#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506022.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_1506022
loop_
_publ_author_name
'Imai, Yoshitane'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Kuroda, Reiko'
_publ_section_title
;
 Visualization of molecular recognition: a novel system based on
 charge-transfer complexes composed of 1,1'-bi-2-naphthol derivatives and
 p-benzoquinone.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2941
_journal_page_last               2944
_journal_paper_doi               10.1021/ol060862q
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C33 H22 Br2 O3'
_chemical_formula_weight         626.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.553(5)
_cell_angle_beta                 83.598(2)
_cell_angle_gamma                78.989(7)
_cell_formula_units_Z            2
_cell_length_a                   9.5126(6)
_cell_length_b                   9.8661(14)
_cell_length_c                   14.6056(12)
_cell_measurement_reflns_used    7473
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.19
_cell_volume                     1328.9(2)
_computing_cell_refinement       RIGAKU-TEXSAN
_computing_data_collection       RIGAKU-TEXSAN
_computing_data_reduction        RIGAKU-TEXSAN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9489
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.084
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_correction_T_min  0.4116
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   RIGAKU-TEXSAN
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0607P)²+1.0878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                4971
_reflns_number_total             5961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060862qsi20060410_104601.cif
_cod_data_source_block           imai62_3
_cod_database_code               1506022
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7257(3) 0.2957(3) 0.86373(18) 0.0153(5) Uani 1 1 d .
C2 C 0.6116(3) 0.3240(3) 0.93029(19) 0.0157(5) Uani 1 1 d .
C3 C 0.6301(3) 0.2935(3) 1.02590(19) 0.0172(5) Uani 1 1 d .
H3 H 0.5513 0.3098 1.0693 0.021 Uiso 1 1 calc R
C4 C 0.7627(3) 0.2403(3) 1.05469(19) 0.0170(5) Uani 1 1 d .
H4 H 0.7737 0.2219 1.1178 0.020 Uiso 1 1 calc R
C5 C 1.0240(3) 0.1645(3) 1.01961(19) 0.0162(5) Uani 1 1 d .
H5 H 1.0370 0.1472 1.0825 0.019 Uiso 1 1 calc R
C6 C 1.1388(3) 0.1436(3) 0.9555(2) 0.0170(5) Uani 1 1 d .
C7 C 1.1225(3) 0.1625(3) 0.8599(2) 0.0181(5) Uani 1 1 d .
H7 H 1.2022 0.1439 0.8175 0.022 Uiso 1 1 calc R
C8 C 0.9881(3) 0.2088(3) 0.82978(19) 0.0172(5) Uani 1 1 d .
H8 H 0.9775 0.2209 0.7666 0.021 Uiso 1 1 calc R
C9 C 0.8652(3) 0.2384(3) 0.89356(19) 0.0146(5) Uani 1 1 d .
C10 C 0.8840(3) 0.2127(3) 0.98999(18) 0.0149(5) Uani 1 1 d .
O2 O 0.4814(2) 0.3836(2) 0.90078(14) 0.0205(4) Uani 1 1 d .
H2 H 0.4233 0.3990 0.9457 0.031 Uiso 1 1 calc R
Br6 Br 1.32647(3) 0.08783(3) 0.99455(2) 0.02265(10) Uani 1 1 d .
C11 C 0.7045(3) 0.3277(3) 0.76323(19) 0.0153(5) Uani 1 1 d .
C12 C 0.6948(3) 0.4620(3) 0.72072(19) 0.0169(5) Uani 1 1 d .
C13 C 0.6798(3) 0.4928(3) 0.6244(2) 0.0201(6) Uani 1 1 d .
H13 H 0.6746 0.5838 0.5969 0.024 Uiso 1 1 calc R
C14 C 0.6729(3) 0.3909(3) 0.5720(2) 0.0203(6) Uani 1 1 d .
H14 H 0.6633 0.4127 0.5088 0.024 Uiso 1 1 calc R
C15 C 0.6737(3) 0.1450(3) 0.5579(2) 0.0206(6) Uani 1 1 d .
