#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225592.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225592
loop_
_publ_author_name
'Meng, Qing-Yang'
'Jia, Jiong'
'Yin, Ling'
'Zhan, Fu-Xu'
'Wang, Jian-Wu'
_publ_section_title
;
 Ethyl
 3-{5-[(diethylamino)methyl]isoxazol-3-yl}-2-phenylpyrazolo[1,5-a]pyridine-5-carboxylate
;
_journal_coeditor_code           IS2515
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o723
_journal_paper_doi               10.1107/S1600536810004174
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H26 N4 O3'
_chemical_formula_moiety         'C24 H26 N4 O3'
_chemical_formula_sum            'C24 H26 N4 O3'
_chemical_formula_weight         418.49
_chemical_name_systematic
;
Ethyl 3-{5-[(diethylamino)methyl]isoxazol-3-yl}-2-
phenylpyrazolo[1,5-a]pyridine-5-carboxylate
;
_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                93.600(2)
_cell_angle_beta                 95.514(2)
_cell_angle_gamma                95.637(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1250(7)
_cell_length_b                   13.1425(16)
_cell_length_c                   13.7139(16)
_cell_measurement_reflns_used    1181
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.45
_cell_volume                     1090.6(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5453
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.50
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0993P)²+0.4336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1865
_reflns_number_gt                2842
_reflns_number_total             3800
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2515.cif
_cod_data_source_block           I
_cod_database_code               2225592
_cod_database_fobs_code          2225592
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
C C1 0.2802(5) -0.0313(2) 0.0758(3) 0.0669(9) Uani d . 1 . .
H H1A 0.4008 -0.0724 0.0722 0.100 Uiso calc R 1 . .
H H1B 0.2200 -0.0200 0.0106 0.100 Uiso calc R 1 . .
H H1C 0.1680 -0.0663 0.1094 0.100 Uiso calc R 1 . .
C C2 0.3600(5) 0.0686(2) 0.1300(2) 0.0585(8) Uani d . 1 . .
H H2A 0.4219 0.0570 0.1957 0.070 Uiso calc R 1 . .
H H2B 0.4758 0.1031 0.0968 0.070 Uiso calc R 1 . .
C C3 0.1430(4) 0.19374(19) 0.06317(19) 0.0441(6) Uani d . 1 . .
C C4 -0.0421(4) 0.25659(18) 0.07983(17) 0.0393(6) Uani d . 1 . .
C C5 -0.1456(4) 0.25212(18) 0.16402(17) 0.0366(5) Uani d . 1 . .
H H5 -0.1060 0.2073 0.2109 0.044 Uiso calc R 1 . .
C C6 -0.3125(4) 0.31605(17) 0.17869(16) 0.0346(5) Uani d . 1 . .
C C7 -0.2687(4) 0.3840(2) 0.02118(18) 0.0451(6) Uani d . 1 . .
H H7 -0.3130 0.4270 -0.0266 0.054 Uiso calc R 1 . .
C C8 -0.1074(5) 0.3235(2) 0.00756(18) 0.0470(6) Uani d . 1 . .
H H8 -0.0380 0.3255 -0.0498 0.056 Uiso calc R 1 . .
C C9 -0.4470(4) 0.33567(17) 0.25335(16) 0.0358(5) Uani d . 1 . .
C C10 -0.5678(4) 0.41490(18) 0.22118(17) 0.0366(5) Uani d . 1 . .
C C11 -0.7208(4) 0.47407(18) 0.27307(18) 0.0387(6) Uani d . 1 . .
C C12 -0.6795(5) 0.5013(2) 0.3729(2) 0.0556(7) Uani d . 1 . .
H H12 -0.5587 0.4790 0.4087 0.067 Uiso calc R 1 . .
C C13 -0.8164(6) 0.5616(3) 0.4199(2) 0.0686(9) Uani d . 1 . .
H H13 -0.7867 0.5799 0.4868 0.082 Uiso calc R 1 . .
C C14 -0.9967(6) 0.5946(2) 0.3677(3) 0.0675(9) Uani d . 1 . .
H H14 -1.0897 0.6345 0.3993 0.081 Uiso calc R 1 . .
