#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503658.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_4503658
loop_
_publ_author_name
'Imai, Yoshitane'
'Kamon, Kensaku'
'Kinuta, Takafumi'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Preparation and Crystal Structure of Guest-Dependent Charge-Transfer Host
 System Using 1,1′-Bi-2-naphthol and 2-Chloro-5-methyl-benzoquinone
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3493
_journal_paper_doi               10.1021/cg800211v
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C28 H22 Cl O4.5'
_chemical_formula_weight         465.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           152
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31 2"'
_symmetry_space_group_name_H-M   'P 31 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   14.483(1)
_cell_length_b                   14.483(1)
_cell_length_c                   20.036(2)
_cell_measurement_reflns_used    5401
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.62
_cell_volume                     3639.6(5)
_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      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33117
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9449
_exptl_absorpt_correction_T_min  0.9189
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1458
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1317P)²+1.0593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                5401
_reflns_number_total             5764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800211v_si_002.cif
_cod_data_source_block           imai714_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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_cell_volume        3639.6(4)
_cod_original_sg_symbol_H-M      P3(1)21
_cod_original_formula_sum        'C28 H22 Cl O4.50'
_cod_database_code               4503658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -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 0.47956(19) 0.52727(18) 0.52238(10) 0.0179(4) Uani 1 1 d .
C2 C 0.37549(19) 0.50365(19) 0.51331(11) 0.0191(4) Uani 1 1 d .
C3 C 0.32792(19) 0.5467(2) 0.55617(11) 0.0215(5) Uani 1 1 d .
H3 H 0.2564 0.5298 0.5487 0.026 Uiso 1 1 calc R
C4 C 0.3837(2) 0.6111(2) 0.60710(11) 0.0228(5) Uani 1 1 d .
H4 H 0.3504 0.6383 0.6356 0.027 Uiso 1 1 calc R
C5 C 0.5511(2) 0.7073(2) 0.67212(12) 0.0261(5) Uani 1 1 d .
H5 H 0.5179 0.7328 0.7019 0.031 Uiso 1 1 calc R
C6 C 0.6568(2) 0.7372(2) 0.68145(12) 0.0288(5) Uani 1 1 d .
H6 H 0.6967 0.7840 0.7168 0.035 Uiso 1 1 calc R
C7 C 0.7049(2) 0.6969(2) 0.63738(12) 0.0265(5) Uani 1 1 d .
H7 H 0.7778 0.7174 0.6433 0.032 Uiso 1 1 calc R
C8 C 0.6484(2) 0.6289(2) 0.58645(12) 0.0220(5) Uani 1 1 d .
H8 H 0.6824 0.6025 0.5580 0.026 Uiso 1 1 calc R
C9 C 0.54008(19) 0.59744(18) 0.57552(11) 0.0182(4) Uani 1 1 d .
C10 C 0.4914(2) 0.63943(19) 0.61898(11) 0.0203(4) Uani 1 1 d .
O2 O 0.31112(15) 0.44024(16) 0.46335(9) 0.0265(4) Uani 1 1 d .
H2 H 0.3392 0.4079 0.4453 0.040 Uiso 1 1 calc R
C11 C 0.58617(19) 0.95879(17) 0.36036(10) 0.0172(4) Uani 1 1 d .
C12 C 0.48211(19) 0.87612(18) 0.35855(11) 0.0195(4) Uani 1 1 d .
C13 C 0.4412(2) 0.79755(19) 0.40936(12) 0.0233(5) Uani 1 1 d .
H13 H 0.3691 0.7416 0.4075 0.028 Uiso 1 1 calc R
C14 C 0.5045(2) 0.80170(18) 0.46066(11) 0.0221(5) Uani 1 1 d .
H14 H 0.4759 0.7491 0.4947 0.026 Uiso 1 1 calc R
C15 C 0.6810(2) 0.8874(2) 0.51637(12) 0.0264(5) Uani 1 1 d .
H15 H 0.6537 0.8352 0.5507 0.032 Uiso 1 1 calc R
C16 C 0.7857(2) 0.9661(3) 0.51741(14) 0.0355(6) Uani 1 1 d .
H16 H 0.8312 0.9671 0.5519 0.043 Uiso 1 1 calc R
C17 C 0.8267(2) 1.0457(3) 0.46780(14) 0.0370(7) Uani 1 1 d .
H17 H 0.8994 1.1003 0.4694 0.044 Uiso 1 1 calc R
C18 C 0.7629(2) 1.0450(2) 0.41743(12) 0.0262(5) Uani 1 1 d .
H18 H 0.7915 1.0997 0.3846 0.031 Uiso 1 1 calc R
C19 C 0.65398(19) 0.96319(18) 0.41344(11) 0.0188(4) Uani 1 1 d .
C20 C 0.6129(2) 0.88367(18) 0.46397(11) 0.0200(4) Uani 1 1 d .
O12 O 0.41141(14) 0.86311(15) 0.30926(9) 0.0263(4) Uani 1 1 d .
H12 H 0.4369 0.9184 0.2857 0.040 Uiso 1 1 calc R
C31 C 0.4947(2) 0.5123(2) 0.80768(11) 0.0227(5) Uani 1 1 d .
C32 C 0.54981(19) 0.4853(2) 0.75467(12) 0.0218(5) Uani 1 1 d .
C33 C 0.4991(2) 0.4331(2) 0.69957(11) 0.0220(5) Uani 1 1 d .
H33 H 0.5361 0.4165 0.6669 0.026 Uiso 1 1 calc R
C34 C 0.38642(19) 0.40088(19) 0.68874(11) 0.0200(4) Uani 1 1 d .
