#------------------------------------------------------------------------------
#$Date: 2015-06-06 05:29:33 +0300 (Sat, 06 Jun 2015) $
#$Revision: 138435 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240804.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_2240804
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 H9 N3 O6'
_chemical_formula_moiety         'C13 H9 N3 O6'
_chemical_formula_sum            'C13 H9 N3 O6'
_chemical_formula_weight         303.23
_chemical_name_systematic
;
Phenyl N-(3,5-dinitrophenyl)carbamate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.673(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2549(4)
_cell_length_b                   8.8717(4)
_cell_length_c                   12.1470(5)
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.66
_cell_volume                     1320.08(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
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0201
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.134
_diffrn_reflns_theta_min         1.662
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0617P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2355
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5141sup1.cif
_cod_data_source_block           II
_cod_database_code               2240804
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.61513(10) 0.32392(15) 0.60653(10) 0.0637(4) Uani d 1
O O2 0.79022(12) 0.31538(18) 0.63113(11) 0.0785(4) Uani d 1
O O3 1.00811(10) 0.0409(2) 0.37541(12) 0.0824(5) Uani d 1
O O4 0.93014(11) -0.11517(17) 0.26319(12) 0.0722(4) Uani d 1
O O5 0.42568(8) 0.16533(11) 0.29697(8) 0.0433(3) Uani d 1
O O6 0.38141(10) -0.04444(13) 0.20033(12) 0.0667(4) Uani d 1
N N1 0.70568(11) 0.27772(15) 0.58344(10) 0.0488(3) Uani d 1
N N2 0.92743(10) -0.01973(18) 0.33498(11) 0.0522(4) Uani d 1
N N3 0.53349(9) -0.04417(13) 0.30003(10) 0.0416(3) Uani d 1
H H3A 0.5327 -0.1390 0.2852 0.050 Uiso calc 1
C C1 0.72796(11) -0.03251(16) 0.32278(11) 0.0382(3) Uani d 1
H H5 0.7340 -0.1028 0.2665 0.046 Uiso calc 1
C C2 0.81974(11) 0.02594(17) 0.37459(11) 0.0397(3) Uani d 1
C C3 0.81594(12) 0.12779(17) 0.46001(11) 0.0423(3) Uani d 1
H H3 0.8789 0.1657 0.4944 0.051 Uiso calc 1
C C4 0.71342(12) 0.17011(15) 0.49145(11) 0.0382(3) Uani d 1
C C5 0.61827(11) 0.11716(15) 0.44186(11) 0.0370(3) Uani d 1
H H1 0.5506 0.1491 0.4655 0.044 Uiso calc 1
C C6 0.62602(11) 0.01493(14) 0.35580(11) 0.0352(3) Uani d 1
C C7 0.44606(11) 0.03875(15) 0.26836(12) 0.0383(3) Uani d 1
C C8 0.29939(12) 0.03219(17) 0.13844(14) 0.0475(4) Uani d 1
C C9 0.19265(13) 0.0095(2) 0.16418(15) 0.0569(4) Uani d 1
H H13 0.1747 -0.0481 0.2250 0.068 Uiso calc 1
C C10 0.11244(14) 0.0740(2) 0.09776(16) 0.0644(5) Uani d 1
H H12 0.0394 0.0593 0.1137 0.077 Uiso calc 1
C C11 0.13885(15) 0.1595(2) 0.00871(15) 0.0610(5) Uani d 1
