#------------------------------------------------------------------------------
#$Date: 2019-09-18 14:05:15 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200219.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_7200219
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+, 2(C7 H5 O2 -)'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2621(6)
_cell_length_b                   11.5931(7)
_cell_length_c                   34.720(2)
_cell_measurement_reflns_used    8532
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.49
_cell_volume                     3728.1(4)
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT 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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            37128
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.906444
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0377
_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)+(0.0516P)²+1.1313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                2450
_reflns_number_total             3280
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            B810660F.txt
_cod_data_source_block           1b
_cod_depositor_comments
;
 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_database_code               7200219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.62430(14) 0.71555(10) 0.52862(3) 0.0415(3) Uani 1 1 d . . .
O12 O 0.70126(15) 0.88532(11) 0.50677(4) 0.0515(4) Uani 1 1 d . . .
C11 C 0.65070(16) 0.86692(13) 0.57368(5) 0.0263(4) Uani 1 1 d . . .
C12 C 0.66633(18) 0.98394(14) 0.58139(5) 0.0339(4) Uani 1 1 d . . .
H12 H 0.6824 1.0367 0.5609 0.041 Uiso 1 1 calc R . .
C13 C 0.6584(2) 1.02352(15) 0.61890(6) 0.0410(5) Uani 1 1 d . . .
H13 H 0.6675 1.1037 0.6239 0.049 Uiso 1 1 calc R . .
C14 C 0.63763(19) 0.94803(16) 0.64914(5) 0.0407(5) Uani 1 1 d . . .
H14 H 0.6338 0.9760 0.6748 0.049 Uiso 1 1 calc R . .
C15 C 0.62248(18) 0.83151(15) 0.64176(5) 0.0363(4) Uani 1 1 d . . .
H15 H 0.6085 0.7788 0.6624 0.044 Uiso 1 1 calc R . .
C16 C 0.62773(16) 0.79184(14) 0.60411(5) 0.0295(4) Uani 1 1 d . . .
H16 H 0.6154 0.7119 0.5991 0.035 Uiso 1 1 calc R . .
C17 C 0.66015(17) 0.82169(14) 0.53297(5) 0.0314(4) Uani 1 1 d . . .
O21 O 0.60186(13) 0.49417(10) 0.32203(3) 0.0390(3) Uani 1 1 d . . .
O22 O 0.74375(16) 0.35852(11) 0.34651(4) 0.0497(4) Uani 1 1 d . . .
C21 C 0.64306(17) 0.32735(14) 0.28433(5) 0.0305(4) Uani 1 1 d . . .
C22 C 0.56765(18) 0.37365(14) 0.25345(5) 0.0348(4) Uani 1 1 d . . .
H22 H 0.5294 0.4495 0.2551 0.042 Uiso 1 1 calc R . .
C23 C 0.5480(2) 0.30976(16) 0.22030(5) 0.0435(5) Uani 1 1 d . . .
H23 H 0.4963 0.3417 0.1992 0.052 Uiso 1 1 calc R . .
C24 C 0.6037(2) 0.19944(17) 0.21782(6) 0.0478(5) Uani 1 1 d . . .
H24 H 0.5906 0.1556 0.1950 0.057 Uiso 1 1 calc R . .
C25 C 0.6782(2) 0.15276(16) 0.24849(6) 0.0481(5) Uani 1 1 d . . .
H25 H 0.7156 0.0766 0.2468 0.058 Uiso 1 1 calc R . .
C26 C 0.69835(19) 0.21636(15) 0.28154(5) 0.0391(4) Uani 1 1 d . . .
H26 H 0.7503 0.1841 0.3025 0.047 Uiso 1 1 calc R . .
C27 C 0.66772(18) 0.39431(14) 0.32042(5) 0.0317(4) Uani 1 1 d . . .
N31 N 0.62860(13) 0.58570(10) 0.38926(4) 0.0256(3) Uani 1 1 d . . .
H31C H 0.6277 0.5610 0.3638 0.031 Uiso 1 1 calc R . .
N32 N 0.63070(14) 0.65198(11) 0.45826(4) 0.0296(3) Uani 1 1 d . . .
H32C H 0.6313 0.6765 0.4838 0.036 Uiso 1 1 calc R . .
