M-CPOnes: transition metal complexes with cyclopropenone-based ligands for light-triggered carbon monoxide release
Lehr, Marc; Neumann, Tjorge; Näther, Christian; McConnell, Anna J.; Dalton Transactions  (2022) –; doi:10.1039/D2DT00835A

data_7710099
_publ_section_title
;
 M-CPOnes: transition metal complexes with cyclopropenone-based ligands
 for light-triggered carbon monoxide release
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00835A
_journal_year                    2022
_chemical_formula_moiety         'C19 H12 F2 N2'
_chemical_formula_sum            'C19 H12 F2 N2'
_chemical_formula_weight         306.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                82.2840(10)
_cell_angle_beta                 84.2680(10)
_cell_angle_gamma                77.2190(10)
_cell_formula_units_Z            2
_cell_length_a                   6.91900(10)
_cell_length_b                   8.13080(10)
_cell_length_c                   13.4122(2)
_cell_measurement_reflns_used    12656
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.5000
_cell_measurement_theta_min      3.3250
_cell_volume                     727.248(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-1997 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.980
_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    -72.00 -25.00   0.50    2.00    --  -47.54 -77.00 -90.00   94
  2  \w    -59.00 -25.00   0.50    2.00    --  -47.54 -77.00 -30.00   68
  3  \w    -70.00 -25.00   0.50    2.00    --  -47.54 -77.00  30.00   90
  4  \w    -74.00 -34.00   0.50    2.00    --  -47.54 -38.00-150.00   80
  5  \w    -71.00 -30.00   0.50    2.00    --  -47.54 -63.00  53.00   82
  6  \w    -59.00 -25.00   0.50    2.00    --  -47.54 -77.00  90.00   68
  7  \w   -116.00 -80.00   0.50    2.00    --  -47.54 -77.00  30.00   72
  8  \w   -116.00 -89.00   0.50    2.00    --  -47.54 -77.00  90.00   54
  9  \w    -61.00 -26.00   0.50    2.00    --  -47.54 -77.00-180.00   70
 10  \w    -67.00 -33.00   0.50    2.00    --  -47.54 -57.00 120.00   68
 11  \w    -77.00 -35.00   0.50    2.00    --  -47.54 -19.00-120.00   84
 12  \w    -73.00 -27.00   0.50    2.00    --  -47.54 -77.00-150.00   92
 13  \w    -59.00 -34.00   0.50    2.00    --  -47.54 -57.00-150.00   50
 14  \w   -118.00 -65.00   0.50    2.00    --  -47.54 -77.00-180.00  106
 15  \w   -118.00 -93.00   0.50    2.00    --  -47.54 -57.00 120.00   50
 16  \w     35.00  90.00   0.50    2.00    --   47.54-125.00-150.00  110
 17  \w     37.00  90.00   0.50    2.00    --   47.54-125.00  30.00  106
 18  \w     26.00  62.00   0.50    2.00    --   47.54  77.00-180.00   72
 19  \w     27.00  53.00   0.50    2.00    --   47.54  77.00  30.00   52
 20  \w     42.00  94.00   0.50    2.00    --   47.54-125.00 -60.00  104
 21  \w     52.00 122.00   0.50    2.00    --   47.54  19.00   0.00  140
 22  \w    -99.00 -70.00   0.50    6.00    --  -87.75 -63.00 -60.91   58
 23  \w    -92.00 -66.00   0.50    6.00    --  -87.75 -74.00 172.05   52
 24  \w    -91.00 -65.00   0.50    6.00    --  -87.75 -76.00   1.51   52
 25  \w    -95.00 -69.00   0.50    6.00    --  -87.75 -68.00-176.49   52
 26  \w   -160.00-131.00   0.50    6.00    --  -87.75 -72.00-114.09   58
