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_7219496
_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         'C28 H24 Br2 N4 O5 S, C4 H10 O'
_chemical_formula_sum            'C32 H34 Br2 N4 O6 S'
_chemical_formula_weight         762.51
_chemical_name_systematic
(3aS*,5S*,10bS*)-5-((2,6-dibromophenyl)(hydroxy)amino)-N,N-dimethyl-1,3-dioxo-2-phenyl-1,3,3a,4,5,10b-hexahydropyrrolo[3,4-a]carbazole-10(2H)-sulfonamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_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                87.321(10)
_cell_angle_beta                 78.605(10)
_cell_angle_gamma                70.030(11)
_cell_formula_units_Z            2
_cell_length_a                   10.0627(11)
_cell_length_b                   12.5064(17)
_cell_length_c                   13.7858(16)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.7130
_cell_measurement_theta_min      2.9480
_cell_volume                     1598.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details
;
  1 omega  -67.00  -37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   77.0000  -60.0000 30

  2 omega  -92.00  -42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000   90.0000 50

  3 omega -118.00  -42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000 -150.0000 76

  4 omega -104.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   38.0000  150.0000 182

  5 omega   92.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  159.0000 -143.0000 38

  6 omega  -61.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  -38.0000 -120.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0419430000
_diffrn_orient_matrix_UB_12      0.0087615000
_diffrn_orient_matrix_UB_13      0.0486336000
_diffrn_orient_matrix_UB_21      -0.0598782000
_diffrn_orient_matrix_UB_22      0.0373809000
_diffrn_orient_matrix_UB_23      -0.0184265000
_diffrn_orient_matrix_UB_31      -0.0223313000
_diffrn_orient_matrix_UB_32      -0.0465732000
_diffrn_orient_matrix_UB_33      -0.0071723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10012
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.798
_diffrn_reflns_theta_min         2.894
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  0.698
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.585
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.7113
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.1482
_refine_diff_density_max         3.753
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+7.5386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4915
_reflns_number_total             6056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00499c2.cif
_cod_data_source_block           mjh69
_cod_original_cell_volume        1598.0(4)
_cod_database_code               7219496
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C32 H34 O6 S1 Br2 N4'
_reflns_odcompleteness_completeness 92.08
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C13(H13), C4(H4), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C31(H31A,H31B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C9(H9), C20(H20), C8(H8), C23(H23), C25(H25), C16(H16),
 C18(H18), C19(H19), C24(H24), C17(H17)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              41747
_olex2_submission_special_instructions 'No special instructions were received'