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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2285230'
loop_
_audit_author_name
_audit_author_address
'Mirta Rubcic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'salt of 4-chlorobenzoic acid and 4-(2-aminoethyl)morpholine)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Cl O2, C6 H15 N2 O'
_chemical_formula_sum            'C13 H19 Cl N2 O3'
_chemical_formula_weight         286.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   19.8713(4)
_cell_length_b                   6.40620(10)
_cell_length_c                   24.5625(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.679(2)
_cell_angle_gamma                90
_cell_volume                     2995.24(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    31525
_cell_measurement_theta_min      2.6340
_cell_measurement_theta_max      79.0440

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.318
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57483
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.413
_oxdiff_exptl_absorpt_empirical_full_max 2.184
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            54789
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0382
_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       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.380
_diffrn_reflns_theta_max         67.992
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5461
_reflns_number_gt                4972
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0711P)²+1.1127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00090(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5461
_refine_ls_number_parameters     340
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_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
Cl1B Cl 0.57886(3) 0.44547(13) 0.84559(2) 0.0883(3) Uani 1 1 d . . . . .
Cl1A Cl 0.38058(5) -0.2631(2) 0.01044(3) 0.1439(5) Uani 1 1 d . . . . .
O2B O 0.51886(9) 0.9482(2) 0.59956(6) 0.0690(4) Uani 1 1 d . . . . .
O1B O 0.54499(9) 0.6418(2) 0.57017(5) 0.0688(4) Uani 1 1 d . . . . .
O1A O 0.70478(8) -0.0568(3) 0.17459(7) 0.0764(5) Uani 1 1 d . . . . .
N1B N 0.55440(9) 1.2373(2) 0.53108(6) 0.0524(4) Uani 1 1 d . . . . .
H1BA H 0.519550 1.262600 0.499752 0.063 Uiso 1 1 calc R U . . .
H1BB H 0.564560 1.353311 0.551732 0.063 Uiso 1 1 calc R U . . .
H1BC H 0.541336 1.138028 0.551291 0.063 Uiso 1 1 calc R U . . .
N2B N 0.69704(9) 1.2682(2) 0.60856(7) 0.0549(4) Uani 1 1 d . U . . .
N1A N 0.68296(8) 0.5944(3) 0.23589(8) 0.0577(4) Uani 1 1 d . . . . .
H1AA H 0.684565 0.480180 0.215673 0.069 Uiso 1 1 calc R U . . .
H1AB H 0.715151 0.585349 0.269539 0.069 Uiso 1 1 calc R U . . .
H1AC H 0.691598 0.706083 0.217419 0.069 Uiso 1 1 calc R U . . .
N2A N 0.65755(10) 0.8204(3) 0.33093(8) 0.0644(4) Uani 1 1 d . . . . .
O3B O 0.80132(10) 1.5050(3) 0.68892(9) 0.0993(7) Uani 1 1 d . . . . .
C2B C 0.54873(8) 0.6782(3) 0.66754(7) 0.0429(4) Uani 1 1 d . . . . .
C1B C 0.53692(10) 0.7624(3) 0.60812(7) 0.0491(4) Uani 1 1 d . . . . .
O2A O 0.65718(12) 0.2567(3) 0.16985(10) 0.1033(7) Uani 1 1 d . . . . .
C5B C 0.56822(10) 0.5362(3) 0.77711(8) 0.0554(5) Uani 1 1 d . . . . .
C2A C 0.58712(10) -0.0106(3) 0.11797(8) 0.0532(4) Uani 1 1 d . . . . .
C3B C 0.57129(11) 0.4760(3) 0.68228(8) 0.0556(5) Uani 1 1 d . . . . .
H3B H 0.579619 0.387182 0.654963 0.067 Uiso 1 1 calc R U . . .
C7B C 0.53733(11) 0.8081(3) 0.70902(8) 0.0552(5) Uani 1 1 d . . . . .
H7B H 0.523039 0.945001 0.699714 0.066 Uiso 1 1 calc R U . . .
C4B C 0.58156(11) 0.4046(3) 0.73720(9) 0.0592(5) Uani 1 1 d . . . . .
H4B H 0.597296 0.269229 0.747021 0.071 Uiso 1 1 calc R U . . .
O3A O 0.71169(13) 0.9078(5) 0.44812(10) 0.1199(8) Uani 1 1 d . . . . .
C1A C 0.65500(12) 0.0710(3) 0.15707(9) 0.0611(5) Uani 1 1 d . . . . .
C10B C 0.73826(12) 1.1831(3) 0.66295(9) 0.0629(5) Uani 1 1 d . . . . .
H10A H 0.778575 1.109344 0.657707 0.075 Uiso 1 1 calc R U . . .
H10B H 0.709877 1.083504 0.676368 0.075 Uiso 1 1 calc R U . . .
C6B C 0.54674(12) 0.7387(4) 0.76396(9) 0.0654(6) Uani 1 1 d . . . . .
H6B H 0.538709 0.827162 0.791474 0.078 Uiso 1 1 calc R U . . .
C3A C 0.58236(13) -0.2106(4) 0.09581(9) 0.0646(5) Uani 1 1 d . . . . .
H3A H 0.622211 -0.294437 0.103787 0.078 Uiso 1 1 calc R U . . .
C9B C 0.67517(12) 1.1010(4) 0.56695(9) 0.0658(6) Uani 1 1 d . . . . .
H9BA H 0.659180 0.983147 0.584720 0.079 Uiso 1 1 calc R U . . .
H9BB H 0.715307 1.055534 0.555026 0.079 Uiso 1 1 calc R U . . .
C8A C 0.61253(11) 0.6136(4) 0.24427(11) 0.0717(6) Uani 1 1 d . . . . .
H8AA H 0.603999 0.494656 0.265827 0.086 Uiso 1 1 calc R U . . .
H8AB H 0.577226 0.612642 0.207597 0.086 Uiso 1 1 calc R U . . .
