#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/37/2003773.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_2003773
loop_
_publ_author_name
'Zhang, H.'
'Refat, H. M.'
'Biehl, E.'
_publ_section_title
;
 α-(2,3,5,6-Tetrachlorophenyl)-α-(3-thienyl)acetonitrile and
 α-(3-Methoxyphenyl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1667
_journal_page_last               1670
_journal_paper_doi               10.1107/S0108270195004288
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C15 H8 Cl5 N O'
_chemical_formula_weight         395.47
_chemical_name_common            pentachlorophenyl
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                100.24(2)
_cell_angle_beta                 99.65(2)
_cell_angle_gamma                108.39(2)
_cell_formula_units_Z            2
_cell_length_a                   7.681(2)
_cell_length_b                   8.780(2)
_cell_length_c                   12.761(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      8
_cell_volume                     780.2(4)
_computing_cell_refinement       'R3m/V diffractometer control program'
_computing_data_collection       'R3m/V diffractometer control program'
_computing_data_reduction        'R3m/V diffractometer control program'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990a)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990b)'
_diffrn_ambient_temperature      230(2)
_diffrn_measurement_device       R3m/V
_diffrn_measurement_method       ω/2θ
_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  0.042
_diffrn_reflns_av_sigmaI/netI    0.1266
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1841
_diffrn_reflns_theta_max         21
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       needles
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.016
_refine_ls_goodness_of_fit_obs   1.161
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_restrained_S_obs      1.161
_refine_ls_R_factor_all          0.144
_refine_ls_R_factor_obs          0.056
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(Fo^2^) + (0.0156P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.105
_refine_ls_wR_factor_obs         0.075
_reflns_number_observed          882
_reflns_number_total             1679
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cr1176.cif
_cod_data_source_block           2
_cod_original_cell_volume        780.2(3)
_cod_database_code               2003773
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
Cl(2) 1 0.1317(4) 0.4144(3) 0.8622(2) 0.0468(8) Uani d . Cl
Cl(3) 1 0.3504(4) 0.5960(3) 1.0992(2) 0.0480(8) Uani d . Cl
Cl(4) 1 0.4258(4) 0.9697(3) 1.1845(2) 0.0451(8) Uani d . Cl
Cl(5) 1 0.2778(4) 1.1601(3) 1.0301(2) 0.0397(7) Uani d . Cl
Cl(6) 1 0.0383(3) 0.9755(3) 0.7965(2) 0.0360(7) Uani d . Cl
C(1) 1 0.0950(12) 0.7027(11) 0.8381(7) 0.024(2) Uani d . C
C(2) 1 0.1657(12) 0.6221(10) 0.9072(7) 0.029(2) Uani d . C
C(3) 1 0.2661(12) 0.7029(12) 1.0144(7) 0.031(2) Uani d . C
C(4) 1 0.3004(12) 0.8681(11) 1.0526(7) 0.027(3) Uani d . C
C(5) 1 0.2306(12) 0.9545(10) 0.9842(7) 0.025(2) Uani d . C
