# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_p212121_a
_database_code_depnum_ccdc_archive 'CCDC 1581871'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-((S)-2,2-dimethyl-1-(pyridin-2-yl)propyl)-2-((S)-tetrahydrofuran-2-yl)acetamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 N2 O2'
_chemical_formula_weight         275.36

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8237(4)
_cell_length_b                   9.6779(6)
_cell_length_c                   23.2090(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1532.70(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9325
_cell_measurement_theta_min      3.372
_cell_measurement_theta_max      33.139

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega phi scan'
_diffrn_reflns_number            90932
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.371
_diffrn_reflns_theta_max         33.198
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5861
_reflns_number_gt                5677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0609P)²+0.2023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap


_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(9)
_chemical_absolute_configuration .
_refine_ls_number_reflns         5861
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.45626(14) 0.52886(10) 0.24509(4) 0.01414(16) Uani 1 1 d . . . . .
C2 C 0.36723(15) 0.60637(11) 0.19467(4) 0.01708(17) Uani 1 1 d . . . . .
H2A H 0.2284 0.5789 0.1899 0.020 Uiso 1 1 calc R U . . .
H2B H 0.3713 0.7070 0.2024 0.020 Uiso 1 1 calc R U . . .
C3 C 0.47960(18) 0.57462(11) 0.13987(4) 0.01928(19) Uani 1 1 d . . . . .
H3 H 0.4770 0.4727 0.1328 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6918(2) 0.62495(18) 0.13888(5) 0.0312(3) Uani 1 1 d . . . . .
H4A H 0.7827 0.5504 0.1506 0.037 Uiso 1 1 calc R U . . .
H4B H 0.7098 0.7050 0.1649 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7262(2) 0.66676(16) 0.07535(6) 0.0314(3) Uani 1 1 d . . . . .
H5A H 0.7621 0.7656 0.0723 0.038 Uiso 1 1 calc R U . . .
H5B H 0.8311 0.6101 0.0577 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5297(3) 0.63875(15) 0.04690(5) 0.0310(3) Uani 1 1 d . . . . .
H6A H 0.5013 0.7095 0.0172 0.037 Uiso 1 1 calc R U . . .
H6B H 0.5293 0.5466 0.0284 0.037 Uiso 1 1 calc R U . . .
C7 C 0.61097(14) 0.54798(9) 0.34031(4) 0.01298(15) Uani 1 1 d . . . . .
H7 H 0.5926 0.4457 0.3377 0.016 Uiso 1 1 calc R U . . .
C8 C 0.83686(14) 0.57487(12) 0.34206(4) 0.01760(18) Uani 1 1 d . . . . .
C9 C 0.92922(19) 0.50656(19) 0.28900(6) 0.0326(3) Uani 1 1 d . . . . .
H9A H 1.0722 0.5150 0.2911 0.049 Uiso 1 1 calc R U . . .
H9B H 0.8816 0.5524 0.2541 0.049 Uiso 1 1 calc R U . . .
H9C H 0.8929 0.4086 0.2879 0.049 Uiso 1 1 calc R U . . .
C10 C 0.88281(18) 0.72995(13) 0.34188(6) 0.0258(2) Uani 1 1 d . . . . .
H10A H 0.8268 0.7729 0.3764 0.039 Uiso 1 1 calc R U . . .
H10B H 0.8259 0.7726 0.3074 0.039 Uiso 1 1 calc R U . . .
H10C H 1.0251 0.7435 0.3417 0.039 Uiso 1 1 calc R U . . .
C11 C 0.92537(17) 0.50758(13) 0.39593(5) 0.0239(2) Uani 1 1 d . . . . .
H11A H 0.8901 0.4094 0.3969 0.036 Uiso 1 1 calc R U . . .
H11B H 0.8742 0.5535 0.4304 0.036 Uiso 1 1 calc R U . . .
H11C H 1.0683 0.5168 0.3949 0.036 Uiso 1 1 calc R U . . .
C12 C 0.50077(14) 0.59612(10) 0.39357(4) 0.01322(15) Uani 1 1 d . . . . .
C13 C 0.48697(16) 0.50915(11) 0.44107(4) 0.01815(18) Uani 1 1 d . . . . .
H13 H 0.5494 0.4214 0.4408 0.022 Uiso 1 1 calc R U . . .
C14 C 0.38127(17) 0.55179(14) 0.48881(5) 0.0230(2) Uani 1 1 d . . . . .
H14 H 0.3707 0.4938 0.5217 0.028 Uiso 1 1 calc R U . . .
C15 C 0.29091(16) 0.68042(14) 0.48801(5) 0.0217(2) Uani 1 1 d . . . . .
H15 H 0.2171 0.7122 0.5201 0.026 Uiso 1 1 calc R U . . .
C16 C 0.31172(17) 0.76097(12) 0.43906(5) 0.02017(19) Uani 1 1 d . . . . .
H16 H 0.2499 0.8489 0.4383 0.024 Uiso 1 1 calc R U . . .
N1 N 0.52222(13) 0.60760(9) 0.28881(3) 0.01324(14) Uani 1 1 d . . . . .
N2 N 0.41521(14) 0.72114(9) 0.39241(4) 0.01694(16) Uani 1 1 d . . . . .
O1 O 0.46714(15) 0.40123(8) 0.24504(4) 0.02403(18) Uani 1 1 d . . . . .
O2 O 0.38717(16) 0.64447(10) 0.09230(4) 0.02638(19) Uani 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 O1 1.2374(12) . ?
C1 N1 1.3464(12) . ?
C1 C2 1.5170(14) . ?
C2 C3 1.5166(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.4400(14) . ?
C3 C4 1.5278(19) . ?
C3 H3 1.0000 . ?
C4 C5 1.5468(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.4351(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.4589(12) . ?
C7 C12 1.5201(13) . ?
C7 C8 1.5638(14) . ?
C7 H7 1.0000 . ?
C8 C9 1.5331(16) . ?
C8 C10 1.5333(17) . ?
C8 C11 1.5337(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.3437(13) . ?
C12 C13 1.3902(13) . ?
C13 C14 1.3850(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3893(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3852(17) . ?
C15 H15 0.9500 . ?
C16 N2 1.3488(13) . ?
C16 H16 0.9500 . ?

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 C1 N1 123.06(9) . . ?
O1 C1 C2 121.13(9) . . ?
N1 C1 C2 115.81(8) . . ?
C3 C2 C1 110.13(8) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C2 109.05(9) . . ?
O2 C3 C4 104.71(9) . . ?
C2 C3 C4 115.29(9) . . ?
O2 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C3 C4 C5 103.98(11) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C4 103.52(11) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
O2 C6 C5 105.79(10) . . ?
O2 C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
O2 C6 H6B 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
N1 C7 C12 109.86(7) . . ?
N1 C7 C8 111.39(8) . . ?
C12 C7 C8 114.55(8) . . ?
N1 C7 H7 106.9 . . ?
C12 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C9 C8 C10 109.62(11) . . ?
C9 C8 C11 108.05(10) . . ?
C10 C8 C11 109.72(9) . . ?
C9 C8 C7 108.21(9) . . ?
C10 C8 C7 111.37(9) . . ?
C11 C8 C7 109.80(8) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 122.11(9) . . ?
N2 C12 C7 118.34(8) . . ?
C13 C12 C7 119.52(9) . . ?
C14 C13 C12 119.29(10) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 119.18(10) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 118.01(10) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
N2 C16 C15 123.45(11) . . ?
N2 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C1 N1 C7 122.17(8) . . ?
C12 N2 C16 117.96(9) . . ?
C6 O2 C3 104.36(10) . . ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045