 27  \w   -157.00-131.00   0.50    6.00    --  -87.75 -68.00-176.49   52
 28  \w   -104.00 -66.00   0.50    6.00    --  -87.75 -75.00-124.92   76
 29  \w   -157.00-132.00   0.50    6.00    --  -87.75 -75.00-124.92   50
 30  \w   -155.00-129.00   0.50    6.00    --  -87.75 -77.00 -30.00   52
 31  \w    -93.00 -66.00   0.50    6.00    --  -87.75 -77.00 120.00   54
 32  \w    -98.00 -71.00   0.50    6.00    --  -87.75 -61.00 120.00   54
 33  \w   -125.00 -72.00   0.50    6.00    --  -87.75 -68.00-150.99  106
 34  \w    -93.00 -65.00   0.50    6.00    --  -87.75 -77.00 -30.00   56
 35  \w    -91.00 -65.00   0.50    6.00    --  -87.75 -77.00 -60.00   52
 36  \w    -97.00 -70.00   0.50    6.00    --  -87.75 -64.00 -31.11   54
 37  \w   -135.00 -66.00   0.50    6.00    --  -87.75 -75.00  76.32  138
 38  \w    -94.00 -69.00   0.50    6.00    --  -87.75 -67.00 144.15   50
 39  \w    -98.00 -65.00   0.50    6.00    --  -87.75 -77.00  60.00   66
 40  \w    -97.00 -70.00   0.50    6.00    --  -87.75 -64.00  23.48   54
 41  \w    -92.00 -66.00   0.50    6.00    --  -87.75 -75.00 -84.16   52
 42  \w    -91.00 -66.00   0.50    6.00    --  -87.75 -77.00  30.00   50
 43  \w    -93.00 -66.00   0.50    6.00    --  -87.75 -77.00 -90.00   54
 44  \w   -114.00 -69.00   0.50    6.00    --  -87.75 -72.00-114.09   90
 45  \w    -92.00 -66.00   0.50    6.00    --  -87.75 -77.00  90.00   52
 46  \w     94.00 119.00   0.50    6.00    --  109.25  63.00-169.00   50
 47  \w     57.00 106.00   0.50    6.00    --  109.25 -95.00-180.00   98
 48  \w     39.00  75.00   0.50    6.00    --  109.25-106.00 -84.55   72
 49  \w    108.00 178.00   0.50    6.00    --  109.25  15.00-180.00  140
 50  \w     93.00 120.00   0.50    6.00    --  109.25  77.00-180.00   54
 51  \w    143.00 174.00   0.50    6.00    --  109.25  61.00 120.00   62
 52  \w     46.00 109.00   0.50    6.00    --  109.25-125.00  30.00  126
 53  \w     96.00 138.00   0.50    6.00    --  109.25  61.00 120.00   84
 54  \w     43.00 109.00   0.50    6.00    --  109.25-125.00-180.00  132
 55  \w     91.00 131.00   0.50    6.00    --  109.25  77.00 150.00   80
 56  \w     89.00 133.00   0.50    6.00    --  109.25  77.00   0.00   88
 57  \w    135.00 172.00   0.50    6.00    --  109.25  77.00-180.00   74
 58  \w     88.00 128.00   0.50    6.00    --  109.25  77.00 -60.00   80
 59  \w    145.00 171.00   0.50    6.00    --  109.25  77.00 -60.00   52
 60  \w     47.00  93.00   0.50    6.00    --  109.25 -95.00 -90.00   92
 61  \w     94.00 172.00   0.50    6.00    --  109.25  61.00  30.00  156
 62  \w     39.00  84.00   0.50    6.00    --  109.25 -95.00 -30.00   90
 63  \w    118.00 148.00   0.50    6.00    --  109.25  77.00-120.00   60
 64  \w     93.00 133.00   0.50    6.00    --  109.25  77.00 -90.00   80
 65  \w     89.00 116.00   0.50    6.00    --  109.25  77.00-120.00   54
 66  \w     77.00 104.00   0.50    6.00    --  109.25-125.00 -90.00   54
 67  \w     40.00  70.00   0.50    6.00    --  109.25 -61.00   0.00   60
 68  \w     81.00 106.00   0.50    6.00    --  109.25 -95.00 -60.00   50
 69  \w    101.00 127.00   0.50    6.00    --  109.25  45.00 120.00   52
