# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_PHSP1070_a
_database_code_depnum_ccdc_archive 'CCDC 2268806'
loop_
_audit_author_name
_audit_author_address
'Tim Gruene'
;Centre of Xray Structure Analysis, University of Vienna
Austria
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_audit_creation_method           'STOE LANA'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         244.29
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_symmetry_cell_setting           orthorhombic
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_audit_creation_date             2023-06-08
_space_group_name_Hall           'P 2ac 2ab'
_audit_contact_author            'J. Richter'
_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.
;
_diffrn_source_power             0.050

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

_cell_length_a                   9.8956(5)
_cell_length_b                   10.1319(5)
_cell_length_c                   11.9988(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1203.01(12)
_STOE_detector_size_x            '7.7 cm'
_STOE_detector_size_y            '3.8 cm'
_STOE_detector_pixelsize_x       '0.075 mm'
_STOE_detector_pixelsize_y       '0.075 mm'
_STOE_detector_distance          '40.0 mm'
_STOE_measurement_identifier     PHSP1070
_STOE_measurement_tube_power     '49.8 W'
_STOE_measurement_total_run_number 21
_STOE_measurement_total_frame_number 1641
_STOE_measurement_min_exposure_per_frame '4.0 s'
_STOE_measurement_max_exposure_per_frame '4.0 s'
_STOE_measurement_mean_exposure_per_frame '4.0 s'
_STOE_measurement_total_exposure_time '109 min'
_STOE_evaluation_integration_A   15.0
_STOE_evaluation_integration_B   1.5
_STOE_evaluation_integration_EMS 0.040
_STOE_evaluation_LANA_point_group 222
_STOE_evaluation_LANA_FS_max_order -
_STOE_evaluation_LANA_DXS_max_order -
_STOE_evaluation_LANA_DYS_max_order -
_STOE_evaluation_LANA_BIS_l_even_max -
_STOE_evaluation_LANA_BIS_l_odd_max -
_STOE_evaluation_LANA_BOS_l_even_max -
_STOE_evaluation_LANA_BOS_l_odd_max -
_STOE_evaluation_LANA_OR_c1      0.050
_STOE_evaluation_LANA_OR_c2      0
_STOE_evaluation_LANA_OR_c3      0
_STOE_evaluation_LANA_OR_c4      1.0
_STOE_evaluation_LANA_max_2theta_available 61.5
_STOE_evaluation_LANA_max_2theta_desired 61.5
_STOE_evaluation_LANA_number_refls_total 15923
_STOE_evaluation_LANA_number_refls_outliers 1332
_STOE_evaluation_LANA_number_refls_after_OR 14591
_STOE_evaluation_LANA_number_refls_unique 3583
_STOE_evaluation_LANA_number_refls_written 14591
_STOE_evaluation_LANA_completeness 94.9
_STOE_evaluation_LANA_mean_redundancy 4.1
_STOE_evaluation_LANA_table      
;
#----------------------------------------------------------------------------
2Theta           7.8   14.2   20.6   27.0   33.4   39.8   46.2   52.6   59.0
#----------------------------------------------------------------------------
<Resolution>    4.47   2.78   1.96   1.54   1.23   1.04   0.90   0.80   0.73
N(total)         214    996   2069   2076   1958   2170   2411   2306   1723
<Redundancy>     6.8   11.5   11.9    7.0    4.6    3.9    3.5    2.8    2.4
Complet. [%%]   100.0  100.0  100.0  100.0   99.7   99.8   99.7   97.3   81.1
<I/sigma>      212.9  100.4   53.2   27.0   17.0   11.3    5.6    3.5    2.9
R(int)         0.072  0.083  0.060  0.042  0.037  0.043  0.066  0.081  0.091
#----------------------------------------------------------------------------
;
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    26059
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.79
_exptl_crystal_description       'orthorhombic brick'
_exptl_crystal_colour            clear
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_size_rad          0.145
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.9904
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   
;
STOE LANA, spherical absorption correction
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100
_diffrn_ambient_environment      ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Axo Mo'
_diffrn_source_type              ?
