# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_KB1716_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2463047'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid oxalate dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C2 H O4, 2(H2 O)'
_chemical_formula_sum            'C8 H19 N O8'
_chemical_formula_weight         257.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.7514(3)
_cell_length_b                   5.68736(12)
_cell_length_c                   13.0019(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.8233(9)
_cell_angle_gamma                90
_cell_volume                     1226.91(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9621
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.93

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22791
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3063
_reflns_number_gt                2252
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.0595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.79921(8) 0.5453(2) 0.51074(12) 0.0384(3) Uani 1 1 d . . . . .
H1A H 0.831991 0.654525 0.487503 0.046 Uiso 1 1 calc R U . . .
H1B H 0.801100 0.592799 0.583271 0.046 Uiso 1 1 calc R U . . .
C2 C 0.71304(7) 0.5582(2) 0.43115(11) 0.0349(3) Uani 1 1 d . . . . .
H2A H 0.712739 0.532209 0.357273 0.042 Uiso 1 1 calc R U . . .
H2B H 0.692810 0.715693 0.433609 0.042 Uiso 1 1 calc R U . . .
C3 C 0.65596(7) 0.3838(2) 0.45308(11) 0.0339(3) Uani 1 1 d . . . . .
H3A H 0.661354 0.394663 0.529828 0.041 Uiso 1 1 calc R U . . .
H3B H 0.671459 0.226042 0.440313 0.041 Uiso 1 1 calc R U . . .
C4 C 0.56809(7) 0.4235(2) 0.38155(11) 0.0360(3) Uani 1 1 d . . . . .
H4A H 0.552137 0.581065 0.393847 0.043 Uiso 1 1 calc R U . . .
H4B H 0.562054 0.410407 0.304638 0.043 Uiso 1 1 calc R U . . .
C5 C 0.51357(7) 0.2460(2) 0.40739(12) 0.0400(3) Uani 1 1 d . . . . .
H5A H 0.525603 0.092254 0.384782 0.048 Uiso 1 1 calc R U . . .
H5B H 0.527879 0.241410 0.486640 0.048 Uiso 1 1 calc R U . . .
N1 N 0.83346(7) 0.3048(2) 0.51727(11) 0.0379(3) Uani 1 1 d . . . . .
H1N H 0.8179(14) 0.245(4) 0.441(2) 0.099(8) Uiso 1 1 d . . . . .
H2N H 0.8117(13) 0.218(4) 0.5659(18) 0.089(7) Uiso 1 1 d . . . . .
H3N H 0.8905(15) 0.323(4) 0.5583(18) 0.094(7) Uiso 1 1 d . . . . .
O1 O 0.40172(6) 0.4612(2) 0.28857(9) 0.0486(3) Uani 1 1 d . . . . .
H1O H 0.3450(12) 0.476(4) 0.2629(16) 0.077(6) Uiso 1 1 d . . . . .
O2 O 0.37679(6) 0.1582(2) 0.37859(11) 0.0611(3) Uani 1 1 d . . . . .
C6 C 0.42389(7) 0.2832(2) 0.35660(11) 0.0357(3) Uani 1 1 d . . . . .
C7 C 1.05338(7) 0.21050(19) 0.65479(10) 0.0274(2) Uani 1 1 d . . . . .
C8 C 1.01661(7) -0.0398(2) 0.63157(10) 0.0279(2) Uani 1 1 d . . . . .
O3 O 1.00349(5) 0.37498(15) 0.62803(8) 0.0389(2) Uani 1 1 d . . . . .
O4 O 1.12796(5) 0.23005(15) 0.69713(9) 0.0401(2) Uani 1 1 d . . . . .
O5 O 1.06988(5) -0.20884(15) 0.66386(9) 0.0409(3) Uani 1 1 d . . . . .
H5O H 1.0458(13) -0.361(4) 0.6538(17) 0.087(7) Uiso 1 1 d . . . . .
O6 O 0.94527(5) -0.06896(16) 0.58640(9) 0.0468(3) Uani 1 1 d . . . . .
O1W O 0.24698(6) 0.57669(18) 0.20959(9) 0.0400(2) Uani 1 1 d . . . . .
H1W H 0.2046(13) 0.472(4) 0.2085(17) 0.085(7) Uiso 1 1 d . . . . .
H2W H 0.2392(12) 0.693(4) 0.2525(17) 0.076(7) Uiso 1 1 d . . . . .
O2W O 0.77209(6) 0.04895(16) 0.66397(9) 0.0387(2) Uani 1 1 d . . . . .
H3W H 0.8097(14) -0.055(4) 0.7094(19) 0.086(7) Uiso 1 1 d . . . . .
H4W H 0.7281(12) -0.026(3) 0.6517(15) 0.060(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
C1 N1 1.4870(17) . ?
C1 C2 1.5135(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.5153(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5225(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.5166(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5059(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N1 H1N 0.99(3) . ?
N1 H2N 0.98(2) . ?
N1 H3N 0.97(2) . ?
O1 C6 1.3093(16) . ?
O1 H1O 0.94(2) . ?
O2 C6 1.2068(16) . ?
C7 O4 1.2450(13) . ?
C7 O3 1.2496(13) . ?
C7 C8 1.5503(16) . ?
C8 O6 1.2032(13) . ?
C8 O5 1.3086(13) . ?
O5 H5O 0.95(2) . ?
O1W H1W 0.96(2) . ?
O1W H2W 0.91(2) . ?
O2W H3W 0.93(2) . ?
O2W H4W 0.852(19) . ?

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 C2 112.14(11) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 114.87(11) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 113.36(11) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 111.22(11) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 117.87(11) . . ?
C6 C5 H5A 107.8 . . ?
C4 C5 H5A 107.8 . . ?
C6 C5 H5B 107.8 . . ?
C4 C5 H5B 107.8 . . ?
H5A C5 H5B 107.2 . . ?
C1 N1 H1N 107.2(13) . . ?
C1 N1 H2N 104.7(13) . . ?
H1N N1 H2N 115.9(18) . . ?
C1 N1 H3N 105.1(14) . . ?
H1N N1 H3N 117.0(18) . . ?
H2N N1 H3N 105.8(17) . . ?
C6 O1 H1O 109.6(12) . . ?
O2 C6 O1 123.25(12) . . ?
O2 C6 C5 121.78(13) . . ?
O1 C6 C5 114.97(11) . . ?
O4 C7 O3 126.39(11) . . ?
O4 C7 C8 118.43(10) . . ?
O3 C7 C8 115.18(10) . . ?
O6 C8 O5 124.78(11) . . ?
O6 C8 C7 121.26(10) . . ?
O5 C8 C7 113.95(10) . . ?
C8 O5 H5O 112.6(13) . . ?
H1W O1W H2W 99.8(16) . . ?
H3W O2W H4W 102.0(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1W 0.99(3) 2.12(3) 3.0704(17) 161.6(19) 2_645 yes
O5 H5O O3 0.95(2) 1.66(2) 2.6111(13) 176(2) 1_545 yes
O1W H1W O4 0.96(2) 1.75(2) 2.7000(13) 175.3(19) 4_465 yes
O1W H2W O2W 0.91(2) 1.88(2) 2.7831(15) 175.0(18) 3_666 yes
O2W H3W O4 0.93(2) 1.80(2) 2.7241(13) 172(2) 2_746 yes
O2W H4W O2 0.852(19) 1.916(19) 2.7639(14) 173.3(17) 3_656 yes
N1 H2N O2W 0.98(2) 1.92(2) 2.9016(17) 178(2) . yes
N1 H3N O3 0.97(2) 1.91(2) 2.8729(14) 175(2) . yes
O1 H1O O1W 0.94(2) 1.73(2) 2.6505(13) 165.3(19) . yes

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methano'
####################################################################### 
# 
# 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_KB1151_0m
_database_code_depnum_ccdc_archive 'CCDC 2463057'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'Aminomethyl benzoic acid 2-chloro-4-nitrobenzoate monohydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Cl N2 O7'
_chemical_formula_weight         370.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.3098(3)
_cell_length_b                   9.6361(4)
_cell_length_c                   10.8666(4)
_cell_angle_alpha                96.5031(13)
_cell_angle_beta                 106.9551(13)
_cell_angle_gamma                101.1189(13)
_cell_volume                     803.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.52

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6660
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22156
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         30.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4899
_reflns_number_gt                3771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.2583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4899
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C -0.11478(18) -0.43957(14) 0.18806(15) 0.0371(3) Uani 1 1 d . . . . .
H1A H -0.225787 -0.448123 0.202550 0.045 Uiso 1 1 calc R U . . .
H1B H -0.135918 -0.484076 0.098379 0.045 Uiso 1 1 calc R U . . .
C2 C -0.02628(17) -0.28252(14) 0.20862(14) 0.0324(3) Uani 1 1 d . . . . .
C3 C -0.0103(2) -0.18774(15) 0.32062(15) 0.0399(3) Uani 1 1 d . . . . .
H3 H -0.052395 -0.221398 0.384852 0.048 Uiso 1 1 calc R U . . .
C4 C 0.0683(2) -0.04342(15) 0.33654(15) 0.0399(3) Uani 1 1 d . . . . .
H4 H 0.076598 0.019733 0.410702 0.048 Uiso 1 1 calc R U . . .
C5 C 0.13460(18) 0.00749(13) 0.24273(14) 0.0332(3) Uani 1 1 d . . . . .
C6 C 0.1200(2) -0.08720(15) 0.13170(15) 0.0394(3) Uani 1 1 d . . . . .
H6 H 0.165391 -0.054054 0.068786 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0380(2) -0.23111(14) 0.11424(15) 0.0387(3) Uani 1 1 d . . . . .
H7 H 0.026180 -0.293491 0.038588 0.046 Uiso 1 1 calc R U . . .
C8 C 0.21788(19) 0.16345(14) 0.26148(15) 0.0370(3) Uani 1 1 d . . . . .
N1 N -0.00797(18) -0.51584(14) 0.27804(15) 0.0391(3) Uani 1 1 d . . . . .
H1N H -0.059(3) -0.608(3) 0.266(2) 0.078(7) Uiso 1 1 d . . . . .
H2N H 0.021(3) -0.480(3) 0.358(2) 0.065(7) Uiso 1 1 d . . . . .
H3N H 0.092(3) -0.513(2) 0.259(2) 0.062(6) Uiso 1 1 d . . . . .
O1 O 0.32693(16) 0.19177(11) 0.19684(13) 0.0504(3) Uani 1 1 d . . . . .
H1O H 0.376(3) 0.292(3) 0.209(2) 0.084(8) Uiso 1 1 d . . . . .
O2 O 0.18417(18) 0.25415(12) 0.33116(13) 0.0526(3) Uani 1 1 d . . . . .
C9 C 0.38965(17) 0.53798(13) 0.18778(13) 0.0310(3) Uani 1 1 d . . . . .
C10 C 0.47851(16) 0.69396(13) 0.19926(13) 0.0295(2) Uani 1 1 d . . . . .
C11 C 0.50495(17) 0.79493(14) 0.30999(13) 0.0322(3) Uani 1 1 d . . . . .
C12 C 0.58574(18) 0.93808(14) 0.32210(15) 0.0359(3) Uani 1 1 d . . . . .
H12 H 0.604247 1.004640 0.396787 0.043 Uiso 1 1 calc R U . . .
C13 C 0.63763(18) 0.97798(13) 0.21900(15) 0.0351(3) Uani 1 1 d . . . . .
C14 C 0.6121(2) 0.88296(15) 0.10664(15) 0.0388(3) Uani 1 1 d . . . . .
H14 H 0.647546 0.913662 0.038558 0.047 Uiso 1 1 calc R U . . .
C15 C 0.53187(19) 0.73996(14) 0.09769(14) 0.0366(3) Uani 1 1 d . . . . .
H15 H 0.513625 0.674048 0.022640 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43350(6) 0.74072(4) 0.43515(4) 0.05001(13) Uani 1 1 d . . . . .
N2 N 0.72725(17) 1.12897(13) 0.23257(15) 0.0445(3) Uani 1 1 d . . . . .
O3 O 0.48721(14) 0.45532(11) 0.22437(14) 0.0501(3) Uani 1 1 d . . . . .
O4 O 0.23055(13) 0.50369(11) 0.14233(12) 0.0439(3) Uani 1 1 d . . . . .
O5 O 0.7636(2) 1.20878(13) 0.33680(16) 0.0707(4) Uani 1 1 d . . . . .
O6 O 0.7646(2) 1.16810(13) 0.13946(15) 0.0631(4) Uani 1 1 d . . . . .
O1W O 0.20890(18) 0.46219(16) 0.54106(13) 0.0534(3) Uani 1 1 d . . . . .
H1 H 0.226(4) 0.403(3) 0.492(3) 0.080 Uiso 1 1 d . U . . .
H2 H 0.309(4) 0.493(3) 0.591(3) 0.080 Uiso 1 1 d . U . . .


_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
C1 N1 1.481(2) . ?
C1 C2 1.5097(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.384(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3877(19) . ?
C5 C8 1.4921(18) . ?
C6 C7 1.3870(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.2182(17) . ?
C8 O1 1.3070(19) . ?
N1 H1N 0.88(3) . ?
N1 H2N 0.85(2) . ?
N1 H3N 0.91(2) . ?
O1 H1O 0.95(3) . ?
C9 O4 1.2308(16) . ?
C9 O3 1.2580(17) . ?
C9 C10 1.5151(17) . ?
C10 C15 1.3899(19) . ?
C10 C11 1.3932(18) . ?
C11 C12 1.3860(18) . ?
C11 Cl1 1.7284(14) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(2) . ?
C13 N2 1.4707(17) . ?
C14 C15 1.3893(19) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N2 O5 1.2162(19) . ?
N2 O6 1.219(2) . ?
O1W H1 0.80(3) . ?
O1W H2 0.83(3) . ?

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 C2 111.31(12) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C7 C2 C3 119.31(12) . . ?
C7 C2 C1 119.71(12) . . ?
C3 C2 C1 120.97(13) . . ?
C4 C3 C2 120.13(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.46(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.39(12) . . ?
C4 C5 C8 119.59(12) . . ?
C6 C5 C8 121.01(13) . . ?
C7 C6 C5 120.22(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C2 C7 C6 120.46(13) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O2 C8 O1 124.27(13) . . ?
O2 C8 C5 121.63(14) . . ?
O1 C8 C5 114.10(12) . . ?
C1 N1 H1N 111.5(16) . . ?
C1 N1 H2N 114.9(16) . . ?
H1N N1 H2N 109(2) . . ?
C1 N1 H3N 108.6(14) . . ?
H1N N1 H3N 106(2) . . ?
H2N N1 H3N 106(2) . . ?
C8 O1 H1O 111.9(16) . . ?
O4 C9 O3 126.27(12) . . ?
O4 C9 C10 117.50(12) . . ?
O3 C9 C10 116.22(11) . . ?
C15 C10 C11 118.53(12) . . ?
C15 C10 C9 120.45(11) . . ?
C11 C10 C9 121.00(12) . . ?
C12 C11 C10 121.79(12) . . ?
C12 C11 Cl1 119.04(10) . . ?
C10 C11 Cl1 119.17(10) . . ?
C13 C12 C11 117.39(13) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C14 C13 C12 123.10(12) . . ?
C14 C13 N2 119.23(13) . . ?
C12 C13 N2 117.66(13) . . ?
C13 C14 C15 118.21(13) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C10 120.96(13) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O5 N2 O6 122.83(14) . . ?
O5 N2 C13 118.64(14) . . ?
O6 N2 C13 118.52(14) . . ?
H1 O1W H2 99(3) . . ?

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
N1 C1 C2 C7 109.73(16) . . . . ?
N1 C1 C2 C3 -71.15(17) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -178.71(14) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 C8 179.69(14) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C8 C5 C6 C7 -178.25(14) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C1 C2 C7 C6 -179.86(14) . . . . ?
C5 C6 C7 C2 -1.6(2) . . . . ?
C4 C5 C8 O2 -23.4(2) . . . . ?
C6 C5 C8 O2 155.60(16) . . . . ?
C4 C5 C8 O1 156.87(15) . . . . ?
C6 C5 C8 O1 -24.1(2) . . . . ?
O4 C9 C10 C15 -91.06(16) . . . . ?
O3 C9 C10 C15 87.97(17) . . . . ?
O4 C9 C10 C11 87.43(17) . . . . ?
O3 C9 C10 C11 -93.54(16) . . . . ?
C15 C10 C11 C12 -1.4(2) . . . . ?
C9 C10 C11 C12 -179.90(12) . . . . ?
C15 C10 C11 Cl1 178.05(11) . . . . ?
C9 C10 C11 Cl1 -0.47(18) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
Cl1 C11 C12 C13 -178.62(11) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C11 C12 C13 N2 -178.53(12) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
N2 C13 C14 C15 178.05(13) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C11 C10 C15 C14 0.9(2) . . . . ?
C9 C10 C15 C14 179.42(13) . . . . ?
C14 C13 N2 O5 -173.19(16) . . . . ?
C12 C13 N2 O5 5.6(2) . . . . ?
C14 C13 N2 O6 5.6(2) . . . . ?
C12 C13 N2 O6 -175.61(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O5 0.88(3) 2.42(3) 3.1940(18) 147(2) 1_435 yes
N1 H1N O6 0.88(3) 2.37(3) 3.1931(19) 155(2) 1_435 yes
N1 H2N O1W 0.85(2) 2.34(2) 2.957(2) 130(2) 1_545 yes
N1 H3N O4 0.91(2) 1.95(2) 2.7861(18) 153(2) 1_545 yes
N1 H2N O1W 0.85(2) 2.49(2) 2.9894(19) 118.9(19) 2_556 yes
O1W H2 O3 0.83(3) 2.14(3) 2.9187(19) 156(3) 2_666 yes
O1 H1O O3 0.95(3) 1.63(3) 2.5698(15) 170(2) . yes
O1 H1O O4 0.95(3) 2.63(3) 3.3289(16) 131(2) . yes
O1W H1 O2 0.80(3) 2.03(3) 2.7920(17) 160(3) . yes

_refine_diff_density_max         0.811
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_KB1176_0m
_database_code_depnum_ccdc_archive 'CCDC 2463051'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid orotate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N2 O4, C6 H14 N O2'
_chemical_formula_sum            'C11 H17 N3 O6'
_chemical_formula_weight         287.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   5.5781(5)
_cell_length_b                   9.1736(8)
_cell_length_c                   25.930(2)
_cell_angle_alpha                91.052(3)
_cell_angle_beta                 92.193(3)
_cell_angle_gamma                90.552(3)
_cell_volume                     1325.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9066
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      30.62

