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#$Date: 2023-01-17 12:02:59 +0200 (Tue, 17 Jan 2023) $
#$Revision: 280375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106480.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_8106480
loop_
_publ_author_name
'Radi, Smaail'
'Tighadouini, Said'
'Eddike, Driss'
'Tillard, Monique'
'Mabkhot, Yahia N.'
_publ_section_title
;
 Crystal structure of
 (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(4-methoxyphenyl)prop-2-en-1-one,
 C15H16N2O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              199
_journal_page_last               200
_journal_paper_doi               10.1515/ncrs-2016-0190
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety
;
'C15 H16 N2 O3'
;
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 117.43(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.223(2)
_cell_length_b                   11.9339(15)
_cell_length_c                   11.945(2)
_cell_measurement_reflns_used    10796
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.947
_cell_measurement_theta_min      2.045
_cell_volume                     1420.0(5)
_computing_cell_refinement       'CrysAlisRed 171 Oxford Diffraction,2009'
_computing_data_collection       'CrysAlis 171 Oxford Diffraction,2009'
_computing_data_reduction        'CrysAlisRed 171 Oxford Diffraction,2009'
_computing_molecular_graphics    'ortep3 for windows (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97, Sheldrick 1997'
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10796
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.947
_diffrn_reflns_theta_min         2.045
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallepiped
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0528
_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)+(0.0552P)²+0.1452P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2193
_reflns_number_total             3274
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0190_suppl.cif
_cod_data_source_block           moni67
_cod_original_cell_volume        1419.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106480
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33437(18) 0.58646(14) 0.41262(17) 0.0603(4) Uani 1 1 d . . . . .
C2 C 0.44193(19) 0.65956(15) 0.45537(18) 0.0689(5) Uani 1 1 d . . . . .
H13 H 0.4613 0.7043 0.5254 0.083 Uiso 1 1 calc R U . . .
C3 C 0.52015(18) 0.66644(14) 0.39523(17) 0.0638(5) Uani 1 1 d . . . . .
H12 H 0.5917 0.7164 0.4247 0.077 Uiso 1 1 calc R U . . .
C4 C 0.49428(16) 0.59970(13) 0.29052(15) 0.0545(4) Uani 1 1 d . . . . .
C5 C 0.57340(17) 0.60809(14) 0.22126(15) 0.0561(4) Uani 1 1 d . . . . .
C6 C 0.76077(17) 0.67033(13) 0.18904(16) 0.0569(4) Uani 1 1 d . . . . .
C7 C 0.88827(17) 0.72914(14) 0.23243(16) 0.0568(4) Uani 1 1 d . . . . .
C8 C 1.0758(2) 0.80374(15) 0.24927(19) 0.0667(5) Uani 1 1 d . . . . .
C9 C 0.9671(2) 0.74205(15) 0.17018(18) 0.0654(5) Uani 1 1 d . . . . .
H2 H 0.9490 0.7143 0.0912 0.079 Uiso 1 1 calc R U . . .
C10 C 1.1934(2) 0.84747(19) 0.2357(2) 0.0934(7) Uani 1 1 d . . . . .
H3 H 1.1851 0.9271 0.2234 0.140 Uiso 1 1 calc R U . . .
H4 H 1.1959 0.8127 0.1643 0.140 Uiso 1 1 calc R U . . .
H5 H 1.2748 0.8306 0.3106 0.140 Uiso 1 1 calc R U . . .
C11 C 1.1482(2) 0.8853(2) 0.4655(2) 0.0985(8) Uani 1 1 d . . . . .
H6 H 1.1072 0.8925 0.5201 0.148 Uiso 1 1 calc R U . . .
H7 H 1.1658 0.9584 0.4430 0.148 Uiso 1 1 calc R U . . .
H8 H 1.2310 0.8447 0.5083 0.148 Uiso 1 1 calc R U . . .
