# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_sn27
_database_code_depnum_ccdc_archive 'CCDC 1455566'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4, 2(C H4 O)'
_chemical_formula_sum            'C46 H38 N4 O6'
_chemical_formula_weight         742.80

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                   10.7414(6)
_cell_length_b                   11.2551(6)
_cell_length_c                   16.1946(8)
_cell_angle_alpha                84.010(3)
_cell_angle_beta                 77.531(3)
_cell_angle_gamma                69.651(3)
_cell_volume                     1791.45(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7027
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      28.4

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            31782
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8910
_reflns_number_gt                7027
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0645P)²+1.6055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8910
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1322
_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
O1 O 1.30673(13) -0.02497(12) 0.43927(8) 0.0218(3) Uani 1 1 d . . . . .
H1 H 1.3987 -0.0644 0.4240 0.033 Uiso 1 1 d R U . . .
O2 O 0.12219(13) 0.66875(13) 0.26129(8) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.0981 0.7392 0.2970 0.036 Uiso 1 1 d R U . . .
O3 O 0.11020(15) 0.85834(12) 0.49679(9) 0.0266(3) Uani 1 1 d . . . . .
H3 H 0.1839 0.9034 0.4905 0.040 Uiso 1 1 d R U . . .
O4 O 0.97717(15) 0.19312(13) -0.11984(9) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.9540 0.2430 -0.1681 0.043 Uiso 1 1 d R U . . .
O5 O 0.80270(19) 0.06132(16) -0.06947(8) 0.0393(4) Uani 1 1 d . . . . .
H5 H 0.8658 0.1090 -0.0866 0.059 Uiso 1 1 d R U . . .
O6 O 0.00980(17) 0.87927(14) 0.35026(10) 0.0372(4) Uani 1 1 d . . . . .
H6 H 0.0148 0.8918 0.4064 0.056 Uiso 1 1 d R U . . .
N1 N 0.49313(14) 0.15229(13) 0.41167(8) 0.0134(3) Uani 1 1 d . . . . .
H7 H 0.5046 0.0879 0.4472 0.016 Uiso 1 1 d R U . . .
N2 N 0.91613(14) 0.44686(13) 0.11890(9) 0.0151(3) Uani 1 1 d . . . . .
H2A H 0.9546 0.4748 0.0709 0.018 Uiso 0.5 1 calc R U P . .
N3 N 0.41185(14) 0.12458(13) 0.59760(8) 0.0139(3) Uani 1 1 d . . . . .
N4 N 1.18781(14) 0.38936(13) 0.02335(9) 0.0146(3) Uani 1 1 d . . . . .
H4A H 1.1066 0.4355 0.0145 0.018 Uiso 0.5 1 calc R U P . .
C1 C 0.77977(17) 0.47980(15) 0.15024(10) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.98183(17) 0.36251(15) 0.17590(10) 0.0150(3) Uani 1 1 d . . . . .
C3 C 1.17359(17) 0.21622(15) 0.23762(10) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.60803(16) 0.02802(15) 0.28244(10) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.35976(16) 0.09425(15) 0.67889(10) 0.0144(3) Uani 1 1 d . . . . .
C6 C 0.42425(16) 0.27712(15) 0.43136(10) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.67547(17) 0.56135(15) 0.11141(10) 0.0147(3) Uani 1 1 d . . . . .
C8 C 1.12243(17) 0.30221(15) 0.16652(10) 0.0147(3) Uani 1 1 d . . . . .
C9 C 1.30803(17) 0.37773(15) -0.03158(10) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.42729(17) 0.34864(16) 0.35305(10) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.3898 0.4382 0.3466 0.019 Uiso 1 1 calc R U . . .
C11 C 0.34566(17) 0.25219(15) 0.58685(10) 0.0142(3) Uani 1 1 d . . . . .
C12 C 1.21729(17) 0.31587(15) 0.09468(10) 0.0145(3) Uani 1 1 d . . . . .
C13 C 0.53262(17) 0.58309(15) 0.15684(10) 0.0147(3) Uani 1 1 d . . . . .
C14 C 0.28641(17) 0.46513(15) 0.51388(10) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.35745(17) 0.32474(15) 0.51145(10) 0.0143(3) Uani 1 1 d . . . . .
C16 C 0.17110(18) 0.52111(16) 0.47912(11) 0.0182(3) Uani 1 1 d . . . . .
H16 H 0.1332 0.4690 0.4575 0.022 Uiso 1 1 calc R U . . .
C17 C 0.53617(16) 0.14088(15) 0.32550(10) 0.0142(3) Uani 1 1 d . . . . .
C18 C 0.47663(18) 0.65488(16) 0.22914(11) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.5320 0.6859 0.2533 0.022 Uiso 1 1 calc R U . . .
C19 C 0.75888(17) 0.41396(16) 0.23028(10) 0.0163(3) Uani 1 1 d . . . . .
H19 H 0.6741 0.4198 0.2656 0.020 Uiso 1 1 calc R U . . .
C20 C 0.65782(17) 0.03936(15) 0.18968(10) 0.0151(3) Uani 1 1 d . . . . .
C21 C 1.36186(17) 0.25618(15) 0.08404(11) 0.0158(3) Uani 1 1 d . . . . .
H21 H 1.4096 0.2014 0.1240 0.019 Uiso 1 1 calc R U . . .
C22 C 1.18815(18) 0.17983(17) 0.38613(11) 0.0185(3) Uani 1 1 d . . . . .
H22 H 1.1657 0.2109 0.4417 0.022 Uiso 1 1 calc R U . . .
C23 C 0.25863(17) 0.63832(16) 0.23068(11) 0.0180(3) Uani 1 1 d . . . . .
C24 C 1.41727(17) 0.29270(15) 0.00631(11) 0.0162(3) Uani 1 1 d . . . . .
H24 H 1.5108 0.2669 -0.0185 0.019 Uiso 1 1 calc R U . . .
C25 C 0.25942(18) 0.20516(16) 0.72032(11) 0.0176(3) Uani 1 1 d . . . . .
H25 H 0.2092 0.2084 0.7765 0.021 Uiso 1 1 calc R U . . .
C26 C 0.25107(18) 0.30315(16) 0.66345(11) 0.0174(3) Uani 1 1 d . . . . .
H26 H 0.1942 0.3887 0.6720 0.021 Uiso 1 1 calc R U . . .
C27 C 0.49335(17) 0.26609(16) 0.28927(11) 0.0164(3) Uani 1 1 d . . . . .
H27 H 0.5083 0.2882 0.2306 0.020 Uiso 1 1 calc R U . . .
C28 C 0.34077(18) 0.68180(16) 0.26640(11) 0.0192(3) Uani 1 1 d . . . . .
H28 H 0.3042 0.7298 0.3162 0.023 Uiso 1 1 calc R U . . .
C29 C 0.88250(17) 0.34213(16) 0.24593(10) 0.0166(3) Uani 1 1 d . . . . .
H29 H 0.9003 0.2882 0.2943 0.020 Uiso 1 1 calc R U . . .
C30 C 0.62997(18) -0.02879(16) 0.13284(11) 0.0176(3) Uani 1 1 d . . . . .
H30 H 0.5773 -0.0820 0.1536 0.021 Uiso 1 1 calc R U . . .
C31 C 0.45024(18) 0.53425(16) 0.12505(11) 0.0180(3) Uani 1 1 d . . . . .
H31 H 0.4879 0.4814 0.0776 0.022 Uiso 1 1 calc R U . . .
C32 C 1.14384(17) 0.26045(16) 0.31949(11) 0.0176(3) Uani 1 1 d . . . . .
H32 H 1.0925 0.3471 0.3298 0.021 Uiso 1 1 calc R U . . .
C33 C 0.33755(18) 0.54321(16) 0.54754(10) 0.0179(3) Uani 1 1 d . . . . .
H33 H 0.4133 0.5062 0.5743 0.021 Uiso 1 1 calc R U . . .
C34 C 1.26511(17) 0.05397(16) 0.37126(10) 0.0166(3) Uani 1 1 d . . . . .
C35 C 1.25009(18) 0.08863(16) 0.22435(11) 0.0170(3) Uani 1 1 d . . . . .
H35 H 1.2706 0.0563 0.1693 0.020 Uiso 1 1 calc R U . . .
C36 C 0.73481(19) 0.11719(17) 0.15714(11) 0.0191(3) Uani 1 1 d . . . . .
H36 H 0.7541 0.1649 0.1948 0.023 Uiso 1 1 calc R U . . .
C37 C 0.16757(19) 0.72864(16) 0.50544(11) 0.0195(4) Uani 1 1 d . . . . .
C38 C 1.29671(18) 0.00823(16) 0.29051(11) 0.0184(3) Uani 1 1 d . . . . .
H38 H 1.3501 -0.0779 0.2803 0.022 Uiso 1 1 calc R U . . .
C39 C 0.27954(19) 0.67474(17) 0.54272(11) 0.0207(4) Uani 1 1 d . . . . .
H39 H 0.3167 0.7269 0.5649 0.025 Uiso 1 1 calc R U . . .
C40 C 0.31441(18) 0.56122(17) 0.16125(11) 0.0201(4) Uani 1 1 d . . . . .
H40 H 0.2599 0.5271 0.1387 0.024 Uiso 1 1 calc R U . . .
C41 C 0.11052(18) 0.65184(16) 0.47545(11) 0.0194(3) Uani 1 1 d . . . . .
H41 H 0.0306 0.6888 0.4526 0.023 Uiso 1 1 calc R U . . .
C42 C 0.6781(2) -0.01986(17) 0.04650(11) 0.0219(4) Uani 1 1 d . . . . .
H42 H 0.6578 -0.0663 0.0086 0.026 Uiso 1 1 calc R U . . .
C43 C 0.7562(2) 0.05706(18) 0.01541(11) 0.0241(4) Uani 1 1 d . . . . .
C44 C 0.7835(2) 0.12629(18) 0.07126(11) 0.0235(4) Uani 1 1 d . . . . .
H44 H 0.8357 0.1799 0.0504 0.028 Uiso 1 1 calc R U . . .
C45 C 1.0095(2) 0.2674(2) -0.06776(13) 0.0317(5) Uani 1 1 d . . . . .
H45A H 0.9268 0.3339 -0.0426 0.048 Uiso 1 1 calc R U . . .
H45B H 1.0731 0.3064 -0.1019 0.048 Uiso 1 1 calc R U . . .
H45C H 1.0509 0.2133 -0.0227 0.048 Uiso 1 1 calc R U . . .
C46 C -0.0508(2) 0.9941(2) 0.30856(15) 0.0350(5) Uani 1 1 d . . . . .
H46A H -0.1397 1.0386 0.3423 0.052 Uiso 1 1 calc R U . . .
H46B H -0.0616 0.9766 0.2530 0.052 Uiso 1 1 calc R U . . .
H46C H 0.0067 1.0470 0.3013 0.052 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
O1 C34 1.3909(19) . ?
O1 H1 0.9199 . ?
O2 C23 1.372(2) . ?
O2 H2 0.9579 . ?
O3 C37 1.378(2) . ?
O3 H3 1.0616 . ?
O4 C45 1.416(2) . ?
O4 H4 0.9400 . ?
O5 C43 1.359(2) . ?
O5 H5 0.9824 . ?
O6 C46 1.404(3) . ?
O6 H6 0.9498 . ?
N1 C6 1.375(2) . ?
N1 C17 1.377(2) . ?
N1 H7 0.8674 . ?
N2 C1 1.371(2) . ?
N2 C2 1.373(2) . ?
N2 H2A 0.8800 . ?
N3 C5 1.372(2) . ?
N3 C11 1.375(2) . ?
N4 C9 1.374(2) . ?
N4 C12 1.377(2) . ?
N4 H4A 0.8800 . ?
C1 C7 1.401(2) . ?
C1 C19 1.438(2) . ?
C2 C8 1.405(2) . ?
C2 C29 1.439(2) . ?
C3 C35 1.397(2) . ?
C3 C32 1.397(2) . ?
C3 C8 1.495(2) . ?
C4 C17 1.402(2) . ?
C4 C5 1.410(2) 2_656 ?
C4 C20 1.490(2) . ?
C5 C4 1.410(2) 2_656 ?
C5 C25 1.448(2) . ?
C6 C15 1.400(2) . ?
C6 C10 1.430(2) . ?
C7 C9 1.405(2) 2_765 ?
C7 C13 1.498(2) . ?
C8 C12 1.405(2) . ?
C9 C7 1.405(2) 2_765 ?
C9 C24 1.441(2) . ?
C10 C27 1.363(2) . ?
C10 H10 0.9500 . ?
C11 C15 1.404(2) . ?
C11 C26 1.449(2) . ?
C12 C21 1.441(2) . ?
C13 C18 1.393(2) . ?
C13 C31 1.394(2) . ?
C14 C16 1.390(2) . ?
C14 C33 1.392(2) . ?
C14 C15 1.497(2) . ?
C16 C41 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C27 1.426(2) . ?
C18 C28 1.391(2) . ?
C18 H18 0.9500 . ?
C19 C29 1.355(2) . ?
C19 H19 0.9500 . ?
C20 C36 1.396(2) . ?
C20 C30 1.397(2) . ?
C21 C24 1.359(2) . ?
C21 H21 0.9500 . ?
C22 C34 1.385(2) . ?
C22 C32 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C40 1.388(3) . ?
C23 C28 1.390(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.352(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C42 1.388(2) . ?
C30 H30 0.9500 . ?
C31 C40 1.387(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C39 1.393(2) . ?
C33 H33 0.9500 . ?
C34 C38 1.385(2) . ?
C35 C38 1.390(2) . ?
C35 H35 0.9500 . ?
C36 C44 1.383(2) . ?
C36 H36 0.9500 . ?
C37 C39 1.382(3) . ?
C37 C41 1.394(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 C43 1.392(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.390(3) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
C34 O1 H1 106.9 . . ?
C23 O2 H2 105.6 . . ?
C37 O3 H3 111.1 . . ?
C45 O4 H4 107.7 . . ?
C43 O5 H5 113.9 . . ?
C46 O6 H6 111.9 . . ?
C6 N1 C17 110.49(13) . . ?
C6 N1 H7 126.1 . . ?
C17 N1 H7 123.4 . . ?
C1 N2 C2 107.68(13) . . ?
C1 N2 H2A 126.2 . . ?
C2 N2 H2A 126.2 . . ?
C5 N3 C11 105.19(13) . . ?
C9 N4 C12 107.67(14) . . ?
C9 N4 H4A 126.2 . . ?
C12 N4 H4A 126.2 . . ?
N2 C1 C7 126.80(15) . . ?
N2 C1 C19 108.83(14) . . ?
C7 C1 C19 124.36(15) . . ?
N2 C2 C8 125.95(15) . . ?
N2 C2 C29 108.70(14) . . ?
C8 C2 C29 125.31(15) . . ?
C35 C3 C32 118.14(15) . . ?
C35 C3 C8 120.84(15) . . ?
C32 C3 C8 121.00(15) . . ?
C17 C4 C5 124.70(15) . 2_656 ?
C17 C4 C20 117.21(14) . . ?
C5 C4 C20 118.05(14) 2_656 . ?
N3 C5 C4 126.04(15) . 2_656 ?
N3 C5 C25 110.79(14) . . ?
C4 C5 C25 123.10(15) 2_656 . ?
N1 C6 C15 127.06(14) . . ?
N1 C6 C10 106.45(14) . . ?
C15 C6 C10 126.40(15) . . ?
C1 C7 C9 125.87(15) . 2_765 ?
C1 C7 C13 117.87(14) . . ?
C9 C7 C13 116.23(14) 2_765 . ?
C2 C8 C12 124.51(15) . . ?
C2 C8 C3 117.35(15) . . ?
C12 C8 C3 118.13(15) . . ?
N4 C9 C7 126.53(15) . 2_765 ?
N4 C9 C24 108.79(14) . . ?
C7 C9 C24 124.68(15) 2_765 . ?
C27 C10 C6 108.17(14) . . ?
C27 C10 H10 125.9 . . ?
C6 C10 H10 125.9 . . ?
N3 C11 C15 126.26(15) . . ?
N3 C11 C26 110.71(14) . . ?
C15 C11 C26 122.87(15) . . ?
N4 C12 C8 125.77(15) . . ?
N4 C12 C21 108.74(14) . . ?
C8 C12 C21 125.48(15) . . ?
C18 C13 C31 118.13(15) . . ?
C18 C13 C7 122.07(15) . . ?
C31 C13 C7 119.77(15) . . ?
C16 C14 C33 118.40(15) . . ?
C16 C14 C15 120.71(15) . . ?
C33 C14 C15 120.83(15) . . ?
C6 C15 C11 125.82(15) . . ?
C6 C15 C14 115.58(14) . . ?
C11 C15 C14 118.49(14) . . ?
C41 C16 C14 121.06(16) . . ?
C41 C16 H16 119.5 . . ?
C14 C16 H16 119.5 . . ?
N1 C17 C4 126.44(15) . . ?
N1 C17 C27 106.41(14) . . ?
C4 C17 C27 127.15(15) . . ?
C28 C18 C13 120.93(16) . . ?
C28 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C29 C19 C1 107.34(15) . . ?
C29 C19 H19 126.3 . . ?
C1 C19 H19 126.3 . . ?
C36 C20 C30 118.10(15) . . ?
C36 C20 C4 121.03(15) . . ?
C30 C20 C4 120.87(15) . . ?
C24 C21 C12 107.37(14) . . ?
C24 C21 H21 126.3 . . ?
C12 C21 H21 126.3 . . ?
C34 C22 C32 119.73(16) . . ?
C34 C22 H22 120.1 . . ?
C32 C22 H22 120.1 . . ?
O2 C23 C40 117.65(16) . . ?
O2 C23 C28 122.52(16) . . ?
C40 C23 C28 119.83(16) . . ?
C21 C24 C9 107.41(15) . . ?
C21 C24 H24 126.3 . . ?
C9 C24 H24 126.3 . . ?
C26 C25 C5 106.68(15) . . ?
C26 C25 H25 126.7 . . ?
C5 C25 H25 126.7 . . ?
C25 C26 C11 106.64(15) . . ?
C25 C26 H26 126.7 . . ?
C11 C26 H26 126.7 . . ?
C10 C27 C17 108.46(15) . . ?
C10 C27 H27 125.8 . . ?
C17 C27 H27 125.8 . . ?
C23 C28 C18 119.89(16) . . ?
C23 C28 H28 120.1 . . ?
C18 C28 H28 120.1 . . ?
C19 C29 C2 107.45(15) . . ?
C19 C29 H29 126.3 . . ?
C2 C29 H29 126.3 . . ?
C42 C30 C20 120.93(16) . . ?
C42 C30 H30 119.5 . . ?
C20 C30 H30 119.5 . . ?
C40 C31 C13 121.41(16) . . ?
C40 C31 H31 119.3 . . ?
C13 C31 H31 119.3 . . ?
C22 C32 C3 121.08(16) . . ?
C22 C32 H32 119.5 . . ?
C3 C32 H32 119.5 . . ?
C14 C33 C39 121.15(16) . . ?
C14 C33 H33 119.4 . . ?
C39 C33 H33 119.4 . . ?
C38 C34 C22 120.19(15) . . ?
C38 C34 O1 121.26(15) . . ?
C22 C34 O1 118.53(15) . . ?
C38 C35 C3 120.95(16) . . ?
C38 C35 H35 119.5 . . ?
C3 C35 H35 119.5 . . ?
C44 C36 C20 121.33(16) . . ?
C44 C36 H36 119.3 . . ?
C20 C36 H36 119.3 . . ?
O3 C37 C39 121.22(17) . . ?
O3 C37 C41 118.62(16) . . ?
C39 C37 C41 120.17(16) . . ?
C34 C38 C35 119.88(16) . . ?
C34 C38 H38 120.1 . . ?
C35 C38 H38 120.1 . . ?
C37 C39 C33 119.49(17) . . ?
C37 C39 H39 120.3 . . ?
C33 C39 H39 120.3 . . ?
C31 C40 C23 119.62(16) . . ?
C31 C40 H40 120.2 . . ?
C23 C40 H40 120.2 . . ?
C16 C41 C37 119.60(16) . . ?
C16 C41 H41 120.2 . . ?
C37 C41 H41 120.2 . . ?
C30 C42 C43 120.08(16) . . ?
C30 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
O5 C43 C44 122.53(17) . . ?
O5 C43 C42 117.94(17) . . ?
C44 C43 C42 119.53(16) . . ?
C36 C44 C43 120.03(17) . . ?
C36 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
O4 C45 H45A 109.5 . . ?
O4 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O4 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O6 C46 H46A 109.5 . . ?
O6 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O6 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.92 1.87 2.7846(19) 171 2_756
O2 H2 O6 0.96 1.74 2.668(2) 163 .
O3 H3 O1 1.06 1.79 2.806(2) 158 1_465
O4 H4 O2 0.94 1.89 2.822(2) 168 2_665
O5 H5 O4 0.98 1.74 2.720(2) 178 .
O6 H6 O3 0.95 1.90 2.768(2) 151 .

