# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound8
_database_code_depnum_ccdc_archive 'CCDC 1569191'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;
#==============================================================================

_audit_creation_date             2016-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C27 H6 F15 N3 O3)'
_chemical_formula_sum            'C27 H6 F15 N3 O3'
_chemical_formula_weight         705.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   21.834(4)
_cell_length_b                   4.9270(10)
_cell_length_c                   22.042(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.23(3)
_cell_angle_gamma                90
_cell_volume                     2352.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      29.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0596 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.6934.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35158
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.411
_diffrn_reflns_theta_max         27.311
_diffrn_reflns_theta_min         0.911
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'MAR300 CCD'
_diffrn_measurement_method       'κ and ω scans'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.68879
_diffrn_source                   synchrotron
_diffrn_radiation_source         'bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                9991
_reflns_number_total             11208
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1102
_refine_ls_number_reflns         11208
_refine_ls_number_restraints     1136
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(4) 0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C6A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C3A)
\\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C28A) \\sim Ueq,
Uanis(C29A) \\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C31A) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(C33A) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.02
Uanis(N2) = Uanis(N2A)
Uanis(N3) = Uanis(N3A)
Uanis(N3A) = Uanis(N3)
Uanis(N1A) = Uanis(N1)
Uanis(N6A) = Uanis(N6)
Uanis(N4A) = Uanis(N4)
Uanis(N5A) = Uanis(N5)
Uanis(O4) = Uanis(O4A)
Uanis(O5A) = Uanis(O5)
Uanis(O6) = Uanis(O6A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C7A)=Sof(H7A)=Sof(C14A)=Sof(H14A)=Sof(N3A)=Sof(C21A)=Sof(H21A)=Sof(O2A)=
 Sof(H2A)=Sof(N1A)=Sof(C2A)=Sof(C6A)=Sof(C1A)=Sof(C5A)=Sof(O1A)=Sof(H1A)=
 Sof(O3A)=Sof(H3A)=Sof(N2A)=Sof(C4A)=Sof(C3A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(N1)=Sof(H1)=Sof(N2)=Sof(H2)=Sof(N3)=Sof(H3)=
 Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C14)=
 Sof(H14)=Sof(C21)=Sof(H21)=FVAR(1)
 Sof(N4A)=Sof(O6A)=Sof(H6A)=Sof(C41A)=Sof(H41A)=Sof(O4A)=Sof(H4A)=Sof(C48A)=
 Sof(H48A)=Sof(O5A)=Sof(H5A)=Sof(N5A)=Sof(N6A)=Sof(C32A)=Sof(C31A)=Sof(C28A)=
 Sof(C30A)=Sof(C29A)=Sof(C33A)=Sof(C34A)=Sof(H34A)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(O6)=Sof(N4)=Sof(H4)=Sof(N5)=Sof(H5)=Sof(N6)=Sof(H6)=
 Sof(C28)=Sof(C29)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(C33)=Sof(C34)=Sof(H34)=
 Sof(C41)=Sof(H41)=Sof(C48)=Sof(H48)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C14(H14), C21(H21), N4(H4), C34(H34), C41(H41), C48(H48),
 C7A(H7A), C14A(H14A), C21A(H21A), C41A(H41A), C48A(H48A), C34A(H34A)
6.b Idealised tetrahedral OH refined as rotating group:
 O6A(H6A), O4A(H4A), O2A(H2A), O5A(H5A), O1A(H1A), O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.15335(9) 0.7862(4) 0.41848(9) 0.0287(4) Uani 1 1 d . U . . .
F2 F 0.14760(10) 1.1391(4) 0.32563(9) 0.0332(5) Uani 1 1 d . U . . .
F3 F 0.23894(10) 1.5201(4) 0.32229(8) 0.0304(5) Uani 1 1 d . U . . .
F4 F 0.33513(9) 1.5267(4) 0.41232(9) 0.0262(4) Uani 1 1 d . U . . .
F5 F 0.34196(9) 1.1731(4) 0.50447(9) 0.0285(4) Uani 1 1 d . U . . .
F6 F 0.49068(9) 0.6971(4) 0.78256(8) 0.0243(4) Uani 1 1 d . U . . .
F7 F 0.58110(9) 0.6646(4) 0.87647(9) 0.0282(4) Uani 1 1 d . U . . .
F8 F 0.57831(9) 0.2617(4) 0.96256(9) 0.0293(4) Uani 1 1 d . U . . .
F9 F 0.48174(10) -0.0863(4) 0.95275(9) 0.0304(5) Uani 1 1 d . U . . .
F10 F 0.39134(9) -0.0539(4) 0.86104(10) 0.0286(4) Uani 1 1 d . U . . .
F11 F 0.12779(10) -0.5864(4) 0.74330(9) 0.0291(4) Uani 1 1 d . U . . .
F12 F 0.03832(10) -0.9612(4) 0.73602(9) 0.0340(5) Uani 1 1 d . U . . .
F13 F -0.04787(10) -0.9867(5) 0.63527(11) 0.0393(5) Uani 1 1 d . U . . .
F14 F -0.04129(11) -0.6341(5) 0.54195(12) 0.0459(6) Uani 1 1 d . U . . .
F15 F 0.04873(12) -0.2607(5) 0.54853(11) 0.0416(6) Uani 1 1 d . U . . .
C8 C 0.24755(15) 0.9670(6) 0.46461(14) 0.0186(6) Uani 1 1 d . U . . .
C9 C 0.19898(14) 0.9669(7) 0.41773(15) 0.0211(6) Uani 1 1 d . U . . .
C10 C 0.19573(15) 1.1467(7) 0.36929(14) 0.0212(6) Uani 1 1 d . U . . .
C11 C 0.24163(15) 1.3375(6) 0.36730(14) 0.0197(6) Uani 1 1 d . U . . .
C12 C 0.29026(14) 1.3421(6) 0.41334(14) 0.0185(6) Uani 1 1 d . U . . .
C13 C 0.29326(15) 1.1586(6) 0.46115(14) 0.0190(6) Uani 1 1 d . U . . .
C15 C 0.43761(14) 0.3261(6) 0.81853(14) 0.0183(6) Uani 1 1 d . U . . .
C16 C 0.48767(15) 0.4995(6) 0.82509(13) 0.0185(6) Uani 1 1 d . U . . .
C17 C 0.53490(14) 0.4824(6) 0.87189(14) 0.0198(6) Uani 1 1 d . U . . .
C18 C 0.53378(14) 0.2845(6) 0.91591(13) 0.0192(6) Uani 1 1 d . U . . .
C19 C 0.48416(15) 0.1069(7) 0.91104(14) 0.0198(6) Uani 1 1 d . U . . .
C20 C 0.43727(14) 0.1293(7) 0.86368(15) 0.0199(6) Uani 1 1 d . U . . .
C22 C 0.09051(13) -0.4090(6) 0.64623(14) 0.0182(6) Uani 1 1 d . U . . .
C23 C 0.08623(14) -0.5938(6) 0.69364(14) 0.0194(6) Uani 1 1 d . U . . .
C24 C 0.04000(15) -0.7873(6) 0.68993(15) 0.0217(6) Uani 1 1 d . U . . .
C25 C -0.00294(15) -0.8007(7) 0.63897(17) 0.0258(7) Uani 1 1 d . U . . .
C26 C 0.00024(16) -0.6213(7) 0.59128(17) 0.0280(7) Uani 1 1 d . U . . .
C27 C 0.04732(15) -0.4309(7) 0.59561(16) 0.0256(7) Uani 1 1 d . U . . .
O1 O 0.36003(12) 0.6385(5) 0.66663(12) 0.0183(5) Uani 0.817(3) 1 d . U P A 1
O2 O 0.23818(12) -0.0764(5) 0.72776(12) 0.0201(5) Uani 0.817(3) 1 d . U P A 1
O3 O 0.17657(12) 0.3804(6) 0.54279(12) 0.0192(5) Uani 0.817(3) 1 d . U P A 1
N1 N 0.24310(17) 0.7694(7) 0.50934(15) 0.0165(6) Uani 0.817(3) 1 d . U P A 1
H1 H 0.212(2) 0.677(9) 0.5065(19) 0.020 Uiso 0.817(3) 1 d R . P A 1
N2 N 0.39412(16) 0.3685(7) 0.76692(15) 0.0165(6) Uani 0.817(3) 1 d . U P A 1
H2 H 0.402(2) 0.495(10) 0.745(2) 0.020 Uiso 0.817(3) 1 d R . P A 1
N3 N 0.14030(16) -0.2268(7) 0.65713(16) 0.0156(7) Uani 0.817(3) 1 d . U P A 1
H3 H 0.1647 -0.2463 0.6918 0.019 Uiso 0.817(3) 1 calc R . P A 1
C1 C 0.2696(2) 0.5219(9) 0.6011(2) 0.0148(8) Uani 0.817(3) 1 d . U P A 1
C2 C 0.31377(18) 0.4886(8) 0.6563(2) 0.0139(7) Uani 0.817(3) 1 d . U P A 1
C3 C 0.3020(2) 0.2760(10) 0.7000(2) 0.0165(9) Uani 0.817(3) 1 d . U P A 1
C4 C 0.2480(2) 0.1027(8) 0.6895(2) 0.0156(8) Uani 0.817(3) 1 d . U P A 1
C5 C 0.20500(19) 0.1400(8) 0.6337(2) 0.0138(8) Uani 0.817(3) 1 d . U P A 1
C6 C 0.21523(18) 0.3494(10) 0.58983(18) 0.0147(7) Uani 0.817(3) 1 d . U P A 1
C7 C 0.28040(16) 0.7251(7) 0.56073(16) 0.0158(7) Uani 0.817(3) 1 d . U P A 1
H7 H 0.3158 0.8370 0.5700 0.019 Uiso 0.817(3) 1 calc R . P A 1
C14 C 0.34226(18) 0.2287(7) 0.75139(17) 0.0167(7) Uani 0.817(3) 1 d . U P A 1
H14 H 0.3327 0.0868 0.7778 0.020 Uiso 0.817(3) 1 calc R . P A 1
C21 C 0.15451(17) -0.0258(7) 0.62003(16) 0.0148(7) Uani 0.817(3) 1 d . U P A 1
H21 H 0.1285 0.0028 0.5827 0.018 Uiso 0.817(3) 1 calc R . P A 1
F16 F 0.52494(10) -0.1800(4) 0.21590(9) 0.0258(4) Uani 1 1 d . U . . .
F17 F 0.42851(9) -0.1521(4) 0.12853(10) 0.0294(5) Uani 1 1 d . U . . .
F18 F 0.42293(9) 0.2424(4) 0.04037(9) 0.0323(5) Uani 1 1 d . U . . .
F19 F 0.51645(10) 0.6004(4) 0.04200(9) 0.0293(4) Uani 1 1 d . U . . .
F20 F 0.61349(9) 0.5770(4) 0.12908(9) 0.0263(4) Uani 1 1 d . U . . .
F21 F 0.87986(9) 1.0549(4) 0.25529(8) 0.0290(4) Uani 1 1 d . U . . .
F22 F 0.96364(10) 1.4485(4) 0.25810(9) 0.0333(5) Uani 1 1 d . U . . .
F23 F 1.04995(9) 1.5155(4) 0.35650(11) 0.0371(5) Uani 1 1 d . U . . .
F24 F 1.04906(11) 1.1830(5) 0.45488(12) 0.0464(6) Uani 1 1 d . U . . .
F25 F 0.96120(11) 0.7942(5) 0.45422(10) 0.0421(6) Uani 1 1 d . U . . .
F26 F 0.84642(9) -0.2642(4) 0.57356(9) 0.0286(4) Uani 1 1 d . U . . .
F27 F 0.85567(10) -0.6005(5) 0.66820(10) 0.0350(5) Uani 1 1 d . U . . .
F28 F 0.76967(10) -0.9973(4) 0.67665(8) 0.0282(4) Uani 1 1 d . U . . .
F29 F 0.67230(8) -1.0394(4) 0.58719(9) 0.0240(4) Uani 1 1 d . U . . .
F30 F 0.66101(8) -0.6977(4) 0.49201(8) 0.0256(4) Uani 1 1 d . U . . .
C35 C 0.57235(14) 0.1973(6) 0.17568(13) 0.0172(6) Uani 1 1 d . U . . .
C36 C 0.52355(15) 0.0154(6) 0.17358(13) 0.0185(6) Uani 1 1 d . U . . .
C37 C 0.47351(14) 0.0289(6) 0.12889(14) 0.0192(6) Uani 1 1 d . U . . .
C38 C 0.47070(14) 0.2259(7) 0.08403(14) 0.0201(6) Uani 1 1 d . U . . .
C39 C 0.51839(14) 0.4062(6) 0.08438(14) 0.0186(6) Uani 1 1 d . U . . .
C40 C 0.56801(14) 0.3920(6) 0.12974(14) 0.0184(6) Uani 1 1 d . U . . .
C42 C 0.91866(13) 0.9103(6) 0.35523(14) 0.0188(6) Uani 1 1 d . U . . .
C43 C 0.92087(14) 1.0797(6) 0.30534(14) 0.0193(6) Uani 1 1 d . U . . .
C44 C 0.96451(15) 1.2834(6) 0.30641(15) 0.0217(6) Uani 1 1 d . U . . .
C45 C 1.00786(15) 1.3180(7) 0.35664(17) 0.0255(7) Uani 1 1 d . U . . .
C46 C 1.00683(15) 1.1533(8) 0.40601(16) 0.0281(7) Uani 1 1 d . U . . .
C47 C 0.96263(16) 0.9532(7) 0.40551(15) 0.0261(7) Uani 1 1 d . U . . .
C49 C 0.75265(14) -0.4669(6) 0.52907(13) 0.0172(6) Uani 1 1 d . U . . .
C50 C 0.80223(15) -0.4543(6) 0.57545(14) 0.0203(6) Uani 1 1 d . U . . .
C51 C 0.80771(15) -0.6266(7) 0.62480(14) 0.0219(7) Uani 1 1 d . U . . .
C52 C 0.76412(15) -0.8236(6) 0.62948(13) 0.0203(6) Uani 1 1 d . U . . .
C53 C 0.71487(14) -0.8471(6) 0.58393(14) 0.0179(6) Uani 1 1 d . U . . .
C54 C 0.70938(14) -0.6697(6) 0.53502(13) 0.0170(6) Uani 1 1 d . U . . .
O4 O 0.72575(13) 0.4920(6) 0.24605(13) 0.0198(6) Uani 0.783(2) 1 d . U P B 1
O5 O 0.84740(13) 0.3204(6) 0.43379(12) 0.0191(5) Uani 0.783(2) 1 d . U P B 1
O6 O 0.66870(13) -0.1997(6) 0.37525(13) 0.0185(5) Uani 0.783(2) 1 d . U P B 1
N4 N 0.62611(16) 0.2199(7) 0.21704(15) 0.0156(6) Uani 0.783(2) 1 d . U P B 1
H4 H 0.6535 0.3379 0.2073 0.019 Uiso 0.783(2) 1 calc R . P B 1
N5 N 0.87747(18) 0.7007(8) 0.36304(17) 0.0167(7) Uani 0.783(2) 1 d . U P B 1
H5 H 0.887(2) 0.634(9) 0.400(2) 0.020 Uiso 0.783(2) 1 d R . P B 1
N6 N 0.73982(17) -0.3024(7) 0.47698(16) 0.0151(6) Uani 0.783(2) 1 d . U P B 1
H6 H 0.708(2) -0.327(9) 0.450(2) 0.018 Uiso 0.783(2) 1 d R . P B 1
C28 C 0.6938(2) 0.1420(10) 0.3079(2) 0.0147(9) Uani 0.783(2) 1 d . U P B 1
C29 C 0.7361(2) 0.3588(8) 0.29426(18) 0.0130(7) Uani 0.783(2) 1 d . U P B 1
C30 C 0.7895(2) 0.4157(9) 0.3384(2) 0.0135(8) Uani 0.783(2) 1 d . U P B 1
C31 C 0.80145(18) 0.2670(10) 0.3954(2) 0.0142(7) Uani 0.783(2) 1 d . U P B 1
C32 C 0.7598(2) 0.0497(10) 0.4074(2) 0.0150(9) Uani 0.783(2) 1 d . U P B 1
C33 C 0.7049(2) -0.0150(9) 0.3649(2) 0.0158(9) Uani 0.783(2) 1 d . U P B 1
C34 C 0.64119(17) 0.0854(8) 0.26937(17) 0.0157(7) Uani 0.783(2) 1 d . U P B 1
H34 H 0.6146 -0.0541 0.2802 0.019 Uiso 0.783(2) 1 calc R . P B 1
C41 C 0.82733(17) 0.6261(7) 0.32503(17) 0.0157(7) Uani 0.783(2) 1 d . U P B 1
H41 H 0.8176 0.7214 0.2876 0.019 Uiso 0.783(2) 1 calc R . P B 1
C48 C 0.77379(18) -0.1009(7) 0.45971(16) 0.0152(7) Uani 0.783(2) 1 d . U P B 1
H48 H 0.8107 -0.0571 0.4855 0.018 Uiso 0.783(2) 1 calc R . P B 1
C7A C 0.2321(8) 0.601(3) 0.5361(7) 0.017(3) Uani 0.183(3) 1 d . U P A 2
H7A H 0.1945 0.5612 0.5110 0.020 Uiso 0.183(3) 1 calc R . P A 2
N4A N 0.6140(6) 0.130(3) 0.2293(6) 0.0156(6) Uani 0.217(2) 1 d . U P B 2
C14A C 0.3657(8) 0.414(3) 0.7274(8) 0.018(3) Uani 0.183(3) 1 d . U P A 2
H14A H 0.3931 0.5506 0.7167 0.021 Uiso 0.183(3) 1 calc R . P A 2
O6A O 0.6467(5) -0.143(2) 0.3310(5) 0.0185(5) Uani 0.217(2) 1 d . U P B 2
H6A H 0.6572 -0.3067 0.3310 0.028 Uiso 0.217(2) 1 calc GR . P B 2
N3A N 0.1309(9) -0.192(4) 0.6350(8) 0.0156(7) Uani 0.183(3) 1 d . U P A 2
C21A C 0.1804(7) -0.122(3) 0.6719(7) 0.015(3) Uani 0.183(3) 1 d . U P A 2
H21A H 0.1907 -0.2196 0.7090 0.018 Uiso 0.183(3) 1 calc R . P A 2
C41A C 0.8515(7) 0.526(3) 0.3764(6) 0.019(3) Uani 0.217(2) 1 d . U P B 2
H41A H 0.8770 0.4962 0.4140 0.023 Uiso 0.217(2) 1 calc R . P B 2
O4A O 0.7702(5) 0.568(2) 0.2679(5) 0.0198(6) Uani 0.217(2) 1 d . U P B 2
H4A H 0.7422 0.5503 0.2383 0.030 Uiso 0.217(2) 1 calc GR . P B 2
O2A O 0.2826(6) 0.005(3) 0.7521(5) 0.022(3) Uani 0.183(3) 1 d . U P A 2
H2A H 0.3127 -0.0989 0.7498 0.032 Uiso 0.183(3) 1 calc GR . P A 2
N1A N 0.2697(8) 0.802(3) 0.5193(8) 0.0165(6) Uani 0.183(3) 1 d . U P A 2
C2A C 0.2992(9) 0.519(3) 0.6304(10) 0.008(3) Uani 0.183(3) 1 d . U P A 2
C48A C 0.7264(6) -0.217(3) 0.4354(6) 0.016(3) Uani 0.217(2) 1 d . U P B 2
H48A H 0.6901 -0.3224 0.4260 0.019 Uiso 0.217(2) 1 calc R . P B 2
C6A C 0.2069(8) 0.240(4) 0.6025(9) 0.013(3) Uani 0.183(3) 1 d . U P A 2
C1A C 0.2482(10) 0.455(4) 0.5892(8) 0.010(3) Uani 0.183(3) 1 d . U P A 2
C5A C 0.2187(9) 0.093(3) 0.6577(10) 0.006(3) Uani 0.183(3) 1 d . U P A 2
O5A O 0.8285(5) 0.127(2) 0.4550(4) 0.0191(5) Uani 0.217(2) 1 d . U P B 2
H5A H 0.8196 -0.0139 0.4736 0.029 Uiso 0.217(2) 1 calc GR . P B 2
O1A O 0.3381(6) 0.707(2) 0.6206(5) 0.021(3) Uani 0.183(3) 1 d . U P A 2
H1A H 0.3732 0.6384 0.6199 0.031 Uiso 0.183(3) 1 calc GR . P A 2
O3A O 0.1591(6) 0.184(3) 0.5619(6) 0.024(3) Uani 0.183(3) 1 d . U P A 2
H3A H 0.1426 0.0388 0.5716 0.035 Uiso 0.183(3) 1 calc GR . P A 2
N5A N 0.8665(7) 0.717(3) 0.3405(7) 0.0167(7) Uani 0.217(2) 1 d . U P B 2
N6A N 0.7645(7) -0.267(3) 0.4871(7) 0.0151(6) Uani 0.217(2) 1 d . U P B 2
N2A N 0.3794(8) 0.277(3) 0.7806(7) 0.0165(6) Uani 0.183(3) 1 d . U P A 2
C32A C 0.7397(8) -0.008(3) 0.3950(7) 0.005(3) Uani 0.217(2) 1 d . U P B 2
C31A C 0.7911(7) 0.155(4) 0.4075(6) 0.009(2) Uani 0.217(2) 1 d . U P B 2
C28A C 0.7060(8) 0.218(4) 0.2971(7) 0.007(3) Uani 0.217(2) 1 d . U P B 2
C30A C 0.8014(7) 0.367(3) 0.3626(9) 0.008(3) Uani 0.217(2) 1 d . U P B 2
C29A C 0.7621(8) 0.398(3) 0.3091(8) 0.010(3) Uani 0.217(2) 1 d . U P B 2
C33A C 0.6961(7) 0.010(3) 0.3407(7) 0.004(3) Uani 0.217(2) 1 d . U P B 2
C4A C 0.2718(10) 0.147(4) 0.7017(9) 0.014(3) Uani 0.183(3) 1 d . U P A 2
C3A C 0.3112(9) 0.357(5) 0.6874(9) 0.011(3) Uani 0.183(3) 1 d . U P A 2
C34A C 0.6663(6) 0.275(3) 0.2449(6) 0.014(2) Uani 0.217(2) 1 d . U P B 2
H34A H 0.6760 0.4194 0.2193 0.017 Uiso 0.217(2) 1 calc R . P B 2


