# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 
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data_p16478
_database_code_depnum_ccdc_archive 'CCDC 1999209'
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2017-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227),
 SHELXL-2014,
 and manual edit
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_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                   6.0356(4)
_cell_length_b                   10.8751(9)
_cell_length_c                   10.5262(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.925(3)
_cell_angle_gamma                90
_cell_volume                     684.32(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.21
_cell_measurement_theta_min      4.24
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.8741
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0620
0.00 0.00 -1.00 0.0520
0.00 1.00 0.00 0.1050
0.00 -1.00 0.00 0.1150
-1.00 0.00 0.00 0.0570
1.00 0.00 0.00 0.0830
0.00 1.00 1.00 0.0680
-3.00 -1.00 4.00 0.0760
5.00 0.00 -3.00 0.0930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         78.780
_diffrn_reflns_theta_min         4.240
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2867
_reflns_number_total             2909
_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_data_collection       
'APEX3 BIS V6.2.1/2016-03-01 (Bruker-AXS, 2007)'
_computing_cell_refinement       'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(5)
_refine_ls_abs_structure_Hooft   0.15(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.085
_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)+(0.0452P)²+0.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.4857(2) 0.61503(12) 0.61173(12) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.6609(2) 0.35555(12) 0.44462(12) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.612(5) 0.277(3) 0.431(3) 0.038(7) Uiso 1 1 d . . . . .
O3 O 0.5125(3) 0.35452(15) 0.89447(13) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.4456(2) 0.41892(14) 0.68892(14) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.4223(3) 0.50887(16) 0.59537(16) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.3074(3) 0.45543(15) 0.47047(16) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.2088(3) 0.33321(16) 0.51106(16) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.047(4) 0.342(2) 0.515(2) 0.014(5) Uiso 1 1 d . . . . .
H3B H 0.225(4) 0.268(2) 0.454(2) 0.017(5) Uiso 1 1 d . . . . .
C4 C 0.3292(3) 0.30430(17) 0.64617(18) 0.0207(4) Uani 1 1 d . . . . .
H4A H 0.224(4) 0.280(3) 0.708(2) 0.027(6) Uiso 1 1 d . . . . .
H4B H 0.444(4) 0.240(2) 0.644(2) 0.021(6) Uiso 1 1 d . . . . .
C5 C 0.4948(3) 0.43727(16) 0.38427(16) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.565(3) 0.521(2) 0.377(2) 0.013(5) Uiso 1 1 d . . . . .
C6 C 0.4003(3) 0.39714(16) 0.24910(17) 0.0188(4) Uani 1 1 d . . . . .
H6A H 0.332(4) 0.315(2) 0.252(2) 0.023(6) Uiso 1 1 d . . . . .
H6B H 0.525(4) 0.391(2) 0.198(2) 0.017(5) Uiso 1 1 d . . . . .
C7 C 0.2230(3) 0.48783(17) 0.18695(17) 0.0195(4) Uani 1 1 d . . . . .
H7A H 0.289(4) 0.567(2) 0.178(2) 0.018(5) Uiso 1 1 d . . . . .
H7B H 0.163(4) 0.459(2) 0.100(2) 0.025(6) Uiso 1 1 d . . . . .
C8 C 0.0363(3) 0.50140(17) 0.27045(17) 0.0195(4) Uani 1 1 d . . . . .
H8A H -0.078(4) 0.563(2) 0.230(2) 0.016(5) Uiso 1 1 d . . . . .
H8B H -0.044(4) 0.420(2) 0.275(2) 0.014(5) Uiso 1 1 d . . . . .
C9 C 0.1301(3) 0.54541(16) 0.40487(16) 0.0167(3) Uani 1 1 d . . . . .
H9A H 0.004(3) 0.5526(19) 0.4600(17) 0.005(4) Uiso 1 1 d . . . . .
H9B H 0.200(4) 0.628(2) 0.405(2) 0.022(6) Uiso 1 1 d . . . . .
C10 C 0.5527(3) 0.42928(18) 0.81534(17) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.7218(3) 0.52872(17) 0.84707(16) 0.0177(4) Uani 1 1 d . . . . .
C12 C 0.7088(3) 0.60306(19) 0.95351(17) 0.0209(4) Uani 1 1 d . . . . .
H12 H 0.582(4) 0.593(3) 0.998(3) 0.027(6) Uiso 1 1 d . . . . .
