#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:20:41 +0300 (Thu, 05 May 2022) $
#$Revision: 274950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/98/7129832.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_7129832
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         'C30 H28 F3 N O4'
_chemical_formula_sum            'C30 H28 F3 N O4'
_chemical_formula_weight         523.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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
;
2021-12-21 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.806(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.520(8)
_cell_length_b                   11.215(3)
_cell_length_c                   20.049(7)
_cell_measurement_reflns_used    6068
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.45
_cell_volume                     5290(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0919
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38214
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.8482.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.1225
_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)+(0.0873P)²+35.9231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2644
_refine_ls_wR_factor_ref         0.2859
_reflns_number_gt                3138
_reflns_number_total             4667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01324j2.cif
_cod_data_source_block           sust_3208_0m
_cod_depositor_comments
'Adding full bibliography for 7129831--7129837.cif.'
_cod_database_code               7129832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C18(H18),
 C22(H22)
3.b Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C25(H25a,H25b,H25c), C26(H26a,H26b,H26c), C28(H28a,H28b,
 H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
3.c Idealised tetrahedral OH refined as rotating group:
 O4(H4a)
;
_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+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.5415(3) -0.0245(6) 0.6444(3) 0.0489(16) Uani 1 d . . . .
H1 H 0.5389 -0.0757 0.6795 0.059 Uiso 1 calc . . R .
C2 C 0.5864(3) -0.0373(7) 0.6217(3) 0.0593(19) Uani 1 d . . . .
H2 H 0.6136 -0.0966 0.6408 0.071 Uiso 1 calc . . R .
C3 C 0.5891(3) 0.0397(6) 0.5706(3) 0.0507(16) Uani 1 d . . . .
C4 C 0.5488(3) 0.1258(6) 0.5387(3) 0.0503(16) Uani 1 d . . . .
H4 H 0.5515 0.1757 0.5031 0.060 Uiso 1 calc . . R .
C5 C 0.5044(3) 0.1359(5) 0.5607(3) 0.0454(15) Uani 1 d . . . .
H5 H 0.4761 0.1922 0.5388 0.054 Uiso 1 calc . . R .
C6 C 0.5009(2) 0.0630(5) 0.6156(3) 0.0356(13) Uani 1 d . . . .
C7 C 0.4276(3) -0.0396(5) 0.6570(3) 0.0431(14) Uani 1 d . . . .
C8 C 0.4522(2) 0.0709(5) 0.6380(3) 0.0352(13) Uani 1 d . . . .
C9 C 0.4213(2) 0.1667(5) 0.6415(3) 0.0361(13) Uani 1 d . . . .
C10 C 0.3747(2) 0.1248(5) 0.6654(3) 0.0373(13) Uani 1 d . . . .
C11 C 0.3765(3) 0.0019(5) 0.6716(3) 0.0447(14) Uani 1 d . . . .
C12 C 0.3391(3) -0.0602(6) 0.6918(3) 0.0585(18) Uani 1 d . . . .
H12 H 0.3405 -0.1429 0.6949 0.070 Uiso 1 calc . . R .
C13 C 0.2987(3) 0.0041(6) 0.7075(3) 0.0524(16) Uani 1 d . . . .
H13 H 0.2724 -0.0366 0.7206 0.063 Uiso 1 calc . . R .
C14 C 0.2967(2) 0.1242(6) 0.7041(3) 0.0477(15) Uani 1 d . . . .
C15 C 0.3350(2) 0.1892(5) 0.6817(3) 0.0468(15) Uani 1 d . . . .
H15 H 0.3334 0.2719 0.6782 0.056 Uiso 1 calc . . R .
C16 C 0.2565(3) 0.1901(8) 0.7240(5) 0.077(2) Uani 1 d . . . .
C17 C 0.4273(2) 0.2927(4) 0.6259(3) 0.0319(12) Uani 1 d . . . .
C18 C 0.4807(2) 0.3482(5) 0.6488(3) 0.0364(13) Uani 1 d . . . .
H18 H 0.5129 0.3040 0.6753 0.044 Uiso 1 calc . . R .
C19 C 0.4872(2) 0.4669(4) 0.6334(3) 0.0299(12) Uani 1 d . . . .
C20 C 0.4372(2) 0.5305(5) 0.5954(3) 0.0326(12) Uani 1 d . . . .
C21 C 0.3825(2) 0.4773(5) 0.5710(3) 0.0356(13) Uani 1 d . . . .
