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

#######################################################################
#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
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data_demb25
#TrackingRef 'DEMB25_pub.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   10.2819(9)
_cell_length_b                   10.7707(9)
_cell_length_c                   15.6284(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1730.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6015
_cell_measurement_theta_min      4.104
_cell_measurement_theta_max      66.564

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28483
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.99
_diffrn_reflns_theta_max         67.79
_reflns_number_total             3134
_reflns_number_gt                2901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

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

All nonhydrogen atoms were located in a difference Fourier electron
density map and refined using anisotropic diplacement parameters. All C-H
hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
(1.5Ueq for methyl groups) of the connected C atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.8657P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_number_reflns         3134
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09895(16) 0.34660(15) -0.05585(10) 0.0253(4) Uani 1 1 d . . .
N5 N 0.04255(19) 0.24263(16) 0.12135(11) 0.0334(4) Uani 1 1 d . . .
C2 C 0.02118(19) 0.25550(18) -0.07123(12) 0.0253(4) Uani 1 1 d . . .
C3 C -0.0884(2) 0.22553(19) -0.00934(13) 0.0293(5) Uani 1 1 d . . .
H3A H -0.1391 0.3012 0.0040 0.035 Uiso 1 1 calc R . .
H3B H -0.1478 0.1630 -0.0344 0.035 Uiso 1 1 calc R . .
C4 C -0.0250(2) 0.17530(19) 0.07024(13) 0.0306(5) Uani 1 1 d . . .
C6 C 0.0752(2) 0.4487(2) 0.17291(13) 0.0337(5) Uani 1 1 d . . .
H6 H 0.0630 0.4162 0.2288 0.040 Uiso 1 1 calc R . .
C7 C 0.1022(2) 0.5727(2) 0.16363(14) 0.0355(5) Uani 1 1 d . . .
H7 H 0.1050 0.6255 0.2123 0.043 Uiso 1 1 calc R . .
C8 C 0.1253(2) 0.62057(19) 0.08216(14) 0.0330(5) Uani 1 1 d . . .
H8 H 0.1430 0.7065 0.0749 0.040 Uiso 1 1 calc R . .
C9 C 0.12247(19) 0.54309(19) 0.01239(14) 0.0297(5) Uani 1 1 d . . .
H9 H 0.1430 0.5757 -0.0424 0.036 Uiso 1 1 calc R . .
C10 C 0.09021(18) 0.41754(18) 0.01989(13) 0.0268(4) Uani 1 1 d . . .
C11 C 0.0652(2) 0.36822(19) 0.10250(13) 0.0291(5) Uani 1 1 d . . .
C12 C 0.04160(19) 0.17893(18) -0.14856(12) 0.0266(4) Uani 1 1 d . . .
C13 C -0.0563(2) 0.1055(2) -0.18332(13) 0.0326(5) Uani 1 1 d . . .
H13 H -0.1392 0.1036 -0.1566 0.039 Uiso 1 1 calc R . .
C14 C -0.0352(2) 0.0351(2) -0.25626(14) 0.0376(5) Uani 1 1 d . . .
H14 H -0.1035 -0.0141 -0.2792 0.045 Uiso 1 1 calc R . .
C15 C 0.0853(2) 0.0364(2) -0.29569(14) 0.0390(5) Uani 1 1 d . . .
H15 H 0.1004 -0.0120 -0.3455 0.047 Uiso 1 1 calc R . .
C16 C 0.1841(2) 0.1093(2) -0.26169(15) 0.0411(6) Uani 1 1 d . . .
H16 H 0.2670 0.1107 -0.2886 0.049 Uiso 1 1 calc R . .
C17 C 0.1632(2) 0.1797(2) -0.18920(14) 0.0348(5) Uani 1 1 d . . .
H17 H 0.2316 0.2291 -0.1667 0.042 Uiso 1 1 calc R . .
C18 C -0.0352(3) 0.0376(2) 0.08876(14) 0.0386(5) Uani 1 1 d . . .
