#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/51/2005147.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2005147
loop_
_publ_author_name
'Hori, K.'
'Kurosaki, M.'
'Wu, H.'
'Itoh, K.'
_publ_section_title
;
 Two Crystal Forms of 4'-octyloxy-4-cyanobiphenyl (8OCB)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1751
_journal_page_last               1754
_journal_paper_doi               10.1107/S0108270196003447
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C21 H25 N1 O1'
_chemical_formula_sum            'C21 H25 N O'
_chemical_formula_weight         307.42
_chemical_name_common            8OCB
_chemical_name_systematic
;
4'-octyloxy-4-cyanobiphenyl
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                99.86(3)
_cell_angle_beta                 99.44(3)
_cell_angle_gamma                92.55(2)
_cell_formula_units_Z            4
_cell_length_a                   12.710(4)
_cell_length_b                   20.410(6)
_cell_length_c                   7.325(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      27.0
_cell_volume                     1841.6(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992a)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992b)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC-7R'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.06
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5776
_diffrn_reflns_theta_max         60.16
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.911
_refine_ls_goodness_of_fit_obs   0.906
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_restrained_S_obs      0.906
_refine_ls_R_factor_all          0.2183
_refine_ls_R_factor_obs          0.0845
_refine_ls_shift/esd_max         -0.052
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.2318P)^2^ + 0.6965P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.3781
_refine_ls_wR_factor_obs         0.2315
_reflns_number_observed          2181
_reflns_number_total             5487
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            kh1089.cif
_cod_data_source_block           I
_cod_original_cell_volume        1841.7(13)
_cod_original_formula_sum        'C21 H25 N1 O1'
_cod_database_code               2005147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1A 1 0.8031(4) 0.3189(3) 0.4249(7) 0.0792(15) Uani d . O
N1A 1 0.8115(6) 0.6600(4) -0.5862(10) 0.095(2) Uani d . N
C1A 1 0.8016(6) 0.6245(4) -0.4833(11) 0.075(2) Uani d . C
C2A 1 0.7961(5) 0.5801(4) -0.3531(10) 0.063(2) Uani d . C
C3A 1 0.8395(5) 0.6027(4) -0.1662(10) 0.068(2) Uani d . C
H3A 1 0.8677 0.6467 -0.1265 0.082 Uiso calc R H
C4A 1 0.8412(5) 0.5602(4) -0.0378(10) 0.067(2) Uani d . C
H4A 1 0.8708 0.5759 0.0878 0.081 Uiso calc R H
C5A 1 0.7995(5) 0.4945(4) -0.0933(9) 0.061(2) Uani d . C
C6A 1 0.7528(5) 0.4732(3) -0.2815(10) 0.067(2) Uani d . C
H6A 1 0.7214 0.4299 -0.3208 0.081 Uiso calc R H
C7A 1 0.7525(6) 0.5155(4) -0.4116(10) 0.069(2) Uani d . C
H7A 1 0.7229 0.5003 -0.5374 0.082 Uiso calc R H
C8A 1 0.8031(5) 0.4482(3) 0.0405(9) 0.061(2) Uani d . C
