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#$Date: 2023-03-23 11:36:01 +0200 (Thu, 23 Mar 2023) $
#$Revision: 282006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106955.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_8106955
loop_
_publ_author_name
'Radi, Smaail'
'Tighadouini, Said'
'Hadda, Taibi Ben'
'Akkurt, Mehmet'
'Özdemir, Namık'
'Sirajuddin, Muhammad'
'Mabkhot, Yahia N.'
_publ_section_title
;
 Crystal structure of
 (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxybut-2-en-1-one C9H12N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              617
_journal_page_last               618
_journal_paper_doi               10.1515/ncrs-2015-0212
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C9 H12 N2 O2'
_chemical_formula_sum            'C9 H12 N2 O2'
_chemical_formula_weight         180.21
_chemical_name_systematic
;
(2Z)-3-hydroxy-1-(1,5-dimethyl-1H-pyrazol-3-yl)but-2-en-1-one
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                95.908(9)
_cell_angle_beta                 92.810(9)
_cell_angle_gamma                108.360(8)
_cell_formula_units_Z            2
_cell_length_a                   6.6954(7)
_cell_length_b                   7.6325(8)
_cell_length_c                   9.8928(11)
_cell_measurement_reflns_used    11066
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.30
_cell_measurement_theta_min      2.83
_cell_volume                     475.49(9)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      ' 398 frames, detector distance = 60 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9019
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         2.83
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0606
_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/[Σ²(FO²)+(0.0593P)²+0.0258P] WHERE P=(FO²+2FC²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                1573
_reflns_number_total             2509
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0212_suppl.cif
_cod_data_source_block           I
_cod_database_code               8106955
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.1092(2) 0.3321(2) -0.06708(14) 1.000 0.0788(6) d . . .
O2 O Uani 0.4218(2) 0.3925(2) 0.10720(14) 1.000 0.0769(5) d . . .
N1 N Uani 0.2620(2) 0.2152(2) 0.41691(15) 1.000 0.0586(5) d . . .
N2 N Uani 0.3994(3) 0.2154(2) 0.52120(15) 1.000 0.0605(5) d . . .
C1 C Uani -0.2376(3) 0.1722(4) -0.0188(2) 1.000 0.0829(9) d . . .
C2 C Uani -0.0075(3) 0.2498(3) 0.0239(2) 1.000 0.0623(6) d . . .
C3 C Uani 0.0754(3) 0.2360(3) 0.15005(19) 1.000 0.0600(6) d . . .
C4 C Uani 0.2944(3) 0.3072(2) 0.18732(18) 1.000 0.0549(6) d . . .
C5 C Uani 0.3857(3) 0.2848(2) 0.32015(17) 1.000 0.0528(5) d . . .
C6 C Uani 0.5988(3) 0.3282(3) 0.36322(19) 1.000 0.0612(6) d . . .
C7 C Uani 0.6036(3) 0.2820(3) 0.4932(2) 1.000 0.0610(6) d . . .
C8 C Uani 0.7841(4) 0.2925(4) 0.5918(2) 1.000 0.0829(9) d . . .
C9 C Uani 0.3176(4) 0.1554(4) 0.6484(2) 1.000 0.0829(9) d . . .
H1 H Uiso 0.23410 0.36110 -0.03940 1.000 0.1180 c RU . .
H1A H Uiso -0.29240 0.27200 -0.03140 1.000 0.1240 c RU . .
H1B H Uiso -0.30910 0.10330 0.05030 1.000 0.1240 c RU . .
H1C H Uiso -0.25980 0.09120 -0.10300 1.000 0.1240 c RU . .
H3 H Uiso -0.01470 0.17830 0.21250 1.000 0.0720 c RU . .
H6 H Uiso 0.71370 0.37810 0.31400 1.000 0.0730 c RU . .
H8A H Uiso 0.79510 0.38560 0.66740 1.000 0.1240 c RU . .
H8B H Uiso 0.91250 0.32450 0.54720 1.000 0.1240 c RU . .
H8C H Uiso 0.76070 0.17400 0.62440 1.000 0.1240 c RU . .
H9A H Uiso 0.33810 0.26240 0.71430 1.000 0.1240 c RU . .
H9B H Uiso 0.39130 0.07730 0.68240 1.000 0.1240 c RU . .
