#------------------------------------------------------------------------------
#$Date: 2016-03-24 13:58:10 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179647 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/00/4510097.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_4510097
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            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 100.795(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2990(16)
_cell_length_b                   8.0627(10)
_cell_length_c                   22.101(3)
_cell_measurement_reflns_used    11721
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2327.9(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11246
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0426
_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)+(0.0646P)²+0.9008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                2052
_reflns_number_total             2669
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg401851z_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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.

'_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        2327.8(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4510097
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
H1A H 0.1644(14) 0.105(2) 0.2788(9) 0.040(5) Uiso 1 1 d .
H1B H 0.1549(15) 0.000(2) 0.3342(10) 0.050(6) Uiso 1 1 d .
H2O H 0.6341(17) 0.342(3) 0.5276(10) 0.058(6) Uiso 1 1 d .
C1 C 0.28381(10) 0.12177(17) 0.34185(6) 0.0223(3) Uani 1 1 d .
N2 N 0.73982(9) 0.43175(15) 0.57786(5) 0.0251(3) Uani 1 1 d .
C5 C 0.41534(10) 0.12956(17) 0.43331(6) 0.0223(3) Uani 1 1 d .
H5 H 0.4438 0.0864 0.4728 0.027 Uiso 1 1 calc R
O2 O 0.57489(8) 0.28980(14) 0.50506(5) 0.0329(3) Uani 1 1 d .
N1 N 0.19470(10) 0.05121(17) 0.30970(6) 0.0290(3) Uani 1 1 d .
O1 O 0.60397(8) 0.45184(13) 0.42758(5) 0.0329(3) Uani 1 1 d .
C4 C 0.46266(10) 0.26463(17) 0.41016(6) 0.0216(3) Uani 1 1 d .
C3 C 0.42040(10) 0.32357(18) 0.35149(6) 0.0247(3) Uani 1 1 d .
H3 H 0.4525 0.4130 0.3346 0.030 Uiso 1 1 calc R
C10 C 0.91318(10) 0.58946(17) 0.64104(6) 0.0220(3) Uani 1 1 d .
C2 C 0.33262(11) 0.25396(17) 0.31766(6) 0.0245(3) Uani 1 1 d .
H2 H 0.3051 0.2957 0.2778 0.029 Uiso 1 1 calc R
C11 C 0.87014(11) 0.45806(18) 0.66824(6) 0.0259(3) Uani 1 1 d .
H11 H 0.8993 0.4208 0.7085 0.031 Uiso 1 1 calc R
C13 C 1.00505(11) 0.67054(18) 0.67282(6) 0.0259(3) Uani 1 1 d .
C6 C 0.32814(10) 0.05801(17) 0.39979(6) 0.0236(3) Uani 1 1 d .
H6 H 0.2980 -0.0348 0.4160 0.028 Uiso 1 1 calc R
C7 C 0.55356(10) 0.34500(17) 0.44744(6) 0.0239(3) Uani 1 1 d .
C9 C 0.86762(11) 0.64319(18) 0.58274(6) 0.0267(3) Uani 1 1 d .
H9 H 0.8947 0.7343 0.5638 0.032 Uiso 1 1 calc R
C8 C 0.78134(11) 0.55986(18) 0.55310(6) 0.0276(3) Uani 1 1 d .
H8 H 0.7500 0.5957 0.5130 0.033 Uiso 1 1 calc R
C12 C 0.78324(11) 0.38332(18) 0.63464(6) 0.0267(3) Uani 1 1 d .
H12 H 0.7533 0.2937 0.6528 0.032 Uiso 1 1 calc R
N3 N 1.07750(10) 0.73500(18) 0.69806(6) 0.0341(3) 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 C6 119.39(13)
N1 C1 C2 121.90(13)
C6 C1 C2 118.70(12)
C8 N2 C12 118.10(12)
C6 C5 C4 121.23(12)
C3 C4 C5 118.24(12)
C3 C4 C7 120.87(12)
C5 C4 C7 120.88(12)
C2 C3 C4 121.10(13)
C9 C10 C11 119.68(12)
C9 C10 C13 119.51(13)
C11 C10 C13 120.81(12)
C3 C2 C1 120.39(12)
C12 C11 C10 117.86(13)
N3 C13 C10 179.76(18)
C5 C6 C1 120.26(13)
O1 C7 O2 123.18(13)
O1 C7 C4 123.70(13)
O2 C7 C4 113.12(12)
C8 C9 C10 117.87(13)
N2 C8 C9 123.45(13)
N2 C12 C11 123.01(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3847(17)
C1 C6 1.4031(18)
C1 C2 1.405(2)
N2 C8 1.3357(18)
N2 C12 1.3377(18)
C5 C6 1.3801(18)
C5 C4 1.4016(19)
O2 C7 1.3286(17)
O1 C7 1.2224(17)
C4 C3 1.3963(19)
C4 C7 1.4788(19)
C3 C2 1.382(2)
C10 C9 1.3865(19)
C10 C11 1.393(2)
C10 C13 1.4463(18)
C11 C12 1.3888(19)
C13 N3 1.1438(19)
C9 C8 1.384(2)
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
C6 C5 C4 C3 -1.2(2)
C6 C5 C4 C7 177.42(12)
C5 C4 C3 C2 1.8(2)
C7 C4 C3 C2 -176.88(12)
C4 C3 C2 C1 0.1(2)
N1 C1 C2 C3 178.75(13)
C6 C1 C2 C3 -2.5(2)
C9 C10 C11 C12 1.3(2)
C13 C10 C11 C12 -178.56(13)
C4 C5 C6 C1 -1.2(2)
N1 C1 C6 C5 -178.19(12)
C2 C1 C6 C5 3.0(2)
C3 C4 C7 O1 -9.0(2)
C5 C4 C7 O1 172.41(13)
C3 C4 C7 O2 170.75(12)
C5 C4 C7 O2 -7.86(19)
C11 C10 C9 C8 -1.5(2)
C13 C10 C9 C8 178.36(12)
C12 N2 C8 C9 1.0(2)
C10 C9 C8 N2 0.4(2)
C8 N2 C12 C11 -1.2(2)
C10 C11 C12 N2 0.1(2)
