#------------------------------------------------------------------------------
#$Date: 2022-09-14 00:53:18 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277810 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/07/7130708.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_7130708
loop_
_publ_author_name
'Corcoran, James C.'
'Guo, Rui'
'Xia, Yue'
'Wang, Yiming'
_publ_section_title
;
 Vinyl Cation-Mediated Intramolecular Hydroarylation of Alkynes Using
 Pyridinium Reagents
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03794G
_journal_year                    2022
_chemical_formula_sum            'C23 H24 O3'
_chemical_formula_weight         348.42
_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   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2022-06-14 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                62.4089(9)
_cell_angle_beta                 80.6019(9)
_cell_angle_gamma                88.2485(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3486(2)
_cell_length_b                   10.8563(2)
_cell_length_c                   11.6441(2)
_cell_measurement_reflns_used    7868
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      68.154
_cell_measurement_theta_min      4.346
_cell_volume                     921.56(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15722
_diffrn_reflns_theta_full        68.29
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_min         4.35
_diffrn_source                   'Bruker X8 Prospector Ultra IMuS'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.340
_refine_ls_extinction_coef       0.0089(12)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0445
_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)+(0.0737P)²+0.1773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3010
_reflns_number_total             3290
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03794g2.cif
_cod_data_source_block           RuiGuo082020
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130708
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.46961(11) 0.48762(9) 0.17573(9) 0.0275(2) Uani d . . . 1 . .
C C1 0.13886(15) 0.30453(13) 0.26446(11) 0.0204(3) Uani d . . . 1 . .
O O2 0.31871(12) 1.25204(10) -0.24668(9) 0.0311(3) Uani d . . . 1 . .
C C2 0.03388(15) 0.35497(13) 0.17183(12) 0.0228(3) Uani d . . . 1 . .
H H2 -0.010(2) 0.4485(18) 0.1492(16) 0.029(4) Uiso d . . . 1 . .
O O3 0.55034(11) 1.19596(9) -0.33720(9) 0.0276(3) Uani d . . . 1 . .
C C3 -0.00881(17) 0.27657(14) 0.11436(12) 0.0262(3) Uani d . . . 1 . .
H H3 -0.081(2) 0.3135(19) 0.0522(19) 0.038(4) Uiso d . . . 1 . .
C C4 0.05542(17) 0.14752(14) 0.14744(13) 0.0270(3) Uani d . . . 1 . .
H H4 0.0220(18) 0.0902(16) 0.1091(15) 0.025(4) Uiso d . . . 1 . .
C C5 0.16323(16) 0.09773(14) 0.23643(12) 0.0253(3) Uani d . . . 1 . .
H H5 0.213(2) 0.0061(19) 0.2606(17) 0.032(4) Uiso d . . . 1 . .
C C6 0.20618(15) 0.17453(13) 0.29628(12) 0.0220(3) Uani d . . . 1 . .
C C7 0.32535(17) 0.12198(15) 0.39134(13) 0.0274(3) Uani d . . . 1 . .
H H7A 0.407(2) 0.2021(17) 0.3669(16) 0.029(4) Uiso d . . . 1 . .
H H7B 0.383(2) 0.0459(19) 0.3819(18) 0.037(4) Uiso d . . . 1 . .
C C8 0.24599(18) 0.07477(15) 0.53526(13) 0.0300(3) Uani d . . . 1 . .
H H8A 0.194(2) -0.0189(19) 0.5740(17) 0.034(4) Uiso d . . . 1 . .
H H8B 0.332(2) 0.067(2) 0.588(2) 0.045(5) Uiso d . . . 1 . .
C C9 0.11838(17) 0.17467(14) 0.54870(12) 0.0268(3) Uani d . . . 1 . .
H H9B 0.0956(19) 0.1558(16) 0.6408(17) 0.026(4) Uiso d . . . 1 . .
H H9A 0.015(2) 0.1530(18) 0.5257(17) 0.035(4) Uiso d . . . 1 . .
C C10 0.16506(15) 0.32679(13) 0.46130(12) 0.0231(3) Uani d . . . 1 . .
H H10 0.1868(19) 0.3837(17) 0.5034(16) 0.025(4) Uiso d . . . 1 . .
C C11 0.17329(14) 0.38721(13) 0.33105(12) 0.0207(3) Uani d . . . 1 . .
