Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives.
Ma, Shanshan; Yu, Aimin; Meng, Xiangtai; Organic & biomolecular chemistry 16 (2018) 2885–2892; doi:10.1039/c8ob00004b

data_7156175
_publ_section_title
;
 Phosphine-catalyzed [4 + 2] annulation of \g-benzyl allenoates: facile
 synthesis of benzothieno[3,2-b]pyran derivatives.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2885
_journal_page_last               2892
_journal_paper_doi               10.1039/c8ob00004b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H21 Cl O7 S'
_chemical_formula_sum            'C24 H21 Cl O7 S'
_chemical_formula_weight         488.92
_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     dual
_audit_creation_date             2017-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-12-12 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                103.441(10)
_cell_angle_beta                 110.162(11)
_cell_angle_gamma                103.530(10)
_cell_formula_units_Z            2
_cell_length_a                   10.8783(12)
_cell_length_b                   11.1724(13)
_cell_length_c                   11.9506(14)
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3240
_cell_measurement_theta_min      2.2740
_cell_volume                     1245.2(3)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    5.00    --   30.00  54.00   0.00  195
  2  \w    -75.00  30.00   1.00    5.00    --   30.00  54.00 120.00  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      0.0351256000
_diffrn_orient_matrix_UB_12      -0.0444351000
_diffrn_orient_matrix_UB_13      -0.0110874000
_diffrn_orient_matrix_UB_21      0.0647567000
_diffrn_orient_matrix_UB_22      0.0524792000
_diffrn_orient_matrix_UB_23      0.0324626000
_diffrn_orient_matrix_UB_31      0.0067111000
_diffrn_orient_matrix_UB_32      -0.0102050000
_diffrn_orient_matrix_UB_33      0.0579149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5978
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35153
_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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_refine_diff_density_max         1.220
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.080
_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     300
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0802
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1352P)^2^+0.6414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2120
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             4359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00004b2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7156174--7156175.cif.'
_cod_original_cell_volume        1245.1(3)
_cod_database_code               7156175
_reflns_odcompleteness_completeness 83.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.86
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C17(H17), C3(H3), C14(H14), C16(H16), C2(H2), C15(H15)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              70541
_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 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.642