Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis.
Smith, Courtney A.; Motika, Stephen E.; Wojtas, Lukasz; Shi, Xiaodong; Chemical communications (Cambridge, England) 53 (2017) 2315–2318; doi:10.1039/c6cc09794d

data_7119261
_publ_section_title
;
 Accessing alternative reaction pathways of the intermolecular
 condensation between homo-propargyl alcohols and terminal alkynes through
 divergent gold catalysis.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2315
_journal_page_last               2318
_journal_paper_doi               10.1039/c6cc09794d
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C25 H15 F3 N4 O'
_chemical_formula_sum            'C25 H15 F3 N4 O'
_chemical_formula_weight         444.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
_audit_creation_date             2016-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                80.3565(12)
_cell_angle_beta                 89.9964(14)
_cell_angle_gamma                76.6551(13)
_cell_formula_units_Z            4
_cell_length_a                   10.3921(3)
_cell_length_b                   11.9914(3)
_cell_length_c                   17.5331(4)
_cell_measurement_reflns_used    5391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.45
_cell_measurement_theta_min      3.85
_cell_volume                     2094.17(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.04
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30098
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.194
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9238.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00301(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         8427
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+1.5991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6375
_reflns_number_total             8427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09794d4.cif
_cod_data_source_block           cas_2057d_0m
_cod_depositor_comments
'Adding full bibliography for 7119261--7119263.cif.'
_cod_database_code               7119261
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F72-C70A = F71-C70A = F73-C70A
 1.32 with sigma of 0.02
 F74-C70B = F76-C70B = F75-C70B
 1.32 with sigma of 0.01
 F75-F76 = F74-F75 = F76-F74
 2.12 with sigma of 0.02
 F73-F72 = F72-F71 = F71-F73
 2.12 with sigma of 0.04
 F75-C67 = F74-C67 = F76-C67
 2.35 with sigma of 0.04
 C70B-C67 \\sim C70A-C67
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C70B) = Uanis(C70A)
4. Rigid body (RIGU) restrains
 F73, F72, C70A, F71
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C70B)=Sof(F74)=Sof(F75)=Sof(F76)=1-FVAR(1)
 Sof(F71)=Sof(F72)=Sof(F73)=Sof(C70A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C50(H50)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C61(H61A,H61B), C62(H62A,H62B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C25(H25), C26(H26), C28(H28),
 C29(H29), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C48(H48), C65(H65),
  C66(H66), C68(H68), C69(H69)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'