#------------------------------------------------------------------------------
#$Date: 2022-03-30 10:36:24 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104941.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_8104941
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              263
_journal_page_last               265
_journal_paper_doi               10.1515/ncrs-2020-0513
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C6 H6 Cl N'
_chemical_formula_sum            'C6 H6 Cl N'
_chemical_formula_weight         127.57
_chemical_name_common            2-(chloromethyl)pyridine
_chemical_name_systematic        2-(chloromethyl)pyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.1771(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5211(2)
_cell_length_b                   10.2467(3)
_cell_length_c                   9.1436(3)
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.99
_cell_volume                     609.35(3)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5519
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.990
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9406
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.583
_exptl_crystal_size_mid          0.485
_exptl_crystal_size_min          0.396
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0260
_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)+(0.0311P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1403
_reflns_number_total             1507
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0513_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104941
_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_min   0.693
_shelx_estimated_absorpt_t_max   0.753
loop_
_space_group_symop_operation_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_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
Cl1 Cl 0.02414(4) 0.82516(3) 0.50239(3) 0.03785(11) Uani 1 1 d . . . . .
N1 N 0.22254(14) 0.55172(9) 0.65344(10) 0.0310(2) Uani 1 1 d . . . . .
C1 C 0.30493(15) 0.63345(10) 0.55941(11) 0.0253(2) Uani 1 1 d . . . . .
C2 C 0.51110(17) 0.66870(10) 0.57089(12) 0.0302(2) Uani 1 1 d . . . . .
H2 H 0.563695 0.727197 0.502222 0.036 Uiso 1 1 calc R U . . .
C3 C 0.63882(17) 0.61713(12) 0.68414(13) 0.0359(2) Uani 1 1 d . . . . .
H3 H 0.780588 0.639325 0.694399 0.043 Uiso 1 1 calc R U . . .
C4 C 0.55584(18) 0.53282(12) 0.78181(12) 0.0357(2) Uani 1 1 d . . . . .
H4 H 0.639175 0.496038 0.860857 0.043 Uiso 1 1 calc R U . . .
C5 C 0.34853(19) 0.50303(11) 0.76203(13) 0.0347(2) Uani 1 1 d . . . . .
H5 H 0.292563 0.444706 0.829386 0.042 Uiso 1 1 calc R U . . .
C6 C 0.16048(18) 0.68530(11) 0.43813(12) 0.0325(2) Uani 1 1 d . . . . .
H6A H 0.061065 0.616568 0.404856 0.039 Uiso 1 1 calc R U . . .
H6B H 0.238804 0.710831 0.353874 0.039 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C5 N1 C1 117.11(9) . .
N1 C1 C2 123.03(9) . .
N1 C1 C6 115.87(9) . .
C2 C1 C6 121.09(10) . .
C3 C2 C1 118.90(10) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C4 C3 C2 118.65(10) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
C3 C4 C5 118.56(10) . .
C3 C4 H4 120.7 . .
C5 C4 H4 120.7 . .
N1 C5 C4 123.75(11) . .
N1 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
C1 C6 Cl1 109.76(7) . .
C1 C6 H6A 109.7 . .
Cl1 C6 H6A 109.7 . .
C1 C6 H6B 109.7 . .
Cl1 C6 H6B 109.7 . .
H6A C6 H6B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.8072(11) .
N1 C5 1.3382(15) .
N1 C1 1.3403(13) .
C1 C2 1.3887(14) .
C1 C6 1.4990(14) .
C2 C3 1.3855(16) .
C2 H2 0.9500 .
C3 C4 1.3810(17) .
C3 H3 0.9500 .
C4 C5 1.3849(17) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A N1 0.99 2.56 3.5403(15) 172.6 3_566
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
C5 N1 C1 C2 -0.22(16) . . . .
C5 N1 C1 C6 179.40(9) . . . .
N1 C1 C2 C3 0.23(16) . . . .
C6 C1 C2 C3 -179.38(10) . . . .
C1 C2 C3 C4 -0.23(17) . . . .
C2 C3 C4 C5 0.23(17) . . . .
C1 N1 C5 C4 0.23(17) . . . .
C3 C4 C5 N1 -0.24(18) . . . .
N1 C1 C6 Cl1 83.88(10) . . . .
C2 C1 C6 Cl1 -96.49(11) . . . .
