# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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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# 
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#  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_red
#TrackingRef '15153_web_deposit_cif_file_0_AhipaT.N._1352093899.ahi8valid.cif'



#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H30 N2 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C27 H30 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         414.53
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.1481(3)
_cell_length_b                   10.7263(3)
_cell_length_c                   13.4085(4)
_cell_angle_alpha                86.933(2)
_cell_angle_beta                 84.680(3)
_cell_angle_gamma                81.508(3)
_cell_volume                     1153.11(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    7945
_cell_measurement_theta_min      2.4005
_cell_measurement_theta_max      27.4241
_cell_special_details            
;

;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.71703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0839

# number of measured reflections (redundant set)
_diffrn_reflns_number            23543
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4529
# number of observed reflections (> n sig(I))
_reflns_number_gt                3711
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
Refinement on F² for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S
are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The
observed criterion of F² > 2sigma(F²) is used only
for calculating -R-factor-obs 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     
'calc w=1/[σ²(Fo²)+(0.0472P)²+0.2538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall - refined all H parameters
# refxyz - refined H coordinates only
# refU - refined H U only
# noref - no refinement of H parameters
# constr - H parameters constrained
# mixed - some constrained, some independent
# undef - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.51150(11) -0.11040(8) 0.87315(7) 1.000 0.0352(3) . .
O2 O Uani -0.05325(12) 0.57307(9) 0.64981(8) 1.000 0.0427(3) . .
N1 N Uani -0.83716(16) 0.10930(11) 0.35500(10) 1.000 0.0476(5) . .
N2 N Uani 0.05253(13) 0.36539(10) 0.68883(8) 1.000 0.0320(3) . .
C1 C Uani -0.72975(17) 0.14047(13) 0.39276(11) 1.000 0.0365(4) . .
C2 C Uani -0.59582(16) 0.17855(12) 0.44126(10) 1.000 0.0322(4) . .
C3 C Uani -0.43568(16) 0.11166(13) 0.42748(10) 1.000 0.0336(4) . .
C4 C Uani -0.30814(16) 0.14818(13) 0.47549(10) 1.000 0.0326(4) . .
C5 C Uani -0.33812(16) 0.25042(12) 0.53779(9) 1.000 0.0304(4) . .
C6 C Uani -0.49922(17) 0.31652(13) 0.55050(10) 1.000 0.0339(4) . .
C7 C Uani -0.62779(16) 0.28057(13) 0.50340(10) 1.000 0.0335(4) . .
C8 C Uani -0.20161(16) 0.28964(12) 0.58982(10) 1.000 0.0315(4) . .
C9 C Uani -0.08318(16) 0.20049(13) 0.63345(9) 1.000 0.0309(4) . .
C10 C Uani 0.03935(15) 0.24109(12) 0.68391(9) 1.000 0.0296(4) . .
C11 C Uani -0.06022(17) 0.44772(12) 0.64650(10) 1.000 0.0344(4) . .
C12 C Uani -0.19089(17) 0.41572(13) 0.59747(10) 1.000 0.0357(4) . .
C13 C Uani 0.08402(18) 0.60858(14) 0.69579(12) 1.000 0.0439(5) . .
C14 C Uani 0.16360(15) 0.15088(12) 0.73553(9) 1.000 0.0282(4) . .
C15 C Uani 0.14141(15) 0.02484(12) 0.75632(9) 1.000 0.0296(4) . .
C16 C Uani 0.25875(15) -0.05857(12) 0.80260(10) 1.000 0.0303(4) . .
C17 C Uani 0.40333(15) -0.01903(12) 0.82970(9) 1.000 0.0298(4) . .
C18 C Uani 0.42712(16) 0.10598(12) 0.81145(10) 1.000 0.0322(4) . .
C19 C Uani 0.30745(16) 0.18931(12) 0.76522(10) 1.000 0.0316(4) . .
C20 C Uani 0.66654(15) -0.07903(13) 0.90053(10) 1.000 0.0325(4) . .
C21 C Uani 0.76272(16) -0.20112(13) 0.93786(11) 1.000 0.0346(4) . .
C22 C Uani 0.92367(16) -0.18412(13) 0.98141(10) 1.000 0.0329(4) . .
C23 C Uani 1.01839(17) -0.30944(13) 1.01616(11) 1.000 0.0364(4) . .
C24 C Uani 1.17982(16) -0.30009(13) 1.06214(10) 1.000 0.0338(4) . .
C25 C Uani 1.26652(16) -0.42902(13) 1.09646(11) 1.000 0.0347(4) . .
C26 C Uani 1.42298(17) -0.42438(14) 1.14951(12) 1.000 0.0403(5) . .
C27 C Uani 1.4986(2) -0.55487(16) 1.18784(14) 1.000 0.0563(6) . .