C C15 -1.0381(5) 0.5682(2) 0.2687(3) 0.0610(8) Uani d . 1 . .
H H15 -1.1597 0.5904 0.2335 0.073 Uiso calc R 1 . .
C C16 -0.9014(4) 0.50908(19) 0.2210(2) 0.0464(6) Uani d . 1 . .
H H16 -0.9301 0.4925 0.1538 0.056 Uiso calc R 1 . .
C C17 -0.4706(4) 0.27444(18) 0.33801(17) 0.0369(5) Uani d . 1 . .
C C18 -0.6611(4) 0.2496(2) 0.38597(18) 0.0437(6) Uani d . 1 . .
H H18 -0.7981 0.2739 0.3743 0.052 Uiso calc R 1 . .
C C19 -0.6021(5) 0.1835(2) 0.45177(19) 0.0467(6) Uani d . 1 . .
C C20 -0.7261(5) 0.1236(2) 0.5216(2) 0.0582(8) Uani d . 1 . .
H H20A -0.8790 0.1091 0.4945 0.070 Uiso calc R 1 . .
H H20B -0.6655 0.0586 0.5283 0.070 Uiso calc R 1 . .
C C21 -0.4753(6) 0.2470(3) 0.7671(2) 0.0775(10) Uani d U 1 . .
H H21A -0.3289 0.2451 0.7985 0.116 Uiso calc R 1 . .
H H21B -0.5810 0.2223 0.8097 0.116 Uiso calc R 1 . .
H H21C -0.4972 0.3162 0.7534 0.116 Uiso calc R 1 . .
C C22 -0.5053(6) 0.1792(3) 0.6711(2) 0.0719(9) Uani d U 1 . .
H H22A -0.3953 0.2038 0.6293 0.086 Uiso calc R 1 . .
H H22B -0.4793 0.1099 0.6855 0.086 Uiso calc R 1 . .
C C23 -0.9023(6) 0.1347(3) 0.6722(3) 0.0747(10) Uani d . 1 . .
H H23A -0.9082 0.1799 0.7304 0.090 Uiso calc R 1 . .
H H23B -1.0389 0.1367 0.6305 0.090 Uiso calc R 1 . .
C C24 -0.8942(7) 0.0293(3) 0.7027(3) 0.0898(12) Uani d . 1 . .
H H24A -1.0212 0.0102 0.7361 0.135 Uiso calc R 1 . .
H H24B -0.7628 0.0263 0.7462 0.135 Uiso calc R 1 . .
H H24C -0.8935 -0.0170 0.6458 0.135 Uiso calc R 1 . .
N N1 -0.3662(3) 0.38084(15) 0.10689(14) 0.0374(5) Uani d . 1 . .
N N2 -0.5209(3) 0.44225(16) 0.13189(15) 0.0419(5) Uani d . 1 . .
N N3 -0.3039(4) 0.22794(19) 0.37371(17) 0.0572(7) Uani d . 1 . .
N N4 -0.7175(4) 0.1771(2) 0.61889(18) 0.0590(7) Uani d . 1 . .
O O1 0.1826(3) 0.13349(14) 0.13639(14) 0.0520(5) Uani d . 1 . .
O O2 0.2449(4) 0.19763(17) -0.00730(16) 0.0689(6) Uani d . 1 . .
O O3 -0.3882(4) 0.16863(16) 0.44714(14) 0.0633(6) Uani 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
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C1 . . 111.2(2) ?
O1 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
O1 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O2 C3 O1 . . 124.2(2) ?
O2 C3 C4 . . 123.9(3) ?
O1 C3 C4 . . 111.9(2) ?
C5 C4 C8 . . 120.0(2) ?
C5 C4 C3 . . 121.2(2) ?
C8 C4 C3 . . 118.8(2) ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
N1 C6 C9 . . 105.8(2) ?
N1 C6 C5 . . 118.2(2) ?
C9 C6 C5 . . 136.0(2) ?
C8 C7 N1 . . 118.6(2) ?
C8 C7 H7 . . 120.7 ?
N1 C7 H7 . . 120.7 ?
