Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects
Chen, Gen-Qiang; Fang, Wei; Wei, Yin; Tang, Xiang-Ying; Shi, Min; Chem. Sci. 7 (2016) 4318–; doi:10.1039/C6SC00058D

data_1542730
_publ_section_title
;
 Divergent reaction pathways in gold-catalyzed cycloisomerization of
 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and
 temperature effects
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4318
_journal_paper_doi               10.1039/C6SC00058D
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H18'
_chemical_formula_weight         282.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-11-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.283(3)
_cell_length_b                   10.1485(15)
_cell_length_c                   6.7864(11)
_cell_measurement_reflns_used    3545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.340
_cell_measurement_theta_min      4.410
_cell_volume                     1534.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8789
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.828
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
; 
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -2.6(10)
_refine_ls_extinction_coef       0.041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0673P)^2^+0.0452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                2634
_reflns_number_total             2894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00058d2.cif
_cod_data_source_block           cd214654
_cod_depositor_comments
'Adding full bibliography for 1542730--1542732.cif.'
_cod_database_code               1542730
_shelxl_version_number           2013-4
_shelx_res_checksum              34227