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#$Date: 2024-08-05 23:00:47 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160034.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_7160034
loop_
_publ_author_name
'Prasanna, Ram'
'Banik, Swarnayu'
'Ajay, Chidrawar'
'Sridhar, B.'
'Mohapatra, Debendra K.'
'Subba Reddy, B. V.'
_publ_section_title
;
 Catalyst-free photoarylation of 2-aryl-2H-indazoles by
 carbon-iodine bond activation.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6129
_journal_page_last               6134
_journal_paper_doi               10.1039/d4ob00820k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_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
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-12-05 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.449(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.420(3)
_cell_length_b                   9.1758(11)
_cell_length_c                   13.2477(17)
_cell_measurement_reflns_used    6299
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.6905
_cell_measurement_theta_min      2.373
_cell_volume                     2949.7(6)
_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 0.991
_diffrn_measured_fraction_theta_max 0.965
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17945
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.494
_diffrn_reflns_theta_min         2.373
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6624
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_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     201
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0511
_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)+(0.0786P)²+1.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2319
_reflns_number_total             4331
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00820k2.cif
_cod_data_source_block           KB824_0m
_cod_depositor_comments          'Adding full bibliography for 7160034.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160034
_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   0.976
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_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 0.27183(8) 0.4976(2) 0.41946(15) 0.0657(5) Uani 1 1 d . . . . .
H1 H 0.284459 0.494582 0.355827 0.079 Uiso 1 1 calc R U . . .
C2 C 0.22614(8) 0.5801(2) 0.43324(18) 0.0761(6) Uani 1 1 d . . . . .
H2 H 0.207885 0.631220 0.378904 0.091 Uiso 1 1 calc R U . . .
C3 C 0.20731(9) 0.5869(2) 0.5283(2) 0.0771(6) Uani 1 1 d . . . . .
H3 H 0.177178 0.645260 0.537845 0.093 Uiso 1 1 calc R U . . .
C4 C 0.23288(8) 0.5082(2) 0.60799(17) 0.0694(5) Uani 1 1 d . . . . .
H4 H 0.220138 0.512495 0.671484 0.083 Uiso 1 1 calc R U . . .
C5 C 0.27776(7) 0.42244(19) 0.59313(13) 0.0556(4) Uani 1 1 d . . . . .
C6 C 0.29958(7) 0.41826(17) 0.49990(13) 0.0526(4) Uani 1 1 d . . . . .
C7 C 0.34873(7) 0.33119(16) 0.49229(12) 0.0484(4) Uani 1 1 d . . . . .
C8 C 0.36877(7) 0.25037(17) 0.57438(12) 0.0498(4) Uani 1 1 d . . . . .
C9 C 0.34340(7) 0.24899(19) 0.66868(13) 0.0547(4) Uani 1 1 d . . . . .
C10 C 0.41929(7) 0.15862(17) 0.57739(12) 0.0511(4) Uani 1 1 d . . . . .
C11 C 0.51560(8) 0.1523(3) 0.61972(18) 0.0789(6) Uani 1 1 d . . . . .
H11A H 0.524755 0.127414 0.553247 0.118 Uiso 1 1 calc R U . . .
H11B H 0.511603 0.064797 0.657957 0.118 Uiso 1 1 calc R U . . .
H11C H 0.544438 0.211109 0.653981 0.118 Uiso 1 1 calc R U . . .
C12 C 0.37564(7) 0.33275(16) 0.39669(12) 0.0492(4) Uani 1 1 d . . . . .
C13 C 0.39330(8) 0.46278(18) 0.35704(12) 0.0561(4) Uani 1 1 d . . . . .
H13 H 0.389053 0.549774 0.391332 0.067 Uiso 1 1 calc R U . . .
C14 C 0.41710(8) 0.46388(19) 0.26714(13) 0.0592(4) Uani 1 1 d . . . . .
H14 H 0.429486 0.551537 0.242739 0.071 Uiso 1 1 calc R U . . .
C15 C 0.42285(7) 0.33706(19) 0.21277(12) 0.0562(4) Uani 1 1 d . . . . .
C16 C 0.40561(8) 0.2074(2) 0.25292(13) 0.0610(5) Uani 1 1 d . . . . .
H16 H 0.409408 0.120748 0.217956 0.073 Uiso 1 1 calc R U . . .
C17 C 0.38287(8) 0.20459(18) 0.34404(13) 0.0560(4) Uani 1 1 d . . . . .
H17 H 0.372353 0.116138 0.370202 0.067 Uiso 1 1 calc R U . . .
C18 C 0.44707(10) 0.3395(2) 0.11270(14) 0.0768(6) Uani 1 1 d . . . . .
H18A H 0.420373 0.303417 0.059903 0.115 Uiso 1 1 calc R U . . .
H18B H 0.479336 0.279068 0.117433 0.115 Uiso 1 1 calc R U . . .
