# 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
#  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_shelxl
#TrackingRef 'CCDC.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11.50 Br0.50 N O2'
_chemical_formula_weight         205.65
_chemical_absolute_configuration rm


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   5.28800(10)
_cell_length_b                   31.171(2)
_cell_length_c                   11.3120(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.158(2)
_cell_angle_gamma                90.00
_cell_volume                     1864.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5445
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6641
_exptl_absorpt_correction_T_max  0.8078
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15229
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.50
_reflns_number_total             6871
_reflns_number_gt                5394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+4.5061P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.043(14)
_refine_ls_number_reflns         6871
_refine_ls_number_parameters     455
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7029(12) 0.2171(3) 0.3601(6) 0.0363(17) Uani 1 1 d . . .
C2 C 0.4367(14) 0.2099(3) 0.3076(6) 0.033(2) Uani 1 1 d . . .
H2 H 0.3157 0.2249 0.3586 0.040 Uiso 1 1 calc R . .
C3 C 0.3515(15) 0.1629(3) 0.2985(7) 0.041(2) Uani 1 1 d . . .
H3A H 0.3362 0.1516 0.3781 0.050 Uiso 1 1 calc R . .
H3B H 0.1840 0.1625 0.2634 0.050 Uiso 1 1 calc R . .
C4 C 0.5153(15) 0.1333(3) 0.2298(7) 0.0396(19) Uani 1 1 d . . .
C5 C 0.4634(19) 0.1246(3) 0.1114(8) 0.052(2) Uani 1 1 d . . .
H5 H 0.3259 0.1379 0.0756 0.062 Uiso 1 1 calc R . .
C6 C 0.609(2) 0.0967(3) 0.0453(9) 0.061(3) Uani 1 1 d . . .
H6 H 0.5698 0.0921 -0.0339 0.073 Uiso 1 1 calc R . .
C7 C 0.808(2) 0.0761(3) 0.0950(12) 0.072(3) Uani 1 1 d . . .
H7 H 0.9047 0.0567 0.0517 0.086 Uiso 1 1 calc R . .
C8 C 0.8639(19) 0.0848(3) 0.2125(12) 0.070(3) Uani 1 1 d . . .
H8 H 0.9999 0.0709 0.2481 0.084 Uiso 1 1 calc R . .
C9 C 0.7264(18) 0.1130(3) 0.2770(9) 0.054(2) Uani 1 1 d . . .
H9 H 0.7744 0.1188 0.3545 0.065 Uiso 1 1 calc R . .
C10 C 0.1595(12) 0.2171(3) 0.6552(6) 0.0299(15) Uani 1 1 d . . .
C11 C 0.4025(13) 0.2076(3) 0.7219(7) 0.032(2) Uani 1 1 d . . .
H11 H 0.5426 0.2064 0.6654 0.038 Uiso 1 1 calc R . .
C12 C 0.3978(17) 0.1660(3) 0.7934(7) 0.043(2) Uani 1 1 d . . .
H12A H 0.5643 0.1617 0.8276 0.051 Uiso 1 1 calc R . .
H12B H 0.2799 0.1696 0.8582 0.051 Uiso 1 1 calc R . .
C13 C 0.3257(18) 0.1264(3) 0.7262(8) 0.050(2) Uani 1 1 d U . .
C14 C 0.465(2) 0.1125(4) 0.6286(10) 0.065(3) Uani 1 1 d U . .
H14 H 0.6056 0.1280 0.6034 0.079 Uiso 1 1 calc R . .
C15 C 0.392(3) 0.0752(4) 0.5695(13) 0.090(4) Uani 1 1 d U . .
H15 H 0.4866 0.0653 0.5058 0.108 Uiso 1 1 calc R . .
C16 C 0.184(3) 0.0533(5) 0.6046(15) 0.109(5) Uani 1 1 d U . .
H16 H 0.1296 0.0295 0.5621 0.131 Uiso 1 1 calc R . .
C17 C 0.060(3) 0.0659(6) 0.6993(17) 0.126(5) Uani 1 1 d U . .
H17 H -0.0774 0.0498 0.7249 0.151 Uiso 1 1 calc R . .
C18 C 0.128(2) 0.1028(4) 0.7625(13) 0.087(4) Uani 1 1 d U . .
