#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238829.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_2238829
loop_
_publ_author_name
'Kavitha, Channappa N.'
'Jasinski, Jerry P.'
'Anderson, Brian J.'
'Yathirajan, H.S.'
'Kaur, Manpreet'
_publ_section_title
;
4-Methyl-N-(4-nitrobenzylidene)piperazin-1-amine
;
_journal_coeditor_code ZL2568
_journal_issue 11
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1687
_journal_page_last o1688
_journal_paper_doi 10.1107/S1600536813028493
_journal_volume 69
_journal_year 2013
_chemical_formula_iupac 'C12 H16 N4 O2'
_chemical_formula_moiety 'C12 H16 N4 O2'
_chemical_formula_sum 'C12 H16 N4 O2'
_chemical_formula_weight 248.29
_chemical_name_systematic
;
4-Methyl-N-(4-nitrobenzylidene)piperazin-1-amine
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_Hall '-C 2yc'
_space_group_name_H-M_alt 'C 1 2/c 1'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.2
(compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha 90
_cell_angle_beta 126.527(3)
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 27.9353(14)
_cell_length_b 5.9247(3)
_cell_length_c 18.7763(7)
_cell_measurement_reflns_used 2934
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 72.3048
_cell_measurement_theta_min 3.2131
_cell_volume 2497.2(2)
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material 'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type 'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0307
_diffrn_reflns_limit_h_max 32
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 7200
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 72.315
_diffrn_reflns_theta_min 3.938
_exptl_absorpt_coefficient_mu 0.765
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.86840
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.321
_exptl_crystal_description irregular
_exptl_crystal_F_000 1056
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.32
_exptl_crystal_size_min 0.22
_refine_diff_density_max 0.215
_refine_diff_density_min -0.175
_refine_ls_extinction_coef 0.00056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL2012 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.024
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 165
_refine_ls_number_reflns 2439
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.024
_refine_ls_R_factor_all 0.0491
_refine_ls_R_factor_gt 0.0405
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.9105P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1101
_refine_ls_wR_factor_ref 0.1189
_reflns_number_gt 2022
_reflns_number_total 2439
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL HSY-608B in I2/a #15 New: C2/c
CELL 1.54184 27.9353 5.9247 18.7763 90 126.527 90
ZERR 8 0.0014 0.0003 0.0007 0 0.003 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 96 128 32 16
EQIV $1 1.5-X,2.5-Y,2-Z
L.S. 15
PLAN -15
TEMP -100(2)
HTAB C2 O1_$1
BOND $H
MORE -1
fmap 2
acta
CONF
REM F:/Collaborators%20Stuff-Sept-2013/Yathi-2013-New/HSY-608-B-I2a%20to%
REM 20C2c/hsy-608b.hkl
WGHT 0.063600 0.910500
EXTI 0.000559
FVAR 2.38353
O1 4 0.935620 1.150353 1.269705 11.00000 0.05265 0.06977 =
0.04119 -0.02401 0.01317 0.00083
O2 4 0.969243 0.809509 1.295076 11.00000 0.03256 0.07920 =
0.02946 0.00139 0.01229 0.00961
N1 3 0.604372 0.768477 0.558650 11.00000 0.02777 0.03469 =
0.02561 -0.00313 0.01460 -0.00258