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14117
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.786
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5253
_reflns_number_gt                4550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0849P)²+1.2080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5253
_refine_ls_number_parameters     409
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1A C -1.0369(6) 0.7299(3) 0.86062(11) 0.0451(6) Uani 1 1 d . . . . .
H1AA H -0.930395 0.795959 0.880403 0.054 Uiso 1 1 calc R U . . .
H1AB H -1.156830 0.788346 0.842795 0.054 Uiso 1 1 calc R U . . .
C2A C -0.8957(5) 0.6510(3) 0.82162(11) 0.0449(6) Uani 1 1 d . . . . .
H2AA H -1.003430 0.590854 0.799836 0.054 Uiso 1 1 calc R U . . .
H2AB H -0.783074 0.587055 0.839185 0.054 Uiso 1 1 calc R U . . .
C3A C -0.7592(5) 0.7538(3) 0.78818(10) 0.0427(6) Uani 1 1 d . . . . .
H3AA H -0.872187 0.818039 0.770862 0.051 Uiso 1 1 calc R U . . .
H3AB H -0.651655 0.813796 0.810079 0.051 Uiso 1 1 calc R U . . .
C4A C -0.6152(6) 0.6761(3) 0.74819(11) 0.0451(6) Uani 1 1 d . . . . .
H4AA H -0.724189 0.624790 0.723933 0.054 Uiso 1 1 calc R U . . .
H4AB H -0.514651 0.604198 0.765094 0.054 Uiso 1 1 calc R U . . .
C5A C -0.4584(6) 0.7787(3) 0.71883(11) 0.0462(7) Uani 1 1 d . . . . .
H5AA H -0.560099 0.849047 0.701353 0.055 Uiso 1 1 calc R U . . .
H5AB H -0.353417 0.832078 0.743332 0.055 Uiso 1 1 calc R U . . .
C6A C -0.3082(5) 0.7044(3) 0.67979(10) 0.0408(6) Uani 1 1 d . . . . .
N1A N -1.1585(4) 0.6329(2) 0.89672(9) 0.0389(5) Uani 1 1 d D . . . .
H1N H -1.280(5) 0.682(4) 0.9124(13) 0.069(11) Uiso 1 1 d D . . . .
H2N H -1.049(7) 0.590(5) 0.9179(15) 0.099(15) Uiso 1 1 d D . . . .
H3N H -1.247(8) 0.565(4) 0.8793(16) 0.105(16) Uiso 1 1 d D . . . .
O1A O -0.3398(4) 0.5797(2) 0.66500(9) 0.0615(6) Uani 1 1 d . . . . .
O2A O -0.1402(4) 0.7908(2) 0.66259(8) 0.0522(5) Uani 1 1 d D . . . .
H2O H -0.043(6) 0.748(4) 0.6412(13) 0.082(13) Uiso 1 1 d D . . . .
C1B C 0.0829(5) 0.3108(3) 0.63628(10) 0.0419(6) Uani 1 1 d . . . . .
H1BA H 0.187925 0.390673 0.647866 0.050 Uiso 1 1 calc R U . . .
H1BB H 0.178874 0.239309 0.618612 0.050 Uiso 1 1 calc R U . . .
C2B C -0.0262(5) 0.2417(3) 0.68247(11) 0.0484(7) Uani 1 1 d . . . . .
H2BA H -0.150189 0.172818 0.670582 0.058 Uiso 1 1 calc R U . . .
H2BB H -0.101217 0.316755 0.702966 0.058 Uiso 1 1 calc R U . . .
C3B C 0.1586(6) 0.1629(3) 0.71632(12) 0.0511(7) Uani 1 1 d . . . . .
H3BA H 0.074668 0.099565 0.739317 0.061 Uiso 1 1 calc R U . . .
H3BB H 0.254279 0.101617 0.694398 0.061 Uiso 1 1 calc R U . . .
C4B C 0.3263(5) 0.2634(3) 0.74859(11) 0.0441(6) Uani 1 1 d . . . . .
H4BA H 0.413434 0.325970 0.725879 0.053 Uiso 1 1 calc R U . . .
H4BB H 0.232253 0.325141 0.770687 0.053 Uiso 1 1 calc R U . . .
C5B C 0.5040(5) 0.1781(3) 0.78169(11) 0.0437(6) Uani 1 1 d . . . . .
H5BA H 0.415650 0.107634 0.801195 0.052 Uiso 1 1 calc R U . . .
H5BB H 0.607361 0.124078 0.759119 0.052 Uiso 1 1 calc R U . . .
C6B C 0.6575(5) 0.2686(3) 0.81851(10) 0.0372(5) Uani 1 1 d . . . . .
N1B N -0.1061(4) 0.3665(2) 0.59965(8) 0.0346(5) Uani 1 1 d D . . . .
H4N H -0.032(5) 0.394(3) 0.5714(9) 0.050(9) Uiso 1 1 d D . . . .
H5N H -0.186(6) 0.439(3) 0.6145(14) 0.073(11) Uiso 1 1 d D . . . .
H6N H -0.211(6) 0.295(3) 0.5914(14) 0.070(11) Uiso 1 1 d D . . . .
O1B O 0.8360(4) 0.1939(2) 0.83965(9) 0.0520(5) Uani 1 1 d D . . . .
H1O H 0.902(7) 0.249(4) 0.8630(12) 0.070(11) Uiso 1 1 d D . . . .
O2B O 0.6207(4) 0.3950(2) 0.82932(8) 0.0536(5) Uani 1 1 d . . . . .
C1 C 0.2454(5) 0.6287(3) 0.56283(10) 0.0364(6) Uani 1 1 d . . . . .
C2 C 0.4180(4) 0.7556(2) 0.55631(8) 0.0285(5) Uani 1 1 d . . . . .
C3 C 0.3961(4) 0.8842(2) 0.58063(9) 0.0289(5) Uani 1 1 d . . . . .
H3 H 0.269856 0.899440 0.602448 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5677(4) 0.9991(2) 0.57305(9) 0.0297(5) Uani 1 1 d . . . . .
C5 C 0.7698(4) 0.8329(2) 0.51426(8) 0.0281(5) Uani 1 1 d . . . . .
N1 N 0.7461(3) 0.9633(2) 0.53976(7) 0.0300(4) Uani 1 1 d . . . . .
H7N H 0.865(6) 1.040(3) 0.5357(11) 0.043(8) Uiso 1 1 d . . . . .
N2 N 0.6018(3) 0.7294(2) 0.52349(8) 0.0306(4) Uani 1 1 d . . . . .
H8N H 0.611(6) 0.641(4) 0.5060(12) 0.047(8) Uiso 1 1 d . . . . .
O1 O 0.0783(4) 0.6512(2) 0.59217(8) 0.0493(5) Uani 1 1 d . . . . .
O2 O 0.2834(4) 0.5155(2) 0.53861(10) 0.0652(7) Uani 1 1 d . . . . .
O3 O 0.5634(3) 1.12223(18) 0.59288(7) 0.0409(4) Uani 1 1 d . . . . .
O4 O 0.9334(3) 0.81264(18) 0.48414(7) 0.0370(4) Uani 1 1 d . . . . .
C6 C 1.2499(5) 0.3794(3) 0.93348(9) 0.0361(5) Uani 1 1 d . . . . .
C7 C 1.4113(4) 0.2480(2) 0.94213(8) 0.0272(5) Uani 1 1 d . . . . .
C8 C 1.3721(4) 0.1177(2) 0.91886(9) 0.0296(5) Uani 1 1 d . . . . .
H8 H 1.237675 0.102752 0.897009 0.035 Uiso 1 1 calc R U . . .
C9 C 1.5381(4) 0.0013(2) 0.92774(8) 0.0283(5) Uani 1 1 d . . . . .
C10 C 1.7724(4) 0.1690(2) 0.98544(8) 0.0269(5) Uani 1 1 d . . . . .
N3 N 1.6060(3) 0.2728(2) 0.97485(8) 0.0301(4) Uani 1 1 d . . . . .
H9N H 1.635(6) 0.359(4) 0.9914(12) 0.047(8) Uiso 1 1 d . . . . .
N4 N 1.7318(3) 0.0372(2) 0.96061(7) 0.0295(4) Uani 1 1 d . . . . .
H10N H 1.844(5) -0.037(3) 0.9669(9) 0.027(6) Uiso 1 1 d . . . . .
O5 O 1.0597(3) 0.3577(2) 0.90762(8) 0.0459(5) Uani 1 1 d . . . . .
O6 O 1.3204(5) 0.4967(2) 0.95205(10) 0.0701(8) Uani 1 1 d . . . . .
O7 O 1.5193(3) -0.12272(18) 0.90929(7) 0.0409(4) Uani 1 1 d . . . . .
O8 O 1.9469(3) 0.18979(18) 1.01516(6) 0.0354(4) Uani 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
C1A N1A 1.482(3) . ?
C1A C2A 1.488(4) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A C3A 1.513(4) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3A C4A 1.509(4) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A C5A 1.514(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5A C6A 1.498(4) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6A O1A 1.209(3) . ?
C6A O2A 1.317(3) . ?
N1A H1N 0.921(19) . ?
N1A H2N 0.902(19) . ?
N1A H3N 0.90(2) . ?
O2A H2O 0.880(19) . ?
C1B N1B 1.492(3) . ?
C1B C2B 1.511(4) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C2B C3B 1.525(4) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C3B C4B 1.524(4) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C5B 1.519(4) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C5B C6B 1.493(4) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C6B O2B 1.209(3) . ?
C6B O1B 1.321(3) . ?
N1B H4N 0.893(18) . ?
N1B H5N 0.898(19) . ?
N1B H6N 0.897(19) . ?
O1B H1O 0.850(19) . ?
C1 O2 1.228(3) . ?
C1 O1 1.242(3) . ?
C1 C2 1.520(3) . ?
C2 C3 1.337(3) . ?
C2 N2 1.377(3) . ?
C3 C4 1.439(3) . ?
C3 H3 0.9300 . ?
C4 O3 1.233(3) . ?
C4 N1 1.380(3) . ?
C5 O4 1.237(3) . ?
C5 N2 1.358(3) . ?
C5 N1 1.367(3) . ?
N1 H7N 0.97(3) . ?
N2 H8N 0.92(3) . ?
C6 O6 1.226(3) . ?
C6 O5 1.246(3) . ?
C6 C7 1.526(3) . ?
C7 C8 1.341(3) . ?
C7 N3 1.367(3) . ?
C8 C9 1.436(3) . ?
C8 H8 0.9300 . ?
C9 O7 1.228(3) . ?
C9 N4 1.384(3) . ?
C10 O8 1.229(3) . ?
C10 N3 1.361(3) . ?
C10 N4 1.372(3) . ?
N3 H9N 0.90(3) . ?
N4 H10N 0.94(3) . ?

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
N1A C1A C2A 113.9(2) . . ?
N1A C1A H1AA 108.8 . . ?
C2A C1A H1AA 108.8 . . ?
N1A C1A H1AB 108.8 . . ?
C2A C1A H1AB 108.8 . . ?
H1AA C1A H1AB 107.7 . . ?
C1A C2A C3A 112.3(2) . . ?
C1A C2A H2AA 109.2 . . ?
C3A C2A H2AA 109.2 . . ?
C1A C2A H2AB 109.2 . . ?
C3A C2A H2AB 109.2 . . ?
H2AA C2A H2AB 107.9 . . ?
C4A C3A C2A 113.2(2) . . ?
C4A C3A H3AA 108.9 . . ?
C2A C3A H3AA 108.9 . . ?
C4A C3A H3AB 108.9 . . ?
C2A C3A H3AB 108.9 . . ?
H3AA C3A H3AB 107.8 . . ?
C3A C4A C5A 112.8(2) . . ?
C3A C4A H4AA 109.0 . . ?
C5A C4A H4AA 109.0 . . ?
C3A C4A H4AB 109.0 . . ?
C5A C4A H4AB 109.0 . . ?
H4AA C4A H4AB 107.8 . . ?
C6A C5A C4A 114.1(2) . . ?
C6A C5A H5AA 108.7 . . ?
C4A C5A H5AA 108.7 . . ?
C6A C5A H5AB 108.7 . . ?
C4A C5A H5AB 108.7 . . ?
H5AA C5A H5AB 107.6 . . ?
O1A C6A O2A 123.6(2) . . ?
O1A C6A C5A 123.8(3) . . ?
O2A C6A C5A 112.5(2) . . ?
C1A N1A H1N 110(2) . . ?
C1A N1A H2N 110(3) . . ?
H1N N1A H2N 116(4) . . ?
C1A N1A H3N 111(3) . . ?
H1N N1A H3N 99(4) . . ?
H2N N1A H3N 110(4) . . ?
C6A O2A H2O 114(3) . . ?
N1B C1B C2B 111.3(2) . . ?
N1B C1B H1BA 109.4 . . ?
C2B C1B H1BA 109.4 . . ?
N1B C1B H1BB 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
H1BA C1B H1BB 108.0 . . ?
C1B C2B C3B 112.6(2) . . ?
C1B C2B H2BA 109.1 . . ?
C3B C2B H2BA 109.1 . . ?
C1B C2B H2BB 109.1 . . ?
C3B C2B H2BB 109.1 . . ?
H2BA C2B H2BB 107.8 . . ?
C4B C3B C2B 114.4(2) . . ?
C4B C3B H3BA 108.7 . . ?
C2B C3B H3BA 108.7 . . ?
C4B C3B H3BB 108.7 . . ?
C2B C3B H3BB 108.7 . . ?
H3BA C3B H3BB 107.6 . . ?
C5B C4B C3B 111.7(2) . . ?
C5B C4B H4BA 109.3 . . ?
C3B C4B H4BA 109.3 . . ?
C5B C4B H4BB 109.3 . . ?
C3B C4B H4BB 109.3 . . ?
H4BA C4B H4BB 107.9 . . ?
C6B C5B C4B 114.8(2) . . ?
C6B C5B H5BA 108.6 . . ?
C4B C5B H5BA 108.6 . . ?
C6B C5B H5BB 108.6 . . ?
C4B C5B H5BB 108.6 . . ?
H5BA C5B H5BB 107.5 . . ?
O2B C6B O1B 123.1(2) . . ?
O2B C6B C5B 124.4(2) . . ?
O1B C6B C5B 112.5(2) . . ?
C1B N1B H4N 107(2) . . ?
C1B N1B H5N 110(3) . . ?
H4N N1B H5N 113(3) . . ?
C1B N1B H6N 109(2) . . ?
H4N N1B H6N 109(3) . . ?
H5N N1B H6N 108(4) . . ?
C6B O1B H1O 107(3) . . ?
O2 C1 O1 126.7(2) . . ?
O2 C1 C2 117.3(2) . . ?
O1 C1 C2 116.0(2) . . ?
C3 C2 N2 121.6(2) . . ?
C3 C2 C1 123.0(2) . . ?
N2 C2 C1 115.40(19) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O3 C4 N1 119.9(2) . . ?
O3 C4 C3 125.6(2) . . ?
N1 C4 C3 114.51(19) . . ?
O4 C5 N2 122.7(2) . . ?
O4 C5 N1 121.26(19) . . ?
N2 C5 N1 115.99(19) . . ?
C5 N1 C4 126.19(18) . . ?
C5 N1 H7N 119.3(17) . . ?
C4 N1 H7N 114.5(17) . . ?
C5 N2 C2 121.7(2) . . ?
C5 N2 H8N 118(2) . . ?
C2 N2 H8N 121(2) . . ?
O6 C6 O5 126.0(2) . . ?
O6 C6 C7 117.1(2) . . ?
O5 C6 C7 116.8(2) . . ?
C8 C7 N3 121.4(2) . . ?
C8 C7 C6 123.5(2) . . ?
N3 C7 C6 115.0(2) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O7 C9 N4 119.6(2) . . ?
O7 C9 C8 125.7(2) . . ?
N4 C9 C8 114.65(19) . . ?
O8 C10 N3 123.2(2) . . ?
O8 C10 N4 121.67(19) . . ?
N3 C10 N4 115.15(19) . . ?
C10 N3 C7 122.7(2) . . ?
C10 N3 H9N 114(2) . . ?
C7 N3 H9N 123(2) . . ?
C10 N4 C9 126.21(18) . . ?
C10 N4 H10N 117.3(16) . . ?
C9 N4 H10N 116.5(16) . . ?

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
N1A C1A C2A C3A -175.6(2) . . . . ?
C1A C2A C3A C4A -179.8(3) . . . . ?
C2A C3A C4A C5A -173.8(3) . . . . ?
C3A C4A C5A C6A 178.4(3) . . . . ?
C4A C5A C6A O1A 14.1(4) . . . . ?
C4A C5A C6A O2A -167.0(3) . . . . ?
N1B C1B C2B C3B 171.0(2) . . . . ?
C1B C2B C3B C4B 73.8(3) . . . . ?
C2B C3B C4B C5B 179.5(3) . . . . ?
C3B C4B C5B C6B -173.9(2) . . . . ?
C4B C5B C6B O2B 13.3(4) . . . . ?
C4B C5B C6B O1B -168.7(2) . . . . ?
O2 C1 C2 C3 -179.9(3) . . . . ?
O1 C1 C2 C3 0.6(4) . . . . ?
O2 C1 C2 N2 -0.1(4) . . . . ?
O1 C1 C2 N2 -179.7(2) . . . . ?
N2 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 179.3(2) . . . . ?
C2 C3 C4 O3 179.0(2) . . . . ?
C2 C3 C4 N1 0.1(3) . . . . ?
O4 C5 N1 C4 178.2(2) . . . . ?
N2 C5 N1 C4 -0.8(3) . . . . ?
O3 C4 N1 C5 -178.5(2) . . . . ?
C3 C4 N1 C5 0.5(3) . . . . ?
O4 C5 N2 C2 -178.5(2) . . . . ?
N1 C5 N2 C2 0.5(3) . . . . ?
C3 C2 N2 C5 0.0(4) . . . . ?
C1 C2 N2 C5 -179.7(2) . . . . ?
O6 C6 C7 C8 -171.4(3) . . . . ?
O5 C6 C7 C8 7.8(4) . . . . ?
O6 C6 C7 N3 7.0(4) . . . . ?
O5 C6 C7 N3 -173.8(2) . . . . ?
N3 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 177.7(2) . . . . ?
C7 C8 C9 O7 178.8(2) . . . . ?
C7 C8 C9 N4 -0.5(3) . . . . ?
O8 C10 N3 C7 -179.3(2) . . . . ?
N4 C10 N3 C7 0.4(3) . . . . ?
C8 C7 N3 C10 0.7(3) . . . . ?
C6 C7 N3 C10 -177.7(2) . . . . ?
O8 C10 N4 C9 178.0(2) . . . . ?
N3 C10 N4 C9 -1.7(3) . . . . ?
O7 C9 N4 C10 -177.6(2) . . . . ?
C8 C9 N4 C10 1.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1N O7 0.921(19) 2.12(3) 2.908(3) 143(3) 1_265 yes
N1A H2N O5 0.902(19) 2.24(4) 2.828(3) 123(4) 1_355 yes
N1A H2N O6 0.902(19) 2.39(2) 3.255(3) 162(4) 1_355 yes
N1A H3N O2B 0.90(2) 2.12(2) 2.997(3) 166(5) 1_355 yes
N1B H6N O3 0.897(19) 2.01(2) 2.887(3) 165(3) 1_445 yes
N2 H8N O2 0.92(3) 1.94(3) 2.833(3) 163(3) 2_666 yes
N1B H4N O4 0.893(18) 2.44(3) 2.900(3) 113(2) 2_666 yes
N1 H7N O4 0.97(3) 1.84(3) 2.804(2) 169(3) 2_776 yes
N3 H9N O6 0.90(3) 1.97(3) 2.830(3) 160(3) 2_867 yes
N4 H10N O8 0.94(3) 1.89(3) 2.824(2) 175(2) 2_957 yes
O2A H2O O1 0.880(19) 1.70(2) 2.564(3) 165(4) . yes
N1B H4N O2 0.893(18) 2.28(2) 3.062(3) 147(3) . yes
N1B H5N O1A 0.898(19) 2.04(2) 2.914(3) 166(3) . yes
O1B H1O O5 0.850(19) 1.725(19) 2.572(3) 175(4) . yes

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_KB1107_0m
_database_code_depnum_ccdc_archive 'CCDC 2463055'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid saccharate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, C8 H10 N O2'
_chemical_formula_sum            'C15 H14 N2 O5 S'
_chemical_formula_weight         334.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   14.340(5)
_cell_length_b                   13.802(13)
_cell_length_c                   14.671(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2904(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9721
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.12

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            30905
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.475
_diffrn_reflns_theta_max         28.911
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7174
_reflns_number_gt                5755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.997