H18A H -0.1273 0.0113 0.0855 0.046 Uiso 1 1 calc R . .
H18B H -0.0031 0.0204 0.1473 0.046 Uiso 1 1 calc R . .
C19 C 0.0447(2) -0.03475(18) 0.02427(13) 0.0303(5) Uani 1 1 d . . .
C20 C -0.0119(2) -0.11293(19) -0.03601(14) 0.0331(5) Uani 1 1 d . . .
H20 H -0.1035 -0.1249 -0.0359 0.040 Uiso 1 1 calc R . .
C21 C 0.0644(2) -0.1737(2) -0.09647(14) 0.0343(5) Uani 1 1 d . . .
H21 H 0.0241 -0.2270 -0.1370 0.041 Uiso 1 1 calc R . .
C22 C 0.2809(2) -0.2215(2) -0.16496(16) 0.0422(6) Uani 1 1 d . . .
H22A H 0.2335 -0.2929 -0.1882 0.063 Uiso 1 1 calc R . .
H22C H 0.3620 -0.2501 -0.1386 0.063 Uiso 1 1 calc R . .
H22B H 0.3009 -0.1632 -0.2112 0.063 Uiso 1 1 calc R . .
C23 C 0.1984(2) -0.15780(19) -0.09876(14) 0.0337(5) Uani 1 1 d . . .
C24 C 0.2545(2) -0.0808(2) -0.03773(15) 0.0362(5) Uani 1 1 d . . .
H24 H 0.3462 -0.0697 -0.0372 0.043 Uiso 1 1 calc R . .
C25 C 0.1788(2) -0.0198(2) 0.02238(14) 0.0350(5) Uani 1 1 d . . .
H25 H 0.2194 0.0332 0.0630 0.042 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0250(8) 0.0250(8) 0.0258(8) 0.0019(7) -0.0008(6) 0.0027(6)
N5 0.0459(10) 0.0271(8) 0.0274(8) -0.0006(7) 0.0025(8) 0.0059(8)
C2 0.0246(9) 0.0238(9) 0.0276(9) 0.0044(8) -0.0016(8) 0.0049(8)
C3 0.0303(10) 0.0247(9) 0.0329(10) -0.0018(8) 0.0051(8) 0.0001(8)
C4 0.0372(11) 0.0276(9) 0.0270(10) 0.0006(9) 0.0056(8) 0.0019(9)
C6 0.0414(11) 0.0307(10) 0.0291(10) -0.0027(9) -0.0026(9) 0.0086(9)
C7 0.0368(11) 0.0313(10) 0.0385(11) -0.0096(9) -0.0054(9) 0.0039(9)
C8 0.0316(10) 0.0252(10) 0.0421(11) -0.0030(9) -0.0017(9) 0.0007(9)
C9 0.0260(9) 0.0286(10) 0.0346(10) 0.0000(9) 0.0016(8) 0.0007(8)
C10 0.0231(9) 0.0265(9) 0.0309(9) -0.0005(8) -0.0011(8) 0.0054(8)
C11 0.0314(10) 0.0257(10) 0.0301(10) -0.0009(8) -0.0028(8) 0.0052(8)
C12 0.0297(9) 0.0256(9) 0.0245(9) 0.0038(8) -0.0038(8) 0.0021(8)
C13 0.0333(10) 0.0324(10) 0.0320(10) 0.0018(9) -0.0009(8) -0.0023(9)
C14 0.0441(12) 0.0357(11) 0.0328(10) -0.0029(10) -0.0060(9) -0.0075(10)
C15 0.0501(13) 0.0341(11) 0.0326(10) -0.0071(10) -0.0016(10) 0.0046(10)
C16 0.0361(11) 0.0495(14) 0.0375(11) -0.0061(11) 0.0038(10) 0.0020(11)
C17 0.0311(11) 0.0409(12) 0.0325(10) -0.0059(10) -0.0008(9) -0.0016(10)
C18 0.0594(14) 0.0253(10) 0.0310(10) 0.0025(9) 0.0086(10) 0.0015(10)
C19 0.0411(11) 0.0195(9) 0.0304(10) 0.0058(8) 0.0006(9) 0.0025(9)
C20 0.0344(11) 0.0258(10) 0.0390(11) 0.0010(9) -0.0038(9) 0.0024(9)
C21 0.0376(11) 0.0280(10) 0.0373(11) -0.0038(9) -0.0045(9) 0.0032(9)
C22 0.0394(12) 0.0382(12) 0.0491(13) -0.0046(11) 0.0077(11) -0.0008(10)
C23 0.0384(11) 0.0235(10) 0.0390(11) -0.0004(9) 0.0011(9) -0.0007(9)
C24 0.0346(11) 0.0289(10) 0.0453(12) 0.0020(9) -0.0014(9) -0.0052(9)
C25 0.0449(12) 0.0252(10) 0.0348(10) -0.0002(9) -0.0058(10) -0.0087(9)

_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 C2 1.288(3) . ?
