FeCl<sub>3</sub> mediated dimerization of dihydropyrrolo[2,1-a]isoquinolines and chlorination of tetrasubstituted pyrroles.
Jiang, Xue-Fei; Tan, Hao; Cui, Hai-Lei; Organic & biomolecular chemistry 18 (2020) 660–665; doi:10.1039/c9ob02607j

data_7157258
_publ_section_title
;
 FeCl<sub>3</sub> mediated dimerization of
 dihydropyrrolo[2,1-a]isoquinolines and chlorination of tetrasubstituted
 pyrroles.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              660
_journal_page_last               665
_journal_paper_doi               10.1039/c9ob02607j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 Cl N O4'
_chemical_formula_sum            'C22 H19 Cl N O4'
_chemical_formula_weight         396.83
_space_group_crystal_system      tetragonal
_space_group_IT_number           106
_space_group_name_Hall           'P 4c -2ab'
_space_group_name_H-M_alt        'P 42 b c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-03 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7456(5)
_cell_length_b                   16.7456(5)
_cell_length_c                   13.5915(9)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5360
_cell_measurement_theta_min      3.7700
_cell_volume                     3811.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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   -105.00 -80.00   1.00    2.50    --  -33.50 -19.00-120.00   25
  2  \w    -21.00   4.00   1.00    2.50    --  -33.50 -19.00-120.00   25
  3  \w     18.00  97.00   1.00    2.50    --   36.80  57.00-150.00   79
  4  \w    -31.00  48.00   1.00    2.50    --   36.80 -57.00  30.00   79
  5  \w     19.00  45.00   1.00    2.50    --   36.80-125.00 -30.00   26
  6  \w      9.00  38.00   1.00    2.50    --   36.80  77.00  60.00   29
  7  \w     73.00  99.00   1.00    2.50    --   36.80  77.00  60.00   26
  8  \w     53.00  91.00   1.00    2.50    --   36.80-125.00 -30.00   38
  9  \w    -31.00  52.00   1.00    2.50    --   36.80 -57.00 -30.00   83
 10  \w     18.00  95.00   1.00    2.50    --   36.80  57.00 150.00   77
 11  \w     58.00  83.00   1.00    2.50    --   36.80  57.00  30.00   25
 12  \w     39.00 143.00   1.00    2.50    --  108.00 -91.00 -90.00  104
 13  \w    140.00 173.00   1.00    2.50    --  108.00  50.00 -60.00   33
 14  \w    103.00 160.00   1.00    2.50    --  108.00 111.00-150.00   57
 15  \w    102.00 128.00   1.00    2.50    --  108.00  50.00 -60.00   26
 16  \w     89.00 163.00   1.00    2.50    --  108.00  50.00-180.00   74
 17  \w    109.00 139.00   1.00    2.50    --  108.00 111.00  60.00   30
 18  \w     94.00 153.00   1.00    2.50    --  108.00  50.00-150.00   59
 19  \w     47.00 118.00   1.00    2.50    --  108.00 -63.00  90.00   71
 20  \w     61.00 115.00   1.00    2.50    --  108.00-111.00  90.00   54
 21  \w     39.00 106.00   1.00    2.50    --  108.00 -50.00-120.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640146000
_diffrn_orient_matrix_UB_12      0.0597557000
_diffrn_orient_matrix_UB_13      0.0345263000
_diffrn_orient_matrix_UB_21      0.0647870000
_diffrn_orient_matrix_UB_22      -0.0489074000
_diffrn_orient_matrix_UB_23      -0.0534431000
_diffrn_orient_matrix_UB_31      -0.0132651000
_diffrn_orient_matrix_UB_32      0.0500148000
_diffrn_orient_matrix_UB_33      -0.0937388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16477
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.616
_diffrn_reflns_theta_min         3.733
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_coef       0.00132(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.728
_reflns_Friedel_fraction_max     0.689
_reflns_number_gt                2121
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02607j3.cif
_cod_data_source_block           exp_10666
_cod_depositor_comments          'Adding full bibliography for 7157258.cif.'
_cod_database_code               7157258
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              80195
_shelx_hkl_checksum              39889
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.772