N2 3 0.669594 0.802376 0.746193 11.00000 0.02788 0.02886 =
0.02446 -0.00353 0.01377 -0.00010
N3 3 0.713663 0.867480 0.831176 11.00000 0.02777 0.03260 =
0.02569 -0.00423 0.01544 -0.00377
N4 3 0.934369 0.956686 1.245755 11.00000 0.02804 0.06241 =
0.02866 -0.00655 0.01586 -0.00112
C1 1 0.587839 0.934889 0.597739 11.00000 0.02905 0.03271 =
0.03011 -0.00046 0.01405 0.00311
AFIX 23
H1A 2 0.557023 0.870919 0.602311 11.00000 -1.20000
H1B 2 0.570994 1.070241 0.559361 11.00000 -1.20000
AFIX 0
C2 1 0.642076 1.000662 0.688941 11.00000 0.03347 0.02744 =
0.03104 -0.00220 0.01559 0.00274
AFIX 23
H2A 2 0.671405 1.076141 0.683556 11.00000 -1.20000
H2B 2 0.630243 1.108956 0.716041 11.00000 -1.20000
AFIX 0
C3 1 0.680861 0.618266 0.706439 11.00000 0.03118 0.02863 =
0.02839 -0.00313 0.01500 0.00210
AFIX 23
H3A 2 0.692810 0.481588 0.743778 11.00000 -1.20000
H3B 2 0.714027 0.660052 0.703655 11.00000 -1.20000
AFIX 0
C4 1 0.625819 0.567662 0.614099 11.00000 0.03339 0.02914 =
0.03020 -0.00613 0.01771 -0.00290
AFIX 23
H4A 2 0.635182 0.449443 0.586848 11.00000 -1.20000
H4B 2 0.594128 0.509023 0.617691 11.00000 -1.20000
AFIX 0
C5 1 0.756442 0.731131 0.884722 11.00000 0.02909 0.03036 =
0.02902 -0.00263 0.01810 -0.00235
AFIX 43
H5 2 0.758648 0.588033 0.864000 11.00000 -1.20000
AFIX 0
C6 1 0.801529 0.794791 0.976947 11.00000 0.02714 0.03315 =
0.02779 -0.00099 0.01829 -0.00358
C7 1 0.801001 1.003885 1.011267 11.00000 0.02911 0.03537 =
0.02891 -0.00019 0.01631 0.00087
AFIX 43
H7 2 0.770570 1.110137 0.973727 11.00000 -1.20000
AFIX 0
C8 1 0.844161 1.057185 1.098932 11.00000 0.03254 0.03651 =
0.03295 -0.00654 0.02017 -0.00351
AFIX 43
H8 2 0.843752 1.199109 1.122111 11.00000 -1.20000
AFIX 0
C9 1 0.888211 0.899684 1.152684 11.00000 0.02611 0.04674 =
0.02642 -0.00406 0.01650 -0.00495
C10 1 0.890295 0.692209 1.121290 11.00000 0.02818 0.04367 =
0.02945 0.00372 0.01610 0.00366
AFIX 43
H10 2 0.920764 0.586709 1.159442 11.00000 -1.20000
AFIX 0
C11 1 0.847024 0.641059 1.032985 11.00000 0.03253 0.03412 =
0.03335 -0.00180 0.02013 0.00036
AFIX 43
H11 2 0.848214 0.499839 1.010117 11.00000 -1.20000
AFIX 0
C12 1 0.553528 0.713637 0.468258 11.00000 0.03327 0.04977 =
0.02648 -0.00523 0.01425 -0.00393
AFIX 137
H12A 2 0.521080 0.653716 0.468879 11.00000 -1.50000
H12B 2 0.565414 0.600164 0.443566 11.00000 -1.50000
H12C 2 0.539981 0.850239 0.431687 11.00000 -1.50000
AFIX 0
HKLF 4 1 -1 0 -1 0 1 0 1 0 0
REM HSY-608B in I2/a #15 New: C2/c
REM R1 = 0.0405 for 2022 Fo > 4sig(Fo) and 0.0491 for all 2439 data
REM 165 parameters refined using 0 restraints
END
WGHT 0.0636 0.9055
REM Highest difference peak 0.215, deepest hole -0.175, 1-sigma level 0.044
Q1 1 0.8210 0.7105 1.0087 11.00000 0.05 0.22
Q2 1 0.8732 0.9882 1.1232 11.00000 0.05 0.18
Q3 1 0.7915 0.8700 0.9958 11.00000 0.05 0.18
Q4 1 0.6139 0.9587 0.6480 11.00000 0.05 0.17
Q5 1 0.7227 0.7657 0.8684 11.00000 0.05 0.17
Q6 1 0.6555 0.8920 0.7193 11.00000 0.05 0.16
Q7 1 0.8063 0.9068 0.9828 11.00000 0.05 0.15
Q8 1 0.7763 0.7621 0.9336 11.00000 0.05 0.15
Q9 1 0.6339 0.8053 0.5608 11.00000 0.05 0.15
Q10 1 0.6512 0.5972 0.6591 11.00000 0.05 0.15
Q11 1 0.7437 0.8188 0.8538 11.00000 0.05 0.15
Q12 1 0.6380 0.8406 0.7280 11.00000 0.05 0.14
Q13 1 0.8954 0.8313 1.1338 11.00000 0.05 0.14
Q14 1 0.8786 0.7873 1.1441 11.00000 0.05 0.14
Q15 1 0.5957 0.8303 0.5764 11.00000 0.05 0.14
REM The information below was added by Olex2.
