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_4038448
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                91.482(8)
_cell_angle_beta                 91.077(8)
_cell_angle_gamma                98.721(8)
_cell_formula_units_Z            2
_cell_length_a                   8.0583(8)
_cell_length_b                   10.8415(10)
_cell_length_c                   14.8495(14)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9640
_cell_measurement_theta_min      2.4510
_cell_volume                     1281.5(2)
_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    -75.00 120.00   1.00    8.00    --   30.00  54.00 240.00  195
  2  \w    -75.00  30.00   1.00    8.00    --   30.00  54.00   0.00  105
;
_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      -0.0073573000
_diffrn_orient_matrix_UB_12      -0.0424729000
_diffrn_orient_matrix_UB_13      0.0357620000
_diffrn_orient_matrix_UB_21      -0.0053722000
_diffrn_orient_matrix_UB_22      -0.0506794000
_diffrn_orient_matrix_UB_23      -0.0316346000
_diffrn_orient_matrix_UB_31      0.0886065000
_diffrn_orient_matrix_UB_32      0.0035311000
_diffrn_orient_matrix_UB_33      0.0021557000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6238
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         2.312
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76597
_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    1.394
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             560
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0478P)^2^+0.1649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3566
_reflns_number_total             4513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00566_si_003.cif
_cod_data_source_block           3
_cod_database_code               4038448
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 82.81
_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:
 C009(H009), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00Y(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C00Z(H00G,H00H,H00I), C010(H01A,H01B,H01C)
;
_shelx_res_checksum              55309
_shelx_hkl_checksum              6201
_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.717