Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic
Jurásek, Bronislav; Králík, František; Rimpelová, Silvie; Čejka, Jan; Setnička, Vladimír; Ruml, Tomáš; Kuchař, Martin; Kohout, Michal; New Journal of Chemistry 42 (2018) 19360–; doi:10.1039/C8NJ03107J

data_7057862
_publ_section_title
;
 Synthesis, absolute configuration and in vitro cytotoxicity of
 deschloroketamine enantiomers: rediscovered and abused dissociative
 anaesthetic
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19360
_journal_paper_doi               10.1039/C8NJ03107J
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18.00 Cl1 N1 O1'
_chemical_formula_sum            'C13 H18 Cl N O'
_chemical_formula_weight         239.74
_chemical_name_systematic        (S)-deschloroketamine
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2018-04-20 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4163(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5215(3)
_cell_length_b                   13.1197(5)
_cell_length_c                   15.0635(6)
_cell_measurement_reflns_used    106
_cell_measurement_temperature    180
_cell_measurement_theta_max      59
_cell_measurement_theta_min      14
_cell_volume                     1288.44(9)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21595
_diffrn_reflns_theta_full        70.034
_diffrn_reflns_theta_max         70.034
_diffrn_reflns_theta_min         2.934
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.40
_exptl_absorpt_correction_T_min  0.34
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             511.996
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.374
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 2186 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.095(10)
_refine_ls_extinction_coef       259(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.0009435
_refine_ls_shift/su_mean         0.0001990
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 6.82 10.9 6.07 2.41 0.570 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0677
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0677
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4701
_reflns_number_total             4737
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.78
_oxford_diffrn_Wilson_scale      9.45
_oxford_refine_ls_r_factor_ref   0.0253
_oxford_refine_ls_scale          0.3372(3)
_oxford_reflns_number_all        4737
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c8nj03107j2.cif
_cod_data_source_block           SDCK
_cod_depositor_comments
'Adding full bibliography for 7057861--7057863.cif.'
_cod_original_cell_volume        1288.44(5)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C13 H18.00 Cl1 N1 O1'
_cod_database_code               7057862