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_7120409
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1p3kv6
_audit_creation_date             2017-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-05-26 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9530(11)
_cell_length_b                   16.5209(14)
_cell_length_c                   31.646(3)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.253
_cell_measurement_theta_min      2.20
_cell_volume                     6249.3(10)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0505
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            60012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.605
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0705 before and 0.0466 after correction. The Ratio of minimum to maximum transmission is 0.9114. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         9594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+5.3755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5649
_reflns_number_total             9594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04126h2.cif
_cod_data_source_block           mo_dm17188_0m
_cod_original_cell_volume        6249.3(9)
_cod_database_code               7120409
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.927
_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:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              77355
_olex2_submission_special_instructions 'No special instructions were received'