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.2713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2380 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7174
_refine_ls_number_parameters     447
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.6167(2) -0.2028(2) 0.6806(3) 0.0426(8) Uani 1 1 d . . . . .
H1AA H 0.668928 -0.187309 0.719963 0.051 Uiso 1 1 calc R U . . .
H1AB H 0.579115 -0.251569 0.710807 0.051 Uiso 1 1 calc R U . . .
C2A C 0.5591(2) -0.1134(2) 0.6656(2) 0.0360(7) Uani 1 1 d . . . . .
C3A C 0.4658(2) -0.1219(2) 0.6506(3) 0.0476(9) Uani 1 1 d . . . . .
H3A H 0.438718 -0.183089 0.647574 0.057 Uiso 1 1 calc R U . . .
C4A C 0.4117(2) -0.0414(2) 0.6399(3) 0.0454(8) Uani 1 1 d . . . . .
H4A H 0.348373 -0.048429 0.627968 0.054 Uiso 1 1 calc R U . . .
C5A C 0.4496(2) 0.0505(2) 0.6467(2) 0.0329(6) Uani 1 1 d . . . . .
C6A C 0.5431(2) 0.0591(2) 0.6614(3) 0.0403(8) Uani 1 1 d . . . . .
H6A H 0.570137 0.120160 0.666005 0.048 Uiso 1 1 calc R U . . .
C7A C 0.5970(2) -0.0219(2) 0.6693(3) 0.0441(9) Uani 1 1 d . . . . .
H7A H 0.660979 -0.015057 0.677414 0.053 Uiso 1 1 calc R U . . .
C8A C 0.3887(2) 0.1354(2) 0.6365(3) 0.0376(7) Uani 1 1 d . . . . .
N1A N 0.6523(2) -0.2423(2) 0.5924(3) 0.0493(8) Uani 1 1 d D . . . .
H1N H 0.694(3) -0.295(3) 0.597(3) 0.084(15) Uiso 1 1 d D . . . .
H2N H 0.682(3) -0.197(3) 0.558(3) 0.053(12) Uiso 1 1 d . . . . .
H3N H 0.602(4) -0.266(3) 0.563(3) 0.082(16) Uiso 1 1 d . . . . .
O1A O 0.30886(17) 0.12777(18) 0.6160(2) 0.0597(8) Uani 1 1 d . . . . .
O2A O 0.42920(18) 0.22017(16) 0.6496(2) 0.0510(7) Uani 1 1 d . . . . .
H2AO H 0.390(3) 0.261(3) 0.651(3) 0.070(15) Uiso 1 1 d . . . . .
C1B C 0.4263(2) 0.6944(2) 0.3101(2) 0.0395(7) Uani 1 1 d . . . . .
H1BA H 0.393753 0.738140 0.269224 0.047 Uiso 1 1 calc R U . . .
H1BB H 0.483851 0.674563 0.280789 0.047 Uiso 1 1 calc R U . . .
O2B O 0.23936(17) 0.27461(15) 0.3584(3) 0.0537(7) Uani 1 1 d . . . . .
H2BO H 0.200(4) 0.234(4) 0.382(4) 0.11(2) Uiso 1 1 d . . . . .
C2B C 0.3668(2) 0.6072(2) 0.3282(2) 0.0318(7) Uani 1 1 d . . . . .
C3B C 0.4057(2) 0.5160(2) 0.3283(3) 0.0452(9) Uani 1 1 d . . . . .
H3B H 0.469556 0.509238 0.319500 0.054 Uiso 1 1 calc R U . . .
C4B C 0.3516(2) 0.4346(2) 0.3413(3) 0.0443(9) Uani 1 1 d . . . . .
H4B H 0.378560 0.373363 0.339409 0.053 Uiso 1 1 calc R U . . .
C5B C 0.2592(2) 0.4444(2) 0.3567(2) 0.0306(6) Uani 1 1 d . . . . .
C6B C 0.2207(2) 0.5360(2) 0.3565(3) 0.0368(7) Uani 1 1 d . . . . .
H6B H 0.157238 0.543460 0.367324 0.044 Uiso 1 1 calc R U . . .
C7B C 0.2746(2) 0.6162(2) 0.3407(3) 0.0389(8) Uani 1 1 d . . . . .
H7B H 0.247151 0.677160 0.338563 0.047 Uiso 1 1 calc R U . . .
C8B C 0.1996(2) 0.3583(2) 0.3736(2) 0.0356(7) Uani 1 1 d . . . . .
N1B N 0.4482(2) 0.7462(2) 0.3989(2) 0.0392(7) Uani 1 1 d . . . . .
H4N H 0.498(3) 0.787(3) 0.390(3) 0.079(15) Uiso 1 1 d . . . . .
H5N H 0.463(3) 0.701(3) 0.439(3) 0.068(13) Uiso 1 1 d . . . . .
H6N H 0.400(3) 0.788(2) 0.417(2) 0.038(9) Uiso 1 1 d . . . . .
O1B O 0.12216(16) 0.36475(17) 0.4015(2) 0.0558(8) Uani 1 1 d . . . . .
C1 C 0.3297(2) 0.4473(2) 0.6221(2) 0.0341(7) Uani 1 1 d . . . . .
C2 C 0.2630(2) 0.5275(2) 0.6060(2) 0.0293(6) Uani 1 1 d . . . . .
C3 C 0.1704(2) 0.5234(2) 0.5888(3) 0.0396(8) Uani 1 1 d . . . . .
H3 H 0.139296 0.464380 0.584549 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1237(2) 0.6103(3) 0.5777(3) 0.0427(8) Uani 1 1 d . . . . .
H4 H 0.059934 0.609096 0.566100 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1676(2) 0.6977(2) 0.5831(2) 0.0408(8) Uani 1 1 d . . . . .
H5 H 0.133570 0.754288 0.574199 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2613(2) 0.7036(2) 0.6015(3) 0.0373(7) Uani 1 1 d . . . . .
H6 H 0.292132 0.762626 0.606592 0.045 Uiso 1 1 calc R U . . .
C7 C 0.3062(2) 0.6170(2) 0.6119(2) 0.0311(7) Uani 1 1 d . . . . .
S1 S 0.42142(5) 0.59247(5) 0.63727(6) 0.03141(18) Uani 1 1 d . . . . .
N1 N 0.41504(17) 0.47596(15) 0.6381(2) 0.0373(6) Uani 1 1 d . . . . .
O1 O 0.30571(16) 0.35967(15) 0.6199(2) 0.0473(6) Uani 1 1 d . . . . .
O2 O 0.44660(17) 0.63074(16) 0.72688(17) 0.0440(6) Uani 1 1 d . . . . .
O3 O 0.47925(15) 0.62648(16) 0.56245(18) 0.0428(6) Uani 1 1 d . . . . .
C8 C 0.1398(2) 0.0519(2) 0.3844(2) 0.0348(7) Uani 1 1 d . . . . .
C9 C 0.0730(2) -0.0294(2) 0.3944(2) 0.0298(7) Uani 1 1 d . . . . .
C10 C -0.0193(2) -0.0262(2) 0.4091(3) 0.0377(7) Uani 1 1 d . . . . .
H10 H -0.050544 0.032647 0.414253 0.045 Uiso 1 1 calc R U . . .
C11 C -0.0664(2) -0.1132(2) 0.4165(3) 0.0434(8) Uani 1 1 d . . . . .
H11 H -0.130532 -0.112813 0.426073 0.052 Uiso 1 1 calc R U . . .
C12 C -0.0205(2) -0.2005(2) 0.4099(3) 0.0423(8) Uani 1 1 d . . . . .
H12 H -0.053909 -0.257714 0.417279 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0714(2) -0.2048(2) 0.3931(2) 0.0380(8) Uani 1 1 d . . . . .
H13 H 0.102339 -0.263598 0.386415 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1176(2) -0.1177(2) 0.3862(2) 0.0298(6) Uani 1 1 d . . . . .
S2 S 0.23305(5) -0.09194(5) 0.36381(7) 0.0371(2) Uani 1 1 d . . . . .
N2 N 0.22476(16) 0.02504(16) 0.3668(3) 0.0414(7) Uani 1 1 d . . . . .
O4 O 0.11567(16) 0.13932(15) 0.3924(2) 0.0506(7) Uani 1 1 d . . . . .
O5 O 0.25946(19) -0.12648(17) 0.27379(19) 0.0520(7) Uani 1 1 d . . . . .
O6 O 0.29020(17) -0.12678(17) 0.4389(2) 0.0514(7) Uani 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
C1A N1A 1.494(5) . ?
C1A C2A 1.500(4) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A C3A 1.361(4) . ?
C2A C7A 1.377(4) . ?
C3A C4A 1.364(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.364(4) . ?
C5A C8A 1.469(4) . ?
C6A C7A 1.363(5) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A O1A 1.188(4) . ?
C8A O2A 1.320(4) . ?
N1A H1N 0.95(3) . ?
N1A H2N 0.90(4) . ?
N1A H3N 0.90(5) . ?
O2A H2AO 0.79(5) . ?
C1B C2B 1.499(4) . ?
C1B N1B 1.520(5) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
O2B C8B 1.307(4) . ?
O2B H2BO 0.87(6) . ?
C2B C7B 1.340(4) . ?
C2B C3B 1.376(4) . ?
C3B C4B 1.378(5) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.351(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.380(4) . ?
C5B C8B 1.485(4) . ?
C6B C7B 1.369(4) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B O1B 1.187(4) . ?
N1B H4N 0.92(5) . ?
N1B H5N 0.88(5) . ?
N1B H6N 0.93(4) . ?
C1 O1 1.258(4) . ?
C1 N1 1.307(4) . ?
C1 C2 1.482(4) . ?
C2 C3 1.354(5) . ?
C2 C7 1.384(4) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(4) . ?
C6 H6 0.9300 . ?
C7 S1 1.727(3) . ?
S1 O3 1.454(3) . ?
S1 O2 1.462(3) . ?
S1 N1 1.611(3) . ?
C8 O4 1.260(4) . ?
C8 N2 1.300(4) . ?
C8 C9 1.482(4) . ?
C9 C10 1.342(4) . ?
C9 C14 1.381(4) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.343(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 S2 1.725(3) . ?
S2 O5 1.454(3) . ?
S2 O6 1.455(3) . ?
S2 N2 1.620(3) . ?

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
N1A C1A C2A 111.2(3) . . ?
N1A C1A H1AA 109.4 . . ?
C2A C1A H1AA 109.4 . . ?
N1A C1A H1AB 109.4 . . ?
C2A C1A H1AB 109.4 . . ?
H1AA C1A H1AB 108.0 . . ?
C3A C2A C7A 118.3(3) . . ?
C3A C2A C1A 119.6(3) . . ?
C7A C2A C1A 122.1(3) . . ?
C2A C3A C4A 120.5(3) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A C5A 121.0(3) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C6A C5A C4A 118.5(3) . . ?
C6A C5A C8A 122.1(3) . . ?
C4A C5A C8A 119.4(3) . . ?
C7A C6A C5A 120.0(3) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C2A 121.7(3) . . ?
C6A C7A H7A 119.2 . . ?
C2A C7A H7A 119.2 . . ?
O1A C8A O2A 122.6(3) . . ?
O1A C8A C5A 121.8(3) . . ?
O2A C8A C5A 115.5(3) . . ?
C1A N1A H1N 116(3) . . ?
C1A N1A H2N 113(3) . . ?
H1N N1A H2N 105(4) . . ?
C1A N1A H3N 106(3) . . ?
H1N N1A H3N 105(4) . . ?
H2N N1A H3N 112(4) . . ?
C8A O2A H2AO 108(3) . . ?
C2B C1B N1B 110.1(3) . . ?
C2B C1B H1BA 109.6 . . ?
N1B C1B H1BA 109.6 . . ?
C2B C1B H1BB 109.6 . . ?
N1B C1B H1BB 109.6 . . ?
H1BA C1B H1BB 108.2 . . ?
C8B O2B H2BO 103(4) . . ?
C7B C2B C3B 119.0(3) . . ?
C7B C2B C1B 120.7(3) . . ?
C3B C2B C1B 120.3(3) . . ?
C2B C3B C4B 121.2(3) . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B H3B 119.4 . . ?
C5B C4B C3B 119.6(3) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C4B C5B C6B 118.9(3) . . ?
C4B C5B C8B 120.8(3) . . ?
C6B C5B C8B 120.2(3) . . ?
C7B C6B C5B 121.0(3) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C2B C7B C6B 120.3(3) . . ?
C2B C7B H7B 119.8 . . ?
C6B C7B H7B 119.8 . . ?
O1B C8B O2B 122.3(3) . . ?
O1B C8B C5B 122.4(3) . . ?
O2B C8B C5B 115.3(3) . . ?
C1B N1B H4N 109(3) . . ?
C1B N1B H5N 106(3) . . ?
H4N N1B H5N 111(4) . . ?
C1B N1B H6N 112(2) . . ?
H4N N1B H6N 104(4) . . ?
H5N N1B H6N 115(4) . . ?
O1 C1 N1 123.5(3) . . ?
O1 C1 C2 122.5(3) . . ?
N1 C1 C2 114.0(3) . . ?
C3 C2 C7 119.2(3) . . ?
C3 C2 C1 129.1(3) . . ?
C7 C2 C1 111.6(3) . . ?
C2 C3 C4 117.4(3) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 115.6(3) . . ?
C7 C6 H6 122.2 . . ?
C5 C6 H6 122.2 . . ?
C6 C7 C2 124.3(3) . . ?
C6 C7 S1 130.3(2) . . ?
C2 C7 S1 105.5(2) . . ?
O3 S1 O2 114.93(14) . . ?
O3 S1 N1 111.13(16) . . ?
O2 S1 N1 111.58(16) . . ?
O3 S1 C7 108.65(15) . . ?
O2 S1 C7 111.06(15) . . ?
N1 S1 C7 98.21(13) . . ?
C1 N1 S1 110.7(2) . . ?
O4 C8 N2 123.3(3) . . ?
O4 C8 C9 122.6(3) . . ?
N2 C8 C9 114.1(3) . . ?
C10 C9 C14 120.0(3) . . ?
C10 C9 C8 128.9(3) . . ?
C14 C9 C8 111.1(3) . . ?
C9 C10 C11 117.7(3) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 116.6(3) . . ?
C12 C13 H13 121.7 . . ?
C14 C13 H13 121.7 . . ?
C13 C14 C9 122.8(3) . . ?
C13 C14 S2 131.0(2) . . ?
C9 C14 S2 106.2(2) . . ?
O5 S2 O6 115.64(16) . . ?
O5 S2 N2 111.75(18) . . ?
O6 S2 N2 110.50(17) . . ?
O5 S2 C14 110.82(16) . . ?
O6 S2 C14 109.17(16) . . ?
N2 S2 C14 97.46(13) . . ?
C8 N2 S2 111.0(2) . . ?

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
N1A C1A C2A C3A 89.0(4) . . . . ?
N1A C1A C2A C7A -93.1(4) . . . . ?
C7A C2A C3A C4A -0.3(6) . . . . ?
C1A C2A C3A C4A 177.8(4) . . . . ?
C2A C3A C4A C5A -1.9(7) . . . . ?
C3A C4A C5A C6A 2.1(6) . . . . ?
C3A C4A C5A C8A -178.8(4) . . . . ?
C4A C5A C6A C7A -0.2(6) . . . . ?
C8A C5A C6A C7A -179.2(3) . . . . ?
C5A C6A C7A C2A -2.0(6) . . . . ?
C3A C2A C7A C6A 2.2(6) . . . . ?
C1A C2A C7A C6A -175.8(3) . . . . ?
C6A C5A C8A O1A 173.4(4) . . . . ?
C4A C5A C8A O1A -5.7(6) . . . . ?
C6A C5A C8A O2A -5.0(5) . . . . ?
C4A C5A C8A O2A 175.9(4) . . . . ?
N1B C1B C2B C7B 80.6(4) . . . . ?
N1B C1B C2B C3B -102.3(4) . . . . ?
C7B C2B C3B C4B -0.2(6) . . . . ?
C1B C2B C3B C4B -177.4(3) . . . . ?
C2B C3B C4B C5B -1.9(6) . . . . ?
C3B C4B C5B C6B 1.9(5) . . . . ?
C3B C4B C5B C8B -178.3(3) . . . . ?
C4B C5B C6B C7B 0.2(6) . . . . ?
C8B C5B C6B C7B -179.7(3) . . . . ?
C3B C2B C7B C6B 2.3(5) . . . . ?
C1B C2B C7B C6B 179.5(3) . . . . ?
C5B C6B C7B C2B -2.4(6) . . . . ?
C4B C5B C8B O1B 167.6(4) . . . . ?
C6B C5B C8B O1B -12.5(5) . . . . ?
C4B C5B C8B O2B -10.1(5) . . . . ?
C6B C5B C8B O2B 169.8(4) . . . . ?
O1 C1 C2 C3 1.3(6) . . . . ?
N1 C1 C2 C3 -179.1(4) . . . . ?
O1 C1 C2 C7 -179.9(3) . . . . ?
N1 C1 C2 C7 -0.3(4) . . . . ?
C7 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C2 -0.8(5) . . . . ?
C5 C6 C7 S1 -178.6(3) . . . . ?
C3 C2 C7 C6 0.1(5) . . . . ?
C1 C2 C7 C6 -178.9(3) . . . . ?
C3 C2 C7 S1 178.4(3) . . . . ?
C1 C2 C7 S1 -0.6(3) . . . . ?
C6 C7 S1 O3 -65.1(4) . . . . ?
C2 C7 S1 O3 116.7(2) . . . . ?
C6 C7 S1 O2 62.2(4) . . . . ?
C2 C7 S1 O2 -115.9(2) . . . . ?
C6 C7 S1 N1 179.2(3) . . . . ?
C2 C7 S1 N1 1.1(3) . . . . ?
O1 C1 N1 S1 -179.3(3) . . . . ?
C2 C1 N1 S1 1.1(4) . . . . ?
O3 S1 N1 C1 -115.0(3) . . . . ?
O2 S1 N1 C1 115.3(3) . . . . ?
C7 S1 N1 C1 -1.3(3) . . . . ?
O4 C8 C9 C10 2.8(6) . . . . ?
N2 C8 C9 C10 -177.4(4) . . . . ?
O4 C8 C9 C14 -177.5(3) . . . . ?
N2 C8 C9 C14 2.4(4) . . . . ?
C14 C9 C10 C11 0.6(5) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -2.2(6) . . . . ?
C11 C12 C13 C14 2.3(5) . . . . ?
C12 C13 C14 C9 -1.1(5) . . . . ?
C12 C13 C14 S2 -178.8(3) . . . . ?
C10 C9 C14 C13 -0.4(5) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C10 C9 C14 S2 177.8(3) . . . . ?
C8 C9 C14 S2 -1.9(3) . . . . ?
C13 C14 S2 O5 62.3(4) . . . . ?
C9 C14 S2 O5 -115.7(2) . . . . ?
C13 C14 S2 O6 -66.1(4) . . . . ?
C9 C14 S2 O6 115.8(2) . . . . ?
C13 C14 S2 N2 179.1(3) . . . . ?
C9 C14 S2 N2 1.0(3) . . . . ?
O4 C8 N2 S2 178.3(3) . . . . ?
C9 C8 N2 S2 -1.6(4) . . . . ?
O5 S2 N2 C8 116.3(3) . . . . ?
O6 S2 N2 C8 -113.4(3) . . . . ?
C14 S2 N2 C8 0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H3N O3 0.90(5) 2.30(5) 3.103(4) 148(4) 1_545 yes
N1A H1N O1 0.95(3) 1.86(3) 2.761(4) 158(4) 4 yes
N1A H2N O1A 0.90(4) 2.22(4) 2.767(5) 118(3) 4 yes
N1B H4N O4 0.92(5) 1.97(5) 2.876(4) 168(4) 4_565 yes
O2A H2AO O1 0.79(5) 1.88(5) 2.652(4) 164(5) . yes
O2B H2BO O4 0.87(6) 1.79(6) 2.623(3) 162(6) . yes
N1B H6N S2 0.93(4) 3.02(4) 3.844(3) 149(3) 1_565 yes
N1B H6N O6 0.93(4) 2.00(4) 2.924(4) 173(3) 1_565 yes
N1B H5N O3 0.88(5) 2.10(5) 2.947(4) 161(4) . yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_KB1245_0m
_database_code_depnum_ccdc_archive 'CCDC 2463054'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'Aminomethyl benzoic acid tartarate mono hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 N O2), C4 H4 O6, H2 O '
_chemical_formula_sum            'C20 H26 N2 O11'
_chemical_formula_weight         470.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3917(2)
_cell_length_b                   11.7324(2)
_cell_length_c                   14.9593(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.5494(7)
_cell_angle_gamma                90
_cell_volume                     2138.09(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.52

