Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence.
Chennamadhavuni, Spandan; Panek, James S.; Porco, Jr, John A; Brown, Lauren E.; The Journal of organic chemistry 83 (2018) 15449–15462; doi:10.1021/acs.joc.8b02724

data_4034772
_publ_section_title
;
 Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones
 via a One-Pot Intramolecular aza-Michael/Lactamization Sequence.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15449
_journal_page_last               15462
_journal_paper_doi               10.1021/acs.joc.8b02724
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43
_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             2018-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-31 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5750(3)
_cell_length_b                   9.8384(6)
_cell_length_c                   28.6228(15)
_cell_measurement_reflns_used    9476
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.503
_cell_measurement_theta_min      4.753
_cell_volume                     1851.54(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX3 (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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_temperature      99.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Proteum-R'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            86745
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.005
_diffrn_reflns_theta_max         66.005
_diffrn_reflns_theta_min         4.753
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0807 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9128.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1301 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0279P)^2^+0.6802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3189
_reflns_number_total             3214
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {d61cf108-1210-4be2-9910-c8874c726c18}
_cod_data_source_file            jo8b02724_si_002.cif
_cod_data_source_block           spandan1_0m
_cod_database_code               4034772
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              20662
_shelx_hkl_checksum              9527
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;