C13 C 0.8724(3) 0.69131(18) 0.98827(17) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.870(4) 0.745(3) 1.062(2) 0.026(6) Uiso 1 1 d . . . . .
C14 C 1.0521(3) 0.70318(18) 0.92020(18) 0.0213(4) Uani 1 1 d . . . . .
H14 H 1.170(5) 0.761(3) 0.948(3) 0.034(7) Uiso 1 1 d . . . . .
C15 C 1.0660(3) 0.62821(18) 0.81440(18) 0.0219(4) Uani 1 1 d . . . . .
H15 H 1.194(4) 0.636(2) 0.764(2) 0.016(5) Uiso 1 1 d . . . . .
C16 C 0.9002(3) 0.54185(16) 0.77680(17) 0.0204(4) Uani 1 1 d . . . . .
H16 H 0.910(4) 0.489(3) 0.699(2) 0.029(7) 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
O1 C1 1.221(2) . ?
O2 H2 0.91(4) . ?
O2 C5 1.422(2) . ?
O3 C10 1.212(2) . ?
N1 C1 1.381(2) . ?
N1 C4 1.471(2) . ?
N1 C10 1.401(2) . ?
C1 C2 1.515(2) . ?
C2 C3 1.541(2) . ?
C2 C5 1.557(2) . ?
C2 C9 1.541(2) . ?
C3 H3A 0.99(2) . ?
C3 H3B 0.94(2) . ?
C3 C4 1.538(2) . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.99(3) . ?
C5 H5 1.02(2) . ?
C5 C6 1.522(2) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.99(2) . ?
C6 C7 1.534(2) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.98(3) . ?
C7 C8 1.529(2) . ?
C8 H8A 1.01(2) . ?
C8 H8B 1.01(2) . ?
C8 C9 1.527(2) . ?
C9 H9A 1.020(19) . ?
C9 H9B 0.99(3) . ?
C10 C11 1.493(2) . ?
C11 C12 1.392(3) . ?
C11 C16 1.395(2) . ?
C12 H12 0.96(3) . ?
C12 C13 1.389(3) . ?
C13 H13 0.97(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.96(3) . ?
C14 C15 1.392(3) . ?
C15 H15 0.99(2) . ?
C15 C16 1.390(3) . ?
C16 H16 1.01(3) . ?

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 O2 H2 108.9(19) . . ?
C1 N1 C4 112.62(14) . . ?
C1 N1 C10 127.47(16) . . ?
C10 N1 C4 119.80(14) . . ?
O1 C1 N1 124.74(16) . . ?
O1 C1 C2 125.60(15) . . ?
N1 C1 C2 109.66(15) . . ?
C1 C2 C3 103.79(13) . . ?
C1 C2 C5 105.78(13) . . ?
C1 C2 C9 110.59(13) . . ?
C3 C2 C5 113.05(14) . . ?
C3 C2 C9 113.64(13) . . ?
C9 C2 C5 109.56(13) . . ?
C2 C3 H3A 110.4(14) . . ?
C2 C3 H3B 113.5(15) . . ?
H3A C3 H3B 106.9(19) . . ?
C4 C3 C2 106.35(14) . . ?
C4 C3 H3A 108.9(12) . . ?
C4 C3 H3B 110.8(14) . . ?
N1 C4 C3 104.75(14) . . ?
N1 C4 H4A 109.8(15) . . ?
N1 C4 H4B 107.4(14) . . ?
C3 C4 H4A 113.3(14) . . ?
C3 C4 H4B 111.4(14) . . ?
H4A C4 H4B 110(2) . . ?
O2 C5 C2 110.05(13) . . ?
O2 C5 H5 108.8(12) . . ?
O2 C5 C6 112.88(14) . . ?
C2 C5 H5 105.8(12) . . ?
C6 C5 C2 111.85(13) . . ?
C6 C5 H5 107.2(12) . . ?
C5 C6 H6A 109.8(15) . . ?
C5 C6 H6B 108.3(13) . . ?
C5 C6 C7 111.34(14) . . ?
H6A C6 H6B 108(2) . . ?
C7 C6 H6A 109.0(15) . . ?
C7 C6 H6B 110.7(13) . . ?
C6 C7 H7A 110.0(14) . . ?
C6 C7 H7B 109.7(15) . . ?
H7A C7 H7B 107(2) . . ?
C8 C7 C6 110.05(14) . . ?
C8 C7 H7A 108.6(13) . . ?
