Enantioselective photoredox- and Cu-catalyzed alkoxycyanation of styrenes to synthesize chiral β-cyanoethers.
Yu, Xiang; Niu, Mengru; Chen, Huan; Wu, Jiajia; Fang, Fang; Zhai, Xiaoting; Zhang, Guoyu; Chemical communications (Cambridge, England) 62 (2026) 6132–6136; doi:10.1039/d6cc00758a

data_7135568
_publ_section_title
;
 Enantioselective photoredox- and Cu-catalyzed alkoxycyanation of styrenes
 to synthesize chiral &#x3b2;-cyanoethers.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6132
_journal_page_last               6136
_journal_paper_doi               10.1039/d6cc00758a
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 F3 N O'
_chemical_formula_sum            'C17 H14 F3 N O'
_chemical_formula_weight         305.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-01-11 deposited with the CCDC.	2026-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.416(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   5.54510(10)
_cell_length_b                   23.8249(8)
_cell_length_c                   32.5396(16)
_cell_measurement_reflns_used    18273
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.9480
_cell_measurement_theta_min      2.2700
_cell_volume                     4298.7(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            28270
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.093
_diffrn_reflns_theta_min         2.298
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56956
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 4073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1189
_refine_ls_number_reflns         13016
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0779P)^2^+2.3997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.614
_reflns_Friedel_fraction_max     0.582
_reflns_number_gt                12158
_reflns_number_total             13016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00758a2.cif
_cod_data_source_block           zgy
_cod_depositor_comments          'Adding full bibliography for 7135568.cif.'
_cod_database_code               7135568
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.883
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C42(H42), C50(H50), C56(H56), C68(H68), C76(H76), C61(H61)
2.b Secondary CH2 refined with riding coordinates:
 C66(H66A,H66B), C27(H27A,H27B), C57(H57A,H57B), C65(H65A,H65B), C75(H75A,
 H75B), C5(H5A,H5B), C43(H43A,H43B), C23(H23A,H23B), C93(H93A,H93B), C95(H95A,
 H95B), C99(H99A,H99B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C38(H38), C58(H58), C60(H60), C62(H62), C64(H64), C70(H70),
 C72(H72), C74(H74), C78(H78), C80(H80), C82(H82), C86(H86), C90(H90), C92(H92),
  C94(H94), C98(H98), C100(H100), C102(H102), C51(H51), C13(H13), C53(H53),
 C55(H55), C7(H7), C29(H29), C59(H59), C15(H15), C31(H31), C63(H63), C2(H2),
 C33(H33), C67(H67), C17(H17), C35(H35), C71(H71), C9(H9), C73(H73), C37(H37),
 C19(H19), C77(H77), C39(H39), C79(H79), C83(H83), C21(H21), C85(H85), C87(H87),
  C11(H11), C89(H89), C45(H45), C47(H47), C3(H3), C97(H97), C49(H49), C101(H101)
;
_shelx_res_checksum              53066
_shelx_hkl_checksum              32560
_olex2_submission_special_instructions 'No special instructions were received'