Ring-Opening Carbonyl-Olefin Metathesis of Norbornenes
Jermaks, Janis; Quach, Phong; Seibel, Zara M.; Pomarole, Julien; Lambert, Tristan; Chemical Science  (2020) –; doi:10.1039/D0SC02243H

data_1558463
_publ_section_title
;
 Ring-Opening Carbonyl-Olefin Metathesis of Norbornenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02243H
_journal_year                    2020
_chemical_formula_moiety         'C2 F3 O2, C20 H27 N2'
_chemical_formula_sum            'C22 H27 F3 N2 O2'
_chemical_formula_weight         408.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-04-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.36910(10)
_cell_length_b                   13.80880(10)
_cell_length_c                   12.46330(10)
_cell_measurement_reflns_used    67726
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6770
_cell_measurement_theta_min      4.7850
_cell_volume                     1947.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     -2.00  28.00   0.50    0.18    --   26.00  96.00-122.95   60
  2  \w     27.00  54.00   0.50    0.18    --   48.42  77.00-150.00   54
  3  \w     44.00  72.00   0.50    0.18    --   62.00  72.00-143.36   56
  4  \w     68.00  94.00   0.50    0.18    --   54.00  77.00 -95.72   52
  5  \w    100.00 126.00   0.50    0.18    --   58.00  77.00 -54.87   52
  6  \w     83.00 118.00   0.50    0.73    --  102.00  75.00 -72.98   70
  7  \w    120.00 159.00   0.50    0.73    --  107.75  77.00 -60.00   78
  8  \w    132.00 178.00   0.50    0.73    --  107.75  77.00-120.00   92
  9  \w    146.00 172.00   0.50    0.73    --  107.75  77.00-180.00   52
 10  \w    141.00 167.00   0.50    0.73    --  107.75  77.00-150.00   52
 11  \w    126.00 151.00   0.50    0.73    --  107.75  45.00-120.00   50
 12  \w    125.00 172.00   0.50    0.73    --  107.75  77.00 -90.00   94
 13  \w    133.00 177.00   0.50    0.73    --  107.75 125.00-120.00   88
 14  \w    138.00 175.00   0.50    0.73    --  107.75 116.00   4.00   74
 15  \w    153.00 178.00   0.50    0.73    --  107.75 125.00  90.00   50
 16  \w    141.00 177.00   0.50    0.73    --  107.75  77.00 120.00   72
 17  \w    134.00 160.00   0.50    0.73    --  107.75  61.00 150.00   52
 18  \w    143.00 176.00   0.50    0.73    --  107.75  30.00 150.00   66
 19  \w    153.00 178.00   0.50    0.73    --  107.75  30.00 120.00   50
 20  \w    143.00 171.00   0.50    0.73    --  107.75  61.00  90.00   56
 21  \w    140.00 172.00   0.50    0.73    --  107.75  77.00  60.00   64
 22  \w    134.00 161.00   0.50    0.73    --  107.75  15.00 120.00   54
 23  \w    108.00 133.00   0.50    0.18    --   66.00  78.00 171.77   50
 24  \w     89.00 128.00   0.50    0.73    --  107.75  71.00 112.23   78
 25  \w    113.00 165.00   0.50    0.73    --   94.00  82.00  62.33  104
 26  \w    133.00 169.00   0.50    0.73    --  107.75  77.00  30.00   72
 27  \w    119.00 145.00   0.50    0.73    --  107.75 163.00 152.00   52
 28  \w    110.00 161.00   0.50    0.73    --  107.75 125.00 150.00  102
 29  \w     95.00 135.00   0.50    0.73    --  107.75  61.00  60.00   80
 30  \w    104.00 140.00   0.50    0.73    --  107.75  30.00 120.00   72
 31  \w    105.00 130.00   0.50    0.73    --  107.75  30.00 150.00   50
 32  \w     87.00 118.00   0.50    0.73    --  107.75  77.00 120.00   62
 33  \w     93.00 120.00   0.50    0.73    --  107.75  61.00 150.00   54
 34  \w     93.00 119.00   0.50    0.73    --  107.75  61.00  90.00   52
 35  \w     86.00 125.00   0.50    0.73    --  107.75  77.00  30.00   78
