#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/46/2214613.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_2214613
loop_
_publ_author_name
'Cherif Alaoui, L. '
'Kandri Rodi, Y.'
'Haoudi , A.'
'Obbade, S.'
'Essassi,   E. M.'
_publ_section_title
;
 2,4-Dioxo-1,5-benzodiazepino-15-crown-3
;
_journal_coeditor_code           DN2198
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3494
_journal_page_last               o3494
_journal_paper_doi               10.1107/S1600536807029753
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H22 N2 O5'
_chemical_formula_moiety         'C17 H22 N2 O5'
_chemical_formula_sum            'C17 H22 N2 O5'
_chemical_formula_weight         334.37
_chemical_name_systematic
;
4,7,10-Trioxa-1,13-diazatricyclo[11.6.3.0^14,19^]icosa-14,16,18-triene-
20,22-dione
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.692(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.786(3)
_cell_length_b                   8.092(2)
_cell_length_c                   18.062(5)
_cell_measurement_reflns_used    8091
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.20
_cell_measurement_theta_min      2.32
_cell_volume                     1673.7(8)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58268
_diffrn_reflns_theta_full        28.57
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0486
_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)+(0.0687P)²+0.6508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                2847
_reflns_number_total             4249
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2198.cif
_cod_data_source_block           I
_cod_original_cell_volume        1673.8(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214613
_cod_database_fobs_code          2214613
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_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_refinement_flags
_atom_site_occupancy
N N1 0.20967(11) 0.18321(16) 0.97933(8) 0.0311(3) Uani d . 1
N N2 0.30717(12) 0.48339(16) 0.93351(8) 0.0346(3) Uani d . 1
O O1 0.33317(11) -0.01059(14) 0.95379(9) 0.0491(4) Uani d . 1
O O2 0.46850(13) 0.39526(18) 0.89713(9) 0.0593(4) Uani d . 1
O O3 -0.03654(12) 0.00746(18) 0.84001(8) 0.0523(4) Uani d . 1
O O4 0.11484(14) 0.5203(2) 0.78801(8) 0.0608(4) Uani d . 1
O O5 -0.02232(14) 0.2477(2) 0.71616(9) 0.0708(5) Uani d . 1
C C1 0.10071(17) 0.4975(3) 1.09477(11) 0.0501(5) Uani d . 1
H H1 0.0511 0.5030 1.1278 0.060 Uiso calc R 1
C C2 0.15493(17) 0.6394(3) 1.07702(11) 0.0494(5) Uani d . 1
H H2 0.1443 0.7393 1.0999 0.059 Uiso calc R 1
C C3 0.12066(15) 0.3484(2) 1.06322(9) 0.0396(4) Uani d . 1
H H3 0.0875 0.2525 1.0772 0.047 Uiso calc R 1
C C4 0.22434(16) 0.6323(2) 1.02571(10) 0.0420(4) Uani d . 1
H H4 0.2614 0.7276 1.0148 0.050 Uiso calc R 1
C C5 0.19048(13) 0.3397(2) 1.01025(9) 0.0304(3) Uani d . 1
C C6 0.24003(14) 0.4840(2) 0.98966(9) 0.0322(3) Uani d . 1
C C7 0.40197(14) 0.3828(2) 0.93951(10) 0.0375(4) Uani d . 1
C C8 0.31806(14) 0.12811(19) 0.97673(10) 0.0333(4) Uani d . 1
C C9 0.41718(13) 0.2502(2) 0.99990(11) 0.0374(4) Uani d . 1
H H9A 0.4161 0.2991 1.0488 0.045 Uiso calc R 1
H H9B 0.4914 0.1946 1.0046 0.045 Uiso calc R 1
C C10 0.10919(14) 0.0749(2) 0.94951(10) 0.0355(4) Uani d . 1
H H10A 0.0443 0.1072 0.9709 0.043 Uiso calc R 1
H H10B 0.1296 -0.0384 0.9645 0.043 Uiso calc R 1
C C11 0.07348(16) 0.0865(3) 0.86399(11) 0.0474(5) Uani d . 1
H H11A 0.0676 0.2013 0.8481 0.057 Uiso calc R 1
H H11B 0.1308 0.0324 0.8416 0.057 Uiso calc R 1
