#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/11/4511162.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_4511162
loop_
_publ_author_name
'Imai, Yoshitane'
'Kamon, Kensaku'
'Kinuta, Takafumi'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Multiple Molecular Recognition Host System using Charge-Transfer Complex
 of 3,3′-Disubstituted-1,1′-bi-2-naphthol and Methylviologen
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4096
_journal_paper_doi               10.1021/cg9003388
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C31 H28 Br2 Cl N O3.5'
_chemical_formula_weight         665.81
_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                106.9810(10)
_cell_angle_beta                 90.4400(10)
_cell_angle_gamma                112.1640(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2111(8)
_cell_length_b                   10.7567(9)
_cell_length_c                   13.8409(11)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.55
_cell_volume                     1334.56(19)
_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      115(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_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            11544
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    3.175
_exptl_absorpt_correction_T_max  0.5693
_exptl_absorpt_correction_T_min  0.3292
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5925
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.8153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                5112
_reflns_number_total             5925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9003388_si_001.cif
_cod_data_source_block           imaiNN71_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C31 H28 Br2 Cl N O3.50'
_cod_database_code               4511162
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9046(2) 0.2757(2) 1.18132(17) 0.0151(5) Uani 1 1 d . . .
C2 C 0.8971(3) 0.1939(2) 1.24317(18) 0.0169(5) Uani 1 1 d . . .
C3 C 1.0219(3) 0.2230(2) 1.30680(18) 0.0167(5) Uani 1 1 d . . .
C4 C 1.1468(3) 0.3329(3) 1.31224(18) 0.0178(5) Uani 1 1 d . . .
H4 H 1.2279 0.3504 1.3564 0.021 Uiso 1 1 calc R . .
C5 C 1.2845(3) 0.5394(3) 1.25742(19) 0.0200(5) Uani 1 1 d . . .
H5 H 1.3657 0.5605 1.3030 0.024 Uiso 1 1 calc R . .
C6 C 1.2925(3) 0.6228(3) 1.1981(2) 0.0241(5) Uani 1 1 d . . .
H6 H 1.3791 0.7006 1.2016 0.029 Uiso 1 1 calc R . .
C7 C 1.1716(3) 0.5927(3) 1.1316(2) 0.0281(6) Uani 1 1 d . . .
H7 H 1.1771 0.6510 1.0905 0.034 Uiso 1 1 calc R . .
C8 C 1.0468(3) 0.4809(3) 1.12547(19) 0.0230(5) Uani 1 1 d . . .
H8 H 0.9665 0.4628 1.0802 0.028 Uiso 1 1 calc R . .
C9 C 1.0347(2) 0.3914(2) 1.18524(18) 0.0164(5) Uani 1 1 d . . .
C10 C 1.1565(3) 0.4216(2) 1.25197(18) 0.0167(5) Uani 1 1 d . . .
O2 O 0.76999(19) 0.08753(19) 1.23801(15) 0.0251(4) Uani 1 1 d . . .
H2 H 0.7736 0.0533 1.2848 0.038 Uiso 1 1 calc R . .
Br3 Br 1.01400(3) 0.10338(3) 1.385473(19) 0.02212(8) Uani 1 1 d . . .
C11 C 0.7778(2) 0.2412(2) 1.10894(18) 0.0150(5) Uani 1 1 d . . .
C12 C 0.6984(3) 0.3220(3) 1.13176(18) 0.0175(5) Uani 1 1 d . . .
C13 C 0.5774(3) 0.2896(3) 1.06287(19) 0.0187(5) Uani 1 1 d . . .
C14 C 0.5417(3) 0.1838(3) 0.97186(18) 0.0179(5) Uani 1 1 d . . .
H14 H 0.4606 0.1644 0.9269 0.021 Uiso 1 1 calc R . .
C15 C 0.5937(3) -0.0029(3) 0.84823(19) 0.0215(5) Uani 1 1 d . . .
H15 H 0.5153 -0.0210 0.8013 0.026 Uiso 1 1 calc R . .
C16 C 0.6758(3) -0.0789(3) 0.8229(2) 0.0282(6) Uani 1 1 d . . .
H16 H 0.6559 -0.1482 0.7576 0.034 Uiso 1 1 calc R . .
C17 C 0.7898(3) -0.0557(3) 0.8926(2) 0.0328(7) Uani 1 1 d . . .
H17 H 0.8452 -0.1108 0.8746 0.039 Uiso 1 1 calc R . .
C18 C 0.8218(3) 0.0450(3) 0.9859(2) 0.0249(6) Uani 1 1 d . . .
H18 H 0.8987 0.0586 1.0324 0.030 Uiso 1 1 calc R . .
C19 C 0.7420(2) 0.1295(2) 1.01447(18) 0.0160(5) Uani 1 1 d . . .
C20 C 0.6246(2) 0.1031(2) 0.94422(18) 0.0159(5) Uani 1 1 d . . .
O12 O 0.7354(2) 0.4283(2) 1.22223(14) 0.0274(4) Uani 1 1 d . . .