H18C H 0.456878 0.437675 0.097204 0.115 Uiso 1 1 calc R U . . .
O1 O 0.29948(5) 0.33949(13) 0.67451(9) 0.0619(3) Uani 1 1 d . . . . .
O2 O 0.35903(6) 0.17651(15) 0.74244(10) 0.0716(4) Uani 1 1 d . . . . .
O3 O 0.41954(6) 0.03188(14) 0.55482(12) 0.0757(4) Uani 1 1 d . . . . .
O4 O 0.46428(5) 0.23306(14) 0.61060(10) 0.0658(4) 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
C2 C1 C6 120.97(19) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.38(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.38(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O1 C5 C4 116.46(16) . . ?
O1 C5 C6 121.64(15) . . ?
C4 C5 C6 121.89(18) . . ?
C5 C6 C1 117.22(16) . . ?
C5 C6 C7 118.37(15) . . ?
C1 C6 C7 124.41(16) . . ?
C8 C7 C6 117.98(15) . . ?
C8 C7 C12 122.06(15) . . ?
C6 C7 C12 119.96(14) . . ?
C7 C8 C9 122.76(16) . . ?
C7 C8 C10 123.46(14) . . ?
C9 C8 C10 113.76(14) . . ?
O2 C9 O1 117.89(15) . . ?
O2 C9 C8 124.95(17) . . ?
O1 C9 C8 117.13(15) . . ?
O3 C10 O4 123.65(16) . . ?
O3 C10 C8 124.58(16) . . ?
O4 C10 C8 111.74(14) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.31(15) . . ?
C17 C12 C7 120.78(14) . . ?
C13 C12 C7 120.91(13) . . ?
C14 C13 C12 120.63(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.28(16) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 117.93(16) . . ?
C14 C15 C18 121.10(16) . . ?
C16 C15 C18 120.97(16) . . ?
C17 C16 C15 121.25(16) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 120.55(15) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 O1 C5 121.87(13) . . ?
C10 O4 C11 116.15(15) . . ?
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 1.377(3) . ?
C1 C6 1.401(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 O1 1.376(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.455(2) . ?
C7 C8 1.361(2) . ?
C7 C12 1.491(2) . ?
C8 C9 1.455(2) . ?
C8 C10 1.491(2) . ?
C9 O2 1.208(2) . ?
C9 O1 1.366(2) . ?
C10 O3 1.201(2) . ?
C10 O4 1.326(2) . ?
C11 O4 1.449(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.389(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 C18 1.511(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 0.8(3) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 O1 -176.23(16) . . . . ?
C3 C4 C5 C6 2.9(3) . . . . ?
O1 C5 C6 C1 174.98(15) . . . . ?
C4 C5 C6 C1 -4.1(2) . . . . ?
O1 C5 C6 C7 -4.3(2) . . . . ?
C4 C5 C6 C7 176.69(16) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C1 C6 C7 -178.61(17) . . . . ?
C5 C6 C7 C8 4.4(2) . . . . ?
C1 C6 C7 C8 -174.79(16) . . . . ?
C5 C6 C7 C12 -175.44(14) . . . . ?
C1 C6 C7 C12 5.4(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C12 C7 C8 C9 179.24(14) . . . . ?
C6 C7 C8 C10 -178.86(14) . . . . ?
C12 C7 C8 C10 1.0(2) . . . . ?
C7 C8 C9 O2 178.24(17) . . . . ?
C10 C8 C9 O2 -3.3(2) . . . . ?
C7 C8 C9 O1 -3.5(2) . . . . ?
C10 C8 C9 O1 174.93(13) . . . . ?
C7 C8 C10 O3 -92.3(2) . . . . ?
C9 C8 C10 O3 89.3(2) . . . . ?
C7 C8 C10 O4 89.28(19) . . . . ?
C9 C8 C10 O4 -89.13(17) . . . . ?
C8 C7 C12 C17 58.0(2) . . . . ?
C6 C7 C12 C17 -122.22(17) . . . . ?
C8 C7 C12 C13 -123.12(18) . . . . ?
C6 C7 C12 C13 56.7(2) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C7 C12 C13 C14 -178.54(16) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C13 C14 C15 C18 177.84(17) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C18 C15 C16 C17 -179.33(17) . . . . ?
C15 C16 C17 C12 1.4(3) . . . . ?
C13 C12 C17 C16 -1.9(3) . . . . ?
C7 C12 C17 C16 177.07(16) . . . . ?
O2 C9 O1 C5 -177.83(15) . . . . ?
C8 C9 O1 C5 3.8(2) . . . . ?
C4 C5 O1 C9 179.15(15) . . . . ?
C6 C5 O1 C9 0.1(2) . . . . ?
O3 C10 O4 C11 -0.5(2) . . . . ?
C8 C10 O4 C11 177.97(15) . . . . ?
