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

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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_compound_cis_2a

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40

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'
O O 0.0492 0.0322 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   6.3774(3)
_cell_length_b                   10.6140(5)
_cell_length_c                   26.4051(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.339(6)
_cell_angle_gamma                90
_cell_volume                     1739.13(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2395
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      68.0

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.617
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_type            
'RAPID II large area curved imaging plate detector '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8145
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.440
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3103
_reflns_number_gt                1792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0513P)²+1.6323P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3103
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1894
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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_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 0.0198(5) -0.6539(2) -0.07678(9) 0.0741(8) Uani 1 1 d . . . . .
O2 O -0.0984(4) -0.7284(2) -0.22413(9) 0.0706(8) Uani 1 1 d . . . . .
N1 N 0.1667(4) -0.8759(3) -0.13065(9) 0.0449(6) Uani 1 1 d . . . . .
H1N H 0.068(5) -0.814(3) -0.1345(12) 0.054 Uiso 1 1 d . U . . .
C2 C 0.3345(5) -0.8309(3) -0.08669(11) 0.0486(8) Uani 1 1 d . . . . .
H2 H 0.3811 -0.7467 -0.0947 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5264(5) -0.9210(3) -0.07817(14) 0.0618(9) Uani 1 1 d . . . . .
H3A H 0.6422 -0.8883 -0.0508 0.074 Uiso 1 1 calc R U . . .
H3B H 0.4842 -1.0023 -0.0670 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6060(5) -0.9374(4) -0.12740(15) 0.0702(11) Uani 1 1 d . . . . .
H4A H 0.6623 -0.8580 -0.1367 0.084 Uiso 1 1 calc R U . . .
H4B H 0.7219 -0.9988 -0.1215 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4256(5) -0.9811(3) -0.17120(13) 0.0562(9) Uani 1 1 d . . . . .
H5A H 0.3772 -1.0638 -0.1631 0.067 Uiso 1 1 calc R U . . .
H5B H 0.4770 -0.9879 -0.2029 0.067 Uiso 1 1 calc R U . . .
C6 C 0.2384(5) -0.8889(3) -0.17944(11) 0.0470(7) Uani 1 1 d . . . . .
H6 H 0.2862 -0.8066 -0.1894 0.056 Uiso 1 1 calc R U . . .
C7 C 0.0491(5) -0.9341(3) -0.22148(11) 0.0491(8) Uani 1 1 d . . . . .
H7A H 0.1027 -0.9624 -0.2511 0.059 Uiso 1 1 calc R U . . .
H7B H -0.0153 -1.0062 -0.2083 0.059 Uiso 1 1 calc R U . . .
C8 C -0.1241(5) -0.8368(3) -0.24006(11) 0.0482(8) Uani 1 1 d . . . . .
C9 C -0.3273(5) -0.8741(3) -0.27775(10) 0.0422(7) Uani 1 1 d . . . . .
C10 C -0.3504(6) -0.9880(3) -0.30421(12) 0.0559(9) Uani 1 1 d . . . . .
H10 H -0.2366 -1.0449 -0.2989 0.067 Uiso 1 1 calc R U . . .
C11 C -0.5443(6) -1.0164(3) -0.33866(13) 0.0649(10) Uani 1 1 d . . . . .
H11 H -0.5596 -1.0927 -0.3564 0.078 Uiso 1 1 calc R U . . .
C12 C -0.7142(6) -0.9332(3) -0.34690(13) 0.0637(9) Uani 1 1 d . . . . .
H12 H -0.8441 -0.9528 -0.3699 0.076 Uiso 1 1 calc R U . . .
C13 C -0.6886(6) -0.8203(3) -0.32057(12) 0.0589(9) Uani 1 1 d . . . . .
H13 H -0.8020 -0.7630 -0.3262 0.071 Uiso 1 1 calc R U . . .
C14 C -0.4977(5) -0.7906(3) -0.28590(11) 0.0499(8) Uani 1 1 d . . . . .
H14 H -0.4838 -0.7144 -0.2681 0.060 Uiso 1 1 calc R U . . .
C15 C 0.2430(5) -0.8240(3) -0.03865(11) 0.0537(8) Uani 1 1 d . . . . .
H15A H 0.1853 -0.9061 -0.0331 0.064 Uiso 1 1 calc R U . . .
H15B H 0.3601 -0.8062 -0.0089 0.064 Uiso 1 1 calc R U . . .
C16 C 0.0695(6) -0.7273(3) -0.04037(11) 0.0519(8) Uani 1 1 d . . . . .
C17 C -0.0423(5) -0.7214(3) 0.00340(11) 0.0479(8) Uani 1 1 d . . . . .
C18 C -0.1864(6) -0.6235(3) 0.00482(13) 0.0591(9) Uani 1 1 d . . . . .
H18 H -0.2086 -0.5616 -0.0208 0.071 Uiso 1 1 calc R U . . .
C19 C -0.2964(6) -0.6180(4) 0.04412(14) 0.0652(10) Uani 1 1 d . . . . .
H19 H -0.3899 -0.5514 0.0453 0.078 Uiso 1 1 calc R U . . .
C20 C -0.2680(6) -0.7109(4) 0.08168(13) 0.0628(10) Uani 1 1 d . . . . .
H20 H -0.3436 -0.7074 0.1078 0.075 Uiso 1 1 calc R U . . .
C21 C -0.1284(6) -0.8083(3) 0.08036(12) 0.0575(9) Uani 1 1 d . . . . .
H21 H -0.1114 -0.8716 0.1054 0.069 Uiso 1 1 calc R U . . .
C22 C -0.0128(5) -0.8132(3) 0.04215(12) 0.0537(8) Uani 1 1 d . . . . .
H22 H 0.0854 -0.8781 0.0423 0.064 Uiso 1 1 calc R U . . .


