Ring-expansion synthesis and crystal structure of dimethyl 4-ethyl-1,4,5,6,7,8-hexahydroazonino[5,6-<i>b</i>]indole-2,3-dicarboxylate
Nguyen, Van Tuyen; Sorokina, Elena A.; Listratova, Anna V.; Voskressensky, Leonid G.; Lobanov, Nikolai N.; Dorovatovskii, Pavel V.; Zubavichus, Yan V.; Khrustalev, Victor N.; Acta Crystallographica Section E 73 (2017) 338–340; doi:10.1107/S205698901700161X

data_2242173
_publ_section_title
;
 Ring-expansion synthesis and crystal structure of dimethyl
 4-ethyl-1,4,5,6,7,8-hexahydroazonino[5,6-<i>b</i>]indole-2,3-dicarboxylate
;
_journal_coeditor_code           HB7645
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              338
_journal_page_last               340
_journal_paper_doi               10.1107/S205698901700161X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C20 H24 N2 O4'
_chemical_formula_moiety         'C20 H24 N2 O4'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41
_chemical_name_systematic
;
Dimethyl
4-ethyl-1,4,5,6,7,8-hexahydroazonino[5,6-<i>b</i>]indole-2,3-dicarboxylate
;
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           '<i>SHELXTL</i> (Sheldrick, 2015)'
_cell_angle_alpha                90
_cell_angle_beta                 98.45(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5900(17)
_cell_length_b                   10.450(2)
_cell_length_c                   20.670(4)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.0
_cell_measurement_theta_min      3.8
_cell_volume                     1835.3(6)
_computing_cell_refinement
;
<i>iMosflm</i> (Battye <i>et al.</i>, 2011)
;
_computing_data_collection
;
<i>Automar</i> (MarXperts, 2015)
;
_computing_data_reduction
;
<i>iMosflm</i> (Battye <i>et al.</i>, 2011)
;
_computing_molecular_graphics
;
<i>SHELXTL</i> (Sheldrick, 2015)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2015)
;
_computing_structure_refinement
;
<i>SHELXTL</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXTL</i> (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20559
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.451
_diffrn_reflns_theta_min         3.805
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>Scala</i>; Evans, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.236
_refine_ls_extinction_coef       0.0139(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3123
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7645sup1.cif
_cod_data_source_block           I
_cod_database_code               2242173
_cod_database_fobs_code          2242173
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              3864
_shelx_res_checksum              37361
_shelxl_version_number           2015/7