#------------------------------------------------------------------------------
#$Date: 2015-06-06 05:29:33 +0300 (Sat, 06 Jun 2015) $
#$Revision: 138435 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240803.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240803
loop_
_publ_author_name
'Raja, Rajamani'
'Sathiyaraj, Subramaniyan'
'Ali, B. Mohamad'
'Nasar, A. Sultan'
_publ_section_title
;
 Crystal structures of 4-chlorophenyl
 N-(3,5-dinitrophenyl)carbamate and phenyl
 N-(3,5-dinitrophenyl)carbamate
;
_journal_coeditor_code           SU5141
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              744
_journal_page_last               747
_journal_paper_doi               10.1107/S2056989015010245
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H8 Cl N3 O6'
_chemical_formula_moiety         'C13 H8 Cl N3 O6'
_chemical_formula_sum            'C13 H8 Cl N3 O6'
_chemical_formula_weight         337.67
_chemical_name_systematic
;
4-Chlorophenyl N-(3,5-dinitrophenyl)carbamate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.183(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9103(4)
_cell_length_b                   12.5791(4)
_cell_length_c                   10.9772(5)
_cell_measurement_reflns_used    2013
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.47
_cell_volume                     1364.80(9)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ 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  0.0154
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8697
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.671
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²+0.4574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                2134
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5141sup1.cif
_cod_data_source_block           I
_cod_database_code               2240803
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_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_occupancy
Cl Cl1 1.06146(5) -0.35304(4) 1.04085(5) 0.06328(18) Uani d 1
O O1 0.9159(2) 0.44697(12) 0.70274(14) 0.0966(7) Uani d 1
O O2 0.86323(17) 0.55251(10) 0.55446(13) 0.0687(4) Uani d 1
O O3 0.69275(17) 0.41624(12) 0.16853(12) 0.0701(4) Uani d 1
O O4 0.66305(14) 0.24728(12) 0.14188(12) 0.0629(4) Uani d 1
O O5 0.88633(15) 0.10055(9) 0.73898(11) 0.0570(4) Uani d 1
O O6 0.89504(13) -0.05893(9) 0.64269(10) 0.0471(3) Uani d 1
N N1 0.87388(17) 0.46386(12) 0.59848(14) 0.0514(4) Uani d 1
N N2 0.69860(15) 0.32352(13) 0.20431(13) 0.0472(4) Uani d 1
N N3 0.83153(15) 0.07996(10) 0.53417(12) 0.0421(3) Uani d 1
H H3A 0.8133 0.0312 0.4806 0.051 Uiso calc 1
C C1 0.76419(15) 0.20217(13) 0.37383(14) 0.0367(4) Uani d 1
H H1 0.7386 0.1452 0.3234 0.044 Uiso calc 1
C C2 0.75199(15) 0.30533(13) 0.33135(14) 0.0369(4) Uani d 1
C C3 0.78764(16) 0.39277(13) 0.40121(15) 0.0403(4) Uani d 1
H H3 0.7800 0.4615 0.3704 0.048 Uiso calc 1
C C4 0.83533(16) 0.37228(12) 0.51973(14) 0.0376(4) Uani d 1
C C5 0.85006(16) 0.27193(12) 0.56865(14) 0.0367(4) Uani d 1
H H5 0.8822 0.2623 0.6496 0.044 Uiso calc 1
C C6 0.81578(15) 0.18518(12) 0.49431(14) 0.0344(3) Uani d 1
C C7 0.87274(16) 0.04673(12) 0.64903(14) 0.0362(4) Uani d 1