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24392
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6435
_reflns_number_gt                5246
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.5880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6435
_refine_ls_number_parameters     346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 1.32438(10) 0.85478(13) 0.40726(9) 0.0431(3) Uani 1 1 d . . . . .
H1AD H 1.343086 0.813881 0.355846 0.052 Uiso 1 1 calc R U . . .
H1AE H 1.324582 0.935630 0.393743 0.052 Uiso 1 1 calc R U . . .
C2A C 1.21123(9) 0.81988(11) 0.42021(8) 0.0343(2) Uani 1 1 d . . . . .
C3A C 1.18325(9) 0.70569(11) 0.42097(9) 0.0387(3) Uani 1 1 d . . . . .
H3A H 1.234943 0.650509 0.413979 0.046 Uiso 1 1 calc R U . . .
C4A C 1.07906(9) 0.67263(10) 0.43203(9) 0.0380(3) Uani 1 1 d . . . . .
H4A H 1.061587 0.595674 0.433863 0.046 Uiso 1 1 calc R U . . .
C5A C 1.00105(9) 0.75473(10) 0.44034(8) 0.0327(2) Uani 1 1 d . . . . .
C6A C 1.02852(11) 0.86887(12) 0.43952(11) 0.0466(3) Uani 1 1 d . . . . .
H6A H 0.976291 0.924137 0.444909 0.056 Uiso 1 1 calc R U . . .
C7A C 1.13375(11) 0.90128(12) 0.43067(11) 0.0471(3) Uani 1 1 d . . . . .
H7A H 1.152280 0.978149 0.431781 0.057 Uiso 1 1 calc R U . . .
C8A C 0.88749(9) 0.72305(12) 0.44992(9) 0.0381(3) Uani 1 1 d . . . . .
N1A N 1.40821(8) 0.83073(9) 0.48949(7) 0.0331(2) Uani 1 1 d . . . . .
H1 H 1.4774(15) 0.8484(15) 0.4779(12) 0.051(5) Uiso 1 1 d . . . . .
H2N H 1.4091(14) 0.7516(16) 0.5053(11) 0.050(4) Uiso 1 1 d . . . . .
H3N H 1.4005(14) 0.8714(15) 0.5397(12) 0.049(4) Uiso 1 1 d . . . . .
O1A O 0.86641(8) 0.61384(10) 0.44069(8) 0.0535(3) Uani 1 1 d D . . . .
H1AO H 0.8002(14) 0.600(2) 0.4502(16) 0.089(7) Uiso 1 1 d D . . . .
O2A O 0.82143(8) 0.79286(11) 0.46536(11) 0.0691(4) Uani 1 1 d . . . . .
C1B C -0.27271(10) 0.82759(12) 0.21767(9) 0.0402(3) Uani 1 1 d . . . . .
H1BD H -0.292039 0.779697 0.265195 0.048 Uiso 1 1 calc R U . . .
H1BE H -0.272564 0.906120 0.237961 0.048 Uiso 1 1 calc R U . . .
C2B C -0.15937(9) 0.79633(10) 0.20282(8) 0.0321(2) Uani 1 1 d . . . . .
C3B C -0.12517(9) 0.68388(11) 0.20579(9) 0.0380(3) Uani 1 1 d . . . . .
H3B H -0.173730 0.626150 0.214264 0.046 Uiso 1 1 calc R U . . .
C4B C -0.01871(9) 0.65664(10) 0.19619(9) 0.0370(3) Uani 1 1 d . . . . .
H4B H 0.003483 0.580822 0.197895 0.044 Uiso 1 1 calc R U . . .
C5B C 0.05457(8) 0.74228(10) 0.18406(8) 0.0301(2) Uani 1 1 d . . . . .
C6B C 0.01945(10) 0.85476(11) 0.17841(10) 0.0411(3) Uani 1 1 d . . . . .
H6B H 0.067299 0.912490 0.168444 0.049 Uiso 1 1 calc R U . . .
C7B C -0.08693(10) 0.88100(11) 0.18764(10) 0.0421(3) Uani 1 1 d . . . . .
H7B H -0.110063 0.956540 0.183576 0.051 Uiso 1 1 calc R U . . .
C8B C 0.17175(9) 0.71673(11) 0.18068(8) 0.0342(2) Uani 1 1 d . . . . .
N1B N -0.35647(8) 0.81384(9) 0.13372(8) 0.0346(2) Uani 1 1 d . . . . .
H4N H -0.3402(16) 0.8528(16) 0.0833(13) 0.058(5) Uiso 1 1 d . . . . .
H5N H -0.4235(15) 0.8408(15) 0.1452(12) 0.053(5) Uiso 1 1 d . . . . .
H6N H -0.3663(14) 0.7363(16) 0.1204(12) 0.050(4) Uiso 1 1 d . . . . .
O1B O 0.19739(8) 0.60861(9) 0.18921(8) 0.0483(3) Uani 1 1 d . . . . .
H1BO H 0.2675(18) 0.6007(19) 0.1885(14) 0.074(6) Uiso 1 1 d . . . . .
O2B O 0.23715(8) 0.79086(10) 0.17263(10) 0.0595(3) Uani 1 1 d . . . . .
C1 C 0.62002(8) 0.47881(9) 0.44308(7) 0.0273(2) Uani 1 1 d . . . . .
C2 C 0.59713(7) 0.48209(9) 0.33904(7) 0.02609(19) Uani 1 1 d . . . . .
H2 H 0.665610 0.498635 0.317588 0.031 Uiso 1 1 calc R U . . .
C3 C 0.51346(8) 0.57638(9) 0.30625(7) 0.0274(2) Uani 1 1 d . . . . .
H3 H 0.544220 0.649633 0.329972 0.033 Uiso 1 1 calc R U . . .
C4 C 0.49329(9) 0.58039(9) 0.20211(7) 0.0293(2) Uani 1 1 d . . . . .
O1 O 0.68062(7) 0.55666(8) 0.48299(6) 0.0392(2) Uani 1 1 d . . . . .
O2 O 0.57503(7) 0.40319(7) 0.48200(6) 0.03443(18) Uani 1 1 d . . . . .
O3 O 0.55347(6) 0.37721(7) 0.30068(6) 0.03247(18) Uani 1 1 d . . . . .
H3O H 0.6067(15) 0.3301(15) 0.3075(11) 0.046(4) Uiso 1 1 d . . . . .
O4 O 0.41259(6) 0.55893(8) 0.33574(6) 0.03540(19) Uani 1 1 d . . . . .
H4O H 0.4203(15) 0.5695(15) 0.3948(13) 0.057(5) Uiso 1 1 d . . . . .
O5 O 0.39574(7) 0.56811(9) 0.15887(6) 0.0415(2) Uani 1 1 d . . . . .
O6 O 0.57448(7) 0.59515(8) 0.16571(6) 0.0392(2) Uani 1 1 d . . . . .
O1W O 0.60793(10) 0.85919(15) 0.43611(12) 0.0814(5) Uani 1 1 d . . . . .
H1W H 0.612(2) 0.919(2) 0.4063(16) 0.083(7) Uiso 1 1 d . . . . .
H2W H 0.670(2) 0.8299(19) 0.4438(15) 0.075(6) 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
C1A N1A 1.4845(15) . ?
C1A C2A 1.5069(16) . ?
C1A H1AD 0.9700 . ?
C1A H1AE 0.9700 . ?
C2A C7A 1.3833(19) . ?
C2A C3A 1.3843(18) . ?
C3A C4A 1.3868(16) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3863(16) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3823(18) . ?
C5A C8A 1.4876(15) . ?
C6A C7A 1.3876(18) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A O2A 1.2098(16) . ?
C8A O1A 1.3098(17) . ?
N1A H1 0.929(19) . ?
N1A H2N 0.957(19) . ?
N1A H3N 0.910(18) . ?
O1A H1AO 0.874(16) . ?
C1B N1B 1.4843(16) . ?
C1B C2B 1.5068(15) . ?
C1B H1BD 0.9700 . ?
C1B H1BE 0.9700 . ?
C2B C3B 1.3839(17) . ?
C2B C7B 1.3853(17) . ?
C3B C4B 1.3901(15) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.3883(15) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.3873(17) . ?
C5B C8B 1.4927(15) . ?
C6B C7B 1.3850(17) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B O2B 1.2097(15) . ?
C8B O1B 1.3082(16) . ?
N1B H4N 0.935(19) . ?
N1B H5N 0.934(19) . ?
N1B H6N 0.935(18) . ?
O1B H1BO 0.88(2) . ?
C1 O2 1.2473(13) . ?
C1 O1 1.2612(13) . ?
C1 C2 1.5305(14) . ?
C2 O3 1.4221(13) . ?
C2 C3 1.5340(14) . ?
C2 H2 0.9800 . ?
C3 O4 1.4144(12) . ?
C3 C4 1.5327(15) . ?
C3 H3 0.9800 . ?
C4 O6 1.2406(13) . ?
C4 O5 1.2705(14) . ?
O3 H3O 0.852(18) . ?
O4 H4O 0.880(19) . ?
O1W H1W 0.83(3) . ?
O1W H2W 0.83(2) . ?

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
N1A C1A C2A 111.61(9) . . ?
N1A C1A H1AD 109.3 . . ?
C2A C1A H1AD 109.3 . . ?
N1A C1A H1AE 109.3 . . ?
C2A C1A H1AE 109.3 . . ?
H1AD C1A H1AE 108.0 . . ?
C7A C2A C3A 119.16(11) . . ?
C7A C2A C1A 120.55(12) . . ?
C3A C2A C1A 120.29(12) . . ?
C2A C3A C4A 120.78(11) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C5A C4A C3A 119.74(11) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C6A C5A C4A 119.70(11) . . ?
C6A C5A C8A 118.80(11) . . ?
C4A C5A C8A 121.50(11) . . ?
C5A C6A C7A 120.23(12) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
C2A C7A C6A 120.36(12) . . ?
C2A C7A H7A 119.8 . . ?
C6A C7A H7A 119.8 . . ?
O2A C8A O1A 123.62(12) . . ?
O2A C8A C5A 122.30(13) . . ?
O1A C8A C5A 114.09(11) . . ?
C1A N1A H1 109.4(11) . . ?
C1A N1A H2N 111.3(10) . . ?
H1 N1A H2N 107.0(15) . . ?
C1A N1A H3N 114.9(11) . . ?
H1 N1A H3N 106.1(15) . . ?
H2N N1A H3N 107.6(15) . . ?
C8A O1A H1AO 110.1(17) . . ?
N1B C1B C2B 112.03(10) . . ?
N1B C1B H1BD 109.2 . . ?
C2B C1B H1BD 109.2 . . ?
N1B C1B H1BE 109.2 . . ?
C2B C1B H1BE 109.2 . . ?
H1BD C1B H1BE 107.9 . . ?
C3B C2B C7B 119.02(10) . . ?
C3B C2B C1B 121.03(11) . . ?
C7B C2B C1B 119.94(11) . . ?
C2B C3B C4B 120.45(11) . . ?
C2B C3B H3B 119.8 . . ?
C4B C3B H3B 119.8 . . ?
C5B C4B C3B 120.19(11) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6B C5B C4B 119.41(10) . . ?
C6B C5B C8B 119.03(10) . . ?
C4B C5B C8B 121.51(10) . . ?
C7B C6B C5B 119.94(11) . . ?
C7B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C6B C7B C2B 120.94(11) . . ?
C6B C7B H7B 119.5 . . ?
C2B C7B H7B 119.5 . . ?
O2B C8B O1B 123.49(11) . . ?
O2B C8B C5B 122.18(11) . . ?
O1B C8B C5B 114.32(10) . . ?
C1B N1B H4N 114.1(12) . . ?
C1B N1B H5N 108.3(11) . . ?
H4N N1B H5N 108.3(16) . . ?
C1B N1B H6N 109.3(10) . . ?
H4N N1B H6N 110.0(15) . . ?
H5N N1B H6N 106.5(15) . . ?
C8B O1B H1BO 109.0(15) . . ?
O2 C1 O1 124.92(10) . . ?
O2 C1 C2 118.50(9) . . ?
O1 C1 C2 116.53(9) . . ?
O3 C2 C1 111.99(8) . . ?
O3 C2 C3 108.06(8) . . ?
C1 C2 C3 109.38(8) . . ?
O3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
O4 C3 C4 109.42(8) . . ?
O4 C3 C2 112.34(8) . . ?
C4 C3 C2 108.79(8) . . ?
O4 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
O6 C4 O5 124.40(11) . . ?
O6 C4 C3 117.13(10) . . ?
O5 C4 C3 118.48(9) . . ?
C2 O3 H3O 106.5(11) . . ?
C3 O4 H4O 110.7(12) . . ?
H1W O1W H2W 106(2) . . ?

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
N1A C1A C2A C7A 107.82(14) . . . . ?
N1A C1A C2A C3A -72.74(16) . . . . ?
C7A C2A C3A C4A 0.0(2) . . . . ?
C1A C2A C3A C4A -179.43(12) . . . . ?
C2A C3A C4A C5A 1.5(2) . . . . ?
C3A C4A C5A C6A -1.4(2) . . . . ?
C3A C4A C5A C8A 178.40(12) . . . . ?
C4A C5A C6A C7A -0.2(2) . . . . ?
C8A C5A C6A C7A -179.98(13) . . . . ?
C3A C2A C7A C6A -1.6(2) . . . . ?
C1A C2A C7A C6A 177.84(13) . . . . ?
C5A C6A C7A C2A 1.7(2) . . . . ?
C6A C5A C8A O2A -7.0(2) . . . . ?
C4A C5A C8A O2A 173.24(14) . . . . ?
C6A C5A C8A O1A 173.41(13) . . . . ?
C4A C5A C8A O1A -6.38(18) . . . . ?
N1B C1B C2B C3B -82.24(15) . . . . ?
N1B C1B C2B C7B 99.00(14) . . . . ?
C7B C2B C3B C4B 1.77(19) . . . . ?
C1B C2B C3B C4B -177.00(12) . . . . ?
C2B C3B C4B C5B 0.4(2) . . . . ?
C3B C4B C5B C6B -2.25(19) . . . . ?
C3B C4B C5B C8B 175.23(12) . . . . ?
C4B C5B C6B C7B 2.0(2) . . . . ?
C8B C5B C6B C7B -175.60(12) . . . . ?
C5B C6B C7B C2B 0.2(2) . . . . ?
C3B C2B C7B C6B -2.1(2) . . . . ?
C1B C2B C7B C6B 176.70(13) . . . . ?
C6B C5B C8B O2B -0.4(2) . . . . ?
C4B C5B C8B O2B -177.94(13) . . . . ?
C6B C5B C8B O1B 178.07(12) . . . . ?
C4B C5B C8B O1B 0.58(17) . . . . ?
O2 C1 C2 O3 -17.93(12) . . . . ?
O1 C1 C2 O3 164.64(9) . . . . ?
O2 C1 C2 C3 101.84(11) . . . . ?
O1 C1 C2 C3 -75.59(11) . . . . ?
O3 C2 C3 O4 62.22(11) . . . . ?
C1 C2 C3 O4 -59.94(11) . . . . ?
O3 C2 C3 C4 -59.08(10) . . . . ?
C1 C2 C3 C4 178.76(8) . . . . ?
O4 C3 C4 O6 -179.91(9) . . . . ?
C2 C3 C4 O6 -56.84(12) . . . . ?
O4 C3 C4 O5 -0.18(14) . . . . ?
C2 C3 C4 O5 122.89(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1AO O1 0.874(16) 1.720(17) 2.5854(12) 170(2) . yes
O3 H3O O2B 0.852(18) 1.958(18) 2.7457(12) 153.2(16) 2_645 yes
N1A H1 O1W 0.929(19) 1.842(19) 2.7564(15) 167.6(16) 1_655 yes
N1A H2N O2 0.957(19) 1.833(19) 2.7794(14) 169.2(16) 3_766 yes
N1A H3N O5 0.910(18) 1.929(18) 2.8278(14) 169.0(16) 4_676 yes
N1A H3N O6 0.910(18) 2.620(17) 3.1562(13) 118.4(13) 4_676 yes
O4 H4O O2 0.880(19) 1.861(19) 2.7389(12) 175.3(18) 3_666 yes
C1A H1AE O6 0.97 2.50 3.3491(16) 145.7 2_755 yes
O1W H1W O5 0.83(3) 2.00(3) 2.8294(18) 172(2) 2_655 yes
O1W H2W O2A 0.83(2) 1.90(2) 2.7152(16) 169(2) . yes
O1B H1BO O4 0.88(2) 2.62(2) 3.1805(13) 122.6(17) . yes
O1B H1BO O5 0.88(2) 1.77(2) 2.6233(12) 165(2) . yes
N1B H4N O1 0.935(19) 1.89(2) 2.8255(14) 173.6(17) 4_475 yes
C1B H1BE O4 0.97 2.60 3.2408(16) 124.1 2 yes
N1B H5N O2 0.934(19) 2.525(18) 3.1167(13) 121.5(13) 2 yes
N1B H5N O3 0.934(19) 1.977(19) 2.8900(13) 165.4(16) 2 yes
N1B H6N O6 0.935(18) 1.980(18) 2.7739(14) 141.5(15) 1_455 yes

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol-water'
####################################################################### 
# 
# 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_KB1276_0m
_database_code_depnum_ccdc_archive 'CCDC 2463053'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminomethylbenzoic acid oxalate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N O2, 0.5(C2 O4)'
_chemical_formula_sum            'C9 H10 N O4'
_chemical_formula_weight         196.18

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.6096(4)
_cell_length_b                   7.0278(4)
_cell_length_c                   11.2902(8)
_cell_angle_alpha                72.9234(19)
_cell_angle_beta                 74.834(2)
_cell_angle_gamma                69.8700(17)
_cell_volume                     463.10(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6134
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      30.55

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             206
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11773
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2801
_reflns_number_gt                2310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²+0.0663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     143
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.7427(2) 0.7659(2) 0.31190(11) 0.0446(3) Uani 1 1 d . . . . .
H1A H 0.894609 0.701654 0.279039 0.054 Uiso 1 1 calc R U . . .
H1B H 0.718135 0.915265 0.290085 0.054 Uiso 1 1 calc R U . . .
C2 C 0.59677(18) 0.71393(18) 0.25054(10) 0.0373(2) Uani 1 1 d . . . . .
C3 C 0.6087(2) 0.50887(19) 0.26177(13) 0.0468(3) Uani 1 1 d . . . . .
H3 H 0.708878 0.402280 0.306398 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4726(2) 0.46108(18) 0.20707(13) 0.0457(3) Uani 1 1 d . . . . .
H4 H 0.479309 0.323019 0.217061 0.055 Uiso 1 1 calc R U . . .
C5 C 0.32670(17) 0.61846(16) 0.13753(10) 0.0349(2) Uani 1 1 d . . . . .
C6 C 0.3159(2) 0.82315(18) 0.12481(13) 0.0461(3) Uani 1 1 d . . . . .
H6 H 0.219128 0.929649 0.077903 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4496(2) 0.87007(19) 0.18205(13) 0.0486(3) Uani 1 1 d . . . . .
H7 H 0.439856 1.008296 0.174153 0.058 Uiso 1 1 calc R U . . .
C8 C 0.18324(17) 0.56677(17) 0.07775(11) 0.0378(2) Uani 1 1 d . . . . .
N1 N 0.70245(13) 0.69435(13) 0.45038(8) 0.0301(2) Uani 1 1 d . . . . .
H1N H 0.742(2) 0.555(2) 0.4750(14) 0.048(4) Uiso 1 1 d . . . . .
H2N H 0.556(3) 0.753(3) 0.4814(15) 0.058(4) Uiso 1 1 d . . . . .
H3N H 0.792(2) 0.740(2) 0.4841(14) 0.050(4) Uiso 1 1 d . . . . .
O1 O 0.06061(16) 0.71492(14) 0.00950(10) 0.0556(3) Uani 1 1 d D . . . .
H1O H -0.007(5) 0.666(5) -0.030(3) 0.175(13) Uiso 1 1 d D . . . .
O2 O 0.18749(17) 0.38006(14) 0.09734(10) 0.0552(3) Uani 1 1 d . . . . .
C9 C -0.10229(14) 1.09800(14) 0.49610(10) 0.0290(2) Uani 1 1 d . . . . .
O3 O -0.27543(11) 1.07158(12) 0.48878(9) 0.0438(2) Uani 1 1 d . . . . .
O4 O -0.07640(12) 1.26592(11) 0.49632(9) 0.0432(2) Uani 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
C1 N1 1.4767(15) . ?
C1 C2 1.5114(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.3816(16) . ?
C2 C3 1.3852(16) . ?
C3 C4 1.3870(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.3864(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.3815(16) . ?
C5 C8 1.4841(13) . ?
C6 C7 1.3897(15) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.2565(14) . ?
C8 O1 1.2687(13) . ?
N1 H1N 0.901(16) . ?
N1 H2N 0.931(17) . ?
N1 H3N 0.954(15) . ?
O1 H1O 0.902(18) . ?
C9 O3 1.2472(10) . ?
C9 O4 1.2502(11) . ?
C9 C9 1.5629(16) 2_576 ?

