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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_tllm013

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N4 O2, C4 H6 O5'
_chemical_formula_sum            'C12 H16 N4 O7'
_chemical_formula_weight         328.29

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.1390(11)
_cell_length_b                   9.3060(10)
_cell_length_c                   9.7714(12)
_cell_angle_alpha                85.131(10)
_cell_angle_beta                 65.297(13)
_cell_angle_gamma                71.185(11)
_cell_volume                     713.43(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4122
_cell_measurement_theta_min      2.2935
_cell_measurement_theta_max      25.2981

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.95964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5903
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.894
_reflns_number_total             4640
_reflns_number_gt                4347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.852
_reflns_Friedel_fraction_full    0.859

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0997P)²+0.2849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4640
_refine_ls_number_parameters     505
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.6600(6) -0.1132(5) 0.5645(6) 0.0443(12) Uani 1 1 d . . . . .
C2 C 0.7080(8) -0.1549(6) 0.4201(7) 0.0463(14) Uani 1 1 d . . . . .
H2 H 0.6811 -0.2340 0.3901 0.056 Uiso 1 1 calc R U . . .
N3 N 0.7989(6) -0.0719(5) 0.3219(5) 0.0394(11) Uani 1 1 d . . . . .
C4 C 0.8109(7) 0.0300(6) 0.4076(6) 0.0350(11) Uani 1 1 d . . . . .
C5 C 0.7228(7) 0.0025(5) 0.5553(6) 0.0361(12) Uani 1 1 d . . . . .
N6 N 0.7115(6) 0.0810(5) 0.6736(5) 0.0381(11) Uani 1 1 d . . . . .
C7 C 0.7830(7) 0.1949(6) 0.6468(6) 0.0380(13) Uani 1 1 d . . . . .
N8 N 0.8649(6) 0.2256(5) 0.4946(5) 0.0356(10) Uani 1 1 d . . . . .
C9 C 0.8877(7) 0.1467(6) 0.3686(6) 0.0341(12) Uani 1 1 d . . . . .
C10 C 0.8753(9) -0.0925(7) 0.1562(7) 0.0524(15) Uani 1 1 d . . . . .
H10A H 0.8433 -0.1716 0.1263 0.079 Uiso 1 1 calc R U . . .
H10B H 0.9993 -0.1229 0.1184 0.079 Uiso 1 1 calc R U . . .
H10C H 0.8343 0.0033 0.1137 0.079 Uiso 1 1 calc R U . . .
C11 C 0.6198(8) 0.0459(7) 0.8301(7) 0.0484(15) Uani 1 1 d . . . . .
H11A H 0.6687 0.0696 0.8941 0.073 Uiso 1 1 calc R U . . .
H11B H 0.6300 -0.0623 0.8335 0.073 Uiso 1 1 calc R U . . .
H11C H 0.4997 0.1070 0.8668 0.073 Uiso 1 1 calc R U . . .
O12 O 0.7779(6) 0.2661(5) 0.7497(5) 0.0505(11) Uani 1 1 d . . . . .
C13 C 0.9341(8) 0.3532(6) 0.4660(7) 0.0463(14) Uani 1 1 d . . . . .
H13A H 1.0578 0.3135 0.4305 0.069 Uiso 1 1 calc R U . . .
H13B H 0.8853 0.4163 0.5595 0.069 Uiso 1 1 calc R U . . .
H13C H 0.9051 0.4147 0.3889 0.069 Uiso 1 1 calc R U . . .
O14 O 0.9678(5) 0.1786(4) 0.2389(4) 0.0418(9) Uani 1 1 d . . . . .
N15 N 0.3424(6) 1.1074(5) 0.4379(5) 0.0413(11) Uani 1 1 d . . . . .
C16 C 0.2902(8) 1.1469(7) 0.5838(7) 0.0438(13) Uani 1 1 d . . . . .
H16 H 0.3175 1.2242 0.6163 0.053 Uiso 1 1 calc R U . . .
N17 N 0.1967(6) 1.0671(5) 0.6783(5) 0.0420(11) Uani 1 1 d . . . . .
C18 C 0.1879(7) 0.9655(6) 0.5880(6) 0.0367(12) Uani 1 1 d . . . . .
C19 C 0.2745(7) 0.9953(5) 0.4432(5) 0.0335(12) Uani 1 1 d . . . . .
N20 N 0.2883(6) 0.9203(5) 0.3231(5) 0.0370(10) Uani 1 1 d . . . . .
C21 C 0.2137(8) 0.8060(6) 0.3482(7) 0.0396(13) Uani 1 1 d . . . . .
N22 N 0.1319(6) 0.7743(5) 0.4978(6) 0.0433(11) Uani 1 1 d . . . . .
C23 C 0.1082(7) 0.8487(6) 0.6281(6) 0.0407(14) Uani 1 1 d . . . . .
C24 C 0.1182(9) 1.0893(9) 0.8427(7) 0.0575(17) Uani 1 1 d . . . . .
H24A H -0.0046 1.1103 0.8797 0.086 Uiso 1 1 calc R U . . .
H24B H 0.1404 1.1754 0.8724 0.086 Uiso 1 1 calc R U . . .
H24C H 0.1662 0.9972 0.8863 0.086 Uiso 1 1 calc R U . . .
C25 C 0.3864(9) 0.9512(7) 0.1670(6) 0.0502(15) Uani 1 1 d . . . . .
H25A H 0.3407 1.0587 0.1506 0.075 Uiso 1 1 calc R U . . .
H25B H 0.3784 0.8877 0.0970 0.075 Uiso 1 1 calc R U . . .
H25C H 0.5057 0.9277 0.1493 0.075 Uiso 1 1 calc R U . . .
O26 O 0.2193(6) 0.7396(5) 0.2449(6) 0.0572(12) Uani 1 1 d . . . . .
C27 C 0.0626(9) 0.6468(7) 0.5215(10) 0.0608(19) Uani 1 1 d . . . . .
H27A H -0.0542 0.6779 0.5994 0.091 Uiso 1 1 calc R U . . .
H27B H 0.1326 0.5595 0.5540 0.091 Uiso 1 1 calc R U . . .
H27C H 0.0632 0.6182 0.4270 0.091 Uiso 1 1 calc R U . . .
O28 O 0.0303(6) 0.8131(6) 0.7540(5) 0.0567(12) Uani 1 1 d . . . . .
C31 C 0.5332(7) 0.3675(6) 0.2919(8) 0.0515(17) Uani 1 1 d D . . . .
O32 O 0.5066(6) 0.3638(5) 0.4228(5) 0.0601(13) Uani 1 1 d D . . . .
O33 O 0.5096(6) 0.2683(5) 0.2189(5) 0.0571(11) Uani 1 1 d D . . . .
H33 H 0.4810 0.2008 0.2770 0.086 Uiso 1 1 calc R U . . .
C34 C 0.5838(8) 0.4975(6) 0.2003(7) 0.0552(16) Uani 1 1 d D . . . .
H34 H 0.4936 0.5531 0.1650 0.066 Uiso 1 1 calc R U . . .
O35 O 0.5972(7) 0.6016(5) 0.2891(6) 0.0674(14) Uani 1 1 d D . . . .
H35 H 0.5733 0.5726 0.3774 0.101 Uiso 1 1 calc R U . . .
C36 C 0.7499(8) 0.4397(6) 0.0635(7) 0.0525(14) Uani 1 1 d D . . . .
H36A H 0.7416 0.3643 0.0037 0.063 Uiso 1 1 calc R U . . .
H36B H 0.8414 0.3875 0.0968 0.063 Uiso 1 1 calc R U . . .
C37 C 0.7958(9) 0.5662(7) -0.0353(7) 0.0577(18) Uani 1 1 d D . . . .
O38 O 0.6915(10) 0.6754(9) -0.0503(12) 0.185(6) Uani 1 1 d D . . . .
O39 O 0.9498(7) 0.5366(9) -0.1194(8) 0.115(3) Uani 1 1 d D . . . .
H39 H 0.9661 0.6117 -0.1705 0.172 Uiso 1 1 calc R U . . .
C41 C 0.462(2) 0.6265(16) 0.7167(14) 0.033(4) Uani 0.622(12) 1 d D . P A 1
O42 O 0.5534(17) 0.5897(16) 0.5864(11) 0.049(2) Uani 0.622(12) 1 d D . P A 1
O43 O 0.452(2) 0.7468(14) 0.7881(15) 0.052(3) Uani 0.622(12) 1 d D . P A 1
H43 H 0.5238 0.7870 0.7303 0.078 Uiso 0.622(12) 1 calc R U P A 1
C44 C 0.3368(12) 0.5453(9) 0.8127(9) 0.042(2) Uani 0.622(12) 1 d D . P A 1
H44 H 0.2195 0.6157 0.8357 0.051 Uiso 0.622(12) 1 calc R U P A 1
O45 O 0.365(2) 0.4181(14) 0.7243(11) 0.065(4) Uani 0.622(12) 1 d D . P A 1
H45 H 0.3827 0.4428 0.6354 0.097 Uiso 0.622(12) 1 calc R U P A 1
C46 C 0.3483(10) 0.4970(9) 0.9601(8) 0.039(2) Uani 0.622(12) 1 d D . P A 1
H46A H 0.3493 0.5836 1.0117 0.046 Uiso 0.622(12) 1 calc R U P A 1
H46B H 0.4558 0.4135 0.9401 0.046 Uiso 0.622(12) 1 calc R U P A 1
C47 C 0.1983(13) 0.4435(13) 1.0623(14) 0.031(2) Uani 0.622(12) 1 d D . P A 1
O48 O 0.0624(9) 0.5371(11) 1.1306(11) 0.048(2) Uani 0.622(12) 1 d D . P A 1
O49 O 0.2273(12) 0.3000(9) 1.0697(12) 0.046(2) Uani 0.622(12) 1 d D . P A 1
H49 H 0.1454 0.2821 1.1421 0.069 Uiso 0.622(12) 1 calc R U P A 1
C41B C 0.214(4) 0.405(3) 1.041(2) 0.092(16) Uani 0.378(12) 1 d D . P A 2
O42B O 0.123(5) 0.490(3) 1.150(2) 0.154(16) Uani 0.378(12) 1 d D . P A 2
O43B O 0.205(2) 0.2667(15) 1.0300(15) 0.040(3) Uani 0.378(12) 1 d D . P A 2
H43B H 0.1124 0.2604 1.0967 0.061 Uiso 0.378(12) 1 calc R U P A 2
C44B C 0.3511(15) 0.4415(12) 0.9002(12) 0.033(3) Uani 0.378(12) 1 d D . P A 2
H44B H 0.4629 0.3944 0.9067 0.039 Uiso 0.378(12) 1 calc R U P A 2
O45B O 0.3576(18) 0.3733(15) 0.7719(12) 0.042(3) Uani 0.378(12) 1 d D . P A 2
H45B H 0.4042 0.4162 0.6942 0.063 Uiso 0.378(12) 1 calc R U P A 2
C46B C 0.3163(16) 0.6101(12) 0.8958(11) 0.031(3) Uani 0.378(12) 1 d D . P A 2
H46C H 0.3190 0.6467 0.9866 0.037 Uiso 0.378(12) 1 calc R U P A 2
H46D H 0.1996 0.6577 0.9023 0.037 Uiso 0.378(12) 1 calc R U P A 2
C47B C 0.436(3) 0.665(2) 0.759(2) 0.027(5) Uani 0.378(12) 1 d D . P A 2
O48B O 0.528(3) 0.586(2) 0.6455(18) 0.057(6) Uani 0.378(12) 1 d D . P A 2
O49B O 0.432(3) 0.7988(19) 0.774(3) 0.053(6) Uani 0.378(12) 1 d D . P A 2
H49B H 0.5168 0.8147 0.7034 0.080 Uiso 0.378(12) 1 calc R U P A 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
N1 C2 1.342(8) . ?
N1 C5 1.355(7) . ?
C2 N3 1.352(8) . ?
C2 H2 0.9500 . ?
N3 C4 1.375(7) . ?
N3 C10 1.472(7) . ?
C4 C5 1.376(8) . ?
C4 C9 1.420(7) . ?
C5 N6 1.370(7) . ?
N6 C7 1.369(7) . ?
N6 C11 1.472(7) . ?
C7 O12 1.228(7) . ?
C7 N8 1.410(7) . ?
N8 C9 1.393(7) . ?
N8 C13 1.472(7) . ?
C9 O14 1.238(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N15 C16 1.343(7) . ?
N15 C19 1.363(7) . ?
C16 N17 1.329(8) . ?
C16 H16 0.9500 . ?
N17 C18 1.390(8) . ?
N17 C24 1.461(8) . ?
C18 C19 1.357(7) . ?
C18 C23 1.436(8) . ?
C19 N20 1.356(7) . ?
N20 C21 1.393(7) . ?
N20 C25 1.470(7) . ?
C21 O26 1.202(7) . ?
C21 N22 1.392(8) . ?
N22 C23 1.404(8) . ?
N22 C27 1.476(8) . ?
C23 O28 1.217(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 O32 1.198(8) . ?
C31 O33 1.333(7) . ?
C31 C34 1.519(7) . ?
O33 H33 0.8400 . ?
C34 O35 1.420(7) . ?
C34 C36 1.510(7) . ?
C34 H34 1.0000 . ?
O35 H35 0.8400 . ?
C36 C37 1.510(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 O38 1.195(9) . ?
C37 O39 1.246(8) . ?
O39 H39 0.8400 . ?
C41 O42 1.198(11) . ?
C41 O43 1.326(12) . ?
C41 C44 1.517(11) . ?
O43 H43 0.8400 . ?
C44 O45 1.416(9) . ?
C44 C46 1.508(9) . ?
C44 H44 1.0000 . ?
O45 H45 0.8400 . ?
C46 C47 1.529(10) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 O48 1.206(12) . ?
C47 O49 1.277(12) . ?
O49 H49 0.8400 . ?
C41B O42B 1.196(13) . ?
C41B O43B 1.331(14) . ?
C41B C44B 1.527(13) . ?
O43B H43B 0.8400 . ?
C44B O45B 1.424(12) . ?
C44B C46B 1.497(11) . ?
C44B H44B 1.0000 . ?
O45B H45B 0.8400 . ?
C46B C47B 1.504(13) . ?
C46B H46C 0.9900 . ?
C46B H46D 0.9900 . ?
C47B O48B 1.201(13) . ?
C47B O49B 1.256(13) . ?
O49B H49B 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 104.0(5) . . ?
N1 C2 N3 112.6(5) . . ?
N1 C2 H2 123.7 . . ?
N3 C2 H2 123.7 . . ?
C2 N3 C4 106.4(5) . . ?
C2 N3 C10 126.2(5) . . ?
C4 N3 C10 127.4(5) . . ?
N3 C4 C5 105.5(5) . . ?
N3 C4 C9 132.3(5) . . ?
C5 C4 C9 122.1(5) . . ?
N1 C5 N6 126.5(5) . . ?
N1 C5 C4 111.5(5) . . ?
N6 C5 C4 121.9(5) . . ?
C7 N6 C5 119.9(4) . . ?
C7 N6 C11 119.6(5) . . ?
C5 N6 C11 120.4(5) . . ?
O12 C7 N6 121.8(5) . . ?
O12 C7 N8 121.4(5) . . ?
N6 C7 N8 116.8(5) . . ?
C9 N8 C7 126.4(5) . . ?
C9 N8 C13 116.7(4) . . ?
C7 N8 C13 116.8(5) . . ?
O14 C9 N8 121.6(5) . . ?
O14 C9 C4 125.8(5) . . ?
N8 C9 C4 112.6(5) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N15 C19 103.6(5) . . ?
N17 C16 N15 113.5(5) . . ?
N17 C16 H16 123.3 . . ?
N15 C16 H16 123.3 . . ?
C16 N17 C18 105.8(5) . . ?
C16 N17 C24 125.3(5) . . ?
C18 N17 C24 128.9(5) . . ?
C19 C18 N17 106.1(5) . . ?
C19 C18 C23 123.4(5) . . ?
N17 C18 C23 130.5(5) . . ?
N20 C19 C18 122.7(5) . . ?
N20 C19 N15 126.3(5) . . ?
C18 C19 N15 111.1(5) . . ?
C19 N20 C21 119.0(5) . . ?
C19 N20 C25 122.0(5) . . ?
C21 N20 C25 118.9(5) . . ?
O26 C21 N22 122.2(6) . . ?
O26 C21 N20 121.1(6) . . ?
N22 C21 N20 116.8(5) . . ?
C21 N22 C23 127.7(5) . . ?
C21 N22 C27 115.9(5) . . ?
C23 N22 C27 116.4(5) . . ?
O28 C23 N22 121.9(6) . . ?
O28 C23 C18 127.8(6) . . ?
N22 C23 C18 110.3(5) . . ?
N17 C24 H24A 109.5 . . ?
N17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N20 C25 H25A 109.5 . . ?
N20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O32 C31 O33 124.0(5) . . ?
O32 C31 C34 120.6(6) . . ?
O33 C31 C34 115.1(6) . . ?
C31 O33 H33 109.5 . . ?
O35 C34 C36 109.3(5) . . ?
O35 C34 C31 111.2(5) . . ?
C36 C34 C31 111.4(4) . . ?
O35 C34 H34 108.2 . . ?
C36 C34 H34 108.2 . . ?
C31 C34 H34 108.2 . . ?
C34 O35 H35 109.5 . . ?
C34 C36 C37 112.2(4) . . ?
C34 C36 H36A 109.2 . . ?
C37 C36 H36A 109.2 . . ?
C34 C36 H36B 109.2 . . ?
C37 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
O38 C37 O39 121.6(6) . . ?
O38 C37 C36 122.6(7) . . ?
O39 C37 C36 114.6(6) . . ?
C37 O39 H39 109.5 . . ?
O42 C41 O43 123.9(11) . . ?
O42 C41 C44 122.5(11) . . ?
O43 C41 C44 113.4(11) . . ?
C41 O43 H43 109.5 . . ?
O45 C44 C46 110.8(8) . . ?
O45 C44 C41 107.3(8) . . ?
C46 C44 C41 114.1(8) . . ?
O45 C44 H44 108.2 . . ?
C46 C44 H44 108.2 . . ?
C41 C44 H44 108.2 . . ?
C44 O45 H45 109.5 . . ?
C44 C46 C47 110.9(7) . . ?
C44 C46 H46A 109.5 . . ?
C47 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
C47 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?
O48 C47 O49 124.3(10) . . ?
O48 C47 C46 119.1(10) . . ?
O49 C47 C46 116.6(9) . . ?
C47 O49 H49 109.5 . . ?
O42B C41B O43B 122.7(15) . . ?
O42B C41B C44B 124.5(15) . . ?
O43B C41B C44B 112.9(12) . . ?
C41B O43B H43B 109.5 . . ?
O45B C44B C46B 113.9(10) . . ?
O45B C44B C41B 108.0(12) . . ?
C46B C44B C41B 109.6(11) . . ?
O45B C44B H44B 108.4 . . ?
C46B C44B H44B 108.4 . . ?
C41B C44B H44B 108.4 . . ?
C44B O45B H45B 109.5 . . ?
C44B C46B C47B 116.1(10) . . ?
C44B C46B H46C 108.3 . . ?
C47B C46B H46C 108.3 . . ?
C44B C46B H46D 108.3 . . ?
C47B C46B H46D 108.3 . . ?
H46C C46B H46D 107.4 . . ?
O48B C47B O49B 123.1(16) . . ?
O48B C47B C46B 122.2(14) . . ?
O49B C47B C46B 114.7(14) . . ?
C47B O49B H49B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.7(7) . . . . ?
N1 C2 N3 C4 0.0(7) . . . . ?
N1 C2 N3 C10 177.7(5) . . . . ?
C2 N3 C4 C5 -0.7(6) . . . . ?
C10 N3 C4 C5 -178.3(5) . . . . ?
C2 N3 C4 C9 -178.8(6) . . . . ?
C10 N3 C4 C9 3.5(10) . . . . ?
C2 N1 C5 N6 -178.0(5) . . . . ?
C2 N1 C5 C4 -1.1(7) . . . . ?
N3 C4 C5 N1 1.1(6) . . . . ?
C9 C4 C5 N1 179.5(5) . . . . ?
N3 C4 C5 N6 178.2(5) . . . . ?
C9 C4 C5 N6 -3.4(8) . . . . ?
N1 C5 N6 C7 179.4(5) . . . . ?
C4 C5 N6 C7 2.8(8) . . . . ?
N1 C5 N6 C11 -1.9(9) . . . . ?
C4 C5 N6 C11 -178.5(5) . . . . ?
C5 N6 C7 O12 -178.8(5) . . . . ?
C11 N6 C7 O12 2.5(9) . . . . ?
C5 N6 C7 N8 0.5(8) . . . . ?
C11 N6 C7 N8 -178.3(5) . . . . ?
O12 C7 N8 C9 175.8(5) . . . . ?
N6 C7 N8 C9 -3.4(8) . . . . ?
O12 C7 N8 C13 -3.8(8) . . . . ?
N6 C7 N8 C13 176.9(5) . . . . ?
C7 N8 C9 O14 -177.0(5) . . . . ?
C13 N8 C9 O14 2.7(7) . . . . ?
C7 N8 C9 C4 2.8(7) . . . . ?
C13 N8 C9 C4 -177.6(5) . . . . ?
N3 C4 C9 O14 -1.7(10) . . . . ?
C5 C4 C9 O14 -179.6(5) . . . . ?
N3 C4 C9 N8 178.6(5) . . . . ?
C5 C4 C9 N8 0.7(7) . . . . ?
C19 N15 C16 N17 0.5(7) . . . . ?
N15 C16 N17 C18 0.8(7) . . . . ?
N15 C16 N17 C24 -177.7(5) . . . . ?
C16 N17 C18 C19 -1.7(6) . . . . ?
C24 N17 C18 C19 176.8(5) . . . . ?
C16 N17 C18 C23 177.9(6) . . . . ?
C24 N17 C18 C23 -3.6(10) . . . . ?
N17 C18 C19 N20 -178.0(5) . . . . ?
C23 C18 C19 N20 2.4(9) . . . . ?
N17 C18 C19 N15 2.1(6) . . . . ?
C23 C18 C19 N15 -177.6(5) . . . . ?
C16 N15 C19 N20 178.4(5) . . . . ?
C16 N15 C19 C18 -1.6(6) . . . . ?
C18 C19 N20 C21 -1.3(8) . . . . ?
N15 C19 N20 C21 178.7(5) . . . . ?
C18 C19 N20 C25 -178.3(5) . . . . ?
N15 C19 N20 C25 1.6(9) . . . . ?
C19 N20 C21 O26 178.0(5) . . . . ?
C25 N20 C21 O26 -4.8(9) . . . . ?
C19 N20 C21 N22 -1.3(7) . . . . ?
C25 N20 C21 N22 175.8(5) . . . . ?
O26 C21 N22 C23 -176.1(5) . . . . ?
N20 C21 N22 C23 3.2(8) . . . . ?
O26 C21 N22 C27 4.1(8) . . . . ?
N20 C21 N22 C27 -176.5(5) . . . . ?
C21 N22 C23 O28 178.1(6) . . . . ?
C27 N22 C23 O28 -2.1(8) . . . . ?
C21 N22 C23 C18 -2.1(8) . . . . ?
C27 N22 C23 C18 177.6(5) . . . . ?
C19 C18 C23 O28 179.0(6) . . . . ?
N17 C18 C23 O28 -0.5(11) . . . . ?
C19 C18 C23 N22 -0.7(8) . . . . ?
N17 C18 C23 N22 179.7(5) . . . . ?
O32 C31 C34 O35 1.5(8) . . . . ?
O33 C31 C34 O35 176.9(5) . . . . ?
O32 C31 C34 C36 123.8(6) . . . . ?
O33 C31 C34 C36 -60.9(7) . . . . ?
O35 C34 C36 C37 -60.9(7) . . . . ?
C31 C34 C36 C37 175.7(6) . . . . ?
C34 C36 C37 O38 -33.6(13) . . . . ?
C34 C36 C37 O39 158.0(7) . . . . ?
O42 C41 C44 O45 6(2) . . . . ?
O43 C41 C44 O45 -178.5(15) . . . . ?
O42 C41 C44 C46 129.0(16) . . . . ?
O43 C41 C44 C46 -55.4(17) . . . . ?
O45 C44 C46 C47 -69.4(11) . . . . ?
C41 C44 C46 C47 169.4(9) . . . . ?
C44 C46 C47 O48 -78.2(14) . . . . ?
C44 C46 C47 O49 102.1(11) . . . . ?
O42B C41B C44B O45B -144(4) . . . . ?
O43B C41B C44B O45B 36(4) . . . . ?
O42B C41B C44B C46B -20(5) . . . . ?
O43B C41B C44B C46B 161(3) . . . . ?
O45B C44B C46B C47B -55.7(19) . . . . ?
C41B C44B C46B C47B -177(2) . . . . ?
C44B C46B C47B O48B 17(4) . . . . ?
C44B C46B C47B O49B -163(2) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994949'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tl