C12 C 0.69219(17) 0.66641(13) 0.26202(16) 0.0568(4) Uani 1 1 d . . . . .
H9 H 0.7274 0.7037 0.3390 0.068 Uiso 1 1 calc R U . . .
C13 C 0.38824(19) 0.52484(14) 0.25148(16) 0.0625(5) Uani 1 1 d . . . . .
H11 H 0.3704 0.4780 0.1834 0.075 Uiso 1 1 calc R U . . .
C14 C 0.30858(19) 0.51805(14) 0.31091(17) 0.0651(5) Uani 1 1 d . . . . .
H10 H 0.2376 0.4675 0.2826 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1469(2) 0.5168(2) 0.4333(2) 0.0930(7) Uani 1 1 d . . . . .
H14 H 0.0877 0.5323 0.3462 0.140 Uiso 1 1 calc R U . . .
H15 H 0.1003 0.5289 0.4824 0.140 Uiso 1 1 calc R U . . .
H16 H 0.1762 0.4402 0.4420 0.140 Uiso 1 1 calc R U . . .
N1 N 0.94514(15) 0.78047(12) 0.34485(14) 0.0641(4) Uani 1 1 d . . . . .
N2 N 1.05841(15) 0.82513(12) 0.35234(14) 0.0670(4) Uani 1 1 d . . . . .
O1 O 0.26014(14) 0.58896(12) 0.47654(13) 0.0811(4) Uani 1 1 d . . . . .
O2 O 0.52254(13) 0.55531(11) 0.11275(11) 0.0745(4) Uani 1 1 d . . . . .
H1 H 0.6030 0.5720 0.0780 0.112 Uiso 1 1 d R U . . .
O3 O 0.71546(13) 0.62190(10) 0.08166(11) 0.0703(4) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C14 124.82(16) . .
O1 C1 C2 115.70(16) . .
C14 C1 C2 119.48(17) . .
C3 C2 C1 120.39(16) . .
C3 C2 H13 119.8 . .
C1 C2 H13 119.8 . .
C2 C3 C4 121.12(16) . .
C2 C3 H12 119.4 . .
C4 C3 H12 119.4 . .
C13 C4 C3 117.47(16) . .
C13 C4 C5 120.16(15) . .
C3 C4 C5 122.37(15) . .
O2 C5 C12 120.08(16) . .
O2 C5 C4 115.01(15) . .
C12 C5 C4 124.91(15) . .
O3 C6 C12 121.93(16) . .
O3 C6 C7 116.46(16) . .
C12 C6 C7 121.61(15) . .
N1 C7 C9 110.83(16) . .
N1 C7 C6 120.84(15) . .
C9 C7 C6 128.33(17) . .
N2 C8 C9 105.89(16) . .
N2 C8 C10 122.39(19) . .
C9 C8 C10 131.69(19) . .
C8 C9 C7 105.86(16) . .
C8 C9 H2 127.1 . .
C7 C9 H2 127.1 . .
C8 C10 H3 109.5 . .
C8 C10 H4 109.5 . .
H3 C10 H4 109.5 . .
C8 C10 H5 109.5 . .
H3 C10 H5 109.5 . .
H4 C10 H5 109.5 . .
N2 C11 H6 109.5 . .
N2 C11 H7 109.5 . .
H6 C11 H7 109.5 . .
N2 C11 H8 109.5 . .
H6 C11 H8 109.5 . .
H7 C11 H8 109.5 . .
C5 C12 C6 120.99(15) . .
C5 C12 H9 119.5 . .
C6 C12 H9 119.5 . .
C14 C13 C4 121.70(16) . .
C14 C13 H11 119.2 . .
C4 C13 H11 119.2 . .
C13 C14 C1 119.80(16) . .
C13 C14 H10 120.1 . .
C1 C14 H10 120.1 . .
O1 C15 H14 109.5 . .
O1 C15 H15 109.5 . .
