# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2309977'
loop_
_audit_author_name
_audit_author_address
'Xingchen Yan'
;Jiangsu University
China
;
_audit_update_record             
;
2024-01-04 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_audit_creation_date             2023-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
(2S,3R)-N,N-Dimethyl-2-carboxyl-3-methyl-hexanamide
_chemical_formula_moiety         'C10 H19 N O3'
_chemical_formula_sum            'C10 H19 N O3'
_chemical_formula_weight         201.26
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4153(5)
_cell_length_b                   11.2753(12)
_cell_length_c                   9.4479(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.633(7)
_cell_angle_gamma                90
_cell_volume                     570.34(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      79.23
_cell_measurement_theta_min      4.73
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.5605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1413 before and 0.0915 after correction.
The Ratio of minimum to maximum transmission is 0.7432.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9916
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.660
_diffrn_reflns_theta_min         6.152
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                2124
_reflns_number_total             2324
_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       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2324
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.065
_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)+(0.0701P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1239
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.1986(4) 0.75193(19) 0.5235(2) 0.0524(6) Uani 1 1 d . . . . .
H1 H 0.079612 0.799720 0.523532 0.079 Uiso 1 1 calc R U . . .
O2 O 0.0224(4) 0.6654(2) 0.6936(3) 0.0604(6) Uani 1 1 d . . . . .
O3 O 0.1423(3) 0.42136(19) 0.5131(2) 0.0488(5) Uani 1 1 d . . . . .
N1 N 0.4145(4) 0.4997(2) 0.3808(2) 0.0414(5) Uani 1 1 d . . . . .
C1 C 0.3334(7) 0.4174(3) 0.2634(3) 0.0581(8) Uani 1 1 d . . . . .
H1A H 0.214542 0.360441 0.293147 0.087 Uiso 1 1 calc R U . . .
H1B H 0.478674 0.374758 0.238441 0.087 Uiso 1 1 calc R U . . .
H1C H 0.252848 0.461749 0.179813 0.087 Uiso 1 1 calc R U . . .
C2 C 0.6134(5) 0.5820(3) 0.3575(3) 0.0512(7) Uani 1 1 d . . . . .
H2A H 0.586838 0.658414 0.402427 0.077 Uiso 1 1 calc R U . . .
H2B H 0.611160 0.593518 0.254509 0.077 Uiso 1 1 calc R U . . .
H2C H 0.775272 0.549347 0.400020 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3111(4) 0.4933(2) 0.5000(2) 0.0355(5) Uani 1 1 d . . . . .
C4 C 0.3941(4) 0.5783(2) 0.6240(2) 0.0326(5) Uani 1 1 d . . . . .
H4 H 0.549338 0.619973 0.605793 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1857(4) 0.6691(2) 0.6208(3) 0.0356(5) Uani 1 1 d . . . . .
C6 C 0.4501(4) 0.5117(2) 0.7671(3) 0.0356(5) Uani 1 1 d . . . . .
H6 H 0.294981 0.470057 0.785485 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5286(6) 0.5996(3) 0.8878(3) 0.0502(7) Uani 1 1 d . . . . .
H7A H 0.682260 0.639900 0.871621 0.075 Uiso 1 1 calc R U . . .
H7B H 0.558274 0.557155 0.979288 0.075 Uiso 1 1 calc R U . . .
H7C H 0.395833 0.658293 0.890152 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6548(5) 0.4190(3) 0.7580(3) 0.0409(6) Uani 1 1 d . . . . .
H8A H 0.600768 0.367123 0.674538 0.049 Uiso 1 1 calc R U . . .
H8B H 0.808108 0.460716 0.740207 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7188(6) 0.3419(3) 0.8895(3) 0.0569(8) Uani 1 1 d . . . . .
H9A H 0.565638 0.301310 0.909579 0.068 Uiso 1 1 calc R U . . .
H9B H 0.780325 0.392699 0.972759 0.068 Uiso 1 1 calc R U . . .
C10 C 0.9166(6) 0.2492(4) 0.8714(4) 0.0682(10) Uani 1 1 d . . . . .
H10A H 0.860469 0.201334 0.785991 0.102 Uiso 1 1 calc R U . . .
H10B H 0.942734 0.197629 0.955853 0.102 Uiso 1 1 calc R U . . .
H10C H 1.073648 0.288897 0.860702 0.102 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 H1 0.8400 . ?
O1 C5 1.320(3) . ?
O2 C5 1.200(3) . ?
O3 C3 1.242(3) . ?
N1 C1 1.463(4) . ?
N1 C2 1.463(4) . ?
N1 C3 1.333(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.528(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.520(3) . ?
C4 C6 1.536(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.523(4) . ?
C6 C8 1.535(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.514(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C5 O1 H1 109.5 . . ?
C1 N1 C2 115.6(2) . . ?
C3 N1 C1 119.3(2) . . ?
C3 N1 C2 125.0(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 N1 121.9(2) . . ?
O3 C3 C4 118.0(2) . . ?
N1 C3 C4 120.1(2) . . ?
C3 C4 H4 108.7 . . ?
C3 C4 C6 111.3(2) . . ?
C5 C4 C3 105.98(18) . . ?
C5 C4 H4 108.7 . . ?
C5 C4 C6 113.22(19) . . ?
C6 C4 H4 108.7 . . ?
O1 C5 C4 111.93(19) . . ?
O2 C5 O1 123.0(2) . . ?
O2 C5 C4 125.1(2) . . ?
C4 C6 H6 108.8 . . ?
C7 C6 C4 109.7(2) . . ?
C7 C6 H6 108.8 . . ?
C7 C6 C8 111.2(2) . . ?
C8 C6 C4 109.40(19) . . ?
C8 C6 H6 108.8 . . ?
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 108.5 . . ?
C6 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C6 115.0(2) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.3(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
