Stereo- and regiochemical transannular cyclization of a common hexahydro-1H-azonine to afford three different indolizidinone dipeptide mimetics.
Atmuri, N. D. Prasad; Lubell, William D.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01861

data_4036068
_publ_section_title
;
 Stereo- and regiochemical transannular cyclization of a common
 hexahydro-1H-azonine to afford three different indolizidinone dipeptide
 mimetics.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01861
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 I N2 O5'
_chemical_formula_sum            'C18 H17 I N2 O5'
_chemical_formula_weight         468.23
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                73.120(2)
_cell_angle_beta                 78.857(2)
_cell_angle_gamma                64.829(2)
_cell_formula_units_Z            4
_cell_length_a                   10.4928(3)
_cell_length_b                   10.9595(3)
_cell_length_c                   18.3029(6)
_cell_measurement_reflns_used    9417
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.812
_cell_measurement_theta_min      2.203
_cell_volume                     1816.90(10)
_computing_cell_refinement
'SAINT (2013) V8.37A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.37A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28778
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.972
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    9.682
_exptl_absorpt_correction_T_max  0.3027
_exptl_absorpt_correction_T_min  0.1637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1267 before and 0.0884 after correction. The Ratio of minimum to maximum transmission is 0.5408. The \l/2 correction factor is Not present.'
_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    1.712
_exptl_crystal_description       rod
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.059(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     942
_refine_ls_number_reflns         12189
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0493
_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^)+4.9501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.791
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                9657
_reflns_number_total             12189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01861_si_004.cif
_cod_data_source_block           lub1303
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4036068
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.476
_shelx_estimated_absorpt_t_min   0.196
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.941(10)
 0.059(10)
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. Uiso/Uaniso restraints and constraints
C17A \\sim O4A \\sim O5A \\sim C18A: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C9A(H9A), C11A(H11A), C12A(H12A), C16A(H16A), C9B(H9B), C11B(H11B),
 C12B(H12B), C16B(H16B), C9C(H9C), C11C(H11C), C12C(H12C), C16C(H16C), C9D(H9D),
  C11D(H11D), C12D(H12D), C16D(H16D)
4.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C14A(H14A,H14B), C15A(H15A,H15B), C10B(H10C,H10D), C14B(H14C,
 H14D), C15B(H15C,H15D), C10C(H10E,H10F), C14C(H14E,H14F), C15C(H15E,H15F),
 C10D(H10G,H10H), C14D(H14G,H14H), C15D(H15G,H15H)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C3B(H3B), C4B(H4B), C5B(H5B),
 C6B(H6B), C3C(H3C), C4C(H4C), C5C(H5C), C6C(H6C), C3D(H3D), C4D(H4D), C5D(H5D),
  C6D(H6D)
4.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F), C18C(H18G,H18H,H18I), C18D(H18J,
 H18K,H18L)
;
_shelx_res_checksum              94357
_shelx_hkl_checksum              13151
_olex2_submission_special_instructions 'No special instructions were received'