# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wxx_1_2
_database_code_depnum_ccdc_archive 'CCDC 1419796'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;
_audit_creation_date             2015-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 N'
_chemical_formula_sum            'C18 H17 N'
_chemical_formula_weight         247.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.7592(8)
_cell_length_b                   21.8617(17)
_cell_length_c                   8.2702(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.794(12)
_cell_angle_gamma                90.00
_cell_volume                     1283.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    294.76(10)
_cell_measurement_theta_max      69.8140
_cell_measurement_theta_min      8.9680
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4261
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         4.04
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.76(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   51.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega   44.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  108.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   87.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 12 omega   23.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
 13 omega   10.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 15 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000   90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2075830000
_diffrn_orient_matrix_UB_12      -0.0053223000
_diffrn_orient_matrix_UB_13      -0.1310031000
_diffrn_orient_matrix_UB_21      -0.0571555000
_diffrn_orient_matrix_UB_22      0.0441527000
_diffrn_orient_matrix_UB_23      0.1150859000
_diffrn_orient_matrix_UB_31      0.0260917000
_diffrn_orient_matrix_UB_32      0.0547030000
_diffrn_orient_matrix_UB_33      -0.1052873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2042
_reflns_number_total             2339
_reflns_odcompleteness_completeness 97.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.1970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1197
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.32338(18) 0.32994(6) 0.06021(17) 0.0384(3) Uani 1 d . . .
C1 C 0.1310(2) 0.32293(6) 0.03332(18) 0.0322(3) Uani 1 d . . .
C2 C -0.0083(2) 0.29316(6) -0.10670(19) 0.0385(3) Uani 1 d . . .
H2 H 0.0182 0.2749 -0.1957 0.046 Uiso 1 calc . . R
C3 C -0.1885(2) 0.29144(7) -0.10993(19) 0.0406(4) Uani 1 d . . .
H3 H -0.2834 0.2708 -0.2008 0.049 Uiso 1 calc . . R
C4 C -0.2292(2) 0.31999(7) 0.0200(2) 0.0388(4) Uani 1 d . . .
H4 H -0.3514 0.3190 0.0141 0.047 Uiso 1 calc . . R
C5 C -0.0877(2) 0.35032(6) 0.16001(19) 0.0342(3) Uani 1 d . . .
H5 H -0.1151 0.3699 0.2467 0.041 Uiso 1 calc . . R
C6 C 0.09268(19) 0.35061(6) 0.16704(17) 0.0287(3) Uani 1 d . . .
C7 C 0.27779(19) 0.37550(6) 0.30177(17) 0.0300(3) Uani 1 d . . .
C8 C 0.3995(2) 0.36180(6) 0.20181(19) 0.0360(3) Uani 1 d . . .
H8 H 0.5230 0.3757 0.2410 0.043 Uiso 1 calc . . R
C9 C 0.3587(2) 0.33205(7) 0.46461(19) 0.0379(3) Uani 1 d . . .
H9A H 0.3440 0.2900 0.4240 0.046 Uiso 1 calc . . R
H9B H 0.4923 0.3400 0.5281 0.046 Uiso 1 calc . . R
C10 C 0.2615(2) 0.34043(7) 0.5884(2) 0.0420(4) Uani 1 d . . .
H10A H 0.3105 0.3112 0.6845 0.050 Uiso 1 calc . . R
H10B H 0.1274 0.3332 0.5255 0.050 Uiso 1 calc . . R
C11 C 0.2947(2) 0.40502(7) 0.66173(18) 0.0425(4) Uani 1 d . . .
H11A H 0.2110 0.4127 0.7206 0.051 Uiso 1 calc . . R
H11B H 0.4230 0.4081 0.7497 0.051 Uiso 1 calc . . R
C12 C 0.26317(19) 0.45365(6) 0.52315(17) 0.0329(3) Uani 1 d . . .
C13 C 0.2326(2) 0.51332(7) 0.5658(2) 0.0402(4) Uani 1 d . . .
H13 H 0.2297 0.5212 0.6752 0.048 Uiso 1 calc . . R
C14 C 0.2066(2) 0.56062(7) 0.4489(2) 0.0413(4) Uani 1 d . . .
H14 H 0.1840 0.6000 0.4780 0.050 Uiso 1 calc . . R
C15 C 0.2141(2) 0.54921(6) 0.2884(2) 0.0387(4) Uani 1 d . . .
H15 H 0.1996 0.5815 0.2106 0.046 Uiso 1 calc . . R
C16 C 0.24293(19) 0.49064(6) 0.23999(18) 0.0331(3) Uani 1 d . . .