 36  \w    100.00 128.00   0.50    0.73    --  107.75  45.00 -30.00   56
 37  \w    104.00 177.00   0.50    0.73    --  107.75  45.00 -90.00  146
 38  \w    112.00 170.00   0.50    0.73    --  107.75 125.00-180.00  116
 39  \w    101.00 178.00   0.50    0.73    --  107.75  45.00 -60.00  154
 40  \w     99.00 125.00   0.50    0.73    --  107.75  45.00-180.00   52
 41  \w     97.00 123.00   0.50    0.73    --  107.75  45.00-120.00   52
 42  \w     93.00 175.00   0.50    0.73    --  107.75  61.00-120.00  164
 43  \w     94.00 173.00   0.50    0.73    --  107.75  61.00   0.00  158
 44  \w     93.00 144.00   0.50    0.73    --  107.75  61.00 -90.00  102
 45  \w     93.00 141.00   0.50    0.73    --  107.75  61.00-150.00   96
 46  \w     98.00 178.00   0.50    0.73    --  107.75  45.00-150.00  160
 47  \w     95.00 141.00   0.50    0.73    --  107.75  61.00-180.00   92
 48  \w     86.00 112.00   0.50    0.73    --  107.75  77.00 -90.00   52
 49  \w     86.00 112.00   0.50    0.73    --  107.75  77.00 -60.00   52
 50  \w     94.00 149.00   0.50    0.73    --  107.75  61.00 -30.00  110
 51  \w     88.00 155.00   0.50    0.73    --  107.75  73.00  25.94  134
 52  \w     86.00 158.00   0.50    0.73    --  107.75  77.00 150.00  144
 53  \w     95.00 132.00   0.50    0.73    --  107.75 125.00  90.00   74
 54  \w     86.00 153.00   0.50    0.73    --  107.75  77.00   0.00  134
 55  \w     86.00 112.00   0.50    0.73    --  107.75  77.00-120.00   52
 56  \w     86.00 115.00   0.50    0.73    --  107.75  77.00-180.00   58
 57  \w     87.00 113.00   0.50    0.73    --  107.75  77.00-150.00   52
 58  \w     44.00  79.00   0.50    0.18    --   66.00  78.00 -30.45   70
 59  \w     36.00  78.00   0.50    0.18    --   58.00  77.00 -54.87   84
 60  \w     34.00  59.00   0.50    0.18    --   58.00  83.00  -8.67   50
 61  \w     35.00  68.00   0.50    0.18    --   58.00  80.00  15.53   66
 62  \w     46.00  84.00   0.50    0.18    --   66.00  73.00  75.69   76
 63  \w     70.00 108.00   0.50    0.73    --   94.00  82.00  62.33   76
 64  \w     86.00 115.00   0.50    0.73    --  107.75  77.00  90.00   58
 65  \w     87.00 117.00   0.50    0.73    --  107.75  77.00  60.00   60
 66  \w     97.00 131.00   0.50    0.73    --  107.75  15.00 120.00   68
 67  \w    101.00 127.00   0.50    0.73    --  107.75 -82.00 127.28   52
 68  \w     92.00 127.00   0.50    0.73    --  107.75-138.00 138.30   70
 69  \w    107.00 143.00   0.50    0.73    --  107.75-163.00 127.00   72
 70  \w     84.00 109.00   0.50    0.73    --  107.75 -94.00  90.00   50
 71  \w     66.00  95.00   0.50    0.73    --  107.75 -77.00  60.00   58
 72  \w     66.00  92.00   0.50    0.73    --  107.75 -94.00   0.00   52
 73  \w     86.00 111.00   0.50    0.73    --  107.75-105.00 -15.87   50
 74  \w     90.00 116.00   0.50    0.73    --  107.75-125.00 -30.00   52
 75  \w     65.00 113.00   0.50    0.73    --  107.75-116.00 -84.00   96
 76  \w     71.00  96.00   0.50    0.73    --  107.75 -77.00-120.00   50
 77  \w     76.00 116.00   0.50    0.73    --  107.75-125.00-120.00   80
 78  \w     48.00  74.00   0.50    0.73    --  107.75-105.00 -15.87   52
 79  \w     45.00  71.00   0.50    0.73    --  107.75-125.00 -30.00   52
 80  \w     41.00  99.00   0.50    0.73    --  107.75 -94.00  30.00  116
 81  \w     50.00  76.00   0.50    0.73    --  107.75-138.00 138.30   52
 82  \w     64.00 113.00   0.50    0.73    --  107.75-125.00 150.00   98
 83  \w     53.00 116.00   0.50    0.18    --   48.42-163.00 127.00  126
