Synthesis and N-Methyl-d-aspartate (NMDA) Receptor Activity of Ketamine Metabolites.
Morris, Patrick J.; Moaddel, Ruin; Zanos, Panos; Moore, Curtis E.; Gould, Todd; Zarate, Jr, Carlos A; Thomas, Craig J.; Organic letters 19 (2017) 4572–4575; doi:10.1021/acs.orglett.7b02177

data_1547046
_publ_section_title
;
 Synthesis and N-Methyl-d-aspartate (NMDA) Receptor Activity of Ketamine
 Metabolites.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4572
_journal_page_last               4575
_journal_paper_doi               10.1021/acs.orglett.7b02177
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H15 Cl N O2, Cl, H2 O'
_chemical_formula_sum            'C12 H17 Cl2 N O3'
_chemical_formula_weight         294.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.542(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4047(4)
_cell_length_b                   8.7079(5)
_cell_length_c                   11.7729(6)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.270
_cell_measurement_theta_min      2.885
_cell_volume                     723.81(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25445
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         1.814
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.0891
_exptl_absorpt_correction_T_min  0.0635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1057 before and 0.0817 after correction. The Ratio of minimum to maximum transmission is 0.7127. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       Block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_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/[\s^2^(Fo^2^)+(0.0376P)^2^+0.0706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3508
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02177_si_012.cif
_cod_data_source_block           NIH26
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1547046
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1S-H1SB = O1S-H1SA = N1-H1A = N1-H1C = N1-H1B = O2-H2
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              28934
_shelx_hkl_checksum              73076
_olex2_submission_special_instructions 'No special instructions were received'