#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/70/1517072.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_1517072
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            'C20 H22'
_chemical_formula_weight         262.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9388(12)
_cell_length_b                   12.164(2)
_cell_length_c                   21.118(4)
_cell_measurement_reflns_used    4844
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4839
_cell_measurement_theta_min      1.6741
_cell_volume                     1511.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9752
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7814
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0725
_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)+(0.1752P)²+0.3413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2614
_reflns_number_gt                3088
_reflns_number_total             3439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501655g_si_002.cif
_cod_data_source_block           mx2323
_cod_depositor_comments
'Adding full bibliography for 1517072--1517074.cif.'
_cod_original_sg_symbol_H-M      p_1_21/n_1
_cod_database_code               1517072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C8 C 0.0209(3) 0.87267(14) 0.14536(8) 0.0229(4) Uani 1 1 d .
C6 C -0.1354(3) 0.68259(14) 0.16144(8) 0.0232(4) Uani 1 1 d .
C19 C -0.6618(3) 0.59402(16) 0.05414(9) 0.0316(5) Uani 1 1 d .
H19A H -0.7866 0.5491 0.0572 0.038 Uiso 1 1 calc R
C9 C 0.1998(3) 0.89420(15) 0.11035(9) 0.0269(4) Uani 1 1 d .
H9A H 0.3137 0.8421 0.1090 0.032 Uiso 1 1 calc R
C14 C -0.3066(3) 0.67242(13) 0.10451(8) 0.0223(4) Uani 1 1 d .
C15 C -0.2917(3) 0.72800(16) 0.04711(9) 0.0281(4) Uani 1 1 d .
H15A H -0.1681 0.7737 0.0440 0.034 Uiso 1 1 calc R
C13 C -0.1457(3) 0.95267(15) 0.14737(9) 0.0287(4) Uani 1 1 d .
H13A H -0.2654 0.9397 0.1706 0.034 Uiso 1 1 calc R
C7 C 0.0065(3) 0.76641(14) 0.17928(8) 0.0225(4) Uani 1 1 d .
C10 C 0.2088(4) 0.99302(17) 0.07758(9) 0.0333(5) Uani 1 1 d .
H10A H 0.3271 1.0062 0.0539 0.040 Uiso 1 1 calc R
C17 C -0.6466(3) 0.64929(15) -0.00286(9) 0.0270(4) Uani 1 1 d .
C3 C 0.1421(3) 0.74744(15) 0.24511(8) 0.0255(4) Uani 1 1 d .
C2 C 0.3915(3) 0.78161(18) 0.24983(9) 0.0328(5) Uani 1 1 d .
H2A H 0.4011 0.8598 0.2448 0.049 Uiso 1 1 calc R
H2B H 0.4605 0.7457 0.2168 0.049 Uiso 1 1 calc R
H2C H 0.4696 0.7607 0.2908 0.049 Uiso 1 1 calc R
C16 C -0.4580(3) 0.71609(16) -0.00498(9) 0.0299(5) Uani 1 1 d .
H16A H -0.4431 0.7539 -0.0425 0.036 Uiso 1 1 calc R
C1 C 0.0313(4) 0.81213(19) 0.29505(9) 0.0358(5) Uani 1 1 d .
H1A H 0.0519 0.8895 0.2888 0.054 Uiso 1 1 calc R
H1B H 0.1008 0.7918 0.3371 0.054 Uiso 1 1 calc R
H1C H -0.1281 0.7956 0.2906 0.054 Uiso 1 1 calc R
C18 C -0.8249(4) 0.63404(17) -0.05986(10) 0.0350(5) Uani 1 1 d .
H18A H -0.7883 0.6788 -0.0945 0.053 Uiso 1 1 calc R
H18B H -0.9704 0.6554 -0.0489 0.053 Uiso 1 1 calc R
H18C H -0.8298 0.5582 -0.0725 0.053 Uiso 1 1 calc R
C20 C -0.4957(3) 0.60442(15) 0.10623(9) 0.0292(4) Uani 1 1 d .
H20A H -0.5098 0.5653 0.1433 0.035 Uiso 1 1 calc R
C12 C -0.1352(4) 1.05175(16) 0.11501(10) 0.0337(5) Uani 1 1 d .
H12A H -0.2472 1.1047 0.1167 0.040 Uiso 1 1 calc R
C5 C -0.1095(3) 0.59272(15) 0.21201(9) 0.0297(4) Uani 1 1 d .
H5A H -0.1005 0.5207 0.1928 0.036 Uiso 1 1 calc R
H5B H -0.2354 0.5936 0.2369 0.036 Uiso 1 1 calc R
C4 C 0.1135(4) 0.62257(17) 0.25323(10) 0.0335(5) Uani 1 1 d .
H4A H 0.2395 0.5832 0.2390 0.040 Uiso 1 1 calc R
H4B H 0.1068 0.6044 0.2977 0.040 Uiso 1 1 calc R
C11 C 0.0427(4) 1.07143(16) 0.08019(10) 0.0358(5) Uani 1 1 d .
H11A H 0.0500 1.1377 0.0585 0.043 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
C13 C8 C9 118.60(16)
C13 C8 C7 120.42(15)
C9 C8 C7 120.97(16)
C7 C6 C14 129.13(16)
C7 C6 C5 110.36(16)
C14 C6 C5 120.43(15)
C20 C19 C17 121.46(17)
C10 C9 C8 120.48(18)
C20 C14 C15 116.86(17)
C20 C14 C6 119.81(15)
C15 C14 C6 123.33(15)
C16 C15 C14 121.08(17)
C12 C13 C8 120.78(18)
C6 C7 C8 126.81(16)
C6 C7 C3 111.99(15)
C8 C7 C3 120.86(15)
C11 C10 C9 120.16(18)
C16 C17 C19 117.16(18)
C16 C17 C18 122.03(17)
C19 C17 C18 120.79(17)
C7 C3 C2 113.94(15)
C7 C3 C1 109.03(15)
C2 C3 C1 108.49(16)
C7 C3 C4 101.41(14)
C2 C3 C4 112.40(16)
C1 C3 C4 111.45(16)
C15 C16 C17 121.88(17)
C19 C20 C14 121.56(17)
C11 C12 C13 119.84(19)
C6 C5 C4 103.13(15)
C5 C4 C3 105.73(15)
C10 C11 C12 120.14(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 C13 1.392(3)
C8 C9 1.399(2)
C8 C7 1.486(2)
C6 C7 1.344(2)
C6 C14 1.472(2)
C6 C5 1.521(2)
C19 C20 1.382(3)
C19 C17 1.392(3)
C9 C10 1.392(3)
C14 C20 1.399(2)
C14 C15 1.401(2)
C15 C16 1.384(3)
C13 C12 1.391(3)
C7 C3 1.528(2)
C10 C11 1.379(3)
C17 C16 1.389(3)
C17 C18 1.504(3)
C3 C2 1.529(3)
C3 C1 1.533(3)
C3 C4 1.540(3)
C12 C11 1.387(3)
C5 C4 1.528(3)
