#------------------------------------------------------------------------------
#$Date: 2016-08-07 10:58:28 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185120 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/27/1542730.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1542730
loop_
_publ_author_name
'Chen, Gen-Qiang'
'Fang, Wei'
'Wei, Yin'
'Tang, Xiang-Ying'
'Shi, Min'
_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
_chemical_name_systematic
; 
 ? 
;
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0673P)²+0.0452P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.42151(10) 0.4828(2) 0.2561(4) 0.0386(5) Uani 1 1 d . .
C2 C 0.44620(13) 0.5783(2) 0.1314(5) 0.0540(6) Uani 1 1 d . .
H2 H 0.4753 0.5537 0.0403 0.065 Uiso 1 1 calc R U
C3 C 0.42847(13) 0.7067(2) 0.1409(5) 0.0594(7) Uani 1 1 d . .
H3 H 0.4455 0.7683 0.0563 0.071 Uiso 1 1 calc R U
C4 C 0.38532(12) 0.7463(2) 0.2755(5) 0.0551(7) Uani 1 1 d . .
H4 H 0.3737 0.8342 0.2820 0.066 Uiso 1 1 calc R U
C5 C 0.36001(10) 0.6558(2) 0.3982(4) 0.0476(6) Uani 1 1 d . .
H5 H 0.3312 0.6826 0.4888 0.057 Uiso 1 1 calc R U
C6 C 0.37693(10) 0.5221(2) 0.3896(4) 0.0398(5) Uani 1 1 d . .
C7 C 0.34948(10) 0.4270(2) 0.5154(4) 0.0416(5) Uani 1 1 d . .
H7 H 0.3197 0.4546 0.6021 0.050 Uiso 1 1 calc R U
C8 C 0.36502(9) 0.2984(2) 0.5133(3) 0.0368(5) Uani 1 1 d . .
C9 C 0.41212(9) 0.25494(19) 0.3833(4) 0.0353(5) Uani 1 1 d . .
C10 C 0.44051(9) 0.3458(2) 0.2560(4) 0.0374(5) Uani 1 1 d . .
C11 C 0.48816(10) 0.3004(2) 0.1385(4) 0.0461(6) Uani 1 1 d . .
H11 H 0.5078 0.3593 0.0556 0.055 Uiso 1 1 calc R U
C12 C 0.50625(11) 0.1725(2) 0.1430(4) 0.0501(6) Uani 1 1 d . .
H12 H 0.5381 0.1454 0.0643 0.060 Uiso 1 1 calc R U
C13 C 0.47764(11) 0.0822(2) 0.2638(4) 0.0493(6) Uani 1 1 d . .
H13 H 0.4898 -0.0054 0.2648 0.059 Uiso 1 1 calc R U
C14 C 0.43147(10) 0.1230(2) 0.3814(4) 0.0425(6) Uani 1 1 d . .
H14 H 0.4124 0.0620 0.4622 0.051 Uiso 1 1 calc R U
C15 C 0.33363(9) 0.2028(2) 0.6445(4) 0.0383(5) Uani 1 1 d . .
C16 C 0.31793(13) 0.2415(3) 0.8507(4) 0.0531(7) Uani 1 1 d . .
H16A H 0.2789 0.2157 0.9005 0.064 Uiso 1 1 calc R U
H16B H 0.3322 0.3262 0.8978 0.064 Uiso 1 1 calc R U
C17 C 0.36372(11) 0.1345(3) 0.8180(4) 0.0535(6) Uani 1 1 d . .
H17 H 0.4062 0.1504 0.8470 0.064 Uiso 1 1 calc R U
C18 C 0.33947(14) -0.0012(3) 0.8182(5) 0.0615(8) Uani 1 1 d . .
H18 H 0.3514 -0.0666 0.9060 0.074 Uiso 1 1 calc R U
C19 C 0.29911(13) -0.0183(2) 0.6796(5) 0.0550(7) Uani 1 1 d . .