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062

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

data_sn31
_database_code_depnum_ccdc_archive 'CCDC 1455567'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4, 3(C16 H10)'
_chemical_formula_sum            'C92 H60 N4 O4'
_chemical_formula_weight         1285.44

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                   13.8522(15)
_cell_length_b                   15.6089(16)
_cell_length_c                   15.8464(15)
_cell_angle_alpha                65.532(3)
_cell_angle_beta                 83.496(3)
_cell_angle_gamma                89.872(3)
_cell_volume                     3094.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7769
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      25.07

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            29773
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.923
_diffrn_reflns_theta_max         25.075
_diffrn_reflns_theta_full        25.075
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             10685
_reflns_number_gt                7769
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0679P)²+4.0360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10685
_refine_ls_number_parameters     901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02173(13) 0.04423(13) 1.04491(13) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.0334 0.0117 1.0996 0.032 Uiso 1 1 d R U . . .
O2 O 0.93961(13) 0.06449(13) 0.77380(13) 0.0254(5) Uani 1 1 d D . . . .
H2 H 0.9366 0.0561 0.7245 0.038 Uiso 1 1 d DR U . . .
O3 O 0.98564(13) 0.95905(13) 0.39366(14) 0.0267(5) Uani 1 1 d . . . . .
H3 H 0.9656 0.9866 0.3410 0.040 Uiso 1 1 d R U . . .
O4 O 0.09155(15) 0.93460(14) 0.80885(15) 0.0307(5) Uani 1 1 d D . . . .
H4 H 0.0705 0.9258 0.8645 0.046 Uiso 1 1 d DR U . . .
N1 N 0.51903(15) 0.65281(15) 0.70683(15) 0.0160(5) Uani 1 1 d . . . . .
H5 H 0.5142 0.5924 0.7194 0.019 Uiso 1 1 calc R U . . .
N2 N 0.49241(15) 0.36210(15) 0.78190(15) 0.0161(5) Uani 1 1 d . . . . .
H6 H 0.4953 0.4235 0.7644 0.019 Uiso 1 1 calc R U . . .
N3 N 0.36878(16) 0.49680(15) 0.81613(16) 0.0186(5) Uani 1 1 d . . . . .
N4 N 0.64177(16) 0.51568(15) 0.67552(16) 0.0182(5) Uani 1 1 d . . . . .
C1 C 0.31820(19) 0.57407(18) 0.81389(18) 0.0155(6) Uani 1 1 d . . . . .
C2 C 0.44926(19) 0.70168(18) 0.73431(18) 0.0161(6) Uani 1 1 d . . . . .
C3 C 0.70407(19) 0.59360(19) 0.63415(18) 0.0164(6) Uani 1 1 d . . . . .
C4 C 0.41167(19) 0.30284(18) 0.82713(18) 0.0161(6) Uani 1 1 d . . . . .
C5 C 0.76109(18) 0.76165(18) 0.55962(19) 0.0175(6) Uani 1 1 d . . . . .
C6 C 0.24258(18) 0.25449(18) 0.90472(19) 0.0168(6) Uani 1 1 d . . . . .
C7 C 0.35559(19) 0.66732(18) 0.78128(18) 0.0166(6) Uani 1 1 d . . . . .
C8 C 0.30267(19) 0.42094(18) 0.84785(18) 0.0156(6) Uani 1 1 d . . . . .
C9 C 0.68353(19) 0.68730(18) 0.61853(18) 0.0162(6) Uani 1 1 d . . . . .
C10 C 0.69656(19) 0.43853(19) 0.68746(18) 0.0170(6) Uani 1 1 d . . . . .
C11 C 0.56750(19) 0.31007(18) 0.76852(18) 0.0171(6) Uani 1 1 d . . . . .
C12 C 0.28640(19) 0.73722(18) 0.79102(19) 0.0187(6) Uani 1 1 d . . . . .
C13 C 0.20773(19) 0.45203(19) 0.86513(19) 0.0184(6) Uani 1 1 d . . . . .
H13 H 0.1488 0.4142 0.8869 0.022 Uiso 1 1 calc R U . . .
C14 C 0.73648(19) 0.27071(18) 0.73999(19) 0.0179(6) Uani 1 1 d . . . . .
C15 C 0.57706(19) 0.80371(18) 0.65412(19) 0.0181(6) Uani 1 1 d . . . . .
H15 H 0.6184 0.8591 0.6242 0.022 Uiso 1 1 calc R U . . .
C16 C 0.59758(18) 0.71273(18) 0.65661(18) 0.0150(6) Uani 1 1 d . . . . .
C17 C 0.32227(19) 0.32925(18) 0.85714(18) 0.0158(6) Uani 1 1 d . . . . .
C18 C 0.09379(18) 0.11190(18) 0.99788(19) 0.0179(6) Uani 1 1 d . . . . .
C19 C 0.4876(2) 0.79615(19) 0.70242(19) 0.0203(6) Uani 1 1 d . . . . .
H19 H 0.4559 0.8454 0.7131 0.024 Uiso 1 1 calc R U . . .
C20 C 0.5666(2) 1.01235(18) 0.7036(2) 0.0212(6) Uani 1 1 d . . . . .
C21 C 0.20688(19) 0.20140(19) 0.86136(19) 0.0188(6) Uani 1 1 d . . . . .
H21 H 0.2334 0.2136 0.7993 0.023 Uiso 1 1 calc R U . . .
C22 C 0.78006(19) 0.25559(19) 0.66412(19) 0.0196(6) Uani 1 1 d . . . . .
H22 H 0.7632 0.2927 0.6035 0.024 Uiso 1 1 calc R U . . .
C23 C 0.13403(19) 0.13167(19) 0.90648(19) 0.0204(6) Uani 1 1 d . . . . .
H23 H 0.1111 0.0969 0.8751 0.024 Uiso 1 1 calc R U . . .
C24 C 0.1284(2) 0.16483(19) 1.04181(19) 0.0200(6) Uani 1 1 d . . . . .
H24 H 0.1019 0.1527 1.1039 0.024 Uiso 1 1 calc R U . . .
C25 C 0.9112(2) 0.89442(19) 0.4456(2) 0.0219(6) Uani 1 1 d . . . . .
C26 C 0.87234(19) 0.13207(19) 0.7645(2) 0.0202(6) Uani 1 1 d . . . . .
C27 C 0.43708(19) 0.20969(19) 0.83983(19) 0.0189(6) Uani 1 1 d . . . . .
H27 H 0.3952 0.1545 0.8680 0.023 Uiso 1 1 calc R U . . .
C28 C 0.8476(2) 0.18731(19) 0.67556(19) 0.0217(6) Uani 1 1 d . . . . .
H28 H 0.8770 0.1781 0.6230 0.026 Uiso 1 1 calc R U . . .
C29 C 0.21766(19) 0.54525(19) 0.84455(18) 0.0182(6) Uani 1 1 d . . . . .
H29 H 0.1668 0.5845 0.8496 0.022 Uiso 1 1 calc R U . . .
C30 C 0.66356(19) 0.34422(19) 0.72942(18) 0.0170(6) Uani 1 1 d . . . . .
C31 C 0.79028(19) 0.77463(19) 0.46790(19) 0.0205(6) Uani 1 1 d . . . . .
H31 H 0.7590 0.7374 0.4433 0.025 Uiso 1 1 calc R U . . .
C32 C 0.8095(2) 0.8176(2) 0.5933(2) 0.0223(6) Uani 1 1 d . . . . .
H32 H 0.7914 0.8109 0.6554 0.027 Uiso 1 1 calc R U . . .
C33 C 1.01672(19) 0.4903(2) 0.72095(19) 0.0204(6) Uani 1 1 d . . . . .
C34 C 0.1823(2) 0.79704(19) 0.8861(2) 0.0221(6) Uani 1 1 d . . . . .
H34 H 0.1571 0.7928 0.9461 0.027 Uiso 1 1 calc R U . . .
C35 C 0.4926(2) 0.99412(18) 0.7794(2) 0.0213(6) Uani 1 1 d . . . . .
C36 C 0.5323(2) 0.21438(19) 0.80425(19) 0.0204(6) Uani 1 1 d . . . . .
H36 H 0.5686 0.1630 0.8034 0.024 Uiso 1 1 calc R U . . .
C37 C 0.15476(19) 0.8674(2) 0.8068(2) 0.0223(6) Uani 1 1 d . . . . .
C38 C 0.80137(19) 0.56496(19) 0.61887(19) 0.0180(6) Uani 1 1 d . . . . .
H38 H 0.8581 0.6053 0.5904 0.022 Uiso 1 1 calc R U . . .
C39 C 0.3947(2) 1.01380(19) 0.7634(2) 0.0256(7) Uani 1 1 d . . . . .
C40 C 0.8843(2) 0.8831(2) 0.5365(2) 0.0234(6) Uani 1 1 d . . . . .
H40 H 0.9167 0.9200 0.5606 0.028 Uiso 1 1 calc R U . . .
C41 C 1.0025(2) 0.3904(2) 0.7706(2) 0.0246(7) Uani 1 1 d . . . . .
C42 C 0.79640(19) 0.47012(19) 0.65265(18) 0.0184(6) Uani 1 1 d . . . . .
H42 H 0.8494 0.4312 0.6533 0.022 Uiso 1 1 calc R U . . .
C43 C 0.20115(19) 0.23509(19) 0.99547(19) 0.0182(6) Uani 1 1 d . . . . .
H43 H 0.2232 0.2708 1.0263 0.022 Uiso 1 1 calc R U . . .
C44 C 0.5423(2) 1.04898(19) 0.6105(2) 0.0248(7) Uani 1 1 d . . . . .
C45 C 0.8298(2) 0.14582(19) 0.8409(2) 0.0214(6) Uani 1 1 d . . . . .
H45 H 0.8466 0.1084 0.9015 0.026 Uiso 1 1 calc R U . . .
C46 C 0.1911(2) 0.8735(2) 0.7192(2) 0.0252(7) Uani 1 1 d . . . . .
H46 H 0.1714 0.9216 0.6646 0.030 Uiso 1 1 calc R U . . .
C47 C 0.2568(2) 0.80851(19) 0.7120(2) 0.0225(6) Uani 1 1 d . . . . .
H47 H 0.2818 0.8129 0.6520 0.027 Uiso 1 1 calc R U . . .
C48 C 0.8640(2) 0.84062(19) 0.4111(2) 0.0222(6) Uani 1 1 d . . . . .
H48 H 0.8817 0.8485 0.3485 0.027 Uiso 1 1 calc R U . . .
C49 C 0.2475(2) 0.73225(19) 0.8777(2) 0.0214(6) Uani 1 1 d . . . . .
H49 H 0.2659 0.6834 0.9327 0.026 Uiso 1 1 calc R U . . .
C50 C 0.6647(2) 0.9937(2) 0.7194(2) 0.0254(7) Uani 1 1 d . . . . .
C51 C 0.5165(2) 0.9563(2) 0.8728(2) 0.0270(7) Uani 1 1 d . . . . .
C52 C 0.7624(2) 0.21477(19) 0.8285(2) 0.0212(6) Uani 1 1 d . . . . .
H52 H 0.7334 0.2241 0.8811 0.025 Uiso 1 1 calc R U . . .
C53 C 1.0541(2) 0.5296(2) 0.6253(2) 0.0244(7) Uani 1 1 d . . . . .
C54 C 0.99452(19) 0.5504(2) 0.7668(2) 0.0229(6) Uani 1 1 d . . . . .
C55 C 1.0103(2) 0.6486(2) 0.7178(2) 0.0282(7) Uani 1 1 d . . . . .
C56 C 0.9572(2) 0.5095(2) 0.8639(2) 0.0283(7) Uani 1 1 d . . . . .
C57 C 0.3725(2) 1.0509(2) 0.6687(2) 0.0312(7) Uani 1 1 d . . . . .
H57 H 0.3072 1.0643 0.6568 0.037 Uiso 1 1 calc R U . . .
C58 C 0.6206(2) 0.5086(2) 0.4279(2) 0.0308(7) Uani 1 1 d . . . . .
C59 C 1.0258(2) 0.3340(2) 0.7227(2) 0.0309(7) Uani 1 1 d . . . . .
H59 H 1.0170 0.2674 0.7551 0.037 Uiso 1 1 calc R U . . .
C60 C 0.4413(2) 1.0668(2) 0.5972(2) 0.0304(7) Uani 1 1 d . . . . .
H60 H 0.4235 1.0906 0.5357 0.037 Uiso 1 1 calc R U . . .
C61 C 0.7358(2) 1.0124(2) 0.6431(2) 0.0308(7) Uani 1 1 d . . . . .
H61 H 0.8019 1.0007 0.6530 0.037 Uiso 1 1 calc R U . . .
C62 C 1.0674(2) 0.6304(2) 0.5767(2) 0.0333(8) Uani 1 1 d . . . . .
H62 H 1.0912 0.6576 0.5121 0.040 Uiso 1 1 calc R U . . .
C63 C 0.5095(2) 0.3717(2) 0.5250(2) 0.0318(8) Uani 1 1 d . . . . .
C64 C 0.4429(3) 0.9395(2) 0.9456(2) 0.0351(8) Uani 1 1 d . . . . .
H64 H 0.4581 0.9132 1.0081 0.042 Uiso 1 1 calc R U . . .
C65 C 1.0471(2) 0.6869(2) 0.6203(2) 0.0338(8) Uani 1 1 d . . . . .
H65 H 1.0572 0.7532 0.5862 0.041 Uiso 1 1 calc R U . . .
C66 C 0.6867(2) 0.9562(2) 0.8140(2) 0.0319(7) Uani 1 1 d . . . . .
H66 H 0.7522 0.9437 0.8259 0.038 Uiso 1 1 calc R U . . .
C67 C 0.6171(2) 0.9384(2) 0.8865(2) 0.0322(7) Uani 1 1 d . . . . .
H67 H 0.6346 0.9133 0.9481 0.039 Uiso 1 1 calc R U . . .
C68 C 0.5326(2) 0.4700(2) 0.4883(2) 0.0251(7) Uani 1 1 d . . . . .
C69 C 0.9419(2) 0.4093(2) 0.9108(2) 0.0327(8) Uani 1 1 d . . . . .
H69 H 0.9154 0.3819 0.9747 0.039 Uiso 1 1 calc R U . . .
C70 C 0.9639(2) 0.3528(2) 0.8676(2) 0.0308(7) Uani 1 1 d . . . . .
H70 H 0.9537 0.2865 0.9017 0.037 Uiso 1 1 calc R U . . .
C71 C 0.7106(2) 1.0476(2) 0.5533(2) 0.0339(8) Uani 1 1 d . . . . .
H71 H 0.7596 1.0597 0.5022 0.041 Uiso 1 1 calc R U . . .
C72 C 0.3483(3) 0.9601(2) 0.9294(2) 0.0367(8) Uani 1 1 d . . . . .
H72 H 0.2995 0.9490 0.9804 0.044 Uiso 1 1 calc R U . . .
C73 C 0.6154(2) 1.0655(2) 0.5371(2) 0.0324(8) Uani 1 1 d . . . . .
H73 H 0.5996 1.0894 0.4749 0.039 Uiso 1 1 calc R U . . .
C74 C 0.3240(2) 0.9967(2) 0.8395(2) 0.0330(8) Uani 1 1 d . . . . .
H74 H 0.2583 1.0104 0.8292 0.040 Uiso 1 1 calc R U . . .
C75 C 1.0614(2) 0.3737(3) 0.6289(2) 0.0373(8) Uani 1 1 d . . . . .
H75 H 1.0760 0.3342 0.5974 0.045 Uiso 1 1 calc R U . . .
C76 C 0.3587(2) 0.3916(2) 0.6071(2) 0.0356(8) Uani 1 1 d . . . . .
H76 H 0.2998 0.3647 0.6466 0.043 Uiso 1 1 calc R U . . .
C77 C 0.5431(2) 0.5198(3) 0.9693(2) 0.0370(8) Uani 1 1 d . . . . .
C78 C 0.9394(2) 0.5692(3) 0.9086(2) 0.0383(8) Uani 1 1 d . . . . .
H78 H 0.9148 0.5434 0.9731 0.046 Uiso 1 1 calc R U . . .
C79 C 0.4203(3) 0.3357(2) 0.5855(2) 0.0383(8) Uani 1 1 d . . . . .
H79 H 0.4044 0.2700 0.6111 0.046 Uiso 1 1 calc R U . . .
C80 C 0.9913(2) 0.7058(2) 0.7667(3) 0.0368(8) Uani 1 1 d . . . . .
H80 H 1.0020 0.7723 0.7349 0.044 Uiso 1 1 calc R U . . .
C81 C 1.0758(2) 0.4698(3) 0.5807(2) 0.0355(8) Uani 1 1 d . . . . .
H81 H 1.1009 0.4959 0.5163 0.043 Uiso 1 1 calc R U . . .
C82 C 0.5749(3) 0.3153(2) 0.5001(3) 0.0413(9) Uani 1 1 d . . . . .
H82 H 0.5608 0.2493 0.5245 0.050 Uiso 1 1 calc R U . . .
C83 C 0.9572(2) 0.6652(3) 0.8606(3) 0.0427(9) Uani 1 1 d . . . . .
H83 H 0.9456 0.7043 0.8930 0.051 Uiso 1 1 calc R U . . .
C84 C 0.6826(3) 0.4494(3) 0.4046(2) 0.0413(9) Uani 1 1 d . . . . .
H84 H 0.7411 0.4747 0.3638 0.050 Uiso 1 1 calc R U . . .
C85 C 0.6592(3) 0.3534(3) 0.4408(3) 0.0446(9) Uani 1 1 d . . . . .
H85 H 0.7019 0.3135 0.4245 0.053 Uiso 1 1 calc R U . . .
C86 C 0.4357(4) 0.6426(3) 1.0237(3) 0.0541(12) Uani 1 1 d . . . . .
H86 H 0.4006 0.6862 1.0413 0.065 Uiso 1 1 calc R U . . .
C87 C 0.6020(3) 0.4569(4) 0.9390(3) 0.0641(14) Uani 1 1 d . . . . .
C88 C 0.6636(3) 0.6473(4) 0.8737(3) 0.0698(15) Uani 1 1 d . . . . .
H88 H 0.6861 0.7114 0.8493 0.084 Uiso 1 1 calc R U . . .
C89 C 0.5755(4) 0.6137(3) 0.9362(3) 0.0616(13) Uani 1 1 d . . . . .
C90 C 0.5200(4) 0.6716(4) 0.9649(3) 0.0728(15) Uani 1 1 d . . . . .
H90 H 0.5416 0.7358 0.9423 0.087 Uiso 1 1 calc R U . . .
