#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239742.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_2239742
loop_
_publ_author_name
'Glöcklhofer, Florian'
'Fröhlich, Johannes'
'Stöger, Berthold'
'Weil, Matthias'
_publ_section_title
;
 Crystal structures of 2,5-diazido-1,4-phenylene diacetate and
 2,5-diazido-1,4-phenylene dibutyrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              39
_journal_page_last               42
_journal_paper_doi               10.1107/S1600536814013762
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H8 N6 O4'
_chemical_formula_moiety         'C10 H8 N6 O4'
_chemical_formula_sum            'C10 H8 N6 O4'
_chemical_formula_weight         276.2
_chemical_name_systematic
;
2,5-Diazido-1,4-phenylene diacetate
;
_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                101.508(3)
_cell_angle_beta                 104.544(3)
_cell_angle_gamma                97.057(3)
_cell_formula_units_Z            1
_cell_length_a                   5.4293(6)
_cell_length_b                   5.5678(6)
_cell_length_c                   10.4945(12)
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.8
_cell_measurement_theta_min      3.8
_cell_volume                     295.86(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'JANA2006 (Petříček, et al., 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15989
_diffrn_reflns_theta_full        32.87
_diffrn_reflns_theta_max         32.87
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            light-orange
_exptl_crystal_density_diffrn    1.5498
_exptl_crystal_description       irregular
_exptl_crystal_F_000             142
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.22
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    16
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.0109
_refine_ls_shift/su_mean         0.0024
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0558
_reflns_number_gt                1983
_reflns_number_total             2182
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            su0008sup1.cif
_cod_data_source_block           I
_cod_database_code               2239742
_cod_database_fobs_code          2239742
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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
O O1 0.25671(10) 0.01146(10) 0.20279(5) 0.01189(16) Uani d 1
O O2 0.59540(11) 0.28134(10) 0.35546(6) 0.01772(18) Uani d 1
N N1 0.36886(13) 0.27117(12) -0.19926(6) 0.0141(2) Uani d 1
N N2 0.19623(12) 0.39755(11) -0.19328(6) 0.01377(19) Uani d 1
N N3 0.04446(14) 0.51922(13) -0.19896(8) 0.0208(2) Uani d 1
C C1 0.42743(13) 0.13837(12) -0.09681(7) 0.0106(2) Uani d 1
C C2 0.38596(13) 0.01109(13) 0.10373(7) 0.01038(19) Uani d 1
C C3 0.31388(13) 0.14839(12) 0.00901(7) 0.0108(2) Uani d 1
C C4 0.38466(14) 0.15794(13) 0.33011(7) 0.0119(2) Uani d 1
C C5 0.22479(16) 0.13357(15) 0.42495(7) 0.0174(2) Uani d 1
H H1c3 0.185611 0.250721 0.016023 0.013 Uiso d 1
H H1c5 0.054271 0.162226 0.38606 0.0208 Uiso d 1
H H2c5 0.213484 -0.031171 0.440361 0.0208 Uiso d 1
H H3c5 0.303627 0.253962 0.509525 0.0208 Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1 0.0113(3) 0.0152(2) 0.0096(2) 0.00109(19) 0.00522(18) 0.00195(18) O
O2 0.0164(3) 0.0197(3) 0.0148(3) -0.0021(2) 0.0057(2) 0.0004(2) O
N1 0.0169(3) 0.0155(3) 0.0139(3) 0.0069(2) 0.0072(2) 0.0064(2) N
N2 0.0161(3) 0.0132(3) 0.0137(3) 0.0024(2) 0.0056(2) 0.0056(2) N
N3 0.0214(4) 0.0201(3) 0.0276(4) 0.0089(3) 0.0118(3) 0.0119(3) N
C1 0.0113(3) 0.0107(3) 0.0096(3) 0.0016(2) 0.0032(2) 0.0021(2) C
C2 0.0105(3) 0.0116(3) 0.0091(3) 0.0012(2) 0.0042(2) 0.0011(2) C
C3 0.0106(3) 0.0115(3) 0.0107(3) 0.0027(2) 0.0040(2) 0.0018(2) C
C4 0.0144(3) 0.0124(3) 0.0102(3) 0.0039(2) 0.0049(2) 0.0028(2) C
C5 0.0186(4) 0.0228(4) 0.0129(3) 0.0030(3) 0.0091(3) 0.0037(3) C
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
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
C2 O1 C4 . . 116.60(5)
N2 N1 C1 . . 115.40(7)
N1 N2 N3 . . 173.01(9)
N1 C1 C2 . 2_655 116.58(7)
N1 C1 C3 . . 124.83(7)
C2 C1 C3 2_655 . 118.59(7)
O1 C2 C1 . 2_655 119.80(7)
O1 C2 C3 . . 118.66(7)
C1 C2 C3 2_655 . 121.42(7)
C1 C3 C2 . . 120.00(7)
C1 C3 H1c3 . . 120
C2 C3 H1c3 . . 120
O1 C4 O2 . . 122.32(7)
O1 C4 C5 . . 110.16(6)
O2 C4 C5 . . 127.51(6)
C4 C5 H1c5 . . 109.47
C4 C5 H2c5 . . 109.47
C4 C5 H3c5 . . 109.47
H1c5 C5 H2c5 . . 109.47
H1c5 C5 H3c5 . . 109.47
H2c5 C5 H3c5 . . 109.47
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.3924(10)
O1 C4 . 1.3758(8)
O2 C4 . 1.1971(9)
N1 N2 . 1.2456(10)
N1 C1 . 1.4167(10)
N2 N3 . 1.1269(10)
C1 C2 2_655 1.3944(11)
C1 C3 . 1.3943(11)
C2 C3 . 1.3810(11)
C3 H1c3 . 0.96
C4 C5 . 1.4904(12)
C5 H1c5 . 0.96
C5 H2c5 . 0.96
C5 H3c5 . 0.96
