Catalyst-Controlled Structural Divergence: Selective Intramolecular 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of Benzoxazepinones and Benzoxazinones.
Singh, Karandeep; Malviya, Bhanwar Kumar; Roy, Tapta Kanchan; Mithu, Venus Singh; Bhardwaj, Vimal K.; Verma, Ved Prakash; Chimni, Swapandeep Singh; Sharma, Siddharth; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02123

data_4033273
_publ_section_title
;
 Catalyst-Controlled Structural Divergence: Selective Intramolecular
 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of
 Benzoxazepinones and Benzoxazinones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02123
_journal_year                    2017
_chemical_formula_moiety         'C29 H30 N2 O5'
_chemical_formula_sum            'C29 H30 N2 O5'
_chemical_formula_weight         486.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.775(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.0109(8)
_cell_length_b                   9.0540(3)
_cell_length_c                   26.4648(10)
_cell_measurement_reflns_used    4520
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.21
_cell_volume                     5225.6(3)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1356
_diffrn_reflns_av_unetI/netI     0.1314
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            52412
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'
_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    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         12907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.2507
_refine_ls_R_factor_gt           0.0899
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+1.9904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2581
_reflns_number_gt                4798
_reflns_number_total             12907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02123_si_003.cif
_cod_data_source_block           s343
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C29 H30 N2 O5)'
_cod_original_formula_sum        'C58 H60 N4 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     973.10
_cod_database_code               4033273
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C16(H16), C45(H45)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C18(H18), C14(H14), C32(H32), C3(H3), C47(H47), C43(H43),
 C13(H13), C11(H11), C21(H21), C9(H9), C5(H5), C34(H34), C42(H42), C20(H20),
 C49(H49), C38(H38), C12(H12), C50(H50), C41(H41), C35(H35), C40(H40), C6(H6),
 C37(H37), C36(H36), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C53(H53A,H53B,H53C), C29(H29A,H29B,H29C), C58(H58A,H58B,
 H58C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C23(H23A,H23B,H23C), C57(H57A,
 H57B,H57C), C52(H52A,H52B,H52C), C56(H56A,H56B,H56C)
;
_olex2_submission_special_instructions 'No special instructions were received'