# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#                                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
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data_md143

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N2 O3'
_chemical_formula_sum            'C22 H30 N2 O3'
_chemical_formula_weight         370.48

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   7.5478(11)
_cell_length_b                   9.9201(14)
_cell_length_c                   13.996(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.024(10)
_cell_angle_gamma                90.00
_cell_volume                     1032.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2025
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      17.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9961
_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         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex II '
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15398
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         25.15
_reflns_number_total             1945
_reflns_number_gt                1336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0615P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         1945
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O1 O 0.6185(4) 0.0408(2) 0.2822(2) 0.0742(8) Uani 1 1 d . . .
O2 O 0.5134(4) -0.1107(3) 0.3771(2) 0.0783(8) Uani 1 1 d . . .
O3 O 0.7651(4) -0.4442(3) 0.5968(2) 0.0738(8) Uani 1 1 d . . .
H3D H 0.6719 -0.4843 0.6013 0.111 Uiso 1 1 calc R . .
N1 N 0.7467(4) -0.1620(3) 0.29678(19) 0.0561(8) Uani 1 1 d . . .
N2 N 0.7310(4) -0.3051(3) 0.3004(2) 0.0583(8) Uani 1 1 d . . .
C1 C 0.9908(5) -0.1144(4) 0.1933(3) 0.0690(10) Uani 1 1 d . . .
H1A H 1.0306 -0.2071 0.1904 0.083 Uiso 1 1 calc R . .
H1B H 1.0729 -0.0662 0.2426 0.083 Uiso 1 1 calc R . .
C2 C 0.9722(7) -0.0443(5) 0.0932(3) 0.0884(14) Uani 1 1 d . . .
H2A H 1.0399 0.0393 0.0980 0.106 Uiso 1 1 calc R . .
H2B H 1.0143 -0.1025 0.0461 0.106 Uiso 1 1 calc R . .
C3 C 0.7723(7) -0.0176(5) 0.0652(3) 0.0862(14) Uani 1 1 d . . .
H3A H 0.7315 -0.0070 -0.0048 0.103 Uiso 1 1 calc R . .
C4 C 0.7239(8) 0.1023(5) 0.1256(3) 0.0903(14) Uani 1 1 d . . .
H4A H 0.7985 0.1803 0.1193 0.108 Uiso 1 1 calc R . .
H4B H 0.5981 0.1270 0.1077 0.108 Uiso 1 1 calc R . .
C5 C 0.7645(5) 0.0427(4) 0.2271(3) 0.0671(10) Uani 1 1 d . . .
H5A H 0.8715 0.0852 0.2648 0.081 Uiso 1 1 calc R . .
C6 C 0.7996(5) -0.1064(4) 0.2109(2) 0.0564(9) Uani 1 1 d . . .
C7 C 0.6859(6) -0.1366(5) 0.1092(3) 0.0728(11) Uani 1 1 d . . .
C8 C 0.7287(7) -0.2752(5) 0.0668(3) 0.0988(15) Uani 1 1 d . . .
H8A H 0.6550 -0.2874 0.0043 0.148 Uiso 1 1 calc R . .
H8B H 0.7042 -0.3459 0.1096 0.148 Uiso 1 1 calc R . .
H8C H 0.8533 -0.2781 0.0606 0.148 Uiso 1 1 calc R . .
C9 C 0.4824(6) -0.1318(6) 0.1052(4) 0.1024(16) Uani 1 1 d . . .
H9A H 0.4498 -0.0466 0.1296 0.154 Uiso 1 1 calc R . .
H9B H 0.4470 -0.2032 0.1441 0.154 Uiso 1 1 calc R . .
H9C H 0.4226 -0.1425 0.0392 0.154 Uiso 1 1 calc R . .
C10 C 0.6181(6) -0.0824(4) 0.3243(3) 0.0638(10) Uani 1 1 d . . .
C11 C 0.7725(4) -0.3595(3) 0.3841(3) 0.0513(8) Uani 1 1 d . . .
C12 C 0.7561(6) -0.5112(3) 0.3844(3) 0.0726(11) Uani 1 1 d . . .
H12A H 0.6635 -0.5355 0.4214 0.087 Uiso 1 1 calc R . .
H12B H 0.8688 -0.5485 0.4179 0.087 Uiso 1 1 calc R . .
C13 C 0.7114(6) -0.5765(4) 0.2856(3) 0.0833(13) Uani 1 1 d . . .
H13A H 0.7040 -0.6724 0.2930 0.125 Uiso 1 1 calc R . .
H13B H 0.8038 -0.5557 0.2486 0.125 Uiso 1 1 calc R . .
H13C H 0.5980 -0.5429 0.2523 0.125 Uiso 1 1 calc R . .
C14 C 0.8407(4) -0.2886(3) 0.4792(2) 0.0502(8) Uani 1 1 d . . .
H14A H 0.8372 -0.1916 0.4658 0.060 Uiso 1 1 calc R . .