H3 H Uiso -0.41420 0.04150 0.38550 1.000 0.0400 calc R
H4 H Uiso -0.19890 0.10300 0.46580 1.000 0.0390 calc R
H6 H Uiso -0.52080 0.38710 0.59210 1.000 0.0410 calc R
H7 H Uiso -0.73730 0.32530 0.51350 1.000 0.0400 calc R
H9 H Uiso -0.08660 0.11290 0.62860 1.000 0.0370 calc R
H12 H Uiso -0.27030 0.47910 0.57010 1.000 0.0430 calc R
H13A H Uiso 0.18870 0.57480 0.65830 1.000 0.0660 calc R
H13B H Uiso 0.08320 0.57450 0.76510 1.000 0.0660 calc R
H13C H Uiso 0.07400 0.70080 0.69540 1.000 0.0660 calc R
H15 H Uiso 0.04370 -0.00370 0.73820 1.000 0.0350 calc R
H16 H Uiso 0.24100 -0.14360 0.81610 1.000 0.0360 calc R
H18 H Uiso 0.52440 0.13430 0.83040 1.000 0.0390 calc R
H19 H Uiso 0.32400 0.27490 0.75350 1.000 0.0380 calc R
H20A H Uiso 0.64640 -0.01680 0.95380 1.000 0.0390 calc R
H20B H Uiso 0.72900 -0.04290 0.84180 1.000 0.0390 calc R
H21A H Uiso 0.78950 -0.25890 0.88160 1.000 0.0410 calc R
H21B H Uiso 0.69120 -0.24130 0.99000 1.000 0.0410 calc R
H22A H Uiso 0.99510 -0.14280 0.92990 1.000 0.0390 calc R
H22B H Uiso 0.89740 -0.12820 1.03890 1.000 0.0390 calc R
H23A H Uiso 1.04430 -0.36440 0.95810 1.000 0.0440 calc R
H23B H Uiso 0.94480 -0.35090 1.06620 1.000 0.0440 calc R
H24A H Uiso 1.15530 -0.24510 1.12020 1.000 0.0400 calc R
H24B H Uiso 1.25560 -0.26070 1.01210 1.000 0.0400 calc R
H25A H Uiso 1.18700 -0.47060 1.14240 1.000 0.0420 calc R
H25B H Uiso 1.29680 -0.48170 1.03730 1.000 0.0420 calc R
H26A H Uiso 1.39500 -0.36810 1.20670 1.000 0.0480 calc R
H26B H Uiso 1.50630 -0.38840 1.10240 1.000 0.0480 calc R
H27A H Uiso 1.52800 -0.61050 1.13130 1.000 0.0840 calc R
H27B H Uiso 1.41750 -0.58990 1.23580 1.000 0.0840 calc R
H27C H Uiso 1.59890 -0.54790 1.22100 1.000 0.0840 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.3623(15) . . yes
O1 C20 1.4383(16) . . yes
O2 C11 1.3574(16) . . yes
O2 C13 1.4335(18) . . yes
N1 C1 1.1493(19) . . yes
N2 C10 1.3589(17) . . yes
N2 C11 1.3227(17) . . yes
C1 C2 1.4396(19) . . no
C2 C3 1.3945(19) . . no
C2 C7 1.3902(19) . . no
C3 C4 1.3853(19) . . no
C4 C5 1.3933(18) . . no
C5 C6 1.3969(19) . . no
C5 C8 1.4881(18) . . no
C6 C7 1.3831(19) . . no
C8 C9 1.4001(19) . . no
C8 C12 1.3778(19) . . no
C9 C10 1.3890(18) . . no
C10 C14 1.4864(18) . . no
C11 C12 1.395(2) . . no
C14 C15 1.4002(18) . . no
C14 C19 1.3961(18) . . no
C15 C16 1.3775(18) . . no
C16 C17 1.3940(18) . . no
C17 C18 1.3886(18) . . no
C18 C19 1.3890(18) . . no
C20 C21 1.5097(19) . . no
C21 C22 1.5225(19) . . no
C22 C23 1.521(2) . . no
C23 C24 1.5219(19) . . no
C24 C25 1.5255(19) . . no
C25 C26 1.525(2) . . no
C26 C27 1.526(2) . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C9 H9 0.9500 . . no
C12 H12 0.9500 . . no
C13 H13A 0.9800 . . no
C13 H13B 0.9800 . . no
C13 H13C 0.9800 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C18 H18 0.9500 . . no
C19 H19 0.9500 . . no
C20 H20A 0.9900 . . no
C20 H20B 0.9900 . . no
C21 H21A 0.9900 . . no
C21 H21B 0.9900 . . no
C22 H22A 0.9900 . . no
C22 H22B 0.9900 . . no
C23 H23A 0.9900 . . no
C23 H23B 0.9900 . . no
C24 H24A 0.9900 . . no
C24 H24B 0.9900 . . no
C25 H25A 0.9900 . . no
C25 H25B 0.9900 . . no
C26 H26A 0.9900 . . no
C26 H26B 0.9900 . . no
C27 H27A 0.9800 . . no
C27 H27B 0.9800 . . no
C27 H27C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O1 C20 118.94(10) . . . yes
C11 O2 C13 116.93(11) . . . yes
C10 N2 C11 117.35(11) . . . yes
N1 C1 C2 179.23(16) . . . yes
