##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
 ;
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H20 N4 O'
_chemical_formula_sum     'C15 H20 N4 O'
_chemical_formula_weight     272.35
_chemical_melting_point     513
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     12.7129(2)
_cell_length_b     11.20670(10)
_cell_length_c     11.6822(2)
_cell_angle_alpha     90
_cell_angle_beta     109.5780(10)
_cell_angle_gamma     90
_cell_volume     1568.14(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5891
_cell_measurement_theta_min     1
_cell_measurement_theta_max     25
_cell_measurement_temperature     140(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .40
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .08
_exptl_crystal_density_diffrn     1.154
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu      .075
_exptl_absorpt_correction_type     Empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min      .970
_exptl_absorpt_correction_T_max      .994
_exptl_special_details
;
 ;
;
_diffrn_ambient_temperature     140(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10199
_diffrn_reflns_av_R_equivalents      .051
_diffrn_reflns_av_sigmaI/netI      .049
_diffrn_reflns_theta_min     1.7
_diffrn_reflns_theta_max     26.4
_diffrn_reflns_theta_full     26.4
_diffrn_measured_fraction_theta_max      .99
_diffrn_measured_fraction_theta_full      .99
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     512
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     900
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3174
_reflns_number_gt     2135
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .084
_refine_ls_R_factor_gt      .050
_refine_ls_wR_factor_ref      .136
_refine_ls_goodness_of_fit_ref     1.02
_refine_ls_restrained_S_all     1.02
_refine_ls_number_reflns     3174
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0636P)²+0.4824P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.02
_refine_ls_shift/su_mean      .00
_refine_diff_density_max      .29
_refine_diff_density_min      -.23
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef      .014(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Siemens, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material     ?
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    N1  .85531(12)  .54915(14)  .48862(14)  .0231(4) Uani d . 1 . . N
    H1  .8923(16)  .4926(19)  .4634(18)  .026(5) Uiso d . 1 . . H
    C2  .92330(14)  .63554(16)  .56465(15)  .0205(4) Uani d . 1 . . C
    O2 1.02662(9)  .62078(11)  .59955(11)  .0254(3) Uani d . 1 . . O
    N3  .87183(13)  .72830(14)  .59484(14)  .0249(4) Uani d . 1 . . N
    H3  .7957(19)  .7260(19)  .563(2)  .042(6) Uiso d . 1 . . H
    C4  .92836(15)  .82712(16)  .67685(17)  .0257(4) Uani d . 1 . . C
    C41 1.00999(19)  .8910(2)  .6270(2)  .0410(6) Uani d . 1 . . C
    H41A  .9697  .9211  .5453  .062 Uiso calc R 1 . . H
    H41B 1.0679  .8349  .6233  .062 Uiso calc R 1 . . H
    H41C 1.0447  .9578  .6804  .062 Uiso calc R 1 . . H
    C42  .83422(17)  .91287(19)  .6775(2)  .0416(6) Uani d . 1 . . C
    H42A  .7820  .8714  .7093  .062 Uiso calc R 1 . . H
    H42B  .7945  .9401  .5945  .062 Uiso calc R 1 . . H
    H42C  .8661  .9817  .7292  .062 Uiso calc R 1 . . H
    C43  .98812(17)  .77897(19)  .80489(18)  .0356(5) Uani d . 1 . . C
    H43A  .9341  .7383  .8347  .053 Uiso calc R 1 . . H
    H43B 1.0223  .8453  .8593  .053 Uiso calc R 1 . . H
    H43C 1.0462  .7224  .8026  .053 Uiso calc R 1 . . H
    C11  .73957(14)  .54333(16)  .43817(16)  .0218(4) Uani d . 1 . . C
    N12  .67811(12)  .62899(13)  .46135(14)  .0239(4) Uani d . 1 . . N
    C13  .56386(14)  .61944(17)  .41554(17)  .0248(4) Uani d . 1 . . C
    N14  .50809(12)  .71130(15)  .44676(15)  .0301(4) Uani d . 1 . . N
    C15  .39668(15)  .70527(19)  .40751(19)  .0341(5) Uani d . 1 . . C
    C15'  .33656(17)  .8068(2)  .4442(2)  .0458(6) Uani d . 1 . . C
    H15A  .3651  .8158  .5327  .069 Uiso calc R 1 . . H
    H15B  .2564  .7896  .4175  .069 Uiso calc R 1 . . H
    H15C  .3492  .8808  .4061  .069 Uiso calc R 1 . . H
    C16  .33698(16)  .6101(2)  .3365(2)  .0382(5) Uani d . 1 . . C
    H16  .2577  .6103  .3111  .046 Uiso calc R 1 . . H
    C17  .39086(16)  .5164(2)  .30286(18)  .0352(5) Uani d . 1 . . C
    C17'  .32876(18)  .4114(2)  .2298(2)  .0522(7) Uani d . 1 . . C
    H17A  .3469  .3391  .2798  .078 Uiso calc R 1 . . H
    H17B  .3509  .4008  .1578  .078 Uiso calc R 1 . . H
    H17C  .2482  .4263  .2046  .078 Uiso calc R 1 . . H
    C18  .51024(15)  .52085(18)  .34368(17)  .0276(4) Uani d . 1 . . C
    C19  .57963(15)  .43159(18)  .31861(18)  .0298(5) Uani d . 1 . . C
    H19  .5467  .3649  .2695  .036 Uiso calc R 1 . . H
    C20  .69254(15)  .44170(17)  .36482(17)  .0270(4) Uani d . 1 . . C
    H20  .7393  .3825  .3487  .032 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C11 . 1.391(2) y
    N1 C2 . 1.400(2) y
    N1 H1 .  .90(2) ?
