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

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#
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#                                CCDC 
# 
#######################################################################
# 
#  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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_a40329b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43

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                   8.435(4)
_cell_length_b                   11.876(5)
_cell_length_c                   19.470(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1950.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2368
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9856
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.59
_reflns_number_total             3625
_reflns_number_gt                2933
_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)+(0.0730P)²+0.0000P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(17)
_refine_ls_number_reflns         3625
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.4611(3) 0.5942(2) 0.28202(12) 0.0658(6) Uani 1 1 d . . .
H1A H 0.5679 0.6029 0.2644 0.079 Uiso 1 1 calc R . .
H1B H 0.4107 0.6675 0.2839 0.079 Uiso 1 1 calc R . .
C2 C 0.4627(3) 0.5390(2) 0.35255(13) 0.0760(8) Uani 1 1 d . . .
H2A H 0.5467 0.4835 0.3559 0.091 Uiso 1 1 calc R . .
H2B H 0.4766 0.5947 0.3885 0.091 Uiso 1 1 calc R . .
C3 C 0.3040(3) 0.48475(19) 0.35737(11) 0.0637(6) Uani 1 1 d . . .
H3A H 0.3062 0.4214 0.3888 0.076 Uiso 1 1 calc R . .
H3B H 0.2245 0.5381 0.3727 0.076 Uiso 1 1 calc R . .
C4 C 0.2405(2) 0.57274(14) 0.19101(9) 0.0377(4) Uani 1 1 d . . .
H4A H 0.1731 0.6178 0.2214 0.045 Uiso 1 1 calc R . .
C5 C 0.1322(2) 0.49107(13) 0.15233(9) 0.0368(4) Uani 1 1 d . . .
H5A H 0.1960 0.4491 0.1189 0.044 Uiso 1 1 calc R . .
C6 C 0.0649(2) 0.40827(14) 0.20494(9) 0.0402(4) Uani 1 1 d . . .
C7 C 0.1313(3) 0.39888(15) 0.26719(10) 0.0473(5) Uani 1 1 d . . .
H7A H 0.0778 0.3557 0.2996 0.057 Uiso 1 1 calc R . .
C8 C 0.3644(3) 0.51211(16) 0.23691(10) 0.0476(5) Uani 1 1 d . . .
C9 C 0.0034(2) 0.55562(13) 0.11400(9) 0.0372(4) Uani 1 1 d . . .
C10 C -0.1194(2) 0.60939(15) 0.14930(10) 0.0461(5) Uani 1 1 d . . .
H10A H -0.1235 0.6049 0.1970 0.055 Uiso 1 1 calc R . .
C11 C -0.2349(3) 0.66922(16) 0.11438(12) 0.0537(5) Uani 1 1 d . . .
H11A H -0.3166 0.7037 0.1386 0.064 Uiso 1 1 calc R . .
C12 C -0.2294(3) 0.67786(18) 0.04448(13) 0.0635(6) Uani 1 1 d . . .
H12A H -0.3066 0.7187 0.0212 0.076 Uiso 1 1 calc R . .
C13 C -0.1088(3) 0.62570(19) 0.00855(11) 0.0630(6) Uani 1 1 d . . .
H13A H -0.1052 0.6313 -0.0391 0.076 Uiso 1 1 calc R . .
C14 C 0.0068(3) 0.56516(16) 0.04299(10) 0.0488(5) Uani 1 1 d . . .
H14A H 0.0876 0.5305 0.0183 0.059 Uiso 1 1 calc R . .
C15 C -0.0742(3) 0.33706(17) 0.18385(11) 0.0507(5) Uani 1 1 d . . .
H15A H -0.1601 0.3863 0.1699 0.061 Uiso 1 1 calc R . .
H15B H -0.1101 0.2945 0.2234 0.061 Uiso 1 1 calc R . .
C16 C -0.0389(2) 0.25549(16) 0.12560(10) 0.0482(5) Uani 1 1 d . . .
C17 C 0.0768(3) 0.1752(2) 0.13201(13) 0.0651(6) Uani 1 1 d . . .
H17A H 0.1378 0.1726 0.1718 0.078 Uiso 1 1 calc R . .
C18 C 0.1044(4) 0.0972(2) 0.07973(17) 0.0897(9) Uani 1 1 d . . .
H18A H 0.1820 0.0422 0.0852 0.108 Uiso 1 1 calc R . .
C19 C 0.0178(5) 0.1014(3) 0.02051(16) 0.0946(10) Uani 1 1 d . . .
H19A H 0.0362 0.0496 -0.0144 0.113 Uiso 1 1 calc R . .
C20 C -0.0954(5) 0.1816(3) 0.01284(15) 0.1025(12) Uani 1 1 d . . .
H20A H -0.1540 0.1849 -0.0276 0.123 Uiso 1 1 calc R . .
C21 C -0.1242(4) 0.2589(2) 0.06504(13) 0.0792(8) Uani 1 1 d . . .
H21A H -0.2018 0.3136 0.0591 0.095 Uiso 1 1 calc R . .
C22 C 0.4718(3) 0.4311(2) 0.19631(13) 0.0639(6) Uani 1 1 d . . .
H22A H 0.4073 0.3810 0.1695 0.096 Uiso 1 1 calc R . .
H22B H 0.5353 0.3881 0.2277 0.096 Uiso 1 1 calc R . .
H22C H 0.5397 0.4736 0.1664 0.096 Uiso 1 1 calc R . .
N1 N 0.2722(2) 0.44766(14) 0.28741(8) 0.0504(4) Uani 1 1 d . . .
N2 N 0.3200(2) 0.65264(13) 0.14202(9) 0.0486(4) Uani 1 1 d . . .
O1 O 0.3745(2) 0.61684(13) 0.08880(8) 0.0648(4) Uani 1 1 d . . .
O2 O 0.3282(3) 0.75146(12) 0.15923(9) 0.0857(6) 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 C2 1.522(3) . ?
C1 C8 1.545(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.488(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.457(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.503(2) . ?
C4 C5 1.530(2) . ?
C4 C8 1.552(3) . ?
C4 H4A 0.9800 . ?
C5 C9 1.525(2) . ?
C5 C6 1.530(2) . ?
C5 H5A 0.9800 . ?
C6 C7 1.340(3) . ?
C6 C15 1.503(3) . ?
C7 N1 1.380(3) . ?
C7 H7A 0.9300 . ?
C8 N1 1.469(3) . ?
C8 C22 1.540(3) . ?
C9 C14 1.387(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.385(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.521(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.370(3) . ?
C16 C21 1.382(3) . ?
C17 C18 1.396(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.356(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.391(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N2 O1 1.211(2) . ?
N2 O2 1.223(2) . ?

