#------------------------------------------------------------------------------
#$Date: 2022-01-08 04:48:22 +0200 (Sat, 08 Jan 2022) $
#$Revision: 271964 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244001.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_2244001
loop_
_publ_author_name
'Kirchhoff, Jan-Lukas'
'Brieger, Lukas'
'Strohmann, Carsten'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (S)-N-methyl-1-phenylethan-1-aminium chloride
;
_journal_coeditor_code           DX2041
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021013645
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C9 H14 N +, Cl -'
_chemical_formula_moiety         'C9 H14 N +, Cl -'
_chemical_formula_sum            'C9 H14 Cl N'
_chemical_formula_weight         171.671
_chemical_name_systematic
;
(S)-N-Methyl-1-phenylethan-1-aminium chloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7723(6)
_cell_length_b                   7.1806(5)
_cell_length_c                   20.542(2)
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      3.17
_cell_volume                     998.94(15)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_reduction
;
APEX4 (Bruker, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
APEX4 (Bruker, 2021), CrystalExplorer21 (Spackman et
al.,  2021;
Turner et al.,  2017), publCIF (Westrip, 2010),
Mercury (Macrae et al.,  2020),
NoSpherA2 (Kleemiss et al.,  2021),
GaussView 6.016 (Frisch et al.,  2016), Gaussian 09
Revision A.02
(Frisch et al.,  2016), Molekel 4.3 (Flükiger et
al.,  2000),
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            45327
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         36.37
_diffrn_reflns_theta_min         3.01
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.6499
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             368.574
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.371
_refine_diff_density_max         0.1355
_refine_diff_density_min         -0.2181
_refine_ls_abs_structure_details
;
Hooft et al., 2010
;
_refine_ls_abs_structure_Flack   -0.011(7)
_refine_ls_goodness_of_fit_ref   1.1409
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1409
_refine_ls_R_factor_all          0.0114
_refine_ls_R_factor_gt           0.0110
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0056P)²+0.0168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0242
_refine_ls_wR_factor_ref         0.0244
_reflns_number_gt                4785
_reflns_number_total             4856
_reflns_threshold_expression     I>=2σ(I)
_cod_data_source_file            dx2041sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        998.96(16)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               2244001
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
loop_
_atom_site_type_symbol
_atom_site_label
_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
Cl Cl1 0.592521(11) 0.543691(10) 0.179385(3) 0.016339(15) Uani 1.000000
N N1 0.41684(4) 0.47620(3) 0.316327(11) 0.01307(4) Uani 1.000000
H H1a 0.4079(9) 0.3344(8) 0.3230(3) 0.0295(14) Uani 1.000000
H H1b 0.4763(8) 0.4952(8) 0.2706(3) 0.0192(14) Uiso 1.000000
C C1 0.09588(5) 0.45714(5) 0.262760(15) 0.01939(5) Uani 1.000000
H H1c 0.1708(9) 0.4643(10) 0.2151(3) 0.0406(16) Uani 1.000000
H H1d 0.0800(10) 0.3125(8) 0.2759(3) 0.0423(17) Uani 1.000000
H H1e -0.0497(8) 0.5137(10) 0.2588(3) 0.0407(17) Uani 1.000000
C C2 0.21347(4) 0.56000(4) 0.314781(13) 0.01314(4) Uani 1.000000
H H2 0.2339(7) 0.7048(6) 0.3009(2) 0.0231(12) Uani 1.000000
C C3 0.55360(4) 0.55695(5) 0.365038(15) 0.01794(5) Uani 1.000000
H H3a 0.5664(10) 0.7052(8) 0.3574(3) 0.0433(17) Uani 1.000000
H H3b 0.4987(8) 0.5322(10) 0.4134(3) 0.0409(16) Uani 1.000000
H H3c 0.6979(9) 0.4918(9) 0.3592(3) 0.0420(18) Uani 1.000000
C C4 0.11585(4) 0.55281(5) 0.380803(13) 0.01459(4) Uani 1.000000
C C5 0.10068(6) 0.38632(5) 0.415554(17) 0.02390(6) Uani 1.000000
H H5 0.1630(10) 0.2592(8) 0.3963(3) 0.0438(17) Uani 1.000000
C C6 0.00496(6) 0.38292(6) 0.47550(2) 0.02996(8) Uani 1.000000
H H6 -0.0039(10) 0.2515(11) 0.5014(4) 0.062(2) Uani 1.000000
C C7 -0.07980(5) 0.54394(7) 0.500661(15) 0.02628(6) Uani 1.000000
H H7 -0.1515(9) 0.5389(10) 0.5478(3) 0.0464(17) Uani 1.000000
C C8 -0.06743(5) 0.70924(5) 0.465812(16) 0.02150(6) Uani 1.000000
H H8 -0.1335(10) 0.8354(8) 0.4853(3) 0.0462(18) Uani 1.000000
C C9 0.03231(5) 0.71413(5) 0.406506(15) 0.01653(5) Uani 1.000000
H H9 0.0436(8) 0.8430(8) 0.3791(3) 0.0330(15) Uani 1.000000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C custom 0.00211 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
Cl custom 0.13244 0.15913 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
H custom 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
N custom 0.00411 0.00331 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1b N1 H1a . . 106.0(5) ?
