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_1553844
_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         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-06-03 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.759(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8310(8)
_cell_length_b                   8.4718(5)
_cell_length_c                   16.4581(10)
_cell_measurement_reflns_used    1487
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3720
_cell_measurement_theta_min      3.1910
_cell_volume                     1649.45(18)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0517275000
_diffrn_orient_matrix_UB_12      0.0342020000
_diffrn_orient_matrix_UB_13      0.0123820000
_diffrn_orient_matrix_UB_21      0.0031279000
_diffrn_orient_matrix_UB_22      -0.0430544000
_diffrn_orient_matrix_UB_23      0.0368763000
_diffrn_orient_matrix_UB_31      0.0301915000
_diffrn_orient_matrix_UB_32      0.0631473000
_diffrn_orient_matrix_UB_33      0.0185239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6441
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.20
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93029
_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    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.1469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2013
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00588a2.cif
_cod_data_source_block           160112_wsz_8_51
_cod_original_cell_volume        1649.45(17)
_cod_database_code               1553844
_chemical_oxdiff_formula         'C10 H10 N2 O8'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;