#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510109.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_4510109
loop_
_publ_author_name
'Mukherjee, Arijit'
'Desiraju, Gautam R.'
_publ_section_title
;
 Combinatorial Exploration of the Structural Landscape of Acid--Pyridine
 Cocrystals
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1375
_journal_paper_doi               10.1021/cg401851z
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C23 H26 N2 O6'
_chemical_formula_weight         426.46
_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                72.85(4)
_cell_angle_beta                 84.64(6)
_cell_angle_gamma                71.17(5)
_cell_formula_units_Z            2
_cell_length_a                   9.612(2)
_cell_length_b                   10.0841(2)
_cell_length_c                   12.239(3)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1072.9(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_av_sigmaI/netI    0.1160
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11459
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.328
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.0315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.2061
_reflns_number_gt                2973
_reflns_number_total             4872
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg401851z_si_002.cif
_cod_data_source_block           33
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1072.9(4)
_cod_database_code               4510109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
H1N H 0.179(4) 0.588(4) 0.413(3) 0.075(14) Uiso 1 1 d .
H3O H 0.330(6) 0.283(6) 0.567(5) 0.14(2) Uiso 1 1 d .
C1 C 0.2928(3) 0.6803(3) 0.4770(2) 0.0305(7) Uani 1 1 d .
H1 H 0.3837 0.6422 0.4458 0.037 Uiso 1 1 calc R
C3 C 0.2808(3) 0.7721(3) 0.5416(2) 0.0267(6) Uani 1 1 d .
H3 H 0.3623 0.7972 0.5529 0.032 Uiso 1 1 calc R
C4 C 0.1443(3) 0.8297(3) 0.5920(2) 0.0228(6) Uani 1 1 d .
C5 C 0.0266(3) 0.7868(3) 0.5685(2) 0.0264(7) Uani 1 1 d .
H5 H -0.0655 0.8213 0.5994 0.032 Uiso 1 1 calc R
C6 C 0.0459(3) 0.6962(3) 0.5018(2) 0.0307(7) Uani 1 1 d .
H6 H -0.0337 0.6707 0.4870 0.037 Uiso 1 1 calc R
C7 C 0.2519(4) 0.9668(4) 0.6758(3) 0.0370(8) Uani 1 1 d .
H7A H 0.3221 0.8877 0.7271 0.055 Uiso 1 1 calc R
H7B H 0.2154 1.0474 0.7083 0.055 Uiso 1 1 calc R
H7C H 0.2984 0.9969 0.6040 0.055 Uiso 1 1 calc R
C8 C -0.0075(3) 0.9676(3) 0.7161(3) 0.0361(8) Uani 1 1 d .
H8A H -0.0840 1.0249 0.6608 0.054 Uiso 1 1 calc R
H8B H 0.0036 1.0257 0.7623 0.054 Uiso 1 1 calc R
H8C H -0.0327 0.8843 0.7640 0.054 Uiso 1 1 calc R
C9 C 0.3264(3) 0.2243(3) 0.2863(2) 0.0225(6) Uani 1 1 d .
C10 C 0.2836(3) 0.2954(3) 0.1723(2) 0.0258(6) Uani 1 1 d .
H10 H 0.2501 0.3969 0.1486 0.031 Uiso 1 1 calc R
C11 C 0.2898(3) 0.2193(3) 0.0942(2) 0.0275(7) Uani 1 1 d .
H11 H 0.2625 0.2691 0.0185 0.033 Uiso 1 1 calc R
C12 C 0.3375(3) 0.0662(3) 0.1298(2) 0.0254(6) Uani 1 1 d .
C13 C 0.3832(3) -0.0071(3) 0.2430(2) 0.0274(7) Uani 1 1 d .
H13 H 0.4173 -0.1086 0.2665 0.033 Uiso 1 1 calc R
C14 C 0.3777(3) 0.0703(3) 0.3193(2) 0.0250(6) Uani 1 1 d .
H14 H 0.4084 0.0204 0.3943 0.030 Uiso 1 1 calc R
C15 C 0.3142(3) 0.3081(3) 0.3700(2) 0.0285(7) Uani 1 1 d .
C16 C 0.3011(4) 0.0492(4) -0.0553(2) 0.0401(8) Uani 1 1 d .
H16A H 0.1987 0.1047 -0.0590 0.060 Uiso 1 1 calc R
H16B H 0.3173 -0.0233 -0.0953 0.060 Uiso 1 1 calc R
H16C H 0.3581 0.1132 -0.0902 0.060 Uiso 1 1 calc R
C17 C 0.2556(3) 0.4545(3) 0.7728(2) 0.0245(6) Uani 1 1 d .
C18 C 0.3849(3) 0.4784(3) 0.7928(2) 0.0287(7) Uani 1 1 d .
