ?
C18 C19 H14 119.6 . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H15 120.6 . . ?
C21 C20 H15 120.6 . . ?
C20 C21 C16 121.3(3) . . ?
C20 C21 O1 118.9(3) . . ?
C16 C21 O1 119.9(3) . . ?
O1 C22 N1 110.8(3) . . ?
O1 C22 H16 109.5 . . ?
N1 C22 H16 109.5 . . ?
O1 C22 H17 109.5 . . ?
N1 C22 H17 109.5 . . ?
H16 C22 H17 108.1 . . ?
C24 C23 C28 118.8(3) . . ?
C24 C23 H18 120.6 . . ?
C28 C23 H18 120.6 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H19 119.9 . . ?
C23 C24 H19 119.9 . . ?
C26 C25 C24 120.8(4) . . ?
C26 C25 H20 119.6 . . ?
C24 C25 H20 119.6 . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H21 119.8 . . ?
C25 C26 H21 119.8 . . ?
C26 C27 C28 120.3(4) . . ?
C26 C27 H22 119.9 . . ?
C28 C27 H22 119.9 . . ?
C27 C28 C23 119.5(3) . . ?
C27 C28 C29 119.5(3) . . ?
C23 C28 C29 120.9(3) . . ?
C30 C29 C28 177.4(4) . . ?
C29 C30 C31 178.1(4) . . ?
C32 C31 C36 117.8(3) . . ?
C32 C31 C30 121.7(3) . . ?
C36 C31 C30 120.4(3) . . ?
C31 C32 C33 121.3(3) . . ?
C31 C32 H23 119.4 . . ?
C33 C32 H23 119.4 . . ?
C32 C33 C34 121.0(3) . . ?
C32 C33 H24 119.5 . . ?
C34 C33 H24 119.5 . . ?
N2 C34 C33 120.6(3) . . ?
N2 C34 C35 121.7(3) . . ?
C33 C34 C35 117.7(3) . . ?
C36 C35 C34 121.3(3) . . ?
C36 C35 H25 119.4 . . ?
C34 C35 H25 119.4 . . ?
C35 C36 C31 120.9(3) . . ?
C35 C36 H26 119.6 . . ?
C31 C36 H26 119.6 . . ?
N2 C37 C38 110.0(3) . . ?
N2 C37 H27 109.7 . . ?
C38 C37 H27 109.7 . . ?
N2 C37 H28 109.7 . . ?
C38 C37 H28 109.7 . . ?
H27 C37 H28 108.2 . . ?
C39 C38 C43 117.2(3) . . ?
C39 C38 C37 121.0(3) . . ?
C43 C38 C37 121.8(3) . . ?
C38 C39 C40 123.0(3) . . ?
C38 C39 H29 118.5 . . ?
C40 C39 H29 118.5 . . ?
C41 C40 C39 119.6(3) . . ?
C41 C40 H30 120.2 . . ?
C39 C40 H30 120.2 . . ?
C40 C41 C42 119.1(3) . . ?
C40 C41 H31 120.4 . . ?
C42 C41 H31 120.4 . . ?
C41 C42 C43 119.5(3) . . ?
C41 C42 H32 120.3 . . ?
C43 C42 H32 120.3 . . ?
O2 C43 C38 120.6(3) . . ?
O2 C43 C42 117.8(3) . . ?
C38 C43 C42 121.6(3) . . ?
O2 C44 N2 110.2(3) . . ?
O2 C44 H33 109.6 . . ?
N2 C44 H33 109.6 . . ?
O2 C44 H34 109.6 . . ?
N2 C44 H34 109.6 . . ?
H33 C44 H34 108.1 . . ?
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
O1 C21 1.394(4) . ?
O1 C22 1.426(4) . ?
O2 C43 1.380(4) . ?
O2 C44 1.431(4) . ?
N1 C12 1.388(4) . ?
N1 C22 1.440(4) . ?
N1 C15 1.458(4) . ?
N2 C34 1.395(4) . ?
N2 C44 1.441(4) . ?
N2 C37 1.446(4) . ?
C1 C2 1.377(5) . ?
C1 C6 1.392(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(5) . ?
C7 C8 1.196(5) . ?
C8 C9 1.437(5) . ?
C9 C10 1.385(5) . ?
C9 C14 1.412(5) . ?
C10 C11 1.388(5) . ?
C10 H6 0.9500 . ?
C11 C12 1.414(5) . ?
C11 H7 0.9500 . ?
C12 C13 1.397(5) . ?
C13 C14 1.374(5) . ?
C13 H8 0.9500 . ?
C14 H9 0.9500 . ?
C15 C16 1.522(4) . ?
C15 H10 0.9900 . ?
C15 H11 0.9900 . ?
C16 C21 1.389(5) . ?
C16 C17 1.396(4) . ?
C17 C18 1.375(5) . ?
C17 H12 0.9500 . ?
C18 C19 1.404(6) . ?
C18 H13 0.9500 . ?
C19 C20 1.382(6) . ?
C19 H14 0.9500 . ?
C20 C21 1.383(5) . ?
C20 H15 0.9500 . ?
C22 H16 0.9900 . ?
C22 H17 0.9900 . ?
C23 C24 1.387(5) . ?
C23 C28 1.411(5) . ?
C23 H18 0.9500 . ?
C24 C25 1.385(5) . ?
C24 H19 0.9500 . ?
C25 C26 1.368(5) . ?
C25 H20 0.9500 . ?
C26 C27 1.367(6) . ?