REM
REM R1 = 0.0405 for 2022 Fo > 4sig(Fo) and 0.0491 for all 7701 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.22, deepest hole -0.17
REM Mean Shift 0, Max Shift 0.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0491
REM R1_gt = 0.0405
REM wR_ref = 0.1189
REM GOOF = 1.024
REM Shift_max = 0
REM Shift_mean = 0
REM Reflections_all = 7701
REM Reflections_gt = 2022
REM Parameters = n/a
REM Hole = -0.17
REM Peak = 0.22
REM Flack = n/a
;
_cod_data_source_file zl2568.cif
_cod_data_source_block I
_cod_database_code 2238829
#BEGIN Tags that were not found in dictionaries:
_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.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.93562(6) 1.1504(2) 1.26970(8) 0.0636(4) Uani d 1
O O2 0.96924(5) 0.8095(2) 1.29508(7) 0.0509(3) Uani d 1
N N1 0.60437(5) 0.7685(2) 0.55865(7) 0.0301(3) Uani d 1
N N2 0.66959(5) 0.80238(19) 0.74619(7) 0.0282(3) Uani d 1
N N3 0.71366(5) 0.8675(2) 0.83118(7) 0.0290(3) Uani d 1
N N4 0.93437(5) 0.9567(3) 1.24576(8) 0.0403(3) Uani d 1
C C1 0.58784(6) 0.9349(2) 0.59774(9) 0.0328(3) Uani d 1
H H1A 0.5570 0.8709 0.6023 0.039 Uiso calc 1
H H1B 0.5710 1.0702 0.5594 0.039 Uiso calc 1
C C2 0.64208(6) 1.0007(2) 0.68894(9) 0.0329(3) Uani d 1
H H2A 0.6714 1.0761 0.6836 0.039 Uiso calc 1
H H2B 0.6302 1.1090 0.7160 0.039 Uiso calc 1
C C3 0.68086(6) 0.6183(2) 0.70644(9) 0.0311(3) Uani d 1
H H3A 0.6928 0.4816 0.7438 0.037 Uiso calc 1
H H3B 0.7140 0.6601 0.7037 0.037 Uiso calc 1
C C4 0.62582(6) 0.5677(2) 0.61410(9) 0.0317(3) Uani d 1
H H4A 0.6352 0.4494 0.5868 0.038 Uiso calc 1
H H4B 0.5941 0.5090 0.6177 0.038 Uiso calc 1
C C5 0.75644(6) 0.7311(2) 0.88472(8) 0.0290(3) Uani d 1
H H5 0.7586 0.5880 0.8640 0.035 Uiso calc 1
C C6 0.80153(6) 0.7948(2) 0.97695(9) 0.0282(3) Uani d 1
C C7 0.80100(6) 1.0039(2) 1.01127(9) 0.0317(3) Uani d 1
H H7 0.7706 1.1101 0.9737 0.038 Uiso calc 1
C C8 0.84416(6) 1.0572(3) 1.09893(9) 0.0336(3) Uani d 1
H H8 0.8438 1.1991 1.1221 0.040 Uiso calc 1
C C9 0.88821(6) 0.8997(3) 1.15268(9) 0.0326(3) Uani d 1