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 C2 112.51(9) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C7 C2 C3 118.87(9) . . ?
C7 C2 C1 120.59(10) . . ?
C3 C2 C1 120.54(10) . . ?
C2 C3 C4 120.60(10) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.21(11) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.41(9) . . ?
C6 C5 C8 120.49(9) . . ?
C4 C5 C8 120.10(10) . . ?
C5 C6 C7 120.06(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.83(11) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O2 C8 O1 123.13(10) . . ?
O2 C8 C5 118.93(9) . . ?
O1 C8 C5 117.93(10) . . ?
C1 N1 H1N 112.0(9) . . ?
C1 N1 H2N 108.9(10) . . ?
H1N N1 H2N 111.7(14) . . ?
C1 N1 H3N 108.7(9) . . ?
H1N N1 H3N 106.2(13) . . ?
H2N N1 H3N 109.2(14) . . ?
C8 O1 H1O 111(2) . . ?
O3 C9 O4 126.35(8) . . ?
O3 C9 C9 116.50(9) . 2_576 ?
O4 C9 C9 117.15(9) . 2_576 ?

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
N1 C1 C2 C7 118.04(13) . . . . ?
N1 C1 C2 C3 -62.12(16) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 179.05(12) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 C5 C8 179.23(12) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C8 C5 C6 C7 179.44(12) . . . . ?
C3 C2 C7 C6 -0.2(2) . . . . ?
C1 C2 C7 C6 179.62(12) . . . . ?
C5 C6 C7 C2 1.0(2) . . . . ?
C6 C5 C8 O2 -175.75(12) . . . . ?
C4 C5 C8 O2 4.08(18) . . . . ?
C6 C5 C8 O1 3.84(18) . . . . ?
C4 C5 C8 O1 -176.33(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H2N O3 0.931(17) 1.846(17) 2.7564(11) 165.3(15) 2_576 yes
N1 H1N O4 0.901(16) 1.950(16) 2.8145(11) 160.1(13) 1_645 yes
N1 H3N O3 0.954(15) 2.234(15) 2.8658(11) 122.9(12) 1_655 yes
N1 H3N O4 0.954(15) 1.938(15) 2.8108(10) 150.9(13) 2_676 yes
O1 H1O O2 0.902(18) 1.730(19) 2.6174(11) 167(3) 2_565 yes

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol-water'
####################################################################### 
# 
# 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_KB914_0m
_database_code_depnum_ccdc_archive 'CCDC 2463049'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-11-12 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid-tartarate'
_chemical_name_common            'Aminocaproic acid-tartarate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N O2), C4 H6 O6, C4 H4 O6'
_chemical_formula_sum            'C20 H38 N2 O16'
_chemical_formula_weight         562.52

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.6376(3)
_cell_length_b                   9.5114(4)
_cell_length_c                   15.9873(6)
_cell_angle_alpha                79.9178(12)
_cell_angle_beta                 80.8899(12)
_cell_angle_gamma                88.4671(13)
_cell_volume                     1276.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.388
_cell_measurement_theta_max      30.204

_exptl_crystal_description       needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            38215
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7796
_reflns_number_gt                5417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.3086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7796
_refine_ls_number_parameters     456
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1A C 0.63389(17) 0.41018(15) 0.56568(9) 0.0355(3) Uani 1 1 d . . . . .
C2A C 0.69571(18) 0.32107(16) 0.49899(9) 0.0419(3) Uani 1 1 d . . . . .
H2AA H 0.607537 0.291428 0.475426 0.050 Uiso 1 1 calc R U . . .
H2AB H 0.741893 0.235412 0.527504 0.050 Uiso 1 1 calc R U . . .
C3A C 0.81529(17) 0.38994(15) 0.42533(9) 0.0370(3) Uani 1 1 d . . . . .
H3AA H 0.903575 0.422613 0.447522 0.044 Uiso 1 1 calc R U . . .
H3AB H 0.769131 0.472297 0.393404 0.044 Uiso 1 1 calc R U . . .
C4A C 0.87220(17) 0.28451(16) 0.36560(9) 0.0378(3) Uani 1 1 d . . . . .
H4AA H 0.917696 0.202516 0.398237 0.045 Uiso 1 1 calc R U . . .
H4AB H 0.782749 0.251159 0.344718 0.045 Uiso 1 1 calc R U . . .
C5A C 0.99267(17) 0.34655(15) 0.28899(9) 0.0363(3) Uani 1 1 d . . . . .
H5AA H 0.943826 0.419874 0.251542 0.044 Uiso 1 1 calc R U . . .
H5AB H 1.076740 0.390608 0.308934 0.044 Uiso 1 1 calc R U . . .
C6A C 1.05959(16) 0.23198(14) 0.23909(8) 0.0335(3) Uani 1 1 d . . . . .
H6AA H 1.107251 0.158224 0.276847 0.040 Uiso 1 1 calc R U . . .
H6AB H 0.975418 0.188547 0.218880 0.040 Uiso 1 1 calc R U . . .
N1A N 1.17846(14) 0.29055(13) 0.16458(7) 0.0323(2) Uani 1 1 d D . . . .
H1N H 1.211(2) 0.2176(15) 0.1373(11) 0.062(6) Uiso 1 1 d D . . . .
H2N H 1.2599(16) 0.3289(18) 0.1802(11) 0.053(5) Uiso 1 1 d D . . . .
H3N H 1.135(2) 0.3587(16) 0.1302(11) 0.065(6) Uiso 1 1 d D . . . .
O1A O 0.67684(18) 0.53154(13) 0.56089(8) 0.0689(4) Uani 1 1 d . . . . .
O2A O 0.53311(16) 0.34426(14) 0.62699(8) 0.0583(3) Uani 1 1 d D . . . .
H2AO H 0.497(3) 0.394(2) 0.6678(13) 0.109(9) Uiso 1 1 d D . . . .
C1B C 0.6883(4) 0.8727(4) 0.5826(2) 0.0363(6) Uani 0.819(7) 1 d . U P A 1
C2B C 0.7082(6) 0.8698(8) 0.4883(3) 0.0407(10) Uani 0.819(7) 1 d . U P A 1
H2BA H 0.632423 0.803985 0.477931 0.049 Uiso 0.819(7) 1 calc R U P A 1
H2BB H 0.685730 0.964091 0.458277 0.049 Uiso 0.819(7) 1 calc R U P A 1
O1B O 0.7040(3) 0.98198(17) 0.61076(11) 0.0523(7) Uani 0.819(7) 1 d . U P A 1
O2B O 0.6584(5) 0.7546(3) 0.6367(3) 0.0468(7) Uani 0.819(7) 1 d . U P A 1
H2BO H 0.657(4) 0.669(3) 0.610(2) 0.091(12) Uiso 0.819(7) 1 d . . P A 1
C1' C 0.6369(17) 0.873(2) 0.5748(11) 0.041(3) Uani 0.181(7) 1 d . U P A 2
C2' C 0.684(3) 0.872(3) 0.4777(14) 0.034(2) Uani 0.181(7) 1 d . U P A 2
H2'A H 0.666848 0.966265 0.446180 0.041 Uiso 0.181(7) 1 calc R U P A 2
H2'B H 0.617076 0.805529 0.460456 0.041 Uiso 0.181(7) 1 calc R U P A 2
O1' O 0.594(2) 0.9738(9) 0.5977(5) 0.074(5) Uani 0.181(7) 1 d . U P A 2
O2' O 0.617(3) 0.751(3) 0.6279(15) 0.088(7) Uani 0.181(7) 1 d . U P A 2
H2'O H 0.559020 0.762417 0.671894 0.132 Uiso 0.181(7) 1 calc R U P A 2
C3B C 0.86889(17) 0.82640(17) 0.45160(8) 0.0385(3) Uani 1 1 d . U . . .
H3BA H 0.893278 0.733570 0.482726 0.046 Uiso 1 1 calc R U . A 1
H3BB H 0.944683 0.894340 0.459633 0.046 Uiso 1 1 calc R U . A 1
C4B C 0.88397(16) 0.81907(17) 0.35674(8) 0.0372(3) Uani 1 1 d . U . . .
H4BA H 0.858864 0.912033 0.326065 0.045 Uiso 1 1 calc R U . . .
H4BB H 0.807344 0.751560 0.349124 0.045 Uiso 1 1 calc R U . . .
C5B C 1.04506(16) 0.77523(16) 0.31676(8) 0.0355(3) Uani 1 1 d . . . . .
H5BA H 1.122745 0.842796 0.323095 0.043 Uiso 1 1 calc R U . . .
H5BB H 1.071171 0.681786 0.346396 0.043 Uiso 1 1 calc R U . . .
C6B C 1.04844(16) 0.77072(16) 0.22282(8) 0.0362(3) Uani 1 1 d . . . . .
H6BA H 0.976037 0.697810 0.217397 0.043 Uiso 1 1 calc R U . . .
H6BB H 1.012408 0.861794 0.194882 0.043 Uiso 1 1 calc R U . . .
N1B N 1.20588(15) 0.74046(14) 0.17787(8) 0.0371(3) Uani 1 1 d D . . . .
H4N H 1.197(3) 0.719(2) 0.1265(9) 0.081(7) Uiso 1 1 d D . . . .
H5N H 1.249(2) 0.6632(14) 0.2058(11) 0.058(5) Uiso 1 1 d D . . . .
H6N H 1.2756(18) 0.8100(15) 0.1745(12) 0.056(5) Uiso 1 1 d D . . . .
C1 C 0.48054(14) 0.51858(13) 0.79003(7) 0.0269(2) Uani 1 1 d . . . . .
C2 C 0.38554(14) 0.60308(12) 0.85374(7) 0.0250(2) Uani 1 1 d . . . . .
H2 H 0.330433 0.680908 0.821848 0.030 Uiso 1 1 calc R U . . .
C3 C 0.26465(13) 0.50499(12) 0.91634(7) 0.0243(2) Uani 1 1 d . . . . .
H3 H 0.196381 0.465691 0.882645 0.029 Uiso 1 1 calc R U . . .
C4 C 0.16316(13) 0.59146(12) 0.97635(8) 0.0246(2) Uani 1 1 d . . . . .
O1 O 0.39920(12) 0.45984(12) 0.74673(6) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.62570(10) 0.51302(10) 0.78450(6) 0.0350(2) Uani 1 1 d . . . . .
O3 O 0.48786(10) 0.66183(9) 0.89979(6) 0.0313(2) Uani 1 1 d . . . . .
H3O H 0.447054 0.732458 0.916985 0.047 Uiso 1 1 calc R U . . .
O4 O 0.33947(11) 0.38952(9) 0.96312(6) 0.0306(2) Uani 1 1 d . . . . .
H4O H 0.378617 0.417825 1.000644 0.046 Uiso 1 1 calc R U . . .
O5 O 0.07573(10) 0.68413(10) 0.93897(6) 0.0331(2) Uani 1 1 d . . . . .
O6 O 0.17245(12) 0.57025(10) 1.05337(6) 0.0378(2) Uani 1 1 d . . . . .
C5 C -0.17184(14) 0.91917(12) 1.00627(8) 0.0264(2) Uani 1 1 d . . . . .
C6 C -0.26132(14) 1.00065(12) 1.07274(8) 0.0266(2) Uani 1 1 d . . . . .
H6 H -0.185440 1.042366 1.100940 0.032 Uiso 1 1 calc R U . . .
C7 C -0.36701(14) 0.89696(13) 1.14101(8) 0.0277(2) Uani 1 1 d . U . . .
H7 H -0.300838 0.820130 1.165326 0.033 Uiso 1 1 calc R U . B 1
C8 C -0.4351(7) 0.9770(6) 1.2120(4) 0.0292(8) Uani 0.78(2) 1 d . U P C 1
O11 O -0.3587(7) 1.0512(6) 1.2442(4) 0.0426(8) Uani 0.78(2) 1 d . U P C 1
O12 O -0.5895(7) 0.9559(8) 1.2366(4) 0.0422(8) Uani 0.78(2) 1 d . U P C 1
H12O H -0.617(3) 0.988(3) 1.2848(19) 0.078(9) Uiso 0.78(2) 1 d . . P C 1
C8D C -0.480(2) 0.970(2) 1.2106(12) 0.028(3) Uani 0.22(2) 1 d . U P C 2
O11D O -0.395(3) 1.023(3) 1.2528(14) 0.051(3) Uani 0.22(2) 1 d D U P C 2
H11D H -0.416(12) 1.050(10) 1.302(3) 0.076 Uiso 0.22(2) 1 d D U P C 2
O12D O -0.619(3) 0.964(3) 1.2174(17) 0.051(4) Uani 0.22(2) 1 d . U P C 2
O7 O -0.07061(11) 0.83141(10) 1.03704(6) 0.0338(2) Uani 1 1 d D . . . .
H7O H -0.022(2) 0.777(2) 0.9997(12) 0.097(8) Uiso 1 1 d D . . . .
O8 O -0.20156(12) 0.93851(10) 0.93291(6) 0.0368(2) Uani 1 1 d . . . . .
O9 O -0.35064(11) 1.11201(9) 1.03329(6) 0.0330(2) Uani 1 1 d . . . . .
H9O H -0.386447 1.085809 0.994015 0.050 Uiso 1 1 calc R U . . .
O10 O -0.47988(10) 0.83483(9) 1.10368(6) 0.0320(2) Uani 1 1 d . . . . .
H10O H -0.442672 0.763607 1.085672 0.048 Uiso 1 1 calc R U . . .


_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
C1A O1A 1.2079(18) . ?
C1A O2A 1.2866(18) . ?
C1A C2A 1.5007(19) . ?
C2A C3A 1.5045(19) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3A C4A 1.5229(19) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A C5A 1.5190(19) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5A C6A 1.5109(18) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6A N1A 1.4814(17) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
N1A H1N 0.898(9) . ?
N1A H2N 0.890(9) . ?
N1A H3N 0.891(9) . ?
O2A H2AO 0.884(10) . ?
C1B O1B 1.222(4) . ?
C1B O2B 1.296(5) . ?
C1B C2B 1.496(6) . ?
C2B C3B 1.495(5) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
O2B H2BO 0.98(3) . ?
C1' O1' 1.123(19) . ?
C1' O2' 1.31(3) . ?
C1' C2' 1.54(2) . ?
C2' C3B 1.65(2) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
O2' H2'O 0.8200 . ?
C3B C4B 1.5152(18) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C5B 1.5163(18) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C5B C6B 1.5057(18) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C6B N1B 1.4800(17) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
N1B H4N 0.895(9) . ?
N1B H5N 0.896(9) . ?
N1B H6N 0.895(9) . ?
C1 O2 1.2432(15) . ?
C1 O1 1.2631(15) . ?
C1 C2 1.5309(16) . ?
C2 O3 1.4184(14) . ?
C2 C3 1.5352(17) . ?
C2 H2 0.9800 . ?
C3 O4 1.4180(14) . ?
C3 C4 1.5286(15) . ?
C3 H3 0.9800 . ?
C4 O6 1.2276(15) . ?
C4 O5 1.2757(14) . ?
O3 H3O 0.8200 . ?
O4 H4O 0.8200 . ?
C5 O8 1.2217(15) . ?
C5 O7 1.2871(15) . ?
C5 C6 1.5244(16) . ?
C6 O9 1.4111(14) . ?
C6 C7 1.5340(17) . ?
C6 H6 0.9800 . ?
C7 O10 1.4123(15) . ?
C7 C8 1.510(6) . ?
C7 C8D 1.601(17) . ?
C7 H7 0.9800 . ?
C8 O11 1.208(7) . ?
C8 O12 1.339(7) . ?
O12 H12O 0.87(3) . ?
C8D O12D 1.19(2) . ?
C8D O11D 1.24(2) . ?
O11D H11D 0.863(10) . ?
O7 H7O 0.904(9) . ?
O9 H9O 0.8200 . ?
O10 H10O 0.8200 . ?