_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
F1 C9 1.338(4) . ?
F2 C10 1.333(4) . ?
F3 C11 1.335(3) . ?
F4 C12 1.339(4) . ?
F5 C13 1.339(4) . ?
F6 C16 1.359(3) . ?
F7 C17 1.345(4) . ?
F8 C18 1.328(3) . ?
F9 C19 1.329(3) . ?
F10 C20 1.345(4) . ?
F11 C23 1.332(4) . ?
F12 C24 1.333(4) . ?
F13 C25 1.337(4) . ?
F14 C26 1.327(4) . ?
F15 C27 1.338(4) . ?
C8 C9 1.384(4) . ?
C8 C13 1.382(5) . ?
C8 N1 1.398(4) . ?
C8 N1A 1.483(17) . ?
C9 C10 1.382(4) . ?
C10 C11 1.379(5) . ?
C11 C12 1.373(4) . ?
C12 C13 1.384(4) . ?
C15 C16 1.380(5) . ?
C15 C20 1.390(4) . ?
C15 N2 1.403(4) . ?
C15 N2A 1.450(17) . ?
C16 C17 1.366(5) . ?
C17 C18 1.378(4) . ?
C18 C19 1.386(4) . ?
C19 C20 1.371(5) . ?
C22 C23 1.398(4) . ?
C22 C27 1.372(4) . ?
C22 N3 1.407(4) . ?
C22 N3A 1.426(19) . ?
C23 C24 1.384(4) . ?
C24 C25 1.371(5) . ?
C25 C26 1.382(5) . ?
C26 C27 1.386(5) . ?
O1 C2 1.249(5) . ?
O2 C4 1.257(5) . ?
O3 C6 1.261(5) . ?
N1 H1 0.82(4) . ?
N1 C7 1.328(5) . ?
N2 H2 0.82(5) . ?
N2 C14 1.333(5) . ?
N3 H3 0.8800 . ?
N3 C21 1.345(5) . ?
C1 C2 1.464(6) . ?
C1 C6 1.455(6) . ?
C1 C7 1.380(5) . ?
C2 C3 1.467(6) . ?
C3 C4 1.451(7) . ?
C3 C14 1.364(6) . ?
C4 C5 1.463(6) . ?
C5 C6 1.450(6) . ?
C5 C21 1.375(5) . ?
C7 H7 0.9500 . ?
C14 H14 0.9500 . ?
C21 H21 0.9500 . ?
F16 C36 1.338(3) . ?
F17 C37 1.326(4) . ?
F18 C38 1.330(3) . ?
F19 C39 1.334(4) . ?
F20 C40 1.350(3) . ?
F21 C43 1.336(4) . ?
F22 C44 1.338(4) . ?
F23 C45 1.339(4) . ?
F24 C46 1.335(4) . ?
F25 C47 1.332(4) . ?
F26 C50 1.349(4) . ?
F27 C51 1.333(4) . ?
F28 C52 1.340(3) . ?
F29 C53 1.336(4) . ?
F30 C54 1.335(3) . ?
C35 C36 1.388(4) . ?
C35 C40 1.390(4) . ?
C35 N4 1.397(5) . ?
C35 N4A 1.435(14) . ?
C36 C37 1.378(4) . ?
C37 C38 1.381(4) . ?
C38 C39 1.368(4) . ?
C39 C40 1.381(4) . ?
C42 C43 1.386(4) . ?
C42 C47 1.388(5) . ?
C42 N5 1.394(5) . ?
C42 N5A 1.488(16) . ?
C43 C44 1.382(4) . ?
C44 C45 1.374(5) . ?
C45 C46 1.360(5) . ?
C46 C47 1.379(5) . ?
C49 C50 1.394(4) . ?
C49 C54 1.393(4) . ?
C49 N6 1.404(4) . ?
C49 N6A 1.396(15) . ?
C50 C51 1.373(4) . ?
C51 C52 1.373(5) . ?
C52 C53 1.381(4) . ?
C53 C54 1.382(4) . ?
O4 C29 1.245(5) . ?
O5 C31 1.256(5) . ?
O6 C33 1.245(5) . ?
N4 H4 0.8800 . ?
N4 C34 1.335(5) . ?
N5 H5 0.88(5) . ?
N5 C41 1.344(5) . ?
N6 H6 0.86(5) . ?
N6 C48 1.323(5) . ?
C28 C29 1.468(6) . ?
C28 C33 1.469(6) . ?
C28 C34 1.368(6) . ?
C29 C30 1.449(6) . ?
C30 C31 1.449(6) . ?
C30 C41 1.381(6) . ?
C31 C32 1.450(7) . ?
C32 C33 1.460(7) . ?
C32 C48 1.373(6) . ?
C34 H34 0.9500 . ?
C41 H41 0.9500 . ?
C48 H48 0.9500 . ?
C7A H7A 0.9500 . ?
C7A N1A 1.37(2) . ?
C7A C1A 1.38(2) . ?
N4A C34A 1.355(19) . ?
C14A H14A 0.9500 . ?
C14A N2A 1.35(2) . ?
C14A C3A 1.42(3) . ?
O6A H6A 0.8400 . ?
O6A C33A 1.312(17) . ?
N3A C21A 1.31(2) . ?
C21A H21A 0.9500 . ?
C21A C5A 1.41(2) . ?
C41A H41A 0.9500 . ?
C41A N5A 1.30(2) . ?
C41A C30A 1.35(2) . ?
O4A H4A 0.8400 . ?
O4A C29A 1.267(17) . ?
O2A H2A 0.8400 . ?
O2A C4A 1.31(2) . ?
C2A C1A 1.38(3) . ?
C2A O1A 1.29(2) . ?
C2A C3A 1.48(3) . ?
C48A H48A 0.9500 . ?
C48A N6A 1.346(19) . ?
C48A C32A 1.413(19) . ?
C6A C1A 1.45(3) . ?
C6A C5A 1.41(3) . ?
C6A O3A 1.32(2) . ?
C5A C4A 1.44(3) . ?
O5A H5A 0.8400 . ?
O5A C31A 1.251(17) . ?
O1A H1A 0.8400 . ?
O3A H3A 0.8400 . ?
C32A C31A 1.38(2) . ?
C32A C33A 1.43(2) . ?
C31A C30A 1.48(2) . ?
C28A C29A 1.51(2) . ?
C28A C33A 1.44(2) . ?
C28A C34A 1.38(2) . ?
C30A C29A 1.38(2) . ?
C4A C3A 1.41(3) . ?
C34A H34A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C8 N1 114.3(3) . . ?
C9 C8 N1A 138.3(7) . . ?
C13 C8 C9 116.7(3) . . ?
C13 C8 N1 129.0(3) . . ?
C13 C8 N1A 104.8(7) . . ?
F1 C9 C8 119.5(3) . . ?
F1 C9 C10 118.0(3) . . ?
C10 C9 C8 122.4(3) . . ?
F2 C10 C9 119.9(3) . . ?
F2 C10 C11 120.4(3) . . ?
C11 C10 C9 119.6(3) . . ?
F3 C11 C10 121.3(3) . . ?
F3 C11 C12 119.7(3) . . ?
C12 C11 C10 119.0(3) . . ?
F4 C12 C11 119.9(3) . . ?
F4 C12 C13 119.5(3) . . ?
C11 C12 C13 120.7(3) . . ?
F5 C13 C8 120.7(3) . . ?
F5 C13 C12 117.7(3) . . ?
C8 C13 C12 121.5(3) . . ?
C16 C15 C20 115.6(3) . . ?
C16 C15 N2 116.1(3) . . ?
C16 C15 N2A 142.1(7) . . ?
C20 C15 N2 128.3(3) . . ?
C20 C15 N2A 102.3(7) . . ?
F6 C16 C15 118.5(3) . . ?
F6 C16 C17 117.9(3) . . ?
C17 C16 C15 123.6(3) . . ?
F7 C17 C16 120.2(3) . . ?
F7 C17 C18 119.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
F8 C18 C17 121.9(3) . . ?
F8 C18 C19 119.7(3) . . ?
C17 C18 C19 118.4(3) . . ?
F9 C19 C18 119.8(3) . . ?
F9 C19 C20 119.6(3) . . ?
C20 C19 C18 120.6(3) . . ?
F10 C20 C15 120.5(3) . . ?
F10 C20 C19 117.4(3) . . ?
C19 C20 C15 122.0(3) . . ?
C23 C22 N3 114.3(3) . . ?
C23 C22 N3A 135.9(7) . . ?
C27 C22 C23 116.9(3) . . ?
C27 C22 N3 128.8(3) . . ?
C27 C22 N3A 107.1(7) . . ?
F11 C23 C22 119.6(3) . . ?
F11 C23 C24 119.0(3) . . ?
C24 C23 C22 121.4(3) . . ?
F12 C24 C23 119.2(3) . . ?
F12 C24 C25 120.8(3) . . ?
C25 C24 C23 120.0(3) . . ?
F13 C25 C24 120.2(3) . . ?
F13 C25 C26 119.9(3) . . ?
C24 C25 C26 119.9(3) . . ?
F14 C26 C25 119.9(3) . . ?
F14 C26 C27 120.9(3) . . ?
C25 C26 C27 119.2(3) . . ?
F15 C27 C22 120.1(3) . . ?
F15 C27 C26 117.4(3) . . ?
C22 C27 C26 122.5(3) . . ?
C8 N1 H1 118(3) . . ?
C7 N1 C8 128.8(4) . . ?
C7 N1 H1 113(3) . . ?
C15 N2 H2 115(3) . . ?
C14 N2 C15 126.7(3) . . ?
C14 N2 H2 118(3) . . ?
C22 N3 H3 116.6 . . ?
C21 N3 C22 126.7(3) . . ?
C21 N3 H3 116.6 . . ?
C6 C1 C2 121.0(4) . . ?
C7 C1 C2 118.0(4) . . ?
C7 C1 C6 121.0(4) . . ?
O1 C2 C1 121.2(4) . . ?
O1 C2 C3 120.5(4) . . ?
C1 C2 C3 118.3(4) . . ?
C4 C3 C2 121.5(4) . . ?
C14 C3 C2 121.3(4) . . ?
C14 C3 C4 117.3(4) . . ?
O2 C4 C3 120.7(5) . . ?
O2 C4 C5 120.5(4) . . ?
C3 C4 C5 118.9(4) . . ?
C6 C5 C4 120.9(4) . . ?
C21 C5 C4 121.4(4) . . ?
C21 C5 C6 117.6(4) . . ?
O3 C6 C1 121.1(4) . . ?
O3 C6 C5 119.4(4) . . ?
C5 C6 C1 119.5(3) . . ?
N1 C7 C1 122.2(4) . . ?
N1 C7 H7 118.9 . . ?
C1 C7 H7 118.9 . . ?
N2 C14 C3 124.3(4) . . ?
N2 C14 H14 117.9 . . ?
C3 C14 H14 117.9 . . ?
N3 C21 C5 123.0(4) . . ?
N3 C21 H21 118.5 . . ?
C5 C21 H21 118.5 . . ?
C36 C35 C40 116.1(3) . . ?
C36 C35 N4 130.6(3) . . ?
C36 C35 N4A 106.4(6) . . ?
C40 C35 N4 113.3(3) . . ?
C40 C35 N4A 137.5(6) . . ?
F16 C36 C35 119.4(3) . . ?
F16 C36 C37 118.6(3) . . ?
C37 C36 C35 121.9(3) . . ?
F17 C37 C36 119.5(3) . . ?
F17 C37 C38 120.1(3) . . ?
C36 C37 C38 120.4(3) . . ?
F18 C38 C37 121.4(3) . . ?
F18 C38 C39 119.5(3) . . ?
C39 C38 C37 119.1(3) . . ?
F19 C39 C38 120.3(3) . . ?
F19 C39 C40 119.8(3) . . ?
C38 C39 C40 119.9(3) . . ?
F20 C40 C35 119.4(3) . . ?
F20 C40 C39 118.0(3) . . ?
C39 C40 C35 122.6(3) . . ?
C43 C42 C47 116.9(3) . . ?
C43 C42 N5 129.2(3) . . ?
C43 C42 N5A 108.3(6) . . ?
C47 C42 N5 114.0(3) . . ?
C47 C42 N5A 134.8(6) . . ?
F21 C43 C42 120.9(3) . . ?
F21 C43 C44 118.0(3) . . ?
C44 C43 C42 121.1(3) . . ?
F22 C44 C43 119.2(3) . . ?
F22 C44 C45 120.3(3) . . ?
C45 C44 C43 120.5(3) . . ?
F23 C45 C44 119.5(3) . . ?
F23 C45 C46 121.1(3) . . ?
C46 C45 C44 119.5(3) . . ?
F24 C46 C45 120.1(3) . . ?
F24 C46 C47 119.8(3) . . ?
C45 C46 C47 120.2(3) . . ?
F25 C47 C42 118.0(3) . . ?
F25 C47 C46 120.1(3) . . ?
C46 C47 C42 121.9(3) . . ?
C50 C49 N6 129.1(3) . . ?
C50 C49 N6A 105.3(6) . . ?
C54 C49 C50 115.9(3) . . ?
C54 C49 N6 115.0(3) . . ?
C54 C49 N6A 138.8(6) . . ?
F26 C50 C49 120.1(3) . . ?
F26 C50 C51 117.5(3) . . ?
C51 C50 C49 122.4(3) . . ?
F27 C51 C50 119.4(3) . . ?
F27 C51 C52 120.3(3) . . ?
C52 C51 C50 120.3(3) . . ?
F28 C52 C51 120.9(3) . . ?
F28 C52 C53 119.8(3) . . ?
C51 C52 C53 119.2(3) . . ?
F29 C53 C52 120.3(3) . . ?
F29 C53 C54 119.9(3) . . ?
C52 C53 C54 119.8(3) . . ?
F30 C54 C49 119.5(3) . . ?
F30 C54 C53 118.2(3) . . ?
C53 C54 C49 122.3(3) . . ?
C35 N4 H4 115.8 . . ?
C34 N4 C35 128.3(4) . . ?
C34 N4 H4 115.8 . . ?
C42 N5 H5 108(3) . . ?
C41 N5 C42 127.8(4) . . ?
C41 N5 H5 123(3) . . ?
C49 N6 H6 123(3) . . ?
C48 N6 C49 127.4(4) . . ?
C48 N6 H6 110(3) . . ?
C29 C28 C33 121.2(4) . . ?
C34 C28 C29 121.4(4) . . ?
C34 C28 C33 117.3(5) . . ?
O4 C29 C28 120.5(4) . . ?
O4 C29 C30 121.0(4) . . ?
C30 C29 C28 118.5(4) . . ?
C29 C30 C31 121.8(4) . . ?
C41 C30 C29 117.0(5) . . ?
C41 C30 C31 121.1(4) . . ?
O5 C31 C30 121.3(4) . . ?
O5 C31 C32 119.9(5) . . ?
C30 C31 C32 118.8(4) . . ?
C31 C32 C33 121.9(4) . . ?
C48 C32 C31 118.2(5) . . ?
C48 C32 C33 119.9(5) . . ?
O6 C33 C28 120.1(5) . . ?
O6 C33 C32 122.1(5) . . ?
C32 C33 C28 117.9(4) . . ?
N4 C34 C28 122.1(4) . . ?
N4 C34 H34 118.9 . . ?
C28 C34 H34 118.9 . . ?
N5 C41 C30 122.3(4) . . ?
N5 C41 H41 118.8 . . ?
C30 C41 H41 118.8 . . ?
N6 C48 C32 125.0(4) . . ?
N6 C48 H48 117.5 . . ?
C32 C48 H48 117.5 . . ?
N1A C7A H7A 119.7 . . ?
N1A C7A C1A 120.6(17) . . ?
C1A C7A H7A 119.7 . . ?
C34A N4A C35 121.0(11) . . ?
N2A C14A H14A 119.4 . . ?
N2A C14A C3A 121.3(18) . . ?
C3A C14A H14A 119.4 . . ?
C33A O6A H6A 109.5 . . ?
C21A N3A C22 124.5(15) . . ?
N3A C21A H21A 119.2 . . ?
N3A C21A C5A 121.6(17) . . ?
C5A C21A H21A 119.2 . . ?
N5A C41A H41A 118.5 . . ?
N5A C41A C30A 122.9(15) . . ?
C30A C41A H41A 118.5 . . ?
C29A O4A H4A 109.5 . . ?
C4A O2A H2A 109.5 . . ?
C7A N1A C8 118.1(14) . . ?
C1A C2A C3A 118.4(16) . . ?
O1A C2A C1A 123.1(19) . . ?
O1A C2A C3A 118(2) . . ?
N6A C48A H48A 119.5 . . ?
N6A C48A C32A 121.0(14) . . ?
C32A C48A H48A 119.5 . . ?
C5A C6A C1A 119.9(17) . . ?
O3A C6A C1A 119(2) . . ?
O3A C6A C5A 121.5(19) . . ?
C7A C1A C2A 122(2) . . ?
C7A C1A C6A 117.0(19) . . ?
C2A C1A C6A 120.4(17) . . ?
C21A C5A C4A 116.0(18) . . ?
C6A C5A C21A 121.8(19) . . ?
C6A C5A C4A 122.1(17) . . ?
C31A O5A H5A 109.5 . . ?
C2A O1A H1A 109.5 . . ?
C6A O3A H3A 109.5 . . ?
C41A N5A C42 125.2(12) . . ?
C48A N6A C49 123.1(12) . . ?
C14A N2A C15 119.9(15) . . ?
C48A C32A C33A 113.9(14) . . ?
C31A C32A C48A 121.5(15) . . ?
C31A C32A C33A 124.6(14) . . ?
O5A C31A C32A 122.1(16) . . ?
O5A C31A C30A 120.2(16) . . ?
C32A C31A C30A 117.7(13) . . ?
C33A C28A C29A 119.1(14) . . ?
C34A C28A C29A 116.0(15) . . ?
C34A C28A C33A 124.9(16) . . ?
C41A C30A C31A 116.5(16) . . ?
C41A C30A C29A 122.0(16) . . ?
C29A C30A C31A 121.5(13) . . ?
O4A C29A C28A 116.6(17) . . ?
O4A C29A C30A 124.0(16) . . ?
C30A C29A C28A 119.4(13) . . ?
O6A C33A C32A 123.0(14) . . ?
O6A C33A C28A 119.2(14) . . ?
C32A C33A C28A 117.6(14) . . ?
O2A C4A C5A 121(2) . . ?
O2A C4A C3A 122.3(19) . . ?
C3A C4A C5A 116.6(18) . . ?
C14A C3A C2A 117.9(19) . . ?
C4A C3A C14A 119.6(19) . . ?
C4A C3A C2A 122.5(18) . . ?
N4A C34A C28A 121.8(14) . . ?
N4A C34A H34A 119.1 . . ?
C28A C34A H34A 119.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.82(4) 1.87(4) 2.569(5) 142(4) .
N2 H2 O1 0.82(5) 1.97(4) 2.607(4) 133(4) .
N3 H3 O2 0.88 1.89 2.589(5) 134.7 .
C7 H7 F5 0.95 2.32 2.939(4) 122.6 .
C14 H14 F10 0.95 2.21 2.877(4) 126.2 .
C21 H21 F15 0.95 2.23 2.871(4) 124.3 .
N4 H4 O4 0.88 1.86 2.567(5) 136.3 .
N5 H5 O5 0.88(5) 1.96(4) 2.575(5) 126(4) .
N6 H6 O6 0.86(5) 1.87(5) 2.611(5) 143(4) .
C34 H34 F16 0.95 2.35 2.965(4) 121.9 .
C41 H41 F21 0.95 2.30 2.930(4) 123.0 .
C48 H48 F26 0.95 2.24 2.908(4) 126.2 .
O5A H5A N6A 0.84 1.78 2.544(18) 149.4 .
O3A H3A N3A 0.84 1.85 2.58(2) 145.4 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C9 C10 F2 1.0(4) . . . . ?
F1 C9 C10 C11 179.4(3) . . . . ?
F2 C10 C11 F3 0.6(5) . . . . ?
F2 C10 C11 C12 179.3(3) . . . . ?
F3 C11 C12 F4 -1.0(4) . . . . ?
F3 C11 C12 C13 178.6(3) . . . . ?
F4 C12 C13 F5 -0.6(4) . . . . ?
F4 C12 C13 C8 179.0(3) . . . . ?
F6 C16 C17 F7 2.9(4) . . . . ?
F6 C16 C17 C18 -179.8(3) . . . . ?
F7 C17 C18 F8 -2.0(5) . . . . ?
F7 C17 C18 C19 177.4(3) . . . . ?
