Unprecedented access to functionalized pyrrolo[2,1-<i>a</i>]isoquinolines from the domino reaction of isoquinolinium ylides and electrophilic benzannulated heterocycles.
Babu, Sheba Ann; A R, Rajalekshmi; P R, Nitha; Omanakuttan, Vishnu K.; P, Rahul; Varughese, Sunil; John, Jubi; Organic & biomolecular chemistry 19 (2021) 1807–1817; doi:10.1039/d1ob00005e

data_7157857
_publ_section_title
;
 Unprecedented access to functionalized pyrrolo[2,1-<i>a</i>]isoquinolines
 from the domino reaction of isoquinolinium ylides and electrophilic
 benzannulated heterocycles.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1807
_journal_page_last               1817
_journal_paper_doi               10.1039/d1ob00005e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C26 H18 Br N3 O2 S'
_chemical_formula_sum            'C26 H18 Br N3 O2 S'
_chemical_formula_weight         516.40
_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   geom
_audit_creation_date             2020-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-03 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                64.87(5)
_cell_angle_beta                 73.59(6)
_cell_angle_gamma                66.24(5)
_cell_formula_units_Z            2
_cell_length_a                   10.479(6)
_cell_length_b                   11.171(5)
_cell_length_c                   12.250(6)
_cell_measurement_reflns_used    1309
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1177.4(12)
_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)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0897
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9288
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.016
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.863
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0627P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2055
_reflns_number_total             4280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00005e2.cif
_cod_data_source_block           datam
_cod_depositor_comments
'Adding full bibliography for 7157857--7157858.cif.'
_cod_original_cell_volume        1177.5(12)
_cod_database_code               7157857
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.730
_shelx_estimated_absorpt_t_min   0.685
_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
2. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N22(H22), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C17(H17), C19(H19), C20(H20), C27(H27), C28(H28), C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              5211
_olex2_submission_special_instructions 'No special instructions were received'