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_1516566
_publ_section_title
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 Catalytic enantioselective synthesis of 2-aryl-chromenes
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_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         'C59 H67 N O4 P Pd, C H2 Cl2, B F4'
_chemical_formula_sum            'C60 H69 B Cl2 F4 N O4 P Pd'
_chemical_formula_weight         1163.24
_chemical_name_systematic
;
 ? 
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_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2225(2)
_cell_length_b                   20.8872(3)
_cell_length_c                   21.6966(3)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.10
_cell_measurement_theta_min      4.08
_cell_volume                     5539.01(14)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.08
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25224
_diffrn_reflns_theta_full        65.11
_diffrn_reflns_theta_max         65.11
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.363
_exptl_absorpt_correction_T_max  0.6784
_exptl_absorpt_correction_T_min  0.5350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0898 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.7886.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         9289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0526
_reflns_number_gt                8799
_reflns_number_total             9289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00423j2.cif
_cod_data_source_block           cu_bz8_52_0m
_cod_database_code               1516566
_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:
 C7(H7), C8(H8), C51(H51), C52(H52), C53(H53)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C60(H60A,H60B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15), C19(H19), C21(H21), C23(H23), C27(H27),
 C29(H29), C31(H31), C35(H35), C37(H37), C39(H39), C45(H45), C46(H46), C47(H47),
  C48(H48), C49(H49), C55(H55), C56(H56), C57(H57), C58(H58), C59(H59)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
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