#------------------------------------------------------------------------------
#$Date: 2023-12-22 16:07:40 +0100 (Fri 22 de Dec de 2023) $
#$Revision: 288505 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/78/7227838.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7227838
loop_
_publ_author_name
'Bauzá, Antonio'
'Sharko, Anastasiya V.'
'Senchyk, Ganna A.'
'Rusanov, Eduard B.'
'Frontera, Antonio'
'Domasevitch, Kostiantyn V.'
_publ_section_title
;
 π--hole interactions at work: crystal engineering with nitro-derivatives
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              1933
_journal_paper_doi               10.1039/C7CE00267J
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C5 H6 N2 O4'
_chemical_formula_sum            'C5 H6 N2 O4'
_chemical_formula_weight         158.12
_chemical_name_systematic
;
1,4-Dinitro-1,3-pentadiene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-01-26 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.546(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0360(7)
_cell_length_b                   10.7787(8)
_cell_length_c                   10.9735(10)
_cell_measurement_reflns_used    5955
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.65
_cell_volume                     711.69(12)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe Image plate diffraction system'
_diffrn_measurement_method       'φ oscillation 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    0.0230
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5955
_diffrn_reflns_theta_full        28.11
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0357
_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)+(0.0683P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                1275
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00267j2.cif
_cod_data_source_block           2
_cod_depositor_comments
;Adding full bibliography for 7227838--7227841.cif.

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7227838
loop_
_symmetry_equiv_pos_as_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.67633(18) -0.16942(10) -0.26809(10) 0.0591(3) Uani 1 1 d
O2 O 0.82680(15) 0.01208(10) -0.24241(9) 0.0533(3) Uani 1 1 d
O3 O -0.10550(16) 0.17130(9) 0.03737(10) 0.0559(3) Uani 1 1 d
O4 O -0.02729(17) 0.36474(10) 0.05858(11) 0.0590(3) Uani 1 1 d
N1 N 0.67343(16) -0.06039(10) -0.23480(8) 0.0394(3) Uani 1 1 d
N2 N 0.01618(16) 0.26031(9) 0.02551(9) 0.0377(2) Uani 1 1 d
C1 C 0.47348(19) -0.01992(12) -0.18056(10) 0.0371(3) Uani 1 1 d
C2 C 0.45216(18) 0.09487(11) -0.14157(9) 0.0339(3) Uani 1 1 d
C3 C 0.25634(18) 0.13172(11) -0.08235(10) 0.0337(3) Uani 1 1 d
C4 C 0.22758(17) 0.24267(10) -0.03342(10) 0.0335(2) Uani 1 1 d
C5 C 0.3742(2) 0.35309(14) -0.02748(16) 0.0520(4) Uani 1 1 d
H1 H 0.369(2) -0.0876(14) -0.1761(12) 0.042(3) Uiso 1 1 d
H2 H 0.564(2) 0.1512(13) -0.1491(13) 0.042(4) Uiso 1 1 d
H3 H 0.145(2) 0.0712(14) -0.0805(12) 0.044(4) Uiso 1 1 d
H5A H 0.419(3) 0.3718(18) 0.058(2) 0.082(6) Uiso 1 1 d
H5B H 0.292(4) 0.424(2) -0.0582(19) 0.091(6) Uiso 1 1 d
H5C H 0.514(4) 0.3360(16) -0.0668(18) 0.075(5) Uiso 1 1 d
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
O2 N1 O1 124.23(10)
O2 N1 C1 119.67(11)
O1 N1 C1 116.07(10)
O4 N2 O3 123.29(10)
O4 N2 C4 117.40(10)
O3 N2 C4 119.31(10)
C2 C1 N1 121.31(11)
C2 C1 H1 127.6(8)
N1 C1 H1 111.1(8)
C1 C2 C3 120.45(11)
C1 C2 H2 120.0(9)
C3 C2 H2 119.5(9)
C4 C3 C2 124.45(10)
C4 C3 H3 120.0(9)
C2 C3 H3 115.6(9)
C3 C4 C5 130.13(11)
C3 C4 N2 115.79(10)
C5 C4 N2 114.08(10)
C4 C5 H5A 109.0(11)
C4 C5 H5B 109.5(13)
H5A C5 H5B 105.8(17)
C4 C5 H5C 110.9(10)
H5A C5 H5C 106.0(16)
H5B C5 H5C 115.4(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2311(14)
O2 N1 1.2192(14)
O3 N2 1.2215(13)
O4 N2 1.2176(13)
N1 C1 1.4543(14)
N2 C4 1.4878(14)
C1 C2 1.3188(17)
C1 H1 0.967(15)
C2 C3 1.4488(15)
C2 H2 0.918(15)
C3 C4 1.3279(16)
C3 H3 0.939(15)
C4 C5 1.4814(17)
C5 H5A 0.98(2)
C5 H5B 0.95(2)
C5 H5C 0.99(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O3 0.967(15) 2.460(14) 3.2585(15) 139.8(11) 3_555 yes
C2 H2 O1 0.918(15) 2.691(15) 3.5804(15) 163.5(12) 2_654 yes
C3 H3 O3 0.939(15) 2.670(15) 3.4368(15) 139.3(11) 3_555 yes
C3 H3 O2 0.939(15) 2.589(14) 3.2785(15) 130.5(11) 1_455 yes
C5 H5A O2 0.98(2) 2.62(2) 3.4816(19) 147.3(15) 4_566 yes
C5 H5B O4 0.95(2) 2.79(2) 3.693(2) 159.2(17) 3_565 yes
C5 H5C O1 0.99(2) 2.71(2) 3.6630(18) 161.7(15) 2_654 yes
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
O2 N1 C1 C2 1.49(17)
O1 N1 C1 C2 179.95(11)
N1 C1 C2 C3 -176.94(10)
C1 C2 C3 C4 175.47(11)
C2 C3 C4 C5 1.1(2)
C2 C3 C4 N2 -178.63(10)
O4 N2 C4 C3 -171.68(11)
O3 N2 C4 C3 7.59(16)
O4 N2 C4 C5 8.55(16)
O3 N2 C4 C5 -172.19(12)
