#------------------------------------------------------------------------------
#$Date: 2023-05-15 11:43:25 +0300 (Mon, 15 May 2023) $
#$Revision: 283770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107205.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107205
loop_
_publ_author_name
'Miao, Mingzhi'
'Li, Ji'
_publ_section_title
;
 The crystal structure of 4-(chloromethyl)benzonitrile, C8H6ClN
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              749
_journal_page_last               750
_journal_paper_doi               10.1515/ncrs-2022-0196
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C8 H6 Cl N'
_chemical_formula_sum            'C8 H6 Cl N'
_chemical_formula_weight         151.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.3965(7)
_cell_length_b                   7.8164(3)
_cell_length_c                   4.5015(2)
_cell_measurement_reflns_used    7922
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      3.77
_cell_volume                     717.66(5)
_computing_cell_refinement       'SAINT V8.40B Bruker-AXS, (Bruker, 2018) (1)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.40B Bruker-AXS, (Bruker, 2018) '
_computing_molecular_graphics    'Diamond (Brandenburg, 2006)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2   (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9401
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.305
_diffrn_reflns_theta_min         3.771
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.638
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2, (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0240P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0670
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1088
_reflns_number_total             1133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0196_suppl.cif
_cod_data_source_block           t
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8107205
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.621
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
2.a Riding coordinates: 
 C5(H5) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3) 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66112(6) 0.750000 0.7612(2) 0.0181(2) Uani 1 2 d S T P . .
C2 C 0.63468(4) 0.59550(11) 0.66214(19) 0.01925(19) Uani 1 1 d . . . . .
H2 H 0.652284 0.490416 0.731977 0.023 Uiso 1 1 calc R U . . .
C3 C 0.58281(4) 0.59428(11) 0.46221(19) 0.01922(19) Uani 1 1 d . . . . .
H3 H 0.565069 0.489089 0.393539 0.023 Uiso 1 1 calc R U . . .
C4 C 0.55707(6) 0.750000 0.3634(3) 0.0175(2) Uani 1 2 d S T P . .
C5 C 0.71880(6) 0.750000 0.9670(3) 0.0225(3) Uani 1 2 d S T P . .
H5 H 0.721030 0.852230 1.093672 0.027 Uiso 1 1 d R U . . .
C6 C 0.50238(6) 0.750000 0.1599(3) 0.0204(2) Uani 1 2 d S T P . .
Cl1 Cl 0.79446(2) 0.750000 0.75268(6) 0.02108(12) Uani 1 2 d S T P . .
N1 N 0.45819(6) 0.750000 0.0025(3) 0.0265(3) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C2 119.82(11) . 7_575
C2 C1 C5 120.08(6) 7_575 .
C2 C1 C5 120.08(6) . .
C1 C2 H2 119.8 . .
C3 C2 C1 120.48(8) . .
C3 C2 H2 119.8 . .
C2 C3 H3 120.5 . .
C2 C3 C4 119.08(8) . .
C4 C3 H3 120.5 . .
C3 C4 C3 121.05(11) 7_575 .
C3 C4 C6 119.47(5) 7_575 .
C3 C4 C6 119.47(5) . .
C1 C5 H5 113.29(3) . 7_575
C1 C5 H5 113.3 . .
C1 C5 Cl1 109.77(9) . .
H5 C5 H5 108.8 . 7_575
Cl1 C5 H5 105.6 . .
Cl1 C5 H5 105.56(2) . 7_575
N1 C6 C4 178.77(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3957(11) .
C1 C2 1.3957(11) 7_575
C1 C5 1.4974(17) .
C2 H2 0.9500 .
C2 C3 1.3890(12) .
C3 H3 0.9500 .
C3 C4 1.3982(10) .
C4 C6 1.4435(17) .
C5 H5 0.9828 .
C5 H5 0.9828 7_575
C5 Cl1 1.8199(13) .
C6 N1 1.1463(17) .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -0.54(13) . . . .
C2 C1 C2 C3 0.94(17) 7_575 . . .
C2 C1 C5 Cl1 89.22(9) . . . .
C2 C1 C5 Cl1 -89.22(9) 7_575 . . .
C2 C3 C4 C3 0.14(17) . . . 7_575
C2 C3 C4 C6 -178.86(9) . . . .
C5 C1 C2 C3 -177.49(9) . . . .
