#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506023.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_1506023
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            'C37 H24 Br2 O3'
_chemical_formula_weight         676.38
_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                84.1020(10)
_cell_angle_beta                 87.9970(10)
_cell_angle_gamma                76.1560(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6793(6)
_cell_length_b                   10.6282(6)
_cell_length_c                   14.0039(8)
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.35
_cell_volume                     1391.30(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'ω scans'
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12696
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.952
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0408P)²+0.6934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                5937
_reflns_number_total             6502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060862qsi20060410_104601.cif
_cod_data_source_block           imai62_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506023
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 0.83353(17) 0.57186(16) 0.79243(11) 0.0116(3) Uani 1 1 d .
C2 C 0.94762(17) 0.50656(16) 0.84959(12) 0.0137(3) Uani 1 1 d .
C3 C 0.95420(17) 0.37973(17) 0.89547(12) 0.0146(3) Uani 1 1 d .
H3 H 1.0329 0.3368 0.9321 0.017 Uiso 1 1 calc R
C4 C 0.84558(18) 0.32059(17) 0.88604(12) 0.0149(3) Uani 1 1 d .
H4 H 0.8505 0.2380 0.9171 0.018 Uiso 1 1 calc R
C5 C 0.60925(18) 0.32512(16) 0.82178(12) 0.0151(3) Uani 1 1 d .
H5 H 0.6107 0.2438 0.8540 0.018 Uiso 1 1 calc R
C6 C 0.49492(18) 0.38947(17) 0.76643(12) 0.0150(3) Uani 1 1 d .
C7 C 0.49159(18) 0.51071(17) 0.71416(12) 0.0153(3) Uani 1 1 d .
H7 H 0.4152 0.5507 0.6746 0.018 Uiso 1 1 calc R
C8 C 0.60163(17) 0.56919(16) 0.72204(12) 0.0143(3) Uani 1 1 d .
H8 H 0.5984 0.6499 0.6883 0.017 Uiso 1 1 calc R
C9 C 0.72081(17) 0.50901(16) 0.78085(11) 0.0120(3) Uani 1 1 d .
C10 C 0.72507(17) 0.38340(16) 0.82950(12) 0.0128(3) Uani 1 1 d .
O2 O 1.05348(13) 0.56778(12) 0.86154(9) 0.0175(2) Uani 1 1 d .
H2 H 1.1139 0.5207 0.8974 0.026 Uiso 1 1 calc R
Br6 Br 0.334982(17) 0.317707(17) 0.757415(12) 0.01802(6) Uani 1 1 d .
C11 C 0.82863(17) 0.70588(16) 0.74557(12) 0.0129(3) Uani 1 1 d .
C12 C 0.80992(17) 0.80949(17) 0.80051(12) 0.0150(3) Uani 1 1 d .
C13 C 0.80978(18) 0.93654(17) 0.75802(13) 0.0175(3) Uani 1 1 d .
H13 H 0.7967 1.0047 0.7966 0.021 Uiso 1 1 calc R
C14 C 0.82839(18) 0.96014(16) 0.66176(13) 0.0166(3) Uani 1 1 d .
H14 H 0.8290 1.0439 0.6352 0.020 Uiso 1 1 calc R
C15 C 0.87121(17) 0.87932(17) 0.50136(13) 0.0158(3) Uani 1 1 d .
H15 H 0.8737 0.9622 0.4737 0.019 Uiso 1 1 calc R
C16 C 0.89092(17) 0.77786(17) 0.44577(12) 0.0153(3) Uani 1 1 d .
C17 C 0.88356(18) 0.65226(17) 0.48491(12) 0.0155(3) Uani 1 1 d .
H17 H 0.8926 0.5856 0.4453 0.019 Uiso 1 1 calc R
C18 C 0.86300(17) 0.62872(16) 0.58177(12) 0.0141(3) Uani 1 1 d .
H18 H 0.8602 0.5451 0.6075 0.017 Uiso 1 1 calc R
C19 C 0.84590(17) 0.72938(16) 0.64392(12) 0.0131(3) Uani 1 1 d .
