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_1547044
_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 H14 Cl N O2'
_chemical_formula_sum            'C12 H14 Cl N O2'
_chemical_formula_weight         239.69
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.1094(2)
_cell_length_b                   8.6923(2)
_cell_length_c                   33.1247(7)
_cell_measurement_reflns_used    6051
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.256
_cell_measurement_theta_min      2.668
_cell_volume                     2334.94(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            13135
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.306
_diffrn_reflns_theta_min         2.668
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.778
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.4136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0757 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.7939. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3706
_reflns_number_total             4251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02177_si_011.cif
_cod_data_source_block           NIH29
_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               1547044
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.744
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = O2-H2 = O2'-H2' = N1'-H1'B = N1'-H1'A
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C11'(H11')
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C9'(H9'A,H9'B), C10'(H10C,H10D),
 C12'(H12C,H12D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C2'(H2'A), C3'(H3'), C4'(H4'), C5'(H5')
;
_shelx_res_checksum              92635
_shelx_hkl_checksum              44594
_olex2_submission_special_instructions 'No special instructions were received'