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#$Date: 2022-03-18 12:33:12 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104808.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_8104808
loop_
_publ_author_name
'Muller, Kina'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride,
 C4H11Cl2N
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              287
_journal_page_last               289
_journal_paper_doi               10.1515/ncrs-2020-0520
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C4 H11 Cl N, Cl'
_chemical_formula_sum            'C4 H11 Cl2 N'
_chemical_formula_weight         144.04
_chemical_name_common
'1-chloro-2-(dimethylamino)ethane hydrochloride'
_chemical_name_systematic
'1-chloro-2-(dimethylamino)ethane hydrochloride'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.294(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2374(12)
_cell_length_b                   8.2108(6)
_cell_length_c                   14.0114(14)
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.88
_cell_volume                     1520.4(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.377
_diffrn_reflns_theta_min         2.877
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9193
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0398
_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)+(0.0540P)²+1.8188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1606
_reflns_number_total             1901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0520_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               8104808
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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 0.21545(5) 0.22414(9) 0.36596(6) 0.0670(2) Uani 1 1 d . . . . .
Cl2 Cl -0.07570(4) 0.25918(6) 0.60437(3) 0.04119(17) Uani 1 1 d . . . . .
N1 N -0.08466(13) 0.2735(2) 0.38777(11) 0.0387(4) Uani 1 1 d . . . . .
C4 C -0.13420(18) 0.1187(3) 0.35806(15) 0.0513(5) Uani 1 1 d . . . . .
H4A H -0.094722 0.027046 0.385107 0.077 Uiso 1 1 calc R U . . .
H4B H -0.138063 0.111050 0.288144 0.077 Uiso 1 1 calc R U . . .
H4C H -0.202621 0.115459 0.381237 0.077 Uiso 1 1 calc R U . . .
C3 C -0.14678(18) 0.4140(3) 0.35420(17) 0.0563(6) Uani 1 1 d . . . . .
H3A H -0.115731 0.514961 0.378940 0.084 Uiso 1 1 calc R U . . .
H3B H -0.214995 0.403503 0.377232 0.084 Uiso 1 1 calc R U . . .
H3C H -0.150823 0.416578 0.284159 0.084 Uiso 1 1 calc R U . . .
H1 H -0.0803(18) 0.274(3) 0.4456(19) 0.045(6) Uiso 1 1 d . . . . .
C21 C 0.02001(16) 0.2981(3) 0.35545(14) 0.0353(5) Uani 0.876(5) 1 d D . P A 1
H21A H 0.040290 0.413162 0.365292 0.042 Uiso 0.876(5) 1 calc R U P A 1
H21B H 0.021096 0.273617 0.286324 0.042 Uiso 0.876(5) 1 calc R U P A 1
C11 C 0.09394(17) 0.1886(4) 0.41057(17) 0.0448(6) Uani 0.876(5) 1 d D . P A 1
H11A H 0.074303 0.073068 0.401402 0.054 Uiso 0.876(5) 1 calc R U P A 1
H11B H 0.094933 0.214080 0.479679 0.054 Uiso 0.876(5) 1 calc R U P A 1
C22 C 0.0212(10) 0.197(2) 0.3579(9) 0.030(4) Uani 0.124(5) 1 d D . P A 2
H22A H 0.026750 0.080790 0.376338 0.036 Uiso 0.124(5) 1 calc R U P A 2
H22B H 0.028635 0.206991 0.288247 0.036 Uiso 0.124(5) 1 calc R U P A 2
C12 C 0.0985(10) 0.2983(19) 0.4134(11) 0.036(4) Uani 0.124(5) 1 d D . P A 2
H12A H 0.097105 0.278220 0.482941 0.043 Uiso 0.124(5) 1 calc R U P A 2
H12B H 0.088493 0.415947 0.400542 0.043 Uiso 0.124(5) 1 calc R U P A 2
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
C3 N1 C4 110.58(18) . .
C3 N1 C21 107.88(17) . .
C4 N1 C21 115.70(18) . .
C3 N1 C22 134.2(6) . .
C4 N1 C22 88.3(5) . .
C3 N1 H1 108.9(16) . .
C4 N1 H1 106.8(16) . .
C21 N1 H1 106.8(18) . .
C22 N1 H1 104.3(18) . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N1 C3 H3A 109.5 . .
N1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N1 C21 C11 110.48(19) . .
N1 C21 H21A 109.6 . .
C11 C21 H21A 109.6 . .
N1 C21 H21B 109.6 . .
C11 C21 H21B 109.6 . .
H21A C21 H21B 108.1 . .
C21 C11 Cl1 107.15(17) . .
C21 C11 H11A 110.3 . .
Cl1 C11 H11A 110.3 . .
C21 C11 H11B 110.3 . .
Cl1 C11 H11B 110.3 . .
H11A C11 H11B 108.5 . .
C12 C22 N1 103.1(10) . .
C12 C22 H22A 111.1 . .
N1 C22 H22A 111.1 . .
C12 C22 H22B 111.1 . .
N1 C22 H22B 111.1 . .
H22A C22 H22B 109.1 . .
C22 C12 Cl1 101.2(10) . .
C22 C12 H12A 111.5 . .
Cl1 C12 H12A 111.5 . .
C22 C12 H12B 111.5 . .
Cl1 C12 H12B 111.5 . .
H12A C12 H12B 109.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C11 1.783(2) .
Cl1 C12 1.824(13) .
N1 C3 1.477(3) .
N1 C4 1.479(3) .
N1 C21 1.496(3) .
N1 C22 1.613(14) .
N1 H1 0.81(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C21 C11 1.508(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C22 C12 1.501(15) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 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
N1 H1 Cl2 0.81(3) 2.23(3) 3.0327(16) 176(2) .
C21^a H21A^a Cl2 0.99 2.76 3.746(3) 174.0 5_566
C21^a H21B^a Cl2 0.99 2.80 3.700(2) 151.5 8_554
C11^a H11A^a Cl2 0.99 2.73 3.690(3) 163.6 5_556
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
C3 N1 C21 C11 163.2(2) . . . .
C4 N1 C21 C11 -72.4(2) . . . .
N1 C21 C11 Cl1 179.12(15) . . . .
C3 N1 C22 C12 83.8(11) . . . .
C4 N1 C22 C12 -158.7(10) . . . .
N1 C22 C12 Cl1 -173.3(7) . . . .
