# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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:
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#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xxx

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O3'
# 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            'C16 H14 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         282.29
_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           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   16.558(5)
_cell_length_b                   11.363(4)
_cell_length_c                   17.351(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.49(2)
_cell_angle_gamma                90
_cell_volume                     2841.6(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3792
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       ' Block'
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.981

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            21437
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.36
_reflns_number_total             5152
_reflns_number_gt                4160
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.989


_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_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)+(0.0969P)²+0.0162P] where P=(Fo²+2Fc²)/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_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         5152
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1663
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.099

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

# 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 0.59706(10) 0.90101(11) 0.99842(10) 1.000 0.0623(5) . .
O2 O Uani 0.68037(9) 0.70801(11) 1.09316(9) 1.000 0.0529(5) . .
O3 O Uani 0.66588(10) 0.52362(12) 1.18110(10) 1.000 0.0614(5) . .
N1 N Uani 0.57788(13) 0.99390(15) 0.93774(12) 1.000 0.0639(6) . .
N2 N Uani 0.45495(10) 0.87322(13) 0.88970(11) 1.000 0.0465(5) . .
C1 C Uani 0.51559(12) 0.73190(15) 1.01352(12) 1.000 0.0435(6) . .
C2 C Uani 0.42762(13) 0.69195(16) 0.99458(13) 1.000 0.0509(7) . .
C3 C Uani 0.41937(14) 0.59738(17) 1.03955(14) 1.000 0.0553(7) . .
C4 C Uani 0.49780(14) 0.53988(16) 1.10418(14) 1.000 0.0526(7) . .
C5 C Uani 0.58491(13) 0.57656(16) 1.12258(13) 1.000 0.0477(6) . .
C6 C Uani 0.59455(13) 0.67417(15) 1.07829(13) 1.000 0.0442(6) . .
C7 C Uani 0.52051(12) 0.83402(15) 0.96513(12) 1.000 0.0425(6) . .
C8 C Uani 0.49325(13) 0.97228(15) 0.87530(13) 1.000 0.0433(6) . .
C9 C Uani 0.44463(13) 1.04718(15) 0.79666(12) 1.000 0.0439(6) . .
C10 C Uani 0.36270(14) 1.00832(18) 0.72371(13) 1.000 0.0519(7) . .
C11 C Uani 0.31825(15) 1.0777(2) 0.64960(15) 1.000 0.0629(8) . .
C12 C Uani 0.35331(17) 1.1862(2) 0.64633(16) 1.000 0.0692(9) . .
C13 C Uani 0.43336(17) 1.22620(19) 0.71835(16) 1.000 0.0632(8) . .
C14 C Uani 0.47955(14) 1.15756(17) 0.79343(14) 1.000 0.0527(7) . .
C15 C Uani 0.66309(18) 0.4352(2) 1.23802(18) 1.000 0.0774(10) . .
C16 C Uani 0.74186(15) 0.7518(2) 1.18030(17) 1.000 0.0703(9) . .
O4 O Uani 0.08483(10) 0.60044(12) 0.59607(11) 1.000 0.0628(5) . .
O5 O Uani 0.17019(9) 0.79123(11) 0.57586(9) 1.000 0.0539(5) . .
O6 O Uani 0.15707(9) 0.95798(13) 0.46187(9) 1.000 0.0631(5) . .
N3 N Uani 0.06335(12) 0.50778(14) 0.63772(13) 1.000 0.0629(7) . .
N4 N Uani -0.06083(11) 0.62473(13) 0.56089(11) 1.000 0.0471(5) . .
C17 C Uani 0.00517(12) 0.76441(15) 0.49781(12) 1.000 0.0431(6) . .
C18 C Uani -0.08244(14) 0.80319(16) 0.43227(14) 1.000 0.0535(7) . .
C19 C Uani -0.08965(14) 0.89425(17) 0.37716(14) 1.000 0.0559(7) . .