N1 C10 1.412(3) . ?
N5 C4 1.283(3) . ?
N5 C11 1.404(3) . ?
C2 C12 1.478(3) . ?
C2 C3 1.520(3) . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C18 1.515(3) . ?
C6 C7 1.371(3) . ?
C6 C11 1.405(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.420(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.402(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.516(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C25 1.389(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C23 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.504(3) . ?
C22 H22A 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.389(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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 C10 121.95(17) . . ?
C4 N5 C11 120.25(18) . . ?
N1 C2 C12 119.30(18) . . ?
N1 C2 C3 120.21(18) . . ?
C12 C2 C3 120.48(17) . . ?
C4 C3 C2 106.32(16) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N5 C4 C3 123.08(19) . . ?
N5 C4 C18 118.17(19) . . ?
C3 C4 C18 118.67(18) . . ?
C7 C6 C11 122.2(2) . . ?
C7 C6 H6 118.9 . . ?
C11 C6 H6 118.9 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 119.78(19) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 N1 116.00(18) . . ?
C9 C10 C11 118.78(19) . . ?
N1 C10 C11 124.86(17) . . ?
N5 C11 C6 116.26(18) . . ?
N5 C11 C10 125.55(18) . . ?
C6 C11 C10 117.92(19) . . ?
C13 C12 C17 118.14(19) . . ?
C13 C12 C2 122.28(18) . . ?
C17 C12 C2 119.58(18) . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C4 C18 C19 109.79(18) . . ?
C4 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
C4 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C25 C19 C20 118.1(2) . . ?
C25 C19 C18 119.5(2) . . ?
C20 C19 C18 122.3(2) . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C23 C21 C20 121.3(2) . . ?
C23 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
C21 C23 C24 117.9(2) . . ?
C21 C23 C22 121.4(2) . . ?
C24 C23 C22 120.7(2) . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C19 121.1(2) . . ?
C24 C25 H25 119.4 . . ?
C19 C25 H25 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C12 -175.43(17) . . . . ?
C10 N1 C2 C3 3.2(3) . . . . ?
N1 C2 C3 C4 -69.5(2) . . . . ?
C12 C2 C3 C4 109.12(19) . . . . ?
C11 N5 C4 C3 -2.8(3) . . . . ?
C11 N5 C4 C18 173.92(19) . . . . ?
C2 C3 C4 N5 69.7(2) . . . . ?
C2 C3 C4 C18 -107.0(2) . . . . ?
C11 C6 C7 C8 -2.5(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 3.4(3) . . . . ?
C8 C9 C10 N1 -176.13(18) . . . . ?
C8 C9 C10 C11 -2.7(3) . . . . ?
C2 N1 C10 C9 -146.61(18) . . . . ?
C2 N1 C10 C11 40.4(3) . . . . ?
C4 N5 C11 C6 147.5(2) . . . . ?
C4 N5 C11 C10 -38.5(3) . . . . ?
C7 C6 C11 N5 177.5(2) . . . . ?
C7 C6 C11 C10 3.0(3) . . . . ?
C9 C10 C11 N5 -174.3(2) . . . . ?