C1 C2 C3 120.04(12) . . . no
C1 C2 C7 119.65(12) . . . no
C3 C2 C7 120.30(12) . . . no
C2 C3 C4 119.56(12) . . . no
C3 C4 C5 120.82(12) . . . no
C4 C5 C6 118.83(12) . . . no
C4 C5 C8 120.99(12) . . . no
C6 C5 C8 120.18(11) . . . no
C5 C6 C7 120.89(12) . . . no
C2 C7 C6 119.59(12) . . . no
C5 C8 C9 121.30(12) . . . no
C5 C8 C12 120.29(12) . . . no
C9 C8 C12 118.40(12) . . . no
C8 C9 C10 119.50(12) . . . no
N2 C10 C9 121.94(12) . . . yes
N2 C10 C14 116.23(11) . . . yes
C9 C10 C14 121.83(12) . . . no
O2 C11 N2 119.70(12) . . . yes
O2 C11 C12 115.71(12) . . . yes
N2 C11 C12 124.59(12) . . . yes
C8 C12 C11 118.15(12) . . . no
C10 C14 C15 121.64(11) . . . no
C10 C14 C19 120.87(11) . . . no
C15 C14 C19 117.49(11) . . . no
C14 C15 C16 121.18(12) . . . no
C15 C16 C17 120.45(12) . . . no
O1 C17 C16 115.13(11) . . . yes
O1 C17 C18 125.34(11) . . . yes
C16 C17 C18 119.52(12) . . . no
C17 C18 C19 119.46(12) . . . no
C14 C19 C18 121.87(12) . . . no
O1 C20 C21 105.94(10) . . . yes
C20 C21 C22 113.49(11) . . . no
C21 C22 C23 111.82(11) . . . no
C22 C23 C24 114.97(11) . . . no
C23 C24 C25 111.99(11) . . . no
C24 C25 C26 114.21(11) . . . no
C25 C26 C27 112.01(12) . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C2 C7 H7 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C8 C12 H12 121.00 . . . no
C11 C12 H12 121.00 . . . no
O2 C13 H13A 109.00 . . . no
O2 C13 H13B 109.00 . . . no
O2 C13 H13C 109.00 . . . no
H13A C13 H13B 109.00 . . . no
H13A C13 H13C 109.00 . . . no
H13B C13 H13C 109.00 . . . no
C14 C15 H15 119.00 . . . no
C16 C15 H15 119.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C14 C19 H19 119.00 . . . no
C18 C19 H19 119.00 . . . no
O1 C20 H20A 111.00 . . . no
O1 C20 H20B 111.00 . . . no
C21 C20 H20A 111.00 . . . no
C21 C20 H20B 111.00 . . . no
H20A C20 H20B 109.00 . . . no
C20 C21 H21A 109.00 . . . no
C20 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C23 C22 H22A 109.00 . . . no
C23 C22 H22B 109.00 . . . no
H22A C22 H22B 108.00 . . . no
C22 C23 H23A 109.00 . . . no
C22 C23 H23B 109.00 . . . no
C24 C23 H23A 109.00 . . . no
C24 C23 H23B 109.00 . . . no
H23A C23 H23B 107.00 . . . no
C23 C24 H24A 109.00 . . . no
C23 C24 H24B 109.00 . . . no
C25 C24 H24A 109.00 . . . no
C25 C24 H24B 109.00 . . . no
H24A C24 H24B 108.00 . . . no
C24 C25 H25A 109.00 . . . no
C24 C25 H25B 109.00 . . . no
C26 C25 H25A 109.00 . . . no
C26 C25 H25B 109.00 . . . no
H25A C25 H25B 108.00 . . . no
C25 C26 H26A 109.00 . . . no
C25 C26 H26B 109.00 . . . no
C27 C26 H26A 109.00 . . . no
C27 C26 H26B 109.00 . . . no
H26A C26 H26B 108.00 . . . no
C26 C27 H27A 109.00 . . . no
C26 C27 H27B 109.00 . . . no
C26 C27 H27C 109.00 . . . no
H27A C27 H27B 110.00 . . . no
H27A C27 H27C 109.00 . . . no
H27B C27 H27C 109.00 . . . no

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 O1 C20 C21 -175.29(11) . . . . no
C20 O1 C17 C16 177.97(11) . . . . no
C20 O1 C17 C18 -2.02(18) . . . . no
C13 O2 C11 N2 3.06(18) . . . . no
C13 O2 C11 C12 -177.29(12) . . . . no
C10 N2 C11 C12 0.0(2) . . . . no
C11 N2 C10 C9 2.38(18) . . . . no
C10 N2 C11 O2 179.62(11) . . . . no
C11 N2 C10 C14 -177.67(11) . . . . no
C7 C2 C3 C4 -0.5(2) . . . . no
C3 C2 C7 C6 0.9(2) . . . . no
C1 C2 C3 C4 -179.21(13) . . . . no
C1 C2 C7 C6 179.56(13) . . . . no
C2 C3 C4 C5 0.4(2) . . . . no
C3 C4 C5 C8 179.76(12) . . . . no
C3 C4 C5 C6 -0.5(2) . . . . no
C4 C5 C8 C12 139.79(14) . . . . no