C20 C Uani -0.01132(14) 0.94740(17) 0.38437(14) 1.000 0.0525(7) . .
C21 C Uani 0.07563(13) 0.91101(16) 0.44896(13) 1.000 0.0474(6) . .
C22 C Uani 0.08447(12) 0.81986(15) 0.50701(12) 1.000 0.0425(6) . .
C23 C Uani 0.00747(12) 0.66498(15) 0.55193(12) 1.000 0.0432(6) . .
C24 C Uani -0.02340(13) 0.52724(15) 0.61407(12) 1.000 0.0436(6) . .
C25 C Uani -0.07516(13) 0.45189(15) 0.64352(12) 1.000 0.0447(6) . .
C26 C Uani -0.16334(15) 0.48425(17) 0.62602(14) 1.000 0.0560(7) . .
C27 C Uani -0.21196(17) 0.4153(2) 0.65507(16) 1.000 0.0695(9) . .
C28 C Uani -0.17336(19) 0.3151(2) 0.70091(17) 1.000 0.0751(10) . .
C29 C Uani -0.08618(18) 0.28025(19) 0.71768(15) 1.000 0.0697(9) . .
C30 C Uani -0.03681(15) 0.34786(17) 0.68886(13) 1.000 0.0542(7) . .
C31 C Uani 0.15224(17) 1.0471(2) 0.40084(18) 1.000 0.0823(10) . .
C32 C Uani 0.22931(15) 0.7277(2) 0.55159(16) 1.000 0.0704(9) . .
H1 H Uiso 0.37470 0.72960 0.95150 1.000 0.0610 calc R
H2 H Uiso 0.36080 0.57150 1.02670 1.000 0.0660 calc R
H3 H Uiso 0.49150 0.47680 1.13490 1.000 0.0630 calc R
H10 H Uiso 0.33820 0.93530 0.72530 1.000 0.0620 calc R
H11 H Uiso 0.26390 1.05110 0.60110 1.000 0.0750 calc R
H12 H Uiso 0.32300 1.23230 0.59570 1.000 0.0830 calc R
H13 H Uiso 0.45660 1.30000 0.71650 1.000 0.0760 calc R
H14 H Uiso 0.53380 1.18500 0.84170 1.000 0.0630 calc R
H15A H Uiso 0.72500 0.40900 1.27810 1.000 0.1160 calc R
H15B H Uiso 0.62660 0.37000 1.20320 1.000 0.1160 calc R
H15C H Uiso 0.63580 0.46720 1.27110 1.000 0.1160 calc R
H16A H Uiso 0.79690 0.78260 1.18230 1.000 0.1050 calc R
H16B H Uiso 0.75840 0.68900 1.22240 1.000 0.1050 calc R
H16C H Uiso 0.71150 0.81320 1.19450 1.000 0.1050 calc R
H15 H Uiso -0.13570 0.76720 0.42610 1.000 0.0640 calc R
H16 H Uiso -0.14800 0.92040 0.33450 1.000 0.0670 calc R
H17 H Uiso -0.01700 1.00770 0.34580 1.000 0.0630 calc R
H26 H Uiso -0.19000 0.55290 0.59450 1.000 0.0670 calc R
H27 H Uiso -0.27100 0.43770 0.64320 1.000 0.0830 calc R
H28 H Uiso -0.20570 0.26940 0.72120 1.000 0.0900 calc R
H29 H Uiso -0.06060 0.21090 0.74860 1.000 0.0840 calc R
H30 H Uiso 0.02160 0.32390 0.69970 1.000 0.0650 calc R
H31A H Uiso 0.21390 1.07150 0.41620 1.000 0.1230 calc R
H31B H Uiso 0.11800 1.11340 0.40380 1.000 0.1230 calc R
H31C H Uiso 0.12170 1.01570 0.34180 1.000 0.1230 calc R
H32A H Uiso 0.29200 0.72980 0.59970 1.000 0.1060 calc R
