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#$Date: 2022-07-05 11:40:20 +0300 (Tue, 05 Jul 2022) $
#$Revision: 276566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105657.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_8105657
loop_
_publ_author_name
'Fang, Bo'
'Meng, Jiang Ping'
'Luo, Yan'
_publ_section_title
;
 Crystal structure of methyl
 2-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H13N3O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              395
_journal_page_last               396
_journal_paper_doi               10.1515/ncrs-2018-0224
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                115.26(4)
_cell_angle_beta                 94.81(5)
_cell_angle_gamma                96.49(5)
_cell_formula_units_Z            2
_cell_length_a                   4.6502(18)
_cell_length_b                   11.937(3)
_cell_length_c                   13.1822(19)
_cell_measurement_temperature    296(2)
_cell_volume                     650.4(4)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3225
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.931
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0762
_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)+(0.0300P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1794
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                993
_reflns_number_total             2261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0224_suppl.cif
_cod_data_source_block           A
_cod_database_code               8105657
_shelx_shelxl_version_number     2018/1
_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   0.974
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.5390(7) 0.1469(3) -0.1336(3) 0.0596(10) Uani 1 1 d . . . . .
O2 O 0.7261(9) -0.0100(3) -0.1211(3) 0.0934(14) Uani 1 1 d . . . . .
N1 N -0.1024(10) 0.6792(4) 0.5519(4) 0.0642(12) Uani 1 1 d . . . . .
N2 N 0.0355(8) 0.6778(3) 0.4638(3) 0.0460(10) Uani 1 1 d . . . . .
N3 N 0.1338(10) 0.7950(4) 0.3600(4) 0.0616(12) Uani 1 1 d . . . . .
C1 C -0.2031(11) 0.7896(5) 0.5885(4) 0.0623(15) Uani 1 1 d . . . . .
H1A H -0.305936 0.818184 0.649841 0.075 Uiso 1 1 calc R U . . .
C2 C -0.1412(11) 0.8560(4) 0.5279(4) 0.0590(14) Uani 1 1 d . . . . .
H2A H -0.190943 0.933395 0.539520 0.071 Uiso 1 1 calc R U . . .
C3 C 0.0139(11) 0.7812(4) 0.4443(4) 0.0490(13) Uani 1 1 d . . . . .
C4 C 0.2762(11) 0.7030(4) 0.2969(4) 0.0587(14) Uani 1 1 d . . . . .
H4A H 0.357454 0.711280 0.237830 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3135(10) 0.5941(4) 0.3122(4) 0.0429(11) Uani 1 1 d . U . . .
C6 C 0.1825(10) 0.5849(4) 0.3977(4) 0.0488(13) Uani 1 1 d . U . . .
H6A H 0.192296 0.515144 0.411541 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4705(10) 0.4969(4) 0.2400(4) 0.0397(11) Uani 1 1 d . . . . .
C8 C 0.5866(11) 0.5032(4) 0.1494(4) 0.0552(14) Uani 1 1 d . . . . .
H8A H 0.565289 0.571320 0.134184 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7386(10) 0.4088(4) 0.0782(4) 0.0549(13) Uani 1 1 d . . . . .
H9A H 0.816233 0.417095 0.018477 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7711(10) 0.3065(4) 0.0968(4) 0.0460(12) Uani 1 1 d . . . . .
C11 C 0.6616(11) 0.3000(4) 0.1896(4) 0.0568(14) Uani 1 1 d . . . . .
H11A H 0.685333 0.232334 0.205252 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5155(11) 0.3944(4) 0.2601(4) 0.0558(14) Uani 1 1 d . . . . .
H12A H 0.447019 0.388152 0.322112 0.067 Uiso 1 1 calc R U . . .
C13 C 0.9187(10) 0.2019(4) 0.0182(4) 0.0572(14) Uani 1 1 d . . . . .
H13A H 1.074829 0.238814 -0.007988 0.069 Uiso 1 1 calc R U . . .
