#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/39/7123926.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_7123926
loop_
_publ_author_name
'An, Taeyang'
'Kang, Byeongwoo'
'Kang, Sunyoung'
'Pac, Jinyoung'
'Youk, Jihea'
'Lin, Dian'
'Lee, Yan'
_publ_section_title
;
 Guanidine cyclic diimides and their polymers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04522H
_journal_year                    2019
_chemical_formula_moiety         C13H17N3O4
_chemical_formula_sum            'C13 H17 N3 O4'
_chemical_formula_weight         279.29
_chemical_name_systematic
1,1'-((butylimino)methylene)bis(pyrrolidine-2,5-dione)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-24 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1674(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.69440(10)
_cell_length_b                   8.73060(10)
_cell_length_c                   16.4787(2)
_cell_measurement_reflns_used    4115
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.37
_cell_volume                     1391.04(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.1023
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         2.365
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0525
_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)+(0.0820P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2598
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc04522h2.cif
_cod_data_source_block           aty_3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7123926
_shelx_shelxl_version_number     2014/7
_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. 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.53839(11) 0.48881(11) 0.11976(6) 0.0385(3) Uani 1 1 d . .
O2 O 0.11984(11) 0.32212(13) 0.00789(7) 0.0450(3) Uani 1 1 d . .
O3 O 0.22141(11) -0.03778(12) 0.02602(6) 0.0398(3) Uani 1 1 d . .
O4 O 0.22765(12) 0.30426(15) 0.23459(6) 0.0487(3) Uani 1 1 d . .
N1 N 0.33641(11) 0.36939(12) 0.06939(6) 0.0244(3) Uani 1 1 d . .
N2 N 0.25499(11) 0.14150(13) 0.12776(6) 0.0247(3) Uani 1 1 d . .
N3 N 0.48593(11) 0.16293(13) 0.08559(6) 0.0259(3) Uani 1 1 d . .
C1 C 0.42340(15) 0.49661(14) 0.08676(7) 0.0265(3) Uani 1 1 d . .
C2 C 0.34510(15) 0.63749(16) 0.05920(8) 0.0322(3) Uani 1 1 d . .
H2A H 0.4008 0.7010 0.0240 0.039 Uiso 1 1 calc R U
H2B H 0.3216 0.6996 0.1065 0.039 Uiso 1 1 calc R U
C3 C 0.21519(16) 0.58103(17) 0.01214(9) 0.0385(4) Uani 1 1 d . .
H3A H 0.1324 0.6318 0.0316 0.046 Uiso 1 1 calc R U
H3B H 0.2190 0.6022 -0.0467 0.046 Uiso 1 1 calc R U
C4 C 0.21054(14) 0.41135(17) 0.02748(8) 0.0307(3) Uani 1 1 d . .
C5 C 0.18260(15) 0.02287(16) 0.08571(8) 0.0294(3) Uani 1 1 d . .
C6 C 0.05523(17) -0.00910(19) 0.12912(10) 0.0422(4) Uani 1 1 d . .
H6A H 0.0594 -0.1130 0.1533 0.051 Uiso 1 1 calc R U
H6B H -0.0284 -0.0017 0.0911 0.051 Uiso 1 1 calc R U
C7 C 0.05260(18) 0.1110(3) 0.19467(9) 0.0529(5) Uani 1 1 d . .
H7A H -0.0282 0.1794 0.1843 0.064 Uiso 1 1 calc R U
H7B H 0.0473 0.0625 0.2486 0.064 Uiso 1 1 calc R U
C8 C 0.18511(15) 0.19984(19) 0.19166(8) 0.0356(4) Uani 1 1 d . .
C9 C 0.36903(13) 0.21706(14) 0.09454(7) 0.0221(3) Uani 1 1 d . .
C10 C 0.52597(15) 0.01261(15) 0.11787(8) 0.0306(3) Uani 1 1 d . .
H10A H 0.5352 -0.0604 0.0726 0.037 Uiso 1 1 calc R U
H10B H 0.4542 -0.0266 0.1522 0.037 Uiso 1 1 calc R U
C11 C 0.66320(16) 0.0271(2) 0.16816(10) 0.0419(4) Uani 1 1 d . .
H11A H 0.6952 -0.0765 0.1851 0.050 Uiso 1 1 calc R U
H11B H 0.7326 0.0707 0.1335 0.050 Uiso 1 1 calc R U
C12 C 0.65707(19) 0.1262(2) 0.24330(10) 0.0498(5) Uani 1 1 d . .
H12A H 0.7511 0.1337 0.2708 0.060 Uiso 1 1 calc R U
H12B H 0.6279 0.2307 0.2263 0.060 Uiso 1 1 calc R U
C13 C 0.5599(2) 0.0671(3) 0.30310(10) 0.0704(6) Uani 1 1 d . .
H13A H 0.5611 0.1364 0.3500 0.106 Uiso 1 1 calc R U
H13B H 0.4660 0.0619 0.2769 0.106 Uiso 1 1 calc R U
H13C H 0.5893 -0.0353 0.3215 0.106 Uiso 1 1 calc R U
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
C4 N1 C1 112.27(11)
C4 N1 C9 123.60(11)
C1 N1 C9 124.06(10)
C8 N2 C5 112.97(12)
C8 N2 C9 123.65(12)
C5 N2 C9 121.57(10)
C9 N3 C10 121.21(12)
O1 C1 N1 124.48(12)
O1 C1 C2 127.89(12)
N1 C1 C2 107.61(11)
C1 C2 C3 105.81(11)
C4 C3 C2 105.59(11)
O2 C4 N1 123.72(13)
O2 C4 C3 128.60(12)
N1 C4 C3 107.67(11)
O3 C5 N2 123.62(13)
O3 C5 C6 128.84(13)
N2 C5 C6 107.54(12)
C5 C6 C7 105.67(12)
C8 C7 C6 106.03(13)
O4 C8 N2 123.77(14)
O4 C8 C7 128.73(14)
N2 C8 C7 107.50(13)
N3 C9 N1 120.33(12)
N3 C9 N2 127.25(12)
N1 C9 N2 112.42(10)
N3 C10 C11 108.84(12)
C12 C11 C10 114.09(13)
C13 C12 C11 113.80(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2062(16)
O2 C4 1.2012(17)
O3 C5 1.2014(17)
O4 C8 1.2080(18)
N1 C4 1.4063(16)
N1 C1 1.4112(17)
N1 C9 1.4218(16)
N2 C8 1.3895(17)
N2 C5 1.4052(17)
N2 C9 1.4300(16)
N3 C9 1.2465(16)
N3 C10 1.4581(16)
C1 C2 1.4983(19)
C2 C3 1.513(2)
C3 C4 1.504(2)
C5 C6 1.498(2)
C6 C7 1.507(2)
C7 C8 1.504(2)
C10 C11 1.5207(19)
C11 C12 1.515(2)
C12 C13 1.503(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350866
