#------------------------------------------------------------------------------
#$Date: 2020-12-16 03:48:46 +0200 (Wed, 16 Dec 2020) $
#$Revision: 259908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/75/7127599.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_7127599
loop_
_publ_author_name
'Wu, Li-Jun'
'Yang, Liang-Feng'
'Lv, Gui-Fen'
'Li, Jin-Heng'
_publ_section_title
;
 Divergent functionalization of terminal alkynes enabled alkynylative
 [5+1] benzannulation of 3-acetoxy-1,4-enynes.
;
_journal_issue                   97
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15329
_journal_page_last               15332
_journal_paper_doi               10.1039/d0cc06793h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         C33H24
_chemical_formula_sum            'C33 H24'
_chemical_formula_weight         420.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-28 deposited with the CCDC.	2020-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.7620(10)
_cell_angle_beta                 99.0220(10)
_cell_angle_gamma                105.2660(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9996(8)
_cell_length_b                   10.3778(12)
_cell_length_c                   17.063(2)
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.29
_cell_volume                     1177.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9179
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         2.293
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6674
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             4363
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc06793h2.cif
_cod_data_source_block           A
_cod_database_code               7127599
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0046(2) 0.26320(13) 0.01291(8) 0.0517(3) Uani 1 1 d . . . . .
C2 C -0.1566(2) 0.27661(15) 0.04622(9) 0.0636(4) Uani 1 1 d . . . . .
H2 H -0.1724 0.2455 0.0960 0.076 Uiso 1 1 calc R U . . .
C3 C -0.2943(2) 0.33544(17) 0.00681(10) 0.0739(5) Uani 1 1 d . . . . .
H3 H -0.4024 0.3441 0.0300 0.089 Uiso 1 1 calc R U . . .
C4 C -0.2729(3) 0.38142(16) -0.06679(11) 0.0728(5) Uani 1 1 d . . . . .
H4 H -0.3651 0.4223 -0.0932 0.087 Uiso 1 1 calc R U . . .
C5 C -0.1151(3) 0.36660(18) -0.10089(10) 0.0783(5) Uani 1 1 d . . . . .
H5 H -0.1011 0.3967 -0.1510 0.094 Uiso 1 1 calc R U . . .
C6 C 0.0226(2) 0.30768(17) -0.06190(9) 0.0701(4) Uani 1 1 d . . . . .
H6 H 0.1288 0.2976 -0.0859 0.084 Uiso 1 1 calc R U . . .
C7 C 0.1531(2) 0.20791(14) 0.05628(8) 0.0563(4) Uani 1 1 d . . . . .
C8 C 0.2791(2) 0.16790(14) 0.09529(8) 0.0552(4) Uani 1 1 d . . . . .
C9 C 0.43111(19) 0.11896(13) 0.14190(8) 0.0500(3) Uani 1 1 d . . . . .
C10 C 0.55138(18) 0.19373(12) 0.21038(7) 0.0455(3) Uani 1 1 d . . . . .
C11 C 0.69699(18) 0.14321(12) 0.25609(7) 0.0459(3) Uani 1 1 d . . . . .
C12 C 0.72315(19) 0.01926(13) 0.23168(8) 0.0491(3) Uani 1 1 d . . . . .
C13 C 0.6061(2) -0.04985(14) 0.16180(8) 0.0580(4) Uani 1 1 d . . . . .
H13 H 0.6266 -0.1303 0.1445 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4617(2) -0.00238(14) 0.11787(8) 0.0586(4) Uani 1 1 d . . . . .
H14 H 0.3840 -0.0513 0.0719 0.070 Uiso 1 1 calc R U . . .
C15 C 0.8725(2) -0.04247(13) 0.27678(8) 0.0523(3) Uani 1 1 d . . . . .
C16 C 0.8601(2) -0.08132(16) 0.35307(9) 0.0677(4) Uani 1 1 d . . . . .
H16 H 0.7602 -0.0645 0.3786 0.081 Uiso 1 1 calc R U . . .
C17 C 0.9938(3) -0.14458(18) 0.39160(11) 0.0816(5) Uani 1 1 d . . . . .
H17 H 0.9832 -0.1707 0.4427 0.098 Uiso 1 1 calc R U . . .
C18 C 1.1428(3) -0.16913(18) 0.35470(13) 0.0847(5) Uani 1 1 d . . . . .
H18 H 1.2332 -0.2117 0.3808 0.102 Uiso 1 1 calc R U . . .