C(6) 1 0.1300(11) 0.8685(11) 0.8790(6) 0.020(2) Uani d . C
C(7) 1 -0.0191(12) 0.6101(11) 0.7207(7) 0.030(3) Uani d . C
H7 1 -0.0214(12) 0.4962(11) 0.7109(7) 0.040(10) Uiso calc R H
C(8) 1 -0.2153(16) 0.6005(11) 0.7078(7) 0.034(3) Uani d . C
N(9) 1 -0.3673(13) 0.5905(10) 0.6984(6) 0.050(3) Uani d . N
C(10) 1 0.0690(13) 0.6778(10) 0.6321(7) 0.028(2) Uani d . C
C(11) 1 -0.0335(13) 0.7204(10) 0.5490(7) 0.028(2) Uani d . C
H11 1 -0.1573(13) 0.7123(10) 0.5486(7) 0.040(10) Uiso calc R H
C(12) 1 0.0452(14) 0.7738(11) 0.4680(7) 0.032(2) Uani d . C
C(13) 1 0.2318(15) 0.7911(11) 0.4681(9) 0.048(3) Uani d . C
H13 1 0.2871(15) 0.8297(11) 0.4139(9) 0.040(10) Uiso calc R H
C(14) 1 0.3324(14) 0.7487(11) 0.5520(9) 0.045(3) Uani d . C
H14 1 0.4570(14) 0.7586(11) 0.5534(9) 0.040(10) Uiso calc R H
C(15) 1 0.2538(13) 0.6930(10) 0.6321(8) 0.037(3) Uani d . C
H15 1 0.3244(13) 0.6650(10) 0.6871(8) 0.040(10) Uiso calc R H
O(16) 1 -0.0459(10) 0.8193(8) 0.3840(5) 0.055(2) Uani d . O
C(17) 1 -0.2381(15) 0.7969(12) 0.3789(7) 0.059(3) Uani d . C
H17A 1 -0.2878(15) 0.8325(12) 0.3174(7) 0.040(10) Uiso calc R H
H17B 1 -0.2484(15) 0.8609(12) 0.4453(7) 0.040(10) Uiso calc R H
H17C 1 -0.3086(15) 0.6818(12) 0.3705(7) 0.040(10) Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.0060
Cl Cl 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1484 0.1585
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
C(2) C(1) C(6) 117.2(8) y
C(2) C(1) C(7) 120.8(8) y
C(6) C(1) C(7) 122.1(8) y
C(1) C(2) C(3) 121.6(8) y
C(1) C(2) Cl(2) 120.4(7) y
C(3) C(2) Cl(2) 118.0(7) y
C(4) C(3) C(2) 119.9(8) y
C(4) C(3) Cl(3) 120.0(7) y
C(2) C(3) Cl(3) 120.1(7) y
C(3) C(4) C(5) 120.0(8) y
C(3) C(4) Cl(4) 120.4(7) y
C(5) C(4) Cl(4) 119.6(7) y
C(6) C(5) C(4) 117.9(8) y
C(6) C(5) Cl(5) 122.0(7) y
C(4) C(5) Cl(5) 120.1(7) y
C(5) C(6) C(1) 123.4(8) y
C(5) C(6) Cl(6) 117.4(6) y
C(1) C(6) Cl(6) 119.2(6) y
C(8) C(7) C(10) 112.4(8) y
C(8) C(7) C(1) 110.3(7) y
C(10) C(7) C(1) 114.1(7) y
N(9) C(8) C(7) 178.8(11) y
C(15) C(10) C(11) 118.8(9) y
C(15) C(10) C(7) 119.5(9) y
C(11) C(10) C(7) 121.7(8) y
C(12) C(11) C(10) 120.8(9) y
C(11) C(12) O(16) 124.3(10) ?
C(11) C(12) C(13) 120.7(9) y
O(16) C(12) C(13) 115.0(9) ?
C(14) C(13) C(12) 117.7(10) y
C(15) C(14) C(13) 121.8(10) y
C(14) C(15) C(10) 120.2(9) y
C(12) O(16) C(17) 116.4(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(2) C(2) 1.732(9) y
Cl(3) C(3) 1.726(9) y
Cl(4) C(4) 1.715(8) y
Cl(5) C(5) 1.695(9) y
Cl(6) C(6) 1.734(8) y
C(1) C(2) 1.369(11) y
C(1) C(6) 1.379(10) y
C(1) C(7) 1.533(11) y
C(2) C(3) 1.389(11) y
C(3) C(4) 1.369(11) y
C(4) C(5) 1.400(11) y
C(5) C(6) 1.376(10) y
C(7) C(8) 1.462(13) y
C(7) C(10) 1.527(11) y
C(8) N(9) 1.127(11) y
C(10) C(15) 1.383(11) y
C(10) C(11) 1.389(11) y
C(11) C(12) 1.363(11) y
C(12) O(16) 1.370(10) ?
C(12) C(13) 1.393(13) y
C(13) C(14) 1.388(12) y
C(14) C(15) 1.360(12) y
O(16) C(17) 1.415(11) ?
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
C(11) C(10) C(7) C(8) -1.3(12)
C(11) C(10) C(7) C(1) -127.8(8)
C(2) C(1) C(7) C(8) 113.3(10)
C(2) C(1) C(7) C(10) -119.1(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8425588
