# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_130427hzl_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   10.2469(9)
_cell_length_b                   10.4606(9)
_cell_length_c                   13.5437(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1451.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9608
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.49
_reflns_number_total             3002
_reflns_number_gt                2805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0214P)²+0.2728P] 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       0.0178(12)
_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   -0.5(10)
_refine_ls_number_reflns         3002
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
C1 C 0.28977(13) 1.07836(13) 1.01751(11) 0.0399(3) Uani 1 1 d . . .
C2 C 0.20589(15) 1.04265(14) 1.09266(11) 0.0455(3) Uani 1 1 d . . .
H2 H 0.2300 1.0553 1.1581 0.055 Uiso 1 1 calc R . .
C3 C 0.08713(14) 0.98849(14) 1.07088(10) 0.0408(3) Uani 1 1 d . . .
H3 H 0.0316 0.9654 1.1222 0.049 Uiso 1 1 calc R . .
C4 C 0.04792(12) 0.96735(11) 0.97394(9) 0.0320(3) Uani 1 1 d . . .
C5 C 0.13350(14) 1.00222(14) 0.90013(10) 0.0402(3) Uani 1 1 d . . .
H5 H 0.1102 0.9881 0.8347 0.048 Uiso 1 1 calc R . .
C6 C 0.25337(14) 1.05773(15) 0.92079(11) 0.0442(3) Uani 1 1 d . . .
H6 H 0.3090 1.0810 0.8696 0.053 Uiso 1 1 calc R . .
C7 C 0.48597(17) 1.18574(18) 0.97323(15) 0.0662(5) Uani 1 1 d . . .
H7A H 0.5202 1.1180 0.9331 0.099 Uiso 1 1 calc R . .
H7B H 0.5567 1.2311 1.0037 0.099 Uiso 1 1 calc R . .
H7C H 0.4365 1.2434 0.9327 0.099 Uiso 1 1 calc R . .
C8 C -0.08486(12) 0.90787(12) 0.95207(9) 0.0310(3) Uani 1 1 d . . .
H8 H -0.1432 0.9274 1.0074 0.037 Uiso 1 1 calc R . .
C9 C -0.14712(12) 0.95755(12) 0.85898(10) 0.0335(3) Uani 1 1 d . . .
C10 C -0.13167(13) 0.88934(13) 0.76768(10) 0.0380(3) Uani 1 1 d . . .
C11 C -0.05956(14) 0.77963(14) 0.76430(10) 0.0417(3) Uani 1 1 d . . .
H11 H -0.0356 0.7456 0.7035 0.050 Uiso 1 1 calc R . .
C12 C -0.07713(13) 0.75966(12) 0.94121(9) 0.0331(3) Uani 1 1 d . . .
H12 H -0.1662 0.7259 0.9455 0.040 Uiso 1 1 calc R . .
C13 C -0.18843(14) 0.96625(16) 0.69084(11) 0.0471(4) Uani 1 1 d . . .
H13 H -0.1919 0.9461 0.6240 0.057 Uiso 1 1 calc R . .
C14 C -0.23576(14) 1.07337(15) 0.73394(12) 0.0485(4) Uani 1 1 d . . .
H14 H -0.2795 1.1389 0.7014 0.058 Uiso 1 1 calc R . .
C15 C -0.20790(13) 1.07013(14) 0.83821(11) 0.0412(3) Uani 1 1 d . . .
H15 H -0.2280 1.1340 0.8835 0.049 Uiso 1 1 calc R . .
C16 C 0.00221(13) 0.69796(12) 1.02168(11) 0.0362(3) Uani 1 1 d . . .
C17 C 0.01987(19) 0.6694(2) 1.19335(11) 0.0641(5) Uani 1 1 d . . .
H17A H 0.0304 0.5787 1.1868 0.096 Uiso 1 1 calc R . .
H17B H -0.0274 0.6879 1.2528 0.096 Uiso 1 1 calc R . .
H17C H 0.1041 0.7094 1.1961 0.096 Uiso 1 1 calc R . .
N1 N -0.02322(12) 0.72088(11) 0.84688(8) 0.0410(3) Uani 1 1 d . . .
H1 H 0.0326 0.6595 0.8443 0.049 Uiso 1 1 calc R . .
O1 O 0.40445(10) 1.13391(11) 1.04687(8) 0.0576(3) Uani 1 1 d . . .
O2 O 0.10077(12) 0.64020(12) 1.00842(8) 0.0631(3) Uani 1 1 d . . .
O3 O -0.05141(10) 0.71802(10) 1.10966(7) 0.0446(2) 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 1.3699(16) . ?
C1 C6 1.379(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.374(2) . ?
C3 C4 1.3908(18) . ?
C4 C5 1.3788(18) . ?
