#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:11:12 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291044 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159843.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_7159843
loop_
_publ_author_name
'Kumar, Madan'
'Goswami, Avijit'
_publ_section_title
;
 Synthesis of trifluoroethoxy/aryloxy cinnolines, cinnolinones and
 indazoles from o-alkynylanilines via metal-free
 diazotization reagent.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2608
_journal_page_last               2619
_journal_paper_doi               10.1039/d4ob00058g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H10 Cl F3 N2 O'
_chemical_formula_sum            'C16 H10 Cl F3 N2 O'
_chemical_formula_weight         338.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.347(2)
_cell_length_b                   7.581(2)
_cell_length_c                   29.868(3)
_cell_measurement_reflns_used    312
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      3.34
_cell_volume                     3022.2(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            60482
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.721
_diffrn_reflns_theta_min         3.126
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4399
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0931 after correction.
The Ratio of minimum to maximum transmission is 0.5902.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0530
_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)+(0.0577P)²+1.6984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2361
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00058g2.cif
_cod_data_source_block           agmk_442b_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7159839--7159843.cif.'
_cod_original_cell_volume        3022.0(10)
_cod_database_code               7159843
_shelx_shelxl_version_number     2019/1
_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_max   0.984
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C15(H15), C14(H14), C5(H5), C13(H13), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Cl1 Cl 0.61841(9) 0.91824(14) 0.53057(3) 0.1127(4) Uani 1 1 d . . . . .
O1 O 0.52970(10) 0.7291(2) 0.36371(5) 0.0540(4) Uani 1 1 d . . . . .
F1 F 0.43720(14) 0.5278(3) 0.42864(5) 0.0969(6) Uani 1 1 d . . . . .
F2 F 0.33682(13) 0.6810(3) 0.39002(8) 0.1176(8) Uani 1 1 d . . . . .
F3 F 0.34475(14) 0.4028(3) 0.37966(6) 0.1052(7) Uani 1 1 d . . . . .
N1 N 0.79324(14) 0.6811(3) 0.33093(7) 0.0639(6) Uani 1 1 d . . . . .
C7 C 0.7850(3) 0.8577(4) 0.48196(11) 0.0894(10) Uani 1 1 d . . . . .
H7 H 0.819473 0.887221 0.507972 0.107 Uiso 1 1 calc R U . . .
C8 C 0.8361(2) 0.8115(4) 0.44470(11) 0.0839(9) Uani 1 1 d . . . . .
H8 H 0.905797 0.808687 0.445214 0.101 Uiso 1 1 calc R U . . .
C9 C 0.78434(18) 0.7676(3) 0.40488(9) 0.0619(6) Uani 1 1 d . . . . .
C4 C 0.67855(17) 0.7719(3) 0.40470(8) 0.0525(5) Uani 1 1 d . . . . .
C3 C 0.63239(15) 0.7245(3) 0.36422(7) 0.0463(5) Uani 1 1 d . . . . .
C10 C 0.69085(15) 0.6843(3) 0.32749(7) 0.0489(5) Uani 1 1 d . . . . .
C11 C 0.65347(16) 0.6458(3) 0.28180(7) 0.0488(5) Uani 1 1 d . . . . .
C16 C 0.56761(17) 0.7252(3) 0.26476(8) 0.0553(6) Uani 1 1 d . . . . .
H16 H 0.530765 0.801537 0.282748 0.066 Uiso 1 1 calc R U . . .
C15 C 0.5363(2) 0.6922(4) 0.22139(9) 0.0729(8) Uani 1 1 d . . . . .
H15 H 0.478315 0.745316 0.210627 0.088 Uiso 1 1 calc R U . . .
C14 C 0.5901(3) 0.5819(4) 0.19425(10) 0.0862(10) Uani 1 1 d . . . . .
H14 H 0.568858 0.559914 0.165125 0.103 Uiso 1 1 calc R U . . .
C6 C 0.6799(3) 0.8608(4) 0.48133(9) 0.0755(8) Uani 1 1 d . . . . .
C5 C 0.6264(2) 0.8194(3) 0.44417(8) 0.0627(6) Uani 1 1 d . . . . .
H5 H 0.556751 0.822236 0.444614 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6756(3) 0.5041(4) 0.21040(10) 0.0868(10) Uani 1 1 d . . . . .
H13 H 0.712566 0.429848 0.191923 0.104 Uiso 1 1 calc R U . . .
C12 C 0.7074(2) 0.5344(3) 0.25369(9) 0.0667(7) Uani 1 1 d . . . . .
H12 H 0.765318 0.479957 0.264140 0.080 Uiso 1 1 calc R U . . .
N2 N 0.83902(15) 0.7209(3) 0.36826(8) 0.0731(6) Uani 1 1 d . . . . .
C2 C 0.47799(16) 0.5694(3) 0.35336(8) 0.0572(6) Uani 1 1 d . . . . .