C7 C8 C4 . . 120.7(2) ?
C7 C8 H8 . . 119.6 ?
C4 C8 H8 . . 119.6 ?
C6 C9 C10 . . 104.9(2) ?
C6 C9 C17 . . 125.0(2) ?
C10 C9 C17 . . 129.6(2) ?
N2 C10 C9 . . 112.2(2) ?
N2 C10 C11 . . 118.0(2) ?
C9 C10 C11 . . 129.7(2) ?
C12 C11 C16 . . 118.7(2) ?
C12 C11 C10 . . 120.9(2) ?
C16 C11 C10 . . 120.3(2) ?
C13 C12 C11 . . 120.6(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 120.1(3) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 119.6(3) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.7(3) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 120.3(3) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
N3 C17 C18 . . 111.6(2) ?
N3 C17 C9 . . 119.6(2) ?
C18 C17 C9 . . 128.7(2) ?
C19 C18 C17 . . 105.3(2) ?
C19 C18 H18 . . 127.4 ?
C17 C18 H18 . . 127.4 ?
C18 C19 O3 . . 109.4(2) ?
C18 C19 C20 . . 133.0(3) ?
O3 C19 C20 . . 117.5(2) ?
N4 C20 C19 . . 113.1(2) ?
N4 C20 H20A . . 109.0 ?
C19 C20 H20A . . 109.0 ?
N4 C20 H20B . . 109.0 ?
C19 C20 H20B . . 109.0 ?
H20A C20 H20B . . 107.8 ?
C22 C21 H21A . . 109.5 ?
C22 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C22 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N4 C22 C21 . . 113.7(3) ?
N4 C22 H22A . . 108.8 ?
C21 C22 H22A . . 108.8 ?
N4 C22 H22B . . 108.8 ?
C21 C22 H22B . . 108.8 ?
H22A C22 H22B . . 107.7 ?
C24 C23 N4 . . 116.8(3) ?
C24 C23 H23A . . 108.1 ?
N4 C23 H23A . . 108.1 ?
C24 C23 H23B . . 108.1 ?
N4 C23 H23B . . 108.1 ?
H23A C23 H23B . . 107.3 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
N2 N1 C7 . . 124.3(2) ?
N2 N1 C6 . . 112.60(19) ?
C7 N1 C6 . . 123.1(2) ?
C10 N2 N1 . . 104.49(18) ?
C17 N3 O3 . . 104.9(2) ?
C22 N4 C20 . . 111.2(3) ?
C22 N4 C23 . . 114.6(3) ?
C20 N4 C23 . . 110.5(3) ?
C3 O1 C2 . . 117.7(2) ?
C19 O3 N3 . . 108.85(19) ?
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
C1 C2 . 1.482(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O1 . 1.451(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O2 . 1.201(3) ?
C3 O1 . 1.336(3) ?
C3 C4 . 1.493(4) ?
C4 C5 . 1.371(3) ?
C4 C8 . 1.420(4) ?
C5 C6 . 1.407(3) ?
C5 H5 . 0.9300 ?
C6 N1 . 1.379(3) ?
C6 C9 . 1.402(3) ?
C7 C8 . 1.347(4) ?
C7 N1 . 1.370(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.404(3) ?
C9 C17 . 1.464(3) ?
C10 N2 . 1.347(3) ?
C10 C11 . 1.480(3) ?
C11 C12 . 1.386(4) ?
C11 C16 . 1.391(3) ?
C12 C13 . 1.384(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.373(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.379(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 N3 . 1.311(3) ?
C17 C18 . 1.415(3) ?
C18 C19 . 1.340(4) ?
C18 H18 . 0.9300 ?
C19 O3 . 1.350(3) ?
C19 C20 . 1.494(4) ?
C20 N4 . 1.462(4) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.528(5) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 N4 . 1.419(4) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 C24 . 1.476(5) ?
C23 N4 . 1.487(4) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
N1 N2 . 1.358(3) ?
N3 O3 . 1.417(3) ?
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
C7 H7 N2 2_465 0.93 2.54 3.456(3) 169
C22 H22A O3 . 0.97 2.52 3.218(3) 129
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744437