C91 C 0.6847(4) 0.4863(5) 0.8833(3) 0.0766(16) Uani 1 1 d . . . . .
H91 H 0.7230 0.4445 0.8657 0.092 Uiso 1 1 calc R U . . .
C92 C 0.7143(4) 0.5827(5) 0.8506(3) 0.0786(16) Uani 1 1 d . . . . .
H92 H 0.7735 0.6042 0.8099 0.094 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
O1 C18 1.361(3) . ?
O1 H1 0.8372 . ?
O2 C26 1.379(3) . ?
O2 H2 0.8493 . ?
O3 C25 1.373(3) . ?
O3 H3 0.8443 . ?
O4 C37 1.373(3) . ?
O4 H4 0.8508 . ?
N1 C16 1.373(3) . ?
N1 C2 1.372(3) . ?
N1 H5 0.8800 . ?
N2 C11 1.370(3) . ?
N2 C4 1.376(3) . ?
N2 H6 0.8800 . ?
N3 C8 1.379(3) . ?
N3 C1 1.383(3) . ?
N4 C3 1.367(3) . ?
N4 C10 1.379(3) . ?
C1 C7 1.405(4) . ?
C1 C29 1.430(4) . ?
C2 C7 1.407(4) . ?
C2 C19 1.427(4) . ?
C3 C9 1.413(4) . ?
C3 C38 1.445(4) . ?
C4 C17 1.399(4) . ?
C4 C27 1.432(4) . ?
C5 C31 1.393(4) . ?
C5 C32 1.402(4) . ?
C5 C9 1.501(4) . ?
C6 C43 1.394(4) . ?
C6 C21 1.398(4) . ?
C6 C17 1.496(4) . ?
C7 C12 1.495(4) . ?
C8 C17 1.406(4) . ?
C8 C13 1.437(4) . ?
C9 C16 1.405(4) . ?
C10 C30 1.393(4) . ?
C10 C42 1.437(4) . ?
C11 C30 1.408(4) . ?
C11 C36 1.425(4) . ?
C12 C49 1.389(4) . ?
C12 C47 1.391(4) . ?
C13 C29 1.357(4) . ?
C13 H13 0.9500 . ?
C14 C22 1.391(4) . ?
C14 C52 1.399(4) . ?
C14 C30 1.496(4) . ?
C15 C19 1.359(4) . ?
C15 C16 1.433(4) . ?
C15 H15 0.9500 . ?
C18 C23 1.397(4) . ?
C18 C24 1.396(4) . ?
C19 H19 0.9500 . ?
C20 C35 1.419(4) . ?
C20 C50 1.418(4) . ?
C20 C44 1.425(4) . ?
C21 C23 1.382(4) . ?
C21 H21 0.9500 . ?
C22 C28 1.385(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C43 1.389(4) . ?
C24 H24 0.9500 . ?
C25 C48 1.377(4) . ?
C25 C40 1.382(4) . ?
C26 C45 1.383(4) . ?
C26 C28 1.397(4) . ?
C27 C36 1.364(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C31 C48 1.394(4) . ?
C31 H31 0.9500 . ?
C32 C40 1.399(4) . ?
C32 H32 0.9500 . ?
C33 C53 1.413(4) . ?
C33 C54 1.418(4) . ?
C33 C41 1.429(4) . ?
C34 C37 1.376(4) . ?
C34 C49 1.391(4) . ?
C34 H34 0.9500 . ?
C35 C39 1.418(4) . ?
C35 C51 1.426(4) . ?
C36 H36 0.9500 . ?
C37 C46 1.387(4) . ?
C38 C42 1.348(4) . ?
C38 H38 0.9500 . ?
C39 C74 1.398(4) . ?
C39 C57 1.437(4) . ?
C40 H40 0.9500 . ?
C41 C59 1.397(4) . ?
C41 C70 1.435(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C73 1.389(4) . ?
C44 C60 1.447(4) . ?
C45 C52 1.389(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.391(4) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C61 1.399(4) . ?
C50 C66 1.435(4) . ?
C51 C64 1.387(4) . ?
C51 C67 1.443(4) . ?
C52 H52 0.9500 . ?
C53 C81 1.399(4) . ?
C53 C62 1.439(4) . ?
C54 C55 1.406(4) . ?
C54 C56 1.432(4) . ?
C55 C80 1.413(4) . ?
C55 C65 1.437(5) . ?
C56 C78 1.392(4) . ?
C56 C69 1.431(5) . ?
C57 C60 1.333(4) . ?
C57 H57 0.9500 . ?
C58 C84 1.391(5) . ?
C58 C68 1.423(4) . ?
C58 C76 1.438(5) 2_666 ?
C59 C75 1.382(5) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
C61 C71 1.382(5) . ?
C61 H61 0.9500 . ?
C62 C65 1.339(5) . ?
C62 H62 0.9500 . ?
C63 C82 1.398(5) . ?
C63 C68 1.420(4) . ?
C63 C79 1.432(5) . ?
C64 C72 1.375(5) . ?
C64 H64 0.9500 . ?
C65 H65 0.9500 . ?
C66 C67 1.345(4) . ?
C66 H66 0.9500 . ?
C67 H67 0.9500 . ?
C68 C68 1.426(6) 2_666 ?
C69 C70 1.339(4) . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C73 1.378(5) . ?
C71 H71 0.9500 . ?
C72 C74 1.380(5) . ?
C72 H72 0.9500 . ?
C73 H73 0.9500 . ?
C74 H74 0.9500 . ?
C75 C81 1.375(5) . ?
C75 H75 0.9500 . ?
C76 C79 1.335(5) . ?
C76 C58 1.438(5) 2_666 ?
C76 H76 0.9500 . ?
C77 C89 1.392(5) . ?
C77 C77 1.412(7) 2_667 ?
C77 C87 1.469(6) . ?
C78 C83 1.378(5) . ?
C78 H78 0.9500 . ?
C79 H79 0.9500 . ?
C80 C83 1.378(5) . ?
C80 H80 0.9500 . ?
C81 H81 0.9500 . ?
C82 C85 1.375(5) . ?
C82 H82 0.9500 . ?
C83 H83 0.9500 . ?
C84 C85 1.387(5) . ?
C84 H84 0.9500 . ?
C85 H85 0.9500 . ?
C86 C90 1.358(7) . ?
C86 C87 1.485(7) 2_667 ?
C86 H86 0.9500 . ?
C87 C91 1.320(6) . ?
C87 C86 1.485(6) 2_667 ?
C88 C92 1.373(7) . ?
C88 C89 1.430(6) . ?
C88 H88 0.9500 . ?
C89 C90 1.368(6) . ?
C90 H90 0.9500 . ?
C91 C92 1.418(7) . ?
C91 H91 0.9500 . ?
C92 H92 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 H1 110.7 . . ?
C26 O2 H2 101.6 . . ?
C25 O3 H3 103.4 . . ?
C37 O4 H4 111.7 . . ?
C16 N1 C2 109.4(2) . . ?
C16 N1 H5 125.3 . . ?
C2 N1 H5 125.3 . . ?
C11 N2 C4 109.0(2) . . ?
C11 N2 H6 125.5 . . ?
C4 N2 H6 125.5 . . ?
C8 N3 C1 107.5(2) . . ?
C3 N4 C10 106.9(2) . . ?
N3 C1 C7 127.0(2) . . ?
N3 C1 C29 108.5(2) . . ?
C7 C1 C29 124.3(2) . . ?
N1 C2 C7 127.0(2) . . ?
N1 C2 C19 107.1(2) . . ?
C7 C2 C19 125.8(2) . . ?
N4 C3 C9 127.4(2) . . ?
N4 C3 C38 109.4(2) . . ?
C9 C3 C38 122.7(2) . . ?
N2 C4 C17 125.8(2) . . ?
N2 C4 C27 107.5(2) . . ?
C17 C4 C27 126.7(2) . . ?
C31 C5 C32 117.2(2) . . ?
C31 C5 C9 119.5(2) . . ?
C32 C5 C9 123.2(2) . . ?
C43 C6 C21 117.4(2) . . ?
C43 C6 C17 120.4(2) . . ?
C21 C6 C17 122.2(2) . . ?
C1 C7 C2 125.9(2) . . ?
C1 C7 C12 116.4(2) . . ?
C2 C7 C12 117.5(2) . . ?
N3 C8 C17 126.5(2) . . ?
N3 C8 C13 108.6(2) . . ?
C17 C8 C13 124.8(2) . . ?
C16 C9 C3 123.8(2) . . ?
C16 C9 C5 119.8(2) . . ?
C3 C9 C5 116.3(2) . . ?
N4 C10 C30 126.8(2) . . ?
N4 C10 C42 109.0(2) . . ?
C30 C10 C42 124.2(2) . . ?
N2 C11 C30 126.2(2) . . ?
N2 C11 C36 108.0(2) . . ?
C30 C11 C36 125.8(2) . . ?
C49 C12 C47 117.8(2) . . ?
C49 C12 C7 122.0(2) . . ?
C47 C12 C7 120.2(2) . . ?
C29 C13 C8 107.4(2) . . ?
C29 C13 H13 126.3 . . ?
C8 C13 H13 126.3 . . ?
C22 C14 C52 118.2(2) . . ?
C22 C14 C30 122.1(2) . . ?
C52 C14 C30 119.7(2) . . ?
C19 C15 C16 107.4(2) . . ?
C19 C15 H15 126.3 . . ?
C16 C15 H15 126.3 . . ?
N1 C16 C9 125.6(2) . . ?
N1 C16 C15 107.5(2) . . ?
C9 C16 C15 126.9(2) . . ?
C4 C17 C8 124.5(2) . . ?
C4 C17 C6 117.9(2) . . ?
C8 C17 C6 117.5(2) . . ?
O1 C18 C23 122.6(2) . . ?
O1 C18 C24 119.1(2) . . ?
C23 C18 C24 118.3(2) . . ?
C15 C19 C2 108.4(2) . . ?
C15 C19 H19 125.8 . . ?
C2 C19 H19 125.8 . . ?
C35 C20 C50 120.7(3) . . ?
C35 C20 C44 119.9(3) . . ?
C50 C20 C44 119.4(3) . . ?
C23 C21 C6 121.7(2) . . ?
C23 C21 H21 119.1 . . ?
C6 C21 H21 119.1 . . ?
C28 C22 C14 121.1(3) . . ?
C28 C22 H22 119.5 . . ?
C14 C22 H22 119.5 . . ?
C21 C23 C18 120.5(2) . . ?
C21 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C43 C24 C18 120.5(3) . . ?
C43 C24 H24 119.7 . . ?
C18 C24 H24 119.7 . . ?
C48 C25 O3 122.6(3) . . ?
C48 C25 C40 119.5(3) . . ?
O3 C25 C40 117.8(2) . . ?
O2 C26 C45 121.4(3) . . ?
O2 C26 C28 118.5(2) . . ?
C45 C26 C28 120.1(2) . . ?
C36 C27 C4 107.7(2) . . ?
C36 C27 H27 126.2 . . ?
C4 C27 H27 126.2 . . ?
C22 C28 C26 119.8(3) . . ?
C22 C28 H28 120.1 . . ?
C26 C28 H28 120.1 . . ?
C13 C29 C1 107.9(2) . . ?
C13 C29 H29 126.0 . . ?
C1 C29 H29 126.0 . . ?
C10 C30 C11 126.0(2) . . ?
C10 C30 C14 118.2(2) . . ?
C11 C30 C14 115.7(2) . . ?
C5 C31 C48 121.9(3) . . ?
C5 C31 H31 119.0 . . ?
C48 C31 H31 119.0 . . ?
C40 C32 C5 120.8(3) . . ?
C40 C32 H32 119.6 . . ?
C5 C32 H32 119.6 . . ?
C53 C33 C54 119.7(3) . . ?
C53 C33 C41 119.5(3) . . ?
C54 C33 C41 120.8(3) . . ?
C37 C34 C49 119.5(3) . . ?
C37 C34 H34 120.3 . . ?
C49 C34 H34 120.3 . . ?
C20 C35 C39 120.6(3) . . ?
C20 C35 C51 120.0(3) . . ?
C39 C35 C51 119.4(3) . . ?
C27 C36 C11 107.8(2) . . ?
C27 C36 H36 126.1 . . ?
C11 C36 H36 126.1 . . ?
C34 C37 O4 123.2(3) . . ?
C34 C37 C46 120.4(3) . . ?
O4 C37 C46 116.4(3) . . ?
C42 C38 C3 106.9(2) . . ?
C42 C38 H38 126.5 . . ?
C3 C38 H38 126.5 . . ?
C74 C39 C35 119.1(3) . . ?
C74 C39 C57 122.7(3) . . ?
C35 C39 C57 118.2(3) . . ?
C25 C40 C32 120.5(3) . . ?
C25 C40 H40 119.8 . . ?
C32 C40 H40 119.8 . . ?
C59 C41 C33 118.8(3) . . ?
C59 C41 C70 123.1(3) . . ?
C33 C41 C70 118.1(3) . . ?
C38 C42 C10 107.7(2) . . ?
C38 C42 H42 126.1 . . ?
C10 C42 H42 126.1 . . ?
C24 C43 C6 121.5(2) . . ?
C24 C43 H43 119.2 . . ?
C6 C43 H43 119.2 . . ?
C73 C44 C20 119.2(3) . . ?
C73 C44 C60 123.1(3) . . ?
C20 C44 C60 117.7(3) . . ?
C26 C45 C52 119.5(3) . . ?
C26 C45 H45 120.2 . . ?
C52 C45 H45 120.2 . . ?
C37 C46 C47 119.4(3) . . ?
C37 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C12 C47 C46 121.3(3) . . ?
C12 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C25 C48 C31 120.0(3) . . ?
C25 C48 H48 120.0 . . ?
C31 C48 H48 120.0 . . ?
C12 C49 C34 121.6(3) . . ?
C12 C49 H49 119.2 . . ?
C34 C49 H49 119.2 . . ?
C61 C50 C20 119.3(3) . . ?
C61 C50 C66 122.7(3) . . ?
C20 C50 C66 118.0(3) . . ?
C64 C51 C35 118.8(3) . . ?
C64 C51 C67 123.3(3) . . ?
C35 C51 C67 117.9(3) . . ?
C45 C52 C14 121.3(3) . . ?
C45 C52 H52 119.4 . . ?
C14 C52 H52 119.4 . . ?
C81 C53 C33 119.3(3) . . ?
C81 C53 C62 122.2(3) . . ?
C33 C53 C62 118.4(3) . . ?
C55 C54 C33 120.4(3) . . ?
C55 C54 C56 120.5(3) . . ?
C33 C54 C56 119.1(3) . . ?
C54 C55 C80 118.8(3) . . ?
C54 C55 C65 118.8(3) . . ?
C80 C55 C65 122.3(3) . . ?
C78 C56 C69 123.1(3) . . ?
C78 C56 C54 118.4(3) . . ?
C69 C56 C54 118.5(3) . . ?
C60 C57 C39 121.5(3) . . ?
C60 C57 H57 119.2 . . ?
C39 C57 H57 119.2 . . ?
C84 C58 C68 119.5(3) . . ?
C84 C58 C76 122.6(3) . 2_666 ?
C68 C58 C76 117.9(3) . 2_666 ?
C75 C59 C41 120.9(3) . . ?
C75 C59 H59 119.6 . . ?
C41 C59 H59 119.6 . . ?
C57 C60 C44 122.0(3) . . ?
C57 C60 H60 119.0 . . ?
C44 C60 H60 119.0 . . ?
C71 C61 C50 120.4(3) . . ?
C71 C61 H61 119.8 . . ?
C50 C61 H61 119.8 . . ?
C65 C62 C53 121.8(3) . . ?
C65 C62 H62 119.1 . . ?
C53 C62 H62 119.1 . . ?
C82 C63 C68 118.3(3) . . ?
C82 C63 C79 123.6(3) . . ?
C68 C63 C79 118.1(3) . . ?
C72 C64 C51 121.5(3) . . ?
C72 C64 H64 119.3 . . ?
C51 C64 H64 119.3 . . ?
C62 C65 C55 120.8(3) . . ?
C62 C65 H65 119.6 . . ?
C55 C65 H65 119.6 . . ?
C67 C66 C50 121.8(3) . . ?
C67 C66 H66 119.1 . . ?
C50 C66 H66 119.1 . . ?
C66 C67 C51 121.6(3) . . ?
C66 C67 H67 119.2 . . ?
C51 C67 H67 119.2 . . ?
C58 C68 C63 119.8(3) . . ?
C58 C68 C68 120.2(3) . 2_666 ?
C63 C68 C68 120.0(4) . 2_666 ?
C70 C69 C56 122.2(3) . . ?
C70 C69 H69 118.9 . . ?
C56 C69 H69 118.9 . . ?
C69 C70 C41 121.3(3) . . ?
C69 C70 H70 119.4 . . ?
C41 C70 H70 119.4 . . ?
C73 C71 C61 120.9(3) . . ?
C73 C71 H71 119.5 . . ?
C61 C71 H71 119.5 . . ?
C64 C72 C74 120.4(3) . . ?
C64 C72 H72 119.8 . . ?
C74 C72 H72 119.8 . . ?
C71 C73 C44 120.9(3) . . ?
C71 C73 H73 119.6 . . ?
C44 C73 H73 119.6 . . ?
C72 C74 C39 120.8(3) . . ?
C72 C74 H74 119.6 . . ?
C39 C74 H74 119.6 . . ?
C81 C75 C59 120.7(3) . . ?
C81 C75 H75 119.6 . . ?
C59 C75 H75 119.6 . . ?
C79 C76 C58 121.6(3) . 2_666 ?
C79 C76 H76 119.2 . . ?
C58 C76 H76 119.2 2_666 . ?
C89 C77 C77 124.4(5) . 2_667 ?
C89 C77 C87 118.3(4) . . ?
C77 C77 C87 117.3(4) 2_667 . ?
C83 C78 C56 120.8(3) . . ?
C83 C78 H78 119.6 . . ?
C56 C78 H78 119.6 . . ?
C76 C79 C63 122.2(3) . . ?
C76 C79 H79 118.9 . . ?
C63 C79 H79 118.9 . . ?
C83 C80 C55 119.9(3) . . ?
C83 C80 H80 120.1 . . ?
C55 C80 H80 120.1 . . ?
C75 C81 C53 120.8(3) . . ?
C75 C81 H81 119.6 . . ?
C53 C81 H81 119.6 . . ?
C85 C82 C63 121.4(3) . . ?
C85 C82 H82 119.3 . . ?
C63 C82 H82 119.3 . . ?
C80 C83 C78 121.6(3) . . ?
C80 C83 H83 119.2 . . ?
C78 C83 H83 119.2 . . ?
C85 C84 C58 120.1(3) . . ?
C85 C84 H84 119.9 . . ?
C58 C84 H84 119.9 . . ?
C82 C85 C84 120.9(3) . . ?
C82 C85 H85 119.6 . . ?
C84 C85 H85 119.6 . . ?
C90 C86 C87 120.5(4) . 2_667 ?
C90 C86 H86 119.7 . . ?
C87 C86 H86 119.7 2_667 . ?
C91 C87 C77 122.1(5) . . ?
C91 C87 C86 121.6(5) . 2_667 ?
C77 C87 C86 116.3(4) . 2_667 ?
C92 C88 C89 117.1(5) . . ?
C92 C88 H88 121.4 . . ?
C89 C88 H88 121.4 . . ?
C90 C89 C77 117.8(5) . . ?
C90 C89 C88 122.0(5) . . ?
C77 C89 C88 120.2(5) . . ?
C86 C90 C89 123.8(5) . . ?
C86 C90 H90 118.1 . . ?
C89 C90 H90 118.1 . . ?
C87 C91 C92 117.6(5) . . ?
C87 C91 H91 121.2 . . ?
C92 C91 H91 121.2 . . ?
C88 C92 C91 124.6(5) . . ?
C88 C92 H92 117.7 . . ?
C91 C92 H92 117.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.94 2.780(3) 180 2_657
O2 H2 O3 0.85 2.15 2.904(2) 147 2_766
O3 H3 O4 0.84 2.40 3.249(3) 180 2_676
O4 H4 O1 0.85 2.01 2.784(3) 150 2_567

