Quinoline alkaloids with anti-inflammatory activity from <i>Zanthoxylum avicennae</i>.
Ji, Kai-Long; Liu, Wei; Yin, Wei-Hang; Li, Jing-Ya; Yue, Jian-Min; Organic & biomolecular chemistry 20 (2022) 4176–4182; doi:10.1039/d2ob00711h

data_7158687
_publ_section_title
;
 Quinoline alkaloids with anti-inflammatory activity from <i>Zanthoxylum
 avicennae</i>.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4176
_journal_page_last               4182
_journal_paper_doi               10.1039/d2ob00711h
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.29
_chemical_name_systematic        (+)-Myrtopsine
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-19 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5948(3)
_cell_length_b                   8.5216(3)
_cell_length_c                   18.7212(6)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.964
_cell_measurement_theta_min      4.546
_cell_volume                     1350.19(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      169.99
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14913
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.944
_diffrn_reflns_theta_min         4.545
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1050 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.8330. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2045 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0427P)^2^+0.1309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4762
_reflns_number_total             5038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00711h2.cif
_cod_data_source_block           mj19351_0m
_cod_depositor_comments
'Adding full bibliography for 7158685--7158687.cif.'
_cod_database_code               7158687
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3), C2B(H2BA), C3B(H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C2'(H2'A,H2'B,H2'C), C3'(H3'A,H3'B,H3'C), C2'B(H2'D,H2'E,
 H2'F), C3'B(H3'D,H3'E,H3'F), C10B(H10D,H10E,H10F)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O2B(H2B), O4B(H4B)
;
_shelx_res_checksum              62624
_olex2_submission_special_instructions 'No special instructions were received'