#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/11/4511163.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_4511163
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 H26.5 Br2 Cl N O4.5'
_chemical_formula_weight         680.30
_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
_cell_angle_alpha                106.993(2)
_cell_angle_beta                 91.265(2)
_cell_angle_gamma                112.231(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2449(10)
_cell_length_b                   10.7942(10)
_cell_length_c                   14.1490(14)
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.52
_cell_volume                     1369.5(2)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12154
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    3.099
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.5113
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             685
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0420
_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)+(0.0451P)²+0.9354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                4958
_reflns_number_total             6134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9003388_si_001.cif
_cod_data_source_block           imaiNN71_3_audit_creation_method_SHELXL-97
_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 H26.50 Br2 Cl N O4.50'
_cod_database_code               4511163
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 0.9067(3) 0.2795(3) 0.1815(2) 0.0168(6) Uani 1 1 d . . .
C2 C 0.9009(3) 0.1991(3) 0.2434(2) 0.0192(6) Uani 1 1 d . . .
C3 C 1.0270(3) 0.2308(3) 0.3062(2) 0.0196(6) Uani 1 1 d . . .
C4 C 1.1525(3) 0.3410(3) 0.3111(2) 0.0193(6) Uani 1 1 d . . .
H4 H 1.2348 0.3596 0.3543 0.023 Uiso 1 1 calc R . .
C5 C 1.2871(3) 0.5444(3) 0.2554(2) 0.0216(6) Uani 1 1 d . . .
H5 H 1.3696 0.5656 0.2995 0.026 Uiso 1 1 calc R . .
C6 C 1.2936(3) 0.6267(3) 0.1975(2) 0.0243(7) Uani 1 1 d . . .
H6 H 1.3803 0.7038 0.2004 0.029 Uiso 1 1 calc R . .
C7 C 1.1707(3) 0.5969(4) 0.1330(2) 0.0277(7) Uani 1 1 d . . .
H7 H 1.1748 0.6553 0.0933 0.033 Uiso 1 1 calc R . .
C8 C 1.0459(3) 0.4853(3) 0.1270(2) 0.0240(7) Uani 1 1 d . . .
H8 H 0.9645 0.4672 0.0832 0.029 Uiso 1 1 calc R . .
C9 C 1.0357(3) 0.3954(3) 0.1853(2) 0.0184(6) Uani 1 1 d . . .
C10 C 1.1595(3) 0.4275(3) 0.2513(2) 0.0185(6) Uani 1 1 d . . .
O2 O 0.7741(2) 0.0930(2) 0.23875(16) 0.0262(5) Uani 1 1 d . . .
H2 H 0.7796 0.0583 0.2839 0.039 Uiso 1 1 calc R . .
Br3 Br 1.02218(3) 0.11531(3) 0.38596(2) 0.02533(10) Uani 1 1 d . . .
C11 C 0.7781(3) 0.2423(3) 0.1094(2) 0.0169(6) Uani 1 1 d . . .
C12 C 0.6967(3) 0.3199(3) 0.1306(2) 0.0188(6) Uani 1 1 d . . .
C13 C 0.5770(3) 0.2893(3) 0.0617(2) 0.0195(6) Uani 1 1 d . . .
C14 C 0.5421(3) 0.1839(3) -0.0282(2) 0.0196(6) Uani 1 1 d . . .
H14 H 0.4614 0.1641 -0.0734 0.023 Uiso 1 1 calc R . .
C15 C 0.5967(3) -0.0015(3) -0.1492(2) 0.0244(7) Uani 1 1 d . . .
H15 H 0.5186 -0.0201 -0.1964 0.029 Uiso 1 1 calc R . .
C16 C 0.6794(4) -0.0759(4) -0.1733(3) 0.0312(8) Uani 1 1 d . . .
H16 H 0.6603 -0.1443 -0.2377 0.037 Uiso 1 1 calc R . .
C17 C 0.7933(4) -0.0518(4) -0.1031(3) 0.0326(8) Uani 1 1 d . . .
H17 H 0.8491 -0.1059 -0.1199 0.039 Uiso 1 1 calc R . .
C18 C 0.8243(4) 0.0488(3) -0.0110(2) 0.0257(7) Uani 1 1 d . . .
H18 H 0.9010 0.0629 0.0356 0.031 Uiso 1 1 calc R . .
C19 C 0.7445(3) 0.1318(3) 0.0159(2) 0.0181(6) Uani 1 1 d . . .
C20 C 0.6259(3) 0.1041(3) -0.0539(2) 0.0184(6) Uani 1 1 d . . .
O12 O 0.7310(2) 0.4251(2) 0.22124(15) 0.0256(5) Uani 1 1 d . . .
H12 H 0.7139 0.4925 0.2144 0.038 Uiso 1 1 calc R . .