C C12 0.20879(15) 0.53965(13) 0.24479(12) 0.0207(3) Uani d . . . 1 . .
C C13 0.09438(16) 0.63682(14) 0.23949(12) 0.0236(3) Uani d . . . 1 . .
H H13 -0.010(2) 0.6081(17) 0.2964(17) 0.029(4) Uiso d . . . 1 . .
C C14 0.12414(16) 0.77709(14) 0.14966(12) 0.0237(3) Uani d . . . 1 . .
H H14 0.043(2) 0.8411(18) 0.1460(16) 0.028(4) Uiso d . . . 1 . .
C C15 0.26986(15) 0.82295(13) 0.06169(12) 0.0217(3) Uani d . . . 1 . .
C C16 0.38987(15) 0.72669(13) 0.06958(12) 0.0224(3) Uani d . . . 1 . .
H H16] 0.495(2) 0.7549(17) 0.0110(17) 0.031(4) Uiso d . . . 1 . .
C C17 0.35989(15) 0.58778(13) 0.16018(12) 0.0212(3) Uani d . . . 1 . .
C C18 0.62850(17) 0.53204(16) 0.09770(14) 0.0303(3) Uani d . . . 1 . .
H H18A 0.623(2) 0.5703(18) 0.0037(19) 0.035(4) Uiso d . . . 1 . .
H H18B 0.681(2) 0.6011(18) 0.1171(17) 0.033(4) Uiso d . . . 1 . .
H H18C 0.684(2) 0.443(2) 0.1243(18) 0.038(4) Uiso d . . . 1 . .
C C19 0.29245(16) 0.96809(14) -0.04086(12) 0.0234(3) Uani d . . . 1 . .
H H19 0.210(2) 1.0332(18) -0.0328(17) 0.034(4) Uiso d . . . 1 . .
C C20 0.41029(16) 1.02075(14) -0.14474(13) 0.0256(3) Uani d . . . 1 . .
H H20 0.492(2) 0.9691(19) -0.1617(18) 0.037(4) Uiso d . . . 1 . .
C C21 0.41747(16) 1.16760(13) -0.24477(12) 0.0237(3) Uani d . . . 1 . .
C C22 0.56879(18) 1.33731(14) -0.44370(14) 0.0300(3) Uani d . . . 1 . .
H H22A 0.578(2) 1.398(2) -0.4031(19) 0.041(5) Uiso d . . . 1 . .
H H22B 0.472(2) 1.3565(19) -0.4837(19) 0.041(5) Uiso d . . . 1 . .
C C23 0.7155(2) 1.34821(19) -0.53984(17) 0.0466(4) Uani d . . . 1 . .
H H23A 0.725(3) 1.443(2) -0.617(2) 0.054(6) Uiso d . . . 1 . .
H H23B 0.708(3) 1.282(2) -0.571(2) 0.054(6) Uiso d . . . 1 . .
H H23C 0.816(3) 1.324(2) -0.497(2) 0.063(6) Uiso d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 O1 C18 . . 117.25(10) ?
C2 C1 C6 . . 119.49(11) ?
C2 C1 C11 . . 119.52(11) ?
C6 C1 C11 . . 120.96(11) ?
C3 C2 C1 . . 120.93(12) ?
C3 C2 H2 . . 121.2(9) ?
C1 C2 H2 . . 117.9(9) ?
C21 O3 C22 . . 115.44(10) ?
C4 C3 C2 . . 119.50(12) ?
C4 C3 H3 . . 121.6(11) ?
C2 C3 H3 . . 118.9(11) ?
C3 C4 C5 . . 120.24(12) ?
C3 C4 H4 . . 119.5(9) ?
C5 C4 H4 . . 120.2(9) ?
C4 C5 C6 . . 121.03(12) ?
C4 C5 H5 . . 121.9(10) ?
C6 C5 H5 . . 117.1(10) ?
C5 C6 C1 . . 118.76(12) ?
C5 C6 C7 . . 121.24(11) ?
C1 C6 C7 . . 119.99(12) ?
C6 C7 C8 . . 113.60(11) ?
C6 C7 H7A . . 108.2(9) ?
C8 C7 H7A . . 106.3(9) ?
C6 C7 H7B . . 108.6(11) ?
C8 C7 H7B . . 111.0(11) ?
H7A C7 H7B . . 109.1(14) ?
