Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of <i>Monanthotaxis trichocarpa</i>.
Maeda, Gasper; van der Wal, Jelle; Gupta, Arvind Kumar; Munissi, Joan J. E.; Orthaber, Andreas; Sunnerhagen, Per; Nyandoro, Stephen S.; Erdélyi, Máté; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.9b00363

data_1557170
_publ_section_title
;
 Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots
 of <i>Monanthotaxis trichocarpa</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00363
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 Cl O6'
_chemical_formula_sum            'C22 H21 Cl O6'
_chemical_formula_weight         416.84
_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
_audit_creation_date             2019-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9330(5)
_cell_length_b                   13.4485(11)
_cell_length_c                   12.3282(10)
_cell_measurement_reflns_used    4310
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      2.25
_cell_volume                     977.74(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0353
_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       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.780
_diffrn_reflns_theta_min         1.662
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0767 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.9551. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0339P)^2^+0.2053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4358
_reflns_number_total             5067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00363_si_002.cif
_cod_data_source_block           2_a
_cod_database_code               1557170
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_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, All O(H) groups
2. Others
 Fixed Sof: C18(0.5) H18(0.5) C19(0.5) H19(0.5) C18B(0.5) H18B(0.5) C19B(0.5)
 H19B(0.5) H20(0.5) H20A(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C21B(0.5)
 H21B(0.5) C22B(0.5) H22B(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18),
 C19(H19), C18B(H18B), C19B(H19B), C20(H20), C20(H20A), C21(H21), C22(H22),
 C21B(H21B), C22B(H22B)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              29016
_shelx_hkl_checksum              17247
_olex2_submission_special_instructions 'No special instructions were received'