Peptidomimetic Synthesis by Way of Diastereoselective Iodoacetoxylation and Transannular Amidation of 7-9-Membered Lactams.
Atmuri, N. D. Prasad; Reilley, David J.; Lubell, William D.; Organic letters 19 (2017) 5066–5069; doi:10.1021/acs.orglett.7b02275

data_1547359
_publ_section_title
;
 Peptidomimetic Synthesis by Way of Diastereoselective Iodoacetoxylation
 and Transannular Amidation of 7-9-Membered Lactams.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5066
_journal_page_last               5069
_journal_paper_doi               10.1021/acs.orglett.7b02275
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H22 N2 O5'
_chemical_formula_sum            'C23 H22 N2 O5'
_chemical_formula_weight         406.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-20
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3495(5)
_cell_length_b                   36.3258(17)
_cell_length_c                   4.7864(2)
_cell_measurement_reflns_used    9776
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.892
_cell_measurement_theta_min      3.550
_cell_volume                     1973.34(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 1.000
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            51210
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.970
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1524 before and 0.0762 after correction. The Ratio of minimum to maximum transmission is 0.8752. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_coef       0.0115(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0417P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3503
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02275_si_005.cif
_cod_data_source_block           lub106
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547358--1547364.cif.
;
_cod_database_code               1547359
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C32 \\sim N2-C2
 with sigma of 0.02
 O5-C9 \\sim O50-C9
 with sigma of 0.02
3. Same fragment restrains
{N1, O1, C1, C2, C3, C4, C5, C6, C7, O2, O3, C8, O5, C10, C11, C12, C13, C14,
C15, C16, C17, C18, C19, C20, C21, C22, C23} sigma for 1-2: 0.02, 1-3: 0.04
as
{N31, O31, C31, C32, C33, C34, C35, C36, C37, O32, O33, C38, O50, C40, C41,
C42, C43, C44, C45, C46, C47, C48, C49, C50, C51, C52, C53}
4. Others
 Sof(H2B)=Sof(N31)=Sof(H31)=Sof(O31)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=
 Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36)=
 Sof(C37)=Sof(O32)=Sof(O33)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(O50)=
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(C43)=Sof(H43)=
 Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(C48)=
 Sof(C49)=Sof(H49)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=
 Sof(C53)=1-FVAR(1)
 Sof(H2A)=Sof(N1)=Sof(H1)=Sof(O1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(O2)=
 Sof(O3)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(O5)=Sof(C10)=Sof(H10A)=
 Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=Sof(C19)=Sof(H19)=
 Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C11(H11), C32(H32), C36(H36), C41(H41)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B), C35(H35A,H35B), C40(H40A,H40B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), N2(H2B), N1(H1), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), N31(H31), C33(H33), C34(H34),
  C43(H43), C44(H44), C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              1990
_shelx_hkl_checksum              36026
_olex2_submission_special_instructions 'No special instructions were received'