#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217548.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_2217548
loop_
_publ_author_name
'Mahon, Andrew B.'
'Jensen, Paul'
'Try, Andrew C.'
_publ_section_title
5,11-Dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione
_journal_coeditor_code           HK2415
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o469
_journal_page_last               o469
_journal_paper_doi               10.1107/S1600536808001281
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H14 N2 O2'
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_chemical_melting_point          484
_chemical_name_common
;
N,N'-dimethyldianthranilide
;
_chemical_name_systematic
;
5,11-Dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.6110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2715(10)
_cell_length_b                   7.9113(7)
_cell_length_c                   15.4100(14)
_cell_measurement_reflns_used    5797
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.2912
_cell_measurement_theta_min      2.6988
_cell_volume                     1346.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics
;
X-SEED (Barbour, 2001) and SHELXTL (Bruker, 2003)
;
_computing_publication_material
'modiCIFer (Version Dec-16-2005; Guzei, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker 1000 CCD area-detector'
_diffrn_measurement_method       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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12897
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0.24
_diffrn_standards_number         141
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0371
_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)+(0.0528P)²+0.3606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2686
_reflns_number_total             3175
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2415.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217548
_cod_database_fobs_code          2217548
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.03631(7) 0.20770(12) 0.36470(6) 0.0392(2) Uani d . 1 . .
O O2 0.32157(9) 0.56190(11) 0.51403(6) 0.0384(2) Uani d . 1 . .
N N1 0.26191(9) 0.43083(12) 0.38154(6) 0.0293(2) Uani d . 1 . .
N N2 0.11807(8) 0.19261(12) 0.48395(6) 0.0280(2) Uani d . 1 . .
C C1 0.07223(10) 0.19025(14) 0.39558(8) 0.0283(2) Uani d . 1 A .
C C2 0.15986(10) 0.16141(14) 0.33568(7) 0.0270(2) Uani d . 1 . .
C C3 0.14642(11) 0.01939(15) 0.28107(7) 0.0313(3) Uani d . 1 A .
H H3 0.0832 -0.0590 0.2833 0.038 Uiso calc R 1 . .
C C4 0.22439(12) -0.00839(16) 0.22364(8) 0.0346(3) Uani d . 1 . .
H H4 0.2150 -0.1059 0.1869 0.042 Uiso calc R 1 A .
C C5 0.31624(12) 0.10641(17) 0.21977(7) 0.0356(3) Uani d . 1 A .
H H5 0.3706 0.0864 0.1811 0.043 Uiso calc R 1 . .
C C6 0.32876(11) 0.25014(15) 0.27217(8) 0.0323(3) Uani d . 1 . .
H H6 0.3905 0.3299 0.2683 0.039 Uiso calc R 1 A .
C C7 0.25127(10) 0.27809(14) 0.33037(7) 0.0271(2) Uani d . 1 A .
C C8 0.23206(13) 0.59028(16) 0.33401(9) 0.0410(3) Uani d P 0.75 A 1
H H8A 0.2291 0.6813 0.3766 0.049 Uiso calc PRD 0.75 A 1
H H8B 0.1530 0.5801 0.2939 0.049 Uiso calc PR 0.75 A 1
H H8C 0.2941 0.6162 0.2996 0.049 Uiso calc PRD 0.75 A 1
C C8' 0.23206(13) 0.59028(16) 0.33401(9) 0.0410(3) Uani d P 0.25 A 2
H H8D 0.2974 0.6720 0.3534 0.049 Uiso calc PRD 0.25 A 2
H H8E 0.1562 0.6349 0.3466 0.049 Uiso calc PR 0.25 A 2
H H8F 0.2226 0.5707 0.2702 0.049 Uiso calc PR 0.25 A 2
C C9 0.30500(10) 0.43187(14) 0.47035(7) 0.0271(2) Uani d . 1 A .
C C10 0.33394(10) 0.26308(13) 0.51321(7) 0.0239(2) Uani d . 1 . .
C C11 0.45333(10) 0.22278(15) 0.55095(7) 0.0272(2) Uani d . 1 A .
H H11 0.5166 0.2994 0.5460 0.033 Uiso calc R 1 . .
C C12 0.48022(10) 0.07159(15) 0.59559(7) 0.0304(3) Uani d . 1 . .
H H12 0.5619 0.0443 0.6210 0.036 Uiso calc R 1 A .
C C13 0.38820(11) -0.04021(15) 0.60338(7) 0.0309(3) Uani d . 1 A .
H H13 0.4071 -0.1439 0.6342 0.037 Uiso calc R 1 . .
C C14 0.26895(11) -0.00143(14) 0.56646(7) 0.0291(2) Uani d . 1 . .
H H14 0.2059 -0.0777 0.5723 0.035 Uiso calc R 1 A .
C C15 0.24198(9) 0.14978(14) 0.52073(7) 0.0243(2) Uani d . 1 A .