C17 C 0.26529(18) 0.44171(6) 0.35733(17) 0.0290(3) Uani 1 d . . .
C18 C 0.2489(3) 0.48271(8) 0.0615(2) 0.0453(4) Uani 1 d . . .
H18A H 0.3751 0.4731 0.0763 0.068 Uiso 1 calc . . GR
H18B H 0.2092 0.5199 -0.0049 0.068 Uiso 1 calc . . GR
H18C H 0.1661 0.4500 -0.0008 0.068 Uiso 1 calc . . GR


_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
N1 C1 1.4259(18) . ?
N1 C8 1.2834(18) . ?
C1 C2 1.387(2) . ?
C1 C6 1.3940(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3775(19) . ?
C6 C7 1.5196(18) . ?
C7 C8 1.5152(19) . ?
C7 C9 1.5582(19) . ?
C7 C17 1.5335(18) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(2) . ?
C12 C13 1.396(2) . ?
C12 C17 1.4026(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C16 C17 1.4071(19) . ?
C16 C18 1.505(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C8 N1 C1 105.57(12) . . ?
C2 C1 N1 126.51(13) . . ?
C2 C1 C6 121.49(14) . . ?
C6 C1 N1 111.99(12) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.94(14) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.06(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.51(14) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.75(13) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 107.22(12) . . ?
C5 C6 C1 120.20(12) . . ?
C5 C6 C7 132.56(12) . . ?
C6 C7 C9 110.34(11) . . ?
C6 C7 C17 113.73(11) . . ?
C8 C7 C6 98.16(10) . . ?
C8 C7 C9 103.21(11) . . ?
C8 C7 C17 118.61(11) . . ?
C17 C7 C9 111.63(11) . . ?
N1 C8 C7 116.50(13) . . ?
N1 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
C7 C9 H9A 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C7 112.02(12) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C9 C10 C11 109.51(13) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.73(12) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C13 C12 C11 117.28(13) . . ?
C13 C12 C17 119.39(13) . . ?
C17 C12 C11 123.32(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.15(14) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.44(13) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.38(14) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 119.50(13) . . ?
C15 C16 C18 117.49(13) . . ?
C17 C16 C18 123.01(13) . . ?
C12 C17 C7 119.71(12) . . ?
C12 C17 C16 119.08(12) . . ?
C16 C17 C7 121.06(11) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N1 C1 C2 C3 -179.69(13) . . . . ?
N1 C1 C6 C5 177.77(12) . . . . ?
N1 C1 C6 C7 -3.41(15) . . . . ?
C1 N1 C8 C7 6.08(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C1 C6 C7 C8 5.99(13) . . . . ?
C1 C6 C7 C9 -101.43(13) . . . . ?
C1 C6 C7 C17 132.25(12) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C2 C1 C6 C7 177.07(12) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C4 C5 C6 C7 -176.29(13) . . . . ?
C5 C6 C7 C8 -175.39(14) . . . . ?
C5 C6 C7 C9 77.19(18) . . . . ?
C5 C6 C7 C17 -49.13(19) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C7 C8 N1 -7.74(16) . . . . ?
C6 C7 C9 C10 -78.53(15) . . . . ?
C6 C7 C17 C12 104.84(14) . . . . ?
C6 C7 C17 C16 -70.78(16) . . . . ?
C7 C9 C10 C11 -62.55(16) . . . . ?
C8 N1 C1 C2 178.03(14) . . . . ?
C8 N1 C1 C6 -1.46(16) . . . . ?
C8 C7 C9 C10 177.43(12) . . . . ?
C8 C7 C17 C12 -140.55(13) . . . . ?
C8 C7 C17 C16 43.83(17) . . . . ?
C9 C7 C8 N1 105.48(14) . . . . ?
C9 C7 C17 C12 -20.80(17) . . . . ?
C9 C7 C17 C16 163.58(12) . . . . ?
C9 C10 C11 C12 46.65(18) . . . . ?
C10 C11 C12 C13 160.55(14) . . . . ?
C10 C11 C12 C17 -20.1(2) . . . . ?
C11 C12 C13 C14 178.63(14) . . . . ?
C11 C12 C17 C7 7.2(2) . . . . ?
C11 C12 C17 C16 -177.14(13) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C13 C12 C17 C7 -173.54(12) . . . . ?
C13 C12 C17 C16 2.2(2) . . . . ?
C13 C14 C15 C16 1.6(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C14 C15 C16 C18 179.95(14) . . . . ?
