#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018170.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_2018170
loop_
_publ_author_name
'Cheng, Yuan'
'Chen, Lu-Sheng'
'Liu, Qi-Kui'
'Wu, Jun'
'Guo, Dian-Shun'
_publ_section_title
;
 Supramolecular structures constructed by
 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol
 monohydrate and
 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol
;
_journal_coeditor_code           YP3004
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o244
_journal_page_last               o248
_journal_paper_doi               10.1107/S0108270111019895
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H17 N3 O2'
_chemical_formula_moiety         'C14 H17 N3 O2'
_chemical_formula_sum            'C14 H17 N3 O2'
_chemical_formula_weight         259.31
_chemical_name_systematic
;
3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-
dimethylprop-2-yn-1-ol
;
_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                78.976(3)
_cell_angle_beta                 86.217(3)
_cell_angle_gamma                73.104(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9966(17)
_cell_length_b                   9.737(2)
_cell_length_c                   9.833(2)
_cell_measurement_reflns_used    1820
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.939
_cell_measurement_theta_min      2.222
_cell_volume                     719.0(3)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3832
_diffrn_reflns_theta_full        25.60
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[s²(Fo²)+(0.0570P)²+0.1916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                2316
_reflns_number_total             2644
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yp3004.cif
_cod_data_source_block           II
_cod_database_code               2018170
_cod_database_fobs_code          2018170
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.34240(19) 0.66320(16) 0.32687(15) 0.0248(3) Uani d . 1 1 . .
C C2 0.34401(19) 0.75848(16) 0.09525(15) 0.0246(3) Uani d . 1 1 . .
C C3 0.50003(19) 0.65441(16) 0.07843(15) 0.0264(3) Uani d . 1 1 . .
H H3 0.5511 0.6468 -0.0086 0.032 Uiso calc R 1 1 . .
C C4 0.57674(19) 0.56205(15) 0.19699(15) 0.0243(3) Uani d . 1 1 . .
C C5 0.2707(2) 0.86548(16) -0.02401(15) 0.0270(3) Uani d . 1 1 . .
C C6 0.23337(19) 0.94368(16) -0.13373(15) 0.0270(3) Uani d . 1 1 . .
C C7 0.1960(2) 1.03140(16) -0.27470(15) 0.0272(3) Uani d . 1 1 . .
C C8 0.2097(3) 1.18504(19) -0.28019(19) 0.0443(5) Uani d . 1 1 . .
H H8A 0.1894 1.2388 -0.3731 0.066 Uiso calc R 1 1 . .
H H8B 0.3244 1.1799 -0.2522 0.066 Uiso calc R 1 1 . .
H H8C 0.1240 1.2333 -0.2188 0.066 Uiso calc R 1 1 . .
C C9 0.3231(2) 0.9527(2) -0.37571(17) 0.0405(4) Uani d . 1 1 . .
H H9A 0.3109 0.8565 -0.3699 0.061 Uiso calc R 1 1 . .
H H9B 0.4405 0.9457 -0.3527 0.061 Uiso calc R 1 1 . .
H H9C 0.2981 1.0062 -0.4682 0.061 Uiso calc R 1 1 . .
C C10 0.7498(2) 0.46297(16) 0.19517(15) 0.0276(4) Uani d . 1 1 . .
C C11 0.8969(2) 0.38734(16) 0.20745(15) 0.0270(4) Uani d . 1 1 . .
C C12 1.0798(2) 0.29629(16) 0.23353(16) 0.0270(3) Uani d . 1 1 . .
C C13 1.1890(2) 0.39394(19) 0.2572(2) 0.0394(4) Uani d . 1 1 . .
H H13A 1.1429 0.4395 0.3354 0.059 Uiso calc R 1 1 . .
H H13B 1.1854 0.4677 0.1763 0.059 Uiso calc R 1 1 . .
H H13C 1.3078 0.3363 0.2748 0.059 Uiso calc R 1 1 . .
C C14 1.1506(2) 0.21818(18) 0.11305(18) 0.0343(4) Uani d . 1 1 . .
H H14A 1.2697 0.1614 0.1306 0.051 Uiso calc R 1 1 . .
H H14B 1.1455 0.2888 0.0295 0.051 Uiso calc R 1 1 . .
H H14C 1.0815 0.1551 0.1029 0.051 Uiso calc R 1 1 . .
N N1 0.26248(16) 0.76481(13) 0.21849(12) 0.0261(3) Uani d . 1 1 . .
N N2 0.49961(16) 0.56418(13) 0.32144(12) 0.0256(3) Uani d . 1 1 . .
N N3 0.26122(18) 0.65977(14) 0.44984(13) 0.0330(3) Uani d . 1 1 . .
H H3A 0.1631 0.7245 0.4595 0.040 Uiso d R 1 1 . .
H H3B 0.3173 0.5997 0.5208 0.040 Uiso d R 1 1 . .
O O1 0.02489(13) 1.03693(11) -0.31459(11) 0.0275(3) Uani d . 1 1 . .