H13B H 1.007457 0.162990 0.061494 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7181(11) 0.1002(5) -0.0845(4) 0.0520(13) Uani 1 1 d . . . . .
C15 C 0.3461(12) 0.0569(4) -0.2352(4) 0.0673(16) Uani 1 1 d . . . . .
H15A H 0.226183 0.100510 -0.263780 0.101 Uiso 1 1 calc R U . . .
H15B H 0.460872 0.011239 -0.291673 0.101 Uiso 1 1 calc R U . . .
H15C H 0.223614 -0.000651 -0.217492 0.101 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 0.0033 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
C14 O1 C15 116.3(4) . .
C1 N1 N2 102.4(4) . .
N1 N2 C3 113.1(4) . .
N1 N2 C6 126.0(4) . .
C3 N2 C6 120.9(4) . .
C3 N3 C4 116.5(4) . .
N1 C1 C2 114.4(5) . .
N1 C1 H1A 122.8 . .
C2 C1 H1A 122.8 . .
C1 C2 C3 104.7(4) . .
C1 C2 H2A 127.6 . .
C3 C2 H2A 127.6 . .
N3 C3 N2 121.3(4) . .
N3 C3 C2 133.3(5) . .
N2 C3 C2 105.4(4) . .
N3 C4 C5 125.9(5) . .
N3 C4 H4A 117.0 . .
C5 C4 H4A 117.0 . .
C6 C5 C4 114.5(4) . .
C6 C5 C7 122.2(4) . .
C4 C5 C7 123.3(4) . .
C5 C6 N2 120.7(4) . .
C5 C6 H6A 119.6 . .
N2 C6 H6A 119.6 . .
C8 C7 C12 116.2(4) . .
C8 C7 C5 121.7(4) . .
C12 C7 C5 122.1(4) . .
C7 C8 C9 122.2(4) . .
C7 C8 H8A 118.9 . .
C9 C8 H8A 118.9 . .
C10 C9 C8 120.7(5) . .
C10 C9 H9A 119.7 . .
C8 C9 H9A 119.7 . .
C9 C10 C11 117.9(4) . .
C9 C10 C13 121.3(5) . .
C11 C10 C13 120.8(4) . .
C10 C11 C12 120.9(4) . .
C10 C11 H11A 119.6 . .
C12 C11 H11A 119.6 . .
C7 C12 C11 122.0(5) . .
C7 C12 H12A 119.0 . .
C11 C12 H12A 119.0 . .
C14 C13 C10 115.1(4) . .
C14 C13 H13A 108.5 . .
C10 C13 H13A 108.5 . .
C14 C13 H13B 108.5 . .
C10 C13 H13B 108.5 . .
H13A C13 H13B 107.5 . .
O2 C14 O1 122.8(5) . .
O2 C14 C13 124.8(5) . .
O1 C14 C13 112.3(4) . .
O1 C15 H15A 109.5 . .
O1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.321(5) .
O1 C15 1.452(5) .
O2 C14 1.198(5) .
N1 C1 1.350(5) .
N1 N2 1.367(5) .
N2 C3 1.377(5) .
N2 C6 1.380(5) .
N3 C3 1.345(6) .
N3 C4 1.347(6) .
C1 C2 1.370(6) .
C1 H1A 0.9300 .
C2 C3 1.403(7) .
C2 H2A 0.9300 .
C4 C5 1.425(6) .
C4 H4A 0.9300 .
C5 C6 1.363(6) .
C5 C7 1.467(6) .
C6 H6A 0.9300 .
C7 C8 1.378(6) .
C7 C12 1.391(6) .
C8 C9 1.428(6) .
C8 H8A 0.9300 .
C9 C10 1.367(6) .
C9 H9A 0.9300 .
C10 C11 1.392(6) .
C10 C13 1.520(6) .
C11 C12 1.408(6) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C13 C14 1.519(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
