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_4034881
_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_formula_moiety         'C25 H28 Br F N2 O3'
_chemical_formula_sum            'C25 H28 Br F N2 O3'
_chemical_formula_weight         503.40
_chemical_name_systematic
'(1S,8S)-tert-butyl 8-(3-bromophenyl)-6-(4-fluorobenzyl)-7-oxo-2,6-diazabicyclo[6.1.0]nonane-2-carboxylate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.944(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2579(2)
_cell_length_b                   26.1617(4)
_cell_length_c                   6.91560(10)
_cell_measurement_reflns_used    6264
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.0800
_cell_measurement_theta_min      4.7800
_cell_volume                     2346.74(6)
_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 0.996
_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    -63.00  21.00   1.00    1.00    --  -41.72  57.00 -30.00   84
  2  \w   -101.00 -32.00   1.00    1.00    --  -41.72 -38.00 150.00   69
  3  \w     67.00  98.00   1.00    1.00    --   41.72-125.00   0.00   31
  4  \w     42.00  92.00   1.00    1.00    --   41.72-125.00-120.00   50
  5  \w     44.00 144.00   1.00    4.00    --  112.00 -77.00-120.00  100
  6  \w     84.00 125.00   1.00    4.00    --  112.00  30.00 -90.00   41
  7  \w     87.00 113.00   1.00    4.00    --  112.00  45.00  30.00   26
  8  \w    129.00 157.00   1.00    4.00    --  112.00  45.00  30.00   28
  9  \w    125.00 178.00   1.00    4.00    --  112.00  61.00 120.00   53
 10  \w    105.00 131.00   1.00    4.00    --  112.00  90.00 130.00   26
 11  \w    101.00 174.00   1.00    4.00    --  112.00 111.00 -30.00   73
 12  \w     46.00 119.00   1.00    4.00    --  112.00 -30.00  30.00   73
 13  \w     54.00  80.00   1.00    4.00    --  112.00 -95.00  60.00   26
 14  \w     31.00 108.00   1.00    4.00    --  112.00 -95.00  90.00   77
 15  \w     31.00  75.00   1.00    4.00    --  112.00 -95.00-120.00   44
 16  \w     57.00 107.00   1.00    4.00    --  112.00-111.00-180.00   50
;
_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      -0.1030861000
_diffrn_orient_matrix_UB_12      -0.0149825000
_diffrn_orient_matrix_UB_13      0.0541100000
_diffrn_orient_matrix_UB_21      0.0469039000
_diffrn_orient_matrix_UB_22      -0.0514837000
_diffrn_orient_matrix_UB_23      0.0815114000
_diffrn_orient_matrix_UB_31      0.0357490000
_diffrn_orient_matrix_UB_32      0.0243331000
_diffrn_orient_matrix_UB_33      0.2056368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_min         3.804
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.425
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Compound was cristalized from Hexane-Ethyl Acetate mixtures'
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+1.0019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4205
_reflns_number_total             4785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02062_si_004.cif
_cod_data_source_block           anna_vm373_1
_cod_database_code               4034881
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.72
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C19(H19), C20(H20), C14(H14), C10(H10), C13(H13), C11(H11)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              428
_shelx_hkl_checksum              3132
_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 1.896
_oxdiff_exptl_absorpt_empirical_full_min 0.679