H18 H 0.0370 0.1108 0.8291 0.104 Uiso 1 1 calc R . .
C19 C 0.6381(11) 0.3335(3) 0.6702(6) 0.0300(16) Uani 1 1 d U . .
C20 C 0.8962(14) 0.3435(2) 0.6048(6) 0.0305(19) Uani 1 1 d . . .
H20 H 1.0335 0.3445 0.6631 0.037 Uiso 1 1 calc R . .
C21 C 0.8909(18) 0.3859(3) 0.5350(7) 0.046(2) Uani 1 1 d . . .
H21A H 1.0596 0.3915 0.5053 0.055 Uiso 1 1 calc R . .
H21B H 0.7802 0.3823 0.4672 0.055 Uiso 1 1 calc R . .
C22 C 0.8034(17) 0.4249(3) 0.6042(7) 0.044(2) Uani 1 1 d . . .
C23 C 0.930(2) 0.4390(3) 0.7023(9) 0.059(3) Uani 1 1 d . . .
H23 H 1.0756 0.4248 0.7274 0.071 Uiso 1 1 calc R . .
C24 C 0.845(3) 0.4741(4) 0.7638(11) 0.079(4) Uani 1 1 d . . .
H24 H 0.9335 0.4835 0.8299 0.095 Uiso 1 1 calc R . .
C25 C 0.630(3) 0.4953(4) 0.7290(15) 0.093(5) Uani 1 1 d . . .
H25 H 0.5701 0.5187 0.7714 0.111 Uiso 1 1 calc R . .
C26 C 0.507(3) 0.4810(4) 0.6303(16) 0.094(4) Uani 1 1 d . . .
H26 H 0.3629 0.4953 0.6041 0.113 Uiso 1 1 calc R . .
C27 C 0.593(2) 0.4461(3) 0.5695(11) 0.069(3) Uani 1 1 d . . .
H27 H 0.5050 0.4368 0.5031 0.083 Uiso 1 1 calc R . .
C28 C 0.1886(12) 0.3337(3) -0.0341(6) 0.0312(16) Uani 1 1 d . . .
C29 C -0.0637(14) 0.3414(3) 0.0168(6) 0.034(2) Uani 1 1 d . . .
H29 H -0.1877 0.3269 -0.0338 0.041 Uiso 1 1 calc R . .
C30 C -0.1408(16) 0.3877(3) 0.0257(7) 0.042(2) Uani 1 1 d . . .
H30A H -0.3066 0.3889 0.0620 0.051 Uiso 1 1 calc R . .
H30B H -0.1581 0.3990 -0.0539 0.051 Uiso 1 1 calc R . .
C31 C 0.0322(15) 0.4173(3) 0.0938(7) 0.0391(18) Uani 1 1 d . . .
C32 C -0.012(2) 0.4245(3) 0.2133(8) 0.054(2) Uani 1 1 d . . .
H32 H -0.1481 0.4110 0.2499 0.065 Uiso 1 1 calc R . .
C33 C 0.142(3) 0.4515(4) 0.2787(11) 0.072(3) Uani 1 1 d . . .
H33 H 0.1121 0.4557 0.3589 0.086 Uiso 1 1 calc R . .
C34 C 0.337(3) 0.4717(4) 0.2247(13) 0.081(4) Uani 1 1 d . . .
H34 H 0.4401 0.4899 0.2687 0.098 Uiso 1 1 calc R . .
C35 C 0.385(2) 0.4659(4) 0.1048(12) 0.070(3) Uani 1 1 d . . .
H35 H 0.5202 0.4800 0.0693 0.084 Uiso 1 1 calc R . .
C36 C 0.2291(16) 0.4384(3) 0.0376(10) 0.056(3) Uani 1 1 d . . .
H36 H 0.2575 0.4345 -0.0428 0.067 Uiso 1 1 calc R . .
N1 N 0.4313(11) 0.2314(2) 0.1901(5) 0.0373(18) Uani 1 1 d . . .
H1A H 0.5605 0.2221 0.1467 0.056 Uiso 1 1 calc R . .
H1B H 0.4437 0.2596 0.1998 0.056 Uiso 1 1 calc R . .
H1C H 0.2867 0.2252 0.1534 0.056 Uiso 1 1 calc R . .
