#------------------------------------------------------------------------------
#$Date: 2022-03-03 22:20:04 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519330.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_4519330
loop_
_publ_author_name
'Abel-Snape, Xavier'
'Wycich, Gina'
'Lautens, Mark'
_publ_section_title
;
 Synthesis of Indenes and Benzofulvenes via a Palladium-Catalyzed
 Three-Component Reaction
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3291
_journal_page_last               3301
_journal_paper_doi               10.1021/acscatal.1c06046
_journal_year                    2022
_chemical_formula_moiety         'C23 H18 O'
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                93.225(4)
_cell_angle_beta                 112.881(4)
_cell_angle_gamma                109.629(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8621(13)
_cell_length_b                   10.1071(15)
_cell_length_c                   10.9059(15)
_cell_measurement_reflns_used    6913
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.19
_cell_volume                     827.8(2)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34832
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.076
_diffrn_source
'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       Shard
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0413
_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)+(0.0335P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2767
_reflns_number_total             3793
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c06046_si_002.cif
_cod_data_source_block           d2182_a
_cod_database_code               4519330
_shelx_shelxl_version_number     2018/3
_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   0.982
_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
O1 O 0.23646(12) 0.43891(9) 0.76787(9) 0.0273(2) Uani 1 1 d . . . . .
C1 C 0.65531(18) 0.74445(14) 0.81127(13) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.50376(18) 0.69759(14) 0.66976(13) 0.0286(3) Uani 1 1 d . . . . .
H2 H 0.387606 0.692578 0.650612 0.034 Uiso 1 1 calc R U . . .
C3 C 0.55296(17) 0.66415(14) 0.57510(13) 0.0266(3) Uani 1 1 d . . . . .
H3A H 0.478200 0.632855 0.480005 0.032 Uiso 1 1 calc R U . . .
C4 C 0.73901(17) 0.68302(13) 0.64007(12) 0.0235(3) Uani 1 1 d . . . . .
C5 C 0.84982(18) 0.66174(14) 0.58675(14) 0.0292(3) Uani 1 1 d . . . . .
H5A H 0.806177 0.627437 0.491673 0.035 Uiso 1 1 calc R U . . .
C6 C 1.0248(2) 0.69121(16) 0.67408(15) 0.0362(3) Uani 1 1 d . . . . .
H6A H 1.102046 0.677743 0.638369 0.043 Uiso 1 1 calc R U . . .
C7 C 1.08915(19) 0.74011(17) 0.81299(15) 0.0385(4) Uani 1 1 d . . . . .
H7A H 1.209912 0.760176 0.871564 0.046 Uiso 1 1 calc R U . . .
C8 C 0.97753(18) 0.76003(15) 0.86730(14) 0.0328(3) Uani 1 1 d . . . . .
H8A H 1.021079 0.792669 0.962629 0.039 Uiso 1 1 calc R U . . .
C9 C 0.80300(17) 0.73167(13) 0.78059(12) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.7010(2) 0.89924(15) 0.87788(16) 0.0402(4) Uani 1 1 d . . . . .
H10A H 0.733946 0.964592 0.821193 0.060 Uiso 1 1 calc R U . . .
H10B H 0.800844 0.926546 0.968461 0.060 Uiso 1 1 calc R U . . .
H10C H 0.597420 0.905393 0.886509 0.060 Uiso 1 1 calc R U . . .
C11 C 0.61255(19) 0.64586(14) 0.90731(13) 0.0301(3) Uani 1 1 d . . . . .
H11A H 0.719839 0.676986 0.995362 0.036 Uiso 1 1 calc R U . . .
H11B H 0.517868 0.661312 0.925349 0.036 Uiso 1 1 calc R U . . .
C12 C 0.55399(18) 0.48711(14) 0.85687(12) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.67232(19) 0.41976(15) 0.87615(13) 0.0315(3) Uani 1 1 d . . . . .
H13A H 0.796223 0.476967 0.919255 0.038 Uiso 1 1 calc R U . . .
C14 C 0.61645(19) 0.27161(16) 0.83476(14) 0.0343(3) Uani 1 1 d . . . . .
H14A H 0.702716 0.230978 0.849210 0.041 Uiso 1 1 calc R U . . .
C15 C 0.43779(19) 0.18252(15) 0.77303(13) 0.0309(3) Uani 1 1 d . . . . .