C4 C8 1.5251(17) . ?
C5 C6 1.387(2) . ?
C7 O1 1.409(2) . ?
C8 C9 1.5056(17) . ?
C8 C12 1.5594(17) . ?
C9 C15 1.3616(19) . ?
C9 C10 1.4363(19) . ?
C10 C11 1.366(2) . ?
C10 C13 1.4382(19) . ?
C11 N1 1.3294(18) . ?
C12 N1 1.4498(17) . ?
C12 C16 1.5052(18) . ?
C13 C14 1.353(2) . ?
C14 C15 1.441(2) . ?
C16 O2 1.1906(16) . ?
C16 O3 1.3287(16) . ?
C17 O3 1.4410(18) . ?

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 C6 125.04(14) . . ?
O1 C1 C2 115.71(13) . . ?
C6 C1 C2 119.24(13) . . ?
C3 C2 C1 120.23(13) . . ?
C2 C3 C4 121.60(13) . . ?
C5 C4 C3 117.29(12) . . ?
C5 C4 C8 122.31(11) . . ?
C3 C4 C8 120.39(11) . . ?
C4 C5 C6 121.85(13) . . ?
C1 C6 C5 119.78(13) . . ?
C9 C8 C4 113.57(10) . . ?
C9 C8 C12 106.60(10) . . ?
C4 C8 C12 112.25(10) . . ?
C15 C9 C10 107.59(12) . . ?
C15 C9 C8 131.71(13) . . ?
C10 C9 C8 120.19(11) . . ?
C11 C10 C9 120.39(12) . . ?
C11 C10 C13 131.65(14) . . ?
C9 C10 C13 107.49(12) . . ?
N1 C11 C10 120.78(13) . . ?
N1 C12 C16 108.20(11) . . ?
N1 C12 C8 112.38(10) . . ?
C16 C12 C8 112.67(11) . . ?
C14 C13 C10 107.21(14) . . ?
C13 C14 C15 109.40(13) . . ?
C9 C15 C14 108.26(14) . . ?
O2 C16 O3 124.49(13) . . ?
O2 C16 C12 124.51(13) . . ?
O3 C16 C12 110.99(11) . . ?
C11 N1 C12 120.35(11) . . ?
C1 O1 C7 117.79(13) . . ?
C16 O3 C17 116.11(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
O1 C1 C2 C3 178.67(13) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C8 -179.59(12) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C8 C4 C5 C6 179.17(13) . . . . ?
O1 C1 C6 C5 -179.02(14) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C5 C4 C8 C9 -33.95(17) . . . . ?
C3 C4 C8 C9 146.05(12) . . . . ?
C5 C4 C8 C12 87.06(15) . . . . ?
C3 C4 C8 C12 -92.94(14) . . . . ?
C4 C8 C9 C15 -75.55(17) . . . . ?
C12 C8 C9 C15 160.32(13) . . . . ?
C4 C8 C9 C10 95.10(14) . . . . ?
C12 C8 C9 C10 -29.03(15) . . . . ?
C15 C9 C10 C11 172.12(13) . . . . ?
C8 C9 C10 C11 -0.57(19) . . . . ?
C15 C9 C10 C13 -0.90(15) . . . . ?
C8 C9 C10 C13 -173.58(11) . . . . ?
C9 C10 C11 N1 12.8(2) . . . . ?
C13 C10 C11 N1 -176.16(15) . . . . ?
C9 C8 C12 N1 48.37(14) . . . . ?
C4 C8 C12 N1 -76.57(14) . . . . ?
C9 C8 C12 C16 170.92(10) . . . . ?
C4 C8 C12 C16 45.98(14) . . . . ?
C11 C10 C13 C14 -172.38(15) . . . . ?
C9 C10 C13 C14 -0.45(16) . . . . ?
C10 C13 C14 C15 1.57(17) . . . . ?
C10 C9 C15 C14 1.83(15) . . . . ?
C8 C9 C15 C14 173.35(13) . . . . ?
C13 C14 C15 C9 -2.18(17) . . . . ?
N1 C12 C16 O2 8.01(19) . . . . ?
C8 C12 C16 O2 -116.86(15) . . . . ?
N1 C12 C16 O3 -172.86(11) . . . . ?
C8 C12 C16 O3 62.28(14) . . . . ?
C10 C11 N1 C12 10.3(2) . . . . ?
C16 C12 N1 C11 -167.70(12) . . . . ?
C8 C12 N1 C11 -42.66(17) . . . . ?
C6 C1 O1 C7 6.8(2) . . . . ?
C2 C1 O1 C7 -172.55(14) . . . . ?
O2 C16 O3 C17 2.5(2) . . . . ?
C12 C16 O3 C17 -176.66(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 1030081'
