#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/96/7109669.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_7109669
loop_
_publ_author_name
'Srinu Tothadi'
'Gautam R. Desiraju'
_publ_section_title
;
 Designing ternary cocrystals with hydrogen bonds and halogen bonds
;
_journal_name_full               Chem.Commun.
_journal_page_first              7791
_journal_paper_doi               10.1039/c3cc43822h
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C9 H9 N2 O5'
_chemical_formula_weight         225.18
_chemical_name_common            '4-nitrobenzamide: succinic acid'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 107.206(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.134(8)
_cell_length_b                   5.1606(13)
_cell_length_c                   12.670(3)
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.2
_cell_volume                     1944.6(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from 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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9806
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'colour less'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0336
_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)+(0.0431P)²+1.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                2020
_reflns_number_total             2235
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3cc43822h.txt
_cod_data_source_block           datam
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7109669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
H4 H 0.3795(5) 0.525(3) 0.8074(11) 0.022(3) Uiso 1 1 d
H5 H 0.3320(5) 0.200(3) 0.8348(12) 0.026(4) Uiso 1 1 d
H7 H 0.3378(5) 0.378(3) 0.4762(11) 0.024(3) Uiso 1 1 d
H6 H 0.2886(5) 0.055(3) 0.5052(12) 0.026(4) Uiso 1 1 d
H3 H 0.4145(5) 0.830(3) 0.7613(13) 0.032(4) Uiso 1 1 d
H9 H 0.4596(5) 1.539(3) 0.4101(12) 0.036(4) Uiso 1 1 d
H8 H 0.4964(5) 1.334(3) 0.4068(13) 0.035(4) Uiso 1 1 d
H2 H 0.4356(5) 0.954(4) 0.6765(13) 0.041(4) Uiso 1 1 d
H1 H 0.4162(6) 0.968(4) 0.4693(15) 0.056(5) Uiso 1 1 d
O3 O 0.39561(3) 0.70707(17) 0.51603(6) 0.0255(2) Uani 1 1 d
O2 O 0.28463(3) -0.18357(17) 0.78711(7) 0.0271(2) Uani 1 1 d
O1 O 0.24717(3) -0.17865(18) 0.61328(7) 0.0311(2) Uani 1 1 d
O4 O 0.42749(3) 1.09784(18) 0.43581(7) 0.0267(2) Uani 1 1 d
C7 C 0.30718(3) 0.1030(2) 0.67291(9) 0.0176(2) Uani 1 1 d
C4 C 0.36324(4) 0.4816(2) 0.63711(8) 0.0172(2) Uani 1 1 d
O5 O 0.47090(4) 1.1784(2) 0.60653(7) 0.0403(3) Uani 1 1 d
N1 N 0.41684(3) 0.8359(2) 0.69353(8) 0.0224(2) Uani 1 1 d
N2 N 0.27741(3) -0.10187(18) 0.69270(8) 0.0200(2) Uani 1 1 d
C6 C 0.33347(4) 0.2381(2) 0.76273(9) 0.0191(2) Uani 1 1 d
C5 C 0.36149(4) 0.4306(2) 0.74425(9) 0.0189(2) Uani 1 1 d
C9 C 0.33633(4) 0.3404(2) 0.54858(9) 0.0207(2) Uani 1 1 d
C3 C 0.39334(4) 0.6852(2) 0.61236(9) 0.0180(2) Uani 1 1 d
C8 C 0.30759(4) 0.1499(2) 0.56555(9) 0.0210(2) Uani 1 1 d
C2 C 0.46017(4) 1.2235(2) 0.50897(9) 0.0219(2) Uani 1 1 d
C1 C 0.48253(4) 1.4241(2) 0.45713(9) 0.0233(3) Uani 1 1 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'
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
C2 O4 H1 110.7(11) . .
C6 C7 C8 123.12(10) . .
C6 C7 N2 118.14(10) . .
C8 C7 N2 118.74(10) . .
C9 C4 C5 119.79(10) . .
C9 C4 C3 117.54(9) . .
C5 C4 C3 122.67(10) . .
C3 N1 H3 123.3(10) . .
C3 N1 H2 117.0(10) . .
H3 N1 H2 119.6(14) . .
O1 N2 O2 124.49(10) . .
O1 N2 C7 117.51(9) . .
O2 N2 C7 118.01(9) . .
C7 C6 C5 118.20(10) . .
C7 C6 H5 120.3(9) . .
C5 C6 H5 121.5(9) . .
C6 C5 C4 120.34(10) . .
C6 C5 H4 117.5(8) . .
C4 C5 H4 122.1(8) . .
C8 C9 C4 120.53(10) . .
C8 C9 H7 120.8(9) . .
C4 C9 H7 118.6(9) . .
O3 C3 N1 121.90(10) . .
O3 C3 C4 119.12(10) . .
N1 C3 C4 118.98(10) . .
C7 C8 C9 118.00(10) . .
C7 C8 H6 120.9(9) . .
C9 C8 H6 121.1(9) . .
O5 C2 O4 123.07(11) . .
O5 C2 C1 123.94(10) . .
O4 C2 C1 112.98(9) . .
C2 C1 C1 111.80(12) . 5_686
C2 C1 H9 109.6(9) . .
C1 C1 H9 111.2(10) 5_686 .
C2 C1 H8 107.7(9) . .
C1 C1 H8 110.5(9) 5_686 .
H9 C1 H8 105.8(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C3 1.2484(13) .
O2 N2 1.2248(13) .
O1 N2 1.2229(13) .
O4 C2 1.3256(14) .
O4 H1 0.92(2) .
C7 C6 1.3785(15) .
C7 C8 1.3854(15) .
C7 N2 1.4754(14) .
C4 C9 1.3910(15) .
C4 C5 1.3994(15) .
C4 C3 1.5017(15) .
O5 C2 1.2039(14) .
N1 C3 1.3236(14) .
N1 H3 0.884(16) .
N1 H2 0.914(18) .
C6 C5 1.3871(16) .
C6 H5 0.949(14) .
C5 H4 0.961(14) .
C9 C8 1.3882(16) .
C9 H7 0.952(14) .
C8 H6 0.953(14) .
C2 C1 1.5026(15) .
C1 C1 1.509(2) 5_686
C1 H9 0.984(16) .
C1 H8 0.986(16) .
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_4
C6 C7 N2 O1 163.51(10) .
C8 C7 N2 O1 -16.75(15) .
C6 C7 N2 O2 -16.57(15) .
C8 C7 N2 O2 163.18(10) .
C8 C7 C6 C5 0.22(17) .
N2 C7 C6 C5 179.95(10) .
C7 C6 C5 C4 -0.99(16) .
C9 C4 C5 C6 0.75(17) .
C3 C4 C5 C6 -179.23(10) .
C5 C4 C9 C8 0.27(17) .
C3 C4 C9 C8 -179.74(10) .
C9 C4 C3 O3 -5.23(16) .
C5 C4 C3 O3 174.76(10) .
C9 C4 C3 N1 175.02(10) .
C5 C4 C3 N1 -4.99(16) .
C6 C7 C8 C9 0.78(17) .
N2 C7 C8 C9 -178.96(10) .
C4 C9 C8 C7 -1.01(17) .
O5 C2 C1 C1 -4.5(2) 5_686
O4 C2 C1 C1 176.27(13) 5_686
