#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150589.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_7150589
loop_
_publ_author_name
'Ko, Young Ok'
'Chun, Yu Sung'
'Park, Cho-Long'
'Kim, Youngmee'
'Shin, Hyunik'
'Ahn, Sungho'
'Hong, Jongki'
'Lee, Sang-gi'
_publ_section_title
;
 An effective and general method for the highly regioselective
 synthesis of 1-phenylpyrazoles from β-enaminoketoesters, tandem
 Blaise--acylation adducts
;
_journal_issue                   6
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1132
_journal_page_last               1136
_journal_paper_doi               10.1039/b820324e
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C25 H19 F3 N2 O2'
_chemical_formula_weight         436.42
_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
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.535(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.182(2)
_cell_length_b                   19.321(4)
_cell_length_c                   9.0766(17)
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.50
_cell_volume                     2112.7(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.1132
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11696
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.676
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0151P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                1985
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820324e.txt
_cod_data_source_block           2e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150589
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42143(12) -0.00783(8) 0.23918(17) 0.0269(4) Uani 1 1 d . . .
C2 C 0.52595(12) 0.01402(8) 0.21314(17) 0.0262(4) Uani 1 1 d . . .
C3 C 0.59930(13) -0.04107(8) 0.26291(18) 0.0287(4) Uani 1 1 d . . .
C4 C 0.31282(12) 0.02830(8) 0.22084(19) 0.0267(4) Uani 1 1 d . . .
C5 C 0.28976(13) 0.07314(8) 0.33191(19) 0.0348(4) Uani 1 1 d . . .
H5 H 0.3408 0.0777 0.4213 0.042 Uiso 1 1 calc R . .
C6 C 0.19227(14) 0.11111(8) 0.3121(2) 0.0388(5) Uani 1 1 d . . .
H6 H 0.1771 0.1423 0.3875 0.047 Uiso 1 1 calc R . .
C7 C 0.11738(13) 0.10385(8) 0.1839(2) 0.0335(5) Uani 1 1 d . . .
C8 C 0.13863(13) 0.05771(8) 0.07556(19) 0.0383(5) Uani 1 1 d . . .
H8 H 0.0862 0.0518 -0.0120 0.046 Uiso 1 1 calc R . .
C9 C 0.23633(13) 0.02005(8) 0.09460(19) 0.0346(4) Uani 1 1 d . . .
H9 H 0.2507 -0.0117 0.0199 0.041 Uiso 1 1 calc R . .
C10 C 0.01777(16) 0.14902(10) 0.1537(2) 0.0502(6) Uani 1 1 d . . .
C11 C 0.55085(14) 0.07813(8) 0.13835(19) 0.0305(4) Uani 1 1 d . . .
C12 C 0.47894(14) 0.18771(8) 0.0530(2) 0.0444(5) Uani 1 1 d . . .
H12A H 0.4822 0.1785 -0.0535 0.053 Uiso 1 1 calc R . .
H12B H 0.5478 0.2120 0.0965 0.053 Uiso 1 1 calc R . .
C13 C 0.37908(14) 0.23078(8) 0.0697(2) 0.0583(6) Uani 1 1 d . . .
H13A H 0.3117 0.2061 0.0264 0.087 Uiso 1 1 calc R . .
H13B H 0.3834 0.2750 0.0180 0.087 Uiso 1 1 calc R . .
H13C H 0.3769 0.2394 0.1757 0.087 Uiso 1 1 calc R . .
C14 C 0.72133(13) -0.04934(8) 0.27682(18) 0.0288(4) Uani 1 1 d . . .
C15 C 0.76554(13) -0.11515(8) 0.26629(19) 0.0379(5) Uani 1 1 d . . .
H15 H 0.7172 -0.1534 0.2425 0.045 Uiso 1 1 calc R . .
C16 C 0.87861(14) -0.12555(10) 0.2899(2) 0.0469(5) Uani 1 1 d . . .
H16 H 0.9076 -0.1708 0.2816 0.056 Uiso 1 1 calc R . .
C17 C 0.95017(14) -0.07062(10) 0.3255(2) 0.0466(5) Uani 1 1 d . . .
H17 H 1.0282 -0.0779 0.3427 0.056 Uiso 1 1 calc R . .
C18 C 0.90699(13) -0.00500(9) 0.33558(18) 0.0418(5) Uani 1 1 d . . .
H18 H 0.9557 0.0331 0.3590 0.050 Uiso 1 1 calc R . .