# start Validation Reply Form
_vrf_PLAT417_sn31                
;
PROBLEM:
RESPONSE:
The positions of the hydroxylic H-atoms OH(1), OH(2), OH(3) and OH(4) couldn't
be determined reliably.
;
_vrf_PLAT250_sn31                
;
PROBLEM:
RESPONSE:
One of the pyrene moieties reveals partial rotational disorder, which is
associated with wide-amplitude ADPs of its peripheral atoms.
;
# end Validation Reply Form

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.059

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

data_sn26
_database_code_depnum_ccdc_archive 'CCDC 1455568'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4, 2(C16 H10), 2(C5 H5 N)'
_chemical_formula_sum            'C43 H30 N3 O2'
_chemical_formula_weight         620.70

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/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                   13.5292(5)
_cell_length_b                   20.5192(6)
_cell_length_c                   11.5369(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.6570(10)
_cell_angle_gamma                90
_cell_volume                     3051.86(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4456
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      25.07

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            21293
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.580
_diffrn_reflns_theta_max         25.070
_diffrn_reflns_theta_full        25.070
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5387
_reflns_number_gt                4456
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0509P)²+1.8102P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5387
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.93245(9) 0.81128(6) 0.94843(12) 0.0277(3) Uani 1 1 d . . . . .
H1 H 0.9008 0.8450 0.9614 0.042 Uiso 1 1 d R U . . .
O2 O 0.86456(10) 0.19614(6) 1.03755(11) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.9255 0.1943 1.0337 0.039 Uiso 1 1 calc R U . . .
N1 N 0.51318(10) 0.59753(6) 0.48721(12) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.62334(11) 0.50036(6) 0.66244(12) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.5723 0.4997 0.5930 0.020 Uiso 1 1 d R U . . .
N3 N 0.84920(12) 0.92200(7) 0.99019(14) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.45523(13) 0.63756(8) 0.39696(15) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.66143(13) 0.44614(8) 0.73068(15) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.67707(13) 0.55480(8) 0.71582(15) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.80855(13) 0.23945(8) 0.95339(15) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.66050(13) 0.61881(8) 0.67202(15) 0.0176(4) Uani 1 1 d . . . . .
C6 C 0.62744(12) 0.38168(8) 0.70393(15) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.58343(13) 0.63774(8) 0.56520(15) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.56968(13) 0.70463(8) 0.52212(16) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.6093 0.7413 0.5598 0.024 Uiso 1 1 calc R U . . .
C9 C 0.73154(13) 0.67014(8) 0.74504(15) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.78939(13) 0.31639(8) 0.79122(15) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.8180 0.3383 0.7363 0.023 Uiso 1 1 calc R U . . .
C11 C 0.74191(13) 0.46787(8) 0.83487(15) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.7819 0.4412 0.8994 0.024 Uiso 1 1 calc R U . . .
C12 C 0.68825(13) 0.33063(8) 0.78946(15) 0.0171(4) Uani 1 1 d . . . . .
C13 C 0.75138(13) 0.53365(8) 0.82570(15) 0.0204(4) Uani 1 1 d . . . . .
H13 H 0.7992 0.5607 0.8827 0.024 Uiso 1 1 calc R U . . .
C14 C 0.84930(13) 0.27090(8) 0.87149(15) 0.0193(4) Uani 1 1 d . . . . .
H14 H 0.9177 0.2614 0.8704 0.023 Uiso 1 1 calc R U . . .
C15 C 0.86495(13) 0.76604(8) 0.88171(16) 0.0203(4) Uani 1 1 d . . . . .
C16 C 0.49010(13) 0.70455(8) 0.41888(16) 0.0199(4) Uani 1 1 d . . . . .
H16 H 0.4620 0.7412 0.3697 0.024 Uiso 1 1 calc R U . . .
C17 C 0.70706(14) 0.25186(8) 0.95082(16) 0.0219(4) Uani 1 1 d . . . . .
H17 H 0.6782 0.2294 1.0049 0.026 Uiso 1 1 calc R U . . .
C18 C 0.76124(14) 0.76486(8) 0.87649(16) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.7352 0.7965 0.9199 0.027 Uiso 1 1 calc R U . . .
C19 C 0.69553(14) 0.71781(8) 0.80825(16) 0.0226(4) Uani 1 1 d . . . . .
H19 H 0.6244 0.7180 0.8045 0.027 Uiso 1 1 calc R U . . .
C20 C 0.64779(13) 0.29686(8) 0.86987(16) 0.0209(4) Uani 1 1 d . . . . .
H20 H 0.5784 0.3049 0.8690 0.025 Uiso 1 1 calc R U . . .
C21 C 0.83586(13) 0.67174(8) 0.75143(16) 0.0230(4) Uani 1 1 d . . . . .
H21 H 0.8623 0.6398 0.7090 0.028 Uiso 1 1 calc R U . . .
C22 C 0.90213(14) 0.71915(8) 0.81867(17) 0.0247(4) Uani 1 1 d . . . . .
H22 H 0.9730 0.7195 0.8215 0.030 Uiso 1 1 calc R U . . .
C23 C 0.71067(14) 1.02396(9) 0.64862(15) 0.0230(4) Uani 1 1 d . . . . .
C24 C 0.78659(15) 0.97885(9) 0.63526(16) 0.0265(4) Uani 1 1 d . . . . .
C25 C 0.73640(15) 1.09127(9) 0.66612(16) 0.0244(4) Uani 1 1 d . . . . .
C26 C 0.83653(15) 1.11197(10) 0.66381(17) 0.0302(5) Uani 1 1 d . . . . .
H26 H 0.8539 1.1569 0.6739 0.036 Uiso 1 1 calc R U . . .
C27 C 0.71778(16) 1.00393(9) 0.94402(18) 0.0310(5) Uani 1 1 d . . . . .
H27 H 0.6479 1.0156 0.9034 0.037 Uiso 1 1 calc R U . . .
C28 C 0.61020(16) 1.00296(10) 0.64625(18) 0.0339(5) Uani 1 1 d . . . . .
C29 C 0.88521(15) 1.00133(10) 0.63470(17) 0.0319(5) Uani 1 1 d . . . . .
C30 C 0.75234(16) 0.94181(9) 0.93457(18) 0.0297(4) Uani 1 1 d . . . . .
H30 H 0.7048 0.9113 0.8859 0.036 Uiso 1 1 calc R U . . .
C31 C 0.90648(15) 1.06975(11) 0.64777(18) 0.0357(5) Uani 1 1 d . . . . .
H31 H 0.9718 1.0855 0.6450 0.043 Uiso 1 1 calc R U . . .
C32 C 0.91425(16) 0.96599(9) 1.05913(17) 0.0315(5) Uani 1 1 d . . . . .
H32 H 0.9832 0.9528 1.1009 0.038 Uiso 1 1 calc R U . . .
C33 C 0.66366(17) 1.13466(10) 0.68580(18) 0.0336(5) Uani 1 1 d . . . . .
H33 H 0.6812 1.1794 0.7005 0.040 Uiso 1 1 calc R U . . .
C34 C 0.88576(19) 1.02964(10) 1.07230(19) 0.0391(5) Uani 1 1 d . . . . .
H34 H 0.9343 1.0595 1.1214 0.047 Uiso 1 1 calc R U . . .
C35 C 0.78556(18) 1.04890(10) 1.01291(19) 0.0362(5) Uani 1 1 d . . . . .
H35 H 0.7639 1.0924 1.0196 0.043 Uiso 1 1 calc R U . . .
C36 C 0.7609(2) 0.91128(10) 0.62186(18) 0.0412(6) Uani 1 1 d . . . . .
C37 C 0.56725(18) 1.11343(11) 0.6842(2) 0.0425(6) Uani 1 1 d . . . . .
H37 H 0.5190 1.1437 0.6980 0.051 Uiso 1 1 calc R U . . .
C38 C 0.6567(2) 0.89228(11) 0.6203(2) 0.0513(7) Uani 1 1 d . . . . .
H38 H 0.6382 0.8475 0.6117 0.062 Uiso 1 1 calc R U . . .
C39 C 0.53912(17) 1.04953(12) 0.6630(2) 0.0427(6) Uani 1 1 d . . . . .
H39 H 0.4710 1.0363 0.6595 0.051 Uiso 1 1 calc R U . . .
C40 C 0.5868(2) 0.93544(12) 0.6305(2) 0.0484(6) Uani 1 1 d . . . . .
H40 H 0.5193 0.9208 0.6272 0.058 Uiso 1 1 calc R U . . .
C41 C 0.95730(19) 0.95509(14) 0.6200(2) 0.0554(7) Uani 1 1 d . . . . .
H41 H 1.0239 0.9688 0.6182 0.067 Uiso 1 1 calc R U . . .
C42 C 0.8350(3) 0.86807(12) 0.6090(2) 0.0605(8) Uani 1 1 d . . . . .
H42 H 0.8192 0.8229 0.6006 0.073 Uiso 1 1 calc R U . . .
C43 C 0.9308(3) 0.88899(15) 0.6080(2) 0.0681(10) Uani 1 1 d . . . . .
H43 H 0.9802 0.8581 0.5990 0.082 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
O1 C15 1.364(2) . ?
O1 H1 0.8508 . ?
O2 C4 1.364(2) . ?
O2 H2 0.8400 . ?
N1 C7 1.369(2) . ?
N1 C1 1.370(2) . ?
N2 C2 1.370(2) . ?
N2 C3 1.373(2) . ?
N2 H3 0.8855 . ?
N3 C30 1.336(2) . ?
N3 C32 1.341(2) . ?
C1 C6 1.404(2) 3_666 ?
C1 C16 1.450(2) . ?
C2 C6 1.404(2) . ?
C2 C11 1.427(2) . ?
C3 C5 1.401(2) . ?
C3 C13 1.426(2) . ?
C4 C17 1.388(2) . ?
C4 C14 1.389(2) . ?
C5 C7 1.406(2) . ?
C5 C9 1.501(2) . ?
C6 C1 1.404(2) 3_666 ?
C6 C12 1.502(2) . ?
C7 C8 1.452(2) . ?
C8 C16 1.342(2) . ?
C8 H8 0.9500 . ?
C9 C21 1.391(2) . ?
C9 C19 1.393(2) . ?
C10 C14 1.389(2) . ?
C10 C12 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C13 1.363(2) . ?
C11 H11 0.9500 . ?
C12 C20 1.396(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C18 1.386(2) . ?
C15 C22 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C20 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.418(3) . ?
C23 C25 1.424(3) . ?
C23 C24 1.425(3) . ?
C24 C29 1.413(3) . ?
C24 C36 1.426(3) . ?
C25 C33 1.396(3) . ?
C25 C26 1.428(3) . ?
C26 C31 1.337(3) . ?
C26 H26 0.9500 . ?
C27 C35 1.372(3) . ?
C27 C30 1.373(3) . ?
C27 H27 0.9500 . ?
C28 C39 1.410(3) . ?
C28 C40 1.421(3) . ?
C29 C41 1.407(3) . ?
C29 C31 1.432(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C34 1.383(3) . ?
C32 H32 0.9500 . ?
C33 C37 1.370(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C42 1.380(3) . ?
C36 C38 1.458(4) . ?
C37 C39 1.367(3) . ?
C37 H37 0.9500 . ?
C38 C40 1.327(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C43 1.399(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.369(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 H1 111.5 . . ?
C4 O2 H2 109.5 . . ?
C7 N1 C1 105.15(13) . . ?
C2 N2 C3 110.33(14) . . ?
C2 N2 H3 124.2 . . ?
C3 N2 H3 125.5 . . ?
C30 N3 C32 116.87(17) . . ?
N1 C1 C6 126.12(15) . 3_666 ?
N1 C1 C16 110.78(14) . . ?
C6 C1 C16 123.10(15) 3_666 . ?
N2 C2 C6 126.72(15) . . ?
N2 C2 C11 106.76(14) . . ?
C6 C2 C11 126.52(15) . . ?
N2 C3 C5 126.60(15) . . ?
N2 C3 C13 106.60(14) . . ?
C5 C3 C13 126.79(15) . . ?
O2 C4 C17 117.85(15) . . ?
O2 C4 C14 122.52(15) . . ?
C17 C4 C14 119.63(15) . . ?
C3 C5 C7 124.77(15) . . ?
C3 C5 C9 116.77(15) . . ?
C7 C5 C9 118.46(14) . . ?
C2 C6 C1 124.93(15) . 3_666 ?
C2 C6 C12 115.80(14) . . ?
C1 C6 C12 119.23(14) 3_666 . ?
N1 C7 C5 126.29(15) . . ?
N1 C7 C8 110.69(14) . . ?
C5 C7 C8 123.01(15) . . ?
C16 C8 C7 106.72(15) . . ?
C16 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
C21 C9 C19 117.77(15) . . ?
C21 C9 C5 120.87(15) . . ?
C19 C9 C5 121.36(15) . . ?
C14 C10 C12 121.49(16) . . ?
C14 C10 H10 119.3 . . ?
C12 C10 H10 119.3 . . ?
C13 C11 C2 108.04(15) . . ?
C13 C11 H11 126.0 . . ?
C2 C11 H11 126.0 . . ?
C10 C12 C20 117.88(15) . . ?
C10 C12 C6 119.71(15) . . ?
C20 C12 C6 122.40(15) . . ?
C11 C13 C3 108.24(15) . . ?
C11 C13 H13 125.9 . . ?
C3 C13 H13 125.9 . . ?
C4 C14 C10 119.59(16) . . ?
C4 C14 H14 120.2 . . ?
C10 C14 H14 120.2 . . ?
O1 C15 C18 122.12(15) . . ?
O1 C15 C22 118.68(15) . . ?
C18 C15 C22 119.19(16) . . ?
C8 C16 C1 106.67(15) . . ?
C8 C16 H16 126.7 . . ?
C1 C16 H16 126.7 . . ?
C20 C17 C4 120.27(16) . . ?
C20 C17 H17 119.9 . . ?
C4 C17 H17 119.9 . . ?
C19 C18 C15 120.24(16) . . ?
C19 C18 H18 119.9 . . ?
C15 C18 H18 119.9 . . ?
C18 C19 C9 121.39(16) . . ?
C18 C19 H19 119.3 . . ?
C9 C19 H19 119.3 . . ?
C17 C20 C12 121.08(16) . . ?
C17 C20 H20 119.5 . . ?
C12 C20 H20 119.5 . . ?
C22 C21 C9 121.25(16) . . ?
C22 C21 H21 119.4 . . ?
C9 C21 H21 119.4 . . ?
C15 C22 C21 120.16(16) . . ?
C15 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C28 C23 C25 119.28(17) . . ?
C28 C23 C24 121.24(18) . . ?
C25 C23 C24 119.48(17) . . ?
C29 C24 C23 120.05(17) . . ?
C29 C24 C36 121.06(19) . . ?
C23 C24 C36 118.89(19) . . ?
C33 C25 C23 119.19(18) . . ?
C33 C25 C26 122.22(18) . . ?
C23 C25 C26 118.59(17) . . ?
C31 C26 C25 121.70(18) . . ?
C31 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C35 C27 C30 119.1(2) . . ?
C35 C27 H27 120.4 . . ?
C30 C27 H27 120.4 . . ?
C39 C28 C23 118.76(19) . . ?
C39 C28 C40 122.9(2) . . ?
C23 C28 C40 118.3(2) . . ?
C41 C29 C24 118.0(2) . . ?
C41 C29 C31 123.3(2) . . ?
C24 C29 C31 118.64(17) . . ?
N3 C30 C27 123.52(19) . . ?
N3 C30 H30 118.2 . . ?
C27 C30 H30 118.2 . . ?
C26 C31 C29 121.46(19) . . ?
C26 C31 H31 119.3 . . ?
C29 C31 H31 119.3 . . ?
N3 C32 C34 123.1(2) . . ?
N3 C32 H32 118.4 . . ?
C34 C32 H32 118.4 . . ?
C37 C33 C25 120.69(19) . . ?
C37 C33 H33 119.7 . . ?
C25 C33 H33 119.7 . . ?
C35 C34 C32 118.75(19) . . ?
C35 C34 H34 120.6 . . ?
C32 C34 H34 120.6 . . ?
C27 C35 C34 118.62(19) . . ?
C27 C35 H35 120.7 . . ?
C34 C35 H35 120.7 . . ?
C42 C36 C24 118.4(3) . . ?
C42 C36 C38 124.0(2) . . ?
C24 C36 C38 117.7(2) . . ?
C39 C37 C33 121.3(2) . . ?
C39 C37 H37 119.3 . . ?
C33 C37 H37 119.3 . . ?
C40 C38 C36 122.2(2) . . ?
C40 C38 H38 118.9 . . ?
C36 C38 H38 118.9 . . ?
C37 C39 C28 120.7(2) . . ?
C37 C39 H39 119.7 . . ?
C28 C39 H39 119.7 . . ?
C38 C40 C28 121.7(2) . . ?
C38 C40 H40 119.2 . . ?
C28 C40 H40 119.2 . . ?
C43 C41 C29 120.0(3) . . ?
C43 C41 H41 120.0 . . ?
C29 C41 H41 120.0 . . ?
C43 C42 C36 121.3(3) . . ?
C43 C42 H42 119.3 . . ?
C36 C42 H42 119.3 . . ?
C42 C43 C41 121.2(2) . . ?
C42 C43 H43 119.4 . . ?
C41 C43 H43 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.85 1.80 2.6441(19) 173 .
O2 H2 O1 0.84 1.87 2.7059(18) 171 3_767

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.045

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

data_sn29
_database_code_depnum_ccdc_archive 'CCDC 1455569'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4, 2(C20 H12), 2(C5 H5 N)'
_chemical_formula_sum            'C94 H64 N6 O4'
_chemical_formula_weight         1341.51

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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.4400(7)
_cell_length_b                   20.5920(12)
_cell_length_c                   14.7450(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.377(3)
_cell_angle_gamma                90
_cell_volume                     3256.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3226
_cell_measurement_theta_min      1.47
_cell_measurement_theta_max      28.33

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            16102
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.473
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4143
_reflns_number_gt                3226
_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.

