# 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_AX2340
_database_code_depnum_ccdc_archive 'CCDC 2256162'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT Rostock
Germany
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-13 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         'C11 H19 N O3'
_chemical_formula_sum            'C11 H19 N O3'
_chemical_formula_weight         213.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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                   11.3947(2)
_cell_length_b                   8.8485(2)
_cell_length_c                   12.0913(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.8193(7)
_cell_angle_gamma                90
_cell_volume                     1160.63(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    8162
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      66.59

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microfocus
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            12257
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.075
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_full        66.582
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2057
_reflns_number_gt                1967
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0583P)²+0.2222P] 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_number_reflns         2057
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.52351(11) 0.24310(14) 0.94927(11) 0.0427(3) Uani 1 1 d . . . . .
H1B H 0.518088 0.220643 1.027763 0.051 Uiso 1 1 calc R U . . .
C2 C 0.40528(11) 0.26314(13) 0.85757(10) 0.0395(3) Uani 1 1 d . . . . .
H2 H 0.330966 0.251309 0.882875 0.047 Uiso 1 1 calc R U . . .
C3 C 0.63588(11) 0.32824(14) 0.94539(10) 0.0386(3) Uani 1 1 d . . . . .
C4 C 0.39023(10) 0.36514(13) 0.75472(10) 0.0372(3) Uani 1 1 d . . . . .
H4 H 0.472212 0.387638 0.746394 0.045 Uiso 1 1 calc R U . . .
C5 C 0.30888(14) 0.29524(18) 0.64351(12) 0.0566(4) Uani 1 1 d . . . . .
H5A H 0.229052 0.271357 0.652129 0.085 Uiso 1 1 calc R U . . .
H5B H 0.347030 0.203455 0.627083 0.085 Uiso 1 1 calc R U . . .
H5C H 0.298376 0.366079 0.579986 0.085 Uiso 1 1 calc R U . . .
C6 C 0.79707(10) 0.35459(13) 0.85080(10) 0.0376(3) Uani 1 1 d . . . . .
H6 H 0.803920 0.456406 0.886169 0.045 Uiso 1 1 calc R U . . .
C7 C 0.91816(11) 0.27167(16) 0.90519(11) 0.0465(3) Uani 1 1 d . . . . .
H7A H 0.934794 0.266290 0.989558 0.056 Uiso 1 1 calc R U . . .
H7B H 0.911628 0.168175 0.875046 0.056 Uiso 1 1 calc R U . . .
C8 C 1.02404(12) 0.35256(19) 0.87800(12) 0.0557(4) Uani 1 1 d . . . . .
H8A H 1.036679 0.451405 0.916406 0.067 Uiso 1 1 calc R U . . .
H8B H 1.099788 0.293636 0.909370 0.067 Uiso 1 1 calc R U . . .
C9 C 0.99993(12) 0.37446(17) 0.74921(13) 0.0528(3) Uani 1 1 d . . . . .
H9A H 0.998285 0.275749 0.712009 0.063 Uiso 1 1 calc R U . . .
H9B H 1.067134 0.433692 0.736101 0.063 Uiso 1 1 calc R U . . .
C10 C 0.87855(13) 0.45498(15) 0.69431(13) 0.0502(3) Uani 1 1 d . . . . .
H10A H 0.862374 0.459887 0.609986 0.060 Uiso 1 1 calc R U . . .
H10B H 0.884062 0.558690 0.723918 0.060 Uiso 1 1 calc R U . . .
C11 C 0.77281(11) 0.37372(14) 0.72089(11) 0.0429(3) Uani 1 1 d . . . . .
H11A H 0.696623 0.431481 0.688429 0.051 Uiso 1 1 calc R U . . .
H11B H 0.761406 0.274092 0.683705 0.051 Uiso 1 1 calc R U . . .
N1 N 0.69346(9) 0.27668(12) 0.87314(9) 0.0409(3) Uani 1 1 d . . . . .
O1 O 0.66834(9) 0.44058(11) 1.00773(8) 0.0515(3) Uani 1 1 d . . . . .
O2 O 0.47759(8) 0.12783(9) 0.86331(9) 0.0481(3) Uani 1 1 d . . . . .
O3 O 0.33327(10) 0.50220(10) 0.77261(8) 0.0516(3) Uani 1 1 d . . . . .
H1A H 0.6674(13) 0.1974(18) 0.8360(13) 0.047(4) Uiso 1 1 d . . . . .
H3 H 0.3435(17) 0.520(2) 0.8494(17) 0.076(5) Uiso 1 1 d . . . . .


