#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512376.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_1512376
loop_
_publ_author_name
'Liu, Zhenxing'
'Xia, Ying'
'Zhou, Shiyi'
'Wang, Long'
'Zhang, Yan'
'Wang, Jianbo'
_publ_section_title
;
 Pd-Catalyzed Cyclization and Carbene Migratory Insertion: New Approach to
 3-Vinylindoles and 3-Vinylbenzofurans.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5032
_journal_page_last               5035
_journal_paper_doi               10.1021/ol402368h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C26 H18 O'
_chemical_formula_sum            'C26 H18 O'
_chemical_formula_weight         346.40
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-09-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.828(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6916(12)
_cell_length_b                   5.7783(5)
_cell_length_c                   33.895(2)
_cell_measurement_reflns_used    3653
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.2340
_cell_measurement_theta_min      3.6690
_cell_volume                     3569.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.15
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8524
_diffrn_measurement_details
;
  1 omega   38.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  178.0000 -180.0000 31

  2 omega  -20.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -99.0000 -150.0000 35

  3 omega  -33.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -38.0000 -150.0000 68

  4 omega  -38.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392   38.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0217167000
_diffrn_orient_matrix_UB_12      0.0593238000
_diffrn_orient_matrix_UB_13      0.0167617000
_diffrn_orient_matrix_UB_21      0.0321225000
_diffrn_orient_matrix_UB_22      -0.0308736000
_diffrn_orient_matrix_UB_23      -0.0066329000
_diffrn_orient_matrix_UB_31      -0.0028816000
_diffrn_orient_matrix_UB_32      0.1030764000
_diffrn_orient_matrix_UB_33      -0.0116366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            8312
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0068(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0447P)²+1.6394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2700
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol402368h_si_003.cif
_cod_data_source_block           exp_2276
_cod_original_cell_volume        3569.5(5)
_cod_database_code               1512376
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C26 H17 O1'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23),
  C25(H25), C26(H26)
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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 0.87011(8) 0.4090(3) 0.41890(4) 0.0423(4) Uani 1 1 d . .
C2 C 0.92135(9) 0.5717(3) 0.41441(5) 0.0508(5) Uani 1 1 d . .
H2 H 0.9678 0.5801 0.4327 0.061 Uiso 1 1 calc R U
C3 C 0.90249(10) 0.7209(3) 0.38249(5) 0.0549(5) Uani 1 1 d . .
H3 H 0.9364 0.8357 0.3782 0.066 Uiso 1 1 calc R U
C4 C 0.83415(10) 0.7058(3) 0.35625(5) 0.0564(5) Uani 1 1 d . .
H4 H 0.8219 0.8119 0.3344 0.068 Uiso 1 1 calc R U
C5 C 0.78360(9) 0.5407(3) 0.36114(5) 0.0495(4) Uani 1 1 d . .
H5 H 0.7370 0.5333 0.3429 0.059 Uiso 1 1 calc R U
C6 C 0.80168(8) 0.3845(3) 0.39320(4) 0.0370(4) Uani 1 1 d . .
C7 C 0.76484(8) 0.2014(3) 0.41063(4) 0.0371(4) Uani 1 1 d . .
C8 C 0.81340(8) 0.1373(3) 0.44447(5) 0.0492(4) Uani 1 1 d . .
H8 H 0.8035 0.0213 0.4624 0.059 Uiso 1 1 calc R U
C9 C 0.69135(8) 0.1028(3) 0.39615(4) 0.0368(4) Uani 1 1 d . .
C10 C 0.65947(8) -0.0299(3) 0.42591(4) 0.0362(4) Uani 1 1 d . .
C11 C 0.59666(8) 0.0526(3) 0.43648(5) 0.0439(4) Uani 1 1 d . .
H11 H 0.5767 0.1973 0.4262 0.053 Uiso 1 1 calc R U
C12 C 0.56293(10) -0.0724(4) 0.46171(5) 0.0596(5) Uani 1 1 d . .
H12 H 0.5193 -0.0154 0.4682 0.071 Uiso 1 1 calc R U
C13 C 0.59207(11) -0.2790(4) 0.47758(5) 0.0651(6) Uani 1 1 d . .
