#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:20:21 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179625 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/89/4508906.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508906
loop_
_publ_author_name
'Bis, Joanna A.'
'McLaughlin, Olga L.'
'Vishweshwar, Peddy'
'Zaworotko, Michael J.'
_publ_section_title
;
 Supramolecular Heterocatemers and Their Role in Cocrystal Design
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2648
_journal_paper_doi               10.1021/cg060516f
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C23 H21 N2 O3'
_chemical_formula_weight         373.42
_chemical_name_common
;
3:2 co-crystal of 4,4'-biphenol and 2-aminopyridine
;
_chemical_name_systematic
; 
 3:2 co-crystal of 4,4'-biphenol and 2-aminopyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.359(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3359(16)
_cell_length_b                   20.632(3)
_cell_length_c                   8.0994(12)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      2.67
_cell_volume                     1888.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9377
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.124
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1054P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                2036
_reflns_number_total             3250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060516fsup1.cif
_cod_data_source_block           ommay164
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4508906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.73346(14) 0.28403(7) -0.1871(2) 0.0638(5) Uani 1 1 d .
H1 H 0.6580 0.2617 -0.1948 0.077 Uiso 1 1 d R
O2 O 0.72551(13) 0.73145(7) 0.2364(2) 0.0543(5) Uani 1 1 d .
H2 H 0.7826 0.7620 0.2199 0.065 Uiso 1 1 d R
C1 C 0.7355(2) 0.34555(10) -0.1228(3) 0.0480(6) Uani 1 1 d .
C2 C 0.8326(2) 0.38403(11) -0.1398(3) 0.0525(6) Uani 1 1 d .
H2 H 0.8963 0.3681 -0.1931 0.063 Uiso 1 1 calc R
C3 C 0.8357(2) 0.44638(10) -0.0780(3) 0.0487(6) Uani 1 1 d .
H3 H 0.9022 0.4717 -0.0912 0.058 Uiso 1 1 calc R
C4 C 0.74329(17) 0.47277(9) 0.0031(3) 0.0395(5) Uani 1 1 d .
C5 C 0.6465(2) 0.43236(10) 0.0193(3) 0.0496(6) Uani 1 1 d .
H5 H 0.5825 0.4481 0.0723 0.059 Uiso 1 1 calc R
C6 C 0.6425(2) 0.36975(11) -0.0406(3) 0.0516(6) Uani 1 1 d .
H6 H 0.5771 0.3438 -0.0257 0.062 Uiso 1 1 calc R
C7 C 0.74442(17) 0.54070(9) 0.0656(2) 0.0388(5) Uani 1 1 d .
C8 C 0.82362(19) 0.58738(10) 0.0191(3) 0.0459(6) Uani 1 1 d .
H8 H 0.8813 0.5756 -0.0509 0.055 Uiso 1 1 calc R
C9 C 0.81978(19) 0.65074(10) 0.0733(3) 0.0456(6) Uani 1 1 d .
H9 H 0.8740 0.6808 0.0390 0.055 Uiso 1 1 calc R
C10 C 0.73573(18) 0.66976(10) 0.1782(3) 0.0413(5) Uani 1 1 d .
C11 C 0.6568(2) 0.62408(10) 0.2282(3) 0.0499(6) Uani 1 1 d .
H11 H 0.5998 0.6361 0.2991 0.060 Uiso 1 1 calc R
C12 C 0.6619(2) 0.56104(10) 0.1741(3) 0.0494(6) Uani 1 1 d .
H12 H 0.6086 0.5310 0.2110 0.059 Uiso 1 1 calc R
N21 N 1.09729(16) 0.18750(9) 0.8288(2) 0.0489(5) Uani 1 1 d .
N22 N 0.96165(18) 0.23947(9) 0.6491(3) 0.0634(6) Uani 1 1 d .
H22A H 0.8842 0.2502 0.6287 0.076 Uiso 1 1 d R
H22B H 1.0226 0.2693 0.6557 0.076 Uiso 1 1 d R
C21 C 0.9865(2) 0.19133(10) 0.7618(3) 0.0461(6) Uani 1 1 d .
C22 C 0.9001(2) 0.14679(12) 0.8006(3) 0.0602(7) Uani 1 1 d .
H22 H 0.8234 0.1500 0.7519 0.072 Uiso 1 1 calc R
C23 C 0.9297(3) 0.09889(13) 0.9101(4) 0.0740(8) Uani 1 1 d .
H23 H 0.8730 0.0690 0.9376 0.089 Uiso 1 1 calc R
C24 C 1.0444(3) 0.09426(13) 0.9813(4) 0.0751(8) Uani 1 1 d .
C25 C 1.1233(2) 0.13926(13) 0.9371(3) 0.0611(7) Uani 1 1 d .
H25 H 1.2004 0.1366 0.9848 0.073 Uiso 1 1 calc R
O31 O 0.50849(13) 0.22630(7) 0.8042(2) 0.0610(5) Uani 1 1 d .
H31 H 0.4281 0.2395 0.7754 0.073 Uiso 1 1 d R
C31 C 0.50443(18) 0.16261(10) 0.8561(3) 0.0450(6) Uani 1 1 d .
C32 C 0.59387(18) 0.13997(11) 0.9652(3) 0.0516(6) Uani 1 1 d .
H32 H 0.6556 0.1673 1.0022 0.062 Uiso 1 1 calc R
C33 C 0.59174(19) 0.07656(11) 1.0196(3) 0.0492(6) Uani 1 1 d .
H33 H 0.6529 0.0620 1.0934 0.059 Uiso 1 1 calc R
C34 C 0.50195(17) 0.03389(9) 0.9684(3) 0.0390(5) Uani 1 1 d .