 The pyridine moiety is located on and disordered about the
 symmetry axis of twofold rotation.
 The -OH group exhibits a disordered H-bond to the -OH group of an adjacent
 porphyrin and to the pyridine heterocycle.
;

_computing_data_collection       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0575P)²+3.6996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4143
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.007
_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
O1 O 0.40558(14) 0.31063(5) 0.40995(8) 0.0396(3) Uani 1 1 d . . . . .
H1 H 0.4687 0.3107 0.4607 0.047 Uiso 0.5 1 d R U P . .
H1A H 0.3791 0.3472 0.3859 0.047 Uiso 0.5 1 d R U P . .
N1 N 0.5000 0.09819(7) 0.0000 0.0172(3) Uani 1 2 d S T P . .
N2 N 0.46612(15) 0.0000 0.13019(12) 0.0159(3) Uani 1 2 d S T P . .
H2 H 0.4764 0.0000 0.0730 0.019 Uiso 1 2 d R U P . .
C1 C 0.52788(15) 0.22836(7) 0.37184(10) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.5932 0.2354 0.4319 0.028 Uiso 1 1 calc R U . . .
C2 C 0.46170(13) 0.11907(6) 0.15217(10) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.45304(12) 0.05464(6) 0.17920(10) 0.0156(3) Uani 1 1 d . . . . .
C4 C 0.49035(15) 0.20628(7) 0.04261(11) 0.0232(3) Uani 1 1 d . . . . .
H4 H 0.4829 0.2432 0.0788 0.028 Uiso 1 1 calc R U . . .
C5 C 0.48319(13) 0.13852(6) 0.06818(10) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.34027(14) 0.20908(7) 0.19479(11) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.2761 0.2031 0.1339 0.027 Uiso 1 1 calc R U . . .
C7 C 0.54024(14) 0.18070(7) 0.30883(10) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.6134 0.1547 0.3271 0.024 Uiso 1 1 calc R U . . .
C8 C 0.42008(16) 0.26564(7) 0.34704(11) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.44696(13) 0.17047(6) 0.21945(10) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.42623(13) 0.03324(6) 0.26206(10) 0.0167(3) Uani 1 1 d . . . . .
H10 H 0.4111 0.0604 0.3089 0.020 Uiso 1 1 calc R U . . .
C11 C 0.32616(15) 0.25619(7) 0.25771(11) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.2526 0.2819 0.2399 0.032 Uiso 1 1 calc R U . . .
C12 C 0.13512(13) 0.06043(7) 0.29223(11) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.2815(2) 0.0000 0.42945(15) 0.0265(5) Uani 1 2 d S T P . .
C14 C 0.18297(18) 0.0000 0.33758(14) 0.0184(4) Uani 1 2 d S T P . .
C15 C 0.03610(14) 0.06028(7) 0.19676(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.32910(17) 0.05997(10) 0.47341(12) 0.0362(4) Uani 1 1 d . . . . .
H16 H 0.3947 0.0604 0.5344 0.043 Uiso 1 1 calc R U . . .
C17 C -0.0091(2) 0.0000 0.15027(16) 0.0229(4) Uani 1 2 d S T P . .
C18 C 0.28225(18) 0.11683(9) 0.42951(13) 0.0377(4) Uani 1 1 d . . . . .
H18 H 0.3154 0.1567 0.4600 0.045 Uiso 1 1 calc R U . . .
C19 C 0.18548(16) 0.11736(8) 0.33973(13) 0.0294(4) Uani 1 1 d . . . . .
H19 H 0.1535 0.1578 0.3106 0.035 Uiso 1 1 calc R U . . .
C20 C -0.1047(2) 0.0000 0.05734(18) 0.0336(5) Uani 1 2 d S T P . .
C21 C -0.01728(18) 0.11731(9) 0.15154(16) 0.0452(5) Uani 1 1 d . . . . .
H21 H 0.0103 0.1577 0.1830 0.054 Uiso 1 1 calc R U . . .
C22 C -0.15293(19) -0.05996(11) 0.01346(15) 0.0490(6) Uani 1 1 d . . . . .
H22 H -0.2150 -0.0605 -0.0493 0.059 Uiso 1 1 calc R U . . .
C23 C -0.1114(2) 0.11659(11) 0.06002(18) 0.0613(7) Uani 1 1 d . . . . .
H23 H -0.1465 0.1564 0.0304 0.074 Uiso 1 1 calc R U . . .
N3 N 0.3244(3) 0.42254(15) 0.3362(2) 0.0238(6) Uani 0.5 1 d . . P . .
C24 C 0.35291(19) 0.46736(8) 0.39508(17) 0.0431(5) Uani 1 1 d . . . . .
H24 H 0.3842 0.4510 0.4593 0.052 Uiso 1 1 d R U . . .
C25 C 0.2536(2) 0.5000 0.2171(2) 0.0446(7) Uani 1 2 d S T P . .
H25 H 0.2108 0.5000 0.1491 0.053 Uiso 1 2 d R U P . .
C26 C 0.2703(5) 0.4439(3) 0.2434(4) 0.0347(13) Uani 0.5 1 d . . P . .
H26 H 0.2429 0.4115 0.1947 0.042 Uiso 0.5 1 d R U P . .
C27 C 0.2931(5) 0.4453(2) 0.2901(5) 0.0392(13) Uani 0.5 1 d . . P . .
H27 H 0.2817 0.4008 0.2723 0.047 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3613(17) . ?
O1 H1 0.8400 . ?
O1 H1A 0.8426 . ?
N1 C5 1.3683(16) . ?
N1 C5 1.3684(16) 2_655 ?
N2 C3 1.3732(15) 6 ?
N2 C3 1.3733(15) . ?
N2 H2 0.8904 . ?
C1 C8 1.389(2) . ?
C1 C7 1.392(2) . ?
C1 H3 0.9500 . ?
C2 C3 1.3988(18) . ?
C2 C5 1.4023(18) . ?
C2 C9 1.4997(18) . ?
C3 C10 1.4289(18) . ?
C4 C4 1.349(3) 2_655 ?
C4 C5 1.4550(18) . ?
C4 H4 0.9500 . ?
C6 C11 1.390(2) . ?
C6 C9 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C9 1.393(2) . ?
C7 H7 0.9500 . ?
C8 C11 1.393(2) . ?
C10 C10 1.369(3) 6 ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C19 1.384(2) . ?
C12 C14 1.4283(17) . ?
C12 C15 1.468(2) . ?
C13 C16 1.413(2) . ?
C13 C16 1.413(2) 6 ?
C13 C14 1.429(3) . ?
C14 C12 1.4283(17) 6 ?
C15 C21 1.383(2) . ?
C15 C17 1.4254(18) . ?
C16 C18 1.355(3) . ?
C16 H16 0.9500 . ?
C17 C20 1.425(3) . ?
C17 C15 1.4254(18) 6 ?
C18 C19 1.399(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C22 1.414(2) . ?
C20 C22 1.414(2) 6 ?
C21 C23 1.403(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.353(3) 6 ?
C22 H22 0.9500 . ?
C23 C22 1.353(3) 6 ?
C23 H23 0.9500 . ?
N3 C27 0.800(6) . ?
N3 C24 1.231(3) . ?
N3 C26 1.363(5) . ?
N3 H27 1.0035 . ?
C24 C24 1.344(3) 6_565 ?
C24 C27 1.527(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.213(6) 6_565 ?
C25 C26 1.213(6) . ?
C25 C27 1.515(6) 6_565 ?
C25 C27 1.515(6) . ?
C25 H25 0.9500 . ?
C26 C27 0.646(6) . ?
C26 H26 0.9500 . ?
C26 H27 0.9736 . ?
C27 H26 1.4939 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.8 . . ?
C8 O1 H1A 115.6 . . ?
H1 O1 H1A 116.4 . . ?
C5 N1 C5 105.25(15) . 2_655 ?
C3 N2 C3 110.03(15) 6 . ?
C3 N2 H2 124.9 6 . ?
C3 N2 H2 124.9 . . ?
C8 C1 C7 120.08(14) . . ?
C8 C1 H3 120.0 . . ?
C7 C1 H3 120.0 . . ?
C3 C2 C5 125.04(12) . . ?
C3 C2 C9 116.45(12) . . ?
C5 C2 C9 118.51(11) . . ?
N2 C3 C2 126.56(12) . . ?
N2 C3 C10 107.00(11) . . ?
C2 C3 C10 126.42(12) . . ?
C4 C4 C5 106.48(8) 2_655 . ?
C4 C4 H4 126.8 2_655 . ?
C5 C4 H4 126.8 . . ?
N1 C5 C2 126.03(12) . . ?
N1 C5 C4 110.89(12) . . ?
C2 C5 C4 123.08(12) . . ?
C11 C6 C9 121.22(14) . . ?
C11 C6 H6 119.4 . . ?
C9 C6 H6 119.4 . . ?
C9 C7 C1 121.04(13) . . ?
C9 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
O1 C8 C1 120.29(14) . . ?
O1 C8 C11 120.15(14) . . ?
C1 C8 C11 119.55(13) . . ?
C7 C9 C6 118.23(12) . . ?
C7 C9 C2 120.46(12) . . ?
C6 C9 C2 121.31(13) . . ?
C10 C10 C3 107.96(7) 6 . ?
C10 C10 H10 126.0 6 . ?
C3 C10 H10 126.0 . . ?
C6 C11 C8 119.86(14) . . ?
C6 C11 H11 120.1 . . ?
C8 C11 H11 120.1 . . ?
C19 C12 C14 118.48(14) . . ?
C19 C12 C15 122.22(14) . . ?
C14 C12 C15 119.29(13) . . ?
C16 C13 C16 121.9(2) . 6 ?
C16 C13 C14 119.05(11) . . ?
C16 C13 C14 119.05(11) 6 . ?
C13 C14 C12 119.41(9) . 6 ?
C13 C14 C12 119.41(9) . . ?
C12 C14 C12 121.18(18) 6 . ?
C21 C15 C17 118.82(16) . . ?
C21 C15 C12 121.63(15) . . ?
C17 C15 C12 119.52(14) . . ?
C18 C16 C13 120.74(16) . . ?
C18 C16 H16 119.6 . . ?
C13 C16 H16 119.6 . . ?
C20 C17 C15 119.41(10) . . ?
C20 C17 C15 119.41(10) . 6 ?
C15 C17 C15 121.13(19) . 6 ?
C16 C18 C19 120.65(15) . . ?
C16 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C12 C19 C18 121.67(16) . . ?
C12 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C22 C20 C22 121.7(2) . 6 ?
C22 C20 C17 119.12(12) . . ?
C22 C20 C17 119.12(12) 6 . ?
C15 C21 C23 121.13(19) . . ?
C15 C21 H21 119.4 . . ?
C23 C21 H21 119.4 . . ?
C23 C22 C20 120.57(18) 6 . ?
C23 C22 H22 119.7 6 . ?
C20 C22 H22 119.7 . . ?
C22 C23 C21 120.89(18) 6 . ?
C22 C23 H23 119.6 6 . ?
C21 C23 H23 119.6 . . ?
C27 N3 C24 95.2(6) . . ?
C24 N3 C26 112.5(3) . . ?
C24 C24 C27 107.3(2) 6_565 . ?
N3 C24 H24 110.7 . . ?
C24 C24 H24 110.7 6_565 . ?
C26 C25 C27 120.4(4) . 6_565 ?
C26 C25 C27 120.4(4) 6_565 . ?
C27 C25 C27 96.1(5) 6_565 . ?
C26 C25 H25 107.7 6_565 . ?
C26 C25 H25 107.7 . . ?
C27 C25 H25 131.8 6_565 . ?
C27 C25 H25 131.8 . . ?
C27 C26 C25 105.0(11) . . ?
C25 C26 N3 126.5(5) . . ?
C27 C26 H26 137.9 . . ?
C25 C26 H26 116.9 . . ?
N3 C26 H26 116.7 . . ?
C26 C27 N3 140.7(12) . . ?
C25 C27 C24 114.6(3) . . ?
N3 C27 H26 116.1 . . ?
C25 C27 H27 122.9 . . ?
C24 C27 H27 122.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N3 0.84 1.74 2.579(4) 180 .
O1 H1 O1 0.84 1.95 2.779(3) 170 2_656

# start Validation Reply Form
_vrf_PLAT770_sn29                
;
PROBLEM:
RESPONSE:
The pyridine entity is located on and disordered about the axis of twofold
rotation. The indicated distance is between atoms of differently oriented fragments 
of the disordered molecule.
;
_vrf_PLAT410_sn29                
;
PROBLEM:
RESPONSE:
The pyridine entity is located on and disordered about the axis of twofold
rotation. The indicated distance is between atoms of differently oriented fragments 
of the disordered molecule.
;
# end Validation Reply Form

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.049

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

data_sn33sq
_database_code_depnum_ccdc_archive 'CCDC 1455570'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C44 H30 N4 O4, 0.5(C20 H12), C10 H8 N2, 2.7(C H4 O)'
_chemical_formula_sum            'C66.7 H54.8 N6 O6.7'
_chemical_formula_weight         1047.56

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'
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'
H H 0.0000 0.0000 '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                   16.1034(6)
_cell_length_b                   23.3602(9)
_cell_length_c                   15.3638(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.178(2)
_cell_angle_gamma                90
_cell_volume                     5313.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    6406
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      25.06

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             2202
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            27212
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.685
_diffrn_reflns_theta_max         25.060
_diffrn_reflns_theta_full        25.060
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9365
_reflns_number_gt                6406
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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.

 The structure contains additional severely disorder molecules of the
 methanol crystallization solvent, which couldn't be modeled by discrete
 atoms. Its contribution to the diffraction pattern was subtracted by the
 Squeeze technique, using the PLATON software (Spek, 2015).
;

