δ-Azaproline and its oxidized variants.
Elbatrawi, Yassin M.; Pedretty, Kyle P.; Giddings, Nicole; Woodcock, H. Lee; Del Valle, Juan R.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03384

data_4038049
_publ_section_title
;
 \d-Azaproline and its oxidized variants.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03384
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H10 N2 O4'
_chemical_formula_sum            'C7 H10 N2 O4'
_chemical_formula_weight         186.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.86370(10)
_cell_length_b                   11.1251(3)
_cell_length_c                   15.4131(4)
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.44
_cell_measurement_theta_min      4.90
_cell_volume                     833.99(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7679
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         4.902
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0770 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.9039.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0268P)^2^+0.2324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0641
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                1502
_reflns_number_total             1548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03384_si_003.cif
_cod_data_source_block           yb_07_01
_cod_database_code               4038049
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.829
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              28129
_shelx_hkl_checksum              24640
_olex2_submission_special_instructions 'No special instructions were received'