C19 C 0.79367(13) 0.00565(9) 0.31188(18) 0.0347(4) Uani 1 1 d . . .
H19 H 0.7650 0.0510 0.3197 0.042 Uiso 1 1 calc R . .
C20 C 0.35647(13) -0.11804(8) 0.3481(2) 0.0280(4) Uani 1 1 d . . .
C21 C 0.26654(13) -0.14078(8) 0.2516(2) 0.0369(5) Uani 1 1 d . . .
H21 H 0.2554 -0.1261 0.1506 0.044 Uiso 1 1 calc R . .
C22 C 0.19217(14) -0.18546(8) 0.3036(2) 0.0423(5) Uani 1 1 d . . .
H22 H 0.1290 -0.2013 0.2381 0.051 Uiso 1 1 calc R . .
C23 C 0.20920(15) -0.20697(8) 0.4493(2) 0.0428(5) Uani 1 1 d . . .
H23 H 0.1574 -0.2372 0.4847 0.051 Uiso 1 1 calc R . .
C24 C 0.30126(15) -0.18489(8) 0.5444(2) 0.0440(5) Uani 1 1 d . . .
H24 H 0.3134 -0.2005 0.6448 0.053 Uiso 1 1 calc R . .
C25 C 0.37601(13) -0.14001(8) 0.4940(2) 0.0360(5) Uani 1 1 d . . .
H25 H 0.4397 -0.1246 0.5589 0.043 Uiso 1 1 calc R . .
F1 F -0.06937(8) 0.11876(5) 0.07527(14) 0.0703(4) Uani 1 1 d . . .
F2 F -0.01637(9) 0.17234(6) 0.27744(14) 0.0863(4) Uani 1 1 d . . .
F3 F 0.03729(9) 0.20557(6) 0.07641(15) 0.0810(4) Uani 1 1 d . . .
N1 N 0.43624(10) -0.07213(6) 0.29780(14) 0.0295(4) Uani 1 1 d . . .
N2 N 0.54415(10) -0.09326(6) 0.31487(15) 0.0315(4) Uani 1 1 d . . .
O1 O 0.63517(9) 0.09023(5) 0.08833(13) 0.0402(3) Uani 1 1 d . . .
O2 O 0.46719(9) 0.12354(5) 0.13156(13) 0.0399(3) 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
N1 C1 C2 105.84(13) . . ?
N1 C1 C4 122.75(13) . . ?
C2 C1 C4 131.30(14) . . ?
C1 C2 C3 105.45(14) . . ?
C1 C2 C11 126.26(15) . . ?
C3 C2 C11 128.11(14) . . ?
N2 C3 C2 110.65(13) . . ?
N2 C3 C14 116.05(14) . . ?
C2 C3 C14 133.16(15) . . ?
C9 C4 C5 119.48(15) . . ?
C9 C4 C1 121.46(15) . . ?
C5 C4 C1 119.02(16) . . ?
C6 C5 C4 119.89(17) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.26(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.86(15) . . ?
C6 C7 C10 121.10(17) . . ?
C8 C7 C10 118.85(18) . . ?
C7 C8 C9 119.98(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 120.47(16) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
F1 C10 F2 106.08(16) . . ?
F1 C10 F3 105.63(17) . . ?
F2 C10 F3 105.52(16) . . ?
F1 C10 C7 114.03(16) . . ?
F2 C10 C7 113.05(18) . . ?
F3 C10 C7 111.84(15) . . ?
O1 C11 O2 122.72(15) . . ?
O1 C11 C2 125.78(15) . . ?
O2 C11 C2 111.50(14) . . ?
O2 C12 C13 106.53(12) . . ?
O2 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.50(15) . . ?
C19 C14 C3 122.15(15) . . ?
C15 C14 C3 119.14(15) . . ?
C16 C15 C14 120.78(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.43(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.18(17) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 120.56(16) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.54(16) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C25 121.60(15) . . ?
C21 C20 N1 120.54(16) . . ?
C25 C20 N1 117.82(15) . . ?
C20 C21 C22 118.93(17) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.30(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.18(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 120.09(17) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 118.87(17) . . ?
C20 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C1 N1 N2 112.94(12) . . ?
C1 N1 C20 129.33(13) . . ?
N2 N1 C20 117.67(12) . . ?
C3 N2 N1 105.11(12) . . ?
C11 O2 C12 116.97(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3529(17) . ?
