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#$Date: 2023-06-01 04:06:51 +0300 (Thu, 01 Jun 2023) $
#$Revision: 284116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246858.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_7246858
loop_
_publ_author_name
'Arias-Gómez, Andres'
'Macías, Mario A.'
'Portilla, Jaime'
_publ_section_title
;
 Synthesis of structural analogues of Reversan by ester aminolysis: an
 access to pyrazolo[1,5-a]pyrimidines from chalcones
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              16377
_journal_page_last               16386
_journal_paper_doi               10.1039/D3RA02553E
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.977(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2765(7)
_cell_length_b                   14.1241(8)
_cell_length_c                   10.5227(5)
_cell_measurement_reflns_used    7176
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.0410
_cell_measurement_theta_min      4.2660
_cell_volume                     1754.10(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.574
_diffrn_reflns_theta_min         3.745
_diffrn_source
'SuperNova (Cu) micro-focus sealed X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0497
_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)+(0.0768P)²+0.1503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3045
_reflns_number_total             3642
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra02553e2.cif
_cod_data_source_block           4a
_cod_original_cell_volume        1754.12(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246858
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.886
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
C4 C 0.45182(12) 0.63415(9) 0.57087(13) 0.0499(3) Uani 1 1 d . . . . .
N2 N 0.54626(10) 0.63785(8) 0.68028(11) 0.0504(3) Uani 1 1 d . . . . .
O2 O 0.32422(10) 0.61133(8) 0.29739(10) 0.0635(3) Uani 1 1 d . . . . .
C2 C 0.49482(13) 0.62012(10) 0.46234(14) 0.0551(3) Uani 1 1 d . . . . .
C3 C 0.61199(13) 0.61545(11) 0.51702(15) 0.0609(4) Uani 1 1 d . . . . .
H3 H 0.662148 0.605951 0.466176 0.073 Uiso 1 1 calc R U . . .
N3 N 0.64593(11) 0.62560(10) 0.64689(13) 0.0601(3) Uani 1 1 d . . . . .
C19 C 0.18848(13) 0.69011(12) 0.82161(14) 0.0609(4) Uani 1 1 d . . . . .
H19 H 0.244835 0.717978 0.888860 0.073 Uiso 1 1 calc R U . . .
C14 C 0.21581(12) 0.65019(10) 0.71349(13) 0.0523(3) Uani 1 1 d . . . . .
C13 C 0.74085(13) 0.68423(12) 0.91832(16) 0.0657(4) Uani 1 1 d . . . . .
H13 H 0.748007 0.713840 0.842090 0.079 Uiso 1 1 calc R U . . .
N1 N 0.34564(10) 0.64044(8) 0.58185(11) 0.0525(3) Uani 1 1 d . . . . .
C1 C 0.43642(14) 0.60589(11) 0.32330(14) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.48434(12) 0.58886(13) 0.24079(12) 0.0953(5) Uani 1 1 d . . . . .
C8 C 0.63719(11) 0.64506(10) 0.92132(13) 0.0515(3) Uani 1 1 d . . . . .
C7 C 0.53636(12) 0.64660(9) 0.80637(13) 0.0495(3) Uani 1 1 d . . . . .
C6 C 0.42754(11) 0.65258(10) 0.81614(13) 0.0507(3) Uani 1 1 d . . . . .
H6 H 0.415130 0.659365 0.898950 0.061 Uiso 1 1 calc R U . . .
C5 C 0.33377(11) 0.64863(9) 0.70248(12) 0.0493(3) Uani 1 1 d . . . . .
C18 C 0.07752(14) 0.68858(14) 0.82961(17) 0.0716(4) Uani 1 1 d . . . . .
H18 H 0.059948 0.715695 0.902058 0.086 Uiso 1 1 calc R U . . .
C20 C 0.25883(17) 0.59258(14) 0.16406(15) 0.0752(5) Uani 1 1 d . . . . .
H20A H 0.290721 0.539197 0.128666 0.090 Uiso 1 1 calc R U . . .
H20B H 0.260005 0.647328 0.108792 0.090 Uiso 1 1 calc R U . . .
C9 C 0.62853(13) 0.60289(11) 1.03741(14) 0.0587(4) Uani 1 1 d . . . . .
