# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20200811b
_database_code_depnum_ccdc_archive 'CCDC 2046373'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'piperazine-1,4-diium di-sorbate'
_chemical_name_systematic        'piperazine-1,4-diium di-2e,4e-hexadienoicate'
_chemical_formula_moiety         '2(C6 H7 O2), C4 H12 N2'
_chemical_formula_sum            'C16 H26 N2 O4'
_chemical_formula_weight         310.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6474(9)
_cell_length_b                   7.3558(11)
_cell_length_c                   10.9693(15)
_cell_angle_alpha                108.023(13)
_cell_angle_beta                 94.575(12)
_cell_angle_gamma                99.275(13)
_cell_volume                     423.55(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5170
_cell_measurement_theta_min      1.9250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.971
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   2.00    2.00    --  -25.00  45.00   0.00   90
  2  ω   -115.00  65.00   2.00    2.00    --  -25.00  45.00  90.00   90
  3  ω   -115.00  65.00   2.00    2.00    --  -25.00  45.00 180.00   90
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1129797000
_diffrn_orient_matrix_UB_12      0.0177895000
_diffrn_orient_matrix_UB_13      -0.0217535000
_diffrn_orient_matrix_UB_21      -0.0175894000
_diffrn_orient_matrix_UB_22      -0.0872751000
_diffrn_orient_matrix_UB_23      -0.0534627000
_diffrn_orient_matrix_UB_31      -0.0586247000
_diffrn_orient_matrix_UB_32      -0.0525385000
_diffrn_orient_matrix_UB_33      0.0371786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1413
_reflns_number_total             1731
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.100(12)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.043
_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)+(0.0494P)²+0.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1A-N1
 0.92 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C2(H2), C5(H5)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.24039(18) 0.66193(15) 0.68678(10) 0.0230(3) Uani 1 1 d . . . . .
O2 O 0.54410(19) 0.80203(16) 0.60828(11) 0.0255(3) Uani 1 1 d . . . . .
N1 N 0.0056(2) 0.86009(18) 0.56623(12) 0.0174(3) Uani 1 1 d D . . . .
C1 C 0.4611(3) 0.6956(2) 0.67227(14) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.5639(3) 0.4874(2) 0.80160(14) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.401355 0.465947 0.812580 0.022 Uiso 1 1 calc R U . . .
C7 C 0.0293(3) 0.8067(2) 0.42608(14) 0.0191(3) Uani 1 1 d . . . . .
H7A H -0.039174 0.669491 0.383130 0.023 Uiso 1 1 calc R U . . .
H7B H 0.199128 0.828830 0.415220 0.023 Uiso 1 1 calc R U . . .
C8 C 0.1021(3) 1.0713(2) 0.63430(14) 0.0195(4) Uani 1 1 d . . . . .
H8A H 0.273960 1.100776 0.628990 0.023 Uiso 1 1 calc R U . . .
H8B H 0.081560 1.103148 0.724981 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7231(3) 0.3908(2) 0.85965(14) 0.0197(4) Uani 1 1 d . . . . .
H4 H 0.888424 0.421658 0.856806 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6331(3) 0.6045(2) 0.73369(14) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.795992 0.630545 0.724201 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6460(3) 0.2605(2) 0.91684(15) 0.0232(4) Uani 1 1 d . . . . .
H5 H 0.480760 0.233856 0.921178 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8018(3) 0.1537(2) 0.97446(16) 0.0298(4) Uani 1 1 d . . . . .
H6A H 0.752027 0.016030 0.930316 0.045 Uiso 1 1 calc R U . . .
H6B H 0.785762 0.181539 1.064542 0.045 Uiso 1 1 calc R U . . .
H6C H 0.967847 0.194782 0.965539 0.045 Uiso 1 1 calc R U . . .
H1A H 0.096(3) 0.790(2) 0.6086(17) 0.036(5) Uiso 1 1 d D . . . .
H1B H -0.165(4) 0.827(3) 0.5803(18) 0.041(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C1 1.2636(18) . ?
O2 C1 1.2647(18) . ?
N1 C7 1.4871(19) . ?
N1 C8 1.4874(19) . ?