C15 C 1.0362(4) -0.3256(4) 0.5165(3) 0.0608(10) Uani 1 1 d . . .
H15A H 1.1065 -0.3081 0.4670 0.091 Uiso 1 1 calc R . .
H15B H 1.0441 -0.4195 0.5333 0.091 Uiso 1 1 calc R . .
H15C H 1.0812 -0.2724 0.5729 0.091 Uiso 1 1 calc R . .
C16 C 0.7225(5) -0.3138(3) 0.5561(3) 0.0579(9) Uani 1 1 d . . .
H16A H 0.5961 -0.3133 0.5244 0.069 Uiso 1 1 calc R . .
C17 C 0.7487(4) -0.2071(3) 0.6355(3) 0.0562(10) Uani 1 1 d . . .
C18 C 0.7211(6) -0.0718(4) 0.6130(3) 0.0699(11) Uani 1 1 d . . .
H18A H 0.6854 -0.0460 0.5486 0.084 Uiso 1 1 calc R . .
C19 C 0.7459(6) 0.0257(4) 0.6852(3) 0.0809(13) Uani 1 1 d . . .
H19A H 0.7266 0.1160 0.6688 0.097 Uiso 1 1 calc R . .
C20 C 0.7982(6) -0.0096(5) 0.7795(3) 0.0842(13) Uani 1 1 d . . .
H20A H 0.8172 0.0560 0.8277 0.101 Uiso 1 1 calc R . .
C21 C 0.8227(7) -0.1437(5) 0.8030(3) 0.0892(14) Uani 1 1 d . . .
H21A H 0.8553 -0.1691 0.8676 0.107 Uiso 1 1 calc R . .
C22 C 0.7994(5) -0.2402(5) 0.7319(3) 0.0743(11) Uani 1 1 d . . .
H22A H 0.8183 -0.3302 0.7492 0.089 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
O1 0.098(2) 0.0435(15) 0.0819(18) 0.0051(13) 0.0178(15) 0.0225(14)
O2 0.0892(19) 0.0617(17) 0.0902(19) -0.0001(15) 0.0332(16) 0.0243(16)
O3 0.0803(17) 0.0458(14) 0.099(2) 0.0142(14) 0.0252(14) -0.0048(14)
N1 0.078(2) 0.0380(16) 0.0523(17) -0.0045(14) 0.0101(15) 0.0073(14)
N2 0.0697(19) 0.0383(17) 0.067(2) -0.0060(15) 0.0123(15) 0.0050(15)
C1 0.078(3) 0.063(2) 0.065(2) -0.007(2) 0.0090(18) -0.001(2)
C2 0.113(4) 0.089(3) 0.066(3) -0.005(2) 0.023(3) -0.015(3)
C3 0.119(4) 0.085(3) 0.051(2) 0.006(2) 0.004(2) 0.001(3)
C4 0.128(4) 0.065(3) 0.073(3) 0.011(2) 0.004(3) 0.008(3)
C5 0.092(3) 0.046(2) 0.060(2) 0.0026(18) 0.005(2) 0.004(2)
C6 0.072(2) 0.047(2) 0.048(2) -0.0020(16) 0.0046(17) 0.0054(18)
C7 0.084(3) 0.071(3) 0.056(2) -0.013(2) -0.007(2) 0.000(2)
C8 0.130(4) 0.089(3) 0.072(3) -0.033(3) 0.002(3) -0.015(3)
C9 0.093(3) 0.108(4) 0.092(3) -0.014(3) -0.022(3) 0.003(3)
C10 0.079(3) 0.051(2) 0.063(2) -0.0050(19) 0.014(2) 0.019(2)
C11 0.053(2) 0.0376(18) 0.063(2) -0.0022(18) 0.0094(17) 0.0037(16)
C12 0.079(3) 0.036(2) 0.096(3) -0.006(2) -0.004(2) -0.0011(19)
C13 0.090(3) 0.046(2) 0.111(4) -0.024(2) 0.008(3) 0.001(2)
C14 0.057(2) 0.0332(17) 0.061(2) -0.0009(16) 0.0122(16) -0.0040(15)
C15 0.062(2) 0.054(2) 0.068(2) -0.0005(17) 0.0130(18) -0.0010(18)
C16 0.060(2) 0.0417(19) 0.073(2) 0.0052(18) 0.0161(18) -0.0025(18)
C17 0.054(2) 0.054(2) 0.065(2) 0.0003(17) 0.0199(17) -0.0020(17)
C18 0.092(3) 0.051(2) 0.071(3) 0.000(2) 0.027(2) 0.002(2)
C19 0.113(3) 0.054(2) 0.086(3) -0.012(2) 0.048(3) -0.007(2)
C20 0.098(3) 0.082(3) 0.078(3) -0.023(3) 0.029(2) -0.016(3)
C21 0.112(4) 0.092(4) 0.066(3) -0.004(3) 0.020(2) 0.010(3)
C22 0.086(3) 0.071(3) 0.069(3) 0.004(2) 0.022(2) 0.011(2)

_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 C10 1.358(4) . ?