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
O1A C1A O2A 124.50(13) . . ?
O1A C1A C2A 122.12(13) . . ?
O2A C1A C2A 113.38(12) . . ?
C1A C2A C3A 116.75(12) . . ?
C1A C2A H2AA 108.1 . . ?
C3A C2A H2AA 108.1 . . ?
C1A C2A H2AB 108.1 . . ?
C3A C2A H2AB 108.1 . . ?
H2AA C2A H2AB 107.3 . . ?
C2A C3A C4A 110.58(12) . . ?
C2A C3A H3AA 109.5 . . ?
C4A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
C4A C3A H3AB 109.5 . . ?
H3AA C3A H3AB 108.1 . . ?
C5A C4A C3A 113.78(12) . . ?
C5A C4A H4AA 108.8 . . ?
C3A C4A H4AA 108.8 . . ?
C5A C4A H4AB 108.8 . . ?
C3A C4A H4AB 108.8 . . ?
H4AA C4A H4AB 107.7 . . ?
C6A C5A C4A 110.99(11) . . ?
C6A C5A H5AA 109.4 . . ?
C4A C5A H5AA 109.4 . . ?
C6A C5A H5AB 109.4 . . ?
C4A C5A H5AB 109.4 . . ?
H5AA C5A H5AB 108.0 . . ?
N1A C6A C5A 111.66(11) . . ?
N1A C6A H6AA 109.3 . . ?
C5A C6A H6AA 109.3 . . ?
N1A C6A H6AB 109.3 . . ?
C5A C6A H6AB 109.3 . . ?
H6AA C6A H6AB 107.9 . . ?
C6A N1A H1N 106.8(13) . . ?
C6A N1A H2N 112.5(12) . . ?
H1N N1A H2N 109.9(17) . . ?
C6A N1A H3N 109.1(13) . . ?
H1N N1A H3N 110.8(17) . . ?
H2N N1A H3N 107.8(17) . . ?
C1A O2A H2AO 115.1(17) . . ?
O1B C1B O2B 118.5(3) . . ?
O1B C1B C2B 122.3(4) . . ?
O2B C1B C2B 119.2(4) . . ?
C3B C2B C1B 113.6(3) . . ?
C3B C2B H2BA 108.8 . . ?
C1B C2B H2BA 108.8 . . ?
C3B C2B H2BB 108.8 . . ?
C1B C2B H2BB 108.8 . . ?
H2BA C2B H2BB 107.7 . . ?
C1B O2B H2BO 114.9(18) . . ?
O1' C1' O2' 119.6(18) . . ?
O1' C1' C2' 119.9(16) . . ?
O2' C1' C2' 119.1(19) . . ?
C1' C2' C3B 113.0(15) . . ?
C1' C2' H2'A 109.0 . . ?
C3B C2' H2'A 109.0 . . ?
C1' C2' H2'B 109.0 . . ?
C3B C2' H2'B 109.0 . . ?
H2'A C2' H2'B 107.8 . . ?
C1' O2' H2'O 109.5 . . ?
C2B C3B C4B 112.5(2) . . ?
C4B C3B C2' 103.8(8) . . ?
C2B C3B H3BA 109.1 . . ?
C4B C3B H3BA 109.1 . . ?
C2B C3B H3BB 109.1 . . ?
C4B C3B H3BB 109.1 . . ?
H3BA C3B H3BB 107.8 . . ?
C3B C4B C5B 114.33(12) . . ?
C3B C4B H4BA 108.7 . . ?
C5B C4B H4BA 108.7 . . ?
C3B C4B H4BB 108.7 . . ?
C5B C4B H4BB 108.7 . . ?
H4BA C4B H4BB 107.6 . . ?
C6B C5B C4B 110.44(11) . . ?
C6B C5B H5BA 109.6 . . ?
C4B C5B H5BA 109.6 . . ?
C6B C5B H5BB 109.6 . . ?
C4B C5B H5BB 109.6 . . ?
H5BA C5B H5BB 108.1 . . ?
N1B C6B C5B 113.37(12) . . ?
N1B C6B H6BA 108.9 . . ?
C5B C6B H6BA 108.9 . . ?
N1B C6B H6BB 108.9 . . ?
C5B C6B H6BB 108.9 . . ?
H6BA C6B H6BB 107.7 . . ?
C6B N1B H4N 109.1(15) . . ?
C6B N1B H5N 111.9(12) . . ?
H4N N1B H5N 105.5(18) . . ?
C6B N1B H6N 113.4(12) . . ?
H4N N1B H6N 112.9(19) . . ?
H5N N1B H6N 103.8(17) . . ?
O2 C1 O1 125.89(11) . . ?
O2 C1 C2 119.64(11) . . ?
O1 C1 C2 114.47(11) . . ?
O3 C2 C1 109.66(9) . . ?
O3 C2 C3 110.12(9) . . ?
C1 C2 C3 109.91(9) . . ?
O3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
O4 C3 C4 111.51(9) . . ?
O4 C3 C2 110.91(9) . . ?
C4 C3 C2 109.85(9) . . ?
O4 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
O6 C4 O5 125.62(11) . . ?
O6 C4 C3 119.93(10) . . ?
O5 C4 C3 114.44(10) . . ?
C2 O3 H3O 109.5 . . ?
C3 O4 H4O 109.5 . . ?
O8 C5 O7 126.72(11) . . ?
O8 C5 C6 120.28(10) . . ?
O7 C5 C6 112.99(10) . . ?
O9 C6 C5 110.91(10) . . ?
O9 C6 C7 110.70(10) . . ?
C5 C6 C7 109.49(9) . . ?
O9 C6 H6 108.6 . . ?
C5 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
O10 C7 C8 114.4(2) . . ?
O10 C7 C6 110.81(10) . . ?
C8 C7 C6 107.8(2) . . ?
O10 C7 C8D 99.9(9) . . ?
C6 C7 C8D 115.2(7) . . ?
O10 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
O11 C8 O12 123.2(6) . . ?
O11 C8 C7 123.8(4) . . ?
O12 C8 C7 113.0(5) . . ?
C8 O12 H12O 107.9(19) . . ?
O12D C8D O11D 130.8(19) . . ?
O12D C8D C7 122.0(17) . . ?
O11D C8D C7 107.1(13) . . ?
C8D O11D H11D 131(7) . . ?
C5 O7 H7O 114.2(15) . . ?
C6 O9 H9O 109.5 . . ?
C7 O10 H10O 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
O1A C1A C2A C3A 0.3(2) . . . . ?
O2A C1A C2A C3A -179.52(14) . . . . ?
C1A C2A C3A C4A 177.33(13) . . . . ?
C2A C3A C4A C5A 179.56(13) . . . . ?
C3A C4A C5A C6A 172.54(12) . . . . ?
C4A C5A C6A N1A -179.46(12) . . . . ?
O1B C1B C2B C3B 95.3(5) . . . . ?
O2B C1B C2B C3B -82.4(5) . . . . ?
O1' C1' C2' C3B 120.1(19) . . . . ?
O2' C1' C2' C3B -74(2) . . . . ?
C1B C2B C3B C4B 177.8(3) . . . . ?
C1' C2' C3B C4B 174.8(15) . . . . ?
C2B C3B C4B C5B -179.9(3) . . . . ?
C2' C3B C4B C5B -178.7(11) . . . . ?
C3B C4B C5B C6B 179.89(13) . . . . ?
C4B C5B C6B N1B 175.15(12) . . . . ?
O2 C1 C2 O3 -1.31(15) . . . . ?
O1 C1 C2 O3 178.88(11) . . . . ?
O2 C1 C2 C3 -122.51(12) . . . . ?
O1 C1 C2 C3 57.68(14) . . . . ?
O3 C2 C3 O4 -61.18(11) . . . . ?
C1 C2 C3 O4 59.74(12) . . . . ?
O3 C2 C3 C4 62.55(12) . . . . ?
C1 C2 C3 C4 -176.53(9) . . . . ?
O4 C3 C4 O6 10.64(16) . . . . ?
C2 C3 C4 O6 -112.73(12) . . . . ?
O4 C3 C4 O5 -170.60(10) . . . . ?
C2 C3 C4 O5 66.02(13) . . . . ?
O8 C5 C6 O9 -11.45(16) . . . . ?
O7 C5 C6 O9 169.92(10) . . . . ?
O8 C5 C6 C7 111.01(13) . . . . ?
O7 C5 C6 C7 -67.63(13) . . . . ?
O9 C6 C7 O10 60.34(12) . . . . ?
C5 C6 C7 O10 -62.24(12) . . . . ?
O9 C6 C7 C8 -65.5(3) . . . . ?
C5 C6 C7 C8 171.9(2) . . . . ?
O9 C6 C7 C8D -52.1(9) . . . . ?
C5 C6 C7 C8D -174.7(9) . . . . ?
O10 C7 C8 O11 -170.6(5) . . . . ?
C6 C7 C8 O11 -46.9(6) . . . . ?
O10 C7 C8 O12 10.1(6) . . . . ?
C6 C7 C8 O12 133.8(5) . . . . ?
O10 C7 C8D O12D -2(2) . . . . ?
C6 C7 C8D O12D 117(2) . . . . ?
O10 C7 C8D O11D 176.1(16) . . . . ?
C6 C7 C8D O11D -65.2(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1N O8 0.898(9) 2.022(11) 2.8780(15) 158.9(18) 2_666 yes
N1A H3N O5 0.891(9) 2.350(17) 2.9330(15) 123.1(15) 2_666 yes
N1A H2N O2 0.890(9) 2.027(11) 2.8553(15) 154.3(16) 2_766 yes
N1A H2N O3 0.890(9) 2.341(16) 2.9221(14) 123.0(14) 2_766 yes
N1B H5N O2 0.896(9) 1.966(12) 2.8058(16) 155.4(17) 2_766 yes
N1B H4N O6 0.895(9) 2.023(14) 2.8286(15) 149.0(19) 1_654 yes
N1A H3N O6 0.891(9) 2.170(14) 2.9338(15) 143.4(17) 1_654 yes
O3 H3O O9 0.82 1.91 2.7285(12) 175.1 2_577 yes
O12 H12O O1B 0.87(3) 1.79(3) 2.644(6) 166(3) 2_577 yes
N1B H6N O10 0.895(9) 2.231(15) 2.8841(15) 129.5(15) 1_754 yes
N1B H6N O12 0.895(9) 2.281(13) 3.098(6) 151.6(16) 1_754 yes
O4 H4O O3 0.82 2.13 2.8085(13) 139.6 2_667 yes
O9 H9O O10 0.82 2.11 2.7895(13) 140.1 2_477 yes
O10 H10O O4 0.82 1.91 2.7229(12) 174.1 2_567 yes
O7 H7O O5 0.904(9) 1.561(10) 2.4626(12) 175(2) . yes
O2A H2AO O1 0.884(10) 1.615(11) 2.4857(14) 168(3) . yes
O2B H2BO O1A 0.98(3) 1.64(3) 2.611(3) 173(3) . yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_KB878_0m
_database_code_depnum_ccdc_archive 'CCDC 2463048'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid oxalate hemi trihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N O2), 2(C2 H O4), 3(H2 O)'
_chemical_formula_sum            'C16 H36 N2 O15'
_chemical_formula_weight         496.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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'

_cell_length_a                   30.203(4)
_cell_length_b                   5.6916(8)
_cell_length_c                   14.254(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.433(6)
_cell_angle_gamma                90
_cell_volume                     2417.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7033
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      30.415

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14805
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.401
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3660
_reflns_number_gt                2951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.9402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3660
_refine_ls_number_parameters     182
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.79037(4) 1.2806(2) 0.88537(9) 0.0409(3) Uani 1 1 d . . . . .
C2 C 0.76001(4) 1.0700(2) 0.87746(10) 0.0435(3) Uani 1 1 d . . . . .
H2A H 0.767022 0.979446 0.935665 0.052 Uiso 1 1 calc R U . . .
H2B H 0.766725 0.972023 0.825896 0.052 Uiso 1 1 calc R U . . .
C3 C 0.71008(4) 1.1220(2) 0.86015(9) 0.0401(3) Uani 1 1 d . . . . .
H3A H 0.702026 1.202569 0.799788 0.048 Uiso 1 1 calc R U . . .
H3B H 0.702875 1.224493 0.909904 0.048 Uiso 1 1 calc R U . . .
C4 C 0.68324(4) 0.8953(2) 0.85895(9) 0.0421(3) Uani 1 1 d . . . . .
H4A H 0.690811 0.793883 0.809244 0.050 Uiso 1 1 calc R U . . .
H4B H 0.691882 0.815030 0.919189 0.050 Uiso 1 1 calc R U . . .
C5 C 0.63284(4) 0.9343(2) 0.84240(9) 0.0408(3) Uani 1 1 d . . . . .
H5A H 0.624832 1.026790 0.894279 0.049 Uiso 1 1 calc R U . . .
H5B H 0.624235 1.022507 0.784026 0.049 Uiso 1 1 calc R U . . .
C6 C 0.60731(4) 0.7043(2) 0.83557(8) 0.0385(2) Uani 1 1 d . . . . .
H6A H 0.613216 0.617542 0.780366 0.046 Uiso 1 1 calc R U . . .
H6B H 0.617635 0.610181 0.891615 0.046 Uiso 1 1 calc R U . . .
N1 N 0.55825(3) 0.74620(19) 0.82761(7) 0.0357(2) Uani 1 1 d . . . . .
H1NA H 0.5504(5) 0.834(3) 0.7759(11) 0.052(4) Uiso 1 1 d . . . . .
H2NB H 0.5520(5) 0.815(3) 0.8780(11) 0.047(4) Uiso 1 1 d . . . . .
H3NC H 0.5419(6) 0.603(3) 0.8189(11) 0.064(5) Uiso 1 1 d . . . . .
O1 O 0.77774(3) 1.48210(17) 0.88063(8) 0.0587(3) Uani 1 1 d . . . . .
O2 O 0.83405(3) 1.23741(19) 0.89855(9) 0.0567(3) Uani 1 1 d D . . . .
H2O H 0.8386(6) 1.090(3) 0.9054(13) 0.073(6) Uiso 1 1 d D . . . .
C7 C 0.54727(3) -0.00436(16) 0.57784(6) 0.02517(18) Uani 1 1 d . . . . .
C8 C 0.55184(3) -0.25221(16) 0.53596(7) 0.02630(19) Uani 1 1 d . . . . .
O3 O 0.53559(3) 0.01175(14) 0.65645(5) 0.0430(2) Uani 1 1 d . . . . .
O4 O 0.55570(3) 0.16315(13) 0.52612(5) 0.03816(19) Uani 1 1 d . . . . .
O5 O 0.55944(3) -0.28180(15) 0.45689(6) 0.0458(2) Uani 1 1 d . . . . .
O6 O 0.54620(3) -0.41896(14) 0.59625(6) 0.0445(2) Uani 1 1 d D . . . .
H6O H 0.5490(6) -0.557(3) 0.5731(11) 0.066(5) Uiso 1 1 d D . . . .
O1W O 0.500000 0.3796(2) 0.750000 0.0366(2) Uani 1 2 d DS T P . .
H1W H 0.5117(5) 0.288(3) 0.7135(10) 0.057(4) Uiso 1 1 d D . . . .
O2W O 0.85199(4) 0.7920(2) 0.89973(12) 0.0778(4) Uani 1 1 d D . . . .
H2W H 0.8324(7) 0.692(4) 0.9046(15) 0.102(8) Uiso 1 1 d D . . . .
H3W H 0.8771(6) 0.731(4) 0.9214(14) 0.091(7) Uiso 1 1 d 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
C1 O1 1.2069(16) . ?
C1 O2 1.3248(15) . ?
C1 C2 1.5024(16) . ?
C2 C3 1.5169(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5224(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.5179(15) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5143(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.4868(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N1 H1NA 0.890(16) . ?
N1 H2NB 0.867(15) . ?
N1 H3NC 0.951(19) . ?
O2 H2O 0.856(15) . ?
C7 O3 1.2321(12) . ?
C7 O4 1.2564(11) . ?
C7 C8 1.5468(13) . ?
C8 O5 1.1983(12) . ?
C8 O6 1.3100(12) . ?
O6 H6O 0.862(14) . ?
O1W H1W 0.853(12) . ?
O1W H1W 0.853(12) 2_656 ?
O2W H2W 0.831(16) . ?
O2W H3W 0.844(15) . ?

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 O2 118.86(11) . . ?
O1 C1 C2 124.79(11) . . ?
O2 C1 C2 116.35(11) . . ?
C1 C2 C3 115.75(11) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 C3 C4 110.46(10) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 113.36(10) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.76(10) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 110.92(10) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C6 N1 H1NA 106.3(9) . . ?
C6 N1 H2NB 111.1(10) . . ?
H1NA N1 H2NB 111.5(14) . . ?
C6 N1 H3NC 111.2(10) . . ?
H1NA N1 H3NC 108.2(14) . . ?
H2NB N1 H3NC 108.6(14) . . ?
C1 O2 H2O 109.7(13) . . ?
O3 C7 O4 126.36(9) . . ?
O3 C7 C8 118.41(8) . . ?
O4 C7 C8 115.22(8) . . ?
O5 C8 O6 125.50(9) . . ?
O5 C8 C7 122.28(9) . . ?
O6 C8 C7 112.22(8) . . ?
C8 O6 H6O 112.2(11) . . ?
H1W O1W H1W 104(2) . 2_656 ?
H2W O2W H3W 107(2) . . ?

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 1.4(2) . . . . ?
O2 C1 C2 C3 -178.66(11) . . . . ?
C1 C2 C3 C4 -176.93(11) . . . . ?
C2 C3 C4 C5 179.71(10) . . . . ?
C3 C4 C5 C6 176.45(10) . . . . ?
C4 C5 C6 N1 175.19(9) . . . . ?
O3 C7 C8 O5 173.76(10) . . . . ?
O4 C7 C8 O5 -5.57(14) . . . . ?
O3 C7 C8 O6 -5.85(13) . . . . ?
O4 C7 C8 O6 174.82(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1NA O3 0.890(16) 1.968(16) 2.8562(13) 175.6(14) 1_565 yes
N1 H2NB O4 0.867(15) 2.099(15) 2.8897(13) 151.3(14) 6_566 yes
N1 H3NC O1W 0.951(19) 1.943(19) 2.8347(13) 155.3(15) . yes
O2 H2O O2W 0.856(15) 1.746(16) 2.5917(16) 169.3(19) . yes
O6 H6O O4 0.862(14) 1.752(14) 2.6138(11) 179.0(17) 1_545 yes
O1W H1W O3 0.853(12) 1.961(13) 2.7903(11) 163.9(15) . yes
O2W H2W O1 0.831(16) 2.022(17) 2.8310(15) 164(2) 1_545 yes
O2W H2W O2 0.831(16) 2.59(2) 3.2023(16) 132(2) 1_545 yes
O2W H3W O4 0.844(15) 2.082(16) 2.9090(14) 166(2) 4_656 yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_KB1720_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2463052'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminomethyl benzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.6402(3)
_cell_length_b                   8.6125(3)
_cell_length_c                   6.3343(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     744.13(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4199
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      29.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9260
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.797
_diffrn_reflns_theta_max         30.641
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2176
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.892
_reflns_Friedel_fraction_full    0.952

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.0612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2176
_refine_ls_number_parameters     112
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.44924(13) 0.7078(2) 0.1996(4) 0.0399(5) Uani 1 1 d . . . . .
H1A H 0.448597 0.653229 0.065603 0.048 Uiso 1 1 calc R U . . .
H1B H 0.392219 0.675030 0.279519 0.048 Uiso 1 1 calc R U . . .
C2 C 0.54159(12) 0.6651(2) 0.3205(3) 0.0332(4) Uani 1 1 d . . . . .
C3 C 0.61377(13) 0.5781(2) 0.2219(3) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.604412 0.544159 0.083986 0.044 Uiso 1 1 calc R U . . .
C4 C 0.70038(11) 0.5410(2) 0.3278(3) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.747884 0.481142 0.260955 0.042 Uiso 1 1 calc R U . . .
C5 C 0.71593(11) 0.59320(18) 0.5326(3) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.64336(12) 0.68021(19) 0.6322(3) 0.0329(4) Uani 1 1 d . . . . .
H6 H 0.653011 0.715364 0.769464 0.039 Uiso 1 1 calc R U . . .
C7 C 0.55635(12) 0.71479(19) 0.5270(4) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.507787 0.771527 0.595342 0.042 Uiso 1 1 calc R U . . .
C8 C 0.81005(12) 0.5554(2) 0.6477(3) 0.0342(4) Uani 1 1 d . . . . .
N1 N 0.44357(10) 0.87759(18) 0.1606(3) 0.0312(3) Uani 1 1 d . . . . .
H1N H 0.505(2) 0.914(3) 0.135(5) 0.070(9) Uiso 1 1 d . . . . .
H2N H 0.4197(18) 0.931(3) 0.275(5) 0.049(7) Uiso 1 1 d . . . . .
H3N H 0.3998(17) 0.900(2) 0.054(5) 0.041(6) Uiso 1 1 d . . . . .
O1 O 0.87913(8) 0.49799(17) 0.5397(3) 0.0454(4) Uani 1 1 d . . . . .
O2 O 0.81383(12) 0.5834(2) 0.8392(3) 0.0633(5) Uani 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
C1 N1 1.485(2) . ?
C1 C2 1.519(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.386(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 C8 1.512(2) . ?
C6 C7 1.393(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.238(3) . ?
C8 O1 1.265(2) . ?
N1 H1N 0.91(3) . ?
N1 H2N 0.92(3) . ?
N1 H3N 0.92(3) . ?

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 C2 111.42(14) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C7 119.16(16) . . ?
C3 C2 C1 119.52(19) . . ?
C7 C2 C1 121.30(17) . . ?
C2 C3 C4 120.57(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.26(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.26(15) . . ?
C4 C5 C8 120.70(15) . . ?
C6 C5 C8 120.05(16) . . ?
C5 C6 C7 120.24(17) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.48(17) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O2 C8 O1 125.10(17) . . ?
O2 C8 C5 117.79(17) . . ?
O1 C8 C5 117.11(16) . . ?
C1 N1 H1N 108.4(17) . . ?
C1 N1 H2N 112.4(16) . . ?
H1N N1 H2N 107(2) . . ?
C1 N1 H3N 111.2(13) . . ?
H1N N1 H3N 113(2) . . ?
H2N N1 H3N 104(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.91(3) 1.84(3) 2.7407(19) 170(3) 4_654 yes
N1 H2N O1 0.92(3) 1.87(3) 2.772(2) 168(2) 3_465 yes
N1 H3N O2 0.92(3) 1.80(3) 2.718(2) 172(2) 3_464 yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_KB1170_0m
_database_code_depnum_ccdc_archive 'CCDC 2463056'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminomethyl benzoic acid orotate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N O2 +, C5 H3 N2 O4 -'
_chemical_formula_sum            'C13 H13 N3 O6'
_chemical_formula_weight         307.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   5.8889(6)
_cell_length_b                   10.2677(10)
_cell_length_c                   11.2466(10)
_cell_angle_alpha                102.250(3)
_cell_angle_beta                 93.673(3)
_cell_angle_gamma                91.141(4)
_cell_volume                     662.79(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5693
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.4

