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

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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_vc1401
_audit_creation_date             2014-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H19NO
_chemical_oxdiff_usercomment     "Rob (Thom's Imine)"
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3365(2)
_cell_length_b                   16.4543(3)
_cell_length_c                   8.11930(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.8902(19)
_cell_angle_gamma                90
_cell_volume                     1632.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4790
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      29.8400
_cell_measurement_theta_min      3.4380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1871
_exptl_crystal_size_mid          0.1768
_exptl_crystal_size_min          0.0841
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.023
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      111(2)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0104837000
_diffrn_orient_matrix_UB_12      -0.0420599000
_diffrn_orient_matrix_UB_13      0.0085396000
_diffrn_orient_matrix_UB_21      0.0407295000
_diffrn_orient_matrix_UB_22      -0.0017723000
_diffrn_orient_matrix_UB_23      0.0706351000
_diffrn_orient_matrix_UB_31      -0.0400051000
_diffrn_orient_matrix_UB_32      0.0092373000
_diffrn_orient_matrix_UB_33      0.0521411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71071
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3503
_reflns_number_total             4337
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.8670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C8A-C7 \\sim C8-C7
 with sigma of 0.02
 C9A-C8A \\sim C9-C8
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C12-C11 \\sim C12-C11A
 with sigma of 0.02
 C16-C11 \\sim C16A-C11A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15
 with sigma of 0.02
 C17-C10 \\sim C17A-C10A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C11A)
Uanis(C8) = Uanis(C8A)
Uanis(C16) = Uanis(C16A)
4. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10A)=
 Sof(C11A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C22A)=Sof(H22A)=
 Sof(C21A)=Sof(H21A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=
 Sof(H18A)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10)=
 Sof(C11)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C22)=Sof(H22)=Sof(C21)=
 Sof(H21)=Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10A(H10A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,H9B), C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C15(H15A),
 C16(H16), C16A(H16A), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18),
 C22A(H22A), C21A(H21A), C20A(H20A), C19A(H19A), C18A(H18A)
5.d Fitted hexagon refined as free rotating group:
 C17(C22,C21,C20,C19,C18), C17A(C22A,C21A,C20A,C19A,C18A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1 O 0.26583(9) 0.77193(8) 0.16165(15) 0.0302(3) Uani 1 1 d . . . . .
H1 H 0.269(2) 0.7991(17) 0.264(4) 0.073(8) Uiso 1 1 d . . . . .
N1 N 0.30172(9) 0.64826(7) -0.04104(15) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.18160(12) 0.71808(9) 0.12710(19) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.08086(12) 0.72604(10) 0.1831(2) 0.0250(3) Uani 1 1 d . . . . .
H2 H 0.0688 0.7685 0.2539 0.030 Uiso 1 1 calc R . . . .
C3 C -0.00215(12) 0.67049(10) 0.1333(2) 0.0255(3) Uani 1 1 d . . . . .
H3 H -0.0693 0.6755 0.1723 0.031 Uiso 1 1 calc R . . . .
C4 C 0.01449(12) 0.60784(9) 0.0262(2) 0.0247(3) Uani 1 1 d . . . . .
H4 H -0.0419 0.5717 -0.0092 0.030 Uiso 1 1 calc R . . . .
C5 C 0.11585(12) 0.59916(9) -0.02834(19) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.1271 0.5571 -0.1005 0.026 Uiso 1 1 calc R . . . .
C6 C 0.20020(11) 0.65269(9) 0.02405(17) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.38878(11) 0.62756(9) 0.05559(18) 0.0196(3) Uani 1 1 d . . . . .