C20 C 0.84696(17) 0.85735(16) 0.60155(12) 0.0145(3) Uani 1 1 d .
O12 O 0.79093(14) 0.80006(12) 0.89766(9) 0.0184(3) Uani 1 1 d .
H12 H 0.7877 0.7253 0.9170 0.028 Uiso 1 1 calc R
Br16 Br 0.940820(18) 0.801099(17) 0.313622(12) 0.01925(6) Uani 1 1 d .
C21 C 0.62498(17) 0.54625(17) 1.00913(12) 0.0139(3) Uani 1 1 d .
C22 C 0.60990(17) 0.42283(17) 1.06103(12) 0.0152(3) Uani 1 1 d .
H22 H 0.6827 0.3748 1.1009 0.018 Uiso 1 1 calc R
C23 C 0.49335(18) 0.37814(17) 1.05201(12) 0.0148(3) Uani 1 1 d .
H23 H 0.4869 0.2989 1.0845 0.018 Uiso 1 1 calc R
O21 O 0.73456(13) 0.58532(12) 1.01600(9) 0.0163(2) Uani 1 1 d .
C31 C 0.46625(19) 0.83182(19) 0.52688(13) 0.0209(4) Uani 1 1 d .
H31 H 0.5461 0.8655 0.5146 0.025 Uiso 1 1 calc R
C32 C 0.4227(2) 0.7659(2) 0.46004(14) 0.0246(4) Uani 1 1 d .
H32 H 0.4734 0.7546 0.4027 0.030 Uiso 1 1 calc R
C33 C 0.3006(2) 0.71391(19) 0.47673(14) 0.0238(4) Uani 1 1 d .
H33 H 0.2725 0.6685 0.4305 0.029 Uiso 1 1 calc R
C34 C 0.22441(19) 0.73024(18) 0.56010(13) 0.0195(4) Uani 1 1 d .
H34 H 0.1440 0.6969 0.5698 0.023 Uiso 1 1 calc R
C35 C 0.1569(2) 0.90065(18) 0.87863(13) 0.0201(4) Uani 1 1 d .
H35 H 0.0750 0.8700 0.8899 0.024 Uiso 1 1 calc R
C36 C 0.2008(2) 0.96671(18) 0.94541(14) 0.0221(4) Uani 1 1 d .
H36 H 0.1462 0.9840 1.0006 0.027 Uiso 1 1 calc R
C37 C 0.3293(2) 1.00965(18) 0.93179(14) 0.0229(4) Uani 1 1 d .
H37 H 0.3597 1.0519 0.9791 0.027 Uiso 1 1 calc R
C38 C 0.4078(2) 0.98909(17) 0.84991(14) 0.0200(4) Uani 1 1 d .
H38 H 0.4924 1.0163 0.8424 0.024 Uiso 1 1 calc R
C39 C 0.43597(18) 0.91244(17) 0.68786(13) 0.0172(3) Uani 1 1 d .
H39 H 0.5166 0.9453 0.6773 0.021 Uiso 1 1 calc R
C40 C 0.19222(18) 0.81339(17) 0.71999(13) 0.0169(3) Uani 1 1 d .
H40 H 0.1120 0.7799 0.7308 0.020 Uiso 1 1 calc R
C41 C 0.23601(18) 0.87809(16) 0.79117(13) 0.0164(3) Uani 1 1 d .
C42 C 0.36239(18) 0.92631(16) 0.77525(13) 0.0166(3) Uani 1 1 d .
C43 C 0.39040(18) 0.84986(17) 0.61595(13) 0.0167(3) Uani 1 1 d .
C44 C 0.26660(18) 0.79803(17) 0.63297(13) 0.0162(3) 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 118.50(15) .
C2 C1 C11 120.23(14) .
C9 C1 C11 121.26(14) .
O2 C2 C1 118.20(15) .
O2 C2 C3 120.49(15) .
C1 C2 C3 121.30(15) .
C4 C3 C2 120.31(15) .
C3 C4 C10 120.92(16) .
C6 C5 C10 119.52(15) .
C5 C6 C7 121.61(15) .
C5 C6 Br6 120.93(13) .