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 N4 O2), C6 H10 O4'
_chemical_formula_sum            'C22 H30 N8 O8'
_chemical_formula_weight         534.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 '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 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   21.3368(9)
_cell_length_b                   17.0520(5)
_cell_length_c                   6.7877(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.674(4)
_cell_angle_gamma                90
_cell_volume                     2464.52(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3449
_cell_measurement_theta_min      1.7710
_cell_measurement_theta_max      29.6320

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
3 datasets were measured (psi scan), all were twinned (180 deg 
around the direct a-axis) 
5 twin domains were integrated seperately, hklf5 datasets were 
generated by platon for all individual datasets.
All data were combind into one file with unique batch numbers 
(after checking the overal scale factor based on intensity - in
wingx)
All datasets were thus treated as different experiments, but refined 
simultaniously.

_cell_measurement, _exptl_absorpt_correction entries are given
for dataset1, domain1
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82103
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  'pilatus 2M'
_diffrn_measurement_method       '359 images, ΔΦ 1.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16281
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         29.644
_diffrn_reflns_theta_full        29.513
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             16281
_reflns_number_gt                12903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'SNBL Pilatus control'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          
;
 Refined as a 10-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16281
_refine_ls_number_parameters     407
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.13072(10) 0.64919(13) 0.3838(4) 0.0226(6) Uani 1 1 d D . . . .
C2 C 0.17419(12) 0.70485(17) 0.4248(5) 0.0266(8) Uani 1 1 d D . . . .
H2 H 0.2168 0.6936 0.4643 0.032 Uiso 1 1 calc R U . . .
N3 N 0.15137(10) 0.77796(14) 0.4042(4) 0.0242(6) Uani 1 1 d D . . . .
C4 C 0.08833(11) 0.77007(15) 0.3442(4) 0.0189(7) Uani 1 1 d D . . . .
C5 C 0.07783(11) 0.69129(16) 0.3345(4) 0.0194(7) Uani 1 1 d D . . . .
N6 N 0.02010(9) 0.66040(13) 0.2805(4) 0.0190(6) Uani 1 1 d D . . . .
C7 C -0.02949(12) 0.71042(16) 0.2319(4) 0.0200(7) Uani 1 1 d D . . . .
N8 N -0.01730(9) 0.79105(13) 0.2468(4) 0.0205(6) Uani 1 1 d D . . . .
C9 C 0.04069(12) 0.82696(16) 0.2999(4) 0.0203(7) Uani 1 1 d D . . . .
C10 C 0.18662(13) 0.85102(18) 0.4355(5) 0.0319(8) Uani 1 1 d D . . . .
H10A H 0.1972 0.8724 0.3077 0.048 Uiso 1 1 calc R U . . .
H10B H 0.2253 0.8406 0.5168 0.048 Uiso 1 1 calc R U . . .
H10C H 0.1610 0.8890 0.5028 0.048 Uiso 1 1 calc R U . . .
C11 C 0.01033(13) 0.57466(15) 0.2723(5) 0.0258(8) Uani 1 1 d D . . . .
H11A H 0.0283 0.5507 0.3944 0.039 Uiso 1 1 calc R U . . .
H11B H 0.0309 0.5530 0.1594 0.039 Uiso 1 1 calc R U . . .
H11C H -0.0348 0.5634 0.2576 0.039 Uiso 1 1 calc R U . . .
O12 O -0.08168(8) 0.68635(12) 0.1791(3) 0.0272(5) Uani 1 1 d D . . . .
C13 C -0.07179(12) 0.84298(18) 0.2031(5) 0.0285(8) Uani 1 1 d D . . . .
H13A H -0.1023 0.8356 0.3034 0.043 Uiso 1 1 calc R U . . .
H13B H -0.0915 0.8301 0.0727 0.043 Uiso 1 1 calc R U . . .
H13C H -0.0578 0.8977 0.2042 0.043 Uiso 1 1 calc R U . . .
O14 O 0.04681(9) 0.89829(11) 0.3061(3) 0.0276(5) Uani 1 1 d D . . . .
N15A N 0.53229(9) 0.63311(10) 0.3483(8) 0.0215(11) Uani 0.4652(17) 1 d D . P A
3
C16A C 0.49539(8) 0.56906(12) 0.3319(11) 0.0287(14) Uani 0.4652(17) 1 d D U P A
3
H16A H 0.5114 0.5171 0.3347 0.034 Uiso 0.4652(17) 1 calc R U P A 3
N17A N 0.43342(8) 0.58586(9) 0.3112(8) 0.0208(7) Uani 0.4652(17) 1 d D . P A 3
C18A C 0.42983(7) 0.66678(8) 0.3111(10) 0.0141(8) Uani 0.4652(17) 1 d D U P A 3
C19A C 0.49032(8) 0.69295(8) 0.3323(9) 0.0136(13) Uani 0.4652(17) 1 d D . P A 3
N20A N 0.50440(7) 0.77163(9) 0.3365(9) 0.0187(14) Uani 0.4652(17) 1 d D . P A 3
C21A C 0.45651(7) 0.82589(9) 0.3118(11) 0.0232(11) Uani 0.4652(17) 1 d D U P A
3
N22A N 0.39546(7) 0.79717(9) 0.2906(9) 0.0179(6) Uani 0.4652(17) 1 d D U P A 3
C23A C 0.37753(7) 0.71788(9) 0.2866(11) 0.0188(7) Uani 0.4652(17) 1 d D U P A 3
C24A C 0.38293(12) 0.52875(15) 0.2991(14) 0.0423(12) Uani 0.4652(17) 1 d D . P
A 3
H24A H 0.3985 0.4785 0.3527 0.064 Uiso 0.4652(17) 1 calc R U P A 3
H24B H 0.3678 0.5218 0.1609 0.064 Uiso 0.4652(17) 1 calc R U P A 3
H24C H 0.3484 0.5473 0.3757 0.064 Uiso 0.4652(17) 1 calc R U P A 3
C25A C 0.56949(9) 0.8013(2) 0.3611(11) 0.0277(13) Uani 0.4652(17) 1 d D . P A 3
H25A H 0.5816 0.8235 0.2360 0.042 Uiso 0.4652(17) 1 calc R U P A 3
H25B H 0.5979 0.7580 0.4003 0.042 Uiso 0.4652(17) 1 calc R U P A 3
H25C H 0.5721 0.8419 0.4633 0.042 Uiso 0.4652(17) 1 calc R U P A 3
O26A O 0.46772(14) 0.89617(10) 0.3201(8) 0.0259(11) Uani 0.4652(17) 1 d D . P A
3
C27A C 0.34450(11) 0.85591(14) 0.2640(12) 0.0227(10) Uani 0.4652(17) 1 d D . P
A 3
H27A H 0.3628 0.9081 0.2493 0.034 Uiso 0.4652(17) 1 calc R U P A 3
H27B H 0.3192 0.8553 0.3795 0.034 Uiso 0.4652(17) 1 calc R U P A 3
H27C H 0.3178 0.8431 0.1455 0.034 Uiso 0.4652(17) 1 calc R U P A 3
O28A O 0.32143(8) 0.69897(18) 0.2580(8) 0.0288(9) Uani 0.4652(17) 1 d D . P A 3
N15B N 0.51861(8) 0.62236(10) 0.2247(4) 0.0215(11) Uani 0.5348(17) 1 d D . P A
4
C16B C 0.47775(8) 0.56313(12) 0.2446(3) 0.0287(14) Uani 0.5348(17) 1 d D . P A
4
H16B H 0.4893 0.5094 0.2386 0.034 Uiso 0.5348(17) 1 calc R U P A 4
N17B N 0.41879(7) 0.58743(9) 0.2740(4) 0.0208(7) Uani 0.5348(17) 1 d D . P A 4
C18B C 0.42171(7) 0.66839(8) 0.2756(7) 0.0141(8) Uani 0.5348(17) 1 d D . P A 4
C19B C 0.48261(8) 0.68705(8) 0.2463(6) 0.0136(13) Uani 0.5348(17) 1 d D . P A 4
N20B N 0.50237(7) 0.76364(8) 0.2377(6) 0.0187(14) Uani 0.5348(17) 1 d D . P A 4
C21B C 0.45961(7) 0.82355(9) 0.2563(8) 0.0232(11) Uani 0.5348(17) 1 d D . P A 4
N22B N 0.39799(7) 0.80241(9) 0.2858(7) 0.0179(6) Uani 0.5348(17) 1 d D . P A 4
C23B C 0.37452(7) 0.72568(9) 0.2971(8) 0.0188(7) Uani 0.5348(17) 1 d D . P A 4
C24B C 0.36597(11) 0.53667(16) 0.3077(9) 0.0423(12) Uani 0.5348(17) 1 d D . P A
4
H24D H 0.3709 0.4868 0.2385 0.064 Uiso 0.5348(17) 1 calc R U P A 4
H24E H 0.3269 0.5621 0.2578 0.064 Uiso 0.5348(17) 1 calc R U P A 4
H24F H 0.3644 0.5268 0.4495 0.064 Uiso 0.5348(17) 1 calc R U P A 4
C25B C 0.56822(9) 0.7854(2) 0.2096(8) 0.0277(13) Uani 0.5348(17) 1 d D . P A 4
H25D H 0.5709 0.8099 0.0798 0.042 Uiso 0.5348(17) 1 calc R U P A 4
H25E H 0.5946 0.7383 0.2176 0.042 Uiso 0.5348(17) 1 calc R U P A 4
H25F H 0.5829 0.8225 0.3128 0.042 Uiso 0.5348(17) 1 calc R U P A 4
O26B O 0.47524(12) 0.89192(10) 0.2361(6) 0.0259(11) Uani 0.5348(17) 1 d D . P A
4
C27B C 0.35279(11) 0.86715(13) 0.3088(9) 0.0227(10) Uani 0.5348(17) 1 d D . P A
4
H27D H 0.3752 0.9174 0.3119 0.034 Uiso 0.5348(17) 1 calc R U P A 4
H27E H 0.3321 0.8602 0.4324 0.034 Uiso 0.5348(17) 1 calc R U P A 4
H27F H 0.3212 0.8667 0.1975 0.034 Uiso 0.5348(17) 1 calc R U P A 4
O28B O 0.31830(8) 0.71380(17) 0.3248(6) 0.0288(9) Uani 0.5348(17) 1 d D . P A 4
C31 C 0.20286(11) 0.48115(16) 0.5607(5) 0.0203(7) Uani 1 1 d . . . . .
O42 O 0.24369(8) 0.53026(11) 0.5844(3) 0.0267(5) Uani 1 1 d . . . . .
O43 O 0.14884(8) 0.49417(11) 0.4590(3) 0.0314(6) Uani 1 1 d . . . . .
H43 H 0.1483 0.5403 0.4152 0.047 Uiso 1 1 calc R U . . .
C44 C 0.20663(12) 0.39926(15) 0.6428(5) 0.0220(7) Uani 1 1 d . . . . .
H44A H 0.2185 0.3632 0.5372 0.026 Uiso 1 1 calc R U . . .
H44B H 0.1644 0.3836 0.6807 0.026 Uiso 1 1 calc R U . . .
C45 C 0.25284(12) 0.38871(16) 0.8206(5) 0.0222(7) Uani 1 1 d . . . . .
C46 C 0.31963(13) 0.39926(19) 0.7628(6) 0.0435(10) Uani 1 1 d . . . . .
O47 O 0.33497(10) 0.37345(13) 0.6004(4) 0.0510(7) Uani 1 1 d . . . . .
H47 H 0.3731 0.3833 0.5872 0.077 Uiso 0.4652(17) 1 calc R U P . .
O48 O 0.35963(10) 0.42754(19) 0.8892(4) 0.0747(10) Uani 1 1 d . . . . .
H48 H 0.3960 0.4159 0.8582 0.112 Uiso 0.5348(17) 1 calc R U P . .
C49 C 0.24871(13) 0.30340(16) 0.8940(5) 0.0290(8) Uani 1 1 d . . . . .
H49A H 0.2558 0.2674 0.7852 0.044 Uiso 1 1 calc R U . . .
H49B H 0.2070 0.2940 0.9416 0.044 Uiso 1 1 calc R U . . .
H49C H 0.2807 0.2947 1.0019 0.044 Uiso 1 1 calc R U . . .
C50 C 0.23776(16) 0.44275(19) 0.9906(5) 0.0407(9) Uani 1 1 d . . . . .
H50A H 0.2649 0.4296 1.1079 0.061 Uiso 1 1 calc R U . . .
H50B H 0.1937 0.4360 1.0198 0.061 Uiso 1 1 calc R U . . .
H50C H 0.2450 0.4974 0.9532 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.344(4) . ?
N1 C5 1.361(3) . ?
C2 N3 1.343(4) . ?
C2 H2 0.9500 . ?
N3 C4 1.387(3) . ?
N3 C10 1.464(3) . ?
C4 C5 1.363(4) . ?
C4 C9 1.423(4) . ?
C5 N6 1.368(3) . ?
N6 C7 1.382(3) . ?
N6 C11 1.477(3) . ?
C7 O12 1.219(3) . ?
C7 N8 1.402(3) . ?
N8 C9 1.407(3) . ?
N8 C13 1.476(3) . ?
C9 O14 1.224(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N15A C16A 1.347(2) . ?
N15A C19A 1.357(2) . ?
C16A N17A 1.351(2) . ?
C16A H16A 0.9500 . ?
N17A C18A 1.3820(19) . ?