O1 C5 1.451(5) . ?
O2 C10 1.205(5) . ?
O3 C16 1.427(4) . ?
O3 H3D 0.8200 . ?
N1 C10 1.359(5) . ?
N1 N2 1.426(4) . ?
N1 C6 1.441(4) . ?
N2 C11 1.277(4) . ?
C1 C6 1.508(5) . ?
C1 C2 1.549(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.515(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.529(6) . ?
C3 C4 1.540(6) . ?
C3 H3A 0.9800 . ?
C4 C5 1.520(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.526(5) . ?
C5 H5A 0.9800 . ?
C6 C7 1.559(5) . ?
C7 C9 1.528(6) . ?
C7 C8 1.553(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.511(5) . ?
C11 C14 1.515(5) . ?
C12 C13 1.511(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.522(5) . ?
C14 C16 1.534(5) . ?
C14 H14A 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.522(5) . ?
C16 H16A 0.9800 . ?
C17 C22 1.377(5) . ?
C17 C18 1.387(5) . ?
C18 C19 1.388(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.356(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.370(6) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?

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
C10 O1 C5 107.5(3) . . ?
C16 O3 H3D 109.5 . . ?
C10 N1 N2 120.0(3) . . ?
C10 N1 C6 109.2(3) . . ?
N2 N1 C6 116.6(3) . . ?
C11 N2 N1 116.4(3) . . ?
C6 C1 C2 100.7(3) . . ?
C6 C1 H1A 111.6 . . ?
C2 C1 H1A 111.6 . . ?
C6 C1 H1B 111.6 . . ?
C2 C1 H1B 111.6 . . ?
H1A C1 H1B 109.4 . . ?
C3 C2 C1 104.0(3) . . ?
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 . . ?
C2 C3 C7 103.7(4) . . ?
C2 C3 C4 108.3(4) . . ?
C7 C3 C4 102.5(3) . . ?
C2 C3 H3A 113.8 . . ?
C7 C3 H3A 113.8 . . ?
C4 C3 H3A 113.8 . . ?
C5 C4 C3 100.6(3) . . ?
C5 C4 H4A 111.7 . . ?
C3 C4 H4A 111.7 . . ?
C5 C4 H4B 111.7 . . ?
C3 C4 H4B 111.7 . . ?
H4A C4 H4B 109.4 . . ?
O1 C5 C4 117.0(3) . . ?
O1 C5 C6 103.6(3) . . ?
C4 C5 C6 104.5(3) . . ?
O1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
N1 C6 C1 121.9(3) . . ?
N1 C6 C5 99.6(3) . . ?
C1 C6 C5 105.7(3) . . ?
N1 C6 C7 120.0(3) . . ?
C1 C6 C7 103.4(3) . . ?
C5 C6 C7 103.9(3) . . ?
C9 C7 C3 117.2(4) . . ?
C9 C7 C8 106.8(4) . . ?
C3 C7 C8 113.5(3) . . ?
C9 C7 C6 114.7(3) . . ?
C3 C7 C6 90.8(3) . . ?
C8 C7 C6 113.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O1 121.8(3) . . ?
O2 C10 N1 128.0(4) . . ?
O1 C10 N1 110.2(3) . . ?
N2 C11 C12 114.6(3) . . ?
N2 C11 C14 126.9(3) . . ?
C12 C11 C14 118.4(3) . . ?
C11 C12 C13 115.4(4) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 C15 110.5(3) . . ?
C11 C14 C16 113.0(3) . . ?
C15 C14 C16 111.5(3) . . ?
C11 C14 H14A 107.1 . . ?
C15 C14 H14A 107.1 . . ?
C16 C14 H14A 107.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 110.3(3) . . ?
O3 C16 C14 108.0(3) . . ?
C17 C16 C14 112.4(3) . . ?
O3 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C14 C16 H16A 108.7 . . ?
C22 C17 C18 117.3(4) . . ?
C22 C17 C16 121.9(3) . . ?
C18 C17 C16 120.8(3) . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C20 C19 C18 120.6(4) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C21 119.1(4) . . ?
C19 C20 H20A 120.5 . . ?
C21 C20 H20A 120.5 . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C21 C22 C17 121.6(4) . . ?
C21 C22 H22A 119.2 . . ?
C17 C22 H22A 119.2 . . ?

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
C10 N1 N2 C11 -77.8(4) . . . . ?
C6 N1 N2 C11 146.5(3) . . . . ?
C6 C1 C2 C3 -4.5(4) . . . . ?
C1 C2 C3 C7 -33.0(4) . . . . ?
C1 C2 C3 C4 75.4(4) . . . . ?
C2 C3 C4 C5 -64.8(4) . . . . ?
C7 C3 C4 C5 44.4(4) . . . . ?
