#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227578.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227578
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 3-(2,5-Dimethylfuran-3-yl)-1H-pyrazol-5-ol--ethyl
 3-(propan-2-ylidene)carbazate (1/1)
;
_journal_coeditor_code           HB5696
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3020
_journal_page_last               o3021
_journal_paper_doi               10.1107/S1600536810043886
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H12 N2 O2, C9 H10 N2 O2'
_chemical_formula_moiety         'C6 H12 N2 O2, C9 H10 N2 O2'
_chemical_formula_sum            'C15 H22 N4 O4'
_chemical_formula_weight         322.37
_chemical_name_systematic
;
3-(2,5-Dimethylfuran-3-yl)-1H-pyrazol-5-ol--ethyl
3-(propan-2-ylidene)carbazate (1/1)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.293(4)
_cell_angle_beta                 100.354(5)
_cell_angle_gamma                108.346(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6988(17)
_cell_length_b                   9.4830(19)
_cell_length_c                   11.837(4)
_cell_measurement_reflns_used    7782
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.67
_cell_measurement_theta_min      2.59
_cell_volume                     843.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13322
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.2939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                2911
_reflns_number_total             3264
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5696.cif
_cod_data_source_block           I
_cod_original_cell_volume        843.7(3)
_cod_database_code               2227578
_cod_database_fobs_code          2227578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.72298(12) 0.49965(12) -0.03577(8) 0.0272(2) Uani d . 1 . .
O O2 1.41202(12) 1.13027(10) 0.43430(9) 0.0232(2) Uani d . 1 . .
N N1 1.21447(13) 0.71967(13) 0.29969(10) 0.0197(2) Uani d . 1 . .
N N2 1.34466(13) 0.85605(12) 0.38574(9) 0.0190(2) Uani d . 1 . .
C C1 1.31074(15) 0.97528(15) 0.36573(11) 0.0185(3) Uani d . 1 . .
C C2 1.16205(16) 0.91874(15) 0.26795(12) 0.0211(3) Uani d . 1 . .
H H2A 1.1136 0.9791 0.2366 0.025 Uiso calc R 1 . .
C C3 1.10286(15) 0.75316(15) 0.22806(11) 0.0185(3) Uani d . 1 . .
C C4 0.95185(16) 0.62751(15) 0.13126(11) 0.0201(3) Uani d . 1 . .
C C5 0.87164(16) 0.46384(15) 0.11997(12) 0.0222(3) Uani d . 1 . .
H H5A 0.9076 0.4169 0.1725 0.027 Uiso calc R 1 . .
C C6 0.73478(17) 0.39202(16) 0.01874(12) 0.0252(3) Uani d . 1 . .
C C7 0.85745(16) 0.64286(16) 0.03429(12) 0.0240(3) Uani d . 1 . .
C C8 0.8742(2) 0.77483(18) -0.01199(14) 0.0344(3) Uani d . 1 . .
H H8A 0.9922 0.8414 0.0089 0.052 Uiso calc R 1 . .
H H8B 0.8166 0.8382 0.0257 0.052 Uiso calc R 1 . .
H H8C 0.8246 0.7301 -0.1005 0.052 Uiso calc R 1 . .
C C9 0.59939(19) 0.22804(18) -0.04258(14) 0.0342(3) Uani d . 1 . .
H H9A 0.6186 0.1632 0.0027 0.051 Uiso calc R 1 . .
H H9B 0.6011 0.1810 -0.1260 0.051 Uiso calc R 1 . .
H H9C 0.4909 0.2338 -0.0441 0.051 Uiso calc R 1 . .
O O3 0.08857(11) 0.22838(11) 0.42456(9) 0.0236(2) Uani d . 1 . .
O O4 0.06433(11) 0.42612(11) 0.36063(9) 0.0244(2) Uani d . 1 . .
N N3 0.29597(14) 0.35988(13) 0.36500(10) 0.0209(2) Uani d . 1 . .
N N4 0.37772(13) 0.48909(12) 0.33504(10) 0.0201(2) Uani d . 1 . .