H34 H 1.0648 0.0607 1.0717 0.047 Uiso 1 1 d R
C35 C 0.41410(19) 0.05840(10) 0.8560(3) 0.0499(6) Uani 1 1 d .
H35 H 0.3522 0.0314 0.8182 0.060 Uiso 1 1 calc R
C36 C 0.41555(19) 0.12145(10) 0.7985(3) 0.0500(6) Uani 1 1 d .
H36 H 0.3566 0.1359 0.7210 0.060 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_3
O1 C1 C2 119.2(2) .
O1 C1 C6 121.7(2) .
C2 C1 C6 119.1(2) .
C1 C2 C3 120.1(2) .
C2 C3 C4 122.5(2) .
C3 C4 C5 116.0(2) .
C3 C4 C7 122.83(18) .
C5 C4 C7 121.2(2) .
C6 C5 C4 122.2(2) .
C5 C6 C1 120.1(2) .
C8 C7 C12 116.1(2) .
C8 C7 C4 123.4(2) .
C12 C7 C4 120.52(18) .
C9 C8 C7 122.3(2) .
C8 C9 C10 120.3(2) .
O2 C10 C9 123.93(19) .
O2 C10 C11 117.4(2) .
C9 C10 C11 118.6(2) .
C12 C11 C10 120.5(2) .
C11 C12 C7 122.1(2) .
C21 N21 C25 117.6(2) .
N21 C21 N22 117.2(2) .
N21 C21 C22 121.7(2) .
N22 C21 C22 121.1(2) .
C23 C22 C21 119.0(2) .
C22 C23 C24 120.1(2) .
C25 C24 C23 117.4(2) .
N21 C25 C24 124.2(2) .
C36 C31 C32 119.7(2) .
C36 C31 O31 121.72(18) .
C32 C31 O31 118.60(18) .
C31 C32 C33 119.80(19) .
C32 C33 C34 122.45(19) .
C33 C34 C35 115.96(19) .
C33 C34 C34 122.2(2) 3_657
C35 C34 C34 121.8(2) 3_657
C36 C35 C34 122.42(19) .
C31 C36 C35 119.66(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.371(2) .
O2 C10 1.365(2) .
C1 C2 1.373(3) .
C1 C6 1.381(3) .
C2 C3 1.380(3) .
C3 C4 1.389(3) .
C4 C5 1.392(3) .
C4 C7 1.490(3) .
C5 C6 1.379(3) .
C7 C8 1.388(3) .
C7 C12 1.396(3) .
C8 C9 1.381(3) .
C9 C10 1.381(3) .
C10 C11 1.382(3) .
C11 C12 1.375(3) .
N21 C21 1.332(3) .
N21 C25 1.345(3) .
N22 C21 1.364(3) .
C21 C22 1.396(3) .
C22 C23 1.353(3) .
C23 C24 1.384(4) .
C24 C25 1.356(4) .
O31 C31 1.382(2) .
C31 C36 1.372(3) .
C31 C32 1.375(3) .
C32 C33 1.381(3) .
C33 C34 1.385(3) .
C34 C35 1.392(3) .
C34 C34 1.491(4) 3_657
C35 C36 1.382(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 O2 0.96 1.84 2.788(2) 168.8 3_666
N22 H22A O1 0.91 2.45 3.134(3) 131.8 1_556
O2 H2 N21 0.92 1.78 2.697(2) 171.9 3_766
O1 H1 O31 0.97 1.84 2.811(2) 173.8 1_554
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 179.1(2) . .
C6 C1 C2 C3 -1.2(3) . .
C1 C2 C3 C4 0.2(3) . .
C2 C3 C4 C5 0.2(3) . .
C2 C3 C4 C7 -178.1(2) . .
C3 C4 C5 C6 0.3(3) . .
C7 C4 C5 C6 178.65(19) . .
C4 C5 C6 C1 -1.3(3) . .
O1 C1 C6 C5 -178.6(2) . .
C2 C1 C6 C5 1.7(3) . .
C3 C4 C7 C8 14.2(3) . .
C5 C4 C7 C8 -164.1(2) . .
C3 C4 C7 C12 -167.1(2) . .
C5 C4 C7 C12 14.6(3) . .
C12 C7 C8 C9 -1.5(3) . .
C4 C7 C8 C9 177.21(19) . .
C7 C8 C9 C10 0.4(3) . .
C8 C9 C10 O2 -179.57(19) . .
C8 C9 C10 C11 0.5(3) . .
O2 C10 C11 C12 179.89(19) . .
C9 C10 C11 C12 -0.2(3) . .
C10 C11 C12 C7 -1.1(3) . .
C8 C7 C12 C11 1.9(3) . .
C4 C7 C12 C11 -176.93(19) . .
C25 N21 C21 N22 -178.5(2) . .
C25 N21 C21 C22 -0.6(3) . .
N21 C21 C22 C23 0.6(4) . .
N22 C21 C22 C23 178.4(2) . .
C21 C22 C23 C24 -0.4(4) . .
C22 C23 C24 C25 0.2(5) . .
C21 N21 C25 C24 0.4(4) . .
C23 C24 C25 N21 -0.3(5) . .
C36 C31 C32 C33 -1.9(4) . .
O31 C31 C32 C33 179.7(2) . .
C31 C32 C33 C34 0.0(4) . .
C32 C33 C34 C35 1.0(4) . .
C32 C33 C34 C34 -178.0(2) . 3_657
C33 C34 C35 C36 -0.1(3) . .
C34 C34 C35 C36 178.9(2) 3_657 .
C32 C31 C36 C35 2.8(4) . .
O31 C31 C36 C35 -178.9(2) . .
C34 C35 C36 C31 -1.8(4) . .