C22 C 0.3797(2) 0.3588(5) 0.5872(3) 0.0384(13) Uani 1 d . . . .
H22 H 0.3443 0.3220 0.5713 0.046 Uiso 1 calc . . R .
C23 C 0.5470(2) 0.5236(5) 0.6557(3) 0.0340(12) Uani 1 d . . . .
C24 C 0.5550(3) 0.6249(6) 0.7097(4) 0.0598(18) Uani 1 d . . . .
H24A H 0.5296 0.6890 0.6864 0.090 Uiso 1 calc . . GR .
H24B H 0.5935 0.6531 0.7266 0.090 Uiso 1 calc . . GR .
H24C H 0.5471 0.5964 0.7499 0.090 Uiso 1 calc . . GR .
C25 C 0.5556(3) 0.5688(7) 0.5884(3) 0.0583(18) Uani 1 d . . . .
H25A H 0.5281 0.6298 0.5653 0.087 Uiso 1 calc . . GR .
H25B H 0.5508 0.5039 0.5553 0.087 Uiso 1 calc . . GR .
H25C H 0.5932 0.6011 0.6025 0.087 Uiso 1 calc . . GR .
C26 C 0.5933(3) 0.4310(7) 0.6924(4) 0.070(2) Uani 1 d . . . .
H26A H 0.6299 0.4655 0.7021 0.105 Uiso 1 calc . . GR .
H26B H 0.5878 0.3633 0.6610 0.105 Uiso 1 calc . . GR .
H26C H 0.5911 0.4060 0.7370 0.105 Uiso 1 calc . . GR .
C27 C 0.3271(2) 0.5479(6) 0.5290(3) 0.0455(15) Uani 1 d . . . .
C28 C 0.3279(3) 0.6023(7) 0.4589(3) 0.0598(18) Uani 1 d . . . .
H28A H 0.3305 0.5396 0.4277 0.090 Uiso 1 calc . . GR .
H28B H 0.3601 0.6544 0.4704 0.090 Uiso 1 calc . . GR .
H28C H 0.2936 0.6468 0.4348 0.090 Uiso 1 calc . . GR .
C29 C 0.3192(3) 0.6457(7) 0.5780(4) 0.071(2) Uani 1 d . . . .
H29A H 0.2828 0.6829 0.5542 0.106 Uiso 1 calc . . GR .
H29B H 0.3486 0.7045 0.5878 0.106 Uiso 1 calc . . GR .
H29C H 0.3213 0.6109 0.6227 0.106 Uiso 1 calc . . GR .
C30 C 0.2747(3) 0.4660(7) 0.5059(4) 0.074(2) Uani 1 d . . . .
H30A H 0.2814 0.3963 0.4827 0.110 Uiso 1 calc . . GR .
H30B H 0.2422 0.5079 0.4729 0.110 Uiso 1 calc . . GR .
H30C H 0.2677 0.4428 0.5478 0.110 Uiso 1 calc . . GR .
F1 F 0.2202(4) 0.1332(7) 0.7367(7) 0.220(5) Uani 1 d . . . .
F2 F 0.2276(5) 0.2649(13) 0.6804(6) 0.300(9) Uani 1 d . . . U
F3 F 0.2761(3) 0.2530(11) 0.7780(7) 0.249(6) Uani 1 d . . . .
N1 N 0.6347(3) 0.0240(8) 0.5441(4) 0.090(2) Uani 1 d . . . .
O1 O 0.6658(4) -0.0569(11) 0.5665(7) 0.240(7) Uani 1 d . . . U
O2 O 0.6387(2) 0.0910(6) 0.4993(3) 0.0904(18) Uani 1 d . . . .
O3 O 0.4435(2) -0.1413(4) 0.6616(3) 0.0633(13) Uani 1 d . . . .
O4 O 0.44144(18) 0.6478(3) 0.5794(2) 0.0454(10) Uani 1 d . . . .
H4A H 0.4485 0.6883 0.6159 0.068 Uiso 1 calc . . GR .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 121.1(6) . . ?
C3 C2 C1 117.8(6) . . ?
C2 C3 C4 123.3(6) . . ?
C2 C3 N1 118.3(6) . . ?
C4 C3 N1 118.1(6) . . ?
C5 C4 C3 118.1(5) . . ?
C4 C5 C6 121.1(6) . . ?
C1 C6 C5 118.4(5) . . ?
C1 C6 C8 120.0(5) . . ?
C5 C6 C8 121.3(5) . . ?