_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 C16 1.221(3) . ?
O2 C8 1.223(3) . ?
N1 C2 1.465(4) . ?
N1 C6 1.470(3) . ?
N1 H1N 0.90(3) . ?
C2 C15 1.515(4) . ?
C2 C3 1.528(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.511(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.504(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.520(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.517(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.509(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.494(4) . ?
C9 C14 1.380(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.389(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.503(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.493(4) . ?
C17 C18 1.394(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
C2 N1 C6 114.0(2) . . ?
C2 N1 H1N 102(2) . . ?
C6 N1 H1N 109(2) . . ?
N1 C2 C15 109.1(2) . . ?
N1 C2 C3 109.1(3) . . ?
C15 C2 C3 110.9(3) . . ?
N1 C2 H2 109.3 . . ?
C15 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C4 C3 C2 111.2(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.3(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.3(3) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C7 108.3(2) . . ?
N1 C6 C5 109.1(2) . . ?
C7 C6 C5 111.5(3) . . ?
N1 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C8 C7 C6 114.9(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O2 C8 C9 120.4(3) . . ?
O2 C8 C7 120.1(3) . . ?
C9 C8 C7 119.5(3) . . ?
C14 C9 C10 119.6(3) . . ?
C14 C9 C8 117.6(3) . . ?
C10 C9 C8 122.8(3) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 119.9(3) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C2 115.5(3) . . ?
C16 C15 H15A 108.4 . . ?
C2 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C2 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
O1 C16 C17 120.0(3) . . ?
O1 C16 C15 121.0(3) . . ?
C17 C16 C15 119.0(3) . . ?
C18 C17 C22 118.7(3) . . ?
C18 C17 C16 119.2(3) . . ?
C22 C17 C16 122.1(3) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?

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
C6 N1 C2 C15 -178.9(3) . . . . ?
C6 N1 C2 C3 -57.6(3) . . . . ?
N1 C2 C3 C4 54.8(4) . . . . ?
C15 C2 C3 C4 174.9(3) . . . . ?
C2 C3 C4 C5 -55.8(4) . . . . ?
C3 C4 C5 C6 56.9(4) . . . . ?
C2 N1 C6 C7 -179.2(2) . . . . ?
C2 N1 C6 C5 59.2(3) . . . . ?
C4 C5 C6 N1 -57.3(3) . . . . ?
C4 C5 C6 C7 -176.9(3) . . . . ?
N1 C6 C7 C8 72.2(3) . . . . ?
C5 C6 C7 C8 -167.7(2) . . . . ?
C6 C7 C8 O2 5.3(4) . . . . ?
C6 C7 C8 C9 -174.4(2) . . . . ?
O2 C8 C9 C14 -12.2(4) . . . . ?
C7 C8 C9 C14 167.5(3) . . . . ?
O2 C8 C9 C10 168.0(3) . . . . ?
C7 C8 C9 C10 -12.3(4) . . . . ?
C14 C9 C10 C11 0.1(5) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C8 C9 C14 C13 179.6(3) . . . . ?
C12 C13 C14 C9 0.9(5) . . . . ?
N1 C2 C15 C16 -66.5(3) . . . . ?
C3 C2 C15 C16 173.4(3) . . . . ?
C2 C15 C16 O1 -5.3(5) . . . . ?
C2 C15 C16 C17 174.9(3) . . . . ?
O1 C16 C17 C18 -6.8(5) . . . . ?
C15 C16 C17 C18 173.1(3) . . . . ?
O1 C16 C17 C22 171.1(3) . . . . ?
C15 C16 C17 C22 -9.0(4) . . . . ?
C22 C17 C18 C19 0.2(5) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 1.1(5) . . . . ?
C20 C21 C22 C17 -2.2(5) . . . . ?
C18 C17 C22 C21 1.6(5) . . . . ?
C16 C17 C22 C21 -176.3(3) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.063