C35 C 0.3295(2) 0.4279(2) 0.74016(11) 0.0219(5) Uani 1 1 d .
C36 C 0.3828(2) 0.4815(2) 0.79493(12) 0.0243(5) Uani 1 1 d .
H36 H 0.3467 0.5003 0.8269 0.029 Uiso 1 1 calc R
C37 C 0.21252(18) 0.3945(2) 0.72639(10) 0.0194(4) Uani 1 1 d .
H37A H 0.1835 0.4139 0.7646 0.029 Uiso 1 1 calc R
H37B H 0.1712 0.3172 0.7195 0.029 Uiso 1 1 calc R
H37C H 0.2083 0.4309 0.6863 0.029 Uiso 1 1 calc R
O31 O 0.54042(17) 0.55817(16) 0.85922(9) 0.0292(4) Uani 1 1 d .
O34 O 0.34072(15) 0.35359(15) 0.63793(8) 0.0253(4) Uani 1 1 d .
Cl32 Cl 0.68059(5) 0.52429(6) 0.76870(3) 0.03443(19) Uani 1 1 d .
O41 O 0.0832(9) 0.2562(16) 0.5589(5) 0.218(11) Uani 0.50 1 d P
C42 C 0.1332(12) 0.1924(15) 0.5294(8) 0.125(7) Uani 0.50 1 d P
H42A H 0.2118 0.2380 0.5287 0.150 Uiso 0.50 1 calc PR
H42B H 0.1151 0.1301 0.5582 0.150 Uiso 0.50 1 calc PR
C43 C 0.0993(11) 0.1601(11) 0.4696(11) 0.132(8) Uani 0.50 1 d P
H43A H 0.1284 0.1160 0.4534 0.199 Uiso 0.50 1 calc PR
H43B H 0.1226 0.2219 0.4401 0.199 Uiso 0.50 1 calc PR
H43C H 0.0213 0.1180 0.4698 0.199 Uiso 0.50 1 calc PR
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'
Cl Cl 0.1484 0.1585 '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 C1 120.39(18) 6_556
C9 C1 C1 120.95(18) 6_556
O2 C2 C1 123.9(2) .
O2 C2 C3 114.8(2) .
C1 C2 C3 121.3(2) .
C4 C3 C2 120.4(2) .
C3 C4 C10 121.2(2) .
C6 C5 C10 121.1(2) .
C5 C6 C7 118.9(2) .
C8 C7 C6 121.3(2) .
C7 C8 C9 121.1(2) .
C8 C9 C1 122.1(2) .
C8 C9 C10 118.1(2) .
C1 C9 C10 119.8(2) .
C5 C10 C4 121.9(2) .
C5 C10 C9 119.6(2) .
C4 C10 C9 118.6(2) .
C12 C11 C19 119.2(2) .
C12 C11 C11 120.01(18) 4_675
C19 C11 C11 120.81(18) 4_675
O12 C12 C11 123.9(2) .
O12 C12 C13 115.2(2) .
C11 C12 C13 121.0(2) .
C14 C13 C12 120.4(2) .
C13 C14 C20 120.8(2) .
C16 C15 C20 120.1(2) .
C15 C16 C17 120.6(2) .
C18 C17 C16 120.6(3) .
C17 C18 C19 120.8(2) .
C20 C19 C18 118.4(2) .
C20 C19 C11 119.6(2) .
C18 C19 C11 122.0(2) .
C14 C20 C19 119.0(2) .
C14 C20 C15 121.5(2) .
C19 C20 C15 119.5(2) .
O31 C31 C36 121.6(2) .
O31 C31 C32 121.7(2) .
C36 C31 C32 116.7(2) .
C33 C32 C31 121.5(2) .
C33 C32 Cl32 121.99(19) .
C31 C32 Cl32 116.48(18) .
C32 C33 C34 120.7(2) .
O34 C34 C33 120.3(2) .
O34 C34 C35 120.6(2) .
C33 C34 C35 119.1(2) .
C36 C35 C34 118.9(2) .
C36 C35 C37 123.7(2) .
C34 C35 C37 117.4(2) .
C35 C36 C31 123.0(2) .
C43 C42 O41 111.4(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.381(3) .
C1 C9 1.430(3) .
C1 C1 1.496(4) 6_556
C2 O2 1.363(3) .
C2 C3 1.425(3) .
C3 C4 1.346(4) .
C4 C10 1.421(3) .
C5 C6 1.380(4) .
C5 C10 1.413(3) .
C6 C7 1.419(4) .
C7 C8 1.369(3) .
C8 C9 1.414(3) .
C9 C10 1.433(3) .
C11 C12 1.379(3) .
C11 C19 1.427(3) .
C11 C11 1.497(4) 4_675
C12 O12 1.366(3) .
C12 C13 1.417(3) .
C13 C14 1.358(3) .
C14 C20 1.419(4) .
C15 C16 1.367(4) .
C15 C20 1.423(3) .
C16 C17 1.409(4) .
C17 C18 1.365(4) .
C18 C19 1.425(3) .
C19 C20 1.421(3) .
C31 O31 1.227(3) .
C31 C36 1.472(4) .
C31 C32 1.493(3) .
C32 C33 1.332(4) .
C32 Cl32 1.707(3) .
C33 C34 1.472(3) .
C34 O34 1.221(3) .
C34 C35 1.489(3) .
C35 C36 1.343(3) .
C35 C37 1.536(3) .
O41 C42 1.55(3) .
C42 C43 1.29(2) .