C31 C 0.57085(19) 0.49412(13) 0.41433(5) 0.0321(4) Uani 1 1 d . . .
H31B H 0.6357 0.4263 0.4136 0.038 Uiso 1 1 calc R . .
H31A H 0.4746 0.4699 0.4049 0.038 Uiso 1 1 calc R . .
C32 C 0.55844(18) 0.53818(14) 0.45563(5) 0.0313(4) Uani 1 1 d . . .
H32B H 0.4555 0.5457 0.4629 0.038 Uiso 1 1 calc R . .
H32A H 0.6048 0.4830 0.4735 0.038 Uiso 1 1 calc R . .
C33 C 0.78171(17) 0.64106(15) 0.44420(5) 0.0338(4) Uani 1 1 d . . .
H33B H 0.8320 0.5787 0.4583 0.041 Uiso 1 1 calc R . .
H33A H 0.8346 0.7141 0.4486 0.041 Uiso 1 1 calc R . .
C34 C 0.77770(16) 0.61320(14) 0.40100(5) 0.0313(4) Uani 1 1 d . . .
H34B H 0.8133 0.6802 0.3861 0.038 Uiso 1 1 calc R . .
H34A H 0.8415 0.5467 0.3955 0.038 Uiso 1 1 calc R . .
C35 C 0.55176(18) 0.73737(14) 0.43428(5) 0.0323(4) Uani 1 1 d . . .
H35B H 0.6050 0.8114 0.4338 0.039 Uiso 1 1 calc R . .
H35A H 0.4547 0.7515 0.4453 0.039 Uiso 1 1 calc R . .
C36 C 0.53792(17) 0.68955(13) 0.39334(4) 0.0292(4) Uani 1 1 d . . .
H36B H 0.4359 0.6699 0.3880 0.035 Uiso 1 1 calc R . .
H36A H 0.5689 0.7487 0.3745 0.035 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'
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
_geom_angle_publ_flag
C16 C11 C12 118.84(15) . . ?
C16 C11 C17 120.30(14) . . ?
C12 C11 C17 120.86(15) . . ?
C13 C12 C11 119.97(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.89(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.53(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.69(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 121.06(15) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
O12 C17 O11 124.55(16) . . ?
O12 C17 C11 120.09(15) . . ?
O11 C17 C11 115.35(15) . . ?
C22 C21 C26 119.37(16) . . ?
C22 C21 C27 121.66(14) . . ?
C26 C21 C27 118.97(15) . . ?
C23 C22 C21 120.18(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.96(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.12(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.08(17) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.29(17) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
O22 C27 O21 122.55(16) . . ?
O22 C27 C21 122.35(15) . . ?
O21 C27 C21 115.10(14) . . ?
C31 N31 C34 109.42(12) . . ?
C31 N31 C36 108.95(12) . . ?
C34 N31 C36 109.29(12) . . ?
C31 N31 H31C 109.7 . . ?
C34 N31 H31C 109.7 . . ?
C36 N31 H31C 109.7 . . ?
C32 N32 C35 109.67(12) . . ?
C32 N32 C33 109.20(12) . . ?
C35 N32 C33 109.62(13) . . ?
C32 N32 H32C 109.4 . . ?
C35 N32 H32C 109.4 . . ?
C33 N32 H32C 109.4 . . ?
N31 C31 C32 109.94(12) . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
H31B C31 H31A 108.2 . . ?
N32 C32 C31 108.75(12) . . ?
N32 C32 H32B 109.9 . . ?
C31 C32 H32B 109.9 . . ?
N32 C32 H32A 109.9 . . ?
C31 C32 H32A 109.9 . . ?
H32B C32 H32A 108.3 . . ?
N32 C33 C34 108.41(13) . . ?
N32 C33 H33B 110.0 . . ?
C34 C33 H33B 110.0 . . ?
N32 C33 H33A 110.0 . . ?
C34 C33 H33A 110.0 . . ?
H33B C33 H33A 108.4 . . ?
N31 C34 C33 109.77(12) . . ?
N31 C34 H34B 109.7 . . ?
C33 C34 H34B 109.7 . . ?
N31 C34 H34A 109.7 . . ?
C33 C34 H34A 109.7 . . ?
H34B C34 H34A 108.2 . . ?
N32 C35 C36 108.66(12) . . ?
N32 C35 H35B 110.0 . . ?
