#------------------------------------------------------------------------------
#$Date: 2023-07-27 01:00:32 +0300 (Thu, 27 Jul 2023) $
#$Revision: 285354 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/19/7131934.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_7131934
loop_
_publ_author_name
'Tsuchiya, Takahiro'
'Hamano, Tomohiro'
'Inoue, Masahiro'
'Nakamura, Tomoya'
'Wakamiya, Atsushi'
'Mazaki, Yasuhiro'
_publ_section_title
;
 Intense Absorption of Azulene Realized by Molecular Orbital Inversion
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02311G
_journal_year                    2023
_chemical_formula_sum            'C38 H32 Br2 N2 O4'
_chemical_formula_weight         740.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2023-07-12 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4361(3)
_cell_length_b                   17.0463(10)
_cell_length_c                   20.2087(9)
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      69.3870
_cell_measurement_theta_min      5.1690
_cell_volume                     3250.6(3)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8672
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.493
_diffrn_reflns_theta_max         67.493
_diffrn_reflns_theta_min         3.392
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0451
_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)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    0.698
_reflns_Friedel_fraction_max     0.698
_reflns_number_gt                4208
_reflns_number_total             5059
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02311g2.cif
_cod_data_source_block           2b-Br2
_cod_database_code               7131934
_shelx_shelxl_version_number     2018/1
_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   0.890
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br45 Br 0.59417(8) 0.43816(5) 0.49068(4) 0.0351(2) Uani 1 1 d . . . . .
Br46 Br 0.51255(7) 0.57784(5) 0.74916(4) 0.0358(2) Uani 1 1 d . . . . .
O41 O 0.6288(6) 1.1417(3) 0.6197(3) 0.0387(13) Uani 1 1 d . . . . .
O24 O 0.0854(6) 0.2258(3) 0.5751(3) 0.0379(13) Uani 1 1 d . . . . .
O43 O 0.5171(6) 0.9550(3) 0.2302(3) 0.0411(13) Uani 1 1 d . . . . .
O26 O 0.9845(6) 0.3250(4) 0.8124(3) 0.0468(14) Uani 1 1 d . . . . .
N11 N 0.5364(6) 0.4220(4) 0.6517(3) 0.0330(14) Uani 1 1 d . . . . .
N28 N 0.5652(6) 0.8542(4) 0.4910(3) 0.0332(14) Uani 1 1 d . . . . .
C9 C 0.5666(7) 0.5969(5) 0.5473(4) 0.0297(16) Uani 1 1 d . . . . .
C32 C 0.5233(7) 0.9227(5) 0.2922(4) 0.0318(16) Uani 1 1 d . . . . .
C3 C 0.5492(7) 0.6310(5) 0.6124(4) 0.0276(16) Uani 1 1 d . . . . .
C29 C 0.5524(8) 0.8699(5) 0.4210(4) 0.0316(18) Uani 1 1 d . . . . .
C22 C 0.1942(8) 0.3570(5) 0.5792(4) 0.0330(18) Uani 1 1 d . . . . .
H22 H 0.118974 0.379441 0.556228 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3064(8) 0.4036(5) 0.5988(4) 0.0351(18) Uani 1 1 d . . . . .
H23 H 0.305159 0.456715 0.588449 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5637(7) 0.7799(5) 0.5181(4) 0.0326(17) Uani 1 1 d . . . . .
C34 C 0.6686(8) 0.9016(5) 0.3880(4) 0.0350(19) Uani 1 1 d . . . . .
H34 H 0.756310 0.904669 0.408843 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5778(7) 0.6359(4) 0.4869(4) 0.0319(16) Uani 1 1 d . . . . .
H8 H 0.587376 0.603826 0.449937 0.038 Uiso 1 1 calc R U . . .
C33 C 0.6522(8) 0.9282(5) 0.3244(4) 0.0358(18) Uani 1 1 d . . . . .
H33 H 0.729180 0.950346 0.302486 0.043 Uiso 1 1 calc R U . . .
C31 C 0.4082(9) 0.8878(5) 0.3242(4) 0.0355(17) Uani 1 1 d . . . . .
H31 H 0.321922 0.881893 0.302502 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5389(7) 0.5683(5) 0.6571(4) 0.0340(17) Uani 1 1 d . . . . .
C1 C 0.5479(7) 0.4975(5) 0.6237(4) 0.0293(17) Uani 1 1 d . . . . .
C4 C 0.5421(7) 0.7103(5) 0.6282(4) 0.0323(18) Uani 1 1 d . . . . .
H4 H 0.531817 0.721040 0.673045 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5662(8) 0.5149(4) 0.5568(4) 0.0286(16) Uani 1 1 d . . . . .
C30 C 0.4246(8) 0.8619(5) 0.3893(4) 0.0372(18) Uani 1 1 d . . . . .
H30 H 0.348474 0.839063 0.411272 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6513(8) 0.3945(5) 0.6917(4) 0.0304(17) Uani 1 1 d . . . . .
C38 C 0.6200(8) 1.0674(5) 0.5934(4) 0.0339(17) Uani 1 1 d . . . . .
