#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/36/4503665.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_4503665
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_sum            'C13 H17 N3 O3'
_chemical_formula_weight         263.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1628(9)
_cell_length_b                   9.7560(10)
_cell_length_c                   30.271(3)
_cell_measurement_temperature    120(2)
_cell_volume                     2706.0(5)
_computing_cell_refinement       'SMART for WNT/2000 (Bruker, 2003)'
_computing_data_collection       'SMART for WNT/2000 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'X-Seed (Barbour)'
_computing_publication_material  'Cif2Cif (Barbour)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9132
_diffrn_reflns_theta_full        24.76
_diffrn_reflns_theta_max         24.76
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   'Semi-empirical from equivalents'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.419
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.382
_refine_ls_R_factor_all          0.2075
_refine_ls_R_factor_gt           0.1855
_refine_ls_shift/su_max          0.172
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+55.9652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3396
_refine_ls_wR_factor_ref         0.3477
_reflns_number_gt                1696
_reflns_number_total             2068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800247f_si_003.cif
_cod_data_source_block           mtup2h2o
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      Pbcn
_cod_database_code               4503665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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 0.0411(7) 0.7558(8) -0.0004(3) 0.0185(17) Uani 1 1 d U
N1 N 0.1498(10) 0.9126(9) -0.1485(3) 0.017(2) Uani 1 1 d U
C1 C 0.0552(12) 1.0146(11) -0.1395(4) 0.020(3) Uani 1 1 d U
H1 H 0.0088 1.0609 -0.1633 0.024 Uiso 1 1 calc R
H1O H 0.153(12) 0.864(12) -0.2113(8) 0.02(3) Uiso 1 1 d D
O2 O 0.1526(9) 0.8533(9) -0.2408(2) 0.024(2) Uani 1 1 d DU
N2 N 0.2540(10) 0.8077(9) -0.0353(2) 0.013(2) Uani 1 1 d U
H2N H 0.3497 0.8003 -0.0351 0.015 Uiso 1 1 calc R
C2 C 0.0240(12) 1.0531(12) -0.0974(3) 0.022(3) Uani 1 1 d U
H2 H -0.0444 1.1247 -0.0925 0.026 Uiso 1 1 calc R
H2O H 0.20(2) 0.770(10) -0.243(8) 0.14(9) Uiso 1 1 d D
O3 O 0.1469(11) 1.1450(10) -0.2620(3) 0.038(2) Uani 1 1 d DU
N3 N 0.2577(9) 0.6896(9) 0.0303(2) 0.015(2) Uani 1 1 d U
H3N H 0.3531 0.6868 0.0272 0.017 Uiso 1 1 calc R
C3 C 0.0890(11) 0.9912(10) -0.0614(3) 0.010(2) Uani 1 1 d U
H3 H 0.0714 1.0210 -0.0320 0.012 Uiso 1 1 calc R
H3O H 0.168(10) 1.056(3) -0.261(3) 0.00(2) Uiso 1 1 d D
C4 C 0.1839(11) 0.8799(11) -0.0712(3) 0.010(2) Uani 1 1 d U
H4O H 0.08(3) 1.141(13) -0.239(9) 0.4(3) Uiso 1 1 d D
C5 C 0.2130(12) 0.8441(13) -0.1142(3) 0.020(3) Uani 1 1 d U
H5 H 0.2780 0.7705 -0.1201 0.023 Uiso 1 1 calc R
C6 C 0.1757(10) 0.7508(13) -0.0019(4) 0.016(2) Uani 1 1 d U
C7 C 0.1936(11) 0.6303(11) 0.0685(3) 0.014(2) Uani 1 1 d U
C8 C 0.2411(12) 0.6673(12) 0.1102(3) 0.018(2) Uani 1 1 d U
H8 H 0.3180 0.7320 0.1129 0.022 Uiso 1 1 calc R
C9 C 0.1796(12) 0.6126(12) 0.1480(3) 0.020(3) Uani 1 1 d U
H9 H 0.2129 0.6414 0.1763 0.024 Uiso 1 1 calc R
C10 C 0.0685(11) 0.5149(11) 0.1447(3) 0.013(2) Uani 1 1 d U
C11 C 0.0227(12) 0.4760(12) 0.1037(3) 0.021(3) Uani 1 1 d U
H11 H -0.0530 0.4099 0.1009 0.026 Uiso 1 1 calc R
C12 C 0.0857(11) 0.5322(10) 0.0654(3) 0.014(2) Uani 1 1 d U
H12 H 0.0537 0.5024 0.0371 0.016 Uiso 1 1 calc R
C13 C -0.0002(15) 0.4519(14) 0.1859(4) 0.035(3) Uani 1 1 d U
H13A H 0.0167 0.5122 0.2113 0.053 Uiso 1 1 calc R
H13B H 0.0440 0.3622 0.1916 0.053 Uiso 1 1 calc R
H13C H -0.1054 0.4408 0.1813 0.053 Uiso 1 1 calc R
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 C5 118.7(9)
N1 C1 C2 121.9(10)
C6 N2 C4 121.6(9)
C1 C2 C3 121.9(11)
C6 N3 C7 122.1(9)
C2 C3 C4 115.7(9)
C5 C4 C3 120.7(9)
C5 C4 N2 120.1(9)
C3 C4 N2 119.2(8)
N1 C5 C4 121.0(10)
O1 C6 N2 122.5(11)
O1 C6 N3 122.7(10)
N2 C6 N3 114.8(8)
C12 C7 C8 118.0(10)
C12 C7 N3 121.5(9)
C8 C7 N3 120.5(10)
C7 C8 C9 121.8(11)
C8 C9 C10 119.9(10)
C11 C10 C9 118.7(10)
C11 C10 C13 120.3(10)
C9 C10 C13 121.0(10)
C10 C11 C12 120.9(10)
C7 C12 C11 120.6(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.235(11)
N1 C1 1.348(14)
N1 C5 1.364(13)
C1 C2 1.360(15)
N2 C6 1.360(14)
N2 C4 1.445(12)
C2 C3 1.379(15)
N3 C6 1.366(14)
N3 C7 1.421(13)
C3 C4 1.422(14)
C4 C5 1.374(14)
C7 C12 1.379(15)
C7 C8 1.381(14)
C8 C9 1.384(15)
C9 C10 1.398(15)
C10 C11 1.365(15)
C10 C13 1.527(15)
C11 C12 1.406(15)
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
N3 H3N O1 0.88 1.98 2.801(11) 153.8 3_565
N2 H2N O1 0.88 2.13 2.911(11) 147.7 3_565
O2 H1O N1 0.90(2) 1.96(3) 2.854(10) 172(11) .
O2 H2O O3 0.90(2) 1.98(10) 2.813(12) 152(20) 7_655
O3 H3O O2 0.89(2) 2.07(4) 2.918(12) 158(8) .
O3 H4O O3 0.90(2) 2.1(3) 2.79(2) 130(33) 4_554
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661425