H12 H 0.7188 0.4960 1.2149 0.041 Uiso 1 1 calc R . .
Br13 Br 0.46437(3) 0.39530(3) 1.10298(2) 0.02914(9) Uani 1 1 d . . .
C21 C 0.9624(3) 0.4396(3) 1.51910(18) 0.0191(5) Uani 1 1 d . . .
C22 C 1.0298(3) 0.4140(3) 1.59368(19) 0.0240(5) Uani 1 1 d . . .
H22 H 1.1267 0.4735 1.6204 0.029 Uiso 1 1 calc R . .
C23 C 0.9586(3) 0.3039(3) 1.6293(2) 0.0255(6) Uani 1 1 d . . .
H23 H 1.0065 0.2877 1.6805 0.031 Uiso 1 1 calc R . .
N24 N 0.8223(2) 0.2190(2) 1.59284(18) 0.0255(5) Uani 1 1 d . . .
C25 C 0.7542(3) 0.2398(3) 1.5195(2) 0.0308(6) Uani 1 1 d . . .
H25 H 0.6576 0.1782 1.4937 0.037 Uiso 1 1 calc R . .
C26 C 0.8211(3) 0.3477(3) 1.4815(2) 0.0270(6) Uani 1 1 d . . .
H26 H 0.7715 0.3602 1.4292 0.032 Uiso 1 1 calc R . .
C27 C 0.7462(3) 0.0993(3) 1.6310(3) 0.0350(7) Uani 1 1 d . . .
H27A H 0.7972 0.1144 1.6964 0.052 Uiso 1 1 calc R . .
H27B H 0.7416 0.0109 1.5816 0.052 Uiso 1 1 calc R . .
H27C H 0.6492 0.0935 1.6403 0.052 Uiso 1 1 calc R . .
Cl Cl 0.62418(7) 0.89010(7) 1.36304(6) 0.03067(16) Uani 1 1 d . . .
C31 C 0.4706(6) 0.3778(6) 0.4891(4) 0.0209(14) Uiso 0.50 1 d PD . .
C32 C 0.5423(6) 0.4491(7) 0.4216(5) 0.0255(15) Uiso 0.50 1 d PD . .
H32 H 0.5667 0.3991 0.3606 0.031 Uiso 0.50 1 calc PR . .
C33 C 0.5762(7) 0.5927(7) 0.4459(5) 0.0269(15) Uiso 0.50 1 d PD . .
H33 H 0.6250 0.6421 0.4016 0.032 Uiso 0.50 1 calc PR . .
C34 C 0.5398(7) 0.6643(8) 0.5338(5) 0.0257(14) Uiso 0.50 1 d PD . .
H34 H 0.5635 0.7630 0.5499 0.031 Uiso 0.50 1 calc PR . .
C35 C 0.4697(6) 0.5944(7) 0.5980(5) 0.0212(13) Uiso 0.50 1 d PD . .
H35 H 0.4458 0.6456 0.6587 0.025 Uiso 0.50 1 calc PR . .
C36 C 0.4327(6) 0.4499(6) 0.5763(4) 0.0157(11) Uiso 0.50 1 d PD . .
H36 H 0.3822 0.4019 0.6208 0.019 Uiso 0.50 1 calc PR . .
O31 O 0.4437(4) 0.2348(4) 0.4602(3) 0.0285(8) Uiso 0.50 1 d PD . .
H31 H 0.4292 0.2067 0.5112 0.043 Uiso 0.50 1 calc PR . .
O41 O 0.7702(6) 0.6845(6) 0.2367(4) 0.0248(16) Uiso 0.50 1 d PD A 1
H41 H 0.7380 0.7222 0.2875 0.037 Uiso 0.50 1 calc PR A 1
C42 C 0.7834(5) 0.7621(6) 0.1592(4) 0.0235(11) Uiso 0.50 1 d PD A 1
H42A H 0.7014 0.7031 0.1048 0.028 Uiso 0.50 1 calc PR A 1
H42B H 0.7705 0.8505 0.1936 0.028 Uiso 0.50 1 calc PR A 1
C43 C 0.8988(7) 0.7972(7) 0.1136(5) 0.0405(15) Uiso 0.50 1 d PD A 1
H43A H 0.8870 0.8449 0.0658 0.061 Uiso 0.50 1 calc PR A 1
H43B H 0.9133 0.7117 0.0765 0.061 Uiso 0.50 1 calc PR A 1
H43C H 0.9818 0.8612 0.1649 0.061 Uiso 0.50 1 calc PR A 1
O51 O 0.7823(6) 0.7168(7) 0.2443(4) 0.0240(15) Uiso 0.50 1 d PD B 2
H51 H 0.7268 0.7537 0.2715 0.036 Uiso 0.50 1 calc PR B 2
C52 C 0.7626(7) 0.6888(8) 0.1331(5) 0.0361(14) Uiso 0.50 1 d PD B 2
H52A H 0.6808 0.5964 0.1051 0.043 Uiso 0.50 1 calc PR B 2
H52B H 0.7304 0.7607 0.1230 0.043 Uiso 0.50 1 calc PR B 2
C53 C 0.8524(6) 0.6851(6) 0.0777(4) 0.0245(11) Uiso 0.50 1 d PD B 2
H53A H 0.8126 0.6650 0.0076 0.037 Uiso 0.50 1 calc PR B 2
H53B H 0.8836 0.6105 0.0811 0.037 Uiso 0.50 1 calc PR B 2
H53C H 0.9342 0.7767 0.0995 0.037 Uiso 0.50 1 calc PR B 2
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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 119.9(2) .
