A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction.
Bakthadoss, Manickam; Vinayagam, Varathan; Organic & biomolecular chemistry 13 (2015) 10007–10014; doi:10.1039/c5ob01060h

data_7154738
_publ_section_title
;
 A novel protocol for the facile construction of tetrahydroquinoline fused
 tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide
 cycloaddition reaction.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10007
_journal_page_last               10014
_journal_paper_doi               10.1039/c5ob01060h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C25 H22 N2 O5 S'
_chemical_formula_sum            'C25 H22 N2 O5 S'
_chemical_formula_weight         462.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_audit_creation_date             2015-04-17
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Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
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_audit_update_record
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2015-04-18 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.140(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1205(7)
_cell_length_b                   22.1481(18)
_cell_length_c                   11.2162(10)
_cell_measurement_reflns_used    4005
_cell_measurement_theta_max      29.1043
_cell_measurement_theta_min      3.5657
_cell_volume                     2230.3(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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CrysAlisPro, Agilent Technologies,
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(compiled Sep 14 2012,17:21:16)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.8760
_diffrn_measured_fraction_theta_max 0.8760
_diffrn_measurement_details
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  1 omega  -20.00    5.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -88.00  -63.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 25

  3 omega  -92.00  -33.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  178.0000  120.0000 59

  4 omega  -86.00   27.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 113

  5 omega  -74.00  -48.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  178.0000  150.0000 26

  6 omega   -7.00   19.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  106.0000   66.0000 26

  7 omega  -22.00    5.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 27

  8 omega  -23.00   24.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 47

  9 omega  -84.00  -58.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000 -180.0000 26
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_diffrn_orient_matrix_UB_22      0.0088967000
_diffrn_orient_matrix_UB_23      -0.0603565000
_diffrn_orient_matrix_UB_31      0.0770765000
_diffrn_orient_matrix_UB_32      -0.0068913000
_diffrn_orient_matrix_UB_33      0.0091824000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0746
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_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15406
_diffrn_reflns_theta_full        29.1686
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
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_exptl_crystal_density_diffrn    1.3774
_exptl_crystal_F_000             968.9877
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_refine_diff_density_rms         0.1232
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_refine_ls_goodness_of_fit_ref   1.0250
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_constraints    39
_refine_ls_number_parameters     299
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_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.5249
_refine_ls_shift/su_mean         0.0104
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.0423P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_limit_l_min              -7
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_cod_data_source_file            c5ob01060h2.cif
_cod_data_source_block           MB-PVK-VV-27A
_cod_database_code               7154738
_chemical_oxdiff_formula         'C25 H22 N2 O5 S1'
_chemical_oxdiff_usercomment     '298K, COLORLESS, 0.35 0.2 0.2'
_reflns_odcompleteness_completeness 99.45
_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.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C9(H9), C31(H31), C8(H8), C7(H7), C15(H15), C28(H28), C6(H6),
 C29(H29), C16(H16), C18(H18), C19(H19), C17(H17)
2.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C33(H33a,H33b,H33c)
;
_olex2_date_sample_data_collection 2013-10-12
_olex2_submission_special_instructions 'No special instructions were received'