2-Cyano-3-(2,3,6,7-tetrahydro-1<i>H</i>,5<i>H</i>-benzo[<i>ij</i>]quinolizin-9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate
Yennawar, Hemant; He, Gang; Rumble, Christopher; Maroncelli, Mark; Acta Crystallographica Section E 68 (2012) o3204–o3205; doi:10.1107/S1600536812043383

data_2236520
_publ_section_title
;
 2-Cyano-3-(2,3,6,7-tetrahydro-1<i>H</i>,5<i>H</i>-benzo[<i>ij</i>]quinolizin-9-yl)prop-2-enoic
 acid dimethyl sulfoxide monosolvate
;
_journal_coeditor_code           NG5301
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3204
_journal_page_last               o3205
_journal_paper_doi               10.1107/S1600536812043383
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H16 N2 O2, C2 H6 O S'
_chemical_formula_moiety         'C16 H16 N2 O2, C2 H6 O S'
_chemical_formula_sum            'C18 H22 N2 O3 S'
_chemical_formula_weight         346.44
_chemical_name_common
;
9-(2-carboxy-2-cyanovinyl) julolidine or CCVJ
;
_chemical_name_systematic
;
2-Cyano-3-(2,3,6,7-tetrahydro-1<i>H</i>,5<i>H</i>-benzo[<i>ij</i>]quinolizin-
9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.170(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.215(3)
_cell_length_b                   7.4588(19)
_cell_length_c                   11.819(3)
_cell_measurement_reflns_used    1427
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.323
_cell_measurement_theta_min      2.432
_cell_volume                     886.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5962
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.231
_refine_ls_abs_structure_details 'Flack (1983), 1096 Friedel pairs'
_refine_ls_abs_structure_Flack   0.51(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0864P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                2520
_reflns_number_total             3443
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ng5301.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2236520
_cod_database_fobs_code          2236520