#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/57/2015720.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_2015720
loop_
_publ_author_name
'Đilović, Ivica'
'Matković-Čalogović, Dubravka'
'Kos, Ivan'
'Biruš, Mladen'
'Jadrijević-Mladar Takač, Milena'
_publ_section_title
;
 Cyclic trihydroxamic acid derivatives
;
_journal_coeditor_code           AV3046
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o45
_journal_page_last               o47
_journal_paper_doi               10.1107/S0108270106049985
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C24 H21 N3 O6'
_chemical_formula_moiety         'C24 H21 N3 O6'
_chemical_formula_sum            'C24 H21 N3 O6'
_chemical_formula_weight         447.44
_chemical_name_systematic
;
1,3,5-benzyloxy-1,3,5-triazinane-2,4,6-trione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.36(2)
_cell_angle_beta                 76.78(2)
_cell_angle_gamma                82.79(2)
_cell_formula_units_Z            2
_cell_length_a                   7.765(2)
_cell_length_b                   12.139(3)
_cell_length_c                   12.783(3)
_cell_measurement_temperature    113(2)
_cell_volume                     1073.8(5)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction,2003)'
_computing_data_reduction
'CrysAlis CCD [or RED?] (Oxford Diffraction,2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       '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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8404
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.350
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0545
_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)+(0.1119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1669
_reflns_number_gt                3183
_reflns_number_total             4600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            av3046.cif
_cod_data_source_block           II
_cod_database_code               2015720
_cod_database_fobs_code          2015720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
C C1 0.8588(2) 0.82131(14) 0.06410(14) 0.0220(4) Uani d 1
C C2 0.7641(2) 1.03328(15) -0.04282(14) 0.0230(4) Uani d 1
C C3 0.6172(2) 0.92207(15) 0.16315(15) 0.0249(4) Uani d 1
C C11 0.9340(2) 0.89208(18) -0.20064(16) 0.0302(4) Uani d 1
H H11A 0.924(3) 0.802(2) -0.1598(17) 0.033(5) Uiso d 1
H H11B 0.817(3) 0.9311(18) -0.2107(17) 0.033(5) Uiso d 1
C C12 1.0661(2) 0.92506(16) -0.31238(15) 0.0260(4) Uani d 1
C C13 1.1794(2) 0.84032(19) -0.34206(18) 0.0337(4) Uani d 1
H H13 1.169(3) 0.758(2) -0.2854(18) 0.032(5) Uiso d 1
C C14 1.2971(3) 0.8745(2) -0.44955(19) 0.0401(5) Uani d 1
H H14 1.374(3) 0.8143(19) -0.4721(19) 0.041(6) Uiso d 1
C C15 1.3014(2) 0.9929(2) -0.52610(18) 0.0369(5) Uani d 1
H H15 1.385(3) 1.017(2) -0.605(2) 0.049(6) Uiso d 1
C C16 1.1900(3) 1.07803(19) -0.49648(17) 0.0358(5) Uani d 1
H H16 1.196(3) 1.1678(19) -0.5558(18) 0.034(5) Uiso d 1
C C17 1.0731(2) 1.04489(17) -0.39132(16) 0.0297(4) Uani d 1
H H17 0.992(3) 1.101(2) -0.3667(19) 0.041(6) Uiso d 1
C C21 0.6012(2) 1.20535(17) 0.08107(19) 0.0305(4) Uani d 1
H H21A 0.695(3) 1.2410(18) 0.0214(18) 0.031(5) Uiso d 1
H H21B 0.639(3) 1.1573(19) 0.1587(19) 0.039(5) Uiso d 1
