Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity.
Maslivetc, Vladimir A.; Turner, Danielle N.; McNair, Kimberly N.; Frolova, Liliya; Rogelj, Snezna; Maslivetc, Anna A.; Aksenov, Nicolai A.; Rubina, Marina; Rubin, Michael; The Journal of organic chemistry 83 (2018) 5650–5664; doi:10.1021/acs.joc.8b00640

data_4034783
_publ_section_title
;
 Desymmetrization of Cyclopropenes via the Potassium-Templated
 Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols
 toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial
 Activity.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5650
_journal_page_last               5664
_journal_paper_doi               10.1021/acs.joc.8b00640
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 F N O2'
_chemical_formula_sum            'C23 H26 F N O2'
_chemical_formula_weight         367.45
_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                 90.4490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.83870(10)
_cell_length_b                   15.5575(2)
_cell_length_c                   15.9678(2)
_cell_measurement_reflns_used    20461
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      75.7990
_cell_measurement_theta_min      5.5200
_cell_volume                     1947.22(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      149.98(10)
_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 0.989
_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    -64.00   5.00   1.00    1.00    --  -41.60  74.00   4.00   69
  2  \w   -116.00 -19.00   1.00    1.00    --  -41.60 -38.00 150.00   97
  3  \w     35.00  85.00   1.00    1.00    --   41.60-131.00 173.00   50
  4  \w     42.00  83.00   1.00    4.00    --  112.00-131.00 173.00   41
  5  \w     31.00  65.00   1.00    4.00    --  112.00 -95.00  60.00   34
  6  \w     57.00  83.00   1.00    4.00    --  112.00 -46.00  41.00   26
  7  \w     77.00 103.00   1.00    4.00    --  112.00 -30.00   0.00   26
  8  \w     84.00 115.00   1.00    4.00    --  112.00  30.00 -90.00   31
  9  \w    121.00 148.00   1.00    4.00    --  112.00  46.00-168.00   27
 10  \w    104.00 176.00   1.00    4.00    --  112.00 111.00-180.00   72
 11  \w     93.00 139.00   1.00    4.00    --  112.00 178.00  30.00   46
 12  \w    102.00 127.00   1.00    4.00    --  112.00 111.00 120.00   25
 13  \w    140.00 166.00   1.00    4.00    --  112.00 111.00 120.00   26
 14  \w    117.00 154.00   1.00    4.00    --  112.00 111.00  60.00   37
 15  \w     96.00 136.00   1.00    4.00    --  112.00 -45.00 150.00   40
 16  \w     53.00  81.00   1.00    1.00    --   41.60 -99.00 -30.00   28
 17  \w     71.00  97.00   1.00    4.00    --  112.00 -74.00-124.00   26
 18  \w     73.00 101.00   1.00    4.00    --  112.00-111.00-120.00   28
 19  \w     37.00  98.00   1.00    4.00    --  112.00-111.00-180.00   61
 20  \w     37.00  91.00   1.00    4.00    --  112.00 -77.00-150.00   54
 21  \w     51.00 165.00   1.00    4.00    --  112.00 -15.00-180.00  114
 22  \w     37.00  95.00   1.00    4.00    --  112.00 -95.00 -30.00   58
 23  \w     32.00 125.00   1.00    4.00    --  112.00 -15.00  30.00   93
 24  \w     42.00 124.00   1.00    4.00    --  112.00 -30.00 120.00   82
 25  \w   -128.00 -20.00   1.00    1.00    --  -41.85   0.00  30.00  108
 26  \w     11.00  74.00   1.00    1.00    --   41.85 -99.00-120.00   63
 27  \w     33.00  59.00   1.00    4.00    --  112.00 -22.00 140.15   26
 28  \w     84.00 116.00   1.00    4.00    --  112.00-111.00-150.00   32
 29  \w     90.00 116.00   1.00    4.00    --  112.00  30.00   0.00   26
 30  \w     72.00 113.00   1.00    4.00    --  112.00-111.00 150.00   41
 31  \w     86.00 112.00   1.00    4.00    --  112.00-111.00  30.00   26
 32  \w     61.00 106.00   1.00    4.00    --  112.00 -95.00   0.00   45
 33  \w     60.00  86.00   1.00    4.00    --  112.00 -95.00-150.00   26