    C2 O2 . 1.249(2) y
    C2 N3 . 1.337(2) y
    N3 C4 . 1.483(2) y
    N3 H3 .  .91(2) ?
    C4 C41 . 1.527(3) ?
    C4 C43 . 1.531(3) ?
    C4 C42 . 1.537(3) ?
    C41 H41A .  .9800 ?
    C41 H41B .  .9800 ?
    C41 H41C .  .9800 ?
    C42 H42A .  .9800 ?
    C42 H42B .  .9800 ?
    C42 H42C .  .9800 ?
    C43 H43A .  .9800 ?
    C43 H43B .  .9800 ?
    C43 H43C .  .9800 ?
    C11 N12 . 1.322(2) y
    C11 C20 . 1.430(3) ?
    N12 C13 . 1.374(2) y
    C13 N14 . 1.367(2) y
    C13 C18 . 1.417(3) ?
    N14 C15 . 1.336(2) y
    C15 C16 . 1.407(3) ?
    C15 C15' . 1.510(3) ?
    C15' H15A .  .9800 ?
    C15' H15B .  .9800 ?
    C15' H15C .  .9800 ?
    C16 C17 . 1.381(3) ?
    C16 H16 .  .9500 ?
    C17 C18 . 1.431(3) ?
    C17 C17' . 1.512(3) ?
    C17' H17A .  .9800 ?
    C17' H17B .  .9800 ?
    C17' H17C .  .9800 ?
    C18 C19 . 1.427(3) ?
    C19 C20 . 1.358(3) ?
    C19 H19 .  .9500 ?
    C20 H20 .  .9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C11 N1 C2 . . 129.94(16) y
    C11 N1 H1 . . 115.2(12) ?
    C2 N1 H1 . . 114.6(12) ?
    O2 C2 N3 . . 124.82(16) y
    O2 C2 N1 . . 118.28(15) y
    N3 C2 N1 . . 116.90(15) y
    C2 N3 C4 . . 125.23(15) y
    C2 N3 H3 . . 114.6(14) ?
    C4 N3 H3 . . 120.1(14) ?
    N3 C4 C41 . . 110.34(15) ?
    N3 C4 C43 . . 110.01(16) ?
    C41 C4 C43 . . 111.07(16) ?
    N3 C4 C42 . . 105.11(14) ?
    C41 C4 C42 . . 109.80(17) ?
    C43 C4 C42 . . 110.34(17) ?
    C4 C41 H41A . . 109.5 ?
    C4 C41 H41B . . 109.5 ?
    H41A C41 H41B . . 109.5 ?
    C4 C41 H41C . . 109.5 ?
    H41A C41 H41C . . 109.5 ?
    H41B C41 H41C . . 109.5 ?
    C4 C42 H42A . . 109.5 ?
    C4 C42 H42B . . 109.5 ?
    H42A C42 H42B . . 109.5 ?
    C4 C42 H42C . . 109.5 ?
    H42A C42 H42C . . 109.5 ?
    H42B C42 H42C . . 109.5 ?
    C4 C43 H43A . . 109.5 ?
    C4 C43 H43B . . 109.5 ?
    H43A C43 H43B . . 109.5 ?
    C4 C43 H43C . . 109.5 ?
    H43A C43 H43C . . 109.5 ?
    H43B C43 H43C . . 109.5 ?
    N12 C11 N1 . . 119.54(16) ?
    N12 C11 C20 . . 122.95(16) ?
    N1 C11 C20 . . 117.50(16) ?
    C11 N12 C13 . . 118.95(16) y
    N14 C13 N12 . . 114.37(16) ?
    N14 C13 C18 . . 123.78(16) ?
    N12 C13 C18 . . 121.85(17) ?
    C15 N14 C13 . . 117.08(18) y
    N14 C15 C16 . . 122.74(19) ?
    N14 C15 C15' . . 116.3(2) ?
    C16 C15 C15' . . 120.93(18) ?
    C15 C15' H15A . . 109.5 ?
    C15 C15' H15B . . 109.5 ?
    H15A C15' H15B . . 109.5 ?
