#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206870.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_2206870
loop_
_publ_author_name
'Williamson, Craig'
'Storey, John M. D.'
'Harrison, William T. A.'
_publ_section_title
;
 {N-[(S)-1-Phenylethyl]carbamoyl}methylaminium chloride
;
_journal_coeditor_code           BT6726
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3133
_journal_page_last               o3135
_journal_paper_doi               10.1107/S1600536805027182
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H15 N2 O +, Cl -'
_chemical_formula_moiety         'C10 H15 N2 O +, Cl -'
_chemical_formula_sum            'C10 H15 Cl N2 O'
_chemical_formula_weight         214.69
_chemical_name_systematic
;
{N-[(S)-1-Phenylethyl]carbamoyl}methylaminium chloride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6309(3)
_cell_length_b                   5.8963(4)
_cell_length_c                   39.939(3)
_cell_measurement_reflns_used    856
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1090.54(13)
_computing_cell_refinement       'Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
Denzo (Otwinowski & Minor 1997), Scalepack and SORTAV (Blessing
1995)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            3682
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         4.01
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from needle'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.389
_refine_ls_abs_structure_details 'Flack (1983), 439 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0431P)²+1.5926P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1578
_reflns_number_total             1768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6726.cif
_cod_data_source_block           I
_cod_database_code               2206870
_cod_database_fobs_code          2206870
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.3476(8) 0.2857(6) 0.57786(9) 0.0241(8) Uani d . 1 C
H1 0.3220 0.1673 0.5937 0.029 Uiso calc R 1 H
C2 0.5263(9) 0.2492(7) 0.55044(10) 0.0282(9) Uani d . 1 C
H2 0.6220 0.1079 0.5477 0.034 Uiso calc R 1 H
C3 0.5636(9) 0.4212(7) 0.52715(10) 0.0286(9) Uani d . 1 C
H3 0.6860 0.3984 0.5084 0.034 Uiso calc R 1 H
C4 0.4228(9) 0.6256(7) 0.53132(10) 0.0303(10) Uani d . 1 C
H4 0.4475 0.7432 0.5153 0.036 Uiso calc R 1 H
C5 0.2449(8) 0.6596(7) 0.55885(9) 0.0263(9) Uani d . 1 C
H5 0.1485 0.8007 0.5614 0.032 Uiso calc R 1 H
C6 0.2054(8) 0.4904(7) 0.58274(9) 0.0222(8) Uani d . 1 C
C7 0.0020(9) 0.5204(7) 0.61243(10) 0.0247(9) Uani d . 1 C
H7 -0.1827 0.4417 0.6067 0.030 Uiso calc R 1 H
C8 -0.0733(10) 0.7653(7) 0.62115(11) 0.0368(11) Uani d . 1 C
H8A -0.2023 0.7676 0.6406 0.055 Uiso calc R 1 H
H8B -0.1699 0.8368 0.6020 0.055 Uiso calc R 1 H
H8C 0.1039 0.8489 0.6264 0.055 Uiso calc R 1 H
C9 -0.0481(7) 0.3063(6) 0.66460(8) 0.0167(7) Uani d . 1 C
C10 0.1047(7) 0.2278(6) 0.69611(8) 0.0192(7) Uani d . 1 C
H10A 0.2041 0.0819 0.6919 0.023 Uiso calc R 1 H
H10B 0.2515 0.3410 0.7028 0.023 Uiso calc R 1 H