N17A C24A 1.451(3) . ?
C18A C19A 1.365(2) . ?
C18A C23A 1.417(2) . ?
C19A N20A 1.3748(19) . ?
N20A C21A 1.381(2) . ?
N20A C25A 1.477(2) . ?
C21A O26A 1.223(2) . ?
C21A N22A 1.390(2) . ?
N22A C23A 1.4050(19) . ?
N22A C27A 1.481(2) . ?
C23A O28A 1.243(2) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
N15B C16B 1.347(2) . ?
N15B C19B 1.358(2) . ?
C16B N17B 1.351(2) . ?
C16B H16B 0.9500 . ?
N17B C18B 1.3820(19) . ?
N17B C24B 1.451(3) . ?
C18B C19B 1.365(2) . ?
C18B C23B 1.417(2) . ?
C19B N20B 1.3746(19) . ?
N20B C21B 1.381(2) . ?
N20B C25B 1.477(2) . ?
C21B O26B 1.223(2) . ?
C21B N22B 1.390(2) . ?
N22B C23B 1.4050(19) . ?
N22B C27B 1.481(2) . ?
C23B O28B 1.243(2) . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
C31 O42 1.212(3) . ?
C31 O43 1.324(3) . ?
C31 C44 1.504(4) . ?
O43 H43 0.8400 . ?
C44 C45 1.519(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.513(4) . ?
C45 C50 1.527(4) . ?
C45 C49 1.542(4) . ?
C46 O47 1.250(5) . ?
C46 O48 1.266(4) . ?
O47 H47 0.8400 . ?
O48 H48 0.8400 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 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 N1 C5 103.2(2) . . ?
N3 C2 N1 113.2(2) . . ?
N3 C2 H2 123.4 . . ?
N1 C2 H2 123.4 . . ?
C2 N3 C4 106.2(2) . . ?
C2 N3 C10 126.6(2) . . ?
C4 N3 C10 127.2(2) . . ?
C5 C4 N3 105.3(2) . . ?
C5 C4 C9 123.3(2) . . ?
N3 C4 C9 131.5(2) . . ?
N1 C5 C4 112.1(2) . . ?
N1 C5 N6 125.5(2) . . ?
C4 C5 N6 122.3(2) . . ?
C5 N6 C7 119.3(2) . . ?
C5 N6 C11 120.9(2) . . ?
C7 N6 C11 119.8(2) . . ?
O12 C7 N6 122.2(3) . . ?
O12 C7 N8 120.9(2) . . ?
N6 C7 N8 116.9(2) . . ?
C7 N8 C9 127.0(2) . . ?
C7 N8 C13 115.7(2) . . ?
C9 N8 C13 117.3(2) . . ?
O14 C9 N8 122.1(2) . . ?
O14 C9 C4 126.7(2) . . ?
N8 C9 C4 111.2(2) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16A N15A C19A 102.93(16) . . ?
N15A C16A N17A 113.56(17) . . ?
N15A C16A H16A 123.2 . . ?
N17A C16A H16A 123.2 . . ?
C16A N17A C18A 105.40(14) . . ?
C16A N17A C24A 125.57(17) . . ?
C18A N17A C24A 129.00(17) . . ?
C19A C18A N17A 105.92(13) . . ?
C19A C18A C23A 122.94(14) . . ?
N17A C18A C23A 131.09(15) . . ?
N15A C19A C18A 112.17(14) . . ?
N15A C19A N20A 126.14(15) . . ?
C18A C19A N20A 121.69(14) . . ?
C19A N20A C21A 119.50(15) . . ?
C19A N20A C25A 122.61(18) . . ?
C21A N20A C25A 117.87(17) . . ?
O26A C21A N20A 120.7(2) . . ?
O26A C21A N22A 121.95(19) . . ?
N20A C21A N22A 117.24(14) . . ?
C21A N22A C23A 126.38(14) . . ?
C21A N22A C27A 116.75(15) . . ?
C23A N22A C27A 116.85(16) . . ?
O28A C23A N22A 120.73(19) . . ?
O28A C23A C18A 127.02(19) . . ?
N22A C23A C18A 112.21(14) . . ?
N17A C24A H24A 109.5 . . ?
N17A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
N17A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
N20A C25A H25A 109.5 . . ?
N20A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
N20A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
N22A C27A H27A 109.5 . . ?
N22A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
N22A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C16B N15B C19B 102.96(16) . . ?
N15B C16B N17B 113.56(17) . . ?
N15B C16B H16B 123.2 . . ?
N17B C16B H16B 123.2 . . ?
C16B N17B C18B 105.40(15) . . ?
C16B N17B C24B 125.47(18) . . ?
C18B N17B C24B 129.04(18) . . ?
C19B C18B N17B 105.94(13) . . ?
C19B C18B C23B 122.94(14) . . ?
N17B C18B C23B 131.11(15) . . ?
N15B C19B C18B 112.14(14) . . ?
N15B C19B N20B 126.17(16) . . ?
C18B C19B N20B 121.69(14) . . ?
C19B N20B C21B 119.52(15) . . ?
C19B N20B C25B 122.76(18) . . ?
C21B N20B C25B 117.72(18) . . ?
O26B C21B N20B 120.58(19) . . ?
O26B C21B N22B 122.04(18) . . ?
N20B C21B N22B 117.25(14) . . ?
C21B N22B C23B 126.38(15) . . ?
C21B N22B C27B 116.77(15) . . ?
C23B N22B C27B 116.85(16) . . ?
O28B C23B N22B 120.73(19) . . ?
O28B C23B C18B 127.04(19) . . ?
N22B C23B C18B 112.23(14) . . ?
N17B C24B H24D 109.5 . . ?
N17B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
N17B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
N20B C25B H25D 109.5 . . ?
N20B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
N20B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
N22B C27B H27D 109.5 . . ?
N22B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
N22B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
O42 C31 O43 123.2(3) . . ?
O42 C31 C44 124.9(2) . . ?
O43 C31 C44 111.9(2) . . ?
C31 O43 H43 109.5 . . ?
C31 C44 C45 114.9(2) . . ?
C31 C44 H44A 108.5 . . ?
C45 C44 H44A 108.5 . . ?
C31 C44 H44B 108.5 . . ?
C45 C44 H44B 108.5 . . ?
H44A C44 H44B 107.5 . . ?
C46 C45 C44 110.7(3) . . ?
C46 C45 C50 111.8(3) . . ?
C44 C45 C50 111.8(2) . . ?
C46 C45 C49 105.7(2) . . ?
C44 C45 C49 108.7(2) . . ?
C50 C45 C49 107.8(3) . . ?
O47 C46 O48 121.9(3) . . ?
O47 C46 C45 119.4(3) . . ?
O48 C46 C45 118.4(3) . . ?
C46 O47 H47 109.5 . . ?
C46 O48 H48 109.5 . . ?
C45 C49 H49A 109.5 . . ?
C45 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C45 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C45 C50 H50A 109.5 . . ?
C45 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C45 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.1(4) . . . . ?
N1 C2 N3 C4 -0.3(4) . . . . ?
N1 C2 N3 C10 -179.3(3) . . . . ?
C2 N3 C4 C5 0.4(3) . . . . ?
C10 N3 C4 C5 179.3(3) . . . . ?
C2 N3 C4 C9 180.0(3) . . . . ?
C10 N3 C4 C9 -1.1(5) . . . . ?
C2 N1 C5 C4 0.2(3) . . . . ?
C2 N1 C5 N6 -179.9(3) . . . . ?
N3 C4 C5 N1 -0.4(3) . . . . ?
C9 C4 C5 N1 -180.0(3) . . . . ?
N3 C4 C5 N6 179.7(3) . . . . ?
C9 C4 C5 N6 0.1(5) . . . . ?
N1 C5 N6 C7 -179.2(3) . . . . ?
C4 C5 N6 C7 0.7(4) . . . . ?
N1 C5 N6 C11 0.3(4) . . . . ?
C4 C5 N6 C11 -179.8(3) . . . . ?
C5 N6 C7 O12 178.6(3) . . . . ?
C11 N6 C7 O12 -1.0(4) . . . . ?
C5 N6 C7 N8 -1.7(4) . . . . ?
C11 N6 C7 N8 178.7(2) . . . . ?
O12 C7 N8 C9 -178.1(3) . . . . ?
N6 C7 N8 C9 2.2(4) . . . . ?
O12 C7 N8 C13 2.5(4) . . . . ?
N6 C7 N8 C13 -177.2(2) . . . . ?
C7 N8 C9 O14 179.0(3) . . . . ?
C13 N8 C9 O14 -1.6(4) . . . . ?
C7 N8 C9 C4 -1.4(4) . . . . ?
C13 N8 C9 C4 178.0(3) . . . . ?
C5 C4 C9 O14 179.8(3) . . . . ?
N3 C4 C9 O14 0.3(5) . . . . ?
C5 C4 C9 N8 0.2(4) . . . . ?
N3 C4 C9 N8 -179.3(3) . . . . ?
C19A N15A C16A N17A -1.3(8) . . . . ?
N15A C16A N17A C18A 0.9(8) . . . . ?
N15A C16A N17A C24A -177.2(7) . . . . ?
C16A N17A C18A C19A -0.1(7) . . . . ?
C24A N17A C18A C19A 177.9(7) . . . . ?
C16A N17A C18A C23A 177.3(7) . . . . ?
C24A N17A C18A C23A -4.7(12) . . . . ?
C16A N15A C19A C18A 1.2(7) . . . . ?
C16A N15A C19A N20A -178.9(6) . . . . ?
N17A C18A C19A N15A -0.7(8) . . . . ?
C23A C18A C19A N15A -178.4(6) . . . . ?
N17A C18A C19A N20A 179.4(6) . . . . ?
C23A C18A C19A N20A 1.8(10) . . . . ?
N15A C19A N20A C21A 177.8(6) . . . . ?
C18A C19A N20A C21A -2.3(10) . . . . ?
N15A C19A N20A C25A -0.4(10) . . . . ?
C18A C19A N20A C25A 179.4(6) . . . . ?
C19A N20A C21A O26A 178.1(6) . . . . ?
C25A N20A C21A O26A -3.6(10) . . . . ?
C19A N20A C21A N22A 2.2(10) . . . . ?
C25A N20A C21A N22A -179.4(6) . . . . ?
O26A C21A N22A C23A -177.6(7) . . . . ?
N20A C21A N22A C23A -1.8(11) . . . . ?
O26A C21A N22A C27A 4.2(11) . . . . ?
N20A C21A N22A C27A -179.9(6) . . . . ?
C21A N22A C23A O28A -176.8(7) . . . . ?
C27A N22A C23A O28A 1.3(10) . . . . ?
C21A N22A C23A C18A 1.2(10) . . . . ?
C27A N22A C23A C18A 179.3(6) . . . . ?
C19A C18A C23A O28A 176.7(7) . . . . ?
N17A C18A C23A O28A -0.3(13) . . . . ?
C19A C18A C23A N22A -1.1(10) . . . . ?
N17A C18A C23A N22A -178.1(7) . . . . ?
C19B N15B C16B N17B 0.9(2) . . . . ?
N15B C16B N17B C18B -0.7(3) . . . . ?
N15B C16B N17B C24B -177.5(4) . . . . ?
C16B N17B C18B C19B 0.2(4) . . . . ?
C24B N17B C18B C19B 176.8(4) . . . . ?
C16B N17B C18B C23B 178.8(5) . . . . ?
C24B N17B C18B C23B -4.6(8) . . . . ?
C16B N15B C19B C18B -0.8(4) . . . . ?
C16B N15B C19B N20B -179.8(4) . . . . ?
N17B C18B C19B N15B 0.4(5) . . . . ?
C23B C18B C19B N15B -178.3(4) . . . . ?
N17B C18B C19B N20B 179.5(4) . . . . ?
C23B C18B C19B N20B 0.7(7) . . . . ?
N15B C19B N20B C21B 178.0(4) . . . . ?
C18B C19B N20B C21B -1.0(7) . . . . ?
N15B C19B N20B C25B -2.2(7) . . . . ?
C18B C19B N20B C25B 178.9(4) . . . . ?
C19B N20B C21B O26B -175.1(5) . . . . ?
C25B N20B C21B O26B 5.0(7) . . . . ?
C19B N20B C21B N22B 0.8(7) . . . . ?
C25B N20B C21B N22B -179.0(4) . . . . ?
O26B C21B N22B C23B 175.4(5) . . . . ?
N20B C21B N22B C23B -0.5(8) . . . . ?
O26B C21B N22B C27B -5.1(7) . . . . ?
N20B C21B N22B C27B 179.0(4) . . . . ?
C21B N22B C23B O28B 179.7(5) . . . . ?
C27B N22B C23B O28B 0.2(7) . . . . ?
C21B N22B C23B C18B 0.3(7) . . . . ?
C27B N22B C23B C18B -179.3(4) . . . . ?
C19B C18B C23B O28B -179.7(5) . . . . ?
N17B C18B C23B O28B 1.9(9) . . . . ?
C19B C18B C23B N22B -0.3(7) . . . . ?
N17B C18B C23B N22B -178.7(4) . . . . ?
O42 C31 C44 C45 22.3(4) . . . . ?
O43 C31 C44 C45 -157.3(2) . . . . ?
C31 C44 C45 C46 -67.3(3) . . . . ?
C31 C44 C45 C50 58.1(3) . . . . ?
C31 C44 C45 C49 177.0(2) . . . . ?
C44 C45 C46 O47 -38.3(4) . . . . ?
C50 C45 C46 O47 -163.7(3) . . . . ?
C49 C45 C46 O47 79.3(3) . . . . ?
C44 C45 C46 O48 148.3(3) . . . . ?
C50 C45 C46 O48 22.9(4) . . . . ?
C49 C45 C46 O48 -94.2(3) . . . . ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.099

