#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:30 +0100 (lun 21 de mar de 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028464.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_4028464
loop_
_publ_author_name
'Borys Ośmiałowski'
'Karina Mroczyńska'
'Erkki Kolehmainen'
'Magdalena Kowalska'
'Arto Valkonen'
'Marek Pietrzak'
'Kari Rissanen'
_publ_section_title
;
 Association of N-(Pyridin-2-yl),N'-substituted Ureas with
 2-Amino-1,8-naphthyridines and Benzoates: NMR and Quantum Chemical
 Studies of the Substituent Effect on Complexation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7582
_journal_page_last               7593
_journal_paper_doi               10.1021/jo4011393
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C8 H11 N3 O'
_chemical_formula_sum            'C8 H11 N3 O'
_chemical_formula_weight         165.20
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.547(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1734(4)
_cell_length_b                   5.0975(2)
_cell_length_c                   13.3805(4)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     823.12(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω 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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11647
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0447
_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)+(0.0217P)²+0.3884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                1516
_reflns_number_total             2042
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo4011393_si_001.cif
_cod_data_source_block           uet
_cod_database_code               4028464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O8 O -0.00927(8) 0.2084(2) 0.60988(7) 0.0258(2) Uani 1 1 d .
N1 N 0.27027(9) 0.5065(2) 0.49663(8) 0.0234(3) Uani 1 1 d .
N7 N 0.11976(9) 0.2175(2) 0.50265(8) 0.0225(3) Uani 1 1 d D
H7 H 0.0825(12) 0.081(3) 0.4726(11) 0.027 Uiso 1 1 d D
N9 N 0.12354(10) 0.5244(2) 0.63236(8) 0.0241(3) Uani 1 1 d D
H9 H 0.1820(12) 0.588(3) 0.6078(12) 0.029 Uiso 1 1 d D
C2 C 0.21101(11) 0.3005(3) 0.45878(10) 0.0204(3) Uani 1 1 d .
C3 C 0.23699(11) 0.1571(3) 0.37524(10) 0.0235(3) Uani 1 1 d .
H3 H 0.1928 0.0122 0.3499 0.028 Uiso 1 1 calc R
C4 C 0.32789(12) 0.2315(3) 0.33112(11) 0.0273(3) Uani 1 1 d .
H4 H 0.3478 0.1376 0.2749 0.033 Uiso 1 1 calc R
C5 C 0.39039(12) 0.4456(3) 0.36966(11) 0.0281(3) Uani 1 1 d .
H5 H 0.4534 0.5011 0.3403 0.034 Uiso 1 1 calc R
C6 C 0.35865(11) 0.5753(3) 0.45148(10) 0.0257(3) Uani 1 1 d .
H6 H 0.4015 0.7215 0.4776 0.031 Uiso 1 1 calc R
C8 C 0.07419(11) 0.3169(3) 0.58448(10) 0.0213(3) Uani 1 1 d .
C10 C 0.08242(12) 0.6380(3) 0.71994(10) 0.0244(3) Uani 1 1 d .
H10A H 0.0007 0.6210 0.7121 0.029 Uiso 1 1 calc R
H10B H 0.1007 0.8273 0.7234 0.029 Uiso 1 1 calc R
C11 C 0.13129(13) 0.5071(3) 0.81785(11) 0.0309(3) Uani 1 1 d .
H11A H 0.1012 0.5901 0.8745 0.046 Uiso 1 1 calc R
H11B H 0.2121 0.5266 0.8268 0.046 Uiso 1 1 calc R
H11C H 0.1121 0.3203 0.8154 0.046 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
O8 0.0245(5) 0.0280(6) 0.0259(5) -0.0003(4) 0.0074(4) -0.0041(4)
N1 0.0213(6) 0.0251(6) 0.0238(5) 0.0012(5) 0.0027(5) -0.0014(5)
N7 0.0219(6) 0.0234(6) 0.0229(6) -0.0033(5) 0.0052(5) -0.0046(5)
N9 0.0239(6) 0.0258(6) 0.0239(6) -0.0028(5) 0.0076(5) -0.0031(5)
C2 0.0194(6) 0.0213(7) 0.0203(6) 0.0044(5) 0.0015(5) 0.0018(5)
C3 0.0255(7) 0.0224(7) 0.0228(6) -0.0001(6) 0.0034(5) 0.0004(6)
C4 0.0298(7) 0.0283(8) 0.0250(7) 0.0017(6) 0.0079(6) 0.0051(6)
C5 0.0234(7) 0.0321(8) 0.0298(7) 0.0074(6) 0.0077(6) 0.0012(6)
C6 0.0206(6) 0.0271(8) 0.0291(7) 0.0047(6) 0.0019(5) -0.0021(6)
C8 0.0213(6) 0.0221(7) 0.0203(6) 0.0028(5) 0.0019(5) 0.0013(5)
C10 0.0261(7) 0.0235(7) 0.0248(7) -0.0027(6) 0.0073(5) 0.0007(6)
C11 0.0358(8) 0.0314(8) 0.0251(7) -0.0021(6) 0.0032(6) 0.0003(7)
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
C2 N1 C6 117.24(12)
C8 N7 C2 130.35(12)
C8 N7 H7 114.0(10)
C2 N7 H7 115.6(10)
C8 N9 C10 121.37(12)
C8 N9 H9 116.3(10)
C10 N9 H9 122.3(11)
N1 C2 N7 120.10(12)
N1 C2 C3 122.93(12)
N7 C2 C3 116.97(12)
C4 C3 C2 118.42(13)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 119.32(13)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 118.33(13)
C6 C5 H5 120.8
C4 C5 H5 120.8
N1 C6 C5 123.76(14)
N1 C6 H6 118.1
C5 C6 H6 118.1
O8 C8 N9 123.57(12)
O8 C8 N7 118.65(12)
N9 C8 N7 117.78(12)
N9 C10 C11 112.51(12)
N9 C10 H10A 109.1
C11 C10 H10A 109.1
N9 C10 H10B 109.1
C11 C10 H10B 109.1
H10A C10 H10B 107.8
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C8 1.2426(16)
N1 C2 1.3355(18)
N1 C6 1.3476(17)
N7 C8 1.3868(17)
N7 C2 1.3888(17)
N7 H7 0.895(13)
N9 C8 1.3375(18)
N9 C10 1.4535(17)
N9 H9 0.883(13)
C2 C3 1.4060(19)
C3 C4 1.3742(19)
C3 H3 0.9500
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.377(2)
C5 H5 0.9500
C6 H6 0.9500
C10 C11 1.520(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
N7 H7 O8 0.895(13) 1.984(14) 2.8736(16) 172.5(14) 3_556
N9 H9 N1 0.883(13) 1.990(15) 2.7110(16) 138.0(14) .
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
C6 N1 C2 N7 179.18(12)
C6 N1 C2 C3 -0.19(19)
C8 N7 C2 N1 0.6(2)
C8 N7 C2 C3 179.99(13)
N1 C2 C3 C4 0.4(2)
N7 C2 C3 C4 -178.95(12)
C2 C3 C4 C5 -0.4(2)
C3 C4 C5 C6 0.2(2)
C2 N1 C6 C5 -0.1(2)
C4 C5 C6 N1 0.0(2)
C10 N9 C8 O8 0.6(2)
C10 N9 C8 N7 -178.87(12)
C2 N7 C8 O8 179.67(13)
C2 N7 C8 N9 -0.8(2)
C8 N9 C10 C11 87.59(16)
