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_1546297
_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         'C19 H29 N O4 S'
_chemical_formula_sum            'C19 H29 N O4 S'
_chemical_formula_weight         367.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1557(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4991(2)
_cell_length_b                   5.67440(6)
_cell_length_c                   20.5923(3)
_cell_measurement_reflns_used    7438
_cell_measurement_temperature    181(2)
_cell_measurement_theta_max      73.9240
_cell_measurement_theta_min      4.4650
_cell_volume                     1953.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      181(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -78.00  30.00   1.00    2.00    --  -39.51  19.00  30.00  108
  2  \w    -46.00  30.00   1.00    2.00    --  -39.51  38.00  60.00   76
  3  \w   -129.00 -35.00   1.00    2.00    --  -39.51-178.00   0.00   94
  4  \w    -35.00  24.00   1.00    2.00    --   39.51 -77.00-120.00   59
  5  \w     43.00  74.00   1.00    2.00    --   39.51 -99.00 150.00   31
  6  \w     83.00 127.00   1.00    2.00    --   39.51 178.00  30.00   44
  7  \w     49.00 107.00   1.00   10.00    --  109.05 -94.00  90.00   58
  8  \w     95.00 171.00   1.00   10.00    --  109.05 125.00  30.00   76
  9  \w     40.00  85.00   1.00   10.00    --  109.05 -45.00  60.00   45
 10  \w     38.00  89.00   1.00   10.00    --  109.05 -30.00   0.00   51
 11  \w     40.00  95.00   1.00   10.00    --  109.05 -45.00 -90.00   55
 12  \w     84.00 178.00   1.00   10.00    --  109.05  30.00 150.00   94
 13  \w     36.00 101.00   1.00   10.00    --  109.05-108.00  58.00   65
 14  \w     38.00  65.00   1.00   10.00    --  109.05 -94.00-180.00   27
 15  \w    153.00 178.00   1.00   10.00    --  109.05  45.00 -60.00   25
 16  \w     95.00 121.00   1.00   10.00    --  109.05  45.00 -60.00   26
 17  \w     58.00  90.00   1.00   10.00    --  109.05 -30.00-150.00   32
 18  \w     84.00 120.00   1.00   10.00    --  109.05  45.00-180.00   36
 19  \w    134.00 175.00   1.00   10.00    --  109.05  45.00-180.00   41
 20  \w     68.00 121.00   1.00   10.00    --  109.05-125.00-120.00   53
 21  \w     37.00  93.00   1.00   10.00    --  109.05 -45.00 150.00   56
 22  \w     58.00 100.00   1.00   10.00    --  109.05 -98.00 -41.00   42
;
_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      -0.0303506000
_diffrn_orient_matrix_UB_12      -0.2508354000
_diffrn_orient_matrix_UB_13      -0.0221729000
_diffrn_orient_matrix_UB_21      -0.0014957000
_diffrn_orient_matrix_UB_22      -0.0544382000
_diffrn_orient_matrix_UB_23      0.0729054000
_diffrn_orient_matrix_UB_31      -0.0869763000
_diffrn_orient_matrix_UB_32      0.0885170000
_diffrn_orient_matrix_UB_33      -0.0179771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.911
_diffrn_reflns_theta_min         4.492
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.683
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0661P)^2^+0.3514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3513
_reflns_number_total             3874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00964j2.cif
_cod_data_source_block           ajgi409-2-4
_cod_original_cell_volume        1953.78(4)
_cod_database_code               1546297
_chemical_oxdiff_formula         'C19 H29 N1 O4 S1'
_reflns_odcompleteness_completeness 99.90
_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), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.358