Divergent synthesis of pyrrolizine derivatives through C-H bond functionalization of pyrroles.
Wang, Manqing; Xu, Yuanshuang; Hou, Huihang; Zhang, Xinying; Fan, Xuesen; Chemical communications (Cambridge, England) 60 (2024) 6536–6539; doi:10.1039/d4cc02158d

data_7133115
_publ_section_title
;
 Divergent synthesis of pyrrolizine derivatives through C-H bond
 functionalization of pyrroles.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6536
_journal_page_last               6539
_journal_paper_doi               10.1039/d4cc02158d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H11 F3 N2 O4'
_chemical_formula_sum            'C17 H11 F3 N2 O4'
_chemical_formula_weight         364.28
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-03-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-30 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.001(4)
_cell_angle_beta                 112.552(4)
_cell_angle_gamma                105.120(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7758(4)
_cell_length_b                   10.5130(5)
_cell_length_c                   11.2193(5)
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8630
_cell_measurement_theta_min      4.2870
_cell_volume                     1021.51(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_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   -103.00 -78.00   1.00    1.89    --  -35.62-160.00  76.00   25
  2  \w    -65.00 -39.00   1.00    1.89    --  -35.62 118.00 -44.00   26
  3  \w     41.00  82.00   1.00    1.89    --   35.62-118.00-131.00   41
  4  \w     76.00 106.00   1.00    1.89    --   35.62-160.00  76.00   30
  5  \w     83.00 110.00   1.00    7.57    --  106.81 160.00 107.00   27
  6  \w     42.00 108.00   1.00    7.57    --  106.81-118.00-131.00   66
  7  \w     67.00  92.00   1.00    7.57    --  106.81-160.00  76.00   25
  8  \w    119.00 144.00   1.00    7.57    --  106.81 160.00 107.00   25
  9  \w    113.00 138.00   1.00    7.57    --  106.81 118.00 -44.00   25
 10  \w   -104.00 -17.00   1.00    1.89    --  -35.62 -38.00  60.00   87
 11  \w    -91.00 -66.00   1.00    1.89    --  -35.62 160.00 107.00   25
 12  \w     17.00  74.00   1.00    1.89    --   35.62 -99.00  90.00   57
 13  \w    -24.00  48.00   1.00    1.89    --   35.62 -38.00 -60.00   72
 14  \w    -14.00  23.00   1.00    1.89    --   35.62 -77.00  30.00   37
 15  \w     19.00  98.00   1.00    1.89    --   35.62  38.00-150.00   79
 16  \w    -23.00  53.00   1.00    1.89    --   35.62 -38.00-150.00   76
 17  \w    -18.00  33.00   1.00    1.89    --   35.62 -77.00 -60.00   51
 18  \w     91.00 174.00   1.00    7.57    --  106.81  45.00 -30.00   83
 19  \w    104.00 135.00   1.00    7.57    --  106.81 111.00  60.00   31
 20  \w     40.00 124.00   1.00    7.57    --  106.81 -45.00-180.00   84
 21  \w    147.00 172.00   1.00    7.57    --  106.81 111.00  60.00   25
 22  \w     65.00 108.00   1.00    7.57    --  106.81-111.00   0.00   43
 23  \w     58.00 114.00   1.00    7.57    --  106.81 -45.00 -90.00   56
 24  \w     40.00 105.00   1.00    7.57    --  106.81 -95.00  60.00   65
 25  \w     70.00 132.00   1.00    7.57    --  106.81 178.00-120.00   62
 26  \w     90.00 115.00   1.00    7.57    --  106.81 -45.00  90.00   25
 27  \w     53.00  83.00   1.00    7.57    --  106.81 -45.00  90.00   30
 28  \w     65.00 105.00   1.00    7.57    --  106.81-111.00 -90.00   40
 29  \w     41.00  68.00   1.00    7.57    --  106.81-111.00 120.00   27
 30  \w     92.00 175.00   1.00    7.57    --  106.81  30.00-120.00   83
 31  \w    118.00 162.00   1.00    7.57    --  106.81  77.00-180.00   44
 32  \w     52.00 127.00   1.00    7.57    --  106.81 -30.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0223132000
_diffrn_orient_matrix_UB_12      -0.1391167000
_diffrn_orient_matrix_UB_13      -0.0072718000
_diffrn_orient_matrix_UB_21      0.0932966000
_diffrn_orient_matrix_UB_22      0.0188442000
_diffrn_orient_matrix_UB_23      0.1480347000
_diffrn_orient_matrix_UB_31      -0.1497986000
_diffrn_orient_matrix_UB_32      -0.0602202000
_diffrn_orient_matrix_UB_33      0.0205267000
_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     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7312
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.621
_diffrn_reflns_theta_min         4.294
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.109a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0680
_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^)+(0.1079P)^2^+0.4647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2915
_reflns_number_total             3851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02158d2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7133115--7133116.cif.'
_cod_database_code               7133115
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.841
_reflns_odcompleteness_completeness 99.75
_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 N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 O3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3A), C4(H4), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              24589
_shelx_hkl_checksum              47251
_shelx_fab_checksum              15365
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.724