# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ks105entry3
_database_code_depnum_ccdc_archive 'CCDC 2312097'
loop_
_audit_author_name
_audit_author_address
'Ryo murakami'
;Kobe Gakuin University
Japan
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
_chemical_name_common            GAB
_chemical_name_systematic        
'(E)-amino((4-(4-(dimethylamino)styryl)phenyl)amino)methaniminium ethyl carbonate'
_chemical_formula_moiety         'C3 H5 O3, C15 H19 N6'
_chemical_formula_sum            'C18 H24 N6 O3'
_chemical_formula_weight         372.43
_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                   7.6781(4)
_cell_length_b                   27.9980(13)
_cell_length_c                   9.1512(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.736(4)
_cell_angle_gamma                90
_cell_volume                     1963.07(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7975
_cell_measurement_temperature    ?
_cell_measurement_theta_max      23.2070
_cell_measurement_theta_min      2.3240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_preparation       
'After dissolving in ethanol, it was left standing in air.'
_exptl_crystal_recrystallization_method 'Vapor diffusion method (EtOH)'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.670
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_temperature      300
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00-150.00  368
  2  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00 150.00  368
  3  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00  90.00  368
  4  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00 120.00  368
  5  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00   0.00  368
  6  ω    -74.00 101.00   0.50   23.83    --   20.00  54.00 -90.00  350
  7  ω    -74.00 110.00   0.50   23.83    --   20.00  54.00 -60.00  368
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454567000
_diffrn_orient_matrix_UB_12      0.0215780000
_diffrn_orient_matrix_UB_13      0.0116352000
_diffrn_orient_matrix_UB_21      0.0587906000
_diffrn_orient_matrix_UB_22      0.0125052000
_diffrn_orient_matrix_UB_23      -0.0428788000
_diffrn_orient_matrix_UB_31      -0.0553201000
_diffrn_orient_matrix_UB_32      -0.0044553000
_diffrn_orient_matrix_UB_33      -0.0636425000
_diffrn_oxdiff_digest_frames     
;
018015ea8f3fde7e82fe93c442e773062a000254a5d
;
_diffrn_oxdiff_digest_hkl        
;
01fd0302f65dbb3f6687176f36f9f2f0df7791
;
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2921
_reflns_number_total             5917
_reflns_odcompleteness_completeness 99.85
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_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     247
_refine_ls_number_reflns         5917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0747
_refine_ls_restrained_S_all      1.034
_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)+(0.0647P)²+0.8318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00H,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C00D(H00D), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C00O(H00Q,H00R,H00S), C00Q(H00A,H00B,H00C), C00R(H00E,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_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 1.2315(2) 0.81181(6) 0.60533(15) 0.0688(5) Uani 1 1 d . . . . .
O002 O 0.9756(2) 0.78127(7) 0.54372(16) 0.0770(5) Uani 1 1 d . . . . .
O003 O 1.0537(2) 0.79192(7) 0.77902(16) 0.0831(6) Uani 1 1 d . . . . .
N3 N 0.5120(3) 0.69370(7) 0.75373(19) 0.0656(5) Uani 1 1 d . . . . .
H3 H 0.495221 0.695317 0.845609 0.079 Uiso 1 1 calc R . . . .
N5 N 0.6904(3) 0.72144(8) 0.57412(19) 0.0709(6) Uani 1 1 d . . . . .
H5A H 0.781932 0.737099 0.553256 0.085 Uiso 1 1 calc R . . . .
H5B H 0.624782 0.708535 0.505339 0.085 Uiso 1 1 calc R . . . .
N4 N 0.7544(3) 0.73750(9) 0.8146(2) 0.0905(8) Uani 1 1 d . . . . .
H4A H 0.845290 0.752995 0.791408 0.109 Uiso 1 1 calc R . . . .
H4B H 0.730923 0.735179 0.904969 0.109 Uiso 1 1 calc R . . . .
