#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/76/4317629.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_4317629
loop_
_publ_author_name
'Augusto Cingolani'
Effendy
'Fabio Marchetti'
'Claudio Pettinari'
'Riccardo Pettinari'
'Brian W. Skelton'
'Allan H. White'
_publ_contact_author_address
;
    Department of Chemistry
    University of Western Australia
    Nedlands
    Western Australia 6907
    Australia
;
_publ_contact_author_email       bws@crystal.uwa.edu.au
_publ_contact_author_fax         (+61)_08_9380_1118
_publ_contact_author_name        'Skelton, B. W.'
_publ_contact_author_phone       (+61)_08-9380_3481
_publ_section_title
;
 First Structurally Characterized Silver(I) Derivatives with
 Nonfluorinated β-Diketones
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1151
_journal_page_last               1161
_journal_paper_doi               10.1021/ic0109391
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00000
_cell_angle_beta                 99.67(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   17.981(6)
_cell_length_b                   5.064(4)
_cell_length_c                   24.271(6)
_cell_measurement_reflns_used    8
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.8
_cell_measurement_theta_min      18.6
_cell_volume                     2178.6(19)
_computing_cell_refinement       'Enraf Nonius software'
_computing_data_collection       'Enraf Nonius software'
_computing_data_reduction        'xtal ADDREF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  xtal
_computing_structure_solution    xtal
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type
;
  CAD4 diffractometer
;
_diffrn_measurement_method       '2θ-ω scans'
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .026
_diffrn_reflns_av_sigmaI/netI    .024
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5874
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         8
_exptl_absorpt_coefficient_mu    .092
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
  ?
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         .16
_refine_diff_density_min         -.12
_refine_ls_goodness_of_fit_all   1.58
_refine_ls_goodness_of_fit_ref   1.68
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .048
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          .048
_refine_ls_shift/su_mean         .008
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .059
_refine_ls_wR_factor_ref         .057
_reflns_d_resolution_high        .842
_reflns_d_resolution_low         11.963
_reflns_limit_h_max              21
_reflns_limit_h_min              0
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -28
_reflns_number_gt                1610
_reflns_number_total             1900
_reflns_threshold_expression     'I    > 2.00 sig(I   )'
_cod_data_source_file            ic0109391_1.cif
_cod_data_source_block           HQ3
_cod_original_cell_volume        2179(2)
_cod_original_sg_symbol_Hall     -c_2yc
_cod_database_code               4317629
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,+y,1/2-z
-x,-y,-z
+x,-y,1/2+z
1/2+x,1/2+y,+z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 .61912(7) .3781(3) .37269(5) .0544(7) Uani ? ? 1.00000 ? ?
C11 .67422(9) .5706(3) .36459(7) .0554(8) Uani ? ? 1.00000 ? ?
C12 .73224(12) .6349(4) .40669(9) .0795(12) Uani ? ? 1.00000 ? ?
C13 .78380(13) .8253(5) .39735(11) .0917(14) Uani ? ? 1.00000 ? ?
C14 .77706(12) .9505(4) .34673(10) .0834(12) Uani ? ? 1.00000 ? ?
C15 .71925(12) .8850(4) .30505(10) .0819(12) Uani ? ? 1.00000 ? ?
C16 .66731(11) .6950(4) .31365(8) .0697(10) Uani ? ? 1.00000 ? ?
N2 .55804(7) .3344(3) .33001(5) .0590(7) Uani ? ? 1.00000 ? ?
C3 .51840(9) .1444(3) .34769(6) .0556(8) Uani ? ? 1.00000 ? ?
C31 .44900(12) .0472(5) .31075(9) .0770(12) Uani ? ? 1.00000 ? ?
C4 .55138(9) .0573(3) .40209(6) .0539(8) Uani ? ? 1.00000 ? ?
C41 .53337(10) -.1365(3) .44053(7) .0606(9) Uani ? ? 1.00000 ? ?
C42 .46339(13) -.2973(4) .42805(10) .0740(12) Uani ? ? 1.00000 ? ?
O4 .57762(8) -.1692(3) .48541(5) .0786(8) Uani ? ? 1.00000 ? ?
C5 .61565(8) .2131(3) .41557(6) .0539(8) Uani ? ? 1.00000 ? ?
O5 .66502(7) .2059(3) .46221(5) .0723(7) Uani ? ? 1.00000 ? ?
H12 .7362(12) .549(5) .4433(9) .101(7) Uiso ? ? 1.00000 ? ?