C15 C16 C17 C7 173.88(12) . . . . ?
C15 C16 C17 C12 -1.8(2) . . . . ?
C17 C7 C8 N1 -130.51(14) . . . . ?
C17 C7 C9 C10 48.96(16) . . . . ?
C17 C12 C13 C14 -0.7(2) . . . . ?
C18 C16 C17 C7 -6.2(2) . . . . ?
C18 C16 C17 C12 178.17(13) . . . . ?

_olex2_date_sample_data_collection 2015-07-16
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wuxx_35_3
_database_code_depnum_ccdc_archive 'CCDC 1419797'
_audit_update_record             
;
2015-08-20 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;
_audit_creation_date             2015-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N'
_chemical_formula_sum            'C22 H25 N'
_chemical_formula_weight         303.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3630(6)
_cell_length_b                   16.4293(8)
_cell_length_c                   25.6720(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3527.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1860
_cell_measurement_temperature    294.76(10)
_cell_measurement_theta_max      68.5740
_cell_measurement_theta_min      8.2870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.165
_diffrn_reflns_theta_min         3.443
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.76(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   64.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   49.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega   15.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega  106.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega  113.00  139.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  100.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 61

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
 13 omega    9.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0393957000
_diffrn_orient_matrix_UB_12      -0.0029597000
_diffrn_orient_matrix_UB_13      -0.0586418000
_diffrn_orient_matrix_UB_21      -0.1576873000
_diffrn_orient_matrix_UB_22      -0.0456815000
_diffrn_orient_matrix_UB_23      -0.0102716000
_diffrn_orient_matrix_UB_31      -0.0865140000
_diffrn_orient_matrix_UB_32      0.0818230000
_diffrn_orient_matrix_UB_33      -0.0078103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2168
_reflns_number_total             3289
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.018
_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)+(0.1093P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2038
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C8(H8), C14(H14), C3(H3), C2(H2), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C17 C 0.1895(3) 0.45048(12) 0.16909(7) 0.0408(5) Uani 1 1 d . . . . .
C16 C 0.3187(3) 0.40345(14) 0.15100(8) 0.0497(6) Uani 1 1 d . . . . .
C5 C -0.1015(3) 0.39976(12) 0.08832(8) 0.0432(5) Uani 1 1 d . . . . .
H5 H -0.0676 0.4509 0.0774 0.052 Uiso 1 1 calc R . . . .
C6 C -0.0592(3) 0.37150(12) 0.13709(8) 0.0423(5) Uani 1 1 d . . . . .
C7 C 0.0294(3) 0.41059(12) 0.18242(8) 0.0438(5) Uani 1 1 d . . . . .
C15 C 0.4636(3) 0.44037(16) 0.13943(10) 0.0590(7) Uani 1 1 d . . . . .
H15 H 0.5486 0.4091 0.1274 0.071 Uiso 1 1 calc R . . . .
C4 C -0.1952(3) 0.35168(13) 0.05524(8) 0.0457(5) Uani 1 1 d . . . . .
C8 C 0.0346(3) 0.33685(14) 0.21829(9) 0.0564(6) Uani 1 1 d . . . . .
H8 H 0.0935 0.3370 0.2490 0.068 Uiso 1 1 calc R . . . .
C12 C 0.2099(3) 0.53456(13) 0.17466(8) 0.0475(6) Uani 1 1 d . . . . .
C19 C -0.2436(3) 0.38150(15) 0.00102(9) 0.0519(6) Uani 1 1 d . . . . .
C9 C -0.0857(3) 0.46996(15) 0.21086(9) 0.0555(6) Uani 1 1 d . . . . .
H9A H -0.1932 0.4478 0.2100 0.067 Uiso 1 1 calc R . . . .
H9B H -0.0537 0.4746 0.2471 0.067 Uiso 1 1 calc R . . . .
C14 C 0.4824(4) 0.52317(16) 0.14573(10) 0.0645(7) Uani 1 1 d . . . . .
H14 H 0.5803 0.5475 0.1383 0.077 Uiso 1 1 calc R . . . .
C3 C -0.2408(3) 0.27523(14) 0.07297(10) 0.0565(6) Uani 1 1 d . . . . .
H3 H -0.3026 0.2424 0.0514 0.068 Uiso 1 1 calc R . . . .
N1 N -0.0459(3) 0.27511(12) 0.20410(8) 0.0625(6) Uani 1 1 d . . . . .
C1 C -0.1061(3) 0.29435(13) 0.15343(9) 0.0505(6) Uani 1 1 d . . . . .
