#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100233.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_2100233
loop_
_publ_author_name
'Oswald, Iain D. H.'
'Motherwell, W. D. Samuel'
'Parsons, Simon'
_publ_section_title
;
 Formation of quinol co-crystals with hydrogen-bond acceptors
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              46
_journal_page_last               57
_journal_paper_doi               10.1107/S0108768104028605
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         2(C10H8N2)(C6H6O2)
_chemical_formula_sum            'C26 H22 N4 O2'
_chemical_formula_weight         422.49
_chemical_name_common            quinol:2(4,4'-bipyridine)
_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                111.897(7)
_cell_angle_beta                 109.851(7)
_cell_angle_gamma                94.657(8)
_cell_formula_units_Z            1
_cell_length_a                   7.820(4)
_cell_length_b                   8.619(4)
_cell_length_c                   9.201(4)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.603
_cell_volume                     525.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.892
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4641
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lath
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.260
_refine_ls_extinction_coef       0.013(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0803P)²+0.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2067
_reflns_number_total             2428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ws5013.cif
_cod_data_source_block           6
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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        525.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2100233
_cod_database_fobs_code          2100233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1A 0.39246(15) 0.29172(13) 0.97975(14) 0.0289(3) Uani d . 1 . . O
H1A 0.267(3) 0.272(3) 0.928(3) 0.051(6) Uiso d . 1 . . H
C1A 0.44173(19) 0.14592(18) 0.98779(18) 0.0218(3) Uani d . 1 . . C
C2A 0.31417(19) -0.01306(18) 0.90679(17) 0.0223(3) Uani d . 1 . . C
H2A 0.1865 -0.0227 0.8425 0.027 Uiso calc R 1 . . H
C3A 0.37157(19) -0.15719(18) 0.91898(18) 0.0226(3) Uani d . 1 . . C
H3A 0.2829 -0.2647 0.8633 0.027 Uiso calc R 1 . . H
N1S 0.01390(17) 0.24543(17) 0.81825(18) 0.0292(3) Uani d . 1 . . N
C2S -0.0475(2) 0.1999(2) 0.6504(2) 0.0304(4) Uani d . 1 . . C
H2S 0.0343 0.1614 0.5955 0.036 Uiso calc R 1 . . H
C3S -0.2233(2) 0.2057(2) 0.5520(2) 0.0282(3) Uani d . 1 . . C
H3S -0.2608 0.1710 0.4327 0.034 Uiso calc R 1 . . H
C4S -0.34486(19) 0.26309(18) 0.63051(19) 0.0223(3) Uani d . 1 . . C
C5S -0.2830(2) 0.30806(19) 0.80472(19) 0.0253(3) Uani d . 1 . . C
H5S -0.3620 0.3460 0.8629 0.030 Uiso calc R 1 . . H
C6S -0.1046(2) 0.2968(2) 0.8925(2) 0.0276(3) Uani d . 1 . . C
H6S -0.0645 0.3271 1.0113 0.033 Uiso calc R 1 . . H
N7S -0.87985(18) 0.32257(18) 0.34555(17) 0.0319(3) Uani d . 1 . . N
C8S -0.7857(2) 0.4193(2) 0.5134(2) 0.0295(4) Uani d . 1 . . C
H8S -0.8402 0.5043 0.5695 0.035 Uiso calc R 1 . . H
C9S -0.6146(2) 0.40417(19) 0.6110(2) 0.0258(3) Uani d . 1 . . C
