# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zwang1cult
_database_code_depnum_ccdc_archive 'CCDC 2045204'
loop_
_audit_author_name
_audit_author_address
'Herman H. Y. Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2020-11-18 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2020-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H22 N O3'
_chemical_formula_sum            'C12 H22 N O3'
_chemical_formula_weight         228.30
_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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.81660(10)
_cell_length_b                   11.4718(2)
_cell_length_c                   9.5696(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.897(2)
_cell_angle_gamma                90
_cell_volume                     619.86(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2336
_cell_measurement_temperature    100.2(8)
_cell_measurement_theta_max      73.2200
_cell_measurement_theta_min      4.7440
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0099
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3277
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.331
_diffrn_reflns_theta_min         4.760
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 110.00   1.00    3.00    --  106.99 -94.00-180.00   86
  2  ω   -115.00 -25.00   1.00    2.00    --  -40.57 -57.00  60.00   90
  3  ω   -115.00 -90.00   1.00    2.00    --  -40.57-132.00-133.00   25
  4  ω    -64.00  33.00   1.00    2.00    --  -40.57  37.00-150.00   97
  5  ω      1.00  83.00   1.00    2.00    --   40.57 -99.00 -60.00   82
  6  ω     79.00 109.00   1.00    3.00    --  106.99  45.00 150.00   30
  7  ω     49.00 128.00   1.00    3.00    --  106.99 -77.00-120.00   79
  8  ω     40.00 135.00   1.00    3.00    --  106.99 -30.00 -30.00   95
  9  ω    143.00 178.00   1.00    3.00    --  106.99  45.00 150.00   35
 10  ω     30.00 117.00   1.00    3.00    --  106.99 -30.00 150.00   87
 11  ω     78.00 175.00   1.00    3.00    --  106.99  30.00 -30.00   97
 12  ω     42.00 110.00   1.00    3.00    --  106.99 -94.00  60.00   68
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2466544000
_diffrn_orient_matrix_UB_12      -0.0204755000
_diffrn_orient_matrix_UB_13      -0.1003415000
_diffrn_orient_matrix_UB_21      0.0397321000
_diffrn_orient_matrix_UB_22      -0.1326771000
_diffrn_orient_matrix_UB_23      0.0136331000
_diffrn_orient_matrix_UB_31      -0.1097306000
_diffrn_orient_matrix_UB_32      -0.0018851000
_diffrn_orient_matrix_UB_33      0.1313672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1210
_reflns_number_total             1266
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.047
_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)+(0.0476P)²+0.1813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1(0.5) O2(0.5) H1A(0.5) H1B(0.5) H2(0.5) C3(0.5) H3A(0.5) H3B(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.6266(3) 0.35565(13) 0.26589(16) 0.0291(4) Uani 0.5 1 d . . . A -1
O2 O 0.3021(2) 0.27902(10) 0.45522(13) 0.0204(4) Uani 0.5 1 d . . . A -1
O3 O -0.1350(2) 0.2500 0.89816(12) 0.0297(3) Uani 1 2 d S T P . .
N1 N -0.02376(19) 0.2500 0.79719(12) 0.0174(3) Uani 1 2 d S T P . .
C1 C 0.7237(3) 0.2500 0.22785(15) 0.0239(3) Uani 1 2 d S T P . .
H1A H 0.8654 0.2180 0.2959 0.029 Uiso 0.5 1 calc R . . A -1
H1B H 0.7173 0.2364 0.1248 0.029 Uiso 0.5 1 calc R . . A -1
C2 C 0.5000(2) 0.2500 0.27239(14) 0.0204(3) Uani 1 2 d S T P A .
H2 H 0.3536 0.2382 0.1939 0.025 Uiso 0.5 1 calc R . . B -1
C3 C 0.4854(3) 0.21248(16) 0.41974(19) 0.0186(4) Uani 0.5 1 d . . . A -1
H3A H 0.4486 0.1282 0.4204 0.022 Uiso 0.5 1 calc R . . A -1
H3B H 0.6377 0.2270 0.4901 0.022 Uiso 0.5 1 calc R . . A -1
C4 C 0.2770(2) 0.2500 0.59942(14) 0.0254(3) Uani 1 2 d S T P . .
H4 H 0.4357 0.2500 0.6690 0.031 Uiso 1 2 calc RS T P A .
C5 C 0.13999(17) 0.35804(9) 0.62017(11) 0.0249(3) Uani 1 1 d . . . . .
