#------------------------------------------------------------------------------
#$Date: 2022-07-23 01:18:14 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/03/7130367.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_7130367
loop_
_publ_author_name
'Zhao, Shuwen'
'Cai, Xiaojia'
'Lu, Yuying'
'Hu, Jinhui'
'Xiong, Zhuang'
'Jin, Jingwei'
'Li, Yin'
'Wang, Honggen'
'Wu, Jia-Qiang'
_publ_section_title
;
 Cp*Ir(III) and Cp*Rh(III)-catalyzed annulation of salicylaldehydes with
 fluorinated vinyl tosylates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc02194c
_journal_year                    2022
_chemical_formula_moiety         'C11 H6 Cl F3 O3'
_chemical_formula_sum            'C11 H6 Cl F3 O3'
_chemical_formula_weight         278.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-06-07 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.625(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.72550(10)
_cell_length_b                   22.4433(7)
_cell_length_c                   10.8444(3)
_cell_measurement_reflns_used    4377
_cell_measurement_temperature    297.56(10)
_cell_measurement_theta_max      75.1880
_cell_measurement_theta_min      3.9350
_cell_volume                     1146.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.56(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 167.00   0.50    0.88    --  108.86  57.00 -90.00  146
  2  ω    145.00 177.00   0.50    0.88    --  108.86 125.00-150.00   64
  3  ω     96.00 123.00   0.50    0.88    --  108.86 125.00-150.00   54
  4  ω    105.00 130.00   0.50    0.88    --  108.86 140.00  -9.00   50
  5  ω    -62.00 -37.00   0.50    0.88    --  -91.75 140.00  -9.00   50
  6  ω    -73.00 -25.00   0.50    0.22    --  -48.55 140.00  -9.00   96
  7  ω   -115.00 -27.00   0.50    0.22    --  -48.55 -77.00   0.00  176
  8  ω   -163.00 -77.00   0.50    0.88    --  -91.75-130.00 104.00  172
  9  ω   -120.00 -95.00   0.50    0.22    --  -48.55-130.00 104.00   50
 10  ω   -116.00 -91.00   0.50    0.22    --  -48.55-140.00 -69.00   50
 11  ω   -163.00 -91.00   0.50    0.88    --  -91.75 -57.00 -60.00  144
 12  ω    -24.00  24.00   0.50    0.22    --  -48.55  19.00 -60.00   96
 13  ω    -45.00 -20.00   0.50    0.88    --  -91.75  57.00-150.00   50
 14  ω   -104.00 -75.00   0.50    0.88    --  -91.75  77.00   0.00   58
 15  ω    -61.00 -20.00   0.50    0.88    --  -91.75  57.00 -30.00   82
 16  ω    -53.00 -22.00   0.50    0.88    --  -91.75  57.00   0.00   62
 17  ω     38.00  66.00   0.50    0.88    --  108.86 -57.00  60.00   56
 18  ω     63.00  95.00   0.50    0.88    --  108.86 -77.00  90.00   64
 19  ω     40.00  65.00   0.50    0.88    --  108.86 -57.00 150.00   50
 20  ω     47.00  75.00   0.50    0.88    --  108.86-130.00 104.00   56
 21  ω     89.00 114.00   0.50    0.88    --  108.86-130.00 104.00   50
 22  ω     57.00  82.00   0.50    0.22    --   48.55-130.00 104.00   50
 23  ω     57.00 104.00   0.50    0.22    --   48.55-140.00 -69.00   94
 24  ω     94.00 119.00   0.50    0.88    --  108.86-140.00 -69.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137765000
_diffrn_orient_matrix_UB_12      -0.0524852000
_diffrn_orient_matrix_UB_13      -0.0918128000
_diffrn_orient_matrix_UB_21      0.0003276000
_diffrn_orient_matrix_UB_22      0.0441668000
_diffrn_orient_matrix_UB_23      -0.1087404000
_diffrn_orient_matrix_UB_31      0.3268239000
_diffrn_orient_matrix_UB_32      -0.0022551000
_diffrn_orient_matrix_UB_33      0.0076990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.402
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0654
_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)+(0.0996P)²+0.4930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1861
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02194c2.cif
_cod_data_source_block           exp_3268_auto
_cod_database_code               7130367
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F15B(0.5) F15A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.545
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl18 Cl 0.8917(2) 0.23215(5) 0.60094(10) 0.1014(4) Uani 1 1 d . . . . .
O10 O 0.5781(4) 0.42459(9) 0.25401(17) 0.0654(5) Uani 1 1 d . . . . .
O11 O 0.3674(4) 0.50458(10) 0.18868(18) 0.0716(6) Uani 1 1 d . . . . .
O17 O 0.2058(5) 0.42262(10) 0.57997(19) 0.0729(6) Uani 1 1 d . . . . .
F16 F 0.0950(6) 0.64624(13) 0.1099(3) 0.1250(10) Uani 1 1 d . . . . .
C4 C 0.5196(5) 0.37700(12) 0.4494(2) 0.0541(6) Uani 1 1 d . . . . .
F14 F 0.1368(9) 0.57343(19) -0.0093(3) 0.1644(15) Uani 1 1 d . . . . .
C1 C 0.3892(5) 0.46632(13) 0.2823(2) 0.0575(6) Uani 1 1 d . . . . .
C3 C 0.3137(6) 0.42307(12) 0.4804(2) 0.0566(6) Uani 1 1 d . . . . .
C9 C 0.6418(5) 0.37961(12) 0.3378(2) 0.0571(6) Uani 1 1 d . . . . .