C9A 1 0.8910(5) 0.4496(4) 0.1810(10) 0.069(2) Uani d . C
H9A 1 0.9492 0.4797 0.1878 0.083 Uiso calc R H
C10A 1 0.8951(5) 0.4076(4) 0.3124(10) 0.070(2) Uani d . C
H10A 1 0.9550 0.4102 0.4059 0.084 Uiso calc R H
C11A 1 0.8105(5) 0.3622(3) 0.3038(9) 0.063(2) Uani d . C
C12A 1 0.7208(5) 0.3590(4) 0.1633(10) 0.069(2) Uani d . C
H12A 1 0.6626 0.3288 0.1567 0.082 Uiso calc R H
C13A 1 0.7193(5) 0.4011(4) 0.0343(10) 0.068(2) Uani d . C
H13A 1 0.6599 0.3979 -0.0606 0.082 Uiso calc R H
C14A 1 0.8903(5) 0.3204(4) 0.5780(10) 0.072(2) Uani d . C
H14A 1 0.9030 0.3646 0.6545 0.086 Uiso calc R H
H14B 1 0.9551 0.3088 0.5300 0.086 Uiso calc R H
C15A 1 0.8603(6) 0.2713(4) 0.6916(10) 0.077(2) Uani d . C
H15A 1 0.8468 0.2275 0.6123 0.092 Uiso calc R H
H15B 1 0.7945 0.2830 0.7356 0.092 Uiso calc R H
C16A 1 0.9465(5) 0.2680(4) 0.8608(10) 0.071(2) Uani d . C
H16A 1 1.0129 0.2581 0.8166 0.085 Uiso calc R H
H16B 1 0.9579 0.3114 0.9420 0.085 Uiso calc R H
C17A 1 0.9201(6) 0.2167(4) 0.9742(10) 0.079(2) Uani d . C
H17A 1 0.9067 0.1735 0.8920 0.095 Uiso calc R H
H17B 1 0.8546 0.2272 1.0209 0.095 Uiso calc R H
C18A 1 1.0057(6) 0.2119(4) 1.1379(10) 0.079(2) Uani d . C
H18A 1 1.0715 0.2021 1.0913 0.095 Uiso calc R H
H18B 1 1.0182 0.2550 1.2210 0.095 Uiso calc R H
C19A 1 0.9804(7) 0.1601(4) 1.2499(11) 0.090(3) Uani d . C
H19A 1 0.9150 0.1702 1.2973 0.108 Uiso calc R H
H19B 1 0.9669 0.1172 1.1661 0.108 Uiso calc R H
C20A 1 1.0653(7) 0.1538(4) 1.4126(12) 0.100(3) Uani d . C
H20A 1 1.1308 0.1433 1.3658 0.120 Uiso calc R H
H20B 1 1.0791 0.1966 1.4970 0.120 Uiso calc R H
C21A 1 1.0379(9) 0.1021(5) 1.5217(15) 0.145(5) Uani d . C
H21A 1 1.0958 0.1010 1.6232 0.218 Uiso calc R H
H21B 1 1.0260 0.0592 1.4404 0.218 Uiso calc R H
H21C 1 0.9742 0.1126 1.5718 0.218 Uiso calc R H
O1B 1 0.4848(4) 0.1376(2) 0.8975(7) 0.083(2) Uani d . O
N1B 1 0.4133(6) 0.4485(3) -0.1964(9) 0.090(2) Uani d . N
C1B 1 0.4137(5) 0.4176(4) -0.0809(10) 0.069(2) Uani d . C
C2B 1 0.4203(5) 0.3776(3) 0.0634(9) 0.060(2) Uani d . C
C3B 1 0.4686(5) 0.4043(3) 0.2465(9) 0.065(2) Uani d . C
H3B 1 0.4954 0.4487 0.2776 0.078 Uiso calc R H
C4B 1 0.4766(5) 0.3652(3) 0.3809(9) 0.064(2) Uani d . C
H4B 1 0.5097 0.3835 0.5029 0.077 Uiso calc R H
C5B 1 0.4369(5) 0.2988(3) 0.3415(10) 0.062(2) Uani d . C
C6B 1 0.3851(6) 0.2740(4) 0.1575(10) 0.071(2) Uani d . C
H6B 1 0.3563 0.2301 0.1273 0.086 Uiso calc R H
C7B 1 0.3754(6) 0.3124(4) 0.0199(10) 0.073(2) Uani d . C
H7B 1 0.3393 0.2950 -0.1009 0.088 Uiso calc R H
C8B 1 0.4504(5) 0.2562(3) 0.4853(9) 0.060(2) Uani d . C
C9B 1 0.5454(5) 0.2617(3) 0.6160(10) 0.070(2) Uani d . C
H9B 1 0.6003 0.2925 0.6098 0.084 Uiso calc R H
C10B 1 0.5602(6) 0.2228(4) 0.7541(10) 0.073(2) Uani d . C
H10B 1 0.6244 0.2274 0.8385 0.088 Uiso calc R H
C11B 1 0.4802(6) 0.1775(3) 0.7661(10) 0.067(2) Uani d . C
C12B 1 0.3859(6) 0.1712(4) 0.6385(10) 0.078(2) Uani d . C
H12B 1 0.3310 0.1405 0.6455 0.093 Uiso calc R H
C13B 1 0.3724(6) 0.2092(3) 0.5029(10) 0.070(2) Uani d . C
H13B 1 0.3082 0.2036 0.4183 0.084 Uiso calc R H
C14B 1 0.5768(6) 0.1461(3) 1.0441(10) 0.075(2) Uani d . C
