#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:15:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180496 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/65/7216505.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_7216505
loop_
_publ_author_name
'Ramon, Gaëlle'
'Davies, Kate'
'Nassimbeni, Luigi R.'
_publ_section_title
;
 Structures of benzoic acids with substituted pyridines and quinolines:
 salt versus co-crystal formation
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5802
_journal_paper_doi               10.1039/c3ce41963k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C7 H4 Br O2, C6 H9 N2'
_chemical_formula_sum            'C13 H13 Br N2 O2'
_chemical_formula_weight         309.16
_chemical_melting_point          ?
_chemical_name_common            none
_chemical_name_systematic
; 
4-bromobenzoic acid + 2-amino-4-methylpyridine 
;
_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                 100.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5786(19)
_cell_length_b                   11.539(2)
_cell_length_c                   11.311(2)
_cell_measurement_reflns_used    6862
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      4.07
_cell_volume                     1229.4(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω 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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6862
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.339
_exptl_absorpt_correction_T_max  0.6901
_exptl_absorpt_correction_T_min  0.6343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   DENZO-SMN
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0275P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0557
_reflns_number_gt                2326
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41963k.txt
_cod_data_source_block           data(XIV)-CCDC963021
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_symmetry_cell_setting' value
'Monoclinic' changed to 'monoclinic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 

 Adding full bibliography for 7216492--7216505.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7216505
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
Br1 Br 0.544081(18) 0.648741(15) 0.202285(15) 0.01739(7) Uani 1 1 d .
O1A O 0.09261(13) 1.11360(11) 0.07387(10) 0.0153(3) Uani 1 1 d .
N1B N -0.04656(14) 1.30212(14) -0.02326(12) 0.0119(3) Uani 1 1 d .
C5 C 0.42812(17) 0.77660(15) 0.14104(15) 0.0131(4) Uani 1 1 d .
O2A O 0.18905(13) 1.10955(12) -0.09159(10) 0.0201(3) Uani 1 1 d .
C7 C -0.03449(18) 1.35504(15) -0.12815(15) 0.0125(4) Uani 1 1 d .
C9 C 0.25933(17) 0.96469(15) 0.05436(14) 0.0118(3) Uani 1 1 d .
C10 C 0.24754(18) 0.91369(16) 0.16367(15) 0.0140(4) Uani 1 1 d .
H10 H 0.1812 0.9436 0.2088 0.017 Uiso 1 1 calc R
C11 C -0.13540(19) 1.34313(15) 0.04780(15) 0.0146(4) Uani 1 1 d .
H11 H -0.1415 1.3038 0.1205 0.018 Uiso 1 1 calc R
C12 C -0.20676(18) 1.49720(16) -0.09139(15) 0.0141(4) Uani 1 1 d .
C13 C 0.17338(17) 1.07020(15) 0.00807(14) 0.0122(4) Uani 1 1 d .
C14 C 0.33153(18) 0.81971(16) 0.20745(15) 0.0150(4) Uani 1 1 d .
H14 H 0.3229 0.7853 0.2821 0.018 Uiso 1 1 calc R
C16 C -0.11735(18) 1.45437(16) -0.16288(15) 0.0148(4) Uani 1 1 d .
H16 H -0.1113 1.4920 -0.2365 0.018 Uiso 1 1 calc R
C18 C -0.21561(17) 1.43901(16) 0.01713(15) 0.0155(4) Uani 1 1 d .
H18 H -0.2771 1.4668 0.0679 0.019 Uiso 1 1 calc R
N2B N 0.05501(16) 1.30900(15) -0.19304(13) 0.0172(3) Uani 1 1 d D
C2 C 0.35653(18) 0.91859(15) -0.01158(15) 0.0144(4) Uani 1 1 d .
H2 H 0.3642 0.9517 -0.0871 0.017 Uiso 1 1 calc R
C3 C 0.44166(18) 0.82549(16) 0.03164(16) 0.0162(4) Uani 1 1 d .
H3 H 0.5085 0.7954 -0.0130 0.019 Uiso 1 1 calc R
C1 C -0.29296(19) 1.60442(17) -0.12644(17) 0.0198(4) Uani 1 1 d .