C2 C1 C11 120.1(2) .
C9 C1 C11 120.0(2) .
O2 C2 C1 117.4(2) .
O2 C2 C3 123.5(2) .
C1 C2 C3 119.1(2) .
C4 C3 C2 122.0(2) .
C4 C3 Br3 118.97(18) .
C2 C3 Br3 119.00(18) .
C3 C4 C10 120.0(2) .
C6 C5 C10 120.8(2) .
C5 C6 C7 119.6(2) .
C8 C7 C6 120.8(2) .
C7 C8 C9 121.2(2) .
C8 C9 C10 117.9(2) .
C8 C9 C1 122.1(2) .
C10 C9 C1 120.0(2) .
C9 C10 C4 118.8(2) .
C9 C10 C5 119.6(2) .
C4 C10 C5 121.6(2) .
C12 C11 C19 119.8(2) .
C12 C11 C1 119.5(2) .
C19 C11 C1 120.6(2) .
O12 C12 C11 118.5(2) .
O12 C12 C13 121.7(2) .
C11 C12 C13 119.7(2) .
C14 C13 C12 121.4(2) .
C14 C13 Br13 120.86(18) .
C12 C13 Br13 117.73(18) .
C13 C14 C20 120.3(2) .
C16 C15 C20 120.3(2) .
C15 C16 C17 120.4(3) .
C18 C17 C16 120.7(3) .
C17 C18 C19 120.9(2) .
C18 C19 C20 118.1(2) .
C18 C19 C11 122.3(2) .
C20 C19 C11 119.6(2) .
C14 C20 C15 121.3(2) .
C14 C20 C19 119.1(2) .
C15 C20 C19 119.6(2) .
C22 C21 C26 117.2(2) .
C22 C21 C21 121.3(3) 2_768
C26 C21 C21 121.5(3) 2_768
C23 C22 C21 120.7(3) .
N24 C23 C22 120.6(2) .
C23 N24 C25 120.2(2) .
C23 N24 C27 120.4(2) .
C25 N24 C27 119.4(2) .
N24 C25 C26 121.1(3) .
C25 C26 C21 120.1(3) .
C36 C31 O31 124.5(5) .
C36 C31 C32 120.4(5) .
O31 C31 C32 115.1(5) .
C36 C31 C32 28.9(3) 2_666
O31 C31 C32 153.3(5) 2_666
C32 C31 C32 91.6(4) 2_666
C33 C32 C31 118.8(6) .
C33 C32 C31 30.5(3) 2_666
C31 C32 C31 88.4(4) 2_666
C34 C33 C32 120.4(6) .
C35 C34 C33 120.3(7) .
C34 C35 C36 121.2(6) .
C31 C36 C35 118.7(5) .
C43 C42 O41 121.3(5) .
C53 C52 O51 125.5(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.379(3) .
C1 C9 1.425(3) .
C1 C11 1.490(3) .
C2 O2 1.353(3) .
C2 C3 1.421(3) .
C3 C4 1.356(3) .
C3 Br3 1.894(2) .
C4 C10 1.419(3) .
C5 C6 1.364(4) .
C5 C10 1.419(3) .
C6 C7 1.408(4) .
C7 C8 1.364(4) .
C8 C9 1.415(3) .
C9 C10 1.416(3) .
C11 C12 1.374(3) .
C11 C19 1.425(3) .
C12 O12 1.360(3) .
C12 C13 1.421(3) .
C13 C14 1.363(3) .
C13 Br13 1.887(2) .
C14 C20 1.407(3) .
C15 C16 1.359(4) .
C15 C20 1.415(3) .
C16 C17 1.404(4) .
C17 C18 1.363(4) .
C18 C19 1.414(3) .
C19 C20 1.424(3) .
C21 C22 1.383(3) .
C21 C26 1.393(4) .
C21 C21 1.488(5) 2_768
C22 C23 1.368(4) .
C23 N24 1.337(4) .
N24 C25 1.343(4) .
N24 C27 1.479(4) .
C25 C26 1.362(4) .
C31 C36 1.377(7) .
C31 O31 1.386(6) .
C31 C32 1.416(6) .
C31 C32 1.963(9) 2_666
C32 C33 1.382(7) .
C32 C31 1.963(9) 2_666
C33 C34 1.373(7) .
C34 C35 1.365(6) .
C35 C36 1.390(6) .
O41 C42 1.518(7) .
C42 C43 1.321(6) .
O51 C52 1.476(7) .
C52 C53 1.204(8) .
