#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228146.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_2228146
loop_
_publ_author_name
'Tai, Xiao-Xi'
'Sun, Jing'
_publ_section_title
;
 Isopropyl 4-chloro-3,5-dinitrobenzoate
;
_journal_coeditor_code           XU5065
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2986
_journal_paper_doi               10.1107/S160053681004359X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H9 Cl N2 O6'
_chemical_formula_moiety         'C10 H9 Cl N2 O6'
_chemical_formula_sum            'C10 H9 Cl N2 O6'
_chemical_formula_weight         288.64
_chemical_name_systematic
;
Isopropyl 4-chloro-3,5-dinitrobenzoate
;
_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           SHELXL97
_cell_angle_alpha                69.483(12)
_cell_angle_beta                 87.75(2)
_cell_angle_gamma                89.61(2)
_cell_formula_units_Z            2
_cell_length_a                   4.703(2)
_cell_length_b                   10.783(5)
_cell_length_c                   12.734(5)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.07
_cell_volume                     604.3(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5643
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.8298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0436
_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)+(0.0496P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1756
_reflns_number_total             2689
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5065.cif
_cod_data_source_block           I
_cod_database_code               2228146
_cod_database_fobs_code          2228146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.35262(13) 0.43193(6) 0.65836(5) 0.02487(18) Uani d . 1 . .
O O1 0.4518(3) 0.85871(15) 0.76139(13) 0.0185(4) Uani d . 1 . .
O O2 0.3137(3) 0.67501(15) 0.90566(13) 0.0208(4) Uani d . 1 . .
O O3 1.2776(4) 0.83028(19) 0.51714(14) 0.0338(5) Uani d . 1 . .
O O4 1.1930(4) 0.66488(19) 0.46231(15) 0.0359(5) Uani d . 1 . .
O O5 1.2157(4) 0.31097(18) 0.93908(16) 0.0343(5) Uani d . 1 . .
O O6 0.8756(4) 0.24121(18) 0.86381(17) 0.0364(5) Uani d . 1 . .
N N1 1.1805(4) 0.7201(2) 0.53094(17) 0.0240(5) Uani d . 1 . .
N N2 1.0218(4) 0.3277(2) 0.87522(18) 0.0226(5) Uani d . 1 . .
C C1 0.8350(5) 0.7223(2) 0.67783(18) 0.0170(5) Uani d . 1 . .
H H1 0.7969 0.8119 0.6342 0.020 Uiso calc R 1 . .
C C2 1.0341(5) 0.6512(2) 0.64011(18) 0.0182(5) Uani d . 1 . .
C C3 1.1009(5) 0.5203(2) 0.7020(2) 0.0187(5) Uani d . 1 . .
C C4 0.9569(5) 0.4649(2) 0.80468(19) 0.0170(5) Uani d . 1 . .
C C5 0.7538(5) 0.5317(2) 0.8453(2) 0.0177(5) Uani d . 1 . .
H H5 0.6590 0.4898 0.9161 0.021 Uiso calc R 1 . .
C C6 0.6914(5) 0.6612(2) 0.78022(19) 0.0165(5) Uani d . 1 . .
C C7 0.4638(5) 0.7312(2) 0.82410(19) 0.0160(5) Uani d . 1 . .
C C8 0.2407(5) 0.9393(2) 0.7970(2) 0.0188(5) Uani d . 1 . .
H H8 0.0665 0.8848 0.8302 0.023 Uiso calc R 1 . .
C C9 0.3717(6) 0.9834(3) 0.8837(2) 0.0288(6) Uani d . 1 . .
H H9A 0.4320 0.9057 0.9461 0.043 Uiso calc R 1 . .
H H9B 0.2316 1.0332 0.9117 0.043 Uiso calc R 1 . .
H H9C 0.5372 1.0401 0.8500 0.043 Uiso calc R 1 . .
C C10 0.1679(6) 1.0513(2) 0.6922(2) 0.0290(6) Uani d . 1 . .
H H10A 0.3399 1.1034 0.6591 0.043 Uiso calc R 1 . .
H H10B 0.0261 1.1082 0.7108 0.043 Uiso calc R 1 . .
H H10C 0.0902 1.0155 0.6383 0.043 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C8 . . 116.83(18) ?
