#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230267.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_2230267
loop_
_publ_author_name
'Cai, Qun'
'Fei, Zhuan'
'Li, Lin'
_publ_section_title
;
 Methyl N-(4-nitrophenyl)carbamate
;
_journal_coeditor_code           CV5074
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1494
_journal_paper_doi               10.1107/S1600536811018757
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H8 N2 O4'
_chemical_formula_moiety         'C8 H8 N2 O4'
_chemical_formula_sum            'C8 H8 N2 O4'
_chemical_formula_weight         196.16
_chemical_name_systematic
;
Methyl N-(4-nitrophenyl)carbamate
;
_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                101.634(2)
_cell_angle_beta                 97.914(2)
_cell_angle_gamma                116.660(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4269(11)
_cell_length_b                   8.1003(12)
_cell_length_c                   8.5376(12)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.52
_cell_volume                     434.04(11)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4507
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0739
_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)+(0.0470P)²+0.2842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                1539
_reflns_number_total             1686
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5074.cif
_cod_data_source_block           I
_cod_database_code               2230267
_cod_database_fobs_code          2230267
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2798(6) 0.1171(5) 0.4095(4) 0.0645(10) Uani d . 1 1 . .
H H1A 0.4024 0.2283 0.4846 0.097 Uiso calc R 1 1 . .
H H1B 0.2871 0.0023 0.4122 0.097 Uiso calc R 1 1 . .
H H1C 0.1582 0.1095 0.4419 0.097 Uiso calc R 1 1 . .
C C2 0.2591(4) 0.2904(4) 0.2229(3) 0.0400(6) Uani d . 1 1 . .
C C3 0.2433(4) 0.4234(4) -0.0116(3) 0.0351(6) Uani d . 1 1 . .
C C4 0.2670(4) 0.5997(4) 0.0750(3) 0.0391(6) Uani d . 1 1 . .
H H4 0.2853 0.6318 0.1891 0.047 Uiso calc R 1 1 . .
C C5 0.2633(4) 0.7260(4) -0.0091(3) 0.0399(6) Uani d . 1 1 . .
H H5 0.2796 0.8445 0.0481 0.048 Uiso calc R 1 1 . .
C C6 0.2355(4) 0.6774(4) -0.1782(3) 0.0377(6) Uani d . 1 1 . .
C C7 0.2141(5) 0.5042(4) -0.2666(3) 0.0427(7) Uani d . 1 1 . .
H H7 0.1979 0.4739 -0.3804 0.051 Uiso calc R 1 1 . .
C C8 0.2173(4) 0.3786(4) -0.1826(3) 0.0415(7) Uani d . 1 1 . .
H H8 0.2018 0.2607 -0.2405 0.050 Uiso calc R 1 1 . .
N N2 0.2288(4) 0.8111(4) -0.2670(3) 0.0479(6) Uani d . 1 1 . .
N N1 0.2450(4) 0.2846(4) 0.0624(3) 0.0436(6) Uani d . 1 1 . .
O O1 0.2673(4) 0.1340(3) 0.2437(2) 0.0538(6) Uani d . 1 1 . .
O O2 0.2635(4) 0.4136(3) 0.3310(2) 0.0545(6) Uani d . 1 1 . .
O O3 0.2327(4) 0.9584(3) -0.1911(3) 0.0695(7) Uani d . 1 1 . .
O O4 0.2176(4) 0.7718(4) -0.4139(3) 0.0733(8) Uani d . 1 1 . .
