#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/88/2218883.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_2218883
loop_
_publ_author_name
'Hakey, Patrick'
'Ouellette, Wayne'
'Zubieta, Jon'
'Korter, Timothy'
_publ_section_title
;
 (S)-(+)-Ketamine hydrochloride
;
_journal_coeditor_code           BH2181
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1487
_journal_paper_doi               10.1107/S1600536808021053
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C13 H17 Cl N O, Cl'
_chemical_formula_sum            'C13 H17 Cl2 N O'
_chemical_formula_weight         274.18
_chemical_name_common            '(S)-(+)-Ketamine hydrochloride'
_chemical_name_systematic
;
(S)-(+)-N-[1-(2-chlorophenyl)-2-oxocyclohexyl]methanaminium chloride
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4338(4)
_cell_length_b                   7.0715(4)
_cell_length_c                   11.3524(6)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.47
_cell_volume                     662.56(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6985
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0.001
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_correction_T_min  0.7977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details 'Flack (1983), 1472 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0273
_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)+(0.0378P)²+0.0273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                3146
_reflns_number_total             3251
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2181.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2218883
_cod_database_fobs_code          2218883
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_calc_flag
_atom_site_occupancy
Cl Cl2 0.05227(4) 0.23769(5) 0.35081(3) 0.01627(9) Uani d 1
Cl Cl1 0.34238(5) -0.13679(5) 0.87212(4) 0.02248(10) Uani d 1
O O1 0.38001(14) -0.03746(17) 0.60012(10) 0.0205(2) Uani d 1
N N1 0.11098(16) 0.1291(2) 0.62148(11) 0.0132(3) Uani d 1
C C1 0.27185(19) 0.0822(2) 0.90899(14) 0.0157(3) Uani d 1
C C2 0.2437(2) 0.0998(3) 1.02456(15) 0.0212(3) Uani d 1
C C3 0.1889(2) 0.2691(3) 1.06202(16) 0.0239(4) Uani d 1
C C4 0.1635(2) 0.4199(3) 0.98344(15) 0.0218(4) Uani d 1
C C5 0.19088(19) 0.4012(2) 0.86757(15) 0.0175(3) Uani d 1
C C6 0.24628(16) 0.2315(3) 0.82673(13) 0.0140(3) Uani d 1
C C7 0.26395(16) 0.2136(2) 0.69555(12) 0.0124(3) Uani d 1
C C8 0.40443(19) 0.0878(2) 0.67428(13) 0.0155(3) Uani d 1
C C9 0.57016(19) 0.1543(2) 0.73576(15) 0.0176(3) Uani d 1
C C10 0.59821(19) 0.3492(3) 0.68330(14) 0.0175(3) Uani d 1
C C11 0.46277(19) 0.4860(2) 0.69619(15) 0.0166(3) Uani d 1
C C12 0.29711(19) 0.4052(2) 0.63815(14) 0.0142(3) Uani d 1
C C13 -0.04410(18) 0.2160(3) 0.63712(14) 0.0170(3) Uani d 1
H H11B 0.471(2) 0.511(3) 0.7848(19) 0.024(5) Uiso d 1
H H12A 0.294(2) 0.378(3) 0.5499(16) 0.014(4) Uiso d 1
H H13A -0.060(2) 0.181(3) 0.7166(17) 0.015(5) Uiso d 1
H H10B 0.603(2) 0.334(3) 0.6003(17) 0.016(5) Uiso d 1
H H9A 0.649(2) 0.055(3) 0.7199(18) 0.024(5) Uiso d 1
H H1B 0.116(2) 0.140(3) 0.5461(17) 0.008(4) Uiso d 1
H H10A 0.703(3) 0.397(3) 0.7211(17) 0.021(5) Uiso d 1
H H13B -0.126(2) 0.167(3) 0.5775(18) 0.021(5) Uiso d 1
H H9B 0.574(2) 0.167(3) 0.8215(18) 0.018(5) Uiso d 1
H H5 0.174(2) 0.503(3) 0.8174(19) 0.023(5) Uiso d 1
H H12B 0.209(2) 0.490(3) 0.6419(16) 0.018(5) Uiso d 1
