#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:18:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179571 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503673.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_4503673
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         'C22 H18 N6 O2'
_chemical_formula_sum            'C22 H18 N6 O2'
_chemical_formula_weight         398.42
_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                 106.092(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.2108(17)
_cell_length_b                   4.5671(4)
_cell_length_c                   11.3315(10)
_cell_measurement_temperature    120(2)
_cell_volume                     905.52(14)
_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 0.998
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14787
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.885809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0566
_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)+(0.0634P)²+0.7095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                1662
_reflns_number_total             2442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800247f_si_011.cif
_cod_data_source_block           c:\rawdat~1\peter\08srv213\work\petesad
_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      P2(1)/c
_cod_database_code               4503673
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28440(8) 0.2174(3) 0.74718(13) 0.0294(3) Uani 1 1 d . . .
N2 N 0.23940(10) 0.6555(4) 0.66055(16) 0.0297(4) Uani 1 1 d . . .
H2N H 0.2450(13) 0.849(6) 0.664(2) 0.036 Uiso 1 1 d . . .
N3 N 0.33755(8) 0.6413(3) 0.83765(14) 0.0231(3) Uani 1 1 d . . .
H3N H 0.3359 0.8339 0.8352 0.028 Uiso 1 1 calc R . .
C1 C 0.17118(14) 0.6493(7) 0.4462(2) 0.0487(7) Uani 1 1 d . . .
H1 H 0.2064 0.7910 0.4333 0.058 Uiso 1 1 calc R A 1
C2 C 0.06542(16) 0.3604(6) 0.3709(3) 0.0553(8) Uani 1 1 d . . .
H2 H 0.0246 0.2961 0.3038 0.066 Uiso 1 1 calc R B 1
C4 C 0.12936(14) 0.3398(6) 0.5801(2) 0.0522(7) Uani 1 1 d . . .
H4 H 0.1342 0.2634 0.6599 0.063 Uiso 1 1 calc R C 1
C5 C 0.18018(10) 0.5421(4) 0.56301(17) 0.0251(4) Uani 1 1 d . D .
C6 C 0.28658(10) 0.4866(4) 0.74866(17) 0.0230(4) Uani 1 1 d . . .
C7 C 0.39339(10) 0.5015(4) 0.93428(16) 0.0212(4) Uani 1 1 d . . .
C8 C 0.37172(11) 0.3033(4) 1.00901(17) 0.0243(4) Uani 1 1 d . . .
H8 H 0.3191 0.2604 0.9969 0.029 Uiso 1 1 calc R . .
C9 C 0.47211(10) 0.5701(4) 0.95125(15) 0.0202(4) Uani 1 1 d . . .
C10 C 0.49650(11) 0.7766(4) 0.87632(16) 0.0227(4) Uani 1 1 d . . .
H10 H 0.4598 0.8734 0.8121 0.027 Uiso 1 1 calc R . .
C11 C 0.57263(7) 0.8371(3) 0.89614(12) 0.0245(4) Uani 1 1 d . . .
H11 H 0.5882 0.9756 0.8453 0.029 Uiso 1 1 calc R . .
N1 N 0.11385(7) 0.5591(3) 0.34923(12) 0.057(4) Uani 0.60(3) 1 d PR D 1
C3 C 0.07142(7) 0.2460(3) 0.48318(12) 0.070(5) Uani 0.60(3) 1 d PR D 1
H3 H 0.0360 0.1032 0.4944 0.084 Uiso 0.60(3) 1 d PR D 1
C3A C 0.11385(7) 0.5591(3) 0.34923(12) 0.051(5) Uani 0.40(3) 1 d P D 2
H3A H 0.1083 0.6342 0.2690 0.061 Uiso 0.40(3) 1 calc PR D 2
N1A N 0.07142(7) 0.2460(3) 0.48318(12) 0.071(6) Uani 0.40(3) 1 d P D 2
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_3
C6 N2 C5 123.78(17) .
C6 N3 C7 122.09(15) .
N1 C1 C5 122.1(2) .
N1 C2 C3 123.4(2) .
C5 C4 C3 120.3(2) .
C4 C5 C1 118.3(2) .
C4 C5 N2 122.73(19) .
C1 C5 N2 118.91(19) .
O1 C6 N2 123.00(17) .
O1 C6 N3 122.75(17) .
N2 C6 N3 114.23(16) .
C8 C7 N3 120.37(16) .
C8 C7 C9 120.82(16) .
N3 C7 C9 118.81(16) .
C7 C8 C11 120.14(16) 3_667
C10 C9 C7 122.29(15) .
C10 C9 C9 119.1(2) 3_667
C7 C9 C9 118.6(2) 3_667
C11 C10 C9 120.40(15) .
C10 C11 C8 120.93(15) 3_667
C2 N1 C1 117.29(18) .
C2 C3 C4 118.62(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.230(2) .
N2 C6 1.362(2) .
N2 C5 1.411(2) .
N3 C6 1.363(2) .
N3 C7 1.423(2) .
C1 N1 1.353(3) .
C1 C5 1.378(3) .
C2 N1 1.335(4) .
C2 C3 1.352(3) .
C4 C5 1.359(3) .
C4 C3 1.364(3) .
C7 C8 1.370(3) .
C7 C9 1.427(2) .
C8 C11 1.411(2) 3_667
C9 C10 1.420(3) .
C9 C9 1.428(3) 3_667
C10 C11 1.370(2) .
C11 C8 1.411(2) 3_667