H14 C15 H15 109.5 . .
O1 C15 H16 109.5 . .
H14 C15 H16 109.5 . .
H15 C15 H16 109.5 . .
C7 N1 N2 104.33(14) . .
N1 N2 C8 113.09(16) . .
N1 N2 C11 119.25(16) . .
C8 N2 C11 127.63(17) . .
C1 O1 C15 117.20(15) . .
C5 O2 H1 102.3 . .
C6 O3 H1 99.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.365(2) .
C1 C14 1.379(2) .
C1 C2 1.382(2) .
C2 C3 1.369(3) .
C2 H13 0.9300 .
C3 C4 1.396(2) .
C3 H12 0.9300 .
C4 C13 1.386(2) .
C4 C5 1.470(2) .
C5 O2 1.3118(19) .
C5 C12 1.379(2) .
C6 O3 1.279(2) .
C6 C12 1.404(2) .
C6 C7 1.458(2) .
C7 N1 1.340(2) .
C7 C9 1.402(2) .
C8 N2 1.356(2) .
C8 C9 1.364(3) .
C8 C10 1.497(3) .
C9 H2 0.9300 .
C10 H3 0.9600 .
C10 H4 0.9600 .
C10 H5 0.9600 .
C11 N2 1.450(3) .
C11 H6 0.9600 .
C11 H7 0.9600 .
C11 H8 0.9600 .
C12 H9 0.9300 .
C13 C14 1.376(3) .
C13 H11 0.9300 .
C14 H10 0.9300 .
C15 O1 1.421(2) .
C15 H14 0.9600 .
C15 H15 0.9600 .
C15 H16 0.9600 .
N1 N2 1.3429(19) .
O2 H1 1.1712 .
O3 H1 1.3784 .
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
O1 C1 C2 C3 -177.79(17) . . . .
C14 C1 C2 C3 1.8(3) . . . .
C1 C2 C3 C4 -0.5(3) . . . .
C2 C3 C4 C13 -1.2(3) . . . .
C2 C3 C4 C5 177.74(17) . . . .
C13 C4 C5 O2 10.8(2) . . . .
C3 C4 C5 O2 -168.17(15) . . . .
C13 C4 C5 C12 -169.67(15) . . . .
C3 C4 C5 C12 11.4(3) . . . .
O3 C6 C7 N1 -178.63(14) . . . .
C12 C6 C7 N1 0.8(2) . . . .
O3 C6 C7 C9 1.7(2) . . . .
C12 C6 C7 C9 -178.86(16) . . . .
N2 C8 C9 C7 -0.20(19) . . . .
C10 C8 C9 C7 -178.28(19) . . . .
N1 C7 C9 C8 0.07(19) . . . .
C6 C7 C9 C8 179.79(15) . . . .
O2 C5 C12 C6 -0.1(2) . . . .
C4 C5 C12 C6 -179.65(15) . . . .
O3 C6 C12 C5 1.1(2) . . . .
C7 C6 C12 C5 -178.33(14) . . . .
C3 C4 C13 C14 1.7(3) . . . .
C5 C4 C13 C14 -177.27(16) . . . .
C4 C13 C14 C1 -0.5(3) . . . .
O1 C1 C14 C13 178.24(17) . . . .
C2 C1 C14 C13 -1.3(3) . . . .
C9 C7 N1 N2 0.10(18) . . . .
C6 C7 N1 N2 -179.65(14) . . . .
C7 N1 N2 C8 -0.23(19) . . . .
C7 N1 N2 C11 -178.27(17) . . . .
C9 C8 N2 N1 0.3(2) . . . .
C10 C8 N2 N1 178.58(16) . . . .
C9 C8 N2 C11 178.12(19) . . . .
C10 C8 N2 C11 -3.6(3) . . . .
C14 C1 O1 C15 -1.0(3) . . . .
C2 C1 O1 C15 178.57(17) . . . .
