Enantioselective Deprotonative Ring Contraction of N1-Methyl-N4-Boc-benzo[e][1,4]diazepine-2,5-diones.
Antolak, Stephanie A.; Yao, Zhong-Ke; Richoux, Gary M.; Slebodnick, Carla; Carlier, Paul R.; Organic letters 16 (2014) 5204–5207; doi:10.1021/ol502586n

data_1517816
_publ_section_title
;
 Enantioselective Deprotonative Ring Contraction of
 N1-Methyl-N4-Boc-benzo[e][1,4]diazepine-2,5-diones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5204
_journal_page_last               5207
_journal_paper_doi               10.1021/ol502586n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C13 H16 N2 O2 S'
_chemical_formula_sum            'C13 H16 N2 O2 S'
_chemical_formula_weight         264.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-08-18
_audit_creation_method
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Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.97246(7)
_cell_length_b                   14.38622(13)
_cell_length_c                   10.17414(8)
_cell_measurement_reflns_used    17150
_cell_measurement_temperature    99.90(14)
_cell_measurement_theta_max      74.7370
_cell_measurement_theta_min      3.0540
_cell_volume                     1293.145(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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;
  1 omega -118.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419 -125.0000 -150.0000 45

  2 omega  -98.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  125.0000 -143.0000 96

  3 omega   12.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   37.0000  150.0000 105

  4 omega   15.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   30.0000 100

  5 omega   15.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000  150.0000 100

  6 omega   22.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -120.0000 82

  7 omega   30.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -60.0000 39

  8 omega   30.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  120.0000 39

  9 omega   33.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   30.0000 44

 10 omega   22.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -30.0000 74

 11 omega   77.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000   30.0000 101

 12 omega   33.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  120.0000 103

 13 omega   73.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -180.0000 105

 14 omega   30.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 39

 15 omega   27.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   60.0000 88

 16 omega   22.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  150.0000 87

 17 omega   33.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -120.0000 44

 18 omega   27.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -60.0000 74

 19 omega   79.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000   90.0000 99

 20 omega   27.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 88

 21 omega   27.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  150.0000 88

 22 omega   30.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   30.0000 39

 23 omega   33.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -150.0000 44

 24 omega   77.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000   60.0000 101

 25 omega   28.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  -30.0000 113

 26 omega   27.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   90.0000 88

 27 omega -117.00  -62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419 -145.0000  -28.0000 55

 28 omega   15.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000  -90.0000 100

 29 omega    8.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   77.0000  -30.0000 112

 30 omega   15.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000 -150.0000 100

 31 omega    2.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419 -125.0000  120.0000 96

 32 omega   73.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  125.0000  -90.0000 46

 33 omega   77.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000  -60.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0123373000
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_diffrn_orient_matrix_UB_23      0.0749156000
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
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_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_max         74.767
_diffrn_reflns_theta_min         4.413
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
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_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Crystallized from H2O / ethanol / ethyl acetate. Formed giant plated. Cut off an irregular shaped chunk from one of the plates.'
_exptl_crystal_size_max          0.3378
_exptl_crystal_size_mid          0.269
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_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.172(18)
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_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5257
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0350
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.3852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502586n_si_001.cif
_cod_data_source_block           cs2053
_cod_depositor_comments
'Adding full bibliography for 1517816--1517819.cif.'
_cod_original_cell_volume        1293.14(2)
_cod_database_code               1517816
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C13 H16 N2 O2 S'
_chemical_oxdiff_usercomment     'Zhongke Yao / Carlier ( zky-I-171LS)'
_reflns_odcompleteness_completeness 99.92
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
;
_olex2_exptl_crystal_mounting_method 'Mounted on a Cryoloop with Krytox oil.'
_olex2_submission_original_sample_id ZKY-I-171LS
_olex2_submission_special_instructions 'No special instructions were received'