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_1553846
_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         'C17 H22 I N O2'
_chemical_formula_sum            'C17 H22 I N O2'
_chemical_formula_weight         399.26
_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             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-01-05 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.261(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7810(10)
_cell_length_b                   12.2621(7)
_cell_length_c                   12.7517(10)
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5383
_cell_measurement_theta_min      3.2568
_cell_volume                     1728.1(2)
_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      -0.0228349000
_diffrn_orient_matrix_UB_12      0.0361227000
_diffrn_orient_matrix_UB_13      0.0313510000
_diffrn_orient_matrix_UB_21      0.0200980000
_diffrn_orient_matrix_UB_22      0.0451702000
_diffrn_orient_matrix_UB_23      -0.0236650000
_diffrn_orient_matrix_UB_31      -0.0565105000
_diffrn_orient_matrix_UB_32      0.0014125000
_diffrn_orient_matrix_UB_33      -0.0444033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7006
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45406
_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    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+1.2462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2229
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00588a2.cif
_cod_data_source_block           161102_wsz_9_97
_cod_database_code               1553846
_chemical_oxdiff_formula         'c10 h10 n2 o8 I1'
_reflns_odcompleteness_completeness 99.60
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C17 \\sim C17A \\sim C16A: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Others
 Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C15(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C17A(H17D,H17E,H17F)
;