#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011397.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_2011397
loop_
_publ_author_name
'Pink, Maren'
'Britton, Doyle'
'Noland, Wayland E.'
'Pinnow, Matthew J.'
_publ_section_title
;
 2,4,6-Trichlorophenylisonitrile and 2,4,6-trichlorobenzonitrile
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1271
_journal_page_last               1273
_journal_paper_doi               10.1107/S0108270100010234
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C7 H2 Cl3 N'
_chemical_formula_weight         206.45
_chemical_melting_point          353.5(5)
_chemical_name_systematic
;
 2,4,6-trichlorobenzonitrile
;
_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'
_audit_creation_method           'SHELXL + manual additions'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.975(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8742(3)
_cell_length_b                   15.8897(13)
_cell_length_c                   12.9067(11)
_cell_measurement_reflns_used    4571
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     794.42(11)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXLTL
_computing_publication_material  SHELXLTL
_computing_structure_refinement  SHELXLTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device       'Siemens SMART area detector diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .028
_diffrn_reflns_av_sigmaI/netI    .018
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8166
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_interval_time
;
 first 181 reflections remeasured at the end of the data
 collection 6 hours later
;
_diffrn_standards_number         181
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_T_max  .85
_exptl_absorpt_correction_T_min  .70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .15
_refine_diff_density_max         .295
_refine_diff_density_min         -.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.08
_refine_ls_goodness_of_fit_obs   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_restrained_S_obs      1.130
_refine_ls_R_factor_all          .034
_refine_ls_R_factor_obs          .026
_refine_ls_shift/esd_max         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.038P)²+0.12P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .068
_refine_ls_wR_factor_obs         .066
_reflns_number_observed          1542
_reflns_number_total             1811
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            bk1548.cif
_cod_data_source_block           nitrile
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '353-354' was changed to '353.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '353-354' was changed to '353.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.038P)^2^+0.12P] 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^)+(0.038P)^2^+0.12P] 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/c'
_cod_database_code               2011397
_cod_database_fobs_code          2011397
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl2 .74410(11) -.01756(2) .13222(3) .03703(12) Uani d . 1 . . Cl
Cl4 .24707(10) .10423(3) .48775(3) .03804(12) Uani d . 1 . . Cl
Cl6 .80198(11) .31520(2) .21253(3) .03809(12) Uani d . 1 . . Cl
C1 .7467(4) .14791(9) .18029(11) .0254(3) Uani d . 1 . . C
C2 .6551(4) .06659(9) .21132(12) .0269(3) Uani d . 1 . . C
C3 .5002(4) .05265(10) .30585(11) .0290(3) Uani d . 1 . . C
H3 .4389 -.0026 .3268 .035 Uiso calc R 1 . . H
C4 .4367(4) .12135(10) .36926(12) .0282(3) Uani d . 1 . . C
C5 .5233(4) .20275(10) .34168(12) .0291(3) Uani d . 1 . . C
H5 .4770 .2489 .3862 .035 Uiso calc R 1 . . H
C6 .6788(4) .21476(9) .24764(12) .0266(3) Uani d . 1 . . C
C7 .9101(4) .16173(10) .08227(12) .0295(3) Uani d . 1 . . C
N1 1.0432(4) .17258(9) .00522(11) .0394(3) Uani d . 1 . . N
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
Cl2 .0457(3) .0291(2) .0364(2) .00167(16) .00446(17) -.00609(15)
Cl4 .0365(2) .0507(3) .0271(2) .00261(17) .00544(15) .00534(17)
Cl6 .0440(2) .0265(2) .0439(2) -.00135(15) .00617(18) .00138(16)
C1 .0223(7) .0294(8) .0245(7) .0024(5) -.0021(5) .0013(6)
C2 .0251(7) .0271(7) .0283(7) .0024(6) -.0029(6) -.0017(6)
C3 .0277(8) .0298(8) .0295(8) -.0003(6) -.0021(6) .0034(6)
C4 .0235(7) .0380(8) .0230(7) .0012(6) -.0007(6) .0036(6)
C5 .0266(8) .0333(8) .0275(7) .0038(6) -.0017(6) -.0037(6)
C6 .0228(7) .0265(7) .0303(8) .0004(5) -.0023(6) .0010(6)
C7 .0294(8) .0284(7) .0306(8) .0022(6) -.0005(6) .0003(6)
N1 .0437(9) .0403(8) .0344(8) .0001(6) .0081(6) .0011(6)
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'
Cl Cl .1484 .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
C2 C1 C6 118.1(2)
C2 C1 C7 120.6(2)
C6 C1 C7 121.3(2)
C3 C2 C1 121.0(2)
C3 C2 Cl2 119.5(2)
C1 C2 Cl2 119.5(2)
C2 C3 C4 118.5(2)
C2 C3 H3 120.8
C4 C3 H3 120.8
C5 C4 C3 122.5(2)
C5 C4 Cl4 118.9(2)
C3 C4 Cl4 118.7(2)
C6 C5 C4 117.9(2)
C6 C5 H5 121.1
C4 C5 H5 121.1
C5 C6 C1 122.1(2)
C5 C6 Cl6 119.1(2)
C1 C6 Cl6 118.8(2)
N1 C7 C1 179.2(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
Cl2 C2 . 1.7208(15) ?
Cl4 C4 . 1.7293(16) ?
Cl6 C6 . 1.7284(15) ?
C1 C2 . 1.400(2) ?
C1 C6 . 1.400(2) ?
C1 C7 . 1.441(2) ?
C2 C3 . 1.387(2) ?
C3 C4 . 1.389(2) ?
C3 H3 . .9500 ?
C4 C5 . 1.384(2) ?
C5 C6 . 1.377(2) ?
C5 H5 . .9500 ?
C7 N1 . 1.141(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 455502