C C10 -0.21443(18) 0.07821(18) 0.31978(15) 0.0346(3) Uani d . 1 . .
H H10A -0.3233 0.0471 0.3338 0.052 Uiso calc R 1 . .
H H10B -0.1904 -0.0153 0.2871 0.052 Uiso calc R 1 . .
H H10C -0.2154 0.1302 0.2615 0.052 Uiso calc R 1 . .
C C11 -0.07996(17) 0.19197(17) 0.44018(13) 0.0267(3) Uani d . 1 . .
H H11A -0.0984 0.2905 0.4695 0.032 Uiso calc R 1 . .
H H11B -0.0878 0.1443 0.5021 0.032 Uiso calc R 1 . .
C C12 0.14196(16) 0.34622(14) 0.38212(11) 0.0194(3) Uani d . 1 . .
C C13 0.52197(16) 0.50193(15) 0.31731(11) 0.0212(3) Uani d . 1 . .
C C14 0.60676(18) 0.38865(18) 0.32513(14) 0.0300(3) Uani d . 1 . .
H H14A 0.6155 0.3777 0.4039 0.045 Uiso calc R 1 . .
H H14B 0.7183 0.4299 0.3169 0.045 Uiso calc R 1 . .
H H14C 0.5408 0.2856 0.2596 0.045 Uiso calc R 1 . .
C C15 0.61073(17) 0.64131(16) 0.28562(13) 0.0249(3) Uani d . 1 . .
H H15A 0.5436 0.7044 0.2843 0.037 Uiso calc R 1 . .
H H15B 0.6259 0.6025 0.2054 0.037 Uiso calc R 1 . .
H H15C 0.7196 0.7063 0.3468 0.037 Uiso calc R 1 . .
H H1N1 1.211(2) 0.626(2) 0.3012(15) 0.033(4) Uiso d . 1 . .
H H1N3 0.347(2) 0.304(2) 0.3897(15) 0.031(4) Uiso d . 1 . .
H H1O2 1.496(3) 1.138(2) 0.500(2) 0.057(6) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C6 . . 107.17(10) ?
C1 O2 H1O2 . . 110.5(13) ?
C3 N1 N2 . . 111.95(10) ?
C3 N1 H1N1 . . 129.8(11) ?
N2 N1 H1N1 . . 118.1(11) ?
C1 N2 N1 . . 104.49(10) ?
N2 C1 O2 . . 121.83(11) ?
N2 C1 C2 . . 111.95(11) ?
O2 C1 C2 . . 126.22(11) ?
C3 C2 C1 . . 104.84(11) ?
C3 C2 H2A . . 127.6 ?
C1 C2 H2A . . 127.6 ?
N1 C3 C2 . . 106.77(11) ?
N1 C3 C4 . . 122.08(11) ?
C2 C3 C4 . . 131.15(12) ?
C7 C4 C5 . . 106.49(11) ?
C7 C4 C3 . . 126.43(12) ?
C5 C4 C3 . . 127.08(12) ?
C6 C5 C4 . . 106.74(12) ?
C6 C5 H5A . . 126.6 ?
C4 C5 H5A . . 126.6 ?
C5 C6 O1 . . 109.97(12) ?
C5 C6 C9 . . 134.00(13) ?
O1 C6 C9 . . 116.02(12) ?
C4 C7 O1 . . 109.62(12) ?
C4 C7 C8 . . 134.17(13) ?
O1 C7 C8 . . 116.15(11) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C12 O3 C11 . . 115.88(10) ?
C12 N3 N4 . . 116.20(11) ?
C12 N3 H1N3 . . 119.0(11) ?
N4 N3 H1N3 . . 123.2(11) ?
C13 N4 N3 . . 116.67(11) ?
C11 C10 H10A . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C11 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 C10 . . 110.77(11) ?
O3 C11 H11A . . 109.5 ?
C10 C11 H11A . . 109.5 ?
O3 C11 H11B . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
O4 C12 O3 . . 125.45(12) ?
O4 C12 N3 . . 125.31(12) ?
O3 C12 N3 . . 109.22(10) ?