_computing_data_collection       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0837P)²+5.1827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9365
_refine_ls_number_parameters     680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
O1 O 0.93718(15) 0.76092(9) 0.53813(15) 0.0329(5) Uani 1 1 d . . . . .
H1 H 0.9124 0.7910 0.5462 0.049 Uiso 1 1 calc R U . . .
O2 O 0.62760(14) 0.24096(9) 0.58982(15) 0.0351(5) Uani 1 1 d . . . . .
H2 H 0.6546 0.2117 0.5826 0.053 Uiso 1 1 calc R U . . .
O3 O 0.46876(15) -0.25045(10) 0.15882(18) 0.0439(6) Uani 1 1 d . . . . .
H3 H 0.5128 -0.2390 0.1471 0.066 Uiso 1 1 calc R U . . .
O4 O 0.37278(16) 0.27992(10) 0.35862(19) 0.0498(7) Uani 1 1 d . . . . .
H4 H 0.3917 0.2735 0.4170 0.075 Uiso 1 1 calc R U . . .
N1 N -0.01736(13) 0.08128(9) 0.04621(16) 0.0192(5) Uani 1 1 d . . . . .
H1A H -0.0094 0.0474 0.0255 0.023 Uiso 1 1 calc R U . . .
N2 N 0.13516(14) 0.00535(9) 0.07938(16) 0.0204(5) Uani 1 1 d . . . . .
N3 N 0.92923(15) 0.49907(10) 0.85653(17) 0.0233(5) Uani 1 1 d . . . . .
N4 N 1.03888(15) 0.58399(10) 0.99106(16) 0.0219(5) Uani 1 1 d . . . . .
H4A H 1.0189 0.5495 0.9951 0.026 Uiso 1 1 calc R U . . .
N5 N 0.70310(17) 0.14134(11) 0.58094(19) 0.0338(6) Uani 1 1 d . . . . .
N6 N 0.86898(19) -0.13498(12) 0.5524(2) 0.0398(7) Uani 1 1 d . . . . .
C1 C 0.25855(17) -0.13141(12) 0.07066(19) 0.0191(6) Uani 1 1 d . . . . .
C2 C -0.09892(17) 0.10864(11) 0.02098(19) 0.0192(6) Uani 1 1 d . . . . .
C3 C 0.19907(17) -0.03578(12) 0.08908(19) 0.0205(6) Uani 1 1 d . . . . .
C4 C 0.18282(17) -0.08947(12) 0.04435(19) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.05005(17) 0.11462(11) 0.10865(19) 0.0194(6) Uani 1 1 d . . . . .
C6 C 1.01934(18) 0.61413(12) 0.9087(2) 0.0223(6) Uani 1 1 d . . . . .
C7 C 0.33675(18) -0.12150(12) 0.0540(2) 0.0231(6) Uani 1 1 d . . . . .
H7 H 0.3417 -0.0874 0.0227 0.028 Uiso 1 1 calc R U . . .
C8 C -0.08256(18) 0.16075(12) 0.07342(19) 0.0209(6) Uani 1 1 d . . . . .
H8 H -0.1269 0.1881 0.0718 0.025 Uiso 1 1 calc R U . . .
C9 C 1.09456(18) 0.61616(12) 1.0661(2) 0.0221(6) Uani 1 1 d . . . . .
C10 C 0.95652(18) 0.63725(12) 0.7402(2) 0.0220(6) Uani 1 1 d . . . . .
C11 C 0.20403(17) 0.14846(12) 0.2053(2) 0.0233(6) Uani 1 1 d . . . . .
C12 C 0.00782(18) 0.16440(12) 0.1263(2) 0.0222(6) Uani 1 1 d . . . . .
H12 H 0.0376 0.1949 0.1678 0.027 Uiso 1 1 calc R U . . .
C13 C 0.18118(18) 0.05069(12) 0.1335(2) 0.0224(6) Uani 1 1 d . . . . .
C14 C 0.94092(19) 0.72168(12) 0.6051(2) 0.0238(6) Uani 1 1 d . . . . .
C15 C 0.86873(18) 0.40028(12) 0.8387(2) 0.0234(6) Uani 1 1 d . . . . .
C16 C 0.92945(19) 0.54048(12) 0.7933(2) 0.0249(7) Uani 1 1 d . . . . .
C17 C 0.96841(18) 0.59491(12) 0.8169(2) 0.0223(6) Uani 1 1 d . . . . .
C18 C 0.27702(18) 0.03795(12) 0.1778(2) 0.0254(7) Uani 1 1 d . . . . .
H18 H 0.3234 0.0627 0.2173 0.031 Uiso 1 1 calc R U . . .
C19 C 0.6892(2) 0.27905(12) 0.6476(2) 0.0257(7) Uani 1 1 d . . . . .
C20 C 1.0012(2) 0.63206(13) 0.6791(2) 0.0274(7) Uani 1 1 d . . . . .
H20 H 1.0372 0.5992 0.6831 0.033 Uiso 1 1 calc R U . . .
C21 C 0.14278(17) 0.10214(12) 0.14720(19) 0.0216(6) Uani 1 1 d . . . . .
C22 C 0.78027(19) 0.26596(12) 0.6938(2) 0.0244(6) Uani 1 1 d . . . . .
H22 H 0.8025 0.2301 0.6834 0.029 Uiso 1 1 calc R U . . .
C23 C 0.83865(19) 0.30534(12) 0.7551(2) 0.0250(7) Uani 1 1 d . . . . .
H23 H 0.9007 0.2959 0.7873 0.030 Uiso 1 1 calc R U . . .
C24 C 0.80757(19) 0.35860(12) 0.7703(2) 0.0244(6) Uani 1 1 d . . . . .
C25 C 0.32310(19) -0.22173(13) 0.1437(2) 0.0269(7) Uani 1 1 d . . . . .
H25 H 0.3180 -0.2562 0.1740 0.032 Uiso 1 1 calc R U . . .
C26 C 0.88308(19) 0.45325(12) 0.8035(2) 0.0242(6) Uani 1 1 d . . . . .
C27 C 0.71640(19) 0.37121(13) 0.7216(2) 0.0268(7) Uani 1 1 d . . . . .
H27 H 0.6943 0.4076 0.7303 0.032 Uiso 1 1 calc R U . . .
C28 C 0.28741(18) -0.01585(12) 0.1519(2) 0.0254(7) Uani 1 1 d . . . . .
H28 H 0.3424 -0.0367 0.1713 0.031 Uiso 1 1 calc R U . . .
C29 C 0.25357(18) -0.18246(12) 0.1154(2) 0.0235(6) Uani 1 1 d . . . . .
H29 H 0.2008 -0.1904 0.1268 0.028 Uiso 1 1 calc R U . . .
C30 C 0.89466(19) 0.72736(12) 0.6639(2) 0.0263(7) Uani 1 1 d . . . . .
H30 H 0.8571 0.7597 0.6583 0.032 Uiso 1 1 calc R U . . .
C31 C 0.77344(18) 0.03393(13) 0.5694(2) 0.0260(7) Uani 1 1 d . . . . .
C32 C 0.40096(19) -0.21066(13) 0.1276(2) 0.0274(7) Uani 1 1 d . . . . .
C33 C 1.11046(19) 0.66941(12) 1.0282(2) 0.0259(7) Uani 1 1 d . . . . .
H33 H 1.1468 0.7001 1.0637 0.031 Uiso 1 1 calc R U . . .
C34 C 0.74082(19) 0.06989(13) 0.4916(2) 0.0279(7) Uani 1 1 d . . . . .
H34 H 0.7413 0.0582 0.4326 0.033 Uiso 1 1 calc R U . . .
C35 C 1.06450(19) 0.66812(12) 0.9333(2) 0.0250(6) Uani 1 1 d . . . . .
H35 H 1.0625 0.6979 0.8903 0.030 Uiso 1 1 calc R U . . .
C36 C 0.6573(2) 0.33232(13) 0.6611(2) 0.0285(7) Uani 1 1 d . . . . .
H36 H 0.5953 0.3418 0.6288 0.034 Uiso 1 1 calc R U . . .
C37 C 0.8546(2) 0.46636(13) 0.7046(2) 0.0315(7) Uani 1 1 d . . . . .
H37 H 0.8220 0.4417 0.6532 0.038 Uiso 1 1 calc R U . . .
C38 C 0.40728(18) -0.16073(13) 0.0824(2) 0.0266(7) Uani 1 1 d . . . . .
H38 H 0.4599 -0.1532 0.0706 0.032 Uiso 1 1 calc R U . . .
C39 C 0.80836(19) -0.02389(13) 0.5630(2) 0.0275(7) Uani 1 1 d . . . . .
C40 C 0.25623(18) 0.14164(13) 0.3016(2) 0.0276(7) Uani 1 1 d . . . . .
H40 H 0.2537 0.1065 0.3317 0.033 Uiso 1 1 calc R U . . .
C41 C 0.9939(2) 0.67380(13) 0.6130(2) 0.0277(7) Uani 1 1 d . . . . .
H41 H 1.0254 0.6696 0.5726 0.033 Uiso 1 1 calc R U . . .
C42 C 0.70761(19) 0.12299(13) 0.5009(2) 0.0304(7) Uani 1 1 d . . . . .
H42 H 0.6869 0.1477 0.4475 0.036 Uiso 1 1 calc R U . . .
C43 C 0.90356(19) 0.68559(13) 0.7309(2) 0.0283(7) Uani 1 1 d . . . . .
H43 H 0.8725 0.6901 0.7718 0.034 Uiso 1 1 calc R U . . .
C44 C 0.31161(19) 0.18515(14) 0.3542(2) 0.0331(8) Uani 1 1 d . . . . .
H44 H 0.3458 0.1803 0.4201 0.040 Uiso 1 1 calc R U . . .
C45 C 0.21026(19) 0.19998(13) 0.1629(2) 0.0305(7) Uani 1 1 d . . . . .
H45 H 0.1750 0.2056 0.0975 0.037 Uiso 1 1 calc R U . . .
C46 C 0.31675(19) 0.23588(13) 0.3098(2) 0.0335(8) Uani 1 1 d . . . . .
C47 C 0.8824(2) 0.51987(13) 0.6979(2) 0.0337(7) Uani 1 1 d . . . . .
H47 H 0.8728 0.5402 0.6412 0.040 Uiso 1 1 calc R U . . .
C48 C 0.8809(2) -0.04781(13) 0.6377(2) 0.0315(7) Uani 1 1 d . . . . .
H48 H 0.9113 -0.0265 0.6940 0.038 Uiso 1 1 calc R U . . .
C49 C 0.9083(2) -0.10286(14) 0.6293(2) 0.0342(8) Uani 1 1 d . . . . .
H49 H 0.9578 -0.1186 0.6810 0.041 Uiso 1 1 calc R U . . .
C50 C 0.7705(2) 0.05348(14) 0.6537(2) 0.0346(8) Uani 1 1 d . . . . .
H50 H 0.7934 0.0305 0.7092 0.042 Uiso 1 1 calc R U . . .
C51 C 0.2670(2) 0.24321(13) 0.2147(2) 0.0347(8) Uani 1 1 d . . . . .
H51 H 0.2716 0.2778 0.1844 0.042 Uiso 1 1 calc R U . . .
C52 C 0.7674(2) -0.05741(14) 0.4833(2) 0.0389(8) Uani 1 1 d . . . . .
H52 H 0.7176 -0.0430 0.4305 0.047 Uiso 1 1 calc R U . . .
C53 C 0.7340(2) 0.10667(14) 0.6556(2) 0.0378(8) Uani 1 1 d . . . . .
H53 H 0.7308 0.1191 0.7131 0.045 Uiso 1 1 calc R U . . .
C54 C 0.7995(3) -0.11199(15) 0.4809(3) 0.0462(9) Uani 1 1 d . . . . .
H54 H 0.7706 -0.1343 0.4255 0.055 Uiso 1 1 calc R U . . .
C55 C 0.5003(2) 0.05194(15) 0.4490(3) 0.0454(9) Uani 1 1 d . . . . .
C56 C 0.4914(2) 0.05433(15) 0.5400(3) 0.0467(10) Uani 1 1 d . . . . .
C57 C 0.5094(2) -0.00237(16) 0.4109(3) 0.0468(10) Uani 1 1 d . . . . .
C58 C 0.5194(2) -0.00471(19) 0.3231(3) 0.0558(11) Uani 1 1 d . . . . .
C59 C 0.5006(2) 0.10036(17) 0.3970(3) 0.0555(11) Uani 1 1 d . . . . .
H59 H 0.4939 0.1367 0.4213 0.067 Uiso 1 1 calc R U . . .
C60 C 0.5149(3) -0.10576(18) 0.4173(4) 0.0630(12) Uani 1 1 d . . . . .
H60 H 0.5131 -0.1407 0.4482 0.076 Uiso 1 1 calc R U . . .
C61 C 0.5103(2) 0.0984(2) 0.3111(4) 0.0644(12) Uani 1 1 d . . . . .
H61 H 0.5106 0.1328 0.2783 0.077 Uiso 1 1 calc R U . . .
C62 C 0.5194(2) 0.0470(2) 0.2739(3) 0.0669(13) Uani 1 1 d . . . . .
H62 H 0.5257 0.0455 0.2151 0.080 Uiso 1 1 calc R U . . .
C63 C 0.5236(3) -0.1076(2) 0.3309(4) 0.0733(14) Uani 1 1 d . . . . .
H63 H 0.5276 -0.1435 0.3039 0.088 Uiso 1 1 calc R U . . .
C64 C 0.5263(3) -0.0583(2) 0.2845(3) 0.0678(13) Uani 1 1 d . . . . .
H64 H 0.5330 -0.0601 0.2258 0.081 Uiso 1 1 calc R U . . .
C65 C 0.4299(5) 0.2640(4) 0.6092(6) 0.145(3) Uiso 1 1 d . . . . .
H65A H 0.4783 0.2498 0.6669 0.217 Uiso 1 1 calc R U . . .
H65B H 0.3741 0.2427 0.5982 0.217 Uiso 1 1 calc R U . . .
H65C H 0.4200 0.3048 0.6164 0.217 Uiso 1 1 calc R U . . .
O5 O 0.4522(2) 0.25697(16) 0.5389(3) 0.0919(11) Uiso 1 1 d . . . . .
H5 H 0.5071 0.2520 0.5547 0.111 Uiso 1 1 d 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
O1 C14 1.362(3) . ?
O1 H1 0.8400 . ?
O2 C19 1.367(3) . ?
O2 H2 0.8400 . ?
O3 C32 1.369(3) . ?
O3 H3 0.8400 . ?
O4 C46 1.379(4) . ?
O4 H4 0.8400 . ?
N1 C2 1.372(3) . ?
N1 C5 1.373(3) . ?
N1 H1A 0.8800 . ?
N2 C13 1.370(3) . ?
N2 C3 1.373(3) . ?
N3 C16 1.372(4) . ?
N3 C26 1.373(4) . ?
N4 C6 1.372(4) . ?
N4 C9 1.373(4) . ?
N4 H4A 0.8800 . ?
N5 C42 1.330(4) . ?
N5 C53 1.331(4) . ?
N6 C49 1.330(4) . ?
N6 C54 1.334(4) . ?
C1 C29 1.395(4) . ?
C1 C7 1.400(4) . ?
C1 C4 1.491(4) . ?
C2 C4 1.402(4) 3 ?
C2 C8 1.426(4) . ?
C3 C4 1.404(4) . ?
C3 C28 1.446(4) . ?
C4 C2 1.402(4) 3 ?
C5 C21 1.403(4) . ?
C5 C12 1.426(4) . ?
C6 C17 1.397(4) . ?
C6 C35 1.430(4) . ?
C7 C38 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C12 1.362(4) . ?
C8 H8 0.9500 . ?
C9 C15 1.398(4) 3_767 ?
C9 C33 1.438(4) . ?
C10 C43 1.388(4) . ?
C10 C20 1.394(4) . ?
C10 C17 1.492(4) . ?
C11 C45 1.390(4) . ?
C11 C40 1.394(4) . ?
C11 C21 1.499(4) . ?
C12 H12 0.9500 . ?
C13 C21 1.405(4) . ?
C13 C18 1.452(4) . ?
C14 C41 1.382(4) . ?
C14 C30 1.385(4) . ?
C15 C9 1.398(4) 3_767 ?
C15 C26 1.406(4) . ?
C15 C24 1.486(4) . ?
C16 C17 1.401(4) . ?
C16 C47 1.443(4) . ?
C18 C28 1.348(4) . ?
C18 H18 0.9500 . ?
C19 C22 1.389(4) . ?
C19 C36 1.392(4) . ?
C20 C41 1.380(4) . ?
C20 H20 0.9500 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(4) . ?
C23 H23 0.9500 . ?
C24 C27 1.392(4) . ?
C25 C29 1.379(4) . ?
C25 C32 1.394(4) . ?
C25 H25 0.9500 . ?
C26 C37 1.438(4) . ?
C27 C36 1.378(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C43 1.384(4) . ?
C30 H30 0.9500 . ?
C31 C34 1.384(4) . ?
C31 C50 1.392(4) . ?
C31 C39 1.481(4) . ?
C32 C38 1.382(4) . ?
C33 C35 1.352(4) . ?
C33 H33 0.9500 . ?
C34 C42 1.380(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C47 1.345(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C52 1.383(4) . ?
C39 C48 1.392(4) . ?
C40 C44 1.383(4) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C46 1.386(5) . ?
C44 H44 0.9500 . ?
C45 C51 1.384(4) . ?
C45 H45 0.9500 . ?
C46 C51 1.373(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.382(4) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C53 1.380(5) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C54 1.382(5) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C59 1.386(5) . ?
C55 C57 1.429(5) . ?
C55 C56 1.460(6) . ?
C56 C60 1.392(5) 3_656 ?
C56 C57 1.431(5) 3_656 ?
C57 C58 1.422(6) . ?
C57 C56 1.431(5) 3_656 ?
C58 C64 1.409(6) . ?
C58 C62 1.424(6) . ?
C59 C61 1.391(6) . ?
C59 H59 0.9500 . ?
C60 C63 1.389(7) . ?
C60 C56 1.392(5) 3_656 ?
C60 H60 0.9500 . ?
C61 C62 1.363(6) . ?
C61 H61 0.9500 . ?
C62 H62 0.9500 . ?
C63 C64 1.365(7) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?
C65 O5 1.276(8) . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
O5 H5 0.8300 . ?