_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
C1 O2 1.4358(16) . ?
C1 C2 1.4702(17) . ?
C1 C3 1.4986(17) . ?
C1 H1B 0.9900 . ?
C2 O2 1.4430(14) . ?
C2 C4 1.5033(16) . ?
C2 H2 0.9900 . ?
C3 O1 1.2338(15) . ?
C3 N1 1.3239(15) . ?
C4 O3 1.4230(14) . ?
C4 C5 1.5123(17) . ?
C4 H4 0.9900 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 N1 1.4620(15) . ?
C6 C11 1.5187(17) . ?
C6 C7 1.5229(17) . ?
C6 H6 0.9900 . ?
C7 C8 1.5228(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.509(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.5164(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.5196(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
N1 H1A 0.837(16) . ?
O3 H3 0.91(2) . ?

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
O2 C1 C2 59.53(8) . . ?
O2 C1 C3 117.39(10) . . ?
C2 C1 C3 120.69(10) . . ?
O2 C1 H1B 115.8 . . ?
C2 C1 H1B 115.8 . . ?
C3 C1 H1B 115.8 . . ?
O2 C2 C1 59.05(8) . . ?
O2 C2 C4 117.18(9) . . ?
C1 C2 C4 122.85(10) . . ?
O2 C2 H2 115.3 . . ?
C1 C2 H2 115.3 . . ?
C4 C2 H2 115.3 . . ?
O1 C3 N1 124.35(11) . . ?
O1 C3 C1 119.02(11) . . ?
N1 C3 C1 116.62(11) . . ?
O3 C4 C2 109.14(9) . . ?
O3 C4 C5 107.44(10) . . ?
C2 C4 C5 111.95(11) . . ?
O3 C4 H4 109.4 . . ?
C2 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C11 109.99(9) . . ?
N1 C6 C7 111.66(10) . . ?
C11 C6 C7 110.76(10) . . ?
N1 C6 H6 108.1 . . ?
C11 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C8 C7 C6 110.68(11) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 112.16(11) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 111.45(11) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 111.17(11) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C6 C11 C10 111.49(10) . . ?
C6 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C6 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C3 N1 C6 123.41(10) . . ?
C3 N1 H1A 118.5(10) . . ?
C6 N1 H1A 118.0(10) . . ?
C1 O2 C2 61.42(8) . . ?
C4 O3 H3 112.1(12) . . ?

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
C3 C1 C2 O2 105.76(12) . . . . ?
O2 C1 C2 C4 -104.29(12) . . . . ?
C3 C1 C2 C4 1.47(18) . . . . ?
O2 C1 C3 O1 170.63(10) . . . . ?
C2 C1 C3 O1 101.52(14) . . . . ?
O2 C1 C3 N1 -8.89(16) . . . . ?
C2 C1 C3 N1 -77.99(15) . . . . ?
O2 C2 C4 O3 -171.15(10) . . . . ?
C1 C2 C4 O3 -102.05(13) . . . . ?
O2 C2 C4 C5 70.04(14) . . . . ?
C1 C2 C4 C5 139.14(12) . . . . ?
N1 C6 C7 C8 178.46(10) . . . . ?
C11 C6 C7 C8 55.51(14) . . . . ?
C6 C7 C8 C9 -55.11(16) . . . . ?
C7 C8 C9 C10 54.60(17) . . . . ?
C8 C9 C10 C11 -54.38(16) . . . . ?
N1 C6 C11 C10 179.78(10) . . . . ?
C7 C6 C11 C10 -56.31(13) . . . . ?
C9 C10 C11 C6 55.59(15) . . . . ?
O1 C3 N1 C6 -5.52(19) . . . . ?
C1 C3 N1 C6 173.96(10) . . . . ?
C11 C6 N1 C3 -128.26(12) . . . . ?
C7 C6 N1 C3 108.35(13) . . . . ?
C3 C1 O2 C2 -111.23(11) . . . . ?
C4 C2 O2 C1 113.77(12) . . . . ?

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
N1 H1A O3 0.837(16) 2.168(16) 2.9612(14) 158.1(13) 2_646 yes
O3 H3 O1 0.91(2) 1.81(2) 2.7094(12) 168.9(18) 3_667 yes

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041