H14C 1 0.5859 0.1916 1.1125 0.090 Uiso calc R H
H14D 1 0.6407 0.1363 0.9911 0.090 Uiso calc R H
C15B 1 0.5585(6) 0.0987(4) 1.1732(10) 0.076(2) Uani d . C
H15C 1 0.5447 0.0539 1.1002 0.091 Uiso calc R H
H15D 1 0.4952 0.1100 1.2265 0.091 Uiso calc R H
C16B 1 0.6507(6) 0.0995(4) 1.3306(10) 0.078(2) Uani d . C
H16C 1 0.6633 0.1440 1.4054 0.094 Uiso calc R H
H16D 1 0.7144 0.0893 1.2774 0.094 Uiso calc R H
C17B 1 0.6332(6) 0.0504(4) 1.4581(10) 0.076(2) Uani d . C
H17C 1 0.5705 0.0613 1.5135 0.091 Uiso calc R H
H17D 1 0.6187 0.0061 1.3825 0.091 Uiso calc R H
C18B 1 0.7263(7) 0.0495(4) 1.6138(11) 0.091(3) Uani d . C
H18C 1 0.7403 0.0937 1.6904 0.109 Uiso calc R H
H18D 1 0.7892 0.0391 1.5585 0.109 Uiso calc R H
C19B 1 0.7090(7) -0.0002(4) 1.7396(10) 0.086(2) Uani d . C
H19C 1 0.6448 0.0095 1.7918 0.103 Uiso calc R H
H19D 1 0.6965 -0.0445 1.6631 0.103 Uiso calc R H
C20B 1 0.7991(8) -0.0008(5) 1.8975(13) 0.119(3) Uani d . C
H20C 1 0.8108 0.0432 1.9759 0.143 Uiso calc R H
H20D 1 0.8636 -0.0099 1.8459 0.143 Uiso calc R H
C21B 1 0.7809(10) -0.0515(5) 2.0191(14) 0.146(4) Uani d . C
H21D 1 0.8418 -0.0491 2.1174 0.219 Uiso calc R H
H21E 1 0.7711 -0.0954 1.9435 0.219 Uiso calc R H
H21F 1 0.7182 -0.0422 2.0736 0.219 Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_publ_flag
C11A O1A C14A 118.2(5) yes
N1A C1A C2A 176.6(8) yes
C7A C2A C3A 120.1(6) ?
C7A C2A C1A 121.5(7) ?
C3A C2A C1A 118.3(7) ?
C2A C3A C4A 120.1(7) ?
C3A C4A C5A 121.1(7) ?
C4A C5A C6A 117.9(6) yes
C4A C5A C8A 121.7(7) ?
C6A C5A C8A 120.3(7) ?
C7A C6A C5A 121.1(7) ?
C2A C7A C6A 119.6(7) ?
C9A C8A C13A 116.4(6) yes
C9A C8A C5A 121.1(7) ?
C13A C8A C5A 122.4(6) ?
C8A C9A C10A 122.2(7) ?
C11A C10A C9A 119.9(6) ?
O1A C11A C10A 126.1(6) ?
O1A C11A C12A 114.5(6) ?
C10A C11A C12A 119.4(6) ?
C13A C12A C11A 119.3(7) ?
C12A C13A C8A 122.6(7) ?
O1A C14A C15A 107.4(6) ?
C14A C15A C16A 112.8(6) ?
C17A C16A C15A 114.0(6) ?
C16A C17A C18A 114.3(6) ?
C19A C18A C17A 114.5(6) ?
C20A C19A C18A 115.5(7) ?
C21A C20A C19A 114.3(8) ?
C11B O1B C14B 118.5(6) yes
N1B C1B C2B 176.7(8) yes
C7B C2B C3B 120.0(6) ?
C7B C2B C1B 119.6(7) ?
C3B C2B C1B 120.4(7) ?
C4B C3B C2B 119.7(7) ?
C3B C4B C5B 122.2(7) ?
C4B C5B C6B 116.8(6) yes
C4B C5B C8B 121.7(7) ?
C6B C5B C8B 121.5(7) ?
C7B C6B C5B 122.2(7) ?
C6B C7B C2B 119.1(7) ?
C9B C8B C13B 115.6(6) yes
C13B C8B C5B 123.6(6) ?
C9B C8B C5B 120.8(6) ?
C10B C9B C8B 122.1(7) ?
C11B C10B C9B 119.8(7) ?
O1B C11B C10B 125.1(7) ?
O1B C11B C12B 115.9(7) ?
C10B C11B C12B 119.0(6) ?
C13B C12B C11B 120.6(7) ?
C12B C13B C8B 122.7(7) ?
O1B C14B C15B 107.3(6) ?
C14B C15B C16B 113.7(6) ?
C15B C16B C17B 113.7(6) ?
C18B C17B C16B 114.2(6) ?
C17B C18B C19B 114.0(7) ?
C20B C19B C18B 114.8(7) ?
C19B C20B C21B 113.9(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C11A 1.365(8) yes
O1A C14A 1.437(7) yes
N1A C1A 1.149(8) yes
C1A C2A 1.431(10) yes
C2A C7A 1.375(9) ?
C2A C3A 1.381(9) ?
C3A C4A 1.384(9) ?
C4A C5A 1.386(9) ?
C5A C6A 1.395(9) ?
C5A C8A 1.471(9) yes
C6A C7A 1.391(9) ?
C8A C9A 1.385(9) ?
C8A C13A 1.392(9) ?
C9A C10A 1.391(9) ?
C10A C11A 1.374(9) ?
C11A C12A 1.396(9) ?