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
C14 O1 H1 109.5 . . ?
C19 O2 H2 109.5 . . ?
C32 O3 H3 109.5 . . ?
C46 O4 H4 109.5 . . ?
C2 N1 C5 109.8(2) . . ?
C2 N1 H1A 125.1 . . ?
C5 N1 H1A 125.1 . . ?
C13 N2 C3 105.8(2) . . ?
C16 N3 C26 106.3(2) . . ?
C6 N4 C9 109.3(2) . . ?
C6 N4 H4A 125.4 . . ?
C9 N4 H4A 125.4 . . ?
C42 N5 C53 117.6(3) . . ?
C49 N6 C54 117.1(3) . . ?
C29 C1 C7 117.5(2) . . ?
C29 C1 C4 119.7(2) . . ?
C7 C1 C4 122.7(2) . . ?
N1 C2 C4 126.8(2) . 3 ?
N1 C2 C8 107.1(2) . . ?
C4 C2 C8 126.1(2) 3 . ?
N2 C3 C4 125.8(2) . . ?
N2 C3 C28 110.2(2) . . ?
C4 C3 C28 124.0(2) . . ?
C2 C4 C3 125.2(2) 3 . ?
C2 C4 C1 116.0(2) 3 . ?
C3 C4 C1 118.6(2) . . ?
N1 C5 C21 126.5(2) . . ?
N1 C5 C12 106.9(2) . . ?
C21 C5 C12 126.7(2) . . ?
N4 C6 C17 126.6(3) . . ?
N4 C6 C35 107.5(2) . . ?
C17 C6 C35 125.8(3) . . ?
C38 C7 C1 121.1(3) . . ?
C38 C7 H7 119.4 . . ?
C1 C7 H7 119.4 . . ?
C12 C8 C2 107.9(2) . . ?
C12 C8 H8 126.1 . . ?
C2 C8 H8 126.1 . . ?
N4 C9 C15 126.5(3) . 3_767 ?
N4 C9 C33 107.2(2) . . ?
C15 C9 C33 126.3(3) 3_767 . ?
C43 C10 C20 117.4(3) . . ?
C43 C10 C17 120.2(2) . . ?
C20 C10 C17 122.3(2) . . ?
C45 C11 C40 118.1(3) . . ?
C45 C11 C21 119.9(3) . . ?
C40 C11 C21 122.0(3) . . ?
C8 C12 C5 108.2(2) . . ?
C8 C12 H12 125.9 . . ?
C5 C12 H12 125.9 . . ?
N2 C13 C21 126.0(2) . . ?
N2 C13 C18 110.3(2) . . ?
C21 C13 C18 123.7(2) . . ?
O1 C14 C41 116.9(2) . . ?
O1 C14 C30 123.6(3) . . ?
C41 C14 C30 119.5(3) . . ?
C9 C15 C26 125.4(3) 3_767 . ?
C9 C15 C24 116.7(3) 3_767 . ?
C26 C15 C24 117.9(3) . . ?
N3 C16 C17 125.6(3) . . ?
N3 C16 C47 109.7(3) . . ?
C17 C16 C47 124.6(3) . . ?
C6 C17 C16 125.3(3) . . ?
C6 C17 C10 115.2(2) . . ?
C16 C17 C10 119.5(2) . . ?
C28 C18 C13 106.6(2) . . ?
C28 C18 H18 126.7 . . ?
C13 C18 H18 126.7 . . ?
O2 C19 C22 122.6(3) . . ?
O2 C19 C36 117.5(3) . . ?
C22 C19 C36 119.9(3) . . ?
C41 C20 C10 121.2(3) . . ?
C41 C20 H20 119.4 . . ?
C10 C20 H20 119.4 . . ?
C5 C21 C13 124.9(2) . . ?
C5 C21 C11 116.3(2) . . ?
C13 C21 C11 118.8(2) . . ?
C23 C22 C19 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C19 C22 H22 120.0 . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C27 C24 C23 118.1(3) . . ?
C27 C24 C15 120.5(3) . . ?
C23 C24 C15 121.4(3) . . ?
C29 C25 C32 119.8(3) . . ?
C29 C25 H25 120.1 . . ?
C32 C25 H25 120.1 . . ?
N3 C26 C15 126.2(3) . . ?
N3 C26 C37 109.5(2) . . ?
C15 C26 C37 124.2(3) . . ?
C36 C27 C24 121.7(3) . . ?
C36 C27 H27 119.1 . . ?
C24 C27 H27 119.1 . . ?
C18 C28 C3 107.1(2) . . ?
C18 C28 H28 126.5 . . ?
C3 C28 H28 126.5 . . ?
C25 C29 C1 121.8(3) . . ?
C25 C29 H29 119.1 . . ?
C1 C29 H29 119.1 . . ?
C43 C30 C14 119.5(3) . . ?
C43 C30 H30 120.2 . . ?
C14 C30 H30 120.2 . . ?
C34 C31 C50 117.6(3) . . ?
C34 C31 C39 121.4(3) . . ?
C50 C31 C39 120.9(3) . . ?
O3 C32 C38 122.9(3) . . ?
O3 C32 C25 117.5(3) . . ?
C38 C32 C25 119.7(3) . . ?
C35 C33 C9 108.0(3) . . ?
C35 C33 H33 126.0 . . ?
C9 C33 H33 126.0 . . ?
C42 C34 C31 119.1(3) . . ?
C42 C34 H34 120.4 . . ?
C31 C34 H34 120.4 . . ?
C33 C35 C6 108.1(3) . . ?
C33 C35 H35 126.0 . . ?
C6 C35 H35 126.0 . . ?
C27 C36 C19 119.5(3) . . ?
C27 C36 H36 120.3 . . ?
C19 C36 H36 120.3 . . ?
C47 C37 C26 107.5(3) . . ?
C47 C37 H37 126.2 . . ?
C26 C37 H37 126.2 . . ?
C32 C38 C7 120.1(3) . . ?
C32 C38 H38 119.9 . . ?
C7 C38 H38 119.9 . . ?
C52 C39 C48 117.1(3) . . ?
C52 C39 C31 120.9(3) . . ?
C48 C39 C31 121.9(3) . . ?
C44 C40 C11 121.1(3) . . ?
C44 C40 H40 119.5 . . ?
C11 C40 H40 119.5 . . ?
C20 C41 C14 120.5(3) . . ?
C20 C41 H41 119.8 . . ?
C14 C41 H41 119.8 . . ?
N5 C42 C34 123.3(3) . . ?
N5 C42 H42 118.3 . . ?
C34 C42 H42 118.3 . . ?
C30 C43 C10 121.9(3) . . ?
C30 C43 H43 119.0 . . ?
C10 C43 H43 119.0 . . ?
C40 C44 C46 119.4(3) . . ?
C40 C44 H44 120.3 . . ?
C46 C44 H44 120.3 . . ?
C51 C45 C11 121.1(3) . . ?
C51 C45 H45 119.5 . . ?
C11 C45 H45 119.5 . . ?
C51 C46 O4 118.0(3) . . ?
C51 C46 C44 120.5(3) . . ?
O4 C46 C44 121.5(3) . . ?
C37 C47 C16 106.9(3) . . ?
C37 C47 H47 126.6 . . ?
C16 C47 H47 126.6 . . ?
C49 C48 C39 119.4(3) . . ?
C49 C48 H48 120.3 . . ?
C39 C48 H48 120.3 . . ?
N6 C49 C48 123.4(3) . . ?
N6 C49 H49 118.3 . . ?
C48 C49 H49 118.3 . . ?
C53 C50 C31 119.1(3) . . ?
C53 C50 H50 120.5 . . ?
C31 C50 H50 120.5 . . ?
C46 C51 C45 119.8(3) . . ?
C46 C51 H51 120.1 . . ?
C45 C51 H51 120.1 . . ?
C54 C52 C39 119.5(3) . . ?
C54 C52 H52 120.2 . . ?
C39 C52 H52 120.2 . . ?
N5 C53 C50 123.2(3) . . ?
N5 C53 H53 118.4 . . ?
C50 C53 H53 118.4 . . ?
N6 C54 C52 123.5(3) . . ?
N6 C54 H54 118.3 . . ?
C52 C54 H54 118.3 . . ?
C59 C55 C57 117.6(4) . . ?
C59 C55 C56 123.0(4) . . ?
C57 C55 C56 119.4(3) . . ?
C60 C56 C57 117.8(4) 3_656 3_656 ?
C60 C56 C55 122.5(4) 3_656 . ?
C57 C56 C55 119.7(3) 3_656 . ?
C58 C57 C55 119.4(4) . . ?
C58 C57 C56 119.7(4) . 3_656 ?
C55 C57 C56 120.9(4) . 3_656 ?
C64 C58 C57 119.4(4) . . ?
C64 C58 C62 120.9(5) . . ?
C57 C58 C62 119.7(4) . . ?
C55 C59 C61 123.2(4) . . ?
C55 C59 H59 118.4 . . ?
C61 C59 H59 118.4 . . ?
C63 C60 C56 122.0(4) . 3_656 ?
C63 C60 H60 119.0 . . ?
C56 C60 H60 119.0 3_656 . ?
C62 C61 C59 119.8(4) . . ?
C62 C61 H61 120.1 . . ?
C59 C61 H61 120.1 . . ?
C61 C62 C58 120.2(5) . . ?
C61 C62 H62 119.9 . . ?
C58 C62 H62 119.9 . . ?
C64 C63 C60 120.6(4) . . ?
C64 C63 H63 119.7 . . ?
C60 C63 H63 119.7 . . ?
C63 C64 C58 120.4(5) . . ?
C63 C64 H64 119.8 . . ?
C58 C64 H64 119.8 . . ?
O5 C65 H65A 109.5 . . ?
O5 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
O5 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C65 O5 H5 112.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N6 0.84 1.88 2.713(3) 169 1_565
O2 H2 N5 0.84 1.82 2.654(3) 169 .
O3 H3 O4 0.84 1.93 2.761(3) 170 2_645
O4 H4 O5 0.84 1.78 2.609(5) 169 .
O5 H5 O2 0.83 1.82 2.644(4) 180 .


# SQUEEZE RESULTS (Version =  30715)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 286 61 '3.4 molecules of MeOH '
2 0.500 0.500 0.500 286 61 '3.4 molecules of MeOH '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          'disordered MeOH solvent'

# start Validation Reply Form
_vrf_CHEMW03_sn33sq              
;
PROBLEM:
RESPONSE:
The Sum & Moiety formulae contain additional 1.7 molecules of MeOH 
subtracted by PLATON.
;
# end Validation Reply Form

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.058



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

data_sn32sq
_database_code_depnum_ccdc_archive 'CCDC 1455571'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4. C12 H10 N2, 5.5(C H4 O)'
_chemical_formula_sum            'C61.5 H62 N6 O9.5'
_chemical_formula_weight         1037.17

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   32.937(4)
_cell_length_b                   6.2835(5)
_cell_length_c                   29.547(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.674(4)
_cell_angle_gamma                90
_cell_volume                     5313.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4082
_cell_measurement_theta_min      1.42
_cell_measurement_theta_max      28.26

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             2196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            24499
_diffrn_reflns_av_unetI/netI     0.1113
_diffrn_reflns_av_R_equivalents  0.1648
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.423
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6585
_reflns_number_gt                4082
_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.

 The structure contains also severely disordered crystallization solvent
 in the intra-lattice voids (MeOH and possibly also bpe), which couldn't
 be modeled by discrete atoms. Its contribution to the diffraction pattern
 was subtracted by the Squeeze technique, using the PLATON software 
 (Spek, 2015).
;

_computing_data_collection       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6585
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75563(4) 1.0905(2) 0.82679(5) 0.0304(3) Uani 1 1 d . . . . .
H1 H 0.7575 0.9601 0.8472 0.046 Uiso 1 1 d R U . . .
O2 O 0.63131(6) -0.0722(3) 0.40824(9) 0.0727(6) Uani 1 1 d . . . . .
H2 H 0.6196 -0.1911 0.4080 0.109 Uiso 1 1 calc R U . . .
N1 N 0.56016(5) 0.8060(2) 0.54316(5) 0.0230(3) Uani 1 1 d . . . . .
H1A H 0.5325 0.8675 0.5280 0.028 Uiso 1 1 calc R U . . .
N2 N 0.52206(5) 1.1973(2) 0.56178(5) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.75962(6) 0.7763(3) 0.89198(6) 0.0338(4) Uani 1 1 d . . . . .
C1 C 0.64050(6) 1.0422(3) 0.67649(6) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.57292(6) 0.6441(3) 0.52177(6) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.71771(6) 1.0695(3) 0.77805(6) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.59656(6) 0.8595(3) 0.59170(6) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.56891(6) 0.3930(3) 0.45492(7) 0.0244(4) Uani 1 1 d . . . . .
C6 C 0.49867(6) 1.3693(3) 0.56609(7) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.56331(6) 1.1874(3) 0.60882(6) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.54648(6) 0.5594(3) 0.47144(6) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.59819(6) 1.0298(3) 0.62312(6) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.63429(6) 0.7168(3) 0.60189(7) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.6640 0.7133 0.6327 0.029 Uiso 1 1 calc R U . . .
C11 C 0.65128(6) 0.8768(3) 0.71215(6) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.6321 0.7534 0.7020 0.031 Uiso 1 1 calc R U . . .
C12 C 0.66976(6) 1.2210(3) 0.69260(7) 0.0249(4) Uani 1 1 d . . . . .
H12 H 0.6636 1.3344 0.6688 0.030 Uiso 1 1 calc R U . . .
C13 C 0.70779(6) 1.2352(3) 0.74309(7) 0.0254(4) Uani 1 1 d . . . . .
H13 H 0.7269 1.3588 0.7535 0.030 Uiso 1 1 calc R U . . .
C14 C 0.62008(6) 0.5876(3) 0.55977(7) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.6382 0.4786 0.5561 0.030 Uiso 1 1 calc R U . . .
C15 C 0.68952(6) 0.8886(3) 0.76226(7) 0.0272(4) Uani 1 1 d . . . . .
H15 H 0.6964 0.7732 0.7857 0.033 Uiso 1 1 calc R U . . .
C16 C 0.56606(6) 1.3606(3) 0.64254(7) 0.0291(4) Uani 1 1 d . . . . .
H16 H 0.5910 1.3889 0.6766 0.035 Uiso 1 1 calc R U . . .
C17 C 0.52623(6) 1.4742(3) 0.61617(7) 0.0286(4) Uani 1 1 d . . . . .
H17 H 0.5178 1.5983 0.6280 0.034 Uiso 1 1 calc R U . . .
C18 C 0.74429(7) 0.4765(3) 0.95301(7) 0.0315(4) Uani 1 1 d . . . . .
C19 C 0.58281(7) 0.1966(3) 0.48026(8) 0.0320(5) Uani 1 1 d . . . . .
H19 H 0.5779 0.1673 0.5087 0.038 Uiso 1 1 calc R U . . .
C20 C 0.57698(7) 0.4315(3) 0.41359(8) 0.0332(5) Uani 1 1 d . . . . .
H20 H 0.5683 0.5647 0.3961 0.040 Uiso 1 1 calc R U . . .
C21 C 0.73576(7) 0.3280(3) 0.98577(8) 0.0347(5) Uani 1 1 d . . . . .
H21 H 0.7075 0.3448 0.9867 0.042 Uiso 1 1 calc R U . . .
C22 C 0.71998(7) 0.6688(4) 0.93778(7) 0.0370(5) Uani 1 1 d . . . . .
H22 H 0.6973 0.7010 0.9478 0.044 Uiso 1 1 calc R U . . .
C23 C 0.61062(7) 0.0824(4) 0.42285(10) 0.0417(5) Uani 1 1 d . . . . .
C24 C 0.60371(7) 0.0433(3) 0.46448(10) 0.0422(5) Uani 1 1 d . . . . .
H24 H 0.6133 -0.0887 0.4824 0.051 Uiso 1 1 calc R U . . .
C25 C 0.72866(7) 0.8122(4) 0.90834(7) 0.0376(5) Uani 1 1 d . . . . .
H25 H 0.7120 0.9429 0.8991 0.045 Uiso 1 1 calc R U . . .
C26 C 0.77608(8) 0.4389(4) 0.93534(9) 0.0405(5) Uani 1 1 d . . . . .
H26 H 0.7932 0.3094 0.9438 0.049 Uiso 1 1 calc R U . . .
C27 C 0.59759(7) 0.2769(4) 0.39757(8) 0.0425(6) Uani 1 1 d . . . . .
H27 H 0.6027 0.3051 0.3692 0.051 Uiso 1 1 calc R U . . .
C28 C 0.78238(8) 0.5908(4) 0.90556(9) 0.0418(5) Uani 1 1 d . . . . .
H28 H 0.8041 0.5616 0.8941 0.050 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
O1 C3 1.368(2) . ?
O1 H1 1.0000 . ?
O2 C23 1.373(3) . ?
O2 H2 0.8400 . ?
N1 C2 1.369(2) . ?
N1 C4 1.380(2) . ?
N1 H1A 0.8800 . ?
N2 C6 1.369(2) . ?
N2 C7 1.383(2) . ?
N3 C28 1.336(3) . ?
N3 C25 1.346(3) . ?
C1 C11 1.394(3) . ?
C1 C12 1.402(3) . ?
C1 C9 1.503(2) . ?
C2 C8 1.404(2) . ?
C2 C14 1.440(2) . ?
C3 C13 1.387(3) . ?
C3 C15 1.394(3) . ?
C4 C9 1.400(3) . ?
C4 C10 1.438(3) . ?
C5 C20 1.393(3) . ?
C5 C19 1.398(3) . ?
C5 C8 1.495(3) . ?
C6 C8 1.417(2) 5_676 ?
C6 C17 1.455(2) . ?
C7 C9 1.414(3) . ?
C7 C16 1.448(3) . ?
C8 C6 1.417(2) 5_676 ?
C10 C14 1.360(3) . ?
C10 H10 0.9500 . ?
C11 C15 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.351(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C22 1.395(3) . ?
C18 C26 1.402(3) . ?
C18 C21 1.468(3) . ?
C19 C24 1.392(3) . ?
C19 H19 0.9500 . ?
C20 C27 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C21 1.329(4) 7_657 ?
C21 H21 0.9500 . ?
C22 C25 1.377(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 C27 1.385(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C28 1.382(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 107.9 . . ?
C23 O2 H2 109.5 . . ?
C2 N1 C4 110.70(14) . . ?
C2 N1 H1A 124.6 . . ?
C4 N1 H1A 124.6 . . ?
C6 N2 C7 105.07(14) . . ?
C28 N3 C25 116.76(18) . . ?
C11 C1 C12 117.76(16) . . ?
C11 C1 C9 120.74(16) . . ?
C12 C1 C9 121.49(15) . . ?
N1 C2 C8 126.83(16) . . ?
N1 C2 C14 106.41(14) . . ?
C8 C2 C14 126.63(17) . . ?
O1 C3 C13 117.87(16) . . ?
O1 C3 C15 122.74(16) . . ?
C13 C3 C15 119.38(16) . . ?
N1 C4 C9 127.13(16) . . ?
N1 C4 C10 106.36(15) . . ?
C9 C4 C10 126.31(16) . . ?
C20 C5 C19 117.97(18) . . ?
C20 C5 C8 120.27(17) . . ?
C19 C5 C8 121.76(16) . . ?
N2 C6 C8 126.69(16) . 5_676 ?
N2 C6 C17 110.84(15) . . ?
C8 C6 C17 122.47(17) 5_676 . ?
N2 C7 C9 125.49(16) . . ?
N2 C7 C16 110.72(15) . . ?
C9 C7 C16 123.79(16) . . ?
C2 C8 C6 124.71(17) . 5_676 ?
C2 C8 C5 117.60(15) . . ?
C6 C8 C5 117.54(15) 5_676 . ?
C4 C9 C7 125.34(15) . . ?
C4 C9 C1 116.53(15) . . ?
C7 C9 C1 118.13(15) . . ?
C14 C10 C4 108.07(15) . . ?
C14 C10 H10 126.0 . . ?
C4 C10 H10 126.0 . . ?
C15 C11 C1 121.46(17) . . ?
C15 C11 H11 119.3 . . ?
C1 C11 H11 119.3 . . ?
C13 C12 C1 121.07(16) . . ?
C13 C12 H12 119.5 . . ?
C1 C12 H12 119.5 . . ?
C3 C13 C12 120.23(17) . . ?
C3 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C10 C14 C2 108.43(16) . . ?
C10 C14 H14 125.8 . . ?
C2 C14 H14 125.8 . . ?
C11 C15 C3 120.09(17) . . ?
C11 C15 H15 120.0 . . ?
C3 C15 H15 120.0 . . ?
C17 C16 C7 106.75(16) . . ?
C17 C16 H16 126.6 . . ?
C7 C16 H16 126.6 . . ?
C16 C17 C6 106.60(17) . . ?
C16 C17 H17 126.7 . . ?
C6 C17 H17 126.7 . . ?
C22 C18 C26 116.18(19) . . ?
C22 C18 C21 119.76(17) . . ?
C26 C18 C21 124.06(19) . . ?
C24 C19 C5 121.12(19) . . ?
C24 C19 H19 119.4 . . ?
C5 C19 H19 119.4 . . ?
C5 C20 C27 120.8(2) . . ?
C5 C20 H20 119.6 . . ?
C27 C20 H20 119.6 . . ?
C21 C21 C18 125.5(2) 7_657 . ?
C21 C21 H21 117.3 7_657 . ?
C18 C21 H21 117.3 . . ?
C25 C22 C18 120.32(19) . . ?
C25 C22 H22 119.8 . . ?
C18 C22 H22 119.8 . . ?
O2 C23 C24 118.8(2) . . ?
O2 C23 C27 121.6(2) . . ?
C24 C23 C27 119.63(19) . . ?
C23 C24 C19 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
N3 C25 C22 123.3(2) . . ?
N3 C25 H25 118.4 . . ?
C22 C25 H25 118.4 . . ?
C28 C26 C18 119.7(2) . . ?
C28 C26 H26 120.1 . . ?
C18 C26 H26 120.1 . . ?
C23 C27 C20 120.3(2) . . ?
C23 C27 H27 119.9 . . ?
C20 C27 H27 119.9 . . ?
N3 C28 C26 123.7(2) . . ?
N3 C28 H28 118.1 . . ?
C26 C28 H28 118.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 1.00 1.73 2.715(2) 166 .