C2 C 0.2543(6) 0.46736(12) 0.3863(2) 0.0574(6) Uani 1 1 d . . . . .
H2 H 0.121181 0.496974 0.397625 0.069 Uiso 1 1 calc R U . . .
C5 C 0.5952(6) 0.33033(13) 0.5304(3) 0.0625(7) Uani 1 1 d . . . . .
H5 H 0.514448 0.327326 0.605534 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8355(6) 0.33748(14) 0.3050(3) 0.0673(7) Uani 1 1 d . . . . .
H8 H 0.914357 0.339942 0.229306 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7893(6) 0.28900(14) 0.4983(3) 0.0676(7) Uani 1 1 d . . . . .
F15B F 0.4848(9) 0.5981(2) 0.0601(4) 0.0909(11) Uiso 0.5 1 d . . P A 2
C7 C 0.9097(6) 0.29189(15) 0.3858(3) 0.0712(8) Uani 1 1 d . . . . .
H7 H 1.039822 0.263167 0.365344 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1869(7) 0.55488(15) 0.2015(3) 0.0713(8) Uani 1 1 d . . . . .
H12A H 0.234383 0.574618 0.279988 0.086 Uiso 1 1 calc R U . . .
H12B H -0.010240 0.542464 0.197973 0.086 Uiso 1 1 calc R U . . .
C13 C 0.2333(8) 0.5955(2) 0.0978(4) 0.0914(12) Uani 1 1 d . . . . .
F15A F 0.5093(10) 0.6199(2) 0.1244(5) 0.1036(13) Uiso 0.5 1 d . . P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O10 C9 118.3(2) . . ?
C1 O11 C12 116.6(2) . . ?
C9 C4 C3 119.9(2) . . ?
C9 C4 C5 118.6(2) . . ?
C5 C4 C3 121.5(2) . . ?
O11 C1 O10 106.7(2) . . ?
O11 C1 C2 128.3(3) . . ?
C2 C1 O10 125.0(2) . . ?
O17 C3 C4 121.4(2) . . ?
O17 C3 C2 123.9(3) . . ?
C2 C3 C4 114.7(2) . . ?
O10 C9 C4 121.6(2) . . ?
O10 C9 C8 116.5(2) . . ?
C8 C9 C4 121.9(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C9 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C5 C6 Cl18 119.5(2) . . ?
C5 C6 C7 121.5(3) . . ?
C7 C6 Cl18 119.0(2) . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
O11 C12 H12A 110.4 . . ?
O11 C12 H12B 110.4 . . ?
O11 C12 C13 106.7(3) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
F16 C13 C12 110.5(3) . . ?
F16 C13 F15A 95.7(4) . . ?
F14 C13 F16 105.8(3) . . ?
F14 C13 C12 112.3(4) . . ?
F14 C13 F15A 125.0(4) . . ?
F15B C13 F16 117.8(4) . . ?
F15B C13 F14 90.0(4) . . ?
F15B C13 C12 117.9(3) . . ?
F15A C13 C12 105.9(4) . . ?
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
Cl18 C6 1.736(3) . ?
O10 C1 1.346(3) . ?
O10 C9 1.376(3) . ?
O11 C1 1.328(3) . ?
O11 C12 1.428(4) . ?
O17 C3 1.231(3) . ?
F16 C13 1.326(5) . ?
C4 C3 1.477(4) . ?
C4 C9 1.383(4) . ?
C4 C5 1.395(4) . ?
F14 C13 1.310(6) . ?
C1 C2 1.340(4) . ?
C3 C2 1.436(4) . ?
C9 C8 1.382(4) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.369(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.374(5) . ?
C6 C7 1.388(5) . ?
F15B C13 1.289(6) . ?
C7 H7 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.477(5) . ?
C13 F15A 1.423(7) . ?
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
Cl18 C6 C7 C8 -178.5(2) . . . . ?
O10 C1 C2 C3 2.4(4) . . . . ?
O10 C9 C8 C7 179.2(2) . . . . ?
O11 C1 C2 C3 -177.5(3) . . . . ?
O11 C12 C13 F16 -173.6(3) . . . . ?
O11 C12 C13 F14 68.5(4) . . . . ?
O11 C12 C13 F15B -34.0(6) . . . . ?
O11 C12 C13 F15A -71.1(4) . . . . ?
O17 C3 C2 C1 177.1(3) . . . . ?
C4 C3 C2 C1 -2.5(4) . . . . ?
C4 C9 C8 C7 -0.4(4) . . . . ?
C4 C5 C6 Cl18 178.1(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C1 O10 C9 C4 -0.7(4) . . . . ?
C1 O10 C9 C8 179.7(2) . . . . ?
C1 O11 C12 C13 170.7(3) . . . . ?
C3 C4 C9 O10 0.4(4) . . . . ?
C3 C4 C9 C8 180.0(2) . . . . ?
C3 C4 C5 C6 -179.3(3) . . . . ?
C9 O10 C1 O11 179.2(2) . . . . ?
C9 O10 C1 C2 -0.7(4) . . . . ?
C9 C4 C3 O17 -178.5(3) . . . . ?
C9 C4 C3 C2 1.2(4) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C5 C4 C3 O17 1.5(4) . . . . ?
C5 C4 C3 C2 -178.8(2) . . . . ?
C5 C4 C9 O10 -179.6(2) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C12 O11 C1 O10 -177.0(2) . . . . ?
C12 O11 C1 C2 3.0(4) . . . . ?
