Anti-Markovnikov hydroimination of terminal alkynes in gold-catalyzed pyridine construction from ammonia.
Wang, Liliang; Kong, Lingbing; Li, Yongxin; Ganguly, Rakesh; Kinjo, Rei; Chemical communications (Cambridge, England) 51 (2015) 12419–12422; doi:10.1039/c5cc04091d

data_7117561
_publ_section_title
;
 Anti-Markovnikov hydroimination of terminal alkynes in gold-catalyzed
 pyridine construction from ammonia.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12419
_journal_page_last               12422
_journal_paper_doi               10.1039/c5cc04091d
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         '1(C24 H16 F3 N)'
_chemical_formula_sum            'C24 H16 F3 N'
_chemical_formula_weight         375.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-26
_audit_creation_method           'APEX2 v2014.9-0'
_audit_update_record
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                72.70(3)
_cell_angle_beta                 89.67(3)
_cell_angle_gamma                77.32(3)
_cell_formula_units_Z            4
_cell_length_a                   11.219(5)
_cell_length_b                   11.500(6)
_cell_length_c                   14.861(8)
_cell_measurement_temperature    103(2)
_cell_volume                     1782.3(16)
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2014)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2014)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      103.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_unetI/netI     0.2479
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31698
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.438
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1049
_refine_ls_number_reflns         14348
_refine_ls_number_restraints     596
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1971
_refine_ls_R_factor_gt           0.0777
_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^)+(0.0675P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.2023
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                6610
_reflns_number_total             14348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04091d2.cif
_cod_data_source_block           rei118
_cod_original_cell_volume        1782.2(16)
_cod_database_code               7117561
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C84-F11 \\sim C89A-F11A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim F11 \\sim C84A
\\sim C85A \\sim C86A \\sim C87A \\sim C88A \\sim C89A \\sim F11A: within 1.7A
with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C84) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87)
\\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(C84A) \\sim Ueq, Uanis(C85A) \\sim Ueq, Uanis(C86A) \\sim Ueq,
Uanis(C87A) \\sim Ueq, Uanis(C88A) \\sim Ueq, Uanis(C89A) \\sim Ueq,
Uanis(F11A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(C84A)=Sof(C85A)=Sof(H85A)=Sof(C86A)=Sof(H86A)=Sof(C87A)=Sof(H87A)=
 Sof(C88A)=Sof(H88A)=Sof(C89A)=Sof(F11A)=1-FVAR(1)
 Sof(C84)=Sof(C85)=Sof(H85)=Sof(C86)=Sof(H86)=Sof(C87)=Sof(H87)=Sof(C88)=
 Sof(H88)=Sof(C89)=Sof(F11)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C42(H42A,H42B), C66(H66A,H66B), C90(H90A,H90B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C28(H28),
  C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40),
 C41(H41), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C52(H52), C56(H56),
  C57(H57), C58(H58), C59(H59), C62(H62), C63(H63), C64(H64), C65(H65),
 C69(H69), C70(H70), C71(H71), C72(H72), C74(H74), C76(H76), C80(H80), C81(H81),
  C82(H82), C83(H83), C85(H85), C86(H86), C87(H87), C88(H88), C85A(H85A),
 C86A(H86A), C87A(H87A), C88A(H88A), C93(H93), C94(H94), C95(H95), C96(H96)
6.c Fitted hexagon refined as free rotating group:
 C84(C85,C86,C87,C88,C89), C84A(C85A,C86A,C87A,C88A,C89A)
;
_shelx_res_checksum              67677
_shelx_hkl_checksum              66115
_olex2_submission_special_instructions 'No special instructions were received'