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994950'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tlmo018

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 N4 O2), C5 H6 O4'
_chemical_formula_sum            'C21 H26 N8 O8'
_chemical_formula_weight         518.50

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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

_cell_length_a                   7.6414(6)
_cell_length_b                   15.7487(9)
_cell_length_c                   39.130(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4709.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3987
_cell_measurement_theta_min      2.4460
_cell_measurement_theta_max      25.2528

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.64451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '110 images, ΔΦ 1.5°'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26793
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.639
_diffrn_reflns_theta_max         25.307
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4263
_reflns_number_gt                2821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+1.1222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4263
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.1776(3) 0.29878(14) 0.27790(5) 0.0478(6) Uani 1 1 d . . . . .
C2 C 0.2411(4) 0.36187(19) 0.25870(7) 0.0526(7) Uani 1 1 d . . . . .
H2 H 0.2899 0.4110 0.2678 0.063 Uiso 1 1 calc R U . . .
N3 N 0.2278(3) 0.34746(14) 0.22521(6) 0.0467(6) Uani 1 1 d . . . . .
C4 C 0.1476(3) 0.26890(16) 0.22196(6) 0.0405(6) Uani 1 1 d . . . . .
C5 C 0.1197(3) 0.24158(16) 0.25456(6) 0.0391(6) Uani 1 1 d . . . . .
N6 N 0.0425(3) 0.16480(14) 0.26154(5) 0.0414(5) Uani 1 1 d . . . . .
C7 C -0.0091(3) 0.11369(18) 0.23497(7) 0.0434(6) Uani 1 1 d . . . . .
N8 N 0.0233(3) 0.14324(13) 0.20200(5) 0.0419(5) Uani 1 1 d . . . . .
C9 C 0.1048(3) 0.21958(17) 0.19274(6) 0.0425(6) Uani 1 1 d . . . . .
C10 C 0.2838(5) 0.4037(2) 0.19793(8) 0.0662(9) Uani 1 1 d . . . . .
H10A H 0.3345 0.4541 0.2076 0.099 Uiso 1 1 calc R U . . .
H10B H 0.1847 0.4190 0.1841 0.099 Uiso 1 1 calc R U . . .
H10C H 0.3692 0.3754 0.1840 0.099 Uiso 1 1 calc R U . . .
C11 C 0.0205(4) 0.1343(2) 0.29653(7) 0.0561(8) Uani 1 1 d . . . . .
H11A H -0.0998 0.1194 0.3003 0.084 Uiso 1 1 calc R U . . .
H11B H 0.0540 0.1781 0.3123 0.084 Uiso 1 1 calc R U . . .
H11C H 0.0929 0.0852 0.3001 0.084 Uiso 1 1 calc R U . . .
O12 O -0.0806(3) 0.04610(13) 0.24033(5) 0.0634(6) Uani 1 1 d . . . . .
C13 C -0.0302(4) 0.08851(19) 0.17330(7) 0.0582(8) Uani 1 1 d . . . . .
H13A H -0.1030 0.1203 0.1579 0.087 Uiso 1 1 calc R U . . .
H13B H -0.0943 0.0406 0.1819 0.087 Uiso 1 1 calc R U . . .
H13C H 0.0719 0.0689 0.1614 0.087 Uiso 1 1 calc R U . . .
O14 O 0.1350(3) 0.23655(13) 0.16300(5) 0.0606(6) Uani 1 1 d . . . . .
N15 N 0.7769(3) 1.00389(14) 0.01067(5) 0.0455(6) Uani 1 1 d . . . . .
C16 C 0.8153(4) 1.07593(18) 0.02599(7) 0.0510(7) Uani 1 1 d . . . . .
H16 H 0.7831 1.1286 0.0173 0.061 Uiso 1 1 calc R U . . .
N17 N 0.9047(3) 1.06695(13) 0.05517(5) 0.0464(6) Uani 1 1 d . . . . .
C18 C 0.9258(3) 0.98052(15) 0.05945(6) 0.0390(6) Uani 1 1 d . . . . .
C19 C 0.8464(3) 0.94456(16) 0.03177(6) 0.0380(6) Uani 1 1 d . . . . .
N20 N 0.8411(3) 0.85845(13) 0.02727(5) 0.0435(5) Uani 1 1 d . . . . .
C21 C 0.9161(3) 0.80635(17) 0.05135(6) 0.0426(6) Uani 1 1 d . . . . .
N22 N 1.0013(3) 0.84511(13) 0.07870(5) 0.0417(5) Uani 1 1 d . . . . .
C23 C 1.0088(3) 0.93232(17) 0.08548(6) 0.0403(6) Uani 1 1 d . . . . .
C24 C 0.9654(5) 1.13450(19) 0.07776(8) 0.0683(9) Uani 1 1 d . . . . .
H24A H 0.9574 1.1881 0.0661 0.102 Uiso 1 1 calc R U . . .
H24B H 1.0848 1.1240 0.0841 0.102 Uiso 1 1 calc R U . . .
H24C H 0.8939 1.1359 0.0979 0.102 Uiso 1 1 calc R U . . .
C25 C 0.7431(4) 0.82038(19) -0.00102(7) 0.0590(8) Uani 1 1 d . . . . .
H25A H 0.6304 0.8022 0.0070 0.089 Uiso 1 1 calc R U . . .
H25B H 0.8064 0.7724 -0.0097 0.089 Uiso 1 1 calc R U . . .
H25C H 0.7283 0.8616 -0.0189 0.089 Uiso 1 1 calc R U . . .
O26 O 0.9083(3) 0.72945(12) 0.04892(5) 0.0602(6) Uani 1 1 d . . . . .
C27 C 1.0914(4) 0.78794(19) 0.10269(7) 0.0577(8) Uani 1 1 d . . . . .
H27A H 1.1638 0.8207 0.1178 0.087 Uiso 1 1 calc R U . . .
H27B H 1.1628 0.7487 0.0901 0.087 Uiso 1 1 calc R U . . .
H27C H 1.0063 0.7572 0.1158 0.087 Uiso 1 1 calc R U . . .
O28 O 1.0795(3) 0.95947(12) 0.11130(5) 0.0590(6) Uani 1 1 d . . . . .
C31 C 0.8444(4) 0.37762(18) 0.14883(7) 0.0455(6) Uani 1 1 d . . . . .
O32 O 0.8629(3) 0.43141(13) 0.17045(5) 0.0656(6) Uani 1 1 d . . . . .
O33 O 0.7549(3) 0.30695(13) 0.15395(5) 0.0588(6) Uani 1 1 d . . . . .
H33 H 0.7242 0.3045 0.1740 0.088 Uiso 1 1 calc R U . . .
C34 C 0.9234(4) 0.38042(17) 0.11432(6) 0.0445(6) Uani 1 1 d . . . . .
H34 H 0.9277 0.3296 0.1022 0.053 Uiso 1 1 calc R U . . .
C35 C 0.9883(3) 0.44829(17) 0.09909(6) 0.0422(6) Uani 1 1 d . . . . .
C36 C 0.9891(5) 0.53631(18) 0.11307(8) 0.0655(9) Uani 1 1 d . . . . .
H36A H 0.9098 0.5397 0.1320 0.098 Uiso 1 1 calc R U . . .
H36B H 0.9529 0.5754 0.0956 0.098 Uiso 1 1 calc R U . . .
H36C H 1.1050 0.5505 0.1206 0.098 Uiso 1 1 calc R U . . .
C37 C 1.0687(3) 0.43563(19) 0.06435(7) 0.0446(6) Uani 1 1 d . . . . .
O38 O 1.0847(3) 0.36730(13) 0.05072(5) 0.0613(6) Uani 1 1 d . . . . .
O39 O 1.1218(3) 0.50696(13) 0.05054(5) 0.0613(6) Uani 1 1 d . . . . .
H39 H 1.1586 0.4977 0.0312 0.092 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.337(4) . ?
N1 C5 1.357(3) . ?
C2 N3 1.334(3) . ?
C2 H2 0.9300 . ?
N3 C4 1.386(3) . ?
N3 C10 1.452(3) . ?
C4 C5 1.363(3) . ?
C4 C9 1.420(3) . ?
C5 N6 1.373(3) . ?
N6 C7 1.373(3) . ?
N6 C11 1.461(3) . ?
C7 O12 1.215(3) . ?
C7 N8 1.393(3) . ?
N8 C9 1.402(3) . ?
N8 C13 1.473(3) . ?
C9 O14 1.216(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N15 C16 1.316(3) . ?
N15 C19 1.355(3) . ?
C16 N17 1.338(3) . ?
C16 H16 0.9300 . ?
N17 C18 1.381(3) . ?
N17 C24 1.459(3) . ?
C18 C19 1.365(3) . ?
C18 C23 1.420(3) . ?
C19 N20 1.368(3) . ?
N20 C21 1.375(3) . ?
N20 C25 1.465(3) . ?
C21 O26 1.216(3) . ?
C21 N22 1.393(3) . ?
N22 C23 1.400(3) . ?
N22 C27 1.472(3) . ?
C23 O28 1.223(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C31 O32 1.206(3) . ?
C31 O33 1.322(3) . ?
C31 C34 1.480(4) . ?
O33 H33 0.8200 . ?
C34 C35 1.321(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.490(4) . ?
C35 C37 1.505(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O38 1.207(3) . ?
C37 O39 1.311(3) . ?
O39 H39 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 103.5(2) . . ?
N3 C2 N1 113.5(2) . . ?
N3 C2 H2 123.3 . . ?
N1 C2 H2 123.3 . . ?
C2 N3 C4 106.0(2) . . ?
C2 N3 C10 126.6(2) . . ?
C4 N3 C10 127.4(2) . . ?
C5 C4 N3 105.4(2) . . ?
C5 C4 C9 123.0(2) . . ?
N3 C4 C9 131.6(2) . . ?
N1 C5 C4 111.7(2) . . ?
N1 C5 N6 126.2(2) . . ?
C4 C5 N6 122.1(2) . . ?
C5 N6 C7 119.3(2) . . ?
C5 N6 C11 121.7(2) . . ?
C7 N6 C11 118.9(2) . . ?
O12 C7 N6 120.8(2) . . ?
O12 C7 N8 122.2(2) . . ?
N6 C7 N8 117.0(2) . . ?
C7 N8 C9 127.2(2) . . ?
C7 N8 C13 117.5(2) . . ?
C9 N8 C13 115.3(2) . . ?
O14 C9 N8 121.3(2) . . ?
O14 C9 C4 127.3(3) . . ?
N8 C9 C4 111.3(2) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N15 C19 103.3(2) . . ?
N15 C16 N17 114.3(2) . . ?
N15 C16 H16 122.9 . . ?
N17 C16 H16 122.9 . . ?
C16 N17 C18 105.5(2) . . ?
C16 N17 C24 127.0(2) . . ?
C18 N17 C24 127.5(2) . . ?
C19 C18 N17 105.1(2) . . ?
C19 C18 C23 123.1(2) . . ?
N17 C18 C23 131.8(2) . . ?
N15 C19 C18 111.8(2) . . ?
N15 C19 N20 126.4(2) . . ?
C18 C19 N20 121.8(2) . . ?
C19 N20 C21 119.4(2) . . ?
C19 N20 C25 121.2(2) . . ?
C21 N20 C25 119.1(2) . . ?
O26 C21 N20 121.4(2) . . ?
O26 C21 N22 121.3(2) . . ?
N20 C21 N22 117.4(2) . . ?
C21 N22 C23 126.5(2) . . ?
C21 N22 C27 116.1(2) . . ?
C23 N22 C27 117.4(2) . . ?
O28 C23 N22 121.2(2) . . ?
O28 C23 C18 127.1(3) . . ?
N22 C23 C18 111.8(2) . . ?
N17 C24 H24A 109.5 . . ?
N17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N20 C25 H25A 109.5 . . ?
N20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O32 C31 O33 123.1(2) . . ?
O32 C31 C34 124.9(3) . . ?
O33 C31 C34 112.0(2) . . ?
C31 O33 H33 109.5 . . ?
C35 C34 C31 126.1(3) . . ?
C35 C34 H34 117.0 . . ?
C31 C34 H34 117.0 . . ?
C34 C35 C36 126.1(2) . . ?
C34 C35 C37 117.0(2) . . ?
C36 C35 C37 116.9(2) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O38 C37 O39 123.4(2) . . ?
O38 C37 C35 123.9(3) . . ?
O39 C37 C35 112.7(2) . . ?
C37 O39 H39 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.5(3) . . . . ?
N1 C2 N3 C4 0.6(3) . . . . ?
N1 C2 N3 C10 179.7(3) . . . . ?
C2 N3 C4 C5 -0.4(3) . . . . ?
C10 N3 C4 C5 -179.5(3) . . . . ?
C2 N3 C4 C9 -177.6(3) . . . . ?
C10 N3 C4 C9 3.3(5) . . . . ?
C2 N1 C5 C4 0.2(3) . . . . ?
C2 N1 C5 N6 179.9(2) . . . . ?
N3 C4 C5 N1 0.1(3) . . . . ?
C9 C4 C5 N1 177.6(2) . . . . ?
N3 C4 C5 N6 -179.6(2) . . . . ?
C9 C4 C5 N6 -2.0(4) . . . . ?
N1 C5 N6 C7 -179.9(2) . . . . ?
C4 C5 N6 C7 -0.3(4) . . . . ?
N1 C5 N6 C11 -2.6(4) . . . . ?
C4 C5 N6 C11 177.1(2) . . . . ?
C5 N6 C7 O12 -178.6(2) . . . . ?
C11 N6 C7 O12 4.0(4) . . . . ?
C5 N6 C7 N8 0.9(3) . . . . ?
C11 N6 C7 N8 -176.5(2) . . . . ?
O12 C7 N8 C9 -179.8(3) . . . . ?
N6 C7 N8 C9 0.7(4) . . . . ?
O12 C7 N8 C13 -1.0(4) . . . . ?
N6 C7 N8 C13 179.5(2) . . . . ?
C7 N8 C9 O14 175.8(3) . . . . ?
C13 N8 C9 O14 -3.1(4) . . . . ?
C7 N8 C9 C4 -2.6(4) . . . . ?
C13 N8 C9 C4 178.6(2) . . . . ?
C5 C4 C9 O14 -175.0(3) . . . . ?
N3 C4 C9 O14 1.8(5) . . . . ?
C5 C4 C9 N8 3.2(4) . . . . ?
N3 C4 C9 N8 -180.0(2) . . . . ?
C19 N15 C16 N17 0.3(3) . . . . ?
N15 C16 N17 C18 -0.4(3) . . . . ?
N15 C16 N17 C24 -179.9(3) . . . . ?
C16 N17 C18 C19 0.3(3) . . . . ?
C24 N17 C18 C19 179.9(3) . . . . ?
C16 N17 C18 C23 -179.8(3) . . . . ?
C24 N17 C18 C23 -0.3(5) . . . . ?
C16 N15 C19 C18 0.0(3) . . . . ?
C16 N15 C19 N20 179.7(3) . . . . ?
N17 C18 C19 N15 -0.2(3) . . . . ?
C23 C18 C19 N15 180.0(2) . . . . ?
N17 C18 C19 N20 -180.0(2) . . . . ?
C23 C18 C19 N20 0.2(4) . . . . ?
N15 C19 N20 C21 -179.1(2) . . . . ?
C18 C19 N20 C21 0.6(4) . . . . ?
N15 C19 N20 C25 -4.9(4) . . . . ?
C18 C19 N20 C25 174.9(2) . . . . ?
C19 N20 C21 O26 177.2(2) . . . . ?
C25 N20 C21 O26 2.8(4) . . . . ?
C19 N20 C21 N22 -2.7(4) . . . . ?
C25 N20 C21 N22 -177.1(2) . . . . ?
O26 C21 N22 C23 -175.4(3) . . . . ?
N20 C21 N22 C23 4.5(4) . . . . ?
O26 C21 N22 C27 4.4(4) . . . . ?
N20 C21 N22 C27 -175.7(2) . . . . ?
C21 N22 C23 O28 176.0(2) . . . . ?
C27 N22 C23 O28 -3.7(4) . . . . ?
C21 N22 C23 C18 -3.6(4) . . . . ?
C27 N22 C23 C18 176.6(2) . . . . ?
C19 C18 C23 O28 -178.5(3) . . . . ?
N17 C18 C23 O28 1.7(5) . . . . ?
C19 C18 C23 N22 1.2(4) . . . . ?
N17 C18 C23 N22 -178.6(3) . . . . ?
O32 C31 C34 C35 -17.3(5) . . . . ?
O33 C31 C34 C35 165.0(3) . . . . ?
C31 C34 C35 C36 -2.4(5) . . . . ?
C31 C34 C35 C37 177.7(2) . . . . ?
C34 C35 C37 O38 -3.9(4) . . . . ?
C36 C35 C37 O38 176.2(3) . . . . ?
C34 C35 C37 O39 176.9(2) . . . . ?
C36 C35 C37 O39 -3.0(4) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994951'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tlmo035

