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_1546295
_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         'C32 H42 N2 O7 S'
_chemical_formula_sum            'C32 H42 N2 O7 S'
_chemical_formula_weight         598.73
_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             2014-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                96.6637(11)
_cell_angle_beta                 102.3792(13)
_cell_angle_gamma                102.1801(12)
_cell_formula_units_Z            2
_cell_length_a                   8.58394(13)
_cell_length_b                   10.36548(13)
_cell_length_c                   19.8233(3)
_cell_measurement_reflns_used    5482
_cell_measurement_temperature    210.00(14)
_cell_measurement_theta_max      72.5770
_cell_measurement_theta_min      4.4070
_cell_volume                     1659.82(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_temperature      210.00(14)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1377539000
_diffrn_orient_matrix_UB_12      0.1139263000
_diffrn_orient_matrix_UB_13      -0.0089385000
_diffrn_orient_matrix_UB_21      0.0661729000
_diffrn_orient_matrix_UB_22      0.0355329000
_diffrn_orient_matrix_UB_23      0.0801794000
_diffrn_orient_matrix_UB_31      0.1119243000
_diffrn_orient_matrix_UB_32      -0.0977520000
_diffrn_orient_matrix_UB_33      -0.0027905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11170
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.412
_diffrn_reflns_theta_min         4.427
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3551
_exptl_crystal_size_mid          0.2181
_exptl_crystal_size_min          0.0347
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0620P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5656
_reflns_number_total             6391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00964j2.cif
_cod_data_source_block           agi-7z-1
_cod_original_cell_volume        1659.83(4)
_cod_database_code               1546295
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C32 H42 N2 O7 S1'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C15(H15A,H15B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C20(H20), C21(H21), C22(H22), C23(H23), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C41(H41A,H41B,H41C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              8228