N1 H1A 0.968(14) . ?
N1 H1B 0.99(2) . ?
C1 C2 1.494(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.453(2) . ?
C3 C2 1.336(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(2) 2_576 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.336(2) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.495(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
C7 N1 C8 111.08(11) . . ?
C7 N1 H1A 111.7(11) . . ?
C7 N1 H1B 111.6(11) . . ?
C8 N1 H1A 106.7(11) . . ?
C8 N1 H1B 109.5(11) . . ?
H1A N1 H1B 106.0(15) . . ?
O1 C1 O2 123.50(13) . . ?
O1 C1 C2 118.27(13) . . ?
O2 C1 C2 118.23(13) . . ?
C4 C3 H3 117.5 . . ?
C2 C3 H3 117.5 . . ?
C2 C3 C4 125.05(14) . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.76(11) . 2_576 ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 2_576 . ?
C8 C7 H7B 109.7 2_576 . ?
N1 C8 C7 110.39(12) . 2_576 ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 2_576 . ?
C7 C8 H8B 109.6 2_576 . ?
H8A C8 H8B 108.1 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.86(15) . . ?
C5 C4 H4 118.1 . . ?
C1 C2 H2 118.4 . . ?
C3 C2 C1 123.11(14) . . ?
C3 C2 H2 118.4 . . ?
C4 C5 H5 117.1 . . ?
C4 C5 C6 125.72(15) . . ?
C6 C5 H5 117.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
O1 C1 C2 C3 0.9(2) . . . . ?
O2 C1 C2 C3 -178.95(14) . . . . ?
C3 C4 C5 C6 178.20(14) . . . . ?
C7 N1 C8 C7 58.00(16) . . . 2_576 ?
C8 N1 C7 C8 -57.63(17) . . . 2_576 ?
C4 C3 C2 C1 178.02(13) . . . . ?
C2 C3 C4 C5 -173.58(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.669
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20201020a
_database_code_depnum_ccdc_archive 'CCDC 2046374'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Nicotinamide Sorbic acid'
_chemical_name_systematic        'Nicotinamide  2e,4e-hexadienoicacid'
_chemical_formula_moiety         'C6 H8 O2, C6 H6 N2 O'
_chemical_formula_sum            'C12 H14 N2 O3'
_chemical_formula_weight         234.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H14N2O3
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0241(2)
_cell_length_b                   7.3014(3)
_cell_length_c                   20.0901(10)
_cell_angle_alpha                97.098(4)
_cell_angle_beta                 92.087(4)
_cell_angle_gamma                90.663(3)
_cell_volume                     585.29(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5317
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8480
_cell_measurement_theta_min      2.0490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.844
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   0.50    2.00    --  -25.00  45.00   0.00  360
  2  ω   -115.00  65.00   0.50    2.00    --  -25.00  45.00  90.00  360
  3  ω   -115.00  65.00   0.50    2.00    --  -25.00  45.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0425125000
_diffrn_orient_matrix_UB_12      0.0953194000
_diffrn_orient_matrix_UB_13      0.0032476000
_diffrn_orient_matrix_UB_21      -0.0272596000
_diffrn_orient_matrix_UB_22      -0.0002805000
_diffrn_orient_matrix_UB_23      -0.0350933000
_diffrn_orient_matrix_UB_31      -0.1690179000
_diffrn_orient_matrix_UB_32      0.0223647000
_diffrn_orient_matrix_UB_33      0.0050597000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3369
_reflns_number_total             3943
_reflns_odcompleteness_completeness 90.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.77
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.060(11)
_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   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.093
_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)+(0.0526P)²+0.2413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00J), C00B(H00B), C00C(H00C), C00E(H00K),
 C00F(H00F), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00D,H00E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.5646(2) 0.61667(12) 0.73906(4) 0.0258(2) Uani 1 1 d . . . . .
O002 O 0.5743(3) 0.39225(12) 0.80593(5) 0.0278(2) Uani 1 1 d . . . . .
O003 O -0.3223(3) 0.27344(13) 0.50294(4) 0.0296(2) Uani 1 1 d . . . . .
