#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003521.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003521
loop_
_publ_author_name
'Tamura, H.'
'Oshima, T.'
'Matsubayashi, G.'
'Nagai, T.'
_publ_contact_author
;
    Hatsue Tamura
    Department of Applied Chemistry
    Faculty of Engineering
    Osaka University
    Machikaneyama 1-16, Toyonaka, Osaka 560
    Japan
;
_publ_section_title
;
 Two Conformational Isomers of
 2-Bromo-2,3-dihydro-2,3-(bibenzyl-2,2'-diyl)methano-1,4-naphthoquinone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1148
_journal_page_last               1152
_journal_paper_doi               10.1107/S0108270194013806
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C25 H17 Br O2'
_chemical_formula_sum            'C25 H17 Br O2'
_chemical_formula_weight         429.31
_chemical_melting_point          .464E-305
_chemical_name_systematic
;
2-bromo-2,3-dihydro-2,3-(bibenzyl-2,2'-diyl)methano-1,4-naphthoquinone
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 91.29(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4.00
_cell_length_a                   15.037(3)
_cell_length_b                   9.913(1)
_cell_length_c                   12.547(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15.00
_cell_measurement_theta_min      14.83
_cell_volume                     1869.8(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1988)
;
_computing_data_reduction
'PROCESS TEXSAN (Molecular Structure Corporation, 1992)'
_computing_publication_material  'FINISH TEXSAN'
_computing_structure_refinement  'LS TEXSAN'
_computing_structure_solution
'PROCESS TEXSAN (Molecular Structure Corporation, 1992)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Rigaku AFC5R diffractometer'
_diffrn_measurement_method       '\q/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  6.33
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3002
_diffrn_reflns_theta_max         30.064
_diffrn_reflns_theta_min         1.620
_diffrn_standards_decay_%        -0.57
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.19
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   'empirical, \y scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      1.53
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.387
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.35
_refine_ls_hydrogen_treatment
'refall except H6, H7, H8, H9, which were not refined'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.409
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.035
_reflns_number_observed          1767
_reflns_number_total             2902
_cod_data_source_file            as1150.cif
_cod_data_source_block           II
_cod_depositor_comments
;

    Replacing duplicated symmetry operators
        '   +x,   +y,   +z'
        '   +x,   -y,1/2+z'
    with
        'x+1/2,-y+1/2,z+1/2'
        'x+1/2,y+1/2,z'
    in _symmetry_equiv_pos_as_xyz loop because:

    a) Symmetry operators now constitute full set of 'C 1 c 1' symmetry
       space group symmetry operators;

    b) Crystal voids (up to 4.19 angstroms in diameter) have disappeared
       now.

    Andrius Merkys
    2014-07-15

;