C6 C5 C8 C9 139.00(13) . . . . no
C4 C5 C8 C9 -41.29(19) . . . . no
C4 C5 C6 C7 0.9(2) . . . . no
C8 C5 C6 C7 -179.41(12) . . . . no
C6 C5 C8 C12 -39.92(18) . . . . no
C5 C6 C7 C2 -1.1(2) . . . . no
C5 C8 C12 C11 -179.69(12) . . . . no
C5 C8 C9 C10 -178.09(12) . . . . no
C12 C8 C9 C10 0.85(19) . . . . no
C9 C8 C12 C11 1.36(19) . . . . no
C8 C9 C10 C14 177.22(12) . . . . no
C8 C9 C10 N2 -2.83(19) . . . . no
N2 C10 C14 C15 164.86(11) . . . . no
N2 C10 C14 C19 -15.10(17) . . . . no
C9 C10 C14 C15 -15.19(18) . . . . no
C9 C10 C14 C19 164.86(12) . . . . no
N2 C11 C12 C8 -1.9(2) . . . . no
O2 C11 C12 C8 178.49(12) . . . . no
C15 C14 C19 C18 1.58(19) . . . . no
C10 C14 C15 C16 178.83(12) . . . . no
C10 C14 C19 C18 -178.47(12) . . . . no
C19 C14 C15 C16 -1.22(18) . . . . no
C14 C15 C16 C17 -0.15(19) . . . . no
C15 C16 C17 C18 1.22(19) . . . . no
C15 C16 C17 O1 -178.78(11) . . . . no
C16 C17 C18 C19 -0.87(19) . . . . no
O1 C17 C18 C19 179.13(12) . . . . no
C17 C18 C19 C14 -0.6(2) . . . . no
O1 C20 C21 C22 -173.58(11) . . . . no
C20 C21 C22 C23 -178.84(11) . . . . no
C21 C22 C23 C24 -179.14(11) . . . . no
C22 C23 C24 C25 179.22(12) . . . . no
C23 C24 C25 C26 -176.10(12) . . . . no
C24 C25 C26 C27 176.50(13) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O2 C1 3.3598(17) . 2_466 no
O1 H20A 2.8600 . 2_657 no
N1 H9 2.5400 . 2_456 no
N1 H13C 2.7000 . 2_466 no
N1 H15 2.6000 . 2_456 no
N1 H20B 2.8000 . 2_556 no
N2 H7 2.7900 . 1_655 no
N2 H13A 2.6500 . . no
N2 H13B 2.5700 . . no
N2 H19 2.4900 . . no
C1 O2 3.3598(17) . 2_466 no
C1 C4 3.469(2) . 2_456 no
C2 C3 3.4807(19) . 2_456 no
C3 C2 3.4807(19) . 2_456 no
C3 C3 3.2379(19) . 2_456 no
C3 C15 3.4957(18) . 2_556 no
C3 C16 3.3228(19) . 2_556 no
C4 C1 3.469(2) . 2_456 no
C6 C19 3.4649(19) . 1_455 no
C7 C10 3.5222(18) . 1_455 no
C10 C7 3.5222(18) . 1_655 no
C15 C3 3.4957(18) . 2_556 no
C16 C3 3.3228(19) . 2_556 no
C19 C6 3.4649(19) . 1_655 no
C4 H9 2.8300 . . no
C6 H19 3.0000 . 1_455 no
C6 H12 2.7700 . . no
C7 H12 2.7500 . 2_466 no
C9 H15 2.6700 . . no
C9 H4 2.8200 . . no
C10 H24A 2.9400 . 2_657 no
C10 H7 2.9700 . 1_655 no
C11 H25A 2.9300 . 2_657 no
C12 H26A 3.0400 . 2_657 no
C12 H7 3.0800 . 2_466 no
C12 H6 2.7600 . . no
C13 H27C 2.8800 . 2_757 no
C14 H3 3.0900 . 2_556 no
C14 H22B 3.0200 . 2_657 no
C15 H9 2.6800 . . no
C15 H3 2.8200 . 2_556 no
C15 H22B 2.9900 . 2_657 no
C16 H22A 2.8400 . 1_455 no
C16 H22B 3.0600 . 2_657 no
C16 H3 2.7300 . 2_556 no
C17 H3 2.9000 . 2_556 no
C17 H20A 2.9300 . 2_657 no
C18 H20A 2.8700 . . no
C18 H20B 2.7800 . . no
C19 H22B 3.0700 . 2_657 no
C20 H18 2.5800 . . no
H3 C14 3.0900 . 2_556 no
H3 C15 2.8200 . 2_556 no
H3 C16 2.7300 . 2_556 no
H3 C17 2.9000 . 2_556 no
H4 C9 2.8200 . . no
H4 H9 2.4600 . . no
H6 C12 2.7600 . . no
H6 H12 2.3800 . . no
H7 N2 2.7900 . 1_455 no
H7 C10 2.9700 . 1_455 no
H7 C12 3.0800 . 2_466 no
H7 H12 2.3300 . 2_466 no
H9 C4 2.8300 . . no
H9 C15 2.6800 . . no
H9 H4 2.4600 . . no
H9 H15 2.1300 . . no
H9 N1 2.5400 . 2_456 no
H12 C6 2.7700 . . no
H12 H6 2.3800 . . no
H12 C7 2.7500 . 2_466 no
H12 H7 2.3300 . 2_466 no
H13A N2 2.6500 . . no
H13A H27C 2.4500 . 2_757 no
H13B N2 2.5700 . . no
H13B H27C 2.5900 . 2_757 no
H13C N1 2.7000 . 2_466 no
H15 C9 2.6700 . . no
H15 H9 2.1300 . . no
H15 N1 2.6000 . 2_456 no
H16 H22A 2.4000 . 1_455 no
H18 C20 2.5800 . . no
H18 H20A 2.4300 . . no
H18 H20B 2.3400 . . no
H19 N2 2.4900 . . no