C36 C35 H35B 110.0 . . ?
N32 C35 H35A 110.0 . . ?
C36 C35 H35A 110.0 . . ?
H35B C35 H35A 108.3 . . ?
N31 C36 C35 109.70(12) . . ?
N31 C36 H36B 109.7 . . ?
C35 C36 H36B 109.7 . . ?
N31 C36 H36A 109.7 . . ?
C35 C36 H36A 109.7 . . ?
H36B C36 H36A 108.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C17 1.283(2) . ?
O12 C17 1.232(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.390(2) . ?
C11 C17 1.510(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.950 . ?
C13 C14 1.380(3) . ?
C13 H13 0.950 . ?
C14 C15 1.382(3) . ?
C14 H14 0.950 . ?
C15 C16 1.387(2) . ?
C15 H15 0.950 . ?
C16 H16 0.950 . ?
O21 C27 1.3098(19) . ?
O22 C27 1.220(2) . ?
C21 C22 1.387(2) . ?
C21 C26 1.388(2) . ?
C21 C27 1.492(2) . ?
C22 C23 1.381(2) . ?
C22 H22 0.950 . ?
C23 C24 1.382(3) . ?
C23 H23 0.950 . ?
C24 C25 1.379(3) . ?
C24 H24 0.950 . ?
C25 C26 1.377(3) . ?
C25 H25 0.950 . ?
C26 H26 0.950 . ?
N31 C31 1.4733(19) . ?
N31 C34 1.475(2) . ?
N31 C36 1.4747(19) . ?
N31 H31C 0.930 . ?
N32 C32 1.482(2) . ?
N32 C35 1.486(2) . ?
N32 C33 1.487(2) . ?
N32 H32C 0.930 . ?
C31 C32 1.527(2) . ?
C31 H31B 0.990 . ?
C31 H31A 0.990 . ?
C32 H32B 0.990 . ?
C32 H32A 0.990 . ?
C33 C34 1.535(2) . ?
C33 H33B 0.990 . ?
C33 H33A 0.990 . ?
C34 H34B 0.990 . ?
C34 H34A 0.990 . ?
C35 C36 1.531(2) . ?
C35 H35B 0.990 . ?
C35 H35A 0.990 . ?
C36 H36B 0.990 . ?
C36 H36A 0.990 . ?
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
N31 H31C O21 0.93 1.66 2.5762(17) 167.2 .
N32 H32C O11 0.93 1.62 2.5526(17) 176.9 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.2(2) . . . . ?
C17 C11 C12 C13 -179.50(15) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 -1.0(2) . . . . ?
C17 C11 C16 C15 178.32(14) . . . . ?
C14 C15 C16 C11 1.2(2) . . . . ?
C16 C11 C17 O12 -169.37(15) . . . . ?
C12 C11 C17 O12 9.9(2) . . . . ?
C16 C11 C17 O11 10.0(2) . . . . ?
C12 C11 C17 O11 -170.67(15) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
C27 C21 C22 C23 179.32(16) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C27 C21 C26 C25 -179.56(16) . . . . ?
C22 C21 C27 O22 -173.80(17) . . . . ?
C26 C21 C27 O22 5.6(3) . . . . ?
C22 C21 C27 O21 6.2(2) . . . . ?
C26 C21 C27 O21 -174.45(15) . . . . ?
C34 N31 C31 C32 64.98(16) . . . . ?
C36 N31 C31 C32 -54.44(17) . . . . ?
C35 N32 C32 C31 65.17(16) . . . . ?
C33 N32 C32 C31 -54.97(17) . . . . ?
N31 C31 C32 N32 -9.16(18) . . . . ?
C32 N32 C33 C34 66.16(16) . . . . ?
C35 N32 C33 C34 -54.01(17) . . . . ?
C31 N31 C34 C33 -53.39(16) . . . . ?
C36 N31 C34 C33 65.83(16) . . . . ?
N32 C33 C34 N31 -10.22(18) . . . . ?
C32 N32 C35 C36 -53.96(16) . . . . ?
C33 N32 C35 C36 65.92(16) . . . . ?
C31 N31 C36 C35 65.70(16) . . . . ?
C34 N31 C36 C35 -53.81(16) . . . . ?
N32 C35 C36 N31 -10.06(17) . . . . ?
