Cascade reaction of alkynols and 1-(2-aminophenyl)prop-2-ynols to form a fused 5,5,6-tricyclic system: formation of four bonds in a single reaction
Mao, Xiao Feng; Zhu, Xiao-Ping; Li, Deng Yuan; Jiang, Liang-Liang; Liu, Pei Nian; Chem. Commun.  (2017) –; doi:10.1039/C7CC04126H

data_7120407
_publ_section_title
;
 Cascade reaction of alkynols and 1-(2-aminophenyl)prop-2-ynols to form a
 fused 5,5,6-tricyclic system: formation of four bonds in a single
 reaction
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04126H
_journal_year                    2017
_chemical_formula_moiety         'C38 H30 Cl N O4 S'
_chemical_formula_sum            'C38 H30 Cl N O4 S'
_chemical_formula_weight         632.14
_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     dual
_audit_creation_date             2017-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-05-26 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                104.565(2)
_cell_angle_beta                 104.140(2)
_cell_angle_gamma                101.177(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0712(10)
_cell_length_b                   13.1339(13)
_cell_length_c                   13.3013(14)
_cell_measurement_reflns_used    2583
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.17
_cell_volume                     1589.0(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         1.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0430 before and 0.0336 after correction. The Ratio of minimum to maximum transmission is 0.9138. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0603P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4102
_reflns_number_total             7882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04126h2.cif
_cod_data_source_block           mo_dm17140_0m
_cod_database_code               7120407
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.967
_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 Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C17(H17)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              81922
_olex2_submission_special_instructions 'No special instructions were received'