# Electronic Supplementary Material (ESI) for Chemical Science.
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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_1R

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
6-((1-(naphthalen-2-yl)ethyl)carbamoyl)picolinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.8436(4)
_cell_length_b                   26.8023(14)
_cell_length_c                   8.3932(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.9000(13)
_cell_angle_gamma                90
_cell_volume                     1539.33(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.043
_cell_measurement_theta_max      27.491

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24245
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6996
_reflns_number_gt                6757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2, (Bruker 2012)'
_computing_cell_refinement       'Bruker SAINT, (Bruker 2012)'
_computing_data_reduction        'Bruker SAINT, (Bruker 2012)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL v. 2008/4, (Bruker 2008)'
_computing_publication_material  'Bruker SHELXTL v. 2008/4, (Bruker 2008)'

_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)+(0.0389P)²+0.2216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6996
_refine_ls_number_parameters     455
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.73177(18) 0.65500(4) 0.21643(14) 0.0228(3) Uani 1 1 d . . . . .
O2 O 0.81204(19) 0.57515(4) 0.26499(14) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.818(3) 0.5728(9) 0.162(3) 0.036 Uiso 1 1 d . U . . .
C3 C 0.7693(2) 0.62115(6) 0.30688(19) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.7699(2) 0.62779(6) 0.48516(19) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.7272(2) 0.67447(6) 0.5483(2) 0.0199(3) Uani 1 1 d . . . . .
H5A H 0.7006 0.7021 0.4804 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7246(2) 0.67971(6) 0.7128(2) 0.0210(3) Uani 1 1 d . . . . .
H6A H 0.6972 0.7112 0.7596 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7626(2) 0.63825(6) 0.80798(19) 0.0188(3) Uani 1 1 d . . . . .
H7A H 0.7592 0.6405 0.9209 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8058(2) 0.59346(6) 0.73276(19) 0.0168(3) Uani 1 1 d . . . . .
N9 N 0.81103(19) 0.58786(5) 0.57456(16) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.8545(2) 0.54753(6) 0.82872(18) 0.0179(3) Uani 1 1 d . . . . .
O11 O 0.8308(2) 0.54585(5) 0.97396(14) 0.0314(3) Uani 1 1 d . . . . .
N12 N 0.9247(2) 0.50948(5) 0.74547(16) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.939(3) 0.5158(8) 0.647(3) 0.023(5) Uiso 1 1 d . . . . .
C13 C 0.9964(2) 0.46341(6) 0.81973(17) 0.0170(3) Uani 1 1 d . . . . .
H13 H 0.947(3) 0.4668(8) 0.930(2) 0.020 Uiso 1 1 d . U . . .
C14 C 1.2189(2) 0.46232(6) 0.82281(19) 0.0195(3) Uani 1 1 d . . . . .
H14A H 1.2687 0.4907 0.8848 0.029 Uiso 1 1 calc R U . . .
H14B H 1.2670 0.4644 0.7136 0.029 Uiso 1 1 calc R U . . .
H14C H 1.2642 0.4312 0.8720 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8985(2) 0.41885(6) 0.74095(18) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.9914(2) 0.38742(6) 0.63714(19) 0.0175(3) Uani 1 1 d . . . . .
H16A H 1.1243 0.3934 0.6122 0.021 Uiso 1 1 calc R U . . .
C17 C 0.8925(2) 0.34600(6) 0.56613(19) 0.0182(3) Uani 1 1 d . . . . .
C18 C 0.9854(3) 0.31356(6) 0.45771(19) 0.0209(3) Uani 1 1 d . . . . .
H18A H 1.1182 0.3190 0.4313 0.025 Uiso 1 1 calc R U . . .
C19 C 0.8855(3) 0.27436(6) 0.3906(2) 0.0232(4) Uani 1 1 d . . . . .
H19A H 0.9491 0.2531 0.3172 0.028 Uiso 1 1 calc R U . . .
C20 C 0.6890(3) 0.26525(6) 0.4295(2) 0.0233(4) Uani 1 1 d . . . . .
H20A H 0.6213 0.2378 0.3830 0.028 Uiso 1 1 calc R U . . .
C21 C 0.5955(3) 0.29596(6) 0.5342(2) 0.0222(3) Uani 1 1 d . . . . .
H21A H 0.4630 0.2896 0.5597 0.027 Uiso 1 1 calc R U . . .
C22 C 0.6939(2) 0.33708(6) 0.60516(19) 0.0186(3) Uani 1 1 d . . . . .
C23 C 0.6012(2) 0.36989(6) 0.7129(2) 0.0213(3) Uani 1 1 d . . . . .
H23A H 0.4688 0.3643 0.7403 0.026 Uiso 1 1 calc R U . . .
C24 C 0.6998(2) 0.40948(6) 0.7777(2) 0.0209(3) Uani 1 1 d . . . . .
H24A H 0.6344 0.4312 0.8487 0.025 Uiso 1 1 calc R U . . .
O25 O 0.24178(19) 0.66031(4) -0.24683(14) 0.0233(3) Uani 1 1 d . . . . .
O26 O 0.3212(2) 0.58041(4) -0.20157(14) 0.0230(3) Uani 1 1 d . . . . .
H26 H 0.322(3) 0.5786(9) -0.303(3) 0.035 Uiso 1 1 d . U . . .
C27 C 0.2751(2) 0.62594(6) -0.15744(19) 0.0177(3) Uani 1 1 d . . . . .
C28 C 0.2649(2) 0.63123(6) 0.02090(18) 0.0163(3) Uani 1 1 d . . . . .
C29 C 0.2184(2) 0.67746(6) 0.08506(19) 0.0184(3) Uani 1 1 d . . . . .
H29A H 0.1922 0.7053 0.0179 0.022 Uiso 1 1 calc R U . . .
C30 C 0.2112(2) 0.68200(6) 0.24976(19) 0.0198(3) Uani 1 1 d . . . . .
H30A H 0.1825 0.7132 0.2975 0.024 Uiso 1 1 calc R U . . .
C31 C 0.2468(2) 0.64013(6) 0.34385(19) 0.0181(3) Uani 1 1 d . . . . .
H31A H 0.2428 0.6420 0.4568 0.022 Uiso 1 1 calc R U . . .
C32 C 0.2885(2) 0.59546(6) 0.26729(18) 0.0163(3) Uani 1 1 d . . . . .
N33 N 0.29986(19) 0.59066(5) 0.10895(16) 0.0161(3) Uani 1 1 d . . . . .
C34 C 0.3255(2) 0.54860(6) 0.36143(18) 0.0172(3) Uani 1 1 d . . . . .
O35 O 0.3140(2) 0.54756(5) 0.50832(14) 0.0277(3) Uani 1 1 d . . . . .
N36 N 0.3694(2) 0.50857(5) 0.27488(16) 0.0172(3) Uani 1 1 d . . . . .
H36 H 0.387(3) 0.5155(8) 0.168(3) 0.030(6) Uiso 1 1 d . . . . .
C37 C 0.4339(2) 0.46110(6) 0.34476(18) 0.0183(3) Uani 1 1 d . . . . .
H37 H 0.382(3) 0.4602(8) 0.453(2) 0.022 Uiso 1 1 d . U . . .
C38 C 0.6560(3) 0.46011(6) 0.3552(2) 0.0248(4) Uani 1 1 d . . . . .
H38A H 0.7027 0.4892 0.4156 0.037 Uiso 1 1 calc R U . . .
H38B H 0.7094 0.4611 0.2476 0.037 Uiso 1 1 calc R U . . .
H38C H 0.6990 0.4295 0.4091 0.037 Uiso 1 1 calc R U . . .
C39 C 0.3415(2) 0.41845(6) 0.25130(18) 0.0168(3) Uani 1 1 d . . . . .
C40 C 0.4459(2) 0.37794(6) 0.19998(18) 0.0174(3) Uani 1 1 d . . . . .
H40A H 0.5806 0.3754 0.2278 0.021 Uiso 1 1 calc R U . . .
C41 C 0.3571(2) 0.33972(6) 0.10618(19) 0.0173(3) Uani 1 1 d . . . . .
C42 C 0.4651(2) 0.29860(6) 0.0475(2) 0.0201(3) Uani 1 1 d . . . . .
H42A H 0.5993 0.2952 0.0760 0.024 Uiso 1 1 calc R U . . .
C43 C 0.3776(3) 0.26380(6) -0.0497(2) 0.0223(3) Uani 1 1 d . . . . .
H43A H 0.4516 0.2365 -0.0882 0.027 Uiso 1 1 calc R U . . .
C44 C 0.1785(3) 0.26830(6) -0.0927(2) 0.0234(4) Uani 1 1 d . . . . .
H44A H 0.1198 0.2444 -0.1618 0.028 Uiso 1 1 calc R U . . .
C45 C 0.0692(3) 0.30694(6) -0.0356(2) 0.0213(3) Uani 1 1 d . . . . .
H45A H -0.0653 0.3093 -0.0641 0.026 Uiso 1 1 calc R U . . .
C46 C 0.1552(2) 0.34345(6) 0.06605(19) 0.0177(3) Uani 1 1 d . . . . .
C47 C 0.0476(2) 0.38416(6) 0.12773(19) 0.0188(3) Uani 1 1 d . . . . .
H47A H -0.0890 0.3862 0.1068 0.023 Uiso 1 1 calc R U . . .
C48 C 0.1372(2) 0.42047(6) 0.21674(19) 0.0189(3) Uani 1 1 d . . . . .
H48A H 0.0622 0.4475 0.2562 0.023 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 1.208(2) . ?
O2 C3 1.316(2) . ?
O2 H2 0.87(3) . ?
C3 C4 1.507(2) . ?
C4 N9 1.335(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.388(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7A 0.9500 . ?
C8 N9 1.337(2) . ?
C8 C10 1.506(2) . ?
C10 O11 1.233(2) . ?
C10 N12 1.330(2) . ?
N12 C13 1.464(2) . ?
N12 H12 0.85(2) . ?
C13 C15 1.516(2) . ?
C13 C14 1.523(2) . ?
C13 H13 1.00(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.375(2) . ?
C15 C24 1.421(2) . ?
C16 C17 1.426(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.417(2) . ?
C17 C22 1.423(2) . ?
C18 C19 1.370(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.410(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.370(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.418(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.418(2) . ?
C23 C24 1.366(2) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
O25 C27 1.208(2) . ?
O26 C27 1.315(2) . ?
O26 H26 0.85(3) . ?
C27 C28 1.506(2) . ?
C28 N33 1.334(2) . ?
C28 C29 1.390(2) . ?
C29 C30 1.389(2) . ?
C29 H29A 0.9500 . ?
C30 C31 1.391(2) . ?
C30 H30A 0.9500 . ?
C31 C32 1.391(2) . ?
C31 H31A 0.9500 . ?
C32 N33 1.339(2) . ?
C32 C34 1.503(2) . ?
C34 O35 1.2369(19) . ?
C34 N36 1.333(2) . ?
N36 C37 1.4661(19) . ?
N36 H36 0.92(2) . ?
C37 C39 1.519(2) . ?
C37 C38 1.522(2) . ?
C37 H37 0.98(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.373(2) . ?
C39 C48 1.424(2) . ?
C40 C41 1.422(2) . ?
C40 H40A 0.9500 . ?
C41 C42 1.419(2) . ?
C41 C46 1.420(2) . ?
C42 C43 1.371(2) . ?
C42 H42A 0.9500 . ?
C43 C44 1.409(3) . ?
C43 H43A 0.9500 . ?
C44 C45 1.369(2) . ?
C44 H44A 0.9500 . ?
C45 C46 1.420(2) . ?
C45 H45A 0.9500 . ?
C46 C47 1.419(2) . ?
C47 C48 1.367(2) . ?
C47 H47A 0.9500 . ?
C48 H48A 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 O2 H2 110.3(17) . . ?
O1 C3 O2 125.56(15) . . ?
O1 C3 C4 122.17(14) . . ?
O2 C3 C4 112.27(13) . . ?
N9 C4 C5 123.41(14) . . ?
N9 C4 C3 117.43(13) . . ?
C5 C4 C3 119.15(14) . . ?
C6 C5 C4 118.41(15) . . ?
C6 C5 H5A 120.8 . . ?
C4 C5 H5A 120.8 . . ?
C5 C6 C7 119.04(15) . . ?
C5 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
C8 C7 C6 117.91(15) . . ?
C8 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
N9 C8 C7 123.85(14) . . ?
N9 C8 C10 115.48(13) . . ?
C7 C8 C10 120.66(14) . . ?
C4 N9 C8 117.36(13) . . ?
O11 C10 N12 123.07(15) . . ?
O11 C10 C8 121.80(14) . . ?
N12 C10 C8 115.13(13) . . ?
C10 N12 C13 122.97(13) . . ?
C10 N12 H12 113.9(14) . . ?
C13 N12 H12 122.7(15) . . ?
N12 C13 C15 109.62(12) . . ?
N12 C13 C14 110.58(13) . . ?
C15 C13 C14 115.30(13) . . ?
N12 C13 H13 101.7(12) . . ?
C15 C13 H13 108.9(12) . . ?
C14 C13 H13 109.8(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C24 118.87(15) . . ?
C16 C15 C13 123.59(14) . . ?
C24 C15 C13 117.54(14) . . ?
C15 C16 C17 121.37(15) . . ?
C15 C16 H16A 119.3 . . ?
C17 C16 H16A 119.3 . . ?
C18 C17 C22 119.00(15) . . ?
C18 C17 C16 122.09(16) . . ?
C22 C17 C16 118.91(14) . . ?
C19 C18 C17 120.55(17) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 120.65(16) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C21 C20 C19 120.05(16) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 120.86(17) . . ?
C20 C21 H21A 119.6 . . ?
C22 C21 H21A 119.6 . . ?
C21 C22 C23 122.36(15) . . ?
C21 C22 C17 118.88(15) . . ?
C23 C22 C17 118.76(15) . . ?
C24 C23 C22 120.79(15) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C15 121.30(15) . . ?
C23 C24 H24A 119.4 . . ?
C15 C24 H24A 119.4 . . ?
C27 O26 H26 109.8(17) . . ?
O25 C27 O26 125.21(15) . . ?
O25 C27 C28 122.31(14) . . ?
O26 C27 C28 112.47(13) . . ?
N33 C28 C29 123.51(14) . . ?
N33 C28 C27 117.59(13) . . ?
C29 C28 C27 118.90(14) . . ?
C30 C29 C28 118.38(14) . . ?
C30 C29 H29A 120.8 . . ?
C28 C29 H29A 120.8 . . ?
C29 C30 C31 119.04(14) . . ?
C29 C30 H30A 120.5 . . ?
C31 C30 H30A 120.5 . . ?
C32 C31 C30 117.87(14) . . ?
C32 C31 H31A 121.1 . . ?
C30 C31 H31A 121.1 . . ?
N33 C32 C31 123.84(14) . . ?
N33 C32 C34 115.45(13) . . ?
C31 C32 C34 120.70(14) . . ?
C28 N33 C32 117.32(13) . . ?
O35 C34 N36 122.93(14) . . ?
O35 C34 C32 122.00(14) . . ?
N36 C34 C32 115.07(13) . . ?
C34 N36 C37 123.34(13) . . ?
C34 N36 H36 113.5(14) . . ?
C37 N36 H36 121.4(14) . . ?
N36 C37 C39 109.05(12) . . ?
N36 C37 C38 109.42(13) . . ?
C39 C37 C38 115.08(13) . . ?
N36 C37 H37 106.4(12) . . ?
C39 C37 H37 107.8(12) . . ?
C38 C37 H37 108.7(12) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C48 118.69(15) . . ?
C40 C39 C37 122.91(15) . . ?
C48 C39 C37 118.41(14) . . ?
C39 C40 C41 121.57(15) . . ?
C39 C40 H40A 119.2 . . ?
C41 C40 H40A 119.2 . . ?
C42 C41 C46 118.84(15) . . ?
C42 C41 C40 122.07(15) . . ?
C46 C41 C40 119.07(14) . . ?
C43 C42 C41 120.66(16) . . ?
C43 C42 H42A 119.7 . . ?
C41 C42 H42A 119.7 . . ?
C42 C43 C44 120.38(16) . . ?
C42 C43 H43A 119.8 . . ?
C44 C43 H43A 119.8 . . ?
C45 C44 C43 120.43(16) . . ?
C45 C44 H44A 119.8 . . ?
C43 C44 H44A 119.8 . . ?
C44 C45 C46 120.56(15) . . ?
C44 C45 H45A 119.7 . . ?
C46 C45 H45A 119.7 . . ?
C47 C46 C45 122.46(15) . . ?
C47 C46 C41 118.44(14) . . ?
C45 C46 C41 119.09(15) . . ?
C48 C47 C46 121.07(15) . . ?
C48 C47 H47A 119.5 . . ?
C46 C47 H47A 119.5 . . ?
C47 C48 C39 120.99(14) . . ?
C47 C48 H48A 119.5 . . ?
C39 C48 H48A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 N9 179.21(15) . . . . ?
O2 C3 C4 N9 -0.2(2) . . . . ?
O1 C3 C4 C5 -0.5(2) . . . . ?
O2 C3 C4 C5 -179.97(15) . . . . ?
N9 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 C5 C6 178.76(14) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C6 C7 C8 N9 -0.7(3) . . . . ?
C6 C7 C8 C10 178.10(14) . . . . ?
C5 C4 N9 C8 1.6(2) . . . . ?
C3 C4 N9 C8 -178.08(13) . . . . ?
C7 C8 N9 C4 -0.8(2) . . . . ?
C10 C8 N9 C4 -179.62(13) . . . . ?
N9 C8 C10 O11 -170.53(16) . . . . ?
C7 C8 C10 O11 10.6(3) . . . . ?
N9 C8 C10 N12 9.7(2) . . . . ?
C7 C8 C10 N12 -169.20(15) . . . . ?
O11 C10 N12 C13 -5.4(3) . . . . ?
C8 C10 N12 C13 174.44(14) . . . . ?
C10 N12 C13 C15 128.25(16) . . . . ?
C10 N12 C13 C14 -103.54(17) . . . . ?
N12 C13 C15 C16 106.00(17) . . . . ?
C14 C13 C15 C16 -19.5(2) . . . . ?
N12 C13 C15 C24 -74.08(17) . . . . ?
C14 C13 C15 C24 160.37(14) . . . . ?
C24 C15 C16 C17 0.1(2) . . . . ?
C13 C15 C16 C17 -179.96(14) . . . . ?
C15 C16 C17 C18 179.34(15) . . . . ?
C15 C16 C17 C22 -0.5(2) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
C16 C17 C18 C19 -179.43(15) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C23 179.41(16) . . . . ?
C20 C21 C22 C17 -0.1(2) . . . . ?
C18 C17 C22 C21 0.0(2) . . . . ?
C16 C17 C22 C21 179.85(14) . . . . ?
C18 C17 C22 C23 -179.55(15) . . . . ?
C16 C17 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C24 -179.27(16) . . . . ?
C17 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C15 -0.7(2) . . . . ?
C16 C15 C24 C23 0.5(2) . . . . ?
C13 C15 C24 C23 -179.46(14) . . . . ?
O25 C27 C28 N33 178.47(15) . . . . ?
O26 C27 C28 N33 -0.8(2) . . . . ?
O25 C27 C28 C29 -1.0(2) . . . . ?
O26 C27 C28 C29 179.72(15) . . . . ?
N33 C28 C29 C30 1.2(2) . . . . ?
C27 C28 C29 C30 -179.41(14) . . . . ?
C28 C29 C30 C31 -1.3(2) . . . . ?
C29 C30 C31 C32 0.1(2) . . . . ?
C30 C31 C32 N33 1.3(2) . . . . ?
C30 C31 C32 C34 -179.09(14) . . . . ?
C29 C28 N33 C32 0.1(2) . . . . ?
C27 C28 N33 C32 -179.29(13) . . . . ?
C31 C32 N33 C28 -1.4(2) . . . . ?
C34 C32 N33 C28 178.95(13) . . . . ?
N33 C32 C34 O35 -177.88(15) . . . . ?
C31 C32 C34 O35 2.4(2) . . . . ?
N33 C32 C34 N36 1.5(2) . . . . ?
C31 C32 C34 N36 -178.17(15) . . . . ?
O35 C34 N36 C37 -8.5(3) . . . . ?
C32 C34 N36 C37 172.16(14) . . . . ?
C34 N36 C37 C39 140.91(16) . . . . ?
C34 N36 C37 C38 -92.42(18) . . . . ?
N36 C37 C39 C40 132.73(15) . . . . ?
C38 C37 C39 C40 9.4(2) . . . . ?
N36 C37 C39 C48 -47.82(18) . . . . ?
C38 C37 C39 C48 -171.19(14) . . . . ?
C48 C39 C40 C41 3.6(2) . . . . ?
C37 C39 C40 C41 -176.97(14) . . . . ?
C39 C40 C41 C42 177.64(15) . . . . ?
C39 C40 C41 C46 -0.6(2) . . . . ?
C46 C41 C42 C43 1.8(2) . . . . ?
C40 C41 C42 C43 -176.45(15) . . . . ?
C41 C42 C43 C44 -0.1(2) . . . . ?
C42 C43 C44 C45 -1.2(3) . . . . ?
C43 C44 C45 C46 0.9(3) . . . . ?
C44 C45 C46 C47 179.86(16) . . . . ?
C44 C45 C46 C41 0.8(2) . . . . ?
C42 C41 C46 C47 178.80(14) . . . . ?
C40 C41 C46 C47 -2.9(2) . . . . ?
C42 C41 C46 C45 -2.1(2) . . . . ?
C40 C41 C46 C45 176.20(14) . . . . ?
C45 C46 C47 C48 -175.69(15) . . . . ?
C41 C46 C47 C48 3.4(2) . . . . ?
C46 C47 C48 C39 -0.4(2) . . . . ?
C40 C39 C48 C47 -3.1(2) . . . . ?
C37 C39 C48 C47 177.39(14) . . . . ?