N2 N 0.4463(13) 0.2436(2) 0.8049(6) 0.0369(17) Uani 1 1 d . . .
H2A H 0.4591 0.2680 0.7644 0.055 Uiso 1 1 calc R . .
H2B H 0.5888 0.2391 0.8451 0.055 Uiso 1 1 calc R . .
H2C H 0.3174 0.2455 0.8551 0.055 Uiso 1 1 calc R . .
N3 N 0.9447(13) 0.3084(3) 0.5204(6) 0.0391(18) Uani 1 1 d . . .
H3C H 0.8174 0.3067 0.4690 0.059 Uiso 1 1 calc R . .
H3D H 0.9580 0.2837 0.5595 0.059 Uiso 1 1 calc R . .
H3E H 1.0880 0.3135 0.4818 0.059 Uiso 1 1 calc R . .
N4 N -0.0669(11) 0.3194(2) 0.1363(5) 0.0340(17) Uani 1 1 d . . .
H4A H -0.0751 0.2911 0.1261 0.051 Uiso 1 1 calc R . .
H4B H -0.2010 0.3282 0.1771 0.051 Uiso 1 1 calc R . .
H4C H 0.0735 0.3259 0.1759 0.051 Uiso 1 1 calc R . .
O1 O 0.8537(11) 0.2390(2) 0.3130(5) 0.0488(16) Uani 1 1 d . . .
O2 O 0.7254(11) 0.1975(2) 0.4601(5) 0.0564(17) Uani 1 1 d . . .
H2D H 0.8676 0.2015 0.4870 0.085 Uiso 1 1 calc R . .
O3 O 0.1347(11) 0.1962(2) 0.5587(5) 0.0550(16) Uani 1 1 d . . .
O4 O 0.0095(10) 0.24383(19) 0.6908(5) 0.0399(13) Uani 1 1 d . . .
O5 O 0.5084(10) 0.30729(19) 0.6323(4) 0.0397(13) Uani 1 1 d . . .
O6 O 0.6399(11) 0.3532(2) 0.7692(5) 0.0527(16) Uani 1 1 d . . .
H6A H 0.5082 0.3482 0.8048 0.079 Uiso 1 1 calc R . .
O7 O 0.3630(11) 0.3114(2) 0.0139(5) 0.0465(15) Uani 1 1 d . . .
O8 O 0.2299(11) 0.3525(2) -0.1357(5) 0.0535(16) Uani 1 1 d . . .
Br1 Br 0.92503(14) 0.22082(3) 0.00431(6) 0.0400(2) Uani 1 1 d . . .
Br2 Br 0.42772(14) 0.33005(3) 0.32124(6) 0.0404(2) Uani 1 1 d . . .


_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
C1 O1 1.176(9) . ?
C1 O2 1.292(9) . ?
C1 C2 1.543(10) . ?
C2 N1 1.489(9) . ?
C2 C3 1.536(13) . ?
C2 H2 0.9800 . ?
C3 C4 1.487(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.389(12) . ?
C4 C5 1.394(11) . ?
C5 C6 1.381(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.353(14) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O4 1.219(9) . ?
C10 O3 1.278(9) . ?
C10 C11 1.517(9) . ?
C11 N2 1.482(10) . ?
C11 C12 1.528(12) . ?
C11 H11 0.9800 . ?
C12 C13 1.501(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.344(14) . ?
C13 C14 1.398(14) . ?
C14 C15 1.396(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.35(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.32(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.40(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O5 1.149(9) . ?
C19 O6 1.278(9) . ?
C19 C20 1.585(10) . ?
C20 N3 1.476(10) . ?
C20 C21 1.539(11) . ?
C20 H20 0.9800 . ?
C21 C22 1.518(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.352(13) . ?
C22 C23 1.368(13) . ?
C23 C24 1.374(14) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(17) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O7 1.276(9) . ?
C28 O8 1.309(9) . ?
C28 C29 1.474(10) . ?
C29 C30 1.505(12) . ?
C29 N4 1.516(9) . ?
C29 H29 0.9800 . ?
C30 C31 1.508(11) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C36 1.388(12) . ?
C31 C32 1.391(12) . ?
C32 C33 1.384(14) . ?
C32 H32 0.9300 . ?
C33 C34 1.354(18) . ?