C C16 0.03856(11) 0.22890(17) 0.54596(9) 0.0363(3) Uani d P 0.65 B 1
H H16A -0.0385 0.2743 0.5134 0.044 Uiso calc PR 0.65 B 1
H H16B 0.0774 0.3121 0.5897 0.044 Uiso calc PR 0.65 B 1
H H16C 0.0236 0.1246 0.5763 0.044 Uiso calc PR 0.65 B 1
C C16' 0.03856(11) 0.22890(17) 0.54596(9) 0.0363(3) Uani d P 0.35 B 2
H H16D -0.0348 0.1596 0.5309 0.044 Uiso calc PR 0.35 B 2
H H16E 0.0163 0.3488 0.5421 0.044 Uiso calc PR 0.35 B 2
H H16F 0.0810 0.2026 0.6064 0.044 Uiso calc PR 0.35 B 2
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
C9 N1 C7 122.20(9)
C9 N1 C8 119.94(10)
C7 N1 C8 117.74(9)
C1 N2 C15 122.43(9)
C1 N2 C16 119.90(10)
C15 N2 C16 117.55(9)
O1 C1 N2 122.43(11)
O1 C1 C2 120.47(10)
N2 C1 C2 117.09(9)
C3 C2 C7 119.27(11)
C3 C2 C1 119.31(10)
C7 C2 C1 121.35(10)
C4 C3 C2 120.54(11)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.91(11)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.11(12)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 120.21(11)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C7 C2 119.94(11)
C6 C7 N1 119.66(10)
C2 C7 N1 120.34(10)
N1 C8 H8A 109.5
N1 C8 H8B 109.5
N1 C8 H8C 109.5
O2 C9 N1 122.97(10)
O2 C9 C10 120.80(10)
N1 C9 C10 116.21(9)
C11 C10 C15 119.42(10)
C11 C10 C9 119.71(9)
C15 C10 C9 120.75(10)
C12 C11 C10 120.20(10)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.13(10)
C11 C12 H12 119.9
C13 C12 H12 119.9
C14 C13 C12 120.29(11)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 119.60(10)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C10 120.36(10)
C14 C15 N2 119.89(9)
C10 C15 N2 119.71(10)
N2 C16 H16A 109.5
N2 C16 H16B 109.5
N2 C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2280(13)
O2 C9 1.2229(14)
N1 C9 1.3569(15)
N1 C7 1.4346(15)
N1 C8 1.4635(14)
N2 C1 1.3558(15)
N2 C15 1.4380(14)
N2 C16 1.4642(15)
C1 C2 1.4990(16)
C2 C3 1.3936(16)
C2 C7 1.3980(15)
C3 C4 1.3846(18)
C3 H3 0.9500
C4 C5 1.3874(19)
C4 H4 0.9500
C5 C6 1.3854(18)
C5 H5 0.9500
C6 C7 1.3897(17)
C6 H6 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.4964(15)
C10 C11 1.3913(15)
C10 C15 1.3926(14)
C11 C12 1.3827(16)
C11 H11 0.9500
C12 C13 1.3867(17)
C12 H12 0.9500
C13 C14 1.3844(17)
C13 H13 0.9500
C14 C15 1.3906(15)
C14 H14 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
C15 N2 C1 O1 171.43(10)
C16 N2 C1 O1 -4.45(17)
C15 N2 C1 C2 -7.30(15)
C16 N2 C1 C2 176.82(10)
O1 C1 C2 C3 -60.48(15)
N2 C1 C2 C3 118.28(11)
O1 C1 C2 C7 116.44(12)
N2 C1 C2 C7 -64.81(14)
C7 C2 C3 C4 1.56(16)
C1 C2 C3 C4 178.54(10)
C2 C3 C4 C5 -0.46(17)
C3 C4 C5 C6 -1.08(17)
C4 C5 C6 C7 1.52(17)
C5 C6 C7 C2 -0.41(16)
C5 C6 C7 N1 -177.39(10)
C3 C2 C7 C6 -1.12(15)
C1 C2 C7 C6 -178.04(10)
C3 C2 C7 N1 175.84(9)
C1 C2 C7 N1 -1.08(15)
C9 N1 C7 C6 -109.40(12)
C8 N1 C7 C6 66.63(14)
C9 N1 C7 C2 73.63(14)
C8 N1 C7 C2 -110.33(12)
C7 N1 C9 O2 175.40(11)
C8 N1 C9 O2 -0.55(18)
C7 N1 C9 C10 -3.60(15)
C8 N1 C9 C10 -179.55(10)
O2 C9 C10 C11 -64.70(15)
N1 C9 C10 C11 114.32(11)
O2 C9 C10 C15 111.25(12)
N1 C9 C10 C15 -69.72(14)
C15 C10 C11 C12 -0.08(16)
C9 C10 C11 C12 175.93(10)
C10 C11 C12 C13 -0.36(16)
C11 C12 C13 C14 0.11(17)
C12 C13 C14 C15 0.59(17)
C13 C14 C15 C10 -1.03(16)
C13 C14 C15 N2 -178.59(10)
C11 C10 C15 C14 0.78(16)
C9 C10 C15 C14 -175.18(10)
C11 C10 C15 N2 178.34(9)
C9 C10 C15 N2 2.37(15)
C1 N2 C15 C14 -108.33(12)
C16 N2 C15 C14 67.64(14)
C1 N2 C15 C10 74.10(14)
C16 N2 C15 C10 -109.93(12)
