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_4036070
_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         'C16 H18 I N3 O7 S, 0.5(H2 O)'
_chemical_formula_sum            'C16 H19 I N3 O7.5 S'
_chemical_formula_weight         532.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 91.228(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3654(7)
_cell_length_b                   10.6860(4)
_cell_length_c                   18.0155(7)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.977
_cell_measurement_theta_min      3.779
_cell_volume                     3919.7(3)
_computing_cell_refinement
'SAINT (2013) V8.38A; 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) V8.38A; 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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0473
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29942
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.967
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    9.747
_exptl_absorpt_correction_T_max  0.2006
_exptl_absorpt_correction_T_min  0.0617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1490 before and 0.0920 after correction. The Ratio of minimum to maximum transmission is 0.3076. 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    1.804
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.437
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.092(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         7155
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0127P)^2^+23.8186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                6573
_reflns_number_total             7155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01861_si_002.cif
_cod_data_source_block           lub1312
_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 

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H18 I N3 O7 S), H2 O'
_cod_original_formula_sum        'C32 H38 I2 N6 O15 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1064.60
_cod_database_code               4036070
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.509
_shelx_estimated_absorpt_t_min   0.141
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.908(10)
 0.092(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3.a Riding coordinates:
 N1A(H1A), N1B(H1B)
3.b Free rotating group:
 O1(H1C,H1D)
3.c Ternary CH refined with riding coordinates:
 C9A(H9A), C11A(H11A), C12A(H12A), C16A(H16A), C9B(H9B), C11B(H11B),
 C12B(H12B), C16B(H16B)
3.d Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C14A(H14A,H14B), C15A(H15A,H15B), C10B(H10C,H10D), C14B(H14C,
 H14D), C15B(H15C,H15D)
3.e Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B)
3.f Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_shelx_res_checksum              88194
_shelx_hkl_checksum              45724
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'