C8 C 0.3865(4) 0.5954(3) 0.2299(5) 0.0254(9) Uani 0.790(4) 1 d . . P A 1
H8A H 0.3630 0.5391 0.2233 0.030 Uiso 0.790(4) 1 calc R . P A 1
H8B H 0.3333 0.6261 0.2820 0.030 Uiso 0.790(4) 1 calc R . P A 1
C8A C 0.3877(17) 0.6105(15) 0.238(2) 0.0254(9) Uani 0.210(4) 1 d . . P A 2
H8AA H 0.3236 0.5784 0.2512 0.030 Uiso 0.210(4) 1 calc R . P A 2
H8AB H 0.3826 0.6615 0.2963 0.030 Uiso 0.210(4) 1 calc R . P A 2
C9 C 0.49707(19) 0.60084(17) 0.3377(3) 0.0189(5) Uani 0.790(4) 1 d . . P A 1
H9A H 0.4923 0.5768 0.4455 0.023 Uiso 0.790(4) 1 calc R . P A 1
H9B H 0.5178 0.6574 0.3545 0.023 Uiso 0.790(4) 1 calc R . P A 1
C9A C 0.4895(8) 0.5653(7) 0.3140(14) 0.028(2) Uani 0.210(4) 1 d . . P A 2
H9AA H 0.4874 0.5581 0.4321 0.033 Uiso 0.210(4) 1 calc R . P A 2
H9AB H 0.4905 0.5119 0.2639 0.033 Uiso 0.210(4) 1 calc R . P A 2
C10 C 0.58402(14) 0.55623(12) 0.2545(2) 0.0170(4) Uani 0.790(4) 1 d . . P A 1
H10 H 0.5600 0.4997 0.2377 0.020 Uiso 0.790(4) 1 calc R . P A 1
C10A C 0.5930(5) 0.6106(5) 0.2890(9) 0.024(2) Uani 0.210(4) 1 d . . P A 2
H10A H 0.5847 0.6652 0.3338 0.029 Uiso 0.210(4) 1 calc R . P A 2
C11 C 0.58925(16) 0.59307(14) 0.0835(3) 0.0171(4) Uani 0.790(4) 1 d . . P A 1
C11A C 0.5958(7) 0.6224(6) 0.1033(11) 0.0171(4) Uani 0.210(4) 1 d . . P A 2
C12 C 0.49616(11) 0.62940(9) -0.00812(18) 0.0191(3) Uani 1 1 d . . . . .
C13 C 0.50443(12) 0.66216(9) -0.16511(18) 0.0206(3) Uani 1 1 d . . . . .
H13 H 0.4425 0.6837 -0.2281 0.025 Uiso 1 1 calc R . . . .
C14 C 0.60285(12) 0.66306(10) -0.22808(19) 0.0230(3) Uani 1 1 d . . . . .
H14 H 0.6070 0.6854 -0.3323 0.028 Uiso 1 1 calc R . . . .
C15 C 0.69514(13) 0.63074(11) -0.1359(2) 0.0290(4) Uani 1 1 d . . . . .
H15 H 0.7624 0.6340 -0.1750 0.035 Uiso 0.790(4) 1 calc R . P A 1
H15A H 0.7551 0.6145 -0.1858 0.035 Uiso 0.210(4) 1 calc R . P A 2
C16 C 0.68729(19) 0.59334(16) 0.0155(3) 0.0233(5) Uani 0.790(4) 1 d . . P A 1
H16 H 0.7486 0.5680 0.0727 0.028 Uiso 0.790(4) 1 calc R . P A 1
C16A C 0.6947(8) 0.6233(6) 0.0377(12) 0.0233(5) Uani 0.210(4) 1 d . . P A 2
H16A H 0.7605 0.6189 0.1083 0.028 Uiso 0.210(4) 1 calc R . P A 2
C17 C 0.6939(2) 0.55528(16) 0.3667(4) 0.0180(7) Uani 0.790(4) 1 d . . P A 1
C22 C 0.7366(2) 0.48187(12) 0.4308(4) 0.0243(7) Uani 0.790(4) 1 d G . P A 1
H22 H 0.6989 0.4337 0.4036 0.029 Uiso 0.790(4) 1 calc R . P A 1
C21 C 0.8356(2) 0.48044(16) 0.5356(4) 0.0378(9) Uani 0.790(4) 1 d G . P A 1
H21 H 0.8642 0.4313 0.5785 0.045 Uiso 0.790(4) 1 calc R . P A 1
C20 C 0.89199(16) 0.5524(2) 0.5763(3) 0.0403(11) Uani 0.790(4) 1 d G . P A 1
H20 H 0.9583 0.5515 0.6464 0.048 Uiso 0.790(4) 1 calc R . P A 1
C19 C 0.8493(2) 0.62584(16) 0.5122(4) 0.0364(8) Uani 0.790(4) 1 d G . P A 1
H19 H 0.8870 0.6740 0.5394 0.044 Uiso 0.790(4) 1 calc R . P A 1
C18 C 0.7502(2) 0.62727(11) 0.4074(4) 0.0262(6) Uani 0.790(4) 1 d G . P A 1
H18 H 0.7217 0.6764 0.3645 0.031 Uiso 0.790(4) 1 calc R . P A 1
C17A C 0.6987(8) 0.5780(7) 0.3815(17) 0.026(3) Uani 0.210(4) 1 d . . P A 2
C22A C 0.7106(9) 0.4943(6) 0.4007(18) 0.028(3) Uani 0.210(4) 1 d G . P A 2
H22A H 0.6558 0.4597 0.3520 0.034 Uiso 0.210(4) 1 calc R . P A 2
C21A C 0.8044(10) 0.4625(4) 0.4925(16) 0.042(4) Uani 0.210(4) 1 d G . P A 2
H21A H 0.8123 0.4066 0.5053 0.050 Uiso 0.210(4) 1 calc R . P A 2
C20A C 0.8863(7) 0.5143(6) 0.5652(14) 0.036(4) Uani 0.210(4) 1 d G . P A 2
H20A H 0.9490 0.4931 0.6267 0.043 Uiso 0.210(4) 1 calc R . P A 2
C19A C 0.8744(7) 0.5979(6) 0.5460(13) 0.030(3) Uani 0.210(4) 1 d G . P A 2
H19A H 0.9292 0.6326 0.5947 0.036 Uiso 0.210(4) 1 calc R . P A 2
C18A C 0.7806(9) 0.6298(4) 0.4542(15) 0.026(3) Uani 0.210(4) 1 d G . P A 2
H18A H 0.7726 0.6857 0.4414 0.032 Uiso 0.210(4) 1 calc R . P A 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 H1 0.94(3) . ?
