#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206741.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_2206741
loop_
_publ_author_name
'Watkin, David J.'
'Motherwell, W. D. S.'
'Cooper, Richard I.'
'Pantos, Stefan'
'Steadman, Oliver I.'
_publ_section_title
;
 2-Acetamido-4-nitrotoluene
;
_journal_coeditor_code           LH6479
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2778
_journal_page_last               o2780
_journal_paper_doi               10.1107/S1600536805024049
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C9 H10 N2 O3'
_chemical_formula_sum            'C9 H10 N2 O3'
_chemical_formula_weight         194.19
_chemical_name_systematic        2-Acetamido-4-nitrotoluene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                90
_cell_angle_beta                 107.2307(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2167(2)
_cell_length_b                   13.6406(3)
_cell_length_c                   8.7203(2)
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     933.51(4)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS '
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10098
_diffrn_reflns_theta_full        26.923
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         5.109
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       lath
_exptl_crystal_F_000             408
_exptl_crystal_size_max          1.22
_exptl_crystal_size_mid          0.63
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000416
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(F²) + (0.04P)² + 0.32P] where P = [max(Fo²,0) + 2Fc²]/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0977
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                2110
_reflns_number_total             2110
_reflns_threshold_expression     I>-10.0σ(I)
_cod_data_source_file            lh6479.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206741
_cod_database_fobs_code          2206741
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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_occupancy
_atom_site_type_symbol
C1 0.66060(14) 0.65335(8) 0.13949(12) 0.0205 Uani 1.0000 C
C2 0.69944(14) 0.55296(8) 0.14755(13) 0.0222 Uani 1.0000 C
C3 0.60557(15) 0.49005(9) 0.21537(14) 0.0266 Uani 1.0000 C
C4 0.47870(15) 0.52447(9) 0.27626(14) 0.0272 Uani 1.0000 C
C5 0.44408(15) 0.62402(9) 0.26521(14) 0.0241 Uani 1.0000 C
C6 0.53092(14) 0.68921(8) 0.19623(13) 0.0225 Uani 1.0000 C
N7 0.30928(13) 0.66177(8) 0.32777(13) 0.0311 Uani 1.0000 N
O8 0.23776(16) 0.60433(8) 0.39389(17) 0.0584 Uani 1.0000 O
O9 0.27408(14) 0.74913(7) 0.31277(15) 0.0501 Uani 1.0000 O
C10 0.84177(16) 0.51420(9) 0.08932(15) 0.0289 Uani 1.0000 C
N11 0.75561(12) 0.71876(7) 0.07257(11) 0.0228 Uani 1.0000 N
C12 0.82179(14) 0.80492(8) 0.13955(13) 0.0204 Uani 1.0000 C
O13 0.80172(11) 0.83621(6) 0.26552(10) 0.0276 Uani 1.0000 O
C14 0.92198(16) 0.86113(9) 0.05038(14) 0.0267 Uani 1.0000 C
H31 0.6311 0.4211 0.2200 0.0312 Uiso 1.0000 H
