Catalyst-free [3 + 2] cyclization of dihydroisoquinoline imines and isatin-derived Morita-Baylis-Hillman carbonates via 1,5-electrocyclization: synthesis of tetrahydroisoquinoline-fused spirooxindoles.
Tang, Xue; Gao, Ying-Juan; Deng, Hui-Qing; Lei, Jin-Ju; Liu, Si-Wei; Zhou, Lin; Shi, Yin; Liang, Hao; Qiao, Jie; Guo, Li; Han, Bo; Cui, Hai-Lei; Organic & biomolecular chemistry 16 (2018) 3362–3366; doi:10.1039/c8ob00749g

data_7156216
_publ_section_title
;
 Catalyst-free [3 + 2] cyclization of dihydroisoquinoline imines and
 isatin-derived Morita-Baylis-Hillman carbonates via
 1,5-electrocyclization: synthesis of tetrahydroisoquinoline-fused
 spirooxindoles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3362
_journal_page_last               3366
_journal_paper_doi               10.1039/c8ob00749g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C29 H26 N2 O5'
_chemical_formula_sum            'C29 H26 N2 O5'
_chemical_formula_weight         482.52
_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   geom
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-03-25 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                89.877(6)
_cell_angle_beta                 93.866(6)
_cell_angle_gamma                111.112(5)
_cell_formula_units_Z            4
_cell_length_a                   9.050(4)
_cell_length_b                   10.200(4)
_cell_length_c                   27.541(11)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.233
_cell_measurement_theta_min      2.282
_cell_volume                     2365.6(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8865
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         0.741
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.7548.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         8865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.1072
_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^)+(0.0894P)^2^+9.7781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2780
_refine_ls_wR_factor_ref         0.2967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5811
_reflns_number_total             8865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00749g3.cif
_cod_data_source_block           chl_0m_tw
_cod_depositor_comments          'Adding full bibliography for 7156216.cif.'
_cod_database_code               7156216
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.861(3) 0.139(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C5(H5), C33(H33)
3.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C56(H56A,H56B), C57(H57A,H57B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C26(H26), C32(H32), C38(H38), C39(H39), C40(H40),
  C41(H41), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C54(H54)
3.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C51(H51A,H51B,
 H51C), C53(H53A,H53B,H53C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              42060
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'