#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212754.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_7212754
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Rajbanshi, Arbin'
'Li, Z. Jane'
'Desper, John'
_publ_section_title
;
 Mapping out the synthetic landscape for re-crystallization,
 co-crystallization and salt formation
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4231
_journal_paper_doi               10.1039/c0ce00052c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety
;
(C5 H6 N2) (C7 H5 O2 Cl)
;
_chemical_formula_sum            'C12 H11 Cl N2 O2'
_chemical_formula_weight         250.68
_chemical_name_systematic
;
AR-1g-3 2-aminopyridine, 4-chlorobenzoic acid
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                 99.763(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6153(14)
_cell_length_b                   7.9832(17)
_cell_length_c                   11.143(3)
_cell_measurement_reflns_used    3986
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      3.15
_cell_volume                     580.0(2)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6842
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0297
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.741
_reflns_number_gt                3155
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00052c.txt
_cod_data_source_block           ar0815m(A3)
_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_cell_volume        579.9(2)
_cod_original_sg_symbol_H-M      Pn
_cod_database_code               7212754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
Cl1 Cl 1.31206(5) -0.07140(4) 0.70170(4) 0.02819(9) Uani 1 1 d .
N11 N 0.07154(17) 0.53677(14) 0.61005(10) 0.0185(2) Uani 1 1 d .
H11 H 0.195(3) 0.475(2) 0.6264(17) 0.022 Uiso 1 1 d .
C12 C 0.0012(2) 0.57710(15) 0.49133(11) 0.0183(2) Uani 1 1 d .
N12 N 0.10432(19) 0.52373(17) 0.40639(10) 0.0249(2) Uani 1 1 d .
H12A H 0.215(4) 0.454(2) 0.4275(19) 0.030 Uiso 1 1 d .
H12B H 0.050(4) 0.555(2) 0.332(2) 0.030 Uiso 1 1 d .
C13 C -0.1809(2) 0.67453(17) 0.46475(12) 0.0214(2) Uani 1 1 d .
H13 H -0.2330 0.7062 0.3832 0.026 Uiso 1 1 calc R
C14 C -0.2806(2) 0.72237(17) 0.55703(13) 0.0231(2) Uani 1 1 d .
H14 H -0.4037 0.7856 0.5390 0.028 Uiso 1 1 calc R
C15 C -0.2021(2) 0.67856(16) 0.67958(12) 0.0235(3) Uani 1 1 d .
H15 H -0.2702 0.7125 0.7440 0.028 Uiso 1 1 calc R
C16 C -0.0265(2) 0.58656(16) 0.70216(11) 0.0205(2) Uani 1 1 d .
H16 H 0.0288 0.5565 0.7836 0.025 Uiso 1 1 calc R
C21 C 0.71072(18) 0.20955(15) 0.61766(11) 0.0176(2) Uani 1 1 d .
C27 C 0.50914(19) 0.30194(16) 0.58519(12) 0.0191(2) Uani 1 1 d .
O21 O 0.42670(13) 0.36028(13) 0.67133(8) 0.02077(19) Uani 1 1 d .
O22 O 0.43622(15) 0.31383(15) 0.47398(9) 0.0287(2) Uani 1 1 d .
C22 C 0.82948(19) 0.18274(16) 0.52680(12) 0.0204(2) Uani 1 1 d .
H22 H 0.7818 0.2221 0.4465 0.024 Uiso 1 1 calc R
C23 C 1.0168(2) 0.09907(18) 0.55255(13) 0.0224(3) Uani 1 1 d .
H23 H 1.0986 0.0832 0.4911 0.027 Uiso 1 1 calc R
C24 C 1.08162(19) 0.03923(17) 0.67032(13) 0.0213(2) Uani 1 1 d .
C25 C 0.9662(2) 0.06238(16) 0.76223(12) 0.0210(2) Uani 1 1 d .
H25 H 1.0122 0.0196 0.8417 0.025 Uiso 1 1 calc R
C26 C 0.78107(18) 0.14978(17) 0.73546(11) 0.0195(2) Uani 1 1 d .
