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_7133116
_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 H15 F3 N2 O3'
_chemical_formula_sum            'C17 H15 F3 N2 O3'
_chemical_formula_weight         352.31
_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     direct
_audit_creation_date             2023-12-13
_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
_cell_angle_beta                 113.916(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9356(7)
_cell_length_b                   17.2071(9)
_cell_length_c                   9.5578(5)
_cell_measurement_reflns_used    3881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2390
_cell_measurement_theta_min      5.1110
_cell_volume                     1644.07(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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 0.879
_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    -77.00 -36.00   1.00    1.00    --  -35.62 111.00 133.00   41
  2  \w     34.00  74.00   1.00    1.00    --   35.62-111.00  39.00   40
  3  \w    110.00 168.00   1.00    1.72    --  106.81 111.00 133.00   58
  4  \w     75.00 101.00   1.00    1.72    --  106.81-111.00  39.00   26
  5  \w    -65.00  23.00   1.00    1.00    --  -35.62  19.00-150.00   88
  6  \w     17.00  83.00   1.00    1.00    --   35.62  38.00 -30.00   66
  7  \w    -15.00  52.00   1.00    1.00    --   35.62 -57.00 -60.00   67
  8  \w     68.00 102.00   1.00    1.00    --   35.62 178.00-180.00   34
  9  \w     37.00  95.00   1.00    1.72    --  106.81 -95.00  60.00   58
 10  \w     52.00  96.00   1.00    1.72    --  106.81-111.00-150.00   44
 11  \w    112.00 160.00   1.00    1.72    --  106.81  77.00  30.00   48
 12  \w    106.00 163.00   1.00    1.72    --  106.81  77.00 -60.00   57
 13  \w     54.00 106.00   1.00    1.72    --  106.81-111.00 120.00   52
 14  \w    105.00 175.00   1.00    1.72    --  106.81  45.00-180.00   70
 15  \w     91.00 117.00   1.00    1.72    --  106.81  61.00 -90.00   26
 16  \w    143.00 174.00   1.00    1.72    --  106.81  61.00 -90.00   31
 17  \w     38.00 113.00   1.00    1.72    --  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      0.0936870000
_diffrn_orient_matrix_UB_12      -0.0058360000
_diffrn_orient_matrix_UB_13      -0.0841130000
_diffrn_orient_matrix_UB_21      -0.0326958000
_diffrn_orient_matrix_UB_22      -0.0872008000
_diffrn_orient_matrix_UB_23      -0.0284281000
_diffrn_orient_matrix_UB_31      -0.1179257000
_diffrn_orient_matrix_UB_32      0.0194937000
_diffrn_orient_matrix_UB_33      -0.1522820000
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6475
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.798
_diffrn_reflns_theta_min         4.423
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0631P)^2^+1.0075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2633
_reflns_number_total             3142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02158d2.cif
_cod_data_source_block           3ra
_cod_depositor_comments
'Adding full bibliography for 7133115--7133116.cif.'
_cod_database_code               7133116
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.818
_reflns_odcompleteness_completeness 99.41
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3A), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              93586
_shelx_hkl_checksum              27687
_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 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.578