C7A C 0.52729(13) 0.1106(4) 0.10545(11) 0.0715(6) Uani 1 1 d . . . . .
H7A H 0.529379 0.245207 0.120017 0.086 Uiso 1 1 calc R U . . .
C8B C 0.61704(12) 1.1673(4) 0.51524(9) 0.0713(6) Uani 1 1 d . . . . .
H8BA H 0.633670 1.280099 0.496114 0.086 Uiso 1 1 calc R U . . .
H8BB H 0.604431 1.051026 0.488988 0.086 Uiso 1 1 calc R U . . .
C9A C 0.60608(12) 0.8113(4) 0.27529(11) 0.0742(6) Uani 1 1 d . . . . .
H9AA H 0.612563 0.930271 0.252868 0.089 Uiso 1 1 calc R U . . .
H9AB H 0.559227 0.819973 0.279772 0.089 Uiso 1 1 calc R U . . .
C4A C 0.51907(16) -0.2873(5) 0.06195(10) 0.0813(7) Uani 1 1 d . . . . .
H4A H 0.516245 -0.421585 0.047085 0.098 Uiso 1 1 calc R U . . .
C5A C 0.46077(14) -0.1632(6) 0.05065(10) 0.0839(8) Uani 1 1 d . . . . .
C11B C 0.76291(15) 1.3486(5) 0.70645(11) 0.0833(7) Uani 1 1 d . . . . .
H11A H 0.722576 1.411158 0.714866 0.100 Uiso 1 1 calc R U . . .
H11B H 0.792063 1.285709 0.741147 0.100 Uiso 1 1 calc R U . . .
C6A C 0.46384(14) 0.0331(6) 0.07123(12) 0.0890(9) Uani 1 1 d . . . . .
H6A H 0.423757 0.116092 0.062575 0.107 Uiso 1 1 calc R U . . .
C13A C 0.67222(16) 1.0321(4) 0.35172(13) 0.0878(8) Uani 1 1 d . . . . .
H13C H 0.630282 1.094022 0.357555 0.105 Uiso 1 1 calc R U . . .
H13D H 0.686523 1.115809 0.324065 0.105 Uiso 1 1 calc R U . . .
C13B C 0.73817(18) 1.4281(5) 0.59168(15) 0.1055(8) Uani 1 1 d . U . . .
H13A H 0.710587 1.492785 0.556668 0.127 Uiso 1 1 calc R U . . .
H13B H 0.779433 1.365812 0.584742 0.127 Uiso 1 1 calc R U . . .
C12A C 0.72985(18) 1.0277(6) 0.40679(16) 0.1117(12) Uani 1 1 d . . . . .
H12C H 0.772035 0.970508 0.400187 0.134 Uiso 1 1 calc R U . . .
H12D H 0.740123 1.169214 0.420715 0.134 Uiso 1 1 calc R U . . .
C12B C 0.76033(18) 1.5909(5) 0.63733(15) 0.1055(8) Uani 1 1 d . . . . .
H12A H 0.787153 1.698337 0.625050 0.127 Uiso 1 1 calc R U . . .
H12B H 0.718893 1.655879 0.643240 0.127 Uiso 1 1 calc R U . . .
C10A C 0.6373(2) 0.6987(6) 0.37286(13) 0.1086(11) Uani 1 1 d . . . . .
H10C H 0.627992 0.555804 0.359819 0.130 Uiso 1 1 calc R U . . .
H10D H 0.594851 0.755746 0.378990 0.130 Uiso 1 1 calc R U . . .
C11A C 0.6966(3) 0.7041(7) 0.42782(15) 0.1346(15) Uani 1 1 d . . . . .
H11C H 0.683679 0.620926 0.456256 0.162 Uiso 1 1 calc R U . . .
H11D H 0.738347 0.642719 0.421491 0.162 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
Cl1B C5B 1.7343(19) . ?
Cl1A C5A 1.738(3) . ?
O2B C1B 1.244(2) . ?
O1B C1B 1.256(2) . ?
O1A C1A 1.261(3) . ?
N1B C8B 1.476(3) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B H1BC 0.8900 . ?
N2B C13B 1.443(3) . ?
N2B C10B 1.458(2) . ?
N2B C9B 1.458(3) . ?
N1A C8A 1.477(3) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A H1AC 0.8900 . ?
N2A C10A 1.438(3) . ?
N2A C13A 1.449(3) . ?
N2A C9A 1.454(3) . ?
O3B C11B 1.400(4) . ?
O3B C12B 1.407(3) . ?
C2B C7B 1.384(3) . ?
C2B C3B 1.385(3) . ?
C2B C1B 1.510(2) . ?
O2A C1A 1.228(3) . ?
C5B C6B 1.375(3) . ?
C5B C4B 1.375(3) . ?
C2A C7A 1.379(3) . ?
C2A C3A 1.384(3) . ?
C2A C1A 1.507(3) . ?
C3B C4B 1.383(3) . ?
C3B H3B 0.9300 . ?
C7B C6B 1.382(3) . ?
C7B H7B 0.9300 . ?
C4B H4B 0.9300 . ?
O3A C11A 1.398(5) . ?
O3A C12A 1.400(5) . ?
C10B C11B 1.485(3) . ?
C10B H10A 0.9700 . ?
C10B H10B 0.9700 . ?
C6B H6B 0.9300 . ?
C3A C4A 1.384(3) . ?
C3A H3A 0.9300 . ?
C9B C8B 1.512(3) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C8A C9A 1.503(4) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C7A C6A 1.391(4) . ?
C7A H7A 0.9300 . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C4A C5A 1.366(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.350(4) . ?
C11B H11A 0.9700 . ?
C11B H11B 0.9700 . ?
C6A H6A 0.9300 . ?
C13A C12A 1.501(4) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13B C12B 1.502(5) . ?
C13B H13A 0.9700 . ?
C13B H13B 0.9700 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12B H12A 0.9700 . ?
C12B H12B 0.9700 . ?
C10A C11A 1.516(5) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?

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
C8B N1B H1BA 109.5 . . ?