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12857
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         30.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4021
_reflns_number_gt                2849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+0.0853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C -0.3177(2) -0.03285(15) 0.23528(13) 0.0374(3) Uani 1 1 d . . . . .
H1D H -0.347769 -0.109072 0.270890 0.045 Uiso 1 1 calc R U . . .
H1DE H -0.458837 0.013433 0.230303 0.045 Uiso 1 1 calc R U . . .
C2 C -0.1436(2) 0.05954(13) 0.31765(12) 0.0316(3) Uani 1 1 d . . . . .
C3 C 0.0671(2) 0.01348(14) 0.35060(13) 0.0368(3) Uani 1 1 d . . . . .
H3 H 0.104465 -0.074005 0.318789 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2218(2) 0.09828(14) 0.43106(13) 0.0351(3) Uani 1 1 d . . . . .
H4 H 0.361943 0.067103 0.453354 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1677(2) 0.22937(13) 0.47826(12) 0.0308(3) Uani 1 1 d . . . . .
C6 C -0.0412(2) 0.27589(14) 0.44457(13) 0.0361(3) Uani 1 1 d . . . . .
H6 H -0.077527 0.363803 0.475290 0.043 Uiso 1 1 calc R U . . .
C7 C -0.1959(2) 0.19066(14) 0.36475(13) 0.0362(3) Uani 1 1 d . . . . .
H7 H -0.336137 0.221951 0.342669 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3363(2) 0.31738(13) 0.56445(12) 0.0324(3) Uani 1 1 d . . . . .
N1 N -0.2434(2) -0.08079(13) 0.11036(12) 0.0363(3) Uani 1 1 d . . . . .
H1NA H -0.343(4) -0.155(2) 0.0672(18) 0.063(6) Uiso 1 1 d . . . . .
H1NB H -0.104(4) -0.119(2) 0.110(2) 0.075(7) Uiso 1 1 d . . . . .
H1NC H -0.235(3) -0.016(2) 0.0686(18) 0.056(5) Uiso 1 1 d . . . . .
O1 O 0.50452(18) 0.27543(10) 0.61071(10) 0.0443(3) Uani 1 1 d . . . . .
O2 O 0.2859(2) 0.44440(11) 0.58651(11) 0.0483(3) Uani 1 1 d . . . . .
H2O H 0.388(4) 0.491(2) 0.636(2) 0.064(6) Uiso 1 1 d . . . . .
C9 C 0.7645(2) 0.58420(13) 0.77711(12) 0.0314(3) Uani 1 1 d . . . . .
C10 C 0.9257(2) 0.68007(14) 0.84847(13) 0.0339(3) Uani 1 1 d . . . . .
H10 H 0.898465 0.770568 0.858947 0.041 Uiso 1 1 calc R U . . .
C11 C 1.1172(2) 0.64010(13) 0.90072(12) 0.0316(3) Uani 1 1 d . . . . .
C13 C 1.2938(3) 0.73833(16) 0.97797(13) 0.0422(4) Uani 1 1 d . . . . .
C12 C 1.0127(2) 0.40877(13) 0.82075(12) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.8199(2) 0.45377(11) 0.76918(11) 0.0327(3) Uani 1 1 d . . . . .
H2N H 0.724(4) 0.391(2) 0.7207(19) 0.064(6) Uiso 1 1 d . . . . .
N3 N 1.1607(2) 0.50810(12) 0.88734(11) 0.0350(3) Uani 1 1 d . . . . .
H3N H 1.292(4) 0.482(2) 0.9212(18) 0.055(5) Uiso 1 1 d . . . . .
O3 O 0.58711(18) 0.61240(10) 0.72519(10) 0.0432(3) Uani 1 1 d . . . . .
O4 O 1.0465(2) 0.29057(10) 0.80837(11) 0.0526(3) Uani 1 1 d . . . . .
O5 O 1.4684(2) 0.68891(14) 1.01513(12) 0.0597(4) Uani 1 1 d . . . . .
O6 O 1.2461(3) 0.85899(12) 0.99876(12) 0.0646(4) Uani 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
C1 N1 1.4836(19) . ?
C1 C2 1.5084(18) . ?
C1 H1D 0.9700 . ?
C1 H1DE 0.9700 . ?
C2 C7 1.3866(19) . ?
C2 C3 1.393(2) . ?
C3 C4 1.3909(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3894(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(2) . ?
C5 C8 1.4872(17) . ?
C6 C7 1.3900(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.2179(17) . ?
C8 O2 1.3185(17) . ?
N1 H1NA 0.98(2) . ?
N1 H1NB 0.92(2) . ?
N1 H1NC 0.89(2) . ?
O2 H2O 0.86(2) . ?
C9 O3 1.2334(17) . ?
C9 N2 1.3706(17) . ?
C9 C10 1.4300(18) . ?
C10 C11 1.349(2) . ?
C10 H10 0.9300 . ?
C11 N3 1.3628(18) . ?
C11 C13 1.5246(19) . ?
C13 O5 1.243(2) . ?
C13 O6 1.252(2) . ?
C12 O4 1.2137(16) . ?
C12 N2 1.3746(18) . ?
C12 N3 1.3847(17) . ?
N2 H2N 0.91(2) . ?
N3 H3N 0.91(2) . ?

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 C2 112.95(11) . . ?
N1 C1 H1D 109.0 . . ?
C2 C1 H1D 109.0 . . ?
N1 C1 H1DE 109.0 . . ?
C2 C1 H1DE 109.0 . . ?
H1D C1 H1DE 107.8 . . ?
C7 C2 C3 119.33(12) . . ?
C7 C2 C1 119.91(13) . . ?
C3 C2 C1 120.73(12) . . ?
C4 C3 C2 120.03(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.28(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.80(12) . . ?
C6 C5 C8 121.22(12) . . ?
C4 C5 C8 118.98(12) . . ?
C5 C6 C7 119.79(12) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.77(13) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O1 C8 O2 123.33(12) . . ?
O1 C8 C5 122.90(12) . . ?
O2 C8 C5 113.77(12) . . ?
C1 N1 H1NA 109.6(11) . . ?
C1 N1 H1NB 112.8(14) . . ?
H1NA N1 H1NB 102.1(18) . . ?
C1 N1 H1NC 112.8(12) . . ?
H1NA N1 H1NC 111.8(18) . . ?
H1NB N1 H1NC 107.2(18) . . ?
C8 O2 H2O 110.0(14) . . ?
O3 C9 N2 120.60(12) . . ?
O3 C9 C10 124.49(12) . . ?
N2 C9 C10 114.91(12) . . ?
C11 C10 C9 120.43(13) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 N3 120.97(12) . . ?
C10 C11 C13 122.42(13) . . ?
N3 C11 C13 116.60(13) . . ?
O5 C13 O6 127.17(14) . . ?
O5 C13 C11 115.96(14) . . ?
O6 C13 C11 116.86(15) . . ?
O4 C12 N2 121.56(12) . . ?
O4 C12 N3 123.62(13) . . ?
N2 C12 N3 114.81(12) . . ?
C9 N2 C12 126.53(11) . . ?
C9 N2 H2N 116.4(14) . . ?
C12 N2 H2N 116.9(14) . . ?
C11 N3 C12 122.33(12) . . ?
C11 N3 H3N 120.3(13) . . ?
C12 N3 H3N 117.4(13) . . ?

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
N1 C1 C2 C7 116.87(15) . . . . ?
N1 C1 C2 C3 -65.37(18) . . . . ?
C7 C2 C3 C4 0.7(2) . . . . ?
C1 C2 C3 C4 -177.06(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3 C4 C5 C8 179.77(13) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C8 C5 C6 C7 -179.37(13) . . . . ?
C3 C2 C7 C6 -0.3(2) . . . . ?
C1 C2 C7 C6 177.48(13) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C6 C5 C8 O1 168.20(14) . . . . ?
C4 C5 C8 O1 -11.8(2) . . . . ?
C6 C5 C8 O2 -11.39(19) . . . . ?
C4 C5 C8 O2 168.60(13) . . . . ?
O3 C9 C10 C11 -179.08(13) . . . . ?
N2 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 N3 -0.3(2) . . . . ?
C9 C10 C11 C13 -179.77(12) . . . . ?
C10 C11 C13 O5 -176.10(14) . . . . ?
N3 C11 C13 O5 4.44(19) . . . . ?
C10 C11 C13 O6 5.1(2) . . . . ?
N3 C11 C13 O6 -174.39(14) . . . . ?
O3 C9 N2 C12 178.97(13) . . . . ?
C10 C9 N2 C12 -1.0(2) . . . . ?
O4 C12 N2 C9 -179.97(14) . . . . ?
N3 C12 N2 C9 0.5(2) . . . . ?
C10 C11 N3 C12 -0.3(2) . . . . ?
C13 C11 N3 C12 179.20(12) . . . . ?
O4 C12 N3 C11 -179.31(14) . . . . ?
N2 C12 N3 C11 0.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1NA O5 0.98(2) 1.89(2) 2.8549(17) 168.0(18) 1_344 yes
N1 H1NA O6 0.98(2) 2.51(2) 3.179(2) 125.7(15) 1_344 yes
N1 H1NB O4 0.92(2) 2.18(2) 2.7604(18) 120.7(17) 2_656 yes
N1 H1NB O6 0.92(2) 2.47(2) 3.237(2) 141.6(18) 1_444 yes
N1 H1NC O6 0.89(2) 1.92(2) 2.8067(19) 170.0(17) 2_666 yes
O2 H2O O3 0.86(2) 1.79(2) 2.6338(15) 169(2) . yes
N2 H2N O1 0.91(2) 1.93(2) 2.8344(15) 173(2) . yes
N3 H3N O5 0.91(2) 2.47(2) 3.298(2) 151.7(17) 2_867 yes

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_KB880_0m
_database_code_depnum_ccdc_archive 'CCDC 2463050'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-11-12 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Aminocaproic acid-caffeic acid hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C9 H7 O4), 2(C6 H13.50 N O2), C6 H14 N O2, 2.597(H2 O)'
_chemical_formula_sum            'C36 H60.19 N3 O16.60'
_chemical_formula_weight         800.61

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.5263(19)
_cell_length_b                   12.781(4)
_cell_length_c                   21.505(6)
_cell_angle_alpha                77.876(7)
_cell_angle_beta                 88.418(7)
_cell_angle_gamma                79.491(7)
_cell_volume                     1988.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.14

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5922
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST PHOTON-III'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            38806
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.937
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9819
_reflns_number_gt                6151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.3045P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9819
_refine_ls_number_parameters     577
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1A C 0.4604(2) 0.29886(12) 0.97809(7) 0.0433(4) Uani 1 1 d . . . . .
H1AA H 0.543572 0.293946 1.012673 0.052 Uiso 1 1 calc R U . . .
H1AB H 0.346433 0.342488 0.986692 0.052 Uiso 1 1 calc R U . . .
C2A C 0.5356(2) 0.35371(12) 0.91650(7) 0.0439(4) Uani 1 1 d . . . . .
H2AA H 0.455180 0.355206 0.881723 0.053 Uiso 1 1 calc R U . . .
H2AB H 0.652070 0.311604 0.908985 0.053 Uiso 1 1 calc R U . . .
C3A C 0.5578(2) 0.46958(11) 0.91733(7) 0.0418(3) Uani 1 1 d . . . . .
H3AA H 0.443075 0.510199 0.927800 0.050 Uiso 1 1 calc R U . . .
H3AB H 0.644535 0.467584 0.950293 0.050 Uiso 1 1 calc R U . . .
C4A C 0.6211(2) 0.52774(12) 0.85430(8) 0.0476(4) Uani 1 1 d . . . . .
H4AA H 0.534915 0.529255 0.821267 0.057 Uiso 1 1 calc R U . . .
H4AB H 0.736371 0.487497 0.843994 0.057 Uiso 1 1 calc R U . . .
C5A C 0.6415(2) 0.64309(11) 0.85513(8) 0.0424(4) Uani 1 1 d . . . . .
H5AA H 0.528716 0.680561 0.869238 0.051 Uiso 1 1 calc R U . . .
H5AB H 0.733842 0.640280 0.886341 0.051 Uiso 1 1 calc R U . . .
C6A C 0.6903(2) 0.70921(13) 0.79290(8) 0.0489(4) Uani 1 1 d . . . . .
O1A O 0.6915(2) 0.81060(9) 0.79027(6) 0.0638(4) Uani 1 1 d . . . . .
H1O H 0.740821 0.817438 0.822344 0.096 Uiso 0.5 1 calc R U P . .
O2A O 0.7243(2) 0.67109(10) 0.74534(7) 0.0768(4) Uani 1 1 d . . . . .
N1A N 0.4315(2) 0.18790(10) 0.97525(7) 0.0496(3) Uani 1 1 d . . . . .
H1N H 0.346257 0.192777 0.946388 0.074 Uiso 1 1 calc R U . . .
H2N H 0.396954 0.155205 1.013168 0.074 Uiso 1 1 calc R U . . .
H3N H 0.534114 0.149300 0.964490 0.074 Uiso 1 1 calc R U . . .
C2B C 0.9362(3) 1.00134(12) 0.59552(8) 0.0501(4) Uani 1 1 d . U . . .
H2BA H 0.851364 0.992783 0.564612 0.060 Uiso 1 1 calc R U . A 1
H2BB H 1.056002 0.967598 0.584755 0.060 Uiso 1 1 calc R U . A 1
C3B C 0.9323(2) 1.12174(12) 0.59175(8) 0.0424(4) Uani 1 1 d . . . . .
H3BA H 0.813575 1.154899 0.603833 0.051 Uiso 1 1 calc R U . . .
H3BB H 1.019681 1.130146 0.621835 0.051 Uiso 1 1 calc R U . . .
C4B C 0.9747(2) 1.18045(11) 0.52578(7) 0.0403(3) Uani 1 1 d . . . . .
H4BA H 1.093979 1.147682 0.513966 0.048 Uiso 1 1 calc R U . . .
H4BB H 0.888254 1.171068 0.495677 0.048 Uiso 1 1 calc R U . . .
C5B C 0.9690(2) 1.30071(12) 0.52120(8) 0.0430(4) Uani 1 1 d . . . . .
H5BA H 0.847222 1.333712 0.530419 0.052 Uiso 1 1 calc R U . . .
H5BB H 1.048533 1.309483 0.553720 0.052 Uiso 1 1 calc R U . . .
C6B C 1.0227(2) 1.36159(13) 0.45775(8) 0.0466(4) Uani 1 1 d . . . . .
O1B O 1.0310(2) 1.46280(10) 0.45228(6) 0.0657(4) Uani 1 1 d . . . . .
H2O H 1.011465 1.479875 0.486847 0.099 Uiso 0.5 1 calc R U P . .
O2B O 1.0584(2) 1.31811(10) 0.41221(6) 0.0650(4) Uani 1 1 d . . . . .
C1B C 0.8894(18) 0.9456(10) 0.6596(7) 0.0536(14) Uani 0.683(6) 1 d . U P B 1
H1BA H 0.764161 0.973255 0.667851 0.064 Uiso 0.683(6) 1 calc R U P B 1
H1BB H 0.963538 0.962836 0.690840 0.064 Uiso 0.683(6) 1 calc R U P B 1
N1B N 0.9151(5) 0.82470(18) 0.66769(13) 0.0556(9) Uani 0.683(6) 1 d . U P B 1
H1NA H 0.881987 0.808116 0.632060 0.083 Uiso 0.683(6) 1 calc R U P B 1
H1NB H 0.847768 0.798100 0.699710 0.083 Uiso 0.683(6) 1 calc R U P B 1
H1NC H 1.030964 0.795898 0.676128 0.083 Uiso 0.683(6) 1 calc R U P B 1
C1BD C 0.873(4) 0.937(2) 0.6595(15) 0.054(3) Uani 0.317(6) 1 d . U P B 2
H1BC H 0.974641 0.909335 0.688823 0.065 Uiso 0.317(6) 1 calc R U P B 2
H1BD H 0.782302 0.983811 0.678775 0.065 Uiso 0.317(6) 1 calc R U P B 2
N1BD N 0.7948(11) 0.8428(4) 0.6453(3) 0.0523(16) Uani 0.317(6) 1 d . U P B 2
H1ND H 0.691192 0.868509 0.623834 0.078 Uiso 0.317(6) 1 calc R U P B 2
H1NE H 0.774793 0.798560 0.681654 0.078 Uiso 0.317(6) 1 calc R U P B 2
H1NF H 0.872545 0.806159 0.622108 0.078 Uiso 0.317(6) 1 calc R U P B 2
C1C C 1.1682(3) 1.61175(13) 0.31671(8) 0.0496(4) Uani 1 1 d . . . . .
H1CA H 1.257121 1.611071 0.348659 0.060 Uiso 1 1 calc R U . . .
H1CB H 1.053243 1.650703 0.328256 0.060 Uiso 1 1 calc R U . . .
C2C C 1.2243(2) 1.66964(11) 0.25291(7) 0.0426(4) Uani 1 1 d . . . . .
H2CA H 1.141207 1.663783 0.220638 0.051 Uiso 1 1 calc R U . . .
H2CB H 1.343620 1.633601 0.243286 0.051 Uiso 1 1 calc R U . . .
C3C C 1.2280(2) 1.78899(11) 0.24954(7) 0.0407(3) Uani 1 1 d . . . . .
H3CA H 1.109585 1.825200 0.259985 0.049 Uiso 1 1 calc R U . . .
H3CB H 1.313888 1.795314 0.280749 0.049 Uiso 1 1 calc R U . . .
C4C C 1.2801(2) 1.84468(11) 0.18412(7) 0.0379(3) Uani 1 1 d . . . . .
H4CA H 1.193421 1.838585 0.153099 0.045 Uiso 1 1 calc R U . . .
H4CB H 1.397702 1.807542 0.173592 0.045 Uiso 1 1 calc R U . . .
C5C C 1.2869(2) 1.96378(11) 0.17953(7) 0.0384(3) Uani 1 1 d . . . . .
H5CA H 1.172140 1.999261 0.193444 0.046 Uiso 1 1 calc R U . . .
H5CB H 1.379738 1.969139 0.208515 0.046 Uiso 1 1 calc R U . . .
C6C C 1.3247(2) 2.02380(11) 0.11420(7) 0.0391(3) Uani 1 1 d . . . . .
O1C O 1.33547(17) 1.98396(9) 0.06713(5) 0.0549(3) Uani 1 1 d . . . . .
O2C O 1.34381(17) 2.12502(8) 0.10841(5) 0.0503(3) Uani 1 1 d . . . . .
H3O H 1.335786 2.141114 0.143467 0.075 Uiso 1 1 calc R U . . .
N1C N 1.1514(3) 1.49941(11) 0.31561(8) 0.0693(5) Uani 1 1 d . . . . .
H7N H 1.059578 1.500070 0.290219 0.104 Uiso 1 1 calc R U . . .
H8N H 1.131164 1.464467 0.354796 0.104 Uiso 1 1 calc R U . . .
H9N H 1.253110 1.465633 0.301160 0.104 Uiso 1 1 calc R U . . .
C1 C 0.2108(2) 0.16846(13) 0.83255(8) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.2036(2) 0.05132(12) 0.83854(8) 0.0433(4) Uani 1 1 d . . . . .
H2 H 0.228205 0.020674 0.802959 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1634(2) -0.01133(13) 0.89260(8) 0.0443(4) Uani 1 1 d . . . . .
H3 H 0.147656 0.021584 0.927527 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1404(2) -0.12490(12) 0.90476(8) 0.0423(4) Uani 1 1 d . . . . .
C5 C 0.1613(2) -0.18725(12) 0.85787(8) 0.0454(4) Uani 1 1 d . . . . .
H5 H 0.194341 -0.156254 0.817123 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1340(2) -0.29351(13) 0.87056(8) 0.0449(4) Uani 1 1 d . . . . .
H6D H 0.148264 -0.333398 0.838665 0.054 Uiso 0.188(3) 1 calc R U P C 2
C7 C 0.0847(2) -0.34086(13) 0.93195(8) 0.0445(4) Uani 1 1 d . . . . .
C8 C 0.0623(2) -0.28047(14) 0.97867(8) 0.0488(4) Uani 1 1 d . . . . .
H8 H 0.028462 -0.311515 1.019311 0.059 Uiso 0.812(3) 1 calc R U P C 1
C9 C 0.0898(2) -0.17399(13) 0.96540(8) 0.0477(4) Uani 1 1 d . . . . .
H9 H 0.074328 -0.134306 0.997391 0.057 Uiso 1 1 calc R U . . .
O1 O 0.17889(18) 0.21103(10) 0.88015(6) 0.0596(3) Uani 1 1 d . . . . .
O2 O 0.24760(17) 0.22151(9) 0.77842(6) 0.0550(3) Uani 1 1 d . . . . .
O3 O 0.05983(19) -0.44629(10) 0.94493(7) 0.0647(4) Uani 1 1 d D . . . .
H4O H 0.063(4) -0.471(2) 0.9126(10) 0.097 Uiso 1 1 d D U . . .
O4 O 0.1501(2) -0.35963(11) 0.82642(7) 0.0594(5) Uani 0.812(3) 1 d . . P C 1
H5O H 0.183862 -0.326993 0.792452 0.089 Uiso 0.812(3) 1 calc R U P C 1
O4D O 0.0041(11) -0.3218(6) 1.0422(4) 0.075(3) Uani 0.188(3) 1 d . . P C 2
H4DO H -0.024443 -0.271370 1.060687 0.113 Uiso 0.188(3) 1 calc R U P C 2
C10 C 0.6428(3) 0.34843(14) 0.33324(9) 0.0563(4) Uani 1 1 d . . . . .
C11 C 0.5899(2) 0.28691(14) 0.39484(8) 0.0527(4) Uani 1 1 d . . . . .
H11 H 0.607203 0.211513 0.400933 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5193(2) 0.33252(14) 0.44199(8) 0.0504(4) Uani 1 1 d . . . . .
H12 H 0.496054 0.408172 0.433625 0.060 Uiso 1 1 calc R U . . .
C13 C 0.4738(2) 0.27805(13) 0.50548(8) 0.0438(4) Uani 1 1 d . . . . .
C14 C 0.4765(2) 0.16624(13) 0.52179(8) 0.0448(4) Uani 1 1 d . . . . .
H14 H 0.505120 0.124466 0.491113 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4374(2) 0.11677(12) 0.58251(8) 0.0425(4) Uani 1 1 d . . . . .
C16 C 0.3960(2) 0.17839(13) 0.62942(8) 0.0451(4) Uani 1 1 d . . . . .
C17 C 0.3916(2) 0.28909(14) 0.61389(8) 0.0506(4) Uani 1 1 d . . . . .
H17 H 0.363320 0.330749 0.644642 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4294(2) 0.33825(14) 0.55236(8) 0.0510(4) Uani 1 1 d . . . . .
H18 H 0.424989 0.413097 0.542219 0.061 Uiso 1 1 calc R U . . .
O5 O 0.5670(15) 0.4457(6) 0.3150(5) 0.058(2) Uani 0.55(3) 1 d . U P D 1
O5D O 0.629(3) 0.4571(6) 0.3297(6) 0.072(2) Uani 0.45(3) 1 d . U P D 2
O6 O 0.73680(18) 0.29747(10) 0.29633(6) 0.0632(3) Uani 1 1 d . . . . .
O7 O 0.4393(2) 0.00758(10) 0.59644(6) 0.0638(4) Uani 1 1 d . . . . .
H6O H 0.416237 -0.011625 0.634161 0.096 Uiso 1 1 calc R U . . .
O8 O 0.3619(2) 0.12172(10) 0.68779(6) 0.0626(4) Uani 1 1 d . . . . .
H7O H 0.326643 0.164158 0.711185 0.094 Uiso 1 1 calc R U . . .
O1W O 0.3657(2) -0.10705(12) 0.71069(7) 0.0796(4) Uani 1 1 d D . . . .
H1W H 0.348(4) -0.1751(16) 0.7052(14) 0.119 Uiso 1 1 d D U . . .
H2W H 0.468(3) -0.121(2) 0.7333(13) 0.119 Uiso 1 1 d D U . . .
O2W O 0.1917(3) -0.55685(12) 0.75612(10) 0.0942(6) Uani 1 1 d D . . . .
H3W H 0.284(3) -0.529(3) 0.7355(15) 0.141 Uiso 1 1 d D U . . .
H4W H 0.230(4) -0.6278(15) 0.7621(16) 0.141 Uiso 1 1 d D U . . .
O3W O 0.0701(4) -0.57268(19) 0.86814(13) 0.0768(10) Uani 0.597(5) 1 d D . P . .
H5W H 0.113(6) -0.540(3) 0.8293(14) 0.115 Uiso 0.597(5) 1 d D U P . .
H6W H 0.112(6) -0.6437(17) 0.873(2) 0.115 Uiso 0.597(5) 1 d D U P . .