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 964826'
#######################################################################
#
#                 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_compound_cis-2d

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H33 N O2'
_chemical_formula_sum            'C34 H33 N O2'
_chemical_formula_weight         487.61

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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

_cell_length_a                   23.678(6)
_cell_length_b                   14.550(2)
_cell_length_c                   19.515(4)
_cell_angle_alpha                90
_cell_angle_beta                 126.678(5)
_cell_angle_gamma                90
_cell_volume                     5392.0(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9723
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      20.816

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29604
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.763
_diffrn_reflns_theta_max         20.750
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990

_reflns_number_total             2782
_reflns_number_gt                2048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;

 The CCD detector was placed at a distance and theta angle to afford data measurement
 up to 0.84 Å resolution. Despite reasonable long exposure, data analysis shows that 
 very little data were obtainable beyond θ = 20/% leading to the decision to cut the 
 dataset at the 1.0Å resolution limit. 


 Shell Lower Upper Average      Average     Norm. Linear Square
 limit    Angstrom       I   error   stat. Chi**2  R-fac  R-fac
      50.00   1.81   132.4     3.5     2.2  1.610  0.034  0.038
       1.81   1.44    25.1     1.6     1.4  1.295  0.072  0.039
       1.44   1.25    12.9     1.6     1.5  1.325  0.140  0.069
       1.25   1.14    12.3     1.8     1.8  1.315  0.161  0.074
       1.14   1.06     8.1     1.9     1.9  1.206  0.253  0.109
       1.06   1.00     4.3     2.0     2.0  1.185  0.501  0.201
       1.00   0.95     2.4     2.2     2.2  1.119  0.898  0.380
       0.95   0.90     1.3     2.5     2.5  1.117  0.000  0.541
       0.90   0.87     1.0     3.1     3.1  1.092  0.000  0.813
       0.87   0.84     0.7     3.7     3.7  1.039  0.000  0.891
  All reflections     21.3     2.4     2.2  1.281  0.075  0.041