H15 H 0.6656 0.1649 0.4946 0.025 Uiso 1 1 calc R
C16 C 0.6795(3) 0.0123(3) 0.5995(2) 0.0220(6) Uani 1 1 d .
C17 C 0.6910(3) -0.0217(3) 0.6948(2) 0.0232(6) Uani 1 1 d .
H17 H 0.6935 -0.1128 0.7216 0.028 Uiso 1 1 calc R
C18 C 0.6984(3) 0.0807(3) 0.7484(2) 0.0203(6) Uani 1 1 d .
H18 H 0.7059 0.0582 0.8117 0.024 Uiso 1 1 calc R
C19 C 0.6948(3) 0.2201(3) 0.70892(19) 0.0159(5) Uani 1 1 d .
C20 C 0.6802(3) 0.2522(3) 0.61216(19) 0.0174(5) Uani 1 1 d .
O12 O 0.6995(2) 0.5735(2) 0.76544(14) 0.0223(4) Uani 1 1 d .
H12 H 0.7038 0.5487 0.8210 0.034 Uiso 1 1 calc R
Br16 Br 0.67448(4) -0.13032(3) 0.52479(2) 0.03251(11) Uani 1 1 d .
C21 C 0.8567(3) 0.5425(3) 0.97465(18) 0.0147(5) Uani 1 1 d .
C22 C 0.8864(3) 0.5188(3) 1.07265(19) 0.0165(5) Uani 1 1 d .
H22 H 0.8106 0.5323 1.1186 0.020 Uiso 1 1 calc R
C23 C 1.0212(3) 0.4779(3) 1.09668(18) 0.0156(5) Uani 1 1 d .
H23 H 1.0379 0.4624 1.1590 0.019 Uiso 1 1 calc R
O21 O 0.7326(2) 0.5777(2) 0.95300(13) 0.0176(4) Uani 1 1 d .
C31 C 0.9270(4) 0.1751(6) 1.3506(3) 0.0576(14) Uani 1 1 d .
H31 H 1.0175 0.1354 1.3693 0.069 Uiso 1 1 calc R
C32 C 0.8423(5) 0.0926(5) 1.3264(3) 0.0563(13) Uani 1 1 d .
H32 H 0.8753 -0.0026 1.3279 0.068 Uiso 1 1 calc R
C33 C 0.7049(5) 0.1498(5) 1.2990(2) 0.0484(11) Uani 1 1 d .
H33 H 0.6458 0.0919 1.2847 0.058 Uiso 1 1 calc R
C34 C 0.6574(4) 0.2895(4) 1.2931(2) 0.0366(8) Uani 1 1 d .
H34 H 0.5671 0.3258 1.2729 0.044 Uiso 1 1 calc R
C35 C 0.6940(4) 0.5256(4) 1.3147(2) 0.0355(8) Uani 1 1 d .
H35 H 0.6049 0.5648 1.2934 0.043 Uiso 1 1 calc R
C36 C 0.7757(5) 0.6079(5) 1.3429(3) 0.0482(10) Uani 1 1 d .
H36 H 0.7425 0.7031 1.3416 0.058 Uiso 1 1 calc R
C37 C 0.9135(5) 0.5478(6) 1.3746(3) 0.0575(13) Uani 1 1 d .
H37 H 0.9694 0.6042 1.3943 0.069 Uiso 1 1 calc R
C38 C 0.9626(4) 0.4104(6) 1.3762(3) 0.0577(14) Uani 1 1 d .
H38 H 1.0528 0.3734 1.3963 0.069 Uiso 1 1 calc R
C39 C 0.8803(4) 0.3217(5) 1.3482(3) 0.0436(10) Uani 1 1 d .
C40 C 0.7424(4) 0.3812(4) 1.3172(2) 0.0351(8) Uani 1 1 d .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_3
C2 C1 C9 118.7(2) .
C2 C1 C11 120.7(2) .