C C22 0.4584(2) 1.29766(15) 0.08718(15) 0.0248(4) Uani d 1
C C23 0.3920(2) 1.37283(17) -0.01112(17) 0.0317(4) Uani d 1
H H23 0.445(3) 1.3603(18) -0.0805(18) 0.030(5) Uiso d 1
C C24 0.2580(3) 1.45742(17) -0.0032(2) 0.0398(5) Uani d 1
H H24 0.218(3) 1.508(2) -0.075(2) 0.063(7) Uiso d 1
C C25 0.1894(3) 1.46835(18) 0.1022(2) 0.0410(5) Uani d 1
H H25 0.098(3) 1.534(2) 0.1043(18) 0.041(6) Uiso d 1
C C26 0.2553(3) 1.39466(19) 0.1995(2) 0.0391(5) Uani d 1
H H26 0.203(3) 1.404(2) 0.276(2) 0.057(7) Uiso d 1
C C27 0.3877(2) 1.30899(17) 0.19298(17) 0.0301(4) Uani d 1
H H27 0.427(3) 1.2532(19) 0.2657(19) 0.038(5) Uiso d 1
C C31 0.8050(3) 0.70820(17) 0.33618(17) 0.0322(4) Uani d 1
H H31A 0.755(3) 0.7739(19) 0.3628(18) 0.033(5) Uiso d 1
H H31B 0.932(3) 0.7212(18) 0.2911(18) 0.036(5) Uiso d 1
C C32 0.7795(2) 0.58482(15) 0.42814(15) 0.0267(4) Uani d 1
C C33 0.6716(2) 0.56619(18) 0.53571(16) 0.0321(4) Uani d 1
H H33 0.607(3) 0.632(2) 0.5504(19) 0.043(6) Uiso d 1
C C34 0.6493(3) 0.4502(2) 0.61965(18) 0.0412(5) Uani d 1
H H34 0.579(3) 0.442(2) 0.691(2) 0.047(6) Uiso d 1
C C35 0.7336(3) 0.35286(19) 0.59678(19) 0.0406(5) Uani d 1
H H35 0.724(3) 0.272(2) 0.652(2) 0.053(7) Uiso d 1
C C36 0.8403(3) 0.37212(19) 0.4892(2) 0.0403(5) Uani d 1
H H36 0.904(3) 0.303(2) 0.4707(19) 0.044(6) Uiso d 1
C C37 0.8642(2) 0.48661(17) 0.40526(17) 0.0327(4) Uani d 1
H H37 0.946(3) 0.5002(18) 0.3276(19) 0.035(5) Uiso d 1
N N1 0.87062(18) 0.93029(13) -0.03050(12) 0.0239(3) Uani d 1
N N2 0.64202(18) 1.02157(12) 0.05813(12) 0.0236(3) Uani d 1
N N3 0.72844(18) 0.82497(12) 0.15710(12) 0.0243(3) Uani d 1
O O1 0.95215(15) 0.73418(11) 0.06547(11) 0.0295(3) Uani d 1
O O2 0.77767(17) 1.12336(11) -0.13051(11) 0.0317(3) Uani d 1
O O3 0.51260(16) 0.92042(12) 0.24918(11) 0.0329(3) Uani d 1
O O1N 1.00136(14) 0.93721(11) -0.12697(10) 0.0255(3) Uani d 1
O O2N 0.52359(15) 1.11809(10) 0.05381(11) 0.0270(3) Uani d 1
O O3N 0.69860(15) 0.71741(10) 0.25166(10) 0.0274(3) Uani d 1
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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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
O1 C1 N1 123.72(15) ?
O1 C1 N3 124.07(15) ?
N1 C1 N3 112.21(14) y
O2 C2 N2 123.88(15) ?
O2 C2 N1 124.14(15) ?
N2 C2 N1 111.96(14) y
O3 C3 N3 123.94(16) ?
O3 C3 N2 124.12(15) ?
N3 C3 N2 111.94(14) y
O1N C11 C12 105.94(14) ?
O1N C11 H11A 108.6(12) ?
C12 C11 H11A 111.5(12) ?
O1N C11 H11B 107.2(12) ?
C12 C11 H11B 112.9(12) ?
H11A C11 H11B 110.5(16) ?
C13 C12 C17 118.61(17) ?
C13 C12 C11 122.12(17) ?
C17 C12 C11 119.25(16) ?
C12 C13 C14 120.23(19) ?
C12 C13 H13 116.1(12) ?
C14 C13 H13 123.6(12) ?
C15 C14 C13 120.20(18) ?
C15 C14 H14 119.3(13) ?
C13 C14 H14 120.5(13) ?
C14 C15 C16 119.82(19) ?
C14 C15 H15 119.7(13) ?
C16 C15 H15 120.4(13) ?
C17 C16 C15 120.29(19) ?
C17 C16 H16 121.1(11) ?
C15 C16 H16 118.6(11) ?
C16 C17 C12 120.84(17) ?
C16 C17 H17 123.3(13) ?
C12 C17 H17 115.8(13) ?
O2N C21 C22 105.83(13) ?
O2N C21 H21A 109.2(12) ?
C22 C21 H21A 109.5(12) ?
O2N C21 H21B 105.6(12) ?
C22 C21 H21B 113.2(12) ?
H21A C21 H21B 113.1(17) ?
C23 C22 C27 118.98(16) ?
C23 C22 C21 121.14(17) ?
C27 C22 C21 119.87(17) ?
C24 C23 C22 120.14(19) ?
C24 C23 H23 124.8(12) ?