 The results of X-ray analysis are reasonable however from a chemical/crystallographical 
 point of view.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0724P)²+2.4475P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_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 0.84617(12) 0.19156(16) 0.73625(16) 0.1078(9) Uani 1 1 d . . . . .
O2 O 0.97123(12) 0.57648(17) 0.84932(14) 0.1031(8) Uani 1 1 d . . . . .
N1 N 0.76354(10) 0.47257(15) 0.59670(13) 0.0566(6) Uani 1 1 d . . . . .
C4 C 0.90084(15) 0.4014(3) 0.6637(2) 0.0857(10) Uani 1 1 d . . . . .
H4A H 0.9189 0.3885 0.7223 0.103 Uiso 1 1 calc R U . . .
H4B H 0.9367 0.3846 0.6565 0.103 Uiso 1 1 calc R U . . .
C5 C 0.83431(15) 0.3459(2) 0.60281(18) 0.0732(9) Uani 1 1 d . . . . .
H5A H 0.8447 0.2811 0.6161 0.088 Uiso 1 1 calc R U . . .
H5B H 0.8190 0.3552 0.5448 0.088 Uiso 1 1 calc R U . . .
C6 C 0.77503(13) 0.37282(19) 0.60816(16) 0.0596(8) Uani 1 1 d . . . . .
H6 H 0.7323 0.3446 0.5585 0.072 Uiso 1 1 calc R U . . .
C2 C 0.82540(13) 0.5329(2) 0.65056(16) 0.0610(8) Uani 1 1 d . . . . .
H2 H 0.8109 0.5940 0.6243 0.073 Uiso 1 1 calc R U . . .
C3 C 0.88372(15) 0.5022(2) 0.64495(19) 0.0772(9) Uani 1 1 d . . . . .
H3A H 0.8698 0.5151 0.5880 0.093 Uiso 1 1 calc R U . . .
H3B H 0.9258 0.5378 0.6851 0.093 Uiso 1 1 calc R U . . .
C23 C 0.69946(13) 0.50349(19) 0.58414(17) 0.0621(8) Uani 1 1 d . . . . .
H23 H 0.7049 0.4939 0.6375 0.075 Uiso 1 1 calc R U . . .
C30 C 0.63477(14) 0.45062(19) 0.5134(2) 0.0730(9) Uani 1 1 d . . . . .
C31 C 0.62551(17) 0.4271(2) 0.4388(2) 0.0936(11) Uani 1 1 d . . . . .
H31 H 0.6603 0.4408 0.4320 0.112 Uiso 1 1 calc R U . . .
C32 C 0.5641(3) 0.3828(3) 0.3737(3) 0.1312(18) Uani 1 1 d . . . . .
H32 H 0.5579 0.3660 0.3236 0.157 Uiso 1 1 calc R U . . .
C33 C 0.5129(3) 0.3642(4) 0.3842(5) 0.168(3) Uani 1 1 d . . . . .
H33 H 0.4720 0.3341 0.3411 0.202 Uiso 1 1 calc R U . . .
C34 C 0.5214(2) 0.3892(3) 0.4563(5) 0.152(3) Uani 1 1 d . . . . .
H34 H 0.4856 0.3777 0.4618 0.182 Uiso 1 1 calc R U . . .
C35 C 0.58253(18) 0.4318(2) 0.5220(3) 0.1033(13) Uani 1 1 d . . . . .
H35 H 0.5883 0.4477 0.5720 0.124 Uiso 1 1 calc R U . . .
C24 C 0.68333(13) 0.6047(2) 0.56014(18) 0.0606(8) Uani 1 1 d . . . . .
C29 C 0.66019(14) 0.6574(2) 0.59679(19) 0.0715(9) Uani 1 1 d . . . . .
H29 H 0.6597 0.6328 0.6404 0.086 Uiso 1 1 calc R U . . .
C28 C 0.63746(16) 0.7469(3) 0.5701(3) 0.0896(11) Uani 1 1 d . . . . .
H28 H 0.6220 0.7821 0.5958 0.108 Uiso 1 1 calc R U . . .
C27 C 0.63790(18) 0.7830(3) 0.5061(3) 0.0971(12) Uani 1 1 d . . . . .
H27 H 0.6218 0.8426 0.4870 0.117 Uiso 1 1 calc R U . . .
C26 C 0.66195(18) 0.7320(3) 0.4698(2) 0.0935(11) Uani 1 1 d . . . . .
H26 H 0.6634 0.7575 0.4271 0.112 Uiso 1 1 calc R U . . .
C25 C 0.68416(15) 0.6429(2) 0.4960(2) 0.0772(9) Uani 1 1 d . . . . .
H25 H 0.6998 0.6082 0.4703 0.093 Uiso 1 1 calc R U . . .
C7 C 0.78466(15) 0.33159(19) 0.68794(17) 0.0683(8) Uani 1 1 d . . . . .
H7A H 0.8273 0.3563 0.7390 0.082 Uiso 1 1 calc R U . . .
H7B H 0.7454 0.3503 0.6880 0.082 Uiso 1 1 calc R U . . .
C8 C 0.78904(17) 0.2289(2) 0.69058(19) 0.0752(9) Uani 1 1 d . . . . .
C9 C 0.72503(16) 0.1722(2) 0.63696(18) 0.0682(8) Uani 1 1 d . . . . .
C10 C 0.7321(2) 0.0780(3) 0.6381(2) 0.0911(10) Uani 1 1 d . . . . .
H10 H 0.7768 0.0521 0.6723 0.109 Uiso 1 1 calc R U . . .
C11 C 0.6756(3) 0.0224(3) 0.5907(3) 0.1140(13) Uani 1 1 d . . . . .
H11 H 0.6820 -0.0409 0.5926 0.137 Uiso 1 1 calc R U . . .
C12 C 0.6088(2) 0.0580(3) 0.5400(3) 0.1032(12) Uani 1 1 d . . . . .
H12 H 0.5700 0.0195 0.5075 0.124 Uiso 1 1 calc R U . . .
C13 C 0.60010(19) 0.1516(3) 0.5379(2) 0.0971(11) Uani 1 1 d . . . . .
H13 H 0.5552 0.1770 0.5036 0.116 Uiso 1 1 calc R U . . .
C14 C 0.65810(18) 0.2078(2) 0.5866(2) 0.0809(9) Uani 1 1 d . . . . .
H14 H 0.6518 0.2710 0.5854 0.097 Uiso 1 1 calc R U . . .
C15 C 0.85107(14) 0.5451(2) 0.74390(17) 0.0690(8) Uani 1 1 d . . . . .
H15A H 0.8126 0.5689 0.7435 0.083 Uiso 1 1 calc R U . . .
H15B H 0.8641 0.4856 0.7717 0.083 Uiso 1 1 calc R U . . .
C16 C 0.91324(16) 0.6094(2) 0.79499(19) 0.0737(9) Uani 1 1 d . . . . .
C17 C 0.90527(15) 0.7094(2) 0.78012(18) 0.0708(8) Uani 1 1 d . . . . .
C22 C 0.84099(16) 0.7531(3) 0.7313(2) 0.0839(10) Uani 1 1 d . . . . .
H22 H 0.7999 0.7185 0.7043 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8366(2) 0.8469(3) 0.7220(2) 0.1040(12) Uani 1 1 d . . . . .
H21 H 0.7927 0.8752 0.6895 0.125 Uiso 1 1 calc R U . . .
C20 C 0.8958(3) 0.8989(3) 0.7597(3) 0.1211(14) Uani 1 1 d . . . . .
H20 H 0.8925 0.9623 0.7521 0.145 Uiso 1 1 calc R U . . .
C19 C 0.9594(3) 0.8579(4) 0.8082(3) 0.1335(16) Uani 1 1 d . . . . .
H19 H 1.0001 0.8934 0.8351 0.160 Uiso 1 1 calc R U . . .
C18 C 0.96468(18) 0.7645(3) 0.8182(2) 0.1096(13) Uani 1 1 d . . . . .
H18 H 1.0090 0.7373 0.8512 0.132 Uiso 1 1 calc R U . . .