C10 O1 C5 C4 135.3(4) . . . . ?
C10 O1 C5 C6 21.0(4) . . . . ?
C3 C4 C5 O1 -122.7(4) . . . . ?
C3 C4 C5 C6 -9.0(4) . . . . ?
C10 N1 C6 C1 144.7(3) . . . . ?
N2 N1 C6 C1 -75.1(4) . . . . ?
C10 N1 C6 C5 29.3(4) . . . . ?
N2 N1 C6 C5 169.5(3) . . . . ?
C10 N1 C6 C7 -82.9(4) . . . . ?
N2 N1 C6 C7 57.2(4) . . . . ?
C2 C1 C6 N1 178.9(3) . . . . ?
C2 C1 C6 C5 -68.8(4) . . . . ?
C2 C1 C6 C7 40.1(4) . . . . ?
O1 C5 C6 N1 -29.6(3) . . . . ?
C4 C5 C6 N1 -152.5(3) . . . . ?
O1 C5 C6 C1 -156.7(3) . . . . ?
C4 C5 C6 C1 80.3(4) . . . . ?
O1 C5 C6 C7 94.8(3) . . . . ?
C4 C5 C6 C7 -28.2(4) . . . . ?
C2 C3 C7 C9 172.4(4) . . . . ?
C4 C3 C7 C9 59.8(5) . . . . ?
C2 C3 C7 C8 -62.3(4) . . . . ?
C4 C3 C7 C8 -174.9(4) . . . . ?
C2 C3 C7 C6 54.0(3) . . . . ?
C4 C3 C7 C6 -58.7(4) . . . . ?
N1 C6 C7 C9 41.6(5) . . . . ?
C1 C6 C7 C9 -178.6(4) . . . . ?
C5 C6 C7 C9 -68.4(5) . . . . ?
N1 C6 C7 C3 162.2(3) . . . . ?
C1 C6 C7 C3 -58.0(4) . . . . ?
C5 C6 C7 C3 52.2(3) . . . . ?
N1 C6 C7 C8 -81.6(4) . . . . ?
C1 C6 C7 C8 58.2(4) . . . . ?
C5 C6 C7 C8 168.4(4) . . . . ?
C5 O1 C10 O2 177.7(4) . . . . ?
C5 O1 C10 N1 -3.0(4) . . . . ?
N2 N1 C10 O2 22.6(6) . . . . ?
C6 N1 C10 O2 161.2(4) . . . . ?
N2 N1 C10 O1 -156.6(3) . . . . ?
C6 N1 C10 O1 -18.0(4) . . . . ?
N1 N2 C11 C12 -179.3(3) . . . . ?
N1 N2 C11 C14 -1.6(5) . . . . ?
N2 C11 C12 C13 5.8(5) . . . . ?
C14 C11 C12 C13 -172.1(3) . . . . ?
N2 C11 C14 C15 -111.5(4) . . . . ?
C12 C11 C14 C15 66.2(4) . . . . ?
N2 C11 C14 C16 122.7(4) . . . . ?
C12 C11 C14 C16 -59.7(4) . . . . ?
C11 C14 C16 O3 78.6(3) . . . . ?
C15 C14 C16 O3 -46.7(4) . . . . ?
C11 C14 C16 C17 -159.4(3) . . . . ?
C15 C14 C16 C17 75.3(4) . . . . ?
O3 C16 C17 C22 -2.5(4) . . . . ?
C14 C16 C17 C22 -123.2(3) . . . . ?
O3 C16 C17 C18 177.9(3) . . . . ?
C14 C16 C17 C18 57.2(4) . . . . ?
C22 C17 C18 C19 0.8(6) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C19 C20 C21 -1.3(7) . . . . ?
C19 C20 C21 C22 1.7(7) . . . . ?
C20 C21 C22 C17 -0.9(7) . . . . ?
C18 C17 C22 C21 -0.3(5) . . . . ?
C16 C17 C22 C21 -179.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 938984'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_s1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N2 O3'
_chemical_formula_sum            'C22 H30 N2 O3'
_chemical_formula_weight         370.48

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   'P 21 21 21'

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                   6.9150(4)
_cell_length_b                   12.5529(8)
_cell_length_c                   24.5201(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2128.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1547
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9878
_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         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35155
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.89
_reflns_number_total             2371
_reflns_number_gt                1953
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0541P)^2^+0.3965P] where P=(Fo^2^+2Fc^2^)/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(10)
_refine_ls_number_reflns         2371
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.067
_refine_ls_shift/su_mean         0.006

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
O1 O 0.9196(3) 0.82729(15) 0.25805(7) 0.0598(5) Uani 1 1 d . . .
O2 O 0.9906(3) 0.80110(18) 0.16988(7) 0.0700(6) Uani 1 1 d . . .
O3 O 0.9153(3) 0.77778(16) 0.05653(7) 0.0609(5) Uani 1 1 d . A .
