#------------------------------------------------------------------------------
#$Date: 2017-05-06 02:15:03 +0300 (Sat, 06 May 2017) $
#$Revision: 196534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242102.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_2242102
loop_
_publ_author_name
'Sausa, Rosario C.'
'Pesce-Rodriguez, Rose A.'
'Wingard, Leah A.'
'Guzmán, Pablo E.'
'Sabatini, Jesse J.'
_publ_section_title
;
 Crystal structure of 3,3'-biisoxazole-5,5'-bis(methylene) dinitrate
 (BIDN)
;
_journal_coeditor_code           PK2599
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              644
_journal_page_last               646
_journal_paper_doi               10.1107/S205698901700487X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H6 N4 O8'
_chemical_formula_moiety         'C8 H6 N4 O8'
_chemical_formula_sum            'C8 H6 N4 O8'
_chemical_formula_weight         286.17
_chemical_name_common            BIDN
_chemical_name_systematic
;
3,3'-Biisoxazole-5,5'-bis(methylene) dinitrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.233(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1917(5)
_cell_length_b                   5.5299(5)
_cell_length_c                   17.4769(12)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    296.85(10)
_cell_measurement_theta_max      25.1720
_cell_measurement_theta_min      2.3540
_cell_volume                     590.65(8)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.85(10)
_diffrn_detector_area_resol_mean 8.0945
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4487
_diffrn_reflns_theta_full        25.343
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         2.361
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SCALE3 ABSPACK in CrysAlisPro; Rigaku OD, 2015; Bourhis et al.,
2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       irregular
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.077(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2016/4 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+0.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                903
_reflns_number_total             1079
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2599sup1.cif
_cod_data_source_block           I
_cod_database_code               2242102
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
C C4 0.5869(4) 0.8027(4) 0.63740(11) 0.0621(6) Uani d 1
H H4A 0.714559 0.780169 0.612468 0.075 Uiso calc 1
H H4B 0.553186 0.974123 0.636451 0.075 Uiso calc 1
C C3 0.1082(3) 0.5201(3) 0.52299(9) 0.0446(5) Uani d 1
C C1 0.3989(3) 0.6693(3) 0.59298(10) 0.0513(5) Uani d 1
C C2 0.1987(3) 0.7337(3) 0.55899(10) 0.0512(5) Uani d 1
H H2 0.133409 0.885170 0.559012 0.061 Uiso calc 1
N N1 0.2447(3) 0.3392(3) 0.53455(9) 0.0558(5) Uani d 1
N N2 0.5082(3) 0.8284(4) 0.76635(11) 0.0660(5) Uani d 1
O O2 0.6372(2) 0.7230(3) 0.71689(8) 0.0610(5) Uani d 1
O O1 0.4340(2) 0.4322(2) 0.57971(8) 0.0603(4) Uani d 1
O O4 0.3714(3) 0.9669(4) 0.73937(12) 0.0920(6) Uani d 1
O O3 0.5589(3) 0.7599(4) 0.83151(10) 0.1017(7) Uani d 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_3
_geom_angle
H4A C4 H4B . 107.9
C1 C4 H4A . 109.1
C1 C4 H4B . 109.1
O2 C4 H4A . 109.1
O2 C4 H4B . 109.1
O2 C4 C1 . 112.39(17)
C2 C3 C3 3_566 129.4(2)
N1 C3 C3 3_566 118.8(2)
N1 C3 C2 . 111.83(16)
C2 C1 C4 . 133.91(19)
C2 C1 O1 . 110.19(16)
O1 C1 C4 . 115.83(18)
C3 C2 H2 . 127.8
C1 C2 C3 . 104.42(17)
C1 C2 H2 . 127.8
C3 N1 O1 . 105.57(15)
O4 N2 O2 . 117.91(19)
O4 N2 O3 . 130.4(2)
O3 N2 O2 . 111.70(19)
N2 O2 C4 . 114.35(16)
C1 O1 N1 . 107.99(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C4 H4A . 0.9700
C4 H4B . 0.9700
C4 C1 . 1.487(3)
C4 O2 . 1.443(2)
C3 C3 3_566 1.465(4)
C3 C2 . 1.411(2)
C3 N1 . 1.304(2)
C1 C2 . 1.334(3)
C1 O1 . 1.355(2)
C2 H2 . 0.9300
N1 O1 . 1.402(2)
N2 O2 . 1.395(2)
N2 O4 . 1.182(2)
N2 O3 . 1.193(2)
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
C4 C1 C2 C3 . 176.7(2)
C4 C1 O1 N1 . -177.37(15)
C3 C3 C2 C1 3_566 179.9(2)
C3 C3 N1 O1 3_566 -179.97(18)
C3 N1 O1 C1 . 0.08(19)
C1 C4 O2 N2 . -82.9(2)
C2 C3 N1 O1 . -0.1(2)
C2 C1 O1 N1 . -0.1(2)
N1 C3 C2 C1 . 0.0(2)
O2 C4 C1 C2 . 115.6(2)
O2 C4 C1 O1 . -67.9(2)
O1 C1 C2 C3 . 0.0(2)
O4 N2 O2 C4 . 1.0(3)
O3 N2 O2 C4 . -178.72(19)