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
N36 H36 N33 0.92(2) 2.16(2) 2.6431(18) 112.0(17) .
C31 H31A O25 0.95 2.54 3.479(2) 172 1_556
O26 H26 O35 0.85(3) 1.79(3) 2.5889(16) 155(2) 1_554
C14 H14A O26 0.98 2.54 3.249(2) 129 1_656
C13 H13 O11 1.00(2) 2.29(2) 2.809(2) 110.9(14) .
N12 H12 N9 0.85(2) 2.20(2) 2.6536(19) 113.1(18) .
C7 H7A O1 0.95 2.52 3.467(2) 174.0 1_556
O2 H2 O11 0.87(3) 1.74(3) 2.5709(17) 160(2) 1_554
N36 H36 N33 0.92(2) 2.16(2) 2.6431(18) 112.0(17) .
C31 H31A O25 0.95 2.54 3.479(2) 172 1_556
O26 H26 O35 0.85(3) 1.79(3) 2.5889(16) 155(2) 1_554
C14 H14A O26 0.98 2.54 3.249(2) 129 1_656
C13 H13 O11 1.00(2) 2.29(2) 2.809(2) 110.9(14) .
N12 H12 N9 0.85(2) 2.20(2) 2.6536(19) 113.1(18) .
C7 H7A O1 0.95 2.52 3.467(2) 174.0 1_556
O2 H2 O11 0.87(3) 1.74(3) 2.5709(17) 160(2) 1_554

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999267'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1S

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.8507(4)
_cell_length_b                   26.7770(17)
_cell_length_c                   8.4103(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.840(2)
_cell_angle_gamma                90
_cell_volume                     1542.63(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9553
_cell_measurement_theta_min      2.422
_cell_measurement_theta_max      32.969

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7266
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47256
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.521
_diffrn_reflns_theta_max         32.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10624
_reflns_number_gt                10218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2, (Bruker 2012)'
_computing_cell_refinement       'Bruker SAINT, (Bruker 2012)'
_computing_data_reduction        'Bruker SAINT, (Bruker 2012)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL v. 2008/4, (Bruker 2008)'
_computing_publication_material  'Bruker APEX2, (Bruker 2012)'

