#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227840.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_7227840
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_sum            'C6 H8 N2 O4'
_chemical_formula_weight         172.14
_chemical_name_systematic
;
2,4-Dinitro-2,4-hexadiene
;
_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                 101.006(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4312(8)
_cell_length_b                   6.1004(10)
_cell_length_c                   12.3902(13)
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      3.35
_cell_volume                     402.97(10)
_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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4576
_diffrn_reflns_theta_full        28.68
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9372
_exptl_absorpt_correction_T_min  0.9239
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.77(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         1038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0422
_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)+(0.0501P)²+0.0388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                666
_reflns_number_total             1038
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
#---------------------------------------------------------

TITL dk11 in P2(1)/n
CELL  0.71073   5.4312   6.1004  12.3902   90.000  101.006   90.000
ZERR     2.00   0.0008   0.0010   0.0013    0.000    0.005    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  12   16   4    8
 
MERG   2
SHEL 0.74 8
FMAP   2
PLAN   10
SIZE     0.20   0.22   0.32
ACTA
CONF
BOND
BOND $H
 
EQIV $1 1.5-X, -0.5+Y, 0.5-Z
EQIV $2 1.5-X, 0.5+Y, 0.5-Z
EQIV $3 0.5-X, -0.5+Y, 0.5-Z
 
RTAB XHY C2 H2 O1_$1
RTAB H..O H2 O1_$1
RTAB O..O C2 O1_$1
 
RTAB O..O N1 O1_$2
RTAB O..O N1 O2_$3
 
MPLA 4 C1 N1 O1 O2 O1_$2 O2_$3
 
L.S.   4
TEMP    23.00
WGHT    0.050100    0.038800
EXTI    0.768000
FVAR       2.42405
O1    4    0.686734    0.067064    0.276101    11.00000    0.06837    0.06560 =
         0.03313   -0.00287   -0.00586    0.01840
O2    4    0.384209    0.285946    0.284810    11.00000    0.07094    0.06221 =
         0.03563   -0.00977    0.01548    0.00870
N1    3    0.502517    0.170877    0.232577    11.00000    0.05337    0.04000 =
         0.02770   -0.00275    0.00573    0.00000
C1    1    0.417200    0.160139    0.112146    11.00000    0.04893    0.04691 =
         0.02546   -0.00041    0.00260    0.00343
C2    1    0.530848    0.015986    0.058838    11.00000    0.04629    0.04345 =
         0.02605    0.00119    0.00268    0.00561
C3    1    0.211077    0.311665    0.069895    11.00000    0.10420    0.10663 =
         0.03556   -0.01218   -0.00577    0.05964
H2    2    0.655843   -0.073262    0.098052    11.00000    0.04805
H3A   2    0.166907    0.303785   -0.006455    11.00000    0.11339
H3B   2    0.262571    0.442812    0.088544    11.00000    0.10201
H3C   2    0.068944    0.292622    0.101129    11.00000    0.12354
HKLF    4
 
REM  dk11 in P2(1)/n
REM R1 =  0.0422 for    666 Fo > 4sig(Fo)  and  0.0783 for all   1038 data
REM     72 parameters refined using      0 restraints
 
END
 
WGHT      0.0502      0.0385
REM Highest difference peak  0.154,  deepest hole -0.170,  1-sigma level  0.038
Q1    1   0.5301  0.0338  0.0016  11.00000  0.05    0.15
Q2    1   0.4327  0.1462  0.1662  11.00000  0.05    0.15
Q3    1   0.3765  0.2616  0.3659  11.00000  0.05    0.12
Q4    1   0.7919  0.1432  0.2343  11.00000  0.05    0.12
Q5    1   0.5172  0.1415  0.0779  11.00000  0.05    0.12
Q6    1   0.3913  0.3664  0.2247  11.00000  0.05    0.12
Q7    1   0.3314  0.5047  0.1043  11.00000  0.05    0.11
Q8    1   0.0825  0.2133  0.0051  11.00000  0.05    0.11
Q9    1   0.5660 -0.1377  0.2230  11.00000  0.05    0.10
Q10   1   0.6864  0.1292  0.3580  11.00000  0.05    0.10

;
_cod_data_source_file            c7ce00267j2.cif
_cod_data_source_block           3
_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               7227840
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 0.6867(2) 0.0671(2) 0.27610(9) 0.0578(5) Uani 1 1 d
O2 O 0.3842(2) 0.2859(2) 0.28481(9) 0.0556(5) Uani 1 1 d
N1 N 0.5025(3) 0.1709(2) 0.23258(10) 0.0406(4) Uani 1 1 d
C1 C 0.4172(3) 0.1601(3) 0.11215(11) 0.0410(5) Uani 1 1 d
C2 C 0.5308(3) 0.0160(3) 0.05884(12) 0.0392(4) Uani 1 1 d
C3 C 0.2111(7) 0.3117(6) 0.06990(19) 0.0847(10) Uani 1 1 d
H2 H 0.656(3) -0.073(3) 0.0981(15) 0.048(5) Uiso 1 1 d
H3A H 0.167(5) 0.304(5) -0.006(3) 0.113(9) Uiso 1 1 d
H3B H 0.263(5) 0.443(5) 0.089(2) 0.102(11) Uiso 1 1 d
H3C H 0.069(7) 0.293(5) 0.101(3) 0.124(12) 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 0.0684(9) 0.0656(9) 0.0331(6) -0.0029(6) -0.0059(6) 0.0184(7)
O2 0.0709(9) 0.0622(8) 0.0356(6) -0.0098(6) 0.0155(6) 0.0087(6)
N1 0.0534(9) 0.0400(8) 0.0277(6) -0.0027(5) 0.0057(6) 0.0000(6)
C1 0.0489(10) 0.0469(9) 0.0255(7) -0.0004(6) 0.0026(6) 0.0034(7)
C2 0.0463(10) 0.0435(9) 0.0260(7) 0.0012(6) 0.0027(6) 0.0056(7)
C3 0.104(2) 0.107(2) 0.0356(11) -0.0122(12) -0.0058(12) 0.0596(18)
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
O2 N1 O1 122.41(13) . .
O2 N1 C1 117.83(13) . .
O1 N1 C1 119.76(13) . .
C2 C1 C3 129.61(15) . .
C2 C1 N1 116.62(13) . .
C3 C1 N1 113.76(15) . .
C1 C2 C2 123.61(19) . 3_655
C1 C2 H2 119.5(11) . .
C2 C2 H2 116.9(11) 3_655 .
C1 C3 H3A 111.1(17) . .
C1 C3 H3B 107.5(19) . .
H3A C3 H3B 109(2) . .
C1 C3 H3C 114(2) . .
H3A C3 H3C 110(3) . .
H3B C3 H3C 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.2194(17) .
O2 N1 1.2179(17) .
N1 C1 1.4770(18) .
C1 C2 1.321(2) .
C1 C3 1.469(3) .
C2 C2 1.446(3) 3_655
C2 H2 0.931(19) .
C3 H3A 0.93(4) .
C3 H3B 0.86(3) .
C3 H3C 0.93(3) .
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
C2 H2 O1 0.931(19) 2.733(19) 3.583(2) 152.2(14) 2_645 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
O2 N1 C1 C2 -172.68(15) .
O1 N1 C1 C2 7.7(2) .
O2 N1 C1 C3 6.1(3) .
O1 N1 C1 C3 -173.6(2) .
C3 C1 C2 C2 1.2(4) 3_655
N1 C1 C2 C2 179.69(19) 3_655