_diffrn_source_voltage           60
_diffrn_source_current           0.830
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean 13.33
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_measurement_details      ' 1641 frames, detector distance = 40 mm'
_diffrn_reflns_number            14507
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         30.72
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3565
_reflns_number_gt                2861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.996
_reflns_d_resolution_high        0.696
_reflns_d_resolution_low         7.634
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              -17
_reflns_limit_l_max              16
_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       
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_cell_refinement       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_reduction        
'  X-Area Integrate 2.5.3.0 (STOE, 2021)  X-Area LANA 2.7.5.0 (STOE, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Hübschle 2011)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.1, Darmstadt 2022
;
_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)+(0.0399P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53813(11) 0.78426(12) 0.53891(11) 0.0151(3) Uani 1 1 d . . . . .
O2 O 0.41330(14) 0.27179(13) 0.58094(13) 0.0296(4) Uani 1 1 d . . . . .
N1 N 0.32522(14) 0.78540(14) 0.46731(13) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.244552 0.748941 0.469529 0.017 Uiso 1 1 calc R U . . .
N2 N 0.37561(13) 0.66636(13) 0.62733(13) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.35216(15) 0.88234(17) 0.38412(16) 0.0125(4) Uani 1 1 d . . . . .
C2 C 0.40228(16) 1.00573(16) 0.41231(16) 0.0157(4) Uani 1 1 d . . . . .
H2 H 0.423948 1.025588 0.487595 0.019 Uiso 1 1 calc R U . . .
C3 C 0.42053(17) 1.09990(18) 0.32985(18) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.455774 1.184137 0.348912 0.025 Uiso 1 1 calc R U . . .
C4 C 0.38810(18) 1.07268(19) 0.22046(17) 0.0216(4) Uani 1 1 d . . . . .
H4 H 0.400581 1.137912 0.164526 0.026 Uiso 1 1 calc R U . . .
C5 C 0.33727(18) 0.94979(19) 0.19265(17) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.313751 0.930589 0.117622 0.025 Uiso 1 1 calc R U . . .
C6 C 0.32080(17) 0.85489(18) 0.27462(16) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.287554 0.769997 0.255170 0.019 Uiso 1 1 calc R U . . .
C7 C 0.41966(16) 0.74685(16) 0.54373(15) 0.0116(3) Uani 1 1 d . . . . .
C8 C 0.47261(16) 0.59364(17) 0.69601(14) 0.0124(4) Uani 1 1 d . . . . .
H8 H 0.549429 0.651307 0.719678 0.015 Uiso 1 1 calc R U . . .
C9 C 0.38605(17) 0.55240(19) 0.79550(16) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.395361 0.616358 0.857402 0.021 Uiso 1 1 calc R U . . .
H9B H 0.412579 0.463784 0.822503 0.021 Uiso 1 1 calc R U . . .
C10 C 0.24008(16) 0.55110(19) 0.75056(16) 0.0153(4) Uani 1 1 d . . . . .
H10A H 0.198700 0.462886 0.760248 0.018 Uiso 1 1 calc R U . . .
H10B H 0.183874 0.617225 0.789826 0.018 Uiso 1 1 calc R U . . .
C11 C 0.25292(16) 0.58551(16) 0.62693(15) 0.0121(4) Uani 1 1 d . . . . .
H11 H 0.172901 0.636406 0.599668 0.014 Uiso 1 1 calc R U . . .
C12 C 0.27967(16) 0.46377(18) 0.55513(16) 0.0161(4) Uani 1 1 d . . . . .
H12A H 0.201626 0.403043 0.561082 0.019 Uiso 1 1 calc R U . . .
H12B H 0.287610 0.491252 0.476226 0.019 Uiso 1 1 calc R U . . .
C13 C 0.40595(18) 0.39135(18) 0.58849(16) 0.0171(4) Uani 1 1 d . . . . .
C14 C 0.52276(18) 0.47392(17) 0.62884(17) 0.0169(4) Uani 1 1 d . . . . .
H14A H 0.576067 0.504911 0.564109 0.020 Uiso 1 1 calc R U . . .
H14B H 0.582566 0.419278 0.676238 0.020 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2335(19) . ?
O2 C13 1.217(2) . ?
N1 C7 1.366(2) . ?
N1 C1 1.426(2) . ?