H9 H 0.559571 0.577617 1.041322 0.070 Uiso 1 1 calc R U . . .
C21 C 0.14176(19) 0.57134(19) 0.1649(2) 0.1028(7) Uani 1 1 d . . . . .
H21A H 0.098444 0.553267 0.077720 0.154 Uiso 1 1 calc R U . . .
H21B H 0.108502 0.626510 0.192318 0.154 Uiso 1 1 calc R U . . .
H21C H 0.141911 0.520379 0.225355 0.154 Uiso 1 1 calc R U . . .
C12 C 0.83269(14) 0.67893(17) 1.02866(19) 0.0814(5) Uani 1 1 d . . . . .
H12 H 0.901550 0.705230 1.026283 0.098 Uiso 1 1 calc R U . . .
C15 C 0.12955(14) 0.61039(13) 0.61367(17) 0.0690(4) Uani 1 1 d . . . . .
H15 H 0.146025 0.584748 0.539681 0.083 Uiso 1 1 calc R U . . .
C10 C 0.72130(15) 0.59807(14) 1.14721(16) 0.0723(4) Uani 1 1 d . . . . .
H10 H 0.714466 0.569727 1.224423 0.087 Uiso 1 1 calc R U . . .
C17 C -0.00633(15) 0.64740(14) 0.7316(2) 0.0773(5) Uani 1 1 d . . . . .
H17 H -0.080335 0.645682 0.738083 0.093 Uiso 1 1 calc R U . . .
C11 C 0.82360(15) 0.63513(17) 1.14234(18) 0.0833(6) Uani 1 1 d . . . . .
H11 H 0.886458 0.630661 1.215483 0.100 Uiso 1 1 calc R U . . .
C16 C 0.01954(15) 0.60847(15) 0.6231(2) 0.0829(5) Uani 1 1 d . . . . .
H16 H -0.037296 0.580860 0.556121 0.099 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 C4 N2 122.25(11) . . ?
N1 C4 C2 132.34(13) . . ?
N2 C4 C2 105.38(12) . . ?
C7 N2 N3 125.55(12) . . ?
C7 N2 C4 121.89(11) . . ?
N3 N2 C4 112.43(11) . . ?
C1 O2 C20 117.27(12) . . ?
C3 C2 C4 104.35(13) . . ?
C3 C2 C1 125.06(13) . . ?
C4 C2 C1 130.44(14) . . ?
N3 C3 C2 114.63(12) . . ?
N3 C3 H3 122.7 . . ?
C2 C3 H3 122.7 . . ?
C3 N3 N2 103.20(12) . . ?
C18 C19 C14 120.33(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C15 C14 C19 118.51(14) . . ?
C15 C14 C5 119.48(13) . . ?
C19 C14 C5 122.00(13) . . ?
C12 C13 C8 119.89(16) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C5 N1 C4 117.04(12) . . ?
O1 C1 O2 123.33(15) . . ?
O1 C1 C2 123.46(16) . . ?
O2 C1 C2 113.18(12) . . ?
C9 C8 C13 118.73(14) . . ?
C9 C8 C7 118.54(12) . . ?
C13 C8 C7 122.73(13) . . ?
C6 C7 N2 115.22(12) . . ?
C6 C7 C8 123.73(12) . . ?
N2 C7 C8 120.99(12) . . ?
C7 C6 C5 121.16(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C5 C6 122.42(13) . . ?
N1 C5 C14 116.36(12) . . ?
C6 C5 C14 121.19(12) . . ?
C17 C18 C19 120.49(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O2 C20 C21 108.41(15) . . ?
O2 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
O2 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C10 C9 C8 120.73(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 C13 120.80(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C16 C15 C14 120.71(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C11 C10 C9 120.06(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C18 C17 C16 119.70(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C10 C11 C12 119.76(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C17 C16 C15 120.23(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
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
C4 N1 1.3429(17) . ?
C4 N2 1.3920(18) . ?
C4 C2 1.3978(18) . ?
N2 C7 1.3708(17) . ?
N2 N3 1.3738(15) . ?
O2 C1 1.3308(19) . ?
O2 C20 1.4363(19) . ?
C2 C3 1.396(2) . ?
