Preparation and structural analysis of (±)-<i>cis</i>-ethyl 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and (±)-<i>trans</i>-ethyl 2-oxooctahydro-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridine-5-carboxylate
Schwehm, Carolin; Lewis, William; Blake, Alexander J.; Kellam, Barrie; Stocks, Michael J.; Acta Crystallographica Section C 70 (2014) –; doi:10.1107/S205322961402436X

data_2019736
_publ_section_title
;
 Preparation and structural analysis of (+-)-<i>cis</i>-ethyl
 2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate and
 (+-)-<i>trans</i>-ethyl
 2-oxooctahydro-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridine-5-carboxylate
;
_journal_coeditor_code           KY3066
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961402436X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H18 N2 O2 S'
_chemical_formula_moiety         'C11 H18 N2 O2 S'
_chemical_formula_sum            'C11 H18 N2 O2 S'
_chemical_formula_weight         242.33
_chemical_name_systematic
;
(+-)-<i>cis</i>-Ethyl
2-sulfanylidenedecahydro-1,6-naphthyridine-6-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.06714(17)
_cell_length_b                   8.30759(8)
_cell_length_c                   19.5481(2)
_cell_measurement_reflns_used    13043
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.7920
_cell_measurement_theta_min      4.5160
_cell_volume                     2446.87(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
<i>OLEX2.SOLVE</i> (Bourhis <i>et al.</i>,  2014)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.6296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  GV1000
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21836
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.942
_diffrn_reflns_theta_min         4.524
_exptl_absorpt_coefficient_mu    2.264
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.1532
_exptl_crystal_size_mid          0.1153
_exptl_crystal_size_min          0.0483
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.196
_refine_ls_abs_structure_details
;
Flack x determined using 2311 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack   0.067(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5117
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0615P)^2^+0.4180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                5030
_reflns_number_total             5117
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ky3066sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2446.87(5)
_cod_database_code               2019736
_shelx_hkl_checksum              24719
_shelx_res_checksum              18760
_shelxl_version_number           2013-4