Diversity-Oriented Synthesis of Heterocycles and Macrocycles by Controlled Reactions of Oxetanes with α-Iminocarbenes
Guarnieri-Ibáñez, Alejandro; Medina, Florian; Besnard, Céline; Kidd, Sarah L.; Spring, David R.; Lacour, Jerome; Chem. Sci.  (2017) –; doi:10.1039/C7SC00964J

data_1546296
_publ_section_title
;
 Diversity-Oriented Synthesis of Heterocycles and Macrocycles by
 Controlled Reactions of Oxetanes with \a-Iminocarbenes
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC00964J
_journal_year                    2017
_chemical_formula_moiety         'C20 H25 N O3 S'
_chemical_formula_sum            'C20 H25 N O3 S'
_chemical_formula_weight         359.47
_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     direct
_audit_creation_date             2015-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                70.135(3)
_cell_angle_beta                 77.897(3)
_cell_angle_gamma                68.067(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3686(4)
_cell_length_b                   10.3246(4)
_cell_length_c                   12.6600(5)
_cell_measurement_reflns_used    9074
_cell_measurement_temperature    180.1(9)
_cell_measurement_theta_max      73.2560
_cell_measurement_theta_min      4.8100
_cell_volume                     950.00(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.1(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega  -44.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000    0.0000 34

  2 omega  -65.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000  120.0000 60

  3 omega   47.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -157.0000  121.0000 67

  4 omega   29.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000   30.0000 76

  5 omega   32.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   30.0000 67

  6 omega   57.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   51.0000  -70.2693 34

  7 omega   79.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 42

  8 omega  142.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 26

  9 omega  114.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -18.5739 32

 10 omega  115.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   32.9482 32

 11 omega  113.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000   30.0000 65

 12 omega  110.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   90.0000 26

 13 omega  102.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000  154.1851 38

 14 omega   80.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   60.0000 44

 15 omega   77.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000    0.0000 29

 16 omega   81.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000    0.0000 94

 17 omega   87.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000 -131.0863 64

 18 omega   77.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -76.2649 58

 19 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -150.0000 26

 20 omega   77.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -120.0000 76

 21 omega   74.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -30.0000 68

 22 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -90.0000 26

 23 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 26

 24 omega   77.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 74

 25 omega   74.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   30.0000 25

 26 omega   75.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   60.0000 102

 27 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  150.0000 27

 28 omega   82.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  120.0000 57

 29 omega   76.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  150.0000 66

 30 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   90.0000 27

 31 omega   74.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 103

 32 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   90.0000 26

 33 omega   61.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   32.9482 26

 34 omega   77.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -30.0000 34

 35 omega   74.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -150.0000 25

 36 omega   74.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -180.0000 89

 37 omega   58.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000  -90.0000 66

 38 omega   60.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  178.0000 -120.0000 89

 39 omega   33.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000 -131.0863 29

 40 omega   29.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -76.2649 31

 41 omega   28.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -18.5739 35

 42 omega   36.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   14.5661 26

 43 omega   36.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   68.1148 72

 44 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   32.9482 26

 45 omega   16.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   98.5203 30

 46 omega   24.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000  154.1851 61

 47 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -45.7726 25

 48 omega   16.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000 -146.1132 25

 49 omega  -68.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   57.0000  -30.0000 107

 50 omega   26.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -30.0000 66

 51 omega   25.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -150.0000 82

 52 omega -117.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000 -150.0000 111

 53 omega -117.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000    0.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0568756000
_diffrn_orient_matrix_UB_12      -0.0677274000
_diffrn_orient_matrix_UB_13      -0.0987191000
_diffrn_orient_matrix_UB_21      0.0720172000
_diffrn_orient_matrix_UB_22      -0.1522180000
_diffrn_orient_matrix_UB_23      0.0830244000
_diffrn_orient_matrix_UB_31      -0.1769728000
_diffrn_orient_matrix_UB_32      -0.0215099000
_diffrn_orient_matrix_UB_33      0.0159452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14320
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.418
_diffrn_reflns_theta_min         3.729
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.4844
_exptl_crystal_size_mid          0.2604
_exptl_crystal_size_min          0.1423
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0861P)^2^+0.5692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3464
_reflns_number_total             3724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00964j2.cif
_cod_data_source_block           ajgi230
_cod_original_cell_volume        950.00(7)
_cod_database_code               1546296
_chemical_oxdiff_formula         'C20 H25 N O3 S'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N11-H11
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'