C2 N1 H1a . . 110.2(3) ?
C2 N1 H1b . . 106.6(3) ?
C3 N1 H1a . . 109.5(3) ?
C3 N1 H1b . . 108.6(3) ?
C3 N1 C2 . . 115.49(2) ?
H1d C1 H1c . . 108.3(5) ?
H1e C1 H1c . . 109.8(4) ?
H1e C1 H1d . . 107.0(5) ?
C2 C1 H1c . . 111.1(3) ?
C2 C1 H1d . . 110.0(3) ?
C2 C1 H1e . . 110.6(3) ?
C1 C2 N1 . . 107.44(2) ?
H2 C2 N1 . . 105.8(3) ?
H2 C2 C1 . . 110.3(3) ?
C4 C2 N1 . . 111.62(2) ?
C4 C2 C1 . . 112.62(2) ?
C4 C2 H2 . . 108.9(2) ?
H3a C3 N1 . . 109.7(3) ?
H3b C3 N1 . . 110.1(3) ?
H3b C3 H3a . . 109.0(5) ?
H3c C3 N1 . . 108.5(3) ?
H3c C3 H3a . . 109.6(5) ?
H3c C3 H3b . . 109.9(4) ?
C5 C4 C2 . . 121.39(3) ?
C9 C4 C2 . . 119.33(3) ?
C9 C4 C5 . . 119.23(3) ?
H5 C5 C4 . . 120.5(3) ?
C6 C5 C4 . . 120.11(3) ?
C6 C5 H5 . . 119.4(3) ?
H6 C6 C5 . . 118.4(4) ?
C7 C6 C5 . . 120.44(4) ?
C7 C6 H6 . . 121.2(4) ?
H7 C7 C6 . . 119.3(4) ?
C8 C7 C6 . . 119.62(3) ?
C8 C7 H7 . . 121.1(4) ?
H8 C8 C7 . . 119.9(3) ?
C9 C8 C7 . . 120.10(3) ?
C9 C8 H8 . . 120.0(3) ?
C8 C9 C4 . . 120.48(3) ?
H9 C9 C4 . . 118.9(3) ?
H9 C9 C8 . . 120.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 H1a . 1.029(6) ?
N1 H1b . 1.031(6) ?
N1 C2 . 1.5034(4) ?
N1 C3 . 1.4816(4) ?
C1 H1c . 1.104(6) ?
C1 H1d . 1.079(6) ?
C1 H1e . 1.070(5) ?
C1 C2 . 1.5237(4) ?
C2 H2 . 1.087(4) ?
C2 C4 . 1.5097(4) ?
C3 H3a . 1.080(6) ?
C3 H3b . 1.075(5) ?
C3 H3c . 1.090(6) ?
C4 C5 . 1.3962(4) ?
C4 C9 . 1.3931(4) ?
C5 H5 . 1.080(6) ?
C5 C6 . 1.3919(5) ?
C6 H6 . 1.085(7) ?
C6 C7 . 1.3905(6) ?
C7 H7 . 1.084(5) ?
C7 C8 . 1.3886(6) ?
C8 H8 . 1.087(6) ?
C8 C9 . 1.3935(5) ?
C9 H9 . 1.086(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1a Cl1 3_645 1.029(6) 2.088(6) 3.1075(3) 170.4(5)
N1 H1b Cl1 . 1.031(6) 2.062(6) 3.0925(4) 177.8(5)