C18 C 0.4202(8) 0.3735(4) 0.6332(4) 0.0314(16) Uani 1 1 d . . . . .
C5 C 0.5477(8) 0.7752(5) 0.5883(4) 0.0352(19) Uani 1 1 d . . . . .
H5 H 0.540114 0.823136 0.610047 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5767(8) 0.7163(5) 0.4742(4) 0.0337(17) Uani 1 1 d . . . . .
H7 H 0.586044 0.729946 0.429832 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1918(8) 0.2774(5) 0.5931(4) 0.0314(17) Uani 1 1 d . . . . .
C35 C 0.5814(8) 0.9241(4) 0.5300(4) 0.0350(16) Uani 1 1 d . . . . .
C40 C 0.4711(8) 0.9788(5) 0.5320(4) 0.0351(18) Uani 1 1 d . . . . .
H40 H 0.384322 0.967273 0.512461 0.042 Uiso 1 1 calc R U . . .
C42 C 0.7611(8) 1.1635(5) 0.6497(5) 0.043(2) Uani 1 1 d . . . . .
H42A H 0.836229 1.157409 0.618089 0.064 Uiso 1 1 calc R U . . .
H42B H 0.778895 1.130464 0.687259 0.064 Uiso 1 1 calc R U . . .
H42C H 0.756547 1.217235 0.663770 0.064 Uiso 1 1 calc R U . . .
C15 C 0.8788(8) 0.3474(5) 0.7698(4) 0.039(2) Uani 1 1 d . . . . .
C17 C 0.7881(8) 0.4000(5) 0.6682(4) 0.0337(18) Uani 1 1 d . . . . .
H17 H 0.804124 0.419610 0.625894 0.040 Uiso 1 1 calc R U . . .
C20 C 0.3042(8) 0.2460(5) 0.6279(4) 0.0366(19) Uani 1 1 d . . . . .
H20 H 0.303448 0.192972 0.638576 0.044 Uiso 1 1 calc R U . . .
C36 C 0.7090(8) 0.9417(5) 0.5610(4) 0.0370(18) Uani 1 1 d . . . . .
H36 H 0.782171 0.905173 0.560511 0.044 Uiso 1 1 calc R U . . .
C25 C -0.0153(9) 0.2557(5) 0.5287(4) 0.042(2) Uani 1 1 d . . . . .
H25A H 0.033775 0.279543 0.492278 0.062 Uiso 1 1 calc R U . . .
H25B H -0.074083 0.294044 0.549999 0.062 Uiso 1 1 calc R U . . .
H25C H -0.073155 0.213435 0.512659 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9025(9) 0.3768(5) 0.7069(4) 0.0366(18) Uani 1 1 d . . . . .
H16 H 0.994354 0.380936 0.690561 0.044 Uiso 1 1 calc R U . . .
C39 C 0.4912(9) 1.0497(5) 0.5631(4) 0.0383(18) Uani 1 1 d . . . . .
H39 H 0.418073 1.086297 0.563909 0.046 Uiso 1 1 calc R U . . .
C19 C 0.4192(8) 0.2923(5) 0.6474(4) 0.0338(17) Uani 1 1 d . . . . .
H19 H 0.494989 0.269642 0.669776 0.041 Uiso 1 1 calc R U . . .
C37 C 0.7284(8) 1.0129(5) 0.5928(4) 0.0351(19) Uani 1 1 d . . . . .
H37 H 0.813999 1.023952 0.613544 0.042 Uiso 1 1 calc R U . . .
C44 C 0.3855(9) 0.9523(6) 0.1959(4) 0.045(2) Uani 1 1 d . . . . .
H44A H 0.394528 0.979207 0.154379 0.068 Uiso 1 1 calc R U . . .
H44B H 0.313584 0.977257 0.222103 0.068 Uiso 1 1 calc R U . . .
H44C H 0.359544 0.898646 0.188041 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6281(8) 0.3655(5) 0.7553(4) 0.0399(18) Uani 1 1 d . . . . .
H13 H 0.536429 0.361558 0.771794 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7421(9) 0.3425(6) 0.7937(4) 0.046(2) Uani 1 1 d . . . . .
H14 H 0.726385 0.323469 0.836155 0.055 Uiso 1 1 calc R U . . .
C27 C 1.1249(9) 0.3285(7) 0.7884(5) 0.059(3) Uani 1 1 d . . . . .
H27A H 1.132037 0.298705 0.748261 0.089 Uiso 1 1 calc R U . . .
H27B H 1.188181 0.307014 0.820934 0.089 Uiso 1 1 calc R U . . .
H27C H 1.149925 0.382106 0.779866 0.089 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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C38 O41 C42 117.0(6) . . ?
C21 O24 C25 115.4(6) . . ?
C32 O43 C44 118.1(6) . . ?
C15 O26 C27 117.1(7) . . ?
C1 N11 C18 118.9(6) . . ?
C1 N11 C12 117.8(6) . . ?
C18 N11 C12 122.8(6) . . ?
C6 N28 C35 123.1(6) . . ?
C6 N28 C29 123.9(6) . . ?
C35 N28 C29 113.0(6) . . ?
C8 C9 C10 126.3(7) . . ?