N1 C10 C11 N5 -1.5(3) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
N1 C10 C11 C6 172.34(19) . . . . ?
N1 C2 C12 C13 -160.24(19) . . . . ?
C3 C2 C12 C13 21.1(3) . . . . ?
N1 C2 C12 C17 19.5(3) . . . . ?
C3 C2 C12 C17 -159.11(19) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C2 C12 C13 C14 179.54(19) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C2 C12 C17 C16 -179.7(2) . . . . ?
N5 C4 C18 C19 -107.6(2) . . . . ?
C3 C4 C18 C19 69.3(3) . . . . ?
C4 C18 C19 C25 64.4(3) . . . . ?
C4 C18 C19 C20 -113.0(2) . . . . ?
C25 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 C21 177.26(19) . . . . ?
C19 C20 C21 C23 -0.3(3) . . . . ?
C20 C21 C23 C24 1.1(3) . . . . ?
C20 C21 C23 C22 -178.9(2) . . . . ?
C21 C23 C24 C25 -1.3(3) . . . . ?
C22 C23 C24 C25 178.7(2) . . . . ?
C23 C24 C25 C19 0.7(3) . . . . ?
C20 C19 C25 C24 0.0(3) . . . . ?
C18 C19 C25 C24 -177.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.79
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 929588'
#######################################################################
#
#                 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_demb30

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (Z)-3-[(2-amino-4,5-dimethylphenyl)amino]-4-
 (4-tert-butylphenyl)-1-(4-chlorophenyl)but-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 Cl N2 O'
_chemical_formula_sum            'C28 H31 Cl N2 O'
_chemical_formula_weight         447.00

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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.7713(9)
_cell_length_b                   16.573(2)
_cell_length_c                   25.145(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.354(8)
_cell_angle_gamma                90.00
_cell_volume                     2403.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6787
_cell_measurement_theta_min      3.152
_cell_measurement_theta_max      67.739

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_T_max  0.9090
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26321
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         67.58
_reflns_number_total             4215
_reflns_number_gt                2948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

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

 All nonhydrogen atoms were located in a difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.  The N-H hydrogen atom
 were initially located in a diff map, then fixed by use of AFIX commands, 
 and refined isotropically with Uiso = 1.2xUeqiv and restrained to 0.84(2)
 ang. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.4186P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4215
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28707(8) 0.84136(2) 0.218680(16) 0.03336(11) Uani 1 1 d . . .
O1 O 0.05067(19) 0.52180(7) 0.06673(4) 0.0317(3) Uani 1 1 d . . .
N1 N -0.2376(2) 0.39750(8) 0.05761(5) 0.0277(3) Uani 1 1 d . . .
H1 H -0.1269 0.4261 0.0436 0.033 Uiso 1 1 calc R . .
N2 N -0.6757(3) 0.40192(10) 0.00292(6) 0.0498(5) Uani 1 1 d . . .
H2A H -0.6280 0.4438 0.0219 0.060 Uiso 1 1 calc R . .
H2B H -0.8109 0.4034 -0.0146 0.060 Uiso 1 1 calc R . .
C1 C -0.0426(3) 0.53734(9) 0.10995(6) 0.0251(4) Uani 1 1 d . . .
C2 C -0.2196(3) 0.48815(9) 0.13039(6) 0.0254(4) Uani 1 1 d . . .
H2 H -0.2793 0.5025 0.1638 0.030 Uiso 1 1 calc R . .
C3 C -0.3101(3) 0.42114(9) 0.10501(6) 0.0240(4) Uani 1 1 d . . .
C4 C -0.4884(3) 0.36915(9) 0.13084(6) 0.0249(4) Uani 1 1 d . . .
H4A H -0.6235 0.3616 0.1058 0.030 Uiso 1 1 calc R . .
H4B H -0.5429 0.3968 0.1629 0.030 Uiso 1 1 calc R . .
C5 C 0.0370(3) 0.61166(9) 0.13916(6) 0.0237(4) Uani 1 1 d . . .