H1A H -0.2523 1.6693 -0.0757 0.030 Uiso 1 1 calc R
H1B H -0.3910 1.5913 -0.1157 0.030 Uiso 1 1 calc R
H1C H -0.2920 1.6228 -0.2109 0.030 Uiso 1 1 calc R
H4 H 0.105(2) 1.2405(16) -0.1629(17) 0.031(6) Uiso 1 1 d D
H6 H 0.004(2) 1.236(2) 0.0042(18) 0.023(5) Uiso 1 1 d .
H1 H 0.066(2) 1.3489(18) -0.2661(17) 0.036(7) Uiso 1 1 d 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'
Br Br -0.2901 2.4595 '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
C11 N1B C7 121.50(16)
C11 N1B H6 115.8(12)
C7 N1B H6 122.7(12)
C14 C5 C3 121.15(17)
C14 C5 Br1 118.99(13)
C3 C5 Br1 119.86(13)
N2B C7 N1B 117.78(16)
N2B C7 C16 123.76(15)
N1B C7 C16 118.46(15)
C10 C9 C2 118.79(16)
C10 C9 C13 121.47(14)
C2 C9 C13 119.71(14)
C14 C10 C9 120.82(15)
C14 C10 H10 119.6
C9 C10 H10 119.6
C18 C11 N1B 121.34(16)
C18 C11 H11 119.3
N1B C11 H11 119.3
C16 C12 C18 118.83(17)
C16 C12 C1 120.91(16)
C18 C12 C1 120.25(15)
O2A C13 O1A 124.84(17)
O2A C13 C9 117.32(14)
O1A C13 C9 117.83(14)
C5 C14 C10 119.22(15)
C5 C14 H14 120.4
C10 C14 H14 120.4
C12 C16 C7 120.60(16)
C12 C16 H16 119.7
C7 C16 H16 119.7
C11 C18 C12 119.26(16)
C11 C18 H18 120.4
C12 C18 H18 120.4
C7 N2B H4 117.8(12)
C7 N2B H1 117.2(13)
H4 N2B H1 125.0(17)
C3 C2 C9 120.89(16)
C3 C2 H2 119.6
C9 C2 H2 119.6
C2 C3 C5 119.11(16)
C2 C3 H3 120.4
C5 C3 H3 120.4
C12 C1 H1A 109.5
C12 C1 H1B 109.5
H1A C1 H1B 109.5
C12 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.9003(17)
O1A C13 1.270(2)
N1B C11 1.357(2)
N1B C7 1.358(2)
N1B H6 0.92(2)
C5 C14 1.386(2)
C5 C3 1.387(2)
O2A C13 1.249(2)
C7 N2B 1.336(2)
C7 C16 1.409(2)
C9 C10 1.392(2)
C9 C2 1.399(2)
C9 C13 1.509(2)
C10 C14 1.387(3)
C10 H10 0.9500
C11 C18 1.356(3)
C11 H11 0.9500
C12 C16 1.372(2)
C12 C18 1.415(2)
C12 C1 1.500(3)
C14 H14 0.9500
C16 H16 0.9500
C18 H18 0.9500
N2B H4 0.956(16)
N2B H1 0.967(16)
C2 C3 1.383(3)
C2 H2 0.9500
C3 H3 0.9500
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
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
C11 N1B C7 N2B -179.80(16)
C11 N1B C7 C16 -0.3(2)
C2 C9 C10 C14 0.7(3)
C13 C9 C10 C14 -177.28(16)
C7 N1B C11 C18 -0.2(3)
C10 C9 C13 O2A -179.08(16)
C2 C9 C13 O2A 2.9(2)
C10 C9 C13 O1A 2.1(2)
C2 C9 C13 O1A -175.86(15)
C3 C5 C14 C10 -0.3(3)
Br1 C5 C14 C10 179.42(13)
C9 C10 C14 C5 0.0(3)
C18 C12 C16 C7 -0.8(3)
C1 C12 C16 C7 178.66(16)
N2B C7 C16 C12 -179.73(17)
N1B C7 C16 C12 0.8(2)
N1B C11 C18 C12 0.2(3)
C16 C12 C18 C11 0.3(3)
C1 C12 C18 C11 -179.16(16)
C10 C9 C2 C3 -1.3(3)
C13 C9 C2 C3 176.78(16)
C9 C2 C3 C5 1.0(3)
C14 C5 C3 C2 -0.3(3)
Br1 C5 C3 C2 -179.94(13)
