#------------------------------------------------------------------------------
#$Date: 2022-03-18 12:28:37 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104807.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_8104807
loop_
_publ_author_name
'Muller, Kina'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              285
_journal_page_last               286
_journal_paper_doi               10.1515/ncrs-2020-0527
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C3 H9 Cl N, Cl'
_chemical_formula_sum            'C3 H9 Cl2 N'
_chemical_formula_weight         130.01
_chemical_name_common            '3-chloropropylammonium chloride'
_chemical_name_systematic        '3-chloropropylammonium chloride'
_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   mixed
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.266(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7694(5)
_cell_length_b                   9.6963(6)
_cell_length_c                   14.8577(9)
_cell_measurement_reflns_used    4978
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.52
_cell_volume                     1250.24(13)
_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 0.996
_diffrn_measured_fraction_theta_max 0.993
_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  0.0112
_diffrn_reflns_av_sigmaI/netI    0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.414
_diffrn_reflns_theta_min         2.771
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       platelet
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.393
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0193
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0220P)²+0.8146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0511
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1483
_reflns_number_total             1560
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL ga093_s in C2/c             New:
    ga093.res
    created by SHELXL-2018/3 at 13:55:30 on 28-Aug-2020
CELL  0.71073    8.7694    9.6963   14.8577    90.000    98.266    90.000
ZERR        8    0.0005    0.0006    0.0009     0.000     0.003     0.000
LATT   2
SYMM     0.50000 - X ,              Y ,            - Z
SFAC  C  H Cl  N
UNIT    24   72  16   8
ACTA NOHKL
BOND $H
CONF
HTAB
TEMP -73

EQIV $1 -x+1/2, -y+1/2, -z+1/2
EQIV $2 x+1/2, -y, z

HTAB N1 Cl2
HTAB N1 Cl2_$1
HTAB N1 Cl2_$2

L.S. 10
FMAP 2
PLAN -5

WGHT    0.022000    0.814600
FVAR       0.21866
CL1   3    0.615301    0.529823    0.122297    11.00000    0.03662    0.02862 =
         0.04014    0.00671    0.00651    0.00008
N1    4    0.400807    0.176987    0.169328    11.00000    0.02331    0.02538 =
         0.02797   -0.00247    0.00853   -0.00057
H711  2    0.299194    0.159620    0.165175    11.00000    0.04100
H712  2    0.426369    0.232072    0.214251    11.00000    0.04019
H713  2    0.447820    0.091099    0.180880    11.00000    0.04021
C1    1    0.437679    0.234579    0.082043    11.00000    0.02385    0.03346 =
         0.02508    0.00030    0.00552    0.00025
AFIX  23
H1A   2    0.386245    0.325109    0.070845    11.00000   -1.20000
H1B   2    0.396437    0.172162    0.031636    11.00000   -1.20000
AFIX   0
C2    1    0.609565    0.252447    0.082499    11.00000    0.02441    0.03321 =
         0.03390   -0.00108    0.01272    0.00259
AFIX  23
H2A   2    0.660164    0.162244    0.096840    11.00000   -1.20000
H2B   2    0.627344    0.278402    0.020406    11.00000   -1.20000
AFIX   0
C3    1    0.687222    0.358397    0.148451    11.00000    0.02074    0.03129 =
         0.03514    0.00650    0.00466    0.00288
AFIX  23
H3A   2    0.799623    0.356712    0.146663    11.00000   -1.20000
H3B   2    0.670062    0.333828    0.210888    11.00000   -1.20000
AFIX   0
CL2   3    0.040893    0.120606    0.158462    11.00000    0.02821    0.02610 =
         0.03013   -0.00280    0.00853   -0.00498
HKLF 4 1  0.0000  0.0000 -1.0000  0.0000  1.0000  0.0000  1.0000  0.0000  1.0000




REM  ga093_s in C2/c             New:
REM wR2 = 0.0511, GooF = S = 1.072, Restrained GooF = 1.072 for all data
REM R1 = 0.0193 for 1483 Fo > 4sig(Fo) and 0.0205 for all 1560 data
REM 67 parameters refined using 0 restraints

END

WGHT      0.0220      0.8146

REM Instructions for potential hydrogen bonds
HTAB N1 Cl2
HTAB N1 Cl2_$1
HTAB N1 Cl2_$2
EQIV $3 x-1/2, -y+1, z
HTAB C1 Cl1_$3
HTAB C3 Cl2_$1