H2A H 0.523910 0.470281 0.354116 0.069 Uiso 1 1 calc R U . . .
H2B H 0.448718 0.576376 0.323685 0.069 Uiso 1 1 calc R U . . .
C1 C 0.39824(18) 0.5467(4) 0.38761(9) 0.0675(7) 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'
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
C3 O1 C2 117.65(17) . . ?
N2 N1 C10 121.7(2) . . ?
C8 C7 H7 120.1 . . ?
C8 C7 C6 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 119.1(3) . . ?
N2 C9 C8 118.3(2) . . ?
N2 C9 C4 122.6(2) . . ?
C9 C4 C5 119.6(2) . . ?
C3 C4 C9 115.8(2) . . ?
C3 C4 C5 124.5(2) . . ?
O1 C3 C4 116.21(19) . . ?
O1 C3 C10 124.19(19) . . ?
C10 C3 C4 119.5(2) . . ?
N1 C10 C3 120.5(2) . . ?
N1 C10 C11 113.6(2) . . ?
C3 C10 C11 125.81(19) . . ?
C16 C11 C10 121.9(2) . . ?
C16 C11 C12 117.9(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C7 C6 Cl1 117.7(2) . . ?
C5 C6 Cl1 120.1(3) . . ?
C5 C6 C7 122.2(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
N1 N2 C9 119.6(2) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
O1 C2 C1 107.17(19) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
F1 C1 C2 111.4(2) . . ?
F2 C1 F1 106.0(2) . . ?
F2 C1 F3 108.2(2) . . ?
F2 C1 C2 113.3(2) . . ?
F3 C1 F1 106.6(2) . . ?
F3 C1 C2 111.0(2) . . ?
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
Cl1 C6 1.739(3) . ?
O1 C3 1.371(2) . ?
O1 C2 1.427(3) . ?
F1 C1 1.339(3) . ?
F2 C1 1.309(3) . ?
F3 C1 1.325(3) . ?
N1 C10 1.371(3) . ?
N1 N2 1.307(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(5) . ?
C7 C6 1.404(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.416(4) . ?
C9 C4 1.412(3) . ?
C9 N2 1.361(4) . ?
C4 C3 1.404(3) . ?
C4 C5 1.416(3) . ?
C3 C10 1.380(3) . ?
C10 C11 1.482(3) . ?
C11 C16 1.391(3) . ?
C11 C12 1.392(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.367(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.372(5) . ?
C6 C5 1.356(3) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.380(4) . ?
C12 H12 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.486(3) . ?
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
Cl1 C6 C5 C4 -179.51(18) . . . . ?
O1 C3 C10 N1 -179.4(2) . . . . ?
O1 C3 C10 C11 2.1(3) . . . . ?
O1 C2 C1 F1 -63.1(3) . . . . ?
O1 C2 C1 F2 56.4(3) . . . . ?
O1 C2 C1 F3 178.4(2) . . . . ?
N1 C10 C11 C16 -146.0(2) . . . . ?
N1 C10 C11 C12 30.6(3) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C7 C8 C9 N2 -179.6(3) . . . . ?
C7 C6 C5 C4 -0.2(4) . . . . ?
C8 C7 C6 Cl1 179.1(2) . . . . ?
C8 C7 C6 C5 -0.3(5) . . . . ?
C8 C9 C4 C3 -179.2(2) . . . . ?
C8 C9 C4 C5 -0.2(3) . . . . ?
C8 C9 N2 N1 -179.4(2) . . . . ?
C9 C4 C3 O1 -179.73(19) . . . . ?
C9 C4 C3 C10 -2.5(3) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C4 C9 N2 N1 1.3(4) . . . . ?
C4 C3 C10 N1 3.5(3) . . . . ?
C4 C3 C10 C11 -174.94(19) . . . . ?
C3 O1 C2 C1 132.2(2) . . . . ?
C3 C4 C5 C6 179.3(2) . . . . ?
C3 C10 C11 C16 32.6(3) . . . . ?
C3 C10 C11 C12 -150.8(2) . . . . ?
C10 N1 N2 C9 -0.3(4) . . . . ?
C10 C11 C16 C15 177.6(2) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C11 C16 C15 C14 -0.7(4) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C15 C14 C13 C12 0.6(4) . . . . ?
C14 C13 C12 C11 -0.4(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C5 C4 C3 O1 1.3(3) . . . . ?
C5 C4 C3 C10 178.5(2) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
N2 N1 C10 C3 -2.2(3) . . . . ?
N2 N1 C10 C11 176.5(2) . . . . ?
N2 C9 C4 C3 0.1(3) . . . . ?
N2 C9 C4 C5 179.2(2) . . . . ?
C2 O1 C3 C4 -121.1(2) . . . . ?
C2 O1 C3 C10 61.7(3) . . . . ?