C9 C8 C7 . . 112.40(11) ?
C9 C8 H8A . . 108.8(10) ?
C7 C8 H8A . . 110.4(10) ?
C9 C8 H8B . . 109.6(11) ?
C7 C8 H8B . . 109.3(11) ?
H8A C8 H8B . . 106.1(15) ?
C10 C9 C8 . . 114.78(11) ?
C10 C9 H9B . . 109.8(9) ?
C8 C9 H9B . . 108.6(9) ?
C10 C9 H9A . . 107.9(10) ?
C8 C9 H9A . . 107.8(10) ?
H9B C9 H9A . . 107.8(13) ?
C11 C10 C9 . . 122.75(11) ?
C11 C10 H10 . . 119.4(9) ?
C9 C10 H10 . . 117.9(9) ?
C10 C11 C1 . . 120.74(11) ?
C10 C11 C12 . . 123.03(11) ?
C1 C11 C12 . . 116.17(10) ?
C13 C12 C17 . . 118.10(11) ?
C13 C12 C11 . . 122.12(11) ?
C17 C12 C11 . . 119.69(11) ?
C12 C13 C14 . . 121.29(12) ?
C12 C13 H13 . . 120.7(10) ?
C14 C13 H13 . . 118.0(10) ?
C15 C14 C13 . . 120.38(12) ?
C15 C14 H14 . . 119.8(10) ?
C13 C14 H14 . . 119.7(10) ?
C14 C15 C16 . . 118.98(11) ?
C14 C15 C19 . . 119.61(11) ?
C16 C15 C19 . . 121.35(11) ?
C17 C16 C15 . . 120.15(11) ?
C17 C16 H16] . . 118.3(10) ?
C15 C16 H16] . . 121.6(10) ?
O1 C17 C16 . . 124.15(11) ?
O1 C17 C12 . . 114.90(11) ?
C16 C17 C12 . . 120.95(11) ?
O1 C18 H18A . . 110.8(10) ?
O1 C18 H18B . . 110.1(10) ?
H18A C18 H18B . . 111.8(14) ?
O1 C18 H18C . . 102.7(10) ?
H18A C18 H18C . . 107.3(15) ?
H18B C18 H18C . . 113.8(14) ?
C20 C19 C15 . . 126.37(12) ?
C20 C19 H19 . . 116.9(10) ?
C15 C19 H19 . . 116.7(10) ?
C19 C20 C21 . . 121.74(12) ?
C19 C20 H20 . . 123.7(11) ?
C21 C20 H20 . . 114.5(11) ?
O2 C21 O3 . . 123.81(12) ?
O2 C21 C20 . . 125.98(12) ?
O3 C21 C20 . . 110.21(11) ?
O3 C22 C23 . . 108.30(12) ?
O3 C22 H22A . . 106.2(11) ?
C23 C22 H22A . . 112.7(11) ?
O3 C22 H22B . . 108.1(11) ?
C23 C22 H22B . . 111.2(11) ?
H22A C22 H22B . . 110.2(15) ?
C22 C23 H23A . . 109.1(12) ?
C22 C23 H23B . . 111.0(13) ?
H23A C23 H23B . . 108.1(18) ?
C22 C23 H23C . . 111.3(13) ?
H23A C23 H23C . . 113.1(17) ?
H23B C23 H23C . . 104.2(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 . 1.3657(15) ?
O1 C18 . 1.4343(16) ?
C1 C2 . 1.4013(18) ?
C1 C6 . 1.4072(18) ?
C1 C11 . 1.4908(17) ?
O2 C21 . 1.2090(16) ?
C2 C3 . 1.3869(19) ?
C2 H2 . 0.997(17) ?
O3 C21 . 1.3445(16) ?
O3 C22 . 1.4510(15) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.950(19) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.986(16) ?
C5 C6 . 1.3956(19) ?
C5 H5 . 0.998(18) ?
C6 C7 . 1.5101(18) ?
C7 C8 . 1.5403(19) ?
C7 H7A . 1.024(17) ?
C7 H7B . 0.985(19) ?
C8 C9 . 1.5388(19) ?
C8 H8A . 0.982(18) ?
C8 H8B . 1.00(2) ?
C9 C10 . 1.5060(18) ?
C9 H9B . 0.980(17) ?
