Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives.
Jia, Jiru; Yu, Aimin; Ma, Shanshan; Zhang, Youquan; Li, Ke; Meng, Xiangtai; Organic letters 19 (2017) 6084–6087; doi:10.1021/acs.orglett.7b02916

data_1548606
_publ_section_title
;
 Solvent-Controlled Switchable Domino Reactions of MBH Carbonate:
 Synthesis of Benzothiophene Fused \a-Pyran, 2,3-Dihydrooxepine, and
 Oxatricyclodecene Derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6084
_journal_page_last               6087
_journal_paper_doi               10.1021/acs.orglett.7b02916
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C18 H18 O5 S'
_chemical_formula_sum            'C18 H18 O5 S'
_chemical_formula_weight         346.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                81.945(3)
_cell_angle_beta                 68.341(3)
_cell_angle_gamma                81.982(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1078(9)
_cell_length_b                   9.1877(9)
_cell_length_c                   11.1460(11)
_cell_measurement_reflns_used    6272
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.524
_cell_measurement_theta_min      3.084
_cell_volume                     854.38(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         3.084
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0641 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8864.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001
_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          0.1320
_refine_ls_wR_factor_ref         0.1508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2736
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02916_si_002.cif
_cod_data_source_block           tianj0602_0m
_cod_database_code               1548606
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              2929
_shelx_hkl_checksum              41383
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'