H32B H Uiso 0.22660 0.76330 0.50020 1.000 0.1060 calc R
H32C H Uiso 0.20890 0.64740 0.53860 1.000 0.1060 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 N1 1.412(2) . . yes
O1 C7 1.341(3) . . yes
O2 C6 1.369(3) . . yes
O2 C16 1.433(3) . . yes
O3 C5 1.360(3) . . yes
O3 C15 1.425(3) . . yes
O4 N3 1.418(2) . . yes
O4 C23 1.341(3) . . yes
O5 C22 1.371(3) . . yes
O5 C32 1.436(3) . . yes
O6 C21 1.362(3) . . yes
O6 C31 1.439(3) . . yes
N1 C8 1.305(3) . . yes
N2 C7 1.300(3) . . yes
N2 C8 1.374(3) . . yes
N3 C24 1.304(3) . . yes
N4 C23 1.298(3) . . yes
N4 C24 1.378(2) . . yes
C1 C2 1.402(3) . . no
C1 C6 1.399(3) . . no
C1 C7 1.458(3) . . no
C2 C3 1.374(3) . . no
C3 C4 1.392(3) . . no
C4 C5 1.379(3) . . no
C5 C6 1.403(3) . . no
C8 C9 1.467(3) . . no
C9 C14 1.394(3) . . no
C9 C10 1.395(3) . . no
C10 C11 1.373(3) . . no
C11 C12 1.376(3) . . no
C12 C13 1.376(4) . . no
C13 C14 1.382(3) . . no
C2 H1 0.9300 . . no
C3 H2 0.9300 . . no
C4 H3 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15B 0.9600 . . no
C15 H15C 0.9600 . . no
C15 H15A 0.9600 . . no
C16 H16C 0.9600 . . no
C16 H16A 0.9600 . . no
C16 H16B 0.9600 . . no
C17 C18 1.403(3) . . no
C17 C22 1.393(3) . . no
C17 C23 1.458(3) . . no
C18 C19 1.374(3) . . no
C19 C20 1.379(4) . . no
C20 C21 1.383(3) . . no
C21 C22 1.401(3) . . no
C24 C25 1.470(3) . . no
C25 C26 1.387(4) . . no
C25 C30 1.388(3) . . no
C26 C27 1.384(4) . . no
C27 C28 1.355(3) . . no
C28 C29 1.383(5) . . no
C29 C30 1.382(4) . . no
C18 H15 0.9300 . . no
C19 H16 0.9300 . . no
C20 H17 0.9300 . . no
C26 H26 0.9300 . . no
C27 H27 0.9300 . . no
C28 H28 0.9300 . . no
C29 H29 0.9300 . . no
C30 H30 0.9300 . . no
C31 H31A 0.9600 . . no
C31 H31B 0.9600 . . no
C31 H31C 0.9600 . . no
C32 H32A 0.9600 . . no
C32 H32B 0.9600 . . no
C32 H32C 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
N1 O1 C7 106.57(16) . . . yes
C6 O2 C16 115.40(18) . . . yes
C5 O3 C15 118.2(2) . . . yes
N3 O4 C23 106.76(18) . . . yes
C22 O5 C32 115.26(16) . . . yes
C21 O6 C31 117.57(18) . . . yes
O1 N1 C8 103.52(17) . . . yes
C7 N2 C8 103.43(17) . . . yes
O4 N3 C24 103.15(16) . . . yes
C23 N4 C24 103.43(18) . . . yes
C2 C1 C6 119.28(17) . . . no
C6 C1 C7 122.8(2) . . . no
C2 C1 C7 117.97(18) . . . no
C1 C2 C3 120.2(2) . . . no
C2 C3 C4 120.7(2) . . . no
C3 C4 C5 119.95(19) . . . no
O3 C5 C6 115.0(2) . . . yes
O3 C5 C4 124.98(18) . . . yes
