Total Synthesis of Dactylicapnosines A and B.
Zhao, Yinjiao; Li, Yuda; Wang, Bei; Zhao, Jingfeng; Li, Liang; Luo, Xiao-Dong; Zhang, Hongbin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01900

data_4038908
_publ_section_title
;
 Total Synthesis of Dactylicapnosines A and B.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01900
_journal_year                    2020
_chemical_formula_moiety         'C22 H25 N O8'
_chemical_formula_sum            'C22 H25 N O8'
_chemical_formula_weight         431.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1613(17)
_cell_length_b                   8.9412(7)
_cell_length_c                   10.6525(9)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.77
_cell_measurement_theta_min      2.28
_cell_volume                     2015.5(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 0.999
_diffrn_measured_fraction_theta_max 0.949
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.106
_diffrn_reflns_theta_min         1.925
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.6417
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0554P)^2^+0.3079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                5683
_reflns_number_total             5968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01900_si_002.cif
_cod_data_source_block           mo_zhb_zyj3_0m
_cod_database_code               4038908
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              85941
_shelx_hkl_checksum              3773