H15A H 0.400274 0.081501 0.745674 0.037 Uiso 1 1 calc R U . . .
C16 C 0.31488(18) 0.24567(14) 0.75233(12) 0.0251(3) Uani 1 1 d . . . . .
C17 C 0.12317(17) 0.19241(14) 0.69812(12) 0.0254(3) Uani 1 1 d . . . . .
C18 C -0.01535(19) 0.05780(14) 0.64174(13) 0.0297(3) Uani 1 1 d . . . . .
H18A H 0.007904 -0.026774 0.634582 0.036 Uiso 1 1 calc R U . . .
C19 C -0.18729(19) 0.04997(15) 0.59646(14) 0.0340(3) Uani 1 1 d . . . . .
H19A H -0.283455 -0.041047 0.555919 0.041 Uiso 1 1 calc R U . . .
C20 C -0.22258(19) 0.17326(16) 0.60911(14) 0.0352(3) Uani 1 1 d . . . . .
H20A H -0.342483 0.164309 0.577042 0.042 Uiso 1 1 calc R U . . .
C21 C -0.08679(18) 0.30871(15) 0.66742(14) 0.0328(3) Uani 1 1 d . . . . .
H21A H -0.110053 0.392863 0.677318 0.039 Uiso 1 1 calc R U . . .
C22 C 0.08367(18) 0.31400(14) 0.71008(12) 0.0261(3) Uani 1 1 d . . . . .
C23 C 0.37609(17) 0.39469(14) 0.79303(12) 0.0247(3) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O1 C23 105.41(10) . . ?
C2 C1 C9 101.08(10) . . ?
C2 C1 C10 111.69(12) . . ?
C9 C1 C10 111.92(11) . . ?
C2 C1 C11 112.15(11) . . ?
C9 C1 C11 112.26(11) . . ?
C10 C1 C11 107.75(10) . . ?
C3 C2 C1 111.83(12) . . ?
C3 C2 H2 124.1 . . ?
C1 C2 H2 124.1 . . ?
C2 C3 C4 109.49(11) . . ?
C2 C3 H3A 125.3 . . ?
C4 C3 H3A 125.3 . . ?
C5 C4 C9 120.42(12) . . ?
C5 C4 C3 131.56(12) . . ?
C9 C4 C3 108.02(11) . . ?
C6 C5 C4 118.95(13) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C5 C6 C7 120.90(13) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C8 120.34(13) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 119.05(13) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C4 120.33(12) . . ?
C8 C9 C1 130.08(12) . . ?
C4 C9 C1 109.59(11) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C1 116.32(10) . . ?
C12 C11 H11A 108.2 . . ?
C1 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C1 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C23 C12 C13 114.44(12) . . ?
C23 C12 C11 122.35(12) . . ?
C13 C12 C11 123.14(12) . . ?
C12 C13 C14 122.62(13) . . ?
C12 C13 H13A 118.7 . . ?
C14 C13 H13A 118.7 . . ?
C15 C14 C13 121.32(13) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 117.87(13) . . ?
C14 C15 H15A 121.1 . . ?
C16 C15 H15A 121.1 . . ?
C15 C16 C23 119.07(12) . . ?
C15 C16 C17 134.94(12) . . ?
C23 C16 C17 105.97(11) . . ?
C18 C17 C22 119.06(12) . . ?
C18 C17 C16 135.33(12) . . ?
C22 C17 C16 105.61(11) . . ?
C19 C18 C17 118.41(13) . . ?
C19 C18 H18A 120.8 . . ?
C17 C18 H18A 120.8 . . ?
C18 C19 C20 121.20(13) . . ?
C18 C19 H19A 119.4 . . ?
C20 C19 H19A 119.4 . . ?
C21 C20 C19 121.61(13) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C22 C21 C20 116.12(13) . . ?
C22 C21 H21A 121.9 . . ?
C20 C21 H21A 121.9 . . ?
C21 C22 O1 124.84(12) . . ?
C21 C22 C17 123.57(12) . . ?
O1 C22 C17 111.58(11) . . ?
C12 C23 O1 123.83(12) . . ?
C12 C23 C16 124.67(12) . . ?
O1 C23 C16 111.43(11) . . ?
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
O1 C22 1.3867(16) . ?
