# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_cu_zy1_0m
_database_code_depnum_ccdc_archive 'CCDC 1520169'
_audit_update_record             
;
2016-12-01 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.98420(10)
_cell_length_b                   9.1040(2)
_cell_length_c                   16.0223(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     872.90(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5382
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      69.09

_exptl_crystal_description       chunk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.63
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_T_max  0.8132
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4963
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.59
_diffrn_reflns_theta_max         69.57
_reflns_number_total             1573
_reflns_number_gt                1570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.2054P] 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     SHELXL
_refine_ls_extinction_coef       0.049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.70334(18) 0.62928(11) 0.82889(7) 0.0217(3) Uani 1 1 d . . .
H4 H 0.6069 0.6925 0.8416 0.033 Uiso 1 1 calc R . .
N1 N 0.9308(2) 0.28397(15) 0.76331(7) 0.0191(3) Uani 1 1 d . . .
H1 H 1.0135 0.2079 0.7494 0.023 Uiso 1 1 calc R . .
C9 C 1.0835(3) 0.24456(18) 0.90171(10) 0.0260(4) Uani 1 1 d . . .
H9A H 0.9995 0.1529 0.9082 0.039 Uiso 1 1 calc R . .
H9B H 1.1057 0.2898 0.9566 0.039 Uiso 1 1 calc R . .
H9C H 1.2291 0.2235 0.8764 0.039 Uiso 1 1 calc R . .
C2 C 0.9541(3) 0.34885(18) 0.84608(9) 0.0185(4) Uani 1 1 d . . .
H2 H 1.0386 0.4432 0.8412 0.022 Uiso 1 1 calc R . .
C8A C 0.7811(3) 0.34060(17) 0.70701(8) 0.0174(4) Uani 1 1 d . . .
C4A C 0.6085(3) 0.43569(16) 0.73244(9) 0.0170(4) Uani 1 1 d . . .
C5 C 0.4506(3) 0.48234(17) 0.67424(11) 0.0224(4) Uani 1 1 d . . .
H5 H 0.3315 0.5439 0.6919 0.027 Uiso 1 1 calc R . .
C6 C 0.4637(3) 0.44060(18) 0.59086(10) 0.0258(4) Uani 1 1 d . . .
H6 H 0.3554 0.4735 0.5518 0.031 Uiso 1 1 calc R . .
C4 C 0.5981(3) 0.48688(16) 0.82199(9) 0.0179(4) Uani 1 1 d . . .
H4A H 0.4384 0.4945 0.8398 0.021 Uiso 1 1 calc R . .
C3 C 0.7207(3) 0.38098(17) 0.87940(9) 0.0186(4) Uani 1 1 d . . .
H3A H 0.6352 0.2882 0.8837 0.022 Uiso 1 1 calc R . .
H3B H 0.7320 0.4242 0.9359 0.022 Uiso 1 1 calc R . .
C7 C 0.6383(3) 0.34971(19) 0.56567(10) 0.0252(4) Uani 1 1 d . . .
H7 H 0.6510 0.3224 0.5086 0.030 Uiso 1 1 calc R . .
C8 C 0.7931(3) 0.29887(18) 0.62256(9) 0.0215(4) Uani 1 1 d . . .
H8 H 0.9090 0.2350 0.6045 0.026 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0242(5) 0.0102(5) 0.0307(6) -0.0030(4) 0.0047(5) -0.0011(4)
N1 0.0219(6) 0.0197(6) 0.0157(6) -0.0022(5) 0.0008(5) 0.0063(6)
C9 0.0326(9) 0.0222(9) 0.0232(8) -0.0009(6) -0.0087(7) 0.0031(7)
C2 0.0230(7) 0.0159(7) 0.0165(7) -0.0007(6) -0.0016(6) -0.0011(6)
C8A 0.0219(7) 0.0140(7) 0.0163(7) 0.0019(5) 0.0011(6) -0.0028(6)
C4A 0.0207(7) 0.0116(7) 0.0188(7) 0.0017(6) 0.0006(6) -0.0034(6)
C5 0.0238(8) 0.0136(7) 0.0298(8) 0.0049(6) -0.0029(7) -0.0022(6)
C6 0.0321(9) 0.0217(8) 0.0235(8) 0.0101(6) -0.0109(7) -0.0078(7)
C4 0.0185(7) 0.0129(7) 0.0223(7) -0.0013(6) 0.0047(6) -0.0026(6)
C3 0.0273(8) 0.0142(7) 0.0141(6) -0.0005(5) 0.0025(6) -0.0030(6)
C7 0.0387(9) 0.0220(8) 0.0150(6) 0.0029(6) -0.0026(6) -0.0098(7)
C8 0.0270(8) 0.0202(8) 0.0173(7) -0.0007(6) 0.0038(6) -0.0029(7)

