Construction of [6-5-5-6-6] Pentacyclic Skeleton via Phosphine Catalyzed Domino Reaction and Mechanism Study.
Ma, Shanshan; Yu, Aimin; Zhang, Shunguang; Zhang, Lei; Meng, Xiangtai; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00566

data_4038447
_publ_section_title
;
 Construction of [6-5-5-6-6] Pentacyclic Skeleton via Phosphine Catalyzed
 Domino Reaction and Mechanism Study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00566
_journal_year                    2020
_chemical_formula_moiety         'C28 H24 Cl N O4 S2'
_chemical_formula_sum            'C28 H24 Cl N O4 S2'
_chemical_formula_weight         538.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.458(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9679(17)
_cell_length_b                   17.281(3)
_cell_length_c                   14.158(3)
_cell_measurement_reflns_used    1221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0400
_cell_measurement_theta_min      2.3400
_cell_volume                     2573.5(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -75.00 106.00   1.00   20.00    --   30.00  54.00 120.00  181
  2  \w    -60.00   6.00   1.00   20.00    --   30.00  54.00 240.00   66
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0093997000
_diffrn_orient_matrix_UB_12      0.0396886000
_diffrn_orient_matrix_UB_13      0.0084579000
_diffrn_orient_matrix_UB_21      0.0325401000
_diffrn_orient_matrix_UB_22      0.0103474000
_diffrn_orient_matrix_UB_23      -0.0349316000
_diffrn_orient_matrix_UB_31      -0.0583163000
_diffrn_orient_matrix_UB_32      -0.0006458000
_diffrn_orient_matrix_UB_33      -0.0379301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_unetI/netI     0.1505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9948
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.357
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1120
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0705
_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^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2002
_reflns_number_total             4523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00566_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        2573.6(8)
_cod_database_code               4038447
_reflns_odcompleteness_completeness 87.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.94
_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
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00C), C00U(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00G(H00G), C00K(H00K), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00T(H00T), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y)
2.d Idealised Me refined as rotating group:
 C00Z(H00H,H00J,H00L), C010(H01A,H01B,H01C)
;
_shelx_res_checksum              25701
_shelx_hkl_checksum              50871
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.977
_oxdiff_exptl_absorpt_empirical_full_min 0.445