C19 C 1.1579(2) -0.13074(17) 0.27950(12) 0.0780(5) Uani 1 1 d . . . . .
H19 H 1.2591 -0.1470 0.2545 0.094 Uiso 1 1 calc R U . . .
C20 C 1.0239(2) -0.06806(14) 0.24056(10) 0.0624(4) Uani 1 1 d . . . . .
H20 H 1.0352 -0.0426 0.1893 0.075 Uiso 1 1 calc R U . . .
C21 C 0.82418(19) 0.22419(13) 0.33059(8) 0.0525(3) Uani 1 1 d . . . . .
H21A H 0.9219 0.1782 0.3527 0.063 Uiso 1 1 calc R U . . .
H21B H 0.8978 0.3103 0.3158 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7072(2) 0.24784(13) 0.39451(7) 0.0502(3) Uani 1 1 d . . . . .
C23 C 0.5392(2) 0.15251(15) 0.40830(8) 0.0616(4) Uani 1 1 d . . . . .
H23 H 0.4985 0.0704 0.3785 0.074 Uiso 1 1 calc R U . . .
C24 C 0.4305(3) 0.17627(18) 0.46514(9) 0.0728(4) Uani 1 1 d . . . . .
H24 H 0.3176 0.1106 0.4733 0.087 Uiso 1 1 calc R U . . .
C25 C 0.4881(3) 0.2961(2) 0.50964(10) 0.0786(5) Uani 1 1 d . . . . .
H25 H 0.4142 0.3127 0.5477 0.094 Uiso 1 1 calc R U . . .
C26 C 0.6556(3) 0.39165(18) 0.49763(10) 0.0781(5) Uani 1 1 d . . . . .
H26 H 0.6966 0.4730 0.5282 0.094 Uiso 1 1 calc R U . . .
C27 C 0.7643(2) 0.36798(15) 0.44034(9) 0.0647(4) Uani 1 1 d . . . . .
H27 H 0.8773 0.4339 0.4326 0.078 Uiso 1 1 calc R U . . .
C28 C 0.52719(19) 0.32825(13) 0.23242(7) 0.0459(3) Uani 1 1 d . . . . .
C29 C 0.3594(2) 0.34181(14) 0.26183(8) 0.0559(4) Uani 1 1 d . . . . .
H29 H 0.2580 0.2659 0.2673 0.067 Uiso 1 1 calc R U . . .
C30 C 0.3413(2) 0.46669(16) 0.28307(9) 0.0653(4) Uani 1 1 d . . . . .
H30 H 0.2279 0.4742 0.3028 0.078 Uiso 1 1 calc R U . . .
C31 C 0.4884(2) 0.57963(15) 0.27535(9) 0.0655(4) Uani 1 1 d . . . . .
H31 H 0.4758 0.6635 0.2903 0.079 Uiso 1 1 calc R U . . .
C32 C 0.6552(2) 0.56870(15) 0.24542(9) 0.0643(4) Uani 1 1 d . . . . .
H32 H 0.7554 0.6452 0.2397 0.077 Uiso 1 1 calc R U . . .
C33 C 0.6736(2) 0.44374(13) 0.22380(8) 0.0553(3) Uani 1 1 d . . . . .
H33 H 0.7862 0.4370 0.2031 0.066 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.56(14) . . ?
C2 C1 C7 120.29(13) . . ?
C6 C1 C7 121.12(13) . . ?
C3 C2 C1 120.75(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.16(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.50(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.58(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.41(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C1 176.39(15) . . ?
C7 C8 C9 179.60(15) . . ?
C14 C9 C10 119.80(12) . . ?
C14 C9 C8 119.62(12) . . ?
C10 C9 C8 120.57(12) . . ?
C9 C10 C11 119.81(12) . . ?
C9 C10 C28 119.37(12) . . ?
C11 C10 C28 120.79(11) . . ?
C10 C11 C12 119.53(11) . . ?
C10 C11 C21 119.30(11) . . ?
C12 C11 C21 121.17(12) . . ?
C13 C12 C11 119.06(12) . . ?
C13 C12 C15 117.75(12) . . ?
C11 C12 C15 123.19(12) . . ?
C14 C13 C12 121.65(13) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 120.09(12) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C20 C15 C16 118.18(14) . . ?
C20 C15 C12 119.62(13) . . ?
C16 C15 C12 122.13(13) . . ?
C17 C16 C15 120.80(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.16(17) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.79(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.27(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.79(16) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C11 114.75(11) . . ?
C22 C21 H21A 108.6 . . ?
C11 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C11 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C27 117.66(14) . . ?
