#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:20:41 +0300 (Thu, 05 May 2022) $
#$Revision: 274950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/98/7129834.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_7129834
loop_
_publ_author_name
'Yao, Tuanli'
'Zhao, Shuaijing'
'Liu, Tao'
'Wu, Yuting'
'Ma, Yanhui'
'Li, Tao'
'Qin, Xiangyang'
_publ_section_title
;
 Transition-metal-free approaches to 2,3-diarylated indenones from
 2-alkynylbenzaldehydes and phenols with tunable selectivity.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4592
_journal_page_last               4595
_journal_paper_doi               10.1039/d2cc01324j
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C32 H33 Cl O4'
_chemical_formula_sum            'C32 H33 Cl O4'
_chemical_formula_weight         517.03
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                94.809(2)
_cell_angle_beta                 107.322(2)
_cell_angle_gamma                91.397(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1084(5)
_cell_length_b                   11.8341(7)
_cell_length_c                   13.8157(8)
_cell_measurement_reflns_used    8257
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.35
_cell_volume                     1414.74(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42560
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9304.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4972
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0772P)²+0.5213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                3255
_reflns_number_total             4972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01324j2.cif
_cod_data_source_block           sust_3210_0m
_cod_depositor_comments
'Adding full bibliography for 7129831--7129837.cif.'
_cod_database_code               7129834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H4-H28a
 2.2 with sigma of 0.02
 H4-H27c
 2.45 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16), C20(H20),
 C24(H24)
3.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C26(H26a,H26b,H26c), C27(H27a,H27b,H27c), C28(H28a,H28b,
 H28c), C30(H30a,H30b,H30c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.7689(6) -0.1604(4) 0.1082(3) 0.1019(14) Uani 1 d . . .
H1A H 0.6604 -0.1793 0.0906 0.153 Uiso 1 calc . . GR
H1B H 0.8248 -0.2277 0.1233 0.153 Uiso 1 calc . . GR
H1C H 0.7914 -0.1289 0.0521 0.153 Uiso 1 calc . . GR
C2 C 0.8121(6) -0.0812(3) 0.1932(3) 0.1066(16) Uani 1 d . . .
H2A H 0.9215 -0.0612 0.2110 0.128 Uiso 1 calc . . R
H2B H 0.7921 -0.1133 0.2507 0.128 Uiso 1 calc . . R
C3 C 0.7367(4) 0.0979(3) 0.2461(3) 0.0605(8) Uani 1 d . . .
C4 C 0.6533(3) 0.2016(2) 0.2179(2) 0.0485(7) Uani 1 d . . .
C5 C 0.5855(4) 0.2231(3) 0.1180(2) 0.0561(8) Uani 1 d . . .
H5 H 0.5873 0.1693 0.0653 0.067 Uiso 1 calc . . R
C6 C 0.5151(3) 0.3236(3) 0.0958(2) 0.0521(7) Uani 1 d . . .
H6 H 0.4696 0.3368 0.0283 0.063 Uiso 1 calc . . R
C7 C 0.5110(3) 0.4054(2) 0.1728(2) 0.0417(6) Uani 1 d . . .
C8 C 0.5764(3) 0.3817(2) 0.2732(2) 0.0503(7) Uani 1 d . . .
H8 H 0.5721 0.4342 0.3261 0.060 Uiso 1 calc . . R
C9 C 0.6471(3) 0.2818(2) 0.2950(2) 0.0524(8) Uani 1 d . . .
H9 H 0.6914 0.2679 0.3625 0.063 Uiso 1 calc . . R
C10 C 0.4392(3) 0.5140(2) 0.1492(2) 0.0415(6) Uani 1 d . . .
C11 C 0.2915(3) 0.5226(3) 0.0657(2) 0.0502(7) Uani 1 d . . .
C12 C 0.2546(3) 0.6436(3) 0.0702(2) 0.0479(7) Uani 1 d . . .
C13 C 0.1344(3) 0.6999(3) 0.0123(2) 0.0627(9) Uani 1 d . . .
H13 H 0.0558 0.6603 -0.0394 0.075 Uiso 1 calc . . R
C14 C 0.1317(4) 0.8169(3) 0.0322(3) 0.0677(10) Uani 1 d . . .
H14 H 0.0512 0.8564 -0.0063 0.081 Uiso 1 calc . . R
C15 C 0.2487(4) 0.8738(3) 0.1090(2) 0.0564(8) Uani 1 d . . .
C16 C 0.3718(3) 0.8179(2) 0.1686(2) 0.0485(7) Uani 1 d . . .
