Enantiomeric Pairs of Meroterpenoids with Diverse Heterocyclic Systems from Rhododendron nyingchiense.
Huang, Guang-Hui; Hu, Zhu; Lei, Chun; Wang, Pei-Pei; Yang, Jing; Li, Jing-Ya; Li, Jia; Hou, Ai-Jun; Journal of natural products 81 (2018) 1810–1818; doi:10.1021/acs.jnatprod.8b00273

data_1553371
_publ_section_title
;
 Enantiomeric Pairs of Meroterpenoids with Diverse Heterocyclic Systems
 from Rhododendron nyingchiense.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1810
_journal_page_last               1818
_journal_paper_doi               10.1021/acs.jnatprod.8b00273
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H22 O3, 0.5(C H4 O)'
_chemical_formula_sum            'C17.5 H24 O3.5'
_chemical_formula_weight         290.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 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                   10.27200(10)
_cell_length_b                   16.5830(2)
_cell_length_c                   18.9486(2)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.06
_cell_measurement_theta_min      3.54
_cell_volume                     3227.72(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20904
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.746
_diffrn_reflns_theta_min         3.542
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1175 before and 0.0559 after correction. The Ratio of minimum to maximum transmission is 0.7710. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       0.0051(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0513P)^2^+0.3101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5615
_reflns_number_total             5872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00273_si_005.cif
_cod_data_source_block           cu_dm17280_0m
_cod_original_formula_sum        'C17.50 H24 O3.50'
_cod_database_code               1553371
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.869
_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.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4), C11(H11), C3B(H3BA), C4B(H4B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C9B(H9BA,H9BB), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C6B(H6B), C8B(H8B)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C13B(H13C,H13D)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14B(H14D,H14E,
 H14F), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F), C2S(H2SA,H2SB,H2SC)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O2B(H2B), O3B(H3B), O1S(H1S)
;
_shelx_res_checksum              79551
_shelx_hkl_checksum              17910
_olex2_submission_special_instructions 'No special instructions were received'