H9C H Uiso 0.16960 0.08700 0.63230 1.000 0.1240 c RU . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 1 5 0.1430
-2 -1 -2 0.1820
0 2 1 0.1880
3 -7 -2 0.2980
0 0 -1 0.0360
0 0 1 0.0200
-5 4 -2 0.3130
0 -7 4 0.2790
0 1 5 0.0460
3 0 -8 0.1040
0 -1 -6 0.0800
-3 2 7 0.1450
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.00 . . . no
N2 N1 C5 103.93(15) . . . no
N1 N2 C7 113.04(15) . . . no
N1 N2 C9 118.81(19) . . . no
C7 N2 C9 128.07(19) . . . no
O1 C2 C3 122.39(19) . . . no
C1 C2 C3 122.39(19) . . . no
O1 C2 C1 115.22(17) . . . no
C2 C3 C4 121.41(19) . . . no
O2 C4 C5 116.96(17) . . . no
C3 C4 C5 121.73(16) . . . no
O2 C4 C3 121.31(17) . . . no
N1 C5 C6 111.52(16) . . . no
C4 C5 C6 127.48(17) . . . no
N1 C5 C4 121.00(17) . . . no
C5 C6 C7 105.60(18) . . . no
N2 C7 C8 122.90(18) . . . no
C6 C7 C8 131.2(2) . . . no
N2 C7 C6 105.90(18) . . . no
C2 C1 H1A 109.00 . . . no
C2 C1 H1B 109.00 . . . no
C2 C1 H1C 109.00 . . . no
H1A C1 H1B 109.00 . . . no
H1A C1 H1C 109.00 . . . no
H1B C1 H1C 109.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C5 C6 H6 127.00 . . . no
C7 C6 H6 127.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
C7 C8 H8C 109.00 . . . no
H8A C8 H8B 110.00 . . . no
H8A C8 H8C 109.00 . . . no
H8B C8 H8C 109.00 . . . no
N2 C9 H9A 109.00 . . . no
N2 C9 H9B 109.00 . . . no
N2 C9 H9C 109.00 . . . no
H9A C9 H9B 109.00 . . . no
H9A C9 H9C 109.00 . . . no
H9B C9 H9C 110.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.301(3) . . no
O2 C4 1.266(2) . . no
O1 H1 0.8200 . . no
N1 N2 1.348(2) . . no
N1 C5 1.338(2) . . no
N2 C7 1.354(3) . . no
N2 C9 1.457(3) . . no
C1 C2 1.488(3) . . no
C2 C3 1.368(3) . . no
C3 C4 1.409(3) . . no
C4 C5 1.471(3) . . no
C5 C6 1.393(3) . . no
C6 C7 1.369(3) . . no
C7 C8 1.492(3) . . no
C1 H1A 0.9600 . . no
C1 H1B 0.9600 . . no
C1 H1C 0.9600 . . no
C3 H3 0.9300 . . no
C6 H6 0.9300 . . no
C8 H8A 0.9600 . . no
C8 H8B 0.9600 . . no
C8 H8C 0.9600 . . no
C9 H9A 0.9600 . . no
C9 H9B 0.9600 . . no
C9 H9C 0.9600 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.82 2.538(2) 146 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C7 -0.1(2) . . . . no
C5 N1 N2 C9 177.11(17) . . . . no
N2 N1 C5 C4 179.81(14) . . . . no
N2 N1 C5 C6 0.03(19) . . . . no
C9 N2 C7 C6 -176.8(2) . . . . no
C9 N2 C7 C8 4.3(3) . . . . no
N1 N2 C7 C6 0.1(2) . . . . no
N1 N2 C7 C8 -178.8(2) . . . . no
O1 C2 C3 C4 -1.5(3) . . . . no
C1 C2 C3 C4 178.7(2) . . . . no
C2 C3 C4 C5 -176.94(18) . . . . no
C2 C3 C4 O2 2.6(3) . . . . no
O2 C4 C5 C6 -7.8(3) . . . . no
C3 C4 C5 C6 171.76(19) . . . . no
C3 C4 C5 N1 -8.0(3) . . . . no
O2 C4 C5 N1 172.50(15) . . . . no
C4 C5 C6 C7 -179.71(17) . . . . no
N1 C5 C6 C7 0.0(2) . . . . no
C5 C6 C7 N2 -0.1(2) . . . . no
C5 C6 C7 C8 178.7(2) . . . . no
