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#$Date: 2023-10-06 03:48:24 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159566.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_7159566
loop_
_publ_author_name
'Sreenivasulu, Gottam'
'Sridhar, Balasubramanian'
'Karunakar, Galla V.'
_publ_section_title
;
 Dual gold-catalyzed regioselective synthesis of benzofulvenes via
 5-endo dig cyclization.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7799
_journal_page_last               7807
_journal_paper_doi               10.1039/d3ob01079a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H15 Cl O2'
_chemical_formula_sum            'C19 H15 Cl O2'
_chemical_formula_weight         310.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-04-06 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4838(4)
_cell_length_b                   11.3226(3)
_cell_length_c                   8.5334(2)
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.0735
_cell_measurement_theta_min      2.496
_cell_volume                     1576.99(7)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21052
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.189
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0460
_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)+(0.0625P)²+0.3371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2240
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01079a2.cif
_cod_data_source_block           KB418_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159566.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159566
_shelx_shelxl_version_number     2019/2
_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   0.939
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75160(11) 0.28888(18) 0.8350(2) 0.0591(5) Uani 1 1 d . . . . .
H1 H 0.757197 0.215200 0.789510 0.071 Uiso 1 1 calc R U . . .
C2 C 0.81639(11) 0.3412(2) 0.9312(2) 0.0650(5) Uani 1 1 d . . . . .
C3 C 0.80917(13) 0.4496(2) 1.0006(2) 0.0687(6) Uani 1 1 d . . . . .
H3 H 0.853626 0.481711 1.065826 0.082 Uiso 1 1 calc R U . . .
C4 C 0.73608(12) 0.51105(19) 0.9737(2) 0.0612(5) Uani 1 1 d . . . . .
H4 H 0.730978 0.584632 1.019780 0.073 Uiso 1 1 calc R U . . .
C5 C 0.67069(10) 0.46115(16) 0.8771(2) 0.0508(4) Uani 1 1 d . . . . .
C6 C 0.67840(10) 0.35000(16) 0.8088(2) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.59898(10) 0.32153(17) 0.7124(2) 0.0519(4) Uani 1 1 d . . . . .
C8 C 0.54518(10) 0.42256(18) 0.7318(2) 0.0548(5) Uani 1 1 d . . . . .
C9 C 0.58746(11) 0.50325(18) 0.8261(2) 0.0577(5) Uani 1 1 d . . . . .
H9 H 0.566701 0.575293 0.854572 0.069 Uiso 1 1 calc R U . . .
C10 C 0.58211(14) 0.2273(2) 0.6230(3) 0.0743(6) Uani 1 1 d . . . . .
H00B H 0.530885 0.219471 0.562572 0.089 Uiso 1 1 calc R U . . .
H00C H 0.621427 0.168732 0.620364 0.089 Uiso 1 1 calc R U . . .
C11 C 0.45893(11) 0.4339(2) 0.6504(2) 0.0658(6) Uani 1 1 d . . . . .
H00I H 0.457742 0.409675 0.541071 0.079 Uiso 1 1 calc R U . . .
H00K H 0.443757 0.516657 0.649892 0.079 Uiso 1 1 calc R U . . .
C12 C 0.39450(10) 0.36405(17) 0.7205(2) 0.0519(4) Uani 1 1 d . . . . .
C13 C 0.30857(10) 0.37458(15) 0.6422(2) 0.0476(4) Uani 1 1 d . . . . .
C14 C 0.24890(11) 0.29996(17) 0.6882(2) 0.0591(5) Uani 1 1 d . . . . .
H14 H 0.263421 0.244596 0.767728 0.071 Uiso 1 1 calc R U . . .
C15 C 0.16902(12) 0.30728(19) 0.6176(3) 0.0682(6) Uani 1 1 d . . . . .
H15 H 0.129820 0.257205 0.649927 0.082 Uiso 1 1 calc R U . . .
C16 C 0.14645(11) 0.38849(18) 0.4989(2) 0.0577(5) Uani 1 1 d . . . . .
C17 C 0.20378(11) 0.46438(18) 0.4524(2) 0.0598(5) Uani 1 1 d . . . . .
H17 H 0.188621 0.520557 0.374280 0.072 Uiso 1 1 calc R U . . .
C18 C 0.28415(11) 0.45590(17) 0.5235(2) 0.0578(5) Uani 1 1 d . . . . .
H18 H 0.323060 0.506275 0.490760 0.069 Uiso 1 1 calc R U . . .
C19 C 0.03931(13) 0.4668(2) 0.3085(3) 0.0858(7) Uani 1 1 d . . . . .
H00L H 0.067933 0.450354 0.220411 0.129 Uiso 1 1 calc R U . . .
H19 H 0.050476 0.546387 0.343746 0.129 Uiso 1 1 calc R U . . .
H00N H -0.018514 0.457264 0.276577 0.129 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91024(4) 0.26788(7) 0.96222(10) 0.1044(3) Uani 1 1 d . . . . .
O1 O 0.41234(8) 0.30127(14) 0.83583(17) 0.0740(4) Uani 1 1 d . . . . .