H3A H 0.9475 0.7817 0.0886 0.091 Uiso 1 1 calc R . .
N1 N 0.7055(3) 0.73862(16) 0.20742(7) 0.0443(5) Uani 1 1 d . . .
N2 N 0.6657(3) 0.65758(18) 0.16820(8) 0.0533(5) Uani 1 1 d . A .
C1 C 0.4397(4) 0.7202(3) 0.28011(11) 0.0701(8) Uani 1 1 d . . .
H1A H 0.3613 0.6696 0.2600 0.084 Uiso 1 1 calc R . .
H1B H 0.3863 0.7912 0.2759 0.084 Uiso 1 1 calc R . .
C2 C 0.4603(5) 0.6883(3) 0.34148(12) 0.0817(10) Uani 1 1 d . . .
H2B H 0.4264 0.7475 0.3651 0.098 Uiso 1 1 calc R . .
H2C H 0.3779 0.6281 0.3501 0.098 Uiso 1 1 calc R . .
C3 C 0.6748(5) 0.6588(2) 0.34786(10) 0.0631(8) Uani 1 1 d . . .
H3B H 0.7014 0.6105 0.3783 0.076 Uiso 1 1 calc R . .
C4 C 0.7918(5) 0.7623(2) 0.34933(10) 0.0679(8) Uani 1 1 d . . .
H4A H 0.9283 0.7487 0.3552 0.081 Uiso 1 1 calc R . .
H4B H 0.7448 0.8105 0.3773 0.081 Uiso 1 1 calc R . .
C5 C 0.7530(4) 0.8057(2) 0.29191(9) 0.0529(6) Uani 1 1 d . . .
H5A H 0.6694 0.8687 0.2938 0.063 Uiso 1 1 calc R . .
C6 C 0.6496(4) 0.71562(19) 0.26306(9) 0.0443(5) Uani 1 1 d . . .
C7 C 0.7264(4) 0.6126(2) 0.29139(10) 0.0530(6) Uani 1 1 d . . .
C8 C 0.6157(6) 0.5108(2) 0.27719(12) 0.0856(11) Uani 1 1 d . . .
H8A H 0.6721 0.4516 0.2962 0.128 Uiso 1 1 calc R . .
H8B H 0.6227 0.4986 0.2386 0.128 Uiso 1 1 calc R . .
H8C H 0.4829 0.5185 0.2879 0.128 Uiso 1 1 calc R . .
C9 C 0.9400(5) 0.5892(3) 0.28197(14) 0.0762(9) Uani 1 1 d . . .
H9A H 0.9747 0.5246 0.3005 0.114 Uiso 1 1 calc R . .
H9B H 1.0163 0.6471 0.2958 0.114 Uiso 1 1 calc R . .
H9C H 0.9636 0.5812 0.2436 0.114 Uiso 1 1 calc R . .
C10 C 0.8804(4) 0.7880(2) 0.20776(9) 0.0499(6) Uani 1 1 d . . .
C11 C 0.6221(4) 0.6894(2) 0.12048(9) 0.0530(7) Uani 1 1 d . . .
C12A C 0.6056(9) 0.5935(4) 0.0803(2) 0.0533(15) Uiso 0.55 1 d P A 1
H12A H 0.4765 0.5953 0.0649 0.064 Uiso 0.55 1 calc PR A 1
H12B H 0.6950 0.6067 0.0506 0.064 Uiso 0.55 1 calc PR A 1
C13A C 0.6399(11) 0.4858(6) 0.0993(3) 0.0783(18) Uiso 0.55 1 d P A 1
H13A H 0.6227 0.4368 0.0696 0.117 Uiso 0.55 1 calc PR A 1
H13B H 0.5500 0.4691 0.1279 0.117 Uiso 0.55 1 calc PR A 1
H13C H 0.7696 0.4802 0.1130 0.117 Uiso 0.55 1 calc PR A 1
C12B C 0.5428(12) 0.6132(6) 0.0802(3) 0.059(2) Uiso 0.45 1 d P A 3
H12C H 0.6196 0.6168 0.0472 0.070 Uiso 0.45 1 calc PR A 3
H12D H 0.4118 0.6343 0.0710 0.070 Uiso 0.45 1 calc PR A 3
C13B C 0.5403(14) 0.5007(7) 0.1001(4) 0.078(2) Uiso 0.45 1 d P A 3
H13D H 0.4840 0.4556 0.0728 0.117 Uiso 0.45 1 calc PR A 3
H13E H 0.4650 0.4964 0.1330 0.117 Uiso 0.45 1 calc PR A 3
H13F H 0.6701 0.4778 0.1075 0.117 Uiso 0.45 1 calc PR A 3
C14 C 0.6029(4) 0.8025(2) 0.10123(9) 0.0482(6) Uani 1 1 d . A .
H14A H 0.6503 0.8494 0.1302 0.058 Uiso 1 1 calc R . .
