Enantioselective synthesis of cyclopenta[b]benzofurans via an organocatalytic intramolecular double cyclization
Paz, Bruno Matos; Li, Yang; Thøgersen, Mathias Kirk; Jørgensen, Karl Anker; Chem. Sci.  (2017) –; doi:10.1039/C7SC03006A

data_1547672
_publ_section_title
;
 Enantioselective synthesis of cyclopenta[b]benzofurans via an
 organocatalytic intramolecular double cyclization
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03006A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Br O3'
_chemical_formula_sum            'C17 H13 Br O3'
_chemical_formula_weight         345.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-21 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4889(17)
_cell_length_b                   15.637(2)
_cell_length_c                   17.361(3)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      20.53
_cell_measurement_theta_min      2.25
_cell_volume                     2847.5(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.541
_diffrn_reflns_theta_min         1.383
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.556
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.3435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1833 before and 0.0966 after correction.
The Ratio of minimum to maximum transmission is 0.4614.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.042(4)
_refine_ls_d_res_high            0.7992
_refine_ls_d_res_low             11.6191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.1641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0528
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                5607
_reflns_number_total             5817
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7sc03006a2.cif
_cod_data_source_block           2017_02_02_2_0m
_cod_original_cell_volume        2847.6(8)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1547672
_shelx_shelxl_version_number     2016/6
_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 O(H) groups
2. Restrained distances
 O008-H008
 0.97 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C00N(H00N), C00Q(H00Q), C00S(H00S), C015(H015)
3.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00C), C011(H01A,H01B)
3.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K),
 C00M(H00M), C00P(H00P), C00T(H00T), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C013(H013), C014(H014), C016(H016)
3.d Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_olex2_submission_special_instructions 'No special instructions were received'