H26 H 0.7021 0.1689 0.7978 0.023 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'
Cl Cl 0.1484 0.1585 '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
C16 N11 C12 122.25(12)
C16 N11 H11 120.9(12)
C12 N11 H11 116.9(12)
N12 C12 N11 118.91(12)
N12 C12 C13 123.14(12)
N11 C12 C13 117.95(12)
C12 N12 H12A 119.7(13)
C12 N12 H12B 113.8(14)
H12A N12 H12B 126.3(19)
C14 C13 C12 119.72(12)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.68(13)
C13 C14 H14 119.7
C15 C14 H14 119.7
C16 C15 C14 118.17(13)
C16 C15 H15 120.9
C14 C15 H15 120.9
C15 C16 N11 121.22(12)
C15 C16 H16 119.4
N11 C16 H16 119.4
C22 C21 C26 119.22(11)
C22 C21 C27 118.80(11)
C26 C21 C27 121.98(11)
O22 C27 O21 125.18(12)
O22 C27 C21 116.65(11)
O21 C27 C21 118.16(10)
C23 C22 C21 120.86(12)
C23 C22 H22 119.6
C21 C22 H22 119.6
C24 C23 C22 118.60(12)
C24 C23 H23 120.7
C22 C23 H23 120.7
C25 C24 C23 121.90(12)
C25 C24 Cl1 119.35(11)
C23 C24 Cl1 118.74(11)
C24 C25 C26 118.71(12)
C24 C25 H25 120.6
C26 C25 H25 120.6
C25 C26 C21 120.69(11)
C25 C26 H26 119.7
C21 C26 H26 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C24 1.7452(13)
N11 C16 1.3629(17)
N11 C12 1.3643(16)
N11 H11 0.94(2)
C12 N12 1.3274(18)
C12 C13 1.4221(19)
N12 H12A 0.92(2)
N12 H12B 0.89(2)
C13 C14 1.367(2)
C13 H13 0.9500
C14 C15 1.4199(19)
C14 H14 0.9500
C15 C16 1.361(2)
C15 H15 0.9500
C16 H16 0.9500
C21 C22 1.3992(18)
C21 C26 1.4000(17)
C21 C27 1.5131(17)
C27 O22 1.2549(16)
C27 O21 1.2701(16)
C22 C23 1.3942(19)
C22 H22 0.9500
C23 C24 1.3941(19)
C23 H23 0.9500
C24 C25 1.390(2)
C25 C26 1.3968(17)
C25 H25 0.9500
C26 H26 0.9500
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
N11 H11 O21 0.94(2) 1.78(2) 2.7253(15) 174.9(18) .
N12 H12A O22 0.92(2) 1.85(2) 2.7631(16) 179(2) .
N12 H12B O21 0.89(2) 1.95(2) 2.8381(15) 176.0(18) 2_464
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
C16 N11 C12 N12 -179.78(12)
C16 N11 C12 C13 0.02(18)
N12 C12 C13 C14 178.85(13)
N11 C12 C13 C14 -0.94(19)
C12 C13 C14 C15 1.2(2)
C13 C14 C15 C16 -0.6(2)
C14 C15 C16 N11 -0.31(19)
C12 N11 C16 C15 0.61(19)
C22 C21 C27 O22 16.70(18)
C26 C21 C27 O22 -163.03(12)
C22 C21 C27 O21 -163.63(11)
C26 C21 C27 O21 16.63(18)
C26 C21 C22 C23 -0.61(18)
C27 C21 C22 C23 179.64(11)
C21 C22 C23 C24 1.38(19)
C22 C23 C24 C25 -0.7(2)
C22 C23 C24 Cl1 177.98(10)
C23 C24 C25 C26 -0.69(19)
Cl1 C24 C25 C26 -179.39(9)
C24 C25 C26 C21 1.48(18)
C22 C21 C26 C25 -0.84(18)
C27 C21 C26 C25 178.89(11)