O1 C23 1.3884(15) . ?
C1 C2 1.5127(18) . ?
C1 C9 1.5136(18) . ?
C1 C10 1.5353(19) . ?
C1 C11 1.5512(18) . ?
C2 C3 1.3341(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4567(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3860(18) . ?
C4 C9 1.4014(17) . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.395(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3794(19) . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5051(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C23 1.3880(19) . ?
C12 C13 1.3898(19) . ?
C13 C14 1.394(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3918(19) . ?
C15 H15A 0.9500 . ?
C16 C23 1.3959(18) . ?
C16 C17 1.4471(19) . ?
C17 C18 1.3903(19) . ?
C17 C22 1.3987(18) . ?
C18 C19 1.379(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3775(19) . ?
C21 H21A 0.9500 . ?
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
C9 C1 C2 C3 -0.04(14) . . . . ?
C10 C1 C2 C3 119.12(13) . . . . ?
C11 C1 C2 C3 -119.81(12) . . . . ?
C1 C2 C3 C4 0.40(15) . . . . ?
C2 C3 C4 C5 179.53(13) . . . . ?
C2 C3 C4 C9 -0.62(15) . . . . ?
C9 C4 C5 C6 -0.92(19) . . . . ?
C3 C4 C5 C6 178.91(13) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C4 0.2(2) . . . . ?
C7 C8 C9 C1 -179.67(13) . . . . ?
C5 C4 C9 C8 0.53(19) . . . . ?
C3 C4 C9 C8 -179.34(12) . . . . ?
C5 C4 C9 C1 -179.54(11) . . . . ?
C3 C4 C9 C1 0.59(14) . . . . ?
C2 C1 C9 C8 179.57(13) . . . . ?
C10 C1 C9 C8 60.58(18) . . . . ?
C11 C1 C9 C8 -60.75(18) . . . . ?
C2 C1 C9 C4 -0.35(13) . . . . ?
C10 C1 C9 C4 -119.34(12) . . . . ?
C11 C1 C9 C4 119.33(11) . . . . ?
C2 C1 C11 C12 53.39(16) . . . . ?
C9 C1 C11 C12 -59.61(15) . . . . ?
C10 C1 C11 C12 176.70(12) . . . . ?
C1 C11 C12 C23 -96.94(14) . . . . ?
C1 C11 C12 C13 86.42(16) . . . . ?
C23 C12 C13 C14 -0.05(18) . . . . ?
C11 C12 C13 C14 176.83(12) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C13 C14 C15 C16 0.54(19) . . . . ?
C14 C15 C16 C23 0.60(18) . . . . ?
C14 C15 C16 C17 -177.21(13) . . . . ?
C15 C16 C17 C18 -2.1(2) . . . . ?
C23 C16 C17 C18 179.89(14) . . . . ?
C15 C16 C17 C22 178.17(13) . . . . ?
C23 C16 C17 C22 0.16(12) . . . . ?
C22 C17 C18 C19 1.64(18) . . . . ?
C16 C17 C18 C19 -178.07(13) . . . . ?
C17 C18 C19 C20 -1.34(19) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 0.81(19) . . . . ?
C20 C21 C22 O1 178.53(11) . . . . ?
C20 C21 C22 C17 -0.48(19) . . . . ?
C23 O1 C22 C21 -179.13(12) . . . . ?
C23 O1 C22 C17 -0.02(13) . . . . ?
C18 C17 C22 C21 -0.75(18) . . . . ?
C16 C17 C22 C21 179.03(12) . . . . ?
C18 C17 C22 O1 -179.88(10) . . . . ?
C16 C17 C22 O1 -0.09(13) . . . . ?
C13 C12 C23 O1 177.89(11) . . . . ?
C11 C12 C23 O1 0.97(18) . . . . ?
C13 C12 C23 C16 1.27(17) . . . . ?
C11 C12 C23 C16 -175.64(11) . . . . ?
C22 O1 C23 C12 -176.88(11) . . . . ?
C22 O1 C23 C16 0.12(12) . . . . ?
C15 C16 C23 C12 -1.59(18) . . . . ?
C17 C16 C23 C12 176.80(11) . . . . ?
C15 C16 C23 O1 -178.57(10) . . . . ?
C17 C16 C23 O1 -0.18(13) . . . . ?
