Asymmetric SN2′-type C–H functionalization of arenes with propargylic alcohols
Wu, Shangze; Huang, Xin; Fu, Chunling; Ma, Shengming; Organic Chemistry Frontiers 4 (2017) 2002–; doi:10.1039/C7QO00588A

data_1553845
_publ_section_title
;
 Asymmetric SN2&#x2032;-type C--H functionalization of arenes with
 propargylic alcohols
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2002
_journal_paper_doi               10.1039/C7QO00588A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C24 H27 N O'
_chemical_formula_sum            'C24 H27 N O'
_chemical_formula_weight         345.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
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Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
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_audit_update_record
;
2017-01-11 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                69.905(18)
_cell_angle_beta                 82.818(18)
_cell_angle_gamma                72.230(19)
_cell_formula_units_Z            2
_cell_length_a                   8.316(2)
_cell_length_b                   10.229(2)
_cell_length_c                   13.179(3)
_cell_measurement_reflns_used    489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4108
_cell_measurement_theta_min      2.9044
_cell_volume                     1002.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -62.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871  -38.0000 -120.0000 99

  2 omega  -16.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871   38.0000   60.0000 89

  3 omega  -48.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871  144.0000  -91.0000 29

  4 omega  -81.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  144.0000   88.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0449526000
_diffrn_orient_matrix_UB_12      -0.0728516000
_diffrn_orient_matrix_UB_13      0.0270982000
_diffrn_orient_matrix_UB_21      0.0312222000
_diffrn_orient_matrix_UB_22      -0.0093416000
_diffrn_orient_matrix_UB_23      -0.0504012000
_diffrn_orient_matrix_UB_31      0.0709304000
_diffrn_orient_matrix_UB_32      0.0229290000
_diffrn_orient_matrix_UB_33      0.0033801000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.1812
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6466
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.910
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.145
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.2693
_refine_ls_R_factor_gt           0.0889
_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^)+(0.0663P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1151
_reflns_number_total             3643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00588a2.cif
_cod_data_source_block           170106_wsz_9_9
_cod_original_cell_volume        1002.4(4)
_cod_database_code               1553845
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_cell_oxdiff_angle_alpha         69.905(18)
_cell_oxdiff_angle_beta          82.818(18)
_cell_oxdiff_angle_gamma         72.230(19)
_cell_oxdiff_length_a            8.316(2)
_cell_oxdiff_length_b            10.229(2)
_cell_oxdiff_length_c            13.179(3)
_cell_oxdiff_measurement_reflns_used 489
_cell_oxdiff_volume              1002.4(4)
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10),
 C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              63239
_olex2_submission_special_instructions 'No special instructions were received'