# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_Ch_TEMPO-COO
_database_code_depnum_ccdc_archive 'CCDC 2283380'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2023-07-21 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 N O3, C5 H14 N O, 1.25(C2 H6 O)'
_chemical_formula_sum            'C17.50 H38.50 N2 O5.25'
_chemical_formula_weight         361.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.2287(15)
_cell_length_b                   23.0298(18)
_cell_length_c                   5.8087(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2037.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    760
_cell_measurement_theta_min      3.8560
_cell_measurement_theta_max      23.6270

_exptl_crystal_description       needles
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             798
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            4907
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.818
_diffrn_reflns_theta_max         28.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_point_group_measured_fraction_full 0.749
_reflns_number_total             3016
_reflns_number_gt                1990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.330
_reflns_Friedel_fraction_max     0.328
_reflns_Friedel_fraction_full    0.453

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 479 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3016
_refine_ls_number_parameters     201
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3654(2) 0.47768(11) -0.03857(2) 0.0640(11) Uani 1 1 d D . . . .
H1 H 0.3311(4) 0.5052(2) -0.1022(16) 0.11(2) Uiso 1 1 d D . . . .
C2 C 0.3662(3) 0.50074(14) 0.1863(7) 0.0389(11) Uani 1 1 d . . . . .
H2A H 0.305205 0.503208 0.244630 0.047 Uiso 1 1 calc R U . . .
H2B H 0.390655 0.540548 0.182287 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4195(3) 0.46434(13) 0.3463(7) 0.0287(9) Uani 1 1 d . . . . .
H3A H 0.424140 0.485101 0.495060 0.034 Uiso 1 1 calc R U . . .
H3B H 0.479602 0.461181 0.282367 0.034 Uiso 1 1 calc R U . . .
N4 N 0.38620(19) 0.40368(11) 0.3938(6) 0.0255(7) Uani 1 1 d . . . . .
C5 C 0.4425(3) 0.37824(16) 0.5800(7) 0.0368(10) Uani 1 1 d . . . . .
H5A H 0.503470 0.376138 0.526800 0.055 Uiso 1 1 calc R U . . .
H5B H 0.421536 0.339131 0.617543 0.055 Uiso 1 1 calc R U . . .
H5C H 0.439250 0.402817 0.717503 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3951(3) 0.36561(15) 0.1883(7) 0.0374(10) Uani 1 1 d . . . . .
H6A H 0.356007 0.379467 0.066164 0.056 Uiso 1 1 calc R U . . .
H6B H 0.379326 0.325708 0.229683 0.056 Uiso 1 1 calc R U . . .
H6C H 0.456013 0.366579 0.133631 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2934(3) 0.40373(17) 0.4703(8) 0.0436(11) Uani 1 1 d . . . . .
H7A H 0.275121 0.363920 0.505536 0.065 Uiso 1 1 calc R U . . .
H7B H 0.256240 0.419459 0.347528 0.065 Uiso 1 1 calc R U . . .
H7C H 0.287546 0.427858 0.608410 0.065 Uiso 1 1 calc R U . . .
N11 N 0.2808(2) 0.21730(12) 0.6528(6) 0.0267(7) Uani 1 1 d . . . . .
O11 O 0.31110(17) 0.25614(10) 0.5120(6) 0.0374(7) Uani 1 1 d . . . . .
C12 C 0.3472(2) 0.17665(14) 0.7519(6) 0.0250(8) Uani 1 1 d . . . . .
C13 C 0.3007(2) 0.12598(14) 0.8724(7) 0.0288(9) Uani 1 1 d . . . . .
H13A H 0.278809 0.098610 0.754177 0.035 Uiso 1 1 calc R U . . .