_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 C8 1.216(3) . ?
O2 C16 1.225(3) . ?
N1 C23 1.456(3) . ?
N1 C6 1.469(3) . ?
N1 C2 1.477(3) . ?
C4 C3 1.508(4) . ?
C4 C5 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.520(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.553(4) . ?
C6 H6 0.9800 . ?
C2 C3 1.516(4) . ?
C2 C15 1.548(4) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C23 C30 1.522(4) . ?
C23 C24 1.523(4) . ?
C23 H23 0.9800 . ?
C30 C35 1.372(4) . ?
C30 C31 1.380(4) . ?
C31 C32 1.391(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.348(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.382(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C24 C29 1.367(4) . ?
C24 C25 1.381(4) . ?
C29 C28 1.387(4) . ?
C29 H29 0.9300 . ?
C28 C27 1.361(5) . ?
C28 H28 0.9300 . ?
C27 C26 1.363(5) . ?
C27 H27 0.9300 . ?
C26 C25 1.378(4) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C7 C8 1.497(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.476(4) . ?
C9 C14 1.373(4) . ?
C9 C10 1.380(4) . ?
C10 C11 1.349(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.510(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.474(4) . ?
C17 C22 1.377(4) . ?
C17 C18 1.387(4) . ?
C22 C21 1.373(5) . ?
C22 H22 0.9300 . ?
C21 C20 1.359(5) . ?
C21 H21 0.9300 . ?
C20 C19 1.348(6) . ?
C20 H20 0.9300 . ?
C19 C18 1.369(6) . ?
C19 H19 0.9300 . ?
C18 H18 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
C23 N1 C6 114.2(2) . . ?
C23 N1 C2 115.3(2) . . ?
C6 N1 C2 117.6(2) . . ?
C3 C4 C5 108.9(3) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 C6 112.2(2) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 109.8(2) . . ?
N1 C6 C7 115.9(2) . . ?
C5 C6 C7 112.4(2) . . ?
N1 C6 H6 106.0 . . ?
C5 C6 H6 106.0 . . ?
C7 C6 H6 106.0 . . ?
N1 C2 C3 109.4(2) . . ?
N1 C2 C15 115.6(2) . . ?
C3 C2 C15 112.6(2) . . ?
N1 C2 H2 106.2 . . ?
C3 C2 H2 106.2 . . ?
C15 C2 H2 106.2 . . ?
C4 C3 C2 113.1(2) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C23 C30 112.3(2) . . ?
N1 C23 C24 113.3(2) . . ?
C30 C23 C24 106.1(2) . . ?
N1 C23 H23 108.3 . . ?
C30 C23 H23 108.3 . . ?
C24 C23 H23 108.3 . . ?
C35 C30 C31 119.6(3) . . ?
C35 C30 C23 118.8(3) . . ?
C31 C30 C23 121.4(3) . . ?
C30 C31 C32 120.0(4) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 119.3(5) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C34 C33 C32 120.7(5) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 120.7(6) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C30 C35 C34 119.8(5) . . ?
C30 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C29 C24 C25 118.4(3) . . ?
C29 C24 C23 119.1(3) . . ?
C25 C24 C23 122.1(3) . . ?
C24 C29 C28 121.2(3) . . ?
C24 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C27 C28 C29 119.6(3) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C26 C25 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C8 C7 C6 112.7(2) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C9 119.5(3) . . ?
O1 C8 C7 119.7(3) . . ?
C9 C8 C7 120.9(3) . . ?
C14 C9 C10 117.6(3) . . ?
C14 C9 C8 123.6(3) . . ?
C10 C9 C8 118.8(3) . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 121.2(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C2 113.0(2) . . ?
C16 C15 H15A 109.0 . . ?
C2 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C2 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O2 C16 C17 120.1(3) . . ?
O2 C16 C15 118.4(3) . . ?
C17 C16 C15 121.4(3) . . ?
C22 C17 C18 116.9(3) . . ?
C22 C17 C16 123.4(3) . . ?
C18 C17 C16 119.7(3) . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C20 C21 C22 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C19 C20 C21 119.5(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C18 C17 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?

