#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/24/8102464.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_8102464
loop_
_publ_author_name
'Sanjun Zhi'
_publ_section_title
;
 Crystal structure of
 1-(2-chloro-1-(4-chlorophenyl)-2-nitropropyl)pyrrolidine-2,5-dione,
 C13H12Cl2N2O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              451
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C13 H12 Cl2 N2 O4'
_chemical_formula_sum            'C13 H12 Cl2 N2 O4'
_chemical_formula_weight         331.15
_chemical_melting_point          391
_chemical_name_systematic
; 
 1-(2-chloro-1-(4-chlorophenyl)-2-nitropropyl)pyrrolidine-2,5-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-05-03 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.811(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8902(14)
_cell_length_b                   12.817(3)
_cell_length_c                   16.680(3)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.49
_cell_volume                     1441.9(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7720
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.8962
_exptl_absorpt_correction_T_min  0.8727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0631
_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)+(0.06P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                1847
_reflns_number_total             2828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2646.cff
_cod_data_source_block           New_Global_Publ_Block
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8584(5) 0.7389(3) 0.61224(19) 0.0329(7) Uani 1 1 d . . .
C2 C 0.7106(5) 0.7445(3) 0.5328(2) 0.0417(9) Uani 1 1 d . . .
H2A H 0.7587 0.7890 0.4940 0.050 Uiso 1 1 calc R . .
H2B H 0.5849 0.7717 0.5412 0.050 Uiso 1 1 calc R . .
C3 C 0.6882(6) 0.6331(3) 0.5022(2) 0.0466(9) Uani 1 1 d . . .
H3A H 0.5492 0.6150 0.4850 0.056 Uiso 1 1 calc R . .
H3B H 0.7528 0.6237 0.4563 0.056 Uiso 1 1 calc R . .
C4 C 0.7854(5) 0.5669(3) 0.5734(2) 0.0366(8) Uani 1 1 d . . .
C5 C 1.0058(4) 0.5900(2) 0.70856(17) 0.0259(6) Uani 1 1 d . . .
H5 H 0.9938 0.5146 0.6995 0.031 Uiso 1 1 calc R . .
C6 C 0.9233(4) 0.6060(2) 0.78539(18) 0.0276(7) Uani 1 1 d . . .
C7 C 0.8472(4) 0.7006(3) 0.80699(19) 0.0315(7) Uani 1 1 d . . .
H7 H 0.8482 0.7590 0.7739 0.038 Uiso 1 1 calc R . .
C8 C 0.7705(5) 0.7081(3) 0.8773(2) 0.0357(7) Uani 1 1 d . . .
H8 H 0.7199 0.7712 0.8915 0.043 Uiso 1 1 calc R . .
C9 C 0.7696(5) 0.6209(3) 0.92620(19) 0.0351(7) Uani 1 1 d . . .
C10 C 0.8387(5) 0.5268(3) 0.90559(19) 0.0375(8) Uani 1 1 d . . .
H10 H 0.8346 0.4687 0.9386 0.045 Uiso 1 1 calc R . .
C11 C 0.9149(5) 0.5188(3) 0.83511(19) 0.0329(7) Uani 1 1 d . . .
H11 H 0.9610 0.4547 0.8207 0.039 Uiso 1 1 calc R . .
C12 C 1.2333(4) 0.6105(3) 0.7169(2) 0.0323(7) Uani 1 1 d . . .
C13 C 1.3563(5) 0.5342(3) 0.7791(2) 0.0439(9) Uani 1 1 d . . .
H13A H 1.4950 0.5482 0.7835 0.066 Uiso 1 1 calc R . .
H13B H 1.3281 0.4638 0.7607 0.066 Uiso 1 1 calc R . .
H13C H 1.3222 0.5431 0.8316 0.066 Uiso 1 1 calc R . .
Cl1 Cl 0.67617(15) 0.63047(9) 1.01434(6) 0.0565(3) Uani 1 1 d . . .
Cl2 Cl 1.29023(15) 0.59585(9) 0.61949(6) 0.0566(3) Uani 1 1 d . . .
N1 N 0.8830(4) 0.63328(19) 0.63484(15) 0.0289(6) Uani 1 1 d . . .
N2 N 1.2981(4) 0.7220(2) 0.7484(2) 0.0414(7) Uani 1 1 d . . .
O1 O 0.9333(4) 0.80814(19) 0.65724(15) 0.0430(6) Uani 1 1 d . . .
O2 O 0.7890(4) 0.4731(2) 0.57843(16) 0.0550(7) Uani 1 1 d . . .
O3 O 1.2690(4) 0.7426(2) 0.81621(18) 0.0580(8) Uani 1 1 d . . .
O4 O 1.3808(4) 0.7788(2) 0.7083(2) 0.0624(8) 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'
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
O1 C1 N1 121.9(3) . . ?
O1 C1 C2 129.8(3) . . ?
N1 C1 C2 107.8(3) . . ?
C1 C2 C3 104.9(3) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 105.6(3) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
O2 C4 N1 123.9(3) . . ?
O2 C4 C3 128.2(3) . . ?
N1 C4 C3 107.8(3) . . ?
N1 C5 C6 114.2(2) . . ?
N1 C5 C12 114.2(2) . . ?
C6 C5 C12 116.3(2) . . ?
N1 C5 H5 103.3 . . ?
C6 C5 H5 103.3 . . ?
C12 C5 H5 103.3 . . ?
C7 C6 C11 118.5(3) . . ?
C7 C6 C5 124.0(3) . . ?
C11 C6 C5 117.4(3) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 Cl1 119.1(3) . . ?
C8 C9 Cl1 119.5(3) . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C6 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 N2 106.0(3) . . ?
C13 C12 C5 110.8(3) . . ?
N2 C12 C5 113.4(2) . . ?
C13 C12 Cl2 110.9(2) . . ?
N2 C12 Cl2 107.9(2) . . ?
C5 C12 Cl2 107.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 C1 112.2(3) . . ?
C4 N1 C5 119.9(3) . . ?
C1 N1 C5 127.7(3) . . ?
O4 N2 O3 124.8(3) . . ?
O4 N2 C12 120.1(3) . . ?
O3 N2 C12 114.9(3) . . ?
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
C1 O1 1.208(4) . ?
C1 N1 1.406(4) . ?
C1 C2 1.498(5) . ?
C2 C3 1.513(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.501(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.206(4) . ?
C4 N1 1.394(4) . ?
C5 N1 1.452(4) . ?
C5 C6 1.518(4) . ?
C5 C12 1.568(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.398(4) . ?
C6 C11 1.399(4) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(5) . ?
C9 Cl1 1.726(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.546(5) . ?
C12 N2 1.556(4) . ?
C12 Cl2 1.758(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N2 O4 1.208(4) . ?
N2 O3 1.217(4) . ?