C007 C 1.0781(3) 0.79407(8) 0.6485(2) 0.0595(6) Uani 1 1 d . . . . .
C008 C 0.3882(3) 0.66639(8) 0.6682(2) 0.0607(6) Uani 1 1 d . . . . .
C009 C 0.6508(3) 0.71724(9) 0.7115(2) 0.0608(6) Uani 1 1 d . . . . .
N00A N -0.4850(3) 0.43617(8) 0.0969(3) 0.0893(7) Uani 1 1 d . . . . .
C00B C -0.3716(3) 0.46643(8) 0.1720(3) 0.0678(6) Uani 1 1 d . . . . .
N1 N 0.0355(4) 0.55938(10) 0.3853(3) 0.1036(9) Uani 1 1 d . . . . .
C00D C 0.4345(4) 0.63607(9) 0.5579(3) 0.0744(7) Uani 1 1 d . . . . .
H00D H 0.549348 0.634460 0.531722 0.089 Uiso 1 1 calc R . . . .
N2 N -0.0366(4) 0.57881(12) 0.4662(3) 0.1165(11) Uani 1 1 d . . . . .
C00F C -0.1330(4) 0.52825(10) 0.3215(3) 0.0846(9) Uani 1 1 d . . . . .
C00G C 1.3599(3) 0.82752(11) 0.7163(3) 0.0771(7) Uani 1 1 d . . . . .
H00H H 1.395539 0.801163 0.780283 0.093 Uiso 1 1 calc R . . . .
H00O H 1.312327 0.852598 0.775042 0.093 Uiso 1 1 calc R . . . .
C00H C 0.1347(5) 0.60961(12) 0.5285(4) 0.0974(11) Uani 1 1 d . . . . .
C00I C -0.1984(4) 0.46976(10) 0.1378(3) 0.0845(8) Uani 1 1 d . . . . .
H00I H -0.159338 0.450840 0.063027 0.101 Uiso 1 1 calc R . . . .
C00J C 0.2167(4) 0.66771(11) 0.7055(3) 0.0822(8) Uani 1 1 d . . . . .
H00J H 0.186078 0.688385 0.779057 0.099 Uiso 1 1 calc R . . . .
C00K C 0.3054(5) 0.60802(10) 0.4870(3) 0.0912(10) Uani 1 1 d . . . . .
H00K H 0.333739 0.587992 0.411038 0.109 Uiso 1 1 calc R . . . .
C00L C -0.0848(4) 0.49991(11) 0.2105(4) 0.0904(9) Uani 1 1 d . . . . .
H00L H 0.029755 0.501226 0.183503 0.108 Uiso 1 1 calc R . . . .
C00M C -0.4208(4) 0.49518(10) 0.2862(3) 0.0883(8) Uani 1 1 d . . . . .
H00M H -0.535308 0.494096 0.313586 0.106 Uiso 1 1 calc R . . . .
C00N C -0.3024(5) 0.52537(10) 0.3598(3) 0.0949(9) Uani 1 1 d . . . . .
H00N H -0.338283 0.543991 0.436474 0.114 Uiso 1 1 calc R . . . .
C00O C 1.5125(4) 0.84588(12) 0.6393(3) 0.0932(9) Uani 1 1 d . . . . .
H00Q H 1.477834 0.873527 0.582583 0.140 Uiso 1 1 calc GR . . . .
H00R H 1.552667 0.821536 0.575746 0.140 Uiso 1 1 calc GR . . . .
H00S H 1.604966 0.854368 0.710285 0.140 Uiso 1 1 calc GR . . . .
C00P C 0.0923(4) 0.63981(12) 0.6380(4) 0.0989(10) Uani 1 1 d . . . . .
H00P H -0.021828 0.641158 0.666042 0.119 Uiso 1 1 calc R . . . .
