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_4034883
_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         'C30 H32 N2 O3'
_chemical_formula_sum            'C30 H32 N2 O3'
_chemical_formula_weight         468.57
_chemical_name_systematic
'tert-butyl 6-oxo-5,7,8-triphenyl-2,5-diazabicyclo[5.1.0]octane-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             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.7896(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   46.2855(8)
_cell_length_b                   9.98373(17)
_cell_length_c                   11.17619(19)
_cell_measurement_reflns_used    18372
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8140
_cell_measurement_theta_min      4.4960
_cell_volume                     5128.32(15)
_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 10.5059
_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    -12.00  31.00   0.50    1.00    --  -41.72  70.00   2.00   86
  2  \w    -70.00 -17.00   0.50    1.00    --  -41.72  70.00   2.00  106
  3  \w     12.00  70.00   0.50    1.00    --   41.72 -99.00  60.00  116
  4  \w     36.00 140.00   0.50    4.00    --  112.00 -30.00  60.00  208
  5  \w     88.00 174.00   0.50    4.00    --  112.00  30.00  30.00  172
  6  \w    140.00 166.00   0.50    4.00    --  112.00  70.00   2.00   52
  7  \w    132.00 173.00   0.50    4.00    --  112.00  61.00  90.00   82
  8  \w     90.00 116.00   0.50    4.00    --  112.00  70.00   2.00   52
  9  \w     85.00 111.00   0.50    4.00    --  112.00  61.00  90.00   52
 10  \w    151.00 177.00   0.50    4.00    --  112.00 111.00-120.00   52
 11  \w    116.00 142.00   0.50    4.00    --  112.00 111.00-150.00   52
 12  \w     66.00  92.00   0.50    4.00    --  112.00 -45.00-150.00   52
 13  \w     96.00 137.00   0.50    4.00    --  112.00 -45.00-150.00   82
 14  \w    101.00 137.00   0.50    4.00    --  112.00 -61.00-180.00   72
 15  \w     89.00 139.00   0.50    6.00    --  112.00 -70.00-129.00  100
 16  \w     44.00 116.00   0.50    6.00    --  112.00-111.00-150.00  144
 17  \w     44.00  95.00   0.50    6.00    --  112.00 -61.00-180.00  102
 18  \w     28.00  83.00   0.50    1.50    --   41.72-125.00-150.00  110
 19  \w     36.00 106.00   0.50    6.00    --  112.00 -95.00  60.00  140
 20  \w     75.00 100.00   0.50    6.00    --  112.00-111.00  60.00   50
 21  \w   -104.00 -20.00   0.50    1.50    --  -41.72 -70.00-129.00  168
 22  \w    -46.00  20.00   0.50    1.50    --  -41.72  38.00-180.00  132
 23  \w     68.00  94.00   0.50    6.00    --  112.00 -95.00  90.00   52
 24  \w    104.00 130.00   0.50    6.00    --  112.00 111.00 120.00   52
 25  \w     30.00  61.00   0.50    6.00    --  112.00 -95.00  90.00   62
 26  \w    138.00 164.00   0.50    6.00    --  112.00  30.00 -90.00   52
 27  \w    129.00 155.00   0.50    6.00    --  112.00 111.00-180.00   52
 28  \w     61.00  87.00   0.50    6.00    --  112.00 178.00-120.00   52
 29  \w    117.00 143.00   0.50    6.00    --  112.00 178.00-120.00   52
 30  \w     89.00 122.00   0.50    6.00    --  112.00 178.00 120.00   66
 31  \w     98.00 124.00   0.50    6.00    --  112.00  30.00 -90.00   52
 32  \w     81.00 106.00   0.50    6.00    --  112.00  77.00 120.00   50
 33  \w    152.00 159.50   0.50    6.00    --  112.00  77.00 120.00   15
;
_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      -0.0287102000
_diffrn_orient_matrix_UB_12      0.0597868000
_diffrn_orient_matrix_UB_13      0.0330176000
_diffrn_orient_matrix_UB_21      0.0010886000
_diffrn_orient_matrix_UB_22      0.1079120000
_diffrn_orient_matrix_UB_23      -0.0979682000
_diffrn_orient_matrix_UB_31      -0.0172838000
_diffrn_orient_matrix_UB_32      -0.0926829000
_diffrn_orient_matrix_UB_33      -0.0926955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38486
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_min         3.847
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.909
_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    1.214
_exptl_crystal_description       prism
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.294
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         10467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0896P)^2^+1.5698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9749
_reflns_number_total             10467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02062_si_003.cif
_cod_data_source_block           anna_29092017_vm402_7
_cod_database_code               4034883
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C30H32N2O3
_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:
 C3(H3), C2(H2), C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C38(H38A,H38B), C4(H4A,H4B), C10(H10A,H10B), C31(H31A,H31B),
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C46(H46), C32(H32), C40(H40), C20(H20), C24(H24), C36(H36), C14(H14),
 C44(H44), C51(H51), C21(H21), C22(H22), C18(H18), C43(H43), C23(H23), C33(H33),
  C15(H15), C41(H41), C17(H17), C42(H42), C47(H47), C48(H48), C49(H49),
 C16(H16), C25(H25), C35(H35), C34(H34), C29(H29), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C54(H54A,H54B,H54C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C53(H53A,H53B,H53C), C57(H57A,H57B,H57C)
;
_shelx_res_checksum              12062
_shelx_hkl_checksum              87870
_olex2_exptl_crystal_mounting_method
'A fragment of single crystal was mounted on the glass stick by acrylic glue. Then it was placed into diffractometer.'
_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 2.835
_oxdiff_exptl_absorpt_empirical_full_min 0.729