C6 C -0.0910(3) 0.64846(10) 0.17805(6) 0.0273(4) Uani 1 1 d . . .
H6 H -0.2330 0.6248 0.1878 0.033 Uiso 1 1 calc R . .
C7 C -0.0157(3) 0.71890(10) 0.20286(7) 0.0285(4) Uani 1 1 d . . .
H7 H -0.1046 0.7436 0.2293 0.034 Uiso 1 1 calc R . .
C8 C 0.1902(3) 0.75225(9) 0.18838(6) 0.0253(4) Uani 1 1 d . . .
C9 C 0.3220(3) 0.71719(10) 0.15033(6) 0.0286(4) Uani 1 1 d . . .
H9 H 0.4650 0.7407 0.1412 0.034 Uiso 1 1 calc R . .
C10 C 0.2434(3) 0.64727(10) 0.12560(6) 0.0271(4) Uani 1 1 d . . .
H10 H 0.3326 0.6233 0.0989 0.033 Uiso 1 1 calc R . .
C11 C -0.3893(3) 0.28756(9) 0.14647(6) 0.0227(4) Uani 1 1 d . . .
C12 C -0.4984(3) 0.21606(9) 0.13147(6) 0.0260(4) Uani 1 1 d . . .
H12 H -0.6427 0.2179 0.1119 0.031 Uiso 1 1 calc R . .
C13 C -0.4003(3) 0.14202(10) 0.14459(6) 0.0264(4) Uani 1 1 d . . .
H13 H -0.4783 0.0941 0.1333 0.032 Uiso 1 1 calc R . .
C14 C -0.1910(3) 0.13568(9) 0.17377(6) 0.0228(4) Uani 1 1 d . . .
C15 C -0.0825(3) 0.20777(9) 0.18853(6) 0.0264(4) Uani 1 1 d . . .
H15 H 0.0611 0.2062 0.2084 0.032 Uiso 1 1 calc R . .
C16 C -0.1797(3) 0.28172(10) 0.17485(6) 0.0271(4) Uani 1 1 d . . .
H16 H -0.1002 0.3297 0.1853 0.033 Uiso 1 1 calc R . .
C17 C -0.0843(3) 0.05299(9) 0.18643(6) 0.0228(4) Uani 1 1 d . . .
C18 C 0.0127(3) 0.01880(10) 0.13521(6) 0.0287(4) Uani 1 1 d . . .
H18A H -0.1140 0.0117 0.1085 0.043 Uiso 1 1 calc R . .
H18B H 0.0865 -0.0334 0.1428 0.043 Uiso 1 1 calc R . .
H18C H 0.1274 0.0563 0.1216 0.043 Uiso 1 1 calc R . .
C19 C -0.2670(3) -0.00588(10) 0.20632(7) 0.0286(4) Uani 1 1 d . . .
H19A H -0.3360 0.0164 0.2381 0.043 Uiso 1 1 calc R . .
H19B H -0.1933 -0.0577 0.2151 0.043 Uiso 1 1 calc R . .
H19C H -0.3883 -0.0139 0.1784 0.043 Uiso 1 1 calc R . .
C20 C 0.1134(3) 0.05875(10) 0.22915(6) 0.0269(4) Uani 1 1 d . . .
H20A H 0.2394 0.0917 0.2157 0.040 Uiso 1 1 calc R . .
H20B H 0.1717 0.0045 0.2376 0.040 Uiso 1 1 calc R . .
H20C H 0.0553 0.0837 0.2613 0.040 Uiso 1 1 calc R . .
C21 C -0.3248(3) 0.32961(9) 0.02760(6) 0.0254(4) Uani 1 1 d . . .
C22 C -0.5387(3) 0.33401(10) 0.00053(6) 0.0285(4) Uani 1 1 d . . .
C23 C -0.6120(3) 0.26650(11) -0.02904(6) 0.0322(5) Uani 1 1 d . . .
H23 H -0.7583 0.2681 -0.0478 0.039 Uiso 1 1 calc R . .
C24 C -0.4781(3) 0.19727(10) -0.03190(7) 0.0307(4) Uani 1 1 d . . .