N004 N -0.3735(3) 0.50115(14) 0.58924(5) 0.0230(2) Uani 1 1 d . . . . .
N005 N 0.2219(3) 0.19315(14) 0.70983(5) 0.0217(2) Uani 1 1 d . . . . .
C006 C 0.0592(3) 0.29320(15) 0.66817(6) 0.0201(2) Uani 1 1 d . . . . .
H006 H 0.059094 0.423577 0.679052 0.024 Uiso 1 1 calc R U . . .
C007 C -0.1102(3) 0.21568(15) 0.60958(5) 0.0189(2) Uani 1 1 d . . . . .
C008 C -0.2790(3) 0.33260(15) 0.56294(6) 0.0207(2) Uani 1 1 d . . . . .
C009 C -0.1046(3) 0.02493(16) 0.59310(6) 0.0223(2) Uani 1 1 d . . . . .
H009 H -0.210959 -0.032514 0.552758 0.027 Uiso 1 1 calc R U . . .
C00A C 0.2191(3) 0.00856(16) 0.69429(6) 0.0230(2) Uani 1 1 d . . . . .
H00J H 0.330951 -0.064112 0.723924 0.028 Uiso 1 1 calc R U . . .
C00B C 0.8963(3) 0.85074(17) 0.84758(6) 0.0230(2) Uani 1 1 d . . . . .
H00B H 0.816822 0.906420 0.809887 0.028 Uiso 1 1 calc R U . . .
C00C C 1.0747(3) 0.96768(17) 0.90087(6) 0.0246(2) Uani 1 1 d . . . . .
H00C H 1.164778 0.912730 0.937876 0.030 Uiso 1 1 calc R U . . .
C00D C 0.6459(3) 0.55979(16) 0.79194(6) 0.0220(2) Uani 1 1 d . . . . .
C00E C 0.0595(3) -0.07941(16) 0.63676(6) 0.0237(2) Uani 1 1 d . . . . .
H00K H 0.062230 -0.210109 0.627281 0.028 Uiso 1 1 calc R U . . .
C00F C 1.1186(3) 1.14875(17) 0.90053(6) 0.0257(3) Uani 1 1 d . . . . .
H00F H 1.029106 1.201459 0.862970 0.031 Uiso 1 1 calc R U . . .
C00G C 0.8351(3) 0.67071(17) 0.84735(6) 0.0252(3) Uani 1 1 d . . . . .
H00G H 0.916280 0.611858 0.884160 0.030 Uiso 1 1 calc R U . . .
C00H C 1.2973(4) 1.27522(19) 0.95454(7) 0.0306(3) Uani 1 1 d . . . . .
H00A H 1.484197 1.335656 0.935559 0.046 Uiso 1 1 calc R U . . .
H00D H 1.381088 1.204079 0.989720 0.046 Uiso 1 1 calc R U . . .
H00E H 1.144055 1.368970 0.973801 0.046 Uiso 1 1 calc R U . . .
H00H H -0.475(5) 0.575(3) 0.5616(9) 0.035(5) Uiso 1 1 d . . . . .
H00I H -0.372(4) 0.530(3) 0.6342(9) 0.034(4) Uiso 1 1 d . . . . .
H002 H 0.445(6) 0.319(4) 0.7671(13) 0.073(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O001 C00D 1.2228(15) . ?
O002 C00D 1.3195(15) . ?
O002 H002 1.01(3) . ?
O003 C008 1.2347(14) . ?
N004 C008 1.3427(14) . ?
N004 H00H 0.910(19) . ?
N004 H00I 0.902(19) . ?
N005 C006 1.3361(15) . ?
N005 C00A 1.3452(15) . ?
C006 H006 0.9500 . ?
C006 C007 1.3922(15) . ?
C007 C008 1.4943(16) . ?
C007 C009 1.3918(15) . ?
C009 H009 0.9500 . ?
C009 C00E 1.3857(17) . ?
C00A H00J 0.9500 . ?
C00A C00E 1.3835(17) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.4472(17) . ?
C00B C00G 1.3339(17) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.3327(17) . ?
C00D C00G 1.4751(17) . ?