C23 C22 C21 121.85(12) . . ?
C27 C22 C21 120.48(13) . . ?
C22 C23 C24 121.46(14) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 120.17(16) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.40(16) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 120.42(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.89(16) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C33 C28 C29 118.03(12) . . ?
C33 C28 C10 120.46(12) . . ?
C29 C28 C10 121.51(12) . . ?
C30 C29 C28 120.68(14) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 120.61(14) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 119.73(14) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 119.83(14) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C28 121.10(14) . . ?
C32 C33 H33 119.4 . . ?
C28 C33 H33 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3765(19) . ?
C1 C6 1.384(2) . ?
C1 C7 1.434(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.1914(19) . ?
C8 C9 1.4374(19) . ?
C9 C14 1.3921(18) . ?
C9 C10 1.4028(17) . ?
C10 C11 1.4069(18) . ?
C10 C28 1.4938(17) . ?
C11 C12 1.4060(17) . ?
C11 C21 1.5167(17) . ?
C12 C13 1.3924(18) . ?
C12 C15 1.4920(18) . ?
C13 C14 1.3687(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.3854(19) . ?
C15 C16 1.383(2) . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.5129(19) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.3806(19) . ?
C22 C27 1.3805(18) . ?
C23 C24 1.377(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(2) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.3856(18) . ?
C28 C29 1.3849(18) . ?
C29 C30 1.3781(19) . ?
C29 H29 0.9300 . ?
C30 C31 1.367(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.375(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.3812(19) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.4(2) . . . . ?
C7 C1 C2 C3 176.79(14) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C7 C1 C6 C5 -176.63(14) . . . . ?
C14 C9 C10 C11 -2.46(19) . . . . ?
C8 C9 C10 C11 178.87(12) . . . . ?
C14 C9 C10 C28 175.67(12) . . . . ?
C8 C9 C10 C28 -2.99(18) . . . . ?
C9 C10 C11 C12 1.27(18) . . . . ?
C28 C10 C11 C12 -176.84(11) . . . . ?
C9 C10 C11 C21 -179.20(11) . . . . ?
C28 C10 C11 C21 2.69(18) . . . . ?
C10 C11 C12 C13 1.07(18) . . . . ?
C21 C11 C12 C13 -178.45(12) . . . . ?
C10 C11 C12 C15 -179.45(12) . . . . ?
C21 C11 C12 C15 1.03(19) . . . . ?
C11 C12 C13 C14 -2.3(2) . . . . ?
C15 C12 C13 C14 178.19(13) . . . . ?
C12 C13 C14 C9 1.1(2) . . . . ?
C10 C9 C14 C13 1.3(2) . . . . ?
C8 C9 C14 C13 179.96(13) . . . . ?
C13 C12 C15 C20 60.02(17) . . . . ?
C11 C12 C15 C20 -119.46(15) . . . . ?
C13 C12 C15 C16 -116.90(16) . . . . ?
C11 C12 C15 C16 63.62(18) . . . . ?
C20 C15 C16 C17 -0.5(2) . . . . ?
C12 C15 C16 C17 176.49(14) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 0.2(2) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
C12 C15 C20 C19 -176.90(13) . . . . ?
C10 C11 C21 C22 62.07(16) . . . . ?
C12 C11 C21 C22 -118.41(14) . . . . ?
C11 C21 C22 C23 35.46(18) . . . . ?
C11 C21 C22 C27 -143.35(13) . . . . ?
C27 C22 C23 C24 0.6(2) . . . . ?
C21 C22 C23 C24 -178.21(14) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C23 C22 C27 C26 -0.4(2) . . . . ?
C21 C22 C27 C26 178.50(14) . . . . ?
C25 C26 C27 C22 -0.4(2) . . . . ?
C9 C10 C28 C33 -108.15(14) . . . . ?
C11 C10 C28 C33 69.97(16) . . . . ?
C9 C10 C28 C29 71.82(17) . . . . ?
C11 C10 C28 C29 -110.06(14) . . . . ?
C33 C28 C29 C30 -1.1(2) . . . . ?
C10 C28 C29 C30 178.94(13) . . . . ?
C28 C29 C30 C31 0.1(2) . . . . ?
C29 C30 C31 C32 0.6(2) . . . . ?
C30 C31 C32 C33 -0.4(2) . . . . ?
C31 C32 C33 C28 -0.6(2) . . . . ?
C29 C28 C33 C32 1.3(2) . . . . ?
C10 C28 C33 C32 -178.70(13) . . . . ?