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 N4 O2), C5 H6 O4'
_chemical_formula_sum            'C21 H26 N8 O8'
_chemical_formula_weight         518.50

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   8.5926(3)
_cell_length_b                   18.4382(7)
_cell_length_c                   14.9164(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.437(3)
_cell_angle_gamma                90
_cell_volume                     2361.10(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8242
_cell_measurement_theta_min      2.8998
_cell_measurement_theta_max      25.2035

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18835
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         25.257
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4215
_reflns_number_gt                3338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+3.9213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4215
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.4894(3) 0.35727(14) 0.33343(16) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.4476(4) 0.38324(17) 0.4127(2) 0.0271(7) Uani 1 1 d . . . . .
H2 H 0.3754 0.4218 0.4186 0.033 Uiso 1 1 calc R U . . .
N3 N 0.5177(3) 0.34945(14) 0.48242(16) 0.0244(6) Uani 1 1 d . . . . .
C4 C 0.6139(3) 0.29768(16) 0.44693(18) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.5926(3) 0.30366(16) 0.35598(19) 0.0220(6) Uani 1 1 d . . . . .
N6 N 0.6686(3) 0.25966(14) 0.29736(15) 0.0247(6) Uani 1 1 d . . . . .
C7 C 0.7718(3) 0.20804(17) 0.33113(19) 0.0249(6) Uani 1 1 d . . . . .
N8 N 0.7946(3) 0.20461(14) 0.42454(16) 0.0252(6) Uani 1 1 d . . . . .
C9 C 0.7215(3) 0.24814(16) 0.48884(19) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.4903(4) 0.3636(2) 0.5771(2) 0.0351(8) Uani 1 1 d . . . . .
H10A H 0.5808 0.3887 0.6047 0.053 Uiso 1 1 calc R U . . .
H10B H 0.4743 0.3176 0.6082 0.053 Uiso 1 1 calc R U . . .
H10C H 0.3976 0.3941 0.5816 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6359(4) 0.26524(19) 0.19983(19) 0.0315(7) Uani 1 1 d . . . . .
H11A H 0.6872 0.2252 0.1695 0.047 Uiso 1 1 calc R U . . .
H11B H 0.6756 0.3116 0.1781 0.047 Uiso 1 1 calc R U . . .
H11C H 0.5232 0.2626 0.1871 0.047 Uiso 1 1 calc R U . . .
O12 O 0.8406(3) 0.16727(12) 0.28219(14) 0.0328(5) Uani 1 1 d . . . . .
C13 C 0.9028(4) 0.14896(19) 0.4596(2) 0.0370(8) Uani 1 1 d . . . . .
H13A H 1.0100 0.1664 0.4560 0.055 Uiso 1 1 calc R U . . .
H13B H 0.8894 0.1046 0.4240 0.055 Uiso 1 1 calc R U . . .
H13C H 0.8812 0.1387 0.5223 0.055 Uiso 1 1 calc R U . . .
O14 O 0.7539(2) 0.24212(12) 0.56903(13) 0.0284(5) Uani 1 1 d . . . . .
N15 N 0.4390(3) 0.10896(14) 0.71616(16) 0.0264(6) Uani 1 1 d . . . . .
C16 C 0.5428(4) 0.16338(18) 0.7101(2) 0.0314(7) Uani 1 1 d . . . . .
H16 H 0.5765 0.1818 0.6547 0.038 Uiso 1 1 calc R U . . .
N17 N 0.5942(3) 0.18909(15) 0.79085(17) 0.0294(6) Uani 1 1 d . . . . .
C18 C 0.5189(3) 0.14791(16) 0.85433(19) 0.0219(6) Uani 1 1 d . . . . .
C19 C 0.4257(3) 0.10036(16) 0.80544(18) 0.0218(6) Uani 1 1 d . . . . .
N20 N 0.3322(3) 0.05111(13) 0.84631(15) 0.0226(5) Uani 1 1 d . . . . .
C21 C 0.3319(3) 0.04817(16) 0.9387(2) 0.0248(6) Uani 1 1 d . . . . .
N22 N 0.4303(3) 0.09625(14) 0.98635(15) 0.0238(5) Uani 1 1 d . . . . .
C23 C 0.5302(3) 0.14809(17) 0.94955(19) 0.0246(6) Uani 1 1 d . . . . .
C24 C 0.6917(4) 0.25280(18) 0.8048(2) 0.0339(8) Uani 1 1 d . . . . .
H24A H 0.7628 0.2572 0.7555 0.051 Uiso 1 1 calc R U . . .
H24B H 0.7522 0.2480 0.8617 0.051 Uiso 1 1 calc R U . . .
H24C H 0.6259 0.2961 0.8068 0.051 Uiso 1 1 calc R U . . .
C25 C 0.2280(4) 0.00252(17) 0.7940(2) 0.0275(7) Uani 1 1 d . . . . .
H25A H 0.2233 0.0178 0.7310 0.041 Uiso 1 1 calc R U . . .
H25B H 0.1234 0.0046 0.8177 0.041 Uiso 1 1 calc R U . . .
H25C H 0.2677 -0.0472 0.7984 0.041 Uiso 1 1 calc R U . . .
O26 O 0.2487(3) 0.00506(12) 0.97694(14) 0.0313(5) Uani 1 1 d . . . . .
C27 C 0.4304(4) 0.09348(18) 1.08489(19) 0.0302(7) Uani 1 1 d . . . . .
H27A H 0.3746 0.1357 1.1073 0.045 Uiso 1 1 calc R U . . .
H27B H 0.5380 0.0939 1.1094 0.045 Uiso 1 1 calc R U . . .
H27C H 0.3786 0.0490 1.1036 0.045 Uiso 1 1 calc R U . . .
O28 O 0.6136(3) 0.18740(12) 0.99760(14) 0.0322(5) Uani 1 1 d . . . . .
C31 C 0.3927(4) 0.0899(2) 0.4933(2) 0.0353(8) Uani 1 1 d . . . . .
O32 O 0.4741(4) 0.14199(17) 0.50460(17) 0.0640(10) Uani 1 1 d . . . . .
O33 O 0.3325(3) 0.05258(14) 0.55957(15) 0.0435(7) Uani 1 1 d . . . . .
H33 H 0.3517 0.0741 0.6084 0.065 Uiso 1 1 calc R U . . .
C34 C 0.3531(4) 0.06082(18) 0.4005(2) 0.0315(7) Uani 1 1 d . . . . .
C35 C 0.4497(4) 0.0902(2) 0.3280(2) 0.0377(8) Uani 1 1 d . . . . .
H35A H 0.4215 0.0658 0.2713 0.057 Uiso 1 1 calc R U . . .
H35B H 0.5601 0.0819 0.3436 0.057 Uiso 1 1 calc R U . . .
H35C H 0.4307 0.1424 0.3215 0.057 Uiso 1 1 calc R U . . .
C36 C 0.2399(4) 0.01239(19) 0.3914(2) 0.0342(8) Uani 1 1 d . . . . .
H36 H 0.1881 -0.0012 0.4439 0.041 Uiso 1 1 calc R U . . .
C37 C 0.1870(4) -0.02270(19) 0.3047(2) 0.0328(8) Uani 1 1 d . . . . .
O38 O 0.2175(3) -0.00306(16) 0.22986(17) 0.0525(8) Uani 1 1 d . . . . .
O39 O 0.1008(3) -0.07905(13) 0.32047(14) 0.0379(6) Uani 1 1 d . . . . .
H39 H 0.0783 -0.1006 0.2720 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.338(4) . ?
N1 C5 1.361(4) . ?
C2 N3 1.334(4) . ?
C2 H2 0.9500 . ?
N3 C4 1.383(4) . ?
N3 C10 1.465(4) . ?
C4 C5 1.366(4) . ?
C4 C9 1.425(4) . ?
C5 N6 1.377(4) . ?
N6 C7 1.382(4) . ?
N6 C11 1.474(4) . ?
C7 O12 1.218(4) . ?
C7 N8 1.400(4) . ?
N8 C9 1.417(4) . ?
N8 C13 1.466(4) . ?
C9 O14 1.221(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N15 C16 1.348(4) . ?
N15 C19 1.351(4) . ?
C16 N17 1.351(4) . ?
C16 H16 0.9500 . ?
N17 C18 1.394(4) . ?
N17 C24 1.453(4) . ?
C18 C19 1.375(4) . ?
C18 C23 1.419(4) . ?
C19 N20 1.372(4) . ?
N20 C21 1.379(4) . ?
N20 C25 1.468(4) . ?
C21 O26 1.226(4) . ?
C21 N22 1.399(4) . ?
N22 C23 1.411(4) . ?
N22 C27 1.471(4) . ?
C23 O28 1.228(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 O32 1.197(4) . ?
C31 O33 1.327(4) . ?
C31 C34 1.509(4) . ?
O33 H33 0.8400 . ?
C34 C36 1.323(5) . ?
C34 C35 1.493(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.500(4) . ?
C36 H36 0.9500 . ?
C37 O38 1.212(4) . ?
C37 O39 1.304(4) . ?
O39 H39 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 103.8(2) . . ?
N3 C2 N1 113.1(3) . . ?
N3 C2 H2 123.4 . . ?
N1 C2 H2 123.4 . . ?
C2 N3 C4 106.3(2) . . ?
C2 N3 C10 125.6(3) . . ?
C4 N3 C10 128.0(3) . . ?
C5 C4 N3 105.5(3) . . ?
C5 C4 C9 123.0(3) . . ?
N3 C4 C9 131.4(3) . . ?
N1 C5 C4 111.3(3) . . ?
N1 C5 N6 126.3(3) . . ?
C4 C5 N6 122.4(3) . . ?
C5 N6 C7 119.2(2) . . ?
C5 N6 C11 120.7(3) . . ?
C7 N6 C11 120.0(2) . . ?
O12 C7 N6 121.8(3) . . ?
O12 C7 N8 121.2(3) . . ?
N6 C7 N8 117.0(3) . . ?
C7 N8 C9 126.9(3) . . ?
C7 N8 C13 116.5(3) . . ?
C9 N8 C13 116.6(2) . . ?
O14 C9 N8 121.5(3) . . ?
O14 C9 C4 127.2(3) . . ?
N8 C9 C4 111.3(2) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N15 C19 103.7(2) . . ?
N15 C16 N17 113.2(3) . . ?
N15 C16 H16 123.4 . . ?
N17 C16 H16 123.4 . . ?
C16 N17 C18 105.7(3) . . ?
C16 N17 C24 125.2(3) . . ?
C18 N17 C24 128.6(3) . . ?
C19 C18 N17 105.3(2) . . ?
C19 C18 C23 123.1(3) . . ?
N17 C18 C23 131.6(3) . . ?
N15 C19 N20 126.3(3) . . ?
N15 C19 C18 112.1(3) . . ?
N20 C19 C18 121.6(3) . . ?
C19 N20 C21 119.7(2) . . ?
C19 N20 C25 121.6(2) . . ?
C21 N20 C25 118.7(2) . . ?
O26 C21 N20 121.1(3) . . ?
O26 C21 N22 121.7(3) . . ?
N20 C21 N22 117.2(3) . . ?
C21 N22 C23 126.6(2) . . ?
C21 N22 C27 117.5(2) . . ?
C23 N22 C27 116.0(2) . . ?
O28 C23 N22 121.5(3) . . ?
O28 C23 C18 126.8(3) . . ?
N22 C23 C18 111.8(3) . . ?
N17 C24 H24A 109.5 . . ?
N17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N20 C25 H25A 109.5 . . ?
N20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O32 C31 O33 123.7(3) . . ?
O32 C31 C34 121.5(3) . . ?
O33 C31 C34 114.8(3) . . ?
C31 O33 H33 109.5 . . ?
C36 C34 C35 126.8(3) . . ?
C36 C34 C31 118.0(3) . . ?
C35 C34 C31 115.2(3) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 C37 125.0(3) . . ?
C34 C36 H36 117.5 . . ?
C37 C36 H36 117.5 . . ?
O38 C37 O39 123.5(3) . . ?
O38 C37 C36 126.6(3) . . ?
O39 C37 C36 110.0(3) . . ?
C37 O39 H39 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.0(3) . . . . ?
N1 C2 N3 C4 0.5(3) . . . . ?
N1 C2 N3 C10 -177.1(3) . . . . ?
C2 N3 C4 C5 -0.8(3) . . . . ?
C10 N3 C4 C5 176.8(3) . . . . ?
C2 N3 C4 C9 176.7(3) . . . . ?
C10 N3 C4 C9 -5.7(5) . . . . ?
C2 N1 C5 C4 -0.5(3) . . . . ?
C2 N1 C5 N6 179.4(3) . . . . ?
N3 C4 C5 N1 0.8(3) . . . . ?
C9 C4 C5 N1 -176.9(3) . . . . ?
N3 C4 C5 N6 -179.1(3) . . . . ?
C9 C4 C5 N6 3.2(5) . . . . ?
N1 C5 N6 C7 179.2(3) . . . . ?
C4 C5 N6 C7 -0.9(4) . . . . ?
N1 C5 N6 C11 -3.2(4) . . . . ?
C4 C5 N6 C11 176.7(3) . . . . ?
C5 N6 C7 O12 179.2(3) . . . . ?
C11 N6 C7 O12 1.6(4) . . . . ?
C5 N6 C7 N8 -1.0(4) . . . . ?
C11 N6 C7 N8 -178.5(3) . . . . ?
O12 C7 N8 C9 -179.4(3) . . . . ?
N6 C7 N8 C9 0.7(4) . . . . ?
O12 C7 N8 C13 -0.9(4) . . . . ?
N6 C7 N8 C13 179.2(3) . . . . ?
C7 N8 C9 O14 -177.6(3) . . . . ?
C13 N8 C9 O14 3.9(4) . . . . ?
C7 N8 C9 C4 1.3(4) . . . . ?
C13 N8 C9 C4 -177.2(3) . . . . ?
C5 C4 C9 O14 175.6(3) . . . . ?
N3 C4 C9 O14 -1.4(5) . . . . ?
C5 C4 C9 N8 -3.1(4) . . . . ?
N3 C4 C9 N8 179.8(3) . . . . ?
C19 N15 C16 N17 -0.2(4) . . . . ?
N15 C16 N17 C18 0.4(4) . . . . ?
N15 C16 N17 C24 -172.3(3) . . . . ?
C16 N17 C18 C19 -0.5(3) . . . . ?
C24 N17 C18 C19 172.0(3) . . . . ?
C16 N17 C18 C23 177.4(3) . . . . ?
C24 N17 C18 C23 -10.2(5) . . . . ?
C16 N15 C19 N20 179.8(3) . . . . ?
C16 N15 C19 C18 -0.2(3) . . . . ?
N17 C18 C19 N15 0.4(3) . . . . ?
C23 C18 C19 N15 -177.7(3) . . . . ?
N17 C18 C19 N20 -179.5(3) . . . . ?
C23 C18 C19 N20 2.4(4) . . . . ?
N15 C19 N20 C21 179.4(3) . . . . ?
C18 C19 N20 C21 -0.7(4) . . . . ?
N15 C19 N20 C25 -2.5(4) . . . . ?
C18 C19 N20 C25 177.4(3) . . . . ?
C19 N20 C21 O26 179.5(3) . . . . ?
C25 N20 C21 O26 1.3(4) . . . . ?
C19 N20 C21 N22 -0.6(4) . . . . ?
C25 N20 C21 N22 -178.7(3) . . . . ?
O26 C21 N22 C23 -179.7(3) . . . . ?
N20 C21 N22 C23 0.3(4) . . . . ?
O26 C21 N22 C27 -0.1(4) . . . . ?
N20 C21 N22 C27 179.9(3) . . . . ?
C21 N22 C23 O28 -179.2(3) . . . . ?
C27 N22 C23 O28 1.2(4) . . . . ?
C21 N22 C23 C18 1.1(4) . . . . ?
C27 N22 C23 C18 -178.5(2) . . . . ?
C19 C18 C23 O28 177.9(3) . . . . ?
N17 C18 C23 O28 0.4(5) . . . . ?
C19 C18 C23 N22 -2.5(4) . . . . ?
N17 C18 C23 N22 180.0(3) . . . . ?
O32 C31 C34 C36 -167.2(4) . . . . ?
O33 C31 C34 C36 13.8(5) . . . . ?
O32 C31 C34 C35 13.4(5) . . . . ?
O33 C31 C34 C35 -165.6(3) . . . . ?
C35 C34 C36 C37 0.2(6) . . . . ?
C31 C34 C36 C37 -179.2(3) . . . . ?
C34 C36 C37 O38 -14.8(6) . . . . ?
C34 C36 C37 O39 165.3(3) . . . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994952'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tlmo024

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 N4 O2), C5 H6 O4'
_chemical_formula_sum            'C21 H26 N8 O8'
_chemical_formula_weight         518.50

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9317(6)
_cell_length_b                   8.2797(2)
_cell_length_c                   20.4795(15)
_cell_angle_alpha                89.975(6)
_cell_angle_beta                 83.335(6)
_cell_angle_gamma                61.808(6)
_cell_volume                     1175.10(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5366
_cell_measurement_theta_min      2.9061
_cell_measurement_theta_max      25.2952