H19 H 0.2773 -0.0956 0.6622 0.066 Uiso 1 1 calc R U
C20 C 0.29239(10) 0.0997(2) 0.5547(4) 0.0418(5) Uani 1 1 d . .
C21 C 0.23289(11) 0.1372(3) 0.4668(5) 0.0566(7) Uani 1 1 d . .
H21A H 0.1990 0.0793 0.4908 0.068 Uiso 1 1 calc R U
H21B H 0.2230 0.2302 0.4597 0.068 Uiso 1 1 calc R U
C22 C 0.28202(11) 0.0877(3) 0.3379(4) 0.0520(6) Uani 1 1 d . .
H22A H 0.3019 0.1506 0.2524 0.062 Uiso 1 1 calc R U
H22B H 0.2779 -0.0002 0.2835 0.062 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.2(2)
C2 C1 C10 123.2(2)
C6 C1 C10 118.6(2)
C3 C2 C1 121.3(3)
C3 C2 H2 119.3
C1 C2 H2 119.3
C2 C3 C4 120.6(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 119.7(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 120.9(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 119.3(2)
C1 C6 C7 119.87(19)
C5 C6 C7 120.8(2)
C8 C7 C6 122.5(2)
C8 C7 H7 118.7
C6 C7 H7 118.7
C7 C8 C9 119.27(19)
C7 C8 C15 120.16(19)
C9 C8 C15 120.57(18)
C14 C9 C10 118.6(2)
C14 C9 C8 121.3(2)
C10 C9 C8 120.06(18)
C11 C10 C9 118.08(19)
C11 C10 C1 122.3(2)
C9 C10 C1 119.6(2)
C12 C11 C10 121.6(2)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C13 120.6(2)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 119.5(2)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C14 C9 121.6(2)
C13 C14 H14 119.2
C9 C14 H14 119.2
C8 C15 C16 119.8(2)
C8 C15 C20 119.5(2)
C16 C15 C20 114.5(2)
C8 C15 C17 123.47(19)
C16 C15 C17 59.90(18)
C20 C15 C17 105.27(19)
C15 C16 C17 60.92(17)
C15 C16 H16A 117.7
C17 C16 H16A 117.7
C15 C16 H16B 117.7
C17 C16 H16B 117.7
H16A C16 H16B 114.8
C18 C17 C16 115.1(2)
C18 C17 C15 105.3(2)
C16 C17 C15 59.18(16)
C18 C17 H17 120.4
C16 C17 H17 120.4
C15 C17 H17 120.4
C19 C18 C17 111.8(2)
C19 C18 H18 124.1
C17 C18 H18 124.1
C18 C19 C20 112.0(2)
C18 C19 H19 124.0
C20 C19 H19 124.0
C19 C20 C22 121.0(2)
C19 C20 C21 121.5(2)
C22 C20 C21 59.56(18)
C19 C20 C15 105.5(2)
C22 C20 C15 123.0(2)
C21 C20 C15 121.2(2)
C22 C21 C20 59.93(17)
C22 C21 H21A 117.8
C20 C21 H21A 117.8
C22 C21 H21B 117.8
C20 C21 H21B 117.8
H21A C21 H21B 114.9
C21 C22 C20 60.51(18)
C21 C22 H22A 117.7
C20 C22 H22A 117.7
C21 C22 H22B 117.7
C20 C22 H22B 117.7
H22A C22 H22B 114.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.399(4)
C1 C6 1.402(3)
C1 C10 1.453(3)
C2 C3 1.363(3)
C2 H2 0.9300