 84  \w     36.00  70.00   0.50    0.73    --  107.75-125.00  60.00   68
 85  \w     43.00  93.00   0.50    0.73    --  107.75 -82.00 127.28  100
 86  \w     37.00  65.00   0.50    0.73    --  107.75 -61.00  30.00   56
 87  \w     41.00  98.00   0.50    0.73    --  107.75 -77.00 -30.00  114
 88  \w     41.00  66.00   0.50    0.73    --  107.75-125.00-120.00   50
 89  \w     36.00 114.00   0.50    0.73    --  107.75-125.00-150.00  156
 90  \w     36.00  99.00   0.50    0.73    --  107.75 -77.00-150.00  126
 91  \w     36.00  75.00   0.50    0.73    --  107.75 -77.00-180.00   78
 92  \w     36.00  70.00   0.50    0.73    --  107.75 -61.00-150.00   68
 93  \w     37.00 103.00   0.50    0.73    --  107.75 -77.00 -90.00  132
 94  \w     38.00  64.00   0.50    0.73    --  107.75 -94.00   0.00   52
 95  \w     36.00  89.00   0.50    0.73    --  107.75 -94.00 -30.00  106
 96  \w     36.00  67.00   0.50    0.73    --  107.75 -61.00-120.00   62
 97  \w     40.00  65.00   0.50    0.73    --  107.75 -94.00 -60.00   50
 98  \w     27.00  89.00   0.50    0.18    --   48.42-116.00 -84.00  124
 99  \w     36.00  88.00   0.50    0.73    --  107.75-125.00-180.00  104
100  \w     32.00  64.00   0.50    0.18    --   54.00  77.00 -95.72   64
101  \w     49.00 100.00   0.50    0.18    --   70.00  76.00-146.20  102
102  \w     86.00 178.00   0.50    0.73    --  107.75  77.00 -30.00  184
103  \w     68.00  94.00   0.50    0.18    --   48.42 163.00 152.00   52
104  \w     34.00  61.00   0.50    0.18    --   54.00  74.00 151.37   54
105  \w     42.00  74.00   0.50    0.18    --   62.00  72.00 118.26   64
106  \w     44.00  69.00   0.50    0.18    --   66.00  77.00 162.04   50
107  \w     44.00  70.00   0.50    0.18    --   66.00  78.00 171.77   52
108  \w     20.00  45.00   0.50    0.18    --   46.00  86.00  87.55   50
109  \w     33.00 105.00   0.50    0.18    --   54.00  79.00  78.14  144
110  \w     26.00  52.00   0.50    0.18    --   50.00  83.00 -31.47   52
111  \w     15.00  40.00   0.50    0.18    --   42.00  89.00  48.19   50
112  \w     33.00  76.00   0.50    0.18    --   54.00  77.00  57.16   86
113  \w     18.00  43.00   0.50    0.18    --   46.00  90.00 129.77   50
114  \w    -10.00  15.00   0.50    0.18    --   22.00 101.00  43.46   50
115  \w      3.00  28.00   0.50    0.18    --   34.00  97.00 -17.08   50
116  \w    -14.00  28.00   0.50    0.18    --   18.00  98.00 -58.66   84
117  \w     26.00  69.00   0.50    0.18    --   50.00  82.00-133.26   86
118  \w    -38.00  -8.00   0.50    0.18    --    6.00 122.00-168.12   60
119  \w    -60.00  -7.00   0.50    0.18    --  -48.42 116.00   4.00  106
120  \w    -75.00 -50.00   0.50    0.73    --  -86.25 116.00   4.00   50
121  \w    -97.00 -72.00   0.50    0.18    --  -48.42 163.00 152.00   50
122  \w    -97.00 -72.00   0.50    0.73    --  -86.25 163.00 152.00   50
123  \w    -11.00  17.00   0.50    0.18    --   22.00 102.00 133.10   56
124  \w     45.00  71.00   0.50    0.73    --  107.75 -61.00 120.00   52
125  \w     40.00  77.00   0.50    0.73    --  107.75 -77.00 150.00   74
126  \w     37.00  71.00   0.50    0.73    --  107.75 -94.00  90.00   68
127  \w    -66.00 -25.00   0.50    0.18    --  -50.00 -83.00 -64.91   82
128  \w    -67.00 -41.00   0.50    0.18    --  -66.00 -83.00  16.91   52
129  \w    -77.00 -48.00   0.50    0.18    --  -66.00 -69.00  99.60   58
130  \w    -76.00 -50.00   0.50    0.73    --  -74.00 -81.00 109.99   52
131  \w    -81.00 -55.00   0.50    0.73    --  -78.00 -83.00  77.26   52