C8B N1B H1BB 109.5 . . ?
H1BA N1B H1BB 109.5 . . ?
C8B N1B H1BC 109.5 . . ?
H1BA N1B H1BC 109.5 . . ?
H1BB N1B H1BC 109.5 . . ?
C13B N2B C10B 108.25(19) . . ?
C13B N2B C9B 113.5(2) . . ?
C10B N2B C9B 110.10(16) . . ?
C8A N1A H1AA 109.5 . . ?
C8A N1A H1AB 109.5 . . ?
H1AA N1A H1AB 109.5 . . ?
C8A N1A H1AC 109.5 . . ?
H1AA N1A H1AC 109.5 . . ?
H1AB N1A H1AC 109.5 . . ?
C10A N2A C13A 108.9(2) . . ?
C10A N2A C9A 112.7(2) . . ?
C13A N2A C9A 112.6(2) . . ?
C11B O3B C12B 109.3(2) . . ?
C7B C2B C3B 118.64(17) . . ?
C7B C2B C1B 118.95(16) . . ?
C3B C2B C1B 122.41(16) . . ?
O2B C1B O1B 123.74(17) . . ?
O2B C1B C2B 117.56(16) . . ?
O1B C1B C2B 118.70(16) . . ?
C6B C5B C4B 121.42(18) . . ?
C6B C5B Cl1B 119.16(16) . . ?
C4B C5B Cl1B 119.42(16) . . ?
C7A C2A C3A 118.4(2) . . ?
C7A C2A C1A 120.2(2) . . ?
C3A C2A C1A 121.28(19) . . ?
C4B C3B C2B 120.70(19) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C6B C7B C2B 121.40(19) . . ?
C6B C7B H7B 119.3 . . ?
C2B C7B H7B 119.3 . . ?
C5B C4B C3B 119.22(19) . . ?
C5B C4B H4B 120.4 . . ?
C3B C4B H4B 120.4 . . ?
C11A O3A C12A 109.1(3) . . ?
O2A C1A O1A 125.1(2) . . ?
O2A C1A C2A 117.3(2) . . ?
O1A C1A C2A 117.60(19) . . ?
N2B C10B C11B 112.03(19) . . ?
N2B C10B H10A 109.2 . . ?
C11B C10B H10A 109.2 . . ?
N2B C10B H10B 109.2 . . ?
C11B C10B H10B 109.2 . . ?
H10A C10B H10B 107.9 . . ?
C5B C6B C7B 118.60(19) . . ?
C5B C6B H6B 120.7 . . ?
C7B C6B H6B 120.7 . . ?
C4A C3A C2A 120.8(2) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
N2B C9B C8B 112.61(18) . . ?
N2B C9B H9BA 109.1 . . ?
C8B C9B H9BA 109.1 . . ?
N2B C9B H9BB 109.1 . . ?
C8B C9B H9BB 109.1 . . ?
H9BA C9B H9BB 107.8 . . ?
N1A C8A C9A 111.28(19) . . ?
N1A C8A H8AA 109.4 . . ?
C9A C8A H8AA 109.4 . . ?
N1A C8A H8AB 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
H8AA C8A H8AB 108.0 . . ?
C2A C7A C6A 120.5(3) . . ?
C2A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
N1B C8B C9B 111.26(17) . . ?
N1B C8B H8BA 109.4 . . ?
C9B C8B H8BA 109.4 . . ?
N1B C8B H8BB 109.4 . . ?
C9B C8B H8BB 109.4 . . ?
H8BA C8B H8BB 108.0 . . ?
N2A C9A C8A 111.77(19) . . ?
N2A C9A H9AA 109.3 . . ?
C8A C9A H9AA 109.3 . . ?
N2A C9A H9AB 109.3 . . ?
C8A C9A H9AB 109.3 . . ?
H9AA C9A H9AB 107.9 . . ?
C5A C4A C3A 119.1(3) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C6A C5A C4A 121.4(2) . . ?
C6A C5A Cl1A 119.4(3) . . ?
C4A C5A Cl1A 119.1(3) . . ?
O3B C11B C10B 112.7(2) . . ?
O3B C11B H11A 109.1 . . ?
C10B C11B H11A 109.1 . . ?
O3B C11B H11B 109.1 . . ?
C10B C11B H11B 109.1 . . ?
H11A C11B H11B 107.8 . . ?
C5A C6A C7A 119.6(3) . . ?
C5A C6A H6A 120.2 . . ?
C7A C6A H6A 120.2 . . ?
N2A C13A C12A 108.9(3) . . ?
N2A C13A H13C 109.9 . . ?
C12A C13A H13C 109.9 . . ?
N2A C13A H13D 109.9 . . ?
C12A C13A H13D 109.9 . . ?
H13C C13A H13D 108.3 . . ?
N2B C13B C12B 110.3(3) . . ?
N2B C13B H13A 109.6 . . ?
C12B C13B H13A 109.6 . . ?
N2B C13B H13B 109.6 . . ?
C12B C13B H13B 109.6 . . ?
H13A C13B H13B 108.1 . . ?
O3A C12A C13A 112.0(3) . . ?
O3A C12A H12C 109.2 . . ?
C13A C12A H12C 109.2 . . ?
O3A C12A H12D 109.2 . . ?
C13A C12A H12D 109.2 . . ?
H12C C12A H12D 107.9 . . ?
O3B C12B C13B 111.8(3) . . ?
O3B C12B H12A 109.3 . . ?
C13B C12B H12A 109.3 . . ?
O3B C12B H12B 109.3 . . ?
C13B C12B H12B 109.3 . . ?
H12A C12B H12B 107.9 . . ?
N2A C10A C11A 108.6(3) . . ?
N2A C10A H10C 110.0 . . ?
C11A C10A H10C 110.0 . . ?
N2A C10A H10D 110.0 . . ?
C11A C10A H10D 110.0 . . ?
H10C C10A H10D 108.3 . . ?
O3A C11A C10A 111.8(3) . . ?