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8455
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'150 images, ΔΦ 1.5° '
'120 images, ΔΦ 1.5°  (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17407
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.912
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4159
_reflns_number_gt                3756
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+2.9683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4159
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.6834(4) 0.3654(4) 0.81702(13) 0.0283(6) Uani 1 1 d . . . . .
C2 C 0.7542(5) 0.1892(5) 0.83187(16) 0.0303(7) Uani 1 1 d . . . . .
H2 H 0.8593 0.0901 0.8059 0.036 Uiso 1 1 calc R U . . .
N3 N 0.6605(4) 0.1678(4) 0.88730(13) 0.0276(6) Uani 1 1 d . . . . .
C4 C 0.5192(4) 0.3413(4) 0.91025(14) 0.0224(6) Uani 1 1 d . . . . .
C5 C 0.5362(4) 0.4583(4) 0.86632(14) 0.0230(6) Uani 1 1 d . . . . .
N6 N 0.4171(4) 0.6440(4) 0.87297(12) 0.0250(6) Uani 1 1 d . . . . .
C7 C 0.2722(5) 0.7187(4) 0.92500(15) 0.0273(7) Uani 1 1 d . . . . .
N8 N 0.2551(4) 0.5951(3) 0.96934(12) 0.0231(6) Uani 1 1 d . . . . .
C9 C 0.3739(4) 0.4040(4) 0.96685(15) 0.0243(6) Uani 1 1 d . . . . .
C10 C 0.7006(5) -0.0052(5) 0.91707(18) 0.0358(8) Uani 1 1 d . . . . .
H10A H 0.7973 -0.1081 0.8873 0.054 Uiso 1 1 calc R U . . .
H10B H 0.5815 -0.0149 0.9248 0.054 Uiso 1 1 calc R U . . .
H10C H 0.7497 -0.0084 0.9591 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4485(5) 0.7693(5) 0.82830(17) 0.0351(8) Uani 1 1 d . . . . .
H11A H 0.3434 0.8948 0.8388 0.053 Uiso 1 1 calc R U . . .
H11B H 0.4513 0.7316 0.7827 0.053 Uiso 1 1 calc R U . . .
H11C H 0.5717 0.7651 0.8337 0.053 Uiso 1 1 calc R U . . .
O12 O 0.1631(4) 0.8831(3) 0.93330(12) 0.0369(6) Uani 1 1 d . . . . .
C13 C 0.0943(5) 0.6768(5) 1.02390(16) 0.0297(7) Uani 1 1 d . . . . .
H13A H -0.0165 0.6665 1.0120 0.045 Uiso 1 1 calc R U . . .
H13B H 0.0577 0.8065 1.0321 0.045 Uiso 1 1 calc R U . . .
H13C H 0.1353 0.6114 1.0638 0.045 Uiso 1 1 calc R U . . .
O14 O 0.3487(3) 0.3104(3) 1.00896(11) 0.0332(6) Uani 1 1 d . . . . .
N15 N 0.4272(4) 0.5823(4) 0.39563(13) 0.0292(6) Uani 1 1 d . . . . .
C16 C 0.3154(5) 0.7638(5) 0.40452(16) 0.0321(7) Uani 1 1 d . . . . .
H16 H 0.2163 0.8207 0.4406 0.038 Uiso 1 1 calc R U . . .
N17 N 0.3559(4) 0.8585(4) 0.35784(14) 0.0310(6) Uani 1 1 d . . . . .
C18 C 0.5068(4) 0.7282(4) 0.31516(15) 0.0254(7) Uani 1 1 d . . . . .
C19 C 0.5457(4) 0.5629(4) 0.33945(15) 0.0240(6) Uani 1 1 d . . . . .
N20 N 0.6900(4) 0.3993(4) 0.31003(13) 0.0263(6) Uani 1 1 d . . . . .
C21 C 0.8059(5) 0.4016(5) 0.25421(16) 0.0285(7) Uani 1 1 d . . . . .
N22 N 0.7643(4) 0.5733(4) 0.23073(12) 0.0280(6) Uani 1 1 d . . . . .
C23 C 0.6134(5) 0.7455(5) 0.25660(16) 0.0290(7) Uani 1 1 d . . . . .
C24 C 0.2563(6) 1.0567(5) 0.3523(2) 0.0452(9) Uani 1 1 d . . . . .
H24A H 0.1587 1.1154 0.3908 0.068 Uiso 1 1 calc R U . . .
H24B H 0.1935 1.0848 0.3122 0.068 Uiso 1 1 calc R U . . .
H24C H 0.3496 1.1032 0.3501 0.068 Uiso 1 1 calc R U . . .
C25 C 0.7202(5) 0.2260(5) 0.33699(18) 0.0355(8) Uani 1 1 d . . . . .
H25A H 0.8242 0.1237 0.3088 0.053 Uiso 1 1 calc R U . . .
H25B H 0.6011 0.2167 0.3388 0.053 Uiso 1 1 calc R U . . .
H25C H 0.7557 0.2211 0.3815 0.053 Uiso 1 1 calc R U . . .
O26 O 0.9386(3) 0.2602(3) 0.22653(12) 0.0368(6) Uani 1 1 d . . . . .
C27 C 0.8886(5) 0.5739(6) 0.17186(17) 0.0387(9) Uani 1 1 d . . . . .
H27A H 0.8458 0.7005 0.1596 0.058 Uiso 1 1 calc R U . . .
H27B H 0.8805 0.5021 0.1355 0.058 Uiso 1 1 calc R U . . .
H27C H 1.0223 0.5195 0.1812 0.058 Uiso 1 1 calc R U . . .
O28 O 0.5848(4) 0.8873(4) 0.23070(13) 0.0440(7) Uani 1 1 d . . . . .
C29 C 0.7832(5) 0.5397(5) 0.47653(15) 0.0277(7) Uani 1 1 d . . . . .
O30 O 0.8581(4) 0.3735(3) 0.47026(11) 0.0349(6) Uani 1 1 d . . . . .
O31 O 0.6469(3) 0.6404(3) 0.52467(11) 0.0335(6) Uani 1 1 d . . . . .
H31 H 0.6198 0.5720 0.5490 0.050 Uiso 1 1 calc R U . . .
C32 C 0.8389(4) 0.6532(4) 0.42977(15) 0.0270(7) Uani 1 1 d . . . . .
C33 C 0.7446(6) 0.8560(5) 0.44456(19) 0.0413(9) Uani 1 1 d . . . . .
H33A H 0.8038 0.9097 0.4131 0.062 Uiso 1 1 calc R U . . .
H33B H 0.7616 0.8813 0.4894 0.062 Uiso 1 1 calc R U . . .
H33C H 0.6066 0.9100 0.4409 0.062 Uiso 1 1 calc R U . . .
C34 C 0.9707(5) 0.5603(4) 0.37857(16) 0.0281(7) Uani 1 1 d . . . . .
H34 H 1.0202 0.4309 0.3760 0.034 Uiso 1 1 calc R U . . .
C35 C 1.0489(5) 0.6368(5) 0.32505(15) 0.0285(7) Uani 1 1 d . . . . .
O36 O 0.9935(4) 0.7981(3) 0.31696(13) 0.0438(7) Uani 1 1 d . . . . .
O37 O 1.1905(3) 0.5036(3) 0.28591(11) 0.0337(6) Uani 1 1 d . . . . .
H37 H 1.2245 0.5486 0.2535 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.343(4) . ?
N1 C5 1.361(4) . ?
C2 N3 1.341(4) . ?
C2 H2 0.9500 . ?
N3 C4 1.377(4) . ?
N3 C10 1.463(4) . ?
C4 C5 1.364(4) . ?
C4 C9 1.438(4) . ?
C5 N6 1.368(4) . ?
N6 C7 1.373(4) . ?
N6 C11 1.472(4) . ?
C7 O12 1.218(4) . ?
C7 N8 1.412(4) . ?
N8 C9 1.405(4) . ?
N8 C13 1.479(4) . ?
C9 O14 1.221(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N15 C16 1.335(4) . ?
N15 C19 1.356(4) . ?
C16 N17 1.341(4) . ?
C16 H16 0.9500 . ?
N17 C18 1.378(4) . ?
N17 C24 1.458(5) . ?
C18 C19 1.361(4) . ?
C18 C23 1.432(4) . ?
C19 N20 1.372(4) . ?
N20 C21 1.387(4) . ?
N20 C25 1.458(4) . ?
C21 O26 1.224(4) . ?
C21 N22 1.397(4) . ?
N22 C23 1.410(4) . ?
N22 C27 1.467(4) . ?
C23 O28 1.219(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C29 O30 1.214(4) . ?
C29 O31 1.318(4) . ?
C29 C32 1.513(4) . ?
O31 H31 0.8400 . ?
C32 C34 1.331(4) . ?
C32 C33 1.494(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.483(4) . ?
C34 H34 0.9500 . ?
C35 O36 1.211(4) . ?
C35 O37 1.320(4) . ?
O37 H37 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 103.9(3) . . ?
N3 C2 N1 112.8(3) . . ?
N3 C2 H2 123.6 . . ?
N1 C2 H2 123.6 . . ?
C2 N3 C4 106.2(3) . . ?
C2 N3 C10 126.8(3) . . ?
C4 N3 C10 127.1(3) . . ?
C5 C4 N3 106.1(3) . . ?
C5 C4 C9 122.4(3) . . ?
N3 C4 C9 131.5(3) . . ?
N1 C5 C4 111.1(3) . . ?
N1 C5 N6 126.3(3) . . ?
C4 C5 N6 122.6(3) . . ?
C5 N6 C7 119.9(3) . . ?
C5 N6 C11 121.7(3) . . ?
C7 N6 C11 118.3(3) . . ?
O12 C7 N6 122.5(3) . . ?
O12 C7 N8 120.9(3) . . ?
N6 C7 N8 116.6(3) . . ?
C9 N8 C7 126.9(3) . . ?
C9 N8 C13 117.1(2) . . ?
C7 N8 C13 116.0(2) . . ?
O14 C9 N8 121.4(3) . . ?
O14 C9 C4 127.1(3) . . ?
N8 C9 C4 111.5(3) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N15 C19 103.2(3) . . ?
N15 C16 N17 113.9(3) . . ?
N15 C16 H16 123.1 . . ?
N17 C16 H16 123.1 . . ?
C16 N17 C18 105.3(3) . . ?
C16 N17 C24 127.2(3) . . ?
C18 N17 C24 127.5(3) . . ?
C19 C18 N17 106.0(3) . . ?
C19 C18 C23 122.6(3) . . ?
N17 C18 C23 131.3(3) . . ?
N15 C19 C18 111.6(3) . . ?
N15 C19 N20 125.5(3) . . ?
C18 C19 N20 122.9(3) . . ?
C19 N20 C21 119.0(3) . . ?
C19 N20 C25 120.4(3) . . ?
C21 N20 C25 120.7(3) . . ?
O26 C21 N20 121.8(3) . . ?
O26 C21 N22 121.3(3) . . ?
N20 C21 N22 117.0(3) . . ?
C21 N22 C23 127.0(3) . . ?
C21 N22 C27 116.4(3) . . ?
C23 N22 C27 116.5(3) . . ?
O28 C23 N22 121.8(3) . . ?
O28 C23 C18 126.7(3) . . ?
N22 C23 C18 111.4(3) . . ?
N17 C24 H24A 109.5 . . ?
N17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N20 C25 H25A 109.5 . . ?
N20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O30 C29 O31 124.1(3) . . ?
O30 C29 C32 123.1(3) . . ?
O31 C29 C32 112.8(3) . . ?
C29 O31 H31 109.5 . . ?
C34 C32 C33 125.8(3) . . ?
C34 C32 C29 115.8(3) . . ?
C33 C32 C29 118.4(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 C35 127.1(3) . . ?
C32 C34 H34 116.5 . . ?
C35 C34 H34 116.5 . . ?
O36 C35 O37 123.3(3) . . ?
O36 C35 C34 126.1(3) . . ?
O37 C35 C34 110.6(3) . . ?
C35 O37 H37 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.3(4) . . . . ?
N1 C2 N3 C4 0.0(4) . . . . ?
N1 C2 N3 C10 179.8(3) . . . . ?
C2 N3 C4 C5 0.3(3) . . . . ?
C10 N3 C4 C5 -179.5(3) . . . . ?
C2 N3 C4 C9 179.2(3) . . . . ?
C10 N3 C4 C9 -0.6(5) . . . . ?
C2 N1 C5 C4 0.5(3) . . . . ?
C2 N1 C5 N6 -179.4(3) . . . . ?
N3 C4 C5 N1 -0.5(3) . . . . ?
C9 C4 C5 N1 -179.5(3) . . . . ?
N3 C4 C5 N6 179.4(3) . . . . ?
C9 C4 C5 N6 0.4(5) . . . . ?
N1 C5 N6 C7 179.1(3) . . . . ?
C4 C5 N6 C7 -0.9(4) . . . . ?
N1 C5 N6 C11 -5.5(5) . . . . ?
C4 C5 N6 C11 174.6(3) . . . . ?
C5 N6 C7 O12 179.6(3) . . . . ?
C11 N6 C7 O12 4.0(5) . . . . ?
C5 N6 C7 N8 -0.2(4) . . . . ?
C11 N6 C7 N8 -175.7(3) . . . . ?
O12 C7 N8 C9 -178.0(3) . . . . ?
N6 C7 N8 C9 1.8(4) . . . . ?
O12 C7 N8 C13 2.2(4) . . . . ?
N6 C7 N8 C13 -178.0(3) . . . . ?
C7 N8 C9 O14 178.1(3) . . . . ?
C13 N8 C9 O14 -2.0(4) . . . . ?
C7 N8 C9 C4 -2.2(4) . . . . ?
C13 N8 C9 C4 177.7(3) . . . . ?
C5 C4 C9 O14 -179.3(3) . . . . ?
N3 C4 C9 O14 1.9(6) . . . . ?
C5 C4 C9 N8 1.0(4) . . . . ?
N3 C4 C9 N8 -177.8(3) . . . . ?
C19 N15 C16 N17 0.1(4) . . . . ?
N15 C16 N17 C18 -0.2(4) . . . . ?
N15 C16 N17 C24 177.7(3) . . . . ?
C16 N17 C18 C19 0.3(3) . . . . ?
C24 N17 C18 C19 -177.6(3) . . . . ?
C16 N17 C18 C23 -179.1(3) . . . . ?
C24 N17 C18 C23 3.0(6) . . . . ?
C16 N15 C19 C18 0.1(4) . . . . ?
C16 N15 C19 N20 179.2(3) . . . . ?
N17 C18 C19 N15 -0.3(4) . . . . ?
C23 C18 C19 N15 179.2(3) . . . . ?
N17 C18 C19 N20 -179.4(3) . . . . ?
C23 C18 C19 N20 0.1(5) . . . . ?
N15 C19 N20 C21 -176.9(3) . . . . ?
C18 C19 N20 C21 2.1(5) . . . . ?
N15 C19 N20 C25 3.3(5) . . . . ?
C18 C19 N20 C25 -177.7(3) . . . . ?
C19 N20 C21 O26 178.9(3) . . . . ?
C25 N20 C21 O26 -1.4(5) . . . . ?
C19 N20 C21 N22 -1.2(4) . . . . ?
C25 N20 C21 N22 178.5(3) . . . . ?
O26 C21 N22 C23 178.1(3) . . . . ?
N20 C21 N22 C23 -1.8(5) . . . . ?
O26 C21 N22 C27 -0.4(5) . . . . ?
N20 C21 N22 C27 179.7(3) . . . . ?
C21 N22 C23 O28 -177.0(3) . . . . ?
C27 N22 C23 O28 1.5(5) . . . . ?
C21 N22 C23 C18 3.7(4) . . . . ?
C27 N22 C23 C18 -177.9(3) . . . . ?
C19 C18 C23 O28 178.0(3) . . . . ?
N17 C18 C23 O28 -2.7(6) . . . . ?
C19 C18 C23 N22 -2.7(4) . . . . ?
N17 C18 C23 N22 176.6(3) . . . . ?
O30 C29 C32 C34 3.1(5) . . . . ?
O31 C29 C32 C34 -177.5(3) . . . . ?
O30 C29 C32 C33 -176.6(3) . . . . ?
O31 C29 C32 C33 2.8(4) . . . . ?
C33 C32 C34 C35 -1.4(6) . . . . ?
C29 C32 C34 C35 179.0(3) . . . . ?
C32 C34 C35 O36 -6.1(6) . . . . ?
C32 C34 C35 O37 174.0(3) . . . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994953'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Gam03A

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C8 H10 N4 O2), 2(C5 H6 O4), C2 H3 N'
_chemical_formula_sum            'C44 H55 N17 O16'
_chemical_formula_weight         1078.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 '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 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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

_cell_length_a                   44.164(3)
_cell_length_b                   3.94516(19)
_cell_length_c                   27.676(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.236(8)
_cell_angle_gamma                90
_cell_volume                     4793.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3194
_cell_measurement_theta_min      2.1490
_cell_measurement_theta_max      29.4820

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             2264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.47179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82103
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  'pilatus 2M'
_diffrn_measurement_method       '360 images, ΔΦ 1.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12341
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         29.513
_diffrn_reflns_theta_full        29.513
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.890
_reflns_number_total             12341
_reflns_number_gt                11132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_max     0.881
_reflns_Friedel_fraction_full    0.881

