Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction
Danda, Adithi; Kesava-Reddy, Naredla; Golz, Christopher; Strohmann, Carsten; Kumar, Kamal; Organic Letters  (2016) –; doi:10.1021/acs.orglett.6b01030

data_1543331
_publ_section_title
;
 Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via
 Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b01030
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 Cl N O6'
_chemical_formula_sum            'C20 H18 Cl N O6'
_chemical_formula_weight         403.80
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4088(2)
_cell_length_b                   12.5634(3)
_cell_length_c                   20.4594(7)
_cell_measurement_reflns_used    14685
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.8300
_cell_measurement_theta_min      2.8920
_cell_volume                     1904.36(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39252
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.568
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0380P)^2^+0.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4201
_reflns_number_total             4580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01030_si_002.cif
_cod_data_source_block           3128
_cod_original_cell_volume        1904.36(10)
_cod_database_code               1543331
_shelxl_version_number           2014/6
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C11(H11)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              57981
_shelx_hkl_checksum              89809
_olex2_submission_special_instructions 'No special instructions were received'