_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
O4 C4 1.4454(18) . ?
O4 H4 0.8400 . ?
N1 C8A 1.3718(19) . ?
N1 C2 1.4585(18) . ?
N1 H1 0.8800 . ?
C9 C2 1.515(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C2 C3 1.524(2) . ?
C2 H2 1.0000 . ?
C8A C8 1.407(2) . ?
C8A C4A 1.408(2) . ?
C4A C5 1.394(2) . ?
C4A C4 1.510(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C4 C3 1.521(2) . ?
C4 H4A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 H8 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
C4 O4 H4 109.5 . . ?
C8A N1 C2 120.53(13) . . ?
C8A N1 H1 119.7 . . ?
C2 N1 H1 119.7 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C2 C9 109.27(13) . . ?
N1 C2 C3 107.99(12) . . ?
C9 C2 C3 112.51(13) . . ?
N1 C2 H2 109.0 . . ?
C9 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
N1 C8A C8 119.83(14) . . ?
N1 C8A C4A 121.32(13) . . ?
C8 C8A C4A 118.79(14) . . ?
C5 C4A C8A 119.41(14) . . ?
C5 C4A C4 120.91(14) . . ?
C8A C4A C4 119.67(13) . . ?
C6 C5 C4A 121.39(16) . . ?
C6 C5 H5 119.3 . . ?
C4A C5 H5 119.3 . . ?
C5 C6 C7 118.88(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O4 C4 C4A 109.36(12) . . ?
O4 C4 C3 108.19(13) . . ?
C4A C4 C3 111.05(12) . . ?
O4 C4 H4A 109.4 . . ?
C4A C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C4 C3 C2 110.60(12) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C8 C7 C6 120.78(15) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 120.70(15) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?

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
C8A N1 C2 C9 165.86(13) . . . . ?
C8A N1 C2 C3 43.19(18) . . . . ?
C2 N1 C8A C8 166.35(13) . . . . ?
C2 N1 C8A C4A -16.3(2) . . . . ?
N1 C8A C4A C5 -175.44(14) . . . . ?
C8 C8A C4A C5 1.9(2) . . . . ?
N1 C8A C4A C4 5.1(2) . . . . ?
C8 C8A C4A C4 -177.47(13) . . . . ?
C8A C4A C5 C6 -2.0(2) . . . . ?
C4 C4A C5 C6 177.39(13) . . . . ?
C4A C5 C6 C7 0.3(2) . . . . ?
C5 C4A C4 O4 -83.11(17) . . . . ?
C8A C4A C4 O4 96.30(15) . . . . ?
C5 C4A C4 C3 157.56(14) . . . . ?
C8A C4A C4 C3 -23.03(19) . . . . ?
O4 C4 C3 C2 -69.58(15) . . . . ?
C4A C4 C3 C2 50.44(16) . . . . ?
N1 C2 C3 C4 -59.79(16) . . . . ?
C9 C2 C3 C4 179.54(13) . . . . ?
C5 C6 C7 C8 1.5(2) . . . . ?
C6 C7 C8 C8A -1.5(2) . . . . ?
N1 C8A C8 C7 177.23(14) . . . . ?
C4A C8A C8 C7 -0.2(2) . . . . ?

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
N1 H1 O4 0.88 2.23 2.9930(16) 145.5 3_746

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        69.57
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.052