F8 C18 C19 F9 -0.6(4) . . . . ?
F8 C18 C19 C20 179.1(3) . . . . ?
F9 C19 C20 F10 -1.9(4) . . . . ?
F9 C19 C20 C15 -179.5(3) . . . . ?
F11 C23 C24 F12 -0.1(5) . . . . ?
F11 C23 C24 C25 -179.3(3) . . . . ?
F12 C24 C25 F13 1.1(5) . . . . ?
F12 C24 C25 C26 -178.9(3) . . . . ?
F13 C25 C26 F14 0.0(5) . . . . ?
F13 C25 C26 C27 -179.6(3) . . . . ?
F14 C26 C27 F15 0.5(5) . . . . ?
F14 C26 C27 C22 179.0(3) . . . . ?
C8 C9 C10 F2 -179.4(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C8 N1 C7 C1 179.3(3) . . . . ?
C9 C8 C13 F5 -179.9(3) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C9 C8 N1 C7 -176.9(3) . . . . ?
C9 C8 N1A C7A -8(2) . . . . ?
C9 C10 C11 F3 -177.7(3) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 F4 -179.7(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 F5 179.8(3) . . . . ?
C11 C12 C13 C8 -0.6(5) . . . . ?
C13 C8 C9 F1 179.9(3) . . . . ?
C13 C8 C9 C10 0.4(5) . . . . ?
C13 C8 N1 C7 3.1(6) . . . . ?
C13 C8 N1A C7A 177.0(12) . . . . ?
C15 C16 C17 F7 -177.6(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C15 N2 C14 C3 -178.9(4) . . . . ?
C16 C15 C20 F10 -178.6(3) . . . . ?
C16 C15 C20 C19 -1.0(5) . . . . ?
C16 C15 N2 C14 -179.5(3) . . . . ?
C16 C15 N2A C14A 11(2) . . . . ?
C16 C17 C18 F8 -179.3(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 F9 180.0(3) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C18 C19 C20 F10 178.5(3) . . . . ?
C18 C19 C20 C15 0.8(5) . . . . ?
C20 C15 C16 F6 -179.8(3) . . . . ?
C20 C15 C16 C17 0.8(5) . . . . ?
C20 C15 N2 C14 1.5(6) . . . . ?
C20 C15 N2A C14A -173.3(13) . . . . ?
C22 C23 C24 F12 179.2(3) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C22 N3 C21 C5 -178.6(4) . . . . ?
C22 N3A C21A C5A 179.4(14) . . . . ?
C23 C22 C27 F15 -179.9(3) . . . . ?
C23 C22 C27 C26 1.6(5) . . . . ?
C23 C22 N3 C21 -178.6(3) . . . . ?
C23 C22 N3A C21A 3(2) . . . . ?
C23 C24 C25 F13 -179.7(3) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C24 C25 C26 F14 180.0(3) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C26 C27 F15 -179.9(3) . . . . ?
C25 C26 C27 C22 -1.4(5) . . . . ?
C27 C22 C23 F11 178.4(3) . . . . ?
C27 C22 C23 C24 -0.9(5) . . . . ?
C27 C22 N3 C21 2.7(6) . . . . ?
C27 C22 N3A C21A -175.5(15) . . . . ?
O1 C2 C3 C4 178.9(4) . . . . ?
O1 C2 C3 C14 -2.8(6) . . . . ?
O2 C4 C5 C6 178.8(3) . . . . ?
O2 C4 C5 C21 -2.9(6) . . . . ?
N1 C8 C9 F1 0.0(4) . . . . ?
N1 C8 C9 C10 -179.6(3) . . . . ?
N1 C8 C13 F5 0.0(5) . . . . ?
N1 C8 C13 C12 -179.6(3) . . . . ?
N2 C15 C16 F6 1.0(4) . . . . ?
N2 C15 C16 C17 -178.4(3) . . . . ?
N2 C15 C20 F10 0.5(5) . . . . ?
N2 C15 C20 C19 178.1(3) . . . . ?
N3 C22 C23 F11 -0.4(4) . . . . ?
N3 C22 C23 C24 -179.7(3) . . . . ?
N3 C22 C27 F15 -1.3(5) . . . . ?
N3 C22 C27 C26 -179.8(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C1 C2 C3 C14 178.0(4) . . . . ?
C2 C1 C6 O3 178.9(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C7 N1 179.6(3) . . . . ?
C2 C3 C4 O2 -179.2(4) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C2 C3 C14 N2 0.9(6) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C3 C4 C5 C21 177.1(4) . . . . ?
C4 C3 C14 N2 179.3(4) . . . . ?
C4 C5 C6 O3 -178.4(4) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C21 N3 1.7(6) . . . . ?
C6 C1 C2 O1 -179.1(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C6 C1 C7 N1 -1.6(6) . . . . ?
C6 C5 C21 N3 -180.0(3) . . . . ?
C7 C1 C2 O1 -0.2(5) . . . . ?
C7 C1 C2 C3 179.0(3) . . . . ?
C7 C1 C6 O3 0.1(6) . . . . ?
C7 C1 C6 C5 -179.3(4) . . . . ?
C14 C3 C4 O2 2.5(6) . . . . ?
C14 C3 C4 C5 -177.5(4) . . . . ?
C21 C5 C6 O3 3.2(5) . . . . ?
C21 C5 C6 C1 -177.4(3) . . . . ?
F16 C36 C37 F17 -0.6(4) . . . . ?
F16 C36 C37 C38 -179.3(3) . . . . ?
F17 C37 C38 F18 1.1(5) . . . . ?
F17 C37 C38 C39 -178.3(3) . . . . ?
F18 C38 C39 F19 1.3(5) . . . . ?
F18 C38 C39 C40 179.6(3) . . . . ?
F19 C39 C40 F20 -0.5(4) . . . . ?
F19 C39 C40 C35 179.0(3) . . . . ?
F21 C43 C44 F22 0.8(4) . . . . ?
F21 C43 C44 C45 -179.9(3) . . . . ?
F22 C44 C45 F23 -1.1(5) . . . . ?
F22 C44 C45 C46 178.0(3) . . . . ?
F23 C45 C46 F24 -1.5(5) . . . . ?
F23 C45 C46 C47 179.2(3) . . . . ?
F24 C46 C47 F25 1.6(5) . . . . ?
F24 C46 C47 C42 -178.5(3) . . . . ?
F26 C50 C51 F27 -0.1(5) . . . . ?
F26 C50 C51 C52 179.8(3) . . . . ?
F27 C51 C52 F28 -1.7(5) . . . . ?
F27 C51 C52 C53 -179.9(3) . . . . ?
F28 C52 C53 F29 1.0(4) . . . . ?
F28 C52 C53 C54 -179.4(3) . . . . ?
F29 C53 C54 F30 -0.1(4) . . . . ?
F29 C53 C54 C49 -179.5(3) . . . . ?
C35 C36 C37 F17 179.1(3) . . . . ?
C35 C36 C37 C38 0.4(5) . . . . ?
C35 N4 C34 C28 -175.1(4) . . . . ?
C35 N4A C34A C28A 178.2(12) . . . . ?
C36 C35 C40 F20 179.5(3) . . . . ?
C36 C35 C40 C39 0.0(5) . . . . ?
C36 C35 N4 C34 -7.4(6) . . . . ?
C36 C35 N4A C34A -178.9(11) . . . . ?
C36 C37 C38 F18 179.8(3) . . . . ?
C36 C37 C38 C39 0.4(5) . . . . ?
C37 C38 C39 F19 -179.2(3) . . . . ?
C37 C38 C39 C40 -1.0(5) . . . . ?
C38 C39 C40 F20 -178.7(3) . . . . ?
C38 C39 C40 C35 0.8(5) . . . . ?
C40 C35 C36 F16 179.1(3) . . . . ?
C40 C35 C36 C37 -0.6(4) . . . . ?
C40 C35 N4 C34 172.2(4) . . . . ?
C40 C35 N4A C34A -1.7(18) . . . . ?
C42 C43 C44 F22 -177.7(3) . . . . ?
C42 C43 C44 C45 1.7(5) . . . . ?
C42 N5 C41 C30 -179.1(4) . . . . ?
C43 C42 C47 F25 179.5(3) . . . . ?
C43 C42 C47 C46 -0.4(5) . . . . ?
C43 C42 N5 C41 -4.9(6) . . . . ?
C43 C42 N5A C41A 178.7(14) . . . . ?
C43 C44 C45 F23 179.5(3) . . . . ?
C43 C44 C45 C46 -1.3(5) . . . . ?
C44 C45 C46 F24 179.3(3) . . . . ?
C44 C45 C46 C47 0.1(5) . . . . ?
C45 C46 C47 F25 -179.1(3) . . . . ?
C45 C46 C47 C42 0.8(5) . . . . ?
C47 C42 C43 F21 -179.2(3) . . . . ?
C47 C42 C43 C44 -0.8(5) . . . . ?
C47 C42 N5 C41 174.1(4) . . . . ?
C47 C42 N5A C41A -1(2) . . . . ?
C49 C50 C51 F27 -178.7(3) . . . . ?
C49 C50 C51 C52 1.1(5) . . . . ?
C49 N6 C48 C32 178.3(4) . . . . ?
C50 C49 C54 F30 -179.0(3) . . . . ?
C50 C49 C54 C53 0.3(4) . . . . ?
C50 C49 N6 C48 2.1(6) . . . . ?
C50 C49 N6A C48A -179.9(12) . . . . ?
C50 C51 C52 F28 178.4(3) . . . . ?
C50 C51 C52 C53 0.2(5) . . . . ?
C51 C52 C53 F29 179.2(3) . . . . ?
C51 C52 C53 C54 -1.3(5) . . . . ?
C52 C53 C54 F30 -179.7(3) . . . . ?
C52 C53 C54 C49 1.0(5) . . . . ?
C54 C49 C50 F26 -180.0(3) . . . . ?
C54 C49 C50 C51 -1.4(4) . . . . ?
C54 C49 N6 C48 -178.3(3) . . . . ?
C54 C49 N6A C48A 4.2(19) . . . . ?
O4 C29 C30 C31 178.6(4) . . . . ?
O4 C29 C30 C41 1.1(6) . . . . ?
O5 C31 C32 C33 178.3(4) . . . . ?
O5 C31 C32 C48 -3.0(6) . . . . ?
N4 C35 C36 F16 -1.2(5) . . . . ?
N4 C35 C36 C37 179.1(3) . . . . ?
N4 C35 C40 F20 -0.2(4) . . . . ?
N4 C35 C40 C39 -179.7(3) . . . . ?
N5 C42 C43 F21 -0.2(5) . . . . ?
N5 C42 C43 C44 178.2(3) . . . . ?
N5 C42 C47 F25 0.4(5) . . . . ?
N5 C42 C47 C46 -179.6(3) . . . . ?
N6 C49 C50 F26 -0.3(5) . . . . ?
N6 C49 C50 C51 178.3(3) . . . . ?
N6 C49 C54 F30 1.3(4) . . . . ?
N6 C49 C54 C53 -179.4(3) . . . . ?
C28 C29 C30 C31 -0.7(5) . . . . ?
C28 C29 C30 C41 -178.2(4) . . . . ?
C29 C28 C33 O6 -179.3(4) . . . . ?
C29 C28 C33 C32 -0.6(6) . . . . ?
C29 C28 C34 N4 1.2(6) . . . . ?
C29 C30 C31 O5 -179.0(4) . . . . ?
C29 C30 C31 C32 2.0(5) . . . . ?
C29 C30 C41 N5 178.7(4) . . . . ?
C30 C31 C32 C33 -2.7(6) . . . . ?
C30 C31 C32 C48 175.9(4) . . . . ?
C31 C30 C41 N5 1.2(6) . . . . ?
C31 C32 C33 O6 -179.3(4) . . . . ?
C31 C32 C33 C28 2.0(6) . . . . ?
C31 C32 C48 N6 179.1(4) . . . . ?
C33 C28 C29 O4 -179.3(4) . . . . ?
C33 C28 C29 C30 0.0(6) . . . . ?
C33 C28 C34 N4 178.7(4) . . . . ?
C33 C32 C48 N6 -2.3(6) . . . . ?
C34 C28 C29 O4 -2.0(6) . . . . ?
C34 C28 C29 C30 177.3(4) . . . . ?
C34 C28 C33 O6 3.3(6) . . . . ?
C34 C28 C33 C32 -178.0(4) . . . . ?
C41 C30 C31 O5 -1.6(6) . . . . ?
C41 C30 C31 C32 179.4(4) . . . . ?
C48 C32 C33 O6 2.1(6) . . . . ?
C48 C32 C33 C28 -176.6(4) . . . . ?
N4A C35 C36 F16 -2.9(7) . . . . ?
N4A C35 C36 C37 177.3(6) . . . . ?
N4A C35 C40 F20 2.4(10) . . . . ?
N4A C35 C40 C39 -177.1(9) . . . . ?
N3A C22 C23 F11 -0.2(12) . . . . ?
N3A C22 C23 C24 -179.5(11) . . . . ?
N3A C22 C27 F15 -0.9(9) . . . . ?
N3A C22 C27 C26 -179.4(9) . . . . ?
N3A C21A C5A C6A -2(2) . . . . ?
N3A C21A C5A C4A -179.5(16) . . . . ?
C21A C5A C4A O2A -1(2) . . . . ?
C21A C5A C4A C3A 178.5(16) . . . . ?
C41A C30A C29A O4A 2(2) . . . . ?
C41A C30A C29A C28A -178.5(13) . . . . ?
O2A C4A C3A C14A 2(3) . . . . ?
O2A C4A C3A C2A -179.9(17) . . . . ?
N1A C8 C9 F1 5.7(11) . . . . ?
N1A C8 C9 C10 -173.8(10) . . . . ?
N1A C8 C13 F5 -3.9(8) . . . . ?
N1A C8 C13 C12 176.5(7) . . . . ?
N1A C7A C1A C2A 6(3) . . . . ?
N1A C7A C1A C6A -177.9(16) . . . . ?
C48A C32A C31A O5A 0(2) . . . . ?
C48A C32A C31A C30A 179.8(13) . . . . ?
C48A C32A C33A O6A 3(2) . . . . ?
C48A C32A C33A C28A 179.8(13) . . . . ?
C6A C5A C4A O2A -178.6(16) . . . . ?
C6A C5A C4A C3A 1(2) . . . . ?
C1A C7A N1A C8 -174.9(14) . . . . ?
C1A C2A C3A C14A 176.1(16) . . . . ?
C1A C2A C3A C4A -2(3) . . . . ?
C1A C6A C5A C21A -178.5(15) . . . . ?
C1A C6A C5A C4A -1(2) . . . . ?
C5A C6A C1A C7A -176.4(16) . . . . ?
C5A C6A C1A C2A 0(3) . . . . ?
C5A C4A C3A C14A -177.4(16) . . . . ?
C5A C4A C3A C2A 1(3) . . . . ?
O5A C31A C30A C41A -1(2) . . . . ?
O5A C31A C30A C29A 178.0(14) . . . . ?
O1A C2A C1A C7A -5(3) . . . . ?
O1A C2A C1A C6A 179.1(16) . . . . ?
O1A C2A C3A C14A -1(2) . . . . ?
O1A C2A C3A C4A -179.4(17) . . . . ?
O3A C6A C1A C7A 4(2) . . . . ?
O3A C6A C1A C2A -179.5(16) . . . . ?
O3A C6A C5A C21A 1(3) . . . . ?
O3A C6A C5A C4A 178.1(16) . . . . ?
N5A C42 C43 F21 0.7(8) . . . . ?
N5A C42 C43 C44 179.1(7) . . . . ?
N5A C42 C47 F25 -0.3(11) . . . . ?
N5A C42 C47 C46 179.7(10) . . . . ?
N5A C41A C30A C31A 179.0(14) . . . . ?
N5A C41A C30A C29A 0(2) . . . . ?
N6A C49 C50 F26 3.0(7) . . . . ?
N6A C49 C50 C51 -178.4(7) . . . . ?
N6A C49 C54 F30 -3.4(10) . . . . ?
N6A C49 C54 C53 176.0(9) . . . . ?
N6A C48A C32A C31A -2(2) . . . . ?
N6A C48A C32A C33A 177.1(13) . . . . ?
N2A C15 C16 F6 -4.0(12) . . . . ?
N2A C15 C16 C17 176.6(11) . . . . ?
N2A C15 C20 F10 4.1(7) . . . . ?
N2A C15 C20 C19 -178.3(7) . . . . ?
N2A C14A C3A C2A 179.1(16) . . . . ?
N2A C14A C3A C4A -3(3) . . . . ?
C32A C48A N6A C49 178.6(12) . . . . ?
C32A C31A C30A C41A 179.1(14) . . . . ?
C32A C31A C30A C29A -2(2) . . . . ?
C31A C32A C33A O6A -177.9(14) . . . . ?
C31A C32A C33A C28A -2(2) . . . . ?
C31A C30A C29A O4A -177.0(13) . . . . ?
C31A C30A C29A C28A 2(2) . . . . ?
C30A C41A N5A C42 175.6(13) . . . . ?
C29A C28A C33A O6A 178.6(12) . . . . ?
C29A C28A C33A C32A 2(2) . . . . ?
C29A C28A C34A N4A -179.3(13) . . . . ?
C33A C32A C31A O5A -178.3(13) . . . . ?
C33A C32A C31A C30A 1(2) . . . . ?
C33A C28A C29A O4A 176.7(13) . . . . ?
C33A C28A C29A C30A -2(2) . . . . ?
C33A C28A C34A N4A -2(2) . . . . ?
C3A C14A N2A C15 175.7(15) . . . . ?
C3A C2A C1A C7A 177.6(16) . . . . ?
C3A C2A C1A C6A 2(2) . . . . ?
C34A C28A C29A O4A -5.7(19) . . . . ?
C34A C28A C29A C30A 175.1(13) . . . . ?
C34A C28A C33A O6A 1(2) . . . . ?
C34A C28A C33A C32A -175.2(14) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1569188'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
An initial structural determination of this compound suggested the presence of 
disorder of the entire structure over a major and minor position.  In order to
investigate this further, a high quality dataset was collected using long 
exposure times and collecting to a resolution of 0.7 Å.  Even at this high 
angle, diffraction intensities and Rmerge values were still 
reasonable (approx. 0.10).