N2 C7 1.364(2) . ?
N2 C8 1.464(2) . ?
N2 C11 1.465(2) . ?
C1 C6 1.378(3) . ?
C1 C2 1.387(2) . ?
C2 C3 1.386(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.385(3) . ?
C8 C9 1.527(2) . ?
C8 C14 1.539(2) . ?
C9 C10 1.542(2) . ?
C10 C11 1.529(3) . ?
C11 C12 1.528(3) . ?
C12 C13 1.503(2) . ?
C13 C14 1.507(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
C7 N1 C1 122.62(14) . . ?
C7 N2 C8 120.35(14) . . ?
C7 N2 C11 126.64(14) . . ?
C8 N2 C11 105.30(13) . . ?
C6 C1 C2 119.66(18) . . ?
C6 C1 N1 119.10(16) . . ?
C2 C1 N1 121.15(17) . . ?
C3 C2 C1 119.53(18) . . ?
C4 C3 C2 120.76(18) . . ?
C3 C4 C5 119.61(18) . . ?
C4 C5 C6 119.75(19) . . ?
C1 C6 C5 120.68(18) . . ?
O1 C7 N2 121.45(16) . . ?
O1 C7 N1 122.06(16) . . ?
N2 C7 N1 116.48(14) . . ?
N2 C8 C9 102.12(13) . . ?
N2 C8 C14 108.27(14) . . ?
C9 C8 C14 112.00(14) . . ?
C8 C9 C10 104.74(14) . . ?
C11 C10 C9 105.04(14) . . ?
N2 C11 C12 108.05(14) . . ?
N2 C11 C10 101.14(14) . . ?
C12 C11 C10 112.17(14) . . ?
C13 C12 C11 112.83(15) . . ?
O2 C13 C12 121.04(17) . . ?
O2 C13 C14 122.05(17) . . ?
C12 C13 C14 116.89(15) . . ?
C13 C14 C8 111.01(14) . . ?


####################################################################### 
# 
# 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_PHSP-1071_a
_database_code_depnum_ccdc_archive 'CCDC 2269266'
loop_
_audit_author_name
_audit_author_address
'Tim Gruene'
;Centre of Xray Structure Analysis, University of Vienna
Austria
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_audit_creation_method           'STOE LANA'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C24 H24 N4 O4'
_chemical_formula_moiety         ?
_chemical_formula_weight         432.47
_chemical_melting_point          ?
_symmetry_cell_setting           monoclinic
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_audit_creation_date             2023-06-11
_audit_contact_author            'J. Richter'
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_diffrn_source_power             0.050
_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                   21.3525(12)
_cell_length_b                   8.6525(5)
_cell_length_c                   11.7801(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.852(5)
_STOE_detector_size_x            '7.7 cm'
_STOE_detector_size_y            '3.8 cm'
_STOE_detector_pixelsize_x       '0.075 mm'
_STOE_detector_pixelsize_y       '0.075 mm'
_STOE_detector_distance          '40.0 mm'
_STOE_measurement_identifier     PHSP1071
_STOE_measurement_tube_power     '50.0 W'
_STOE_measurement_total_run_number 30
_STOE_measurement_total_frame_number 6000
_STOE_measurement_min_exposure_per_frame '10.0 s'
_STOE_measurement_max_exposure_per_frame '10.0 s'
_STOE_measurement_mean_exposure_per_frame '10.0 s'
_STOE_measurement_total_exposure_time '16.7 h'
_STOE_evaluation_integration_A   14.0
_STOE_evaluation_integration_B   1.0
_STOE_evaluation_integration_EMS 0.050
_STOE_evaluation_LANA_point_group 2/m
_STOE_evaluation_LANA_FS_max_order 3
_STOE_evaluation_LANA_DXS_max_order -
_STOE_evaluation_LANA_DYS_max_order -
_STOE_evaluation_LANA_BIS_l_even_max -
_STOE_evaluation_LANA_BIS_l_odd_max -
_STOE_evaluation_LANA_BOS_l_even_max 4
_STOE_evaluation_LANA_BOS_l_odd_max 1
_STOE_evaluation_LANA_OR_c1      0.050
_STOE_evaluation_LANA_OR_c2      0
_STOE_evaluation_LANA_OR_c3      0
_STOE_evaluation_LANA_OR_c4      1.0
_STOE_evaluation_LANA_max_2theta_available 137.2
_STOE_evaluation_LANA_max_2theta_desired 137.2
_STOE_evaluation_LANA_number_refls_total 21436
_STOE_evaluation_LANA_number_refls_outliers 1303
_STOE_evaluation_LANA_number_refls_after_OR 20133
_STOE_evaluation_LANA_number_refls_unique 4012
_STOE_evaluation_LANA_number_refls_written 20133
_STOE_evaluation_LANA_completeness 96.6
