Nicotabin A, a Sesquiterpenoid Derivative from Nicotiana tabacum.
Feng, Tao; Li, Xue-Mei; He, Jun; Ai, Hong-Lian; Chen, He-Ping; Li, Xiao-Nian; Li, Zheng-Hui; Liu, Ji-Kai; Organic letters 19 (2017) 5201–5203; doi:10.1021/acs.orglett.7b02559

data_1546964
_publ_section_title
;
 Nicotabin A, a Sesquiterpenoid Derivative from Nicotiana tabacum.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5201
_journal_page_last               5203
_journal_paper_doi               10.1021/acs.orglett.7b02559
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 O7'
_chemical_formula_sum            'C21 H28 O7'
_chemical_formula_weight         392.43
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.70380(10)
_cell_length_b                   8.3662(2)
_cell_length_c                   16.9526(3)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.38
_cell_measurement_theta_min      2.61
_cell_volume                     949.31(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.378
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.4746
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0541
_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^)+(0.1301P)^2^+0.4827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3152
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02559_si_002.cif
_cod_data_source_block           cu_lft25_0m
_cod_depositor_comments          'Adding full bibliography for 1546964.cif.'
_cod_database_code               1546964
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.484
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              62938
_shelx_hkl_checksum              21382