C8 C7 C11 105.7(5) . . ?
O3 C7 C8 129.9(6) . . ?
O3 C7 C11 124.4(5) . . ?
C6 C8 C7 120.6(5) . . ?
C9 C8 C6 129.8(5) . . ?
C9 C8 C7 109.5(5) . . ?
C8 C9 C10 108.3(5) . . ?
C8 C9 C17 130.0(5) . . ?
C17 C9 C10 121.6(5) . . ?
C11 C10 C9 109.6(5) . . ?
C11 C10 C15 120.0(5) . . ?
C15 C10 C9 130.4(5) . . ?
C10 C11 C7 106.8(5) . . ?
C12 C11 C7 130.8(6) . . ?
C12 C11 C10 122.3(6) . . ?
C11 C12 C13 117.9(6) . . ?
C14 C13 C12 121.5(6) . . ?
C13 C14 C15 120.7(6) . . ?
C13 C14 C16 121.0(6) . . ?
C15 C14 C16 118.3(6) . . ?
C10 C15 C14 117.5(5) . . ?
F1 C16 C14 117.8(8) . . ?
F2 C16 C14 116.7(8) . . ?
F2 C16 F1 102.0(10) . . ?
F3 C16 C14 116.7(8) . . ?
F3 C16 F1 101.4(9) . . ?
F3 C16 F2 99.3(11) . . ?
C18 C17 C9 121.7(5) . . ?
C22 C17 C9 119.8(5) . . ?
C22 C17 C18 118.5(5) . . ?
C19 C18 C17 122.4(5) . . ?
C18 C19 C20 116.5(5) . . ?
C18 C19 C23 121.1(5) . . ?
C20 C19 C23 122.4(5) . . ?
C19 C20 C21 122.7(5) . . ?
O4 C20 C19 118.5(5) . . ?
O4 C20 C21 118.7(5) . . ?
C20 C21 C27 122.6(5) . . ?
C22 C21 C20 117.3(5) . . ?
C22 C21 C27 120.1(5) . . ?
C21 C22 C17 122.6(5) . . ?
C24 C23 C19 110.8(4) . . ?
C24 C23 C25 110.6(5) . . ?
C24 C23 C26 107.4(5) . . ?
C25 C23 C19 110.0(4) . . ?
C26 C23 C19 110.5(5) . . ?
C26 C23 C25 107.5(5) . . ?
C28 C27 C21 111.5(5) . . ?
C28 C27 C30 106.3(5) . . ?
C29 C27 C21 109.5(5) . . ?
C29 C27 C28 110.7(6) . . ?
C29 C27 C30 107.6(5) . . ?
C30 C27 C21 111.2(5) . . ?
O1 N1 C3 117.9(7) . . ?
O1 N1 O2 121.7(7) . . ?
O2 N1 C3 120.3(7) . . ?
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 1.394(8) . ?
C1 C6 1.381(8) . ?
C2 C3 1.362(9) . ?
C3 C4 1.374(8) . ?
C3 N1 1.466(9) . ?
C4 C5 1.372(8) . ?
C5 C6 1.403(8) . ?
C6 C8 1.478(7) . ?
C7 C8 1.503(8) . ?
C7 C11 1.517(8) . ?
C7 O3 1.202(7) . ?
C8 C9 1.350(7) . ?
C9 C10 1.518(7) . ?
C9 C17 1.468(7) . ?
C10 C11 1.382(8) . ?
C10 C15 1.383(8) . ?
C11 C12 1.363(8) . ?
C12 C13 1.391(9) . ?
C13 C14 1.348(9) . ?
C14 C15 1.424(8) . ?
C14 C16 1.441(10) . ?
C16 F1 1.231(9) . ?
C16 F2 1.230(11) . ?
C16 F3 1.224(10) . ?
C17 C18 1.404(7) . ?
C17 C22 1.377(7) . ?
C18 C19 1.392(7) . ?
C19 C20 1.401(7) . ?
C19 C23 1.552(7) . ?
C20 C21 1.418(7) . ?
C20 O4 1.369(6) . ?
C21 C22 1.376(8) . ?
C21 C27 1.553(7) . ?
C23 C24 1.528(8) . ?
C23 C25 1.534(8) . ?
C23 C26 1.529(8) . ?
C27 C28 1.539(8) . ?
C27 C29 1.539(9) . ?
C27 C30 1.539(9) . ?
N1 O1 1.176(10) . ?
N1 O2 1.206(8) . ?
