Catalytic enantioselective synthesis of 2-aryl-chromenes
Zeng, Bi-Shun; Yu, Xinyi; Siu, Paul W.; Scheidt, Karl A.; Chemical Science 5 (2014) 2277–; doi:10.1039/c4sc00423j

data_1516565
_publ_section_title
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 Catalytic enantioselective synthesis of 2-aryl-chromenes
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              2277
_journal_paper_doi               10.1039/c4sc00423j
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C52 H70 N O4 P'
_chemical_formula_sum            'C52 H70 N O4 P'
_chemical_formula_weight         804.06
_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
_audit_creation_date             2014-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3371(4)
_cell_length_b                   19.9237(6)
_cell_length_c                   34.7236(10)
_cell_measurement_reflns_used    9580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.02
_cell_measurement_theta_min      2.56
_cell_volume                     9226.9(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.96
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            113484
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.073
_diffrn_reflns_theta_min         2.545
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0729 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       block
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 6735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.014(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1065
_refine_ls_number_reflns         15587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0572P)^2^+3.0097P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                15189
_reflns_number_total             15587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc00423j2.cif
_cod_data_source_block           cu_bz06_94_0m
_cod_database_code               1516565
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.787
_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:
 C60(H60), C59(H59), C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C1(H1A,H1B), C48(H48A,H48B), C53(H53A,H53B), C57(H57A,H57B),
 C90(H90A,H90B), C56(H56A,H56B), C26(H26A,H26B), C78(H78A,H78B), C100(H10J,
 H10K), C68(H68A,H68B), C88(H88A,H88B), C36(H36A,H36B), C2(H2A,H2B), C38(H38A,
 H38B), C46(H46A,H46B), C80(H80A,H80B), C5(H5A,H5B), C16(H16A,H16B), C98(H98A,
 H98B), C54(H54A,H54B), C4(H4A,H4B), C70(H70A,H70B), C18(H18A,H18B), C55(H55A,
 H55B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C33(H33), C67(H67), C31(H31), C85(H85), C95(H95), C45(H45), C77(H77),
 C25(H25), C35(H35), C21(H21), C97(H97), C87(H87), C73(H73), C41(H41), C23(H23),
  C43(H43), C93(H93), C83(H83), C75(H75), C63(H63), C65(H65), C13(H13),
 C15(H15), C11(H11)
2.d Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C103(H10A,H10B,H10C), C51(H51A,H51B,H51C), C49(H49A,H49B,
 H49C), C99(H99A,H99B,H99C), C101(H10D,H10E,H10F), C104(H10G,H10H,H10I),
 C52(H52A,H52B,H52C), C19(H19A,H19B,H19C), C69(H69A,H69B,H69C), C39(H39A,H39B,
 H39C), C71(H71A,H71B,H71C), C37(H37A,H37B,H37C), C81(H81A,H81B,H81C), C17(H17A,
 H17B,H17C), C27(H27A,H27B,H27C), C79(H79A,H79B,H79C), C89(H89A,H89B,H89C),
 C91(H91A,H91B,H91C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              8685
_shelx_hkl_checksum              35376