#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:13:08 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243508.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_7243508
loop_
_publ_author_name
'Xia, Shu-Mei'
'Yang, Zhi-Wen'
'Yao, Xiang-Yang'
'Chen, Kai-Hong'
'Qiu, Li-Qi'
'He, Liang-Nian'
_publ_section_title
;
 The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes
 with formic acid as a CO surrogate as well as a hydrogen source: an
 alternative indirect utilization of CO2
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8089
_journal_page_last               8095
_journal_paper_doi               10.1039/D1GC02735B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C17 H10 F6 O2'
_chemical_formula_sum            'C17 H10 F6 O2'
_chemical_formula_weight         360.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-08 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.429(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5094(3)
_cell_length_b                   15.2120(8)
_cell_length_c                   18.2863(9)
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.3280
_cell_measurement_theta_min      3.6760
_cell_volume                     1522.92(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  19.00   1.00    6.00    --    0.10 -77.00-120.00   64
  2  ω    -77.00 -22.00   1.00    6.00    --    0.10 -38.00-120.00   55
  3  ω      1.00  61.00   1.00    6.00    --    0.10  57.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0864257000
_diffrn_orient_matrix_UB_12      -0.0301265000
_diffrn_orient_matrix_UB_13      0.0116304000
_diffrn_orient_matrix_UB_21      -0.0241230000
_diffrn_orient_matrix_UB_22      -0.0160504000
_diffrn_orient_matrix_UB_23      -0.0364987000
_diffrn_orient_matrix_UB_31      0.0934654000
_diffrn_orient_matrix_UB_32      -0.0317846000
_diffrn_orient_matrix_UB_33      0.0074562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10535
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.389
_diffrn_reflns_theta_min         3.621
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0404
_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)+(0.0424P)²+0.4759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3229
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc02735b2.cif
_cod_data_source_block           2010227289-1
_cod_depositor_comments
'Adding full bibliography for 7243507--7243508.cif.'
_cod_database_code               7243508
_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.
;
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N)
2.b Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.842
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.4261(2) 0.45111(6) 0.68098(5) 0.0443(3) Uani 1 1 d . . . . .
F2 F 0.3522(2) 0.52818(6) 0.58277(6) 0.0475(3) Uani 1 1 d . . . . .
F3 F 0.7207(2) 0.49500(7) 0.62282(6) 0.0500(3) Uani 1 1 d . . . . .
F4 F 1.28755(17) 0.38688(6) 0.25230(5) 0.0325(2) Uani 1 1 d . . . . .
F5 F 0.99128(18) 0.37637(8) 0.16781(5) 0.0461(3) Uani 1 1 d . . . . .
F6 F 1.2811(2) 0.28098(7) 0.17556(6) 0.0475(3) Uani 1 1 d . . . . .
O1 O 0.11012(17) 0.09659(6) 0.51633(5) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.24406(17) -0.00042(6) 0.43813(5) 0.0212(2) Uani 1 1 d . . . . .
H004 H 0.133223 -0.030326 0.451440 0.032 Uiso 1 1 calc GR . . . .
C1 C 0.2463(2) 0.07701(8) 0.47041(6) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.4238(2) 0.14157(8) 0.44582(6) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.5504(2) 0.12025(8) 0.38962(7) 0.0169(2) Uani 1 1 d . . . . .
H00D H 0.534319 0.062327 0.373549 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7109(2) 0.17593(8) 0.35002(6) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.6894(2) 0.26766(9) 0.34627(7) 0.0198(3) Uani 1 1 d . . . . .
H00H H 0.578584 0.296181 0.372902 0.024 Uiso 1 1 calc R . . . .
C6 C 0.8317(2) 0.31618(9) 0.30325(7) 0.0208(3) Uani 1 1 d . . . . .
H00G H 0.815010 0.376973 0.300700 0.025 Uiso 1 1 calc R . . . .
C7 C 0.9998(2) 0.27412(9) 0.26383(6) 0.0186(2) Uani 1 1 d . . . . .
C8 C 1.0266(2) 0.18359(9) 0.26766(7) 0.0212(3) Uani 1 1 d . . . . .
H00M H 1.141409 0.155621 0.242157 0.025 Uiso 1 1 calc R . . . .
C9 C 0.8805(2) 0.13492(9) 0.30990(7) 0.0197(2) Uani 1 1 d . . . . .
