Mixed carboxylic-sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction.
Bakulina, Olga; Dar'in, Dmitry; Krasavin, Mikhail; Organic & biomolecular chemistry 16 (2018) 3989–3998; doi:10.1039/c8ob00768c

data_7156249
_publ_section_title
;
 Mixed carboxylic-sulfonic anhydride in reaction with imines: a
 straightforward route to water-soluble \b-lactams via a Staudinger-type
 reaction.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3989
_journal_page_last               3998
_journal_paper_doi               10.1039/c8ob00768c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 N2 O6 S, C6 H16 N'
_chemical_formula_sum            'C24 H33 N3 O6 S'
_chemical_formula_weight         491.59
_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
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2017-05-05 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.834(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0398(14)
_cell_length_b                   8.7917(5)
_cell_length_c                   15.4377(11)
_cell_measurement_reflns_used    4799
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0270
_cell_measurement_theta_min      4.7810
_cell_volume                     2509.2(3)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9710
_diffrn_measurement_details
;
  1 omega  -70.00   29.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000 -120.0000 99

  2 omega -119.00   -7.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000  -60.0000 112

  3 omega  -30.00    2.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 32

  4 omega   43.00   71.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 28

  5 omega   42.00   90.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 48

  6 omega   63.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 46

  7 omega  146.00  175.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 29

  8 omega   42.00   68.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 26

  9 omega   39.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 56

 10 omega  110.00  137.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 27

 11 omega  143.00  176.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 33

 12 omega  114.00  140.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 26

 13 omega  151.00  176.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 25

 14 omega   40.00   91.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 51

 15 omega   87.00  139.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 52

 16 omega  107.00  139.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 32

 17 omega   48.00  100.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 52

 18 omega  -58.00  -31.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0693830000
_diffrn_orient_matrix_UB_12      -0.0562875000
_diffrn_orient_matrix_UB_13      -0.0251341000
_diffrn_orient_matrix_UB_21      0.0441693000
_diffrn_orient_matrix_UB_22      0.0376410000
_diffrn_orient_matrix_UB_23      0.0948975000
_diffrn_orient_matrix_UB_31      -0.0134064000
_diffrn_orient_matrix_UB_32      -0.1615568000
_diffrn_orient_matrix_UB_33      0.0305980000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_min         4.784
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29893
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4956
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0692P)^2^+2.7727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4128
_reflns_number_total             4956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00768c2.cif
_cod_data_source_block           103-428-6610dvd958
_cod_depositor_comments          'Adding full bibliography for 7156249.cif.'
_cod_database_code               7156249
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C24' = C24-C23
 1.51 with sigma of 0.005
 C23-C24'
 1.51 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C24') = Uanis(C24)
4. Others
 Fixed Sof: H23C(0.75) H23D(0.75) H23A(0.25) H23B(0.25) C24(0.75) H24A(0.75)
 H24B(0.75) H24C(0.75) C24'(0.25) H24D(0.25) H24E(0.25) H24F(0.25)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), N3(H3A)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C21(H21A,H21B), C19(H19A,H19B), C23(H23C,H23D),
 C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C18(H18), C14(H14), C15(H15), C11(H11), C10(H10), C17(H17)
5.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C24(H24A,H24B,
 H24C), C24'(H24D,H24E,H24F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'