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
C2 C1 C8 104.25(18) . . ?
C2 C1 H1A 110.9 . . ?
C8 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C8 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C3 C2 C1 103.6(2) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 C2 103.7(2) . . ?
N1 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
N1 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N2 C4 C5 110.72(14) . . ?
N2 C4 C8 110.97(16) . . ?
C5 C4 C8 113.03(14) . . ?
N2 C4 H4A 107.3 . . ?
C5 C4 H4A 107.3 . . ?
C8 C4 H4A 107.3 . . ?
C9 C5 C6 112.72(16) . . ?
C9 C5 C4 110.33(13) . . ?
C6 C5 C4 107.43(14) . . ?
C9 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C7 C6 C15 121.79(17) . . ?
C7 C6 C5 120.25(18) . . ?
C15 C6 C5 117.95(16) . . ?
C6 C7 N1 125.70(18) . . ?
C6 C7 H7A 117.1 . . ?
N1 C7 H7A 117.1 . . ?
N1 C8 C22 109.23(16) . . ?
N1 C8 C1 103.16(17) . . ?
C22 C8 C1 112.1(2) . . ?
N1 C8 C4 105.69(17) . . ?
C22 C8 C4 112.98(16) . . ?
C1 C8 C4 112.95(16) . . ?
C14 C9 C10 117.91(18) . . ?
C14 C9 C5 120.93(17) . . ?
C10 C9 C5 121.14(16) . . ?
C11 C10 C9 120.98(19) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
C6 C15 C16 114.18(16) . . ?
C6 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C6 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C21 118.0(2) . . ?
C17 C16 C15 120.97(19) . . ?
C21 C16 C15 121.1(2) . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C16 C21 C20 120.9(3) . . ?
C16 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C3 123.54(18) . . ?
C7 N1 C8 118.95(16) . . ?
C3 N1 C8 111.77(17) . . ?
O1 N2 O2 123.37(17) . . ?
O1 N2 C4 119.39(15) . . ?
O2 N2 C4 117.23(17) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.59
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 1017179'