C00E H00K 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00H 1.4924(18) . ?
C00G H00G 0.9500 . ?
C00H H00A 0.9800 . ?
C00H H00D 0.9800 . ?
C00H H00E 0.9800 . ?

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
C00D O002 H002 110.8(14) . . ?
C008 N004 H00H 118.5(11) . . ?
C008 N004 H00I 119.7(12) . . ?
H00H N004 H00I 120.8(16) . . ?
C006 N005 C00A 118.05(10) . . ?
N005 C006 H006 118.4 . . ?
N005 C006 C007 123.19(10) . . ?
C007 C006 H006 118.4 . . ?
C006 C007 C008 121.63(10) . . ?
C009 C007 C006 118.31(11) . . ?
C009 C007 C008 119.96(10) . . ?
O003 C008 N004 123.02(11) . . ?
O003 C008 C007 119.87(10) . . ?
N004 C008 C007 117.10(10) . . ?
C007 C009 H009 120.7 . . ?
C00E C009 C007 118.60(11) . . ?
C00E C009 H009 120.7 . . ?
N005 C00A H00J 118.8 . . ?
N005 C00A C00E 122.45(11) . . ?
C00E C00A H00J 118.8 . . ?
C00C C00B H00B 117.5 . . ?
C00G C00B H00B 117.5 . . ?
C00G C00B C00C 124.98(11) . . ?
C00B C00C H00C 118.4 . . ?
C00F C00C C00B 123.15(12) . . ?
C00F C00C H00C 118.4 . . ?
O001 C00D O002 123.83(11) . . ?
O001 C00D C00G 123.83(11) . . ?
O002 C00D C00G 112.34(10) . . ?
C009 C00E H00K 120.3 . . ?
C00A C00E C009 119.37(11) . . ?
C00A C00E H00K 120.3 . . ?
C00C C00F H00F 117.4 . . ?
C00C C00F C00H 125.12(12) . . ?
C00H C00F H00F 117.4 . . ?
C00B C00G C00D 122.32(11) . . ?
C00B C00G H00G 118.8 . . ?
C00D C00G H00G 118.8 . . ?
C00F C00H H00A 109.5 . . ?
C00F C00H H00D 109.5 . . ?
C00F C00H H00E 109.5 . . ?
H00A C00H H00D 109.5 . . ?
H00A C00H H00E 109.5 . . ?
H00D C00H H00E 109.5 . . ?

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
O001 C00D C00G C00B 8.8(2) . . . . ?
O002 C00D C00G C00B -171.16(12) . . . . ?
N005 C006 C007 C008 -177.74(11) . . . . ?
N005 C006 C007 C009 -1.16(18) . . . . ?
N005 C00A C00E C009 0.01(19) . . . . ?
C006 N005 C00A C00E 1.01(18) . . . . ?
C006 C007 C008 O003 154.35(12) . . . . ?
C006 C007 C008 N004 -24.81(17) . . . . ?
C006 C007 C009 C00E 2.13(18) . . . . ?
C007 C009 C00E C00A -1.60(19) . . . . ?
C008 C007 C009 C00E 178.78(11) . . . . ?
C009 C007 C008 O003 -22.18(18) . . . . ?
C009 C007 C008 N004 158.66(12) . . . . ?
C00A N005 C006 C007 -0.43(18) . . . . ?
C00B C00C C00F C00H 179.35(12) . . . . ?
C00C C00B C00G C00D 178.79(12) . . . . ?
