#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/38/2223805.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_2223805
loop_
_publ_author_name
'Li, Yong-Hong'
'Xie, Ru-Liang'
'Zhang, Tao'
'Mei, Xiang-Dong'
'Ning, Jun'
_publ_section_title
;
 4-(But-3-ynyloxy)-6-(4-iodo-1H-pyrazol-1-yl)pyrimidine
;
_journal_coeditor_code           HB5171
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2937
_journal_paper_doi               10.1107/S1600536809044031
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H9 I N4 O'
_chemical_formula_moiety         'C11 H9 I N4 O'
_chemical_formula_sum            'C11 H9 I N4 O'
_chemical_formula_weight         340.12
_chemical_name_systematic
;
4-(But-3-ynyloxy)-6-(4-iodo-1H-pyrazol-1-yl)pyrimidine
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.511(4)
_cell_length_b                   4.2670(9)
_cell_length_c                   15.129(3)
_cell_measurement_reflns_used    3485
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.21
_cell_volume                     1189.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8082
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_T_max  0.705
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.676
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0244P)²+1.6155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                2577
_reflns_number_total             2713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5171.cif
_cod_data_source_block           I
_cod_original_cell_volume        1189.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223805
_cod_database_fobs_code          2223805
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_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
I I1 0.073003(10) 0.85153(4) 0.354299(12) 0.02946(8) Uani d . 1 . .
O O1 0.28021(11) -0.1265(5) 0.89982(14) 0.0257(4) Uani d . 1 . .
N N1 0.12131(13) 0.5308(7) 0.63643(17) 0.0292(5) Uani d . 1 . .
N N2 0.17939(12) 0.4249(6) 0.61341(15) 0.0217(5) Uani d . 1 . .
N N3 0.29051(13) 0.1759(6) 0.65001(17) 0.0281(5) Uani d . 1 . .
N N4 0.34178(13) -0.1049(6) 0.79327(17) 0.0258(5) Uani d . 1 . .
C C1 0.11287(15) 0.6716(6) 0.48870(19) 0.0236(6) Uani d . 1 . .
C C2 0.08146(17) 0.6802(7) 0.5602(2) 0.0304(7) Uani d . 1 . .
H H2 0.0368 0.7814 0.5544 0.037 Uiso calc R 1 . .
C C3 0.17555(14) 0.5053(7) 0.52485(18) 0.0232(5) Uani d . 1 . .
H H3 0.2097 0.4556 0.4944 0.028 Uiso calc R 1 . .
C C4 0.23353(14) 0.2441(7) 0.67752(18) 0.0202(5) Uani d . 1 . .
C C5 0.34119(16) 0.0049(8) 0.7106(2) 0.0323(7) Uani d . 1 . .
H H5 0.3823 -0.0458 0.6929 0.039 Uiso calc R 1 . .
C C6 0.28450(14) -0.0285(7) 0.81731(18) 0.0218(5) Uani d . 1 . .
C C7 0.22707(15) 0.1515(6) 0.7616(2) 0.0213(5) Uani d . 1 . .
H H7 0.1866 0.2062 0.7801 0.026 Uiso calc R 1 . .
C C8 0.33899(15) -0.3164(7) 0.9591(2) 0.0254(6) Uani d . 1 . .
H H8A 0.3574 -0.4565 0.9198 0.030 Uiso calc R 1 . .
H H8B 0.3209 -0.4486 1.0004 0.030 Uiso calc R 1 . .
C C9 0.40039(15) -0.1086(7) 1.0183(2) 0.0266(6) Uani d . 1 . .
H H9A 0.4196 0.0174 0.9768 0.032 Uiso calc R 1 . .
H H9B 0.3813 0.0378 1.0554 0.032 Uiso calc R 1 . .
C C10 0.45916(15) -0.2943(7) 1.0816(2) 0.0255(6) Uani d . 1 . .
C C11 0.50610(16) -0.4493(8) 1.1313(2) 0.0322(6) Uani d . 1 . .
H H11 0.5439 -0.5741 1.1714 0.039 Uiso calc R 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'
I I -0.4742 1.8119 '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
C6 O1 C8 . . 118.1(2) ?
C2 N1 N2 . . 103.7(2) ?