H9S -0.5546 0.4768 0.7300 0.031 Uiso calc R 1 . . H
C10S -0.53146(19) 0.28020(18) 0.53159(18) 0.0220(3) Uani d . 1 . . C
C11S -0.6276(2) 0.17840(19) 0.35718(19) 0.0265(3) Uani d . 1 . . C
H11S -0.5770 0.0920 0.2975 0.032 Uiso calc R 1 . . H
C12S -0.7979(2) 0.2046(2) 0.2717(2) 0.0308(4) Uani d . 1 . . C
H12S -0.8610 0.1341 0.1525 0.037 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1A 0.0203(6) 0.0278(6) 0.0358(6) 0.0086(4) 0.0068(5) 0.0140(5)
C1A 0.0200(7) 0.0269(7) 0.0207(7) 0.0098(5) 0.0090(6) 0.0107(6)
C2A 0.0151(6) 0.0305(8) 0.0199(7) 0.0072(5) 0.0061(5) 0.0098(6)
C3A 0.0171(7) 0.0254(7) 0.0205(7) 0.0031(5) 0.0056(5) 0.0069(5)
N1S 0.0211(6) 0.0301(7) 0.0368(8) 0.0107(5) 0.0088(6) 0.0162(6)
C2S 0.0246(8) 0.0338(8) 0.0374(9) 0.0142(6) 0.0155(7) 0.0158(7)
C3S 0.0266(8) 0.0324(8) 0.0267(8) 0.0110(6) 0.0112(6) 0.0127(6)
C4S 0.0194(7) 0.0212(7) 0.0272(8) 0.0067(5) 0.0079(6) 0.0123(6)
C5S 0.0232(7) 0.0277(7) 0.0281(8) 0.0094(6) 0.0114(6) 0.0134(6)
C6S 0.0243(7) 0.0314(8) 0.0287(8) 0.0102(6) 0.0081(6) 0.0160(6)
N7S 0.0206(6) 0.0366(8) 0.0320(8) 0.0071(5) 0.0044(6) 0.0135(6)
C8S 0.0221(7) 0.0304(8) 0.0324(8) 0.0106(6) 0.0077(6) 0.0116(7)
C9S 0.0211(7) 0.0266(7) 0.0252(7) 0.0063(6) 0.0062(6) 0.0092(6)
C10S 0.0174(7) 0.0245(7) 0.0261(8) 0.0055(5) 0.0077(6) 0.0137(6)
C11S 0.0233(7) 0.0270(7) 0.0275(8) 0.0070(6) 0.0092(6) 0.0106(6)
C12S 0.0218(7) 0.0356(8) 0.0260(8) 0.0036(6) 0.0040(6) 0.0097(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1A O1A H1A . . 110.5(13)
O1A C1A C2A . . 122.99(13)
O1A C1A C3A . 2_657 118.27(13)
C2A C1A C3A . 2_657 118.74(13)
C3A C2A C1A . . 120.68(13)
C3A C2A H2A . . 119.7
C1A C2A H2A . . 119.7
C2A C3A C1A . 2_657 120.58(13)
C2A C3A H3A . . 119.7
C1A C3A H3A 2_657 . 119.7
C2S N1S C6S . . 117.15(13)
N1S C2S C3S . . 123.70(14)
N1S C2S H2S . . 118.1
C3S C2S H2S . . 118.1
C2S C3S C4S . . 118.98(15)
C2S C3S H3S . . 120.5
C4S C3S H3S . . 120.5
C5S C4S C3S . . 117.62(13)
C5S C4S C10S . . 121.48(13)
C3S C4S C10S . . 120.87(14)
C6S C5S C4S . . 119.21(14)
C6S C5S H5S . . 120.4
C4S C5S H5S . . 120.4
N1S C6S C5S . . 123.30(15)
N1S C6S H6S . . 118.3
C5S C6S H6S . . 118.3
C8S N7S C12S . . 115.72(13)
N7S C8S C9S . . 124.54(14)
N7S C8S H8S . . 117.7
C9S C8S H8S . . 117.7
C8S C9S C10S . . 118.85(14)
C8S C9S H9S . . 120.6
C10S C9S H9S . . 120.6
C11S C10S C9S . . 117.33(13)
C11S C10S C4S . . 122.01(13)
C9S C10S C4S . . 120.64(13)
C12S C11S C10S . . 119.10(14)
C12S C11S H11S . . 120.5
C10S C11S H11S . . 120.5
N7S C12S C11S . . 124.47(15)
N7S C12S H12S . . 117.8
C11S C12S H12S . . 117.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1A . 1.3644(18) ?
O1A H1A . 0.90(2) ?
C1A C2A . 1.393(2) ?
C1A C3A 2_657 1.393(2) ?
C2A C3A . 1.385(2) ?
C2A H2A . 0.9500 ?
C3A C1A 2_657 1.393(2) ?
C3A H3A . 0.9500 ?
N1S C2S . 1.335(2) ?
N1S C6S . 1.339(2) ?
C2S C3S . 1.383(2) ?
C2S H2S . 0.9500 ?
C3S C4S . 1.395(2) ?
C3S H3S . 0.9500 ?
C4S C5S . 1.390(2) ?
C4S C10S . 1.487(2) ?
C5S C6S . 1.387(2) ?
C5S H5S . 0.9500 ?
C6S H6S . 0.9500 ?
N7S C8S . 1.338(2) ?
N7S C12S . 1.339(2) ?
C8S C9S . 1.384(2) ?
C8S H8S . 0.9500 ?
C9S C10S . 1.397(2) ?
C9S H9S . 0.9500 ?
C10S C11S . 1.391(2) ?
C11S C12S . 1.383(2) ?
C11S H11S . 0.9500 ?
C12S H12S . 0.9500 ?