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
C3 C4 C5 C6 -56.6(3) . . . . ?
C23 N1 C6 C5 168.7(2) . . . . ?
C2 N1 C6 C5 -51.5(3) . . . . ?
C23 N1 C6 C7 -62.6(3) . . . . ?
C2 N1 C6 C7 77.2(3) . . . . ?
C4 C5 C6 N1 53.2(3) . . . . ?
C4 C5 C6 C7 -77.5(3) . . . . ?
C23 N1 C2 C3 -169.7(2) . . . . ?
C6 N1 C2 C3 50.8(3) . . . . ?
C23 N1 C2 C15 61.9(3) . . . . ?
C6 N1 C2 C15 -77.5(3) . . . . ?
C5 C4 C3 C2 56.7(3) . . . . ?
N1 C2 C3 C4 -52.5(3) . . . . ?
C15 C2 C3 C4 77.5(3) . . . . ?
C6 N1 C23 C30 -51.7(3) . . . . ?
C2 N1 C23 C30 167.4(2) . . . . ?
C6 N1 C23 C24 -172.0(2) . . . . ?
C2 N1 C23 C24 47.2(3) . . . . ?
N1 C23 C30 C35 144.5(3) . . . . ?
C24 C23 C30 C35 -91.2(3) . . . . ?
N1 C23 C30 C31 -40.1(4) . . . . ?
C24 C23 C30 C31 84.2(3) . . . . ?
C35 C30 C31 C32 -1.4(5) . . . . ?
C23 C30 C31 C32 -176.8(3) . . . . ?
C30 C31 C32 C33 0.9(6) . . . . ?
C31 C32 C33 C34 0.7(8) . . . . ?
C32 C33 C34 C35 -1.8(9) . . . . ?
C31 C30 C35 C34 0.3(5) . . . . ?
C23 C30 C35 C34 175.8(3) . . . . ?
C33 C34 C35 C30 1.3(7) . . . . ?
N1 C23 C24 C29 -138.0(2) . . . . ?
C30 C23 C24 C29 98.4(3) . . . . ?
N1 C23 C24 C25 49.0(3) . . . . ?
C30 C23 C24 C25 -74.7(3) . . . . ?
C25 C24 C29 C28 0.5(4) . . . . ?
C23 C24 C29 C28 -172.8(2) . . . . ?
C24 C29 C28 C27 0.3(4) . . . . ?
C29 C28 C27 C26 -1.4(5) . . . . ?
C28 C27 C26 C25 1.8(5) . . . . ?
C27 C26 C25 C24 -1.0(5) . . . . ?
C29 C24 C25 C26 -0.1(4) . . . . ?
C23 C24 C25 C26 173.0(3) . . . . ?
N1 C6 C7 C8 174.4(2) . . . . ?
C5 C6 C7 C8 -58.2(3) . . . . ?
C6 C7 C8 O1 100.7(3) . . . . ?
C6 C7 C8 C9 -77.9(3) . . . . ?
O1 C8 C9 C14 176.7(3) . . . . ?
C7 C8 C9 C14 -4.7(4) . . . . ?
O1 C8 C9 C10 -2.1(4) . . . . ?
C7 C8 C9 C10 176.5(3) . . . . ?
C14 C9 C10 C11 0.9(5) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
C8 C9 C14 C13 -179.9(3) . . . . ?
C12 C13 C14 C9 0.8(5) . . . . ?
N1 C2 C15 C16 -178.5(2) . . . . ?
C3 C2 C15 C16 54.7(4) . . . . ?
C2 C15 C16 O2 -107.0(3) . . . . ?
C2 C15 C16 C17 72.5(3) . . . . ?
O2 C16 C17 C22 -168.5(3) . . . . ?
C15 C16 C17 C22 12.0(4) . . . . ?
O2 C16 C17 C18 9.8(5) . . . . ?
C15 C16 C17 C18 -169.7(3) . . . . ?
C18 C17 C22 C21 -0.6(5) . . . . ?
C16 C17 C22 C21 177.7(3) . . . . ?
C17 C22 C21 C20 1.0(6) . . . . ?
C22 C21 C20 C19 -1.4(7) . . . . ?
C21 C20 C19 C18 1.4(7) . . . . ?
C20 C19 C18 C17 -1.0(7) . . . . ?
C22 C17 C18 C19 0.6(6) . . . . ?
C16 C17 C18 C19 -177.8(4) . . . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 964827'
#######################################################################
#
#                 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_compound_cis-3a

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_absolute_configuration ?

