#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011827.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_2011827
loop_
_publ_author_name
'Ferguson, George'
'Glidewell, Christopher'
'Low, John N.'
'Skakle, Janet M. S.'
'Wardell, James L.'
_publ_section_title
;
 Hydrogen bonding in C-methylated nitroanilines: the
 three-dimensional framework structure of 2-methyl-4-nitroaniline
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              315
_journal_page_last               316
_journal_paper_doi               10.1107/S0108270100019405
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C7 H8 N2 O2'
_chemical_formula_sum            'C7 H8 N2 O2'
_chemical_formula_weight         152.15
_chemical_name_systematic
;
2-Methyl-4-nitroaniline
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.050(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6113(5)
_cell_length_b                   11.6304(7)
_cell_length_c                   8.2286(5)
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      3.04
_cell_volume                     726.60(8)
_computing_cell_refinement       XPREP
_computing_data_collection       'XPREP (Bruker, 1997)'
_computing_data_reduction        XPREP
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material
'SHELXL97  and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .032
_diffrn_reflns_av_sigmaI/netI    .0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4272
_diffrn_reflns_theta_full        32.54
_diffrn_reflns_theta_max         32.54
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .104
_exptl_absorpt_correction_T_max  .979
_exptl_absorpt_correction_T_min  .969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         .248
_refine_diff_density_min         -.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1316
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      .994
_refine_ls_R_factor_all          .056
_refine_ls_R_factor_gt           .043
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0735P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .113
_reflns_number_gt                1037
_reflns_number_total             1316
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            sk1442.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               2011827
_cod_database_fobs_code          2011827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
loop_
_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
_atom_site_type_symbol
C1 .9082(2) .07296(16) .7383(2) .0344(4) Uani d . 1 . . C
C2 .8859(2) -.04640(14) .71078(18) .0337(4) Uani d . 1 . . C
C3 .8083(3) -.08360(15) .5633(2) .0360(4) Uani d . 1 . . C
C4 .7538(2) -.00392(17) .44279(18) .0352(4) Uani d . 1 . . C
C5 .7736(3) .11337(16) .4687(2) .0405(4) Uani d . 1 . . C
C6 .8508(3) .15102(16) .6156(2) .0399(4) Uani d . 1 . . C
N1 .9814(3) .11329(15) .8825(2) .0478(4) Uani d . 1 . . N
C7 .9475(3) -.13003(19) .8422(3) .0465(5) Uani d . 1 . . C
N2 .6745(2) -.04422(15) .29017(18) .0463(4) Uani d . 1 . . N
O1 .6538(3) -.14825(15) .2675(2) .0621(5) Uani d . 1 . . O
O2 .6279(4) .02700(18) .1852(2) .0811(7) Uani d . 1 . . O
H3 .7922 -.1618 .5440 .043 Uiso calc R 1 . . H
H5 .7354 .1657 .3883 .049 Uiso calc R 1 . . H
H6 .8652 .2295 .6338 .048 Uiso calc R 1 . . H
H1A .9923 .1861 .8981 .057 Uiso calc R 1 . . H
H1B 1.0168 .0660 .9582 .057 Uiso calc R 1 . . H
H7A .9344 -.2071 .8015 .070 Uiso calc R 1 . . H
H7B .8782 -.1206 .9344 .070 Uiso calc R 1 . . H
H7C 1.0692 -.1157 .8747 .070 Uiso calc R 1 . . H
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 .0390(9) .0353(8) .0284(7) -.0033(7) -.0018(6) -.0021(6)
C2 .0384(10) .0309(8) .0310(8) -.0026(6) -.0023(6) .0024(5)
C3 .0448(9) .0310(7) .0312(7) -.0022(7) -.0055(6) -.0015(6)
C4 .0433(9) .0355(8) .0255(6) -.0017(6) -.0063(6) -.0026(5)
C5 .0518(11) .0358(9) .0327(8) .0002(7) -.0051(7) .0050(6)
C6 .0557(11) .0299(8) .0330(8) -.0019(7) -.0046(7) -.0013(6)
N1 .0676(12) .0397(9) .0341(8) -.0040(8) -.0107(7) -.0052(6)
C7 .0579(12) .0408(9) .0387(9) -.0025(8) -.0119(8) .0097(7)
N2 .0584(11) .0479(10) .0304(8) -.0021(8) -.0121(7) -.0046(6)
O1 .0877(12) .0457(8) .0497(8) -.0066(8) -.0182(8) -.0136(7)
O2 .132(2) .0645(12) .0408(9) -.0039(12) -.0375(10) .0062(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
N1 C1 C6 119.51(16) no
N1 C1 C2 121.04(15) no
C6 C1 C2 119.44(15) no
C3 C2 C1 119.13(14) no
C3 C2 C7 121.43(15) no
C1 C2 C7 119.44(14) no
C2 C3 C4 120.16(16) no
C2 C3 H3 119.9 no
C4 C3 H3 119.9 no
C5 C4 C3 121.28(15) no
C5 C4 N2 119.38(16) no
C3 C4 N2 119.34(17) no
C6 C5 C4 118.84(16) no
C6 C5 H5 120.6 no
C4 C5 H5 120.6 no
C5 C6 C1 121.14(17) no
C5 C6 H6 119.4 no
C1 C6 H6 119.4 no
C1 N1 H1A 120.0 no
C1 N1 H1B 120.0 no
H1A N1 H1B 120.0 no
C2 C7 H7A 109.5 no
C2 C7 H7B 109.5 no
H7A C7 H7B 109.5 no
C2 C7 H7C 109.5 no
H7A C7 H7C 109.5 no
H7B C7 H7C 109.5 no
O2 N2 O1 121.80(16) no
O2 N2 C4 118.53(16) no
O1 N2 C4 119.67(16) no
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 C2 . 1.415(2) y
C2 C3 . 1.381(2) y
C3 C4 . 1.398(2) y
C3 H3 . .9300 no
C4 C5 . 1.387(3) y
C5 C6 . 1.377(3) y
C5 H5 . .9300 no
C6 C1 . 1.405(2) y
C6 H6 . .9300 no
C1 N1 . 1.358(2) y
C4 N2 . 1.433(2) y
N2 O1 . 1.233(2) y
N2 O2 . 1.231(2) y
C2 C7 . 1.505(2) y
N1 H1A . .8600 no
N1 H1B . .8600 no
C7 H7A . .9600 no
C7 H7B . .9600 no
C7 H7C . .9600 no
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
N1 H1A O1 3 .86 2.56 3.239(3) 136 y
N1 H1B O2 2_556 .86 2.27 3.117(3) 169 y
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
_geom_torsion_publ_flag
N1 C1 C2 C3 178.99(18) no
N1 C1 C2 C7 -1.2(3) no
C6 C1 C2 C3 .1(2) no
C6 C1 C2 C7 179.93(17) no
N1 C1 C6 C5 -179.0(2) no
C2 C1 C6 C5 -.1(3) no
C1 C2 C3 C4 .4(3) no
C7 C2 C3 C4 -179.40(18) no
C2 C3 C4 N2 179.62(16) no
C2 C3 C4 C5 -.9(3) no
C3 C4 N2 O1 .7(3) no
C3 C4 N2 O2 -179.8(2) no
C5 C4 N2 O1 -178.79(19) no
C5 C4 N2 O2 .8(3) no
N2 C4 C5 C6 -179.66(18) no
C3 C4 C5 C6 .9(3) no
C4 C5 C6 C1 -.4(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7163