C15 C 0.3898(4) 0.8288(3) 0.09113(11) 0.0722(9) Uani 1 1 d . . .
H15A H 0.3171 0.8162 0.1239 0.108 Uiso 1 1 calc R A .
H15B H 0.3409 0.7844 0.0624 0.108 Uiso 1 1 calc R . .
H15C H 0.3778 0.9023 0.0808 0.108 Uiso 1 1 calc R . .
C16 C 0.7274(4) 0.8218(2) 0.04999(9) 0.0481(6) Uani 1 1 d . . .
H16A H 0.6654 0.7842 0.0196 0.058 Uiso 1 1 calc R A .
C17 C 0.7350(4) 0.9379(2) 0.03510(9) 0.0497(6) Uani 1 1 d . A .
C18 C 0.8698(5) 1.0055(2) 0.05779(10) 0.0627(8) Uani 1 1 d . . .
H18A H 0.9604 0.9790 0.0823 0.075 Uiso 1 1 calc R A .
C19 C 0.8712(6) 1.1121(3) 0.04451(12) 0.0807(10) Uani 1 1 d . A .
H19A H 0.9626 1.1568 0.0604 0.097 Uiso 1 1 calc R . .
C20 C 0.7408(7) 1.1532(3) 0.00848(14) 0.0910(11) Uani 1 1 d . . .
H20A H 0.7425 1.2254 0.0000 0.109 Uiso 1 1 calc R A .
C21 C 0.6088(6) 1.0876(3) -0.01476(15) 0.0911(11) Uani 1 1 d . A .
H21A H 0.5198 1.1148 -0.0395 0.109 Uiso 1 1 calc R . .
C22 C 0.6058(5) 0.9803(3) -0.00183(12) 0.0722(8) Uani 1 1 d . . .
H22A H 0.5150 0.9361 -0.0183 0.087 Uiso 1 1 calc R A .

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
O1 0.0731(12) 0.0620(11) 0.0442(9) -0.0010(8) -0.0080(9) -0.0242(10)
O2 0.0587(11) 0.0993(15) 0.0522(10) 0.0020(10) 0.0062(9) -0.0270(12)
O3 0.0518(10) 0.0822(13) 0.0488(9) -0.0004(9) 0.0102(8) 0.0130(10)
N1 0.0472(11) 0.0512(11) 0.0344(9) 0.0013(8) -0.0009(8) -0.0112(9)
N2 0.0628(14) 0.0568(12) 0.0402(10) -0.0024(10) -0.0010(10) -0.0182(11)
C1 0.0546(16) 0.097(2) 0.0583(16) 0.0168(16) 0.0113(13) 0.0002(17)
C2 0.089(2) 0.098(3) 0.0578(16) 0.0128(17) 0.0254(16) -0.002(2)
C3 0.091(2) 0.0598(16) 0.0388(12) 0.0117(12) -0.0033(13) -0.0029(16)
C4 0.100(2) 0.0661(18) 0.0370(12) -0.0041(12) -0.0066(15) -0.0048(18)
C5 0.0713(17) 0.0468(13) 0.0406(11) -0.0006(11) 0.0004(13) -0.0014(13)
C6 0.0480(13) 0.0489(13) 0.0360(11) 0.0043(10) 0.0017(10) -0.0013(11)
C7 0.0673(17) 0.0460(13) 0.0458(12) 0.0051(11) -0.0035(13) -0.0039(13)
C8 0.131(3) 0.0578(17) 0.0675(19) 0.0076(15) -0.005(2) -0.031(2)
C9 0.082(2) 0.0689(19) 0.078(2) 0.0014(16) -0.0093(18) 0.0226(17)
C10 0.0543(14) 0.0536(14) 0.0417(12) 0.0009(11) -0.0027(12) -0.0134(13)
C11 0.0548(15) 0.0664(16) 0.0378(11) -0.0044(11) 0.0023(11) -0.0189(14)
C14 0.0450(13) 0.0668(16) 0.0327(10) -0.0040(11) 0.0015(10) -0.0043(13)
C15 0.0461(15) 0.116(3) 0.0544(15) 0.0039(17) 0.0078(13) 0.0020(18)
C16 0.0451(13) 0.0661(16) 0.0331(10) -0.0059(11) 0.0018(10) -0.0011(13)
C17 0.0468(14) 0.0683(16) 0.0339(11) -0.0020(11) 0.0078(11) -0.0025(13)
C18 0.0699(19) 0.0755(19) 0.0426(13) -0.0037(13) -0.0032(14) -0.0083(17)
C19 0.111(3) 0.074(2) 0.0578(17) -0.0055(15) -0.0018(19) -0.020(2)
C20 0.125(3) 0.071(2) 0.076(2) 0.0124(18) 0.007(2) -0.007(2)
C21 0.095(3) 0.094(3) 0.084(2) 0.031(2) -0.015(2) 0.003(2)
C22 0.0639(18) 0.086(2) 0.0664(17) 0.0171(16) -0.0099(16) -0.0102(18)

_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 C10 1.355(3) . ?
