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_7219495
_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         'C33 H25 N7 O6 S'
_chemical_formula_sum            'C33 H25 N7 O6 S'
_chemical_formula_weight         647.66
_chemical_name_systematic
6-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-2-phenyl-11-tosyl-5,6-dihydro-[1,2,4]triazolo[1',2':1,2]pyridazino[3,4-b]indole-1,3(2H,11H)-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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-12-18 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.991(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1236(3)
_cell_length_b                   20.8432(5)
_cell_length_c                   12.0391(2)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.0850
_cell_measurement_theta_min      3.3860
_cell_volume                     3232.74(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0936454000
_diffrn_orient_matrix_UB_12      -0.0040772000
_diffrn_orient_matrix_UB_13      -0.0987299000
_diffrn_orient_matrix_UB_21      0.0358684000
_diffrn_orient_matrix_UB_22      0.0620523000
_diffrn_orient_matrix_UB_23      -0.0507830000
_diffrn_orient_matrix_UB_31      0.0650071000
_diffrn_orient_matrix_UB_32      -0.0400248000
_diffrn_orient_matrix_UB_33      -0.0683558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23327
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.247
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.331
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0445P)^2^+1.0584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             5646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00499c2.cif
_cod_data_source_block           mjh140002
_cod_original_cell_volume        3232.74(13)
_cod_database_code               7219495
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C33 H25 N7 O6 S1'
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              92362