C25 C -0.2640(3) 0.19348(10) -0.00425(6) 0.0286(4) Uani 1 1 d . . .
C26 C -0.1905(3) 0.26037(10) 0.02478(6) 0.0267(4) Uani 1 1 d . . .
H26 H -0.0438 0.2588 0.0433 0.032 Uiso 1 1 calc R . .
C27 C -0.5631(3) 0.12699(11) -0.06598(8) 0.0434(5) Uani 1 1 d . . .
H28A H -0.7113 0.1412 -0.0840 0.065 Uiso 1 1 calc R . .
H28B H -0.5842 0.0796 -0.0434 0.065 Uiso 1 1 calc R . .
H28C H -0.4487 0.1148 -0.0926 0.065 Uiso 1 1 calc R . .
C28 C -0.1184(3) 0.11767(10) -0.00472(8) 0.0411(5) Uani 1 1 d . . .
H27A H 0.0299 0.1274 0.0146 0.062 Uiso 1 1 calc R . .
H27B H -0.0898 0.1027 -0.0416 0.062 Uiso 1 1 calc R . .
H27C H -0.2008 0.0738 0.0125 0.062 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0424(2) 0.0213(2) 0.0357(2) -0.00141(19) -0.00562(18) -0.00396(18)
O1 0.0386(7) 0.0305(6) 0.0268(6) -0.0063(5) 0.0118(5) -0.0055(5)
N1 0.0337(8) 0.0233(7) 0.0269(7) -0.0042(6) 0.0123(6) -0.0070(6)
N2 0.0500(10) 0.0479(10) 0.0507(10) -0.0171(9) -0.0084(8) 0.0193(8)
C1 0.0293(9) 0.0233(8) 0.0227(8) -0.0003(7) 0.0020(7) 0.0020(7)
C2 0.0325(9) 0.0226(8) 0.0216(8) -0.0011(7) 0.0067(7) 0.0007(7)
C3 0.0295(9) 0.0195(8) 0.0233(8) 0.0000(7) 0.0046(7) 0.0027(7)
C4 0.0299(9) 0.0230(8) 0.0223(8) -0.0023(7) 0.0057(7) -0.0002(7)
C5 0.0289(9) 0.0217(8) 0.0203(8) 0.0026(7) -0.0004(7) 0.0008(7)
C6 0.0265(9) 0.0242(9) 0.0315(9) -0.0002(8) 0.0059(7) -0.0026(7)
C7 0.0309(10) 0.0239(9) 0.0308(9) -0.0042(8) 0.0041(7) 0.0015(7)
C8 0.0316(9) 0.0186(8) 0.0253(8) 0.0019(7) -0.0049(7) 0.0003(7)
C9 0.0315(9) 0.0267(9) 0.0276(8) 0.0043(8) 0.0019(7) -0.0035(8)
C10 0.0292(9) 0.0282(9) 0.0244(8) -0.0007(8) 0.0060(7) -0.0009(8)
C11 0.0245(8) 0.0232(8) 0.0211(8) 0.0001(7) 0.0078(6) -0.0008(7)
C12 0.0236(9) 0.0266(9) 0.0278(8) 0.0019(8) 0.0006(7) -0.0029(7)
C13 0.0243(9) 0.0229(9) 0.0322(9) -0.0015(8) 0.0014(7) -0.0052(7)
C14 0.0233(8) 0.0236(8) 0.0220(8) -0.0009(7) 0.0058(7) -0.0019(7)
C15 0.0268(9) 0.0252(9) 0.0272(9) -0.0006(8) -0.0004(7) -0.0018(7)
C16 0.0303(9) 0.0223(9) 0.0288(9) -0.0017(8) 0.0011(7) -0.0073(7)
C17 0.0228(8) 0.0205(8) 0.0251(8) -0.0020(7) 0.0014(7) -0.0007(7)
C18 0.0303(9) 0.0271(9) 0.0287(9) -0.0049(8) 0.0028(7) 0.0011(8)
C19 0.0268(9) 0.0241(9) 0.0350(10) 0.0032(8) 0.0009(7) -0.0024(7)
C20 0.0255(9) 0.0258(9) 0.0293(9) -0.0026(8) 0.0010(7) 0.0013(7)
C21 0.0322(9) 0.0212(9) 0.0235(8) -0.0030(7) 0.0104(7) -0.0042(7)
C22 0.0335(10) 0.0281(9) 0.0245(8) -0.0028(8) 0.0093(7) 0.0017(8)
C23 0.0291(10) 0.0404(11) 0.0277(9) -0.0045(8) 0.0057(7) -0.0044(8)
C24 0.0362(10) 0.0287(9) 0.0281(9) -0.0070(8) 0.0132(8) -0.0110(8)
C25 0.0371(10) 0.0231(8) 0.0264(9) -0.0035(7) 0.0134(7) -0.0044(8)
C26 0.0300(9) 0.0254(9) 0.0252(9) -0.0016(7) 0.0082(7) -0.0031(7)
C27 0.0498(12) 0.0407(11) 0.0404(10) -0.0137(9) 0.0112(9) -0.0151(9)
