Hydroxynorketamine Pharmacokinetics and Antidepressant Behavioral Effects of (2<i>,</i>6)- and (5<i>R</i>)-Methyl-(2<i>R,</i>6<i>R</i>)-hydroxynorketamines.
Highland, Jaclyn N.; Morris, Patrick J.; Konrath, Kylie M.; Riggs, Lace M.; Hagen, Natalie R.; Zanos, Panos; Powels, Chris F.; Moaddel, Ruin; Thomas, Craig J.; Wang, Amy Q.; Gould, Todd D.; ACS chemical neuroscience 13 (2022) 510–523; doi:10.1021/acschemneuro.1c00761

data_4519344
_publ_section_title
;
 Hydroxynorketamine Pharmacokinetics and Antidepressant Behavioral Effects
 of (2<i>,</i>6)- and
 (5<i>R</i>)-Methyl-(2<i>R,</i>6<i>R</i>)-hydroxynorketamines.
;
_journal_issue                   4
_journal_name_full               'ACS chemical neuroscience'
_journal_page_first              510
_journal_page_last               523
_journal_paper_doi               10.1021/acschemneuro.1c00761
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H16 Cl N O2'
_chemical_formula_sum            'C13 H16 Cl N O2'
_chemical_formula_weight         253.72
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-12-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.266(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5842(9)
_cell_length_b                   11.0230(14)
_cell_length_c                   8.6030(12)
_cell_measurement_reflns_used    7174
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.678
_cell_measurement_theta_min      2.414
_cell_volume                     612.35(14)
_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 0.998
_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_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.414
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.2580
_exptl_absorpt_correction_T_min  0.2321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0725 before and 0.0639 after correction. The Ratio of minimum to maximum transmission is 0.8996. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       Block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0283P)^2^+0.1408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2390
_reflns_number_total             2512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cn1c00761_si_002.cif
_cod_data_source_block           NIH35
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519344
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1B = N1-H1A = O2-H2
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              18025
_shelx_hkl_checksum              94334
_olex2_submission_special_instructions 'No special instructions were received'