O1 C1 1.3651(17) . ?
N1 C6 1.4265(18) . ?
N1 C7 1.2859(18) . ?
C1 C2 1.387(2) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 C8 1.514(4) . ?
C7 C8A 1.507(15) . ?
C7 C12 1.487(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.519(5) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.517(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(3) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.516(11) . ?
C10 H10 0.9800 . ?
C10 C11 1.525(3) . ?
C10 C17 1.526(2) . ?
C10A H10A 0.9800 . ?
C10A C11A 1.525(11) . ?
C10A C17A 1.511(8) . ?
C11 C12 1.413(2) . ?
C11 C16 1.397(3) . ?
C11A C12 1.428(8) . ?
C11A C16A 1.397(11) . ?
C12 C13 1.401(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(2) . ?
C15 H15 0.9300 . ?
C15 H15A 0.9300 . ?
C15 C16 1.390(3) . ?
C15 C16A 1.415(10) . ?
C16 H16 0.9300 . ?
C16A H16A 0.9300 . ?
C17 C22 1.3900 . ?
C17 C18 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C17A C22A 1.3900 . ?
C17A C18A 1.3900 . ?
C22A H22A 0.9300 . ?
C22A C21A 1.3900 . ?
C21A H21A 0.9300 . ?
C21A C20A 1.3900 . ?
C20A H20A 0.9300 . ?
C20A C19A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C18A H18A 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
C1 O1 H1 115.3(17) . . ?
C7 N1 C6 119.33(12) . . ?
O1 C1 C2 124.23(14) . . ?
O1 C1 C6 116.02(13) . . ?
C2 C1 C6 119.72(13) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.00(14) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.40(14) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.66(14) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.51(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 N1 118.98(13) . . ?
C5 C6 N1 120.97(13) . . ?
C5 C6 C1 119.61(13) . . ?
N1 C7 C8 122.8(2) . . ?
N1 C7 C8A 121.9(8) . . ?
N1 C7 C12 119.45(13) . . ?
C12 C7 C8 117.6(2) . . ?
C12 C7 C8A 118.3(8) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.8(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8A H8AA 109.2 . . ?
C7 C8A H8AB 109.2 . . ?
C7 C8A C9A 111.9(13) . . ?
H8AA C8A H8AB 107.9 . . ?
C9A C8A H8AA 109.2 . . ?
C9A C8A H8AB 109.2 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C8 C9 C10 110.2(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8A C9A H9AA 109.3 . . ?
C8A C9A H9AB 109.3 . . ?
H9AA C9A H9AB 107.9 . . ?
C10A C9A C8A 111.7(12) . . ?
C10A C9A H9AA 109.3 . . ?
C10A C9A H9AB 109.3 . . ?
C9 C10 H10 107.5 . . ?
C11 C10 C9 109.31(16) . . ?
C11 C10 H10 107.5 . . ?
C11 C10 C17 113.7(2) . . ?
C17 C10 C9 111.1(2) . . ?
C17 C10 H10 107.5 . . ?
C9A C10A H10A 105.6 . . ?
C9A C10A C11A 109.2(7) . . ?
C11A C10A H10A 105.6 . . ?
C17A C10A C9A 116.3(8) . . ?
C17A C10A H10A 105.6 . . ?
C17A C10A C11A 113.6(8) . . ?
C12 C11 C10 121.00(16) . . ?
C16 C11 C10 120.56(17) . . ?
C16 C11 C12 118.42(18) . . ?
C12 C11A C10A 120.1(6) . . ?
