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#$Date: 2022-04-28 12:43:57 +0300 (Thu, 28 Apr 2022) $
#$Revision: 274753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105089.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_8105089
loop_
_publ_author_name
'Fang, Bo'
'Jiang, Fang Fang'
'Meng, Jiang Ping'
_publ_section_title
;
 Crystal structure of methyl
 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              301
_journal_page_last               302
_journal_paper_doi               10.1515/ncrs-2019-0624
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C15 H12 I N3 O2'
_chemical_formula_sum            'C15 H12 I N3 O2'
_chemical_formula_weight         393.18
_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
_cell_angle_alpha                109.709(9)
_cell_angle_beta                 96.971(9)
_cell_angle_gamma                97.054(9)
_cell_formula_units_Z            2
_cell_length_a                   4.511(2)
_cell_length_b                   11.891(6)
_cell_length_c                   14.557(7)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.08
_cell_measurement_theta_min      2.92
_cell_volume                     718.4(6)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3660
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.923
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_T_max  0.6389
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1797
_reflns_number_total             2512
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0624_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105089
_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_max   0.639
_shelx_estimated_absorpt_t_min   0.563
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.b Me refined with riding coordinates:
 C15(H15A,H15B,H15C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
3.d Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12)
;
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
I1 I 1.51074(10) 0.92313(4) 0.77704(3) 0.0673(2) Uani 1 1 d . . . . .
O1 O -0.3231(16) 0.6328(5) -0.0621(4) 0.123(2) Uani 1 1 d . . . . .
O2 O -0.0358(12) 0.7943(5) 0.0417(3) 0.0865(15) Uani 1 1 d . . . . .
N1 N 0.8841(14) 0.6054(5) 0.6021(4) 0.0794(17) Uani 1 1 d . . . . .
N2 N 0.8300(12) 0.6828(4) 0.5546(3) 0.0570(12) Uani 1 1 d . . . . .
N3 N 0.9939(11) 0.8818(4) 0.5622(3) 0.0503(11) Uani 1 1 d . . . . .
C1 C 1.1978(14) 0.7850(5) 0.6763(4) 0.0538(14) Uani 1 1 d . U . . .
C2 C 1.1077(17) 0.6686(6) 0.6753(5) 0.0729(19) Uani 1 1 d . U . . .
H2 H 1.195792 0.638597 0.721274 0.087 Uiso 1 1 calc R . . . .
C3 C 1.0156(13) 0.7919(5) 0.5972(4) 0.0469(13) Uani 1 1 d . . . . .
C4 C 0.6111(14) 0.6588(5) 0.4756(4) 0.0603(16) Uani 1 1 d . . . . .
H4 H 0.482292 0.583944 0.448748 0.072 Uiso 1 1 calc R . . . .
C5 C 0.5823(13) 0.7453(5) 0.4363(4) 0.0471(13) Uani 1 1 d . . . . .
C6 C 0.7864(13) 0.8562(5) 0.4839(4) 0.0510(14) Uani 1 1 d . . . . .
H6 H 0.771551 0.916454 0.457071 0.061 Uiso 1 1 calc R . . . .
C7 C 0.3472(7) 0.7280(3) 0.3508(2) 0.0476(13) Uani 1 1 d . . . . .
C8 C 0.2200(8) 0.6122(2) 0.2845(3) 0.0529(14) Uani 1 1 d G . . . .
H8 H 0.286246 0.544837 0.293120 0.063 Uiso 1 1 calc R . . . .
C9 C -0.0063(8) 0.5972(2) 0.2054(2) 0.0579(15) Uani 1 1 d G . . . .
H9 H -0.091475 0.519679 0.161014 0.070 Uiso 1 1 calc R . . . .
C10 C -0.1054(7) 0.6979(3) 0.1925(2) 0.0495(14) Uani 1 1 d G . . . .
C11 C 0.0219(8) 0.8137(3) 0.2588(3) 0.0534(14) Uani 1 1 d G . . . .
H11 H -0.044380 0.881110 0.250160 0.064 Uiso 1 1 calc R . . . .
C12 C 0.2482(8) 0.8288(2) 0.3379(2) 0.0517(14) Uani 1 1 d G . . . .
H12 H 0.333343 0.906270 0.382266 0.062 Uiso 1 1 calc R . . . .