C C8 0.93362(16) -0.12190(12) 0.74459(14) 0.0347(4) Uani d 1
C C9 1.00067(18) -0.08512(13) 0.85107(16) 0.0441(4) Uani d 1
H H9 1.0194 -0.0131 0.8613 0.053 Uiso calc 1
C C10 1.03967(18) -0.15731(14) 0.94259(16) 0.0454(4) Uani d 1
H H10 1.0840 -0.1339 1.0153 0.054 Uiso calc 1
C C11 1.01246(16) -0.26366(13) 0.92519(15) 0.0400(4) Uani d 1
C C12 0.94754(17) -0.30018(13) 0.81784(16) 0.0420(4) Uani d 1
H H12 0.9309 -0.3724 0.8067 0.050 Uiso calc 1
C C13 0.90742(16) -0.22847(12) 0.72698(15) 0.0396(4) Uani d 1
H H13 0.8630 -0.2520 0.6544 0.048 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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
C7 O6 C8 123.48(12)
O1 N1 O2 123.46(16)
O1 N1 C4 118.36(14)
O2 N1 C4 118.17(15)
O4 N2 O3 124.24(15)
O4 N2 C2 118.71(15)
O3 N2 C2 117.05(16)
C7 N3 C6 126.78(13)
C7 N3 H3A 116.6
C6 N3 H3A 116.6
C2 C1 C6 118.66(15)
C2 C1 H1 120.7
C6 C1 H1 120.7
C3 C2 C1 123.49(15)
C3 C2 N2 117.68(15)
C1 C2 N2 118.83(15)
C2 C3 C4 115.78(15)
C2 C3 H3 122.1
C4 C3 H3 122.1
C5 C4 C3 124.09(15)
C5 C4 N1 118.22(14)
C3 C4 N1 117.69(14)
C4 C5 C6 118.48(14)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 N3 122.83(14)
C5 C6 C1 119.46(15)
N3 C6 C1 117.71(14)
O5 C7 O6 126.20(15)
O5 C7 N3 126.73(15)
O6 C7 N3 107.07(13)
C13 C8 C9 121.28(15)
C13 C8 O6 113.63(14)
C9 C8 O6 124.94(14)
C8 C9 C10 118.99(15)
C8 C9 H9 120.5
C10 C9 H9 120.5
C11 C10 C9 119.63(16)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 121.14(15)
C10 C11 Cl1 119.09(13)
C12 C11 Cl1 119.77(13)
C11 C12 C13 119.40(15)
C11 C12 H12 120.3
C13 C12 H12 120.3
C8 C13 C12 119.55(15)
C8 C13 H13 120.2
C12 C13 H13 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.7384(16)
O1 N1 1.208(2)
O2 N1 1.2169(19)
O3 N2 1.231(2)
O4 N2 1.216(2)
O5 C7 1.1967(19)
O6 C7 1.3500(19)
O6 C8 1.4009(19)
N1 C4 1.474(2)
N2 C2 1.473(2)
N3 C7 1.362(2)
N3 C6 1.399(2)
N3 H3A 0.8600
C1 C2 1.381(2)
C1 C6 1.399(2)
C1 H1 0.9300
C2 C3 1.372(2)
C3 C4 1.376(2)
C3 H3 0.9300
C4 C5 1.375(2)
C5 C6 1.390(2)
C5 H5 0.9300
C8 C13 1.376(2)
C8 C9 1.381(2)
C9 C10 1.388(2)
C9 H9 0.9300
C10 C11 1.375(2)
C10 H10 0.9300
C11 C12 1.380(2)
C12 C13 1.382(2)
C12 H12 0.9300
C13 H13 0.9300
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
N3 H3A O3 2_645 0.86 2.18 3.0286(19) 168
C12 H12 O1 1_545 0.93 2.54 3.428(2) 159
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
C6 C1 C2 C3 -0.1(2)
C6 C1 C2 N2 179.58(14)
O4 N2 C2 C3 -178.06(15)
O3 N2 C2 C3 1.7(2)
O4 N2 C2 C1 2.2(2)
O3 N2 C2 C1 -177.98(15)
C1 C2 C3 C4 -1.1(2)
N2 C2 C3 C4 179.18(14)
C2 C3 C4 C5 1.0(2)
C2 C3 C4 N1 -179.54(14)
O1 N1 C4 C5 -0.5(3)
O2 N1 C4 C5 178.63(16)
O1 N1 C4 C3 179.99(19)
O2 N1 C4 C3 -0.9(2)
C3 C4 C5 C6 0.4(2)
N1 C4 C5 C6 -179.06(14)
C4 C5 C6 N3 177.72(15)
C4 C5 C6 C1 -1.7(2)
C7 N3 C6 C5 4.4(3)
C7 N3 C6 C1 -176.15(15)
C2 C1 C6 C5 1.6(2)
C2 C1 C6 N3 -177.90(14)
C8 O6 C7 O5 2.4(3)
C8 O6 C7 N3 -177.36(14)
C6 N3 C7 O5 10.1(3)
C6 N3 C7 O6 -170.17(15)
C7 O6 C8 C13 159.36(15)
C7 O6 C8 C9 -25.2(2)
C13 C8 C9 C10 -1.3(3)
O6 C8 C9 C10 -176.42(15)
C8 C9 C10 C11 0.8(3)
C9 C10 C11 C12 0.4(3)
C9 C10 C11 Cl1 -179.80(14)
C10 C11 C12 C13 -1.0(3)
Cl1 C11 C12 C13 179.19(13)
C9 C8 C13 C12 0.7(2)
O6 C8 C13 C12 176.33(15)
C11 C12 C13 C8 0.4(2)

_cod_database_fobs_code 2240803
