#------------------------------------------------------------------------------
#$Date: 2021-12-08 00:56:37 +0200 (Wed, 08 Dec 2021) $
#$Revision: 271251 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/93/7129351.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_7129351
loop_
_publ_author_name
'Zhao, Zihao'
'Li, Yuxuan'
'Chen, Xiaohong'
'Zhang, Yongming'
'Yuan, Wang Zhang'
_publ_section_title
;
 Robust and color-tunable afterglows from guanidine derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06616A
_journal_year                    2021
_chemical_formula_moiety         'C2 H4 N4'
_chemical_formula_sum            'C2 H4 N4'
_chemical_formula_weight         84.09
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-17 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9827(5)
_cell_length_b                   4.49690(10)
_cell_length_c                   13.1144(4)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      6.54
_cell_volume                     798.44(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3685
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.269
_diffrn_reflns_theta_min         6.539
_exptl_absorpt_coefficient_mu    0.876
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6553
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0329
_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)+(0.0537P)²+0.3679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                662
_reflns_number_total             709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06616a2.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7129351
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.844
_shelx_res_file
;
TITL a_a.res in C2/c
    a_a.res
    created by SHELXL-2016/6 at 17:23:07 on 23-May-2018
REM Old TITL a in C2/c
REM SHELXT solution in C2/c
REM R1 0.113,  Rweak 0.001,  Alpha 0.025,  Orientation as input
REM Formula found by SHELXT:  C N2
CELL  1.54178  14.9827   4.4969  13.1144   90.000  115.361   90.000
ZERR   8.000   0.0005   0.0001   0.0004    0.000    0.001    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C H N
UNIT 16 32 32
ACTA
TEMP 23.460
size 0.20 0.20 0.20
conf
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.053700    0.367900
FVAR       1.62690
N1    3    0.335907    0.493779    0.627171    11.00000    0.05536    0.07037 =
         0.03842    0.00858    0.02733   -0.00062
C1    1    0.368234    0.607546    0.571265    11.00000    0.03570    0.04611 =
         0.02674   -0.00009    0.01284    0.00157
N2    3    0.409184    0.750108    0.515008    11.00000    0.03903    0.04525 =
         0.02806   -0.00204    0.01606   -0.00643
C2    1    0.384794    0.670293    0.408234    11.00000    0.02959    0.03157 =
         0.02898    0.00132    0.01340    0.00414
N3    3    0.318821    0.460597    0.353758    11.00000    0.04480    0.04245 =
         0.03430   -0.00634    0.02098   -0.01010
AFIX  93
H3A   2    0.305241    0.420678    0.284531    11.00000   -1.20000
H3B   2    0.289775    0.365033    0.387787    11.00000   -1.20000
AFIX   0
N4    3    0.428274    0.813560    0.353411    11.00000    0.04531    0.04445 =
         0.03076   -0.00277    0.01995   -0.01003
AFIX  93
H4A   2    0.413638    0.770234    0.284190    11.00000   -1.20000
H4B   2    0.471114    0.949823    0.387068    11.00000   -1.20000
AFIX   0
HKLF 4




REM  a_a.res in C2/c
REM R1 =  0.0329 for     662 Fo > 4sig(Fo)  and  0.0346 for all     709 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0523      0.3737

REM Highest difference peak  0.119,  deepest hole -0.145,  1-sigma level  0.030
Q1    1   0.3384  0.3336  0.3051  11.00000  0.05    0.12
Q2    1   0.4510  0.8854  0.5429  11.00000  0.05    0.12
Q3    1   0.4150  0.6581  0.4812  11.00000  0.05    0.10
Q4    1   0.3829  0.7706  0.4598  11.00000  0.05    0.10
Q5    1   0.4302  0.6630  0.3940  11.00000  0.05    0.10
Q6    1   0.3747  0.6394  0.6473  11.00000  0.05    0.09
Q7    1   0.3787  0.8216  0.3601  11.00000  0.05    0.09
Q8    1   0.3087  0.4049  0.6825  11.00000  0.05    0.09
Q9    1   0.3718  0.7658  0.5194  11.00000  0.05    0.07
Q10   1   0.3995  0.5732  0.2334  11.00000  0.05    0.06
Q11   1   0.3742  0.5467  0.3944  11.00000  0.05    0.06
Q12   1   0.2619  0.6271  0.2699  11.00000  0.05    0.06
Q13   1   0.3329  0.2656  0.4041  11.00000  0.05    0.06
Q14   1   0.3564  0.2172  0.3757  11.00000  0.05    0.06
Q15   1   0.4475  0.6260  0.3245  11.00000  0.05    0.05
Q16   1   0.3518  0.3984  0.6013  11.00000  0.05    0.05
Q17   1   0.5068  0.8607  0.4193  11.00000  0.05    0.05
Q18   1   0.3027  0.6586  0.6823  11.00000  0.05    0.05
Q19   1   0.5014  0.6667  0.3871  11.00000  0.05    0.05
Q20   1   0.2531  0.6500  0.3420  11.00000  0.05    0.05
;
_shelx_res_checksum              65157
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33591(9) 0.4938(3) 0.62717(10) 0.0522(4) Uani 1 1 d . . . . .
C1 C 0.36823(9) 0.6075(3) 0.57127(10) 0.0364(4) Uani 1 1 d . . . . .
N2 N 0.40918(8) 0.7501(3) 0.51501(8) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.38479(8) 0.6703(3) 0.40823(10) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.31882(8) 0.4606(3) 0.35376(9) 0.0391(3) Uani 1 1 d . . . . .
H3A H 0.305241 0.420678 0.284531 0.047 Uiso 1 1 calc R U . . .
H3B H 0.289775 0.365033 0.387787 0.047 Uiso 1 1 calc R U . . .
N4 N 0.42827(8) 0.8136(3) 0.35341(9) 0.0389(4) Uani 1 1 d . . . . .
H4A H 0.413638 0.770234 0.284190 0.047 Uiso 1 1 calc R U . . .
H4B H 0.471114 0.949823 0.387068 0.047 Uiso 1 1 calc R U . . .
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
N1 0.0554(7) 0.0704(9) 0.0384(7) 0.0086(6) 0.0273(6) -0.0006(6)
C1 0.0357(7) 0.0461(8) 0.0267(6) -0.0001(5) 0.0128(5) 0.0016(5)
N2 0.0390(6) 0.0452(7) 0.0281(6) -0.0020(4) 0.0161(5) -0.0064(5)
C2 0.0296(6) 0.0316(6) 0.0290(6) 0.0013(4) 0.0134(5) 0.0041(4)
N3 0.0448(6) 0.0425(6) 0.0343(6) -0.0063(5) 0.0210(5) -0.0101(5)
N4 0.0453(6) 0.0445(7) 0.0308(6) -0.0028(4) 0.0200(5) -0.0100(5)
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'
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
_geom_angle_publ_flag
N1 C1 N2 175.32(14) . . ?
C1 N2 C2 118.33(11) . . ?
N4 C2 N3 118.53(11) . . ?
N4 C2 N2 117.42(11) . . ?
N3 C2 N2 124.04(11) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.1567(17) . ?
C1 N2 1.3113(16) . ?
N2 C2 1.3360(16) . ?
C2 N4 1.3257(15) . ?
C2 N3 1.3311(16) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 C2 N4 -178.85(11) . . . . ?
C1 N2 C2 N3 2.27(19) . . . . ?
