#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/52/1505201.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_1505201
loop_
_publ_author_name
'Bis, Joanna A.'
'Vishweshwar, Peddy'
'Weyna, David'
'Zaworotko, Michael J.'
_publ_section_title
;
 Hierarchy of Supramolecular Synthons:  Persistent
 Hydroxyl···Pyridine Hydrogen Bonds in Cocrystals
 That Contain a Cyano Acceptor
;
_journal_issue                   3
_journal_name_full               'Molecular Pharmaceutics'
_journal_page_first              401
_journal_paper_doi               10.1021/mp070012s
_journal_volume                  4
_journal_year                    2007
_chemical_formula_sum            'C24 H18 N4 O2'
_chemical_formula_weight         394.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.972(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   39.87(2)
_cell_length_b                   7.586(5)
_cell_length_c                   6.915(4)
_cell_measurement_temperature    273(2)
_cell_volume                     2090(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_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  0.1942
_diffrn_reflns_av_sigmaI/netI    0.2189
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4455
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.02
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.717
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.717
_refine_ls_R_factor_all          0.1894
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0706P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1970
_reflns_number_gt                669
_reflns_number_total             2425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            mp070012ssi20070321_042532.cif
_cod_data_source_block           jb453b1
_cod_database_code               1505201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.13533(5) 0.2787(3) 0.2239(4) 0.0792(9) Uani 1 1 d .
H1 H 0.1246 0.3875 0.2039 0.095 Uiso 1 1 d R
C1 C 0.16710(8) 0.2749(4) 0.1618(5) 0.0605(9) Uani 1 1 d .
C2 C 0.18759(8) 0.1451(5) 0.2225(6) 0.0828(13) Uani 1 1 d .
H2 H 0.1797 0.0599 0.3061 0.099 Uiso 1 1 calc R
C3 C 0.22017(9) 0.1353(5) 0.1636(6) 0.0846(13) Uani 1 1 d .
H3 H 0.2343 0.0473 0.2129 0.101 Uiso 1 1 calc R
C4 C 0.23222(8) 0.2563(4) 0.0305(5) 0.0582(9) Uani 1 1 d .
C5 C 0.21062(8) 0.3839(5) -0.0295(5) 0.0674(10) Uani 1 1 d .
H5 H 0.2180 0.4686 -0.1154 0.081 Uiso 1 1 calc R
C6 C 0.17826(8) 0.3943(5) 0.0304(5) 0.0650(10) Uani 1 1 d .
H6 H 0.1640 0.4819 -0.0181 0.078 Uiso 1 1 calc R
N11 N 0.10129(8) 0.5841(4) 0.1452(5) 0.0778(10) Uani 1 1 d .
N12 N 0.03093(9) 1.1704(5) 0.0527(6) 0.1050(13) Uani 1 1 d .
C11 C 0.11408(9) 0.7428(6) 0.1759(6) 0.0831(12) Uani 1 1 d .
H11 H 0.1365 0.7496 0.2173 0.100 Uiso 1 1 calc R
C12 C 0.09701(10) 0.8974(5) 0.1515(5) 0.0759(11) Uani 1 1 d .
H12 H 0.1075 1.0057 0.1722 0.091 Uiso 1 1 calc R
C13 C 0.06478(9) 0.8865(5) 0.0969(5) 0.0642(10) Uani 1 1 d .
C14 C 0.05047(9) 0.7264(5) 0.0612(6) 0.0793(12) Uani 1 1 d .
H14 H 0.0282 0.7168 0.0172 0.095 Uiso 1 1 calc R
C15 C 0.06969(9) 0.5817(5) 0.0920(6) 0.0779(12) Uani 1 1 d .
H15 H 0.0596 0.4723 0.0738 0.093 Uiso 1 1 calc R
C16 C 0.04573(10) 1.0459(6) 0.0722(6) 0.0795(12) Uani 1 1 d .
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
C2 C1 O1 119.0(3) .
C2 C1 C6 119.1(3) .
O1 C1 C6 121.8(3) .
C1 C2 C3 121.3(3) .
C2 C3 C4 120.6(3) .
C5 C4 C3 116.3(3) .
C5 C4 C4 124.0(4) 7
C3 C4 C4 119.6(4) 7
C4 C5 C6 123.0(3) .
C1 C6 C5 119.6(3) .
C15 N11 C11 115.0(3) .
N11 C11 C12 125.1(4) .
C13 C12 C11 117.1(4) .
C12 C13 C14 120.1(4) .
C12 C13 C16 118.9(4) .
C14 C13 C16 120.9(3) .
C15 C14 C13 117.7(4) .
N11 C15 C14 124.9(4) .
N12 C16 C13 179.8(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.352(3) .
C1 C2 1.338(5) .
C1 C6 1.368(4) .
C2 C3 1.377(4) .
C3 C4 1.397(5) .
C4 C5 1.352(4) .
C4 C4 1.496(6) 7
C5 C6 1.371(4) .
N11 C15 1.300(4) .
N11 C11 1.322(5) .
N12 C16 1.119(4) .
C11 C12 1.363(5) .
C12 C13 1.330(5) .
C13 C14 1.361(5) .
C13 C16 1.435(5) .
C14 C15 1.351(5) .
