#------------------------------------------------------------------------------
#$Date: 2019-09-18 14:24:37 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215564.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_7215564
loop_
_publ_author_name
'Skovsgaard, Signe'
'Bond, Andrew D.'
_publ_section_title
;
 Co-crystallisation of benzoic acid derivatives with N-containing bases in
 solution and by mechanical grinding: stoichiometric variants,
 polymorphism and twinning
;
_journal_coden_ASTM              CRECF4
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              444
_journal_page_last               453
_journal_paper_doi               10.1039/b810660f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C6 H14 N2 +, 2(C9 H7 O4 -)'
_chemical_formula_sum            'C24 H28 N2 O8'
_chemical_formula_weight         472.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.025(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4937(4)
_cell_length_b                   10.0957(5)
_cell_length_c                   15.2981(10)
_cell_measurement_reflns_used    4209
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.67
_cell_volume                     1146.03(11)
_computing_cell_refinement       'SAINT-plus v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT-plus v.7.06a'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ 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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22769
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.902004
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0535
_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)+(0.0741P)²+0.4957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                2120
_reflns_number_total             2757
_reflns_threshold_expression     I>2σ(I)
_cod_duplicate_entry             7200228
_cod_data_source_file            b810660f.cif
_cod_data_source_block           8
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-18

 Marked entry as a duplicate of entry 7200228.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7215564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.34859(18) 0.58563(14) 0.19597(10) 0.0396(4) Uani 1 1 d .
O2 O 0.5445(2) 0.64935(17) 0.10696(10) 0.0467(4) Uani 1 1 d .
O3 O 0.51993(17) 0.46739(12) 0.34131(8) 0.0282(3) Uani 1 1 d .
O4 O 0.3571(2) 0.60919(19) 0.41002(15) 0.0694(6) Uani 1 1 d .
C1 C 0.6461(2) 0.63981(19) 0.26038(13) 0.0310(4) Uani 1 1 d .
C2 C 0.6504(2) 0.56496(17) 0.33704(12) 0.0263(4) Uani 1 1 d .
C3 C 0.7862(3) 0.5787(2) 0.40751(14) 0.0365(5) Uani 1 1 d .
H3A H 0.7880 0.5243 0.4583 0.044 Uiso 1 1 calc R
C4 C 0.9193(3) 0.6723(3) 0.40334(17) 0.0533(7) Uani 1 1 d .
H4A H 1.0123 0.6834 0.4517 0.064 Uiso 1 1 calc R
C5 C 0.9169(3) 0.7499(3) 0.32843(17) 0.0607(8) Uani 1 1 d .
H5A H 1.0074 0.8152 0.3258 0.073 Uiso 1 1 calc R
C6 C 0.7829(3) 0.7324(2) 0.25736(15) 0.0473(6) Uani 1 1 d .
H6A H 0.7842 0.7844 0.2057 0.057 Uiso 1 1 calc R
C7 C 0.5050(3) 0.62386(19) 0.18010(13) 0.0331(4) Uani 1 1 d .
C8 C 0.3661(3) 0.5082(2) 0.37054(15) 0.0418(5) Uani 1 1 d .
C9 C 0.2183(3) 0.4094(3) 0.34831(17) 0.0580(8) Uani 1 1 d .
