Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.
Maslivetc, Vladimir A.; Frolova, Liliya V.; Rogelj, Snezna; Maslivetc, Anna A.; Rubina, Marina; Rubin, Michael; The Journal of organic chemistry 83 (2018) 13743–13753; doi:10.1021/acs.joc.8b02062

data_4034882
_publ_section_title
;
 Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and
 Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with
 Tethered Carbamates.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13743
_journal_page_last               13753
_journal_paper_doi               10.1021/acs.joc.8b02062
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H27 Cl N2 O3'
_chemical_formula_sum            'C24 H27 Cl N2 O3'
_chemical_formula_weight         426.92
_chemical_name_systematic
'(1S,7S)-tert-butyl 5-benzyl-7-(3-chlorophenyl)-6-oxo-2,5-diazabicyclo[5.1.0]octane-2-carboxylate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4593(2)
_cell_length_b                   6.82970(10)
_cell_length_c                   13.4353(2)
_cell_measurement_reflns_used    10910
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8630
_cell_measurement_theta_min      3.6200
_cell_volume                     1119.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -114.00 -15.00   1.00    1.50    --  -41.72 -50.00  12.00   99
  2  \w    -68.00  31.00   1.00    1.50    --  -41.72  50.00 159.00   99
  3  \w     15.00 114.00   1.00    1.50    --   41.72  50.00 159.00   99
  4  \w     97.00 160.00   1.00    6.00    --  112.00  50.00 159.00   63
  5  \w    105.00 131.00   1.00    6.00    --  112.00 -50.00  12.00   26
  6  \w     60.00  96.00   1.00    6.00    --  112.00 -50.00  12.00   36
  7  \w    -68.00  -2.00   1.00    1.50    --  -41.72 125.00  60.00   66
  8  \w     29.00  94.00   1.00    1.50    --   41.72-125.00   0.00   65
  9  \w     -6.00  19.00   1.00    1.50    --   41.72 -50.00  12.00   25
 10  \w     23.00  93.00   1.00    1.50    --   41.72-125.00 -90.00   70
 11  \w     31.00  88.00   1.00    6.00    --  112.00 -95.00  60.00   57
 12  \w     80.00 140.00   1.00    6.00    --  112.00 -61.00 150.00   60
 13  \w     31.00  84.00   1.00    6.00    --  112.00 -95.00  30.00   53
 14  \w     37.00 130.00   1.00    6.00    --  112.00 -30.00-180.00   93
 15  \w    148.00 178.00   1.00    6.00    --  112.00  45.00 120.00   30
 16  \w     31.00  59.00   1.00    6.00    --  112.00 -95.00-150.00   28
 17  \w    129.00 176.00   1.00    6.00    --  112.00  15.00  90.00   47
 18  \w     45.00  71.00   1.00    6.00    --  112.00 -61.00 150.00   26
 19  \w     64.00  91.00   1.00    6.00    --  112.00  15.00  90.00   27
 20  \w     87.00 142.00   1.00    6.00    --  112.00  45.00 120.00   55
 21  \w     36.00 100.00   1.00    6.00    --  112.00-111.00-120.00   64
 22  \w   -113.00 -87.00   1.00    1.50    --  -41.85 -50.00  12.00   26
 23  \w     40.00  65.00   1.00    1.50    --   41.85  38.00 -90.00   25
 24  \w     73.00  98.00   1.00    1.50    --   41.85-125.00-180.00   25
 25  \w     68.00 110.00   1.00    1.50    --   41.85  38.00 -90.00   42
 26  \w     12.00  37.00   1.00    1.50    --   46.00  84.00 -75.25   25
 27  \w     38.00 105.00   1.00    1.50    --   66.00  55.00 -35.70   67
 28  \w     79.00 105.00   1.00    6.00    --  112.00  77.00-150.00   26
 29  \w     83.00 109.00   1.00    6.00    --  112.00  61.00-120.00   26
 30  \w    135.00 169.00   1.00    6.00    --  112.00  77.00-180.00   34
 31  \w     86.00 113.00   1.00    6.00    --  112.00  45.00 -90.00   27
 32  \w    128.00 168.00   1.00    6.00    --  112.00  77.00-120.00   40
 33  \w     84.00 162.00   1.00    6.00    --  112.00  61.00 -90.00   78
 34  \w     87.00 161.00   1.00    6.00    --  112.00  45.00 -60.00   74
 35  \w     79.00 104.00   1.00    6.00    --  112.00  77.00 -90.00   25
 36  \w     90.00 116.00   1.00    6.00    --  112.00  61.00-150.00   26
 37  \w    127.00 153.00   1.00    6.00    --  112.00  61.00-150.00   26
 38  \w    123.00 172.00   1.00    6.00    --  112.00  77.00-150.00   49
 39  \w     80.00 137.00   1.00    6.00    --  112.00  77.00 -60.00   57
 40  \w     79.00 105.00   1.00    6.00    --  112.00  77.00-120.00   26
 41  \w     89.00 115.00   1.00    6.00    --  112.00  61.00 -60.00   26
 42  \w     59.00 105.00   1.00    6.00    --  112.00  15.00 -90.00   46
 43  \w    -43.00 -18.00   1.00    1.50    --  -41.85  50.00 159.00   25
 44  \w     84.00 109.00   1.00    6.00    --  112.00  61.00 -90.00   25
 45  \w    -43.00 -18.00   1.00    1.50    --  -41.85  50.00 159.00   25
 46  \w     84.00 109.00   1.00    6.00    --  112.00  61.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1214901000
_diffrn_orient_matrix_UB_12      -0.0101324000
_diffrn_orient_matrix_UB_13      0.0080980000
_diffrn_orient_matrix_UB_21      0.0303593000
_diffrn_orient_matrix_UB_22      -0.1359792000
_diffrn_orient_matrix_UB_23      0.0928757000
_diffrn_orient_matrix_UB_31      0.0161102000
_diffrn_orient_matrix_UB_32      0.1796910000
_diffrn_orient_matrix_UB_33      0.0707693000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_min         3.622
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method
'Compound was cristalized from Hexane-Ethyl Acetate mixture'
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.406(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0515P)^2^+0.2109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4389
_reflns_number_total             4558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02062_si_005.cif
_cod_data_source_block           anna_29092017_vm355_6
_cod_database_code               4034882
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C24H27FN2O3
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.594(17)
 0.406(17)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C19(H19), C10(H10), C12(H12), C16(H16), C11(H11), C17(H17),
 C18(H18)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              60434
_shelx_hkl_checksum              5100
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue'
_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 2.194
_oxdiff_exptl_absorpt_empirical_full_min 0.433