#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/32/4503242.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_4503242
loop_
_publ_author_name
'Manzano, Blanca R.'
'Jalón, Félix A.'
'Soriano, M. Laura'
'Rodríguez, Ana M.'
'Hoz, Antonio de la'
'Sánchez-Migallón, Ana'
_publ_section_title
;
 Multiple Hydrogen Bonds in the Self-Assembly of Aminotriazine and
 Glutarimide. Decisive Role of the Triazine Substituents
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1585
_journal_paper_doi               10.1021/cg7008682
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C9 H9 N5, C5 H7 N O2'
_chemical_formula_sum            'C14 H16 N6 O2'
_chemical_formula_weight         300.33
_chemical_name_systematic
;
 ?
;
_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                 106.442(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0114(9)
_cell_length_b                   13.8878(15)
_cell_length_c                   12.4264(13)
_cell_measurement_temperature    180(2)
_cell_volume                     1491.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11641
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.8175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0629P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2536
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg7008682-file004.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4503242
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H5B H 0.1608(19) 0.1984(13) 0.9446(13) 0.039(5) Uiso 1 1 d .
H4B H 0.1785(18) 0.0692(12) 0.5303(14) 0.038(5) Uiso 1 1 d .
H5A H 0.309(2) 0.2545(13) 0.9948(15) 0.043(5) Uiso 1 1 d .
H4A H 0.0533(19) 0.0642(13) 0.5971(13) 0.039(5) Uiso 1 1 d .
H6A H -0.0052(19) 0.0862(13) 0.7859(13) 0.036(5) Uiso 1 1 d .
O1 O -0.02008(11) 0.11673(8) 0.97332(8) 0.0322(3) Uani 1 1 d .
O2 O -0.15359(12) 0.01218(9) 0.61691(9) 0.0372(3) Uani 1 1 d .
N1 N 0.19299(13) 0.14869(10) 0.76748(9) 0.0272(3) Uani 1 1 d .
N2 N 0.37192(13) 0.16969(9) 0.65878(9) 0.0251(3) Uani 1 1 d .
N3 N 0.42551(13) 0.23964(9) 0.84063(9) 0.0266(3) Uani 1 1 d .
N4 N 0.14655(15) 0.08473(11) 0.59116(11) 0.0349(4) Uani 1 1 d .
N5 N 0.24651(16) 0.22257(12) 0.93838(11) 0.0352(4) Uani 1 1 d .
N6 N -0.09265(14) 0.06123(10) 0.79613(10) 0.0277(3) Uani 1 1 d .
C1 C 0.28848(15) 0.20292(12) 0.84677(11) 0.0263(3) Uani 1 1 d .
C2 C 0.23938(15) 0.13512(11) 0.67502(11) 0.0251(3) Uani 1 1 d .
C3 C 0.45948(15) 0.22016(11) 0.74553(11) 0.0234(3) Uani 1 1 d .
C4 C 0.60994(15) 0.25693(11) 0.73489(11) 0.0247(3) Uani 1 1 d .
C5 C 0.65571(16) 0.23910(12) 0.63854(12) 0.0310(4) Uani 1 1 d .
H5 H 0.5890 0.2046 0.5778 0.037 Uiso 1 1 calc R
C6 C 0.79766(17) 0.27125(12) 0.63074(13) 0.0359(4) Uani 1 1 d .
H6 H 0.8280 0.2591 0.5648 0.043 Uiso 1 1 calc R
C7 C 0.89519(17) 0.32110(13) 0.71901(14) 0.0388(4) Uani 1 1 d .
H7 H 0.9929 0.3429 0.7138 0.047 Uiso 1 1 calc R
C8 C 0.85120(18) 0.33927(13) 0.81433(14) 0.0404(4) Uani 1 1 d .
H8 H 0.9188 0.3734 0.8749 0.048 Uiso 1 1 calc R
C9 C 0.70851(16) 0.30793(13) 0.82255(12) 0.0331(4) Uani 1 1 d .
H9 H 0.6782 0.3214 0.8883 0.040 Uiso 1 1 calc R
C10 C -0.11623(16) 0.07433(11) 0.90023(12) 0.0261(3) Uani 1 1 d .
C11 C -0.26377(16) 0.03456(12) 0.91647(13) 0.0316(4) Uani 1 1 d .
H11A H -0.3413 0.0869 0.9050 0.038 Uiso 1 1 calc R
H11B H -0.2435 0.0114 0.9946 0.038 Uiso 1 1 calc R
C12 C -0.32998(18) -0.04758(13) 0.83661(13) 0.0356(4) Uani 1 1 d .
H12A H -0.4342 -0.0644 0.8425 0.043 Uiso 1 1 calc R
H12B H -0.2630 -0.1050 0.8578 0.043 Uiso 1 1 calc R
C13 C -0.34105(16) -0.01941(12) 0.71616(13) 0.0315(4) Uani 1 1 d .
H13A H -0.3728 -0.0763 0.6670 0.038 Uiso 1 1 calc R
H13B H -0.4217 0.0306 0.6910 0.038 Uiso 1 1 calc R
C14 C -0.19072(16) 0.01817(11) 0.70416(12) 0.0277(3) Uani 1 1 d .
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
C1 N1 C2 114.66(12)
C3 N2 C2 114.14(12)
C3 N3 C1 114.54(12)
C14 N6 C10 127.27(13)
N5 C1 N1 117.83(13)
N5 C1 N3 117.13(13)
N1 C1 N3 125.04(13)
N4 C2 N1 117.62(13)
N4 C2 N2 116.99(13)
N1 C2 N2 125.38(13)
N3 C3 N2 126.18(12)
N3 C3 C4 116.97(12)
N2 C3 C4 116.85(12)
C9 C4 C5 119.02(13)
C9 C4 C3 120.08(13)
C5 C4 C3 120.88(13)
C6 C5 C4 120.44(14)
C7 C6 C5 119.93(15)
C8 C7 C6 120.15(14)
C7 C8 C9 120.32(15)
C8 C9 C4 120.13(15)
O1 C10 N6 119.85(13)
O1 C10 C11 123.21(13)
N6 C10 C11 116.95(12)
C10 C11 C12 112.74(12)
C11 C12 C13 110.71(13)
C14 C13 C12 112.20(12)
O2 C14 N6 119.69(13)
O2 C14 C13 123.08(13)
N6 C14 C13 117.23(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.2152(16)
O2 C14 1.2246(17)
N1 C1 1.3411(18)
N1 C2 1.3426(17)
N2 C3 1.3396(18)
N2 C2 1.3543(17)
N3 C3 1.3298(17)
N3 C1 1.3579(17)
N4 C2 1.3348(18)
N5 C1 1.3256(18)
N6 C14 1.3686(18)
N6 C10 1.3810(18)
C3 C4 1.4894(18)
C4 C9 1.389(2)
C4 C5 1.3944(19)
C5 C6 1.384(2)
C6 C7 1.382(2)
C7 C8 1.375(2)
C8 C9 1.388(2)
C10 C11 1.5050(19)
C11 C12 1.519(2)
C12 C13 1.523(2)
C13 C14 1.498(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B O2 0.908(17) 2.107(17) 2.9315(18) 150.4(15) 3_556
N5 H5A N2 0.885(19) 2.220(18) 3.0437(18) 154.7(15) 4_566
N4 H4A O2 0.910(17) 2.078(18) 2.9872(17) 177.0(16) .
N6 H6A N1 0.902(17) 2.057(18) 2.9574(17) 177.2(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661409