N4 C13 C14 . . 125.22(12) ?
N4 C13 C15 . . 116.82(12) ?
C14 C13 C15 . . 117.96(11) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.3719(16) ?
O1 C6 . 1.3792(17) ?
O2 C1 . 1.3468(15) ?
O2 H1O2 . 0.93(2) ?
N1 C3 . 1.3493(16) ?
N1 N2 . 1.3685(14) ?
N1 H1N1 . 0.883(18) ?
N2 C1 . 1.3288(16) ?
C1 C2 . 1.3988(18) ?
C2 C3 . 1.3844(18) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.4561(18) ?
C4 C7 . 1.3597(19) ?
C4 C5 . 1.4405(18) ?
C5 C6 . 1.3448(19) ?
C5 H5A . 0.9300 ?
C6 C9 . 1.4835(19) ?
C7 C8 . 1.486(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
O3 C12 . 1.3445(15) ?
O3 C11 . 1.4558(15) ?
O4 C12 . 1.2124(15) ?
N3 C12 . 1.3625(17) ?
N3 N4 . 1.3905(15) ?
N3 H1N3 . 0.872(18) ?
N4 C13 . 1.2834(17) ?
C10 C11 . 1.502(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C13 C14 . 1.4967(19) ?
C13 C15 . 1.4967(18) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N1 O4 1_655 0.883(18) 2.304(19) 3.0363(19) 140.1(16) yes
N1 H1N1 N4 1_655 0.883(18) 2.288(19) 3.043(2) 143.1(16) yes
N3 H1N3 O2 1_445 0.872(18) 2.076(19) 2.9293(19) 166.7(18) yes
O2 H1O2 N2 2_876 0.93(2) 1.73(2) 2.6602(17) 176(2) yes
C5 H5A O4 1_655 0.93 2.35 3.212(2) 153 yes
C11 H11B Cg2 2_666 0.97 2.71 3.50(2) 138 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C1 . . . . 0.09(13) ?
N1 N2 C1 O2 . . . . 179.58(11) ?
N1 N2 C1 C2 . . . . -0.44(14) ?
N2 C1 C2 C3 . . . . 0.62(14) ?
O2 C1 C2 C3 . . . . -179.40(11) ?
N2 N1 C3 C2 . . . . 0.30(14) ?
N2 N1 C3 C4 . . . . -178.86(10) ?
C1 C2 C3 N1 . . . . -0.53(13) ?
C1 C2 C3 C4 . . . . 178.51(12) ?
N1 C3 C4 C7 . . . . -161.23(13) ?
C2 C3 C4 C7 . . . . 19.8(2) ?
N1 C3 C4 C5 . . . . 19.70(19) ?
C2 C3 C4 C5 . . . . -159.23(13) ?
C7 C4 C5 C6 . . . . -0.50(14) ?
C3 C4 C5 C6 . . . . 178.72(12) ?
C4 C5 C6 O1 . . . . 0.27(14) ?
C4 C5 C6 C9 . . . . -179.15(15) ?
C7 O1 C6 C5 . . . . 0.06(14) ?
C7 O1 C6 C9 . . . . 179.60(11) ?
C5 C4 C7 O1 . . . . 0.55(14) ?
C3 C4 C7 O1 . . . . -178.68(11) ?
C5 C4 C7 C8 . . . . -176.26(16) ?
C3 C4 C7 C8 . . . . 4.5(2) ?
C6 O1 C7 C4 . . . . -0.39(14) ?
C6 O1 C7 C8 . . . . 177.06(12) ?
C12 N3 N4 C13 . . . . -179.21(11) ?
C12 O3 C11 C10 . . . . 84.10(14) ?
C11 O3 C12 O4 . . . . 2.70(18) ?
C11 O3 C12 N3 . . . . -176.27(10) ?
N4 N3 C12 O4 . . . . 8.26(18) ?
N4 N3 C12 O3 . . . . -172.77(10) ?
N3 N4 C13 C14 . . . . 0.65(19) ?
N3 N4 C13 C15 . . . . -179.72(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656249