C10 C -0.0862(3) 0.55313(14) 0.18654(10) 0.0577(6) Uani 1 1 d . . . . .
H10A H -0.1655 0.5872 0.2034 0.069 Uiso 1 1 calc R . . . .
H10B H -0.1130 0.5491 0.1499 0.069 Uiso 1 1 calc R . . . .
C2 C -0.1977(3) 0.24595(14) 0.12161(11) 0.0619(7) Uani 1 1 d . . . . .
H2 H -0.2302 0.1946 0.1325 0.074 Uiso 1 1 calc R . . . .
C11 C 0.0784(3) 0.59011(13) 0.19287(10) 0.0610(7) Uani 1 1 d . . . . .
H11A H 0.0834 0.6405 0.1733 0.073 Uiso 1 1 calc R . . . .
H11B H 0.0955 0.6031 0.2293 0.073 Uiso 1 1 calc R . . . .
C13 C 0.3571(3) 0.56952(14) 0.16287(10) 0.0576(7) Uani 1 1 d . . . . .
H13 H 0.3705 0.6254 0.1667 0.069 Uiso 1 1 calc R . . . .
C20 C -0.2644(5) 0.47412(17) -0.00041(12) 0.0838(10) Uani 1 1 d . . . . .
H20A H -0.3425 0.4901 0.0250 0.126 Uiso 1 1 calc GR . . . .
H20B H -0.2997 0.4904 -0.0344 0.126 Uiso 1 1 calc GR . . . .
H20C H -0.1641 0.4999 0.0073 0.126 Uiso 1 1 calc GR . . . .
C18 C 0.3079(4) 0.31204(17) 0.14364(13) 0.0760(9) Uani 1 1 d . . . . .
H18A H 0.2948 0.2862 0.1769 0.114 Uiso 1 1 calc GR . . . .
H18B H 0.4040 0.2926 0.1274 0.114 Uiso 1 1 calc GR . . . .
H18C H 0.2178 0.2994 0.1219 0.114 Uiso 1 1 calc GR . . . .
C22 C -0.3987(4) 0.3443(2) -0.01737(14) 0.1086(15) Uani 1 1 d . . . . .
H22A H -0.3854 0.2866 -0.0214 0.163 Uiso 1 1 calc GR . . . .
H22B H -0.4284 0.3678 -0.0502 0.163 Uiso 1 1 calc GR . . . .
H22C H -0.4811 0.3548 0.0078 0.163 Uiso 1 1 calc GR . . . .
C21 C -0.1110(5) 0.3608(2) -0.03737(11) 0.0904(11) Uani 1 1 d . . . . .
H21A H -0.0117 0.3831 -0.0252 0.136 Uiso 1 1 calc GR . . . .
H21B H -0.1361 0.3835 -0.0708 0.136 Uiso 1 1 calc GR . . . .
H21C H -0.1014 0.3028 -0.0403 0.136 Uiso 1 1 calc GR . . . .


_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
C17 C16 1.408(3) . ?
C17 C7 1.529(3) . ?
C17 C12 1.399(3) . ?
C16 C15 1.387(4) . ?
C16 C18 1.516(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C5 C4 1.400(3) . ?
C6 C7 1.522(3) . ?
C6 C1 1.391(3) . ?
C7 C8 1.522(3) . ?
C7 C9 1.553(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(3) . ?
C4 C19 1.530(3) . ?
C4 C3 1.389(3) . ?
C8 H8 0.9300 . ?
C8 N1 1.271(3) . ?
C12 C11 1.503(3) . ?
C12 C13 1.392(3) . ?
C19 C20 1.532(3) . ?
C19 C22 1.510(4) . ?
C19 C21 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.502(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.369(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.386(3) . ?
N1 C1 1.430(3) . ?
C1 C2 1.374(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.514(3) . ?
C2 H2 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C16 C17 C7 120.72(19) . . ?
C12 C17 C16 118.8(2) . . ?
C12 C17 C7 120.5(2) . . ?
C17 C16 C18 122.6(2) . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 C18 117.3(2) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.25(19) . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 132.53(18) . . ?
C5 C6 C1 120.5(2) . . ?
C1 C6 C7 106.92(18) . . ?
C17 C7 C9 112.25(18) . . ?
C6 C7 C17 115.85(17) . . ?
C6 C7 C8 98.08(16) . . ?
C6 C7 C9 108.83(19) . . ?
C8 C7 C17 116.85(19) . . ?
