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_7221936
_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_formula_sum            'C25 H23 N3 O3 S'
_chemical_formula_weight         445.52
_chemical_name_systematic
'(S)-ethyl 1-oxo-2-phenethyl-3-thioxo-1,2,3,7,12,12a-hexahydroimidazo[1',5':1,7]azepino[4,5-b]indole-6-carboxylate'
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-10-01 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6842(5)
_cell_length_b                   20.3035(8)
_cell_length_c                   8.2806(3)
_cell_measurement_reflns_used    4870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1290
_cell_measurement_theta_min      2.6900
_cell_volume                     2101.59(14)
_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-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15564
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         1.629
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Monoclinic
_exptl_crystal_F_000             936
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0923P)^2^+0.2124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             4291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra12063b2.cif
_cod_data_source_block           140905LT_a
_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               7221936
_shelxl_version_number           2014-3
_shelx_res_checksum              69093
_shelx_hkl_checksum              83296