C12A C13A 1.381(9) ?
C14A C15A 1.483(9) ?
C15A C16A 1.526(9) ?
C16A C17A 1.502(9) ?
C17A C18A 1.502(9) ?
C18A C19A 1.501(9) ?
C19A C20A 1.497(10) ?
C20A C21A 1.492(11) ?
O1B C11B 1.358(8) yes
O1B C14B 1.435(8) yes
N1B C1B 1.138(8) yes
C1B C2B 1.437(10) yes
C2B C7B 1.386(9) ?
C2B C3B 1.387(9) ?
C3B C4B 1.364(9) ?
C4B C5B 1.390(9) ?
C5B C6B 1.396(9) ?
C5B C8B 1.470(9) yes
C6B C7B 1.373(9) ?
C8B C13B 1.385(9) ?
C8B C9B 1.399(9) ?
C9B C10B 1.384(9) ?
C10B C11B 1.368(9) ?
C11B C12B 1.381(10) ?
C12B C13B 1.356(9) ?
C14B C15B 1.499(9) ?
C15B C16B 1.500(9) ?
C16B C17B 1.514(9) ?
C17B C18B 1.506(10) ?
C18B C19B 1.514(9) ?
C19B C20B 1.491(11) ?
C20B C21B 1.510(12) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1A C1A C2A C7A -111.(15)
N1A C1A C2A C3A 67.(16)
C7A C2A C3A C4A 1.3(10)
C1A C2A C3A C4A -176.3(6)
C2A C3A C4A C5A -0.1(11)
C3A C4A C5A C6A -1.9(10)
C3A C4A C5A C8A 178.5(6)
C4A C5A C6A C7A 2.9(10)
C8A C5A C6A C7A -177.5(6)
C3A C2A C7A C6A -0.3(10)
C1A C2A C7A C6A 177.2(6)
C5A C6A C7A C2A -1.9(11)
C4A C5A C8A C9A -37.9(10)
C6A C5A C8A C9A 142.5(7)
C4A C5A C8A C13A 141.7(7)
C6A C5A C8A C13A -37.9(10)
C13A C8A C9A C10A -1.4(10)
C5A C8A C9A C10A 178.2(7)
C8A C9A C10A C11A 0.7(11)
C14A O1A C11A C10A 0.7(10)
C14A O1A C11A C12A -177.9(6)
C9A C10A C11A O1A -178.8(7)
C9A C10A C11A C12A -0.3(10)
O1A C11A C12A C13A 179.4(6)
C10A C11A C12A C13A 0.7(10)
C11A C12A C13A C8A -1.5(11)
C9A C8A C13A C12A 1.8(10)
C5A C8A C13A C12A -177.8(7)
C11A O1A C14A C15A 177.5(6)
O1A C14A C15A C16A -179.8(6)
C14A C15A C16A C17A -177.7(6)
C15A C16A C17A C18A 178.5(7)
C16A C17A C18A C19A -179.1(7)
C17A C18A C19A C20A 179.3(7)
C18A C19A C20A C21A 179.8(8)
N1B C1B C2B C7B -97.(15)
N1B C1B C2B C3B 85.(15)
C7B C2B C3B C4B 3.4(10)
C1B C2B C3B C4B -178.3(6)
C2B C3B C4B C5B -0.6(10)
C3B C4B C5B C6B -1.8(10)
C3B C4B C5B C8B 177.1(6)
C4B C5B C6B C7B 1.4(11)
C8B C5B C6B C7B -177.5(7)
C5B C6B C7B C2B 1.3(11)
C3B C2B C7B C6B -3.7(10)
C1B C2B C7B C6B 178.0(7)
C4B C5B C8B C13B 141.5(7)
C6B C5B C8B C13B -39.7(11)
C4B C5B C8B C9B -38.0(10)
C6B C5B C8B C9B 140.8(7)
C13B C8B C9B C10B -0.2(11)
C5B C8B C9B C10B 179.4(7)
C8B C9B C10B C11B -0.3(12)
C14B O1B C11B C10B 4.6(11)
C14B O1B C11B C12B -174.5(6)
C9B C10B C11B O1B -178.7(7)
C9B C10B C11B C12B 0.4(11)
O1B C11B C12B C13B 179.2(7)
C10B C11B C12B C13B 0.0(11)
C11B C12B C13B C8B -0.6(12)
C9B C8B C13B C12B 0.6(11)
C5B C8B C13B C12B -179.0(7)
C11B O1B C14B C15B 177.2(6)
O1B C14B C15B C16B 177.5(6)
C14B C15B C16B C17B -178.6(6)
C15B C16B C17B C18B 178.6(7)
C16B C17B C18B C19B -179.3(7)
C17B C18B C19B C20B -178.6(8)
C18B C19B C20B C21B -179.0(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 94049
