#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:15:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180384 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/53/7205318.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_7205318
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Solvates and polymorphic phase transformations of
 2-chloro-4-nitrobenzoic acid
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              1037
_journal_paper_doi               10.1039/c0ce00361a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C7 H4 Cl N O4, C8 H8 O'
_chemical_formula_sum            'C15 H12 Cl N O5'
_chemical_formula_weight         321.71
_chemical_name_common
;
acetophenone solvate of 2-chloro-4-nitrobenzoic acid
;
_chemical_name_systematic
;
acetophenone solvate of 2-chloro-4-nitrobenzoic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.67(3)
_cell_angle_beta                 77.63(3)
_cell_angle_gamma                81.03(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8156(12)
_cell_length_b                   10.387(2)
_cell_length_c                   12.207(2)
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.8149
_cell_measurement_theta_min      2.5217
_cell_volume                     709.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       '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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10021
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9491
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0400
_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)+(0.0625P)²+0.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                3300
_reflns_number_total             3477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00361A.TXT
_cod_data_source_block           CNBA-Acetophenone
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        709.2(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 1.15380(6) 0.35605(3) 0.43986(3) 0.02388(12) Uani 1 1 d . . .
O2 O 0.6536(2) 0.36420(11) 0.54491(10) 0.0261(2) Uani 1 1 d . . .
O1 O 0.5254(2) 0.17054(11) 0.60204(10) 0.0287(3) Uani 1 1 d . . .
O4 O 1.5313(2) 0.01145(12) 0.16170(10) 0.0305(3) Uani 1 1 d . . .
O5 O -0.3641(2) 0.52341(12) 0.28334(10) 0.0334(3) Uani 1 1 d . . .
O3 O 1.2712(2) -0.11209(13) 0.15087(11) 0.0382(3) Uani 1 1 d . . .
C2 C 1.0625(2) 0.22173(13) 0.39837(12) 0.0180(3) Uani 1 1 d . . .
C3 C 1.2239(2) 0.15455(14) 0.31599(12) 0.0197(3) Uani 1 1 d . . .
H3 H 1.3749 0.1819 0.2862 0.024 Uiso 1 1 calc R . .
C1 C 0.8419(2) 0.17949(13) 0.44432(11) 0.0184(3) Uani 1 1 d . . .
C8 C -0.0400(3) 0.42380(13) 0.15706(11) 0.0193(3) Uani 1 1 d . . .
N1 N 1.3339(2) -0.02330(12) 0.19049(11) 0.0243(3) Uani 1 1 d . . .
C4 C 1.1606(2) 0.04692(14) 0.27808(12) 0.0199(3) Uani 1 1 d . . .
C7 C 0.6579(2) 0.23761(14) 0.53901(12) 0.0204(3) Uani 1 1 d . . .
C5 C 0.9434(3) 0.00349(14) 0.31843(12) 0.0215(3) Uani 1 1 d . . .
H5 H 0.9024 -0.0692 0.2896 0.026 Uiso 1 1 calc R . .
C9 C -0.1715(3) 0.32779(14) 0.14177(12) 0.0216(3) Uani 1 1 d . . .
H9 H -0.3321 0.3295 0.1804 0.026 Uiso 1 1 calc R . .
C14 C -0.1576(3) 0.52713(14) 0.23425(12) 0.0223(3) Uani 1 1 d . . .
C13 C 0.1960(3) 0.41975(15) 0.10053(13) 0.0236(3) Uani 1 1 d . . .
H13 H 0.2871 0.4843 0.1106 0.028 Uiso 1 1 calc R . .
C6 C 0.7878(3) 0.07000(14) 0.40260(12) 0.0209(3) Uani 1 1 d . . .
H6 H 0.6390 0.0403 0.4331 0.025 Uiso 1 1 calc R . .
C11 C 0.1653(3) 0.22687(15) 0.01430(13) 0.0259(3) Uani 1 1 d . . .
H11 H 0.2351 0.1600 -0.0345 0.031 Uiso 1 1 calc R . .
C15 C -0.0240(3) 0.63312(15) 0.25021(13) 0.0280(3) Uani 1 1 d . . .
H15A H -0.1283 0.6943 0.3009 0.042 Uiso 1 1 calc R . .
H15B H 0.0304 0.6799 0.1773 0.042 Uiso 1 1 calc R . .
H15C H 0.1135 0.5947 0.2829 0.042 Uiso 1 1 calc R . .
C10 C -0.0695(3) 0.23025(15) 0.07063(13) 0.0255(3) Uani 1 1 d . . .
H10 H -0.1603 0.1656 0.0604 0.031 Uiso 1 1 calc R . .
C12 C 0.2985(3) 0.32148(16) 0.02937(13) 0.0263(3) Uani 1 1 d . . .
H12 H 0.4594 0.3190 -0.0089 0.032 Uiso 1 1 calc R . .
H1 H 0.541(5) 0.390(3) 0.605(2) 0.056(7) Uiso 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'
Cl Cl 0.1484 0.1585 '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
C7 O2 H1 108.3(16) . . ?
C3 C2 C1 120.65(13) . . ?
C3 C2 Cl1 115.82(11) . . ?
C1 C2 Cl1 123.52(11) . . ?
C4 C3 C2 118.73(13) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C6 C1 C2 118.03(13) . . ?
C6 C1 C7 115.82(12) . . ?
C2 C1 C7 126.09(13) . . ?
C13 C8 C9 119.24(14) . . ?
C13 C8 C14 122.17(13) . . ?
C9 C8 C14 118.58(13) . . ?
O3 N1 O4 124.21(13) . . ?
O3 N1 C4 117.98(13) . . ?
O4 N1 C4 117.80(13) . . ?
C5 C4 C3 122.85(13) . . ?
C5 C4 N1 119.08(13) . . ?
C3 C4 N1 118.07(12) . . ?
O1 C7 O2 124.53(14) . . ?
O1 C7 C1 120.75(13) . . ?
O2 C7 C1 114.71(12) . . ?
C4 C5 C6 117.39(13) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C10 C9 C8 120.48(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O5 C14 C8 118.91(13) . . ?
O5 C14 C15 121.16(14) . . ?
C8 C14 C15 119.93(13) . . ?
C12 C13 C8 120.23(14) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C5 C6 C1 122.31(13) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C10 C11 C12 120.00(14) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C10 C11 120.04(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C13 C12 C11 120.00(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
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
Cl1 C2 1.7284(14) . ?
O2 C7 1.3210(18) . ?
O2 H1 0.90(3) . ?
O1 C7 1.2109(18) . ?
O4 N1 1.2247(18) . ?
O5 C14 1.2262(19) . ?
O3 N1 1.2233(18) . ?
C2 C3 1.388(2) . ?
C2 C1 1.4021(19) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C1 C6 1.400(2) . ?
C1 C7 1.506(2) . ?
C8 C13 1.394(2) . ?
C8 C9 1.398(2) . ?
C8 C14 1.492(2) . ?
N1 C4 1.4737(19) . ?
C4 C5 1.380(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C14 C15 1.494(2) . ?
C13 C12 1.391(2) . ?
C13 H13 0.9500 . ?
C6 H6 0.9500 . ?
C11 C10 1.388(2) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