C2 C1 1.455(2) . ?
C3 N3 1.322(2) . ?
C3 H3 0.9300 . ?
C19 C18 1.388(2) . ?
C19 C14 1.391(2) . ?
C19 H19 0.9300 . ?
C14 C15 1.389(2) . ?
C14 C5 1.4843(18) . ?
C13 C12 1.380(2) . ?
C13 C8 1.396(2) . ?
C13 H13 0.9300 . ?
N1 C5 1.3220(17) . ?
C1 O1 1.1996(18) . ?
C8 C9 1.389(2) . ?
C8 C7 1.4736(19) . ?
C7 C6 1.3704(18) . ?
C6 C5 1.4145(19) . ?
C6 H6 0.9300 . ?
C18 C17 1.370(3) . ?
C18 H18 0.9300 . ?
C20 C21 1.471(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C12 C11 1.378(3) . ?
C12 H12 0.9300 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C17 C16 1.380(3) . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
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 C4 N2 C7 1.1(2) . . . . ?
C2 C4 N2 C7 -176.89(12) . . . . ?
N1 C4 N2 N3 177.12(12) . . . . ?
C2 C4 N2 N3 -0.88(15) . . . . ?
N1 C4 C2 C3 -176.98(14) . . . . ?
N2 C4 C2 C3 0.73(15) . . . . ?
N1 C4 C2 C1 -1.2(3) . . . . ?
N2 C4 C2 C1 176.48(14) . . . . ?
C4 C2 C3 N3 -0.39(18) . . . . ?
C1 C2 C3 N3 -176.45(14) . . . . ?
C2 C3 N3 N2 -0.13(18) . . . . ?
C7 N2 N3 C3 176.47(13) . . . . ?
C4 N2 N3 C3 0.63(16) . . . . ?
C18 C19 C14 C15 1.0(2) . . . . ?
C18 C19 C14 C5 -178.73(14) . . . . ?
N2 C4 N1 C5 -1.26(19) . . . . ?
C2 C4 N1 C5 176.13(14) . . . . ?
C20 O2 C1 O1 2.1(2) . . . . ?
C20 O2 C1 C2 -176.36(13) . . . . ?
C3 C2 C1 O1 -0.3(3) . . . . ?
C4 C2 C1 O1 -175.31(17) . . . . ?
C3 C2 C1 O2 178.08(14) . . . . ?
C4 C2 C1 O2 3.1(2) . . . . ?
C12 C13 C8 C9 1.2(2) . . . . ?
C12 C13 C8 C7 -178.81(15) . . . . ?
N3 N2 C7 C6 -176.27(12) . . . . ?
C4 N2 C7 C6 -0.80(18) . . . . ?
N3 N2 C7 C8 1.1(2) . . . . ?
C4 N2 C7 C8 176.58(12) . . . . ?
C9 C8 C7 C6 32.4(2) . . . . ?
C13 C8 C7 C6 -147.59(15) . . . . ?
C9 C8 C7 N2 -144.76(14) . . . . ?
C13 C8 C7 N2 35.3(2) . . . . ?
N2 C7 C6 C5 0.74(19) . . . . ?
C8 C7 C6 C5 -176.55(12) . . . . ?
C4 N1 C5 C6 1.21(19) . . . . ?
C4 N1 C5 C14 -176.75(12) . . . . ?
C7 C6 C5 N1 -1.0(2) . . . . ?
C7 C6 C5 C14 176.86(12) . . . . ?
C15 C14 C5 N1 23.08(19) . . . . ?
C19 C14 C5 N1 -157.22(14) . . . . ?
C15 C14 C5 C6 -154.90(15) . . . . ?
C19 C14 C5 C6 24.8(2) . . . . ?
C14 C19 C18 C17 0.3(3) . . . . ?
C1 O2 C20 C21 161.64(16) . . . . ?
C13 C8 C9 C10 -1.3(2) . . . . ?
C7 C8 C9 C10 178.78(14) . . . . ?
C8 C13 C12 C11 0.1(3) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
C5 C14 C15 C16 178.17(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C19 C18 C17 C16 -1.0(3) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C13 C12 C11 C10 -1.5(3) . . . . ?
C18 C17 C16 C15 0.4(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