_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)+(0.0593P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.31(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         10624
_refine_ls_number_parameters     437
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.011
_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 0.23161(16) 0.39961(4) 0.21623(12) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.31226(18) 0.47961(4) 0.26480(12) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.3174 0.4813 0.1652 0.031 Uiso 1 1 calc R U . . .
C3 C 0.26944(19) 0.43354(5) 0.30706(15) 0.0146(2) Uani 1 1 d . . . . .
C4 C 0.26992(18) 0.42696(5) 0.48474(15) 0.0133(2) Uani 1 1 d . . . . .
C5 C 0.2274(2) 0.38012(5) 0.54795(16) 0.0166(2) Uani 1 1 d . . . . .
H5 H 0.2009 0.3525 0.4803 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2247(2) 0.37487(5) 0.71225(16) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.1975 0.3434 0.7589 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2625(2) 0.41642(5) 0.80773(16) 0.0160(2) Uani 1 1 d . . . . .
H7 H 0.2587 0.4142 0.9204 0.019 Uiso 1 1 calc R U . . .
C8 C 0.30595(19) 0.46128(4) 0.73288(15) 0.0133(2) Uani 1 1 d . . . . .
N9 N 0.31109(16) 0.46684(4) 0.57452(13) 0.01326(19) Uani 1 1 d . . . . .
C10 C 0.3544(2) 0.50709(5) 0.82854(15) 0.0149(2) Uani 1 1 d . . . . .
O11 O 0.3307(2) 0.50875(4) 0.97377(13) 0.0288(3) Uani 1 1 d . . . . .
N12 N 0.42497(17) 0.54522(4) 0.74518(13) 0.01458(19) Uani 1 1 d . . . . .
H12 H 0.4289 0.5426 0.6410 0.017 Uiso 1 1 calc R U . . .
C13 C 0.49617(19) 0.59123(5) 0.81959(14) 0.0133(2) Uani 1 1 d . . . . .
H13 H 0.4532 0.5906 0.9327 0.016 Uiso 1 1 calc R U . . .
C14 C 0.71908(19) 0.59237(5) 0.82267(15) 0.0159(2) Uani 1 1 d . . . . .
H14A H 0.7688 0.5640 0.8848 0.024 Uiso 1 1 calc R U . . .
H14B H 0.7642 0.6236 0.8715 0.024 Uiso 1 1 calc R U . . .
H14C H 0.7673 0.5902 0.7137 0.024 Uiso 1 1 calc R U . . .
C15 C 0.39873(19) 0.63589(4) 0.74112(15) 0.0133(2) Uani 1 1 d . . . . .
C16 C 0.49140(18) 0.66729(5) 0.63720(15) 0.0136(2) Uani 1 1 d . . . . .
H16 H 0.6241 0.6613 0.6121 0.016 Uiso 1 1 calc R U . . .
C17 C 0.39237(19) 0.70869(4) 0.56631(15) 0.0137(2) Uani 1 1 d . . . . .
C18 C 0.4856(2) 0.74095(5) 0.45780(16) 0.0172(2) Uani 1 1 d . . . . .
H18 H 0.6181 0.7353 0.4312 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3855(2) 0.78042(5) 0.39061(16) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.4493 0.8017 0.3175 0.023 Uiso 1 1 calc R U . . .
C20 C 0.1887(2) 0.78949(5) 0.42938(17) 0.0196(3) Uani 1 1 d . . . . .
H20 H 0.1209 0.8169 0.3827 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0953(2) 0.75873(5) 0.53451(17) 0.0185(2) Uani 1 1 d . . . . .
H21 H -0.0370 0.7651 0.5602 0.022 Uiso 1 1 calc R U . . .
C22 C 0.19391(19) 0.71760(5) 0.60523(15) 0.0148(2) Uani 1 1 d . . . . .
C23 C 0.1012(2) 0.68494(5) 0.71343(17) 0.0177(2) Uani 1 1 d . . . . .
H23 H -0.0308 0.6907 0.7412 0.021 Uiso 1 1 calc R U . . .
C24 C 0.1999(2) 0.64526(5) 0.77821(16) 0.0170(2) Uani 1 1 d . . . . .
H24 H 0.1346 0.6236 0.8493 0.020 Uiso 1 1 calc R U . . .
O25 O 0.74172(17) 0.39422(4) -0.24654(12) 0.0202(2) Uani 1 1 d . . . . .
O26 O 0.82131(18) 0.47441(4) -0.20158(11) 0.0197(2) Uani 1 1 d . . . . .
H26 H 0.8202 0.4760 -0.3013 0.030 Uiso 1 1 calc R U . . .
C27 C 0.77521(19) 0.42872(5) -0.15684(15) 0.0141(2) Uani 1 1 d . . . . .
C28 C 0.76520(18) 0.42350(4) 0.02067(14) 0.0123(2) Uani 1 1 d . . . . .
C29 C 0.71867(19) 0.37707(5) 0.08513(16) 0.0150(2) Uani 1 1 d . . . . .
H29 H 0.6927 0.3492 0.0183 0.018 Uiso 1 1 calc R U . . .
C30 C 0.7112(2) 0.37264(5) 0.24983(16) 0.0162(2) Uani 1 1 d . . . . .
H30 H 0.6823 0.3414 0.2975 0.019 Uiso 1 1 calc R U . . .
C31 C 0.7467(2) 0.41449(5) 0.34391(15) 0.0147(2) Uani 1 1 d . . . . .
H31 H 0.7424 0.4126 0.4566 0.018 Uiso 1 1 calc R U . . .
C32 C 0.78861(18) 0.45924(4) 0.26728(14) 0.0123(2) Uani 1 1 d . . . . .
N33 N 0.79995(16) 0.46403(4) 0.10897(13) 0.01255(18) Uani 1 1 d . . . . .
C34 C 0.82541(19) 0.50599(5) 0.36170(14) 0.0138(2) Uani 1 1 d . . . . .
O35 O 0.8138(2) 0.50704(4) 0.50829(12) 0.0243(2) Uani 1 1 d . . . . .
N36 N 0.86977(17) 0.54612(4) 0.27486(12) 0.01404(19) Uani 1 1 d . . . . .
H36 H 0.8603 0.5439 0.1706 0.017 Uiso 1 1 calc R U . . .
C37 C 0.93339(19) 0.59357(5) 0.34517(14) 0.0142(2) Uani 1 1 d . . . . .
H37 H 0.8828 0.5951 0.4560 0.017 Uiso 1 1 calc R U . . .
C38 C 1.1558(2) 0.59462(5) 0.35534(18) 0.0210(3) Uani 1 1 d . . . . .
H38A H 1.2027 0.5654 0.4149 0.031 Uiso 1 1 calc R U . . .
H38B H 1.1986 0.6252 0.4098 0.031 Uiso 1 1 calc R U . . .
H38C H 1.2091 0.5940 0.2479 0.031 Uiso 1 1 calc R U . . .
C39 C 0.84142(19) 0.63616(4) 0.25154(14) 0.0126(2) Uani 1 1 d . . . . .
C40 C 0.94594(18) 0.67674(5) 0.20005(15) 0.0136(2) Uani 1 1 d . . . . .
H40 H 1.0805 0.6793 0.2276 0.016 Uiso 1 1 calc R U . . .
C41 C 0.85710(18) 0.71499(4) 0.10638(15) 0.0127(2) Uani 1 1 d . . . . .
C42 C 0.9650(2) 0.75610(5) 0.04801(16) 0.0167(2) Uani 1 1 d . . . . .
H42 H 1.0989 0.7596 0.0767 0.020 Uiso 1 1 calc R U . . .
C43 C 0.8779(2) 0.79098(5) -0.04949(17) 0.0188(2) Uani 1 1 d . . . . .
H43 H 0.9520 0.8183 -0.0880 0.023 Uiso 1 1 calc R U . . .
C44 C 0.6783(2) 0.78645(5) -0.09281(17) 0.0195(2) Uani 1 1 d . . . . .
H44 H 0.6198 0.8104 -0.1619 0.023 Uiso 1 1 calc R U . . .
C45 C 0.5689(2) 0.74767(5) -0.03554(16) 0.0174(2) Uani 1 1 d . . . . .
H45 H 0.4345 0.7452 -0.0640 0.021 Uiso 1 1 calc R U . . .
C46 C 0.65526(19) 0.71120(4) 0.06604(15) 0.0133(2) Uani 1 1 d . . . . .
C47 C 0.54711(19) 0.67055(5) 0.12767(16) 0.0153(2) Uani 1 1 d . . . . .
H47 H 0.4107 0.6685 0.1069 0.018 Uiso 1 1 calc R U . . .
C48 C 0.63736(19) 0.63413(5) 0.21697(15) 0.0151(2) Uani 1 1 d . . . . .
H48 H 0.5624 0.6071 0.2564 0.018 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 1.2126(16) . ?
O2 C3 1.3179(16) . ?
O2 H2 0.8400 . ?
C3 C4 1.5047(17) . ?
C4 N9 1.3357(15) . ?
C4 C5 1.3946(18) . ?
C5 C6 1.3894(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3941(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3904(17) . ?
C7 H7 0.9500 . ?
C8 N9 1.3412(16) . ?
C8 C10 1.5015(17) . ?
C10 O11 1.2353(16) . ?
C10 N12 1.3333(16) . ?
N12 C13 1.4625(16) . ?
N12 H12 0.8800 . ?
C13 C15 1.5159(17) . ?
C13 C14 1.5272(18) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3748(17) . ?
C15 C24 1.4239(18) . ?
C16 C17 1.4259(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.4158(18) . ?
C17 C22 1.4232(19) . ?
C18 C19 1.3769(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.413(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.4181(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.4189(18) . ?
C23 C24 1.3683(18) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 C27 1.2123(15) . ?
O26 C27 1.3197(16) . ?
O26 H26 0.8400 . ?
C27 C28 1.5020(17) . ?
C28 N33 1.3344(15) . ?
C28 C29 1.3951(17) . ?
C29 C30 1.3920(18) . ?
C29 H29 0.9500 . ?
C30 C31 1.3912(17) . ?
C30 H30 0.9500 . ?
C31 C32 1.3926(17) . ?
C31 H31 0.9500 . ?
C32 N33 1.3410(15) . ?
C32 C34 1.5017(17) . ?
C34 O35 1.2370(15) . ?
C34 N36 1.3368(16) . ?
N36 C37 1.4651(16) . ?
N36 H36 0.8800 . ?
C37 C39 1.5175(17) . ?
C37 C38 1.525(2) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.3749(17) . ?
C39 C48 1.4248(18) . ?
C40 C41 1.4232(17) . ?
C40 H40 0.9500 . ?
C41 C42 1.4176(17) . ?
C41 C46 1.4225(17) . ?
C42 C43 1.3735(18) . ?
C42 H42 0.9500 . ?
C43 C44 1.415(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.372(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.4209(17) . ?
C45 H45 0.9500 . ?
C46 C47 1.4190(18) . ?
C47 C48 1.3727(18) . ?
C47 H47 0.9500 . ?
C48 H48 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 O2 H2 109.5 . . ?
O1 C3 O2 125.29(12) . . ?
O1 C3 C4 122.36(12) . . ?
O2 C3 C4 112.35(11) . . ?
N9 C4 C5 123.17(11) . . ?
N9 C4 C3 117.72(11) . . ?
C5 C4 C3 119.11(11) . . ?
C6 C5 C4 118.43(12) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 119.15(12) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 117.89(12) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
N9 C8 C7 123.68(11) . . ?
N9 C8 C10 115.62(10) . . ?
C7 C8 C10 120.68(11) . . ?
C4 N9 C8 117.65(10) . . ?
O11 C10 N12 123.11(12) . . ?
O11 C10 C8 121.87(11) . . ?
N12 C10 C8 115.02(11) . . ?
C10 N12 C13 122.78(10) . . ?
C10 N12 H12 118.6 . . ?
C13 N12 H12 118.6 . . ?
N12 C13 C15 109.65(9) . . ?
N12 C13 C14 110.56(10) . . ?
C15 C13 C14 115.18(10) . . ?
N12 C13 H13 107.0 . . ?
C15 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C24 118.91(12) . . ?
C16 C15 C13 123.69(11) . . ?
C24 C15 C13 117.40(11) . . ?
C15 C16 C17 121.34(12) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C22 119.20(12) . . ?
C18 C17 C16 121.83(12) . . ?
C22 C17 C16 118.97(11) . . ?
C19 C18 C17 120.39(13) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.59(13) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.03(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.83(14) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 122.19(12) . . ?
C21 C22 C17 118.97(12) . . ?
C23 C22 C17 118.84(11) . . ?
C24 C23 C22 120.70(12) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C15 121.23(12) . . ?
C23 C24 H24 119.4 . . ?
C15 C24 H24 119.4 . . ?
C27 O26 H26 109.5 . . ?
O25 C27 O26 124.95(12) . . ?
O25 C27 C28 122.46(12) . . ?
O26 C27 C28 112.59(10) . . ?
N33 C28 C29 123.26(11) . . ?
N33 C28 C27 117.85(11) . . ?
C29 C28 C27 118.89(11) . . ?
C30 C29 C28 118.34(11) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C31 C30 C29 119.24(11) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 117.74(11) . . ?
C30 C31 H31 121.1 . . ?
C32 C31 H31 121.1 . . ?
N33 C32 C31 123.86(11) . . ?
N33 C32 C34 115.70(10) . . ?
C31 C32 C34 120.45(11) . . ?
C28 N33 C32 117.54(10) . . ?
O35 C34 N36 123.01(12) . . ?
O35 C34 C32 122.22(11) . . ?
N36 C34 C32 114.77(10) . . ?
C34 N36 C37 123.05(10) . . ?
C34 N36 H36 118.5 . . ?
C37 N36 H36 118.5 . . ?
N36 C37 C39 108.87(10) . . ?
N36 C37 C38 109.25(11) . . ?
C39 C37 C38 114.97(11) . . ?
N36 C37 H37 107.8 . . ?
C39 C37 H37 107.8 . . ?
C38 C37 H37 107.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C48 118.68(11) . . ?
C40 C39 C37 122.90(11) . . ?
C48 C39 C37 118.41(11) . . ?
C39 C40 C41 121.51(11) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C40 121.97(11) . . ?
C42 C41 C46 118.86(11) . . ?
C40 C41 C46 119.15(11) . . ?
C43 C42 C41 120.72(13) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C42 C43 C44 120.33(12) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C45 C44 C43 120.35(12) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 120.42(12) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C47 C46 C45 122.12(12) . . ?
C47 C46 C41 118.59(11) . . ?
C45 C46 C41 119.29(11) . . ?
C48 C47 C46 120.76(12) . . ?
C48 C47 H47 119.6 . . ?
C46 C47 H47 119.6 . . ?
C47 C48 C39 121.15(11) . . ?
C47 C48 H48 119.4 . . ?
C39 C48 H48 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 N9 -179.16(13) . . . . ?
O2 C3 C4 N9 0.24(17) . . . . ?
O1 C3 C4 C5 0.68(19) . . . . ?
O2 C3 C4 C5 -179.92(12) . . . . ?
N9 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C6 -178.78(12) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C6 C7 C8 N9 0.8(2) . . . . ?
C6 C7 C8 C10 -178.03(12) . . . . ?
C5 C4 N9 C8 -1.71(19) . . . . ?
C3 C4 N9 C8 178.12(11) . . . . ?
C7 C8 N9 C4 0.74(19) . . . . ?
C10 C8 N9 C4 179.67(11) . . . . ?
N9 C8 C10 O11 170.53(14) . . . . ?
C7 C8 C10 O11 -10.5(2) . . . . ?
N9 C8 C10 N12 -9.75(17) . . . . ?
C7 C8 C10 N12 169.21(12) . . . . ?
O11 C10 N12 C13 5.2(2) . . . . ?
C8 C10 N12 C13 -174.52(11) . . . . ?
C10 N12 C13 C15 -128.25(13) . . . . ?
C10 N12 C13 C14 103.69(14) . . . . ?
N12 C13 C15 C16 -105.62(13) . . . . ?
C14 C13 C15 C16 19.84(17) . . . . ?
N12 C13 C15 C24 74.28(14) . . . . ?
C14 C13 C15 C24 -160.27(11) . . . . ?
C24 C15 C16 C17 -0.12(18) . . . . ?
C13 C15 C16 C17 179.77(11) . . . . ?
C15 C16 C17 C18 -179.29(12) . . . . ?
C15 C16 C17 C22 0.35(18) . . . . ?
C22 C17 C18 C19 -0.07(19) . . . . ?
C16 C17 C18 C19 179.57(12) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C23 -179.57(13) . . . . ?
C20 C21 C22 C17 0.34(19) . . . . ?
C18 C17 C22 C21 -0.25(18) . . . . ?
C16 C17 C22 C21 -179.89(11) . . . . ?
C18 C17 C22 C23 179.67(12) . . . . ?
C16 C17 C22 C23 0.02(18) . . . . ?
C21 C22 C23 C24 179.28(13) . . . . ?
C17 C22 C23 C24 -0.63(19) . . . . ?
C22 C23 C24 C15 0.9(2) . . . . ?
C16 C15 C24 C23 -0.50(19) . . . . ?
C13 C15 C24 C23 179.60(12) . . . . ?
O25 C27 C28 N33 -178.38(12) . . . . ?
O26 C27 C28 N33 0.84(17) . . . . ?
O25 C27 C28 C29 1.04(19) . . . . ?
O26 C27 C28 C29 -179.74(12) . . . . ?
N33 C28 C29 C30 -1.07(19) . . . . ?
C27 C28 C29 C30 179.54(12) . . . . ?
C28 C29 C30 C31 1.14(19) . . . . ?
C29 C30 C31 C32 -0.1(2) . . . . ?
C30 C31 C32 N33 -1.2(2) . . . . ?
C30 C31 C32 C34 179.11(12) . . . . ?
C29 C28 N33 C32 -0.13(18) . . . . ?
C27 C28 N33 C32 179.26(11) . . . . ?
C31 C32 N33 C28 1.29(19) . . . . ?
C34 C32 N33 C28 -178.98(11) . . . . ?
N33 C32 C34 O35 177.84(13) . . . . ?
C31 C32 C34 O35 -2.4(2) . . . . ?
N33 C32 C34 N36 -1.64(17) . . . . ?
C31 C32 C34 N36 178.10(12) . . . . ?
O35 C34 N36 C37 8.1(2) . . . . ?
C32 C34 N36 C37 -172.44(11) . . . . ?
C34 N36 C37 C39 -140.86(13) . . . . ?
C34 N36 C37 C38 92.86(15) . . . . ?
N36 C37 C39 C40 -132.42(12) . . . . ?
C38 C37 C39 C40 -9.50(17) . . . . ?
N36 C37 C39 C48 48.22(14) . . . . ?
C38 C37 C39 C48 171.13(11) . . . . ?
C48 C39 C40 C41 -3.48(18) . . . . ?
C37 C39 C40 C41 177.16(11) . . . . ?
C39 C40 C41 C42 -177.76(12) . . . . ?
C39 C40 C41 C46 0.38(18) . . . . ?
C40 C41 C42 C43 176.32(12) . . . . ?
C46 C41 C42 C43 -1.82(19) . . . . ?
C41 C42 C43 C44 0.2(2) . . . . ?
C42 C43 C44 C45 1.2(2) . . . . ?
C43 C44 C45 C46 -0.9(2) . . . . ?
C44 C45 C46 C47 -179.98(13) . . . . ?
C44 C45 C46 C41 -0.71(19) . . . . ?
C42 C41 C46 C47 -178.65(12) . . . . ?
C40 C41 C46 C47 3.16(17) . . . . ?
C42 C41 C46 C45 2.06(18) . . . . ?
C40 C41 C46 C45 -176.14(12) . . . . ?
C45 C46 C47 C48 175.69(12) . . . . ?
C41 C46 C47 C48 -3.59(18) . . . . ?
C46 C47 C48 C39 0.48(19) . . . . ?
C40 C39 C48 C47 3.08(18) . . . . ?
C37 C39 C48 C47 -177.53(11) . . . . ?

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
C31 H31 O25 0.95 2.54 3.4876(17) 172 1_556
O26 H26 O35 0.84 1.80 2.5915(14) 156 1_554
C14 H14A O26 0.98 2.53 3.2426(17) 129 1_556
C7 H7 O1 0.95 2.53 3.4744(17) 174 1_556
O2 H2 O11 0.84 1.77 2.5740(14) 159 1_554


_refine_diff_density_max         0.352
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999268'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6R

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O3'
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.4249(2)
_cell_length_b                   16.5948(6)
_cell_length_c                   11.4170(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.277(2)
_cell_angle_gamma                90
_cell_volume                     1017.11(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5363
_cell_measurement_theta_min      2.662
_cell_measurement_theta_max      65.817

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5609
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5614
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.912
_diffrn_reflns_theta_max         66.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.676
_diffrn_reflns_point_group_measured_fraction_full 0.653
_reflns_number_total             2414
_reflns_number_gt                2401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.355
_reflns_Friedel_fraction_max     0.368
_reflns_Friedel_fraction_full    0.356

_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       'Bruker APEX2, (Bruker 2012)'
_computing_cell_refinement       'Bruker SAINT, (Bruker 2012)'
_computing_data_reduction        'Bruker SAINT, (Bruker 2012)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL v. 2008/4, (Bruker 2008)'
_computing_publication_material  'Bruker APEX2, (Bruker 2012)'