O3A C11A H11C 109.3 . . ?
C10A C11A H11C 109.3 . . ?
O3A C11A H11D 109.3 . . ?
C10A C11A H11D 109.3 . . ?
H11C C11A H11D 107.9 . . ?

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
C7B C2B C1B O2B 1.7(3) . . . . ?
C3B C2B C1B O2B -177.68(19) . . . . ?
C7B C2B C1B O1B -177.57(18) . . . . ?
C3B C2B C1B O1B 3.1(3) . . . . ?
C7B C2B C3B C4B 0.6(3) . . . . ?
C1B C2B C3B C4B 179.96(18) . . . . ?
C3B C2B C7B C6B -1.2(3) . . . . ?
C1B C2B C7B C6B 179.43(19) . . . . ?
C6B C5B C4B C3B -1.8(3) . . . . ?
Cl1B C5B C4B C3B 178.37(16) . . . . ?
C2B C3B C4B C5B 0.8(3) . . . . ?
C7A C2A C1A O2A -10.7(3) . . . . ?
C3A C2A C1A O2A 172.1(2) . . . . ?
C7A C2A C1A O1A 168.5(2) . . . . ?
C3A C2A C1A O1A -8.6(3) . . . . ?
C13B N2B C10B C11B 54.3(3) . . . . ?
C9B N2B C10B C11B 178.9(2) . . . . ?
C4B C5B C6B C7B 1.2(3) . . . . ?
Cl1B C5B C6B C7B -178.94(17) . . . . ?
C2B C7B C6B C5B 0.3(3) . . . . ?
C7A C2A C3A C4A -0.1(3) . . . . ?
C1A C2A C3A C4A 177.1(2) . . . . ?
C13B N2B C9B C8B -73.9(3) . . . . ?
C10B N2B C9B C8B 164.6(2) . . . . ?
C3A C2A C7A C6A -0.2(3) . . . . ?
C1A C2A C7A C6A -177.4(2) . . . . ?
N2B C9B C8B N1B -59.0(3) . . . . ?
C10A N2A C9A C8A -79.6(3) . . . . ?
C13A N2A C9A C8A 156.7(2) . . . . ?
N1A C8A C9A N2A -59.5(3) . . . . ?
C2A C3A C4A C5A -0.2(4) . . . . ?
C3A C4A C5A C6A 0.8(4) . . . . ?
C3A C4A C5A Cl1A -177.50(18) . . . . ?
C12B O3B C11B C10B 56.3(3) . . . . ?
N2B C10B C11B O3B -55.7(3) . . . . ?
C4A C5A C6A C7A -1.0(4) . . . . ?
Cl1A C5A C6A C7A 177.25(19) . . . . ?
C2A C7A C6A C5A 0.7(4) . . . . ?
C10A N2A C13A C12A 58.9(3) . . . . ?
C9A N2A C13A C12A -175.4(2) . . . . ?
C10B N2B C13B C12B -55.8(3) . . . . ?
C9B N2B C13B C12B -178.4(2) . . . . ?
C11A O3A C12A C13A 58.6(4) . . . . ?
N2A C13A C12A O3A -59.4(3) . . . . ?
C11B O3B C12B C13B -58.4(4) . . . . ?
N2B C13B C12B O3B 60.0(4) . . . . ?
C13A N2A C10A C11A -58.7(4) . . . . ?
C9A N2A C10A C11A 175.5(3) . . . . ?
C12A O3A C11A C10A -58.5(4) . . . . ?
N2A C10A C11A O3A 59.6(5) . . . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_stolar_baptol-24_auto
_database_code_depnum_ccdc_archive 'CCDC 2287225'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_date             2023-02-28T11:57:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C7 H5 O2, C7 H6 O2, C7 H10 N'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   11.5963(2)
_cell_length_b                   6.31630(10)
_cell_length_c                   25.5385(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.362(2)
_cell_angle_gamma                90
_cell_volume                     1869.00(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9173
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      78.033
_cell_measurement_temperature    100(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.48039
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            14783
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_theta_min         3.464
_diffrn_reflns_theta_max         79.643
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3980
_reflns_number_gt                3520
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1602
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_number_reflns         3980
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.5523P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1A 0.60538(8) 0.32776(17) 0.04748(4) 0.0277(3) Uani d 1 . . O
O2A 0.57910(9) 0.02592(17) 0.08911(4) 0.0288(3) Uani d 1 . . O
C1A 0.62389(11) 0.2073(2) 0.08611(5) 0.0235(3) Uani d 1 . . C
C2A 0.70492(11) 0.2813(2) 0.12993(5) 0.0242(3) Uani d 1 . . C
C3A 0.73026(12) 0.1501(3) 0.17271(6) 0.0293(3) Uani d 1 . . C
H3A 0.694175 0.015563 0.17482 0.035 Uiso calc 1 . . H
C4A 0.80821(12) 0.2153(3) 0.21238(6) 0.0344(4) Uani d 1 . . C
H4A 0.824081 0.126016 0.241728 0.041 Uiso calc 1 . . H
C5A 0.86264(12) 0.4093(3) 0.20926(6) 0.0324(4) Uani d 1 . . C
H5A 0.917571 0.451694 0.235844 0.039 Uiso calc 1 . . H
C6A 0.83669(13) 0.5413(3) 0.16726(6) 0.0334(4) Uani d 1 . . C
H6A 0.872714 0.676026 0.16543 0.04 Uiso calc 1 . . H
C7A 0.75827(12) 0.4783(3) 0.12769(6) 0.0294(3) Uani d 1 . . C