_reflns_special_details          
;
 _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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          
;
 Refined as a 4-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1525P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12341
_refine_ls_number_parameters     712
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.2544
_refine_ls_wR_factor_gt          0.2474
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.3809(2) 0.255(2) 0.1810(4) 0.032(2) Uani 1 1 d . . . . .
C2 C 0.3673(3) 0.434(3) 0.1434(5) 0.036(3) Uani 1 1 d . . . . .
H2 H 0.3459 0.4654 0.1378 0.043 Uiso 1 1 calc R U . . .
N3 N 0.3868(2) 0.562(2) 0.1149(4) 0.031(2) Uani 1 1 d . . . . .
C4 C 0.4159(2) 0.460(2) 0.1355(4) 0.028(3) Uani 1 1 d . . . . .
C5 C 0.4106(2) 0.271(3) 0.1755(4) 0.029(3) Uani 1 1 d . . . . .
N6 N 0.4345(2) 0.130(2) 0.2048(4) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.4637(3) 0.173(3) 0.1954(5) 0.036(3) Uani 1 1 d . . . . .
N8 N 0.4680(2) 0.368(2) 0.1530(4) 0.032(2) Uani 1 1 d . . . . .
C9 C 0.4455(3) 0.532(3) 0.1225(5) 0.031(3) Uani 1 1 d . . . . .
C10 C 0.3800(3) 0.750(3) 0.0703(5) 0.031(3) Uani 1 1 d . . . . .
H10A H 0.3793 0.5944 0.0425 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3958 0.9208 0.0676 0.046 Uiso 1 1 calc R U . . .
H10C H 0.3602 0.8620 0.0703 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4284(3) -0.056(3) 0.2484(5) 0.044(3) Uani 1 1 d . . . . .
H11A H 0.4454 -0.2091 0.2582 0.065 Uiso 1 1 calc R U . . .
H11B H 0.4096 -0.1874 0.2416 0.065 Uiso 1 1 calc R U . . .
H11C H 0.4261 0.1053 0.2747 0.065 Uiso 1 1 calc R U . . .
O12 O 0.4855(2) 0.056(2) 0.2200(3) 0.041(2) Uani 1 1 d . . . . .
C13 C 0.4990(3) 0.403(3) 0.1407(6) 0.043(3) Uani 1 1 d . . . . .
H13A H 0.4996 0.3445 0.1064 0.065 Uiso 1 1 calc R U . . .
H13B H 0.5124 0.2496 0.1610 0.065 Uiso 1 1 calc R U . . .
H13C H 0.5058 0.6370 0.1463 0.065 Uiso 1 1 calc R U . . .
O14 O 0.45181(18) 0.7185(18) 0.0894(3) 0.0320(18) Uani 1 1 d . . . . .
N15 N 0.4935(2) -0.064(2) 0.4450(4) 0.031(2) Uani 1 1 d . . . . .
C16 C 0.5070(3) 0.092(3) 0.4107(4) 0.030(3) Uani 1 1 d . . . . .
H16 H 0.5284 0.0907 0.4095 0.036 Uiso 1 1 calc R U . . .
N17 N 0.4874(2) 0.255(2) 0.3776(4) 0.031(2) Uani 1 1 d . . . . .
C18 C 0.4586(2) 0.196(3) 0.3925(4) 0.027(2) Uani 1 1 d . . . . .
C19 C 0.4636(2) -0.002(3) 0.4331(5) 0.028(3) Uani 1 1 d . . . . .
N20 N 0.4399(2) -0.107(2) 0.4578(4) 0.032(2) Uani 1 1 d . . . . .
C21 C 0.4103(3) -0.020(3) 0.4409(5) 0.033(3) Uani 1 1 d . . . . .
N22 N 0.4061(2) 0.180(2) 0.3986(4) 0.032(2) Uani 1 1 d . . . . .
C23 C 0.4290(3) 0.309(3) 0.3721(5) 0.035(3) Uani 1 1 d . . . . .
C24 C 0.4944(3) 0.432(3) 0.3351(5) 0.033(3) Uani 1 1 d . . . . .
H24A H 0.5163 0.4815 0.3378 0.050 Uiso 1 1 calc R U . . .
H24B H 0.4829 0.6451 0.3320 0.050 Uiso 1 1 calc R U . . .
H24C H 0.4888 0.2917 0.3063 0.050 Uiso 1 1 calc R U . . .
C25 C 0.4456(3) -0.299(3) 0.5024(5) 0.039(3) Uani 1 1 d . . . . .
H25A H 0.4631 -0.4481 0.5005 0.059 Uiso 1 1 calc R U . . .
H25B H 0.4276 -0.4359 0.5071 0.059 Uiso 1 1 calc R U . . .
H25C H 0.4498 -0.1428 0.5298 0.059 Uiso 1 1 calc R U . . .
O26 O 0.38883(18) -0.098(2) 0.4623(3) 0.039(2) Uani 1 1 d . . . . .
C27 C 0.3743(3) 0.263(3) 0.3820(5) 0.039(3) Uani 1 1 d . . . . .
H27A H 0.3620 0.0559 0.3812 0.058 Uiso 1 1 calc R U . . .
H27B H 0.3731 0.3612 0.3494 0.058 Uiso 1 1 calc R U . . .
H27C H 0.3667 0.4260 0.4045 0.058 Uiso 1 1 calc R U . . .
O28 O 0.42342(19) 0.5013(18) 0.3374(3) 0.0339(19) Uani 1 1 d . . . . .
N31 N 0.2567(2) -0.112(2) -0.0770(4) 0.029(2) Uani 1 1 d . . . . .
C32 C 0.2263(3) -0.121(3) -0.0835(5) 0.038(3) Uani 1 1 d . . . . .
H32 H 0.2150 -0.2287 -0.1104 0.045 Uiso 1 1 calc R U . . .
N33 N 0.2133(2) 0.037(2) -0.0480(4) 0.033(2) Uani 1 1 d . . . . .
C34 C 0.2369(2) 0.158(3) -0.0166(5) 0.035(3) Uani 1 1 d . . . . .
C35 C 0.2628(3) 0.062(3) -0.0349(5) 0.030(3) Uani 1 1 d . . . . .
N36 N 0.2914(2) 0.138(2) -0.0128(4) 0.032(2) Uani 1 1 d . . . . .
C37 C 0.2938(2) 0.309(3) 0.0315(5) 0.033(3) Uani 1 1 d . . . . .
N38 N 0.2667(2) 0.409(2) 0.0495(4) 0.034(2) Uani 1 1 d . . . . .
C39 C 0.2370(3) 0.350(3) 0.0269(5) 0.036(3) Uani 1 1 d . . . . .
C40 C 0.1806(3) 0.055(3) -0.0423(6) 0.042(3) Uani 1 1 d . . . . .
H40A H 0.1689 -0.0448 -0.0709 0.063 Uiso 1 1 calc R U . . .
H40B H 0.1746 0.2925 -0.0391 0.063 Uiso 1 1 calc R U . . .
H40C H 0.1765 -0.0706 -0.0132 0.063 Uiso 1 1 calc R U . . .
C41 C 0.3190(3) 0.042(3) -0.0339(5) 0.038(3) Uani 1 1 d . . . . .
H41A H 0.3368 0.1303 -0.0136 0.057 Uiso 1 1 calc R U . . .
H41B H 0.3184 0.1378 -0.0667 0.057 Uiso 1 1 calc R U . . .
H41C H 0.3202 -0.2051 -0.0356 0.057 Uiso 1 1 calc R U . . .
O42 O 0.31831(18) 0.371(2) 0.0537(3) 0.039(2) Uani 1 1 d . . . . .
C43 C 0.2707(3) 0.579(3) 0.0959(6) 0.046(3) Uani 1 1 d . . . . .
H43A H 0.2515 0.6837 0.1025 0.069 Uiso 1 1 calc R U . . .
H43B H 0.2864 0.7541 0.0954 0.069 Uiso 1 1 calc R U . . .
H43C H 0.2771 0.4138 0.1215 0.069 Uiso 1 1 calc R U . . .
O44 O 0.21463(19) 0.459(2) 0.0451(4) 0.042(2) Uani 1 1 d . . . . .
N45 N 0.1092(2) -0.130(2) 0.2225(4) 0.030(2) Uani 1 1 d . . . . .
C46 C 0.1390(3) -0.179(3) 0.2268(5) 0.032(3) Uani 1 1 d . . . . .
H46 H 0.1489 -0.3018 0.2036 0.039 Uiso 1 1 calc R U . . .
N47 N 0.1540(2) -0.040(2) 0.2669(4) 0.035(2) Uani 1 1 d . . . . .
C48 C 0.1319(3) 0.125(3) 0.2906(5) 0.031(3) Uani 1 1 d . . . . .
C49 C 0.1053(2) 0.060(3) 0.2619(5) 0.030(3) Uani 1 1 d . . . . .
N50 N 0.0776(2) 0.178(2) 0.2749(4) 0.029(2) Uani 1 1 d . . . . .
C51 C 0.0773(3) 0.360(3) 0.3171(5) 0.036(3) Uani 1 1 d . . . . .
N52 N 0.1053(2) 0.422(2) 0.3442(4) 0.030(2) Uani 1 1 d . . . . .
C53 C 0.1342(3) 0.315(3) 0.3340(5) 0.031(3) Uani 1 1 d . . . . .
C54 C 0.1863(3) -0.068(3) 0.2827(6) 0.043(3) Uani 1 1 d . . . . .
H54A H 0.1960 -0.2123 0.2600 0.065 Uiso 1 1 calc R U . . .
H54B H 0.1892 -0.1675 0.3153 0.065 Uiso 1 1 calc R U . . .
H54C H 0.1956 0.1582 0.2835 0.065 Uiso 1 1 calc R U . . .
C55 C 0.0494(3) 0.105(3) 0.2442(5) 0.033(3) Uani 1 1 d . . . . .
H55A H 0.0444 -0.1352 0.2468 0.050 Uiso 1 1 calc R U . . .
H55B H 0.0521 0.1595 0.2103 0.050 Uiso 1 1 calc R U . . .
H55C H 0.0329 0.2435 0.2547 0.050 Uiso 1 1 calc R U . . .
O56 O 0.05379(17) 0.466(2) 0.3308(3) 0.0328(19) Uani 1 1 d . . . . .
C57 C 0.1038(3) 0.604(3) 0.3899(5) 0.037(3) Uani 1 1 d . . . . .
H57A H 0.0892 0.7914 0.3846 0.056 Uiso 1 1 calc R U . . .
H57B H 0.1240 0.6946 0.4013 0.056 Uiso 1 1 calc R U . . .
H57C H 0.0972 0.4490 0.4143 0.056 Uiso 1 1 calc R U . . .
O58 O 0.15742(17) 0.382(2) 0.3604(3) 0.039(2) Uani 1 1 d . . . . .
C61 C 0.3158(3) 0.963(3) 0.2202(7) 0.050(4) Uani 1 1 d . . . . .
O62 O 0.3100(3) 1.072(3) 0.1807(5) 0.065(3) Uani 1 1 d . . . . .
O63 O 0.3443(2) 0.967(2) 0.2438(4) 0.056(3) Uani 1 1 d . . . . .
H63 H 0.3565 1.0428 0.2252 0.084 Uiso 1 1 calc R U . . .
C64 C 0.2915(3) 0.835(4) 0.2499(6) 0.053(4) Uani 1 1 d . . . . .
C65 C 0.2999(4) 0.700(3) 0.2915(6) 0.055(4) Uani 1 1 d . . . . .
H65 H 0.3210 0.6928 0.3021 0.066 Uiso 1 1 calc R U . . .
C66 C 0.2780(4) 0.551(3) 0.3250(5) 0.045(3) Uani 1 1 d . . . . .
O67 O 0.2498(3) 0.540(2) 0.3187(4) 0.051(3) Uani 1 1 d . . . . .
O68 O 0.2932(2) 0.427(2) 0.3636(4) 0.045(2) Uani 1 1 d . . . . .
H68 H 0.2810 0.3454 0.3818 0.067 Uiso 1 1 calc R U . . .
C69 C 0.2590(3) 0.867(4) 0.2276(6) 0.048(4) Uani 1 1 d . . . . .
H69A H 0.2487 0.6479 0.2296 0.073 Uiso 1 1 calc R U . . .
H69B H 0.2587 0.9337 0.1934 0.073 Uiso 1 1 calc R U . . .
H69C H 0.2485 1.0384 0.2452 0.073 Uiso 1 1 calc R U . . .
C71 C 0.0558(3) -0.048(3) 0.0021(5) 0.030(3) Uani 1 1 d . . . . .
O72 O 0.06259(19) -0.145(2) -0.0371(3) 0.041(2) Uani 1 1 d . . . . .
O73 O 0.02849(17) -0.093(2) 0.0152(3) 0.035(2) Uani 1 1 d . . . . .
H73 H 0.0175 -0.1920 -0.0071 0.052 Uiso 1 1 calc R U . . .
C74 C 0.0782(3) 0.131(3) 0.0378(5) 0.034(3) Uani 1 1 d . . . . .
C75 C 0.1100(3) 0.144(3) 0.0229(5) 0.040(3) Uani 1 1 d . . . . .
H75A H 0.1095 0.2480 -0.0094 0.060 Uiso 1 1 calc R U . . .
H75B H 0.1182 -0.0860 0.0218 0.060 Uiso 1 1 calc R U . . .
H75C H 0.1230 0.2799 0.0464 0.060 Uiso 1 1 calc R U . . .
C76 C 0.0695(3) 0.250(3) 0.0777(5) 0.035(3) Uani 1 1 d . . . . .
H76 H 0.0487 0.2179 0.0824 0.042 Uiso 1 1 calc R U . . .
C77 C 0.0889(3) 0.434(3) 0.1171(4) 0.032(3) Uani 1 1 d . . . . .
O78 O 0.11653(19) 0.456(2) 0.1197(4) 0.042(2) Uani 1 1 d . . . . .
O79 O 0.07247(19) 0.556(2) 0.1506(3) 0.036(2) Uani 1 1 d . . . . .
H79 H 0.0839 0.6616 0.1718 0.054 Uiso 1 1 calc R U . . .
N81 N 0.1940(3) 0.347(3) 0.1844(6) 0.064(4) Uani 1 1 d . . . . .
C82 C 0.1869(3) 0.184(4) 0.1511(6) 0.049(3) Uani 1 1 d . . . . .
C83 C 0.1771(4) -0.011(4) 0.1083(6) 0.056(4) Uani 1 1 d . . . . .
H83A H 0.1774 0.1320 0.0794 0.085 Uiso 1 1 calc R U . . .
H83B H 0.1563 -0.0939 0.1103 0.085 Uiso 1 1 calc R U . . .
H83C H 0.1908 -0.2042 0.1061 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.339(14) . ?
N1 C2 1.344(17) . ?
C2 N3 1.328(16) . ?
C2 H2 0.9500 . ?
N3 C4 1.406(15) . ?
N3 C10 1.444(16) . ?
C4 C5 1.375(17) . ?
C4 C9 1.425(16) . ?
C5 N6 1.375(14) . ?
N6 C7 1.357(15) . ?
N6 C11 1.461(17) . ?
C7 O12 1.209(14) . ?
C7 N8 1.431(17) . ?
N8 C9 1.393(15) . ?
N8 C13 1.450(15) . ?
C9 O14 1.228(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N15 C16 1.326(16) . ?
N15 C19 1.352(14) . ?
C16 N17 1.352(15) . ?
C16 H16 0.9500 . ?
N17 C18 1.396(14) . ?
N17 C24 1.432(16) . ?
C18 C19 1.368(17) . ?
C18 C23 1.437(16) . ?
C19 N20 1.373(15) . ?
N20 C21 1.382(16) . ?
N20 C25 1.447(17) . ?
C21 O26 1.212(15) . ?
C21 N22 1.407(17) . ?
N22 C23 1.409(16) . ?
N22 C27 1.464(15) . ?
C23 O28 1.227(14) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N31 C32 1.334(15) . ?
N31 C35 1.354(16) . ?
C32 N33 1.343(17) . ?
C32 H32 0.9500 . ?
N33 C34 1.368(16) . ?
N33 C40 1.471(15) . ?
C34 C35 1.356(16) . ?
C34 C39 1.421(19) . ?
C35 N36 1.375(15) . ?
N36 C37 1.393(17) . ?
N36 C41 1.456(15) . ?
C37 O42 1.210(14) . ?
C37 N38 1.402(16) . ?
N38 C39 1.408(15) . ?
N38 C43 1.443(17) . ?
C39 O44 1.237(14) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
N45 C46 1.322(15) . ?
N45 C49 1.349(16) . ?
C46 N47 1.347(16) . ?
C46 H46 0.9500 . ?
N47 C48 1.395(15) . ?
N47 C54 1.452(16) . ?
C48 C49 1.367(17) . ?
C48 C53 1.411(18) . ?
C49 N50 1.392(15) . ?
N50 C51 1.373(17) . ?
N50 C55 1.457(15) . ?
C51 O56 1.215(14) . ?
C51 N52 1.397(15) . ?
N52 C53 1.400(15) . ?
N52 C57 1.463(16) . ?
C53 O58 1.222(14) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C61 O62 1.175(19) . ?
C61 O63 1.351(18) . ?
C61 C64 1.51(2) . ?
O63 H63 0.8400 . ?
C64 C65 1.29(2) . ?
C64 C69 1.504(18) . ?
C65 C66 1.53(2) . ?
C65 H65 0.9500 . ?
C66 O67 1.239(18) . ?
C66 O68 1.292(18) . ?