H13B H 0.343872 0.104958 0.968744 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2240(2) 0.14489(14) 1.0234(7) 0.0248(8) Uani 1 1 d . . . . .
H14 H 0.246859 0.174163 1.135565 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1582(2) 0.17534(15) 0.8701(7) 0.0290(9) Uani 1 1 d . . . . .
H15A H 0.138088 0.147693 0.750639 0.035 Uiso 1 1 calc R U . . .
H15B H 0.106418 0.186089 0.964086 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1926(2) 0.22937(14) 0.7524(7) 0.0256(8) Uani 1 1 d . . . . .
C17 C 0.4039(3) 0.15351(17) 0.5546(7) 0.0368(10) Uani 1 1 d . . . . .
H17A H 0.366272 0.134371 0.440626 0.055 Uiso 1 1 calc R U . . .
H17B H 0.446439 0.125501 0.615253 0.055 Uiso 1 1 calc R U . . .
H17C H 0.435148 0.185821 0.481707 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4042(3) 0.21103(16) 0.9239(7) 0.0349(10) Uani 1 1 d . . . . .
H18A H 0.423456 0.247436 0.852553 0.052 Uiso 1 1 calc R U . . .
H18B H 0.455738 0.187839 0.966183 0.052 Uiso 1 1 calc R U . . .
H18C H 0.369787 0.219645 1.062233 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1819(3) 0.09566(17) 1.1622(7) 0.0355(10) Uani 1 1 d . . . . .
O19 O 0.1066(2) 0.10128(13) 1.2275(8) 0.0726(11) Uani 1 1 d . . . . .
O20 O 0.2268(2) 0.05116(12) 1.1995(6) 0.0532(8) Uani 1 1 d . . . . .
C21 C 0.1998(3) 0.28018(14) 0.9235(8) 0.0378(10) Uani 1 1 d . . . . .
H21A H 0.226913 0.313583 0.846816 0.057 Uiso 1 1 calc R U . . .
H21B H 0.236110 0.268433 1.054854 0.057 Uiso 1 1 calc R U . . .
H21C H 0.141091 0.290878 0.977867 0.057 Uiso 1 1 calc R U . . .
C22 C 0.1322(3) 0.24626(17) 0.5555(7) 0.0390(10) Uani 1 1 d . . . . .
H22A H 0.152630 0.282721 0.486950 0.059 Uiso 1 1 calc R U . . .
H22B H 0.072313 0.251371 0.613901 0.059 Uiso 1 1 calc R U . . .
H22C H 0.132657 0.215602 0.438506 0.059 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 C2 1.410(4) . ?
C2 C3 1.492(5) . ?
C3 N4 1.512(4) . ?
N4 C7 1.481(5) . ?
N4 C6 1.487(4) . ?
N4 C5 1.500(4) . ?
N11 O11 1.297(3) . ?
N11 C16 1.490(4) . ?
N11 C12 1.493(4) . ?
C12 C17 1.530(5) . ?
C12 C13 1.534(4) . ?
C12 C18 1.543(5) . ?
C13 C14 1.524(5) . ?
C14 C15 1.514(5) . ?
C14 C19 1.532(5) . ?
C15 C16 1.513(4) . ?
C16 C22 1.518(5) . ?
C16 C21 1.539(5) . ?
C19 O19 1.216(5) . ?
C19 O20 1.251(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
O1 C2 C3 111.7(3) . . ?
C2 C3 N4 116.7(3) . . ?
C7 N4 C6 109.2(3) . . ?
C7 N4 C5 109.2(3) . . ?
C6 N4 C5 107.2(3) . . ?
C7 N4 C3 112.0(3) . . ?
C6 N4 C3 111.6(3) . . ?
C5 N4 C3 107.5(3) . . ?
O11 N11 C16 115.9(3) . . ?
O11 N11 C12 115.8(3) . . ?
C16 N11 C12 125.3(2) . . ?
N11 C12 C17 108.1(3) . . ?
N11 C12 C13 109.9(3) . . ?
C17 C12 C13 109.7(3) . . ?
N11 C12 C18 108.0(3) . . ?
C17 C12 C18 110.3(3) . . ?
C13 C12 C18 110.8(3) . . ?
C14 C13 C12 113.5(3) . . ?
C15 C14 C13 107.6(3) . . ?
C15 C14 C19 112.0(3) . . ?
C13 C14 C19 114.4(3) . . ?
C16 C15 C14 114.7(3) . . ?
N11 C16 C15 109.5(3) . . ?
N11 C16 C22 107.6(3) . . ?
C15 C16 C22 110.0(3) . . ?
N11 C16 C21 109.1(3) . . ?
C15 C16 C21 111.0(3) . . ?
C22 C16 C21 109.6(3) . . ?
O19 C19 O20 123.3(4) . . ?
O19 C19 C14 118.7(4) . . ?
O20 C19 C14 117.9(4) . . ?

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
O1 H1 O19 0.9000(1) 2.603(7) 3.183(4) 122.9(6) 4_553 yes
O1 H1 O20 0.9000(1) 1.796(5) 2.674(4) 164.4(10) 4_553 yes

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039




#===END