H16 H 0.4505 0.8577 0.2201 0.058 Uiso 1 calc . . R
C17 C 0.3729(3) 0.7023(2) 0.1488(2) 0.0425(7) Uani 1 d . . .
C18 C 0.4866(3) 0.6197(2) 0.19695(19) 0.0393(6) Uani 1 d . . .
C19 C 0.6276(3) 0.6540(2) 0.28024(19) 0.0372(6) Uani 1 d . . .
C20 C 0.6228(3) 0.7227(2) 0.3649(2) 0.0403(6) Uani 1 d . . .
H20 H 0.5279 0.7468 0.3681 0.048 Uiso 1 calc . . R
C21 C 0.7533(3) 0.7576(2) 0.44553(19) 0.0388(6) Uani 1 d . . .
C22 C 0.8938(3) 0.7232(2) 0.43412(19) 0.0382(6) Uani 1 d . . .
C23 C 0.9051(3) 0.6505(2) 0.35086(19) 0.0351(6) Uani 1 d . . .
C24 C 0.7693(3) 0.6176(2) 0.27549(19) 0.0373(6) Uani 1 d . . .
H24 H 0.7729 0.5694 0.2196 0.045 Uiso 1 calc . . R
C25 C 0.7395(3) 0.8296(2) 0.5402(2) 0.0475(7) Uani 1 d . . .
C26 C 0.5703(4) 0.8438(3) 0.5352(3) 0.0732(10) Uani 1 d . . .
H26A H 0.5191 0.7704 0.5284 0.110 Uiso 1 calc . . GR
H26B H 0.5206 0.8839 0.4777 0.110 Uiso 1 calc . . GR
H26C H 0.5655 0.8861 0.5966 0.110 Uiso 1 calc . . GR
C27 C 0.8113(4) 0.9505(2) 0.5475(3) 0.0615(9) Uani 1 d . . .
H27A H 0.7494 1.0042 0.5711 0.092 Uiso 1 calc . . GR
H27B H 0.8158 0.9670 0.4816 0.092 Uiso 1 calc . . GR
H27C H 0.9135 0.9555 0.5945 0.092 Uiso 1 calc . . DGR
C28 C 0.8137(5) 0.7720(3) 0.6376(2) 0.0700(10) Uani 1 d . . .
H28A H 0.9187 0.7576 0.6421 0.105 Uiso 1 calc . . DGR
H28B H 0.7578 0.7015 0.6355 0.105 Uiso 1 calc . . GR
H28C H 0.8110 0.8209 0.6960 0.105 Uiso 1 calc . . GR
C29 C 1.0605(3) 0.6110(2) 0.3421(2) 0.0424(7) Uani 1 d . . .
C30 C 1.1620(4) 0.7141(3) 0.3350(3) 0.0705(10) Uani 1 d . . .
H30A H 1.1103 0.7522 0.2766 0.106 Uiso 1 calc . . GR
H30B H 1.2583 0.6888 0.3285 0.106 Uiso 1 calc . . GR
H30C H 1.1807 0.7654 0.3955 0.106 Uiso 1 calc . . GR
C31 C 1.1438(4) 0.5466(3) 0.4333(2) 0.0609(9) Uani 1 d . . .
H31A H 1.1609 0.5952 0.4952 0.091 Uiso 1 calc . . GR
H31B H 1.2409 0.5237 0.4264 0.091 Uiso 1 calc . . GR
H31C H 1.0815 0.4806 0.4351 0.091 Uiso 1 calc . . GR
C32 C 1.0396(3) 0.5288(3) 0.2466(2) 0.0611(9) Uani 1 d . . .
H32A H 0.9747 0.4644 0.2484 0.092 Uiso 1 calc . . GR
H32B H 1.1382 0.5039 0.2445 0.092 Uiso 1 calc . . GR
H32C H 0.9929 0.5667 0.1871 0.092 Uiso 1 calc . . GR
Cl1 Cl 0.24517(13) 1.01931(8) 0.13570(8) 0.0905(4) Uani 1 d . . .
O1 O 0.7235(3) 0.0207(2) 0.16989(18) 0.0852(8) Uani 1 d . . .
O2 O 0.8118(4) 0.0830(2) 0.3311(2) 0.0990(10) Uani 1 d . . .
O3 O 0.2156(3) 0.4452(2) 0.00736(18) 0.0752(7) Uani 1 d . . .
O4 O 1.0318(2) 0.75632(17) 0.50535(15) 0.0577(6) Uani 1 d . . .
