A simple hydrogen-bonded chain in (3<i>Z</i>)-3-{1-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3<i>H</i>)-one, and a hydrogen-bonded ribbon of centrosymmetric rings in the self-assembled adduct (3<i>Z</i>)-3-{1-[(5-methyl-1<i>H</i>-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3<i>H</i>)-one–6-(2-hydroxyethyl)-2,5-dimethylpyrazolo[1,5-<i>a</i>]pyrimidin-7(4<i>H</i>)-one (1/1)
Quiroga, Jairo; Portilla, Jaime; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 66 (2010) o25–o28; doi:10.1107/S0108270109052846

data_2017466
_publ_section_title
;A simple hydrogen-bonded chain in
 (3<i>Z</i>)-3-{1-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3<i>H</i>)-one,
 and a hydrogen-bonded ribbon of centrosymmetric rings in the self-assembled
 adduct
 (3<i>Z</i>)-3-{1-[(5-methyl-1<i>H</i>-pyrazol-3-yl)amino]ethylidene}-4,5-dihydrofuran-2(3<i>H</i>)-one--6-(2-hydroxyethyl)-2,5-dimethylpyrazolo[1,5-<i>a</i>]pyrimidin-7(4<i>H</i>)-one
 (1/1)
;
_journal_coeditor_code           FA3210
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o25
_journal_page_last               o28
_journal_paper_doi               10.1107/S0108270109052846
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N3 O2'
_chemical_formula_moiety         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_chemical_name_systematic
;
(3<i>Z</i>)-3-{1-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]ethylidene}-4,5-
dihydrofuran-2(3<i>H</i>)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.883(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4969(17)
_cell_length_b                   9.8550(9)
_cell_length_c                   12.6739(16)
_cell_measurement_reflns_used    2536
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.26
_cell_volume                     1291.6(3)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg <i>et al.</i>,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19109
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0499P)^2^+0.7664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                1704
_reflns_number_total             2536
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3210.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017466
_cod_database_fobs_code          2017466