_cod_original_cell_volume        1869.7(5)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2003521
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   +x,   -y,1/2+z'
x+1/2,-y+1/2,z+1/2
x+1/2,y+1/2,z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
Br(1) 0.0505(3) 0.0063(4) 0.0022(2) 0.0653(4) -0.0098(4) 0.0371(2)
O(1) 0.147(5) -0.028(3) -0.015(3) 0.077(3) 0.021(2) 0.040(3)
O(2) 0.060(3) -0.002(2) -0.018(2) 0.063(3) 0.006(2) 0.046(2)
C(1) 0.054(3) -0.007(3) -0.001(3) 0.048(3) 0.012(2) 0.040(3)
C(2) 0.041(3) -0.002(2) -0.003(2) 0.044(3) 0.002(2) 0.028(2)
C(3) 0.034(3) 0.005(2) -0.001(2) 0.035(3) 0.003(2) 0.035(2)
C(4) 0.034(3) 0.003(2) 0.000(2) 0.048(3) -0.001(2) 0.039(3)
C(5) 0.037(3) -0.005(2) 0.007(2) 0.046(3) -0.002(2) 0.042(3)
C(6) 0.035(3) 0.000(2) 0.009(2) 0.051(3) 0.010(2) 0.044(3)
C(7) 0.056(4) 0.002(3) 0.010(3) 0.057(4) 0.018(3) 0.061(4)
C(8) 0.101(6) -0.002(4) 0.035(5) 0.045(4) 0.017(4) 0.092(6)
C(9) 0.111(7) -0.025(4) 0.035(5) 0.045(4) -0.014(4) 0.087(6)
C(10) 0.063(4) -0.013(3) 0.012(3) 0.061(4) -0.007(3) 0.059(4)
C(11) 0.035(2) 0.003(2) -0.001(2) 0.038(3) 0.004(2) 0.031(2)
C(12) 0.042(3) -0.003(2) 0.003(2) 0.035(3) -0.003(2) 0.033(2)
C(13) 0.042(3) -0.007(3) 0.002(2) 0.057(4) -0.011(3) 0.048(3)
C(14) 0.110(6) 0.024(5) -0.038(4) 0.080(5) -0.007(4) 0.051(4)
C(15) 0.111(6) -0.012(5) -0.038(5) 0.070(5) 0.023(4) 0.065(5)
C(16) 0.044(3) -0.001(3) -0.008(3) 0.041(3) 0.009(3) 0.062(4)
C(17) 0.031(3) 0.004(2) 0.003(2) 0.034(3) 0.011(2) 0.045(3)
C(18) 0.040(3) 0.003(2) 0.003(2) 0.047(3) 0.003(2) 0.042(3)
C(19) 0.058(4) 0.001(3) 0.021(4) 0.050(4) -0.010(3) 0.071(4)
C(20) 0.045(4) 0.008(3) 0.018(4) 0.043(4) -0.006(4) 0.113(6)
C(21) 0.039(3) 0.004(3) -0.014(4) 0.040(3) 0.012(4) 0.113(6)
C(22) 0.042(4) -0.012(3) 0.006(3) 0.073(5) -0.018(4) 0.069(5)
C(23) 0.077(5) -0.030(4) 0.025(4) 0.060(5) -0.021(4) 0.083(6)
C(24) 0.105(6) -0.006(4) 0.024(4) 0.037(4) 0.008(3) 0.060(4)
C(25) 0.061(4) 0.000(3) 0.001(3) 0.043(3) -0.003(3) 0.042(3)
loop_
_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_calc_attached_atom
Br(1) 0.0 0.01225(6) 0.0 0.0509(1) Uij ? ?
O(1) -0.0399(4) 0.3089(5) -0.0416(4) 0.088(2) Uij ? ?
O(2) 0.0668(3) 0.2149(4) 0.3616(3) 0.057(1) Uij ? ?
C(1) -0.0267(4) 0.2888(6) 0.0519(4) 0.048(2) Uij ? ?
C(2) -0.0339(3) 0.1505(5) 0.0980(4) 0.038(1) Uij ? ?
C(3) -0.0104(3) 0.1258(5) 0.2133(4) 0.035(1) Uij ? ?
C(4) 0.0305(3) 0.2376(5) 0.2757(4) 0.040(1) Uij ? ?
C(5) 0.0274(4) 0.3768(5) 0.2296(4) 0.042(1) Uij ? ?
C(6) -0.0039(3) 0.3996(6) 0.1260(4) 0.043(1) Uij ? ?
C(7) -0.0066(4) 0.5325(7) 0.0870(6) 0.058(2) Uij ? ?
C(8) 0.0216(6) 0.6358(8) 0.1499(7) 0.079(3) Uij ? ?
C(9) 0.0544(6) 0.6123(7) 0.2500(7) 0.081(3) Uij ? ?
C(10) 0.0575(5) 0.4842(7) 0.2913(6) 0.061(2) Uij ? ?
C(11) -0.1077(3) 0.1237(5) 0.1765(4) 0.035(1) Uij ? ?
C(12) -0.1561(4) -0.0084(5) 0.1660(4) 0.037(1) Uij ? ?
C(13) -0.2219(4) -0.0206(6) 0.0862(4) 0.049(2) Uij ? ?
C(14) -0.2408(6) 0.0897(8) 0.0058(6) 0.081(3) Uij ? ?
C(15) -0.2508(6) 0.2317(7) 0.0331(6) 0.083(3) Uij ? ?
C(16) -0.2368(4) 0.2823(6) 0.1450(5) 0.049(2) Uij ? ?
C(17) -0.1694(3) 0.2341(5) 0.2130(4) 0.037(1) Uij ? ?
C(18) -0.1649(4) 0.2779(6) 0.3179(4) 0.043(1) Uij ? ?