REM Highest difference peak  0.372,  deepest hole -0.312,  1-sigma level  0.038
Q1    1   0.6346  0.4968  0.0791  11.00000  0.05    0.37
Q2    1   0.5266  0.2459  0.0868  11.00000  0.05    0.31
Q3    1   0.6479  0.3028  0.1170  11.00000  0.05    0.28
Q4    1   0.4221  0.2115  0.1213  11.00000  0.05    0.21
Q5    1   0.0901  0.0805  0.1880  11.00000  0.05    0.16
;
_cod_data_source_file            suppl_j_ncrs-2020-0527_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               8104807
_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 0.61530(3) 0.52982(3) 0.12230(2) 0.03503(9) Uani 1 1 d . . . . .
N1 N 0.40081(10) 0.17699(9) 0.16933(6) 0.02508(17) Uani 1 1 d . . . . .
H711 H 0.2992(19) 0.1596(15) 0.1652(10) 0.041(4) Uiso 1 1 d . . . . .
H712 H 0.4264(17) 0.2321(16) 0.2143(10) 0.040(4) Uiso 1 1 d . . . . .
H713 H 0.4478(17) 0.0911(16) 0.1809(10) 0.040(4) Uiso 1 1 d . . . . .
C1 C 0.43768(11) 0.23458(11) 0.08204(7) 0.0273(2) Uani 1 1 d . . . . .
H1A H 0.386245 0.325109 0.070845 0.033 Uiso 1 1 calc R U . . .
H1B H 0.396437 0.172162 0.031636 0.033 Uiso 1 1 calc R U . . .
C2 C 0.60956(12) 0.25245(12) 0.08250(7) 0.0297(2) Uani 1 1 d . . . . .
H2A H 0.660164 0.162244 0.096840 0.036 Uiso 1 1 calc R U . . .
H2B H 0.627344 0.278402 0.020406 0.036 Uiso 1 1 calc R U . . .
C3 C 0.68722(11) 0.35840(11) 0.14845(8) 0.0290(2) Uani 1 1 d . . . . .
H3A H 0.799623 0.356712 0.146663 0.035 Uiso 1 1 calc R U . . .
H3B H 0.670062 0.333828 0.210888 0.035 Uiso 1 1 calc R U . . .
Cl2 Cl 0.04089(3) 0.12061(2) 0.15846(2) 0.02772(8) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.03662(15) 0.02862(14) 0.04014(16) 0.00671(10) 0.00651(11) 0.00008(10)
N1 0.0233(4) 0.0254(4) 0.0280(4) -0.0025(3) 0.0085(3) -0.0006(3)
C1 0.0239(4) 0.0335(5) 0.0251(5) 0.0003(4) 0.0055(4) 0.0002(4)
C2 0.0244(5) 0.0332(5) 0.0339(5) -0.0011(4) 0.0127(4) 0.0026(4)
C3 0.0207(4) 0.0313(5) 0.0351(5) 0.0065(4) 0.0047(4) 0.0029(4)
Cl2 0.02821(13) 0.02610(13) 0.03013(13) -0.00280(9) 0.00853(9) -0.00498(8)
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
C1 N1 H711 110.3(10) . .
C1 N1 H712 112.2(10) . .
H711 N1 H712 108.3(13) . .
C1 N1 H713 110.4(9) . .
H711 N1 H713 104.6(13) . .
H712 N1 H713 110.6(13) . .
N1 C1 C2 112.27(8) . .
N1 C1 H1A 109.1 . .
C2 C1 H1A 109.1 . .
N1 C1 H1B 109.1 . .
C2 C1 H1B 109.1 . .
H1A C1 H1B 107.9 . .
C3 C2 C1 115.80(8) . .
C3 C2 H2A 108.3 . .
C1 C2 H2A 108.3 . .
C3 C2 H2B 108.3 . .
C1 C2 H2B 108.3 . .
H2A C2 H2B 107.4 . .
C2 C3 Cl1 112.10(7) . .
C2 C3 H3A 109.2 . .
Cl1 C3 H3A 109.2 . .
C2 C3 H3B 109.2 . .
Cl1 C3 H3B 109.2 . .
H3A C3 H3B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.8003(11) .
N1 C1 1.4896(13) .
N1 H711 0.900(16) .
N1 H712 0.859(16) .
N1 H713 0.934(15) .
C1 C2 1.5163(14) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.5124(16) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 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 H711 Cl2 0.900(16) 2.285(17) 3.1844(9) 178.1(13) .
N1 H712 Cl2 0.859(16) 2.354(16) 3.2068(9) 171.6(13) 7
N1 H713 Cl2 0.934(15) 2.251(16) 3.1494(9) 161.0(13) 6_655
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
N1 C1 C2 C3 -65.88(12) . . . .
C1 C2 C3 Cl1 -63.18(11) . . . .