H9A H 0.1160 0.4520 0.3121 0.087 Uiso 1 1 calc R
H9B H 0.1800 0.3758 0.4028 0.087 Uiso 1 1 calc R
H9C H 0.2619 0.3357 0.3154 0.087 Uiso 1 1 calc R
N1 N 0.11606(19) 0.53488(14) 0.06328(11) 0.0318(4) Uani 1 1 d D
H1A H 0.2006 0.5606 0.1077 0.038 Uiso 1 1 d R
C1A C 0.2056(5) 0.4571(4) 0.0064(2) 0.0329(8) Uani 0.50 1 d PD
H1AA H 0.2458 0.3755 0.0348 0.039 Uiso 0.50 1 d PR
H1AB H 0.3079 0.5031 -0.0101 0.039 Uiso 0.50 1 d PR
C2A C 0.0246(5) 0.6538(3) 0.0294(2) 0.0288(8) Uani 0.50 1 d PD
H2AA H 0.1053 0.7107 0.0033 0.035 Uiso 0.50 1 d PR
H2AB H -0.0215 0.7013 0.0758 0.035 Uiso 0.50 1 d PR
C3A C -0.0196(5) 0.4500(4) 0.1059(2) 0.0311(8) Uani 0.50 1 d PD
H3AA H -0.0842 0.5029 0.1432 0.037 Uiso 0.50 1 d PR
H3AB H 0.0401 0.3791 0.1401 0.037 Uiso 0.50 1 d PR
C4A C -0.1282(5) 0.6084(3) -0.0408(3) 0.0314(8) Uani 0.50 1 d P
H4AA H -0.1285 0.6608 -0.0932 0.038 Uiso 0.50 1 d PR
H4AB H -0.2406 0.6230 -0.0190 0.038 Uiso 0.50 1 d PR
C5A C 0.0670(4) 0.4292(4) -0.0740(3) 0.0356(9) Uani 0.50 1 d P
H5AA H 0.0696 0.3367 -0.0882 0.043 Uiso 0.50 1 d PR
H5AB H 0.1009 0.4776 -0.1231 0.043 Uiso 0.50 1 d PR
C6A C -0.1498(5) 0.3963(4) 0.0256(2) 0.0335(8) Uani 0.50 1 d P
H6AA H -0.2725 0.4102 0.0349 0.040 Uiso 0.50 1 d PR
H6AB H -0.1314 0.3026 0.0206 0.040 Uiso 0.50 1 d PR
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_1
_geom_angle_site_symmetry_3
C8 O3 C2 115.71(14) . .
C2 C1 C6 117.50(17) . .
C2 C1 C7 123.88(16) . .
C6 C1 C7 118.59(17) . .
C3 C2 C1 122.05(17) . .
C3 C2 O3 118.58(16) . .
C1 C2 O3 119.25(16) . .
C4 C3 C2 119.35(18) . .
C4 C3 H3A 120.3 . .
C2 C3 H3A 120.3 . .
C3 C4 C5 119.9(2) . .
C3 C4 H4A 120.0 . .
C5 C4 H4A 120.0 . .
C6 C5 C4 120.1(2) . .
C6 C5 H5A 120.0 . .
C4 C5 H5A 120.0 . .
C5 C6 C1 121.09(19) . .
C5 C6 H6A 119.5 . .
C1 C6 H6A 119.5 . .
O2 C7 O1 125.28(18) . .
O2 C7 C1 119.26(17) . .
O1 C7 C1 115.45(17) . .
O4 C8 O3 122.50(18) . .
O4 C8 C9 126.4(2) . .
O3 C8 C9 111.08(18) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C1A N1 H1A 106.4 . .
C2A N1 H1A 106.2 . .
C3A N1 H1A 106.1 . .
C4A N1 H1A 113.3 3_565 .
C5A N1 H1A 114.8 3_565 .
C6A N1 H1A 110.0 3_565 .
C1A N1 C2A 119.0(3) . .
C1A N1 C3A 110.5(3) . .
C2A N1 C3A 107.8(2) . .
C5A N1 C4A 110.9(3) 3_565 3_565
C5A N1 C6A 104.7(2) 3_565 3_565
C4A N1 C6A 101.9(2) 3_565 3_565
N1 C1A C5A 105.8(2) . .
N1 C1A H1AA 110.2 . .
N1 C1A H1AB 111.1 . .
C5A C1A H1AA 110.0 . .
C5A C1A H1AB 110.9 . .
H1AA C1A H1AB 108.8 . .
N1 C2A C4A 106.0(2) . .
N1 C2A H2AA 110.6 . .
N1 C2A H2AB 110.6 . .