H13 H 0.5688 -0.3647 0.4951 0.078 Uiso 1 1 calc R U
C14 C 0.65498(11) -0.3616(3) 0.46807(5) 0.0601(5) Uani 1 1 d . .
H14 H 0.6755 -0.5039 0.4793 0.072 Uiso 1 1 calc R U
C15 C 0.68873(9) -0.2384(3) 0.44224(5) 0.0465(4) Uani 1 1 d . .
H15 H 0.7321 -0.2970 0.4357 0.056 Uiso 1 1 calc R U
C16 C 0.65291(8) 0.1386(3) 0.35820(4) 0.0414(4) Uani 1 1 d . .
H16 H 0.6767 0.2300 0.3416 0.050 Uiso 1 1 calc R U
C17 C 0.57917(8) 0.0557(3) 0.33874(4) 0.0376(4) Uani 1 1 d . .
C18 C 0.53658(8) 0.1910(3) 0.30932(4) 0.0361(4) Uani 1 1 d . .
H18 H 0.5559 0.3331 0.3022 0.043 Uiso 1 1 calc R U
C19 C 0.46502(8) 0.1254(3) 0.28937(4) 0.0336(3) Uani 1 1 d . .
C20 C 0.42081(8) 0.2642(3) 0.25944(5) 0.0419(4) Uani 1 1 d . .
H20 H 0.4393 0.4076 0.2522 0.050 Uiso 1 1 calc R U
C21 C 0.35209(9) 0.1958(3) 0.24074(5) 0.0489(4) Uani 1 1 d . .
H21 H 0.3230 0.2915 0.2206 0.059 Uiso 1 1 calc R U
C22 C 0.32405(9) -0.0141(3) 0.25097(5) 0.0528(5) Uani 1 1 d . .
H22 H 0.2759 -0.0602 0.2377 0.063 Uiso 1 1 calc R U
C23 C 0.36502(8) -0.1532(3) 0.27971(5) 0.0465(4) Uani 1 1 d . .
H23 H 0.3452 -0.2955 0.2864 0.056 Uiso 1 1 calc R U
C24 C 0.43669(8) -0.0877(3) 0.29961(4) 0.0368(4) Uani 1 1 d . .
C25 C 0.48174(9) -0.2279(3) 0.32914(5) 0.0433(4) Uani 1 1 d . .
H25 H 0.4636 -0.3725 0.3360 0.052 Uiso 1 1 calc R U
C26 C 0.55047(9) -0.1604(3) 0.34787(5) 0.0428(4) Uani 1 1 d . .
H26 H 0.5798 -0.2592 0.3674 0.051 Uiso 1 1 calc R U
O1 O 0.87827(6) 0.2553(2) 0.45050(3) 0.0558(4) Uani 1 1 d . .
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'
O O 0.0106 0.0060 '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 124.66(15)
O1 C1 C2 124.69(14)
O1 C1 C6 110.58(13)
C1 C2 H2 121.4
C3 C2 C1 117.10(16)
C3 C2 H2 121.4
C2 C3 H3 119.8
C2 C3 C4 120.43(16)
C4 C3 H3 119.8
C3 C4 H4 119.2
C5 C4 C3 121.63(17)
C5 C4 H4 119.2
C4 C5 H5 120.4
C4 C5 C6 119.16(15)
C6 C5 H5 120.4
C1 C6 C5 116.99(14)
C1 C6 C7 105.82(13)
C5 C6 C7 136.96(14)
C6 C7 C9 129.63(13)
C8 C7 C6 104.78(13)
C8 C7 C9 125.59(15)
C7 C8 H8 123.3
C7 C8 O1 113.45(15)
O1 C8 H8 123.3
C7 C9 C10 117.26(12)
C16 C9 C7 121.53(14)
C16 C9 C10 121.16(13)
C11 C10 C9 119.09(14)
C11 C10 C15 118.52(15)
C15 C10 C9 122.33(14)
C10 C11 H11 119.6
C12 C11 C10 120.80(17)
C12 C11 H11 119.6
C11 C12 H12 119.9
C13 C12 C11 120.28(17)
C13 C12 H12 119.9
C12 C13 H13 120.1
C14 C13 C12 119.79(17)
C14 C13 H13 120.1
C13 C14 H14 119.8
C13 C14 C15 120.31(19)
C15 C14 H14 119.8
C10 C15 H15 119.9
C14 C15 C10 120.28(17)
C14 C15 H15 119.9
C9 C16 H16 115.5
C9 C16 C17 128.97(15)
C17 C16 H16 115.5
C18 C17 C16 118.37(14)
C18 C17 C26 118.20(14)
C26 C17 C16 123.40(14)
C17 C18 H18 119.0
C17 C18 C19 122.03(14)
C19 C18 H18 119.0
C18 C19 C24 118.91(14)
C20 C19 C18 122.32(14)
C20 C19 C24 118.76(14)
C19 C20 H20 119.6
C21 C20 C19 120.87(16)
C21 C20 H20 119.6
C20 C21 H21 119.8
C20 C21 C22 120.34(16)
C22 C21 H21 119.8
C21 C22 H22 119.7
C23 C22 C21 120.59(16)
C23 C22 H22 119.7
C22 C23 H23 119.7
C22 C23 C24 120.50(16)
C24 C23 H23 119.7
C23 C24 C19 118.93(15)
C23 C24 C25 122.59(15)
C25 C24 C19 118.48(14)
C24 C25 H25 119.3
C26 C25 C24 121.35(15)
C26 C25 H25 119.3
C17 C26 H26 119.5
C25 C26 C17 120.97(15)
C25 C26 H26 119.5
C8 O1 C1 105.35(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(2)
C1 C6 1.386(2)
C1 O1 1.3733(19)
C2 H2 0.9500
C2 C3 1.367(2)
C3 H3 0.9500
C3 C4 1.388(3)
C4 H4 0.9500
C4 C5 1.378(2)
C5 H5 0.9500
C5 C6 1.395(2)
C6 C7 1.457(2)
C7 C8 1.347(2)
C7 C9 1.467(2)
C8 H8 0.9500
C8 O1 1.3666(19)
C9 C10 1.493(2)
C9 C16 1.343(2)
C10 C11 1.386(2)
C10 C15 1.387(2)
C11 H11 0.9500
C11 C12 1.375(2)
C12 H12 0.9500
C12 C13 1.372(3)
C13 H13 0.9500
C13 C14 1.372(3)
C14 H14 0.9500
C14 C15 1.384(2)
C15 H15 0.9500
C16 H16 0.9500
C16 C17 1.470(2)
C17 C18 1.373(2)
C17 C26 1.420(2)
C18 H18 0.9500
C18 C19 1.4102(19)
C19 C20 1.408(2)
C19 C24 1.414(2)
C20 H20 0.9500
C20 C21 1.359(2)
C21 H21 0.9500
C21 C22 1.395(3)
C22 H22 0.9500
C22 C23 1.361(2)
C23 H23 0.9500
C23 C24 1.411(2)
C24 C25 1.412(2)
C25 H25 0.9500
C25 C26 1.358(2)
C26 H26 0.9500