C28 0.0527(12) 0.0297(10) 0.0416(11) -0.0056(9) 0.0096(9) 0.0020(9)

_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
Cl1 C8 1.7433(16) . ?
O1 C1 1.2588(19) . ?
N1 C3 1.338(2) . ?
N1 C21 1.434(2) . ?
N1 H1 0.8800 . ?
N2 C22 1.378(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.420(2) . ?
C1 C5 1.496(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.509(2) . ?
C4 C11 1.514(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.385(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(2) . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.382(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 C17 1.530(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.534(2) . ?
C17 C19 1.535(2) . ?
C17 C20 1.538(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.387(2) . ?
C21 C26 1.388(2) . ?
C22 C23 1.399(2) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(2) . ?
C24 C27 1.516(2) . ?
C25 C26 1.384(2) . ?
C25 C28 1.512(2) . ?
C26 H26 0.9500 . ?
C27 H28A 0.9800 . ?
C27 H28B 0.9800 . ?
C27 H28C 0.9800 . ?
C28 H27A 0.9800 . ?
C28 H27B 0.9800 . ?
C28 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C21 125.65(13) . . ?
C3 N1 H1 117.2 . . ?
C21 N1 H1 117.2 . . ?
C22 N2 H2A 120.0 . . ?
C22 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C1 C2 122.31(14) . . ?
O1 C1 C5 117.31(14) . . ?
C2 C1 C5 120.37(14) . . ?
C3 C2 C1 124.15(15) . . ?
C3 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
N1 C3 C2 121.62(15) . . ?
N1 C3 C4 117.37(13) . . ?
C2 C3 C4 120.96(14) . . ?
C3 C4 C11 111.38(13) . . ?
C3 C4 H4A 109.4 . . ?
C11 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C11 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C10 C5 C6 118.27(15) . . ?
C10 C5 C1 118.66(14) . . ?
C6 C5 C1 123.04(15) . . ?
C7 C6 C5 121.37(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 118.62(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 121.57(15) . . ?
C7 C8 Cl1 119.40(13) . . ?
C9 C8 Cl1 119.03(13) . . ?
C8 C9 C10 119.12(16) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 121.05(15) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C16 C11 C12 117.29(15) . . ?
C16 C11 C4 120.66(14) . . ?
C12 C11 C4 122.00(14) . . ?
C13 C12 C11 121.02(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 122.00(15) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C15 116.56(15) . . ?
C13 C14 C17 120.70(14) . . ?
C15 C14 C17 122.69(14) . . ?
C16 C15 C14 121.31(15) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C11 C16 C15 121.81(15) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C14 C17 C18 108.29(12) . . ?
C14 C17 C19 111.15(13) . . ?
C18 C17 C19 108.53(13) . . ?
C14 C17 C20 111.74(13) . . ?
C18 C17 C20 108.89(13) . . ?
C19 C17 C20 108.17(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.39(15) . . ?