C1 C2 1.3945(18) . ?
C1 C4 1.4833(19) . ?
C2 C3 1.420(2) . ?
C2 C11 1.466(2) . ?
C3 N2 1.3360(16) . ?
C3 C14 1.482(2) . ?
C4 C9 1.375(2) . ?
C4 C5 1.389(2) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 C10 1.487(2) . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 F1 1.323(2) . ?
C10 F2 1.333(2) . ?
C10 F3 1.3387(19) . ?
C11 O1 1.2059(16) . ?
C11 O2 1.3393(17) . ?
C12 O2 1.4476(16) . ?
C12 C13 1.500(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.387(2) . ?
C14 C15 1.3897(19) . ?
C15 C16 1.377(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.370(2) . ?
C20 C25 1.377(2) . ?
C20 N1 1.4393(17) . ?
C21 C22 1.3841(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3836(19) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 N2 1.3633(15) . ?
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
N1 C1 C2 C3 -1.01(17) . . . . ?
C4 C1 C2 C3 175.19(17) . . . . ?
N1 C1 C2 C11 174.38(15) . . . . ?
C4 C1 C2 C11 -9.4(3) . . . . ?
C1 C2 C3 N2 0.40(18) . . . . ?
C11 C2 C3 N2 -174.87(15) . . . . ?
C1 C2 C3 C14 -174.96(17) . . . . ?
C11 C2 C3 C14 9.8(3) . . . . ?
N1 C1 C4 C9 -87.9(2) . . . . ?
C2 C1 C4 C9 96.5(2) . . . . ?
N1 C1 C4 C5 94.24(19) . . . . ?
C2 C1 C4 C5 -81.4(2) . . . . ?
C9 C4 C5 C6 -2.6(2) . . . . ?
C1 C4 C5 C6 175.38(14) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C8 1.1(2) . . . . ?
C5 C6 C7 C10 -173.88(16) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C10 C7 C8 C9 173.56(15) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
C1 C4 C9 C8 -175.75(14) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
C6 C7 C10 F1 -148.71(17) . . . . ?
C8 C7 C10 F1 36.3(2) . . . . ?
C6 C7 C10 F2 -27.4(2) . . . . ?
C8 C7 C10 F2 157.57(16) . . . . ?
C6 C7 C10 F3 91.5(2) . . . . ?
C8 C7 C10 F3 -83.5(2) . . . . ?
C1 C2 C11 O1 -163.38(17) . . . . ?
C3 C2 C11 O1 11.0(3) . . . . ?
C1 C2 C11 O2 16.8(2) . . . . ?
C3 C2 C11 O2 -168.87(16) . . . . ?
N2 C3 C14 C19 -141.99(16) . . . . ?
C2 C3 C14 C19 33.2(3) . . . . ?
N2 C3 C14 C15 32.7(2) . . . . ?
C2 C3 C14 C15 -152.09(18) . . . . ?
C19 C14 C15 C16 -0.1(2) . . . . ?
C3 C14 C15 C16 -175.03(15) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C3 C14 C19 C18 174.81(15) . . . . ?
C25 C20 C21 C22 1.8(2) . . . . ?
N1 C20 C21 C22 179.34(13) . . . . ?
C20 C21 C22 C23 -0.6(2) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C21 C20 C25 C24 -1.5(2) . . . . ?
N1 C20 C25 C24 -179.15(13) . . . . ?
C23 C24 C25 C20 0.1(2) . . . . ?
C2 C1 N1 N2 1.33(18) . . . . ?
C4 C1 N1 N2 -175.28(14) . . . . ?
C2 C1 N1 C20 178.55(15) . . . . ?
C4 C1 N1 C20 1.9(3) . . . . ?
C21 C20 N1 C1 60.7(2) . . . . ?
C25 C20 N1 C1 -121.69(18) . . . . ?
C21 C20 N1 N2 -122.23(16) . . . . ?
C25 C20 N1 N2 55.43(19) . . . . ?
C2 C3 N2 N1 0.37(17) . . . . ?
C14 C3 N2 N1 176.60(13) . . . . ?
C1 N1 N2 C3 -1.07(17) . . . . ?
C20 N1 N2 C3 -178.65(13) . . . . ?
O1 C11 O2 C12 3.4(2) . . . . ?
C2 C11 O2 C12 -176.78(13) . . . . ?
C13 C12 O2 C11 -176.48(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653365
2 PubChem 25243551