C26 H21 0.9500 . ?
C27 C28 1.396(5) . ?
C27 H22 0.9500 . ?
C28 C29 1.438(5) . ?
C29 C30 1.199(5) . ?
C30 C31 1.439(5) . ?
C31 C32 1.389(5) . ?
C31 C36 1.411(5) . ?
C32 C33 1.394(5) . ?
C32 H23 0.9500 . ?
C33 C34 1.398(5) . ?
C33 H24 0.9500 . ?
C34 C35 1.404(5) . ?
C35 C36 1.383(5) . ?
C35 H25 0.9500 . ?
C36 H26 0.9500 . ?
C37 C38 1.525(5) . ?
C37 H27 0.9900 . ?
C37 H28 0.9900 . ?
C38 C39 1.383(5) . ?
C38 C43 1.387(5) . ?
C39 C40 1.392(5) . ?
C39 H29 0.9500 . ?
C40 C41 1.388(5) . ?
C40 H30 0.9500 . ?
C41 C42 1.407(5) . ?
C41 H31 0.9500 . ?
C42 C43 1.412(6) . ?
C42 H32 0.9500 . ?
C44 H33 0.9900 . ?
C44 H34 0.9900 . ?
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C2 C1 C6 C7 174.8(3) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C6 C7 -175.4(3) . . . . ?
C14 C9 C10 C11 -1.5(5) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C22 N1 C12 C13 26.2(5) . . . . ?
C15 N1 C12 C13 -173.8(3) . . . . ?
C22 N1 C12 C11 -156.1(3) . . . . ?
C15 N1 C12 C11 3.8(5) . . . . ?
C10 C11 C12 N1 -177.2(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
N1 C12 C13 C14 176.6(3) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C10 C9 C14 C13 1.0(5) . . . . ?
C8 C9 C14 C13 -178.1(3) . . . . ?
C12 N1 C15 C16 168.5(3) . . . . ?
C22 N1 C15 C16 -29.9(4) . . . . ?
N1 C15 C16 C21 -2.2(5) . . . . ?
N1 C15 C16 C17 178.2(3) . . . . ?
C21 C16 C17 C18 -0.9(5) . . . . ?
C15 C16 C17 C18 178.7(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C19 C20 C21 C16 -1.7(5) . . . . ?
C19 C20 C21 O1 177.1(3) . . . . ?
C17 C16 C21 C20 1.9(5) . . . . ?
C15 C16 C21 C20 -177.7(3) . . . . ?
C17 C16 C21 O1 -176.9(3) . . . . ?
C15 C16 C21 O1 3.5(5) . . . . ?
C22 O1 C21 C20 -151.5(3) . . . . ?
C22 O1 C21 C16 27.4(4) . . . . ?
C21 O1 C22 N1 -60.4(4) . . . . ?
C12 N1 C22 O1 -135.6(3) . . . . ?
C15 N1 C22 O1 63.0(4) . . . . ?
C28 C23 C24 C25 -1.7(5) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
C24 C25 C26 C27 1.9(6) . . . . ?
C25 C26 C27 C28 -0.8(6) . . . . ?
C26 C27 C28 C23 -1.5(6) . . . . ?
C26 C27 C28 C29 175.7(4) . . . . ?
C24 C23 C28 C27 2.7(5) . . . . ?
C24 C23 C28 C29 -174.4(3) . . . . ?
C36 C31 C32 C33 1.2(5) . . . . ?
C30 C31 C32 C33 -177.5(3) . . . . ?
C31 C32 C33 C34 -0.2(5) . . . . ?
C44 N2 C34 C33 155.5(3) . . . . ?
C37 N2 C34 C33 -2.8(5) . . . . ?
C44 N2 C34 C35 -26.9(5) . . . . ?
C37 N2 C34 C35 174.8(3) . . . . ?
C32 C33 C34 N2 176.7(3) . . . . ?
C32 C33 C34 C35 -1.0(5) . . . . ?
N2 C34 C35 C36 -176.5(3) . . . . ?
C33 C34 C35 C36 1.2(5) . . . . ?
C34 C35 C36 C31 -0.2(5) . . . . ?
C32 C31 C36 C35 -1.0(5) . . . . ?
C30 C31 C36 C35 177.7(3) . . . . ?
C34 N2 C37 C38 -169.0(3) . . . . ?
C44 N2 C37 C38 31.1(4) . . . . ?
N2 C37 C38 C39 179.0(3) . . . . ?
N2 C37 C38 C43 1.7(5) . . . . ?
C43 C38 C39 C40 -1.3(5) . . . . ?
C37 C38 C39 C40 -178.7(3) . . . . ?
C38 C39 C40 C41 2.0(5) . . . . ?
C39 C40 C41 C42 -0.7(5) . . . . ?
C40 C41 C42 C43 -1.3(5) . . . . ?
C44 O2 C43 C38 -27.5(4) . . . . ?
C44 O2 C43 C42 152.5(3) . . . . ?
C39 C38 C43 O2 179.2(3) . . . . ?
C37 C38 C43 O2 -3.4(5) . . . . ?
C39 C38 C43 C42 -0.7(5) . . . . ?
C37 C38 C43 C42 176.7(3) . . . . ?
C41 C42 C43 O2 -178.0(3) . . . . ?
C41 C42 C43 C38 2.0(5) . . . . ?
C43 O2 C44 N2 60.5(4) . . . . ?
C34 N2 C44 O2 136.0(3) . . . . ?
C37 N2 C44 O2 -64.4(4) . . . . ?