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.421(2)
_cell_length_b                   11.015(3)
_cell_length_c                   28.258(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.740(4)
_cell_angle_gamma                90.00
_cell_volume                     1657.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3154
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      26.373

_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9647
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.469
_diffrn_reflns_theta_max         26.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3336
_reflns_number_gt                2141
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL2012 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0608P)²+0.1353P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_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_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 0.5684(2) 0.26887(11) 0.22803(5) 0.0798(4) Uani 1 1 d . . . . .
O2 O 0.4366(3) 0.35305(12) 0.07067(5) 0.0889(5) Uani 1 1 d . . . . .
N1 N 0.3278(2) 0.15623(13) 0.13564(5) 0.0558(4) Uani 1 1 d D . . . .
H1N H 0.410(3) 0.2256(11) 0.1420(6) 0.067 Uiso 1 1 d D U . . .
C2 C 0.1225(3) 0.17191(15) 0.09435(6) 0.0552(4) Uani 1 1 d . . . . .
H2 H 0.0394 0.2498 0.0974 0.066 Uiso 1 1 calc R U . . .
C3 C -0.0578(3) 0.06864(17) 0.10042(7) 0.0645(5) Uani 1 1 d . . . . .
H3A H -0.2300 0.0974 0.0945 0.077 Uiso 1 1 calc R U . . .
H3B H -0.0436 0.0030 0.0782 0.077 Uiso 1 1 calc R U . . .
C4 C 0.0198(3) 0.02601(17) 0.15221(7) 0.0641(5) Uani 1 1 d . . . . .
H4A H -0.1238 0.0237 0.1682 0.077 Uiso 1 1 calc R U . . .
H4B H 0.0937 -0.0544 0.1534 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2113(3) 0.11841(15) 0.17604(6) 0.0526(4) Uani 1 1 d . . . . .
H5 H 0.1241 0.1877 0.1872 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4037(3) 0.06982(14) 0.21729(6) 0.0516(4) Uani 1 1 d . . . . .
H6A H 0.3173 0.0380 0.2418 0.062 Uiso 1 1 calc R U . . .
H6B H 0.4925 0.0030 0.2057 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5921(3) 0.16306(15) 0.24000(6) 0.0531(4) Uani 1 1 d . . . . .
C8 C 0.8100(3) 0.12541(14) 0.27729(6) 0.0494(4) Uani 1 1 d . . . . .
C9 C 0.8328(3) 0.01119(16) 0.29768(7) 0.0661(5) Uani 1 1 d . . . . .
H9 H 0.7082 -0.0465 0.2882 0.079 Uiso 1 1 calc R U . . .
C10 C 1.0403(4) -0.01769(18) 0.33221(8) 0.0794(6) Uani 1 1 d . . . . .
H10 H 1.0538 -0.0949 0.3458 0.095 Uiso 1 1 calc R U . . .
C11 C 1.2252(3) 0.06526(19) 0.34668(7) 0.0737(5) Uani 1 1 d . . . . .
H11 H 1.3637 0.0450 0.3700 0.088 Uiso 1 1 calc R U . . .
C12 C 1.2057(3) 0.17886(18) 0.32656(7) 0.0675(5) Uani 1 1 d . . . . .
H12 H 1.3319 0.2358 0.3361 0.081 Uiso 1 1 calc R U . . .
C13 C 0.9995(3) 0.20899(15) 0.29214(6) 0.0577(4) Uani 1 1 d . . . . .
H13 H 0.9875 0.2864 0.2787 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2180(3) 0.17011(15) 0.04770(6) 0.0537(4) Uani 1 1 d . . . . .
H14A H 0.0752 0.1742 0.0213 0.064 Uiso 1 1 calc R U . . .
H14B H 0.3014 0.0931 0.0452 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3975(3) 0.27111(15) 0.04157(6) 0.0562(4) Uani 1 1 d . . . . .
C16 C 0.5263(3) 0.26967(14) -0.00060(6) 0.0508(4) Uani 1 1 d . . . . .
C17 C 0.4956(3) 0.17552(15) -0.03375(6) 0.0571(4) Uani 1 1 d . . . . .
H17 H 0.3902 0.1111 -0.0300 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6187(3) 0.17589(18) -0.07219(7) 0.0668(5) Uani 1 1 d . . . . .
H18 H 0.5964 0.1120 -0.0941 0.080 Uiso 1 1 calc R U . . .
C19 C 0.7743(3) 0.27063(19) -0.07820(8) 0.0726(5) Uani 1 1 d . . . . .
H19 H 0.8584 0.2707 -0.1040 0.087 Uiso 1 1 calc R U . . .
C20 C 0.8054(3) 0.36484(19) -0.04618(8) 0.0757(6) Uani 1 1 d . . . . .
H20 H 0.9091 0.4295 -0.0506 0.091 Uiso 1 1 calc R U . . .
C21 C 0.6840(3) 0.36462(16) -0.00740(7) 0.0662(5) Uani 1 1 d . . . . .
H21 H 0.7082 0.4287 0.0144 0.079 Uiso 1 1 calc R U . . .


