#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:18:16 +0100 (jue 24 de mar de 2016) $
#$Revision: 179571 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503668.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_4503668
loop_
_publ_author_name
'Byrne, Peter'
'Turner, David R.'
'Lloyd, Gareth O.'
'Clarke, Nigel'
'Steed, Jonathan W.'
_publ_section_title
;
 Gradual Transition from NH···Pyridyl Hydrogen
 Bonding to the NH···O Tape Synthon in Pyridyl Ureas
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3335
_journal_paper_doi               10.1021/cg800247f
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C14 H16 N6 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                 112.234(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4334(6)
_cell_length_b                   8.8676(6)
_cell_length_c                   9.8416(7)
_cell_measurement_reflns_used    756
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.983
_cell_measurement_theta_min      3.207
_cell_volume                     681.27(8)
_computing_cell_refinement       Saint
_computing_data_collection       Smart
_computing_data_reduction        Saint
_computing_molecular_graphics    Xseed
_computing_publication_material  Xseed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  Smart-6K
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7672
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         34.98
_diffrn_reflns_theta_min         2.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.088
_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     100
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0555
_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/[σ²(Fo²)+(0.0969P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1612
_reflns_number_gt                1914
_reflns_number_total             2814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800247f_si_006.cif
_cod_data_source_block           z:\xraydata\peter\07srv5~4\work\xm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4503668
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
O1 O 0.43933(11) 0.20193(11) 0.11215(9) 0.0207(2) Uani 1 1 d .
N1 N -0.02756(13) -0.21252(12) -0.12832(11) 0.0185(2) Uani 1 1 d .
N2 N 0.24769(12) 0.11088(12) -0.10934(10) 0.0167(2) Uani 1 1 d .
H2N H 0.2019 0.1302 -0.2040 0.020 Uiso 1 1 calc R
N3 N 0.40514(13) 0.32273(12) -0.10127(10) 0.0177(2) Uani 1 1 d .
H3N H 0.3483 0.3275 -0.1968 0.021 Uiso 1 1 calc R
C1 C 0.05129(16) -0.27447(14) 0.00439(13) 0.0194(2) Uani 1 1 d .
H1 H 0.0029 -0.3622 0.0286 0.023 Uiso 1 1 calc R
C2 C 0.20093(16) -0.21590(14) 0.10824(13) 0.0189(2) Uani 1 1 d .
H2 H 0.2532 -0.2633 0.2012 0.023 Uiso 1 1 calc R
C3 C 0.27321(15) -0.08784(14) 0.07506(12) 0.0175(2) Uani 1 1 d .
H3 H 0.3774 -0.0481 0.1435 0.021 Uiso 1 1 calc R
C4 C 0.19029(14) -0.01815(13) -0.06083(12) 0.0150(2) Uani 1 1 d .
C5 C 0.03942(15) -0.08644(14) -0.15788(12) 0.0172(2) Uani 1 1 d .
H5 H -0.0185 -0.0398 -0.2504 0.021 Uiso 1 1 calc R
C6 C 0.36977(14) 0.21144(13) -0.02276(12) 0.0156(2) Uani 1 1 d .
C7 C 0.53609(15) 0.43432(14) -0.02907(12) 0.0175(2) Uani 1 1 d .
H7A H 0.5847 0.4727 -0.0996 0.021 Uiso 1 1 calc R
H7B H 0.6299 0.3862 0.0534 0.021 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0223(4) 0.0247(5) 0.0133(4) -0.0009(3) 0.0046(3) -0.0048(3)
N1 0.0189(4) 0.0178(5) 0.0180(5) -0.0025(4) 0.0060(4) -0.0008(4)
N2 0.0181(4) 0.0162(5) 0.0131(4) 0.0001(3) 0.0028(3) -0.0024(4)
N3 0.0217(5) 0.0169(5) 0.0129(4) -0.0008(3) 0.0048(3) -0.0035(4)
C1 0.0225(5) 0.0165(6) 0.0198(5) -0.0010(4) 0.0086(4) -0.0011(4)
C2 0.0221(5) 0.0165(6) 0.0168(5) 0.0007(4) 0.0059(4) 0.0027(4)
C3 0.0172(5) 0.0168(5) 0.0166(5) -0.0007(4) 0.0042(4) 0.0011(4)
C4 0.0159(4) 0.0141(5) 0.0152(5) -0.0019(4) 0.0061(4) 0.0004(4)
C5 0.0173(5) 0.0181(5) 0.0151(5) -0.0017(4) 0.0050(4) 0.0003(4)
C6 0.0157(5) 0.0156(5) 0.0156(5) -0.0020(4) 0.0060(4) -0.0001(4)
C7 0.0185(5) 0.0169(5) 0.0174(5) -0.0020(4) 0.0070(4) -0.0024(4)
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
C5 N1 C1 117.50(11) . .
C6 N2 C4 126.23(9) . .
C6 N2 H2N 116.9 . .
C4 N2 H2N 116.9 . .
C6 N3 C7 120.54(9) . .
C6 N3 H3N 119.7 . .
C7 N3 H3N 119.7 . .
N1 C1 C2 122.80(12) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
C3 C2 C1 119.42(11) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C2 C3 C4 118.87(10) . .
C2 C3 H3 120.6 . .
C4 C3 H3 120.6 . .
N2 C4 C3 125.28(10) . .
N2 C4 C5 117.56(10) . .
C3 C4 C5 117.14(11) . .
N1 C5 C4 124.19(11) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
O1 C6 N3 123.06(10) . .
O1 C6 N2 123.91(11) . .
N3 C6 N2 113.03(10) . .
N3 C7 C7 111.52(12) . 3_665
N3 C7 H7A 109.3 . .
C7 C7 H7A 109.3 3_665 .
N3 C7 H7B 109.3 . .
C7 C7 H7B 109.3 3_665 .
H7A C7 H7B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.2348(14) .
N1 C5 1.3334(16) .
N1 C1 1.3389(16) .
N2 C6 1.3846(15) .
N2 C4 1.3950(15) .
N2 H2N 0.8800 .
N3 C6 1.3544(16) .
N3 C7 1.4526(15) .
N3 H3N 0.8800 .
C1 C2 1.3895(17) .
C1 H1 0.9500 .
C2 C3 1.3851(18) .
C2 H2 0.9500 .
C3 C4 1.3971(16) .
C3 H3 0.9500 .
C4 C5 1.4065(15) .
C5 H5 0.9500 .
C7 C7 1.523(2) 3_665
C7 H7A 0.9900 .
C7 H7B 0.9900 .
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
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 -2.31(19) .
N1 C1 C2 C3 0.1(2) .
C1 C2 C3 C4 1.99(18) .
C6 N2 C4 C3 -16.34(19) .
C6 N2 C4 C5 165.61(11) .
C2 C3 C4 N2 -179.94(11) .
C2 C3 C4 C5 -1.88(17) .
C1 N1 C5 C4 2.42(18) .
N2 C4 C5 N1 177.87(11) .
C3 C4 C5 N1 -0.35(18) .
C7 N3 C6 O1 3.19(18) .
C7 N3 C6 N2 -177.10(10) .
C4 N2 C6 O1 -3.09(19) .
C4 N2 C6 N3 177.21(10) .
C6 N3 C7 C7 -86.49(16) 3_665
