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_4034884
_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 rm
_chemical_formula_moiety         'C27 H33 F N2 O3'
_chemical_formula_sum            'C27 H33 F N2 O3'
_chemical_formula_weight         452.55
_chemical_name_systematic
'(1S,4S,7S)-tert-butyl 5-benzyl-7-(4-hydroxyphenyl)-4-isopropyl-6-oxo-2,5-diazabicyclo[5.1.0]octane-2-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.12470(10)
_cell_length_b                   13.30320(10)
_cell_length_c                   18.00260(10)
_cell_measurement_reflns_used    32912
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      75.9080
_cell_measurement_theta_min      4.0950
_cell_volume                     2424.79(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      99(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -91.00   6.00   1.00    1.00    --  -41.72 116.00  13.00   97
  2  \w    -37.00  77.00   1.00    1.00    --   41.72 -23.00 127.00  114
  3  \w     77.00 178.00   1.00    1.00    --  112.00  23.00 -67.00  101
  4  \w     37.00 118.00   1.00    1.00    --  112.00-116.00 -74.00   81
  5  \w    101.00 178.00   1.00    1.00    --  112.00 105.00 111.00   77
  6  \w   -114.00 -14.00   1.00    1.00    --  -41.72 -57.00 -60.00  100
  7  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 150.00   80
  8  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
  9  \w    100.00 178.00   1.00    1.00    --  112.00 111.00-180.00   78
 10  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00  30.00   80
 11  \w    100.00 178.00   1.00    1.00    --  112.00 111.00   0.00   78
 12  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 -30.00   80
 13  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00 -90.00  109
 14  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-180.00  109
 15  \w   -114.00 -14.00   1.00    1.00    --  -41.72 -57.00-150.00  100
 16  \w   -114.00 -14.00   1.00    1.00    --  -41.72 -57.00 120.00  100
 17  \w      9.00 118.00   1.00    1.00    --   41.72  77.00  60.00  109
 18  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-150.00   99
 19  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 120.00   80
 20  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 21  \w     84.00 178.00   1.00    1.00    --  112.00  30.00-180.00   94
 22  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  60.00   95
 23  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   99
 24  \w     83.00 178.00   1.00    1.00    --  112.00  61.00-180.00   95
 25  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 120.00   94
 26  \w     59.00 178.00   1.00    1.00    --  112.00  15.00  60.00  119
 27  \w      9.00 118.00   1.00    1.00    --   41.72  77.00 150.00  109
 28  \w      1.00  83.00   1.00    1.00    --   41.72 -99.00 120.00   82
 29  \w      1.00  83.00   1.00    1.00    --   41.72 -99.00 -30.00   82
 30  \w     61.00 111.00   1.00    1.00    --  112.00-111.00-120.00   50
 31  \w     89.00 115.00   1.00    1.00    --  112.00  45.00   0.00   26
 32  \w    106.00 142.00   1.00    1.00    --  112.00 178.00  60.00   36
 33  \w     66.00  92.00   1.00    1.00    --  112.00-111.00  90.00   26
 34  \w     86.00 112.00   1.00    1.00    --  112.00 178.00 -90.00   26
 35  \w    102.00 128.00   1.00    1.00    --  112.00 -45.00 -90.00   26
 36  \w    116.00 164.00   1.00    1.00    --  112.00   0.00  60.00   48
;
_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      0.0393657000
_diffrn_orient_matrix_UB_12      -0.0988197000
_diffrn_orient_matrix_UB_13      -0.0387311000
_diffrn_orient_matrix_UB_21      0.0228753000
_diffrn_orient_matrix_UB_22      0.0577114000
_diffrn_orient_matrix_UB_23      -0.0730532000
_diffrn_orient_matrix_UB_31      0.1452019000
_diffrn_orient_matrix_UB_32      0.0177164000
_diffrn_orient_matrix_UB_33      0.0220265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.478
_diffrn_reflns_theta_min         4.132
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.571
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0259
_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^)+(0.0377P)^2^+0.3638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0670
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4918
_reflns_number_total             4964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02062_si_002.cif
_cod_data_source_block           anna23062018_masliv_2
_cod_database_code               4034884
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Ternary CH refined with riding coordinates:
 C5(H5), C19(H19), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C23(H23), C16(H16), C18(H18), C17(H17), C14(H14), C15(H15),
 C24(H24), C26(H26)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C11(H11A,H11B,
 H11C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              48181
_shelx_hkl_checksum              59246
_olex2_exptl_crystal_mounting_method
'A fragment of crystal was placed 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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.659