H H1 0.235(5) 0.187(5) 0.001(4) 0.059(10) Uiso d . 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.089(3) 0.073(2) 0.0476(18) 0.045(2) 0.0229(17) 0.0351(17)
C2 0.0426(16) 0.0416(16) 0.0391(14) 0.0211(13) 0.0138(12) 0.0152(13)
C3 0.0356(14) 0.0342(14) 0.0388(14) 0.0188(12) 0.0108(11) 0.0128(11)
C4 0.0481(16) 0.0400(15) 0.0286(12) 0.0224(13) 0.0106(11) 0.0064(11)
C5 0.0458(16) 0.0310(14) 0.0441(15) 0.0224(13) 0.0101(12) 0.0061(11)
C6 0.0362(14) 0.0361(15) 0.0429(14) 0.0185(12) 0.0089(11) 0.0150(12)
C7 0.0567(18) 0.0455(17) 0.0338(14) 0.0307(15) 0.0129(12) 0.0129(12)
C8 0.0562(18) 0.0350(15) 0.0365(14) 0.0271(14) 0.0122(12) 0.0051(11)
N2 0.0539(15) 0.0430(15) 0.0545(15) 0.0282(13) 0.0137(12) 0.0194(12)
N1 0.0675(17) 0.0398(14) 0.0324(12) 0.0334(13) 0.0155(11) 0.0101(10)
O1 0.0864(16) 0.0512(13) 0.0429(11) 0.0426(12) 0.0242(11) 0.0254(10)
O2 0.0838(16) 0.0558(13) 0.0366(11) 0.0421(12) 0.0224(10) 0.0157(10)
O3 0.106(2) 0.0434(13) 0.0709(16) 0.0476(14) 0.0179(14) 0.0174(11)
O4 0.120(2) 0.0758(17) 0.0552(15) 0.0635(17) 0.0334(14) 0.0378(13)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 124.7(3) ?
O2 C2 N1 . . 126.5(3) ?
O1 C2 N1 . . 108.8(2) ?
C4 C3 C8 . . 119.3(2) ?
C4 C3 N1 . . 124.0(2) ?
C8 C3 N1 . . 116.7(2) ?
C5 C4 C3 . . 119.5(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C7 . . 121.6(2) ?
C5 C6 N2 . . 119.7(2) ?
C7 C6 N2 . . 118.7(2) ?
C8 C7 C6 . . 118.3(2) ?
C8 C7 H7 . . 120.9 ?
C6 C7 H7 . . 120.9 ?
C7 C8 C3 . . 121.3(2) ?
C7 C8 H8 . . 119.3 ?
C3 C8 H8 . . 119.3 ?
O4 N2 O3 . . 122.3(3) ?
O4 N2 C6 . . 118.9(2) ?
O3 N2 C6 . . 118.9(2) ?
C2 N1 C3 . . 127.9(2) ?
C2 N1 H1 . . 116(2) ?
C3 N1 H1 . . 116(2) ?
C2 O1 C1 . . 115.7(2) ?
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
C1 O1 . 1.444(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O2 . 1.200(3) ?
C2 O1 . 1.340(3) ?
C2 N1 . 1.350(3) ?
C3 C4 . 1.390(4) ?
C3 C8 . 1.394(4) ?
C3 N1 . 1.400(3) ?
C4 C5 . 1.370(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.379(4) ?
C6 N2 . 1.456(3) ?
C7 C8 . 1.364(4) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
N2 O4 . 1.211(3) ?
N2 O3 . 1.223(3) ?
N1 H1 . 0.82(3) ?
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
C7 H7 O2 1_554 0.93 2.57 3.471(3) 163 yes
C4 H4 O2 . 0.93 2.30 2.892(3) 121 no
C1 H1B O4 1_546 0.96 2.53 3.324(4) 140 yes
N1 H1 O3 1_545 0.82(3) 2.20(4) 3.016(3) 170(3) 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
C8 C3 C4 C5 . . . . 0.4(4) ?
N1 C3 C4 C5 . . . . 179.9(3) ?
C3 C4 C5 C6 . . . . 0.2(4) ?
C4 C5 C6 C7 . . . . -1.0(4) ?
C4 C5 C6 N2 . . . . 179.2(2) ?
C5 C6 C7 C8 . . . . 1.2(4) ?
N2 C6 C7 C8 . . . . -179.0(2) ?
C6 C7 C8 C3 . . . . -0.6(4) ?
C4 C3 C8 C7 . . . . -0.2(4) ?
N1 C3 C8 C7 . . . . -179.8(3) ?
C5 C6 N2 O4 . . . . 175.4(3) ?
C7 C6 N2 O4 . . . . -4.5(4) ?
C5 C6 N2 O3 . . . . -5.3(4) ?
C7 C6 N2 O3 . . . . 174.8(3) ?
O2 C2 N1 C3 . . . . 3.5(5) ?
O1 C2 N1 C3 . . . . -176.5(3) ?
C4 C3 N1 C2 . . . . 3.4(5) ?
C8 C3 N1 C2 . . . . -177.0(3) ?
O2 C2 O1 C1 . . . . 0.8(4) ?
N1 C2 O1 C1 . . . . -179.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67324
