#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/70/1517073.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_1517073
loop_
_publ_author_name
'Peng, Jing'
'Chen, Chao'
'Chen, Junjie'
'Su, Xiang'
'Xi, Chanjuan'
'Chen, Hui'
_publ_section_title
;
 Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts
 through C-C Bond Formation on Inert C(sp3)-H Bond.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3776
_journal_paper_doi               10.1021/ol501655g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C23 H26'
_chemical_formula_weight         302.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   none
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7819(16)
_cell_length_b                   6.1510(12)
_cell_length_c                   18.029(4)
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4504
_cell_measurement_theta_min      2.2801
_cell_volume                     855.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5738
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4569
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.159
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.2045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                3252
_reflns_number_total             3340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501655g_si_003.cif
_cod_data_source_block           pj22
_cod_depositor_comments
'Adding full bibliography for 1517072--1517074.cif.'
_cod_original_sg_symbol_H-M      p2(1)
_cod_database_code               1517073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C13 C 0.3170(2) 0.8466(3) 0.31948(9) 0.0322(4) Uani 1 1 d .
H13A H 0.3167 0.7206 0.2910 0.039 Uiso 1 1 calc R
C17 C 0.1978(2) 1.1957(3) 0.34200(10) 0.0309(4) Uani 1 1 d .
H17A H 0.1180 1.3061 0.3286 0.037 Uiso 1 1 calc R
C18 C -0.1321(2) 0.7036(3) 0.29927(9) 0.0282(4) Uani 1 1 d .
C12 C 0.1930(2) 1.0062(3) 0.29910(9) 0.0255(4) Uani 1 1 d .
C16 C 0.3215(3) 1.2196(4) 0.40465(10) 0.0367(5) Uani 1 1 d .
H16A H 0.3234 1.3456 0.4332 0.044 Uiso 1 1 calc R
C6 C 0.1117(2) 1.3127(3) 0.15942(10) 0.0291(4) Uani 1 1 d .
H6A H 0.0580 1.3811 0.1136 0.035 Uiso 1 1 calc R
H6B H 0.0665 1.3842 0.2007 0.035 Uiso 1 1 calc R
C11 C 0.0510(2) 0.9721(3) 0.23594(9) 0.0258(4) Uani 1 1 d .
C10 C -0.0893(2) 0.8450(3) 0.23779(9) 0.0283(4) Uani 1 1 d .
C8 C -0.1387(2) 1.0491(3) 0.12450(10) 0.0333(4) Uani 1 1 d .
H8A H -0.2041 1.1774 0.1348 0.040 Uiso 1 1 calc R
H8B H -0.1496 1.0281 0.0707 0.040 Uiso 1 1 calc R
C14 C 0.4417(2) 0.8725(4) 0.38197(10) 0.0379(5) Uani 1 1 d .
H14A H 0.5246 0.7652 0.3947 0.045 Uiso 1 1 calc R
C3 C 0.3806(3) 1.1569(3) 0.04881(10) 0.0350(4) Uani 1 1 d .
H3A H 0.4731 1.0672 0.0740 0.042 Uiso 1 1 calc R
H3B H 0.4094 1.1889 -0.0007 0.042 Uiso 1 1 calc R
C2 C 0.2131(3) 1.0238(3) 0.04001(9) 0.0330(4) Uani 1 1 d .
H2A H 0.2237 0.9054 0.0054 0.040 Uiso 1 1 calc R
H2B H 0.1180 1.1156 0.0184 0.040 Uiso 1 1 calc R
C5 C 0.3069(2) 1.3552(3) 0.16707(9) 0.0305(4) Uani 1 1 d .
H5A H 0.3669 1.2390 0.1963 0.037 Uiso 1 1 calc R
H5B H 0.3321 1.4899 0.1943 0.037 Uiso 1 1 calc R
C23 C -0.2347(2) 0.5194(4) 0.28237(10) 0.0340(4) Uani 1 1 d .
H23A H -0.2804 0.4924 0.2329 0.041 Uiso 1 1 calc R
C7 C 0.0544(2) 1.0734(3) 0.15812(9) 0.0264(4) Uani 1 1 d .
C19 C -0.0719(3) 0.7431(4) 0.37532(10) 0.0342(4) Uani 1 1 d .
