Phosphine-Catalyzed Remote 1,7-Addition for Synthesis of Diene Carboxylates
Feng, Jiaxu; Huang, You; ACS Catalysis  (2020) 3541–; doi:10.1021/acscatal.0c00588

data_4517458
_publ_section_title
;
 Phosphine-Catalyzed Remote 1,7-Addition for Synthesis of Diene
 Carboxylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3541
_journal_paper_doi               10.1021/acscatal.0c00588
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H25 N O4'
_chemical_formula_sum            'C24 H25 N O4'
_chemical_formula_weight         391.45
_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     direct
_audit_creation_date             2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 110.11(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   25.487(5)
_cell_length_b                   9.845(2)
_cell_length_c                   26.272(5)
_cell_measurement_reflns_used    6684
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9504
_cell_measurement_theta_min      1.7018
_cell_volume                     6190(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            74657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.842
_diffrn_reflns_theta_min         1.374
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear(Rigaku, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       prism
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 3240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1585
_refine_ls_number_reflns         29294
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0627P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                10039
_reflns_number_total             29294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00588_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4517458
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.983
_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. Uiso/Uaniso restraints and constraints
Uanis(C46) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B), C34(H34A,H34B), C41(H41A,H41B), C58(H58A,
 H58B), C65(H65A,H65B), C82(H82A,H82B), C89(H89A,H89B), C106(H10F,H10G),
 C113(H11D,H11E), C130(H13A,H13B), C137(H13F,H13G)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), C20(H20), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31),
  C35(H35), C36(H36), C37(H37), C38(H38), C43(H43), C44(H44), C46(H46),
 C47(H47), C52(H52), C53(H53), C54(H54), C55(H55), C59(H59), C60(H60), C61(H61),
  C62(H62), C67(H67), C68(H68), C70(H70), C71(H71), C76(H76), C77(H77),
 C78(H78), C79(H79), C83(H83), C84(H84), C85(H85), C86(H86), C91(H91), C92(H92),
  C94(H94), C95(H95), C100(H100), C101(H101), C102(H102), C103(H103),
 C107(H107), C108(H108), C109(H109), C110(H110), C115(H115), C116(H116),
 C118(H118), C119(H119), C124(H124), C125(H125), C126(H126), C127(H127),
 C131(H131), C132(H132), C133(H133), C134(H134), C139(H139), C140(H140),
 C142(H142), C143(H143)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C33(H33A,H33B,
 H33C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C57(H57A,H57B,H57C), C64(H64A,
 H64B,H64C), C72(H72A,H72B,H72C), C81(H81A,H81B,H81C), C88(H88A,H88B,H88C),
 C96(H96A,H96B,H96C), C105(H10C,H10D,H10E), C112(H11A,H11B,H11C), C120(H12A,
 H12B,H12C), C129(H12D,H12E,H12F), C136(H13C,H13D,H13E), C144(H14A,H14B,H14C)
;
_shelx_res_checksum              21025
_shelx_hkl_checksum              4929
_olex2_submission_special_instructions 'No special instructions were received'