H5A H -0.0071 0.3612 0.5425 0.030 Uiso 1 1 calc R . . . .
H5B H 0.2358 0.4274 0.6100 0.030 Uiso 1 1 calc R . . . .
C6 C 0.07393(16) 0.36474(8) 0.76523(10) 0.0205(2) Uani 1 1 d . . . . .
C7 C 0.28900(19) 0.39640(10) 0.88760(12) 0.0301(3) Uani 1 1 d . . . . .
H7A H 0.2476 0.3873 0.9804 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.3349 0.4774 0.8763 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.4215 0.3446 0.8841 0.045 Uiso 1 1 calc GR . . . .
C8 C -0.1204(2) 0.45553(9) 0.75737(14) 0.0329(3) Uani 1 1 d . . . . .
H8A H -0.2616 0.4323 0.6842 0.049 Uiso 1 1 calc GR . . . .
H8B H -0.0648 0.5314 0.7317 0.049 Uiso 1 1 calc GR . . . .
H8C H -0.1596 0.4613 0.8512 0.049 Uiso 1 1 calc GR . . . .


_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 C1 1.4209(16) . ?
O1 C2 1.4271(16) . ?
O2 C3 1.417(2) . ?
O2 C4 1.4604(17) . ?
O3 N1 1.2855(15) . ?
N1 C6 1.4942(10) 4_565 ?
N1 C6 1.4942(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.4630(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.496(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 1.0000 . ?
C4 C5 1.5123(13) . ?
C4 C5 1.5123(13) 4_565 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5287(13) . ?
C6 C7 1.5377(13) . ?
C6 C8 1.5254(14) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C1 O1 C2 61.82(9) . . ?
C3 O2 C4 110.80(12) . . ?
O3 N1 C6 116.02(6) . 4_565 ?
O3 N1 C6 116.02(6) . . ?
C6 N1 C6 123.52(10) 4_565 . ?
O1 C1 H1A 117.8 . . ?
O1 C1 H1B 117.8 . . ?
O1 C1 C2 59.30(7) . . ?
H1A C1 H1B 115.0 . . ?
C2 C1 H1A 117.8 . . ?
C2 C1 H1B 117.8 . . ?
O1 C2 C1 58.88(7) . . ?
O1 C2 H2 115.9 . . ?
O1 C2 C3 115.61(12) . . ?
C1 C2 H2 115.9 . . ?
C1 C2 C3 122.04(13) . . ?
C3 C2 H2 115.9 . . ?
O2 C3 C2 106.69(13) . . ?
O2 C3 H3A 110.4 . . ?
O2 C3 H3B 110.4 . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O2 C4 H4 110.1 . . ?
O2 C4 C5 96.47(7) . . ?
O2 C4 C5 119.09(9) . 4_565 ?
C5 C4 H4 110.1 . . ?
C5 C4 H4 110.1 4_565 . ?
C5 C4 C5 110.08(11) 4_565 . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C4 C5 C6 114.57(8) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
N1 C6 C5 109.42(8) . . ?
N1 C6 C7 109.39(8) . . ?
N1 C6 C8 107.33(8) . . ?
C5 C6 C7 111.56(8) . . ?
C8 C6 C5 109.53(8) . . ?
C8 C6 C7 109.51(9) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O1 C1 C2 C3 -102.58(13) . . . . ?
O1 C2 C3 O2 80.30(17) . . . . ?
O2 C4 C5 C6 -179.66(9) . . . . ?
O3 N1 C6 C5 -164.93(10) . . . . ?
O3 N1 C6 C7 72.58(12) . . . . ?
O3 N1 C6 C8 -46.15(13) . . . . ?
C1 O1 C2 C3 113.45(14) . . . . ?
C1 C2 C3 O2 148.20(9) . . . . ?
C3 O2 C4 C5 -80.69(16) . . . 4_565 ?
C3 O2 C4 C5 162.02(12) . . . . ?
C4 O2 C3 C2 -178.91(10) . . . . ?
C4 C5 C6 N1 -46.08(11) . . . . ?
C4 C5 C6 C7 75.11(11) . . . . ?
C4 C5 C6 C8 -163.48(9) . . . . ?
C5 C4 C5 C6 56.12(14) 4_565 . . . ?
C6 N1 C6 C5 39.73(15) 4_565 . . . ?
C6 N1 C6 C7 -82.76(13) 4_565 . . . ?
C6 N1 C6 C8 158.51(9) 4_565 . . . ?

_olex2_date_sample_data_collection 2019-04-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.865
