# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_mal261
_database_code_depnum_ccdc_archive 'CCDC 2191936'
loop_
_audit_author_name
_audit_author_address
'Alexander Roller'
;University of Vienna
Austria
;
_audit_update_record             
;
2022-07-21 deposited with the CCDC.	2023-08-29 downloaded from the CCDC.
;
_audit_creation_date             2022-05-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O3'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3359(13)
_cell_length_b                   10.169(3)
_cell_length_c                   20.658(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1961.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    618
_cell_measurement_temperature    100
_cell_measurement_theta_max      62.30
_cell_measurement_theta_min      5.09
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.8613
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            'clear collourless'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.275
_diffrn_reflns_theta_min         4.280
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
 2174 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_reflns_d_resolution_high        0.830
_reflns_d_resolution_low         20.658
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2953
_reflns_number_total             3563
_reflns_special_details          'Friedel pairs have not been merged'
_reflns_threshold_expression     I>4u(I)
_computing_cell_refinement       
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_data_reduction        
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_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 1.90, Darmstadt 2020
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0061(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1044P)²+0.8176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1541
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15521(12) 0.69843(11) 0.15044(5) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.41926(13) 0.22554(12) 0.47319(5) 0.0346(4) Uani 1 1 d . . . . .
O3 O 0.04285(11) 0.59040(13) 0.28982(6) 0.0353(4) Uani 1 1 d . . . . .
N4 N 0.26322(14) 0.64010(13) 0.25177(6) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.352723 0.620117 0.252134 0.034 Uiso 1 1 calc R U . . .
C5 C 0.17374(16) 0.57323(16) 0.29113(7) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.35247(17) 0.30443(15) 0.42888(8) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.24016(16) 0.47874(16) 0.33735(7) 0.0268(4) Uani 1 1 d . . . . .
C8 C 0.20812(17) 0.29721(16) 0.41250(8) 0.0305(4) Uani 1 1 d . . . . .
H8 H 0.148948 0.234854 0.431719 0.037 Uiso 1 1 calc R U . . .
C9 C 0.25233(19) 0.62065(17) 0.11346(8) 0.0324(4) Uani 1 1 d . . . . .
H9A H 0.211367 0.602610 0.071776 0.049 Uiso 1 1 calc R U . . .
H9B H 0.270314 0.539358 0.135649 0.049 Uiso 1 1 calc R U . . .
H9C H 0.340746 0.667593 0.108064 0.049 Uiso 1 1 calc R U . . .
C10 C 0.21573(18) 0.74323(16) 0.20925(8) 0.0303(4) Uani 1 1 d . . . . .
H10A H 0.145140 0.796106 0.231832 0.036 Uiso 1 1 calc R U . . .
H10B H 0.296600 0.799638 0.199355 0.036 Uiso 1 1 calc R U . . .
C11 C 0.43971(17) 0.39868(16) 0.39997(8) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.535882 0.403807 0.411430 0.037 Uiso 1 1 calc R U . . .
C12 C 0.38512(17) 0.48460(16) 0.35448(7) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.444747 0.546489 0.335187 0.034 Uiso 1 1 calc R U . . .
C13 C 0.15371(17) 0.38458(16) 0.36701(8) 0.0293(4) Uani 1 1 d . . . . .
H13 H 0.057205 0.380129 0.356070 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3362(2) 0.12373(17) 0.50301(8) 0.0352(4) Uani 1 1 d . . . . .
H14A H 0.300792 0.065038 0.470330 0.053 Uiso 1 1 calc R U . . .
H14B H 0.257055 0.162197 0.525835 0.053 Uiso 1 1 calc R U . . .
H14C H 0.395207 0.075739 0.532865 0.053 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
O1 C9 1.425(2) . ?
O1 C10 1.4153(19) . ?
O2 C6 1.3676(19) . ?
O2 C14 1.433(2) . ?
O3 C5 1.2347(19) . ?
N4 H4 0.8600 . ?
N4 C5 1.349(2) . ?
N4 C10 1.438(2) . ?
C5 C7 1.490(2) . ?
C6 C8 1.391(2) . ?
C6 C11 1.392(2) . ?
C7 C12 1.400(2) . ?
C7 C13 1.394(2) . ?
C8 H8 0.9300 . ?
C8 C13 1.389(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.381(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C9 112.63(12) . . ?
C6 O2 C14 117.72(13) . . ?
C5 N4 H4 118.5 . . ?
C5 N4 C10 122.99(13) . . ?
C10 N4 H4 118.5 . . ?
O3 C5 N4 121.89(15) . . ?
O3 C5 C7 121.14(14) . . ?
N4 C5 C7 116.96(13) . . ?
O2 C6 C8 124.99(14) . . ?
O2 C6 C11 115.10(14) . . ?
C8 C6 C11 119.91(15) . . ?
C12 C7 C5 122.47(14) . . ?
C13 C7 C5 118.93(14) . . ?
C13 C7 C12 118.53(15) . . ?
C6 C8 H8 120.5 . . ?
C13 C8 C6 119.00(15) . . ?
C13 C8 H8 120.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N4 114.37(13) . . ?
O1 C10 H10A 108.7 . . ?
O1 C10 H10B 108.7 . . ?
N4 C10 H10A 108.7 . . ?
N4 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C6 C11 H11 119.6 . . ?
C12 C11 C6 120.77(15) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.13(15) . . ?
C11 C12 H12 119.9 . . ?
C7 C13 H13 119.2 . . ?
C8 C13 C7 121.65(15) . . ?
C8 C13 H13 119.2 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 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
O2 C6 C8 C13 179.35(14) . . . . ?
O2 C6 C11 C12 -179.88(14) . . . . ?
O3 C5 C7 C12 -160.00(15) . . . . ?
O3 C5 C7 C13 17.0(2) . . . . ?
N4 C5 C7 C12 19.0(2) . . . . ?
N4 C5 C7 C13 -164.00(14) . . . . ?
C5 N4 C10 O1 -81.21(18) . . . . ?
C5 C7 C12 C11 176.81(14) . . . . ?
C5 C7 C13 C8 -177.35(14) . . . . ?
C6 C8 C13 C7 0.2(2) . . . . ?
C6 C11 C12 C7 0.7(2) . . . . ?
C8 C6 C11 C12 -0.7(2) . . . . ?
C9 O1 C10 N4 -59.05(17) . . . . ?
C10 N4 C5 O3 5.1(2) . . . . ?
C10 N4 C5 C7 -173.85(13) . . . . ?
C11 C6 C8 C13 0.3(2) . . . . ?
C12 C7 C13 C8 -0.2(2) . . . . ?
C13 C7 C12 C11 -0.2(2) . . . . ?
C14 O2 C6 C8 3.0(2) . . . . ?
C14 O2 C6 C11 -177.95(14) . . . . ?

