Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic Alkylation Reaction of MBH Carbonates: Efficient Construction of Seven-Membered Heterocycles.
Chen, Junlong; Huang, You; Organic letters 19 (2017) 5609–5612; doi:10.1021/acs.orglett.7b02742

data_1547506
_publ_section_title
;
 Phosphine-Catalyzed Sequential [4 + 3] Domino Annulation/Allylic
 Alkylation Reaction of MBH Carbonates: Efficient Construction of
 Seven-Membered Heterocycles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5609
_journal_page_last               5612
_journal_paper_doi               10.1021/acs.orglett.7b02742
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C34 H33 N O7 S'
_chemical_formula_sum            'C34 H33 N O7 S'
_chemical_formula_weight         599.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.688(2)
_cell_length_b                   9.1360(9)
_cell_length_c                   30.698(3)
_cell_measurement_reflns_used    13628
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     6082.5(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      213.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            62530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         3.133
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.590
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.34(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         10691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1497P)^2^+4.4740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.1995
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                9981
_reflns_number_total             10691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02742_si_001.cif
_cod_data_source_block           m20170310a1
_cod_depositor_comments          'Adding full bibliography for 1547506.cif.'
_cod_original_cell_volume        6082.6(10)
_cod_database_code               1547506
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.66(13)
 0.34(13)
2. 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
3.a Riding coordinates:
 C41(H41A,H41B,H41C)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C21(H21A,H21B), C47(H47A,
 H47B), C49(H49A,H49B), C51(H51A,H51B), C55(H55A,H55B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C36(H36), C37(H37),
  C39(H39), C40(H40), C45(H45), C58(H58), C59(H59), C60(H60), C61(H61),
 C62(H62), C64(H64), C65(H65), C66(H66), C67(H67)
3.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B), C53(H53A,H53B)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C50(H50A,H50B,
 H50C), C56(H56A,H56B,H56C)
;
_shelx_res_checksum              88881
_shelx_hkl_checksum              70534
_olex2_submission_special_instructions 'No special instructions were received'