H19 C6 3.0000 . 1_655 no
H20A C18 2.8700 . . no
H20A H18 2.4300 . . no
H20A H22B 2.5500 . . no
H20A O1 2.8600 . 2_657 no
H20A C17 2.9300 . 2_657 no
H20A H20A 2.5700 . 2_657 no
H20B C18 2.7800 . . no
H20B H18 2.3400 . . no
H20B N1 2.8000 . 2_556 no
H21A H23A 2.4900 . . no
H21B H23B 2.5000 . . no
H22A C16 2.8400 . 1_655 no
H22A H16 2.4000 . 1_655 no
H22B H20A 2.5500 . . no
H22B H24A 2.5800 . . no
H22B C14 3.0200 . 2_657 no
H22B C15 2.9900 . 2_657 no
H22B C16 3.0600 . 2_657 no
H22B C19 3.0700 . 2_657 no
H23A H21A 2.4900 . . no
H23A H25B 2.5400 . . no
H23B H21B 2.5000 . . no
H23B H25A 2.4600 . . no
H24A H22B 2.5800 . . no
H24A H26A 2.5300 . . no
H24A C10 2.9400 . 2_657 no
H25A H23B 2.4600 . . no
H25A H27B 2.5100 . . no
H25A C11 2.9300 . 2_657 no
H25B H23A 2.5400 . . no
H25B H27A 2.5600 . . no
H26A H24A 2.5300 . . no
H26A C12 3.0400 . 2_657 no
H27A H25B 2.5600 . . no
H27B H25A 2.5100 . . no
H27C C13 2.8800 . 2_757 no
H27C H13A 2.4500 . 2_757 no
H27C H13B 2.5900 . 2_757 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C9 H9 N1 0.9500 2.5400 3.4714(18) 165.00 2_456 yes
C15 H15 N1 0.9500 2.6000 3.5233(18) 163.00 2_456 yes
C19 H19 N2 0.9500 2.4900 2.8213(17) 100.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END



_database_code_depnum_ccdc_archive 'CCDC 909202'
#######################################################################
#
#                 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_red

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N2 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C23 H22 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         358.43
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.978(3)
_cell_length_b                   10.677(3)
_cell_length_c                   10.877(3)
_cell_angle_alpha                99.677(9)
_cell_angle_beta                 95.437(9)
_cell_angle_gamma                103.089(8)
_cell_volume                     991.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3545
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.08
_cell_special_details            
;
 
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.1662 before and 0.1080 after correction.
The Ratio of minimum to maximum transmission is 0.4751.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9810

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker Smart X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            21008
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3862
# number of observed reflections (> n sig(I))
_reflns_number_gt                2109
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker GIS'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'calc w=1/[σ²(Fo²)+(0.0855P)²]         where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3862
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.53672(16) 0.33556(13) 0.07607(13) 1.000 0.0698(5) . .
O2 O Uani -0.21079(17) 0.22135(13) 0.51178(14) 1.000 0.0808(6) . .
N1 N Uani -0.04279(18) 0.29351(14) 0.37655(14) 1.000 0.0603(6) . .
N2 N Uani -0.5324(3) 0.9991(2) 0.3036(2) 1.000 0.1109(10) . .
C1 C Uani -0.4758(3) 0.9151(2) 0.3125(2) 1.000 0.0784(9) . .
C2 C Uani -0.4048(2) 0.80886(19) 0.32268(19) 1.000 0.0650(8) . .
C3 C Uani -0.4072(2) 0.75557(19) 0.43074(19) 1.000 0.0716(8) . .
C4 C Uani -0.3394(2) 0.65323(19) 0.43915(19) 1.000 0.0670(8) . .