Br13 Br 0.46589(4) 0.39537(4) 0.09911(2) 0.02931(10) Uani 1 1 d . . .
C21 C 0.9635(4) 0.4404(3) 0.5194(2) 0.0280(7) Uani 1 1 d . . .
C22 C 0.8222(4) 0.3441(4) 0.4820(3) 0.0390(9) Uani 1 1 d . . .
H22 H 0.7705 0.3534 0.4299 0.047 Uiso 1 1 calc R . .
C23 C 0.7586(4) 0.2373(4) 0.5199(3) 0.0426(10) Uani 1 1 d . . .
H23 H 0.6628 0.1727 0.4935 0.051 Uiso 1 1 calc R . .
N24 N 0.8279(3) 0.2214(3) 0.5934(2) 0.0355(7) Uani 1 1 d . . .
C25 C 0.9638(4) 0.3102(4) 0.6302(3) 0.0359(9) Uani 1 1 d . . .
H25 H 1.0132 0.2975 0.6818 0.043 Uiso 1 1 calc R . .
C26 C 1.0326(4) 0.4195(4) 0.5942(2) 0.0332(8) Uani 1 1 d . . .
H26 H 1.1290 0.4814 0.6211 0.040 Uiso 1 1 calc R . .
C27 C 0.7545(5) 0.1035(4) 0.6317(3) 0.0491(11) Uani 1 1 d . . .
H27A H 0.6597 0.1000 0.6442 0.074 Uiso 1 1 calc R . .
H27B H 0.8102 0.1179 0.6941 0.074 Uiso 1 1 calc R . .
H27C H 0.7448 0.0141 0.5821 0.074 Uiso 1 1 calc R . .
C31 C 0.4316(3) 0.4438(3) 0.5719(2) 0.0240(7) Uani 1 1 d . . .
C32 C 0.4667(3) 0.3589(3) 0.4901(2) 0.0261(7) Uani 1 1 d . . .
C33 C 0.5342(3) 0.4151(3) 0.4191(2) 0.0253(7) Uani 1 1 d . . .
O31 O 0.3607(5) 0.3912(4) 0.6481(3) 0.0233(9) Uani 0.50 1 d P . .
H31 H 0.3474 0.3059 0.6353 0.035 Uiso 0.50 1 calc PR . .
O32 O 0.4458(5) 0.2287(4) 0.4713(3) 0.0250(10) Uani 0.50 1 d P . .
H32 H 0.4204 0.2037 0.5212 0.037 Uiso 0.50 1 calc PR . .
O33 O 0.5600(5) 0.3237(5) 0.3493(3) 0.0246(10) Uani 0.50 1 d P . .
H33 H 0.5996 0.3612 0.3075 0.037 Uiso 0.50 1 calc PR . .
Cl Cl 0.36498(9) 0.11209(9) 0.63978(7) 0.0340(2) Uani 1 1 d . . .
O41 O 0.2165(8) 0.3099(7) 0.7687(4) 0.0199(16) Uiso 0.400(8) 1 d P A 1
H41 H 0.2528 0.2594 0.7315 0.030 Uiso 0.400(8) 1 calc PR A 1
C42 C 0.2318(12) 0.3041(13) 0.8687(8) 0.050(3) Uiso 0.400(8) 1 d P A 1
H42A H 0.3113 0.2757 0.8777 0.060 Uiso 0.400(8) 1 calc PR A 1
H42B H 0.2566 0.3997 0.9172 0.060 Uiso 0.400(8) 1 calc PR A 1
C43 C 0.1056(14) 0.2074(14) 0.8890(9) 0.058(3) Uiso 0.400(8) 1 d P A 1
H43A H 0.1214 0.2056 0.9570 0.087 Uiso 0.400(8) 1 calc PR A 1
H43B H 0.0807 0.1126 0.8411 0.087 Uiso 0.400(8) 1 calc PR A 1
H43C H 0.0275 0.2373 0.8828 0.087 Uiso 0.400(8) 1 calc PR A 1
O51 O 0.1635(6) 0.2314(7) 0.7624(4) 0.0494(15) Uiso 0.600(8) 1 d P A 2
H51 H 0.2128 0.3157 0.7667 0.074 Uiso 0.600(8) 1 calc PR A 2
C52 C 0.1862(7) 0.2119(7) 0.8522(5) 0.0335(16) Uiso 0.600(8) 1 d P A 2
H52A H 0.2884 0.2337 0.8693 0.040 Uiso 0.600(8) 1 calc PR A 2
H52B H 0.1303 0.1121 0.8470 0.040 Uiso 0.600(8) 1 calc PR A 2
C53 C 0.1411(6) 0.3087(6) 0.9333(4) 0.0221(14) Uiso 0.600(8) 1 d P A 2
H53A H 0.1566 0.2946 0.9973 0.033 Uiso 0.600(8) 1 calc PR A 2
H53B H 0.0399 0.2866 0.9161 0.033 Uiso 0.600(8) 1 calc PR A 2
H53C H 0.1979 0.4075 0.9389 0.033 Uiso 0.600(8) 1 calc PR A 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_1
_geom_angle_site_symmetry_3
C2 C1 C9 120.0(3) . .