This dataset shows that the crystal contains positional disorder between the 
two possible tautomers of the structure, the ketone-enamine form, and the 
phenol-imine form.  This was modelled by having two positions for every atom 
in the structure.  Refinement of the occupancies of the two positions gave 
site occupancy factors of 0.9225(18) for the major ketone-enamine tautomer and 
0.0775(18) for the minor phenol-imine tautomer.

The major occupancy position of the molecule refined smoothly, with all 
non-hydrogen atoms refined anisotropically and no restraints necessary.
Hydrogen atoms for this position were visible in the difference map, their 
positions refined, and then fixed.

The minor occupancy position of the molecule was not as well-behaved,
which is unsurprising given its low occupancy.  It was 
necessary to refine these atoms isotropically, but no restraints were added
to any bond lengths or angles. Hydrogen atoms for this position of the molecule
were inserted at geometric positions. A description of the bond lengths is 
provided in the manuscript.

Warming the crystal used for this data collection to 230 K and collecting 
another dataset gave lower quality data.  However, it was possible to 
determine that the ratio of the two tautomeric positions was the same, 
within experimental error (92:8 ketone-enamine: phenol-imine).
;

_cell_length_a                   15.537(2)
_cell_length_b                   4.4790(7)
_cell_length_c                   14.849(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.182(4)
_cell_angle_gamma                90
_cell_volume                     1017.1(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C9 H12 N6 O3'
_chemical_formula_moiety         'C9 H12 N6 O3'
_chemical_compound_source        synthesized
_chemical_formula_weight         252.23


_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.55
_cell_measurement_temperature    90

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_max          0.43

_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528.0
_exptl_absorpt_coefficient_mu    0.128

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2, (Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'Apex2, (Bruker, 2007)'
_computing_cell_refinement       'Apex2, (Bruker, 2007)'
_computing_data_reduction        'Apex2, (Bruker, 2007)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0

_diffrn_ambient_temperature      90
_diffrn_reflns_number            20240
_reflns_number_total             3116
_diffrn_reflns_av_R_equivalents  0.029

_diffrn_reflns_theta_min         1.332
_diffrn_reflns_theta_max         30.568
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.568
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -22
_reflns_limit_h_max              21
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.95
_oxford_diffrn_Wilson_scale      67.55

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.35
_refine_diff_density_max         0.44

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0578
_refine_ls_wR_factor_ref         0.1091
_refine_ls_goodness_of_fit_ref   0.9843
_refine_ls_shift/su_max          0.0006548
_refine_ls_shift/su_mean         0.0000579

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3104
_refine_ls_R_factor_all          0.0581
_refine_ls_wR_factor_all         0.1092

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2723
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_gt          0.1054