C4 C5 C6 120.02(19) . . . no
O2 C6 C1 119.53(17) . . . yes
O2 C6 C5 120.44(18) . . . yes
C1 C6 C5 119.9(2) . . . no
N2 C7 C1 126.63(19) . . . yes
O1 C7 C1 120.84(17) . . . yes
O1 C7 N2 112.51(16) . . . yes
N1 C8 N2 113.98(17) . . . yes
N2 C8 C9 123.59(19) . . . yes
N1 C8 C9 122.43(18) . . . yes
C8 C9 C10 120.23(17) . . . no
C10 C9 C14 119.06(18) . . . no
C8 C9 C14 120.72(18) . . . no
C9 C10 C11 120.1(2) . . . no
C10 C11 C12 120.7(2) . . . no
C11 C12 C13 119.7(2) . . . no
C12 C13 C14 120.6(2) . . . no
C9 C14 C13 119.9(2) . . . no
C3 C2 H1 120.00 . . . no
C1 C2 H1 120.00 . . . no
C2 C3 H2 120.00 . . . no
C4 C3 H2 120.00 . . . no
C5 C4 H3 120.00 . . . no
C3 C4 H3 120.00 . . . no
C11 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C13 C12 H12 120.00 . . . no
C11 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C9 C14 H14 120.00 . . . no
C13 C14 H14 120.00 . . . no
O3 C15 H15C 109.00 . . . no
H15A C15 H15B 110.00 . . . no
H15A C15 H15C 109.00 . . . no
O3 C15 H15A 109.00 . . . no
O3 C15 H15B 109.00 . . . no
H15B C15 H15C 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 110.00 . . . no
O2 C16 H16A 109.00 . . . no
O2 C16 H16B 109.00 . . . no
O2 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
C18 C17 C22 119.42(17) . . . no
C18 C17 C23 117.03(19) . . . no
C22 C17 C23 123.55(18) . . . no
C17 C18 C19 120.1(2) . . . no
C18 C19 C20 120.7(2) . . . no
C19 C20 C21 120.00(19) . . . no
O6 C21 C20 124.59(18) . . . yes
O6 C21 C22 115.26(18) . . . yes
C20 C21 C22 120.2(2) . . . no
O5 C22 C17 120.39(16) . . . yes
O5 C22 C21 119.93(19) . . . yes
C17 C22 C21 119.54(19) . . . no
O4 C23 N4 112.48(16) . . . yes
O4 C23 C17 120.42(19) . . . yes
N4 C23 C17 127.03(19) . . . yes
N3 C24 N4 114.18(19) . . . yes
N3 C24 C25 122.17(17) . . . yes
N4 C24 C25 123.6(2) . . . yes
C24 C25 C26 120.05(17) . . . no
C24 C25 C30 120.7(2) . . . no
C26 C25 C30 119.2(2) . . . no
C25 C26 C27 120.6(2) . . . no
C26 C27 C28 119.9(3) . . . no
C27 C28 C29 120.4(3) . . . no
C28 C29 C30 120.5(2) . . . no
C25 C30 C29 119.4(2) . . . no
C17 C18 H15 120.00 . . . no
C19 C18 H15 120.00 . . . no
C18 C19 H16 120.00 . . . no
C20 C19 H16 120.00 . . . no
C19 C20 H17 120.00 . . . no
C21 C20 H17 120.00 . . . no
C25 C26 H26 120.00 . . . no
C27 C26 H26 120.00 . . . no
C26 C27 H27 120.00 . . . no
C28 C27 H27 120.00 . . . no
