A convergent formal [4 + 2] cycloaddition of 1,6-diynes and benzyl azides: construction of spiro-polyheterocycles.
Bao, Ming; Lu, Wei; Su, Han; Qiu, Lihua; Xu, Xinfang; Organic & biomolecular chemistry 16 (2018) 3258–3265; doi:10.1039/c8ob00735g

data_1549217
_publ_section_title
;
 A convergent formal [4 + 2] cycloaddition of 1,6-diynes and benzyl
 azides: construction of spiro-polyheterocycles.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3258
_journal_page_last               3265
_journal_paper_doi               10.1039/c8ob00735g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C32 H27 Cl N2 O2 S'
_chemical_formula_sum            'C32 H27 Cl N2 O2 S'
_chemical_formula_weight         539.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-27
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2017-07-27 deposited with the CCDC.
2018-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.004(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6414(12)
_cell_length_b                   17.5960(12)
_cell_length_c                   17.5732(11)
_cell_measurement_reflns_used    4447
_cell_measurement_temperature    120
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.37
_cell_volume                     5315.1(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      119.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         1.877
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1586 before and 0.0858 after correction. The Ratio of minimum to maximum transmission is 0.8881. The \l/2 correction factor is Not present.'
_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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0713P)^2^+5.8324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3449
_reflns_number_total             6080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00735g2.cif
_cod_data_source_block           mo_bm201707241_0m
_cod_depositor_comments          'Adding full bibliography for 1549217.cif.'
_cod_database_code               1549217
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.939
_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 Ternary CH refined with riding coordinates:
 C18(H18)
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:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11),
 C12(H12), C21(H21), C22(H22), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'