C8 C9 C3 127.8(7) . . ?
C10 C9 C3 105.9(7) . . ?
O43 C32 C33 116.1(7) . . ?
O43 C32 C31 124.2(7) . . ?
C33 C32 C31 119.7(7) . . ?
C4 C3 C2 126.2(7) . . ?
C4 C3 C9 127.1(7) . . ?
C2 C3 C9 106.7(7) . . ?
C30 C29 C34 120.5(7) . . ?
C30 C29 N28 120.8(7) . . ?
C34 C29 N28 118.3(7) . . ?
C23 C22 C21 121.1(7) . . ?
C18 C23 C22 121.9(8) . . ?
N28 C6 C7 117.2(7) . . ?
N28 C6 C5 116.5(7) . . ?
C7 C6 C5 126.3(7) . . ?
C33 C34 C29 119.2(7) . . ?
C9 C8 C7 129.0(7) . . ?
C34 C33 C32 121.1(7) . . ?
C30 C31 C32 119.0(7) . . ?
C1 C2 C3 110.3(7) . . ?
C1 C2 Br46 124.4(6) . . ?
C3 C2 Br46 125.4(6) . . ?
C2 C1 C10 107.2(7) . . ?
C2 C1 N11 126.5(7) . . ?
C10 C1 N11 126.3(7) . . ?
C5 C4 C3 130.5(8) . . ?
C1 C10 C9 110.0(7) . . ?
C1 C10 Br45 123.8(6) . . ?
C9 C10 Br45 126.1(6) . . ?
C29 C30 C31 120.4(8) . . ?
C17 C12 C13 119.2(7) . . ?
C17 C12 N11 119.5(7) . . ?
C13 C12 N11 121.2(6) . . ?
O41 C38 C37 125.3(7) . . ?
O41 C38 C39 114.9(7) . . ?
C37 C38 C39 119.8(8) . . ?
C23 C18 C19 117.5(7) . . ?
C23 C18 N11 121.1(7) . . ?
C19 C18 N11 121.3(7) . . ?
C4 C5 C6 129.3(8) . . ?
C8 C7 C6 129.9(7) . . ?
C20 C21 O24 116.4(7) . . ?
C20 C21 C22 118.1(7) . . ?
O24 C21 C22 125.5(7) . . ?
C36 C35 C40 119.1(7) . . ?
C36 C35 N28 121.2(7) . . ?
C40 C35 N28 119.4(7) . . ?
C39 C40 C35 119.8(7) . . ?
O26 C15 C14 116.3(7) . . ?
O26 C15 C16 124.1(7) . . ?
C14 C15 C16 119.6(8) . . ?
C12 C17 C16 120.9(8) . . ?
C21 C20 C19 121.4(8) . . ?
C37 C36 C35 120.9(8) . . ?
C15 C16 C17 119.6(8) . . ?
C40 C39 C38 120.7(8) . . ?
C20 C19 C18 120.0(7) . . ?
C38 C37 C36 119.7(7) . . ?
C14 C13 C12 119.7(7) . . ?
C15 C14 C13 120.9(8) . . ?
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
Br45 C10 1.888(7) . ?
Br46 C2 1.884(8) . ?
O41 C38 1.376(10) . ?
O41 C42 1.436(10) . ?
O24 C21 1.383(9) . ?
O24 C25 1.428(10) . ?
O43 C32 1.369(9) . ?
O43 C44 1.423(9) . ?
O26 C15 1.372(9) . ?
O26 C27 1.412(11) . ?
N11 C1 1.411(10) . ?
N11 C18 1.423(9) . ?
N11 C12 1.431(9) . ?
N28 C6 1.379(9) . ?
N28 C35 1.436(10) . ?
N28 C29 1.447(10) . ?
C9 C8 1.393(11) . ?
C9 C10 1.411(10) . ?
C9 C3 1.449(10) . ?
C32 C33 1.383(10) . ?
C32 C31 1.398(11) . ?
C3 C4 1.390(11) . ?
C3 C2 1.403(11) . ?
C29 C30 1.373(11) . ?
C29 C34 1.392(11) . ?
C22 C23 1.381(11) . ?
C22 C21 1.385(11) . ?
C23 C18 1.378(11) . ?
C6 C7 1.407(11) . ?
C6 C5 1.429(11) . ?
C34 C33 1.373(11) . ?
C8 C7 1.394(10) . ?
C31 C30 1.395(11) . ?
C2 C1 1.386(11) . ?
C1 C10 1.395(10) . ?
C4 C5 1.370(12) . ?
C12 C17 1.379(11) . ?
C12 C13 1.394(11) . ?
C38 C37 1.381(11) . ?
C38 C39 1.394(11) . ?
C18 C19 1.414(11) . ?
C21 C20 1.381(11) . ?
C35 C36 1.391(11) . ?
C35 C40 1.398(11) . ?
C40 C39 1.375(11) . ?
C15 C14 1.380(12) . ?
C15 C16 1.385(11) . ?
C17 C16 1.390(11) . ?
C20 C19 1.398(11) . ?
C36 C37 1.385(11) . ?
C13 C14 1.382(11) . ?