C27 C28 H28 120.00 . . . no
C29 C28 H28 120.00 . . . no
C28 C29 H29 120.00 . . . no
C30 C29 H29 120.00 . . . no
C25 C30 H30 120.00 . . . no
C29 C30 H30 120.00 . . . no
O6 C31 H31A 109.00 . . . no
O6 C31 H31B 109.00 . . . no
O6 C31 H31C 109.00 . . . no
H31A C31 H31B 110.00 . . . no
H31A C31 H31C 109.00 . . . no
H31B C31 H31C 110.00 . . . no
O5 C32 H32A 110.00 . . . no
O5 C32 H32B 109.00 . . . no
O5 C32 H32C 110.00 . . . no
H32A C32 H32B 109.00 . . . no
H32A C32 H32C 109.00 . . . no
H32B C32 H32C 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
C7 O1 N1 C8 -0.4(2) . . . . no
N1 O1 C7 N2 0.5(2) . . . . no
N1 O1 C7 C1 -177.68(18) . . . . no
C16 O2 C6 C1 118.2(2) . . . . no
C16 O2 C6 C5 -66.8(2) . . . . no
C15 O3 C5 C6 170.87(18) . . . . no
C15 O3 C5 C4 -10.3(3) . . . . no
N3 O4 C23 C17 -176.79(16) . . . . no
C23 O4 N3 C24 0.0(2) . . . . no
N3 O4 C23 N4 0.3(2) . . . . no
C32 O5 C22 C17 109.7(2) . . . . no
C32 O5 C22 C21 -74.7(2) . . . . no
C31 O6 C21 C20 -3.7(3) . . . . no
C31 O6 C21 C22 176.42(18) . . . . no
O1 N1 C8 C9 -179.26(19) . . . . no
O1 N1 C8 N2 0.1(2) . . . . no
C8 N2 C7 O1 -0.4(2) . . . . no
C8 N2 C7 C1 177.6(2) . . . . no
C7 N2 C8 N1 0.2(2) . . . . no
C7 N2 C8 C9 179.6(2) . . . . no
O4 N3 C24 C25 -179.27(16) . . . . no
O4 N3 C24 N4 -0.3(2) . . . . no
C24 N4 C23 O4 -0.5(2) . . . . no
C24 N4 C23 C17 176.42(18) . . . . no
C23 N4 C24 C25 179.46(17) . . . . no
C23 N4 C24 N3 0.5(2) . . . . no
C7 C1 C2 C3 -178.81(18) . . . . no
C7 C1 C6 C5 179.81(18) . . . . no
C6 C1 C2 C3 0.3(3) . . . . no
C6 C1 C7 N2 159.9(2) . . . . no
C2 C1 C6 O2 175.90(17) . . . . no
C6 C1 C7 O1 -22.2(3) . . . . no
C2 C1 C7 O1 156.82(19) . . . . no
C2 C1 C7 N2 -21.1(3) . . . . no
C7 C1 C6 O2 -5.1(3) . . . . no
C2 C1 C6 C5 0.8(3) . . . . no
C1 C2 C3 C4 -0.1(3) . . . . no
C2 C3 C4 C5 -1.1(3) . . . . no
C3 C4 C5 C6 2.1(3) . . . . no
C3 C4 C5 O3 -176.68(19) . . . . no
O3 C5 C6 O2 1.9(3) . . . . no
C4 C5 C6 O2 -177.05(18) . . . . no
C4 C5 C6 C1 -2.0(3) . . . . no
O3 C5 C6 C1 176.93(17) . . . . no
N1 C8 C9 C10 166.7(2) . . . . no
N1 C8 C9 C14 -13.0(3) . . . . no
N2 C8 C9 C10 -12.6(3) . . . . no
N2 C8 C9 C14 167.7(2) . . . . no
C14 C9 C10 C11 0.9(4) . . . . no
C8 C9 C14 C13 179.2(2) . . . . no
C10 C9 C14 C13 -0.5(4) . . . . no
C8 C9 C10 C11 -178.8(2) . . . . no
C9 C10 C11 C12 -0.4(4) . . . . no
C10 C11 C12 C13 -0.6(4) . . . . no