C2 C1 C11 120.0(3) . .
C9 C1 C11 120.0(2) . .
O2 C2 C1 117.3(3) . .
O2 C2 C3 123.9(3) . .
C1 C2 C3 118.8(3) . .
C4 C3 C2 122.4(3) . .
C4 C3 Br3 118.5(2) . .
C2 C3 Br3 119.0(2) . .
C3 C4 C10 119.6(3) . .
C6 C5 C10 121.2(3) . .
C5 C6 C7 119.6(3) . .
C8 C7 C6 120.8(3) . .
C7 C8 C9 121.2(3) . .
C1 C9 C10 120.0(3) . .
C1 C9 C8 122.4(3) . .
C10 C9 C8 117.6(3) . .
C4 C10 C5 121.4(3) . .
C4 C10 C9 119.1(3) . .
C5 C10 C9 119.6(3) . .
C12 C11 C19 119.7(3) . .
C12 C11 C1 119.9(3) . .
C19 C11 C1 120.3(3) . .
C11 C12 O12 118.5(3) . .
C11 C12 C13 120.8(3) . .
O12 C12 C13 120.7(3) . .
C14 C13 C12 120.7(3) . .
C14 C13 Br13 121.2(2) . .
C12 C13 Br13 118.1(2) . .
C13 C14 C20 120.1(3) . .
C16 C15 C20 120.7(3) . .
C15 C16 C17 120.1(3) . .
C18 C17 C16 120.7(3) . .
C17 C18 C19 121.1(3) . .
C18 C19 C11 122.6(3) . .
C18 C19 C20 118.3(3) . .
C11 C19 C20 119.1(3) . .
C14 C20 C15 121.4(3) . .
C14 C20 C19 119.5(3) . .
C15 C20 C19 119.0(3) . .
C26 C21 C22 116.7(3) . .
C26 C21 C21 121.3(4) . 2_766
C22 C21 C21 122.0(4) . 2_766
C23 C22 C21 120.4(4) . .
N24 C23 C22 121.3(4) . .
C23 N24 C25 120.0(3) . .
C23 N24 C27 119.3(3) . .
C25 N24 C27 120.6(3) . .
N24 C25 C26 120.7(3) . .
C25 C26 C21 120.8(3) . .
C33 C31 C32 119.1(3) 2_666 .
C33 C31 O31 118.2(3) 2_666 .
C32 C31 O31 122.7(3) . .
O32 C32 C33 112.6(3) . .
O32 C32 C31 127.2(4) . .
C33 C32 C31 120.2(3) . .
O33 C33 C32 112.3(3) . .
O33 C33 C31 126.9(4) . 2_666
C32 C33 C31 120.8(3) . 2_666
C43 C42 O41 112.3(10) . .
O51 C52 C53 109.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.389(4) .
C1 C9 1.421(4) .
C1 C11 1.497(4) .
C2 O2 1.353(4) .
C2 C3 1.418(4) .
C3 C4 1.366(4) .
C3 Br3 1.900(3) .
C4 C10 1.416(4) .
C5 C6 1.360(4) .
C5 C10 1.418(4) .
C6 C7 1.411(4) .
C7 C8 1.365(4) .
C8 C9 1.424(4) .
C9 C10 1.423(4) .
C11 C12 1.371(4) .
C11 C19 1.428(4) .
C12 O12 1.373(3) .
C12 C13 1.420(4) .
C13 C14 1.366(4) .
C13 Br13 1.883(3) .
C14 C20 1.415(4) .
C15 C16 1.358(5) .
C15 C20 1.426(4) .
C16 C17 1.409(5) .
C17 C18 1.368(5) .
C18 C19 1.409(4) .
C19 C20 1.428(4) .
C21 C26 1.377(5) .
C21 C22 1.401(5) .
C21 C21 1.491(7) 2_766
C22 C23 1.359(5) .
C23 N24 1.333(5) .
N24 C25 1.340(5) .
N24 C27 1.475(5) .
C25 C26 1.373(5) .
C31 C33 1.392(4) 2_666
C31 C32 1.399(5) .
C31 O31 1.447(5) .
C32 O32 1.282(5) .
C32 C33 1.388(5) .
C33 O33 1.287(5) .
C33 C31 1.392(4) 2_666
O41 C42 1.442(12) .
C42 C43 1.419(17) .
O51 C52 1.376(8) .
C52 C53 1.520(9) .
