#------------------------------------------------------------------------------
#$Date: 2014-05-02 08:48:16 +0300 (Fri, 02 May 2014) $
#$Revision: 112522 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215558.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_7215558
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_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              444
_journal_paper_doi               10.1039/b810660f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         '2(C7 H6 O2), C4 H5 N3'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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            4
_cell_length_a                   12.5428(10)
_cell_length_b                   34.337(3)
_cell_length_c                   3.8730(3)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      3.25
_cell_volume                     1668.0(2)
_computing_cell_refinement       'SAINTPLUS v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINTPLUS 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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice \w and \f 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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            9518
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.755826
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0306
_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/[\s^2^(Fo^2^)+(0.0332P)^2^+0.4122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1200
_reflns_number_total             1508
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    b810660f.cif
_[local]_cod_data_source_block   3b
_cod_database_code               7215558
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
O11 O 0.33311(7) 0.67286(3) 0.1984(3) 0.0403(3) Uani 1 1 d .
O12 O 0.16990(7) 0.64779(3) 0.2397(3) 0.0414(3) Uani 1 1 d .
H12 H 0.1462(14) 0.6745(6) 0.148(5) 0.080(6) Uiso 1 1 d .
C11 C 0.31410(10) 0.60805(4) 0.4036(3) 0.0296(3) Uani 1 1 d .
C12 C 0.24409(11) 0.58006(4) 0.5299(3) 0.0349(3) Uani 1 1 d .
H12A H 0.1695 0.5849 0.5298 0.042 Uiso 1 1 calc R
C13 C 0.28281(13) 0.54526(4) 0.6553(4) 0.0418(4) Uani 1 1 d .
H13A H 0.2349 0.5263 0.7440 0.050 Uiso 1 1 calc R
C14 C 0.39075(14) 0.53789(4) 0.6524(4) 0.0453(4) Uani 1 1 d .
H14A H 0.4171 0.5138 0.7376 0.054 Uiso 1 1 calc R
C15 C 0.46068(12) 0.56547(4) 0.5259(4) 0.0441(4) Uani 1 1 d .
H15A H 0.5351 0.5603 0.5231 0.053 Uiso 1 1 calc R
C16 C 0.42268(11) 0.60065(4) 0.4034(4) 0.0362(4) Uani 1 1 d .
H16A H 0.4710 0.6197 0.3191 0.043 Uiso 1 1 calc R
C17 C 0.27409(10) 0.64598(4) 0.2708(3) 0.0304(3) Uani 1 1 d .
N2 N 0.09752(8) 0.71530(3) 0.0147(3) 0.0278(3) Uani 1 1 d .
N3 N 0.22947(12) 0.7500 0.2890(4) 0.0303(4) Uani 1 2 d S
H31 H 0.2660(11) 0.7283(4) 0.306(4) 0.041(4) Uiso 1 1 d .
C1 C 0.14033(13) 0.7500 0.0997(4) 0.0249(4) Uani 1 2 d S
C2 C 0.00671(10) 0.71590(4) -0.1645(3) 0.0314(3) Uani 1 1 d .
H2A H -0.0252 0.6919 -0.2286 0.038 Uiso 1 1 calc R
C3 C -0.04243(14) 0.7500 -0.2597(5) 0.0331(5) Uani 1 2 d S
H3A H -0.1074 0.7500 -0.3856 0.040 Uiso 1 2 calc SR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0354(5) 0.0294(5) 0.0562(7) 0.0052(5) 0.0034(5) -0.0056(4)
O12 0.0304(5) 0.0329(5) 0.0608(7) 0.0113(5) -0.0037(5) -0.0046(4)
C11 0.0374(8) 0.0271(7) 0.0242(7) -0.0041(5) -0.0016(6) -0.0029(6)
C12 0.0429(8) 0.0314(7) 0.0305(7) -0.0021(6) 0.0022(6) -0.0033(6)
C13 0.0633(10) 0.0288(7) 0.0333(8) 0.0008(6) 0.0026(7) -0.0035(7)
C14 0.0707(11) 0.0316(8) 0.0335(9) -0.0025(6) -0.0089(8) 0.0104(7)
C15 0.0481(9) 0.0422(9) 0.0421(9) -0.0106(7) -0.0116(7) 0.0103(7)
C16 0.0381(8) 0.0340(8) 0.0365(8) -0.0059(6) -0.0033(6) -0.0024(6)
C17 0.0324(7) 0.0287(7) 0.0303(7) -0.0019(6) 0.0012(6) -0.0065(6)
N2 0.0251(6) 0.0322(6) 0.0260(6) 0.0005(5) 0.0021(5) -0.0030(5)
N3 0.0274(9) 0.0277(9) 0.0359(10) 0.000 -0.0041(7) 0.000
C1 0.0238(9) 0.0311(10) 0.0196(9) 0.000 0.0048(7) 0.000
C2 0.0286(7) 0.0402(8) 0.0255(7) -0.0025(6) 0.0031(6) -0.0068(6)
C3 0.0243(9) 0.0478(12) 0.0271(10) 0.000 -0.0022(8) 0.000
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
C17 O12 H12 111.2(10) . .
C16 C11 C12 119.62(13) . .
C16 C11 C17 119.47(12) . .
C12 C11 C17 120.91(12) . .
C13 C12 C11 120.04(14) . .
C13 C12 H12A 120.0 . .
C11 C12 H12A 120.0 . .
C14 C13 C12 120.18(14) . .
C14 C13 H13A 119.9 . .
C12 C13 H13A 119.9 . .
C13 C14 C15 120.10(14) . .
C13 C14 H14A 120.0 . .
C15 C14 H14A 120.0 . .
C14 C15 C16 120.14(14) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C15 C16 C11 119.92(14) . .
C15 C16 H16A 120.0 . .
C11 C16 H16A 120.0 . .
O11 C17 O12 123.27(12) . .
O11 C17 C11 122.61(12) . .
O12 C17 C11 114.12(11) . .
C2 N2 C1 116.97(12) . .
C1 N3 H31 118.6(10) . .
N3 C1 N2 117.85(8) . 7_575
N3 C1 N2 117.84(8) . .
N2 C1 N2 124.28(16) 7_575 .
N2 C2 C3 122.41(13) . .
N2 C2 H2A 118.8 . .
C3 C2 H2A 118.8 . .
C2 C3 C2 116.95(17) . 7_575
C2 C3 H3A 121.5 . .
C2 C3 H3A 121.5 7_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O11 C17 1.2159(15)
O12 C17 1.3138(16)
O12 H12 1.03(2)
C11 C16 1.3854(18)
C11 C12 1.3907(19)
C11 C17 1.4875(18)
C12 C13 1.3783(19)
C12 H12A 0.950
C13 C14 1.377(2)
C13 H13A 0.950
C14 C15 1.380(2)
C14 H14A 0.950
C15 C16 1.383(2)
C15 H15A 0.950
C16 H16A 0.950
N2 C2 1.3340(16)
N2 C1 1.3477(13)
N3 C1 1.337(2)
N3 H31 0.877(13)
C2 C3 1.3736(16)
C2 H2A 0.950
C3 H3A 0.950
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
O12 H12 N2 1.03(2) 1.61(2) 2.6376(14) 174.4(17)
N3 H31 O11 0.877(13) 2.123(14) 2.9714(12) 162.6(14)