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.16 1.45 0.355 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.78815(11) 0.9196(3) 0.62311(8) 0.0104 0.9254(18) Uani . . P . 1 .
C2 C 0.85402(9) 0.7821(3) 0.57909(9) 0.0106 0.9254(18) Uani . . P . 1 .
C3 C 0.83199(8) 0.5573(3) 0.50860(11) 0.0102 0.9254(18) Uani . . P . 1 .
C4 C 0.74116(13) 0.4811(3) 0.47987(9) 0.0105 0.9254(18) Uani . . P . 1 .
C5 C 0.67244(8) 0.6200(3) 0.52015(10) 0.0110 0.9254(18) Uani . . P . 1 .
C6 C 0.69747(9) 0.8360(3) 0.59280(10) 0.0105 0.9254(18) Uani . . P . 1 .
C7 C 0.94155(8) 0.8688(3) 0.59916(8) 0.0120 0.9254(18) Uani . . P . 1 .
C8 C 0.71474(8) 0.2756(3) 0.41044(8) 0.0122 0.9254(18) Uani . . P . 1 .
C9 C 0.63511(8) 0.9742(3) 0.63567(8) 0.0126 0.9254(18) Uani . . P . 1 .
O10 O 0.81060(6) 1.1053(2) 0.68750(6) 0.0153 0.9254(18) Uani . . P . 1 .
O11 O 0.89011(6) 0.4340(2) 0.47112(7) 0.0159 0.9254(18) Uani . . P . 1 .
O12 O 0.59297(6) 0.5584(2) 0.49266(7) 0.0169 0.9254(18) Uani . . P . 1 .
N13 N 0.97333(7) 1.0769(3) 0.65847(7) 0.0132 0.9254(18) Uani . . P . 1 .
N14 N 1.06170(8) 1.1624(4) 0.66360(9) 0.0149 0.9254(18) Uani . . P . 1 .
N15 N 0.76599(7) 0.1233(2) 0.36617(7) 0.0134 0.9254(18) Uani . . P . 1 .
N16 N 0.72717(10) -0.0608(3) 0.29263(8) 0.0143 0.9254(18) Uani . . P . 1 .
N17 N 0.55094(7) 0.9239(3) 0.62063(8) 0.0145 0.9254(18) Uani . . P . 1 .
N18 N 0.49847(10) 1.0927(4) 0.67171(11) 0.0153 0.9254(18) Uani . . P . 1 .
C21 C 0.7495(15) 0.909(3) 0.6148(10) 0.008(3) 0.0746(18) Uiso . . P . 2 .
C22 C 0.8334(12) 0.848(4) 0.5948(12) 0.010(4) 0.0746(18) Uiso . . P . 2 .
C23 C 0.8424(11) 0.641(4) 0.5331(13) 0.008(3) 0.0746(18) Uiso . . P . 2 .
C25 C 0.6892(17) 0.568(5) 0.4955(17) 0.025(5) 0.0746(18) Uiso . . P . 2 .
C24 C 0.7694(15) 0.497(4) 0.4849(13) 0.010(4) 0.0746(18) Uiso . . P . 2 .
C26 C 0.6793(11) 0.770(4) 0.5676(12) 0.005(3) 0.0746(18) Uiso . . P . 2 .
C27 C 0.9132(10) 0.992(4) 0.6338(10) 0.013(3) 0.0746(18) Uiso . . P . 2 .
C28 C 0.7674(10) 0.262(3) 0.4102(10) 0.010(3) 0.0746(18) Uiso . . P . 2 .
C29 C 0.5949(10) 0.861(3) 0.5938(10) 0.012(3) 0.0746(18) Uiso . . P . 2 .
O30 O 0.7546(8) 1.109(3) 0.6821(8) 0.018(3) 0.0746(18) Uiso . . P . 2 .
O31 O 0.9155(8) 0.533(3) 0.5073(8) 0.014(2) 0.0746(18) Uiso . . P . 2 .
O32 O 0.6068(7) 0.473(3) 0.4504(9) 0.014(2) 0.0746(18) Uiso . . P . 2 .
N33 N 0.9912(11) 0.942(4) 0.6198(11) 0.022(3) 0.0746(18) Uiso . . P . 2 .
N34 N 1.073(2) 1.069(7) 0.656(2) 0.049(9) 0.0746(18) Uiso . . P . 2 .
N35 N 0.7023(9) 0.144(3) 0.3608(10) 0.018(3) 0.0746(18) Uiso . . P . 2 .
N36 N 0.698(3) -0.070(10) 0.295(3) 0.070(13) 0.0746(18) Uiso . . P . 2 .
N37 N 0.5856(10) 1.052(3) 0.6567(10) 0.016(3) 0.0746(18) Uiso . . P . 2 .
N38 N 0.512(2) 1.160(8) 0.683(3) 0.047(11) 0.0746(18) Uiso . . P . 2 .
H71 H 0.9828 0.7696 0.5686 0.0140 0.9254(18) Uiso R . P . 1 .
H81 H 0.6541 0.2414 0.3911 0.0146 0.9254(18) Uiso R . P . 1 .
H91 H 0.6549 1.1227 0.6798 0.0153 0.9254(18) Uiso R . P . 1 .
H161 H 0.7415 -0.0057 0.2421 0.0195 0.9254(18) Uiso R . P . 1 .
H182 H 0.4744 0.9775 0.7074 0.0194 0.9254(18) Uiso R . P . 1 .
H141 H 1.0689 1.3015 0.6253 0.0180 0.9254(18) Uiso R . P . 1 .
H162 H 0.7433 -0.2420 0.3003 0.0186 0.9254(18) Uiso R . P . 1 .
H142 H 1.0829 1.2294 0.7161 0.0198 0.9254(18) Uiso R . P . 1 .
H181 H 0.4592 1.1941 0.6358 0.0189 0.9254(18) Uiso R . P . 1 .
H171 H 0.5295 0.7979 0.5791 0.0192 0.9254(18) Uiso R . P . 1 .
H131 H 0.9376 1.1841 0.6832 0.0202 0.9254(18) Uiso R . P . 1 .
H151 H 0.8218 0.1453 0.3818 0.0184 0.9254(18) Uiso R . P . 1 .
H281 H 0.8230 0.1967 0.3998 0.0158 0.0746(18) Uiso R . P . 2 .
H271 H 0.9087 1.1487 0.6758 0.0205 0.0746(18) Uiso R . P . 2 .
H291 H 0.5431 0.7704 0.5618 0.0200 0.0746(18) Uiso R . P . 2 .
H361 H 0.6694 -0.2175 0.3103 0.0880 0.0746(18) Uiso R . P . 2 .
H362 H 0.6719 -0.0009 0.2440 0.0880 0.0746(18) Uiso R . P . 2 .
H381 H 0.5133 1.1174 0.7393 0.0646 0.0746(18) Uiso R . P . 2 .
H382 H 0.5116 1.3482 0.6766 0.0646 0.0746(18) Uiso R . P . 2 .
H342 H 1.1066 0.9303 0.6814 0.0654 0.0746(18) Uiso R . P . 2 .
H341 H 1.0960 1.1499 0.6144 0.0654 0.0746(18) Uiso R . P . 2 .
H311 H 0.9626 0.6124 0.5348 0.0193 0.0746(18) Uiso R . P . 2 .
H321 H 0.6083 0.3578 0.4053 0.0202 0.0746(18) Uiso R . P . 2 .
H301 H 0.7067 1.1456 0.7001 0.0233 0.0746(18) Uiso R . P . 2 .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13806(10)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.446(2) yes
C1 . C6 . 1.450(2) yes
C1 . O10 . 1.2687(15) yes
C2 . C3 . 1.449(2) yes
C2 . C7 . 1.3950(17) yes
C3 . C4 . 1.441(2) yes
C3 . O11 . 1.2679(16) yes
C4 . C5 . 1.453(2) yes
C4 . C8 . 1.3891(18) yes
C5 . C6 . 1.450(2) yes
C5 . O12 . 1.2605(15) yes
C6 . C9 . 1.3946(16) yes
C7 . N13 . 1.3169(16) yes
C7 . H71 . 0.958 no
C8 . N15 . 1.3102(16) yes
C8 . H81 . 0.948 no
C9 . N17 . 1.3068(15) yes
C9 . H91 . 0.946 no
N13 . N14 . 1.4145(15) yes
N13 . H131 . 0.863 no
N14 . H141 . 0.864 no
N14 . H142 . 0.846 no
N15 . N16 . 1.4154(15) yes
N15 . H151 . 0.863 no
N16 . H161 . 0.856 no
N16 . H162 . 0.851 no
N17 . N18 . 1.4249(17) yes
N17 . H171 . 0.859 no
N18 . H182 . 0.870 no
N18 . H181 . 0.865 no
C21 . C22 . 1.41(3) yes
C21 . C26 . 1.34(2) yes
C21 . O30 . 1.335(19) yes
C22 . C23 . 1.32(3) yes
C22 . C27 . 1.43(2) yes
C23 . C24 . 1.39(3) yes
C23 . O31 . 1.35(2) yes
C25 . C24 . 1.32(3) yes
C25 . C26 . 1.43(3) yes
C25 . O32 . 1.40(3) yes
C24 . C28 . 1.53(2) yes
C26 . C29 . 1.49(2) yes
C27 . N33 . 1.28(2) yes
C27 . H271 . 0.950 no
C28 . N35 . 1.26(2) yes
C28 . H281 . 0.950 no
C29 . N37 . 1.30(2) yes
C29 . H291 . 0.950 no
O30 . H301 . 0.850 no
O31 . H311 . 0.850 no
O32 . H321 . 0.850 no
N33 . N34 . 1.41(4) yes
N34 . H342 . 0.850 no
N34 . H341 . 0.850 no
N35 . N36 . 1.37(4) yes
N36 . H361 . 0.850 no
N36 . H362 . 0.850 no
N37 . N38 . 1.36(4) yes
N38 . H381 . 0.850 no
N38 . H382 . 0.850 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 118.43(11) yes
C2 . C1 . O10 . 119.85(14) yes
C6 . C1 . O10 . 121.71(13) yes
C1 . C2 . C3 . 121.80(11) yes
C1 . C2 . C7 . 121.73(14) yes
C3 . C2 . C7 . 116.40(14) yes
C2 . C3 . C4 . 118.18(12) yes
C2 . C3 . O11 . 121.61(14) yes
C4 . C3 . O11 . 120.19(16) yes
C3 . C4 . C5 . 121.95(13) yes
C3 . C4 . C8 . 121.48(14) yes
C5 . C4 . C8 . 116.55(16) yes
C4 . C5 . C6 . 118.16(12) yes
C4 . C5 . O12 . 121.47(15) yes
C6 . C5 . O12 . 120.36(14) yes
C1 . C6 . C5 . 121.41(11) yes
C1 . C6 . C9 . 117.32(14) yes
C5 . C6 . C9 . 121.27(14) yes
C2 . C7 . N13 . 125.18(13) yes
C2 . C7 . H71 . 118.6 no
N13 . C7 . H71 . 116.3 no
C4 . C8 . N15 . 126.25(13) yes
C4 . C8 . H81 . 118.7 no
N15 . C8 . H81 . 115.1 no
C6 . C9 . N17 . 126.92(13) yes
C6 . C9 . H91 . 117.4 no
N17 . C9 . H91 . 115.6 no
C7 . N13 . N14 . 118.24(11) yes
C7 . N13 . H131 . 119.0 no
N14 . N13 . H131 . 121.1 no
N13 . N14 . H141 . 113.4 no
N13 . N14 . H142 . 111.2 no
H141 . N14 . H142 . 106.0 no
C8 . N15 . N16 . 118.45(11) yes
C8 . N15 . H151 . 118.5 no
N16 . N15 . H151 . 123.1 no
N15 . N16 . H161 . 111.5 no
N15 . N16 . H162 . 112.2 no
H161 . N16 . H162 . 106.0 no
C9 . N17 . N18 . 117.85(12) yes
C9 . N17 . H171 . 119.0 no
N18 . N17 . H171 . 123.1 no
N17 . N18 . H182 . 110.9 no
N17 . N18 . H181 . 111.0 no
H182 . N18 . H181 . 110.8 no
C22 . C21 . C26 . 119.7(14) yes
C22 . C21 . O30 . 110.7(18) yes
C26 . C21 . O30 . 129.6(17) yes
C21 . C22 . C23 . 119.6(15) yes
C21 . C22 . C27 . 126.4(18) yes
C23 . C22 . C27 . 114.0(18) yes
C22 . C23 . C24 . 120.4(17) yes
C22 . C23 . O31 . 129.9(18) yes
C24 . C23 . O31 . 109.7(19) yes
C24 . C25 . C26 . 118(2) yes
C24 . C25 . O32 . 132(2) yes
C26 . C25 . O32 . 110(2) yes
C23 . C24 . C25 . 121.8(20) yes
C23 . C24 . C28 . 127.3(18) yes
C25 . C24 . C28 . 110.7(19) yes
C25 . C26 . C21 . 119.9(16) yes
C25 . C26 . C29 . 125.8(17) yes
C21 . C26 . C29 . 114.1(15) yes
C22 . C27 . N33 . 129.2(17) yes
C22 . C27 . H271 . 116.2 no
N33 . C27 . H271 . 114.5 no
C24 . C28 . N35 . 128.6(15) yes
C24 . C28 . H281 . 115.3 no
N35 . C28 . H281 . 116.0 no
C26 . C29 . N37 . 125.8(15) yes
C26 . C29 . H291 . 117.5 no
N37 . C29 . H291 . 116.7 no
C21 . O30 . H301 . 115.2 no
C23 . O31 . H311 . 114.3 no
C25 . O32 . H321 . 114.3 no
C27 . N33 . N34 . 133.0(20) yes
N33 . N34 . H342 . 108.4 no
N33 . N34 . H341 . 110.8 no
H342 . N34 . H341 . 109.5 no
C28 . N35 . N36 . 130(2) yes
N35 . N36 . H361 . 108.3 no
N35 . N36 . H362 . 109.7 no
H361 . N36 . H362 . 109.5 no
C29 . N37 . N38 . 130.6(19) yes
N37 . N38 . H381 . 109.7 no
N37 . N38 . H382 . 108.4 no
H381 . N38 . H382 . 109.5 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . O11 2_766 164.62(4) 0.958 2.343 3.277(14) yes
C7 . H71 . O31 2_766 174.7(3) 0.958 2.498 3.453(14) yes
N33 . H71 . C3 . 120.4(9) 1.076 2.539 3.220(14) yes
N33 . H71 . O11 . 150.0(9) 1.076 2.385 3.361(14) yes
N33 . H71 . O31 . 147.0(10) 1.076 1.644 2.613(14) yes
N33 . H71 . O31 2_766 134.6(9) 1.076 2.498 3.342(14) yes
N35 . H81 . C5 . 128.0(8) 1.035 2.537 3.277(14) yes
N35 . H81 . O12 . 157.4(8) 1.035 2.387 3.366(14) yes
N35 . H81 . O32 . 159.7(9) 1.035 1.619 2.614(14) yes
N37 . H91 . C1 . 126.6(8) 1.116 2.537 3.326(14) yes
N37 . H91 . O10 . 156.1(8) 1.116 2.402 3.453(14) yes
N37 . H91 . O30 . 154.8(9) 1.116 1.544 2.598(14) yes
N16 . H161 . O10 3_564 137.80(4) 0.856 2.309 2.999(14) yes
N16 . H161 . O30 3_564 134.8(4) 0.856 2.012 2.685(14) yes
N36 . H161 . O10 3_564 143(2) 1.158 2.309 3.305(14) yes
N36 . H161 . O30 3_564 129(2) 1.158 2.012 2.890(14) yes
N18 . H182 . N18 4_646 145.14(7) 0.870 2.470 3.222(14) yes
N38 . H182 . N18 4_646 136.0(20) 1.104 2.470 3.352(14) yes
N18 . H182 . N38 4_646 149.6(9) 0.870 2.140 2.924(14) yes
N38 . H182 . N38 4_646 138.8(12) 1.104 2.140 3.058(14) yes
N14 . H141 . O11 2_776 166.23(5) 0.864 2.045 2.891(14) yes
N14 . H141 . O31 2_776 153.7(3) 0.864 2.157 2.957(14) yes
N34 . H141 . O11 2_776 144.2(17) 1.138 2.045 3.041(14) yes
N34 . H141 . O31 2_776 132.5(17) 1.138 2.157 3.043(14) yes
N16 . H162 . O30 3_554 127.3(3) 0.851 2.435 3.027(14) yes
N36 . H162 . O30 3_554 125(2) 1.037 2.435 3.152(14) yes
N14 . H142 . C27 4_756 158.2(3) 0.846 2.510 3.311(14) yes
N34 . H142 . C27 4_756 166.6(18) 1.133 2.510 3.622(14) yes
N18 . H181 . O12 2_676 153.94(4) 0.865 2.231 3.032(14) yes
N18 . H181 . O32 2_676 163.7(3) 0.865 2.109 2.950(14) yes
N38 . H181 . O12 2_676 144(2) 1.001 2.231 3.098(14) yes
N38 . H181 . O32 2_676 142(2) 1.001 2.109 2.964(14) yes
N17 . H171 . O12 . 128.64(4) 0.859 2.054 2.675(14) yes
N17 . H171 . O12 2_666 150.67(3) 0.859 2.567 3.342(14) yes
C29 . H171 . O12 2_666 151.7(8) 1.039 2.567 3.516(14) yes
N17 . H171 . O32 2_666 132.6(3) 0.859 2.414 3.061(14) yes
C29 . H171 . O32 2_666 165.5(9) 1.039 2.414 3.429(14) yes
N13 . H131 . O10 . 128.46(4) 0.863 2.017 2.642(14) yes
N15 . H151 . O11 . 129.63(4) 0.863 2.015 2.650(14) yes
N15 . H151 . N14 2_766 127.92(4) 0.863 2.462 3.069(14) yes
C28 . H151 . N14 2_766 172.0(7) 1.136 2.462 3.590(14) yes
N15 . H151 . N34 2_766 132.9(9) 0.863 2.054 2.717(14) yes
C28 . H151 . N34 2_766 174.3(12) 1.136 2.054 3.187(14) yes
N15 . H281 . C3 . 122.0(11) 0.993 2.272 2.922(14) yes
N15 . H281 . O11 . 154.9(13) 0.993 1.717 2.650(14) yes
N15 . H281 . O31 . 153.4(12) 0.993 2.466 3.383(14) yes
C28 . H281 . N34 2_766 160.6(9) 0.950 2.275 3.187(14) yes
N13 . H271 . C1 . 122.2(11) 1.127 2.157 2.918(14) yes
N13 . H271 . O10 . 155.3(13) 1.127 1.576 2.642(14) yes
N13 . H271 . O30 . 156.4(12) 1.127 2.419 3.481(14) yes
N17 . H291 . O12 . 146.8(12) 1.102 1.685 2.675(14) yes
N17 . H291 . O12 2_666 125.0(10) 1.102 2.586 3.342(14) yes
C29 . H291 . O12 2_666 166.5(3) 0.950 2.586 3.516(14) yes
N17 . H291 . O32 . 150.3(11) 1.102 2.463 3.464(14) yes
C29 . H291 . O32 2_666 154.3(5) 0.950 2.549 3.429(14) yes
N18 . H381 . N18 4_656 126(3) 0.995 2.529 3.222(14) yes
N38 . H381 . N38 4_646 132.7(15) 0.850 2.417 3.058(14) yes
N18 . H382 . N38 4_656 122(3) 1.162 2.585 3.352(14) yes
N34 . H342 . O10 4_746 157.6(7) 0.850 2.584 3.386(14) yes
N14 . H341 . N15 2_766 122(3) 0.979 2.441 3.069(14) yes
N14 . H341 . O31 2_776 125(3) 0.979 2.280 2.957(14) yes
N34 . H341 . O11 2_776 148.0(8) 0.850 2.287 3.041(14) yes
N34 . H341 . O31 2_776 149.6(9) 0.850 2.280 3.043(14) yes
O31 . H311 . O11 2_766 135.9(3) 0.850 2.314 2.984(14) yes
O31 . H311 . N33 . 134.9(6) 0.850 1.942 2.613(14) yes
O32 . H321 . N35 . 133.5(6) 0.850 1.955 2.614(14) yes
O30 . H301 . N35 3_565 121.9(4) 0.850 2.578 3.112(14) yes
O30 . H301 . N37 . 135.4(6) 0.850 1.923 2.598(14) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 21/09/16 at 10:58:15
#
#LIST     12                                                                    
BLOCK SCALE X'S 
CONT C(1,U'S) UNTIL N(18) 
CONT C(21,U[ISO]) UNTIL N(38) 
EQUIV PART(0001,OCC),PART(0002,OCC) 
WEIGHT -1 PART(0002,OCC) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE N   (  13,X'S) H   ( 131,X'S) 
RIDE N   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE N   (  15,X'S) H   ( 151,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE N   (  17,X'S) H   ( 171,X'S) 
RIDE N   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (   27,X'S) H   (  271,X'S) 
RIDE C   (   28,X'S) H   (  281,X'S) 
RIDE C   (   29,X'S) H   (  291,X'S) 
RIDE N   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE N   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE N   (  38,X'S) H   ( 382,X'S) H   ( 381,X'S) 
RIDE O   (  30,X'S) H   ( 301,X'S) 
RIDE O   (  31,X'S) H   ( 311,X'S) 
RIDE O   (  32,X'S) H   ( 321,X'S) 
END   
;

_iucr_refine_instructions_details_restraints 
;                                                                          
#
# Punched on 21/09/16 at 10:58:15
#
#LIST     16                                                                    
NO 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 1 3 x .
0 1 4 x .
-1 1 3 x .
5 0 2 x .
7 0 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound9
_database_code_depnum_ccdc_archive 'CCDC 1569192'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
The crystal presents pseudo-merohedral twinning, which was treated using ROTAX 
analysis. The structure in general doesnât show significant disorder and 
all the ellipsoids are relatively small. The only bond where it was necessary 
to add some thermal similarity and vibrational restraints is the C(5)-C(17) 
double bond. 
;

_cell_length_a                   4.3393(14)
_cell_length_b                   18.049(6)
_cell_length_c                   20.965(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.408(6)
_cell_angle_gamma                90
_cell_volume                     1641.9(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ' -P 2yn '

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C31 H32 Cl2 N6 O12'
_chemical_formula_moiety         '2(C15 H15 N3 O6), C H2 Cl2'
_chemical_compound_source        ' synthesized '
_chemical_formula_weight         751.53

_cell_measurement_reflns_used    2308
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.74
_cell_measurement_temperature    90

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.79

_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    0.273

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2, (Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'Apex2, (Bruker, 2007)'
_computing_cell_refinement       'Apex2, (Bruker, 2007)'
_computing_data_reduction        'Apex2, (Bruker, 2007)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0

_diffrn_ambient_temperature      90
_diffrn_reflns_number            10634
_reflns_number_total             2983
_diffrn_reflns_av_R_equivalents  0.051

_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         25.374
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        25.374
_diffrn_measured_fraction_theta_full 0.989

_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -5
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.09
_oxford_diffrn_Wilson_scale      3.97

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.47
_refine_diff_density_max         0.63

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     7
_refine_ls_number_parameters     238
_oxford_refine_ls_R_factor_ref   0.0782
_refine_ls_wR_factor_ref         0.1341
_refine_ls_goodness_of_fit_ref   0.9101
_refine_ls_shift/su_max          0.0002013
_refine_ls_shift/su_mean         0.0000173

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2398
_refine_ls_R_factor_all          0.0782
_refine_ls_wR_factor_all         0.1341

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2086
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_gt          0.1305