C8 C7 C9 103.48(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C5 C4 C19 121.30(19) . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C19 121.0(2) . . ?
C7 C8 H8 121.7 . . ?
N1 C8 C7 116.5(2) . . ?
N1 C8 H8 121.7 . . ?
C17 C12 C11 122.8(2) . . ?
C13 C12 C17 119.5(2) . . ?
C13 C12 C11 117.6(2) . . ?
C4 C19 C20 111.7(2) . . ?
C22 C19 C4 112.5(2) . . ?
C22 C19 C20 107.3(3) . . ?
C22 C19 C21 109.5(3) . . ?
C21 C19 C4 108.9(2) . . ?
C21 C19 C20 106.8(3) . . ?
C7 C9 H9A 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C7 112.19(19) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C4 C3 H3 118.7 . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 H3 118.7 . . ?
C8 N1 C1 105.70(19) . . ?
C6 C1 N1 112.1(2) . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 N1 127.5(2) . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C9 C10 C11 108.5(2) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C3 C2 H2 120.7 . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.7 . . ?
C12 C11 C10 112.8(2) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C17 C16 C15 C14 0.3(4) . . . . ?
C17 C7 C8 N1 -132.5(2) . . . . ?
C17 C7 C9 C10 43.3(3) . . . . ?
C17 C12 C11 C10 -19.9(3) . . . . ?
C17 C12 C13 C14 0.2(4) . . . . ?
C16 C17 C7 C6 -64.5(3) . . . . ?
C16 C17 C7 C8 50.3(3) . . . . ?
C16 C17 C7 C9 169.61(19) . . . . ?
C16 C17 C12 C11 179.0(2) . . . . ?
C16 C17 C12 C13 -0.7(3) . . . . ?
C16 C15 C14 C13 -0.8(4) . . . . ?
C5 C6 C7 C17 -51.0(3) . . . . ?
C5 C6 C7 C8 -176.1(3) . . . . ?
C5 C6 C7 C9 76.6(3) . . . . ?
C5 C6 C1 N1 177.8(2) . . . . ?
C5 C6 C1 C2 -1.3(4) . . . . ?
C5 C4 C19 C20 -31.8(3) . . . . ?
C5 C4 C19 C22 -152.5(3) . . . . ?
C5 C4 C19 C21 85.9(3) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
C6 C5 C4 C19 -180.0(2) . . . . ?
C6 C5 C4 C3 -1.0(3) . . . . ?
C6 C7 C8 N1 -8.1(3) . . . . ?
C6 C7 C9 C10 -86.3(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 C17 C16 C15 -179.5(2) . . . . ?
C7 C17 C16 C18 0.1(3) . . . . ?
C7 C17 C12 C11 -0.9(3) . . . . ?
C7 C17 C12 C13 179.3(2) . . . . ?
C7 C6 C1 N1 -4.8(3) . . . . ?
C7 C6 C1 C2 176.1(2) . . . . ?
C7 C8 N1 C1 5.6(3) . . . . ?
C7 C9 C10 C11 -64.3(3) . . . . ?
C15 C14 C13 C12 0.6(4) . . . . ?
C4 C5 C6 C7 -175.1(2) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C3 C2 C1 -0.2(4) . . . . ?
C8 C7 C9 C10 170.2(2) . . . . ?
C8 N1 C1 C6 -0.3(3) . . . . ?
C8 N1 C1 C2 178.8(3) . . . . ?
C12 C17 C16 C15 0.5(3) . . . . ?
C12 C17 C16 C18 -179.9(2) . . . . ?
C12 C17 C7 C6 115.4(2) . . . . ?
C12 C17 C7 C8 -129.7(2) . . . . ?
C12 C17 C7 C9 -10.4(3) . . . . ?
C19 C4 C3 C2 179.3(2) . . . . ?
C9 C7 C8 N1 103.6(3) . . . . ?
C9 C10 C11 C12 51.1(3) . . . . ?
C3 C4 C19 C20 149.2(3) . . . . ?
C3 C4 C19 C22 28.5(4) . . . . ?
C3 C4 C19 C21 -93.1(3) . . . . ?
N1 C1 C2 C3 -178.3(3) . . . . ?
C1 C6 C7 C17 132.1(2) . . . . ?
C1 C6 C7 C8 7.0(2) . . . . ?
C1 C6 C7 C9 -100.3(2) . . . . ?
C11 C12 C13 C14 -179.6(2) . . . . ?
C13 C12 C11 C10 159.9(2) . . . . ?
C18 C16 C15 C14 -179.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