C00G C00B C00C C00F -177.06(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.743
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20201020b
_database_code_depnum_ccdc_archive 'CCDC 2046376'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            '2,6-Diaminopyridinium  Sorbate monohydrate'
_chemical_name_systematic        
'2,6-Diaminopyridinium 2e,4e-hexadienoicate monohydrate'
_chemical_formula_moiety         'C6 H7 O2, C5 H8 N3, H2 O'
_chemical_formula_sum            'C11 H17 N3 O3'
_chemical_formula_weight         239.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   8.8238(3)
_cell_length_b                   11.9190(3)
_cell_length_c                   11.9562(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.671(3)
_cell_angle_gamma                90
_cell_volume                     1251.29(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12195
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.9390
_cell_measurement_theta_min      2.4020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15473
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.691
_diffrn_reflns_theta_min         2.419
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   0.50    1.00    --  -25.00  45.00   0.00  360
  2  ω   -115.00  65.00   0.50    1.00    --  -25.00  45.00  90.00  360
  3  ω   -115.00  65.00   0.50    1.00    --  -25.00  45.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0618791000
_diffrn_orient_matrix_UB_12      0.0143864000
_diffrn_orient_matrix_UB_13      0.0398231000
_diffrn_orient_matrix_UB_21      0.0271569000
_diffrn_orient_matrix_UB_22      0.0380015000
_diffrn_orient_matrix_UB_23      -0.0390677000
_diffrn_orient_matrix_UB_31      -0.0442993000
_diffrn_orient_matrix_UB_32      0.0434636000
_diffrn_orient_matrix_UB_33      0.0209979000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2906
_reflns_number_total             3213
_reflns_odcompleteness_completeness 92.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.89
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.025(5)
_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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.053
_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)+(0.0530P)²+0.2984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.67745(8) 0.42856(6) 0.83880(6) 0.02456(18) Uani 1 1 d . . . . .
O2 O 0.66819(8) 0.30815(6) 0.69579(6) 0.02652(19) Uani 1 1 d . . . . .
C1 C 0.73576(10) 0.38190(8) 0.75783(8) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.89257(11) 0.41652(8) 0.73729(9) 0.0231(2) Uani 1 1 d . . . . .
H2 H 0.949262 0.460184 0.793250 0.028 Uiso 1 1 calc R U . . .
C3 C 0.95851(10) 0.39002(8) 0.64507(8) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.900641 0.347602 0.588701 0.025 Uiso 1 1 calc R U . . .
C4 C 1.11223(11) 0.42137(8) 0.62479(9) 0.0236(2) Uani 1 1 d . . . . .
H4 H 1.171683 0.462550 0.681298 0.028 Uiso 1 1 calc R U . . .
C5 C 1.17426(11) 0.39546(9) 0.53120(9) 0.0262(2) Uani 1 1 d . . . . .
H5 H 1.113381 0.354786 0.475087 0.031 Uiso 1 1 calc R U . . .
C6 C 1.33257(12) 0.42547(10) 0.50751(10) 0.0319(3) Uani 1 1 d . . . . .
H6A H 1.328287 0.480400 0.446290 0.048 Uiso 1 1 calc R U . . .
H6B H 1.385552 0.357890 0.485561 0.048 Uiso 1 1 calc R U . . .
H6C H 1.387586 0.457765 0.575154 0.048 Uiso 1 1 calc R U . . .
N1 N 0.38971(9) 0.21401(7) 0.71685(7) 0.01897(18) Uani 1 1 d . . . . .
N2 N 0.40411(10) 0.30977(7) 0.88548(7) 0.0241(2) Uani 1 1 d . . . . .
N3 N 0.39558(11) 0.12805(8) 0.54371(8) 0.0278(2) Uani 1 1 d . . . . .
C7 C 0.32377(10) 0.24330(8) 0.81120(8) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.17845(11) 0.20181(8) 0.82539(9) 0.0237(2) Uani 1 1 d . . . . .
H8 H 0.131180 0.218148 0.891537 0.028 Uiso 1 1 calc R U . . .
C9 C 0.10540(11) 0.13662(9) 0.74111(9) 0.0259(2) Uani 1 1 d . . . . .
H9 H 0.006233 0.108988 0.749721 0.031 Uiso 1 1 calc R U . . .
C10 C 0.17217(11) 0.11027(8) 0.64445(9) 0.0252(2) Uani 1 1 d . . . . .
H10 H 0.119125 0.066405 0.586885 0.030 Uiso 1 1 calc R U . . .
C11 C 0.31870(11) 0.14934(8) 0.63323(8) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.73264(8) 0.13117(7) 0.57026(6) 0.02394(18) Uani 1 1 d . . . . .
H1 H 0.4840(18) 0.2439(12) 0.7104(12) 0.038(4) Uiso 1 1 d . . . . .
