Hydrogen-bond motifs in <i>N</i>-monosubstituted derivatives of barbituric acid: 5-allyl-5-isopropyl-1-methylbarbituric acid (enallylpropymal) and 1,5-di(but-2-enyl)-5-ethylbarbituric acid
Gelbrich, Thomas; Zencirci, Neslihan; Griesser, Ulrich J.; Acta Crystallographica Section C 66 (2010) o55–o58; doi:10.1107/S0108270109054249

data_2017478
_publ_section_title
;
 Hydrogen-bond motifs in <i>N</i>-monosubstituted derivatives of
 barbituric acid: 5-allyl-5-isopropyl-1-methylbarbituric acid
 (enallylpropymal) and 1,5-di(but-2-enyl)-5-ethylbarbituric acid
;
_journal_coeditor_code           JZ3168
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o55
_journal_page_last               o58
_journal_paper_doi               10.1107/S0108270109054249
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H16 N2 O3'
_chemical_formula_moiety         'C11 H16 N2 O3'
_chemical_formula_sum            'C11 H16 N2 O3'
_chemical_formula_weight         224.26
_chemical_melting_point          332.0(10)
_chemical_name_common            'Narconumal, Enallylpropymal'
_chemical_name_systematic
;
5-allyl-5-isopropyl-1-methylbarbituric acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                77.574(7)
_cell_angle_beta                 80.837(7)
_cell_angle_gamma                75.518(6)
_cell_formula_units_Z            2
_cell_length_a                   6.4160(7)
_cell_length_b                   7.9559(8)
_cell_length_c                   11.9569(12)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.407
_cell_volume                     573.51(10)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
;
EvalCCD (Duisenberg <i>et al.</i>,  2003)
;
_computing_molecular_graphics
'XP/SHELXTL (Sheldrick, 2008) and Mercury (Bruno <i>et al.</i>,  2002)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2000
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       0.027(4)
_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   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0042P)^2^+0.6197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                1386
_reflns_number_total             2000
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jz3168.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2017478
_cod_database_fobs_code          2017478