C16A C11A C10A 121.2(7) . . ?
C16A C11A C12 118.6(8) . . ?
C11 C12 C7 120.45(14) . . ?
C11A C12 C7 120.6(4) . . ?
C13 C12 C7 120.27(13) . . ?
C13 C12 C11 119.13(14) . . ?
C13 C12 C11A 116.4(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.25(13) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.79(14) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 H15A 121.4 . . ?
C14 C15 C16 119.86(16) . . ?
C14 C15 C16A 117.3(4) . . ?
C16 C15 H15 120.1 . . ?
C16A C15 H15A 121.4 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.35(19) . . ?
C15 C16 H16 119.3 . . ?
C11A C16A C15 120.2(8) . . ?
C11A C16A H16A 119.9 . . ?
C15 C16A H16A 119.9 . . ?
C22 C17 C10 119.5(2) . . ?
C22 C17 C18 120.0 . . ?
C18 C17 C10 120.5(2) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C22A C17A C10A 118.6(8) . . ?
C22A C17A C18A 120.0 . . ?
C18A C17A C10A 121.4(8) . . ?
C17A C22A H22A 120.0 . . ?
C17A C22A C21A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C20A C21A C22A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A C20A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?

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
O1 H1 N1 0.94(3) 1.80(3) 2.7303(17) 169(2) 4_576

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 176.25(15) . . . . ?
O1 C1 C6 N1 -2.1(2) . . . . ?
O1 C1 C6 C5 -174.60(13) . . . . ?
N1 C7 C8 C9 -161.5(2) . . . . ?
N1 C7 C8A C9A 164.0(10) . . . . ?
N1 C7 C12 C11 -168.20(17) . . . . ?
N1 C7 C12 C11A 167.7(4) . . . . ?
N1 C7 C12 C13 7.3(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C1 C6 N1 176.03(13) . . . . ?
C2 C1 C6 C5 3.5(2) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 N1 -175.07(13) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
C6 N1 C7 C8 9.3(3) . . . . ?
C6 N1 C7 C8A -2.1(12) . . . . ?
C6 N1 C7 C12 -175.03(13) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
C7 N1 C6 C1 74.27(18) . . . . ?
C7 N1 C6 C5 -113.35(16) . . . . ?
C7 C8 C9 C10 -56.1(4) . . . . ?
C7 C8A C9A C10A 56(2) . . . . ?
C7 C12 C13 C14 -178.73(14) . . . . ?
C8 C7 C8A C9A 66(5) . . . . ?
C8 C7 C12 C11 7.7(3) . . . . ?
C8 C7 C12 C11A -16.5(5) . . . . ?
C8 C7 C12 C13 -176.8(3) . . . . ?
C8 C9 C10 C11 58.0(3) . . . . ?
C8 C9 C10 C17 -175.7(3) . . . . ?
C8A C7 C8 C9 -74(6) . . . . ?
C8A C7 C12 C11 18.6(12) . . . . ?
C8A C7 C12 C11A -5.5(12) . . . . ?
C8A C7 C12 C13 -165.9(12) . . . . ?
C8A C9A C10A C11A -58.6(13) . . . . ?
C8A C9A C10A C17A 171.2(12) . . . . ?
C9 C10 C11 C12 -28.8(2) . . . . ?
C9 C10 C11 C16 149.7(2) . . . . ?
C9 C10 C17 C22 113.7(2) . . . . ?
C9 C10 C17 C18 -65.1(3) . . . . ?
C9A C10A C11A C12 29.8(10) . . . . ?
C9A C10A C11A C16A -147.6(9) . . . . ?
C9A C10A C17A C22A 36.1(12) . . . . ?
C9A C10A C17A C18A -140.5(9) . . . . ?
C10 C11 C12 C7 -4.1(3) . . . . ?
C10 C11 C12 C11A 92.4(12) . . . . ?
C10 C11 C12 C13 -179.69(16) . . . . ?
C10 C11 C16 C15 -176.3(2) . . . . ?
C10 C17 C22 C21 -178.8(3) . . . . ?
C10 C17 C18 C19 178.8(3) . . . . ?
C10A C11A C12 C7 1.6(9) . . . . ?
C10A C11A C12 C11 -94.2(13) . . . . ?
C10A C11A C12 C13 162.7(6) . . . . ?
C10A C11A C16A C15 177.3(7) . . . . ?
C10A C17A C22A C21A -176.6(13) . . . . ?
C10A C17A C18A C19A 176.5(13) . . . . ?
C11 C10 C17 C22 -122.41(19) . . . . ?