O68 H68 0.8400 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C71 O72 1.219(15) . ?
C71 O73 1.308(15) . ?
C71 C74 1.499(17) . ?
O73 H73 0.8400 . ?
C74 C76 1.296(18) . ?
C74 C75 1.507(17) . ?
C75 H75A 0.9800 . ?
C75 H75B 0.9800 . ?
C75 H75C 0.9800 . ?
C76 C77 1.501(16) . ?
C76 H76 0.9500 . ?
C77 O78 1.217(14) . ?
C77 O79 1.329(15) . ?
O79 H79 0.8400 . ?
N81 C82 1.14(2) . ?
C82 C83 1.44(2) . ?
C83 H83A 0.9800 . ?
C83 H83B 0.9800 . ?
C83 H83C 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
C5 N1 C2 104.4(10) . . ?
N3 C2 N1 113.3(11) . . ?
N3 C2 H2 123.3 . . ?
N1 C2 H2 123.3 . . ?
C2 N3 C4 105.7(10) . . ?
C2 N3 C10 128.0(10) . . ?
C4 N3 C10 126.2(10) . . ?
C5 C4 N3 104.8(10) . . ?
C5 C4 C9 123.4(10) . . ?
N3 C4 C9 131.7(11) . . ?
N1 C5 C4 111.7(10) . . ?
N1 C5 N6 127.6(11) . . ?
C4 C5 N6 120.7(10) . . ?
C7 N6 C5 121.3(11) . . ?
C7 N6 C11 119.1(10) . . ?
C5 N6 C11 119.5(10) . . ?
O12 C7 N6 124.0(13) . . ?
O12 C7 N8 119.9(11) . . ?
N6 C7 N8 116.0(10) . . ?
C9 N8 C7 126.7(10) . . ?
C9 N8 C13 116.2(11) . . ?
C7 N8 C13 117.1(10) . . ?
O14 C9 N8 121.8(11) . . ?
O14 C9 C4 126.6(10) . . ?
N8 C9 C4 111.7(11) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N15 C19 104.2(10) . . ?
N15 C16 N17 113.7(10) . . ?
N15 C16 H16 123.2 . . ?
N17 C16 H16 123.2 . . ?
C16 N17 C18 104.9(10) . . ?
C16 N17 C24 127.5(10) . . ?
C18 N17 C24 127.5(9) . . ?
C19 C18 N17 105.6(9) . . ?
C19 C18 C23 123.8(10) . . ?
N17 C18 C23 130.6(11) . . ?
N15 C19 C18 111.6(10) . . ?
N15 C19 N20 127.1(11) . . ?
C18 C19 N20 121.3(10) . . ?
C19 N20 C21 120.0(11) . . ?
C19 N20 C25 120.8(10) . . ?
C21 N20 C25 119.2(10) . . ?
O26 C21 N20 122.2(12) . . ?
O26 C21 N22 120.6(11) . . ?
N20 C21 N22 117.0(10) . . ?
C21 N22 C23 126.8(10) . . ?
C21 N22 C27 114.9(10) . . ?
C23 N22 C27 118.3(10) . . ?
O28 C23 N22 122.4(11) . . ?
O28 C23 C18 126.6(11) . . ?
N22 C23 C18 111.0(10) . . ?
N17 C24 H24A 109.5 . . ?
N17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N20 C25 H25A 109.5 . . ?
N20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C32 N31 C35 103.6(10) . . ?
N31 C32 N33 113.1(11) . . ?
N31 C32 H32 123.5 . . ?
N33 C32 H32 123.5 . . ?
C32 N33 C34 105.7(10) . . ?
C32 N33 C40 127.1(10) . . ?
C34 N33 C40 127.1(11) . . ?
C35 C34 N33 106.3(11) . . ?
C35 C34 C39 122.5(11) . . ?
N33 C34 C39 131.1(11) . . ?
C34 C35 N31 111.3(10) . . ?
C34 C35 N36 123.0(12) . . ?
N31 C35 N36 125.7(10) . . ?
C35 N36 C37 118.4(9) . . ?
C35 N36 C41 122.1(11) . . ?
C37 N36 C41 119.5(10) . . ?
O42 C37 N36 121.4(11) . . ?
O42 C37 N38 121.1(12) . . ?
N36 C37 N38 117.5(10) . . ?
C37 N38 C39 125.7(11) . . ?
C37 N38 C43 114.7(10) . . ?
C39 N38 C43 119.6(11) . . ?
O44 C39 N38 120.4(12) . . ?
O44 C39 C34 127.0(11) . . ?
N38 C39 C34 112.6(10) . . ?
N33 C40 H40A 109.5 . . ?
N33 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N33 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N36 C41 H41A 109.5 . . ?
N36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N38 C43 H43A 109.5 . . ?
N38 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N38 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C46 N45 C49 102.7(9) . . ?
N45 C46 N47 114.3(10) . . ?
N45 C46 H46 122.8 . . ?
N47 C46 H46 122.8 . . ?
C46 N47 C48 105.6(10) . . ?
C46 N47 C54 126.8(10) . . ?
C48 N47 C54 127.6(11) . . ?
C49 C48 N47 103.9(11) . . ?
C49 C48 C53 124.9(11) . . ?
N47 C48 C53 131.2(11) . . ?
N45 C49 C48 113.5(10) . . ?
N45 C49 N50 125.9(10) . . ?
C48 C49 N50 120.6(11) . . ?
C51 N50 C49 119.1(10) . . ?
C51 N50 C55 120.8(10) . . ?
C49 N50 C55 120.1(10) . . ?
O56 C51 N50 122.3(11) . . ?
O56 C51 N52 120.6(13) . . ?
N50 C51 N52 117.1(10) . . ?
C51 N52 C53 128.0(11) . . ?
C51 N52 C57 115.3(10) . . ?
C53 N52 C57 116.7(10) . . ?
O58 C53 N52 122.8(12) . . ?
O58 C53 C48 126.9(11) . . ?
N52 C53 C48 110.3(10) . . ?
N47 C54 H54A 109.5 . . ?
N47 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
N47 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N50 C55 H55A 109.5 . . ?
N50 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
N50 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
N52 C57 H57A 109.5 . . ?
N52 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
N52 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
O62 C61 O63 123.0(13) . . ?
O62 C61 C64 122.0(13) . . ?
O63 C61 C64 114.8(16) . . ?
C61 O63 H63 109.5 . . ?
C65 C64 C61 118.3(14) . . ?
C65 C64 C69 124.8(16) . . ?
C61 C64 C69 116.9(14) . . ?
C64 C65 C66 124.3(16) . . ?
C64 C65 H65 117.8 . . ?
C66 C65 H65 117.8 . . ?
O67 C66 O68 121.7(12) . . ?
O67 C66 C65 128.3(14) . . ?
O68 C66 C65 110.0(14) . . ?
C66 O68 H68 109.5 . . ?
C64 C69 H69A 109.5 . . ?
C64 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C64 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O72 C71 O73 122.0(10) . . ?
O72 C71 C74 121.7(11) . . ?
O73 C71 C74 116.3(11) . . ?
C71 O73 H73 109.5 . . ?
C76 C74 C71 119.8(12) . . ?
C76 C74 C75 126.4(11) . . ?
C71 C74 C75 113.8(11) . . ?
C74 C75 H75A 109.5 . . ?
C74 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C74 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C74 C76 C77 126.6(12) . . ?
C74 C76 H76 116.7 . . ?
C77 C76 H76 116.7 . . ?
O78 C77 O79 123.7(10) . . ?
O78 C77 C76 124.4(11) . . ?
O79 C77 C76 111.8(11) . . ?
C77 O79 H79 109.5 . . ?
N81 C82 C83 177.5(17) . . ?
C82 C83 H83A 109.5 . . ?
C82 C83 H83B 109.5 . . ?
H83A C83 H83B 109.5 . . ?
C82 C83 H83C 109.5 . . ?
H83A C83 H83C 109.5 . . ?
H83B C83 H83C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.4(13) . . . . ?
N1 C2 N3 C4 -0.3(13) . . . . ?
N1 C2 N3 C10 176.5(10) . . . . ?
C2 N3 C4 C5 0.9(11) . . . . ?
C10 N3 C4 C5 -176.1(10) . . . . ?
C2 N3 C4 C9 -176.8(11) . . . . ?
C10 N3 C4 C9 6.2(18) . . . . ?
C2 N1 C5 C4 0.9(12) . . . . ?
C2 N1 C5 N6 179.6(11) . . . . ?
N3 C4 C5 N1 -1.1(12) . . . . ?
C9 C4 C5 N1 176.8(9) . . . . ?
N3 C4 C5 N6 -179.9(9) . . . . ?
C9 C4 C5 N6 -2.0(16) . . . . ?
N1 C5 N6 C7 -178.3(10) . . . . ?
C4 C5 N6 C7 0.3(16) . . . . ?
N1 C5 N6 C11 -1.7(16) . . . . ?
C4 C5 N6 C11 176.8(10) . . . . ?
C5 N6 C7 O12 179.7(10) . . . . ?
C11 N6 C7 O12 3.1(17) . . . . ?
C5 N6 C7 N8 -1.2(15) . . . . ?
C11 N6 C7 N8 -177.8(9) . . . . ?
O12 C7 N8 C9 -176.6(10) . . . . ?
N6 C7 N8 C9 4.3(15) . . . . ?
O12 C7 N8 C13 2.5(15) . . . . ?
N6 C7 N8 C13 -176.7(10) . . . . ?
C7 N8 C9 O14 173.3(10) . . . . ?
C13 N8 C9 O14 -5.7(15) . . . . ?
C7 N8 C9 C4 -5.6(15) . . . . ?
C13 N8 C9 C4 175.4(9) . . . . ?
C5 C4 C9 O14 -174.6(11) . . . . ?
N3 C4 C9 O14 2.8(19) . . . . ?
C5 C4 C9 N8 4.3(14) . . . . ?
N3 C4 C9 N8 -178.4(11) . . . . ?
C19 N15 C16 N17 0.5(12) . . . . ?
N15 C16 N17 C18 0.3(12) . . . . ?
N15 C16 N17 C24 -176.8(10) . . . . ?
C16 N17 C18 C19 -1.0(11) . . . . ?
C24 N17 C18 C19 176.1(10) . . . . ?
C16 N17 C18 C23 178.9(11) . . . . ?
C24 N17 C18 C23 -4.1(18) . . . . ?
C16 N15 C19 C18 -1.2(12) . . . . ?
C16 N15 C19 N20 -179.3(11) . . . . ?
N17 C18 C19 N15 1.3(12) . . . . ?
C23 C18 C19 N15 -178.5(10) . . . . ?
N17 C18 C19 N20 179.6(9) . . . . ?
C23 C18 C19 N20 -0.3(16) . . . . ?
N15 C19 N20 C21 179.6(10) . . . . ?
C18 C19 N20 C21 1.7(15) . . . . ?
N15 C19 N20 C25 1.8(16) . . . . ?
C18 C19 N20 C25 -176.1(10) . . . . ?
C19 N20 C21 O26 -177.6(10) . . . . ?
C25 N20 C21 O26 0.3(16) . . . . ?
C19 N20 C21 N22 -0.7(15) . . . . ?
C25 N20 C21 N22 177.2(10) . . . . ?
O26 C21 N22 C23 175.1(10) . . . . ?
N20 C21 N22 C23 -1.9(16) . . . . ?
O26 C21 N22 C27 -3.5(15) . . . . ?
N20 C21 N22 C27 179.6(10) . . . . ?
C21 N22 C23 O28 -174.8(10) . . . . ?
C27 N22 C23 O28 3.7(15) . . . . ?
C21 N22 C23 C18 3.1(14) . . . . ?
C27 N22 C23 C18 -178.4(10) . . . . ?
C19 C18 C23 O28 175.8(11) . . . . ?
N17 C18 C23 O28 -4.0(19) . . . . ?
C19 C18 C23 N22 -1.9(14) . . . . ?
N17 C18 C23 N22 178.3(10) . . . . ?
C35 N31 C32 N33 0.1(12) . . . . ?
N31 C32 N33 C34 0.4(13) . . . . ?
N31 C32 N33 C40 -175.8(11) . . . . ?
C32 N33 C34 C35 -0.7(12) . . . . ?
C40 N33 C34 C35 175.5(10) . . . . ?
C32 N33 C34 C39 179.0(12) . . . . ?
C40 N33 C34 C39 -5(2) . . . . ?
N33 C34 C35 N31 0.8(13) . . . . ?
C39 C34 C35 N31 -178.9(10) . . . . ?
N33 C34 C35 N36 -179.7(10) . . . . ?
C39 C34 C35 N36 0.5(18) . . . . ?
C32 N31 C35 C34 -0.6(12) . . . . ?
C32 N31 C35 N36 -180.0(11) . . . . ?
C34 C35 N36 C37 3.0(16) . . . . ?
N31 C35 N36 C37 -177.7(10) . . . . ?
C34 C35 N36 C41 -177.8(11) . . . . ?
N31 C35 N36 C41 1.6(17) . . . . ?
C35 N36 C37 O42 176.8(10) . . . . ?
C41 N36 C37 O42 -2.4(16) . . . . ?
C35 N36 C37 N38 -3.3(14) . . . . ?
C41 N36 C37 N38 177.4(10) . . . . ?
O42 C37 N38 C39 -179.7(10) . . . . ?
N36 C37 N38 C39 0.4(16) . . . . ?
O42 C37 N38 C43 -1.3(15) . . . . ?
N36 C37 N38 C43 178.8(10) . . . . ?
C37 N38 C39 O44 -177.4(10) . . . . ?
C43 N38 C39 O44 4.3(17) . . . . ?
C37 N38 C39 C34 2.7(16) . . . . ?
C43 N38 C39 C34 -175.6(10) . . . . ?
C35 C34 C39 O44 176.9(12) . . . . ?
N33 C34 C39 O44 -3(2) . . . . ?
C35 C34 C39 N38 -3.2(16) . . . . ?
N33 C34 C39 N38 177.1(12) . . . . ?
C49 N45 C46 N47 1.5(13) . . . . ?
N45 C46 N47 C48 -1.7(13) . . . . ?
N45 C46 N47 C54 176.3(11) . . . . ?
C46 N47 C48 C49 1.1(12) . . . . ?
C54 N47 C48 C49 -176.9(11) . . . . ?
C46 N47 C48 C53 -179.5(12) . . . . ?
C54 N47 C48 C53 2(2) . . . . ?
C46 N45 C49 C48 -0.7(13) . . . . ?
C46 N45 C49 N50 -179.1(11) . . . . ?
N47 C48 C49 N45 -0.3(13) . . . . ?
C53 C48 C49 N45 -179.6(10) . . . . ?
N47 C48 C49 N50 178.2(9) . . . . ?
C53 C48 C49 N50 -1.2(18) . . . . ?
N45 C49 N50 C51 178.0(10) . . . . ?
C48 C49 N50 C51 -0.2(15) . . . . ?
N45 C49 N50 C55 -1.5(16) . . . . ?
C48 C49 N50 C55 -179.7(10) . . . . ?
C49 N50 C51 O56 -178.9(10) . . . . ?
C55 N50 C51 O56 0.6(15) . . . . ?
C49 N50 C51 N52 1.2(14) . . . . ?
C55 N50 C51 N52 -179.3(9) . . . . ?
O56 C51 N52 C53 179.1(10) . . . . ?
N50 C51 N52 C53 -1.0(16) . . . . ?
O56 C51 N52 C57 2.5(15) . . . . ?
N50 C51 N52 C57 -177.5(9) . . . . ?
C51 N52 C53 O58 -179.6(10) . . . . ?
C57 N52 C53 O58 -3.1(15) . . . . ?
C51 N52 C53 C48 -0.3(15) . . . . ?
C57 N52 C53 C48 176.2(9) . . . . ?
C49 C48 C53 O58 -179.3(11) . . . . ?
N47 C48 C53 O58 1(2) . . . . ?
C49 C48 C53 N52 1.4(16) . . . . ?
N47 C48 C53 N52 -177.8(11) . . . . ?
O62 C61 C64 C65 175.5(14) . . . . ?
O63 C61 C64 C65 -9.3(18) . . . . ?
O62 C61 C64 C69 -3(2) . . . . ?
O63 C61 C64 C69 172.5(11) . . . . ?
C61 C64 C65 C66 -178.2(12) . . . . ?
C69 C64 C65 C66 0(2) . . . . ?
C64 C65 C66 O67 -1(2) . . . . ?
C64 C65 C66 O68 178.6(12) . . . . ?
O72 C71 C74 C76 175.3(11) . . . . ?
O73 C71 C74 C76 -4.2(15) . . . . ?
O72 C71 C74 C75 -6.2(15) . . . . ?
O73 C71 C74 C75 174.3(10) . . . . ?
C71 C74 C76 C77 179.7(10) . . . . ?
C75 C74 C76 C77 1.5(19) . . . . ?
C74 C76 C77 O78 -10.4(19) . . . . ?
C74 C76 C77 O79 173.1(11) . . . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 994954'