H4 H 1.0266 0.8202 0.5316 0.087 Uiso 1 calc . . DGR
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
C1 C2 O1 109.0(3) . . ?
O1 C3 C4 114.6(3) . . ?
O2 C3 C4 124.2(3) . . ?
O2 C3 O1 121.1(3) . . ?
C5 C4 C3 122.9(3) . . ?
C9 C4 C3 118.3(3) . . ?
C9 C4 C5 118.8(3) . . ?
C6 C5 C4 120.5(3) . . ?
C5 C6 C7 121.0(3) . . ?
C6 C7 C8 118.0(3) . . ?
C6 C7 C10 121.0(2) . . ?
C8 C7 C10 121.0(2) . . ?
C9 C8 C7 120.8(3) . . ?
C8 C9 C4 120.8(3) . . ?
C7 C10 C11 123.0(2) . . ?
C18 C10 C7 128.5(2) . . ?
C18 C10 C11 108.5(2) . . ?
C12 C11 C10 106.3(2) . . ?
O3 C11 C10 126.9(3) . . ?
O3 C11 C12 126.8(3) . . ?
C13 C12 C11 131.6(3) . . ?
C13 C12 C17 120.9(3) . . ?
C17 C12 C11 107.5(2) . . ?
C12 C13 C14 119.1(3) . . ?
C15 C14 C13 119.6(3) . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 Cl1 120.0(2) . . ?
C16 C15 Cl1 117.8(3) . . ?
C17 C16 C15 117.8(3) . . ?
C12 C17 C18 108.7(2) . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 C18 130.8(3) . . ?
C10 C18 C17 109.1(2) . . ?
C10 C18 C19 128.2(2) . . ?
C19 C18 C17 122.7(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 C24 118.4(2) . . ?
C24 C19 C18 120.5(2) . . ?
C19 C20 C21 123.1(2) . . ?
C20 C21 C22 115.9(2) . . ?
C20 C21 C25 120.6(2) . . ?
C22 C21 C25 123.5(2) . . ?
C21 C22 C23 123.3(2) . . ?
O4 C22 C21 122.0(2) . . ?
O4 C22 C23 114.7(2) . . ?
C22 C23 C29 122.2(2) . . ?
C24 C23 C22 116.8(2) . . ?
C24 C23 C29 121.0(2) . . ?
C23 C24 C19 122.3(2) . . ?
C21 C25 C27 110.9(2) . . ?
C26 C25 C21 111.4(2) . . ?
C26 C25 C27 106.1(2) . . ?
C26 C25 C28 106.4(3) . . ?
C28 C25 C21 110.8(2) . . ?
C28 C25 C27 110.9(3) . . ?
C23 C29 C30 109.8(2) . . ?
C23 C29 C31 111.1(2) . . ?
C31 C29 C30 110.2(2) . . ?
C32 C29 C23 111.5(2) . . ?
C32 C29 C30 107.8(3) . . ?
C32 C29 C31 106.3(2) . . ?
C3 O1 C2 116.6(3) . . ?
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 1.391(5) . ?
C2 O1 1.473(4) . ?
C3 C4 1.479(4) . ?
C3 O1 1.309(4) . ?
C3 O2 1.200(4) . ?
C4 C5 1.382(4) . ?
C4 C9 1.381(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.386(4) . ?
C7 C8 1.392(4) . ?
C7 C10 1.473(4) . ?
C8 C9 1.373(4) . ?
C10 C11 1.501(4) . ?
C10 C18 1.361(4) . ?
C11 C12 1.479(4) . ?
C11 O3 1.217(3) . ?
C12 C13 1.373(4) . ?
C12 C17 1.401(4) . ?
C13 C14 1.392(5) . ?
C14 C15 1.373(5) . ?
C15 C16 1.397(4) . ?
C15 Cl1 1.734(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.490(4) . ?
C18 C19 1.468(3) . ?
C19 C20 1.379(4) . ?
C19 C24 1.389(3) . ?
C20 C21 1.391(4) . ?
C21 C22 1.401(4) . ?
C21 C25 1.539(4) . ?
C22 C23 1.408(3) . ?
C22 O4 1.370(3) . ?
C23 C24 1.381(3) . ?
C23 C29 1.537(3) . ?
C25 C26 1.536(4) . ?
C25 C27 1.540(4) . ?
C25 C28 1.539(4) . ?
C29 C30 1.539(4) . ?
C29 C31 1.538(4) . ?
C29 C32 1.532(4) . ?
