#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/81/2008144.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_2008144
loop_
_publ_author_name
'Satyen Saha'
'Anunay Samanta'
_publ_section_title
;
 4-Heptamethyleneimino-7-nitrobenzo-2-oxa-1,3-diazole
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              252
_journal_page_last               254
_journal_paper_doi               10.1107/S0108270198012128
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C13 H16 N4 O3'
_chemical_formula_sum            'C13 H16 N4 O3'
_chemical_formula_weight         276.30
_chemical_name_common
4-Heptamethyleneimino-7-nitrobenzo-2-oxa-1,3-diazole
_chemical_name_systematic
;
4-Heptamethyleneimino-7-nitrobenzo-2-oxa-1,3-diazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                93.677(9)
_cell_angle_beta                 98.114(16)
_cell_angle_gamma                90.359(14)
_cell_formula_units_Z            4
_cell_length_a                   6.685(2)
_cell_length_b                   13.2357(11)
_cell_length_c                   14.8763(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      1.54
_cell_volume                     1300.2(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'Xtal3.5 (Hall et al., 199?)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_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  0.000
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4562
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.253
_refine_ls_extinction_coef       0.0070(16)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0610P)²+0.9105P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.148
_reflns_number_gt                2806
_reflns_number_total             4562
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1090.cif
_cod_data_source_block           8nbd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.9105P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.9105P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1300.3(5)
_cod_database_code               2008144
_cod_database_fobs_code          2008144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.0353(3) 0.45340(16) 0.23988(15) 0.0451(5) Uani d . 1 . . N
N4 0.3848(3) 0.33284(18) 0.58640(16) 0.0466(6) Uani d . 1 . . N
O2 0.4415(3) 0.24516(16) 0.59472(15) 0.0636(6) Uani d . 1 . . O
O1 0.1731(3) 0.15631(13) 0.33290(14) 0.0541(5) Uani d . 1 . . O
O3 0.4055(3) 0.39841(16) 0.65001(14) 0.0625(6) Uani d . 1 . . O
N2 0.1159(3) 0.23693(17) 0.28238(16) 0.0499(6) Uani d . 1 . . N
N3 0.2529(3) 0.18649(16) 0.42228(16) 0.0481(6) Uani d . 1 . . N
N5 0.1234(3) 0.82255(18) 0.41805(16) 0.0482(6) Uani d . 1 . . N
N8 0.4574(3) 0.99222(16) 0.76864(15) 0.0464(6) Uani d . 1 . . N
O6 0.1064(3) 0.87900(17) 0.35501(14) 0.0648(6) Uani d . 1 . . O
O4 0.3296(3) 0.68111(13) 0.67148(14) 0.0546(5) Uani d . 1 . . O
N6 0.2528(3) 0.69888(16) 0.58209(16) 0.0482(6) Uani d . 1 . . N
O5 0.0647(3) 0.73358(16) 0.40940(15) 0.0653(6) Uani d . 1 . . O
N7 0.3833(4) 0.76918(17) 0.72346(17) 0.0509(6) Uani d . 1 . . N
C1 0.1186(4) 0.42332(18) 0.32166(17) 0.0385(6) Uiso d . 1 . . C
C2 0.1697(4) 0.4898(2) 0.39794(18) 0.0439(6) Uiso d . 1 . . C
H2 0.1472 0.5586 0.3922 0.053 Uiso calc R 1 . . H