_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 C7 1.2137(19) . ?
O2 C15 1.213(2) . ?
N1 C5 1.464(2) . ?
N1 C2 1.465(2) . ?
N1 H1N 0.886(9) . ?
C2 C14 1.504(2) . ?
C2 C3 1.530(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.510(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.505(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.488(2) . ?
C8 C9 1.380(2) . ?
C8 C13 1.385(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.509(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.489(2) . ?
C16 C17 1.387(2) . ?
C16 C21 1.387(2) . ?
C17 C18 1.377(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C5 N1 C2 106.28(12) . . ?
C5 N1 H1N 111.2(12) . . ?
C2 N1 H1N 109.8(12) . . ?
N1 C2 C14 111.23(12) . . ?
N1 C2 C3 103.27(13) . . ?
C14 C2 C3 114.83(14) . . ?
N1 C2 H2 109.1 . . ?
C14 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C4 C3 C2 105.63(13) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 105.30(14) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C6 111.49(12) . . ?
N1 C5 C4 101.74(13) . . ?
C6 C5 C4 114.93(14) . . ?
N1 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C7 C6 C5 113.79(14) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 C8 119.61(15) . . ?
O1 C7 C6 120.54(15) . . ?
C8 C7 C6 119.85(14) . . ?
C9 C8 C13 118.42(15) . . ?
C9 C8 C7 123.19(15) . . ?
C13 C8 C7 118.38(14) . . ?
C8 C9 C10 120.17(17) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.96(18) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.51(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.14(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.79(17) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C2 C14 C15 115.19(14) . . ?
C2 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C2 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O2 C15 C16 120.12(16) . . ?
O2 C15 C14 120.37(16) . . ?
C16 C15 C14 119.51(14) . . ?
C17 C16 C21 118.03(17) . . ?
C17 C16 C15 122.24(15) . . ?
C21 C16 C15 119.74(16) . . ?
C18 C17 C16 121.06(16) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 119.97(18) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.90(18) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.42(18) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.61(18) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

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
C5 N1 C2 C14 -161.25(13) . . . . ?
C5 N1 C2 C3 -37.57(16) . . . . ?
N1 C2 C3 C4 16.60(17) . . . . ?
C14 C2 C3 C4 137.88(14) . . . . ?
C2 C3 C4 C5 8.90(18) . . . . ?
C2 N1 C5 C6 166.08(13) . . . . ?
C2 N1 C5 C4 43.09(16) . . . . ?
C3 C4 C5 N1 -30.95(16) . . . . ?
C3 C4 C5 C6 -151.57(14) . . . . ?
N1 C5 C6 C7 64.49(18) . . . . ?
C4 C5 C6 C7 179.59(13) . . . . ?
C5 C6 C7 O1 6.7(2) . . . . ?
C5 C6 C7 C8 -173.05(13) . . . . ?
O1 C7 C8 C9 170.75(17) . . . . ?
C6 C7 C8 C9 -9.5(2) . . . . ?
O1 C7 C8 C13 -9.5(2) . . . . ?
C6 C7 C8 C13 170.32(14) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C10 -179.94(17) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
C7 C8 C13 C12 -179.95(15) . . . . ?
N1 C2 C14 C15 -62.73(18) . . . . ?
C3 C2 C14 C15 -179.55(13) . . . . ?
C2 C14 C15 O2 -7.3(2) . . . . ?
C2 C14 C15 C16 172.87(13) . . . . ?
O2 C15 C16 C17 177.32(15) . . . . ?
C14 C15 C16 C17 -2.8(2) . . . . ?
O2 C15 C16 C21 -2.3(2) . . . . ?
C14 C15 C16 C21 177.54(14) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
C15 C16 C17 C18 -179.40(15) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C17 C16 C21 C20 0.2(2) . . . . ?
C15 C16 C21 C20 179.86(16) . . . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032

_shelxl_version_number           2012-9



#===END





_database_code_depnum_ccdc_archive 'CCDC 964828'
