Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source.
Zheng, Kailu; Zhuang, Shiyi; Shu, Wenming; Wu, Yandong; Yang, Chuluo; Wu, Anxin; Chemical communications (Cambridge, England) 54 (2018) 11897–11900; doi:10.1039/c8cc06908e

data_7122407
_publ_section_title
;
 Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to
 pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11897
_journal_page_last               11900
_journal_paper_doi               10.1039/c8cc06908e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C26 H17 Br2 N O2'
_chemical_formula_sum            'C26 H17 Br2 N O2'
_chemical_formula_weight         535.22
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-13 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.507(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7349(8)
_cell_length_b                   22.1152(14)
_cell_length_c                   11.5746(9)
_cell_measurement_reflns_used    2804
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.2070
_cell_measurement_theta_min      2.5970
_cell_volume                     2132.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.839
_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    -25.00  88.00   1.00    1.80    --   11.74  19.00  60.00  113
  2  \w     11.00  36.00   1.00    1.80    --   11.74 -37.00-150.00   25
  3  \w     -4.00  27.00   1.00    1.80    --  -11.59 -99.00-180.00   31
  4  \w    -36.00 -17.00   1.00    1.80    --   11.74 -37.00-150.00   19
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0496057000
_diffrn_orient_matrix_UB_12      0.0258536000
_diffrn_orient_matrix_UB_13      0.0050708000
_diffrn_orient_matrix_UB_21      0.0689056000
_diffrn_orient_matrix_UB_22      -0.0181442000
_diffrn_orient_matrix_UB_23      0.0257684000
_diffrn_orient_matrix_UB_31      0.0065491000
_diffrn_orient_matrix_UB_32      -0.0057424000
_diffrn_orient_matrix_UB_33      -0.0585685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10593
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.489
_diffrn_reflns_theta_min         2.062
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0221P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             4967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06908e2.cif
_cod_data_source_block           exp_1228
_cod_depositor_comments
'Adding full bibliography for 7122405--7122407.cif.'
_cod_original_cell_volume        2132.4(3)
_cod_database_code               7122407
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C2(H2), C15(H15), C19(H19), C26(H26), C18(H18), C22(H22), C12(H12),
 C10(H10), C9(H9), C23(H23), C16(H16), C11(H11)
;
_olex2_date_sample_data_collection 2018-01-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.834