C33 H33 0.9300 . ?
C34 C35 1.394(17) . ?
C34 H34 0.9300 . ?
C35 C36 1.410(14) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N3 H3C 0.8900 . ?
N3 H3D 0.8900 . ?
N3 H3E 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
O2 H2D 0.8200 . ?
O6 H6A 0.8200 . ?

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
O1 C1 O2 127.6(7) . . ?
O1 C1 C2 122.0(7) . . ?
O2 C1 C2 110.4(7) . . ?
N1 C2 C3 111.3(6) . . ?
N1 C2 C1 107.0(6) . . ?
C3 C2 C1 115.6(7) . . ?
N1 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C4 C3 C2 117.1(7) . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3B 108.0 . . ?
C2 C3 H3B 108.0 . . ?
H3A C3 H3B 107.3 . . ?
C9 C4 C5 115.8(8) . . ?
C9 C4 C3 123.5(8) . . ?
C5 C4 C3 120.7(8) . . ?
C6 C5 C4 122.3(9) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C7 C6 C5 120.5(10) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 117.8(10) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C9 C8 C7 122.0(10) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C4 121.4(10) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
O4 C10 O3 124.4(6) . . ?
O4 C10 C11 121.4(6) . . ?
O3 C10 C11 114.1(6) . . ?
N2 C11 C10 107.3(6) . . ?
N2 C11 C12 108.0(6) . . ?
C10 C11 C12 114.5(6) . . ?
N2 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C13 C12 C11 115.8(7) . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C18 C13 C14 119.1(10) . . ?
C18 C13 C12 119.6(10) . . ?
C14 C13 C12 121.3(9) . . ?
C15 C14 C13 119.3(11) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.2(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.7(15) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 122.1(16) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 119.5(13) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
O5 C19 O6 132.3(7) . . ?
O5 C19 C20 118.7(6) . . ?
O6 C19 C20 108.0(6) . . ?
N3 C20 C21 107.9(6) . . ?
N3 C20 C19 107.9(6) . . ?
C21 C20 C19 113.2(6) . . ?
N3 C20 H20 109.3 . . ?
C21 C20 H20 109.3 . . ?
C19 C20 H20 109.3 . . ?
C22 C21 C20 115.3(7) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C27 C22 C23 118.6(10) . . ?
C27 C22 C21 119.6(9) . . ?
C23 C22 C21 121.7(9) . . ?
C22 C23 C24 120.4(11) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.8(12) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 118.1(12) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
C27 C26 C25 120.8(12) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C22 C27 C26 121.3(12) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
O7 C28 O8 119.8(6) . . ?
O7 C28 C29 125.2(7) . . ?
O8 C28 C29 115.1(7) . . ?
C28 C29 C30 115.3(8) . . ?
C28 C29 N4 106.7(6) . . ?
C30 C29 N4 111.8(6) . . ?
C28 C29 H29 107.6 . . ?
C30 C29 H29 107.6 . . ?
N4 C29 H29 107.6 . . ?
C29 C30 C31 117.2(7) . . ?
C29 C30 H30A 108.0 . . ?
C31 C30 H30A 108.0 . . ?
C29 C30 H30B 108.0 . . ?
C31 C30 H30B 108.0 . . ?
H30A C30 H30B 107.2 . . ?
C36 C31 C32 119.9(8) . . ?
C36 C31 C30 120.7(8) . . ?
C32 C31 C30 119.4(8) . . ?
C33 C32 C31 121.1(10) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C32 119.3(11) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C33 C34 C35 121.4(11) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C34 C35 C36 119.6(11) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C31 C36 C35 118.7(10) . . ?
C31 C36 H36 120.7 . . ?
C35 C36 H36 120.7 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C20 N3 H3C 109.5 . . ?
C20 N3 H3D 109.5 . . ?
H3C N3 H3D 109.5 . . ?
C20 N3 H3E 109.5 . . ?
H3C N3 H3E 109.5 . . ?
H3D N3 H3E 109.5 . . ?
C29 N4 H4A 109.5 . . ?
C29 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C29 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C1 O2 H2D 109.5 . . ?
C19 O6 H6A 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 N1 5.3(11) . . . . ?
O2 C1 C2 N1 -176.8(7) . . . . ?