H41 0.4149 0.4821 0.3221 0.0342 Uiso 1.0000 H
H61 0.5018 0.7567 0.1887 0.0272 Uiso 1.0000 H
H101 0.8475 0.4431 0.0964 0.0447 Uiso 1.0000 H
H102 0.9500 0.5403 0.1533 0.0452 Uiso 1.0000 H
H103 0.8276 0.5340 -0.0221 0.0431 Uiso 1.0000 H
H5 0.7748 0.7013 -0.0149 0.0311 Uiso 1.0000 H
H8 1.0336 0.8715 0.1182 0.0457 Uiso 1.0000 H
H9 0.9273 0.8294 -0.0462 0.0438 Uiso 1.0000 H
H10 0.8710 0.9239 0.0250 0.0461 Uiso 1.0000 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 0.0235(5) 0.0222(5) 0.0164(5) -0.0024(4) 0.0070(4) -0.0003(4)
C2 0.0248(6) 0.0239(6) 0.0171(5) 0.0011(4) 0.0051(4) -0.0005(4)
C3 0.0320(6) 0.0212(5) 0.0262(6) -0.0002(5) 0.0080(5) 0.0016(4)
C4 0.0291(6) 0.0261(6) 0.0279(6) -0.0061(5) 0.0106(5) 0.0024(5)
C5 0.0224(5) 0.0280(6) 0.0239(6) -0.0023(5) 0.0099(5) -0.0012(5)
C6 0.0252(6) 0.0215(5) 0.0220(5) -0.0002(4) 0.0087(4) -0.0001(4)
N7 0.0290(5) 0.0327(6) 0.0369(6) -0.0024(4) 0.0181(5) 0.0000(5)
O8 0.0616(7) 0.0468(6) 0.0910(9) 0.0008(5) 0.0600(7) 0.0134(6)
O9 0.0536(7) 0.0333(5) 0.0804(8) 0.0089(5) 0.0462(6) 0.0061(5)
C10 0.0329(6) 0.0285(6) 0.0276(6) 0.0080(5) 0.0124(5) 0.0019(5)
N11 0.0304(5) 0.0236(5) 0.0194(5) -0.0022(4) 0.0153(4) -0.0022(4)
C12 0.0228(5) 0.0222(5) 0.0180(5) 0.0021(4) 0.0088(4) 0.0022(4)
O13 0.0400(5) 0.0258(4) 0.0225(4) -0.0042(4) 0.0178(4) -0.0031(3)
C14 0.0300(6) 0.0317(6) 0.0211(6) -0.0069(5) 0.0119(5) 0.0009(5)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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
C2 C1 C6 120.84(10) no
C2 C1 N11 119.30(10) no
C6 C1 N11 119.86(10) no
C1 C2 C3 118.35(10) no
C1 C2 C10 120.99(10) no
C3 C2 C10 120.64(10) no
C2 C3 C4 121.79(11) no
C2 C3 H31 118.6 no
C4 C3 H31 119.6 no
C3 C4 C5 117.93(11) no
C3 C4 H41 122.0 no
C5 C4 H41 120.1 no
C4 C5 C6 122.58(11) no
C4 C5 N7 118.75(10) no
C6 C5 N7 118.67(10) no
C1 C6 C5 118.48(11) no
C1 C6 H61 121.4 no
C5 C6 H61 120.1 no
C5 N7 O8 118.20(11) no
C5 N7 O9 118.88(10) no
O8 N7 O9 122.91(11) no
C2 C10 H101 111.0 no
C2 C10 H102 110.5 no
H101 C10 H102 108.2 no
C2 C10 H103 111.2 no
H101 C10 H103 109.1 no
H102 C10 H103 106.8 no
C1 N11 C12 124.63(9) no
C1 N11 H5 117.4 no
C12 N11 H5 117.9 no
N11 C12 O13 122.82(10) no
N11 C12 C14 115.63(9) no
O13 C12 C14 121.55(10) no
C12 C14 H8 109.4 no
C12 C14 H9 113.5 no
H8 C14 H9 109.2 no
C12 C14 H10 108.1 no
H8 C14 H10 106.9 no
H9 C14 H10 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.4030(16) no
C1 C6 1.3899(15) no
C1 N11 1.4198(14) no
C2 C3 1.3969(16) no
C2 C10 1.5023(16) no
C3 C4 1.3846(17) no
C3 H31 0.962 no
C4 C5 1.3849(17) no
C4 H41 0.945 no
C5 C6 1.3842(16) no
C5 N7 1.4655(15) no
C6 H61 0.949 no
N7 O8 1.2216(14) no
N7 O9 1.2241(14) no
C10 H101 0.973 no
C10 H102 0.967 no
C10 H103 0.982 no
N11 C12 1.3528(15) no
N11 H5 0.857 no
C12 O13 1.2342(13) no
C12 C14 1.4998(15) no
C14 H8 0.943 no
C14 H9 0.960 no
C14 H10 0.949 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
N11 H5 O13 4_564 0.86 2.06 2.9110(10) 175 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 68628