_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)+(0.0533P)²+0.1345P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.11(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2414
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_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 1.0502(3) 0.57929(10) 0.13092(14) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.3092(3) 0.28945(10) 0.05391(13) 0.0249(3) Uani 1 1 d . . . . .
O3 O 0.0208(2) 0.34158(9) -0.08750(13) 0.0232(3) Uani 1 1 d . . . . .
N1 N 1.0113(3) 0.45290(11) 0.20032(15) 0.0236(4) Uani 1 1 d . . . . .
H1X H 0.9176 0.4065 0.1925 0.050 Uiso 1 1 d . . . . .
N2 N 0.5795(3) 0.43238(11) 0.05143(14) 0.0192(4) Uani 1 1 d . . . . .
C1 C 1.2435(3) 0.57484(14) 0.44493(18) 0.0225(4) Uani 1 1 d . . . . .
H1 H 1.3756 0.5975 0.4095 0.027 Uiso 1 1 calc R U . . .
C2 C 1.1612(4) 0.61518(14) 0.54304(17) 0.0229(4) Uani 1 1 d . . . . .
C3 C 1.2705(4) 0.68691(14) 0.59141(19) 0.0267(5) Uani 1 1 d . . . . .
H3 H 1.4049 0.7103 0.5585 0.032 Uiso 1 1 calc R U . . .
C4 C 1.1849(4) 0.72329(15) 0.6854(2) 0.0301(5) Uani 1 1 d . . . . .
H4 H 1.2628 0.7711 0.7181 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9827(4) 0.69052(15) 0.73409(19) 0.0301(5) Uani 1 1 d . . . . .
H5 H 0.9233 0.7168 0.7985 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8722(4) 0.62145(15) 0.6892(2) 0.0283(5) Uani 1 1 d . . . . .
H6 H 0.7349 0.6001 0.7221 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9594(4) 0.58049(15) 0.59318(18) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.8530(3) 0.50777(15) 0.54701(19) 0.0272(5) Uani 1 1 d . . . . .
H8 H 0.7196 0.4844 0.5807 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9391(3) 0.47021(14) 0.45433(19) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.8664 0.4207 0.4252 0.031 Uiso 1 1 calc R U . . .
C10 C 1.1366(3) 0.50449(13) 0.40098(17) 0.0221(4) Uani 1 1 d . . . . .
C11 C 1.2204(3) 0.46092(14) 0.29677(18) 0.0227(4) Uani 1 1 d . . . . .
H11 H 1.3536 0.4937 0.2674 0.027 Uiso 1 1 calc R U . . .
C12 C 1.3250(4) 0.37763(15) 0.32959(18) 0.0285(5) Uani 1 1 d . . . . .
H12A H 1.3808 0.3526 0.2602 0.043 Uiso 1 1 calc R U . . .
H12B H 1.1953 0.3442 0.3565 0.043 Uiso 1 1 calc R U . . .
H12C H 1.4663 0.3824 0.3932 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9370(3) 0.51542(13) 0.12881(17) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.7013(4) 0.50166(13) 0.04368(17) 0.0203(4) Uani 1 1 d . . . . .
C15 C 0.6217(4) 0.56253(14) -0.03639(19) 0.0250(5) Uani 1 1 d . . . . .
H15 H 0.7148 0.6109 -0.0384 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4034(4) 0.55081(15) -0.11298(19) 0.0277(5) Uani 1 1 d . . . . .
H16 H 0.3435 0.5910 -0.1692 0.033 Uiso 1 1 calc R U . . .
C17 C 0.2730(3) 0.47957(14) -0.10656(18) 0.0251(5) Uani 1 1 d . . . . .
H17 H 0.1217 0.4702 -0.1579 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3679(3) 0.42202(14) -0.02351(17) 0.0196(4) Uani 1 1 d . . . . .
C19 C 0.2348(3) 0.34336(13) -0.01295(16) 0.0197(4) Uani 1 1 d . . . . .
C20 C -0.1286(4) 0.26966(14) -0.08736(18) 0.0233(4) Uani 1 1 d . . . . .
H20A H -0.1913 0.2643 -0.0105 0.028 Uiso 1 1 calc R U . . .
H20B H -0.0262 0.2217 -0.0986 0.028 Uiso 1 1 calc R U . . .
C21 C -0.3447(3) 0.27501(14) -0.18640(17) 0.0212(4) Uani 1 1 d . . . . .
C22 C -0.3956(4) 0.34365(16) -0.2546(2) 0.0278(5) Uani 1 1 d . . . . .
H22 H -0.2879 0.3889 -0.2423 0.033 Uiso 1 1 calc R U . . .
C23 C -0.6045(4) 0.34645(16) -0.3412(2) 0.0322(5) Uani 1 1 d . . . . .
H23 H -0.6397 0.3940 -0.3869 0.039 Uiso 1 1 calc R U . . .
C24 C -0.7602(4) 0.28096(17) -0.36120(19) 0.0302(5) Uani 1 1 d . . . . .
H24 H -0.9016 0.2831 -0.4208 0.036 Uiso 1 1 calc R U . . .
C25 C -0.7097(4) 0.21158(16) -0.2938(2) 0.0301(5) Uani 1 1 d . . . . .
H25 H -0.8164 0.1661 -0.3072 0.036 Uiso 1 1 calc R U . . .
C26 C -0.5027(4) 0.20898(15) -0.2067(2) 0.0268(5) Uani 1 1 d . . . . .
H26 H -0.4688 0.1616 -0.1605 0.032 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 C13 1.224(3) . ?
O2 C19 1.207(3) . ?
O3 C19 1.337(2) . ?
O3 C20 1.443(3) . ?
N1 C13 1.346(3) . ?
N1 C11 1.469(2) . ?
N1 H1X 0.9197 . ?
N2 C14 1.335(3) . ?
N2 C18 1.340(2) . ?
C1 C10 1.366(3) . ?
C1 C2 1.430(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(3) . ?
C2 C7 1.428(3) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.359(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.427(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(3) . ?
C8 C9 1.367(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.517(3) . ?
C11 C12 1.520(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.508(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.505(3) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.385(3) . ?
C21 C26 1.390(3) . ?
C22 C23 1.394(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 H26 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
C19 O3 C20 116.99(16) . . ?
C13 N1 C11 121.09(18) . . ?
C13 N1 H1X 118.3 . . ?
C11 N1 H1X 120.3 . . ?
C14 N2 C18 117.04(17) . . ?
C10 C1 C2 121.58(18) . . ?
C10 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C7 119.20(19) . . ?
C3 C2 C1 122.83(18) . . ?
C7 C2 C1 118.0(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 122.21(19) . . ?
C8 C7 C2 119.50(19) . . ?
C6 C7 C2 118.3(2) . . ?
C9 C8 C7 120.92(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 119.31(19) . . ?
C1 C10 C11 122.41(17) . . ?
C9 C10 C11 118.28(19) . . ?
N1 C11 C10 110.17(15) . . ?
N1 C11 C12 108.84(18) . . ?
C10 C11 C12 112.54(17) . . ?
N1 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 N1 123.39(18) . . ?
O1 C13 C14 121.38(19) . . ?
N1 C13 C14 115.24(17) . . ?
N2 C14 C15 124.05(18) . . ?
N2 C14 C13 118.00(17) . . ?
C15 C14 C13 117.94(18) . . ?
C16 C15 C14 118.12(19) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C17 118.99(19) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 118.70(18) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N2 C18 C17 123.09(19) . . ?
N2 C18 C19 115.91(17) . . ?
C17 C18 C19 121.00(17) . . ?
O2 C19 O3 124.53(19) . . ?
O2 C19 C18 124.92(17) . . ?
O3 C19 C18 110.54(17) . . ?
O3 C20 C21 109.05(17) . . ?
O3 C20 H20A 109.9 . . ?
C21 C20 H20A 109.9 . . ?
O3 C20 H20B 109.9 . . ?
C21 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C26 119.11(19) . . ?
C22 C21 C20 122.68(19) . . ?
C26 C21 C20 118.17(19) . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.71(19) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 178.88(19) . . . . ?
C10 C1 C2 C7 -1.1(3) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 180.0(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 178.24(19) . . . . ?
C5 C6 C7 C2 -1.8(3) . . . . ?
C3 C2 C7 C8 -178.53(19) . . . . ?
C1 C2 C7 C8 1.5(3) . . . . ?
C3 C2 C7 C6 1.6(3) . . . . ?
C1 C2 C7 C6 -178.46(19) . . . . ?
C6 C7 C8 C9 179.4(2) . . . . ?
C2 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C2 C1 C10 C9 -0.2(3) . . . . ?
C2 C1 C10 C11 179.77(18) . . . . ?
C8 C9 C10 C1 1.3(3) . . . . ?
C8 C9 C10 C11 -178.73(19) . . . . ?
C13 N1 C11 C10 78.0(2) . . . . ?
C13 N1 C11 C12 -158.16(17) . . . . ?
C1 C10 C11 N1 -121.07(19) . . . . ?
C9 C10 C11 N1 58.9(2) . . . . ?
C1 C10 C11 C12 117.3(2) . . . . ?
C9 C10 C11 C12 -62.7(2) . . . . ?
C11 N1 C13 O1 7.5(3) . . . . ?
C11 N1 C13 C14 -172.78(16) . . . . ?
C18 N2 C14 C15 0.1(3) . . . . ?
C18 N2 C14 C13 178.74(15) . . . . ?
O1 C13 C14 N2 -175.92(17) . . . . ?
N1 C13 C14 N2 4.3(2) . . . . ?
O1 C13 C14 C15 2.8(3) . . . . ?
N1 C13 C14 C15 -176.93(17) . . . . ?
N2 C14 C15 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 -178.77(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C14 N2 C18 C17 -0.3(3) . . . . ?
C14 N2 C18 C19 179.90(15) . . . . ?
C16 C17 C18 N2 0.4(3) . . . . ?
C16 C17 C18 C19 -179.72(18) . . . . ?
C20 O3 C19 O2 -0.3(3) . . . . ?
C20 O3 C19 C18 -179.89(15) . . . . ?
N2 C18 C19 O2 -2.8(3) . . . . ?
C17 C18 C19 O2 177.39(19) . . . . ?
N2 C18 C19 O3 176.79(15) . . . . ?
C17 C18 C19 O3 -3.1(2) . . . . ?
C19 O3 C20 C21 -173.37(15) . . . . ?
O3 C20 C21 C22 -6.5(3) . . . . ?
O3 C20 C21 C26 175.71(17) . . . . ?
C26 C21 C22 C23 0.8(3) . . . . ?
C20 C21 C22 C23 -176.99(19) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
C20 C21 C26 C25 177.66(19) . . . . ?

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
C12 H12A O2 0.98 2.56 3.461(3) 154 1_655
C20 H20B O1 0.99 2.39 3.236(3) 143 2_645

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999269'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6S

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O3'
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.4288(2)
_cell_length_b                   16.6067(6)
_cell_length_c                   11.4114(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.2867(18)
_cell_angle_gamma                90
_cell_volume                     1018.05(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4911
_cell_measurement_theta_min      5.327
_cell_measurement_theta_max      66.715

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5359
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.327
_diffrn_reflns_theta_max         64.986
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.709
_diffrn_reflns_point_group_measured_fraction_full 0.666
_reflns_number_total             2462
_reflns_number_gt                2448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.395
_reflns_Friedel_fraction_max     0.417
_reflns_Friedel_fraction_full    0.392

_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       'Bruker APEX2, (Bruker 2012)'
_computing_cell_refinement       'Bruker SAINT, (Bruker 2012)'
_computing_data_reduction        'Bruker SAINT, (Bruker 2012)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL v. 2008/4, (Bruker 2008)'
_computing_publication_material  'Bruker APEX2, (Bruker 2012)'

_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)+(0.0451P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.15(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_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 -0.0496(3) 0.42068(10) 0.86915(13) 0.0290(4) Uani 1 1 d . . . . .
O2 O 0.6906(3) 0.71051(9) 0.94596(12) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.9791(2) 0.65846(9) 1.08757(12) 0.0215(3) Uani 1 1 d . . . . .
N1 N -0.0113(3) 0.54697(11) 0.79964(14) 0.0219(4) Uani 1 1 d . . . . .
H1X H 0.0824 0.5935 0.8075 0.050 Uiso 1 1 d . . . . .
N2 N 0.4206(3) 0.56775(10) 0.94844(13) 0.0176(4) Uani 1 1 d . . . . .
C1 C -0.2431(4) 0.42504(13) 0.55492(17) 0.0207(4) Uani 1 1 d . . . . .
H1 H -0.3748 0.4022 0.5904 0.025 Uiso 1 1 calc R U . . .
C2 C -0.1607(4) 0.38500(14) 0.45708(16) 0.0215(4) Uani 1 1 d . . . . .
C3 C -0.2706(4) 0.31300(13) 0.40840(18) 0.0248(5) Uani 1 1 d . . . . .
H3 H -0.4053 0.2896 0.4411 0.030 Uiso 1 1 calc R U . . .
C4 C -0.1848(4) 0.27680(14) 0.31491(19) 0.0285(5) Uani 1 1 d . . . . .
H4 H -0.2627 0.2290 0.2824 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0176(4) 0.30923(15) 0.26574(17) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.0768 0.2828 0.2014 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1279(4) 0.37855(15) 0.31070(19) 0.0265(5) Uani 1 1 d . . . . .
H6 H 0.2649 0.4000 0.2777 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0405(4) 0.41932(14) 0.40659(17) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.1466(4) 0.49215(15) 0.45295(18) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.2801 0.5155 0.4194 0.031 Uiso 1 1 calc R U . . .
C9 C 0.0602(4) 0.52968(14) 0.54550(18) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.1326 0.5792 0.5746 0.030 Uiso 1 1 calc R U . . .
C10 C -0.1369(4) 0.49547(13) 0.59876(16) 0.0207(4) Uani 1 1 d . . . . .
C11 C -0.2201(3) 0.53890(13) 0.70308(17) 0.0210(4) Uani 1 1 d . . . . .
H11 H -0.3531 0.5061 0.7324 0.025 Uiso 1 1 calc R U . . .
C12 C -0.3251(4) 0.62234(15) 0.67041(18) 0.0269(5) Uani 1 1 d . . . . .
H12A H -0.3828 0.6469 0.7397 0.040 Uiso 1 1 calc R U . . .
H12B H -0.4650 0.6177 0.6061 0.040 Uiso 1 1 calc R U . . .
H12C H -0.1951 0.6561 0.6444 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0633(4) 0.48452(13) 0.87106(16) 0.0196(4) Uani 1 1 d . . . . .
C14 C 0.2993(4) 0.49827(12) 0.95633(16) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.3793(4) 0.43741(13) 1.03630(17) 0.0228(4) Uani 1 1 d . . . . .
H15 H 0.2867 0.3890 1.0382 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5976(4) 0.44926(14) 1.11312(18) 0.0261(5) Uani 1 1 d . . . . .
H16 H 0.6576 0.4092 1.1694 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7272(4) 0.52050(14) 1.10659(17) 0.0231(4) Uani 1 1 d . . . . .
H17 H 0.8785 0.5299 1.1578 0.028 Uiso 1 1 calc R U . . .
C18 C 0.6317(4) 0.57813(13) 1.02346(16) 0.0184(4) Uani 1 1 d . . . . .
C19 C 0.7652(3) 0.65654(13) 1.01298(15) 0.0178(4) Uani 1 1 d . . . . .
C20 C 1.1286(4) 0.73051(13) 1.08712(18) 0.0217(4) Uani 1 1 d . . . . .
H20A H 1.0265 0.7785 1.0984 0.026 Uiso 1 1 calc R U . . .
H20B H 1.1912 0.7358 1.0102 0.026 Uiso 1 1 calc R U . . .
C21 C 1.3446(4) 0.72494(13) 1.18620(16) 0.0198(4) Uani 1 1 d . . . . .
C22 C 1.3962(4) 0.65639(15) 1.25475(18) 0.0261(5) Uani 1 1 d . . . . .
H22 H 1.2885 0.6111 1.2425 0.031 Uiso 1 1 calc R U . . .
C23 C 1.6044(4) 0.65347(16) 1.34130(19) 0.0308(5) Uani 1 1 d . . . . .
H23 H 1.6392 0.6060 1.3871 0.037 Uiso 1 1 calc R U . . .
C24 C 1.7608(4) 0.71907(16) 1.36100(18) 0.0285(5) Uani 1 1 d . . . . .
H24 H 1.9029 0.7169 1.4202 0.034 Uiso 1 1 calc R U . . .
C25 C 1.7093(4) 0.78837(15) 1.29376(19) 0.0287(5) Uani 1 1 d . . . . .
H25 H 1.8154 0.8339 1.3074 0.034 Uiso 1 1 calc R U . . .
C26 C 1.5028(4) 0.79105(14) 1.20670(19) 0.0257(4) Uani 1 1 d . . . . .
H26 H 1.4690 0.8385 1.1606 0.031 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 C13 1.223(3) . ?
O2 C19 1.210(2) . ?
O3 C19 1.338(2) . ?
O3 C20 1.446(3) . ?
N1 C13 1.345(3) . ?
N1 C11 1.469(2) . ?
N1 H1X 0.9224 . ?
N2 C14 1.338(3) . ?
N2 C18 1.339(2) . ?
C1 C10 1.367(3) . ?
C1 C2 1.426(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.414(3) . ?
C2 C7 1.425(3) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.425(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(3) . ?
C8 C9 1.366(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.515(3) . ?
C11 C12 1.524(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.510(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.503(3) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.387(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 H26 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
C19 O3 C20 116.97(15) . . ?
C13 N1 C11 121.11(17) . . ?
C13 N1 H1X 118.3 . . ?
C11 N1 H1X 120.3 . . ?
C14 N2 C18 116.88(16) . . ?
C10 C1 C2 121.50(18) . . ?
C10 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C7 118.95(18) . . ?
C3 C2 C1 122.67(19) . . ?
C7 C2 C1 118.38(19) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.17(19) . . ?
C8 C7 C2 119.15(19) . . ?
C6 C7 C2 118.7(2) . . ?
C9 C8 C7 120.95(19) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.74(19) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C1 C10 C9 119.26(18) . . ?
C1 C10 C11 122.49(18) . . ?
C9 C10 C11 118.24(18) . . ?
N1 C11 C10 110.34(16) . . ?
N1 C11 C12 108.75(17) . . ?
C10 C11 C12 112.57(16) . . ?
N1 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 N1 123.44(17) . . ?
O1 C13 C14 121.27(18) . . ?
N1 C13 C14 115.29(17) . . ?
N2 C14 C15 124.16(17) . . ?
N2 C14 C13 117.85(16) . . ?
C15 C14 C13 117.98(17) . . ?
C16 C15 C14 118.12(19) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C17 118.90(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 118.79(17) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N2 C18 C17 123.14(19) . . ?
N2 C18 C19 116.02(16) . . ?
C17 C18 C19 120.84(17) . . ?
O2 C19 O3 124.44(18) . . ?
O2 C19 C18 124.80(16) . . ?
O3 C19 C18 110.75(15) . . ?
O3 C20 C21 108.80(16) . . ?
O3 C20 H20A 109.9 . . ?
C21 C20 H20A 109.9 . . ?
O3 C20 H20B 109.9 . . ?
C21 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C26 118.87(18) . . ?
C22 C21 C20 122.99(18) . . ?
C26 C21 C20 118.10(19) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.60(19) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -178.65(18) . . . . ?
C10 C1 C2 C7 1.3(3) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.84(19) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -178.34(18) . . . . ?
C5 C6 C7 C2 1.8(3) . . . . ?
C3 C2 C7 C8 178.45(18) . . . . ?
C1 C2 C7 C8 -1.5(3) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C1 C2 C7 C6 178.44(18) . . . . ?
C6 C7 C8 C9 -179.54(19) . . . . ?
C2 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C2 C1 C10 C9 0.1(3) . . . . ?
C2 C1 C10 C11 -179.62(17) . . . . ?
C8 C9 C10 C1 -1.2(3) . . . . ?
C8 C9 C10 C11 178.49(18) . . . . ?
C13 N1 C11 C10 -77.9(2) . . . . ?
C13 N1 C11 C12 158.18(18) . . . . ?
C1 C10 C11 N1 120.83(19) . . . . ?
C9 C10 C11 N1 -58.9(2) . . . . ?
C1 C10 C11 C12 -117.5(2) . . . . ?
C9 C10 C11 C12 62.8(2) . . . . ?
C11 N1 C13 O1 -7.7(3) . . . . ?
C11 N1 C13 C14 172.65(16) . . . . ?
C18 N2 C14 C15 -0.2(3) . . . . ?
C18 N2 C14 C13 -178.86(15) . . . . ?
O1 C13 C14 N2 176.07(17) . . . . ?
N1 C13 C14 N2 -4.3(2) . . . . ?
O1 C13 C14 C15 -2.7(3) . . . . ?
N1 C13 C14 C15 176.95(17) . . . . ?
N2 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 C16 178.91(18) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C14 N2 C18 C17 0.4(3) . . . . ?
C14 N2 C18 C19 179.91(15) . . . . ?
C16 C17 C18 N2 -0.6(3) . . . . ?
C16 C17 C18 C19 179.90(18) . . . . ?
C20 O3 C19 O2 0.2(3) . . . . ?
C20 O3 C19 C18 179.87(16) . . . . ?
N2 C18 C19 O2 2.9(3) . . . . ?
C17 C18 C19 O2 -177.48(19) . . . . ?
N2 C18 C19 O3 -176.72(15) . . . . ?
C17 C18 C19 O3 2.8(2) . . . . ?
C19 O3 C20 C21 173.47(15) . . . . ?
O3 C20 C21 C22 6.5(3) . . . . ?
O3 C20 C21 C26 -175.58(17) . . . . ?
C26 C21 C22 C23 -0.9(3) . . . . ?
C20 C21 C22 C23 177.04(19) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C20 C21 C26 C25 -177.7(2) . . . . ?