O1 C1 C2 C3 129.9(9) . . . . ?
O2 C1 C2 C3 -52.2(9) . . . . ?
N1 C2 C3 C4 65.5(9) . . . . ?
C1 C2 C3 C4 -56.9(9) . . . . ?
C2 C3 C4 C9 84.0(10) . . . . ?
C2 C3 C4 C5 -95.7(9) . . . . ?
C9 C4 C5 C6 1.3(13) . . . . ?
C3 C4 C5 C6 -179.0(9) . . . . ?
C4 C5 C6 C7 1.1(16) . . . . ?
C5 C6 C7 C8 -1.7(16) . . . . ?
C6 C7 C8 C9 -0.1(16) . . . . ?
C7 C8 C9 C4 2.7(15) . . . . ?
C5 C4 C9 C8 -3.2(13) . . . . ?
C3 C4 C9 C8 177.2(9) . . . . ?
O4 C10 C11 N2 -16.7(10) . . . . ?
O3 C10 C11 N2 160.7(7) . . . . ?
O4 C10 C11 C12 103.2(9) . . . . ?
O3 C10 C11 C12 -79.4(9) . . . . ?
N2 C11 C12 C13 173.2(7) . . . . ?
C10 C11 C12 C13 53.8(10) . . . . ?
C11 C12 C13 C18 -122.9(10) . . . . ?
C11 C12 C13 C14 59.3(12) . . . . ?
C18 C13 C14 C15 1.7(17) . . . . ?
C12 C13 C14 C15 179.5(10) . . . . ?
C13 C14 C15 C16 2(2) . . . . ?
C14 C15 C16 C17 -4(2) . . . . ?
C15 C16 C17 C18 3(3) . . . . ?
C14 C13 C18 C17 -3(2) . . . . ?
C12 C13 C18 C17 179.6(13) . . . . ?
C16 C17 C18 C13 0(3) . . . . ?
O5 C19 C20 N3 -13.5(10) . . . . ?
O6 C19 C20 N3 156.2(6) . . . . ?
O5 C19 C20 C21 105.8(9) . . . . ?
O6 C19 C20 C21 -84.4(8) . . . . ?
N3 C20 C21 C22 171.0(7) . . . . ?
C19 C20 C21 C22 51.7(10) . . . . ?
C20 C21 C22 C27 -118.2(9) . . . . ?
C20 C21 C22 C23 61.0(11) . . . . ?
C27 C22 C23 C24 0.0(15) . . . . ?
C21 C22 C23 C24 -179.2(10) . . . . ?
C22 C23 C24 C25 0.6(18) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C24 C25 C26 C27 1(2) . . . . ?
C23 C22 C27 C26 0.1(16) . . . . ?
C21 C22 C27 C26 179.3(10) . . . . ?
C25 C26 C27 C22 -0.8(19) . . . . ?
O7 C28 C29 C30 126.9(9) . . . . ?
O8 C28 C29 C30 -51.8(10) . . . . ?
O7 C28 C29 N4 2.1(11) . . . . ?
O8 C28 C29 N4 -176.5(7) . . . . ?
C28 C29 C30 C31 -56.4(9) . . . . ?
N4 C29 C30 C31 65.7(9) . . . . ?
C29 C30 C31 C36 89.1(10) . . . . ?
C29 C30 C31 C32 -93.2(9) . . . . ?
C36 C31 C32 C33 -2.1(13) . . . . ?
C30 C31 C32 C33 -179.9(8) . . . . ?
C31 C32 C33 C34 1.2(15) . . . . ?
C32 C33 C34 C35 -0.1(17) . . . . ?
C33 C34 C35 C36 0.1(17) . . . . ?
C32 C31 C36 C35 2.0(13) . . . . ?
C30 C31 C36 C35 179.8(8) . . . . ?
C34 C35 C36 C31 -1.0(15) . . . . ?

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
N3 H3D O4 0.89 1.95 2.806(9) 159.7 1_655
O2 H2D O3 0.82 1.64 2.433(8) 163.3 1_655
O6 H6A O8 0.82 1.63 2.423(8) 163.4 1_556
N2 H2A O5 0.89 1.95 2.803(9) 160.2 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.940
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.098


_database_code_depnum_ccdc_archive 'CCDC 873527'