H7A 0.740996 0.57015 0.098971 0.035 Uiso calc 1 . . H
O1B 1.07829(10) 0.11331(19) 0.40734(4) 0.0347(3) Uani d 1 . . O
O2B 0.98882(9) 0.26755(19) 0.33793(4) 0.0331(3) Uani d 1 . . O
H2B 0.9692(18) 0.365(3) 0.3625(9) 0.04 Uiso d 1 . . H
C1B 1.05335(11) 0.1171(2) 0.36069(6) 0.0268(3) Uani d 1 . . C
C2B 1.09010(11) -0.0482(2) 0.32356(5) 0.0262(3) Uani d 1 . . C
C3B 1.06265(12) -0.0362(3) 0.26995(6) 0.0303(3) Uani d 1 . . C
H3B 1.022036 0.083068 0.25598 0.036 Uiso calc 1 . . H
C4B 1.09484(12) -0.1989(3) 0.23705(6) 0.0339(4) Uani d 1 . . C
H4B 1.07461 -0.191899 0.200662 0.041 Uiso calc 1 . . H
C5B 1.15603(13) -0.3709(3) 0.25676(6) 0.0338(4) Uani d 1 . . C
H5B 1.178166 -0.481394 0.234012 0.041 Uiso calc 1 . . H
C6B 1.18496(15) -0.3815(3) 0.30991(7) 0.0376(4) Uani d 1 . . C
H6B 1.227229 -0.499347 0.323589 0.045 Uiso calc 1 . . H
C7B 1.15241(14) -0.2206(3) 0.34317(6) 0.0337(4) Uani d 1 . . C
H7B 1.172818 -0.228402 0.379532 0.04 Uiso calc 1 . . H
N1 0.60045(9) 0.7370(2) 0.00990(5) 0.0244(3) Uani d 1 . . N
H1A 0.6035(17) 0.600(3) 0.0260(8) 0.037 Uiso d 1 . . H
H1B 0.5853(17) 0.844(3) 0.0369(8) 0.037 Uiso d 1 . . H
H1C 0.5366(18) 0.722(3) -0.0161(8) 0.037 Uiso d 1 . . H
C8 0.70861(11) 0.7920(2) -0.01459(5) 0.0236(3) Uani d 1 . . C
C9 0.79482(12) 0.6407(3) -0.01759(6) 0.0291(3) Uani d 1 . . C
H9 0.784055 0.502179 -0.004161 0.035 Uiso calc 1 . . H
C10 0.89765(13) 0.6957(3) -0.04069(6) 0.0328(4) Uani d 1 . . C
H10 0.95725 0.593184 -0.042758 0.039 Uiso calc 1 . . H
C11 0.91453(12) 0.8970(3) -0.06068(6) 0.0303(3) Uani d 1 . . C
C12 0.82551(12) 1.0447(3) -0.05752(6) 0.0286(3) Uani d 1 . . C
H12 0.835366 1.182846 -0.071349 0.034 Uiso calc 1 . . H
C13 0.72247(12) 0.9929(2) -0.03442(5) 0.0264(3) Uani d 1 . . C
H13 0.66253 1.094692 -0.032375 0.032 Uiso calc 1 . . H
C14 1.02685(14) 0.9559(3) -0.08502(7) 0.0410(4) Uani d 1 . . C
H14A 1.023139 1.10336 -0.096895 0.061 Uiso calc 1 . . H
H14B 1.090637 0.939411 -0.058961 0.061 Uiso calc 1 . . H
H14C 1.039536 0.863033 -0.114985 0.061 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1A . 1.2571(18) ?
O2A C1A . 1.2617(18) ?
C1A C2A . 1.5058(19) ?
C2A C7A . 1.392(2) ?
C2A C3A . 1.393(2) ?
C3A C4A . 1.392(2) ?
C3A H3A . 0.95 ?
C4A C5A . 1.382(2) ?
C4A H4A . 0.95 ?
C5A C6A . 1.382(2) ?
C5A H5A . 0.95 ?
C6A C7A . 1.390(2) ?
C6A H6A . 0.95 ?
C7A H7A . 0.95 ?
O1B C1B . 1.2144(18) ?
O2B C1B . 1.3287(18) ?
O2B H2B . 0.91(2) ?
C1B C2B . 1.485(2) ?
C2B C7B . 1.389(2) ?
C2B C3B . 1.395(2) ?
C3B C4B . 1.388(2) ?
C3B H3B . 0.95 ?
C4B C5B . 1.381(2) ?
C4B H4B . 0.95 ?
C5B C6B . 1.386(2) ?
C5B H5B . 0.95 ?
C6B C7B . 1.387(2) ?
C6B H6B . 0.95 ?
C7B H7B . 0.95 ?
N1 C8 . 1.4661(16) ?
N1 H1A . 0.96(2) ?
N1 H1B . 0.98(2) ?
N1 H1C . 0.98(2) ?
C8 C13 . 1.378(2) ?
C8 C9 . 1.387(2) ?
C9 C10 . 1.396(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.387(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.396(2) ?
C11 C14 . 1.513(2) ?
C12 C13 . 1.3932(19) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?

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 122.67(13) . . ?
O1A C1A C2A 118.47(13) . . ?
O2A C1A C2A 118.85(13) . . ?
C7A C2A C3A 118.97(13) . . ?
C7A C2A C1A 120.77(13) . . ?
C3A C2A C1A 120.23(13) . . ?
C4A C3A C2A 120.31(15) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C5A C4A C3A 120.31(14) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C6A C5A C4A 119.61(14) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C7A 120.46(15) . . ?
C5A C6A H6A 119.8 . . ?
C7A C6A H6A 119.8 . . ?
C6A C7A C2A 120.31(14) . . ?
C6A C7A H7A 119.8 . . ?
C2A C7A H7A 119.8 . . ?
C1B O2B H2B 109.5(13) . . ?
O1B C1B O2B 123.39(14) . . ?
O1B C1B C2B 123.35(14) . . ?
O2B C1B C2B 113.25(12) . . ?
C7B C2B C3B 119.40(14) . . ?
C7B C2B C1B 118.67(13) . . ?
C3B C2B C1B 121.92(14) . . ?
C4B C3B C2B 119.83(15) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C5B C4B C3B 120.58(14) . . ?
C5B C4B H4B 119.7 . . ?
C3B C4B H4B 119.7 . . ?
C4B C5B C6B 119.64(15) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C5B C6B C7B 120.24(16) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B C2B 120.28(15) . . ?