H H3 0.166(2) 0.278(3) 1.1373(19) 0.026(6) Uiso d 1
H H2 0.259(2) -0.003(3) 1.0735(17) 0.015(5) Uiso d 1
H H4 0.128(2) 0.542(3) 1.0038(18) 0.022(5) Uiso d 1
H H13C -0.038(2) 0.351(3) 0.6318(16) 0.018(5) Uiso d 1
H H1A 0.105(3) 0.015(4) 0.6352(18) 0.024(5) Uiso d 1
H H11A 0.483(3) 0.601(4) 0.6570(18) 0.029(6) Uiso d 1
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
C13 N1 C7 116.17(12)
C13 N1 H1B 107.8(12)
C7 N1 H1B 107.7(12)
C13 N1 H1A 106.8(15)
C7 N1 H1A 111.3(15)
H1B N1 H1A 106.7(19)
C2 C1 C6 122.11(15)
C2 C1 Cl1 116.19(13)
C6 C1 Cl1 121.69(12)
C3 C2 C1 120.18(16)
C3 C2 H2 121.6(12)
C1 C2 H2 118.2(12)
C4 C3 C2 119.23(15)
C4 C3 H3 121.0(14)
C2 C3 H3 119.7(14)
C3 C4 C5 120.40(16)
C3 C4 H4 123.7(13)
C5 C4 H4 115.9(13)
C4 C5 C6 121.81(16)
C4 C5 H5 118.8(13)
C6 C5 H5 119.4(13)
C1 C6 C5 116.27(13)
C1 C6 C7 123.69(15)
C5 C6 C7 119.89(14)
N1 C7 C6 109.33(11)
N1 C7 C8 106.29(12)
C6 C7 C8 115.60(12)
N1 C7 C12 108.57(11)
C6 C7 C12 113.44(13)
C8 C7 C12 103.13(11)
O1 C8 C9 124.09(15)
O1 C8 C7 120.38(14)
C9 C8 C7 114.74(13)
C8 C9 C10 107.60(13)
C8 C9 H9A 106.5(12)
C10 C9 H9A 113.3(12)
C8 C9 H9B 109.6(12)
C10 C9 H9B 109.0(12)
H9A C9 H9B 110.8(16)
C11 C10 C9 110.66(13)
C11 C10 H10B 110.3(11)
C9 C10 H10B 108.8(12)
C11 C10 H10A 111.8(13)
C9 C10 H10A 110.1(13)
H10B C10 H10A 105.0(16)
C10 C11 C12 110.94(14)
C10 C11 H11B 108.0(12)
C12 C11 H11B 111.3(12)
C10 C11 H11A 106.8(14)
C12 C11 H11A 110.4(13)
H11B C11 H11A 109.3(17)
C11 C12 C7 111.90(12)
C11 C12 H12A 109.5(10)
C7 C12 H12A 106.2(12)
C11 C12 H12B 113.2(13)
C7 C12 H12B 108.5(12)
H12A C12 H12B 107.2(15)
N1 C13 H13A 107.3(11)
N1 C13 H13B 107.4(12)
H13A C13 H13B 111.0(17)
N1 C13 H13C 110.3(11)
H13A C13 H13C 109.3(16)
H13B C13 H13C 111.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7403(16)
O1 C8 1.210(2)
N1 C13 1.488(2)
N1 C7 1.5108(19)
N1 H1B 0.869(18)
N1 H1A 0.83(3)
C1 C2 1.386(2)
C1 C6 1.397(2)
C2 C3 1.382(3)
C2 H2 0.91(2)
C3 C4 1.378(3)
C3 H3 0.92(2)
C4 C5 1.388(2)
C4 H4 0.96(2)
C5 C6 1.401(2)
C5 H5 0.91(2)
C6 C7 1.5321(19)
C7 C8 1.540(2)
C7 C12 1.553(2)
C8 C9 1.503(2)
C9 C10 1.539(2)
C9 H9A 1.01(2)
C9 H9B 0.97(2)
C10 C11 1.527(2)
C10 H10B 0.957(18)
C10 H10A 0.96(2)
C11 C12 1.528(2)
C11 H11B 1.01(2)
C11 H11A 0.96(2)
C12 H12A 1.014(17)
C12 H12B 0.96(2)
C13 H13A 0.971(19)
C13 H13B 0.93(2)
C13 H13C 0.96(2)
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
_geom_hbond_publ_flag
N1 H1A Cl2 2_546 0.83(3) 2.39(3) 3.1359(15) 151(2) yes
N1 H1B Cl2 . 0.869(19) 2.278(19) 3.1065(13) 159.4(17) yes
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
C6 C1 C2 C3 -0.2(2)
Cl1 C1 C2 C3 179.44(13)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 0.7(3)
C3 C4 C5 C6 -0.7(3)
C2 C1 C6 C5 0.2(2)
Cl1 C1 C6 C5 -179.37(11)
C2 C1 C6 C7 -175.34(14)
Cl1 C1 C6 C7 5.1(2)
C4 C5 C6 C1 0.2(2)
C4 C5 C6 C7 175.93(14)
C13 N1 C7 C6 48.63(18)
C13 N1 C7 C8 174.05(13)
C13 N1 C7 C12 -75.59(16)
C1 C6 C7 N1 81.64(16)
C5 C6 C7 N1 -93.75(17)
C1 C6 C7 C8 -38.2(2)
C5 C6 C7 C8 146.41(14)
C1 C6 C7 C12 -157.03(14)
C5 C6 C7 C12 27.58(18)
N1 C7 C8 O1 6.73(18)
C6 C7 C8 O1 128.23(15)
C12 C7 C8 O1 -107.40(16)
N1 C7 C8 C9 177.01(12)
C6 C7 C8 C9 -61.50(17)
C12 C7 C8 C9 62.88(15)
O1 C8 C9 C10 107.30(17)
C7 C8 C9 C10 -62.57(16)
C8 C9 C10 C11 55.38(17)
C9 C10 C11 C12 -55.57(17)
C10 C11 C12 C7 59.27(17)
N1 C7 C12 C11 -171.44(12)
C6 C7 C12 C11 66.81(16)
C8 C7 C12 C11 -58.97(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26332012