C5 C Uani -0.2687(2) 0.60127(17) 0.34209(17) 1.000 0.0562(7) . .
C6 C Uani -0.2682(2) 0.6554(2) 0.23416(18) 1.000 0.0686(8) . .
C7 C Uani -0.3351(2) 0.7586(2) 0.2245(2) 1.000 0.0721(8) . .
C8 C Uani -0.1920(2) 0.49352(18) 0.35431(17) 1.000 0.0556(6) . .
C9 C Uani -0.2407(2) 0.40292(18) 0.42812(18) 1.000 0.0631(7) . .
C10 C Uani -0.1607(2) 0.30658(18) 0.43564(18) 1.000 0.0617(7) . .
C11 C Uani 0.0080(2) 0.38279(17) 0.30507(16) 1.000 0.0547(6) . .
C12 C Uani -0.0650(2) 0.48252(17) 0.29257(17) 1.000 0.0582(7) . .
C13 C Uani 0.1444(2) 0.36808(16) 0.24339(16) 1.000 0.0540(6) . .
C14 C Uani 0.2034(2) 0.25890(18) 0.24586(17) 1.000 0.0621(7) . .
C15 C Uani 0.3333(2) 0.24410(18) 0.19243(17) 1.000 0.0620(7) . .
C16 C Uani 0.4085(2) 0.34004(18) 0.13307(17) 1.000 0.0580(7) . .
C17 C Uani 0.3508(2) 0.44952(19) 0.1283(2) 1.000 0.0722(8) . .
C18 C Uani 0.2230(2) 0.46260(19) 0.1830(2) 1.000 0.0712(8) . .
C19 C Uani 0.6028(3) 0.2261(2) 0.0783(2) 1.000 0.0629(8) . .
C20 C Uani 0.7348(2) 0.24241(19) 0.00309(19) 1.000 0.0668(8) . .
C21 C Uani 0.8167(2) 0.1325(2) -0.0008(2) 1.000 0.0780(8) . .
C22 C Uani 0.9467(3) 0.1482(3) -0.0802(2) 1.000 0.1068(11) . .
C23 C Uani -0.1308(3) 0.1209(2) 0.5212(2) 1.000 0.0895(10) . .
H3 H Uiso -0.45430 0.78880 0.49700 1.000 0.0860 calc R
H4 H Uiso -0.34110 0.61820 0.51190 1.000 0.0800 calc R
H6 H Uiso -0.22220 0.62150 0.16740 1.000 0.0820 calc R
H7 H Uiso -0.33300 0.79410 0.15210 1.000 0.0860 calc R
H9 H Uiso -0.32450 0.40630 0.47150 1.000 0.0760 calc R
H12 H Uiso -0.02880 0.54240 0.24270 1.000 0.0700 calc R
H14 H Uiso 0.15360 0.19340 0.28500 1.000 0.0750 calc R
H15 H Uiso 0.37010 0.17000 0.19630 1.000 0.0740 calc R
H17 H Uiso 0.39930 0.51420 0.08760 1.000 0.0870 calc R
H18 H Uiso 0.18720 0.53740 0.17990 1.000 0.0850 calc R
H19A H Uiso 0.518(2) 0.143(2) 0.0373(17) 1.000 0.082(6) . .
H19B H Uiso 0.635(2) 0.2197(19) 0.163(2) 1.000 0.082(7) . .
H20A H Uiso 0.80860 0.32510 0.03910 1.000 0.0800 calc R
H20B H Uiso 0.69650 0.24620 -0.08230 1.000 0.0800 calc R
H21A H Uiso 0.85800 0.13040 0.08430 1.000 0.0940 calc R
H21B H Uiso 0.74260 0.04950 -0.03470 1.000 0.0940 calc R
H22A H Uiso 1.02240 0.22870 -0.04530 1.000 0.1600 calc R
H22B H Uiso 0.90640 0.15010 -0.16470 1.000 0.1600 calc R
H22C H Uiso 0.99380 0.07590 -0.08110 1.000 0.1600 calc R
H23A H Uiso -0.17970 0.06450 0.57350 1.000 0.1340 calc R
H23B H Uiso -0.02550 0.16030 0.55760 1.000 0.1340 calc R
H23C H Uiso -0.13370 0.07040 0.43870 1.000 0.1340 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.365(2) . . yes
O1 C19 1.428(3) . . yes
O2 C10 1.362(2) . . yes
O2 C23 1.431(3) . . yes
N1 C10 1.311(3) . . yes
N1 C11 1.357(2) . . yes
N2 C1 1.139(3) . . yes
C1 C2 1.436(3) . . no
C2 C3 1.389(3) . . no
C2 C7 1.381(3) . . no
C3 C4 1.377(3) . . no
C4 C5 1.384(3) . . no
C5 C6 1.393(3) . . no
C5 C8 1.486(3) . . no
C6 C7 1.383(3) . . no
C8 C9 1.381(3) . . no
C8 C12 1.394(3) . . no
C9 C10 1.390(3) . . no
C11 C12 1.389(3) . . no
C11 C13 1.477(3) . . no
C13 C14 1.388(3) . . no
C13 C18 1.391(3) . . no
C14 C15 1.380(3) . . no
C15 C16 1.383(3) . . no
C16 C17 1.388(3) . . no
C17 C18 1.365(3) . . no
C19 C20 1.497(3) . . no
