Design, synthesis and diversification of natural product-inspired hydantoin-fused tetrahydroazepino indoles
Barve, Indrajeet J.; Dalvi, Prashant B.; Thikekar, Tushar Ulhas; Chanda, Kaushik; Liu, Yu-Li; Fang, Chiu-Ping; Liu, Chia-Chen; Sun, Chung-Ming; RSC Adv. 5 (2015) 73169–; doi:10.1039/C5RA12063B

data_7221938
_publ_section_title
;
 Design, synthesis and diversification of natural product-inspired
 hydantoin-fused tetrahydroazepino indoles
;
_journal_issue                   89
_journal_name_full               'RSC Adv.'
_journal_page_first              73169
_journal_paper_doi               10.1039/C5RA12063B
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_sum            'C17 H18 N2 O4'
_chemical_formula_weight         314.33
_chemical_name_systematic
'(S)-5-ethyl 2-methyl 1, 2, 3, 6 -tetrahydroazepino[4,5-b]indole-2,5-dicarboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-11-07 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                94.238(5)
_cell_angle_beta                 97.302(6)
_cell_angle_gamma                96.834(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9602(7)
_cell_length_b                   8.6689(7)
_cell_length_c                   11.7774(11)
_cell_measurement_reflns_used    6638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.2850
_cell_measurement_theta_min      5.1610
_cell_volume                     797.12(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8958
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.403
_diffrn_reflns_theta_min         5.160
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1513P)^2^+0.0470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2031
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4028
_reflns_number_total             4412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra12063b2.cif
_cod_data_source_block           cu_140110_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               7221938
_shelxl_version_number           2013-4
_shelx_res_checksum              20896
_shelx_hkl_checksum              80356