    C15 C15' H15C . . 109.5 ?
    H15A C15' H15C . . 109.5 ?
    H15B C15' H15C . . 109.5 ?
    C17 C16 C15 . . 121.55(18) ?
    C17 C16 H16 . . 119.2 ?
    C15 C16 H16 . . 119.2 ?
    C16 C17 C18 . . 116.79(19) ?
    C16 C17 C17' . . 122.51(18) ?
    C18 C17 C17' . . 120.7(2) ?
    C17 C17' H17A . . 109.5 ?
    C17 C17' H17B . . 109.5 ?
    H17A C17' H17B . . 109.5 ?
    C17 C17' H17C . . 109.5 ?
    H17A C17' H17C . . 109.5 ?
    H17B C17' H17C . . 109.5 ?
    C13 C18 C19 . . 117.41(16) ?
    C13 C18 C17 . . 118.06(18) ?
    C19 C18 C17 . . 124.52(18) ?
    C20 C19 C18 . . 120.22(18) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C11 . . 118.59(17) ?
    C19 C20 H20 . . 120.7 ?
    C11 C20 H20 . . 120.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C11 N1 C2 O2 . . . . 179.46(17) y
    C11 N1 C2 N3 . . . .  -.3(3) y
    O2 C2 N3 C4 . . . . -1.6(3) y
    N1 C2 N3 C4 . . . . 178.18(16) y
    C2 N3 C4 C41 . . . . 59.2(2) ?
    C2 N3 C4 C43 . . . . -63.7(2) ?
    C2 N3 C4 C42 . . . . 177.53(18) ?
    C2 N1 C11 N12 . . . .  -.2(3) y
    C2 N1 C11 C20 . . . . -178.79(17) ?
    N1 C11 N12 C13 . . . . -177.06(16) ?
    C20 C11 N12 C13 . . . . 1.5(3) ?
    C11 N12 C13 N14 . . . . 178.71(16) ?
    C11 N12 C13 C18 . . . .  -.4(3) ?
    N12 C13 N14 C15 . . . . -178.25(16) ?
    C18 C13 N14 C15 . . . .  .8(3) ?
    C13 N14 C15 C16 . . . .  -.3(3) ?
    C13 N14 C15 C15' . . . . 179.29(18) ?
    N14 C15 C16 C17 . . . .  .0(3) ?
    C15' C15 C16 C17 . . . . -179.7(2) ?
    C15 C16 C17 C18 . . . .  .0(3) ?
    C15 C16 C17 C17' . . . . 178.1(2) ?
    N14 C13 C18 C19 . . . . -179.94(17) ?
    N12 C13 C18 C19 . . . .  -.9(3) ?
    N14 C13 C18 C17 . . . .  -.9(3) ?
    N12 C13 C18 C17 . . . . 178.11(17) ?
    C16 C17 C18 C13 . . . .  .5(3) ?
    C17' C17 C18 C13 . . . . -177.71(19) ?
    C16 C17 C18 C19 . . . . 179.42(19) ?
    C17' C17 C18 C19 . . . . 1.2(3) ?
    C13 C18 C19 C20 . . . . 1.2(3) ?
    C17 C18 C19 C20 . . . . -177.78(19) ?
    C18 C19 C20 C11 . . . .  -.2(3) ?
    N12 C11 C20 C19 . . . . -1.2(3) ?
    N1 C11 C20 C19 . . . . 177.37(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 O2 3_766  .90(2) 1.93(2) 2.824(2) 175.7(19)
    N3 H3 N12 .  .91(2) 1.91(2) 2.676(2) 141(2)
data_global
_journal_date_recd_electronic     2001-04-25
_journal_date_accepted     2001-05-25
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      8
_journal_page_first     989
_journal_page_last     990
_journal_paper_category     FO
_publ_contact_author_name     'Dr. Michael Bolte'
_publ_contact_author_address
;
      Institut für Organische Chemie
      J. W. Goethe-Universität
      Marie-Curie-Str. 11
      60439 Frankfurt/Main
      Germany
;
_publ_contact_author_email     bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax     '49 69 798 29128'
_publ_contact_author_phone     '49 69 798 29136'
_publ_section_title
;
N-(tert-Butyl)-N'-(2,4-dimethyl-1,8-naphthyridin-2-yl)urea
;
loop_
    _publ_author_name
    _publ_author_address
    'Lüning, Ulrich'
;     Institut für Organische Chemie
      Universität Kiel
      Olshausenstr. 40
      24098 Kiel
      Germany
;
    'Kühl, Christine'
;     Institut für Organische Chemie
      Universität Kiel
      Olshausenstr. 40
      24098 Kiel
      Germany
;
    'Bolte, Michael'
;     Institut für Organische Chemie
      J. W. Goethe-Universität Frankfurt
      Marie-Curie-Str. 11
      60439 Frankfurt/Main
      Germany
;