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
C12 H12A O2 0.98 2.56 3.459(3) 153 1_455
C20 H20A O1 0.99 2.39 3.235(3) 143 2_657

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999270'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sal24

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C57 H42 Eu N6 O9, 2.5(H2 O)'
_chemical_formula_sum            'C57 H49.50 Eu N6 O11.50'
_chemical_formula_weight         1154.49
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C222(1)
_symmetry_space_group_name_Hall  'C 2c 2'

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

_cell_length_a                   26.0015(12)
_cell_length_b                   26.4029(11)
_cell_length_c                   30.8305(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     21165.6(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9422
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      46.88

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.038
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             9416
_exptl_absorpt_coefficient_mu    9.048
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.1846
_exptl_absorpt_correction_T_max  0.7249
_exptl_absorpt_process_details   'APEX2 default values. r=0.2'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36491
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.1200
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         50.55
_reflns_number_total             9417
_reflns_number_gt                5646
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1752P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.000104(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_number_reflns         9417
_refine_ls_number_parameters     905
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2618
_refine_ls_wR_factor_gt          0.2161
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.24418(7) 0.33668(5) 0.70231(3) 0.0848(6) Uani 1 1 d . . .
O9 O 0.2932(6) 0.3654(4) 0.7663(4) 0.075(5) Uani 1 1 d . . .
O1 O 0.2783(6) 0.2574(5) 0.7261(4) 0.081(5) Uani 1 1 d . . .
O8 O 0.0961(8) 0.2597(7) 0.7371(4) 0.100(5) Uani 1 1 d . . .
O4 O 0.3216(6) 0.3388(6) 0.6667(4) 0.101(5) Uani 1 1 d . . .
O3 O 0.2116(7) 0.3602(5) 0.6311(4) 0.100(6) Uani 1 1 d . . .
N1 N 0.2497(7) 0.2693(7) 0.6436(5) 0.076(5) Uani 1 1 d U . .
C44 C 0.2306(9) 0.3313(9) 0.8133(6) 0.071(6) Uani 1 1 d U . .
C2 C 0.2724(9) 0.2267(10) 0.6534(7) 0.085(7) Uani 1 1 d U . .
N5 N 0.2044(10) 0.3174(6) 0.7778(4) 0.073(6) Uani 1 1 d . . .
O2 O 0.3055(8) 0.1766(7) 0.7124(4) 0.117(7) Uani 1 1 d . . .
O5 O 0.3823(7) 0.3771(7) 0.6233(5) 0.125(6) Uani 1 1 d . . .
C1 C 0.2854(10) 0.2197(13) 0.7021(7) 0.089(8) Uani 1 1 d . . .
C40 C 0.1574(10) 0.2970(10) 0.7803(6) 0.070(7) Uani 1 1 d . . .
C68 C 0.4787(2) 0.1476(3) 0.43284(17) 0.171(5) Uani 1 1 d G . .
H68 H 0.4912 0.1150 0.4252 0.206 Uiso 1 1 calc R . .
C67 C 0.5110(2) 0.1891(3) 0.43035(15) 0.171(5) Uani 1 1 d GU . .
C76 C 0.4928(2) 0.2365(2) 0.44154(14) 0.171(5) Uani 1 1 d G . .
H76 H 0.5149 0.2651 0.4399 0.206 Uiso 1 1 calc R . .
C75 C 0.4426(2) 0.2424(2) 0.45504(13) 0.171(5) Uani 1 1 d G . .
H75 H 0.4302 0.2750 0.4627 0.206 Uiso 1 1 calc R . .
C74 C 0.4105(2) 0.2009(2) 0.45750(15) 0.171(5) Uani 1 1 d GU . .
C69 C 0.4285(2) 0.1533(3) 0.44633(16) 0.171(5) Uani 1 1 d GU . .
C70 C 0.3964(2) 0.1119(3) 0.44879(19) 0.171(5) Uani 1 1 d GU . .
H70 H 0.4088 0.0793 0.4411 0.206 Uiso 1 1 calc R . .
C71 C 0.3462(2) 0.1178(3) 0.46236(19) 0.171(5) Uani 1 1 d GU . .
H71 H 0.3240 0.0893 0.4640 0.206 Uiso 1 1 calc R . .
C72 C 0.3281(2) 0.1653(3) 0.47357(17) 0.171(5) Uani 1 1 d GU . .
H72 H 0.2935 0.1694 0.4829 0.206 Uiso 1 1 calc R . .
C73 C 0.3603(2) 0.2067(2) 0.47115(15) 0.171(5) Uani 1 1 d GU . .
H73 H 0.3479 0.2393 0.4789 0.206 Uiso 1 1 calc R . .
C98 C 0.7953(3) 0.1805(3) 0.6167(2) 0.087(8) Uani 1 1 d G . .
H98 H 0.8247 0.1661 0.6032 0.105 Uiso 1 1 calc R . .
O14 O 0.5793(2) 0.0941(2) 0.59763(17) 0.165(9) Uani 1 1 d G . .
C83 C 0.53204(19) 0.30437(18) 0.55570(12) 0.084(8) Uani 1 1 d GU . .
C43 C 0.2126(3) 0.3265(3) 0.85309(19) 0.092(8) Uani 1 1 d G . .
H43 H 0.2319 0.3363 0.8779 0.110 Uiso 1 1 calc R . .
C102 C 0.6571(2) 0.2440(2) 0.66501(16) 0.078(7) Uani 1 1 d GU . .
O7 O 0.1622(2) 0.2931(2) 0.70431(18) 0.098(6) Uani 1 1 d G . .
C97 C 0.7586(3) 0.1994(3) 0.59211(19) 0.087(8) Uani 1 1 d G . .
C103 C 0.5952(2) 0.2531(2) 0.72260(15) 0.142(10) Uiso 1 1 d GD . .
C48 C 0.3411(2) 0.4578(2) 0.82079(18) 0.062(6) Uani 1 1 d GU . .
N2 N 0.2039(2) 0.3489(3) 0.55800(16) 0.141(10) Uani 1 1 d GU . .
H2 H 0.2105 0.3304 0.5350 0.169 Uiso 1 1 calc R . .
C6 C 0.2417(2) 0.2802(2) 0.60140(15) 0.079(7) Uani 1 1 d G . .
C65 C 0.5634(2) 0.1854(3) 0.41180(16) 0.119(10) Uani 1 1 d G . .
H65 H 0.5824 0.1601 0.4298 0.142 Uiso 1 1 calc R . .
C5 C 0.2546(2) 0.2463(2) 0.56998(15) 0.099(8) Uani 1 1 d G . .
H5 H 0.2484 0.2543 0.5404 0.119 Uiso 1 1 calc R . .
C100 C 0.7470(3) 0.2029(3) 0.6774(2) 0.080(7) Uani 1 1 d GU . .
H100 H 0.7426 0.2051 0.7079 0.096 Uiso 1 1 calc R . .
C45 C 0.2819(2) 0.3569(2) 0.80277(16) 0.084(8) Uani 1 1 d G . .
C7 C 0.2175(2) 0.3322(2) 0.59710(15) 0.085(7) Uani 1 1 d GU . .
C96 C 0.7574(3) 0.1946(3) 0.54021(19) 0.093(8) Uani 1 1 d G . .
C3 C 0.2864(2) 0.1896(2) 0.62167(16) 0.094(8) Uani 1 1 d G . .
H3 H 0.3023 0.1588 0.6301 0.112 Uiso 1 1 calc R . .
C20 C 0.34327(19) 0.37274(17) 0.65012(12) 0.110(9) Uiso 1 1 d G . .
N6 N 0.3127(2) 0.3737(2) 0.83581(17) 0.091(6) Uani 1 1 d G . .
H6 H 0.3041 0.3668 0.8628 0.110 Uiso 1 1 calc R . .
N10 N 0.49570(18) 0.34066(18) 0.55161(12) 0.099(6) Uani 1 1 d G . .
H10 H 0.4631 0.3323 0.5540 0.118 Uiso 1 1 calc R . .
C64 C 0.6120(2) 0.2488(2) 0.45190(15) 0.075(7) Uani 1 1 d GU . .
C56 C 0.2870(3) 0.5331(3) 0.8385(2) 0.125(11) Uani 1 1 d GU . .
H56 H 0.2601 0.5468 0.8557 0.150 Uiso 1 1 calc R . .
C82 C 0.51238(18) 0.25018(17) 0.56418(11) 0.097(8) Uani 1 1 d GD . .
C49 C 0.3644(2) 0.4851(2) 0.78913(19) 0.099(8) Uani 1 1 d G . .
H49 H 0.3864 0.4687 0.7689 0.119 Uiso 1 1 calc R . .
C26 C 0.2083(2) 0.4516(2) 0.72053(18) 0.111(9) Uiso 1 1 d G . .
C50 C 0.3553(3) 0.5419(3) 0.7859(2) 0.105(9) Uani 1 1 d GU . .
C46 C 0.3595(2) 0.4027(2) 0.82717(17) 0.084(7) Uani 1 1 d G . .
H46 H 0.3787 0.3897 0.8014 0.101 Uiso 1 1 calc R . .
C59 C 0.6801(2) 0.3527(2) 0.50356(18) 0.070(6) Uani 1 1 d GU . .
C63 C 0.6378(2) 0.2968(2) 0.45441(16) 0.087(8) Uani 1 1 d GU . .
C66 C 0.5694(3) 0.1685(3) 0.36382(18) 0.132(11) Uani 1 1 d G . .
H66A H 0.5510 0.1921 0.3449 0.198 Uiso 1 1 calc R . .
H66B H 0.5551 0.1344 0.3603 0.198 Uiso 1 1 calc R . .
H66C H 0.6060 0.1682 0.3560 0.198 Uiso 1 1 calc R . .
C84 C 0.5097(2) 0.39442(19) 0.54314(14) 0.105(9) Uani 1 1 d G . .
H84 H 0.5442 0.3996 0.5567 0.126 Uiso 1 1 calc R . .
C62 C 0.6421(3) 0.3320(3) 0.42241(18) 0.097(8) Uani 1 1 d G . .
H62 H 0.6258 0.3268 0.3952 0.116 Uiso 1 1 calc R . .
C4 C 0.2770(2) 0.1992(2) 0.58088(16) 0.100(9) Uani 1 1 d G . .
H4 H 0.2851 0.1750 0.5590 0.120 Uiso 1 1 calc R . .
C47 C 0.3918(3) 0.4020(3) 0.86803(18) 0.111(9) Uani 1 1 d G . .
H47A H 0.4283 0.4042 0.8603 0.167 Uiso 1 1 calc R . .
H47B H 0.3855 0.3704 0.8838 0.167 Uiso 1 1 calc R . .
H47C H 0.3824 0.4308 0.8864 0.167 Uiso 1 1 calc R . .
C55 C 0.3139(3) 0.5625(3) 0.8085(2) 0.106(9) Uani 1 1 d G . .
C87 C 0.4830(18) 0.3754(17) 0.4639(12) 0.23(3) Uani 1 1 d U . .
H87 H 0.4561 0.3545 0.4746 0.281 Uiso 1 1 calc R . .
C86 C 0.5180(13) 0.4002(10) 0.4932(10) 0.109(9) Uani 1 1 d U . .
C95 C 0.5518(16) 0.4349(13) 0.4786(11) 0.158(14) Uani 1 1 d . . .
H95 H 0.5727 0.4547 0.4974 0.190 Uiso 1 1 calc R . .
C94 C 0.5533(14) 0.4395(13) 0.4290(10) 0.184(19) Uani 1 1 d . . .
H94 H 0.5796 0.4613 0.4184 0.221 Uiso 1 1 calc R . .
C93 C 0.5253(11) 0.4191(12) 0.3990(10) 0.240(12) Uani 1 1 d GD . .
C88 C 0.4904(13) 0.3837(13) 0.4146(6) 0.240(12) Uani 1 1 d G . .
C89 C 0.4595(10) 0.3568(11) 0.3858(10) 0.240(12) Uani 1 1 d GDU . .
H89 H 0.4357 0.3325 0.3964 0.288 Uiso 1 1 calc R . .
C90 C 0.4636(11) 0.3654(12) 0.3414(9) 0.240(12) Uani 1 1 d GDU . .
H90 H 0.4426 0.3471 0.3218 0.288 Uiso 1 1 calc R . .
C91 C 0.4986(12) 0.4009(13) 0.3259(6) 0.240(12) Uani 1 1 d GDU . .
H91 H 0.5014 0.4068 0.2956 0.288 Uiso 1 1 calc R . .
C92 C 0.5294(10) 0.4278(11) 0.3547(11) 0.240(12) Uani 1 1 d GDU . .
H92 H 0.5532 0.4520 0.3440 0.288 Uiso 1 1 calc R . .
C77 C 0.5832(13) 0.1388(12) 0.5858(9) 0.097(8) Uani 1 1 d U . .
C81 C 0.4606(8) 0.2320(10) 0.5601(6) 0.102(9) Uani 1 1 d D . .
H81 H 0.4337 0.2550 0.5533 0.123 Uiso 1 1 calc R . .
C53 C 0.3342(17) 0.6427(12) 0.7768(10) 0.143(13) Uani 1 1 d U . .
H53 H 0.3299 0.6784 0.7758 0.172 Uiso 1 1 calc R . .
C57 C 0.3015(13) 0.4841(9) 0.8417(7) 0.123(11) Uani 1 1 d U . .
H57 H 0.2816 0.4643 0.8612 0.148 Uiso 1 1 calc R . .
C41 C 0.1346(12) 0.2908(9) 0.8187(7) 0.105(9) Uani 1 1 d . . .
H41 H 0.1010 0.2769 0.8208 0.126 Uiso 1 1 calc R . .
C85 C 0.4740(12) 0.4315(10) 0.5651(9) 0.136(11) Uani 1 1 d . . .
H85A H 0.4893 0.4654 0.5644 0.205 Uiso 1 1 calc R . .
H85B H 0.4685 0.4211 0.5952 0.205 Uiso 1 1 calc R . .
H85C H 0.4409 0.4320 0.5498 0.205 Uiso 1 1 calc R . .
C99 C 0.7925(10) 0.1807(10) 0.6620(7) 0.096(8) Uani 1 1 d . . .
H99 H 0.8186 0.1674 0.6803 0.116 Uiso 1 1 calc R . .
C60 C 0.6877(9) 0.3897(8) 0.4736(6) 0.084(8) Uani 1 1 d . . .
H60 H 0.7025 0.4213 0.4813 0.100 Uiso 1 1 calc R . .
C80 C 0.4493(14) 0.1796(12) 0.5661(8) 0.170(16) Uani 1 1 d DU . .
H80 H 0.4153 0.1675 0.5618 0.204 Uiso 1 1 calc R . .
C52 C 0.3714(14) 0.6237(13) 0.7541(12) 0.139(12) Uani 1 1 d U . .
H52 H 0.3917 0.6448 0.7359 0.167 Uiso 1 1 calc R . .
C28 C 0.099(2) 0.512(2) 0.7346(19) 0.29(3) Uiso 1 1 d . . .