H H1 -0.0486 1.0899 -0.2708 0.041 Uiso calc R 1 1 . .
O O2 1.08389(16) 0.19577(12) 0.36028(11) 0.0341(3) Uani d . 1 1 . .
H H2 1.0464 0.1294 0.3475 0.051 Uiso calc R 1 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
N3 C1 N2 . . 116.37(13) ?
N3 C1 N1 . . 118.26(13) ?
N2 C1 N1 . . 125.37(13) ?
N1 C2 C3 . . 122.33(13) ?
N1 C2 C5 . . 119.54(13) ?
C3 C2 C5 . . 118.11(13) ?
C2 C3 C4 . . 116.98(13) ?
C2 C3 H3 . . 121.5 ?
C4 C3 H3 . . 121.5 ?
N2 C4 C3 . . 122.43(14) ?
N2 C4 C10 . . 115.51(13) ?
C3 C4 C10 . . 121.97(13) ?
C6 C5 C2 . . 169.57(16) ?
C5 C6 C7 . . 175.59(16) ?
O1 C7 C6 . . 109.55(12) ?
O1 C7 C9 . . 106.30(13) ?
C6 C7 C9 . . 108.24(13) ?
O1 C7 C8 . . 110.21(13) ?
C6 C7 C8 . . 110.85(13) ?
C9 C7 C8 . . 111.56(14) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C4 . . 171.94(17) ?
C10 C11 C12 . . 175.54(16) ?
O2 C12 C11 . . 108.54(12) ?
O2 C12 C14 . . 111.61(12) ?
C11 C12 C14 . . 110.48(13) ?
O2 C12 C13 . . 105.95(13) ?
C11 C12 C13 . . 108.54(13) ?
C14 C12 C13 . . 111.55(13) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C2 N1 C1 . . 116.12(13) ?
C4 N2 C1 . . 116.47(12) ?
C1 N3 H3A . . 119.7 ?
C1 N3 H3B . . 117.8 ?
H3A N3 H3B . . 121.9 ?
C7 O1 H1 . . 109.5 ?
C12 O2 H2 . . 109.5 ?
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 N3 . 1.333(2) ?
C1 N2 . 1.3487(19) ?
C1 N1 . 1.3573(19) ?
C2 N1 . 1.3410(19) ?
C2 C3 . 1.383(2) ?
C2 C5 . 1.440(2) ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9300 ?
C4 N2 . 1.3346(19) ?
C4 C10 . 1.440(2) ?
C5 C6 . 1.196(2) ?
C6 C7 . 1.481(2) ?
C7 O1 . 1.4312(18) ?
C7 C9 . 1.520(2) ?
C7 C8 . 1.522(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.193(2) ?
C11 C12 . 1.483(2) ?
C12 O2 . 1.4257(18) ?
C12 C14 . 1.519(2) ?
C12 C13 . 1.522(2) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
N3 H3A . 0.8648 ?
N3 H3B . 0.8733 ?
O1 H1 . 0.8200 ?
O2 H2 . 0.8200 ?
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
N3 H3B N2 2_666 0.87 2.26 3.1207(18) 170.3
N3 H3A O2 2_666 0.86 2.61 3.3390(19) 142.5
N3 H3A O1 2_575 0.86 2.58 3.2705(17) 137.2
O1 H1 N1 2_575 0.82 1.99 2.7808(16) 162.9
C9 H9C O2 1_464 0.96 2.56 3.4167(18) 149.2
O2 H2 O1 2_665 0.82 1.95 2.7710(16) 175.7
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
N1 C2 C3 C4 . . . . -4.6(2) ?
C5 C2 C3 C4 . . . . 173.66(14) ?
C2 C3 C4 N2 . . . . 4.9(2) ?
C2 C3 C4 C10 . . . . -171.43(14) ?
N1 C2 C5 C6 . . . . 175.6(8) ?
C3 C2 C5 C6 . . . . -2.7(10) ?
C2 C5 C6 C7 . . . . 24(3) ?
C5 C6 C7 O1 . . . . 105(2) ?
C5 C6 C7 C9 . . . . -11(2) ?
C5 C6 C7 C8 . . . . -133(2) ?
N2 C4 C10 C11 . . . . -44.9(12) ?
C3 C4 C10 C11 . . . . 131.7(11) ?
C4 C10 C11 C12 . . . . 14(3) ?
C10 C11 C12 O2 . . . . 55(2) ?
C10 C11 C12 C14 . . . . 178(2) ?
C10 C11 C12 C13 . . . . -60(2) ?
C3 C2 N1 C1 . . . . 0.3(2) ?
C5 C2 N1 C1 . . . . -177.91(13) ?
N3 C1 N1 C2 . . . . -176.14(13) ?
N2 C1 N1 C2 . . . . 4.2(2) ?
C3 C4 N2 C1 . . . . -0.9(2) ?
C10 C4 N2 C1 . . . . 175.66(13) ?
N3 C1 N2 C4 . . . . 176.42(13) ?
N1 C1 N2 C4 . . . . -3.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654320