C11 C12 C13 C14 1.0(4) . . . . no
C12 C13 C14 C9 -0.4(4) . . . . no
C18 C17 C22 O5 173.65(17) . . . . no
C18 C17 C22 C21 -2.0(3) . . . . no
C23 C17 C22 O5 -7.7(3) . . . . no
C23 C17 C18 C19 -178.10(19) . . . . no
C22 C17 C23 O4 -19.1(3) . . . . no
C22 C17 C23 N4 164.27(19) . . . . no
C18 C17 C23 O4 159.68(18) . . . . no
C22 C17 C18 C19 0.7(3) . . . . no
C23 C17 C22 C21 176.74(18) . . . . no
C18 C17 C23 N4 -17.0(3) . . . . no
C17 C18 C19 C20 1.1(3) . . . . no
C18 C19 C20 C21 -1.5(3) . . . . no
C19 C20 C21 O6 -179.67(19) . . . . no
C19 C20 C21 C22 0.2(3) . . . . no
O6 C21 C22 O5 5.8(3) . . . . no
O6 C21 C22 C17 -178.57(17) . . . . no
C20 C21 C22 O5 -174.12(18) . . . . no
C20 C21 C22 C17 1.5(3) . . . . no
N3 C24 C25 C26 171.87(19) . . . . no
N3 C24 C25 C30 -8.2(3) . . . . no
N4 C24 C25 C26 -7.0(3) . . . . no
N4 C24 C25 C30 172.87(18) . . . . no
C24 C25 C26 C27 -178.61(19) . . . . no
C30 C25 C26 C27 1.5(3) . . . . no
C24 C25 C30 C29 178.39(18) . . . . no
C26 C25 C30 C29 -1.7(3) . . . . no
C25 C26 C27 C28 -0.1(3) . . . . no
C26 C27 C28 C29 -1.0(4) . . . . no
C27 C28 C29 C30 0.8(4) . . . . no
C28 C29 C30 C25 0.6(3) . . . . 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 O2 2.680(2) . . no
O1 N2 2.197(3) . . no
O1 C16 3.337(3) . . no
O2 O1 2.680(2) . . no
O2 O3 2.671(2) . . no
O2 C31 3.279(4) . 2_646 no
O3 O2 2.671(2) . . no
O3 C16 2.885(3) . . no
O4 N4 2.195(3) . . no
O4 C32 3.198(3) . . no
O4 O5 2.703(2) . . no
O5 O4 2.703(2) . . no
O5 O6 2.670(2) . . no
O6 C11 3.320(3) . . no
O6 C32 2.978(3) . . no
O6 O5 2.670(2) . . no
O2 H31A 2.4000 . 2_646 no
O3 H16B 2.3000 . . no
O4 H32C 2.7400 . . no
O4 H15A 2.8200 . 3_667 no
O6 H32B 2.4300 . . no
O6 H11 2.4200 . . no
N1 N2 2.247(3) . . no
N2 N1 2.247(3) . . no
N3 N4 2.252(3) . . no
N4 N3 2.252(3) . . no
N1 H14 2.6100 . . no
N2 H27 2.9000 . 2_556 no
N2 H1 2.6400 . . no
N2 H10 2.6300 . . no
N3 H30 2.5900 . . no
N4 H15 2.6000 . . no
N4 H26 2.6100 . . no
C1 C14 3.541(3) . 3_677 no
C3 C5 3.410(3) . 3_667 no
C5 C3 3.410(3) . 3_667 no
C6 C14 3.578(3) . 3_677 no
C11 C19 3.594(4) . 3_576 no
C11 O6 3.320(3) . . no
C14 C6 3.578(3) . 3_677 no
C14 C1 3.541(3) . 3_677 no
C16 C19 3.562(4) . 1_656 no
C16 O1 3.337(3) . . no
C16 O3 2.885(3) . . no
C16 C31 3.591(4) . 2_646 no
C19 C11 3.594(4) . 3_576 no
C19 C16 3.562(4) . 1_454 no
C31 O2 3.279(4) . 2_656 no