C7 C6 Br6 117.46(12) .
C8 C7 C6 119.52(15) .
C7 C8 C9 121.30(15) .
C8 C9 C10 118.18(14) .
C8 C9 C1 121.60(15) .
C10 C9 C1 120.22(14) .
C5 C10 C4 121.54(15) .
C5 C10 C9 119.76(15) .
C4 C10 C9 118.69(15) .
C12 C11 C19 118.59(15) .
C12 C11 C1 120.19(15) .
C19 C11 C1 121.21(15) .
O12 C12 C11 124.21(16) .
O12 C12 C13 114.62(15) .
C11 C12 C13 121.17(16) .
C14 C13 C12 120.99(16) .
C13 C14 C20 120.28(16) .
C16 C15 C20 119.54(15) .
C15 C16 C17 121.61(15) .
C15 C16 Br16 120.32(13) .
C17 C16 Br16 117.96(13) .
C18 C17 C16 119.59(16) .
C17 C18 C19 121.45(15) .
C18 C19 C20 117.71(15) .
C18 C19 C11 122.27(15) .
C20 C19 C11 120.02(15) .
C15 C20 C14 121.04(16) .
C15 C20 C19 119.99(15) .
C14 C20 C19 118.94(16) .
O21 C21 C22 120.84(15) .
O21 C21 C23 120.87(15) 2_667
C22 C21 C23 118.28(15) 2_667
C23 C22 C21 121.24(15) .
C22 C23 C21 120.47(15) 2_667
C32 C31 C43 120.62(18) .
C31 C32 C33 120.85(18) .
C34 C33 C32 120.38(18) .
C33 C34 C44 120.86(17) .
C36 C35 C41 120.48(17) .
C35 C36 C37 120.82(18) .
C38 C37 C36 120.30(18) .
C37 C38 C42 121.04(17) .
C42 C39 C43 121.13(16) .
C44 C40 C41 121.31(16) .
C40 C41 C35 122.03(16) .
C40 C41 C42 119.12(16) .
C35 C41 C42 118.84(16) .
C39 C42 C38 121.99(16) .
C39 C42 C41 119.64(16) .
C38 C42 C41 118.36(16) .
C39 C43 C31 121.99(17) .
C39 C43 C44 119.25(16) .
C31 C43 C44 118.73(16) .
C40 C44 C34 121.94(16) .
C40 C44 C43 119.51(16) .
C34 C44 C43 118.55(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.387(2) .
C1 C9 1.430(2) .
C1 C11 1.497(2) .
C2 O2 1.362(2) .
C2 C3 1.420(2) .
C3 C4 1.364(2) .
C4 C10 1.420(2) .
C5 C6 1.372(2) .
C5 C10 1.417(2) .
C6 C7 1.409(2) .
C6 Br6 1.8954(16) .
C7 C8 1.368(2) .
C8 C9 1.422(2) .
C9 C10 1.427(2) .
C11 C12 1.381(2) .
C11 C19 1.431(2) .
C12 O12 1.363(2) .
C12 C13 1.418(2) .
C13 C14 1.359(3) .
C14 C20 1.422(2) .
C15 C16 1.367(2) .
C15 C20 1.419(2) .
C16 C17 1.407(2) .
C16 Br16 1.9025(16) .
C17 C18 1.370(2) .
C18 C19 1.423(2) .
C19 C20 1.429(2) .
C21 O21 1.238(2) .
C21 C22 1.469(2) .
C21 C23 1.476(2) 2_667
C22 C23 1.339(2) .
C23 C21 1.476(2) 2_667
C31 C32 1.360(3) .
C31 C43 1.432(2) .
C32 C33 1.423(3) .
C33 C34 1.363(3) .
C34 C44 1.431(2) .
C35 C36 1.361(3) .
C35 C41 1.432(2) .
C36 C37 1.424(3) .
C37 C38 1.361(3) .
C38 C42 1.431(2) .
C39 C42 1.397(2) .
C39 C43 1.400(2) .
C40 C44 1.398(2) .
C40 C41 1.399(3) .
C41 C42 1.437(2) .
C43 C44 1.437(2) .