C00Q C -0.4301(5) 0.40915(12) -0.0274(4) 0.1164(12) Uani 1 1 d . . . . .
H00A H -0.373726 0.430139 -0.092526 0.175 Uiso 1 1 calc GR . . . .
H00B H -0.530168 0.394831 -0.078241 0.175 Uiso 1 1 calc GR . . . .
H00C H -0.349961 0.384607 0.006470 0.175 Uiso 1 1 calc GR . . . .
C00R C -0.6622(4) 0.43098(13) 0.1342(5) 0.1216(13) Uani 1 1 d . . . . .
H00E H -0.665468 0.427628 0.238370 0.182 Uiso 1 1 calc GR . . . .
H00F H -0.712275 0.403136 0.086829 0.182 Uiso 1 1 calc GR . . . .
H00G H -0.727783 0.458710 0.102368 0.182 Uiso 1 1 calc GR . . . .


_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 C007 1.361(3) . ?
O001 C00G 1.438(3) . ?
O002 C007 1.253(3) . ?
O003 C007 1.222(2) . ?
N3 C008 1.416(3) . ?
N3 C009 1.332(3) . ?
N5 C009 1.317(3) . ?
N4 C009 1.322(3) . ?
C008 C00D 1.383(3) . ?
C008 C00J 1.382(4) . ?
N00A C00B 1.368(3) . ?
N00A C00Q 1.451(4) . ?
N00A C00R 1.432(4) . ?
C00B C00I 1.389(4) . ?
C00B C00M 1.391(4) . ?
N1 N2 1.097(3) . ?
N1 C00F 1.636(4) . ?
C00D C00K 1.392(4) . ?
N2 C00H 1.643(4) . ?
C00F C00L 1.359(4) . ?
C00F C00N 1.372(4) . ?
C00G C00O 1.497(4) . ?
C00H C00K 1.389(5) . ?
C00H C00P 1.367(5) . ?
C00I C00L 1.357(4) . ?
C00J C00P 1.352(4) . ?
C00M C00N 1.384(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
C007 O001 C00G 118.25(17) . . ?
C009 N3 C008 128.90(18) . . ?
O002 C007 O001 113.23(18) . . ?
O003 C007 O001 119.5(2) . . ?
O003 C007 O002 127.3(2) . . ?
C00D C008 N3 122.7(2) . . ?
C00J C008 N3 117.7(2) . . ?
C00J C008 C00D 119.4(2) . . ?
N5 C009 N3 124.1(2) . . ?
N5 C009 N4 118.5(2) . . ?
N4 C009 N3 117.42(19) . . ?
C00B N00A C00Q 120.6(3) . . ?
C00B N00A C00R 121.8(3) . . ?
C00R N00A C00Q 117.6(3) . . ?
N00A C00B C00I 121.0(3) . . ?
N00A C00B C00M 122.8(3) . . ?
C00I C00B C00M 116.2(3) . . ?
N2 N1 C00F 94.7(3) . . ?
C008 C00D C00K 118.5(3) . . ?
N1 N2 C00H 93.8(3) . . ?
C00L C00F N1 109.3(3) . . ?
C00L C00F C00N 117.7(3) . . ?
C00N C00F N1 133.0(3) . . ?
O001 C00G C00O 107.1(2) . . ?
C00K C00H N2 129.5(4) . . ?
C00P C00H N2 110.8(3) . . ?
C00P C00H C00K 119.6(3) . . ?
C00L C00I C00B 121.7(3) . . ?
C00P C00J C008 121.9(3) . . ?
C00H C00K C00D 120.7(3) . . ?
C00I C00L C00F 122.2(3) . . ?
C00N C00M C00B 121.1(3) . . ?
C00F C00N C00M 121.0(3) . . ?
C00J C00P C00H 119.8(3) . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Dual-Thickness MicroLoops'
_olex2_submission_original_sample_id KS105
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.889
_chemical_properties_physical    Light-sensitive