C11 C10 C17 C18 58.8(3) . . . . ?
C11 C12 C13 C14 -3.1(2) . . . . ?
C11A C10A C17A C22A -92.0(9) . . . . ?
C11A C10A C17A C18A 91.4(11) . . . . ?
C11A C12 C13 C14 20.1(5) . . . . ?
C12 C7 C8 C9 22.8(4) . . . . ?
C12 C7 C8A C9A -23(2) . . . . ?
C12 C11 C16 C15 2.2(3) . . . . ?
C12 C11A C16A C15 -0.2(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C16 3.6(3) . . . . ?
C13 C14 C15 C16A -20.9(5) . . . . ?
C14 C15 C16 C11 -5.0(3) . . . . ?
C14 C15 C16A C11A 20.7(10) . . . . ?
C16 C11 C12 C7 177.39(16) . . . . ?
C16 C11 C12 C11A -86.1(12) . . . . ?
C16 C11 C12 C13 1.8(3) . . . . ?
C16 C15 C16A C11A -81.9(13) . . . . ?
C16A C11A C12 C7 179.1(6) . . . . ?
C16A C11A C12 C11 83.3(12) . . . . ?
C16A C11A C12 C13 -19.8(8) . . . . ?
C16A C15 C16 C11 84.2(12) . . . . ?
C17 C10 C11 C12 -153.6(2) . . . . ?
C17 C10 C11 C16 24.9(3) . . . . ?
C17 C22 C21 C20 0.0 . . . . ?
C22 C17 C18 C19 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
C18 C17 C22 C21 0.0 . . . . ?
C17A C10A C11A C12 161.6(7) . . . . ?
C17A C10A C11A C16A -15.8(12) . . . . ?
C17A C22A C21A C20A 0.0 . . . . ?
C22A C17A C18A C19A 0.0 . . . . ?
C22A C21A C20A C19A 0.0 . . . . ?
C21A C20A C19A C18A 0.0 . . . . ?
C20A C19A C18A C17A 0.0 . . . . ?
C18A C17A C22A C21A 0.0 . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 -1 0.0503 0.0000 0.9979 -0.9992 -0.0505 -0.0723 -0.0429
0 -1 1 0.0338 -0.0000 -0.9979 0.9992 0.0505 0.0723 0.0429
0 -2 -1 0.0764 -0.0009 -2.0002 -0.9993 0.0756 -0.0671 -0.0705
0 2 1 0.0764 0.0009 2.0002 0.9993 -0.0756 0.0671 0.0705
-1 0 0 0.0753 -0.9991 0.0003 -0.0004 0.0105 -0.0407 0.0400
1 0 0 0.0916 0.9991 -0.0003 0.0004 -0.0105 0.0407 -0.0400
7 -21 0 0.0828 6.9872 -20.9889 0.0019 0.8096 0.3219 -0.4733
1 2 0 0.0905 0.9997 1.9985 0.0005 -0.0945 0.0372 -0.0215
0 -1 0 0.0758 -0.0003 -0.9994 -0.0000 0.0420 0.0018 -0.0092
-2 4 -1 0.0658 -1.9973 3.9966 -0.9998 -0.1557 -0.1591 0.0647

_database_code_depnum_ccdc_archive 'CCDC 987438'
#######################################################################
#
#                 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_vc1402
_audit_creation_date             2014-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H17NO
_chemical_oxdiff_usercomment     "Thom's 312"
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6089(7)
_cell_length_b                   9.9620(9)
_cell_length_c                   10.0051(8)
_cell_angle_alpha                77.586(7)
_cell_angle_beta                 79.970(7)
_cell_angle_gamma                71.479(8)
_cell_volume                     789.38(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      28.4340
_cell_measurement_theta_min      3.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3062
_exptl_crystal_size_mid          0.2371
_exptl_crystal_size_min          0.1567
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9704
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.468
_diffrn_reflns_theta_min         3.080
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0627351000
_diffrn_orient_matrix_UB_12      -0.0386754000
_diffrn_orient_matrix_UB_13      -0.0452928000
_diffrn_orient_matrix_UB_21      -0.0459065000
_diffrn_orient_matrix_UB_22      0.0368975000
_diffrn_orient_matrix_UB_23      -0.0561452000
_diffrn_orient_matrix_UB_31      0.0400892000
_diffrn_orient_matrix_UB_32      0.0543239000
_diffrn_orient_matrix_UB_33      -0.0116397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3076
_reflns_number_total             3500
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C8(H8), C12(H12), C11(H11), C10(H10), C13(H13), C21(H21), C16(H16),
 C14(H14), C9(H9), C15(H15), C19(H19), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1 O 0.44438(10) 0.35194(9) 0.54134(8) 0.01973(19) Uani 1 1 d . . . . .