H28A H 0.0888 0.4973 0.7068 0.436 Uiso 0.50 1 calc PR . .
H28B H 0.1229 0.5403 0.7294 0.436 Uiso 0.50 1 calc PR . .
H28C H 0.0683 0.5251 0.7495 0.436 Uiso 0.50 1 calc PR . .
H28D H 0.0978 0.5445 0.7504 0.436 Uiso 0.50 1 calc PR . .
H28E H 0.0638 0.5015 0.7278 0.436 Uiso 0.50 1 calc PR . .
H28F H 0.1183 0.5167 0.7076 0.436 Uiso 0.50 1 calc PR . .
C61 C 0.6725(11) 0.3790(11) 0.4303(6) 0.117(10) Uani 1 1 d . . .
H61 H 0.6815 0.4010 0.4071 0.141 Uiso 1 1 calc R . .
C42 C 0.1620(16) 0.3056(10) 0.8562(9) 0.146(14) Uani 1 1 d . . .
H42 H 0.1465 0.3015 0.8840 0.175 Uiso 1 1 calc R . .
C27 C 0.1217(14) 0.4772(18) 0.7591(14) 0.193(16) Uiso 1 1 d D . .
H27 H 0.1096 0.4416 0.7547 0.231 Uiso 1 1 calc R . .
C54 C 0.3011(16) 0.6165(11) 0.8017(10) 0.155(13) Uani 1 1 d U . .
H54 H 0.2714 0.6317 0.8141 0.186 Uiso 1 1 calc R . .
C39 C 0.1418(13) 0.2798(10) 0.7380(7) 0.087(8) Uani 1 1 d . . .
C78 C 0.5385(12) 0.1670(10) 0.5773(7) 0.091(7) Uani 1 1 d DU . .
N4 N 0.1806(11) 0.4908(8) 0.7393(9) 0.165(13) Uani 1 1 d D . .
H4A H 0.1933 0.5216 0.7408 0.198 Uiso 1 1 calc R . .
O20 O 0.5770(8) 0.2922(6) 0.3403(4) 0.120(6) Uani 1 1 d . . .
H20A H 0.5831 0.2777 0.3171 0.144 Uiso 1 1 d . . .
H20B H 0.5910 0.3209 0.3404 0.144 Uiso 1 1 d . . .
C79 C 0.4886(12) 0.1458(17) 0.5784(12) 0.187(17) Uani 1 1 d DU . .
H79 H 0.4821 0.1118 0.5867 0.225 Uiso 1 1 calc R . .
O19 O 0.3820(6) 0.3299(7) 0.5428(5) 0.112(5) Uani 1 1 d . . .
H19A H 0.3815 0.3442 0.5667 0.134 Uiso 1 1 d . . .
H19B H 0.3584 0.3274 0.5247 0.134 Uiso 1 1 d . . .
O23 O 0.1918(11) 0.5992(6) 0.7336(6) 0.179(11) Uani 1 1 d . . .
H23A H 0.1920 0.6239 0.7507 0.215 Uiso 1 1 d . . .
H23B H 0.1852 0.5971 0.7062 0.215 Uiso 1 1 d . . .
C8 C 0.1748(12) 0.4039(11) 0.5523(7) 0.150(12) Uani 1 1 d DU . .
H8A H 0.1508 0.4078 0.5774 0.180 Uiso 1 1 calc R . .
C51 C 0.3812(11) 0.5726(12) 0.7566(9) 0.130(11) Uani 1 1 d U . .
H51 H 0.4062 0.5581 0.7380 0.156 Uiso 1 1 calc R . .
C58 C 0.6983(9) 0.3549(10) 0.5506(7) 0.070(7) Uani 1 1 d . . .
C101 C 0.7078(10) 0.2220(8) 0.6511(6) 0.078(7) Uani 1 1 d U . .
N7 N 0.6592(7) 0.3072(6) 0.4945(5) 0.072(5) Uani 1 1 d . . .
N8 N 0.5939(8) 0.2365(7) 0.4155(5) 0.092(6) Uani 1 1 d . . .
H8 H 0.5984 0.2560 0.3927 0.110 Uiso 1 1 calc R . .
N9 N 0.5489(8) 0.2182(8) 0.5682(5) 0.082(6) Uani 1 1 d U . .
N11 N 0.7143(7) 0.2184(6) 0.6074(4) 0.066(5) Uani 1 1 d . . .
N12 N 0.6500(6) 0.2485(8) 0.7053(5) 0.091(6) Uani 1 1 d . A .
H12 H 0.6763 0.2489 0.7233 0.109 Uiso 1 1 calc R . .
O12 O 0.6109(6) 0.2226(6) 0.4850(5) 0.099(5) Uani 1 1 d . . .
O13 O 0.6290(7) 0.1577(5) 0.5774(3) 0.081(4) Uani 1 1 d . . .
O15 O 0.5780(5) 0.3099(5) 0.5542(4) 0.071(4) Uani 1 1 d . . .
O10 O 0.6900(6) 0.3182(6) 0.5741(4) 0.068(4) Uani 1 1 d . . .
O11 O 0.7176(6) 0.3966(7) 0.5610(4) 0.085(4) Uani 1 1 d . . .
O17 O 0.7987(8) 0.1803(8) 0.5229(5) 0.125(7) Uani 1 1 d . . .
O16 O 0.7165(6) 0.2116(6) 0.5249(4) 0.080(5) Uani 1 1 d . . .
O18 O 0.6273(6) 0.2548(5) 0.6354(4) 0.077(4) Uani 1 1 d . . .
Eu2 Eu 0.64255(6) 0.24550(5) 0.55791(3) 0.0743(6) Uani 1 1 d . . .
C23 C 0.3238(13) 0.5166(13) 0.6666(11) 0.136(11) Uani 1 1 d U . .
H23 H 0.3404 0.5483 0.6627 0.164 Uiso 1 1 calc R . .
C24 C 0.2756(12) 0.5133(11) 0.6881(9) 0.117(9) Uani 1 1 d U . .
H24 H 0.2573 0.5433 0.6954 0.140 Uiso 1 1 calc R . .
C25 C 0.2551(10) 0.4665(11) 0.6984(7) 0.087(7) Uiso 1 1 d . . .
N3 N 0.2788(8) 0.4251(7) 0.6842(5) 0.083(6) Uani 1 1 d . . .
C21 C 0.3271(12) 0.4257(10) 0.6623(7) 0.094(7) Uani 1 1 d U . .
C22 C 0.3460(11) 0.4722(10) 0.6513(9) 0.111(8) Uani 1 1 d U . .
H22 H 0.3751 0.4742 0.6328 0.133 Uiso 1 1 calc R . .
O24 O 0.1748(11) 0.5928(8) 0.6440(8) 0.188(11) Uani 1 1 d . . .
H24A H 0.1658 0.6233 0.6406 0.226 Uiso 1 1 d . . .
H24B H 0.1495 0.5743 0.6482 0.226 Uiso 1 1 d . . .
C104 C 0.5671(17) 0.1986(13) 0.7117(15) 0.084(14) Uiso 0.532(13) 1 d PD A -2
H10A H 0.5339 0.2049 0.6977 0.126 Uiso 0.532(13) 1 calc PR A -2
H10B H 0.5617 0.1798 0.7387 0.126 Uiso 0.532(13) 1 calc PR A -2
H10C H 0.5891 0.1788 0.6923 0.126 Uiso 0.532(13) 1 calc PR A -2
C105 C 0.5772(16) 0.2961(15) 0.7178(11) 0.070(12) Uiso 0.532(13) 1 d PD A -2
C9 C 0.1431(17) 0.4048(16) 0.5122(10) 0.23(2) Uani 1 1 d . . .
H9A H 0.1654 0.4101 0.4870 0.349 Uiso 0.50 1 calc PR . .
H9B H 0.1181 0.4325 0.5141 0.349 Uiso 0.50 1 calc PR . .
H9C H 0.1249 0.3725 0.5092 0.349 Uiso 0.50 1 calc PR . .
H9D H 0.1069 0.3999 0.5198 0.349 Uiso 0.50 1 calc PR . .
H9E H 0.1542 0.3776 0.4928 0.349 Uiso 0.50 1 calc PR . .
H9F H 0.1473 0.4375 0.4977 0.349 Uiso 0.50 1 calc PR . .
C15 C 0.363(3) 0.560(2) 0.5468(14) 0.36(2) Uiso 1 1 d D . .
H15 H 0.3850 0.5885 0.5486 0.431 Uiso 1 1 calc R . .
C13 C 0.3463(14) 0.473(3) 0.532(2) 0.36(2) Uiso 1 1 d D . .
H13 H 0.3571 0.4405 0.5212 0.431 Uiso 1 1 calc R . .
C10 C 0.2146(12) 0.4363(10) 0.5590(9) 0.199(7) Uiso 1 1 d GD . .
C19 C 0.1922(8) 0.4827(14) 0.5689(8) 0.199(7) Uiso 1 1 d G . .
H19 H 0.1568 0.4844 0.5764 0.239 Uiso 1 1 calc R . .
C18 C 0.2216(14) 0.5267(9) 0.5678(8) 0.199(7) Uiso 1 1 d GD . .
H18 H 0.2063 0.5584 0.5746 0.239 Uiso 1 1 calc R . .
C17 C 0.2734(13) 0.5242(10) 0.5568(9) 0.199(7) Uiso 1 1 d GD . .
C12 C 0.2958(8) 0.4779(14) 0.5469(9) 0.199(7) Uiso 1 1 d GD . .
C11 C 0.2664(13) 0.4339(10) 0.5480(8) 0.199(7) Uiso 1 1 d GD . .
H11 H 0.2817 0.4022 0.5412 0.239 Uiso 1 1 calc R . .
C30 C 0.1242(12) 0.5299(15) 0.8219(9) 0.319(11) Uiso 1 1 d G . .
H30 H 0.1036 0.5558 0.8094 0.383 Uiso 1 1 calc R . .
C29 C 0.1380(15) 0.4879(18) 0.7974(8) 0.319(11) Uiso 1 1 d G . .
C38 C 0.1682(15) 0.4500(15) 0.8157(12) 0.319(11) Uiso 1 1 d G . .
H38 H 0.1776 0.4213 0.7989 0.383 Uiso 1 1 calc R . .
C37 C 0.1846(12) 0.4542(11) 0.8584(12) 0.319(11) Uiso 1 1 d G . .
H37 H 0.2052 0.4284 0.8709 0.383 Uiso 1 1 calc R . .
C36 C 0.1708(8) 0.4963(10) 0.8829(8) 0.319(11) Uiso 1 1 d G . .
C31 C 0.1406(8) 0.5341(10) 0.8646(8) 0.319(11) Uiso 1 1 d G . .
C32 C 0.1268(12) 0.5762(10) 0.8891(13) 0.319(11) Uiso 1 1 d G . .
H32 H 0.1062 0.6021 0.8766 0.383 Uiso 1 1 calc R . .
C33 C 0.1432(14) 0.5804(14) 0.9319(12) 0.319(11) Uiso 1 1 d G . .
H33 H 0.1337 0.6092 0.9486 0.383 Uiso 1 1 calc R . .
C34 C 0.1733(14) 0.5426(18) 0.9502(8) 0.319(11) Uiso 1 1 d G . .
H34 H 0.1845 0.5455 0.9794 0.383 Uiso 1 1 calc R . .
C35 C 0.1872(11) 0.5005(15) 0.9257(9) 0.319(11) Uiso 1 1 d G . .
H35 H 0.2078 0.4746 0.9382 0.383 Uiso 1 1 calc R . .
O22 O 0.5000 0.123(3) 0.2500 0.33(3) Uani 1 2 d S . .
H22A H 0.4778 0.1420 0.2458 0.402 Uiso 1 1 d . . .
C14 C 0.382(3) 0.513(2) 0.5322(7) 0.36(2) Uiso 1 1 d D . .
H14 H 0.4162 0.5085 0.5229 0.431 Uiso 1 1 calc R . .
O21 O 0.5000 0.2851(17) 0.2500 0.37(5) Uani 1 2 d S . .
H21A H 0.4706 0.2709 0.2461 0.444 Uiso 1 1 d . . .
C114 C 0.5357(15) 0.3075(16) 0.6824(12) 0.072(12) Uiso 0.532(13) 1 d P A -2
H114 H 0.5269 0.2829 0.6612 0.087 Uiso 0.532(13) 1 calc PR A -2
C115 C 0.596(2) 0.2814(18) 0.7696(12) 0.097(18) Uiso 0.468(13) 1 d PD A 1
H11A H 0.5722 0.2639 0.7894 0.146 Uiso 0.234(6) 1 calc PR A 1
H11B H 0.5847 0.3167 0.7660 0.146 Uiso 0.234(6) 1 calc PR A 1
H11C H 0.6306 0.2806 0.7815 0.146 Uiso 0.234(6) 1 calc PR A 1
H11D H 0.6195 0.3102 0.7686 0.146 Uiso 0.234(6) 1 calc PR A 1
H11E H 0.6070 0.2575 0.7919 0.146 Uiso 0.234(6) 1 calc PR A 1
H11F H 0.5610 0.2935 0.7764 0.146 Uiso 0.234(6) 1 calc PR A 1
C112 C 0.5123(10) 0.3897(12) 0.7174(10) 0.089(14) Uiso 0.532(13) 1 d PGD A -2
C111 C 0.4841(12) 0.4344(14) 0.7148(10) 0.14(2) Uiso 0.532(13) 1 d PGD A -2
H111 H 0.4626 0.4405 0.6904 0.163 Uiso 0.532(13) 1 calc PR A -2
C110 C 0.4873(16) 0.4700(11) 0.7479(13) 0.121(18) Uiso 0.532(13) 1 d PGD A -2
H110 H 0.4680 0.5005 0.7461 0.145 Uiso 0.532(13) 1 calc PR A -2
C109 C 0.5187(16) 0.4610(11) 0.7835(11) 0.14(2) Uiso 0.532(13) 1 d PG A -2
H109 H 0.5209 0.4854 0.8061 0.173 Uiso 0.532(13) 1 calc PR A -2
C108 C 0.5469(13) 0.4164(13) 0.7861(10) 0.118(18) Uiso 0.532(13) 1 d PGD A -2
H108 H 0.5683 0.4103 0.8105 0.141 Uiso 0.532(13) 1 calc PR A -2
C107 C 0.5437(11) 0.3808(11) 0.7531(12) 0.124(18) Uiso 0.532(13) 1 d PGD A -2
O6 O 0.1922(6) 0.4078(6) 0.7248(5) 0.097(5) Uiso 1 1 d . . .
C106 C 0.576(2) 0.327(2) 0.7511(17) 0.119(18) Uiso 0.532(13) 1 d P A -2
H106 H 0.5952 0.3172 0.7761 0.143 Uiso 0.532(13) 1 calc PR A -2
C113 C 0.5128(19) 0.354(2) 0.6831(17) 0.112(17) Uiso 0.532(13) 1 d P A -2
H113 H 0.4950 0.3633 0.6574 0.135 Uiso 0.532(13) 1 calc PR A -2
C16 C 0.312(2) 0.562(2) 0.559(2) 0.36(2) Uiso 1 1 d D . .
H16 H 0.3007 0.5933 0.5698 0.431 Uiso 1 1 calc R . .
C124 C 0.4612(10) 0.2404(10) 0.6710(9) 0.100(17) Uiso 0.468(13) 1 d PG A 1
H124 H 0.4318 0.2583 0.6611 0.120 Uiso 0.468(13) 1 calc PR A 1
C125 C 0.5055(12) 0.2667(9) 0.6826(9) 0.082(15) Uiso 0.468(13) 1 d PG A 1
H125 H 0.5063 0.3026 0.6805 0.099 Uiso 0.468(13) 1 calc PR A 1
C116 C 0.5485(10) 0.2405(11) 0.6972(9) 0.064(12) Uiso 0.468(13) 1 d PG A 1
C117 C 0.5473(9) 0.1880(11) 0.7002(10) 0.093(19) Uiso 0.468(13) 1 d PG A 1
H117 H 0.5767 0.1701 0.7101 0.111 Uiso 0.468(13) 1 calc PR A 1
C118 C 0.5030(9) 0.1617(9) 0.6886(7) 0.14(2) Uiso 0.468(13) 1 d PG A 1
C123 C 0.4600(9) 0.1879(10) 0.6741(7) 0.12(2) Uiso 0.468(13) 1 d PG A 1
C122 C 0.4158(10) 0.1616(13) 0.6625(11) 0.15(2) Uiso 0.468(13) 1 d PG A 1
H122 H 0.3864 0.1795 0.6526 0.178 Uiso 0.468(13) 1 calc PR A 1
C121 C 0.4146(13) 0.1091(13) 0.6655(12) 0.14(2) Uiso 0.468(13) 1 d PG A 1
H121 H 0.3843 0.0911 0.6576 0.173 Uiso 0.468(13) 1 calc PR A 1
C120 C 0.4576(16) 0.0828(10) 0.6801(12) 0.17(3) Uiso 0.468(13) 1 d PG A 1
H120 H 0.4568 0.0470 0.6822 0.204 Uiso 0.468(13) 1 calc PR A 1
C119 C 0.5018(14) 0.1092(9) 0.6916(11) 0.15(3) Uiso 0.468(13) 1 d PG A 1
H119 H 0.5312 0.0912 0.7016 0.175 Uiso 0.468(13) 1 calc PR A 1