C31 C16 3.591(4) . 2_656 no
C32 O6 2.978(3) . . no
C32 O4 3.198(3) . . no
C2 H14 2.9400 . 3_677 no
C3 H14 3.0600 . 3_677 no
C4 H15B 2.7600 . . no
C4 H15C 2.7900 . . no
C5 H16B 2.8300 . . no
C8 H13 2.8900 . 2_646 no
C10 H16C 3.0600 . 3_677 no
C11 H2 3.0700 . 4_564 no
C11 H3 3.0700 . 4_564 no
C11 H16 2.9600 . 3_576 no
C12 H3 3.0300 . 4_564 no
C15 H3 2.5500 . . no
C16 H31A 2.9600 . 2_646 no
C16 H16 3.0600 . 1_656 no
C20 H31C 2.7600 . . no
C20 H31B 2.7500 . . no
C21 H32B 2.7700 . . no
C24 H29 2.9500 . 2_556 no
C25 H32C 3.0500 . 3_566 no
C26 H32C 2.9700 . 3_566 no
C26 H16A 3.0100 . 4_464 no
C29 H17 3.0900 . 4_565 no
C30 H31C 3.0800 . 4_565 no
C30 H17 3.0600 . 4_565 no
C31 H17 2.5200 . . no
C31 H11 3.0300 . . no
C32 H15A 3.0800 . 3_667 no
H1 N2 2.6400 . . no
H2 C11 3.0700 . 4_565 no
H3 H15B 2.3000 . . no
H3 C15 2.5500 . . no
H3 C11 3.0700 . 4_565 no
H3 C12 3.0300 . 4_565 no
H3 H15C 2.4000 . . no
H10 N2 2.6300 . . no
H11 C31 3.0300 . . no
H11 O6 2.4200 . . no
H13 C8 2.8900 . 2_656 no
H14 N1 2.6100 . . no
H14 H32A 2.5900 . 2_656 no
H14 C2 2.9400 . 3_677 no
H14 C3 3.0600 . 3_677 no
H15 N4 2.6000 . . no
H15A C32 3.0800 . 3_667 no
H15A O4 2.8200 . 3_667 no
H15B H3 2.3000 . . no
H15B C4 2.7600 . . no
H15C C4 2.7900 . . no
H15C H3 2.4000 . . no
H16 C16 3.0600 . 1_454 no
H16 C11 2.9600 . 3_576 no
H16A C26 3.0100 . 4_665 no
H16A H26 2.4900 . 4_665 no
H16B C5 2.8300 . . no
H16B O3 2.3000 . . no
H16C C10 3.0600 . 3_677 no
H17 C31 2.5200 . . no
H17 H31B 2.2900 . . no
H17 H31C 2.3300 . . no
H17 C29 3.0900 . 4_564 no
H17 C30 3.0600 . 4_564 no
H26 N4 2.6100 . . no
H26 H16A 2.4900 . 4_464 no
H27 N2 2.9000 . 2_546 no
H29 C24 2.9500 . 2_546 no
H30 N3 2.5900 . . no
H31A O2 2.4000 . 2_656 no
H31A C16 2.9600 . 2_656 no
H31B C20 2.7500 . . no
H31B H17 2.2900 . . no
H31C C20 2.7600 . . no
H31C H17 2.3300 . . no
H31C C30 3.0800 . 4_564 no
H32A H14 2.5900 . 2_646 no
H32B O6 2.4300 . . no
H32B C21 2.7700 . . no
H32C O4 2.7400 . . no
H32C C25 3.0500 . 3_566 no
H32C C26 2.9700 . 3_566 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)
#
C11 H11 O6 0.9300 2.4200 3.320(3) 162.00 . yes
C16 H16B O3 0.9600 2.3000 2.885(3) 118.00 . yes
C26 H26 N4 0.9300 2.6100 2.932(3) 101.00 . yes
C31 H31A O2 0.9600 2.4000 3.279(4) 151.00 2_656 yes
C32 H32B O6 0.9600 2.4300 2.978(3) 116.00 . 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 951425'