O1 C5 1.445(3) . ?
O2 C10 1.212(3) . ?
O3 C16 1.421(3) . ?
O3 H3A 0.8200 . ?
N1 C10 1.359(3) . ?
N1 N2 1.427(3) . ?
N1 C6 1.447(3) . ?
N2 C11 1.273(3) . ?
C1 C6 1.511(4) . ?
C1 C2 1.564(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.537(5) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 C4 1.531(4) . ?
C3 C7 1.544(4) . ?
C3 H3B 0.9800 . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9800 . ?
C6 C7 1.561(3) . ?
C7 C9 1.523(4) . ?
C7 C8 1.529(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12B 1.480(7) . ?
C11 C14 1.502(4) . ?
C11 C12A 1.559(6) . ?
C12A C13A 1.450(9) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C12B C13B 1.494(11) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14 C15 1.530(4) . ?
C14 C16 1.543(3) . ?
C14 H14A 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.503(4) . ?
C16 H16A 0.9800 . ?
C17 C22 1.379(4) . ?
C17 C18 1.378(4) . ?
C18 C19 1.377(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.364(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.355(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.384(5) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?

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
C10 O1 C5 107.18(19) . . ?
C16 O3 H3A 109.5 . . ?
C10 N1 N2 120.1(2) . . ?
C10 N1 C6 108.84(18) . . ?
N2 N1 C6 116.21(18) . . ?
C11 N2 N1 116.2(2) . . ?
C6 C1 C2 99.7(2) . . ?
C6 C1 H1A 111.8 . . ?
C2 C1 H1A 111.8 . . ?
C6 C1 H1B 111.8 . . ?
C2 C1 H1B 111.8 . . ?
H1A C1 H1B 109.5 . . ?
C3 C2 C1 104.3(2) . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2C 110.9 . . ?
C1 C2 H2C 110.9 . . ?
H2B C2 H2C 108.9 . . ?
C4 C3 C2 108.0(3) . . ?
C4 C3 C7 102.6(2) . . ?
C2 C3 C7 102.9(2) . . ?
C4 C3 H3B 114.1 . . ?
C2 C3 H3B 114.1 . . ?
C7 C3 H3B 114.1 . . ?
C3 C4 C5 100.8(2) . . ?
C3 C4 H4A 111.6 . . ?
C5 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
C5 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
O1 C5 C6 104.36(18) . . ?
O1 C5 C4 117.0(3) . . ?
C6 C5 C4 104.2(2) . . ?
O1 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 . . ?
N1 C6 C1 120.6(2) . . ?
N1 C6 C5 99.51(18) . . ?
C1 C6 C5 107.2(2) . . ?
N1 C6 C7 119.6(2) . . ?
C1 C6 C7 103.6(2) . . ?
C5 C6 C7 104.50(19) . . ?
C9 C7 C8 106.9(3) . . ?
C9 C7 C3 115.7(3) . . ?
C8 C7 C3 113.7(2) . . ?
C9 C7 C6 115.0(2) . . ?
C8 C7 C6 114.9(2) . . ?
C3 C7 C6 90.50(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N1 128.0(2) . . ?
O2 C10 O1 121.5(2) . . ?
N1 C10 O1 110.4(2) . . ?
N2 C11 C12B 119.9(4) . . ?
N2 C11 C14 127.3(2) . . ?
C12B C11 C14 111.6(3) . . ?
N2 C11 C12A 110.9(3) . . ?
C12B C11 C12A 18.7(4) . . ?
C14 C11 C12A 121.6(3) . . ?
C13A C12A C11 120.3(5) . . ?
C13A C12A H12A 107.3 . . ?
C11 C12A H12A 107.3 . . ?
C13A C12A H12B 107.2 . . ?
C11 C12A H12B 107.3 . . ?
H12A C12A H12B 106.9 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11 C12B C13B 113.4(6) . . ?
C11 C12B H12C 108.9 . . ?
C13B C12B H12C 108.9 . . ?
C11 C12B H12D 108.9 . . ?
C13B C12B H12D 108.9 . . ?
H12C C12B H12D 107.7 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.4 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11 C14 C15 109.9(2) . . ?
C11 C14 C16 110.8(2) . . ?
C15 C14 C16 111.8(2) . . ?
C11 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
C16 C14 H14A 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 111.9(2) . . ?
O3 C16 C14 110.95(19) . . ?
C17 C16 C14 111.7(2) . . ?
O3 C16 H16A 107.4 . . ?
C17 C16 H16A 107.4 . . ?
C14 C16 H16A 107.4 . . ?
C22 C17 C18 117.7(3) . . ?
C22 C17 C16 120.7(3) . . ?
C18 C17 C16 121.5(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19A 119.5 . . ?
C18 C19 H19A 119.5 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C17 C22 C21 121.1(3) . . ?
C17 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?