C6B C7B H7B 119.9 . . ?
C2B C7B H7B 119.9 . . ?
C8 N1 H1A 112.3(12) . . ?
C8 N1 H1B 108.5(12) . . ?
H1A N1 H1B 108.9(17) . . ?
C8 N1 H1C 111.7(12) . . ?
H1A N1 H1C 102.4(17) . . ?
H1B N1 H1C 113.0(17) . . ?
C13 C8 C9 121.24(13) . . ?
C13 C8 N1 119.31(12) . . ?
C9 C8 N1 119.45(13) . . ?
C8 C9 C10 118.83(14) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.29(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 118.39(13) . . ?
C10 C11 C14 120.90(14) . . ?
C12 C11 C14 120.71(15) . . ?
C13 C12 C11 121.10(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C8 C13 C12 119.15(13) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C7A -0.12(19) . . . . ?
O2A C1A C2A C7A 178.54(12) . . . . ?
O1A C1A C2A C3A -178.16(12) . . . . ?
O2A C1A C2A C3A 0.50(19) . . . . ?
C7A C2A C3A C4A -0.3(2) . . . . ?
C1A C2A C3A C4A 177.77(13) . . . . ?
C2A C3A C4A C5A -1.1(2) . . . . ?
C3A C4A C5A C6A 1.9(2) . . . . ?
C4A C5A C6A C7A -1.4(2) . . . . ?
C5A C6A C7A C2A 0.0(2) . . . . ?
C3A C2A C7A C6A 0.8(2) . . . . ?
C1A C2A C7A C6A -177.23(13) . . . . ?
O1B C1B C2B C7B 2.6(2) . . . . ?
O2B C1B C2B C7B -176.33(13) . . . . ?
O1B C1B C2B C3B -178.21(13) . . . . ?
O2B C1B C2B C3B 2.89(19) . . . . ?
C7B C2B C3B C4B 1.8(2) . . . . ?
C1B C2B C3B C4B -177.37(13) . . . . ?
C2B C3B C4B C5B -1.4(2) . . . . ?
C3B C4B C5B C6B 0.3(2) . . . . ?
C4B C5B C6B C7B 0.2(2) . . . . ?
C5B C6B C7B C2B 0.3(3) . . . . ?
C3B C2B C7B C6B -1.3(2) . . . . ?
C1B C2B C7B C6B 177.91(14) . . . . ?
C13 C8 C9 C10 0.7(2) . . . . ?
N1 C8 C9 C10 -179.57(13) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C14 179.23(14) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C14 C11 C12 C13 -178.98(14) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
N1 C8 C13 C12 179.80(12) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_stolar_baptol-32_auto
_database_code_depnum_ccdc_archive 'CCDC 2287226'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_date             2023-02-28T11:39:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_moiety         
'C7 H9 N, 2(C7 H6 O2), 2(C7 H5 O2), 2(C7 H10 N)'
_chemical_formula_sum            'C49 H51 N3 O8'
_chemical_formula_weight         809.93

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   16.3249(3)
_cell_length_b                   6.11590(10)
_cell_length_c                   21.4268(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.6370(10)
_cell_angle_gamma                90
_cell_volume                     2138.41(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10223
_cell_measurement_theta_min      4.125
_cell_measurement_theta_max      78.875
_cell_measurement_temperature    100(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            16943
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_theta_min         3.358
_diffrn_reflns_theta_max         79.876
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             4564
_reflns_number_gt                4081
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.1495
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     281
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0870P)²+0.7424P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0031(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1A 1.00168(6) -0.08374(17) 0.12367(5) 0.0253(3) Uani d 1 . . O
O2A 0.92875(7) -0.27996(17) 0.19066(5) 0.0250(2) Uani d 1 . . O
C1A 0.97610(8) -0.1123(2) 0.17573(6) 0.0199(3) Uani d 1 . . C
C2A 0.99440(8) 0.0379(2) 0.22931(6) 0.0202(3) Uani d 1 . . C
C3A 0.97496(9) -0.0149(2) 0.29053(7) 0.0245(3) Uani d 1 . . C
H3A 0.948922 -0.150054 0.299195 0.029 Uiso calc 1 . . H
C4A 0.99367(10) 0.1300(3) 0.33876(7) 0.0284(3) Uani d 1 . . C
H4A 0.98053 0.093749 0.380404 0.034 Uiso calc 1 . . H
C5A 1.03152(9) 0.3278(3) 0.32621(7) 0.0287(3) Uani d 1 . . C
H5A 1.044154 0.426887 0.359238 0.034 Uiso calc 1 . . H
C6A 1.05090(10) 0.3806(2) 0.26547(7) 0.0279(3) Uani d 1 . . C
H6A 1.076671 0.516171 0.256932 0.033 Uiso calc 1 . . H
C7A 1.03273(9) 0.2358(2) 0.21698(7) 0.0238(3) Uani d 1 . . C