O4 N1 O3 . . 125.7(2) ?
O4 N1 C2 . . 118.2(2) ?
O3 N1 C2 . . 116.1(2) ?
O6 N2 O5 . . 125.8(2) ?
O6 N2 C4 . . 116.5(2) ?
O5 N2 C4 . . 117.61(19) ?
C2 C1 C6 . . 119.1(2) ?
C2 C1 H1 . . 120.4 ?
C6 C1 H1 . . 120.4 ?
C1 C2 C3 . . 122.5(2) ?
C1 C2 N1 . . 117.2(2) ?
C3 C2 N1 . . 120.3(2) ?
C4 C3 C2 . . 116.1(2) ?
C4 C3 Cl1 . . 120.62(18) ?
C2 C3 Cl1 . . 123.26(19) ?
C5 C4 C3 . . 123.4(2) ?
C5 C4 N2 . . 117.8(2) ?
C3 C4 N2 . . 118.8(2) ?
C4 C5 C6 . . 118.5(2) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C1 C6 C5 . . 120.3(2) ?
C1 C6 C7 . . 121.8(2) ?
C5 C6 C7 . . 117.9(2) ?
O2 C7 O1 . . 125.9(2) ?
O2 C7 C6 . . 122.6(2) ?
O1 C7 C6 . . 111.5(2) ?
O1 C8 C9 . . 107.98(19) ?
O1 C8 C10 . . 105.83(19) ?
C9 C8 C10 . . 113.8(2) ?
O1 C8 H8 . . 109.7 ?
C9 C8 H8 . . 109.7 ?
C10 C8 H8 . . 109.7 ?
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 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.709(2) ?
O1 C7 . 1.328(3) ?
O1 C8 . 1.475(3) ?
O2 C7 . 1.205(3) ?
O3 N1 . 1.227(3) ?
O4 N1 . 1.217(3) ?
O5 N2 . 1.216(3) ?
O6 N2 . 1.215(3) ?
N1 C2 . 1.472(3) ?
N2 C4 . 1.474(3) ?
C1 C2 . 1.382(3) ?
C1 C6 . 1.388(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.395(3) ?
C3 C4 . 1.384(3) ?
C4 C5 . 1.382(3) ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.505(3) ?
C8 C9 . 1.500(3) ?
C8 C10 . 1.503(3) ?
C8 H8 . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 O2 2_667 0.95 2.35 3.178(3) 146 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(3) ?
C6 C1 C2 N1 . . . . 179.8(2) ?
O4 N1 C2 C1 . . . . -131.1(2) ?
O3 N1 C2 C1 . . . . 48.2(3) ?
O4 N1 C2 C3 . . . . 49.9(3) ?
O3 N1 C2 C3 . . . . -130.8(2) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
N1 C2 C3 C4 . . . . 178.6(2) ?
C1 C2 C3 Cl1 . . . . -178.36(18) ?
N1 C2 C3 Cl1 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . 1.2(3) ?
Cl1 C3 C4 C5 . . . . 179.18(18) ?
C2 C3 C4 N2 . . . . -178.78(19) ?
Cl1 C3 C4 N2 . . . . -0.8(3) ?
O6 N2 C4 C5 . . . . 87.9(3) ?
O5 N2 C4 C5 . . . . -92.3(3) ?
O6 N2 C4 C3 . . . . -92.1(3) ?
O5 N2 C4 C3 . . . . 87.7(3) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
N2 C4 C5 C6 . . . . 179.6(2) ?
C2 C1 C6 C5 . . . . 2.0(3) ?
C2 C1 C6 C7 . . . . -177.5(2) ?
C4 C5 C6 C1 . . . . -1.3(3) ?
C4 C5 C6 C7 . . . . 178.3(2) ?
C8 O1 C7 O2 . . . . 1.9(3) ?
C8 O1 C7 C6 . . . . -178.73(17) ?
C1 C6 C7 O2 . . . . 170.8(2) ?
C5 C6 C7 O2 . . . . -8.8(3) ?
C1 C6 C7 O1 . . . . -8.7(3) ?
C5 C6 C7 O1 . . . . 171.78(19) ?
C7 O1 C8 C9 . . . . 84.7(2) ?
C7 O1 C8 C10 . . . . -153.16(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3628085