C22 C21 N1 120.20(14) . . ?
C26 C21 N1 119.39(14) . . ?
N2 C22 C21 121.47(15) . . ?
N2 C22 C23 120.98(16) . . ?
C21 C22 C23 117.54(15) . . ?
C24 C23 C22 122.13(16) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C23 C24 C25 119.74(15) . . ?
C23 C24 C27 119.79(16) . . ?
C25 C24 C27 120.46(16) . . ?
C26 C25 C24 118.22(15) . . ?
C26 C25 C28 120.74(16) . . ?
C24 C25 C28 121.01(15) . . ?
C25 C26 C21 121.96(16) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C24 C27 H28A 109.5 . . ?
C24 C27 H28B 109.5 . . ?
H28A C27 H28B 109.5 . . ?
C24 C27 H28C 109.5 . . ?
H28A C27 H28C 109.5 . . ?
H28B C27 H28C 109.5 . . ?
C25 C28 H27A 109.5 . . ?
C25 C28 H27B 109.5 . . ?
H27A C28 H27B 109.5 . . ?
C25 C28 H27C 109.5 . . ?
H27A C28 H27C 109.5 . . ?
H27B C28 H27C 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
O1 C1 C2 C3 -1.8(3) . . . . ?
C5 C1 C2 C3 176.92(15) . . . . ?
C21 N1 C3 C2 -178.60(15) . . . . ?
C21 N1 C3 C4 4.0(2) . . . . ?
C1 C2 C3 N1 -0.9(3) . . . . ?
C1 C2 C3 C4 176.41(15) . . . . ?
N1 C3 C4 C11 66.75(18) . . . . ?
C2 C3 C4 C11 -110.66(16) . . . . ?
O1 C1 C5 C10 -16.4(2) . . . . ?
C2 C1 C5 C10 164.80(15) . . . . ?
O1 C1 C5 C6 161.17(15) . . . . ?
C2 C1 C5 C6 -17.6(2) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C1 C5 C6 C7 -177.60(15) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C6 C7 C8 Cl1 179.46(12) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
Cl1 C8 C9 C10 -178.90(12) . . . . ?
C8 C9 C10 C5 -1.0(2) . . . . ?
C6 C5 C10 C9 0.6(2) . . . . ?
C1 C5 C10 C9 178.28(14) . . . . ?
C3 C4 C11 C16 49.41(19) . . . . ?
C3 C4 C11 C12 -128.14(16) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C4 C11 C12 C13 177.65(15) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C12 C13 C14 C17 -178.48(14) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C17 C14 C15 C16 177.69(15) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C4 C11 C16 C15 -178.41(14) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C13 C14 C17 C18 73.17(18) . . . . ?
C15 C14 C17 C18 -104.19(17) . . . . ?
C13 C14 C17 C19 -46.0(2) . . . . ?
C15 C14 C17 C19 136.68(15) . . . . ?
C13 C14 C17 C20 -166.91(14) . . . . ?
C15 C14 C17 C20 15.7(2) . . . . ?
C3 N1 C21 C22 75.5(2) . . . . ?
C3 N1 C21 C26 -106.17(19) . . . . ?
C26 C21 C22 N2 179.68(15) . . . . ?
N1 C21 C22 N2 -2.0(2) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
N1 C21 C22 C23 178.56(14) . . . . ?
N2 C22 C23 C24 -179.69(16) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C22 C23 C24 C27 -178.06(16) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C27 C24 C25 C26 177.71(15) . . . . ?
C23 C24 C25 C28 177.46(15) . . . . ?
C27 C24 C25 C28 -3.8(2) . . . . ?
C24 C25 C26 C21 1.0(2) . . . . ?
C28 C25 C26 C21 -177.44(15) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
N1 C21 C26 C25 -178.97(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 1.96 2.6520(17) 134.1 .
N2 H2B O1 0.88 2.24 3.006(2) 145.3 3_465
N2 H2A O1 0.88 2.56 3.0370(19) 114.9 1_455

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        67.58
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 950049'