C20 C21 1.516(3) . . no
C21 C22 1.512(3) . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C6 H6 0.9300 . . no
C7 H7 0.9300 . . no
C9 H9 0.9300 . . no
C12 H12 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no
C17 H17 0.9300 . . no
C18 H18 0.9300 . . no
C19 H19A 1.03(2) . . no
C19 H19B 0.96(2) . . no
C20 H20A 0.9700 . . no
C20 H20B 0.9700 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C19 119.03(16) . . . yes
C10 O2 C23 117.16(16) . . . yes
C10 N1 C11 117.66(16) . . . yes
N2 C1 C2 179.6(2) . . . yes
C1 C2 C3 120.17(18) . . . no
C1 C2 C7 120.02(19) . . . no
C3 C2 C7 119.81(18) . . . no
C2 C3 C4 119.64(18) . . . no
C3 C4 C5 121.63(18) . . . no
C4 C5 C6 117.94(17) . . . no
C4 C5 C8 120.90(17) . . . no
C6 C5 C8 121.13(17) . . . no
C5 C6 C7 121.13(18) . . . no
C2 C7 C6 119.85(19) . . . no
C5 C8 C9 121.93(17) . . . no
C5 C8 C12 120.40(17) . . . no
C9 C8 C12 117.66(17) . . . no
C8 C9 C10 118.06(17) . . . no
O2 C10 N1 119.04(17) . . . yes
O2 C10 C9 115.90(17) . . . yes
N1 C10 C9 125.06(18) . . . yes
N1 C11 C12 121.05(17) . . . yes
N1 C11 C13 116.32(16) . . . yes
C12 C11 C13 122.64(16) . . . no
C8 C12 C11 120.50(17) . . . no
C11 C13 C14 120.98(16) . . . no
C11 C13 C18 122.66(16) . . . no
C14 C13 C18 116.34(17) . . . no
C13 C14 C15 122.39(17) . . . no
C14 C15 C16 119.70(18) . . . no
O1 C16 C15 124.91(17) . . . yes
O1 C16 C17 116.12(17) . . . yes
C15 C16 C17 118.97(17) . . . no
C16 C17 C18 120.25(19) . . . no
C13 C18 C17 122.34(18) . . . no
O1 C19 C20 107.75(17) . . . yes
C19 C20 C21 113.06(17) . . . no
C20 C21 C22 112.45(19) . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C5 C6 H6 119.00 . . . no
C7 C6 H6 119.00 . . . no
C2 C7 H7 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C9 H9 121.00 . . . no
C10 C9 H9 121.00 . . . no
C8 C12 H12 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C14 H14 119.00 . . . no
C15 C14 H14 119.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C16 C17 H17 120.00 . . . no
C18 C17 H17 120.00 . . . no
C13 C18 H18 119.00 . . . no
C17 C18 H18 119.00 . . . no
O1 C19 H19A 107.2(11) . . . no
O1 C19 H19B 110.9(12) . . . no
C20 C19 H19A 110.6(10) . . . no
C20 C19 H19B 111.8(11) . . . no
H19A C19 H19B 108.5(16) . . . no
C19 C20 H20A 109.00 . . . no
C19 C20 H20B 109.00 . . . no
C21 C20 H20A 109.00 . . . no
C21 C20 H20B 109.00 . . . no
H20A C20 H20B 108.00 . . . no
C20 C21 H21A 109.00 . . . no
C20 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 110.00 . . . no
H22A C22 H22B 109.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no
O2 C23 H23A 109.00 . . . no
O2 C23 H23B 109.00 . . . no
O2 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 110.00 . . . no

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
C16 O1 C19 C20 176.67(16) . . . . no
C19 O1 C16 C15 -1.3(3) . . . . no
C19 O1 C16 C17 179.53(17) . . . . no
C23 O2 C10 C9 179.88(17) . . . . no
C23 O2 C10 N1 -0.6(3) . . . . no
C11 N1 C10 O2 -177.62(16) . . . . no
C10 N1 C11 C13 177.90(16) . . . . no
C10 N1 C11 C12 -1.6(3) . . . . no
C11 N1 C10 C9 1.8(3) . . . . no
C7 C2 C3 C4 0.2(3) . . . . no
C1 C2 C3 C4 179.7(2) . . . . no
C3 C2 C7 C6 0.1(3) . . . . no