_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
Eu1 O4 2.294(15) . ?
Eu1 O1 2.389(14) . ?
Eu1 O6 2.415(15) . ?
Eu1 O7 2.423(6) . ?
Eu1 O3 2.432(12) . ?
Eu1 O9 2.469(12) . ?
Eu1 N1 2.542(15) . ?
Eu1 N3 2.564(18) . ?
Eu1 N5 2.596(17) . ?
O9 C45 1.183(13) . ?
O1 C1 1.25(3) . ?
O8 C39 1.30(3) . ?
O4 C20 1.175(13) . ?
O3 C7 1.293(13) . ?
N1 C2 1.30(2) . ?
N1 C6 1.349(16) . ?
C44 C43 1.32(2) . ?
C44 N5 1.34(2) . ?
C44 C45 1.53(2) . ?
C2 C3 1.43(2) . ?
C2 C1 1.55(3) . ?
N5 C40 1.34(2) . ?
O2 C1 1.29(3) . ?
O5 C20 1.312(18) . ?
C40 C41 1.33(3) . ?
C40 C39 1.44(3) . ?
C68 C69 1.3788 . ?
C68 C67 1.3803 . ?
C67 C76 1.3823 . ?
C67 C65 1.4821 . ?
C76 C75 1.3775 . ?
C75 C74 1.3799 . ?
C74 C73 1.3807 . ?
C74 C69 1.3839 . ?
C69 C70 1.3785 . ?
C70 C71 1.3790 . ?
C71 C72 1.3823 . ?
C72 C73 1.3780 . ?
C98 C97 1.3177 . ?
C98 C99 1.40(2) . ?
O14 C77 1.24(3) . ?
C83 O15 1.204(14) . ?
C83 N10 1.3515 . ?
C83 C82 1.5418 . ?
C43 C42 1.43(4) . ?
C102 O18 1.233(14) . ?
C102 N12 1.262(15) . ?
C102 C101 1.50(3) . ?
O7 C39 1.22(3) . ?
C97 N11 1.342(18) . ?
C97 C96 1.6053 . ?
C103 C105 1.24(4) . ?
C103 C116 1.48(3) . ?
C103 N12 1.527(16) . ?
C103 C115 1.63(3) . ?
C103 C104 1.65(3) . ?
C48 C49 1.3554 . ?
C48 C57 1.40(3) . ?
C48 C46 1.5429 . ?
N2 C7 1.3318 . ?
N2 C8 1.65(3) . ?
C6 C5 1.3615 . ?
C6 C7 1.5149 . ?
C65 C66 1.5533 . ?
C65 N8 1.57(2) . ?
C5 C4 1.4142 . ?
C100 C101 1.40(2) . ?
C100 C99 1.40(3) . ?
C45 N6 1.3680 . ?
C96 O16 1.248(17) . ?
C96 O17 1.257(18) . ?
C3 C4 1.3058 . ?
C20 C21 1.51(3) . ?
N6 C46 1.4643 . ?
N10 C84 1.4882 . ?
C64 O12 1.233(16) . ?
C64 N8 1.260(17) . ?
C64 C63 1.4352 . ?
C56 C57 1.35(3) . ?
C56 C55 1.3958 . ?
C82 N9 1.28(2) . ?
C82 C81 1.434(18) . ?
C49 C50 1.5219 . ?
C26 O6 1.237(16) . ?
C26 N4 1.39(3) . ?
C26 C25 1.45(3) . ?
C50 C51 1.39(3) . ?
C50 C55 1.3941 . ?
C46 C47 1.5141 . ?
C59 N7 1.348(18) . ?
C59 C60 1.36(2) . ?
C59 C58 1.53(2) . ?
C63 C62 1.3617 . ?
C63 N7 1.384(17) . ?
C84 C85 1.51(3) . ?
C84 C86 1.56(3) . ?
C62 C61 1.49(3) . ?
C55 C54 1.48(3) . ?
C87 C86 1.44(4) . ?
C87 C88 1.55(4) . ?
C86 C95 1.35(4) . ?
C95 C94 1.54(4) . ?
C94 C93 1.30(5) . ?
C93 C88 1.3900 . ?
C93 C92 1.3900 . ?
C88 C89 1.3900 . ?
C89 C90 1.3900 . ?
C90 C91 1.3900 . ?
C91 C92 1.3900 . ?
C77 O13 1.32(3) . ?
C77 C78 1.40(3) . ?
C81 C80 1.427(18) . ?
C53 C52 1.30(4) . ?
C53 C54 1.34(4) . ?
C41 C42 1.41(4) . ?
C60 C61 1.42(3) . ?
C80 C79 1.407(19) . ?
C52 C51 1.37(4) . ?
C28 C27 1.34(6) . ?
C27 C29 1.28(5) . ?
C27 N4 1.688(19) . ?
C78 N9 1.41(3) . ?
C78 C79 1.42(2) . ?
C8 C10 1.358(15) . ?
C8 C9 1.48(3) . ?
C58 O10 1.23(2) . ?
C58 O11 1.25(2) . ?
C101 N11 1.36(2) . ?
N7 Eu2 2.581(15) . ?
N9 Eu2 2.558(19) . ?
N11 Eu2 2.513(17) . ?
O12 Eu2 2.468(14) . ?
O13 Eu2 2.421(14) . ?
O15 Eu2 2.392(14) . ?
O10 Eu2 2.336(14) . ?
O16 Eu2 2.352(15) . ?
O18 Eu2 2.433(11) . ?
C23 C22 1.39(4) . ?
C23 C24 1.42(4) . ?
C24 C25 1.38(3) . ?
C25 N3 1.33(3) . ?
N3 C21 1.43(3) . ?
C21 C22 1.37(3) . ?
C105 C106 1.31(5) . ?
C105 C114 1.56(5) . ?
C15 C16 1.39(3) . ?
C15 C14 1.40(3) . ?
C13 C12 1.40(3) . ?
C13 C14 1.41(3) . ?
C10 C19 1.3900 . ?
C10 C11 1.3900 . ?
C19 C18 1.3900 . ?
C18 C17 1.3900 . ?
C17 C12 1.3900 . ?
C17 C16 1.40(3) . ?
C12 C11 1.3900 . ?
C30 C29 1.3900 . ?
C30 C31 1.3900 . ?
C29 C38 1.3900 . ?
C38 C37 1.3900 . ?
C37 C36 1.3900 . ?
C36 C31 1.3900 . ?
C36 C35 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C114 C113 1.36(5) . ?
C112 C111 1.3900 . ?
C112 C107 1.3900 . ?
C112 C113 1.42(5) . ?
C111 C110 1.3900 . ?
C110 C109 1.3900 . ?
C109 C108 1.3900 . ?
C108 C107 1.3900 . ?
C107 C106 1.66(6) . ?
C124 C125 1.3900 . ?
C124 C123 1.3900 . ?
C125 C116 1.3900 . ?
C116 C117 1.3900 . ?
C117 C118 1.3900 . ?
C118 C123 1.3900 . ?
C118 C119 1.3900 . ?
C123 C122 1.3900 . ?
C122 C121 1.3900 . ?
C121 C120 1.3900 . ?
C120 C119 1.3900 . ?