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 59.2 93.8 56.4 23.1 4.83 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.1141(11) 0.8068(2) 0.2421(2) 0.0241 1.0000 Uani . . . . . .
C2 C 0.0145(11) 0.7847(2) 0.30630(19) 0.0258 1.0000 Uani . . . . . .
C3 C 0.1419(11) 0.7161(2) 0.33362(19) 0.0227 1.0000 Uani . . . . . .
C4 C 0.3634(11) 0.6704(2) 0.2980(2) 0.0236 1.0000 Uani . . . . . .
C5 C 0.4617(10) 0.6955(2) 0.23542(19) 0.0209 1.0000 Uani . U . . . .
C6 C 0.3399(11) 0.7646(2) 0.2070(2) 0.0242 1.0000 Uani . . . . . .
C7 C -0.0370(10) 0.8662(2) 0.21557(19) 0.0219 1.0000 Uani . . . . . .
C8 C -0.1719(11) 0.9556(2) 0.1365(2) 0.0219 1.0000 Uani . . . . . .
C9 C -0.0918(12) 0.9836(2) 0.0721(2) 0.0298 1.0000 Uani . . . . . .
C17 C 0.6632(11) 0.6564(2) 0.1997(2) 0.0255 1.0000 Uani . U . . . .
C18 C 1.0089(12) 0.5598(2) 0.1705(2) 0.0276 1.0000 Uani . . . . . .
C19 C 1.1431(12) 0.4868(2) 0.1905(2) 0.0293 1.0000 Uani . . . . . .
C27 C 0.0502(11) 0.6914(2) 0.39214(19) 0.0245 1.0000 Uani . . . . . .
C28 C -0.2409(11) 0.7021(2) 0.4907(2) 0.0265 1.0000 Uani . . . . . .
C29 C -0.4478(12) 0.7538(2) 0.5247(2) 0.0294 1.0000 Uani . . . . . .
Cl1 Cl -0.0167(6) 0.93180(8) 0.46156(8) 0.0858 1.0000 Uani . . . . . .
O14 O 0.4654(8) 0.61170(15) 0.32159(14) 0.0294 1.0000 Uani . . . . . .
O16 O 0.4318(7) 0.78636(15) 0.15382(13) 0.0274 1.0000 Uani . . . . . .
O1 O -0.3753(8) 0.98103(15) 0.16900(14) 0.0269 1.0000 Uani . . . . . .
O21 O -0.1444(8) 0.64383(15) 0.51116(13) 0.0298 1.0000 Uani . . . . . .
O11 O 1.0689(8) 0.59019(16) 0.12024(14) 0.0359 1.0000 Uani . . . . . .
O12 O -0.1753(8) 0.82333(15) 0.33571(14) 0.0294 1.0000 Uani . . . . . .
N1 N 0.0109(9) 0.89639(17) 0.15837(15) 0.0239 1.0000 Uani . . . . . .
N21 N -0.1497(9) 0.72783(18) 0.43021(16) 0.0248 1.0000 Uani . . . . . .
N11 N 0.8073(9) 0.59274(18) 0.21391(17) 0.0252 1.0000 Uani . . . . . .
C30 C -0.204(4) 1.0029(8) 0.4995(7) 0.0720 0.5000 Uani . . . . . .
H71 H -0.1889 0.8890 0.2400 0.0256 1.0000 Uiso R . . . . .
H93 H -0.2010 1.0284 0.0625 0.0453 1.0000 Uiso R . . . . .
H92 H 0.1256 0.9913 0.0690 0.0448 1.0000 Uiso R . . . . .
H91 H -0.1537 0.9469 0.0419 0.0448 1.0000 Uiso R . . . . .
H171 H 0.7130 0.6750 0.1590 0.0307 1.0000 Uiso R . . . . .
H193 H 1.1767 0.4871 0.2362 0.0440 1.0000 Uiso R . . . . .
H192 H 1.3395 0.4801 0.1694 0.0442 1.0000 Uiso R . . . . .
H191 H 1.0006 0.4476 0.1794 0.0440 1.0000 Uiso R . . . . .
H271 H 0.1290 0.6474 0.4074 0.0293 1.0000 Uiso R . . . . .
H293 H -0.5529 0.7861 0.4948 0.0438 1.0000 Uiso R . . . . .
H292 H -0.3309 0.7827 0.5539 0.0440 1.0000 Uiso R . . . . .
H291 H -0.5966 0.7260 0.5479 0.0440 1.0000 Uiso R . . . . .
H302 H -0.2920 1.0309 0.4647 0.1080 0.5000 Uiso R . . . . .
H301 H -0.3067 0.9781 0.5337 0.1080 0.5000 Uiso R . . . . .
H111 H 0.7638 0.5696 0.2484 0.0300 1.0000 Uiso R . . . . .
H11 H 0.1674 0.8822 0.1363 0.0285 1.0000 Uiso R . . . . .
H211 H -0.2439 0.7653 0.4153 0.0298 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4902(15)

loop_
_oxford_twin_element_scale_factors
0.782(3)
0.150(4)
0.039(4)
0.030(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.471(6) yes
C1 . C6 . 1.447(6) yes
C1 . C7 . 1.373(6) yes
C2 . C3 . 1.470(6) yes
C2 . O12 . 1.246(5) yes
C3 . C4 . 1.474(6) yes
C3 . C27 . 1.367(6) yes
C4 . C5 . 1.454(6) yes
C4 . O14 . 1.249(5) yes
C5 . C6 . 1.478(6) yes
C5 . C17 . 1.354(6) yes
C6 . O16 . 1.250(5) yes
C7 . N1 . 1.335(5) yes
C7 . H71 . 0.933 no
C8 . C9 . 1.485(6) yes
C8 . O1 . 1.209(5) yes
C8 . N1 . 1.406(5) yes
C9 . H93 . 0.957 no
C9 . H92 . 0.956 no
C9 . H91 . 0.954 no
C17 . N11 . 1.340(6) yes
C17 . H171 . 0.944 no
C18 . C19 . 1.500(6) yes
C18 . O11 . 1.218(5) yes
C18 . N11 . 1.400(6) yes
C19 . H193 . 0.968 no
C19 . H192 . 0.971 no
C19 . H191 . 0.966 no
C27 . N21 . 1.353(5) yes
C27 . H271 . 0.921 no
C28 . C29 . 1.481(6) yes
C28 . O21 . 1.209(5) yes
C28 . N21 . 1.410(6) yes
C29 . H293 . 0.966 no
C29 . H292 . 0.950 no
C29 . H291 . 0.955 no
Cl1 . C30 2_576 1.720(13) yes
Cl1 . C30 . 1.717(14) yes
N1 . H11 . 0.864 no
N21 . H211 . 0.848 no
N11 . H111 . 0.857 no
C30 . C30 2_576 1.77(3) yes
C30 . H302 . 0.963 no
C30 . H301 . 0.960 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 121.9(4) yes
C2 . C1 . C7 . 116.1(4) yes
C6 . C1 . C7 . 121.8(4) yes
C1 . C2 . C3 . 118.2(4) yes
C1 . C2 . O12 . 120.1(4) yes
C3 . C2 . O12 . 121.8(4) yes
C2 . C3 . C4 . 121.2(4) yes
C2 . C3 . C27 . 120.9(4) yes
C4 . C3 . C27 . 117.9(4) yes
C3 . C4 . C5 . 118.6(4) yes
C3 . C4 . O14 . 120.3(4) yes
C5 . C4 . O14 . 121.1(4) yes
C4 . C5 . C6 . 121.4(4) yes
C4 . C5 . C17 . 122.1(4) yes
C6 . C5 . C17 . 116.6(4) yes
C5 . C6 . C1 . 118.7(4) yes
C5 . C6 . O16 . 120.7(4) yes
C1 . C6 . O16 . 120.7(4) yes
C1 . C7 . N1 . 127.3(4) yes
C1 . C7 . H71 . 117.3 no
N1 . C7 . H71 . 115.4 no
C9 . C8 . O1 . 124.1(4) yes
C9 . C8 . N1 . 114.8(4) yes
O1 . C8 . N1 . 121.1(4) yes
C8 . C9 . H93 . 111.0 no
C8 . C9 . H92 . 110.4 no
H93 . C9 . H92 . 110.5 no
C8 . C9 . H91 . 107.5 no
H93 . C9 . H91 . 108.1 no
H92 . C9 . H91 . 109.2 no
C5 . C17 . N11 . 128.8(4) yes
C5 . C17 . H171 . 117.9 no
N11 . C17 . H171 . 113.4 no
C19 . C18 . O11 . 123.6(4) yes
C19 . C18 . N11 . 115.8(4) yes
O11 . C18 . N11 . 120.7(4) yes
C18 . C19 . H193 . 109.1 no
C18 . C19 . H192 . 108.8 no
H193 . C19 . H192 . 109.0 no
C18 . C19 . H191 . 109.2 no
H193 . C19 . H191 . 109.5 no
H192 . C19 . H191 . 111.2 no
C3 . C27 . N21 . 124.3(4) yes
C3 . C27 . H271 . 118.9 no
N21 . C27 . H271 . 116.8 no
C29 . C28 . O21 . 126.0(4) yes
C29 . C28 . N21 . 113.6(4) yes
O21 . C28 . N21 . 120.4(4) yes
C28 . C29 . H293 . 110.7 no
C28 . C29 . H292 . 109.5 no
H293 . C29 . H292 . 109.6 no
C28 . C29 . H291 . 109.1 no
H293 . C29 . H291 . 109.3 no
H292 . C29 . H291 . 108.6 no
C30 2_576 Cl1 . C30 . 62.1(9) yes
C8 . N1 . C7 . 120.8(4) yes
C8 . N1 . H11 . 119.6 no
C7 . N1 . H11 . 119.2 no
C28 . N21 . C27 . 123.8(4) yes
C28 . N21 . H211 . 117.2 no
C27 . N21 . H211 . 118.6 no
C18 . N11 . C17 . 120.8(4) yes
C18 . N11 . H111 . 118.9 no
C17 . N11 . H111 . 120.0 no
Cl1 2_576 C30 . Cl1 . 117.9(9) yes
Cl1 2_576 C30 . C30 2_576 58.9(7) yes
Cl1 . C30 . C30 2_576 59.1(8) yes
Cl1 2_576 C30 . H302 . 102.5 no
Cl1 . C30 . H302 . 103.2 no
C30 2_576 C30 . H302 . 115.6 no
Cl1 2_576 C30 . H301 . 103.0 no
Cl1 . C30 . H301 . 102.8 no
C30 2_576 C30 . H301 . 115.6 no
H302 . C30 . H301 . 128.8 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C19 . H193 . O1 3_545 138.02(14) 0.968 2.390 3.176(7) yes
C30 . H302 . O11 3_555 172.5(3) 0.963 2.394 3.352(7) yes
C30 . H301 . O11 4_365 165.9(4) 0.960 2.261 3.201(7) yes
N11 . H111 . O14 . 124.44(12) 0.857 2.154 2.732(7) yes
N11 . H111 . O1 3_545 152.60(11) 0.857 2.404 3.189(7) yes
N1 . H11 . O16 . 125.43(12) 0.864 2.106 2.700(7) yes
N21 . H211 . O12 . 130.74(14) 0.848 1.994 2.628(7) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 20/01/16 at 11:50:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  93,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 193,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 293,X'S) H   ( 292,X'S) H   ( 291,X'S) 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (  21,X'S) H   ( 211,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) 
END                                                                             
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 20/01/16 at 11:50:26
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = C(5) TO C(17) 
VIBRATION 0.0, 0.020000 = C(5) TO C(17) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 3 2 x .
-1 4 3 x .
-1 3 4 x .
1 5 7 x .
-1 1 3 x .
-2 4 5 x .
-1 4 2 x .
-1 4 2 x .
1 3 1 x .
2 12 2 x .
1 5 6 x .
-1 7 4 x .
-1 1 1 x .
-1 2 1 x .
-2 7 5 x .
-2 5 5 x .
-2 6 6 x .
0 4 0 x .
-1 0 3 x .
1 0 3 x .
-1 3 8 x .
3 0 1 x .

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1569190'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
Crystals were obtained as very thin rods, and were weakly-diffracting at high 
angle. Nevertheless, refinement proceeded smoothly, and the structure is of
good quality.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   33.094(4)
_cell_length_b                   33.094(4)
_cell_length_c                   4.6401(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5082.0(8)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I -4 '
_symmetry_space_group_name_Hall  'I -4'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

_chemical_formula_sum            'C30 H27 N3 O6'
_chemical_formula_moiety         'C30 H27 N3 O6'
_chemical_compound_source        synthesized
_chemical_formula_weight         525.56

_cell_measurement_reflns_used    2804
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      65.01
_cell_measurement_temperature    90

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_max          0.67

_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2208
_exptl_absorpt_coefficient_mu    0.796

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2, (Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'Apex2, (Bruker, 2007)'
_computing_cell_refinement       'Apex2, (Bruker, 2007)'
_computing_data_reduction        'Apex2, (Bruker, 2007)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0

_diffrn_ambient_temperature      90
_diffrn_reflns_number            8857
_reflns_number_total             3738
_diffrn_reflns_av_R_equivalents  0.056

_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         65.149
_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        65.149
_diffrn_measured_fraction_theta_full 0.983

_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       4
_reflns_limit_h_min              -38
_reflns_limit_h_max              38
_reflns_limit_k_min              0
_reflns_limit_k_max              38
_reflns_limit_l_min              0
_reflns_limit_l_max              5

_oxford_diffrn_Wilson_B_factor   1.94
_oxford_diffrn_Wilson_scale      99.04

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.25

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     3
_refine_ls_number_parameters     361
_oxford_refine_ls_R_factor_ref   0.0529
_refine_ls_wR_factor_ref         0.1243
_refine_ls_goodness_of_fit_ref   0.9190
_refine_ls_shift/su_max          0.0002540
_refine_ls_shift/su_mean         0.0000292

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3716
_refine_ls_R_factor_all          0.0529
_refine_ls_wR_factor_all         0.1243

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3170
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_gt          0.1138