H18 H 0.4709 0.4405 0.7556 0.034 Uiso 1 1 calc R
C19 C 0.3867(3) 0.5577(3) 0.8674(2) 0.0324(7) Uani 1 1 d .
H19 H 0.4738 0.5718 0.8809 0.039 Uiso 1 1 calc R
C20 C 0.2574(3) 0.6165(3) 0.9224(2) 0.0307(7) Uani 1 1 d .
C21 C 0.1287(3) 0.5944(3) 0.9028(2) 0.0293(7) Uani 1 1 d .
H21 H 0.0425 0.6333 0.9394 0.035 Uiso 1 1 calc R
C22 C 0.1282(3) 0.5138(3) 0.8284(2) 0.0271(7) Uani 1 1 d .
H22 H 0.0411 0.4993 0.8155 0.033 Uiso 1 1 calc R
C23 C 0.2476(3) 0.3730(3) 0.6913(2) 0.0275(7) Uani 1 1 d .
C24 C 0.1478(4) 0.7518(4) 1.0573(3) 0.0484(9) Uani 1 1 d .
H24A H 0.0696 0.8165 1.0054 0.073 Uiso 1 1 calc R
H24B H 0.1730 0.8046 1.1020 0.073 Uiso 1 1 calc R
H24C H 0.1164 0.6735 1.1071 0.073 Uiso 1 1 calc R
N1 N 0.1776(3) 0.6424(3) 0.4565(2) 0.0324(6) Uani 1 1 d .
N2 N 0.1296(3) 0.9188(2) 0.65762(19) 0.0267(6) Uani 1 1 d .
O1 O 0.3444(2) -0.0209(2) 0.06169(17) 0.0355(5) Uani 1 1 d .
O2 O 0.2598(3) 0.4464(2) 0.33606(19) 0.0430(6) Uani 1 1 d .
O3 O 0.3588(2) 0.2345(2) 0.47144(17) 0.0360(5) Uani 1 1 d .
O4 O 0.2732(2) 0.6934(2) 0.99392(18) 0.0419(6) Uani 1 1 d .
O5 O 0.3664(2) 0.3448(2) 0.62728(16) 0.0316(5) Uani 1 1 d .
O6 O 0.1402(2) 0.3365(3) 0.68377(19) 0.0433(6) 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
N1 C1 C3 122.3(3)
C1 C3 C4 120.1(3)
N2 C4 C3 121.4(3)
N2 C4 C5 122.9(3)
C3 C4 C5 115.7(3)
C6 C5 C4 121.1(3)
N1 C6 C5 121.5(3)
C10 C9 C14 117.7(3)
C10 C9 C15 121.0(2)
C14 C9 C15 121.3(2)
C11 C10 C9 121.8(3)
C10 C11 C12 119.5(3)
O1 C12 C13 115.4(2)
O1 C12 C11 125.0(2)
C13 C12 C11 119.6(3)
C14 C13 C12 120.2(3)
C13 C14 C9 121.3(3)
O2 C15 O3 125.0(3)
O2 C15 C9 118.2(3)
O3 C15 C9 116.8(3)
C22 C17 C18 118.5(3)
C22 C17 C23 118.8(3)
C18 C17 C23 122.7(3)
C19 C18 C17 120.8(3)
C18 C19 C20 119.9(3)
O4 C20 C21 125.7(3)
O4 C20 C19 114.4(3)
C21 C20 C19 119.9(3)
C20 C21 C22 119.8(3)
C21 C22 C17 121.2(3)
O6 C23 O5 123.1(3)
O6 C23 C17 122.8(3)
O5 C23 C17 114.1(3)
C6 N1 C1 119.3(3)
C4 N2 C8 120.9(3)
C4 N2 C7 121.5(3)
C8 N2 C7 117.6(3)
C12 O1 C16 117.5(2)
C20 O4 C24 118.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.349(4)
C1 C3 1.357(4)
C3 C4 1.417(4)
C4 N2 1.340(4)
C4 C5 1.414(4)
C5 C6 1.356(4)
C6 N1 1.344(4)
C7 N2 1.465(4)
C8 N2 1.450(4)
C9 C10 1.398(4)
C9 C14 1.411(4)
C9 C15 1.484(4)
C10 C11 1.378(4)
C11 C12 1.403(4)
C12 O1 1.361(3)
C12 C13 1.400(4)
C13 C14 1.371(4)
C15 O2 1.273(4)
C15 O3 1.275(3)
C16 O1 1.431(3)
C17 C22 1.390(4)
C17 C18 1.395(4)
C17 C23 1.488(4)
C18 C19 1.385(4)
C19 C20 1.397(4)
C20 O4 1.375(4)
C20 C21 1.380(4)
C21 C22 1.390(4)
C23 O6 1.223(3)
C23 O5 1.324(4)
C24 O4 1.428(4)