_STOE_evaluation_LANA_mean_redundancy 5.0
_STOE_evaluation_LANA_table      
;
#----------------------------------------------------------------------------
2Theta          14.1   28.7   43.3   57.9   72.5   87.1  101.7  116.3  130.9
#----------------------------------------------------------------------------
<Resolution>    5.38   3.01   2.07   1.56   1.30   1.12   1.00   0.91   0.85
N(total)         168    567    803   2866   4425   4155   3608   3124   1720
<Redundancy>     3.7    4.0    2.9    6.6    7.5    5.9    4.7    4.2    3.0
Complet. [%%]    97.5   99.3   99.2   99.8  100.0  100.0   98.4   95.4   85.3
<I/sigma>       63.2   50.4   17.7    8.2    4.7    4.1    3.0    1.8    1.5
R(int)         0.010  0.014  0.032  0.076  0.125  0.141  0.177  0.264  0.325
#----------------------------------------------------------------------------
;
_cell_angle_gamma                90
_cell_volume                     2093.78(22)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    14561
_cell_measurement_theta_min      6.44
_cell_measurement_theta_max      69.39
_exptl_crystal_description       blade
_exptl_crystal_colour            clear
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_size_rad          0.031
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7974
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100
_diffrn_ambient_environment      ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Primux 100 micro'
_diffrn_source_type              ?
_diffrn_source_voltage           50
_diffrn_source_current           1.00
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean 13.33
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_measurement_details      ' 6000 frames, detector distance = 40 mm'
_diffrn_reflns_number            19219
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_theta_min         4.305
_diffrn_reflns_theta_max         68.588
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3737
_reflns_number_gt                2313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_d_resolution_high        0.828
_reflns_d_resolution_low         11.332
_reflns_limit_h_min              -14
_reflns_limit_h_max              8
_reflns_limit_k_min              -10
_reflns_limit_k_max              6
_reflns_limit_l_min              -24
_reflns_limit_l_max              25
_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       
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_cell_refinement       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_reduction        
'  X-Area Integrate 2.5.3.0 (STOE, 2021)  X-Area LANA 2.7.5.0 (STOE, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Hübschle 2011)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.1, Darmstadt 2022
;
_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)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'
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'

_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_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32071(9) 0.4159(3) 0.85115(18) 0.0303(5) Uani 1 1 d . . . . .
O2 O 0.47394(9) 0.4215(2) 0.68240(17) 0.0250(5) Uani 1 1 d . . . . .
O3 O -0.18590(9) 0.3874(3) 0.44913(18) 0.0302(5) Uani 1 1 d . . . . .
O4 O -0.03000(9) 0.4103(2) 0.79005(17) 0.0266(5) Uani 1 1 d . . . . .
N1 N 0.44841(11) 0.1994(3) 0.7635(2) 0.0246(6) Uani 1 1 d . . . . .
H1 H 0.462418 0.109659 0.795679 0.030 Uiso 1 1 calc R U . . .
N2 N 0.54781(11) 0.2230(3) 0.7267(2) 0.0247(6) Uani 1 1 d . . . . .
H2 H 0.554637 0.128950 0.755848 0.030 Uiso 1 1 calc R U . . .
N3 N -0.05568(11) 0.1951(3) 0.6762(2) 0.0262(6) Uani 1 1 d . . . . .
H3 H -0.041100 0.108261 0.654057 0.031 Uiso 1 1 calc R U . . .
N4 N 0.04140(11) 0.2068(3) 0.8176(2) 0.0247(6) Uani 1 1 d . . . . .
