# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_mmcp151027
_audit_block_doi                 10.5517/ccdc.csd.cc1lbg5k
_database_code_depnum_ccdc_archive 'CCDC 1469808'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N O3'
_chemical_formula_sum            'C10 H15 N O3'
_chemical_formula_weight         197.23

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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   9.9528(10)
_cell_length_b                   5.6608(6)
_cell_length_c                   10.1737(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.444(7)
_cell_angle_gamma                90
_cell_volume                     499.16(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4453
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      30.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5950
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5642
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         30.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2655
_reflns_number_gt                2520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.926

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0447P)²+0.0722P] 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 1101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.71371(17) 0.3810(3) 0.68538(18) 0.0209(3) Uani 1 1 d . . . . .
H1 H 0.6977 0.5349 0.6314 0.025 Uiso 1 1 calc R U . . .
C2 C 0.85404(18) 0.3945(3) 0.84325(19) 0.0254(3) Uani 1 1 d . . . . .
H2A H 0.8219 0.4158 0.9204 0.030 Uiso 1 1 calc R U . . .
H2B H 0.9220 0.5275 0.8506 0.030 Uiso 1 1 calc R U . . .
C3 C 0.93668(19) 0.1580(3) 0.86451(19) 0.0258(3) Uani 1 1 d . . . . .
H3A H 1.0491 0.1821 0.9080 0.031 Uiso 1 1 calc R U . . .
H3B H 0.9188 0.0534 0.9324 0.031 Uiso 1 1 calc R U . . .
C4 C 0.86769(18) 0.0524(3) 0.70805(18) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.6313(2) 0.1261(4) 0.46017(18) 0.0288(4) Uani 1 1 d . . . . .
H5A H 0.6626 -0.0197 0.4285 0.035 Uiso 1 1 calc R U . . .
H5B H 0.6148 0.2521 0.3862 0.035 Uiso 1 1 calc R U . . .
C6 C 0.48235(19) 0.0823(3) 0.46558(19) 0.0256(3) Uani 1 1 d . . . . .
H6A H 0.3950 0.0653 0.3616 0.031 Uiso 1 1 calc R U . . .
H6B H 0.4917 -0.0665 0.5205 0.031 Uiso 1 1 calc R U . . .
C7 C 0.45034(16) 0.2858(3) 0.54398(16) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.4348 0.4338 0.4845 0.024 Uiso 1 1 calc R U . . .
C8 C 0.30886(17) 0.2419(3) 0.56027(18) 0.0223(3) Uani 1 1 d . . . . .
H8A H 0.2214 0.2001 0.4601 0.027 Uiso 1 1 calc R U . . .
H8B H 0.3291 0.1047 0.6278 0.027 Uiso 1 1 calc R U . . .
C9 C 0.26214(17) 0.4501(3) 0.62244(18) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.1602(2) 0.3955(4) 0.6889(2) 0.0309(4) Uani 1 1 d . . . . .
H10A H 0.2228 0.3306 0.7906 0.046 Uiso 1 1 calc R U . . .
H10B H 0.0819 0.2797 0.6252 0.046 Uiso 1 1 calc R U . . .
H10C H 0.1094 0.5407 0.6943 0.046 Uiso 1 1 calc R U . . .
N1 N 0.75197(16) 0.1971(3) 0.61077(16) 0.0232(3) Uani 1 1 d . . . . .
O1 O 0.90782(16) -0.1307(2) 0.67354(16) 0.0352(3) Uani 1 1 d . . . . .
O2 O 0.57944(12) 0.3179(2) 0.69406(12) 0.0205(2) Uani 1 1 d . . . . .
O3 O 0.30342(15) 0.6494(2) 0.61697(18) 0.0363(3) 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 O2 1.4273(18) . ?
C1 N1 1.446(2) . ?
C1 C2 1.527(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.513(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.223(2) . ?
C4 N1 1.362(2) . ?
C5 N1 1.464(2) . ?
C5 C6 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.521(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.4445(17) . ?
C7 C8 1.517(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.211(2) . ?
C9 C10 1.502(2) . ?
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
O2 C1 N1 110.39(12) . . ?
O2 C1 C2 110.35(13) . . ?
N1 C1 C2 104.33(13) . . ?
O2 C1 H1 110.5 . . ?
N1 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C1 C2 C3 104.78(13) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 105.23(13) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
O1 C4 N1 125.44(16) . . ?
O1 C4 C3 126.42(15) . . ?
N1 C4 C3 108.14(14) . . ?
N1 C5 C6 108.52(13) . . ?
N1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C7 C6 C5 110.64(13) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O2 C7 C8 107.24(12) . . ?
O2 C7 C6 110.04(12) . . ?
C8 C7 C6 112.23(13) . . ?
O2 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C6 C7 H7 109.1 . . ?
C9 C8 C7 114.22(13) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O3 C9 C10 122.12(16) . . ?
O3 C9 C8 121.66(16) . . ?
C10 C9 C8 116.21(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N1 C1 113.48(14) . . ?
C4 N1 C5 124.13(15) . . ?
C1 N1 C5 117.07(14) . . ?
C1 O2 C7 109.85(11) . . ?

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
O2 C1 C2 C3 98.75(15) . . . . ?
N1 C1 C2 C3 -19.82(16) . . . . ?
C1 C2 C3 C4 15.00(17) . . . . ?
C2 C3 C4 O1 175.57(16) . . . . ?
C2 C3 C4 N1 -4.43(17) . . . . ?
N1 C5 C6 C7 48.05(19) . . . . ?
C5 C6 C7 O2 -57.12(17) . . . . ?
C5 C6 C7 C8 -176.45(13) . . . . ?
O2 C7 C8 C9 65.25(16) . . . . ?
C6 C7 C8 C9 -173.79(13) . . . . ?
C7 C8 C9 O3 20.6(2) . . . . ?
C7 C8 C9 C10 -160.28(13) . . . . ?
O1 C4 N1 C1 170.94(16) . . . . ?
C3 C4 N1 C1 -9.07(18) . . . . ?
O1 C4 N1 C5 17.6(3) . . . . ?
C3 C4 N1 C5 -162.41(15) . . . . ?
O2 C1 N1 C4 -99.95(15) . . . . ?
C2 C1 N1 C4 18.59(17) . . . . ?
O2 C1 N1 C5 55.40(19) . . . . ?
C2 C1 N1 C5 173.94(14) . . . . ?
C6 C5 N1 C4 103.73(18) . . . . ?
C6 C5 N1 C1 -48.8(2) . . . . ?
N1 C1 O2 C7 -60.30(15) . . . . ?
C2 C1 O2 C7 -175.10(12) . . . . ?
C8 C7 O2 C1 -174.80(12) . . . . ?
C6 C7 O2 C1 62.87(15) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4