C9 C1 C11 120.6(2) .
O2 C2 C1 117.8(2) .
O2 C2 C3 120.9(2) .
C1 C2 C3 121.2(2) .
C4 C3 C2 120.3(3) .
C3 C4 C10 121.0(2) .
C6 C5 C10 119.6(2) .
C5 C6 C7 121.8(2) .
C5 C6 Br6 119.8(2) .
C7 C6 Br6 118.4(2) .
C8 C7 C6 119.5(3) .
C7 C8 C9 121.1(2) .
C8 C9 C10 118.1(2) .
C8 C9 C1 122.1(2) .
C10 C9 C1 119.7(2) .
C4 C10 C5 121.2(2) .
C4 C10 C9 119.0(2) .
C5 C10 C9 119.7(2) .
C12 C11 C19 118.7(2) .
C12 C11 C1 120.5(2) .
C19 C11 C1 120.7(2) .
O12 C12 C11 124.2(2) .
O12 C12 C13 114.9(2) .
C11 C12 C13 121.0(3) .
C14 C13 C12 120.7(3) .
C13 C14 C20 120.7(3) .
C16 C15 C20 119.4(3) .
C15 C16 C17 122.0(3) .
C15 C16 Br16 118.6(2) .
C17 C16 Br16 119.4(2) .
C18 C17 C16 119.4(3) .
C17 C18 C19 121.2(3) .
C18 C19 C20 118.3(2) .
C18 C19 C11 122.0(3) .
C20 C19 C11 119.8(3) .
C14 C20 C15 121.1(3) .
C14 C20 C19 119.1(3) .
C15 C20 C19 119.8(3) .
O21 C21 C22 120.6(2) .
O21 C21 C23 120.9(2) 2_767
C22 C21 C23 118.5(2) 2_767
C23 C22 C21 120.8(2) .
C22 C23 C21 120.7(2) 2_767
C32 C31 C39 121.3(4) .
C31 C32 C33 120.3(5) .
C34 C33 C32 120.4(5) .
C33 C34 C40 121.6(4) .
C36 C35 C40 120.6(4) .
C35 C36 C37 119.7(5) .
C38 C37 C36 120.6(4) .
C37 C38 C39 121.3(4) .
C38 C39 C31 123.2(4) .
C38 C39 C40 118.2(4) .
C31 C39 C40 118.6(4) .
C35 C40 C34 122.7(3) .
C35 C40 C39 119.6(4) .
C34 C40 C39 117.7(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(4) .
C1 C9 1.431(4) .
C1 C11 1.489(4) .
C2 O2 1.356(3) .
C2 C3 1.413(4) .
C3 C4 1.360(4) .
C4 C10 1.415(4) .
C5 C6 1.358(4) .
C5 C10 1.421(4) .
C6 C7 1.406(4) .
C6 Br6 1.894(3) .
C7 C8 1.374(4) .
C8 C9 1.420(4) .
C9 C10 1.423(4) .
C11 C12 1.379(4) .
C11 C19 1.427(4) .
C12 O12 1.360(3) .
C12 C13 1.417(4) .
C13 C14 1.355(4) .
C14 C20 1.410(4) .
C15 C16 1.364(4) .
C15 C20 1.414(4) .
C16 C17 1.401(4) .
C16 Br16 1.900(3) .
C17 C18 1.371(4) .
C18 C19 1.416(4) .
C19 C20 1.424(4) .
C21 O21 1.230(3) .
C21 C22 1.470(4) .
C21 C23 1.473(4) 2_767
C22 C23 1.341(4) .
C23 C21 1.473(4) 2_767
C31 C32 1.350(7) .
C31 C39 1.427(7) .
C32 C33 1.401(6) .
C33 C34 1.360(6) .
C34 C40 1.423(6) .
C35 C36 1.354(6) .
C35 C40 1.408(6) .
C36 C37 1.433(6) .
C37 C38 1.344(7) .
C38 C39 1.404(7) .
C39 C40 1.428(5) .
