#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238038.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_2238038
loop_
_publ_author_name
'Srinivasan, Thothadri'
'Kalpana, Venkatesan'
'Rajakumar, Perumal'
'Velmurugan, Devadasan'
_publ_section_title
;
 8,15-Dioxa-10,13-diazatetracyclo[14.4.0.0^2,7^.0^9,14^]icosa-1(16),2,4,6,9(14),10,12,17,19-nonaene
;
_journal_coeditor_code           SU2586
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o813
_journal_page_last               o814
_journal_paper_doi               10.1107/S1600536813011318
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H10 N2 O2'
_chemical_formula_moiety         'C16 H10 N2 O2'
_chemical_formula_sum            'C16 H10 N2 O2'
_chemical_formula_weight         262.26
_chemical_name_systematic
8,15-Dioxa-10,13-diazatetracyclo[14.4.0.0^2,7^.0^9,14^]icosa-1(16),2,4,6,9(14),10,12,17,19-nonaene
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.429(3)
_cell_length_b                   10.162(2)
_cell_length_c                   8.3313(18)
_cell_measurement_reflns_used    1502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.45
_cell_volume                     1221.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows
(Farrugia, 2012) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6082
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.129
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0325
_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)+(0.0544P)²+0.1721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1226
_reflns_number_total             1502
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2586.cif
_cod_data_source_block           I
_cod_database_code               2238038
_cod_database_fobs_code          2238038
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.53624(10) 1.14890(12) 0.19682(18) 0.0623(4) Uani d . 1 1
H H1 0.5600 1.2289 0.1616 0.075 Uiso calc R 1 1
C C2 0.53746(8) 0.92738(11) 0.19677(13) 0.0426(3) Uani d . 1 1
C C3 0.60493(7) 0.71770(11) 0.24296(13) 0.0395(3) Uani d . 1 1
C C4 0.54878(7) 0.61036(10) 0.27797(12) 0.0390(3) Uani d . 1 1
C C5 0.58736(8) 0.50933(12) 0.36919(14) 0.0480(3) Uani d . 1 1
H H5 0.5523 0.4349 0.3922 0.058 Uiso calc R 1 1
C C6 0.67748(9) 0.51846(14) 0.42609(16) 0.0568(4) Uani d . 1 1
H H6 0.7020 0.4509 0.4883 0.068 Uiso calc R 1 1
C C7 0.73073(8) 0.62674(15) 0.39094(15) 0.0594(4) Uani d . 1 1
H H7 0.7908 0.6328 0.4305 0.071 Uiso calc R 1 1
C C8 0.69529(8) 0.72654(12) 0.29713(15) 0.0505(3) Uani d . 1 1
H H8 0.7317 0.7989 0.2706 0.061 Uiso calc R 1 1
N N1 0.57395(7) 1.03683(10) 0.14200(14) 0.0546(3) Uani d . 1 1
O O1 0.57275(5) 0.81298(8) 0.13462(9) 0.0446(2) Uani d . 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C1 . 3_655 121.95(8)
N1 C1 H1 . . 119.0
C1 C1 H1 3_655 . 119.0
N1 C2 O1 . . 116.01(10)
N1 C2 C2 . 3_655 122.05(7)
O1 C2 C2 . 3_655 121.79(6)
C8 C3 C4 . . 122.16(11)
C8 C3 O1 . . 118.51(10)
C4 C3 O1 . . 118.93(9)
C3 C4 C5 . . 117.38(10)
C3 C4 C4 . 3_655 119.18(8)
C5 C4 C4 . 3_655 123.41(8)
C6 C5 C4 . . 120.77(12)
C6 C5 H5 . . 119.6
C4 C5 H5 . . 119.6
C7 C6 C5 . . 120.33(12)
C7 C6 H6 . . 119.8
C5 C6 H6 . . 119.8
C6 C7 C8 . . 120.18(11)
C6 C7 H7 . . 119.9
C8 C7 H7 . . 119.9
C7 C8 C3 . . 119.14(11)
C7 C8 H8 . . 120.4
C3 C8 H8 . . 120.4
C2 N1 C1 . . 115.99(12)
C2 O1 C3 . . 117.73(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.3423(17)
C1 C1 3_655 1.371(3)
C1 H1 . 0.9300
C2 N1 . 1.3124(15)
C2 O1 . 1.3707(14)
C2 C2 3_655 1.398(2)
C3 C8 . 1.3826(15)
C3 C4 . 1.3897(15)
C3 O1 . 1.4029(13)
C4 C5 . 1.3935(16)
C4 C4 3_655 1.483(2)
C5 C6 . 1.3871(17)
C5 H5 . 0.9300
C6 C7 . 1.374(2)
C6 H6 . 0.9300
C7 C8 . 1.3787(18)
C7 H7 . 0.9300
C8 H8 . 0.9300
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_4
_geom_torsion
C8 C3 C4 C5 . . -0.82(16)
O1 C3 C4 C5 . . 171.84(9)
C8 C3 C4 C4 . 3_655 177.25(11)
O1 C3 C4 C4 . 3_655 -10.09(16)
C3 C4 C5 C6 . . 1.84(16)
C4 C4 C5 C6 3_655 . -176.15(12)
C4 C5 C6 C7 . . -1.07(18)
C5 C6 C7 C8 . . -0.78(19)
C6 C7 C8 C3 . . 1.78(18)
C4 C3 C8 C7 . . -0.97(17)
O1 C3 C8 C7 . . -173.66(10)
O1 C2 N1 C1 . . 176.77(10)
C2 C2 N1 C1 3_655 . 1.3(2)
C1 C1 N1 C2 3_655 . -0.2(2)
N1 C2 O1 C3 . . 126.38(10)
C2 C2 O1 C3 3_655 . -58.13(16)
C8 C3 O1 C2 . . -86.29(12)
C4 C3 O1 C2 . . 100.77(11)