C3 0.2531(4) 0.4580(2) 0.48245(18) 0.0421(6) Uiso d . 1 . . C
H3 0.2827 0.5068 0.5304 0.051 Uiso calc R 1 . . H
C4 0.2939(4) 0.35973(18) 0.49889(17) 0.0393(6) Uiso d . 1 . . C
C5 0.2427(4) 0.28593(18) 0.42563(17) 0.0380(6) Uiso d . 1 . . C
C6 0.1571(4) 0.31727(19) 0.33803(17) 0.0399(6) Uiso d . 1 . . C
C7 0.0225(5) 0.3886(2) 0.15541(19) 0.0551(8) Uani d . 1 . . C
H7A -0.0625 0.4210 0.1076 0.066 Uiso calc R 1 . . H
H7B -0.0420 0.3248 0.1642 0.066 Uiso calc R 1 . . H
C8 0.2281(5) 0.3669(3) 0.1243(2) 0.0642(9) Uani d . 1 . . C
H8A 0.2066 0.3510 0.0591 0.077 Uiso calc R 1 . . H
H8B 0.2827 0.3071 0.1528 0.077 Uiso calc R 1 . . H
C9 0.3883(5) 0.4534(3) 0.1458(2) 0.0670(9) Uani d . 1 . . C
H9A 0.3992 0.4734 0.2102 0.080 Uiso calc R 1 . . H
H9B 0.5177 0.4259 0.1351 0.080 Uiso calc R 1 . . H
C10 0.3554(6) 0.5467(3) 0.0946(3) 0.0755(10) Uani d . 1 . . C
H10A 0.3483 0.5266 0.0304 0.091 Uiso calc R 1 . . H
H10B 0.4744 0.5898 0.1112 0.091 Uiso calc R 1 . . H
C11 0.1729(5) 0.6104(3) 0.1063(2) 0.0661(9) Uani d . 1 . . C
H11A 0.0557 0.5774 0.0702 0.079 Uiso calc R 1 . . H
H11B 0.1916 0.6751 0.0812 0.079 Uiso calc R 1 . . H
C12 0.1256(5) 0.6308(2) 0.2026(2) 0.0553(8) Uani d . 1 . . C
H12A 0.2501 0.6274 0.2444 0.066 Uiso calc R 1 . . H
H12B 0.0758 0.6992 0.2086 0.066 Uiso calc R 1 . . H
C13 -0.0278(4) 0.5588(2) 0.2307(2) 0.0520(7) Uani d . 1 . . C
H13A -0.0638 0.5851 0.2885 0.062 Uiso calc R 1 . . H
H13B -0.1488 0.5590 0.1863 0.062 Uiso calc R 1 . . H
C14 0.2124(4) 0.86164(19) 0.50631(17) 0.0414(6) Uiso d . 1 . . C
C15 0.2534(4) 0.9629(2) 0.52389(18) 0.0439(6) Uiso d . 1 . . C
H15 0.2270 1.0050 0.4761 0.053 Uiso calc R 1 . . H
C16 0.3324(4) 1.0065(2) 0.60924(18) 0.0458(6) Uiso d . 1 . . C
H16 0.3550 1.0761 0.6157 0.055 Uiso calc R 1 . . H
C17 0.3792(4) 0.95069(19) 0.68548(17) 0.0408(6) Uiso d . 1 . . C
C18 0.3428(4) 0.84201(19) 0.66789(17) 0.0397(6) Uiso d . 1 . . C
C19 0.2609(4) 0.79815(18) 0.57943(17) 0.0388(6) Uiso d . 1 . . C
C20 0.5200(4) 1.0994(2) 0.7790(2) 0.0540(7) Uani d . 1 . . C
H20A 0.5616 1.1178 0.7222 0.065 Uiso calc R 1 . . H
H20B 0.6374 1.1069 0.8254 0.065 Uiso calc R 1 . . H
C21 0.3623(5) 1.1741(2) 0.8040(2) 0.0550(7) Uani d . 1 . . C
H21A 0.2407 1.1632 0.7603 0.066 Uiso calc R 1 . . H
H21B 0.4119 1.2421 0.7985 0.066 Uiso calc R 1 . . H
C22 0.3062(5) 1.1675(3) 0.8998(2) 0.0670(9) Uani d . 1 . . C
H22A 0.4205 1.1402 0.9378 0.080 Uiso calc R 1 . . H
H22B 0.2860 1.2357 0.9244 0.080 Uiso calc R 1 . . H
C23 0.1197(6) 1.1040(3) 0.9079(2) 0.0730(10) Uani d . 1 . . C
H23A 0.1208 1.0925 0.9717 0.088 Uiso calc R 1 . . H
H23B 0.0018 1.1441 0.8894 0.088 Uiso calc R 1 . . H
C24 0.0914(5) 1.0023(3) 0.8548(2) 0.0616(8) Uani d . 1 . . C
H24A 0.0875 1.0136 0.7908 0.074 Uiso calc R 1 . . H
H24B -0.0397 0.9750 0.8624 0.074 Uiso calc R 1 . . H
C25 0.2478(5) 0.9224(2) 0.8788(2) 0.0597(8) Uani d . 1 . . C
H25A 0.1958 0.8580 0.8496 0.072 Uiso calc R 1 . . H
H25B 0.2625 0.9162 0.9440 0.072 Uiso calc R 1 . . H
C26 0.4577(5) 0.9403(2) 0.8527(2) 0.0567(8) Uani d . 1 . . C
H26A 0.5382 0.9800 0.9021 0.068 Uiso calc R 1 . . H
H26B 0.5226 0.8754 0.8460 0.068 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C1 N1 C7 123.2(2) y
C1 N1 C13 120.0(2) y
C7 N1 C13 116.5(2) y
O2 N4 O3 123.0(2) ?