N1 0.1207(7) 0.4076(5) 0.64230(7) 0.0219(7) Uani d . 1 N
H1A 0.3087 0.4073 0.6454 0.026 Uiso calc R 1 H
N2 -0.1105(6) 0.1991(5) 0.72335(7) 0.0174(6) Uani d . 1 N
H2A -0.0173 0.1859 0.7433 0.021 Uiso calc R 1 H
H2B -0.2168 0.0720 0.7195 0.021 Uiso calc R 1 H
H2C -0.2293 0.3220 0.7239 0.021 Uiso calc R 1 H
O1 -0.3109(5) 0.2796(5) 0.66108(6) 0.0206(6) Uani d . 1 O
Cl1 0.36806(18) 0.20605(14) 0.78047(2) 0.0210(2) Uani d . 1 Cl
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.032(2) 0.0212(17) 0.0196(16) -0.001(2) -0.0033(16) 0.0040(15)
C2 0.031(2) 0.024(2) 0.030(2) -0.0001(17) 0.0023(17) -0.0045(17)
C3 0.030(2) 0.035(2) 0.0206(17) -0.0040(19) 0.0050(17) 0.0005(18)
C4 0.033(2) 0.033(2) 0.0248(19) -0.0061(19) 0.0027(18) 0.0046(18)
C5 0.030(2) 0.025(2) 0.0239(18) 0.0029(17) -0.0003(16) 0.0030(16)
C6 0.0155(18) 0.028(2) 0.0230(17) -0.0033(16) -0.0024(15) 0.0032(17)
C7 0.021(2) 0.028(2) 0.0247(18) -0.0027(17) -0.0014(16) 0.0001(18)
C8 0.040(2) 0.036(3) 0.035(2) 0.012(2) 0.010(2) 0.011(2)
C9 0.0138(16) 0.0141(16) 0.0220(17) 0.0002(15) 0.0023(14) -0.0001(17)
C10 0.0163(16) 0.0221(18) 0.0193(16) -0.0005(16) 0.0026(14) 0.0041(15)
N1 0.0154(15) 0.0284(16) 0.0219(14) -0.0011(15) -0.0013(13) 0.0044(13)
N2 0.0175(13) 0.0143(13) 0.0202(13) -0.0001(15) -0.0020(12) 0.0020(13)
O1 0.0152(12) 0.0262(13) 0.0204(12) 0.0005(11) 0.0010(10) 0.0003(12)
Cl1 0.0212(4) 0.0177(4) 0.0241(4) 0.0013(4) -0.0005(4) 0.0003(4)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 121.9(4)
C6 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C1 119.3(4)
C3 C2 H2 120.3
C1 C2 H2 120.3
C4 C3 C2 119.9(4)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.1(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 121.1(4)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 117.7(3)
C1 C6 C7 120.2(4)
C5 C6 C7 122.1(4)
N1 C7 C6 110.3(3)
N1 C7 C8 109.1(3)
C6 C7 C8 115.4(3)
N1 C7 H7 107.2
C6 C7 H7 107.2
C8 C7 H7 107.2
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N1 124.1(3)
O1 C9 C10 121.0(3)
N1 C9 C10 114.8(3)
N2 C10 C9 109.2(3)
N2 C10 H10A 109.8
C9 C10 H10A 109.8
N2 C10 H10B 109.8
C9 C10 H10B 109.8
H10A C10 H10B 108.3
C9 N1 C7 121.8(3)
C9 N1 H1A 119.1
C7 N1 H1A 119.1
C10 N2 H2A 109.5
C10 N2 H2B 109.5
H2A N2 H2B 109.5
C10 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.389(5)
C1 C2 1.390(5)
C1 H1 0.9500
C2 C3 1.387(6)
C2 H2 0.9500
C3 C4 1.380(6)
C3 H3 0.9500
C4 C5 1.389(5)
C4 H4 0.9500
C5 C6 1.393(5)
C5 H5 0.9500
C6 C7 1.524(5)
C7 N1 1.472(5)
C7 C8 1.526(6)
C7 H7 1.0000
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 O1 1.235(4)
C9 N1 1.327(4)
C9 C10 1.516(5)
C10 N2 1.485(4)
C10 H10A 0.9900
C10 H10B 0.9900
N1 H1A 0.8800
N2 H2A 0.9100
N2 H2B 0.9100
N2 H2C 0.9100
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 O1 1_655 0.88 2.01 2.839(4) 156
N2 H2A Cl1 . 0.91 2.32 3.181(3) 157
N2 H2B Cl1 3_546 0.91 2.27 3.146(3) 162
N2 H2C Cl1 3_556 0.91 2.36 3.222(3) 158
C7 H7 O1 . 1.00 2.45 2.809(5) 101
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180291