N1 N 0.52717(12) 0.41171(10) 0.77535(10) 0.0190(2) Uani 1 1 d . . . . .
C7 C 0.71566(14) -0.07125(12) 0.72828(12) 0.0171(2) Uani 1 1 d . . . . .
C20 C 0.09026(17) 0.62927(14) 0.77054(15) 0.0291(3) Uani 1 1 d . . . . .
H20 H 0.0086 0.6884 0.8237 0.035 Uiso 1 1 calc R . . . .
C8 C 0.69325(15) -0.08178(13) 0.87057(12) 0.0202(3) Uani 1 1 d . . . . .
H8 H 0.7315 -0.0244 0.9110 0.024 Uiso 1 1 calc R . . . .
C6 C 0.68216(14) 0.14608(12) 0.53943(11) 0.0177(2) Uani 1 1 d . . . . .
H6A H 0.7409 0.2048 0.4733 0.021 Uiso 1 1 calc R . . . .
H6B H 0.6327 0.1002 0.4892 0.021 Uiso 1 1 calc R . . . .
C12 C 0.65553(15) -0.15806(12) 0.67049(12) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.6683 -0.1514 0.5753 0.024 Uiso 1 1 calc R . . . .
C11 C 0.57716(16) -0.25390(13) 0.75282(13) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.5386 -0.3114 0.7128 0.029 Uiso 1 1 calc R . . . .
C10 C 0.55629(16) -0.26403(14) 0.89508(13) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.5041 -0.3283 0.9508 0.030 Uiso 1 1 calc R . . . .
C13 C 0.86913(16) 0.30665(14) 0.81308(13) 0.0227(3) Uani 1 1 d . . . . .
H13 H 0.8105 0.3950 0.8386 0.027 Uiso 1 1 calc R . . . .
C21 C 0.24437(16) 0.56222(13) 0.81480(14) 0.0252(3) Uani 1 1 d . . . . .
H21 H 0.2673 0.5790 0.8961 0.030 Uiso 1 1 calc R . . . .
C16 C 1.04428(15) 0.04239(14) 0.73760(12) 0.0222(3) Uani 1 1 d . . . . .
H16 H 1.1036 -0.0465 0.7134 0.027 Uiso 1 1 calc R . . . .
C5 C 0.80233(14) 0.03145(12) 0.63244(11) 0.0170(2) Uani 1 1 d . . . . .
H5 H 0.8898 -0.0250 0.5726 0.020 Uiso 1 1 calc R . . . .
C14 C 1.03090(17) 0.24389(15) 0.84031(14) 0.0273(3) Uani 1 1 d . . . . .
H14 H 1.0812 0.2905 0.8832 0.033 Uiso 1 1 calc R . . . .
C9 C 0.61399(16) -0.17752(14) 0.95305(13) 0.0232(3) Uani 1 1 d . . . . .
H9 H 0.5996 -0.1834 1.0482 0.028 Uiso 1 1 calc R . . . .
C15 C 1.11833(16) 0.11114(15) 0.80357(14) 0.0269(3) Uani 1 1 d . . . . .
H15 H 1.2266 0.0682 0.8232 0.032 Uiso 1 1 calc R . . . .
C4 C 0.88208(14) 0.10511(13) 0.70730(11) 0.0180(2) Uani 1 1 d . . . . .
C19 C 0.05778(16) 0.60809(14) 0.64639(15) 0.0286(3) Uani 1 1 d . . . . .
H19 H -0.0446 0.6560 0.6154 0.034 Uiso 1 1 calc R . . . .
C18 C 0.17593(16) 0.51658(13) 0.56858(14) 0.0244(3) Uani 1 1 d . . . . .
H18 H 0.1543 0.5036 0.4851 0.029 Uiso 1 1 calc R . . . .
C3 C 0.79289(14) 0.23781(12) 0.74715(11) 0.0179(2) Uani 1 1 d . . . . .
C22 C 0.36532(15) 0.46952(12) 0.73785(12) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.61955(14) 0.30368(12) 0.72005(11) 0.0170(2) Uani 1 1 d . . . . .
C17 C 0.32671(15) 0.44471(12) 0.61679(12) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.55005(14) 0.23852(12) 0.62881(11) 0.0166(2) Uani 1 1 d . . . . .
H1 H 0.4843 0.1794 0.6876 0.020 Uiso 1 1 calc R . . . .


_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 C17 1.3744(14) . ?
O1 C1 1.4386(13) . ?