H14 .8133(12) 1.079(4) .3404(8) .090(6) Uiso ? ? 1.00000 ? ?
H13 .8256(15) .865(5) .4270(11) .112(8) Uiso ? ? 1.00000 ? ?
H15 .7128(12) .965(4) .2695(9) .096(7) Uiso ? ? 1.00000 ? ?
H16 .6281(11) .641(4) .2839(8) .079(6) Uiso ? ? 1.00000 ? ?
H31a .4036(13) .074(4) .3296(9) .102(7) Uiso ? ? 1.00000 ? ?
H31b .4554(15) -.144(6) .3023(10) .118(9) Uiso ? ? 1.00000 ? ?
H31c .4367(11) .145(4) .2749(9) .086(6) Uiso ? ? 1.00000 ? ?
H42a .4175(15) -.185(5) .4203(10) .111(8) Uiso ? ? 1.00000 ? ?
H42b .4590(13) -.377(5) .3918(10) .104(8) Uiso ? ? 1.00000 ? ?
H42c .4615(14) -.417(5) .4564(11) .112(8) Uiso ? ? 1.00000 ? ?
H5 .6373(16) .040(6) .4845(12) .149(10) Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0 96 .002014 .002014 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 96 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N ? 0 16 .004028 .002991 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O ? 0 16 .007996 .005981 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
? ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
9 3 -13
-9 3 13
-9 -3 13
9 -3 -13
11 3 10
-11 -3 -10
-11 3 -10
11 -3 10
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 N2 . . . 118.97(13) ?
C11 N1 C5 . . . 130.91(12) ?
N2 N1 C5 . . . 110.07(13) ?
N1 C11 C12 . . . 121.23(16) ?
N1 C11 C16 . . . 118.50(14) ?
C12 C11 C16 . . . 120.26(17) ?
C11 C12 C13 . . . 119.4(2) ?
C11 C12 H12 . . . 120.0(13) ?
C13 C12 H12 . . . 120.6(13) ?
C12 C13 C14 . . . 120.6(2) ?
C12 C13 H13 . . . 118.7(16) ?
C14 C13 H13 . . . 120.7(16) ?
C13 C14 C15 . . . 119.6(2) ?
C13 C14 H14 . . . 120.1(11) ?
C15 C14 H14 . . . 120.3(11) ?
C14 C15 C16 . . . 120.5(2) ?
C14 C15 H15 . . . 122.4(13) ?
C16 C15 H15 . . . 117.1(13) ?
C11 C16 C15 . . . 119.61(17) ?
C11 C16 H16 . . . 119.3(12) ?
C15 C16 H16 . . . 121.0(12) ?
N1 N2 C3 . . . 106.06(12) ?
N2 C3 C31 . . . 119.40(15) ?
N2 C3 C4 . . . 111.47(13) ?
C31 C3 C4 . . . 129.12(16) ?
C3 C31 H31a . . . 110.0(12) ?
C3 C31 H31b . . . 109.2(14) ?
C3 C31 H31c . . . 113.7(11) ?
H31a C31 H31b . . . 111(2) ?
H31a C31 H31c . . . 104.6(17) ?
H31b C31 H31c . . . 108.6(18) ?
C3 C4 C41 . . . 135.56(15) ?
C3 C4 C5 . . . 104.03(13) ?
C41 C4 C5 . . . 120.41(13) ?
C4 C41 C42 . . . 121.35(15) ?
C4 C41 O4 . . . 118.71(16) ?
C42 C41 O4 . . . 119.94(17) ?
C41 C42 H42a . . . 111.9(15) ?
C41 C42 H42b . . . 110.7(15) ?
C41 C42 H42c . . . 110.1(15) ?
H42a C42 H42b . . . 97(2) ?
H42a C42 H42c . . . 113(2) ?
H42b C42 H42c . . . 114(2) ?
N1 C5 C4 . . . 108.36(12) ?
N1 C5 O5 . . . 124.79(14) ?
C4 C5 O5 . . . 126.84(14) ?
C5 O5 H5 . . . 98.1(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C11 . . 1.427(2) ?
N1 N2 . . 1.3950(16) ?
N1 C5 . . 1.344(2) ?
C11 C12 . . 1.371(3) ?
C11 C16 . . 1.375(3) ?
C12 C13 . . 1.382(3) ?
C12 H12 . . .98(2) ?
C13 C14 . . 1.370(4) ?
C13 H13 . . .97(2) ?
C14 C15 . . 1.364(3) ?
C14 H14 . . .95(2) ?
C15 C16 . . 1.381(3) ?