H4 H 0.046554 0.111609 0.795384 0.030 Uiso 1 1 calc R U . . .
C1 C 0.38057(13) 0.3503(3) 0.8566(3) 0.0237(7) Uani 1 1 d . . . . .
C2 C 0.32985(15) 0.5052(4) 0.9501(3) 0.0326(8) Uani 1 1 d . . . . .
H2A H 0.296704 0.564390 0.969421 0.039 Uiso 1 1 calc R U . . .
C3 C 0.39184(15) 0.4983(4) 1.0162(3) 0.0317(8) Uani 1 1 d . . . . .
H3A H 0.410279 0.550054 1.088804 0.038 Uiso 1 1 calc R U . . .
C4 C 0.42454(15) 0.3969(4) 0.9552(3) 0.0296(7) Uani 1 1 d . . . . .
H4A H 0.469128 0.367949 0.979912 0.036 Uiso 1 1 calc R U . . .
C5 C 0.38243(13) 0.2483(4) 0.7563(3) 0.0263(7) Uani 1 1 d . . . . .
H5A H 0.354967 0.156181 0.756595 0.032 Uiso 1 1 calc R U . . .
H5B H 0.364272 0.304235 0.681200 0.032 Uiso 1 1 calc R U . . .
C6 C 0.48875(13) 0.2901(4) 0.7214(2) 0.0229(7) Uani 1 1 d . . . . .
C7 C 0.59884(13) 0.2936(3) 0.6886(3) 0.0224(6) Uani 1 1 d . . . . .
C8 C 0.66250(13) 0.2681(4) 0.7558(3) 0.0255(7) Uani 1 1 d . . . . .
H8 H 0.670931 0.210775 0.827207 0.031 Uiso 1 1 calc R U . . .
C9 C 0.71380(14) 0.3277(4) 0.7172(3) 0.0295(7) Uani 1 1 d . . . . .
H9 H 0.757436 0.306611 0.760583 0.035 Uiso 1 1 calc R U . . .
C10 C 0.70180(14) 0.4170(4) 0.6166(3) 0.0287(7) Uani 1 1 d . . . . .
H10 H 0.737013 0.460211 0.592569 0.034 Uiso 1 1 calc R U . . .
C11 C 0.63830(14) 0.4435(4) 0.5507(3) 0.0282(7) Uani 1 1 d . . . . .
H11 H 0.630099 0.504385 0.481110 0.034 Uiso 1 1 calc R U . . .
C12 C 0.58633(14) 0.3813(4) 0.5861(3) 0.0249(7) Uani 1 1 d . . . . .
H12 H 0.542809 0.398811 0.540444 0.030 Uiso 1 1 calc R U . . .
C13 C -0.12454(13) 0.3412(4) 0.5129(3) 0.0255(7) Uani 1 1 d . . . . .
C14 C -0.07951(15) 0.4007(4) 0.4650(3) 0.0295(7) Uani 1 1 d . . . . .
H14 H -0.033757 0.385669 0.491953 0.035 Uiso 1 1 calc R U . . .
C15 C -0.11365(15) 0.4910(4) 0.3658(3) 0.0316(7) Uani 1 1 d . . . . .
H15 H -0.094978 0.548348 0.314479 0.038 Uiso 1 1 calc R U . . .
C16 C -0.17695(16) 0.4791(4) 0.3592(3) 0.0337(8) Uani 1 1 d . . . . .
H16 H -0.211008 0.527188 0.300765 0.040 Uiso 1 1 calc R U . . .
C17 C -0.12165(14) 0.2437(4) 0.6182(3) 0.0272(7) Uani 1 1 d . . . . .
H17A H -0.139182 0.302786 0.674672 0.033 Uiso 1 1 calc R U . . .
H17B H -0.149370 0.151237 0.593678 0.033 Uiso 1 1 calc R U . . .
C18 C -0.01604(13) 0.2787(4) 0.7630(3) 0.0241(7) Uani 1 1 d . . . . .
C19 C 0.09328(13) 0.2717(3) 0.9065(3) 0.0243(7) Uani 1 1 d . . . . .
C20 C 0.08377(14) 0.3665(4) 0.9947(3) 0.0268(7) Uani 1 1 d . . . . .