 34  \w     75.00 116.00   1.00    4.00    --  112.00-111.00 -90.00   41
 35  \w     62.00 108.00   1.00    4.00    --  112.00-140.00  -0.00   46
 36  \w    143.00 176.00   1.00    4.00    --  112.00  30.00   0.00   33
 37  \w     67.00 115.00   1.00    4.00    --  112.00-111.00  90.00   48
 38  \w     67.00 116.00   1.00    4.00    --  112.00-111.00 -30.00   49
 39  \w     30.00  58.00   1.00    4.00    --  112.00 -95.00   0.00   28
 40  \w     36.00  68.00   1.00    4.00    --  112.00-111.00  30.00   32
 41  \w    116.00 142.00   1.00    4.00    --  112.00 111.00 -60.00   26
 42  \w    149.00 175.00   1.00    4.00    --  112.00 111.00 -60.00   26
 43  \w     82.00 108.00   1.00    4.00    --  112.00 -22.00 140.15   26
 44  \w    115.00 178.00   1.00    4.00    --  112.00 111.00-150.00   63
 45  \w    124.00 150.00   1.00    4.00    --  112.00 111.00-120.00   26
 46  \w     82.00 107.00   1.00    4.00    --  112.00 -95.00 -60.00   25
 47  \w     90.00 116.00   1.00    4.00    --  112.00 -83.00 -30.58   26
 48  \w    113.00 157.00   1.00    4.00    --  112.00 -15.00  90.00   44
 49  \w     83.00 109.00   1.00    4.00    --  112.00  77.00 -30.00   26
 50  \w     51.00  76.00   1.00    4.00    --  112.00 -77.00-180.00   25
 51  \w     90.00 116.00   1.00    4.00    --  112.00 -77.00-180.00   26
 52  \w    105.00 131.00   1.00    4.00    --  112.00 -77.00  30.00   26
 53  \w     73.00  98.00   1.00    4.00    --  112.00 -95.00-120.00   25
 54  \w     37.00  83.00   1.00    4.00    --  112.00-111.00  60.00   46
 55  \w    150.00 175.00   1.00    4.00    --  112.00  45.00-150.00   25
 56  \w     79.00 105.00   1.00    4.00    --  112.00 -45.00 120.00   26
 57  \w     45.00  71.00   1.00    4.00    --  112.00 -61.00   0.00   26
 58  \w     80.00 110.00   1.00    4.00    --  112.00 -30.00 -90.00   30
 59  \w     34.00  60.00   1.00    4.00    --  112.00 -83.00 -30.58   26
;
_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      -0.0801348000
_diffrn_orient_matrix_UB_12      -0.0868428000
_diffrn_orient_matrix_UB_13      0.0243228000
_diffrn_orient_matrix_UB_21      0.1381860000
_diffrn_orient_matrix_UB_22      -0.0474821000
_diffrn_orient_matrix_UB_23      -0.0500200000
_diffrn_orient_matrix_UB_31      0.1144057000
_diffrn_orient_matrix_UB_32      -0.0033940000
_diffrn_orient_matrix_UB_33      0.0788579000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27840
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.472
_diffrn_reflns_theta_min         3.967
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.259
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         7944
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0452P)^2^+0.2691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                7741
_reflns_number_total             7944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00640_si_004.cif
_cod_data_source_block           anna_29092017_vm251_3
_cod_database_code               4034783
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9705(8)
 0.0295(8)
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:
 C00C(H00f), C00E(H00E), C00G(H00G), C00H(H00H), C00M(H00M), C015(H015)
3.b Secondary CH2 refined with riding coordinates:
 C00P(H00a,H00b), C00Q(H00i,H00j), C00T(H00k,H00l), C00W(H00o,H00p), C011(H01a,
 H01b), C012(H01p,H01q), C017(H01c,H01d), C018(H01e,H01f)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00c), C00D(H00D), C00N(H00N), C00S(H00S), C00V(H00V), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C013(H013), C014(H014), C016(H016),
 C019(H019), C01A(H01g), C01B(H01r), C01C(H01h), C01D(H01s), C01H(H01l)
3.d Idealised Me refined as rotating group:
 C01E(H01t,H01u,H01v), C01F(H01w,H01x,H01y), C01G(H01i,H01j,H01k), C01I(H01m,
 H01n,H01o)
;
_shelx_res_checksum              28879
_shelx_hkl_checksum              53596
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.639