Diastereoselective synthesis of functionalised carbazoles via a sequential Diels–Alder/ene reaction strategy
Cowell, Joseph; Abualnaja, Matokah; Morton, Stephanie; Linder, Ruth; Buckingham, Faye; Waddell, Paul G.; Probert, Michael R.; Hall, Michael J.; RSC Adv. 5 (2015) 16125–; doi:10.1039/C5RA00499C

data_7219493
_publ_section_title
;
 Diastereoselective synthesis of functionalised carbazoles via a
 sequential Diels--Alder/ene reaction strategy
;
_journal_issue                   21
_journal_name_full               'RSC Adv.'
_journal_page_first              16125
_journal_paper_doi               10.1039/C5RA00499C
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C25 H20 N4 O4 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C25.5 H21 Cl N4 O4 S'
_chemical_formula_weight         514.97
_chemical_name_systematic
2-phenyl-11-tosyl-11,11a-dihydro-1H,5H-[1,2,4]triazolo[1',2':1,2]pyridazino[3,4-b]indole-1,3(2H)-dione
_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             2014-12-17
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.12.09 svn.r3114 for OlexSys, GUI svn.r4963)
;
_audit_update_record
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.2586(2)
_cell_length_b                   43.8481(9)
_cell_length_c                   17.0987(3)
_cell_measurement_reflns_used    5338
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      62.2533
_cell_measurement_theta_min      2.0134
_cell_volume                     4685.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
  1 omega   42.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0649  179.0000   90.0000 48

  2 omega   36.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0649  179.0000  -90.0000 33

  3 omega  -21.00   51.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        1.9399   38.0000 -180.0000 72

  4 omega   63.00  144.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   45.0000 -150.0000 81

  5 omega   18.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000   30.0000 32

  6 omega   29.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000  -30.0000 48

  7 omega  107.00  165.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   15.0000 -180.0000 58

  8 omega   37.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210   15.0000 -180.0000 40

  9 omega   19.00   71.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -45.0000   90.0000 52

 10 omega    8.00   71.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       84.6210  -77.0000  -60.0000 63
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1523134000
_diffrn_orient_matrix_UB_12      0.0262335000
_diffrn_orient_matrix_UB_13      -0.0193410000
_diffrn_orient_matrix_UB_21      0.0066997000
_diffrn_orient_matrix_UB_22      0.0103750000
_diffrn_orient_matrix_UB_23      0.0861975000
_diffrn_orient_matrix_UB_31      0.1938529000
_diffrn_orient_matrix_UB_32      -0.0208992000
_diffrn_orient_matrix_UB_33      0.0185258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.846
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13831
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.340
_diffrn_reflns_theta_min         2.015
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         7203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0556P)^2^+8.8883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5694
_reflns_number_total             7203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00499c2.cif
_cod_data_source_block           mjh105
_cod_original_formula_sum        'C25.50 H21 Cl N4 O4 S'
_cod_database_code               7219493
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.779
_shelx_estimated_absorpt_t_min   0.505
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 Ternary CH refined with riding coordinates:
 C8(H8), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C51(H51A,H51B)
2.c Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C50(H50A,H50B,H50C)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C33(H33), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C45(H45), C46(H46), C48(H48), C49(H49)
;
_shelx_res_checksum              18217
_olex2_submission_special_instructions 'No special instructions were received'