C3 C4 1.386(4)
C3 H3 0.9300
C4 C5 1.362(4)
C4 H4 0.9300
C5 C6 1.410(3)
C5 H5 0.9300
C6 C7 1.426(3)
C7 C8 1.351(3)
C7 H7 0.9300
C8 C9 1.440(3)
C8 C15 1.491(3)
C9 C14 1.407(3)
C9 C10 1.413(3)
C10 C11 1.406(3)
C11 C12 1.359(3)
C11 H11 0.9300
C12 C13 1.385(4)
C12 H12 0.9300
C13 C14 1.366(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.495(4)
C15 C20 1.520(3)
C15 C17 1.522(4)
C16 C17 1.507(4)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.480(4)
C17 H17 0.9800
C18 C19 1.313(4)
C18 H18 0.9300
C19 C20 1.475(3)
C19 H19 0.9300
C20 C22 1.494(4)
C20 C21 1.503(4)
C21 C22 1.488(4)
C21 H21A 0.9700
C21 H21B 0.9700
C22 H22A 0.9700
C22 H22B 0.9700
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.2(4)
C10 C1 C2 C3 -177.8(2)
C1 C2 C3 C4 0.1(4)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 -0.3(4)
C2 C1 C6 C5 -2.0(3)
C10 C1 C6 C5 177.0(2)
C2 C1 C6 C7 178.3(2)
C10 C1 C6 C7 -2.8(3)
C4 C5 C6 C1 1.6(4)
C4 C5 C6 C7 -178.7(2)
C1 C6 C7 C8 0.6(3)
C5 C6 C7 C8 -179.1(2)
C6 C7 C8 C9 1.6(3)
C6 C7 C8 C15 -178.4(2)
C7 C8 C9 C14 177.5(2)
C15 C8 C9 C14 -2.5(3)
C7 C8 C9 C10 -1.6(3)
C15 C8 C9 C10 178.4(2)
C14 C9 C10 C11 -2.1(3)
C8 C9 C10 C11 177.0(2)
C14 C9 C10 C1 -179.7(2)
C8 C9 C10 C1 -0.6(3)
C2 C1 C10 C11 4.1(4)
C6 C1 C10 C11 -174.8(2)
C2 C1 C10 C9 -178.4(2)
C6 C1 C10 C9 2.7(3)
C9 C10 C11 C12 1.1(4)
C1 C10 C11 C12 178.6(2)
C10 C11 C12 C13 0.5(4)
C11 C12 C13 C14 -1.0(4)
C12 C13 C14 C9 -0.1(4)
C10 C9 C14 C13 1.6(3)
C8 C9 C14 C13 -177.5(2)
C7 C8 C15 C16 -40.1(3)
C9 C8 C15 C16 139.9(2)
C7 C8 C15 C20 110.8(2)
C9 C8 C15 C20 -69.2(3)
C7 C8 C15 C17 -111.8(3)
C9 C8 C15 C17 68.2(3)
C8 C15 C16 C17 -113.7(2)
C20 C15 C16 C17 94.0(2)
C15 C16 C17 C18 -93.4(3)
C8 C15 C17 C18 -141.8(2)
C16 C15 C17 C18 110.4(3)
C20 C15 C17 C18 0.6(3)
C8 C15 C17 C16 107.8(3)
C20 C15 C17 C16 -109.8(2)
C16 C17 C18 C19 60.0(3)
C15 C17 C18 C19 -2.8(3)
C17 C18 C19 C20 3.9(3)
C18 C19 C20 C22 142.4(3)
C18 C19 C20 C21 -146.6(3)
C18 C19 C20 C15 -3.3(3)
C8 C15 C20 C19 145.6(2)
C16 C15 C20 C19 -62.0(2)
C17 C15 C20 C19 1.4(2)
C8 C15 C20 C22 0.8(3)
C16 C15 C20 C22 153.2(2)
C17 C15 C20 C22 -143.4(2)
C8 C15 C20 C21 -70.9(3)
C16 C15 C20 C21 81.4(3)
C17 C15 C20 C21 144.9(2)
C19 C20 C21 C22 -109.9(3)
C15 C20 C21 C22 112.5(3)
C19 C20 C22 C21 110.8(3)
C15 C20 C22 C21 -109.6(3)