O2 O 0.06600(8) 0.38726(15) 0.4340(2) 0.0821(5) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 117.71(19) . . ?
C6 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 122.04(19) . . ?
C3 C2 Cl1 119.23(16) . . ?
C1 C2 Cl1 118.73(18) . . ?
C2 C3 C4 120.26(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.80(19) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 120.46(17) . . ?
C4 C5 C9 131.75(18) . . ?
C6 C5 C9 107.79(15) . . ?
C1 C6 C5 120.72(16) . . ?
C1 C6 C7 131.67(17) . . ?
C5 C6 C7 107.59(15) . . ?
C10 C7 C8 127.79(18) . . ?
C10 C7 C6 126.59(19) . . ?
C8 C7 C6 105.55(15) . . ?
C9 C8 C7 108.99(15) . . ?
C9 C8 C11 126.71(19) . . ?
C7 C8 C11 124.21(18) . . ?
C8 C9 C5 110.06(17) . . ?
C8 C9 H9 125.0 . . ?
C5 C9 H9 125.0 . . ?
C7 C10 H00B 120.0 . . ?
C7 C10 H00C 120.0 . . ?
H00B C10 H00C 120.0 . . ?
C8 C11 C12 116.44(16) . . ?
C8 C11 H00I 108.2 . . ?
C12 C11 H00I 108.2 . . ?
C8 C11 H00K 108.2 . . ?
C12 C11 H00K 108.2 . . ?
H00I C11 H00K 107.3 . . ?
O1 C12 C13 121.25(16) . . ?
O1 C12 C11 121.45(16) . . ?
C13 C12 C11 117.31(15) . . ?
C18 C13 C14 117.66(16) . . ?
C18 C13 C12 122.93(16) . . ?
C14 C13 C12 119.41(16) . . ?
C15 C14 C13 120.75(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.42(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O2 C16 C17 123.88(18) . . ?
O2 C16 C15 115.98(17) . . ?
C17 C16 C15 120.14(17) . . ?
C16 C17 C18 119.03(18) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.98(17) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
O2 C19 H00L 109.5 . . ?
O2 C19 H19 109.5 . . ?
H00L C19 H19 109.5 . . ?
O2 C19 H00N 109.5 . . ?
H00L C19 H00N 109.5 . . ?
H19 C19 H00N 109.5 . . ?
C16 O2 C19 118.71(17) . . ?
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 C6 1.382(2) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 Cl1 1.743(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 C9 1.460(2) . ?
C6 C7 1.481(2) . ?
C7 C10 1.318(3) . ?
C7 C8 1.471(3) . ?
C8 C9 1.345(3) . ?
C8 C11 1.498(2) . ?
C9 H9 0.9300 . ?
C10 H00B 0.9300 . ?
C10 H00C 0.9300 . ?
C11 C12 1.513(3) . ?
C11 H00I 0.9700 . ?
C11 H00K 0.9700 . ?
C12 O1 1.216(2) . ?
C12 C13 1.484(2) . ?
C13 C18 1.386(2) . ?
C13 C14 1.394(2) . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 O2 1.364(2) . ?
C16 C17 1.376(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.421(3) . ?
C19 H00L 0.9600 . ?
C19 H19 0.9600 . ?
C19 H00N 0.9600 . ?
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 0.5(3) . . . . ?
C6 C1 C2 Cl1 -178.36(14) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
Cl1 C2 C3 C4 177.98(16) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C9 -179.58(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 178.93(18) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C9 C5 C6 C1 179.20(16) . . . . ?
C4 C5 C6 C7 -179.73(16) . . . . ?
C9 C5 C6 C7 0.29(19) . . . . ?
C1 C6 C7 C10 -2.2(3) . . . . ?
C5 C6 C7 C10 176.55(19) . . . . ?
C1 C6 C7 C8 -179.54(19) . . . . ?
C5 C6 C7 C8 -0.79(19) . . . . ?
C10 C7 C8 C9 -176.3(2) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C10 C7 C8 C11 0.6(3) . . . . ?
C6 C7 C8 C11 177.85(16) . . . . ?
C7 C8 C9 C5 -0.9(2) . . . . ?
C11 C8 C9 C5 -177.60(17) . . . . ?
C4 C5 C9 C8 -179.6(2) . . . . ?
C6 C5 C9 C8 0.4(2) . . . . ?
C9 C8 C11 C12 -105.0(2) . . . . ?
C7 C8 C11 C12 78.8(2) . . . . ?
C8 C11 C12 O1 -0.8(3) . . . . ?
C8 C11 C12 C13 179.64(17) . . . . ?
O1 C12 C13 C18 171.68(19) . . . . ?
C11 C12 C13 C18 -8.7(3) . . . . ?
O1 C12 C13 C14 -8.5(3) . . . . ?
C11 C12 C13 C14 171.15(18) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 C15 -179.74(18) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 O2 178.73(19) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
O2 C16 C17 C18 -178.35(18) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C12 C13 C18 C17 -179.87(18) . . . . ?
C17 C16 O2 C19 1.5(3) . . . . ?
C15 C16 O2 C19 -178.5(2) . . . . ?