132  \w    -83.00 -57.00   0.50    0.73    --  -78.00 -74.00 128.75   52
133  \w    -92.00 -63.00   0.50    0.73    --  -82.00 -69.00 152.11   58
134  \w    -93.00 -66.00   0.50    0.73    --  -86.25 -73.00 128.46   54
135  \w    -92.00 -66.00   0.50    0.73    --  -86.25 -74.00  97.97   52
136  \w   -105.00 -66.00   0.50    0.73    --  -86.25 -73.00  14.07   78
137  \w    -83.00 -51.00   0.50    0.73    --  -70.00 -69.00 -23.66   64
138  \w    -68.00 -42.00   0.50    0.18    --  -66.00 -83.00 -79.26   52
139  \w    -69.00 -42.00   0.50    0.18    --  -66.00 -81.00-137.38   54
140  \w    -75.00 -49.00   0.50    0.73    --  -74.00 -83.00-177.70   52
141  \w   -105.00 -53.00   0.50    0.73    --  -74.00 -75.00-100.88  104
142  \w   -100.00 -64.00   0.50    0.73    --  -86.25 -77.00   0.00   72
143  \w   -104.00 -67.00   0.50    0.73    --  -86.25 -71.00 -47.43   74
144  \w   -101.00 -64.00   0.50    0.73    --  -86.25 -77.00  30.00   74
145  \w   -102.00 -67.00   0.50    0.73    --  -86.25 -74.00 -54.55   70
146  \w    -98.00 -65.00   0.50    0.73    --  -86.25 -76.00-137.08   66
147  \w   -117.00 -64.00   0.50    0.73    --  -86.25 -77.00-150.00  106
148  \w   -110.00 -66.00   0.50    0.73    --  -86.25 -77.00 -90.00   88
149  \w   -116.00 -66.00   0.50    0.73    --  -86.25 -74.00 -21.80  100
150  \w   -122.00 -64.00   0.50    0.73    --  -86.25 -77.00  90.00  116
151  \w    -98.00 -64.00   0.50    0.73    --  -86.25 -77.00 120.00   68
152  \w   -101.00 -68.00   0.50    0.73    --  -86.25 -69.00 179.45   66
153  \w   -112.00 -68.00   0.50    0.73    --  -86.25 -67.00 151.41   88
154  \w   -115.00 -66.00   0.50    0.18    --  -48.42-163.00 127.00   98
155  \w   -119.00 -94.00   0.50    0.73    --  -86.25-163.00 127.00   50
156  \w   -158.00 -65.00   0.50    0.73    --  -86.25 -77.00  60.00  186
157  \w   -141.00-116.00   0.50    0.73    --  -86.25-116.00 -84.00   50
158  \w   -152.00 -62.00   0.50    0.73    --  -82.00 -73.00-120.55  180
159  \w   -155.00-123.00   0.50    0.73    --  -86.25 -74.00 -21.80   64
160  \w   -158.00-109.00   0.50    0.73    --  -86.25 -74.00 -54.55   98
;
_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      -0.0383532000
_diffrn_orient_matrix_UB_12      -0.0842970000
_diffrn_orient_matrix_UB_13      0.0697881000
_diffrn_orient_matrix_UB_21      -0.0149316000
_diffrn_orient_matrix_UB_22      0.0711316000
_diffrn_orient_matrix_UB_23      0.0929713000
_diffrn_orient_matrix_UB_31      -0.1297442000
_diffrn_orient_matrix_UB_32      0.0167832000
_diffrn_orient_matrix_UB_33      -0.0435822000
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            87403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.042
_diffrn_reflns_theta_min         4.791
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0476P)^2^+1.0859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4008
_reflns_number_total             4166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02243h2.cif
_cod_data_source_block           rkpq3_abs
_cod_database_code               1558463
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C22H28F3N2O2
_chemical_oxdiff_usercomment     'Crystallized from MeCN'
_reflns_odcompleteness_completeness 97.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,
 H11B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              67410
_shelx_hkl_checksum              78740
_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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.890