C C10 0.89029(6) 0.6922(3) 1.12129(9) 0.0344(3) Uani d 1
H H10 0.9208 0.5867 1.1594 0.041 Uiso calc 1
C C11 0.84702(6) 0.6411(2) 1.03298(9) 0.0330(3) Uani d 1
H H11 0.8482 0.4998 1.0101 0.040 Uiso calc 1
C C12 0.55353(7) 0.7136(3) 0.46826(9) 0.0387(4) Uani d 1
H H12A 0.5211 0.6537 0.4689 0.058 Uiso calc 1
H H12B 0.5654 0.6002 0.4436 0.058 Uiso calc 1
H H12C 0.5400 0.8502 0.4317 0.058 Uiso calc 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
O1 0.0527(8) 0.0698(9) 0.0412(7) 0.0008(6) 0.0132(6) -0.0240(6)
O2 0.0326(6) 0.0792(9) 0.0295(6) 0.0096(6) 0.0123(5) 0.0014(6)
N1 0.0278(6) 0.0347(6) 0.0256(6) -0.0026(5) 0.0146(5) -0.0031(5)
N2 0.0279(6) 0.0289(6) 0.0245(6) -0.0001(4) 0.0138(5) -0.0035(4)
N3 0.0278(6) 0.0326(6) 0.0257(6) -0.0038(5) 0.0154(5) -0.0042(4)
N4 0.0280(6) 0.0624(9) 0.0287(6) -0.0011(6) 0.0159(6) -0.0066(6)
C1 0.0290(7) 0.0327(7) 0.0301(7) 0.0031(5) 0.0140(6) -0.0005(5)
C2 0.0335(7) 0.0274(7) 0.0310(7) 0.0027(5) 0.0156(6) -0.0022(6)
C3 0.0312(7) 0.0286(7) 0.0284(7) 0.0021(5) 0.0150(6) -0.0031(5)
C4 0.0334(7) 0.0291(7) 0.0302(7) -0.0029(5) 0.0177(6) -0.0061(5)
C5 0.0291(7) 0.0304(7) 0.0290(7) -0.0023(5) 0.0181(6) -0.0026(5)
C6 0.0271(7) 0.0331(7) 0.0278(7) -0.0036(5) 0.0183(6) -0.0010(5)
C7 0.0291(7) 0.0354(7) 0.0289(7) 0.0009(6) 0.0163(6) -0.0002(6)
C8 0.0325(7) 0.0365(8) 0.0330(7) -0.0035(6) 0.0202(6) -0.0065(6)
C9 0.0261(7) 0.0467(8) 0.0264(7) -0.0050(6) 0.0165(6) -0.0041(6)
C10 0.0282(7) 0.0437(8) 0.0295(7) 0.0037(6) 0.0161(6) 0.0037(6)
C11 0.0325(7) 0.0341(7) 0.0334(7) 0.0004(6) 0.0201(6) -0.0018(6)
C12 0.0333(8) 0.0498(9) 0.0265(7) -0.0039(6) 0.0142(6) -0.0052(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C12 110.78(11)
C4 N1 C1 108.16(10)
C4 N1 C12 110.55(11)
N3 N2 C2 110.17(10)
N3 N2 C3 119.30(10)
C3 N2 C2 113.80(10)
C5 N3 N2 120.39(12)
O1 N4 C9 117.78(14)
O2 N4 O1 123.67(13)
O2 N4 C9 118.55(14)
N1 C1 H1A 109.7
N1 C1 H1B 109.7
N1 C1 C2 109.86(11)
H1A C1 H1B 108.2
C2 C1 H1A 109.7
C2 C1 H1B 109.7
N2 C2 C1 111.02(11)
N2 C2 H2A 109.4
N2 C2 H2B 109.4
C1 C2 H2A 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