H2A H 0.3583(16) 0.3331(12) 0.9455(12) 0.033(3) Uiso 1 1 d . . . . .
H2B H 0.4897(17) 0.3459(12) 0.8689(12) 0.032(3) Uiso 1 1 d . . . . .
H3C H 0.7356(17) 0.1866(13) 0.6199(13) 0.040(4) Uiso 1 1 d . . . . .
H3A H 0.4975(19) 0.1365(12) 0.5487(13) 0.041(4) Uiso 1 1 d . . . . .
H3B H 0.3441(18) 0.0938(12) 0.4856(13) 0.040(4) Uiso 1 1 d . . . . .
H3D H 0.7605(18) 0.0717(14) 0.6075(14) 0.046(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C1 1.2687(12) . ?
O2 C1 1.2613(12) . ?
C1 C2 1.4874(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3345(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.4503(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.3297(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.4959(14) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N1 C7 1.3648(12) . ?
N1 C11 1.3648(12) . ?
N1 H1 0.915(16) . ?
N2 C7 1.3396(13) . ?
N2 H2A 0.902(15) . ?
N2 H2B 0.908(15) . ?
N3 C11 1.3467(13) . ?
N3 H3A 0.901(16) . ?
N3 H3B 0.890(16) . ?
C7 C8 1.4001(13) . ?
C8 H8 0.9500 . ?
C8 C9 1.3808(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3842(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3931(14) . ?
O3 H3C 0.886(17) . ?
O3 H3D 0.860(17) . ?

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
O1 C1 C2 117.28(8) . . ?
O2 C1 O1 123.40(8) . . ?
O2 C1 C2 119.32(8) . . ?
C1 C2 H2 118.0 . . ?
C3 C2 C1 124.01(9) . . ?
C3 C2 H2 118.0 . . ?
C2 C3 H3 117.7 . . ?
C2 C3 C4 124.64(9) . . ?
C4 C3 H3 117.7 . . ?
C3 C4 H4 118.3 . . ?
C5 C4 C3 123.40(10) . . ?
C5 C4 H4 118.3 . . ?
C4 C5 H5 117.5 . . ?
C4 C5 C6 125.00(10) . . ?
C6 C5 H5 117.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 N1 C11 123.20(8) . . ?
C7 N1 H1 115.9(9) . . ?
C11 N1 H1 120.8(9) . . ?
C7 N2 H2A 117.4(9) . . ?
C7 N2 H2B 122.2(9) . . ?
H2A N2 H2B 118.4(13) . . ?
C11 N3 H3A 120.3(10) . . ?
C11 N3 H3B 116.6(10) . . ?
H3A N3 H3B 122.1(13) . . ?
N1 C7 C8 118.70(9) . . ?
N2 C7 N1 117.28(8) . . ?
N2 C7 C8 124.02(9) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.52(9) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.04(9) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.70(9) . . ?
C11 C10 H10 120.6 . . ?
N1 C11 C10 118.79(9) . . ?
N3 C11 N1 117.24(9) . . ?
N3 C11 C10 123.96(9) . . ?
H3C O3 H3D 106.2(14) . . ?

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
O1 C1 C2 C3 -168.00(9) . . . . ?
O2 C1 C2 C3 12.56(15) . . . . ?
C1 C2 C3 C4 -178.79(9) . . . . ?
C2 C3 C4 C5 -178.81(10) . . . . ?
C3 C4 C5 C6 -179.51(9) . . . . ?
N1 C7 C8 C9 -2.57(14) . . . . ?
N2 C7 C8 C9 178.13(9) . . . . ?
C7 N1 C11 N3 178.96(9) . . . . ?
C7 N1 C11 C10 -0.50(14) . . . . ?
C7 C8 C9 C10 0.81(15) . . . . ?
C8 C9 C10 C11 1.15(15) . . . . ?
C9 C10 C11 N1 -1.32(14) . . . . ?
C9 C10 C11 N3 179.26(9) . . . . ?
C11 N1 C7 N2 -178.18(9) . . . . ?
C11 N1 C7 C8 2.47(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.744
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ??'