C8 C7 H7B 111.1(15) . . ?
C7 C8 H8A 109.8(13) . . ?
C7 C8 H8B 110.0(12) . . ?
H8A C8 H8B 107.1(17) . . ?
C9 C8 C7 110.78(13) . . ?
C9 C8 H8A 108.9(13) . . ?
C9 C8 H8B 110.2(12) . . ?
C2 C9 H9A 108.6(11) . . ?
C2 C9 H9B 107.7(14) . . ?
C8 C9 C2 111.22(14) . . ?
C8 C9 H9A 110.0(10) . . ?
C8 C9 H9B 112.7(14) . . ?
H9A C9 H9B 106.4(18) . . ?
O3 C10 N1 119.27(17) . . ?
O3 C10 C11 121.84(17) . . ?
N1 C10 C11 118.82(15) . . ?
C12 C11 C10 119.22(16) . . ?
C12 C11 C16 120.00(17) . . ?
C16 C11 C10 120.62(16) . . ?
C11 C12 H12 117.5(16) . . ?
C13 C12 C11 119.77(17) . . ?
C13 C12 H12 122.7(16) . . ?
C12 C13 H13 122.3(16) . . ?
C14 C13 C12 120.43(17) . . ?
C14 C13 H13 117.2(16) . . ?
C13 C14 H14 120.1(16) . . ?
C13 C14 C15 119.81(17) . . ?
C15 C14 H14 120.0(17) . . ?
C14 C15 H15 120.5(13) . . ?
C16 C15 C14 120.19(17) . . ?
C16 C15 H15 119.3(13) . . ?
C11 C16 H16 120.5(15) . . ?
C15 C16 C11 119.77(16) . . ?
C15 C16 H16 119.7(15) . . ?

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
O2 H2 O1 0.91(4) 1.89(4) 2.7986(19) 175(3) 2_646

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 -165.21(17) . . . . ?
O1 C1 C2 C5 75.6(2) . . . . ?
O1 C1 C2 C9 -43.0(2) . . . . ?
O2 C5 C6 C7 -179.66(14) . . . . ?
O3 C10 C11 C12 -51.7(3) . . . . ?
O3 C10 C11 C16 123.8(2) . . . . ?
N1 C1 C2 C3 14.98(17) . . . . ?
N1 C1 C2 C5 -104.25(15) . . . . ?
N1 C1 C2 C9 137.20(14) . . . . ?
N1 C10 C11 C12 131.41(18) . . . . ?
N1 C10 C11 C16 -53.1(2) . . . . ?
C1 N1 C4 C3 -3.70(19) . . . . ?
C1 N1 C10 O3 161.61(18) . . . . ?
C1 N1 C10 C11 -21.4(3) . . . . ?
C1 C2 C3 C4 -16.70(17) . . . . ?
C1 C2 C5 O2 60.06(17) . . . . ?
C1 C2 C5 C6 -173.63(14) . . . . ?
C1 C2 C9 C8 171.94(14) . . . . ?
C2 C3 C4 N1 12.86(18) . . . . ?
C2 C5 C6 C7 55.58(18) . . . . ?
C3 C2 C5 O2 -52.86(18) . . . . ?
C3 C2 C5 C6 73.45(18) . . . . ?
C3 C2 C9 C8 -71.81(17) . . . . ?
C4 N1 C1 O1 172.87(17) . . . . ?
C4 N1 C1 C2 -7.32(18) . . . . ?
C4 N1 C10 O3 -14.3(3) . . . . ?
C4 N1 C10 C11 162.72(16) . . . . ?
C5 C2 C3 C4 97.43(16) . . . . ?
C5 C2 C9 C8 55.72(17) . . . . ?
C5 C6 C7 C8 -56.81(19) . . . . ?
C6 C7 C8 C9 58.18(19) . . . . ?
C7 C8 C9 C2 -58.66(18) . . . . ?
C9 C2 C3 C4 -136.87(15) . . . . ?
C9 C2 C5 O2 179.28(13) . . . . ?
C9 C2 C5 C6 -54.41(18) . . . . ?
C10 N1 C1 O1 -3.3(3) . . . . ?
C10 N1 C1 C2 176.56(15) . . . . ?
C10 N1 C4 C3 172.76(15) . . . . ?
C10 C11 C12 C13 176.38(16) . . . . ?
C10 C11 C16 C15 -174.62(17) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