C15 H15 . . .94(2) ?
C16 H16 . . .960(18) ?
N2 C3 . . 1.312(2) ?
C3 C31 . . 1.492(3) ?
C3 C4 . . 1.424(2) ?
C31 H31a . . 1.01(2) ?
C31 H31b . . 1.00(3) ?
C31 H31c . . .99(2) ?
C4 C41 . . 1.428(2) ?
C4 C5 . . 1.392(2) ?
C41 C42 . . 1.487(3) ?
C41 O4 . . 1.247(2) ?
C42 H42a . . .99(3) ?
C42 H42b . . .96(2) ?
C42 H42c . . .92(3) ?
C5 O5 . . 1.3165(18) ?
O5 H5 . . 1.16(3) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 C12 2.438(3) . . ?
N1 C16 2.408(3) . . ?
N1 C3 2.163(2) . . ?
N1 C4 2.219(2) . . ?
N1 O5 2.3580(18) . . ?
N1 H12 2.63(2) . . ?
N1 H16 2.56(2) . . ?
C11 C13 2.377(3) . . ?
C11 C14 2.753(3) . . ?
C11 C15 2.382(3) . . ?
C11 N2 2.431(2) . . ?
C11 C5 2.521(2) . . ?
C11 O5 3.030(2) . . ?
C11 H12 2.05(2) . . ?
C11 H16 2.026(19) . . ?
C12 C14 2.391(3) . . ?
C12 C15 2.748(3) . . ?
C12 C16 2.381(3) . . ?
C12 C5 3.026(3) . . ?
C12 O5 2.923(3) . . ?
C12 H13 2.03(3) . . ?
C13 C15 2.363(3) . . ?
C13 C16 2.742(3) . . ?
C13 H12 2.06(2) . . ?
C13 H14 2.02(2) . . ?
C14 C16 2.383(3) . . ?
C14 H13 2.04(3) . . ?
C14 H15 2.03(2) . . ?
C15 H14 2.02(2) . . ?
C15 H16 2.05(2) . . ?
C16 N2 2.759(3) . . ?
C16 H15 2.00(2) . . ?
N2 C31 2.423(3) . . ?
N2 C4 2.261(2) . . ?
N2 C5 2.2450(19) . . ?
N2 H16 2.39(2) . . ?
N2 H31c 2.74(2) . '2 655' ?
N2 H31c 2.547(19) . . ?
C3 C41 2.640(2) . . ?
C3 C42 3.230(3) . . ?
C3 C5 2.219(2) . . ?
C3 H31a 2.07(2) . . ?
C3 H31b 2.05(3) . . ?
C3 H31c 2.10(2) . . ?
C31 C4 2.633(2) . . ?
C31 C41 3.389(3) . . ?
C31 C42 3.312(3) . . ?
C31 H42b 2.90(2) . . ?
C4 C42 2.542(3) . . ?
C4 O4 2.304(2) . . ?
C4 O5 2.423(2) . . ?
C4 H42a 2.80(3) . . ?
C4 H42b 2.74(2) . . ?
C4 H5 2.31(3) . . ?
C41 O4 3.289(2) . '3 656' ?
C41 C5 2.448(3) . . ?
C41 O5 2.910(2) . . ?
C41 H42a 2.07(3) . . ?
C41 H42b 2.03(2) . . ?
C41 H42c 2.00(3) . . ?
C41 H5 2.18(3) . . ?
C42 O4 3.325(3) . '3 656' ?
C42 O4 2.370(3) . . ?
O4 C5 2.735(2) . . ?
O4 O5 2.587(2) . . ?
O4 H13 2.70(2) . '7 656' ?
O4 H42a 2.90(2) . '3 656' ?
O4 H42c 2.44(2) . . ?
O4 H42c 2.69(3) . '3 646' ?
O4 H5 1.51(3) . . ?
C5 H12 2.75(2) . . ?
C5 H5 1.87(3) . . ?
O5 O5 3.3197(19) . '7 656' ?
O5 H12 2.25(2) . . ?
H12 H13 2.35(4) . . ?
H14 H13 2.34(3) . . ?
H14 H15 2.35(3) . . ?
H15 H16 2.30(3) . . ?
H31a H31b 1.65(4) . . ?
H31a H31c 1.58(3) . . ?
H31b H31c 1.62(4) . . ?
H42a H42b 1.47(4) . . ?
H42a H42c 1.59(3) . . ?
H42b H42c 1.57(4) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?
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
? ? ? ? ? ? ? ? ? ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10195315