C22 C23 H23 115.1(12) ?
C25 C24 C23 120.43(19) ?
C25 C24 H24 123.3(16) ?
C23 C24 H24 116.3(16) ?
C26 C25 C24 119.65(18) ?
C26 C25 H25 121.5(12) ?
C24 C25 H25 118.7(12) ?
C25 C26 C27 120.48(19) ?
C25 C26 H26 118.4(14) ?
C27 C26 H26 121.1(14) ?
C26 C27 C22 120.31(18) ?
C26 C27 H27 118.8(12) ?
C22 C27 H27 120.8(12) ?
O3N C31 C32 105.74(14) ?
O3N C31 H31A 103.9(12) ?
C32 C31 H31A 114.5(12) ?
O3N C31 H31B 105.7(11) ?
C32 C31 H31B 112.8(12) ?
H31A C31 H31B 113.1(17) ?
C33 C32 C37 119.40(17) ?
C33 C32 C31 121.07(16) ?
C37 C32 C31 119.52(17) ?
C32 C33 C34 119.93(19) ?
C32 C33 H33 120.1(14) ?
C34 C33 H33 119.9(14) ?
C35 C34 C33 120.6(2) ?
C35 C34 H34 122.2(15) ?
C33 C34 H34 117.2(15) ?
C36 C35 C34 119.16(19) ?
C36 C35 H35 117.8(15) ?
C34 C35 H35 123.0(15) ?
C37 C36 C35 120.9(2) ?
C37 C36 H36 118.4(13) ?
C35 C36 H36 120.7(13) ?
C36 C37 C32 120.04(19) ?
C36 C37 H37 120.4(12) ?
C32 C37 H37 119.5(12) ?
N1 O1N C11 109.33(12) ?
N2 O2N C21 109.90(12) ?
N3 O3N C31 109.64(12) ?
C2 N1 C1 128.05(14) y
C2 N1 O1N 115.19(13) ?
C1 N1 O1N 116.72(13) ?
C2 N2 O2N 116.70(13) ?
C2 N2 C3 127.98(14) y
O2N N2 C3 115.24(13) ?
O3N N3 C1 115.89(13) ?
O3N N3 C3 116.35(13) ?
C1 N3 C3 127.62(14) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.201(2) y
C1 N1 1.385(2) y
C1 N3 1.386(2) y
C2 O2 1.206(2) y
C2 N2 1.383(2) y
C2 N1 1.383(2) y
C3 O3 1.203(2) y
C3 N3 1.389(2) y
C3 N2 1.392(2) y
C11 O1N 1.474(2) ?
C11 C12 1.493(3) ?
C11 H11A 1.01(2) ?
C11 H11B 0.98(2) ?
C12 C13 1.382(3) ?
C12 C17 1.398(3) ?
C13 C14 1.400(3) ?
C13 H13 0.97(2) ?
C14 C15 1.376(3) ?
C14 H14 0.98(2) ?
C15 C16 1.378(3) ?
C15 H15 1.02(2) ?
C16 C17 1.376(3) ?
C16 H16 1.05(2) ?
C17 H17 0.97(2) ?
C21 O2N 1.469(2) ?
C21 C22 1.486(2) ?
C21 H21A 0.93(2) ?
C21 H21B 1.02(2) ?
C22 C23 1.391(3) ?
C22 C27 1.393(3) ?
C23 C24 1.384(3) ?
C23 H23 0.95(2) ?
C24 C25 1.383(3) ?
C24 H24 0.98(3) ?
C25 C26 1.376(3) ?
C25 H25 1.00(2) ?
C26 C27 1.381(3) ?
C26 H26 1.01(3) ?
C27 H27 0.99(2) ?
C31 O3N 1.466(2) ?
C31 C32 1.490(3) ?
C31 H31A 0.99(2) ?
C31 H31B 1.02(2) ?
C32 C33 1.384(3) ?
C32 C37 1.391(3) ?
C33 C34 1.388(3) ?
C33 H33 0.95(2) ?
C34 C35 1.381(3) ?
C34 H34 0.92(2) ?
C35 C36 1.380(3) ?
C35 H35 0.95(3) ?
C36 C37 1.376(3) ?
C36 H36 1.00(2) ?
C37 H37 1.01(2) ?
O1N N1 1.3872(17) ?
O2N N2 1.3865(17) ?
O3N N3 1.3789(18) ?
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
_geom_hbond_publ_flag
C15 H15 O3 1_654 1.02(2) 2.54(2) 3.350(3) 136(2) y
C25 H25 O1 1_465 1.00(3) 2.46(3) 3.423(3) 161(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9365148