_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
C1A N1A 1.4871(19) . ?
C1A C2A 1.510(2) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A C3A 1.524(2) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3A C4A 1.512(2) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A C5A 1.514(2) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5A C6A 1.500(2) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C6A O2A 1.224(2) . ?
C6A O1A 1.2868(19) . ?
O1A H1O 0.8200 . ?
N1A H1N 0.8900 . ?
N1A H2N 0.8900 . ?
N1A H3N 0.8900 . ?
C2B C1B 1.477(15) . ?
C2B C3B 1.519(2) . ?
C2B C1BD 1.56(3) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C3B C4B 1.514(2) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C5B 1.512(2) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C5B C6B 1.506(2) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C6B O2B 1.225(2) . ?
C6B O1B 1.2869(19) . ?
O1B H2O 0.8200 . ?
C1B N1B 1.494(12) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
N1B H1NA 0.8900 . ?
N1B H1NB 0.8900 . ?
N1B H1NC 0.8900 . ?
C1BD N1BD 1.52(3) . ?
C1BD H1BC 0.9700 . ?
C1BD H1BD 0.9700 . ?
N1BD H1ND 0.8900 . ?
N1BD H1NE 0.8900 . ?
N1BD H1NF 0.8900 . ?
C1C N1C 1.469(2) . ?
C1C C2C 1.504(2) . ?
C1C H1CA 0.9700 . ?
C1C H1CB 0.9700 . ?
C2C C3C 1.5171(19) . ?
C2C H2CA 0.9700 . ?
C2C H2CB 0.9700 . ?
C3C C4C 1.513(2) . ?
C3C H3CA 0.9700 . ?
C3C H3CB 0.9700 . ?
C4C C5C 1.5148(19) . ?
C4C H4CA 0.9700 . ?
C4C H4CB 0.9700 . ?
C5C C6C 1.499(2) . ?
C5C H5CA 0.9700 . ?
C5C H5CB 0.9700 . ?
C6C O1C 1.2195(18) . ?
C6C O2C 1.3074(17) . ?
O2C H3O 0.8200 . ?
N1C H7N 0.8900 . ?
N1C H8N 0.8900 . ?
N1C H9N 0.8900 . ?
C1 O1 1.2546(19) . ?
C1 O2 1.269(2) . ?
C1 C2 1.486(2) . ?
C2 C3 1.327(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.461(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.398(2) . ?
C4 C5 1.400(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 O4 1.387(2) . ?
C6 C7 1.402(2) . ?
C6 H6D 0.9300 . ?
C7 O3 1.364(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.383(2) . ?
C8 O4D 1.444(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O3 H4O 0.819(16) . ?
O4 H5O 0.8200 . ?
O4D H4DO 0.8200 . ?
C10 O6 1.254(2) . ?
C10 O5 1.255(5) . ?
C10 O5D 1.360(10) . ?
C10 C11 1.476(2) . ?
C11 C12 1.325(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.459(2) . ?
C12 H12 0.9300 . ?
C13 C18 1.391(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.375(2) . ?
C14 H14 0.9300 . ?
C15 O7 1.3620(19) . ?
C15 C16 1.401(2) . ?
C16 O8 1.354(2) . ?
C16 C17 1.378(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O7 H6O 0.8200 . ?
O8 H7O 0.8200 . ?
O1W H1W 0.935(17) . ?
O1W H2W 0.894(17) . ?
O2W H3W 0.902(17) . ?
O2W H4W 0.883(18) . ?
O3W H5W 0.93(2) . ?
O3W H6W 0.891(19) . ?

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
N1A C1A C2A 111.37(12) . . ?
N1A C1A H1AA 109.4 . . ?
C2A C1A H1AA 109.4 . . ?
N1A C1A H1AB 109.4 . . ?
C2A C1A H1AB 109.4 . . ?
H1AA C1A H1AB 108.0 . . ?
C1A C2A C3A 112.18(12) . . ?
C1A C2A H2AA 109.2 . . ?
C3A C2A H2AA 109.2 . . ?
C1A C2A H2AB 109.2 . . ?
C3A C2A H2AB 109.2 . . ?
H2AA C2A H2AB 107.9 . . ?
C4A C3A C2A 112.53(13) . . ?
C4A C3A H3AA 109.1 . . ?
C2A C3A H3AA 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
C2A C3A H3AB 109.1 . . ?
H3AA C3A H3AB 107.8 . . ?
C3A C4A C5A 112.38(13) . . ?
C3A C4A H4AA 109.1 . . ?
C5A C4A H4AA 109.1 . . ?
C3A C4A H4AB 109.1 . . ?
C5A C4A H4AB 109.1 . . ?
H4AA C4A H4AB 107.9 . . ?
C6A C5A C4A 115.68(13) . . ?
C6A C5A H5AA 108.4 . . ?
C4A C5A H5AA 108.4 . . ?
C6A C5A H5AB 108.4 . . ?
C4A C5A H5AB 108.4 . . ?
H5AA C5A H5AB 107.4 . . ?
O2A C6A O1A 119.89(16) . . ?
O2A C6A C5A 122.75(14) . . ?
O1A C6A C5A 117.34(14) . . ?
C6A O1A H1O 109.5 . . ?
C1A N1A H1N 109.5 . . ?
C1A N1A H2N 109.5 . . ?
H1N N1A H2N 109.5 . . ?
C1A N1A H3N 109.5 . . ?
H1N N1A H3N 109.5 . . ?
H2N N1A H3N 109.5 . . ?
C1B C2B C3B 111.9(5) . . ?
C3B C2B C1BD 116.0(10) . . ?
C1B C2B H2BA 109.2 . . ?
C3B C2B H2BA 109.2 . . ?
C1B C2B H2BB 109.2 . . ?
C3B C2B H2BB 109.2 . . ?
H2BA C2B H2BB 107.9 . . ?
C4B C3B C2B 112.35(13) . . ?
C4B C3B H3BA 109.1 . . ?
C2B C3B H3BA 109.1 . . ?
C4B C3B H3BB 109.1 . . ?
C2B C3B H3BB 109.1 . . ?
H3BA C3B H3BB 107.9 . . ?
C5B C4B C3B 112.88(13) . . ?
C5B C4B H4BA 109.0 . . ?
C3B C4B H4BA 109.0 . . ?
C5B C4B H4BB 109.0 . . ?
C3B C4B H4BB 109.0 . . ?
H4BA C4B H4BB 107.8 . . ?
C6B C5B C4B 115.04(13) . . ?
C6B C5B H5BA 108.5 . . ?
C4B C5B H5BA 108.5 . . ?
C6B C5B H5BB 108.5 . . ?
C4B C5B H5BB 108.5 . . ?
H5BA C5B H5BB 107.5 . . ?
O2B C6B O1B 119.86(15) . . ?
O2B C6B C5B 122.37(14) . . ?
O1B C6B C5B 117.76(14) . . ?
C6B O1B H2O 109.5 . . ?
C2B C1B N1B 113.5(9) . . ?
C2B C1B H1BA 108.9 . . ?
N1B C1B H1BA 108.9 . . ?
C2B C1B H1BB 108.9 . . ?
N1B C1B H1BB 108.9 . . ?
H1BA C1B H1BB 107.7 . . ?
C1B N1B H1NA 109.5 . . ?
C1B N1B H1NB 109.5 . . ?
H1NA N1B H1NB 109.5 . . ?
C1B N1B H1NC 109.5 . . ?
H1NA N1B H1NC 109.5 . . ?
H1NB N1B H1NC 109.5 . . ?
N1BD C1BD C2B 108.0(19) . . ?
N1BD C1BD H1BC 110.1 . . ?
C2B C1BD H1BC 110.1 . . ?
N1BD C1BD H1BD 110.1 . . ?
C2B C1BD H1BD 110.1 . . ?
H1BC C1BD H1BD 108.4 . . ?
C1BD N1BD H1ND 109.5 . . ?
C1BD N1BD H1NE 109.5 . . ?
H1ND N1BD H1NE 109.5 . . ?
C1BD N1BD H1NF 109.5 . . ?
H1ND N1BD H1NF 109.5 . . ?
H1NE N1BD H1NF 109.5 . . ?
N1C C1C C2C 111.12(13) . . ?
N1C C1C H1CA 109.4 . . ?
C2C C1C H1CA 109.4 . . ?
N1C C1C H1CB 109.4 . . ?
C2C C1C H1CB 109.4 . . ?
H1CA C1C H1CB 108.0 . . ?
C1C C2C C3C 113.46(13) . . ?
C1C C2C H2CA 108.9 . . ?
C3C C2C H2CA 108.9 . . ?
C1C C2C H2CB 108.9 . . ?
C3C C2C H2CB 108.9 . . ?
H2CA C2C H2CB 107.7 . . ?
C4C C3C C2C 111.68(12) . . ?
C4C C3C H3CA 109.3 . . ?
C2C C3C H3CA 109.3 . . ?
C4C C3C H3CB 109.3 . . ?
C2C C3C H3CB 109.3 . . ?
H3CA C3C H3CB 107.9 . . ?
C3C C4C C5C 112.85(12) . . ?
C3C C4C H4CA 109.0 . . ?
C5C C4C H4CA 109.0 . . ?
C3C C4C H4CB 109.0 . . ?
C5C C4C H4CB 109.0 . . ?
H4CA C4C H4CB 107.8 . . ?
C6C C5C C4C 114.42(12) . . ?
C6C C5C H5CA 108.7 . . ?
C4C C5C H5CA 108.7 . . ?
C6C C5C H5CB 108.7 . . ?
C4C C5C H5CB 108.7 . . ?
H5CA C5C H5CB 107.6 . . ?
O1C C6C O2C 119.34(14) . . ?
O1C C6C C5C 123.75(13) . . ?
O2C C6C C5C 116.91(13) . . ?
C6C O2C H3O 109.5 . . ?
C1C N1C H7N 109.5 . . ?
C1C N1C H8N 109.5 . . ?
H7N N1C H8N 109.5 . . ?
C1C N1C H9N 109.5 . . ?
H7N N1C H9N 109.5 . . ?
H8N N1C H9N 109.5 . . ?
O1 C1 O2 122.83(14) . . ?
O1 C1 C2 119.52(15) . . ?
O2 C1 C2 117.64(14) . . ?
C3 C2 C1 122.69(15) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 128.90(15) . . ?
C2 C3 H3 115.6 . . ?
C4 C3 H3 115.6 . . ?
C9 C4 C5 117.58(14) . . ?
C9 C4 C3 119.22(14) . . ?
C5 C4 C3 123.18(14) . . ?
C6 C5 C4 121.69(15) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 O4 124.87(15) . . ?
C5 C6 C7 119.45(15) . . ?
O4 C6 C7 115.67(14) . . ?
C5 C6 H6D 120.3 . . ?
C7 C6 H6D 120.3 . . ?
O3 C7 C8 120.63(15) . . ?
O3 C7 C6 119.67(15) . . ?
C8 C7 C6 119.70(15) . . ?
C7 C8 C9 120.35(15) . . ?
C7 C8 O4D 123.0(3) . . ?
C9 C8 O4D 116.6(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 121.23(15) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C7 O3 H4O 111.5(19) . . ?
C6 O4 H5O 109.5 . . ?
C8 O4D H4DO 109.5 . . ?
O6 C10 O5 121.5(4) . . ?
O6 C10 O5D 123.7(4) . . ?
O6 C10 C11 118.76(16) . . ?
O5 C10 C11 118.5(3) . . ?
O5D C10 C11 114.8(4) . . ?
C12 C11 C10 124.02(16) . . ?
C12 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C11 C12 C13 127.66(16) . . ?
C11 C12 H12 116.2 . . ?
C13 C12 H12 116.2 . . ?
C18 C13 C14 118.02(15) . . ?
C18 C13 C12 119.56(15) . . ?
C14 C13 C12 122.40(15) . . ?
C15 C14 C13 121.06(15) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O7 C15 C14 119.36(14) . . ?
O7 C15 C16 120.50(14) . . ?
C14 C15 C16 120.14(14) . . ?
O8 C16 C17 125.06(14) . . ?
O8 C16 C15 115.49(14) . . ?
C17 C16 C15 119.45(15) . . ?
C16 C17 C18 119.90(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.42(15) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C15 O7 H6O 109.5 . . ?
C16 O8 H7O 109.5 . . ?
H1W O1W H2W 105(3) . . ?
H3W O2W H4W 103(3) . . ?
H5W O3W H6W 106(4) . . ?

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
N1A C1A C2A C3A 177.31(13) . . . . ?
C1A C2A C3A C4A -176.12(14) . . . . ?
C2A C3A C4A C5A 179.53(14) . . . . ?
C3A C4A C5A C6A -175.55(14) . . . . ?
C4A C5A C6A O2A -5.0(3) . . . . ?
C4A C5A C6A O1A 173.36(15) . . . . ?
C1B C2B C3B C4B -178.3(6) . . . . ?
C1BD C2B C3B C4B -173.4(13) . . . . ?
C2B C3B C4B C5B 179.29(14) . . . . ?
C3B C4B C5B C6B 175.95(13) . . . . ?
C4B C5B C6B O2B 4.0(2) . . . . ?
C4B C5B C6B O1B -175.86(15) . . . . ?
C3B C2B C1B N1B -172.4(6) . . . . ?
C3B C2B C1BD N1BD 151.3(12) . . . . ?
N1C C1C C2C C3C 174.97(15) . . . . ?
C1C C2C C3C C4C -178.46(13) . . . . ?
C2C C3C C4C C5C -179.38(13) . . . . ?
C3C C4C C5C C6C -175.72(12) . . . . ?
C4C C5C C6C O1C 5.5(2) . . . . ?
C4C C5C C6C O2C -175.63(13) . . . . ?
O1 C1 C2 C3 0.4(2) . . . . ?
O2 C1 C2 C3 -178.84(15) . . . . ?
C1 C2 C3 C4 175.90(14) . . . . ?
C2 C3 C4 C9 -177.17(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 -178.29(15) . . . . ?
C4 C5 C6 O4 179.21(16) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 O3 -179.18(14) . . . . ?
O4 C6 C7 O3 1.4(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
O4 C6 C7 C8 -178.81(15) . . . . ?
O3 C7 C8 C9 179.23(15) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
O3 C7 C8 O4D -2.9(5) . . . . ?
C6 C7 C8 O4D 177.2(4) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
O4D C8 C9 C4 -177.9(4) . . . . ?
C5 C4 C9 C8 0.4(2) . . . . ?
C3 C4 C9 C8 178.43(14) . . . . ?
O6 C10 C11 C12 167.58(18) . . . . ?
O5 C10 C11 C12 -24.7(9) . . . . ?
O5D C10 C11 C12 5.8(11) . . . . ?
C10 C11 C12 C13 -175.85(16) . . . . ?
C11 C12 C13 C18 169.13(18) . . . . ?
C11 C12 C13 C14 -9.5(3) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
C12 C13 C14 C15 178.32(14) . . . . ?
C13 C14 C15 O7 179.24(15) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
O7 C15 C16 O8 0.9(2) . . . . ?
C14 C15 C16 O8 -179.17(15) . . . . ?
O7 C15 C16 C17 -178.79(15) . . . . ?
C14 C15 C16 C17 1.2(2) . . . . ?
O8 C16 C17 C18 179.87(16) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C12 C13 C18 C17 -177.68(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1O O2C 0.82 1.84 2.4771(18) 133.0 2_786 yes
O1B H2O O1B 0.82 1.63 2.437(3) 169.2 2_786 yes
O2C H3O O1A 0.82 1.66 2.4771(18) 172.8 2_786 yes
N1A H2N O1C 0.89 2.37 3.1089(18) 140.3 1_436 yes
N1A H2N O2C 0.89 2.05 2.8990(19) 160.4 1_436 yes
N1A H3N O1C 0.89 2.04 2.8422(19) 149.1 2_776 yes
N1B H1NA O2B 0.89 2.02 2.737(3) 137.1 2_776 yes
N1C H9N O2A 0.89 2.17 2.780(2) 125.5 2_776 yes
N1B H1NC O6 0.89 1.96 2.830(4) 166.7 2_766 yes
N1C H7N O2W 0.89 2.10 2.939(3) 157.6 2_666 yes
N1C H9N O5 0.89 2.35 3.078(11) 139.1 1_665 yes
O4 H5O O6 0.82 1.96 2.750(2) 160.2 2_656 yes
O1W H1W O6 0.935(17) 1.800(18) 2.718(2) 166(3) 2_656 yes
O2W H3W O5 0.902(17) 1.86(2) 2.744(8) 167(3) 2_656 yes
O1W H2W O1A 0.894(17) 2.054(18) 2.930(2) 166(3) 1_545 yes
O2W H4W O2 0.883(18) 1.86(2) 2.727(2) 165(3) 1_545 yes
O3W H6W O1 0.891(19) 1.81(2) 2.695(3) 175(5) 1_545 yes
N1A H1N O1 0.89 1.88 2.764(2) 174.7 . yes
N1B H1NB O1A 0.89 2.27 3.079(3) 151.7 . yes
N1B H1NB O2A 0.89 2.07 2.868(3) 148.4 . yes
N1C H8N O1B 0.89 2.21 3.018(2) 151.6 . yes
N1C H8N O2B 0.89 2.17 2.9432(19) 145.6 . yes
C5 H5 O1W 0.93 2.61 3.518(2) 164.8 . yes
O3 H4O O4 0.819(16) 2.25(3) 2.679(2) 113(2) . yes
O3 H4O O3W 0.819(16) 1.762(19) 2.532(3) 156(3) . yes
O7 H6O O8 0.82 2.22 2.6753(18) 114.9 . yes
O7 H6O O1W 0.82 1.91 2.683(2) 157.8 . yes
O8 H7O O2 0.82 1.79 2.5916(18) 163.6 . yes
O3W H5W O4 0.93(2) 2.36(4) 2.850(3) 113(3) . yes
O3W H5W O2W 0.93(2) 1.71(3) 2.534(3) 146(4) . yes

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
