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_1546299
_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 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_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     dual
_audit_creation_date             2016-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.545(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0583(3)
_cell_length_b                   12.1489(3)
_cell_length_c                   13.6776(3)
_cell_measurement_reflns_used    7501
_cell_measurement_temperature    180
_cell_measurement_theta_max      73.7180
_cell_measurement_theta_min      3.2470
_cell_volume                     1817.14(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      180
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  33.00   1.00    1.00    --  -37.56  57.00  30.00   99
  2  \w     81.00 122.00   1.00    1.00    --   37.56 178.00 120.00   41
  3  \w    106.00 169.00   1.00    1.50    --  110.40 111.00  60.00   63
  4  \w    103.00 176.00   1.00    1.50    --  110.40 110.00 165.00   73
  5  \w     82.00 146.00   1.00    1.50    --  110.40 -30.00 120.00   64
  6  \w     86.00 114.00   1.00    1.50    --  110.40-111.00   0.00   28
  7  \w     66.00 140.00   1.00    1.50    --  110.40 -30.00  60.00   74
  8  \w     89.00 171.00   1.00    1.50    --  110.40  45.00 -90.00   82
  9  \w     74.00 177.00   1.00    1.50    --  110.40  77.00-150.00  103
 10  \w     82.00 107.00   1.00    1.50    --  110.40 -94.00-180.00   25
 11  \w     45.00 102.00   1.00    1.50    --  110.40-111.00 -60.00   57
 12  \w     81.00 127.00   1.00    1.00    --   37.56-178.00 -90.00   46
 13  \w     34.00  65.00   1.00    1.50    --  110.40-111.00   0.00   31
 14  \w     31.00 134.00   1.00    1.50    --  110.40 -77.00 120.00  103
 15  \w     47.00 110.00   1.00    1.50    --  110.40-111.00 120.00   63
 16  \w    -86.00 -11.00   1.00    1.00    --  -37.56 -57.00 -60.00   75
 17  \w   -116.00 -10.00   1.00    1.00    --  -37.56 -57.00-150.00  106
 18  \w   -109.00 -41.00   1.00    1.00    --  -37.56 178.00-180.00   68
 19  \w     64.00 136.00   1.00    1.50    --  110.40 178.00  90.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1036406000
_diffrn_orient_matrix_UB_12      -0.0598918000
_diffrn_orient_matrix_UB_13      -0.0670902000
_diffrn_orient_matrix_UB_21      -0.0348633000
_diffrn_orient_matrix_UB_22      0.1085222000
_diffrn_orient_matrix_UB_23      -0.0555271000
_diffrn_orient_matrix_UB_31      0.0885722000
_diffrn_orient_matrix_UB_32      -0.0272127000
_diffrn_orient_matrix_UB_33      -0.0734682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11597
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.588
_diffrn_reflns_theta_min         4.893
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.732
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0653P)^2^+0.7398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3360
_reflns_number_total             3592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00964j2.cif
_cod_data_source_block           ajgi543b
_cod_database_code               1546299
_chemical_oxdiff_formula         'C20 H23 N O3 S'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_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:
 C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C20(H20), C21(H21), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.791
_oxdiff_exptl_absorpt_empirical_full_min 0.460