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
C10 N1 N2 C11 -79.0(3) . . . . ?
C6 N1 N2 C11 146.5(2) . . . . ?
C6 C1 C2 C3 -6.0(3) . . . . ?
C1 C2 C3 C4 76.0(3) . . . . ?
C1 C2 C3 C7 -32.0(3) . . . . ?
C2 C3 C4 C5 -64.3(3) . . . . ?
C7 C3 C4 C5 43.9(3) . . . . ?
C10 O1 C5 C6 20.9(3) . . . . ?
C10 O1 C5 C4 135.5(2) . . . . ?
C3 C4 C5 O1 -123.4(2) . . . . ?
C3 C4 C5 C6 -8.8(3) . . . . ?
C10 N1 C6 C1 145.5(3) . . . . ?
N2 N1 C6 C1 -75.2(3) . . . . ?
C10 N1 C6 C5 28.8(2) . . . . ?
N2 N1 C6 C5 168.2(2) . . . . ?
C10 N1 C6 C7 -83.9(3) . . . . ?
N2 N1 C6 C7 55.4(3) . . . . ?
C2 C1 C6 N1 179.3(2) . . . . ?
C2 C1 C6 C5 -68.1(3) . . . . ?
C2 C1 C6 C7 42.1(3) . . . . ?
O1 C5 C6 N1 -29.4(2) . . . . ?
C4 C5 C6 N1 -152.6(2) . . . . ?
O1 C5 C6 C1 -155.7(2) . . . . ?
C4 C5 C6 C1 81.0(3) . . . . ?
O1 C5 C6 C7 94.7(2) . . . . ?
C4 C5 C6 C7 -28.6(3) . . . . ?
C4 C3 C7 C9 60.0(3) . . . . ?
C2 C3 C7 C9 172.0(3) . . . . ?
C4 C3 C7 C8 -175.8(3) . . . . ?
C2 C3 C7 C8 -63.8(3) . . . . ?
C4 C3 C7 C6 -58.2(2) . . . . ?
C2 C3 C7 C6 53.8(3) . . . . ?
N1 C6 C7 C9 43.5(3) . . . . ?
C1 C6 C7 C9 -178.7(2) . . . . ?
C5 C6 C7 C9 -66.6(3) . . . . ?
N1 C6 C7 C8 -81.1(3) . . . . ?
C1 C6 C7 C8 56.7(3) . . . . ?
C5 C6 C7 C8 168.8(3) . . . . ?
N1 C6 C7 C3 162.3(2) . . . . ?
C1 C6 C7 C3 -59.9(3) . . . . ?
C5 C6 C7 C3 52.2(2) . . . . ?
N2 N1 C10 O2 27.0(4) . . . . ?
C6 N1 C10 O2 164.5(3) . . . . ?
N2 N1 C10 O1 -155.2(2) . . . . ?
C6 N1 C10 O1 -17.7(3) . . . . ?
C5 O1 C10 O2 175.1(3) . . . . ?
C5 O1 C10 N1 -2.8(3) . . . . ?
N1 N2 C11 C12B -168.4(4) . . . . ?
N1 N2 C11 C14 -1.7(4) . . . . ?
N1 N2 C11 C12A 173.5(3) . . . . ?
N2 C11 C12A C13A -0.4(7) . . . . ?
C12B C11 C12A C13A -122.9(16) . . . . ?
C14 C11 C12A C13A 175.2(5) . . . . ?
N2 C11 C12B C13B -5.4(9) . . . . ?
C14 C11 C12B C13B -174.0(6) . . . . ?
C12A C11 C12B C13B 59.9(13) . . . . ?
N2 C11 C14 C15 -108.6(3) . . . . ?
C12B C11 C14 C15 58.9(4) . . . . ?
C12A C11 C14 C15 76.7(4) . . . . ?
N2 C11 C14 C16 127.3(3) . . . . ?
C12B C11 C14 C16 -65.1(4) . . . . ?
C12A C11 C14 C16 -47.4(4) . . . . ?
C11 C14 C16 O3 -45.6(3) . . . . ?
C15 C14 C16 O3 -168.5(2) . . . . ?
C11 C14 C16 C17 -171.1(2) . . . . ?
C15 C14 C16 C17 65.9(3) . . . . ?
O3 C16 C17 C22 141.8(2) . . . . ?
C14 C16 C17 C22 -93.2(3) . . . . ?
O3 C16 C17 C18 -38.5(3) . . . . ?
C14 C16 C17 C18 86.5(3) . . . . ?
C22 C17 C18 C19 1.2(4) . . . . ?
C16 C17 C18 C19 -178.5(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C19 C20 C21 C22 0.4(6) . . . . ?
C18 C17 C22 C21 -1.3(5) . . . . ?
C16 C17 C22 C21 178.4(3) . . . . ?
C20 C21 C22 C17 0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.89
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.030

_database_code_depnum_ccdc_archive 'CCDC 938985'