C13 C -0.3502(14) 0.6805(6) 0.1078(4) 0.0631(16) Uani 1 1 d . . . . .
H13A H -0.485778 0.737453 0.130201 0.076 Uiso 1 1 calc R . . . .
H13B H -0.466943 0.599266 0.087190 0.076 Uiso 1 1 calc R . . . .
C14 C -0.2364(16) 0.6974(6) 0.0202(5) 0.0647(17) Uani 1 1 d . U . . .
C15 C 0.0847(19) 0.8153(8) -0.0393(6) 0.107(3) Uani 1 1 d . . . . .
H15A H 0.230316 0.889277 -0.014423 0.160 Uiso 1 1 calc R . . . .
H15B H 0.181385 0.748928 -0.072003 0.160 Uiso 1 1 calc R . . . .
H15C H -0.077200 0.821787 -0.085533 0.160 Uiso 1 1 calc R . . . .
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'
I I -0.4742 1.8119 '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 O2 C15 117.0(6) . .
C2 N1 N2 103.7(5) . .
N1 N2 C3 112.6(5) . .
C4 N2 N1 125.2(5) . .
C4 N2 C3 122.1(5) . .
C6 N3 C3 115.5(5) . .
C2 C1 I1 129.1(5) . .
C3 C1 I1 125.7(4) . .
C3 C1 C2 105.1(6) . .
N1 C2 C1 112.6(6) . .
N1 C2 H2 123.7 . .
C1 C2 H2 123.7 . .
N2 C3 C1 105.9(5) . .
N3 C3 N2 121.7(5) . .
N3 C3 C1 132.3(5) . .
N2 C4 H4 120.7 . .
N2 C4 C5 118.7(5) . .
C5 C4 H4 120.7 . .
C4 C5 C6 116.0(5) . .
C4 C5 C7 122.6(5) . .
C6 C5 C7 121.4(4) . .
N3 C6 C5 126.0(5) . .
N3 C6 H6 117.0 . .
C5 C6 H6 117.0 . .
C8 C7 C5 120.6(3) . .
C8 C7 C12 120.0 . .
C12 C7 C5 119.4(3) . .
C7 C8 H8 120.0 . .
C9 C8 C7 120.0 . .
C9 C8 H8 120.0 . .
C8 C9 H9 120.0 . .
C10 C9 C8 120.0 . .
C10 C9 H9 120.0 . .
C9 C10 C11 120.0 . .
C9 C10 C13 119.5(3) . .
C11 C10 C13 120.5(3) . .
C10 C11 H11 120.0 . .
C12 C11 C10 120.0 . .
C12 C11 H11 120.0 . .
C7 C12 H12 120.0 . .
C11 C12 C7 120.0 . .
C11 C12 H12 120.0 . .
C10 C13 H13A 108.8 . .
C10 C13 H13B 108.8 . .
C10 C13 C14 113.9(5) . .
H13A C13 H13B 107.7 . .
C14 C13 H13A 108.8 . .
C14 C13 H13B 108.8 . .
O1 C14 O2 121.0(7) . .
O1 C14 C13 124.6(7) . .
O2 C14 C13 114.3(6) . .
O2 C15 H15A 109.5 . .
O2 C15 H15B 109.5 . .
O2 C15 H15C 109.5 . .
H15A C15 H15B 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
I1 C1 2.036(6) .
O1 C14 1.171(8) .
O2 C14 1.294(8) .
O2 C15 1.439(8) .
N1 N2 1.351(6) .
N1 C2 1.315(8) .
N2 C3 1.354(7) .
N2 C4 1.347(7) .
N3 C3 1.339(6) .
N3 C6 1.305(7) .
C1 C2 1.388(8) .
C1 C3 1.364(8) .
C2 H2 0.9300 .
C4 H4 0.9300 .
C4 C5 1.347(7) .
C5 C6 1.414(7) .
C5 C7 1.473(6) .
C6 H6 0.9300 .
C7 C8 1.3900 .
C7 C12 1.3900 .
C8 H8 0.9300 .
C8 C9 1.3900 .
C9 H9 0.9300 .
C9 C10 1.3900 .
C10 C11 1.3900 .
C10 C13 1.491(6) .
C11 H11 0.9300 .
C11 C12 1.3900 .
C12 H12 0.9300 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.496(9) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