N2 C3 H3A 109.5
N2 C3 H3B 109.5
N2 C3 C4 110.69(11)
H3A C3 H3B 108.1
C4 C3 H3A 109.5
C4 C3 H3B 109.5
N1 C4 C3 111.29(11)
N1 C4 H4A 109.4
N1 C4 H4B 109.4
C3 C4 H4A 109.4
C3 C4 H4B 109.4
H4A C4 H4B 108.0
N3 C5 H5 119.7
N3 C5 C6 120.54(13)
C6 C5 H5 119.7
C7 C6 C5 122.44(13)
C11 C6 C5 118.67(13)
C11 C6 C7 118.89(13)
C6 C7 H7 119.6
C8 C7 C6 120.72(14)
C8 C7 H7 119.6
C7 C8 H8 120.6
C7 C8 C9 118.76(13)
C9 C8 H8 120.6
C8 C9 N4 118.83(13)
C10 C9 N4 118.94(13)
C10 C9 C8 122.22(13)
C9 C10 H10 120.7
C9 C10 C11 118.56(13)
C11 C10 H10 120.7
C6 C11 H11 119.6
C10 C11 C6 120.84(13)
C10 C11 H11 119.6
N1 C12 H12A 109.5
N1 C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N4 1.2253(19)
O2 N4 1.2219(18)
N1 C1 1.4586(17)
N1 C4 1.4546(18)
N1 C12 1.4608(17)
N2 N3 1.3682(15)
N2 C2 1.4639(17)
N2 C3 1.4580(16)
N3 C5 1.2889(18)
N4 C9 1.4657(18)
C1 H1A 0.9900
C1 H1B 0.9900
C1 C2 1.5137(19)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C3 C4 1.5122(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5 0.9500
C5 C6 1.4598(19)
C6 C7 1.401(2)
C6 C11 1.400(2)
C7 H7 0.9500
C7 C8 1.379(2)
C8 H8 0.9500
C8 C9 1.388(2)
C9 C10 1.379(2)
C10 H10 0.9500
C10 C11 1.384(2)
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2B O1 7_677 0.99 2.47 3.4052(19) 158.4
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
O1 N4 C9 C8 -7.5(2)
O1 N4 C9 C10 171.92(14)
O2 N4 C9 C8 172.30(13)
O2 N4 C9 C10 -8.2(2)
N1 C1 C2 N2 -56.86(15)
N2 N3 C5 C6 -176.24(11)
N2 C3 C4 N1 55.30(15)
N3 N2 C2 C1 -172.24(11)
N3 N2 C3 C4 177.74(11)
N3 C5 C6 C7 -0.5(2)
N3 C5 C6 C11 179.62(12)
N4 C9 C10 C11 -179.07(12)
C1 N1 C4 C3 -62.15(14)
C2 N2 N3 C5 -155.91(12)
C2 N2 C3 C4 -49.44(15)
C3 N2 N3 C5 -21.56(18)
C3 N2 C2 C1 50.72(15)
C4 N1 C1 C2 62.44(14)
C5 C6 C7 C8 179.56(12)
C5 C6 C11 C10 -179.02(12)
C6 C7 C8 C9 0.0(2)
C7 C6 C11 C10 1.1(2)
C7 C8 C9 N4 179.59(12)
C7 C8 C9 C10 0.1(2)
C8 C9 C10 C11 0.4(2)
C9 C10 C11 C6 -1.0(2)
C11 C6 C7 C8 -0.6(2)
C12 N1 C1 C2 -176.25(11)
C12 N1 C4 C3 176.40(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6894195