A catalyst-free 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines and 3-nitroindoles: an easy access to five-ring-fused tetrahydroisoquinolines
Liu, Xihong; Yang, Dongxu; Wang, Kezhou; Zhang, Jinlong; Wang, Rui; Green Chem. 19 (2017) 82–; doi:10.1039/C6GC02517J

data_7226822
_publ_section_title
;
 A catalyst-free 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines
 and 3-nitroindoles: an easy access to five-ring-fused
 tetrahydroisoquinolines
;
_journal_issue                   1
_journal_name_full               'Green Chem.'
_journal_page_first              82
_journal_paper_doi               10.1039/C6GC02517J
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H26 N4 O6 S'
_chemical_formula_sum            'C27 H26 N4 O6 S'
_chemical_formula_weight         534.58
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-17 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.911(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.4184(11)
_cell_length_b                   8.2542(5)
_cell_length_c                   18.8202(12)
_cell_measurement_reflns_used    1772
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      24.8260
_cell_measurement_theta_min      3.7540
_cell_volume                     2614.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -101.00  -61.10   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -120.0000 38

  2 omega  -43.00   59.90   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -180.0000 98

  3 omega  -36.00   59.55   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   90.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0364205000
_diffrn_orient_matrix_UB_12      0.0431552000
_diffrn_orient_matrix_UB_13      -0.0099560000
_diffrn_orient_matrix_UB_21      -0.0125383000
_diffrn_orient_matrix_UB_22      -0.0484236000
_diffrn_orient_matrix_UB_23      -0.0319995000
_diffrn_orient_matrix_UB_31      -0.0171408000
_diffrn_orient_matrix_UB_32      -0.0563335000
_diffrn_orient_matrix_UB_33      0.0199255000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10009
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.8191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                3225
_reflns_number_total             5140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc02517j2.cif
_cod_data_source_block           liuxh_0628
_cod_depositor_comments          'Adding full bibliography for 7226822.cif.'
_cod_original_cell_volume        2614.7(3)
_cod_database_code               7226822
_chemical_oxdiff_formula         'C30 S8 H20 I2'
_reflns_odcompleteness_completeness 99.70
_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:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_olex2_date_sample_data_collection 2016-06-28
_olex2_submission_special_instructions 'No special instructions were received'