#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012138
loop_
_publ_author_name
'Lüning, Ulrich'
'Kühl, Christine'
'Bolte, Michael'
_publ_section_title
N-tert-Butyl-N'-(5,7-dimethyl-1,8-naphthyridin-2-yl)urea
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              989
_journal_page_last               990
_journal_paper_doi               10.1107/S0108270101008605
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C15 H20 N4 O'
_chemical_formula_sum            'C15 H20 N4 O'
_chemical_formula_weight         272.35
_chemical_melting_point          513
_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'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 109.5780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7129(2)
_cell_length_b                   11.20670(10)
_cell_length_c                   11.6822(2)
_cell_measurement_reflns_used    5891
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1568.14(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full .99
_diffrn_measured_fraction_theta_max .99
_diffrn_measurement_device_type  'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .051
_diffrn_reflns_av_sigmaI/netI    .049
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10199
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  900
_diffrn_standards_number         512
_exptl_absorpt_coefficient_mu    .075
_exptl_absorpt_correction_T_max  .994
_exptl_absorpt_correction_T_min  .970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .08
_refine_diff_density_max         .29
_refine_diff_density_min         -.23
_refine_ls_extinction_coef       .014(2)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          .084
_refine_ls_R_factor_gt           .050
_refine_ls_shift/su_max          <0.02
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0636P)²+0.4824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .136
_reflns_number_gt                2135
_reflns_number_total             3174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1059.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' 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      'P 21/c'
_cod_database_code               2012138
_cod_database_fobs_code          2012138
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_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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_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_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)
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_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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9087911