O2 N4 C4 118.2(2) ?
O3 N4 C4 118.8(2) ?
N2 O1 N3 112.26(18) ?
C6 N2 O1 105.4(2) ?
C5 N3 O1 104.1(2) ?
O6 N5 O5 123.3(2) ?
O6 N5 C14 118.9(2) ?
O5 N5 C14 117.8(2) ?
C17 N8 C26 123.4(2) y
C17 N8 C20 119.5(2) y
C26 N8 C20 116.5(2) y
N7 O4 N6 112.27(18) ?
C19 N6 O4 104.5(2) ?
C18 N7 O4 105.2(2) ?
N1 C1 C2 123.3(2) ?
N1 C1 C6 122.5(2) ?
C2 C1 C6 114.3(2) ?
C1 C2 C3 122.9(2) ?
C4 C3 C2 123.8(2) ?
C3 C4 C5 117.4(2) ?
C3 C4 N4 120.9(2) ?
C5 C4 N4 121.7(2) ?
N3 C5 C4 131.1(2) ?
N3 C5 C6 109.3(2) ?
C4 C5 C6 119.6(2) ?
N2 C6 C5 108.9(2) ?
N2 C6 C1 129.0(2) ?
C5 C6 C1 122.0(2) ?
N1 C7 C8 113.8(2) ?
C7 C8 C9 115.8(3) ?
C10 C9 C8 118.0(3) ?
C9 C10 C11 118.9(3) ?
C10 C11 C12 117.0(3) ?
C13 C12 C11 115.0(3) ?
N1 C13 C12 116.4(2) ?
C15 C14 C19 117.2(2) ?
C15 C14 N5 120.8(2) ?
C19 C14 N5 122.0(2) ?
C14 C15 C16 123.8(3) ?
C15 C16 C17 123.1(3) ?
N8 C17 C16 123.6(2) ?
N8 C17 C18 122.2(2) ?
C16 C17 C18 114.2(2) ?
N7 C18 C19 109.0(2) ?
N7 C18 C17 128.9(2) ?
C19 C18 C17 122.0(2) ?
N6 C19 C14 131.2(2) ?
N6 C19 C18 109.1(2) ?
C14 C19 C18 119.7(2) ?
N8 C20 C21 116.1(2) ?
C20 C21 C22 115.1(3) ?
C23 C22 C21 116.6(3) ?
C24 C23 C22 118.3(3) ?
C23 C24 C25 117.4(3) ?
C24 C25 C26 116.7(3) ?
N8 C26 C25 114.3(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.350(3) y
N1 C7 . 1.467(3) ?
N1 C13 . 1.470(3) ?
N4 O2 . 1.231(3) ?
N4 O3 . 1.234(3) ?
N4 C4 . 1.425(3) y
O1 N2 . 1.370(3) ?
O1 N3 . 1.393(3) ?
N2 C6 . 1.308(3) ?
N3 C5 . 1.316(3) ?
N5 O6 . 1.229(3) ?
N5 O5 . 1.232(3) ?
N5 C14 . 1.426(3) y
N8 C17 . 1.354(3) y
N8 C26 . 1.465(4) ?
N8 C20 . 1.469(3) ?
O4 N7 . 1.373(3) ?
O4 N6 . 1.391(3) ?
N6 C19 . 1.318(3) ?
N7 C18 . 1.315(3) ?
C1 C2 . 1.392(4) ?
C1 C6 . 1.458(3) ?
C2 C3 . 1.394(4) ?
C3 C4 . 1.361(3) ?
C4 C5 . 1.419(3) ?
C5 C6 . 1.435(3) ?
C7 C8 . 1.534(4) ?
C8 C9 . 1.550(5) ?
C9 C10 . 1.493(5) ?
C10 C11 . 1.512(5) ?
C11 C12 . 1.517(4) ?
C12 C13 . 1.514(4) ?
C14 C15 . 1.367(4) ?
C14 C19 . 1.420(3) ?
C15 C16 . 1.392(4) ?
C16 C17 . 1.393(4) ?
C17 C18 . 1.458(3) ?
C18 C19 . 1.436(4) ?
C20 C21 . 1.518(4) ?
C21 C22 . 1.531(4) ?
C22 C23 . 1.523(5) ?
C23 C24 . 1.513(5) ?
C24 C25 . 1.516(4) ?
C25 C26 . 1.529(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24729650