H7A 1.046487 0.271938 0.17545 0.029 Uiso calc 1 . . H
H2A 0.9201(12) -0.362(3) 0.1572(9) 0.029 Uiso d 1 . . H
O1B 0.90378(6) 0.18246(16) 0.03010(4) 0.0208(2) Uani d 1 . . O
O2B 0.90421(6) 0.47435(16) 0.09087(4) 0.0233(2) Uani d 1 . . O
C1B 0.87736(8) 0.2868(2) 0.07617(6) 0.0182(3) Uani d 1 . . C
C2B 0.81062(8) 0.1872(2) 0.11361(6) 0.0191(3) Uani d 1 . . C
C3B 0.77495(9) -0.0123(2) 0.09605(7) 0.0240(3) Uani d 1 . . C
H3B 0.794614 -0.088731 0.060903 0.029 Uiso calc 1 . . H
C4B 0.71129(9) -0.0995(3) 0.12937(7) 0.0276(3) Uani d 1 . . C
H4B 0.687223 -0.234462 0.116803 0.033 Uiso calc 1 . . H
C5B 0.68259(9) 0.0099(3) 0.18102(7) 0.0281(3) Uani d 1 . . C
H5B 0.638622 -0.049325 0.203712 0.034 Uiso calc 1 . . H
C6B 0.71839(10) 0.2062(3) 0.19943(7) 0.0294(3) Uani d 1 . . C
H6B 0.699612 0.27974 0.235353 0.035 Uiso calc 1 . . H
C7B 0.78138(9) 0.2955(2) 0.16570(7) 0.0245(3) Uani d 1 . . C
H7B 0.804782 0.431444 0.178167 0.029 Uiso calc 1 . . H
N1 0.93102(7) -0.24226(18) -0.00606(5) 0.0184(3) Uani d 1 . . N
H1A 0.923064 -0.103085 0.007511 0.028 Uiso calc 1 . . H
H1B 0.923179 -0.337394 0.025872 0.028 Uiso calc 1 . . H
H1C 0.983063 -0.256243 -0.019659 0.028 Uiso calc 1 . . H
C8 0.87263(8) -0.2907(2) -0.05748(6) 0.0180(3) Uani d 1 . . C
C9 0.87343(8) -0.4939(2) -0.08554(6) 0.0201(3) Uani d 1 . . C
H9 0.91151 -0.602175 -0.071704 0.024 Uiso calc 1 . . H
C10 0.81783(9) -0.5382(2) -0.13434(6) 0.0220(3) Uani d 1 . . C
H10 0.818426 -0.677511 -0.153905 0.026 Uiso calc 1 . . H
C11 0.76116(8) -0.3813(2) -0.15503(7) 0.0231(3) Uani d 1 . . C
C12 0.76166(9) -0.1784(2) -0.12566(7) 0.0244(3) Uani d 1 . . C
H12 0.723413 -0.070006 -0.139144 0.029 Uiso calc 1 . . H
C13 0.81700(9) -0.1310(2) -0.07693(6) 0.0217(3) Uani d 1 . . C
H13 0.816758 0.008309 -0.057299 0.026 Uiso calc 1 . . H
C14 0.70149(10) -0.4308(3) -0.20819(8) 0.0315(4) Uani d 1 . . C
H14A 0.710217 -0.580579 -0.222855 0.047 Uiso calc 0.5 . . H
H14B 0.645325 -0.416001 -0.193783 0.047 Uiso calc 0.5 . . H
H14C 0.71016 -0.328105 -0.242481 0.047 Uiso calc 0.5 . . H
H14D 0.666918 -0.302544 -0.216557 0.047 Uiso calc 0.5 . . H
H14E 0.731809 -0.467122 -0.245629 0.047 Uiso calc 0.5 . . H
H14F 0.666975 -0.555018 -0.196932 0.047 Uiso calc 0.5 . . H
N2 0.32769(15) 0.5871(5) 0.00365(11) 0.0698(7) Uani d 0.5 . . N
H2B 0.291(3) 0.516(8) 0.022(2) 0.059 Uiso d 0.5 . . H
H2C 0.313(3) 0.739(8) -0.013(2) 0.059 Uiso d 0.5 . . H
C18 0.32769(15) 0.5871(5) 0.00365(11) 0.0698(7) Uani d 0.5 . . C
H18A 0.299499 0.456699 0.018681 0.058 Uiso calc 0.5 . . H
H18B 0.317835 0.709803 0.031893 0.058 Uiso calc 0.5 . . H
H18C 0.306751 0.623773 -0.038377 0.058 Uiso calc 0.5 . . H
C15 0.44681(16) 0.3400(3) 0.01941(9) 0.0495(5) Uani d 1 . . C
H15 0.41058 0.228825 0.032643 0.059 Uiso calc 1 . . H
C16 0.41552(15) 0.5442(3) 0.00180(8) 0.0483(5) Uani d 1 . . C
C17 0.52951(16) 0.2983(3) 0.01782(9) 0.0492(5) Uani d 1 . . C
H17 0.549498 0.158751 0.030397 0.059 Uiso calc 1 . . H




#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1A . 1.2148(17) ?
O2A C1A . 1.3285(17) ?
O2A H2A . 0.88(2) ?
C1A C2A . 1.4940(18) ?
C2A C7A . 1.391(2) ?
C2A C3A . 1.396(2) ?
C3A C4A . 1.389(2) ?
C3A H3A . 0.95 ?
C4A C5A . 1.388(2) ?
C4A H4A . 0.95 ?
C5A C6A . 1.386(2) ?
C5A H5A . 0.95 ?
C6A C7A . 1.391(2) ?
C6A H6A . 0.95 ?
C7A H7A . 0.95 ?
O1B C1B . 1.2617(17) ?
O2B C1B . 1.2647(16) ?
C1B C2B . 1.5004(19) ?
C2B C7B . 1.394(2) ?
C2B C3B . 1.3989(19) ?
C3B C4B . 1.384(2) ?
C3B H3B . 0.95 ?
C4B C5B . 1.386(2) ?
C4B H4B . 0.95 ?
C5B C6B . 1.388(2) ?
C5B H5B . 0.95 ?
C6B C7B . 1.386(2) ?
C6B H6B . 0.95 ?
C7B H7B . 0.95 ?
N1 C8 . 1.4663(16) ?
N1 H1A . 0.91 ?
N1 H1B . 0.91 ?
N1 H1C . 0.91 ?
C8 C9 . 1.3808(19) ?
C8 C13 . 1.3897(19) ?
C9 C10 . 1.3915(18) ?
C9 H9 . 0.95 ?
C10 C11 . 1.396(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.391(2) ?
C11 C14 . 1.5083(18) ?
C12 C13 . 1.3917(19) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C14 H14D . 0.98 ?
C14 H14E . 0.98 ?
C14 H14F . 0.98 ?
N2 C16 . 1.459(3) ?
N2 H2B . 0.85(5) ?
N2 H2C . 1.02(5) ?
C15 C17 . 1.375(4) ?