C(19) -0.2230(5) 0.3742(6) 0.3535(6) 0.059(2) Uij ? ?
C(20) -0.2864(5) 0.4280(7) 0.2871(7) 0.066(2) Uij ? ?
C(21) -0.2939(4) 0.3810(6) 0.1849(7) 0.064(2) Uij ? ?
C(22) -0.2674(4) -0.1419(8) 0.0787(6) 0.061(2) Uij ? ?
C(23) -0.2519(6) -0.2452(8) 0.1455(7) 0.073(3) Uij ? ?
C(24) -0.1875(6) -0.2331(6) 0.2249(6) 0.067(2) Uij ? ?
C(25) -0.1400(4) -0.1147(6) 0.2359(4) 0.049(2) Uij ? ?
H(1) 0.016(3) 0.037(4) 0.229(4) 0.03(1) Uiso ? ?
H(2) -0.033(3) 0.544(5) 0.017(5) 0.04(1) Uiso ? ?
H(3) 0.027(4) 0.719(6) 0.130(5) 0.05(1) Uiso ? ?
H(4) 0.076(4) 0.679(6) 0.298(5) 0.06(1) Uiso ? ?
H(5) 0.072(4) 0.465(5) 0.360(5) 0.05(1) Uiso ? ?
H(6) -0.1919 0.0875 -0.0417 0.101 Uiso calc C14
H(7) -0.2933 0.0646 -0.0312 0.101 Uiso calc C14
H(8) -0.2119 0.2811 -0.0098 0.101 Uiso calc C15
H(9) -0.3111 0.2544 0.0141 0.101 Uiso calc C15
H(10) -0.120(3) 0.241(5) 0.361(4) 0.03(1) Uiso ? ?
H(11) -0.221(5) 0.400(7) 0.426(6) 0.06(2) Uiso ? ?
H(12) -0.329(5) 0.486(6) 0.311(6) 0.05(2) Uiso ? ?
H(13) -0.338(4) 0.407(6) 0.140(4) 0.05(1) Uiso ? ?
H(14) -0.307(5) -0.146(7) 0.023(6) 0.08(2) Uiso ? ?
H(15) -0.286(5) -0.307(7) 0.136(6) 0.07(2) Uiso ? ?
H(16) -0.183(4) -0.305(7) 0.260(5) 0.07(2) Uiso ? ?
H(17) -0.096(4) -0.104(6) 0.291(5) 0.05(1) Uiso ? ?
loop_
_atom_type_symbol
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C IntTabIV_Table_2.2A 0.003 0.002
H IntTabIV_Table_2.2A 0.000 0.000
O IntTabIV_Table_2.2A 0.011 0.006
Br IntTabIV_Table_2.2A -0.290 2.459
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 2 -2
-1 -1 -3
3 1 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) C(1) C(2) 121.3(6) yes
O(1) C(1) C(6) 121.5(5) yes
C(2) C(1) C(6) 117.2(5) yes
Br(1) C(2) C(1) 112.6(4) yes
Br(1) C(2) C(3) 116.2(4) yes
Br(1) C(2) C(11) 119.9(3) yes
C(1) C(2) C(3) 120.4(4) yes
C(1) C(2) C(11) 118.1(5) yes
C(3) C(2) C(11) 60.5(3) yes
C(2) C(3) C(4) 118.2(4) yes
C(2) C(3) C(11) 60.5(3) yes
C(2) C(3) H(1) 114(2) no
C(4) C(3) C(11) 123.7(4) yes
C(4) C(3) H(1) 113(2) no
C(11) C(3) H(1) 115(2) no
O(2) C(4) C(3) 120.1(5) yes
O(2) C(4) C(5) 121.4(5) yes
C(3) C(4) C(5) 118.5(4) yes
C(4) C(5) C(6) 121.2(5) yes
C(6) C(5) C(10) 119.8(5) no
C(1) C(6) C(5) 122.5(5) yes
C(5) C(6) C(7) 118.9(6) no
C(6) C(7) C(8) 120.0(7) no
C(6) C(7) H(2) 115(3) no
C(8) C(7) H(2) 123(3) no
C(7) C(8) C(9) 120.7(7) no
C(7) C(8) H(3) 125(3) no
C(9) C(8) H(3) 113(3) no
C(8) C(9) C(10) 121.1(7) no
C(8) C(9) H(4) 125(3) no
C(10) C(9) H(4) 113(3) no
