#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/90/2009057.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_2009057
loop_
_publ_author_name
'Britton, Doyle'
_publ_section_title
;
 4,5-Dichloro-2-nitroaniline
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900116
_journal_paper_doi               10.1107/S0108270199098698
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C6 H4 Cl2 N2 O2'
_chemical_formula_weight         207.01
_chemical_name_systematic
;
 4,5-dichloro-2-nitroaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'SHELXL plus manual additions'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5729(2)
_cell_length_b                   9.0936(2)
_cell_length_c                   11.3877(3)
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.9
_cell_volume                     779.64(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'ASTRO and SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      175(2)
_diffrn_measurement_device       'Siemens SMART area-detector'
_diffrn_measurement_method       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  0.036
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4662
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time
;
  the first 138 reflections were remeasured at the end of
  the data collection  14 hours later
;
_diffrn_standards_number         138
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996; Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.09
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment
'refined with isotropic displacement parameters'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_restrained_S_obs      1.12
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.045
_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)+(0.059P)²+0.52P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.112
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                1182
_reflns_number_total             1372
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            qa0168.cif
_cod_data_source_block           C6H4Cl2N2O2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.059P)^2^+0.52P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.059P)^2^+0.52P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2009057
loop_
_symmetry_equiv_pos_as_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_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 .0163(13) .0303(14) .037(2) -.0034(11) .0081(11) -.0023(11)
C2 .0171(14) .0416(15) .0280(14) -.0059(12) .0069(11) -.0031(12)
C3 .0162(13) .041(2) .032(2) .0007(12) .0060(11) .0076(13)
C4 .0198(14) .0280(13) .039(2) -.0008(10) .0105(12) .0001(11)
C5 .0217(14) .0376(15) .0278(15) -.0087(11) .0077(11) -.0039(11)
C6 .0168(13) .039(2) .0288(15) -.0009(12) .0007(11) .0055(12)
N1 .040(2) .0392(15) .049(2) .0040(12) .0064(13) -.0026(13)
N2 .0234(13) .0472(15) .0331(14) -.0043(11) .0050(10) -.0045(11)
O1 .0501(14) .066(2) .0382(13) -.0055(12) -.0127(10) .0049(12)
O2 .0398(13) .0533(14) .0542(15) -.0006(11) .0101(11) -.0166(11)
Cl4 .0461(5) .0336(4) .0646(6) .0047(3) .0163(4) -.0049(3)
Cl5 .0436(5) .0543(5) .0341(4) -.0133(3) .0048(3) -.0123(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .3035(3) .3412(3) .4932(2) .0274(6) Uani d . 1 . C
C2 .2064(3) .4275(3) .4045(2) .0286(6) Uani d . 1 . C
C3 .1652(4) .5744(3) .4237(3) .0295(6) Uani d . 1 . C
C4 .2179(4) .6401(3) .5289(3) .0285(6) Uani d . 1 . C
C5 .3143(3) .5563(3) .6187(2) .0286(6) Uani d . 1 . C
C6 .3540(4) .4127(3) .6016(2) .0285(6) Uani d . 1 . C
N1 .3523(4) .1985(3) .4841(3) .0426(7) Uani d . 1 . N
H1A .312(4) .177(3) .411(3) .030(8) Uiso d . 1 . H
H1B .421(7) .146(6) .545(5) .106(18) Uiso d . 1 . H
N2 .1486(3) .3651(3) .2918(2) .0344(6) Uani d . 1 . N
O1 .0648(3) .4406(3) .2152(2) .0525(6) Uani d . 1 . O
O2 .1831(3) .2339(3) .2739(2) .0488(6) Uani d . 1 . O
Cl4 .16603(11) .82297(8) .55079(8) .0474(3) Uani d . 1 . Cl
Cl5 .38468(11) .63593(9) .75390(7) .0440(3) Uani d . 1 . Cl
H3 .104(4) .621(3) .365(3) .037(9) Uiso d . 1 . H
H6 .413(4) .365(3) .662(3) .038(9) Uiso d . 1 . H
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C6 117.2(3)
N1 C1 C2 126.8(3)
C6 C1 C2 116.0(2)
C3 C2 C1 121.7(3)
C3 C2 N2 118.0(3)
C1 C2 N2 120.3(3)
C4 C3 C2 120.6(3)
C4 C3 H3 122.(2)
C2 C3 H3 117.(2)
C3 C4 C5 118.7(2)
C3 C4 Cl4 119.9(2)
C5 C4 Cl4 121.4(2)
C6 C5 C4 121.3(3)
C6 C5 Cl5 118.5(2)
C4 C5 Cl5 120.2(2)
C5 C6 C1 121.6(3)
C5 C6 H6 117.(2)
C1 C6 H6 121.(2)
C1 N1 H1A 102.(2)
C1 N1 H1B 124.(3)
H1A N1 H1B 133.(4)
O1 N2 O2 121.4(3)
O1 N2 C2 120.0(3)
O2 N2 C2 118.6(3)
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 N1 . 1.357(4) ?
C1 C6 . 1.411(4) ?
C1 C2 . 1.420(4) ?
C2 C3 . 1.394(4) ?
C2 N2 . 1.428(4) ?
C3 C4 . 1.360(4) ?
C3 H3 . .88(3) ?
C4 C5 . 1.414(4) ?
C4 Cl4 . 1.733(3) ?
C5 C6 . 1.359(4) ?
C5 Cl5 . 1.732(3) ?
C6 H6 . .88(3) ?
N1 H1A . .88(3) ?
N1 H1B . .95(6) ?
N2 O1 . 1.232(3) ?
N2 O2 . 1.244(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 73215