C4A C2A H2AA 110.0 . .
C4A C2A H2AB 111.0 . .
H2AA C2A H2AB 108.7 . .
N1 C3A C6A 103.7(2) . .
N1 C3A H3AA 111.1 . .
N1 C3A H3AB 111.2 . .
C6A C3A H3AA 110.5 . .
C6A C3A H3AB 111.3 . .
H3AA C3A H3AB 109.0 . .
N1 C4A C2A 112.9(3) 3_565 .
N1 C4A H4AA 109.6 3_565 .
N1 C4A H4AB 108.3 3_565 .
C2A C4A H4AA 109.6 . .
C2A C4A H4AB 108.5 . .
H4AA C4A H4AB 107.8 . .
N1 C5A C1A 114.4(3) 3_565 .
N1 C5A H5AA 108.6 3_565 .
N1 C5A H5AB 108.6 3_565 .
C1A C5A H5AA 109.3 . .
C1A C5A H5AB 108.2 . .
H5AA C5A H5AB 107.5 . .
C3A C6A N1 111.6(2) . 3_565
N1 C6A H6AA 109.6 3_565 .
N1 C6A H6AB 108.8 3_565 .
C3A C6A H6AA 109.9 . .
C3A C6A H6AB 109.0 . .
H6AA C6A H6AB 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.289(2) .
O2 C7 1.224(2) .
O3 C8 1.357(2) .
O3 C2 1.396(2) .
O4 C8 1.192(3) .
C1 C2 1.392(3) .
C1 C6 1.393(3) .
C1 C7 1.513(3) .
C2 C3 1.382(3) .
C3 C4 1.382(3) .
C3 H3A 0.950 .
C4 C5 1.386(3) .
C4 H4A 0.950 .
C5 C6 1.385(3) .
C5 H5A 0.950 .
C6 H6A 0.950 .
C8 C9 1.494(3) .
C9 H9A 0.980 .
C9 H9B 0.980 .
C9 H9C 0.980 .
N1 C1A 1.410(3) .
N1 C2A 1.443(3) .
N1 C5A 1.450(3) 3_565
N1 C4A 1.492(3) 3_565
N1 C3A 1.542(3) .
N1 C6A 1.579(3) 3_565
N1 H1A 0.900 .
C1A C5A 1.521(5) .
C1A H1AA 0.960 .
C1A H1AB 0.960 .
C2A C4A 1.526(5) .
C2A H2AA 0.960 .
C2A H2AB 0.960 .
C3A C6A 1.556(5) .
C3A H3AA 0.960 .
C3A H3AB 0.960 .
C4A N1 1.492(3) 3_565
C4A H4AA 0.960 .
C4A H4AB 0.960 .
C5A N1 1.450(3) 3_565
C5A H5AA 0.960 .
C5A H5AB 0.956 .
C6A N1 1.579(3) 3_565
C6A H6AA 0.960 .
C6A H6AB 0.960 .
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
N1 H1A O1 0.90 1.64 2.536(2) 171.1
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 C1 C2 C3 -1.3(3)
C7 C1 C2 C3 177.11(18)
C6 C1 C2 O3 -177.40(18)
C7 C1 C2 O3 1.0(3)
C8 O3 C2 C3 95.2(2)
C8 O3 C2 C1 -88.6(2)
C1 C2 C3 C4 2.1(3)
O3 C2 C3 C4 178.2(2)
C2 C3 C4 C5 -0.9(4)
C3 C4 C5 C6 -0.9(5)
C4 C5 C6 C1 1.7(5)
C2 C1 C6 C5 -0.6(4)
C7 C1 C6 C5 -179.1(2)
C2 C1 C7 O2 -150.7(2)
C6 C1 C7 O2 27.7(3)
C2 C1 C7 O1 30.4(3)
C6 C1 C7 O1 -151.2(2)
C2 O3 C8 O4 -17.7(3)
C2 O3 C8 C9 163.55(19)