C1 C2 C7 C6 -179.4(2) . . . . no
C2 C3 C4 C5 -0.2(3) . . . . no
C3 C4 C5 C8 178.14(18) . . . . no
C3 C4 C5 C6 -0.2(3) . . . . no
C6 C5 C8 C12 29.0(3) . . . . no
C4 C5 C6 C7 0.5(3) . . . . no
C4 C5 C8 C12 -149.28(19) . . . . no
C4 C5 C8 C9 29.4(3) . . . . no
C6 C5 C8 C9 -152.28(19) . . . . no
C8 C5 C6 C7 -177.82(18) . . . . no
C5 C6 C7 C2 -0.5(3) . . . . no
C5 C8 C12 C11 179.23(17) . . . . no
C9 C8 C12 C11 0.5(3) . . . . no
C12 C8 C9 C10 -0.3(3) . . . . no
C5 C8 C9 C10 -179.03(17) . . . . no
C8 C9 C10 N1 -0.9(3) . . . . no
C8 C9 C10 O2 178.56(17) . . . . no
C13 C11 C12 C8 -178.98(17) . . . . no
N1 C11 C13 C14 8.1(2) . . . . no
C12 C11 C13 C14 -172.44(17) . . . . no
C12 C11 C13 C18 9.3(3) . . . . no
N1 C11 C12 C8 0.5(3) . . . . no
N1 C11 C13 C18 -170.22(17) . . . . no
C14 C13 C18 C17 0.3(3) . . . . no
C11 C13 C14 C15 -178.02(17) . . . . no
C11 C13 C18 C17 178.70(18) . . . . no
C18 C13 C14 C15 0.4(3) . . . . no
C13 C14 C15 C16 -0.5(3) . . . . no
C14 C15 C16 C17 -0.2(3) . . . . no
C14 C15 C16 O1 -179.37(17) . . . . no
C15 C16 C17 C18 0.9(3) . . . . no
O1 C16 C17 C18 -179.87(18) . . . . no
C16 C17 C18 C13 -1.0(3) . . . . no
O1 C19 C20 C21 179.36(16) . . . . no
C19 C20 C21 C22 178.32(18) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 H7 2.8700 . 2_565 no
O1 H17 2.6100 . 2_665 no
N1 H14 2.4600 . . no
N1 H23B 2.6300 . . no
N1 H23C 2.5600 . . no
N2 H15 2.5900 . 1_465 no
N2 H3 2.8900 . 2_476 no
C4 C14 3.423(3) . 2_566 no
C6 C17 3.586(3) . 1_455 no
C9 C11 3.532(3) . 2_566 no
C10 C12 3.532(3) . 2_566 no
C11 C9 3.532(3) . 2_566 no
C12 C10 3.532(3) . 2_566 no
C14 C4 3.423(3) . 2_566 no
C17 C6 3.586(3) . 1_655 no
C1 H20B 3.0400 . 2_565 no
C3 H9 3.0200 . 2_466 no
C4 H9 2.7500 . . no
C6 H12 2.6900 . . no
C9 H4 2.7000 . . no
C12 H18 2.6700 . . no
C12 H6 2.7000 . . no
C12 H20A 2.9500 . 1_455 no
C13 H4 3.0100 . 2_566 no
C14 H4 2.7700 . 2_566 no
C15 H19A 2.737(19) . . no
C15 H19B 2.822(19) . . no
C18 H12 2.6900 . . no
C19 H15 2.5600 . . no
H3 N2 2.8900 . 2_476 no
H4 C9 2.7000 . . no
H4 H9 2.2700 . . no
H4 C13 3.0100 . 2_566 no
H4 C14 2.7700 . 2_566 no
H6 C12 2.7000 . . no
H6 H12 2.2400 . . no
H7 O1 2.8700 . 2_565 no
H9 C4 2.7500 . . no
H9 H4 2.2700 . . no
H9 C3 3.0200 . 2_466 no
H12 C6 2.6900 . . no
H12 C18 2.6900 . . no
H12 H6 2.2400 . . no
H12 H18 2.1300 . . no
H14 N1 2.4600 . . no
H15 N2 2.5900 . 1_645 no
H15 C19 2.5600 . . no
H15 H19A 2.3000 . . no
H15 H19B 2.3900 . . no
H17 O1 2.6100 . 2_665 no
H18 C12 2.6700 . . no
H18 H12 2.1300 . . no
H19A C15 2.737(19) . . no
H19A H15 2.3000 . . no
H19A H21B 2.5700 . . no
H19B C15 2.822(19) . . no
H19B H15 2.3900 . . no
H19B H21A 2.5600 . . no
H20A C12 2.9500 . 1_655 no
H20A H22A 2.5500 . . no
H20B H22B 2.5100 . . no
H20B C1 3.0400 . 2_565 no
H21A H19B 2.5600 . . no
H21B H19A 2.5700 . . no
H22A H20A 2.5500 . . no
H22B H20B 2.5100 . . no
H22C H22C 2.6000 . 2_755 no
H23B N1 2.6300 . . no
H23C N1 2.5600 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C14 H14 N1 0.9300 2.4600 2.799(3) 101.00 . yes
C15 H15 N2 0.9300 2.5900 3.460(3) 156.00 1_645 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
_database_code_depnum_ccdc_archive 'CCDC 958625'