 70  \w    109.00 172.00   0.50    6.00    --  109.25 125.00 -30.00  126
 71  \w    122.00 177.00   0.50    6.00    --  109.25  45.00 -60.00  110
 72  \w     88.00 177.00   0.50    6.00    --  109.25  77.00  60.00  178
 73  \w    131.00 175.00   0.50    6.00    --  109.25  77.00-150.00   88
 74  \w    127.00 152.00   0.50    6.00    --  109.25  61.00-120.00   50
 75  \w     95.00 123.00   0.50    6.00    --  109.25  61.00-120.00   56
 76  \w     87.00 126.00   0.50    6.00    --  109.25  77.00-150.00   78
 77  \w     37.00 102.00   0.50    6.00    --  109.25 -95.00  30.00  130
 78  \w     96.00 123.00   0.50    6.00    --  109.25  61.00   0.00   54
 79  \w     54.00 106.00   0.50    6.00    --  109.25 -95.00  60.00  104
 80  \w    138.00 178.00   0.50    6.00    --  109.25  77.00  30.00   80
 81  \w     94.00 120.00   0.50    6.00    --  109.25  77.00  30.00   52
 82  \w     41.00  82.00   0.50    6.00    --  109.25-125.00 150.00   82
 83  \w     44.00  71.00   0.50    6.00    --  109.25 -61.00 150.00   54
 84  \w    139.00 164.00   0.50    6.00    --  109.25  61.00 150.00   50
 85  \w     95.00 140.00   0.50    6.00    --  109.25  61.00  60.00   90
 86  \w     94.00 121.00   0.50    6.00    --  109.25  61.00 150.00   54
 87  \w     93.00 158.00   0.50    6.00    --  109.25  61.00 -30.00  130
 88  \w     93.00 165.00   0.50    6.00    --  109.25  61.00 -90.00  144
 89  \w     70.00  95.00   0.50    6.00    --  109.25 -95.00  90.00   50
 90  \w     93.00 170.00   0.50    6.00    --  109.25  77.00 -30.00  154
 91  \w    132.00 173.00   0.50    6.00    --  109.25  61.00  90.00   82
 92  \w     42.00  67.00   0.50    6.00    --  109.25 -95.00 -60.00   50
 93  \w     40.00  67.00   0.50    6.00    --  109.25 -95.00  90.00   54
 94  \w     39.00  64.00   0.50    6.00    --  109.25-125.00 -90.00   50
 95  \w     94.00 120.00   0.50    6.00    --  109.25  61.00  90.00   52
 96  \w     96.00 136.00   0.50    6.00    --  109.25  61.00-150.00   80
 97  \w     37.00  62.00   0.50    6.00    --  109.25 -61.00 -60.00   50
 98  \w    153.00 178.00   0.50    6.00    --  109.25  63.00-169.00   50
 99  \w     80.00 107.00   0.50    6.00    --  109.25-106.00 -84.55   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1504931000
_diffrn_orient_matrix_UB_12      -0.1546675000
_diffrn_orient_matrix_UB_13      0.0450668000
_diffrn_orient_matrix_UB_21      0.1670764000
_diffrn_orient_matrix_UB_22      0.0556046000
_diffrn_orient_matrix_UB_23      -0.0724249000
_diffrn_orient_matrix_UB_31      0.0429009000
_diffrn_orient_matrix_UB_32      0.1060382000
_diffrn_orient_matrix_UB_33      0.0789334000
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.047
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0617P)^2^+0.2180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2870
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00835a2.cif
_cod_data_source_block           mcconnell28
_cod_database_code               7710099
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C19H12F2N2
_chemical_oxdiff_usercomment     'M. Lehr  ML-24-16A'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              10235
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.826