_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.14 12.2 5.68 1.42 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.23282(9) 0.50777(9) 0.8047(6) 0.0238 1.0000 Uani . . . . . .
C2 C 0.26295(9) 0.51120(9) 0.5928(6) 0.0244 1.0000 Uani . . . . . .
C3 C 0.27731(8) 0.47740(9) 0.4396(6) 0.0216 1.0000 Uani . . . . . .
C4 C 0.26063(9) 0.43938(9) 0.5044(6) 0.0247 1.0000 Uani . . . . . .
C5 C 0.23063(9) 0.43456(9) 0.7150(6) 0.0257 1.0000 Uani . . . . . .
C6 C 0.21715(9) 0.46909(10) 0.8633(6) 0.0266 1.0000 Uani . . . . . .
O7 O 0.27743(6) 0.54825(6) 0.5407(5) 0.0261 1.0000 Uani D . . . . .
O8 O 0.27434(6) 0.40766(6) 0.3507(5) 0.0284 1.0000 Uani D . . . . .
O9 O 0.18803(6) 0.46352(7) 1.0616(5) 0.0315 1.0000 Uani D . . . . .
C10 C 0.22027(9) 0.54339(10) 0.9632(7) 0.0272 1.0000 Uani . . . . . .
N11 N 0.19235(8) 0.54105(9) 1.1526(6) 0.0325 1.0000 Uani . . . . . .
O12 O 0.18674(7) 0.57808(8) 1.2978(5) 0.0408 1.0000 Uani . . . . . .
C13 C 0.14911(10) 0.57628(13) 1.4541(8) 0.0443 1.0000 Uani . . . . . .
C14 C 0.11327(10) 0.57880(10) 1.2590(7) 0.0297 1.0000 Uani . . . . . .
C15 C 0.09014(11) 0.54525(10) 1.1934(10) 0.0437 1.0000 Uani . . . . . .
C16 C 0.05753(11) 0.54838(12) 1.0083(12) 0.0561 1.0000 Uani . . . . . .
C17 C 0.04823(11) 0.58475(13) 0.8839(9) 0.0467 1.0000 Uani . . . . . .
C18 C 0.07042(11) 0.61798(11) 0.9494(9) 0.0421 1.0000 Uani . . . . . .
C19 C 0.10240(10) 0.61524(9) 1.1333(8) 0.0348 1.0000 Uani . . . . . .
C20 C 0.30774(9) 0.48100(9) 0.2161(6) 0.0240 1.0000 Uani . . . . . .
N21 N 0.32331(7) 0.51538(7) 0.1557(5) 0.0236 1.0000 Uani . . . . . .
O22 O 0.35035(6) 0.51280(6) -0.0740(5) 0.0270 1.0000 Uani . . . . . .
C23 C 0.36499(9) 0.55279(9) -0.1434(6) 0.0280 1.0000 Uani . . . . . .
C24 C 0.39419(9) 0.56905(9) 0.0741(6) 0.0245 1.0000 Uani . . . . . .
C25 C 0.38917(9) 0.60754(9) 0.1918(7) 0.0258 1.0000 Uani . . . . . .
C26 C 0.41680(10) 0.62297(9) 0.3841(7) 0.0303 1.0000 Uani . . . . . .
C27 C 0.44974(9) 0.60012(9) 0.4696(7) 0.0279 1.0000 Uani . . . . . .
C28 C 0.45481(9) 0.56150(9) 0.3534(7) 0.0259 1.0000 Uani . . . . . .
C29 C 0.42777(9) 0.54634(9) 0.1591(7) 0.0262 1.0000 Uani . . . . . .
C30 C 0.21319(10) 0.39549(10) 0.7831(7) 0.0310 1.0000 Uani . . . . . .
N31 N 0.22016(8) 0.36483(8) 0.6210(6) 0.0333 1.0000 Uani . . . . . .
O32 O 0.20209(7) 0.32937(7) 0.7287(5) 0.0391 1.0000 Uani . . . . . .
C33 C 0.19693(14) 0.30188(12) 0.4923(9) 0.0516 1.0000 Uani . . . . . .
C34 C 0.18722(10) 0.26061(10) 0.6074(8) 0.0359 1.0000 Uani . . . . . .
C35 C 0.20828(11) 0.22737(11) 0.5062(8) 0.0409 1.0000 Uani . . . . . .
C36 C 0.19910(11) 0.18874(10) 0.6026(8) 0.0402 1.0000 Uani . . . . . .
C37 C 0.16899(11) 0.18337(11) 0.8003(8) 0.0398 1.0000 Uani . . . . . .
C38 C 0.14794(10) 0.21626(12) 0.9070(9) 0.0439 1.0000 Uani . . . . . .
C39 C 0.15680(10) 0.25462(11) 0.8064(8) 0.0389 1.0000 Uani . . . . . .
H101 H 0.2331 0.5680 0.9277 0.0329 1.0000 Uiso R . . . . .
H131 H 0.1491 0.5995 1.5848 0.0522 1.0000 Uiso R . . . . .
H132 H 0.1484 0.5507 1.5716 0.0532 1.0000 Uiso R . . . . .
H151 H 0.0970 0.5208 1.2769 0.0545 1.0000 Uiso R . . . . .
H161 H 0.0422 0.5263 0.9647 0.0660 1.0000 Uiso R . . . . .
H171 H 0.0268 0.5868 0.7527 0.0576 1.0000 Uiso R . . . . .
H181 H 0.0632 0.6427 0.8569 0.0521 1.0000 Uiso R . . . . .
H191 H 0.1173 0.6383 1.1783 0.0420 1.0000 Uiso R . . . . .
H201 H 0.3155 0.4581 0.1101 0.0299 1.0000 Uiso R . . . . .
H232 H 0.3780 0.5501 -0.3276 0.0332 1.0000 Uiso R . . . . .
H231 H 0.3420 0.5702 -0.1649 0.0333 1.0000 Uiso R . . . . .
H251 H 0.3668 0.6225 0.1337 0.0304 1.0000 Uiso R . . . . .
H261 H 0.4132 0.6490 0.4600 0.0362 1.0000 Uiso R . . . . .
H271 H 0.4681 0.6106 0.6073 0.0342 1.0000 Uiso R . . . . .
H281 H 0.4773 0.5458 0.4072 0.0313 1.0000 Uiso R . . . . .
H291 H 0.4317 0.5209 0.0767 0.0322 1.0000 Uiso R . . . . .
H301 H 0.1967 0.3924 0.9498 0.0375 1.0000 Uiso R . . . . .
H331 H 0.2220 0.3016 0.3750 0.0622 1.0000 Uiso R . . . . .
H332 H 0.1741 0.3124 0.3716 0.0627 1.0000 Uiso R . . . . .
H351 H 0.2291 0.2306 0.3668 0.0488 1.0000 Uiso R . . . . .
H361 H 0.2131 0.1666 0.5312 0.0480 1.0000 Uiso R . . . . .
H371 H 0.1632 0.1572 0.8640 0.0467 1.0000 Uiso R . . . . .
H381 H 0.1286 0.2124 1.0504 0.0543 1.0000 Uiso R . . . . .
H391 H 0.1422 0.2769 0.8764 0.0474 1.0000 Uiso R . . . . .
H81 H 0.2627(10) 0.3868(8) 0.395(9) 0.0425 1.0000 Uiso D . . . . .
H91 H 0.1826(12) 0.4841(9) 1.154(9) 0.0489 1.0000 Uiso D . . . . .
H71 H 0.2925(10) 0.5469(12) 0.400(6) 0.0406 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.10912(5)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.405(4) yes
C1 . C6 . 1.408(4) yes
C1 . C10 . 1.450(4) yes
C2 . C3 . 1.408(4) yes
C2 . O7 . 1.339(4) yes
C3 . C4 . 1.407(4) yes
C3 . C20 . 1.450(4) yes
C4 . C5 . 1.402(4) yes
C4 . O8 . 1.348(4) yes
C5 . C6 . 1.406(4) yes
C5 . C30 . 1.451(4) yes
C6 . O9 . 1.345(4) yes
O7 . H71 . 0.824(18) no
O8 . H81 . 0.816(18) no
O9 . H91 . 0.825(18) no
C10 . N11 . 1.278(4) yes
C10 . H101 . 0.934 no
N11 . O12 . 1.411(4) yes
O12 . C13 . 1.442(4) yes
C13 . C14 . 1.494(5) yes
C13 . H131 . 0.979 no
C13 . H132 . 1.006 no
C14 . C15 . 1.383(5) yes
C14 . C19 . 1.387(5) yes
C15 . C16 . 1.383(6) yes
C15 . H151 . 0.926 no
C16 . C17 . 1.370(6) yes
C16 . H161 . 0.914 no
C17 . C18 . 1.357(5) yes
C17 . H171 . 0.938 no
C18 . C19 . 1.363(5) yes
C18 . H181 . 0.955 no
C19 . H191 . 0.933 no
C20 . N21 . 1.280(4) yes
C20 . H201 . 0.939 no
N21 . O22 . 1.394(3) yes
O22 . C23 . 1.446(4) yes
C23 . C24 . 1.497(4) yes
C23 . H232 . 0.961 no
C23 . H231 . 0.958 no
C24 . C25 . 1.396(4) yes
C24 . C29 . 1.398(4) yes
C25 . C26 . 1.376(4) yes
C25 . H251 . 0.930 no
C26 . C27 . 1.385(4) yes
C26 . H261 . 0.940 no
C27 . C28 . 1.398(4) yes
C27 . H271 . 0.947 no
C28 . C29 . 1.365(4) yes
C28 . H281 . 0.942 no
C29 . H291 . 0.934 no
C30 . N31 . 1.284(4) yes
C30 . H301 . 0.952 no
N31 . O32 . 1.409(3) yes
O32 . C33 . 1.435(5) yes
C33 . C34 . 1.501(5) yes
C33 . H331 . 0.993 no
C33 . H332 . 1.003 no
C34 . C35 . 1.384(5) yes
C34 . C39 . 1.380(5) yes
C35 . C36 . 1.388(5) yes
C35 . H351 . 0.952 no
C36 . C37 . 1.366(5) yes
C36 . H361 . 0.928 no
C37 . C38 . 1.384(5) yes
C37 . H371 . 0.935 no
C38 . C39 . 1.384(5) yes
C38 . H381 . 0.932 no
C39 . H391 . 0.940 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 118.0(3) yes
C2 . C1 . C10 . 119.5(3) yes
C6 . C1 . C10 . 122.4(3) yes
C1 . C2 . C3 . 121.9(3) yes
C1 . C2 . O7 . 117.0(3) yes
C3 . C2 . O7 . 121.0(3) yes
C2 . C3 . C4 . 118.1(3) yes
C2 . C3 . C20 . 122.0(3) yes
C4 . C3 . C20 . 119.9(3) yes
C3 . C4 . C5 . 121.9(3) yes
C3 . C4 . O8 . 116.8(3) yes
C5 . C4 . O8 . 121.2(3) yes
C4 . C5 . C6 . 118.2(3) yes
C4 . C5 . C30 . 122.3(3) yes
C6 . C5 . C30 . 119.4(3) yes
C1 . C6 . C5 . 121.8(3) yes
C1 . C6 . O9 . 121.4(3) yes
C5 . C6 . O9 . 116.8(3) yes
C2 . O7 . H71 . 108(3) no
C4 . O8 . H81 . 112(3) no
C6 . O9 . H91 . 114(3) no
C1 . C10 . N11 . 120.4(3) yes
C1 . C10 . H101 . 119.4 no
N11 . C10 . H101 . 120.2 no
C10 . N11 . O12 . 111.8(3) yes
N11 . O12 . C13 . 108.5(3) yes
O12 . C13 . C14 . 112.3(3) yes
O12 . C13 . H131 . 106.2 no
C14 . C13 . H131 . 109.4 no
O12 . C13 . H132 . 109.0 no
C14 . C13 . H132 . 110.9 no
H131 . C13 . H132 . 108.9 no
C13 . C14 . C15 . 121.9(3) yes
C13 . C14 . C19 . 120.6(3) yes
C15 . C14 . C19 . 117.5(3) yes
C14 . C15 . C16 . 120.6(3) yes
C14 . C15 . H151 . 118.3 no
C16 . C15 . H151 . 121.1 no
C15 . C16 . C17 . 120.2(3) yes
C15 . C16 . H161 . 120.8 no
C17 . C16 . H161 . 119.0 no
C16 . C17 . C18 . 119.7(4) yes
C16 . C17 . H171 . 120.5 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 120.4(3) yes
C17 . C18 . H181 . 117.3 no
C19 . C18 . H181 . 122.3 no
C14 . C19 . C18 . 121.5(3) yes
C14 . C19 . H191 . 118.8 no
C18 . C19 . H191 . 119.7 no
C3 . C20 . N21 . 120.6(3) yes
C3 . C20 . H201 . 119.9 no
N21 . C20 . H201 . 119.5 no
C20 . N21 . O22 . 111.8(2) yes
N21 . O22 . C23 . 109.2(2) yes
O22 . C23 . C24 . 113.3(2) yes
O22 . C23 . H232 . 105.3 no
C24 . C23 . H232 . 110.1 no
O22 . C23 . H231 . 107.9 no
C24 . C23 . H231 . 111.5 no
H232 . C23 . H231 . 108.5 no
C23 . C24 . C25 . 121.0(3) yes
C23 . C24 . C29 . 120.7(3) yes
C25 . C24 . C29 . 118.3(3) yes
C24 . C25 . C26 . 120.9(3) yes
C24 . C25 . H251 . 117.9 no
C26 . C25 . H251 . 121.2 no
C25 . C26 . C27 . 120.4(3) yes
C25 . C26 . H261 . 119.9 no
C27 . C26 . H261 . 119.6 no
C26 . C27 . C28 . 118.9(3) yes
C26 . C27 . H271 . 119.8 no
C28 . C27 . H271 . 121.3 no
C27 . C28 . C29 . 120.8(3) yes
C27 . C28 . H281 . 119.8 no
C29 . C28 . H281 . 119.4 no
C24 . C29 . C28 . 120.6(3) yes
C24 . C29 . H291 . 118.6 no
C28 . C29 . H291 . 120.7 no
C5 . C30 . N31 . 120.3(3) yes
C5 . C30 . H301 . 120.1 no
N31 . C30 . H301 . 119.6 no
C30 . N31 . O32 . 112.0(3) yes
N31 . O32 . C33 . 107.9(3) yes
O32 . C33 . C34 . 109.3(3) yes
O32 . C33 . H331 . 108.9 no
C34 . C33 . H331 . 111.5 no
O32 . C33 . H332 . 107.3 no
C34 . C33 . H332 . 110.7 no
H331 . C33 . H332 . 109.0 no
C33 . C34 . C35 . 119.7(3) yes
C33 . C34 . C39 . 121.6(3) yes
C35 . C34 . C39 . 118.7(3) yes
C34 . C35 . C36 . 120.8(3) yes
C34 . C35 . H351 . 120.4 no
C36 . C35 . H351 . 118.8 no
C35 . C36 . C37 . 119.7(3) yes
C35 . C36 . H361 . 120.1 no
C37 . C36 . H361 . 120.2 no
C36 . C37 . C38 . 120.3(3) yes
C36 . C37 . H371 . 118.8 no
C38 . C37 . H371 . 120.9 no
C37 . C38 . C39 . 119.6(3) yes
C37 . C38 . H381 . 119.6 no
C39 . C38 . H381 . 120.8 no
C38 . C39 . C34 . 120.8(3) yes
C38 . C39 . H391 . 119.6 no
C34 . C39 . H391 . 119.7 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O8 . H81 . N31 . 144(4) 0.816 1.901 2.607(5) yes
O9 . H91 . N11 . 141(4) 0.825 1.912 2.604(5) yes
O7 . H71 . N21 . 148(4) 0.824 1.846 2.584(5) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 14/10/16 at 11:42: 0
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL C    (   39 ) 
CONT H    (   81 ,X'S)  UNTIL H    (   71 ) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
END                   
;

_iucr_refine_instructions_details_restraints 
;                                                          
#
# Punched on 14/10/16 at 11:42: 0
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 7) TO H(71) 
REST 0.040, 0.002 = H(71,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 8) TO H(81) 
REST 0.042, 0.002 = H(81,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 9) TO H(91) 
REST 0.048, 0.002 = H(91,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 4 1 x .
10 14 0 x .
1 2 1 x .
-2 1 1 x .
8 14 0 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1569189'
_audit_update_record             
;
2017-08-16 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;
#==============================================================================