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.902 0.250 327 99 '5.5 molecules of MeOH '
2 1.000 0.402 0.250 327 99 '5.5 molecules of MeOH '
3 0.500 0.087 0.750 327 99 '5.5 molecules of MeOH '
4 1.000 0.587 0.750 327 99 '5.5 molecules of MeOH '
_platon_squeeze_details          
;
 Disordered crystallization solvent.
;

# start Validation Reply Form
_vrf_CHEMW03_sn32sq              
;
PROBLEM:
RESPONSE:
The Sum and Moiety formulae contain 5.5 additional molecules of the
MeOH disordered solvent, subtracted by PLATON.
;
_vrf_PLAT420_sn32sq              
;
PROBLEM:
RESPONSE:
This hydrogen bonding site is most probably solvated by the disordered
crystallization solvent excluded from the structural model.
;
# end Validation Reply Form

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.132

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

data_sn30
_database_code_depnum_ccdc_archive 'CCDC 1455572'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H30 N4 O4, 3(C12 H8 N2), 2(C H4 O)'
_chemical_formula_sum            'C82 H62 N10 O6'
_chemical_formula_weight         1283.41

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.0722(5)
_cell_length_b                   15.4167(16)
_cell_length_c                   16.9383(18)
_cell_angle_alpha                88.096(4)
_cell_angle_beta                 86.696(4)
_cell_angle_gamma                85.177(4)
_cell_volume                     1576.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean 1.75
_diffrn_reflns_number            20500
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.766
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_full        25.035
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5519
_reflns_number_gt                4463
_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       'Apex2, Bruker-AXS'
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0481P)²+1.1493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5519
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.9043(2) 0.82886(9) 0.73979(8) 0.0324(4) Uani 1 1 d . . . . .
H33 H 0.8200 0.8900 0.7419 0.049 Uiso 1 1 d R U . . .
O2 O 0.0851(2) 0.84569(9) 0.05200(7) 0.0244(3) Uani 1 1 d . . . . .
H34 H -0.0570 0.8879 0.0413 0.037 Uiso 1 1 d R U . . .
O3 O -0.7020(4) 0.00904(11) 0.26476(11) 0.0682(7) Uani 1 1 d . . . . .
H35 H -0.6690 -0.0007 0.3190 0.102 Uiso 1 1 d R U . . .
N1 N 0.1687(2) 0.48525(9) 0.60475(8) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.1018 0.4818 0.5590 0.019 Uiso 1 1 d R U . . .
N2 N 0.1926(2) 0.59428(9) 0.45671(8) 0.0169(3) Uani 1 1 d . . . . .
N3 N 0.4715(3) 0.47182(10) 0.92234(9) 0.0251(4) Uani 1 1 d . . . . .
N4 N 0.3070(3) 0.04917(10) 0.97650(9) 0.0229(4) Uani 1 1 d . . . . .
N5 N 0.5759(3) 0.00334(10) 0.57706(9) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.7785(3) 0.77723(12) 0.69996(11) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.8700(3) 0.69518(13) 0.68004(11) 0.0229(4) Uani 1 1 d . . . . .
H3 H 1.0152 0.6759 0.6946 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7497(3) 0.64115(12) 0.63890(11) 0.0211(4) Uani 1 1 d . . . . .
H4 H 0.8132 0.5847 0.6257 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5373(3) 0.66804(11) 0.61645(10) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.3985(3) 0.60903(11) 0.57666(10) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.3146(3) 0.54282(11) 0.62440(10) 0.0164(4) Uani 1 1 d . . . . .
C7 C -0.1132(3) 0.56523(11) 0.33010(10) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.0486(3) 0.62502(11) 0.32472(10) 0.0162(4) Uani 1 1 d . . . . .
C9 C 0.1938(3) 0.63685(11) 0.38444(10) 0.0163(4) Uani 1 1 d . . . . .
C10 C 0.3491(3) 0.62930(11) 0.49798(10) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.0689(3) 0.79141(11) 0.11655(10) 0.0178(4) Uani 1 1 d . . . . .
C12 C 0.2518(3) 0.73491(12) 0.13308(10) 0.0183(4) Uani 1 1 d . . . . .
H12 H 0.3810 0.7337 0.0986 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2468(3) 0.68033(11) 0.19962(10) 0.0174(4) Uani 1 1 d . . . . .
H11 H 0.3732 0.6421 0.2104 0.021 Uiso 1 1 calc R U . . .
C14 C 0.0589(3) 0.68063(11) 0.25108(10) 0.0162(4) Uani 1 1 d . . . . .
C15 C 0.5658(3) 0.80488(12) 0.67892(11) 0.0230(4) Uani 1 1 d . . . . .
H2 H 0.5012 0.8608 0.6932 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4483(3) 0.75041(12) 0.63694(11) 0.0198(4) Uani 1 1 d . . . . .
H36 H 0.3037 0.7700 0.6219 0.024 Uiso 1 1 calc R U . . .
C17 C 0.3607(3) 0.69864(11) 0.37972(10) 0.0176(4) Uani 1 1 d . . . . .
H7 H 0.3959 0.7356 0.3356 0.021 Uiso 1 1 calc R U . . .
C18 C 0.4570(3) 0.69402(12) 0.44960(10) 0.0182(4) Uani 1 1 d . . . . .
H6 H 0.5731 0.7268 0.4642 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3564(3) 0.52637(12) 0.70624(10) 0.0192(4) Uani 1 1 d . . . . .
H8 H 0.4520 0.5564 0.7362 0.023 Uiso 1 1 calc R U . . .
C20 C -0.2356(3) 0.53955(11) 0.26657(10) 0.0179(4) Uani 1 1 d . . . . .
H9 H -0.2329 0.5643 0.2144 0.021 Uiso 1 1 calc R U . . .
C21 C -0.1215(3) 0.79100(12) 0.16579(10) 0.0189(4) Uani 1 1 d . . . . .
H14 H -0.2488 0.8282 0.1541 0.023 Uiso 1 1 calc R U . . .
C22 C -0.1252(3) 0.73614(12) 0.23206(10) 0.0190(4) Uani 1 1 d . . . . .
H13 H -0.2563 0.7362 0.2655 0.023 Uiso 1 1 calc R U . . .
C23 C 0.9402(4) 0.60208(14) 0.88785(12) 0.0301(5) Uani 1 1 d . . . . .
H15 H 1.0361 0.6197 0.8451 0.036 Uiso 1 1 calc R U . . .
C24 C 0.7777(3) 0.55029(14) 0.87422(11) 0.0286(5) Uani 1 1 d . . . . .
H19 H 0.7617 0.5318 0.8221 0.034 Uiso 1 1 calc R U . . .
C25 C 0.6309(3) 0.52327(12) 0.93693(11) 0.0244(4) Uani 1 1 d . . . . .
C26 C 0.6601(3) 0.55180(12) 1.01566(11) 0.0237(4) Uani 1 1 d . . . . .
C27 C 0.8327(3) 0.60599(13) 1.02718(11) 0.0280(5) Uani 1 1 d . . . . .
H18 H 0.8529 0.6254 1.0787 0.034 Uiso 1 1 calc R U . . .
C28 C 0.9691(4) 0.63046(13) 0.96571(12) 0.0297(5) Uani 1 1 d . . . . .
H16 H 1.0842 0.6666 0.9745 0.036 Uiso 1 1 calc R U . . .
C29 C 0.5161(4) 0.19480(15) 1.11242(12) 0.0332(5) Uani 1 1 d . . . . .
H20 H 0.4780 0.2508 1.1333 0.040 Uiso 1 1 calc R U . . .
C30 C 0.3843(3) 0.16320(13) 1.06028(12) 0.0294(5) Uani 1 1 d . . . . .
H22 H 0.2549 0.1970 1.0450 0.035 Uiso 1 1 calc R U . . .
C31 C 0.4386(3) 0.08002(13) 1.02854(11) 0.0221(4) Uani 1 1 d . . . . .
C32 C 0.6343(3) 0.02982(12) 1.05245(11) 0.0218(4) Uani 1 1 d . . . . .
C33 C 0.7675(3) 0.06550(14) 1.10763(11) 0.0267(4) Uani 1 1 d . . . . .
H24 H 0.8973 0.0329 1.1243 0.032 Uiso 1 1 calc R U . . .
C34 C 0.7103(4) 0.14559(14) 1.13636(12) 0.0312(5) Uani 1 1 d . . . . .
H21 H 0.8007 0.1691 1.1729 0.037 Uiso 1 1 calc R U . . .
C35 C -0.0081(3) 0.14085(13) 0.51642(12) 0.0285(5) Uani 1 1 d . . . . .
H25 H -0.1413 0.1737 0.5036 0.034 Uiso 1 1 calc R U . . .
C36 C 0.1081(3) 0.09236(13) 0.46039(12) 0.0264(4) Uani 1 1 d . . . . .
H29 H 0.0552 0.0906 0.4088 0.032 Uiso 1 1 calc R U . . .
C37 C 0.3088(3) 0.04427(12) 0.47890(11) 0.0220(4) Uani 1 1 d . . . . .
C38 C 0.3863(3) 0.04716(12) 0.55682(11) 0.0225(4) Uani 1 1 d . . . . .
C39 C 0.2576(3) 0.09759(13) 0.61406(12) 0.0272(5) Uani 1 1 d . . . . .
H27 H 0.3050 0.0995 0.6664 0.033 Uiso 1 1 calc R U . . .
C40 C 0.0675(3) 0.14293(13) 0.59410(12) 0.0296(5) Uani 1 1 d . . . . .
H26 H -0.0171 0.1768 0.6327 0.036 Uiso 1 1 calc R U . . .
C41 C -0.7108(4) -0.06360(15) 0.22396(14) 0.0427(6) Uani 1 1 d . . . . .
H31 H -0.5851 -0.1050 0.2362 0.064 Uiso 1 1 calc R U . . .
H32 H -0.7042 -0.0490 0.1672 0.064 Uiso 1 1 calc R U . . .
H30 H -0.8494 -0.0898 0.2387 0.064 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
O1 C1 1.367(2) . ?
O1 H33 1.0352 . ?
O2 C11 1.359(2) . ?
O2 H34 1.0572 . ?
O3 C41 1.342(3) . ?
O3 H35 0.9557 . ?
N1 C6 1.367(2) . ?
N1 C7 1.372(2) 2_566 ?
N1 H1 0.9007 . ?
N2 C10 1.368(2) . ?
N2 C9 1.369(2) . ?
N3 C25 1.341(3) . ?
N3 C26 1.342(3) 2_667 ?
N4 C32 1.341(3) 2_657 ?
N4 C31 1.347(2) . ?
N5 C38 1.341(2) . ?
N5 C37 1.345(2) 2_656 ?
C1 C2 1.382(3) . ?
C1 C15 1.388(3) . ?
C2 C3 1.383(3) . ?
C2 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H4 0.9500 . ?
C4 C16 1.385(3) . ?
C4 C5 1.493(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.402(2) . ?
C6 C19 1.434(2) . ?
C7 N1 1.372(2) 2_566 ?
C7 C8 1.400(3) . ?
C7 C20 1.427(2) . ?
C8 C9 1.405(2) . ?
C8 C14 1.491(2) . ?
C9 C17 1.446(3) . ?
C10 C18 1.446(3) . ?
C11 C21 1.386(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 H11 0.9500 . ?
C14 C22 1.396(2) . ?
C15 C16 1.385(3) . ?
C15 H2 0.9500 . ?
C16 H36 0.9500 . ?
C17 C18 1.347(3) . ?
C17 H7 0.9500 . ?
C18 H6 0.9500 . ?
C19 C20 1.356(3) 2_566 ?
C19 H8 0.9500 . ?
C20 C19 1.356(3) 2_566 ?
C20 H9 0.9500 . ?
C21 C22 1.383(3) . ?
C21 H14 0.9500 . ?
C22 H13 0.9500 . ?
C23 C24 1.355(3) . ?
C23 C28 1.428(3) . ?
C23 H15 0.9500 . ?
C24 C25 1.421(3) . ?
C24 H19 0.9500 . ?
C25 C26 1.443(3) . ?
C26 N3 1.342(3) 2_667 ?
C26 C27 1.420(3) . ?
C27 C28 1.356(3) . ?
C27 H18 0.9500 . ?
C28 H16 0.9500 . ?
C29 C30 1.354(3) . ?
C29 C34 1.419(3) . ?
C29 H20 0.9500 . ?
C30 C31 1.413(3) . ?
C30 H22 0.9500 . ?
C31 C32 1.433(3) . ?
C32 N4 1.341(3) 2_657 ?
C32 C33 1.424(3) . ?
C33 C34 1.353(3) . ?
C33 H24 0.9500 . ?
C34 H21 0.9500 . ?
C35 C36 1.356(3) . ?
C35 C40 1.421(3) . ?
C35 H25 0.9500 . ?
C36 C37 1.418(3) . ?
C36 H29 0.9500 . ?
C37 N5 1.345(2) 2_656 ?
C37 C38 1.430(3) . ?
C38 C39 1.420(3) . ?
C39 C40 1.352(3) . ?
C39 H27 0.9500 . ?
C40 H26 0.9500 . ?
C41 H31 0.9800 . ?
C41 H32 0.9800 . ?
C41 H30 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
C1 O1 H33 107.0 . . ?
C11 O2 H34 115.9 . . ?
C41 O3 H35 114.8 . . ?
C6 N1 C7 109.68(14) . 2_566 ?
C6 N1 H1 128.7 . . ?
C7 N1 H1 121.3 2_566 . ?
C10 N2 C9 105.98(14) . . ?
C25 N3 C26 116.89(16) . 2_667 ?
C32 N4 C31 117.80(16) 2_657 . ?
C38 N5 C37 117.37(16) . 2_656 ?
O1 C1 C2 117.89(17) . . ?
O1 C1 C15 122.24(17) . . ?
C2 C1 C15 119.87(17) . . ?
C1 C2 C3 119.86(17) . . ?
C1 C2 H3 120.1 . . ?
C3 C2 H3 120.1 . . ?
C2 C3 C4 121.15(17) . . ?
C2 C3 H4 119.4 . . ?
C4 C3 H4 119.4 . . ?
C16 C4 C3 118.19(17) . . ?
C16 C4 C5 119.46(16) . . ?
C3 C4 C5 122.20(16) . . ?
C6 C5 C10 126.18(17) . . ?
C6 C5 C4 115.75(15) . . ?
C10 C5 C4 117.83(16) . . ?
N1 C6 C5 127.45(16) . . ?
N1 C6 C19 107.05(15) . . ?
C5 C6 C19 125.39(17) . . ?
N1 C7 C8 126.39(16) 2_566 . ?
N1 C7 C20 107.29(15) 2_566 . ?
C8 C7 C20 126.07(16) . . ?
C7 C8 C9 124.29(16) . . ?
C7 C8 C14 116.42(15) . . ?
C9 C8 C14 119.27(16) . . ?
N2 C9 C8 125.25(16) . . ?
N2 C9 C17 109.92(15) . . ?
C8 C9 C17 124.79(16) . . ?
N2 C10 C5 126.40(16) . . ?
N2 C10 C18 110.36(15) . . ?
C5 C10 C18 123.22(16) . . ?
O2 C11 C21 122.49(16) . . ?
O2 C11 C12 117.92(16) . . ?
C21 C11 C12 119.58(16) . . ?
C13 C12 C11 120.29(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.97(16) . . ?
C12 C13 H11 119.5 . . ?
C14 C13 H11 119.5 . . ?
C13 C14 C22 117.72(16) . . ?
C13 C14 C8 122.79(15) . . ?
C22 C14 C8 119.49(16) . . ?
C16 C15 C1 119.61(17) . . ?
C16 C15 H2 120.2 . . ?
C1 C15 H2 120.2 . . ?
C4 C16 C15 121.32(17) . . ?
C4 C16 H36 119.3 . . ?
C15 C16 H36 119.3 . . ?
C18 C17 C9 107.19(16) . . ?
C18 C17 H7 126.4 . . ?
C9 C17 H7 126.4 . . ?
C17 C18 C10 106.53(16) . . ?
C17 C18 H6 126.7 . . ?
C10 C18 H6 126.7 . . ?
C20 C19 C6 108.01(16) 2_566 . ?
C20 C19 H8 126.0 2_566 . ?
C6 C19 H8 126.0 . . ?
C19 C20 C7 107.94(16) 2_566 . ?
C19 C20 H9 126.0 2_566 . ?
C7 C20 H9 126.0 . . ?
C22 C21 C11 119.72(16) . . ?
C22 C21 H14 120.1 . . ?
C11 C21 H14 120.1 . . ?
C21 C22 C14 121.66(17) . . ?
C21 C22 H13 119.2 . . ?
C14 C22 H13 119.2 . . ?
C24 C23 C28 120.8(2) . . ?
C24 C23 H15 119.6 . . ?
C28 C23 H15 119.6 . . ?
C23 C24 C25 120.86(18) . . ?
C23 C24 H19 119.6 . . ?
C25 C24 H19 119.6 . . ?
N3 C25 C24 120.01(17) . . ?
N3 C25 C26 121.60(18) . . ?
C24 C25 C26 118.39(19) . . ?
N3 C26 C27 119.67(17) 2_667 . ?
N3 C26 C25 121.51(19) 2_667 . ?
C27 C26 C25 118.81(18) . . ?
C28 C27 C26 120.98(18) . . ?
C28 C27 H18 119.5 . . ?
C26 C27 H18 119.5 . . ?
C27 C28 C23 120.1(2) . . ?
C27 C28 H16 119.9 . . ?
C23 C28 H16 119.9 . . ?
C30 C29 C34 121.1(2) . . ?
C30 C29 H20 119.5 . . ?
C34 C29 H20 119.5 . . ?
C29 C30 C31 120.20(19) . . ?
C29 C30 H22 119.9 . . ?
C31 C30 H22 119.9 . . ?
N4 C31 C30 119.83(17) . . ?
N4 C31 C32 121.07(17) . . ?
C30 C31 C32 119.10(18) . . ?
N4 C32 C33 120.08(17) 2_657 . ?
N4 C32 C31 121.13(17) 2_657 . ?
C33 C32 C31 118.79(18) . . ?
C34 C33 C32 120.29(18) . . ?
C34 C33 H24 119.9 . . ?
C32 C33 H24 119.9 . . ?
C33 C34 C29 120.54(19) . . ?
C33 C34 H21 119.7 . . ?
C29 C34 H21 119.7 . . ?
C36 C35 C40 120.63(18) . . ?
C36 C35 H25 119.7 . . ?
C40 C35 H25 119.7 . . ?
C35 C36 C37 119.88(18) . . ?
C35 C36 H29 120.1 . . ?
C37 C36 H29 120.1 . . ?
N5 C37 C36 119.62(17) 2_656 . ?
N5 C37 C38 120.87(17) 2_656 . ?
C36 C37 C38 119.51(17) . . ?
N5 C38 C39 119.48(17) . . ?
N5 C38 C37 121.76(17) . . ?
C39 C38 C37 118.77(17) . . ?
C40 C39 C38 120.03(19) . . ?
C40 C39 H27 120.0 . . ?
C38 C39 H27 120.0 . . ?
C39 C40 C35 121.17(18) . . ?
C39 C40 H26 119.4 . . ?
C35 C40 H26 119.4 . . ?
O3 C41 H31 109.5 . . ?
O3 C41 H32 109.5 . . ?
H31 C41 H32 109.5 . . ?
O3 C41 H30 109.5 . . ?
H31 C41 H30 109.5 . . ?
H32 C41 H30 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H33 O3 1.04 1.66 2.691(2) 173.2 2_566
O2 H34 N4 1.06 1.77 2.822(2) 175.3 2_566
O3 H35 N5 0.96 1.88 2.825(2) 170.3 2_556

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.047