C15 C16 . 1.397(3) ?
C15 H15 . 0.95 ?
C16 C17 3_665 1.390(3) ?
C17 H17 . 0.95 ?

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
C1A O2A H2A 108.8(13) . . ?
O1A C1A O2A 123.35(13) . . ?
O1A C1A C2A 123.41(13) . . ?
O2A C1A C2A 113.24(12) . . ?
C7A C2A C3A 119.70(13) . . ?
C7A C2A C1A 118.04(12) . . ?
C3A C2A C1A 122.26(13) . . ?
C4A C3A C2A 120.01(14) . . ?
C4A C3A H3A 120 . . ?
C2A C3A H3A 120 . . ?
C5A C4A C3A 120.12(14) . . ?
C5A C4A H4A 119.9 . . ?
C3A C4A H4A 119.9 . . ?
C6A C5A C4A 119.98(14) . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C5A C6A C7A 120.23(14) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
C6A C7A C2A 119.97(14) . . ?
C6A C7A H7A 120 . . ?
C2A C7A H7A 120 . . ?
O1B C1B O2B 121.99(13) . . ?
O1B C1B C2B 118.86(12) . . ?
O2B C1B C2B 119.13(12) . . ?
C7B C2B C3B 118.71(13) . . ?
C7B C2B C1B 120.38(12) . . ?
C3B C2B C1B 120.88(12) . . ?
C4B C3B C2B 120.67(14) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C5B 120.13(14) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B C6B 119.67(14) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C7B C6B C5B 120.38(14) . . ?
C7B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
C6B C7B C2B 120.42(14) . . ?
C6B C7B H7B 119.8 . . ?
C2B C7B H7B 119.8 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 C8 C13 121.08(12) . . ?
C9 C8 N1 119.67(12) . . ?
C13 C8 N1 119.25(12) . . ?
C8 C9 C10 119.23(12) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 121.12(13) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 118.29(12) . . ?
C12 C11 C14 121.08(13) . . ?
C10 C11 C14 120.62(13) . . ?
C11 C12 C13 121.38(13) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 118.89(13) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C16 N2 H2B 129(4) . . ?
C16 N2 H2C 112(3) . . ?
H2B N2 H2C 118(4) . . ?
C17 C15 C16 120.7(2) . . ?
C17 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 117.8(2) 3_665 . ?
C17 C16 N2 121.8(2) 3_665 . ?
C15 C16 N2 120.4(2) . . ?
C15 C17 C16 121.44(19) . 3_665 ?
C15 C17 H17 119.3 . . ?
C16 C17 H17 119.3 3_665 . ?

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 C7A 9.4(2) . . . . ?
O2A C1A C2A C7A -170.34(12) . . . . ?
O1A C1A C2A C3A -170.07(13) . . . . ?
O2A C1A C2A C3A 10.17(18) . . . . ?
C7A C2A C3A C4A 0.2(2) . . . . ?
C1A C2A C3A C4A 179.66(13) . . . . ?
C2A C3A C4A C5A 0.2(2) . . . . ?
C3A C4A C5A C6A -0.2(2) . . . . ?
C4A C5A C6A C7A -0.2(2) . . . . ?
C5A C6A C7A C2A 0.5(2) . . . . ?
C3A C2A C7A C6A -0.5(2) . . . . ?
C1A C2A C7A C6A 179.99(13) . . . . ?
O1B C1B C2B C7B 178.43(12) . . . . ?
O2B C1B C2B C7B -3.04(19) . . . . ?
O1B C1B C2B C3B -3.41(19) . . . . ?
O2B C1B C2B C3B 175.12(12) . . . . ?
C7B C2B C3B C4B 0.6(2) . . . . ?
C1B C2B C3B C4B -177.54(13) . . . . ?
C2B C3B C4B C5B -0.5(2) . . . . ?
C3B C4B C5B C6B -0.5(2) . . . . ?
C4B C5B C6B C7B 1.4(2) . . . . ?
C5B C6B C7B C2B -1.3(2) . . . . ?
C3B C2B C7B C6B 0.2(2) . . . . ?
C1B C2B C7B C6B 178.44(13) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
N1 C8 C9 C10 -179.94(12) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C14 179.67(14) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C14 C11 C12 C13 -179.45(14) . . . . ?
C9 C8 C13 C12 -0.2(2) . . . . ?
N1 C8 C13 C12 -179.85(12) . . . . ?
C11 C12 C13 C8 -0.1(2) . . . . ?
C17 C15 C16 C17 0.6(3) . . . 3_665 ?
C17 C15 C16 N2 -180.0(2) . . . . ?
C16 C15 C17 C16 -0.6(3) . . . 3_665 ?

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
O2A H2A O2B 0.88(2) 1.75(2) 2.6345(14) 179(2) 1_545 yes
N1 H1A O1B 0.91 1.84 2.7505(15) 176.3 . yes
N1 H1B O2B 0.91 1.84 2.7498(15) 178.2 1_545 yes
N1 H1C O1B 0.91 1.92 2.7841(15) 157.7 3_755 yes
C9 H9 O1A 0.95 2.65 3.4047(18) 136.6 3_745 yes
C9 H9 O1B 0.95 2.55 3.1990(16) 125.3 1_545 yes
C13 H13 O1B 0.95 2.55 3.2795(17) 133.6 . yes
O2A H2A O2B 0.88(2) 1.75(2) 2.6345(14) 179(2) 1_545 yes
N1 H1A O1B 0.91 1.84 2.7505(15) 176.3 . yes
N1 H1B O2B 0.91 1.84 2.7498(15) 178.2 1_545 yes
N1 H1C O1B 0.91 1.92 2.7841(15) 157.7 3_755 yes
C9 H9 O1A 0.95 2.65 3.4047(18) 136.6 3_745 yes
C9 H9 O1B 0.95 2.55 3.1990(16) 125.3 1_545 yes
C13 H13 O1B 0.95 2.55 3.2795(17) 133.6 . yes



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# END of CIF