H20 H 0.040907 0.393318 0.996506 0.032 Uiso 1 1 calc R U . . .
C21 C 0.13730(14) 0.4227(4) 1.0810(3) 0.0288(7) Uani 1 1 d . . . . .
H21 H 0.130962 0.490189 1.140463 0.035 Uiso 1 1 calc R U . . .
C22 C 0.19963(15) 0.3803(4) 1.0802(3) 0.0326(8) Uani 1 1 d . . . . .
H22 H 0.235987 0.418190 1.139624 0.039 Uiso 1 1 calc R U . . .
C23 C 0.20918(14) 0.2834(4) 0.9936(3) 0.0292(7) Uani 1 1 d . . . . .
H23 H 0.252061 0.253356 0.994253 0.035 Uiso 1 1 calc R U . . .
C24 C 0.15637(14) 0.2296(4) 0.9055(3) 0.0281(7) Uani 1 1 d . . . . .
H24 H 0.163037 0.164507 0.844924 0.034 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.368(4) . ?
O1 C1 1.384(3) . ?
O2 C6 1.235(4) . ?
O3 C16 1.378(4) . ?
O3 C13 1.379(3) . ?
O4 C18 1.241(4) . ?
N1 C6 1.355(4) . ?
N1 C5 1.451(4) . ?
N2 C6 1.374(4) . ?
N2 C7 1.424(4) . ?
N3 C18 1.346(4) . ?
N3 C17 1.450(4) . ?
N4 C18 1.369(4) . ?
N4 C19 1.416(4) . ?
C1 C4 1.340(4) . ?
C1 C5 1.484(4) . ?
C2 C3 1.341(4) . ?
C3 C4 1.431(5) . ?
C7 C12 1.390(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.378(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.395(4) . ?
C13 C14 1.343(4) . ?
C13 C17 1.487(4) . ?
C14 C15 1.429(4) . ?
C15 C16 1.336(5) . ?
C19 C20 1.382(4) . ?
C19 C24 1.399(4) . ?
C20 C21 1.393(4) . ?
C21 C22 1.383(4) . ?
C22 C23 1.378(5) . ?
C23 C24 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 106.1(2) . . ?
C16 O3 C13 106.0(2) . . ?
C6 N1 C5 120.9(3) . . ?
C6 N2 C7 125.2(3) . . ?
C18 N3 C17 122.1(3) . . ?
C18 N4 C19 125.9(3) . . ?
C4 C1 O1 109.7(3) . . ?
C4 C1 C5 134.7(3) . . ?
O1 C1 C5 115.6(2) . . ?
C3 C2 O1 111.0(3) . . ?
C2 C3 C4 106.0(3) . . ?
C1 C4 C3 107.3(3) . . ?
N1 C5 C1 111.3(2) . . ?
O2 C6 N1 123.0(3) . . ?
O2 C6 N2 123.0(3) . . ?
N1 C6 N2 114.0(3) . . ?
C12 C7 C8 120.5(3) . . ?
C12 C7 N2 121.7(2) . . ?
C8 C7 N2 117.7(3) . . ?
C7 C8 C9 119.2(3) . . ?
C10 C9 C8 120.6(3) . . ?
C9 C10 C11 119.9(3) . . ?
C10 C11 C12 120.4(3) . . ?
C7 C12 C11 119.4(3) . . ?
C14 C13 O3 110.0(3) . . ?
C14 C13 C17 134.1(3) . . ?
O3 C13 C17 115.8(2) . . ?
C13 C14 C15 106.8(3) . . ?
C16 C15 C14 106.7(3) . . ?
C15 C16 O3 110.5(3) . . ?
N3 C17 C13 111.8(2) . . ?
O4 C18 N3 122.9(3) . . ?
O4 C18 N4 122.9(3) . . ?
N3 C18 N4 114.2(3) . . ?
C20 C19 C24 120.0(3) . . ?
C20 C19 N4 123.1(3) . . ?
C24 C19 N4 116.8(3) . . ?
C19 C20 C21 119.7(3) . . ?
C22 C21 C20 120.2(3) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 120.2(3) . . ?
C23 C24 C19 119.6(3) . . ?