C9 H9A . 1.009(18) ?
C10 C11 . 1.3350(18) ?
C10 H10 . 0.985(16) ?
C11 C12 . 1.4929(17) ?
C12 C13 . 1.3878(18) ?
C12 C17 . 1.4116(18) ?
C13 C14 . 1.3920(18) ?
C13 H13 . 0.969(17) ?
C14 C15 . 1.3910(18) ?
C14 H14 . 0.949(17) ?
C15 C16 . 1.4076(17) ?
C15 C19 . 1.4649(18) ?
C16 C17 . 1.3831(18) ?
C16 H16] . 0.975(18) ?
C18 H18A . 0.983(19) ?
C18 H18B . 1.009(18) ?
C18 H18C . 0.994(19) ?
C19 C20 . 1.3278(19) ?
C19 H19 . 0.999(18) ?
C20 C21 . 1.4713(18) ?
C20 H20 . 0.93(2) ?
C22 C23 . 1.485(2) ?
C22 H22A . 0.98(2) ?
C22 H22B . 0.97(2) ?
C23 H23A . 1.00(2) ?
C23 H23B . 0.94(2) ?
C23 H23C . 1.01(2) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.16(18) ?
C11 C1 C2 C3 . . . . -175.85(11) ?
C1 C2 C3 C4 . . . . -1.07(19) ?
C2 C3 C4 C5 . . . . -0.7(2) ?
C3 C4 C5 C6 . . . . 1.43(19) ?
C4 C5 C6 C1 . . . . -0.33(18) ?
C4 C5 C6 C7 . . . . -178.99(11) ?
C2 C1 C6 C5 . . . . -1.43(17) ?
C11 C1 C6 C5 . . . . 176.55(10) ?
C2 C1 C6 C7 . . . . 177.24(11) ?
C11 C1 C6 C7 . . . . -4.78(17) ?
C5 C6 C7 C8 . . . . -108.66(14) ?
C1 C6 C7 C8 . . . . 72.70(16) ?
C6 C7 C8 C9 . . . . -42.10(17) ?
C7 C8 C9 C10 . . . . -40.53(16) ?
C8 C9 C10 C11 . . . . 70.15(17) ?
C9 C10 C11 C1 . . . . -1.15(19) ?
C9 C10 C11 C12 . . . . 175.85(11) ?
C2 C1 C11 C10 . . . . 132.20(13) ?
C6 C1 C11 C10 . . . . -45.78(17) ?
C2 C1 C11 C12 . . . . -45.00(15) ?
C6 C1 C11 C12 . . . . 137.02(12) ?
C10 C11 C12 C13 . . . . -74.21(17) ?
C1 C11 C12 C13 . . . . 102.92(13) ?
C10 C11 C12 C17 . . . . 109.20(14) ?
C1 C11 C12 C17 . . . . -73.67(14) ?
C17 C12 C13 C14 . . . . 2.74(18) ?
C11 C12 C13 C14 . . . . -173.91(11) ?
C12 C13 C14 C15 . . . . 0.63(19) ?
C13 C14 C15 C16 . . . . -3.30(18) ?
C13 C14 C15 C19 . . . . 173.77(11) ?
C14 C15 C16 C17 . . . . 2.57(18) ?
C19 C15 C16 C17 . . . . -174.45(11) ?
C18 O1 C17 C16 . . . . 3.63(18) ?
C18 O1 C17 C12 . . . . -176.42(11) ?
C15 C16 C17 O1 . . . . -179.22(11) ?
C15 C16 C17 C12 . . . . 0.84(18) ?
C13 C12 C17 O1 . . . . 176.58(10) ?
C11 C12 C17 O1 . . . . -6.69(16) ?
C13 C12 C17 C16 . . . . -3.47(17) ?
C11 C12 C17 C16 . . . . 173.26(11) ?
C14 C15 C19 C20 . . . . -167.16(13) ?
C16 C15 C19 C20 . . . . 9.8(2) ?
C15 C19 C20 C21 . . . . 177.51(12) ?
C22 O3 C21 O2 . . . . -0.71(18) ?
C22 O3 C21 C20 . . . . 178.41(11) ?
C19 C20 C21 O2 . . . . -2.8(2) ?
C19 C20 C21 O3 . . . . 178.10(12) ?
C21 O3 C22 C23 . . . . -176.91(13) ?