H19A H -0.0063 0.8669 0.3886 0.041 Uiso 1 1 calc R
C15 C 0.4417(2) 1.0578(4) 0.42478(10) 0.0388(5) Uani 1 1 d .
H15A H 0.5228 1.0740 0.4673 0.047 Uiso 1 1 calc R
C9 C -0.2046(2) 0.8485(4) 0.16279(10) 0.0342(4) Uani 1 1 d .
H9A H -0.3258 0.8642 0.1692 0.041 Uiso 1 1 calc R
H9B H -0.1904 0.7173 0.1344 0.041 Uiso 1 1 calc R
C22 C -0.2701(3) 0.3759(4) 0.33750(11) 0.0393(5) Uani 1 1 d .
H22A H -0.3362 0.2522 0.3247 0.047 Uiso 1 1 calc R
C4 C 0.3777(3) 1.3706(3) 0.09170(10) 0.0335(4) Uani 1 1 d .
H4A H 0.3078 1.4744 0.0603 0.040 Uiso 1 1 calc R
H4B H 0.4949 1.4275 0.1006 0.040 Uiso 1 1 calc R
C21 C -0.2069(3) 0.4167(4) 0.41191(12) 0.0404(5) Uani 1 1 d .
H21A H -0.2304 0.3205 0.4490 0.048 Uiso 1 1 calc R
C20 C -0.1089(3) 0.6008(4) 0.43064(11) 0.0399(5) Uani 1 1 d .
H20A H -0.0676 0.6293 0.4805 0.048 Uiso 1 1 calc R
C1 C 0.1692(2) 0.9287(3) 0.11454(9) 0.0303(4) Uani 1 1 d .
H1A H 0.2770 0.8995 0.1467 0.036 Uiso 1 1 calc R
H1B H 0.1108 0.7906 0.1041 0.036 Uiso 1 1 calc R
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
C12 C13 C14 121.03(19)
C16 C17 C12 120.16(18)
C23 C18 C19 117.25(17)
C23 C18 C10 119.52(15)
C19 C18 C10 123.22(17)
C13 C12 C17 118.48(16)
C13 C12 C11 121.26(16)
C17 C12 C11 120.15(15)
C15 C16 C17 120.53(19)
C5 C6 C7 116.57(15)
C10 C11 C12 125.64(15)
C10 C11 C7 111.79(14)
C12 C11 C7 122.51(15)
C11 C10 C18 128.57(15)
C11 C10 C9 110.71(16)
C18 C10 C9 120.60(16)
C9 C8 C7 105.45(14)
C15 C14 C13 119.71(19)
C4 C3 C2 116.30(16)
C3 C2 C1 113.42(14)
C6 C5 C4 113.64(14)
C22 C23 C18 121.60(17)
C6 C7 C11 114.49(14)
C6 C7 C1 111.87(15)
C11 C7 C1 108.18(14)
C6 C7 C8 111.21(15)
C11 C7 C8 100.52(14)
C1 C7 C8 109.97(15)
C20 C19 C18 121.13(19)
C14 C15 C16 120.04(16)
C10 C9 C8 102.62(15)
C23 C22 C21 120.0(2)
C3 C4 C5 115.23(17)
C20 C21 C22 119.78(19)
C21 C20 C19 120.20(18)
C2 C1 C7 115.72(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C13 C12 1.391(3)
C13 C14 1.394(2)
C17 C16 1.390(2)
C17 C12 1.397(3)
C18 C23 1.396(3)
C18 C19 1.409(2)
C18 C10 1.482(2)
C12 C11 1.491(2)
C16 C15 1.380(3)
C6 C5 1.529(3)
C6 C7 1.537(3)
C11 C10 1.347(3)
C11 C7 1.539(2)
C10 C9 1.519(2)
C8 C9 1.535(3)
C8 C7 1.551(2)
C14 C15 1.376(3)
C3 C4 1.527(3)
C3 C2 1.529(3)
C2 C1 1.545(3)
C5 C4 1.537(2)
C23 C22 1.384(3)
C7 C1 1.548(3)
C19 C20 1.386(3)
C22 C21 1.388(3)
C21 C20 1.381(3)