N1 C22 1.4119(15) . ?
N1 C2 1.2868(15) . ?
C7 C8 1.3885(16) . ?
C7 C12 1.3977(16) . ?
C7 C5 1.5287(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.3845(19) . ?
C20 C19 1.392(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3911(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.5389(16) . ?
C6 C1 1.5085(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.3866(17) . ?
C11 H11 0.9300 . ?
C11 C10 1.3889(18) . ?
C10 H10 0.9300 . ?
C10 C9 1.3832(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3822(18) . ?
C13 C3 1.4027(17) . ?
C21 H21 0.9300 . ?
C21 C22 1.3947(17) . ?
C16 H16 0.9300 . ?
C16 C15 1.3891(18) . ?
C16 C4 1.3942(17) . ?
C5 H5 0.9800 . ?
C5 C4 1.5187(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(2) . ?
C9 H9 0.9300 . ?
C15 H15 0.9300 . ?
C4 C3 1.4040(17) . ?
C19 H19 0.9300 . ?
C19 C18 1.3827(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.3818(17) . ?
C3 C2 1.4742(16) . ?
C22 C17 1.3999(17) . ?
C2 C1 1.5180(16) . ?
C1 H1 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
C17 O1 C1 111.32(9) . . ?
C2 N1 C22 116.05(10) . . ?
C8 C7 C12 118.39(11) . . ?
C8 C7 C5 122.86(10) . . ?
C12 C7 C5 118.74(10) . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C19 119.88(12) . . ?
C19 C20 H20 120.1 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.50(11) . . ?
C9 C8 H8 119.8 . . ?
H6A C6 H6B 108.4 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
C1 C6 H6A 110.0 . . ?
C1 C6 H6B 110.0 . . ?
C1 C6 C5 108.57(9) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.07(11) . . ?
C11 C12 H12 119.5 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.01(12) . . ?
C10 C11 H11 120.0 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.31(11) . . ?
C9 C10 H10 120.3 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C3 120.39(12) . . ?
C3 C13 H13 119.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.23(12) . . ?
C22 C21 H21 119.9 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C4 120.73(12) . . ?
C4 C16 H16 119.6 . . ?
C7 C5 C6 110.79(9) . . ?
C7 C5 H5 107.6 . . ?
C6 C5 H5 107.6 . . ?
C4 C5 C7 113.83(9) . . ?
C4 C5 C6 109.25(9) . . ?
C4 C5 H5 107.6 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.95(12) . . ?
C15 C14 H14 120.0 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.73(11) . . ?
C10 C9 H9 119.6 . . ?
C16 C15 C14 120.13(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C4 C5 120.73(11) . . ?
C16 C4 C3 119.02(11) . . ?
C3 C4 C5 120.25(10) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.77(12) . . ?
C18 C19 H19 119.6 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 118.96(12) . . ?
C17 C18 H18 120.5 . . ?
C13 C3 C4 119.76(11) . . ?
C13 C3 C2 120.38(11) . . ?
C4 C3 C2 119.85(10) . . ?
C21 C22 N1 120.41(11) . . ?
C21 C22 C17 118.67(11) . . ?
C17 C22 N1 120.71(11) . . ?
N1 C2 C3 120.96(10) . . ?
N1 C2 C1 120.39(10) . . ?
C3 C2 C1 118.62(10) . . ?
O1 C17 C18 119.52(11) . . ?
O1 C17 C22 119.07(11) . . ?
C18 C17 C22 121.33(12) . . ?
O1 C1 C6 108.64(9) . . ?
O1 C1 C2 109.22(9) . . ?
O1 C1 H1 108.7 . . ?
C6 C1 C2 112.93(9) . . ?
C6 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?

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
N1 C22 C17 O1 6.20(16) . . . . ?
N1 C22 C17 C18 -170.72(11) . . . . ?
N1 C2 C1 O1 41.32(14) . . . . ?
N1 C2 C1 C6 162.32(10) . . . . ?
C7 C8 C9 C10 0.09(19) . . . . ?
C7 C12 C11 C10 0.47(19) . . . . ?
C7 C5 C4 C16 89.29(13) . . . . ?
C7 C5 C4 C3 -90.66(13) . . . . ?
C20 C21 C22 N1 173.92(11) . . . . ?
C20 C21 C22 C17 -0.82(18) . . . . ?
C20 C19 C18 C17 0.80(19) . . . . ?
C8 C7 C12 C11 -0.81(17) . . . . ?
C8 C7 C5 C6 -115.55(12) . . . . ?
C8 C7 C5 C4 8.04(16) . . . . ?
