#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:14:38 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295210 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/24/1572422.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_1572422
loop_
_publ_author_name
'Yang, Can'
'Kang, Yuwei'
'Wang, Xuefei'
'Gou, Jie'
'Xiong, Yi'
'Zhu, Zece'
'Chen, Ling'
'Wu, Qi'
_publ_section_title
;
 N₂H₄Zn(HC₃N₃O₃):
 exceptionally strong second harmonic generation and ultra-long
 phosphorescence.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15725
_journal_page_last               15730
_journal_paper_doi               10.1039/d4sc04476b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C3 H5 N5 O3 Zn'
_chemical_formula_sum            'C3 H5 N5 O3 Zn'
_chemical_formula_weight         224.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-06 deposited with the CCDC.	2024-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.333(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4696(5)
_cell_length_b                   9.4104(4)
_cell_length_c                   7.9944(4)
_cell_measurement_reflns_used    4516
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      4.33
_cell_volume                     654.14(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.959
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4648
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         4.331
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.726
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.077(17)
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1404
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0174
_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/[σ²(Fo²)+0.3497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0469
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                1394
_reflns_number_total             1404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04476b2.cif
_cod_data_source_block           20230901001_0m
_cod_depositor_comments          'Adding full bibliography for 1572422.cif.'
_cod_database_code               1572422
_shelx_shelxl_version_number     2018/3
_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_max   0.707
_shelx_estimated_absorpt_t_min   0.685
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.923(17)
 0.077(17)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
Zn1 Zn 0.23278(5) 0.58885(3) 0.48015(5) 0.01653(17) Uani 1 1 d . . . . .
O3 O 0.4191(3) 0.8121(3) 0.7513(4) 0.0263(6) Uani 1 1 d . . . . .
O1 O 0.4993(4) 0.3705(3) 0.5875(4) 0.0311(7) Uani 1 1 d . . . . .
N4 N 0.1787(4) 0.4054(3) 0.3285(4) 0.0173(6) Uani 1 1 d . . . . .
H4A H 0.265596 0.357778 0.351619 0.021 Uiso 1 1 calc R U . . .
H4B H 0.120569 0.352240 0.368303 0.021 Uiso 1 1 calc R U . . .
N2 N 0.7014(3) 0.5163(3) 0.7306(5) 0.0264(7) Uani 1 1 d . . . . .
H2 H 0.763661 0.450155 0.729541 0.032 Uiso 1 1 calc R U . . .
N3 N 0.6632(3) 0.7452(3) 0.8149(4) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.4498(3) 0.5939(3) 0.6537(4) 0.0182(6) Uani 1 1 d . . . . .
O2 O 0.9026(3) 0.6615(3) 0.8699(4) 0.0324(7) Uani 1 1 d . . . . .
N5 N 0.0992(3) 0.4186(3) 0.1316(4) 0.0174(6) Uani 1 1 d . . . . .
H5A H 0.048238 0.500580 0.107761 0.021 Uiso 1 1 calc R U . . .
H5B H 0.029711 0.349340 0.092652 0.021 Uiso 1 1 calc R U . . .
C1 C 0.5466(4) 0.4875(4) 0.6542(5) 0.0192(7) Uani 1 1 d . . . . .
C3 C 0.5084(4) 0.7191(3) 0.7392(5) 0.0153(7) Uani 1 1 d . . . . .
C2 C 0.7631(4) 0.6439(4) 0.8084(5) 0.0203(7) Uani 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'
Zn Zn 0.2839 1.4301 '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
N4 Zn1 N5 104.44(12) . 2_565 ?
N3 Zn1 N4 109.25(13) 4_464 . ?
N3 Zn1 N5 107.30(11) 4_464 2_565 ?
N1 Zn1 N4 112.48(11) . . ?
N1 Zn1 N3 115.38(11) . 4_464 ?
N1 Zn1 N5 107.27(13) . 2_565 ?
Zn1 N4 H4A 107.8 . . ?
Zn1 N4 H4B 107.8 . . ?
H4A N4 H4B 107.2 . . ?
N5 N4 Zn1 117.86(18) . . ?
N5 N4 H4A 107.8 . . ?
N5 N4 H4B 107.8 . . ?
C1 N2 H2 117.9 . . ?
C2 N2 H2 117.9 . . ?
C2 N2 C1 124.2(3) . . ?
C3 N3 Zn1 116.8(2) . 4_565 ?
C2 N3 Zn1 121.7(2) . 4_565 ?
C2 N3 C3 119.8(3) . . ?
C1 N1 Zn1 119.9(2) . . ?
C1 N1 C3 119.7(3) . . ?
C3 N1 Zn1 118.5(2) . . ?
Zn1 N5 H5A 108.0 2_564 . ?
Zn1 N5 H5B 108.0 2_564 . ?
N4 N5 Zn1 117.1(2) . 2_564 ?
N4 N5 H5A 108.0 . . ?
N4 N5 H5B 108.0 . . ?
H5A N5 H5B 107.3 . . ?
O1 C1 N2 120.8(3) . . ?
O1 C1 N1 122.1(3) . . ?
N1 C1 N2 117.2(3) . . ?
O3 C3 N3 118.7(3) . . ?
O3 C3 N1 119.4(3) . . ?
N1 C3 N3 121.9(3) . . ?
N3 C2 N2 117.0(3) . . ?
O2 C2 N2 119.9(3) . . ?
O2 C2 N3 123.1(3) . . ?
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
Zn1 N4 2.055(3) . ?
Zn1 N3 1.982(3) 4_464 ?
Zn1 N1 1.973(3) . ?
Zn1 N5 2.070(3) 2_565 ?
O3 C3 1.247(5) . ?
O1 C1 1.228(4) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 N5 1.457(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.374(4) . ?
N2 C2 1.372(5) . ?
N3 C3 1.368(4) . ?
N3 C2 1.358(4) . ?
N1 C1 1.357(4) . ?
N1 C3 1.365(4) . ?
O2 C2 1.225(4) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
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
Zn1 N4 N5 Zn1 96.8(2) . . . 2_564 ?
Zn1 N3 C3 O3 12.3(4) 4_565 . . . ?
Zn1 N3 C3 N1 -166.7(3) 4_565 . . . ?
Zn1 N3 C2 N2 162.5(3) 4_565 . . . ?
Zn1 N3 C2 O2 -16.7(5) 4_565 . . . ?
Zn1 N1 C1 O1 -19.9(5) . . . . ?
Zn1 N1 C1 N2 159.2(3) . . . . ?
Zn1 N1 C3 O3 21.7(5) . . . . ?
Zn1 N1 C3 N3 -159.4(3) . . . . ?
C1 N2 C2 N3 2.4(6) . . . . ?
C1 N2 C2 O2 -178.4(4) . . . . ?
C1 N1 C3 O3 -174.1(4) . . . . ?
C1 N1 C3 N3 4.8(5) . . . . ?
C3 N3 C2 N2 -2.5(5) . . . . ?
C3 N3 C2 O2 178.3(4) . . . . ?
C3 N1 C1 O1 176.1(4) . . . . ?
C3 N1 C1 N2 -4.8(5) . . . . ?
C2 N2 C1 O1 -179.7(4) . . . . ?
C2 N2 C1 N1 1.3(6) . . . . ?
C2 N3 C3 O3 178.0(3) . . . . ?
C2 N3 C3 N1 -1.0(5) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.923(17)
2 0.077(17)