C3 N2 N1 . . 112.7(2) ?
C3 N2 C4 . . 127.1(2) ?
N1 N2 C4 . . 120.2(2) ?
C5 N3 C4 . . 114.3(2) ?
C6 N4 C5 . . 115.0(2) ?
C3 C1 C2 . . 105.4(2) ?
C3 C1 I1 . . 125.8(2) ?
C2 C1 I1 . . 128.8(2) ?
N1 C2 C1 . . 112.2(3) ?
N1 C2 H2 . . 123.9 ?
C1 C2 H2 . . 123.9 ?
N2 C3 C1 . . 106.2(2) ?
N2 C3 H3 . . 126.9 ?
C1 C3 H3 . . 126.9 ?
N3 C4 C7 . . 124.2(2) ?
N3 C4 N2 . . 114.6(2) ?
C7 C4 N2 . . 121.2(2) ?
N3 C5 N4 . . 128.2(3) ?
N3 C5 H5 . . 115.9 ?
N4 C5 H5 . . 115.9 ?
N4 C6 O1 . . 119.6(2) ?
N4 C6 C7 . . 123.6(2) ?
O1 C6 C7 . . 116.8(2) ?
C4 C7 C6 . . 114.7(2) ?
C4 C7 H7 . . 122.6 ?
C6 C7 H7 . . 122.6 ?
O1 C8 C9 . . 110.4(2) ?
O1 C8 H8A . . 109.6 ?
C9 C8 H8A . . 109.6 ?
O1 C8 H8B . . 109.6 ?
C9 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
C10 C9 C8 . . 111.5(2) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C9 . . 178.6(4) ?
C10 C11 H11 . . 180.0 ?
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
I1 C1 . 2.071(3) ?
O1 C6 . 1.345(3) ?
O1 C8 . 1.449(3) ?
N1 C2 . 1.324(4) ?
N1 N2 . 1.367(3) ?
N2 C3 . 1.361(3) ?
N2 C4 . 1.406(3) ?
N3 C5 . 1.325(4) ?
N3 C4 . 1.341(3) ?
N4 C6 . 1.325(3) ?
N4 C5 . 1.332(4) ?
C1 C3 . 1.363(4) ?
C1 C2 . 1.408(4) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C4 C7 . 1.376(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.391(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.523(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.462(4) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.178(4) ?
C11 H11 . 0.9500 ?
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
C3 H3 O1 4_565 0.95 2.40 3.249(4) 148
C11 H11 N4 3_647 0.95 2.52 3.392(4) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 N2 C3 . . . . -0.3(3) ?
C2 N1 N2 C4 . . . . -178.2(3) ?
N2 N1 C2 C1 . . . . 0.1(4) ?
C3 C1 C2 N1 . . . . 0.1(4) ?
I1 C1 C2 N1 . . . . 177.7(2) ?
N1 N2 C3 C1 . . . . 0.4(3) ?
C4 N2 C3 C1 . . . . 178.1(3) ?
C2 C1 C3 N2 . . . . -0.3(3) ?
I1 C1 C3 N2 . . . . -177.96(19) ?
C5 N3 C4 C7 . . . . 0.8(4) ?
C5 N3 C4 N2 . . . . -179.8(3) ?
C3 N2 C4 N3 . . . . 7.6(4) ?
N1 N2 C4 N3 . . . . -174.8(3) ?
C3 N2 C4 C7 . . . . -173.0(3) ?
N1 N2 C4 C7 . . . . 4.6(4) ?
C4 N3 C5 N4 . . . . 0.3(5) ?
C6 N4 C5 N3 . . . . -0.8(5) ?
C5 N4 C6 O1 . . . . -179.6(3) ?
C5 N4 C6 C7 . . . . 0.3(4) ?
C8 O1 C6 N4 . . . . -0.6(4) ?
C8 O1 C6 C7 . . . . 179.6(2) ?
N3 C4 C7 C6 . . . . -1.3(4) ?
N2 C4 C7 C6 . . . . 179.4(2) ?
N4 C6 C7 C4 . . . . 0.7(4) ?
O1 C6 C7 C4 . . . . -179.5(2) ?
C6 O1 C8 C9 . . . . 84.8(3) ?
O1 C8 C9 C10 . . . . 177.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743669