C6 C5 C4 C16 -146.29(11) . . . . ?
C6 C5 C4 C3 33.76(14) . . . . ?
C12 C7 C8 C9 0.53(17) . . . . ?
C12 C7 C5 C6 64.15(13) . . . . ?
C12 C7 C5 C4 -172.26(10) . . . . ?
C12 C11 C10 C9 0.2(2) . . . . ?
C11 C10 C9 C8 -0.44(19) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C13 C3 C2 N1 -11.56(16) . . . . ?
C13 C3 C2 C1 170.34(10) . . . . ?
C21 C20 C19 C18 2.3(2) . . . . ?
C21 C22 C17 O1 -179.08(10) . . . . ?
C21 C22 C17 C18 4.00(17) . . . . ?
C16 C4 C3 C13 1.69(17) . . . . ?
C16 C4 C3 C2 -178.04(10) . . . . ?
C5 C7 C8 C9 -179.76(11) . . . . ?
C5 C7 C12 C11 179.46(11) . . . . ?
C5 C6 C1 O1 175.96(9) . . . . ?
C5 C6 C1 C2 54.64(12) . . . . ?
C5 C4 C3 C13 -178.36(10) . . . . ?
C5 C4 C3 C2 1.91(16) . . . . ?
C14 C13 C3 C4 -0.68(18) . . . . ?
C14 C13 C3 C2 179.04(11) . . . . ?
C15 C16 C4 C5 178.68(11) . . . . ?
C15 C16 C4 C3 -1.37(18) . . . . ?
C4 C16 C15 C14 0.04(19) . . . . ?
C4 C3 C2 N1 168.16(10) . . . . ?
C4 C3 C2 C1 -9.93(15) . . . . ?
C19 C20 C21 C22 -2.28(19) . . . . ?
C19 C18 C17 O1 179.11(11) . . . . ?
C19 C18 C17 C22 -3.99(18) . . . . ?
C3 C13 C14 C15 -0.67(19) . . . . ?
C3 C2 C1 O1 -140.57(10) . . . . ?
C3 C2 C1 C6 -19.57(14) . . . . ?
C22 N1 C2 C3 177.60(9) . . . . ?
C22 N1 C2 C1 -4.34(15) . . . . ?
C2 N1 C22 C21 164.60(11) . . . . ?
C2 N1 C22 C17 -20.77(16) . . . . ?
C17 O1 C1 C6 -176.61(9) . . . . ?
C17 O1 C1 C2 -53.03(12) . . . . ?
C1 O1 C17 C18 -150.72(10) . . . . ?
C1 O1 C17 C22 32.31(14) . . . . ?
C1 C6 C5 C7 65.02(12) . . . . ?
C1 C6 C5 C4 -61.16(12) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 3 14 0.1524 -0.0144 2.9975 13.9771 -0.7499 -0.6735 -0.0004
-8 -11 3 0.1153 -8.0103 -10.9724 2.9856 -0.2134 -0.2048 -0.9519
0 -4 -14 0.1132 0.0132 -3.9964 -13.9776 0.7885 0.6367 -0.0539
8 13 5 0.1006 8.0024 12.9706 5.0015 -0.2261 -0.1696 0.9672
4 -11 0 0.0667 3.9827 -10.9950 -0.0026 0.6752 -0.5884 -0.4376
9 -6 1 0.0721 8.9830 -6.0099 1.0006 0.7507 -0.6903 0.0220
-3 12 0 0.0838 -2.9824 11.9920 0.0036 -0.6511 0.5792 0.5318
-11 0 -2 0.0960 -10.9874 0.0204 -2.0026 -0.5994 0.6176 -0.4161
11 4 -5 0.0928 11.0014 3.9746 -4.9835 0.7622 -0.0786 0.7150
6 -7 -7 0.0822 5.9949 -7.0037 -6.9877 0.9635 -0.1413 -0.0588
-4 10 7 0.1115 -3.9930 9.9966 6.9901 -0.9537 0.1597 0.3016
-7 5 7 0.1266 -6.9965 5.0079 6.9862 -0.9490 0.1137 -0.0898
-3 8 -9 0.0975 -2.9757 7.9959 -8.9826 -0.0891 0.9360 0.4196
-8 2 -10 0.1218 -7.9772 2.0120 -9.9863 -0.1260 1.0011 -0.0943
3 -9 7 0.0865 2.9770 -8.9949 6.9856 0.2182 -0.8608 -0.4506
-3 -13 3 0.0964 -3.0173 -12.9794 2.9874 0.1774 -0.5081 -0.8608

_database_code_depnum_ccdc_archive 'CCDC 987439'
