A chiral auxiliary-based synthesis of the C5‒C17 trans-decalin framework of anthracimycin
Freeman, Jared L.; Brimble, Margaret A.; Furkert, Daniel P.; Organic Chemistry Frontiers 6 (2019) 2954–; doi:10.1039/C9QO00769E

data_1555042
_publ_section_title
;
 A chiral auxiliary-based synthesis of the C5--C17 trans-decalin framework
 of anthracimycin
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2954
_journal_paper_doi               10.1039/C9QO00769E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C33 H38 N O5'
_chemical_formula_weight         528.64
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-06-13 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                108.986(4)
_cell_angle_beta                 98.417(3)
_cell_angle_gamma                114.037(4)
_cell_formula_units_Z            1
_cell_length_a                   9.1302(3)
_cell_length_b                   9.1578(5)
_cell_length_c                   10.2260(4)
_cell_measurement_reflns_used    4896
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      68.241
_cell_measurement_theta_min      5.606
_cell_volume                     698.83(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16713
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         5.606
_exptl_absorpt_coefficient_mu    0.670
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             283
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(12)
_refine_ls_extinction_coef       0.007(2)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0880P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4695
_reflns_number_total             4896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00769e2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        698.83(6)
_cod_database_code               1555042
_publcif_datablock.id            {15b6339e-7bab-4b86-966b-bdb23dc316d1}
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.924
_shelx_res_checksum              11128
_shelx_hkl_checksum              92658
_publcif_funding_html
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