H H11 0.0839 0.2024 -0.0354 0.073 Uiso calc 1
C C12 0.24650(15) 0.1821(2) -0.01578(14) 0.0590(4) Uani d 1
H H10 0.2643 0.2407 -0.0761 0.071 Uiso calc 1
C C13 0.32810(14) 0.1174(2) 0.04939(15) 0.0548(4) Uani d 1
H H9 0.4011 0.1314 0.0333 0.066 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'
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 117.34(11)
O2 N1 O1 124.29(14)
O2 N1 C4 117.71(13)
O1 N1 C4 118.00(13)
O3 N2 O4 123.94(14)
O3 N2 C2 118.12(14)
O4 N2 C2 117.94(14)
C7 N3 C6 123.92(11)
C7 N3 H3A 118.0
C6 N3 H3A 118.0
C2 C1 C6 118.98(13)
C2 C1 H5 120.5
C6 C1 H5 120.5
C1 C2 C3 123.17(13)
C1 C2 N2 118.37(13)
C3 C2 N2 118.44(13)
C4 C3 C2 116.06(13)
C4 C3 H3 122.0
C2 C3 H3 122.0
C3 C4 C5 123.57(13)
C3 C4 N1 117.80(13)
C5 C4 N1 118.63(12)
C4 C5 C6 118.39(13)
C4 C5 H1 120.8
C6 C5 H1 120.8
C1 C6 C5 119.81(12)
C1 C6 N3 117.89(12)
C5 C6 N3 122.30(12)
O5 C7 N3 126.67(13)
O5 C7 O6 124.37(13)
N3 C7 O6 108.94(12)
C9 C8 C13 121.95(15)
C9 C8 O6 118.54(16)
C13 C8 O6 119.31(15)
C8 C9 C10 118.38(17)
C8 C9 H13 120.8
C10 C9 H13 120.8
C11 C10 C9 120.82(16)
C11 C10 H12 119.6
C9 C10 H12 119.6
C10 C11 C12 120.16(17)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C13 119.89(17)
C11 C12 H10 120.1
C13 C12 H10 120.1
C8 C13 C12 118.81(16)
C8 C13 H9 120.6
C12 C13 H9 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2232(17)
O2 N1 1.2188(17)
O3 N2 1.2165(19)
O4 N2 1.2167(19)
O5 C7 1.2039(16)
O6 C7 1.3480(17)
O6 C8 1.4119(18)
N1 C4 1.4748(18)
N2 C2 1.4745(18)
N3 C7 1.3465(18)
N3 C6 1.4054(17)
N3 H3A 0.8600
C1 C2 1.374(2)
C1 C6 1.3885(19)
C1 H5 0.9300
C2 C3 1.378(2)
C3 C4 1.376(2)
C3 H3 0.9300
C4 C5 1.3791(19)
C5 C6 1.3894(19)
C5 H1 0.9300
C8 C9 1.369(2)
C8 C13 1.374(3)
C9 C10 1.378(2)
C9 H13 0.9300
C10 C11 1.368(3)
C10 H12 0.9300
C11 C12 1.376(3)
C11 H11 0.9300
C12 C13 1.382(2)
C12 H10 0.9300
C13 H9 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 O5 2_645 0.86 2.07 2.8836(15) 157
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 1.4(2)
C6 C1 C2 N2 -177.01(12)
O3 N2 C2 C1 174.49(15)
O4 N2 C2 C1 -5.0(2)
O3 N2 C2 C3 -4.0(2)
O4 N2 C2 C3 176.50(14)
C1 C2 C3 C4 -0.4(2)
N2 C2 C3 C4 178.04(12)
C2 C3 C4 C5 -0.5(2)
C2 C3 C4 N1 179.34(12)
O2 N1 C4 C3 -4.8(2)
O1 N1 C4 C3 174.88(14)
O2 N1 C4 C5 175.11(14)
O1 N1 C4 C5 -5.3(2)
C3 C4 C5 C6 0.3(2)
N1 C4 C5 C6 -179.52(12)
C2 C1 C6 C5 -1.57(19)
C2 C1 C6 N3 178.72(12)
C4 C5 C6 C1 0.73(19)
C4 C5 C6 N3 -179.58(12)
C7 N3 C6 C1 -137.09(14)
C7 N3 C6 C5 43.2(2)
C6 N3 C7 O5 -12.7(2)
C6 N3 C7 O6 168.91(13)
C8 O6 C7 O5 15.9(2)
C8 O6 C7 N3 -165.73(14)
C7 O6 C8 C9 -110.20(18)
C7 O6 C8 C13 74.81(19)
C13 C8 C9 C10 0.4(3)
O6 C8 C9 C10 -174.48(15)
C8 C9 C10 C11 -0.4(3)
C9 C10 C11 C12 0.0(3)
C10 C11 C12 C13 0.4(3)
C9 C8 C13 C12 0.1(2)
O6 C8 C13 C12 174.88(14)
C11 C12 C13 C8 -0.5(2)

_cod_database_fobs_code 2240804