C C12 0.28953(19) 0.6158(2) 0.87579(11) 0.0466(5) Uani d . 1
H H12A 0.3647 0.6648 0.8760 0.056 Uiso calc R 1
H H12B 0.2413 0.7012 0.8904 0.056 Uiso calc R 1
C C13 0.2335(2) 0.5609(3) 0.79602(13) 0.0600(6) Uani d . 1
H H13A 0.2397 0.6486 0.7606 0.072 Uiso calc R 1
H H13B 0.2747 0.4652 0.7834 0.072 Uiso calc R 1
C C14 -0.0747(2) -0.0112(3) 0.75962(13) 0.0693(7) Uani d . 1
H H14A -0.1371 -0.0923 0.7487 0.083 Uiso calc R 1
H H14B -0.0105 -0.0540 0.7402 0.083 Uiso calc R 1
C C15 -0.1168(2) 0.1426(4) 0.71898(15) 0.0842(9) Uani d . 1
H H15A -0.1599 0.1168 0.6676 0.101 Uiso calc R 1
H H15B -0.1693 0.1986 0.7447 0.101 Uiso calc R 1
C C16 0.0551(3) 0.5107(3) 0.70931(13) 0.0714(7) Uani d . 1
H H16A 0.1052 0.4583 0.6806 0.086 Uiso calc R 1
H H16B 0.0369 0.6211 0.6892 0.086 Uiso calc R 1
C C17 -0.0534(2) 0.4149(4) 0.70047(13) 0.0763(8) Uani d . 1
H H17A -0.0980 0.4550 0.7355 0.092 Uiso calc R 1
H H17B -0.1009 0.4260 0.6489 0.092 Uiso calc R 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'
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
C8 N1 C5 122.77(13)
C8 N1 C10 118.20(13)
C5 N1 C10 119.03(13)
C7 N2 C6 121.80(14)
C7 N2 C12 117.70(15)
C6 N2 C12 119.39(14)
C11 O3 C14 113.89(15)
C13 O4 C16 110.95(18)
C15 O5 C17 114.5(2)
C3 C1 C2 119.72(17)
C3 C1 H1 120.1
C2 C1 H1 120.1
C4 C2 C1 120.10(17)
C4 C2 H2 120.0
C1 C2 H2 120.0
C1 C3 C5 120.71(17)
C1 C3 H3 119.6
C5 C3 H3 119.6
C2 C4 C6 120.98(18)
C2 C4 H4 119.5
C6 C4 H4 119.5
C6 C5 C3 119.31(15)
C6 C5 N1 121.65(13)
C3 C5 N1 119.03(15)
C5 C6 C4 118.99(15)
C5 C6 N2 121.60(14)
C4 C6 N2 119.41(15)
O2 C7 N2 122.34(17)
O2 C7 C9 121.79(16)
N2 C7 C9 115.83(14)
O1 C8 N1 121.59(15)
O1 C8 C9 121.89(15)
N1 C8 C9 116.45(14)
C7 C9 C8 108.22(14)
C7 C9 H9A 110.1
C8 C9 H9A 110.1
C7 C9 H9B 110.1
C8 C9 H9B 110.1
H9A C9 H9B 108.4
N1 C10 C11 110.15(13)
N1 C10 H10A 109.6
C11 C10 H10A 109.6
N1 C10 H10B 109.6
C11 C10 H10B 109.6
H10A C10 H10B 108.1
O3 C11 C10 107.38(14)
O3 C11 H11A 110.2
C10 C11 H11A 110.2
O3 C11 H11B 110.2
C10 C11 H11B 110.2
H11A C11 H11B 108.5
N2 C12 C13 114.77(16)
N2 C12 H12A 108.6
C13 C12 H12A 108.6
N2 C12 H12B 108.6
C13 C12 H12B 108.6
H12A C12 H12B 107.6
O4 C13 C12 111.57(17)
O4 C13 H13A 109.3
C12 C13 H13A 109.3
O4 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 108.0
O3 C14 C15 114.1(2)
O3 C14 H14A 108.7
C15 C14 H14A 108.7
O3 C14 H14B 108.7
C15 C14 H14B 108.7
H14A C14 H14B 107.6
O5 C15 C14 110.6(2)
O5 C15 H15A 109.5
C14 C15 H15A 109.5
O5 C15 H15B 109.5
C14 C15 H15B 109.5
H15A C15 H15B 108.1
O4 C16 C17 110.3(2)
O4 C16 H16A 109.6
C17 C16 H16A 109.6
O4 C16 H16B 109.6
C17 C16 H16B 109.6
H16A C16 H16B 108.1
O5 C17 C16 107.8(2)
O5 C17 H17A 110.2
C16 C17 H17A 110.2
O5 C17 H17B 110.2
C16 C17 H17B 110.2
H17A C17 H17B 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.364(2)
N1 C5 1.423(2)
N1 C10 1.469(2)
N2 C7 1.366(2)
N2 C6 1.426(2)
N2 C12 1.475(2)
O1 C8 1.2240(19)
O2 C7 1.223(2)
O3 C11 1.419(2)
O3 C14 1.423(3)
O4 C13 1.410(3)
O4 C16 1.431(3)
O5 C15 1.411(3)
O5 C17 1.413(3)
C1 C3 1.378(3)
C1 C2 1.388(3)
C1 H1 0.9300
C2 C4 1.375(3)
C2 H2 0.9300
C3 C5 1.404(2)
C3 H3 0.9300
C4 C6 1.398(2)
C4 H4 0.9300
C5 C6 1.395(2)
C7 C9 1.510(3)
C8 C9 1.511(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.505(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.503(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.470(4)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
C16 C17 1.471(4)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9700
C17 H17B 0.9700
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123938
