#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227841.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_7227841
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         'C4 H4 N2 O4'
_chemical_formula_sum            'C4 H4 N2 O4'
_chemical_formula_weight         144.09
_chemical_name_systematic
;
1,4-Dinitro-1,3-butadiene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.516(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8306(3)
_cell_length_b                   10.3433(6)
_cell_length_c                   7.9532(6)
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.28
_cell_volume                     307.63(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX2 area-detector diffractometer'
_diffrn_measurement_method       'ω 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3158
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         3.28
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0356
_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)+(0.0372P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                528
_reflns_number_total             762
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
#---------------------------------------------------------

TITL DK10A in P2(1)/c
CELL  0.71073   3.8306  10.3433   7.9532   90.000  102.516   90.000
ZERR     2.00   0.0003   0.0006   0.0006    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  8    8    4    8
MERG   2

EQIV $1 1-X, -0.5+Y, 0.5-Z
EQIV $2 -1+X, 0.5-Y, -0.5+Z
EQIV $3 -1+X, Y, Z
EQIV $4 1-X, -Y, 1-Z

RTAB XHY C1 H1 O1_$1
RTAB XHY C2 H2 O2_$2
RTAB XHY C1 H1 O2_$4

RTAB H..O H1 O1_$1
RTAB H..O H1 O2_$4
RTAB H..O H2 O2_$2

RTAB O..O C1 O1_$1
RTAB O..O C1 O2_$4
RTAB O..O C2 O2_$2

RTAB O..O N1 O2_$3

MPLA 4 C1 N1 O1 O2 O2_$3
FMAP   2
PLAN   10
SIZE     0.22   0.24   0.24
ACTA
BOND   $H
CONF
L.S.   5
TEMP    23.00
WGHT    0.037200    0.067900
FVAR       1.86687
O1    4    0.263569    0.262719    0.261302    11.00000    0.09811    0.04194 =
         0.07826   -0.01733    0.01072   -0.00593
O2    4    0.635964    0.142934    0.434389    11.00000    0.08605    0.09121 =
         0.05716   -0.01080   -0.01540   -0.02804
N1    3    0.398070    0.158605    0.306846    11.00000    0.05588    0.05349 =
         0.04339   -0.01055    0.00924   -0.01670
C1    1    0.278878    0.044878    0.203892    11.00000    0.04819    0.03571 =
         0.04172   -0.00277    0.00420   -0.00332
C2    1    0.058061    0.055507    0.054212    11.00000    0.04097    0.03217 =
         0.03881   -0.00008    0.00935   -0.00236
H1    2    0.384012   -0.028232    0.254763    11.00000    0.05461
H2    2   -0.026342    0.139530    0.015335    11.00000    0.04924
HKLF    4
 
REM  DK10A in P2(1)/c
REM R1 =  0.0356 for    528 Fo > 4sig(Fo)  and  0.0585 for all    762 data
REM     54 parameters refined using      0 restraints
 
END
 
WGHT      0.0372      0.0682
REM Highest difference peak  0.161,  deepest hole -0.149,  1-sigma level  0.032
Q1    1   0.0000  0.0000  0.0000  10.50000  0.05    0.16
Q2    1   0.4385  0.1510  0.4719  11.00000  0.05    0.15
Q3    1   0.2885  0.0575  0.0960  11.00000  0.05    0.14
Q4    1   0.6298  0.1649  0.3559  11.00000  0.05    0.12
Q5    1   0.3724  0.1005  0.2450  11.00000  0.05    0.12
Q6    1   0.0565  0.0324  0.1566  11.00000  0.05    0.12
Q7    1   0.7363  0.1308  0.4560  11.00000  0.05    0.10
Q8    1   0.4507  0.2372  0.2146  11.00000  0.05    0.10
Q9    1   0.7203  0.0771  0.4433  11.00000  0.05    0.09
Q10   1   0.2322 -0.0281  0.2945  11.00000  0.05    0.09

;
_cod_data_source_file            c7ce00267j2.cif
_cod_data_source_block           1
_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/c'
_cod_database_code               7227841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.2636(4) 0.26272(11) 0.26130(18) 0.0740(5) Uani 1 1 d
O2 O 0.6360(4) 0.14293(14) 0.43439(18) 0.0828(5) Uani 1 1 d
N1 N 0.3981(4) 0.15860(13) 0.30685(17) 0.0511(4) Uani 1 1 d
C1 C 0.2789(4) 0.04488(13) 0.20389(19) 0.0427(4) Uani 1 1 d
C2 C 0.0581(4) 0.05551(12) 0.05421(17) 0.0372(3) Uani 1 1 d
H1 H 0.384(5) -0.0282(16) 0.255(2) 0.055(5) Uiso 1 1 d
H2 H -0.026(4) 0.1395(15) 0.015(2) 0.049(4) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0981(11) 0.0419(6) 0.0783(10) -0.0173(6) 0.0107(8) -0.0059(6)
O2 0.0860(10) 0.0912(10) 0.0572(8) -0.0108(7) -0.0154(7) -0.0280(8)
N1 0.0559(8) 0.0535(8) 0.0434(7) -0.0106(6) 0.0092(6) -0.0167(6)
C1 0.0482(9) 0.0357(7) 0.0417(8) -0.0028(6) 0.0042(7) -0.0033(6)
C2 0.0410(7) 0.0322(7) 0.0388(7) -0.0001(5) 0.0094(6) -0.0024(6)
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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 O2 123.95(14) . .
O1 N1 C1 119.32(13) . .
O2 N1 C1 116.71(14) . .
C2 C1 N1 120.58(13) . .
C2 C1 H1 127.7(10) . .
N1 C1 H1 111.6(10) . .
C1 C2 C2 122.06(16) . 3
C1 C2 H2 118.6(10) . .
C2 C2 H2 119.4(10) 3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.2147(17) .
O2 N1 1.2186(18) .
N1 C1 1.4493(18) .
C1 C2 1.307(2) .
C1 H1 0.909(16) .
C2 C2 1.447(3) 3
C2 H2 0.955(16) .
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 O1 0.909(16) 2.567(17) 3.3846(19) 149.9(14) 2_645 yes
C1 H1 O2 0.909(16) 2.758(17) 3.428(2) 131.4(14) 3_656 yes
C2 H2 O2 0.955(16) 2.606(16) 3.5473(19) 168.8(13) 4_465 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
_geom_torsion_site_symmetry_4
O1 N1 C1 C2 7.4(2) .
O2 N1 C1 C2 -171.34(15) .
N1 C1 C2 C2 178.12(16) 3
