Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors
Chear, Nelson Jeng-Yeou; León, Francisco; Sharma, Abhisheak; Kanumuri, Siva Rama Raju; Zwolinski, Grant; Abboud, Khalil A.; Singh, Darshan; Restrepo, Luis F.; Patel, Avi; Hiranita, Takato; Ramanathan, Surash; Hampson, Aidan J.; McMahon, Lance R.; McCurdy, Christopher R.; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.0c01055

data_1560704
_publ_section_title
;
 Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa
 (Kratom) and the Role of Oxindoles on Human Opioid Receptors
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01055
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H30 N2 O5'
_chemical_formula_weight         414.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-09 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 113.5990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5794(7)
_cell_length_b                   9.9646(4)
_cell_length_c                   12.8190(4)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.75
_cell_measurement_theta_min      3.76
_cell_volume                     2291.84(14)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12697
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        64.969
_diffrn_reflns_theta_max         64.969
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'I\mS microsource'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3&#x0096;8.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0839P)^2^+1.9199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.671
_reflns_number_gt                3137
_reflns_number_total             3220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01055_si_002.cif
_cod_data_source_block           jfl1
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1560704
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.682
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              66605
_shelx_hkl_checksum              23971