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
Xia, Shu-Mei; Yang, Zhi-Wen; Yao, Xiang-Yang; Chen, Kai-Hong; Qiu, Li-Qi; He, Liang-Nian; Green Chemistry 23 (2021) 8089–8095; doi:10.1039/D1GC02735B

data_7243508
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -45.00  19.00   1.00    6.00    --    0.10 -77.00-120.00   64
  2  \w    -77.00 -22.00   1.00    6.00    --    0.10 -38.00-120.00   55
  3  \w      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       '\w 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/[\s^2^(Fo^2^)+(0.0424P)^2^+0.4759P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              90366
_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