Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1'H-Spiro[azirine-2,4'-quinolin]-2'(3'H)-ones.
Meng, Qiang; Chen, Fei; Yu, Wei; Han, Bing; Organic letters 19 (2017) 5186–5189; doi:10.1021/acs.orglett.7b02453

data_1547305
_publ_section_title
;
 Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward
 Trifluoromethyl-Substituted
 1'H-Spiro[azirine-2,4'-quinolin]-2'(3'H)-ones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5186
_journal_page_last               5189
_journal_paper_doi               10.1021/acs.orglett.7b02453
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H18 Cl F3 N2 O3 S'
_chemical_formula_sum            'C25 H18 Cl F3 N2 O3 S'
_chemical_formula_weight         518.92
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-03-23 # Formatted by publCIF
;
_cell_angle_alpha                70.038(7)
_cell_angle_beta                 86.459(7)
_cell_angle_gamma                82.520(8)
_cell_formula_units_Z            4
_cell_length_a                   8.9921(10)
_cell_length_b                   14.9910(14)
_cell_length_c                   18.8794(12)
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      23.8130
_cell_measurement_theta_min      3.7930
_cell_volume                     2371.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      292.95(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -101.00  -73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  120.0000 28

  2 omega  -17.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 28

  3 omega  -48.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -57.0000  -60.0000 52

  4 omega   -5.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 26

  5 omega  -11.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   90.0000 64

  6 omega  -40.00    5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 45

  7 omega   54.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   90.0000 41

  8 omega  -25.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -90.0000 124
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0048936000
_diffrn_orient_matrix_UB_12      0.0402456000
_diffrn_orient_matrix_UB_13      0.0110288000
_diffrn_orient_matrix_UB_21      0.0732153000
_diffrn_orient_matrix_UB_22      0.0037573000
_diffrn_orient_matrix_UB_23      -0.0161931000
_diffrn_orient_matrix_UB_31      -0.0307763000
_diffrn_orient_matrix_UB_32      0.0305777000
_diffrn_orient_matrix_UB_33      -0.0348488000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.1151
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15511
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.366
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         9305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0951P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.2400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4614
_reflns_number_total             9305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02453_si_002.cif
_cod_data_source_block           menqiang_0109
_cod_depositor_comments          'Adding full bibliography for 1547305.cif.'
_cod_database_code               1547305
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_cell_oxdiff_angle_alpha         70.038(7)
_cell_oxdiff_angle_beta          86.459(7)
_cell_oxdiff_angle_gamma         82.520(8)
_cell_oxdiff_length_a            8.9921(10)
_cell_oxdiff_length_b            14.9910(14)
_cell_oxdiff_length_c            18.8794(12)
_cell_oxdiff_measurement_reflns_used 2538
_cell_oxdiff_volume              2371.3(4)
_reflns_odcompleteness_completeness 99.67
_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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C46(H46),
 C48(H48), C49(H49), C50(H50)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C42(H42A,H42B,H42C)
;
_olex2_date_sample_data_collection 2017-01-09
_olex2_submission_special_instructions 'No special instructions were received'