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_1546294
_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         'C29 H40 Br N O5 S'
_chemical_formula_sum            'C29 H40 Br N O5 S'
_chemical_formula_weight         594.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.017(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0045(3)
_cell_length_b                   12.0323(2)
_cell_length_c                   17.8455(4)
_cell_measurement_reflns_used    12668
_cell_measurement_temperature    180.10(14)
_cell_measurement_theta_max      72.5620
_cell_measurement_theta_min      3.1290
_cell_volume                     2961.24(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.10(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -117.00  -11.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615  -37.0000   90.0000 212

  2 omega -117.00  -28.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615  -37.0000  -60.0000 178

  3 omega  -71.00  -23.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615   77.0000  -60.0000 96

  4 omega  -67.00   34.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615   57.0000   90.0000 202

  5 omega  -22.00   42.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615   37.0000 -120.0000 128

  6 omega   17.00   58.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615   57.0000  -30.0000 82

  7 omega   73.00  100.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   30.0000  -60.0000 54

  8 omega   80.00  107.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -77.0000   60.0000 54

  9 omega   39.00   96.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716 -112.0000   30.0000 114

 10 omega   40.00   66.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -77.0000   60.0000 52

 11 omega   44.00  109.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -94.0000   60.0000 130

 12 omega   75.00  105.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   61.0000 -120.0000 60

 13 omega  132.00  177.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   61.0000 -120.0000 90

 14 omega   29.00   61.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -30.0000  -60.0000 64

 15 omega   50.00   91.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -30.0000 -120.0000 82

 16 omega   37.00   96.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716 -112.0000 -150.0000 118

 17 omega   43.00   87.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -30.0000 -180.0000 88

 18 omega   70.00  171.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   30.0000  -30.0000 202

 19 omega  112.00  174.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   77.0000   60.0000 124

 20 omega   75.00  101.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   61.0000  -90.0000 52

 21 omega  129.00  161.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   30.0000  -60.0000 64

 22 omega   29.00   87.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -30.0000  -30.0000 116

 23 omega   50.00   99.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716  -45.0000   60.0000 98

 24 omega   98.00  177.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      108.1716   45.0000 -150.0000 158
;
_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      0.0290934000
_diffrn_orient_matrix_UB_12      0.0059392000
_diffrn_orient_matrix_UB_13      -0.0791616000
_diffrn_orient_matrix_UB_21      -0.0700013000
_diffrn_orient_matrix_UB_22      -0.0961489000
_diffrn_orient_matrix_UB_23      -0.0272319000
_diffrn_orient_matrix_UB_31      -0.0821264000
_diffrn_orient_matrix_UB_32      0.0844370000
_diffrn_orient_matrix_UB_33      -0.0258385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20048
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.582
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.850
_exptl_absorpt_correction_T_max  0.538
_exptl_absorpt_correction_T_min  0.297
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.334
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.7111
_exptl_crystal_size_mid          0.5249
_exptl_crystal_size_min          0.2855
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.9863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5560
_reflns_number_total             5813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00964j2.cif
_cod_data_source_block           ajgi-19-2-3
_cod_original_cell_volume        2961.25(11)
_cod_database_code               1546294
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C29 H40 Br1 N1 O5 S1'
_reflns_odcompleteness_completeness 99.98
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C27(H27A,H27B), C16(H16A,H16B), C26(H26A,H26B), C11(H11A,H11B),
 C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C18(H18), C5(H5), C7(H7), C8(H8), C20(H20), C10(H10),
 C13(H13), C21(H21)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,
 H1BC), C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,H1DC)
;
_olex2_submission_special_instructions 'No special instructions were received'