H00I H 0.895866 0.074043 0.311500 0.024 Uiso 1 1 calc R . . . .
C10 C 1.1407(2) 0.32856(9) 0.21497(7) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.4409(2) 0.22580(8) 0.48744(6) 0.0153(2) Uani 1 1 d . . . . .
C12 C 0.6514(2) 0.24462(8) 0.53423(7) 0.0187(2) Uani 1 1 d . . . . .
H00A H 0.781425 0.205296 0.538280 0.022 Uiso 1 1 calc R . . . .
C13 C 0.6679(2) 0.32195(9) 0.57491(7) 0.0221(3) Uani 1 1 d . . . . .
H00K H 0.808062 0.334212 0.606487 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4740(3) 0.38087(8) 0.56820(7) 0.0220(3) Uani 1 1 d . . . . .
C15 C 0.2642(2) 0.36319(9) 0.52167(8) 0.0241(3) Uani 1 1 d . . . . .
H00N H 0.135592 0.403126 0.517119 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2472(2) 0.28542(9) 0.48186(7) 0.0206(3) Uani 1 1 d . . . . .
H00J H 0.105239 0.272868 0.451138 0.025 Uiso 1 1 calc R . . . .
C17 C 0.4932(3) 0.46349(9) 0.61324(8) 0.0310(3) 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'
F F 0.0171 0.0103 '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
O1 C1 O2 123.32(11) . . ?
O1 C1 C2 121.33(11) . . ?
O2 C1 C2 115.33(10) . . ?
C3 C2 C1 119.05(11) . . ?
C3 C2 C11 126.15(11) . . ?
C11 C2 C1 114.79(10) . . ?
C2 C3 C4 128.96(11) . . ?
C5 C4 C3 123.01(11) . . ?
C9 C4 C3 118.36(11) . . ?
C9 C4 C5 118.46(11) . . ?
C6 C5 C4 120.56(12) . . ?
C5 C6 C7 120.09(12) . . ?
C6 C7 C10 118.32(12) . . ?
C8 C7 C6 120.27(12) . . ?
C8 C7 C10 121.35(12) . . ?
C7 C8 C9 119.50(12) . . ?
C8 C9 C4 121.10(12) . . ?
F4 C10 F5 105.19(12) . . ?
F4 C10 C7 112.78(10) . . ?
F5 C10 C7 111.24(11) . . ?
F6 C10 F4 106.45(11) . . ?
F6 C10 F5 107.45(11) . . ?
F6 C10 C7 113.23(12) . . ?
C12 C11 C2 119.49(11) . . ?
C12 C11 C16 119.29(11) . . ?
C16 C11 C2 121.20(11) . . ?
C13 C12 C11 120.23(12) . . ?
C14 C13 C12 119.70(12) . . ?
C13 C14 C17 119.08(13) . . ?
C15 C14 C13 120.69(12) . . ?
C15 C14 C17 120.23(13) . . ?
C14 C15 C16 119.45(12) . . ?
C15 C16 C11 120.64(12) . . ?
F1 C17 C14 112.25(11) . . ?
F2 C17 F1 106.26(12) . . ?
F2 C17 C14 112.72(13) . . ?
F3 C17 F1 106.28(14) . . ?
F3 C17 F2 106.49(12) . . ?
F3 C17 C14 112.35(12) . . ?
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
F1 C17 1.3450(17) . ?
F2 C17 1.336(2) . ?
F3 C17 1.3348(19) . ?
F4 C10 1.3356(16) . ?
F5 C10 1.3385(17) . ?
F6 C10 1.3288(16) . ?
O1 C1 1.2241(15) . ?
O2 C1 1.3168(15) . ?
C2 C1 1.4902(16) . ?
C2 C3 1.3447(17) . ?
C4 C3 1.4722(16) . ?
C4 C5 1.4014(18) . ?
C4 C9 1.3979(17) . ?
C6 C5 1.3844(18) . ?
C7 C6 1.3912(18) . ?
C7 C8 1.3859(19) . ?
C7 C10 1.4975(17) . ?
C9 C8 1.3898(18) . ?
C11 C2 1.4879(16) . ?
C11 C12 1.3915(17) . ?
C11 C16 1.3956(17) . ?
C12 C13 1.3894(18) . ?
C13 C14 1.3889(19) . ?
C14 C15 1.383(2) . ?
C14 C17 1.4999(18) . ?
C16 C15 1.3868(19) . ?