_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N6 O6, 2(C3 H8 O)'
_chemical_formula_sum            'C30 H52 N6 O8'
_chemical_formula_weight         624.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.462(3)
_cell_length_b                   18.842(4)
_cell_length_c                   13.504(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.67(3)
_cell_angle_gamma                90
_cell_volume                     3386.1(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21042
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.996
_cell_measurement_theta_min      1.478
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.6896.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49682
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.783
_diffrn_reflns_theta_min         1.483
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'Rayonix MX300HE CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_device       'MAR300 CCD'
_diffrn_measurement_device_type  'MAR300 CCD'
_diffrn_measurement_method       'κ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68879
_diffrn_source                   synchrotron
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7042
_reflns_number_total             9383
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch (2010)'
_computing_data_collection       'MxDC, (Fodje, 2012)'
_computing_data_reduction        'XDS (Kabsch (2010)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0248(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         9383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+0.9740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups, All C(H,H,H) groups
2. Others
 Sof(H5)=Sof(H1A)=1-FVAR(1)
 Sof(H1)=Sof(H3)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C28(H28), C25(H25)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C19(H19)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66906(7) 0.37845(6) 0.67029(8) 0.0238(2) Uani 1 1 d . . . . .
H1 H 0.6630(17) 0.3393(15) 0.6455(18) 0.019(6) Uiso 0.74(3) 1 d . . P A 1
H5 H 0.609(6) 0.603(4) 0.755(5) 0.029 Uiso 0.26(3) 1 d R . P A 2
O2 O 0.34019(7) 0.38323(5) 0.48993(7) 0.0235(2) Uani 1 1 d . . . . .
H2 H 0.2916(17) 0.4157(12) 0.4769(17) 0.049(6) Uiso 1 1 d . . . . .
O3 O 0.47363(7) 0.58786(5) 0.67010(7) 0.0233(2) Uani 1 1 d . . . . .
H3 H 0.5290(16) 0.6008(10) 0.7054(15) 0.010(5) Uiso 0.74(3) 1 d . . P A 1
O4 O 0.76231(7) 0.19622(5) 0.58606(8) 0.0260(2) Uani 1 1 d . . . . .
O5 O 0.11494(7) 0.45397(5) 0.32657(8) 0.0275(2) Uani 1 1 d . . . . .
O6 O 0.68957(8) 0.67503(7) 0.91404(9) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.59318(9) 0.27146(6) 0.56776(9) 0.0216(2) Uani 1 1 d . . . . .
H1A H 0.641(7) 0.296(5) 0.615(7) 0.05(3) Uiso 0.26(3) 1 d . . P A 2
N2 N 0.59460(9) 0.20112(6) 0.53905(9) 0.0224(2) Uani 1 1 d . . . . .
N3 N 0.24490(8) 0.50013(6) 0.48050(8) 0.0211(2) Uani 1 1 d . . . . .
N4 N 0.16479(8) 0.54123(6) 0.43864(9) 0.0216(2) Uani 1 1 d . . . . .
N5 N 0.65965(9) 0.58043(7) 0.76159(9) 0.0235(2) Uani 1 1 d . . . . .
N6 N 0.75364(9) 0.60682(7) 0.80234(9) 0.0255(2) Uani 1 1 d . . . . .
C1 C 0.57434(9) 0.48296(7) 0.67299(9) 0.0199(2) Uani 1 1 d . . . . .
C2 C 0.58195(9) 0.41229(7) 0.64086(9) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.50257(9) 0.37812(7) 0.57996(9) 0.0195(2) Uani 1 1 d . . . . .
C4 C 0.41366(9) 0.41692(7) 0.54988(9) 0.0192(2) Uani 1 1 d . . . . .
C5 C 0.40317(9) 0.48798(7) 0.58026(9) 0.0190(2) Uani 1 1 d . . . . .
C6 C 0.48414(9) 0.51991(7) 0.64273(9) 0.0189(2) Uani 1 1 d . . . . .
C7 C 0.66200(10) 0.51681(7) 0.72768(10) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.7235 0.4912 0.7390 0.026 Uiso 1 1 calc R . . . .
C8 C 0.76277(10) 0.65408(8) 0.87811(10) 0.0245(3) Uani 1 1 d . . . . .
C9 C 0.86983(11) 0.67875(8) 0.91688(11) 0.0280(3) Uani 1 1 d . . . . .
C10 C 0.86578(13) 0.73815(9) 0.99368(13) 0.0375(4) Uani 1 1 d . . . . .
H10A H 0.8229 0.7767 0.9630 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.9337 0.7563 1.0157 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.8382 0.7194 1.0515 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.92100(14) 0.70577(11) 0.83007(15) 0.0461(5) Uani 1 1 d . . . . .
H11A H 0.9263 0.6669 0.7829 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.9884 0.7233 0.8563 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.8811 0.7444 0.7955 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.92821(14) 0.61596(10) 0.96869(18) 0.0518(5) Uani 1 1 d . . . . .
H12A H 0.8925 0.5974 1.0213 0.078 Uiso 1 1 calc GR . . . .
H12B H 0.9955 0.6317 0.9986 0.078 Uiso 1 1 calc GR . . . .
H12C H 0.9340 0.5786 0.9194 0.078 Uiso 1 1 calc GR . . . .
C13 C 0.50940(10) 0.30492(7) 0.54808(10) 0.0207(2) Uani 1 1 d . . . . .
H13 H 0.4520 0.2818 0.5127 0.025 Uiso 1 1 calc R . . . .
C14 C 0.68346(10) 0.16615(7) 0.55300(10) 0.0216(3) Uani 1 1 d . . . . .
C15 C 0.68005(11) 0.08650(7) 0.52932(11) 0.0263(3) Uani 1 1 d . . . . .
C16 C 0.77974(16) 0.06539(11) 0.4983(2) 0.0641(7) Uani 1 1 d . . . . .
H16A H 0.7887 0.0906 0.4368 0.096 Uiso 1 1 calc GR . . . .
H16B H 0.7803 0.0141 0.4863 0.096 Uiso 1 1 calc GR . . . .
H16C H 0.8346 0.0778 0.5518 0.096 Uiso 1 1 calc GR . . . .
C17 C 0.6661(2) 0.04804(10) 0.62614(15) 0.0568(6) Uani 1 1 d . . . . .
H17A H 0.7203 0.0616 0.6797 0.085 Uiso 1 1 calc GR . . . .
H17B H 0.6679 -0.0034 0.6155 0.085 Uiso 1 1 calc GR . . . .
H17C H 0.6012 0.0613 0.6453 0.085 Uiso 1 1 calc GR . . . .
C18 C 0.59652(16) 0.06560(10) 0.44560(16) 0.0483(5) Uani 1 1 d . . . . .
H18A H 0.5312 0.0744 0.4670 0.072 Uiso 1 1 calc GR . . . .
H18B H 0.6026 0.0151 0.4302 0.072 Uiso 1 1 calc GR . . . .
H18C H 0.6020 0.0939 0.3857 0.072 Uiso 1 1 calc GR . . . .
C19 C 0.31531(9) 0.52979(7) 0.54176(10) 0.0200(2) Uani 1 1 d . . . . .
H19 H 0.3098 0.5779 0.5613 0.024 Uiso 1 1 calc R . . . .
C20 C 0.10295(9) 0.51396(7) 0.35878(10) 0.0217(3) Uani 1 1 d . . . . .
C21 C 0.01846(10) 0.56338(8) 0.31200(10) 0.0239(3) Uani 1 1 d . . . . .
C22 C -0.04641(12) 0.52351(9) 0.22747(13) 0.0359(4) Uani 1 1 d . . . . .
H22A H -0.0060 0.5117 0.1752 0.054 Uiso 1 1 calc GR . . . .
H22B H -0.1031 0.5535 0.1991 0.054 Uiso 1 1 calc GR . . . .
H22C H -0.0718 0.4797 0.2539 0.054 Uiso 1 1 calc GR . . . .
C23 C -0.04490(11) 0.58548(10) 0.39241(12) 0.0361(4) Uani 1 1 d . . . . .
H23A H -0.0697 0.5430 0.4227 0.054 Uiso 1 1 calc GR . . . .
H23B H -0.1020 0.6142 0.3616 0.054 Uiso 1 1 calc GR . . . .
H23C H -0.0034 0.6134 0.4443 0.054 Uiso 1 1 calc GR . . . .
C24 C 0.06397(11) 0.62902(8) 0.26786(12) 0.0299(3) Uani 1 1 d . . . . .
H24A H 0.1022 0.6567 0.3221 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.0099 0.6583 0.2323 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.1088 0.6138 0.2211 0.045 Uiso 1 1 calc GR . . . .
O7 O 0.82607(8) 0.31450(6) 0.49096(8) 0.0281(2) Uani 1 1 d . . . . .
H7A H 0.8026(17) 0.2848(12) 0.5214(17) 0.047(6) Uiso 1 1 d . . . . .
C28 C 0.83345(11) 0.28971(8) 0.39102(11) 0.0266(3) Uani 1 1 d . . . . .
H28 H 0.8780 0.2470 0.3957 0.032 Uiso 1 1 calc R . . . .
C29 C 0.88124(12) 0.34859(10) 0.33906(12) 0.0354(3) Uani 1 1 d . . . . .
H29A H 0.8398 0.3914 0.3376 0.053 Uiso 1 1 calc GR . . . .
H29B H 0.8866 0.3341 0.2704 0.053 Uiso 1 1 calc GR . . . .
H29C H 0.9484 0.3585 0.3754 0.053 Uiso 1 1 calc GR . . . .
C30 C 0.73130(12) 0.27009(9) 0.33504(12) 0.0331(3) Uani 1 1 d . . . . .
H30A H 0.7023 0.2319 0.3707 0.050 Uiso 1 1 calc GR . . . .
H30B H 0.7383 0.2541 0.2674 0.050 Uiso 1 1 calc GR . . . .
H30C H 0.6871 0.3116 0.3307 0.050 Uiso 1 1 calc GR . . . .
O8 O 0.59695(8) 0.67054(6) 1.07585(8) 0.0307(2) Uani 1 1 d . . . . .
H8 H 0.6377(18) 0.6686(12) 1.0346(18) 0.050(6) Uiso 1 1 d . . . . .
C25 C 0.63367(11) 0.70754(8) 1.16773(11) 0.0293(3) Uani 1 1 d . . . . .
H25 H 0.6759 0.7487 1.1527 0.035 Uiso 1 1 calc R . . . .
C26 C 0.54364(12) 0.73440(9) 1.21075(12) 0.0321(3) Uani 1 1 d . . . . .
H26A H 0.5050 0.7669 1.1630 0.048 Uiso 1 1 calc GR . . . .
H26B H 0.5663 0.7595 1.2737 0.048 Uiso 1 1 calc GR . . . .
H26C H 0.5011 0.6942 1.2236 0.048 Uiso 1 1 calc GR . . . .
C27 C 0.69670(15) 0.65737(11) 1.23887(14) 0.0460(4) Uani 1 1 d . . . . .
H27A H 0.6566 0.6156 1.2505 0.069 Uiso 1 1 calc GR . . . .
H27B H 0.7187 0.6816 1.3027 0.069 Uiso 1 1 calc GR . . . .
H27C H 0.7557 0.6425 1.2096 0.069 Uiso 1 1 calc GR . . . .
H2A H 0.5371(14) 0.1825(9) 0.5057(14) 0.030(4) Uiso 1 1 d . . . . .
H6 H 0.8013(16) 0.5910(11) 0.7739(15) 0.037(5) Uiso 1 1 d . . . . .
H4 H 0.1610(16) 0.5857(12) 0.4622(16) 0.043(5) Uiso 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
O1 H1 0.81(3) . ?
O1 C2 1.3414(15) . ?
O2 H2 0.89(2) . ?
O2 C4 1.3397(15) . ?
O3 H3 0.86(2) . ?
O3 C6 1.3459(16) . ?
O4 C14 1.2264(17) . ?
O5 C20 1.2304(17) . ?
O6 C8 1.2274(18) . ?
N1 H1A 0.95(11) . ?
N1 N2 1.3817(16) . ?
N1 C13 1.2845(17) . ?
N2 C14 1.3538(17) . ?
N2 H2A 0.906(19) . ?
N3 N4 1.3779(15) . ?
N3 C19 1.2879(17) . ?
N4 C20 1.3598(18) . ?
N4 H4 0.90(2) . ?
N5 H5 0.80(7) . ?
N5 N6 1.3932(16) . ?
N5 C7 1.2853(19) . ?
N6 C8 1.3479(19) . ?
N6 H6 0.85(2) . ?
C1 C2 1.4089(19) . ?
C1 C6 1.4060(17) . ?
C1 C7 1.4429(18) . ?
C2 C3 1.4028(18) . ?
C3 C4 1.4090(17) . ?
C3 C13 1.4519(18) . ?
C4 C5 1.4137(18) . ?
C5 C6 1.4087(17) . ?
C5 C19 1.4506(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.5296(19) . ?
C9 C10 1.532(2) . ?
C9 C11 1.533(2) . ?
C9 C12 1.530(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 C15 1.534(2) . ?
C15 C16 1.518(2) . ?
C15 C17 1.531(2) . ?
C15 C18 1.521(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C20 C21 1.5307(19) . ?
C21 C22 1.526(2) . ?
C21 C23 1.536(2) . ?
C21 C24 1.540(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O7 H7A 0.79(2) . ?
O7 C28 1.4456(18) . ?
C28 H28 1.0000 . ?
C28 C29 1.508(2) . ?
C28 C30 1.512(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O8 H8 0.84(2) . ?
O8 C25 1.4438(19) . ?
C25 H25 1.0000 . ?
C25 C26 1.508(2) . ?
C25 C27 1.514(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 106.4(16) . . ?
C4 O2 H2 104.3(14) . . ?
C6 O3 H3 107.7(13) . . ?
N2 N1 H1A 128(6) . . ?
C13 N1 H1A 112(6) . . ?
C13 N1 N2 117.49(12) . . ?
N1 N2 H2A 117.7(11) . . ?
C14 N2 N1 118.50(11) . . ?
C14 N2 H2A 123.4(11) . . ?
C19 N3 N4 118.32(11) . . ?
N3 N4 H4 117.4(14) . . ?
C20 N4 N3 117.43(11) . . ?
C20 N4 H4 124.9(14) . . ?
N6 N5 H5 124(5) . . ?
C7 N5 H5 122(5) . . ?
C7 N5 N6 113.83(12) . . ?
N5 N6 H6 113.5(14) . . ?
C8 N6 N5 120.60(12) . . ?
C8 N6 H6 125.8(14) . . ?
C2 C1 C7 118.91(11) . . ?
C6 C1 C2 118.57(11) . . ?
C6 C1 C7 122.26(12) . . ?
O1 C2 C1 117.32(11) . . ?
O1 C2 C3 120.67(12) . . ?
C3 C2 C1 122.00(11) . . ?
C2 C3 C4 118.02(12) . . ?
C2 C3 C13 122.22(11) . . ?
C4 C3 C13 119.76(12) . . ?
O2 C4 C3 116.48(11) . . ?
O2 C4 C5 121.81(11) . . ?
C3 C4 C5 121.70(11) . . ?
C4 C5 C19 121.47(11) . . ?
C6 C5 C4 118.44(11) . . ?
C6 C5 C19 119.88(12) . . ?
O3 C6 C1 120.88(11) . . ?
O3 C6 C5 117.83(11) . . ?
C1 C6 C5 121.26(12) . . ?
N5 C7 C1 122.17(12) . . ?
N5 C7 H7 118.9 . . ?
C1 C7 H7 118.9 . . ?
O6 C8 N6 121.72(13) . . ?
O6 C8 C9 122.56(13) . . ?
N6 C8 C9 115.71(12) . . ?
C8 C9 C10 109.01(12) . . ?
C8 C9 C11 110.36(13) . . ?
C8 C9 C12 108.30(13) . . ?
C10 C9 C11 109.93(14) . . ?
C12 C9 C10 108.88(14) . . ?
C12 C9 C11 110.33(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C3 119.86(12) . . ?
N1 C13 H13 120.1 . . ?
C3 C13 H13 120.1 . . ?
O4 C14 N2 121.60(13) . . ?
O4 C14 C15 121.66(12) . . ?
N2 C14 C15 116.69(12) . . ?
C16 C15 C14 108.31(13) . . ?
C16 C15 C17 109.81(18) . . ?
C16 C15 C18 108.20(17) . . ?
C17 C15 C14 106.78(13) . . ?
C18 C15 C14 113.81(12) . . ?
C18 C15 C17 109.88(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C5 118.42(12) . . ?
N3 C19 H19 120.8 . . ?
C5 C19 H19 120.8 . . ?
O5 C20 N4 122.02(12) . . ?
O5 C20 C21 122.81(12) . . ?
N4 C20 C21 115.17(12) . . ?
C20 C21 C23 109.30(11) . . ?
C20 C21 C24 109.52(11) . . ?
C22 C21 C20 108.36(12) . . ?
C22 C21 C23 110.25(13) . . ?
C22 C21 C24 108.79(12) . . ?
C23 C21 C24 110.59(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 O7 H7A 110.3(16) . . ?
O7 C28 H28 109.1 . . ?
O7 C28 C29 106.91(12) . . ?
O7 C28 C30 111.13(12) . . ?
C29 C28 H28 109.1 . . ?
C29 C28 C30 111.53(13) . . ?
C30 C28 H28 109.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 O8 H8 114.7(16) . . ?
O8 C25 H25 109.4 . . ?
O8 C25 C26 107.59(12) . . ?
O8 C25 C27 109.29(14) . . ?
C26 C25 H25 109.4 . . ?
C26 C25 C27 111.79(14) . . ?
C27 C25 H25 109.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
O1 H1 N1 0.81(3) 1.82(3) 2.5686(16) 153(2) .
N5 H5 O3 0.80(7) 2.02(7) 2.6237(17) 132(7) .
O2 H2 N3 0.89(2) 1.71(2) 2.5424(15) 153(2) .
O3 H3 N5 0.86(2) 1.85(2) 2.6237(17) 149.7(19) .
N1 H1A O1 0.95(11) 1.74(11) 2.5686(16) 144(8) .
O7 H7A O4 0.79(2) 2.00(2) 2.7722(16) 168(2) .
O8 H8 O6 0.84(2) 1.87(2) 2.6755(17) 160(2) .
N2 H2A O8 0.906(19) 1.98(2) 2.8604(18) 163.6(16) 2_646
N6 H6 O5 0.85(2) 2.07(2) 2.8985(17) 164.1(19) 3_666
N4 H4 O7 0.90(2) 1.98(2) 2.8763(17) 171.1(19) 3_666

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 C2 C3 C4 -178.76(12) . . . . ?
O1 C2 C3 C13 1.55(19) . . . . ?
O2 C4 C5 C6 -179.49(11) . . . . ?
O2 C4 C5 C19 -4.86(19) . . . . ?
O4 C14 C15 C16 -30.5(2) . . . . ?
O4 C14 C15 C17 87.69(18) . . . . ?
O4 C14 C15 C18 -150.90(15) . . . . ?
O5 C20 C21 C22 3.20(19) . . . . ?
O5 C20 C21 C23 123.36(15) . . . . ?
O5 C20 C21 C24 -115.33(15) . . . . ?
O6 C8 C9 C10 -7.3(2) . . . . ?
O6 C8 C9 C11 -128.16(17) . . . . ?
O6 C8 C9 C12 110.98(18) . . . . ?
N1 N2 C14 O4 -3.26(19) . . . . ?
N1 N2 C14 C15 174.42(11) . . . . ?
N2 N1 C13 C3 177.62(11) . . . . ?
N2 C14 C15 C16 151.80(17) . . . . ?
N2 C14 C15 C17 -90.00(17) . . . . ?
N2 C14 C15 C18 31.42(19) . . . . ?
N3 N4 C20 O5 2.60(19) . . . . ?
N3 N4 C20 C21 -177.01(11) . . . . ?
N4 N3 C19 C5 -175.57(11) . . . . ?
N4 C20 C21 C22 -177.20(13) . . . . ?
N4 C20 C21 C23 -57.03(16) . . . . ?
N4 C20 C21 C24 64.27(16) . . . . ?
N5 N6 C8 O6 0.5(2) . . . . ?
N5 N6 C8 C9 179.62(12) . . . . ?
N6 N5 C7 C1 -173.15(12) . . . . ?
N6 C8 C9 C10 173.52(13) . . . . ?
N6 C8 C9 C11 52.70(18) . . . . ?
N6 C8 C9 C12 -68.17(18) . . . . ?
C1 C2 C3 C4 0.78(19) . . . . ?
C1 C2 C3 C13 -178.91(12) . . . . ?
C2 C1 C6 O3 -178.95(11) . . . . ?
C2 C1 C6 C5 -1.06(19) . . . . ?
C2 C1 C7 N5 -178.03(13) . . . . ?
C2 C3 C4 O2 178.55(11) . . . . ?
C2 C3 C4 C5 -0.58(19) . . . . ?
C2 C3 C13 N1 -6.6(2) . . . . ?
C3 C4 C5 C6 -0.41(19) . . . . ?
C3 C4 C5 C19 174.22(12) . . . . ?
C4 C3 C13 N1 173.76(12) . . . . ?
C4 C5 C6 O3 179.20(11) . . . . ?
C4 C5 C6 C1 1.25(18) . . . . ?
C4 C5 C19 N3 1.72(19) . . . . ?
C6 C1 C2 O1 179.58(11) . . . . ?
C6 C1 C2 C3 0.02(19) . . . . ?
C6 C1 C7 N5 7.9(2) . . . . ?
C6 C5 C19 N3 176.28(12) . . . . ?
C7 N5 N6 C8 -149.23(13) . . . . ?
C7 C1 C2 O1 5.25(18) . . . . ?
C7 C1 C2 C3 -174.30(12) . . . . ?
C7 C1 C6 O3 -4.83(19) . . . . ?
C7 C1 C6 C5 173.06(12) . . . . ?
C13 N1 N2 C14 175.67(12) . . . . ?
C13 C3 C4 O2 -1.75(18) . . . . ?
C13 C3 C4 C5 179.12(12) . . . . ?
C19 N3 N4 C20 165.98(12) . . . . ?
C19 C5 C6 O3 4.48(18) . . . . ?
C19 C5 C6 C1 -173.47(12) . . . . ?
