Solid State Auto Inversion of C-Centrochirality: Enantioselective Total Synthesis of Furocarbazolones (-)-epi-Claulansine D and (-)-Claulansine D and, Pyranocarbazolone (+)-epi-Claulansine C.
Markad, Shivaji B.; Argade, Narshinha P.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02773

data_4033293
_publ_section_title
;
 Solid State Auto Inversion of C-Centrochirality: Enantioselective Total
 Synthesis of Furocarbazolones (-)-epi-Claulansine D and (-)-Claulansine D
 and, Pyranocarbazolone (+)-epi-Claulansine C.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02773
_journal_year                    2017
_chemical_formula_moiety         'C19 H19 N O5'
_chemical_formula_sum            'C19 H19 N O5'
_chemical_formula_weight         341.35
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                   5.040(4)
_cell_length_b                   15.346(12)
_cell_length_c                   20.856(16)
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.38
_cell_measurement_theta_min      2.36
_cell_volume                     1613(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.4812
_diffrn_reflns_av_unetI/netI     0.4222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31751
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         2.361
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       roadshape
_exptl_crystal_F_000             720.0
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.3228
_refine_ls_R_factor_gt           0.1026
_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^)+(0.1000P)^2^+0.0523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.2271
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1470
_reflns_number_total             4000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02773_si_002.cif
_cod_data_source_block           TR2_a
_cod_database_code               4033293
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              9423
_shelx_hkl_checksum              19621