C(5) C(10) C(9) 119.5(7) no
C(5) C(10) H(5) 115(3) no
C(9) C(10) H(5) 124(3) no
C(2) C(11) C(3) 59.0(3) yes
C(2) C(11) C(12) 117.0(4) yes
C(2) C(11) C(17) 122.0(4) yes
C(3) C(11) C(12) 119.9(4) yes
C(3) C(11) C(17) 119.3(4) yes
C(12) C(11) C(17) 111.0(4) yes
C(11) C(12) C(13) 118.2(5) yes
C(13) C(12) C(25) 119.8(5) no
C(12) C(13) C(14) 122.3(5) yes
C(12) C(13) C(22) 117.7(6) no
C(13) C(14) C(15) 124.1(6) yes
C(14) C(15) C(16) 122.0(5) yes
C(15) C(16) C(17) 122.9(5) yes
C(17) C(16) C(21) 117.6(6) no
C(11) C(17) C(16) 120.3(5) yes
C(16) C(17) C(18) 119.6(5) no
C(17) C(18) C(19) 120.5(6) no
C(17) C(18) H(10) 116(2) no
C(19) C(18) H(10) 122(3) no
C(18) C(19) C(20) 120.9(7) no
C(18) C(19) H(11) 119(4) no
C(20) C(19) H(11) 119(4) no
C(19) C(20) C(21) 118.9(6) no
C(19) C(20) H(12) 121(4) no
C(21) C(20) H(12) 118(4) no
C(16) C(21) C(20) 122.3(6) no
C(16) C(21) H(13) 115(3) no
C(20) C(21) H(13) 122(3) no
C(13) C(22) C(23) 122.8(7) no
C(13) C(22) H(14) 114(4) no
C(23) C(22) H(14) 123(4) no
C(22) C(23) C(24) 119.7(7) no
C(22) C(23) H(15) 112(5) no
C(24) C(23) H(15) 127(5) no
C(23) C(24) C(25) 119.9(7) no
C(23) C(24) H(16) 110(4) no
C(25) C(24) H(16) 129(4) no
C(12) C(25) C(24) 120.1(6) no
C(12) C(25) H(17) 118(3) no
C(24) C(25) H(17) 121(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(1) C(2) 1.918(5) yes
O(1) C(1) 1.202(6) yes
O(2) C(4) 1.217(6) yes
C(1) C(2) 1.493(7) yes
C(1) C(6) 1.474(8) yes
C(2) C(3) 1.501(7) yes
C(2) C(11) 1.524(7) yes
C(3) C(4) 1.483(7) yes
C(3) C(11) 1.525(7) yes
C(3) H(1) 0.99(5) no
C(4) C(5) 1.497(7) yes
C(5) C(6) 1.391(8) no
C(5) C(10) 1.386(8) no
C(6) C(7) 1.406(9) no
C(7) C(8) 1.355(10) no
C(7) H(2) 0.96(6) no
C(8) C(9) 1.359(12) no
C(8) H(3) 0.87(6) no
C(9) C(10) 1.372(10) no
C(9) H(4) 0.95(6) no
C(10) H(5) 0.90(6) no
C(11) C(12) 1.502(7) yes
C(11) C(17) 1.513(7) yes
C(12) C(13) 1.398(8) no
C(12) C(25) 1.388(8) no
C(13) C(14) 1.511(10) yes
C(13) C(22) 1.384(9) no
C(14) C(15) 1.458(11) yes
C(15) C(16) 1.501(9) yes
C(16) C(17) 1.394(7) no
C(16) C(21) 1.402(9) no
C(17) C(18) 1.386(7) no
C(18) C(19) 1.375(8) no
C(18) H(10) 0.93(5) no
C(19) C(20) 1.361(10) no
C(19) H(11) 0.94(7) no
C(20) C(21) 1.366(10) no
C(20) H(12) 0.92(7) no
C(21) H(13) 0.89(6) no
C(22) C(23) 1.341(11) no
C(22) H(14) 0.91(7) no
C(23) C(24) 1.378(11) no
C(23) H(15) 0.81(7) no
C(24) C(25) 1.380(9) no
C(24) H(16) 0.84(7) no
C(25) H(17) 0.96(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139054310