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
O4 Eu1 O1 80.9(5) . . ?
O4 Eu1 O6 127.6(5) . . ?
O1 Eu1 O6 143.2(5) . . ?
O4 Eu1 O7 142.7(4) . . ?
O1 Eu1 O7 84.4(4) . . ?
O6 Eu1 O7 82.5(4) . . ?
O4 Eu1 O3 82.4(6) . . ?
O1 Eu1 O3 129.0(4) . . ?
O6 Eu1 O3 82.3(5) . . ?
O7 Eu1 O3 80.7(4) . . ?
O4 Eu1 O9 85.5(5) . . ?
O1 Eu1 O9 80.3(4) . . ?
O6 Eu1 O9 79.7(5) . . ?
O7 Eu1 O9 125.4(4) . . ?
O3 Eu1 O9 145.3(5) . . ?
O4 Eu1 N1 68.1(5) . . ?
O1 Eu1 N1 65.4(5) . . ?
O6 Eu1 N1 141.3(6) . . ?
O7 Eu1 N1 74.6(4) . . ?
O3 Eu1 N1 63.7(5) . . ?
O9 Eu1 N1 139.0(5) . . ?
O4 Eu1 N3 64.2(7) . . ?
O1 Eu1 N3 137.3(6) . . ?
O6 Eu1 N3 63.3(6) . . ?
O7 Eu1 N3 138.3(5) . . ?
O3 Eu1 N3 72.1(5) . . ?
O9 Eu1 N3 73.3(4) . . ?
N1 Eu1 N3 117.6(6) . . ?
O4 Eu1 N5 141.5(6) . . ?
O1 Eu1 N5 72.6(5) . . ?
O6 Eu1 N5 70.8(5) . . ?
O7 Eu1 N5 62.2(5) . . ?
O3 Eu1 N5 136.0(7) . . ?
O9 Eu1 N5 63.2(6) . . ?
N1 Eu1 N5 121.6(6) . . ?
N3 Eu1 N5 120.9(6) . . ?
C45 O9 Eu1 124.9(10) . . ?
C1 O1 Eu1 124.7(14) . . ?
C20 O4 Eu1 130.3(12) . . ?
C7 O3 Eu1 123.0(9) . . ?
C2 N1 C6 118.4(15) . . ?
C2 N1 Eu1 117.7(13) . . ?
C6 N1 Eu1 121.9(11) . . ?
C43 C44 N5 123.6(19) . . ?
C43 C44 C45 123.4(16) . . ?
N5 C44 C45 112.9(17) . . ?
N1 C2 C3 123.2(18) . . ?
N1 C2 C1 115(2) . . ?
C3 C2 C1 122(2) . . ?
C40 N5 C44 121.7(18) . . ?
C40 N5 Eu1 119.7(12) . . ?
C44 N5 Eu1 118.5(17) . . ?
O1 C1 O2 128(2) . . ?
O1 C1 C2 116(3) . . ?
O2 C1 C2 116(3) . . ?
C41 C40 N5 120(2) . . ?
C41 C40 C39 130(3) . . ?
N5 C40 C39 109(2) . . ?
C69 C68 C67 120.3 . . ?
C68 C67 C76 119.8 . . ?
C68 C67 C65 121.9 . . ?
C76 C67 C65 118.0 . . ?
C75 C76 C67 120.0 . . ?
C76 C75 C74 120.0 . . ?
C75 C74 C73 120.1 . . ?
C75 C74 C69 120.1 . . ?
C73 C74 C69 119.8 . . ?
C70 C69 C68 120.3 . . ?
C70 C69 C74 120.1 . . ?
C68 C69 C74 119.6 . . ?
C69 C70 C71 120.0 . . ?
C70 C71 C72 120.0 . . ?
C73 C72 C71 119.9 . . ?
C72 C73 C74 120.2 . . ?
C97 C98 C99 122.5(11) . . ?
O15 C83 N10 127.1(7) . . ?
O15 C83 C82 116.6(7) . . ?
N10 C83 C82 116.2 . . ?
C44 C43 C42 115.3(15) . . ?
O18 C102 N12 128.1(10) . . ?
O18 C102 C101 115.5(10) . . ?
N12 C102 C101 116.4(11) . . ?
C39 O7 Eu1 122.8(15) . . ?
C98 C97 N11 124.1(7) . . ?
C98 C97 C96 123.9 . . ?
N11 C97 C96 111.3(7) . . ?
C105 C103 C116 80(2) . . ?
C105 C103 N12 113(2) . . ?
C116 C103 N12 124.2(13) . . ?
C105 C103 C115 72(2) . . ?
C116 C103 C115 125(2) . . ?
N12 C103 C115 110(2) . . ?
C105 C103 C104 128(2) . . ?
C116 C103 C104 48.2(19) . . ?
N12 C103 C104 105.8(18) . . ?
C115 C103 C104 126(2) . . ?
C49 C48 C57 113.4(10) . . ?
C49 C48 C46 117.0 . . ?
C57 C48 C46 129.5(10) . . ?
C7 N2 C8 120.8(8) . . ?
N1 C6 C5 120.5(8) . . ?
N1 C6 C7 110.0(8) . . ?
C5 C6 C7 129.5 . . ?
C67 C65 C66 118.6 . . ?
C67 C65 N8 112.5(7) . . ?
C66 C65 N8 105.4(6) . . ?
C6 C5 C4 120.8 . . ?
C101 C100 C99 124.7(13) . . ?
O9 C45 N6 120.0(7) . . ?
O9 C45 C44 120.2(11) . . ?
N6 C45 C44 119.6(7) . . ?
O3 C7 N2 120.9(7) . . ?
O3 C7 C6 119.8(7) . . ?
N2 C7 C6 119.3 . . ?
O16 C96 O17 132.5(11) . . ?
O16 C96 C97 111.4(6) . . ?
O17 C96 C97 115.6(8) . . ?
C4 C3 C2 118.5(10) . . ?
O4 C20 O5 135.2(12) . . ?
O4 C20 C21 117.7(14) . . ?
O5 C20 C21 106.9(14) . . ?
C45 N6 C46 121.3 . . ?
C83 N10 C84 121.5 . . ?
O12 C64 N8 125.8(12) . . ?
O12 C64 C63 117.4(7) . . ?
N8 C64 C63 116.7(9) . . ?
C57 C56 C55 116.2(12) . . ?
N9 C82 C81 119.1(15) . . ?
N9 C82 C83 112.5(9) . . ?
C81 C82 C83 127.4(11) . . ?
C48 C49 C50 120.1 . . ?
O6 C26 N4 118.5(15) . . ?
O6 C26 C25 126.0(15) . . ?
N4 C26 C25 115.4(17) . . ?
C51 C50 C55 118.1(13) . . ?
C51 C50 C49 123.0(14) . . ?
C55 C50 C49 118.2 . . ?
N6 C46 C47 107.6 . . ?
N6 C46 C48 105.1 . . ?
C47 C46 C48 106.9 . . ?
N7 C59 C60 124.0(11) . . ?
N7 C59 C58 110.8(13) . . ?
C60 C59 C58 125.0(14) . . ?
C62 C63 N7 118.5(7) . . ?
C62 C63 C64 127.1 . . ?
N7 C63 C64 114.3(7) . . ?
N10 C84 C85 113.0(11) . . ?
N10 C84 C86 107.4(11) . . ?
C85 C84 C86 117.6(15) . . ?
C63 C62 C61 119.7(8) . . ?
C3 C4 C5 118.4 . . ?
C50 C55 C56 120.1 . . ?
C50 C55 C54 118.7(15) . . ?
C56 C55 C54 121.2(15) . . ?
C86 C87 C88 118(3) . . ?
C95 C86 C87 121(3) . . ?
C95 C86 C84 119(3) . . ?
C87 C86 C84 119(3) . . ?
C86 C95 C94 114(3) . . ?
C93 C94 C95 132(4) . . ?
C94 C93 C88 114(3) . . ?
C94 C93 C92 126(3) . . ?
C88 C93 C92 120.0 . . ?
C89 C88 C93 120.0 . . ?
C89 C88 C87 119(3) . . ?
C93 C88 C87 121(3) . . ?
C88 C89 C90 120.0 . . ?
C91 C90 C89 120.0 . . ?
C90 C91 C92 120.0 . . ?
C91 C92 C93 120.0 . . ?
O14 C77 O13 119(3) . . ?
O14 C77 C78 119(3) . . ?
O13 C77 C78 121(3) . . ?
C80 C81 C82 120(2) . . ?
C52 C53 C54 126(4) . . ?
C56 C57 C48 130(2) . . ?
C40 C41 C42 118(3) . . ?
C98 C99 C100 112.5(17) . . ?
C59 C60 C61 117.1(18) . . ?
C79 C80 C81 120(3) . . ?
C53 C52 C51 119(4) . . ?
C60 C61 C62 117.7(17) . . ?
C41 C42 C43 121(2) . . ?
C29 C27 C28 121(5) . . ?
C29 C27 N4 89(3) . . ?
C28 C27 N4 93(4) . . ?
C53 C54 C55 116(3) . . ?
O7 C39 O8 120(2) . . ?
O7 C39 C40 124(3) . . ?
O8 C39 C40 114(2) . . ?
C77 C78 N9 113(3) . . ?
C77 C78 C79 123(3) . . ?
N9 C78 C79 124(3) . . ?
C26 N4 C27 118(2) . . ?
C80 C79 C78 114(3) . . ?
C10 C8 C9 123(2) . . ?
C10 C8 N2 101(2) . . ?
C9 C8 N2 111(2) . . ?
C52 C51 C50 121(3) . . ?
O10 C58 O11 128(2) . . ?
O10 C58 C59 118.4(19) . . ?
O11 C58 C59 114(2) . . ?
N11 C101 C100 117(2) . . ?
N11 C101 C102 114.7(18) . . ?
C100 C101 C102 127.9(14) . . ?
C59 N7 C63 121.7(12) . . ?
C59 N7 Eu2 118.2(9) . . ?
C63 N7 Eu2 118.9(10) . . ?
C64 N8 C65 118.3(12) . . ?
C82 N9 C78 120.7(19) . . ?
C82 N9 Eu2 120.7(12) . . ?
C78 N9 Eu2 118.6(17) . . ?
C97 N11 C101 118.6(17) . . ?
C97 N11 Eu2 122.1(9) . . ?
C101 N11 Eu2 119.3(15) . . ?
C102 N12 C103 119.2(11) . . ?
C64 O12 Eu2 127.5(10) . . ?
C77 O13 Eu2 122.8(17) . . ?
C83 O15 Eu2 127.5(9) . . ?
C58 O10 Eu2 127.9(13) . . ?
C96 O16 Eu2 132.1(9) . . ?
C102 O18 Eu2 127.0(9) . . ?
O10 Eu2 O16 88.5(5) . . ?
O10 Eu2 O15 78.3(5) . . ?
O16 Eu2 O15 145.4(5) . . ?
O10 Eu2 O13 144.1(5) . . ?
O16 Eu2 O13 82.1(5) . . ?
O15 Eu2 O13 126.2(5) . . ?
O10 Eu2 O18 78.1(4) . . ?
O16 Eu2 O18 126.6(5) . . ?
O15 Eu2 O18 82.0(5) . . ?
O13 Eu2 O18 80.1(4) . . ?
O10 Eu2 O12 124.9(5) . . ?
O16 Eu2 O12 77.6(5) . . ?
O15 Eu2 O12 84.0(5) . . ?
O13 Eu2 O12 86.8(5) . . ?
O18 Eu2 O12 149.7(5) . . ?
O10 Eu2 N11 73.3(5) . . ?
O16 Eu2 N11 63.1(5) . . ?
O15 Eu2 N11 138.8(5) . . ?
O13 Eu2 N11 71.6(5) . . ?
O18 Eu2 N11 63.5(5) . . ?
O12 Eu2 N11 136.9(5) . . ?
O10 Eu2 N9 135.0(6) . . ?
O16 Eu2 N9 136.4(6) . . ?
O15 Eu2 N9 62.5(6) . . ?
O13 Eu2 N9 64.0(7) . . ?
O18 Eu2 N9 75.6(5) . . ?
O12 Eu2 N9 74.1(5) . . ?
N11 Eu2 N9 123.4(6) . . ?
O10 Eu2 N7 63.6(5) . . ?
O16 Eu2 N7 77.0(5) . . ?
O15 Eu2 N7 68.5(5) . . ?
O13 Eu2 N7 144.8(5) . . ?
O18 Eu2 N7 135.0(5) . . ?
O12 Eu2 N7 61.4(5) . . ?
N11 Eu2 N7 121.0(5) . . ?
N9 Eu2 N7 115.6(6) . . ?
C22 C23 C24 118(3) . . ?
C25 C24 C23 120(3) . . ?
N3 C25 C24 119(3) . . ?
N3 C25 C26 109(2) . . ?
C24 C25 C26 132(3) . . ?
C25 N3 C21 124(2) . . ?
C25 N3 Eu1 120.9(17) . . ?
C21 N3 Eu1 114.9(16) . . ?
C22 C21 N3 116(2) . . ?
C22 C21 C20 132(3) . . ?
N3 C21 C20 111(2) . . ?
C21 C22 C23 122(3) . . ?
C103 C105 C106 119(4) . . ?
C103 C105 C114 121(3) . . ?
C106 C105 C114 115(4) . . ?
C16 C15 C14 117(7) . . ?
C12 C13 C14 122(6) . . ?
C8 C10 C19 106(3) . . ?
C8 C10 C11 132(3) . . ?
C19 C10 C11 120.0 . . ?
C18 C19 C10 120.0 . . ?
C19 C18 C17 120.0 . . ?
C12 C17 C18 120.0 . . ?
C12 C17 C16 109(4) . . ?
C18 C17 C16 130(4) . . ?
C11 C12 C17 120.0 . . ?
C11 C12 C13 116(4) . . ?
C17 C12 C13 124(4) . . ?
C12 C11 C10 120.0 . . ?
C29 C30 C31 120.0 . . ?
C27 C29 C30 126(4) . . ?
C27 C29 C38 114(4) . . ?
C30 C29 C38 120.0 . . ?
C37 C38 C29 120.0 . . ?
C38 C37 C36 120.0 . . ?
C31 C36 C37 120.0 . . ?
C31 C36 C35 120.0 . . ?
C37 C36 C35 120.0 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C30 120.0 . . ?
C36 C31 C30 120.0 . . ?
C31 C32 C33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C35 C34 C33 120.0 . . ?
C34 C35 C36 120.0 . . ?
C15 C14 C13 117(7) . . ?
C113 C114 C105 118(4) . . ?
C111 C112 C107 120.0 . . ?
C111 C112 C113 122(3) . . ?
C107 C112 C113 118(3) . . ?
C110 C111 C112 120.0 . . ?
C111 C110 C109 120.0 . . ?
C110 C109 C108 120.0 . . ?
C109 C108 C107 120.0 . . ?
C108 C107 C112 120.0 . . ?
C108 C107 C106 125(3) . . ?
C112 C107 C106 115(3) . . ?
C26 O6 Eu1 120.4(10) . . ?
C105 C106 C107 125(5) . . ?
C114 C113 C112 128(5) . . ?
C15 C16 C17 130(7) . . ?
C125 C124 C123 120.0 . . ?
C116 C125 C124 120.0 . . ?
C125 C116 C117 120.0 . . ?
C125 C116 C103 135.8(17) . . ?
C117 C116 C103 102.0(17) . . ?
C118 C117 C116 120.0 . . ?
C117 C118 C123 120.0 . . ?
C117 C118 C119 120.0 . . ?
C123 C118 C119 120.0 . . ?
C122 C123 C118 120.0 . . ?
C122 C123 C124 120.0 . . ?
C118 C123 C124 120.0 . . ?
C123 C122 C121 120.0 . . ?
C120 C121 C122 120.0 . . ?
C121 C120 C119 120.0 . . ?
C120 C119 C118 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Eu1 O9 C45 -152.0(11) . . . . ?
O1 Eu1 O9 C45 -70.5(11) . . . . ?
O6 Eu1 O9 C45 78.5(11) . . . . ?
O7 Eu1 O9 C45 5.4(12) . . . . ?
O3 Eu1 O9 C45 138.3(11) . . . . ?
N1 Eu1 O9 C45 -103.4(13) . . . . ?
N3 Eu1 O9 C45 143.5(13) . . . . ?
N5 Eu1 O9 C45 4.8(10) . . . . ?
O4 Eu1 O1 C1 -68.2(18) . . . . ?
O6 Eu1 O1 C1 147.0(17) . . . . ?
O7 Eu1 O1 C1 77.5(18) . . . . ?
O3 Eu1 O1 C1 4(2) . . . . ?
O9 Eu1 O1 C1 -155.1(18) . . . . ?
N1 Eu1 O1 C1 1.8(17) . . . . ?
N3 Eu1 O1 C1 -102.9(18) . . . . ?
N5 Eu1 O1 C1 140.1(19) . . . . ?
O1 Eu1 O4 C20 -164.7(13) . . . . ?
O6 Eu1 O4 C20 -10.5(15) . . . . ?
O7 Eu1 O4 C20 127.2(11) . . . . ?
O3 Eu1 O4 C20 63.7(12) . . . . ?
O9 Eu1 O4 C20 -83.8(12) . . . . ?
N1 Eu1 O4 C20 128.3(14) . . . . ?
N3 Eu1 O4 C20 -10.1(11) . . . . ?
N5 Eu1 O4 C20 -118.1(13) . . . . ?
O4 Eu1 O3 C7 60.8(13) . . . . ?
O1 Eu1 O3 C7 -11.0(16) . . . . ?
O6 Eu1 O3 C7 -169.5(14) . . . . ?
O7 Eu1 O3 C7 -85.9(13) . . . . ?
O9 Eu1 O3 C7 131.4(11) . . . . ?
N1 Eu1 O3 C7 -8.5(12) . . . . ?
N3 Eu1 O3 C7 126.1(15) . . . . ?
N5 Eu1 O3 C7 -117.7(13) . . . . ?
O4 Eu1 N1 C2 83.5(17) . . . . ?
O1 Eu1 N1 C2 -6.3(15) . . . . ?
O6 Eu1 N1 C2 -153.2(15) . . . . ?
O7 Eu1 N1 C2 -97.1(16) . . . . ?
O3 Eu1 N1 C2 175.8(18) . . . . ?
O9 Eu1 N1 C2 30(2) . . . . ?
N3 Eu1 N1 C2 126.0(16) . . . . ?
N5 Eu1 N1 C2 -54.5(18) . . . . ?
O4 Eu1 N1 C6 -80.2(12) . . . . ?
O1 Eu1 N1 C6 -170.0(14) . . . . ?
O6 Eu1 N1 C6 43.1(17) . . . . ?
O7 Eu1 N1 C6 99.1(13) . . . . ?
O3 Eu1 N1 C6 12.1(11) . . . . ?
O9 Eu1 N1 C6 -134.0(11) . . . . ?
N3 Eu1 N1 C6 -37.8(15) . . . . ?
N5 Eu1 N1 C6 141.7(12) . . . . ?
C6 N1 C2 C3 -4(3) . . . . ?
Eu1 N1 C2 C3 -168.2(13) . . . . ?
C6 N1 C2 C1 173.7(16) . . . . ?
Eu1 N1 C2 C1 9(3) . . . . ?
C43 C44 N5 C40 -1(3) . . . . ?
C45 C44 N5 C40 -176.2(18) . . . . ?
C43 C44 N5 Eu1 175.2(14) . . . . ?
C45 C44 N5 Eu1 0(2) . . . . ?
O4 Eu1 N5 C40 -146.8(16) . . . . ?
O1 Eu1 N5 C40 -98.1(17) . . . . ?
O6 Eu1 N5 C40 86.3(17) . . . . ?
O7 Eu1 N5 C40 -5.3(15) . . . . ?
O3 Eu1 N5 C40 30.7(19) . . . . ?
O9 Eu1 N5 C40 174.2(18) . . . . ?
N1 Eu1 N5 C40 -52.8(18) . . . . ?
N3 Eu1 N5 C40 126.7(16) . . . . ?
O4 Eu1 N5 C44 37.3(18) . . . . ?
O1 Eu1 N5 C44 86.0(15) . . . . ?
O6 Eu1 N5 C44 -89.6(15) . . . . ?
O7 Eu1 N5 C44 178.8(16) . . . . ?
O3 Eu1 N5 C44 -145.2(14) . . . . ?
O9 Eu1 N5 C44 -1.7(14) . . . . ?
N1 Eu1 N5 C44 131.3(15) . . . . ?
N3 Eu1 N5 C44 -49.2(17) . . . . ?
Eu1 O1 C1 O2 177.0(19) . . . . ?
Eu1 O1 C1 C2 2(3) . . . . ?
N1 C2 C1 O1 -8(3) . . . . ?
C3 C2 C1 O1 169.8(19) . . . . ?
N1 C2 C1 O2 177(2) . . . . ?
C3 C2 C1 O2 -6(3) . . . . ?
C44 N5 C40 C41 1(4) . . . . ?
Eu1 N5 C40 C41 -174.4(18) . . . . ?
C44 N5 C40 C39 -172.2(19) . . . . ?
Eu1 N5 C40 C39 12(3) . . . . ?
C69 C68 C67 C76 0.2 . . . . ?
C69 C68 C67 C65 -173.6 . . . . ?
C68 C67 C76 C75 -0.2 . . . . ?
C65 C67 C76 C75 173.9 . . . . ?
C67 C76 C75 C74 0.1 . . . . ?
C76 C75 C74 C73 179.8 . . . . ?
C76 C75 C74 C69 -0.1 . . . . ?
C67 C68 C69 C70 180.0 . . . . ?
C67 C68 C69 C74 -0.2 . . . . ?
C75 C74 C69 C70 -180.0 . . . . ?
C73 C74 C69 C70 0.1 . . . . ?
C75 C74 C69 C68 0.1 . . . . ?
C73 C74 C69 C68 -179.8 . . . . ?
C68 C69 C70 C71 179.9 . . . . ?
C74 C69 C70 C71 0.0 . . . . ?
C69 C70 C71 C72 -0.1 . . . . ?
C70 C71 C72 C73 0.0 . . . . ?
C71 C72 C73 C74 0.1 . . . . ?
C75 C74 C73 C72 179.9 . . . . ?
C69 C74 C73 C72 -0.1 . . . . ?
N5 C44 C43 C42 -1(3) . . . . ?
C45 C44 C43 C42 174.7(18) . . . . ?
O4 Eu1 O7 C39 136.0(16) . . . . ?
O1 Eu1 O7 C39 69.1(15) . . . . ?
O6 Eu1 O7 C39 -76.5(16) . . . . ?
O3 Eu1 O7 C39 -159.9(16) . . . . ?
O9 Eu1 O7 C39 -4.9(16) . . . . ?
N1 Eu1 O7 C39 135.1(16) . . . . ?
N3 Eu1 O7 C39 -110.5(16) . . . . ?
N5 Eu1 O7 C39 -4.2(15) . . . . ?
C99 C98 C97 N11 -3.5(15) . . . . ?
C99 C98 C97 C96 -173.3(13) . . . . ?
C2 N1 C6 C5 3(2) . . . . ?
Eu1 N1 C6 C5 167.0(6) . . . . ?
C2 N1 C6 C7 -177.1(16) . . . . ?
Eu1 N1 C6 C7 -13.5(13) . . . . ?
C68 C67 C65 C66 60.5 . . . . ?
C76 C67 C65 C66 -113.4 . . . . ?
C68 C67 C65 N8 -176.0(7) . . . . ?
C76 C67 C65 N8 10.1(7) . . . . ?
N1 C6 C5 C4 -0.6(9) . . . . ?
C7 C6 C5 C4 -179.9 . . . . ?
Eu1 O9 C45 N6 178.4(5) . . . . ?
Eu1 O9 C45 C44 -7.1(17) . . . . ?
C43 C44 C45 O9 -171.0(14) . . . . ?
N5 C44 C45 O9 5(2) . . . . ?
C43 C44 C45 N6 3(2) . . . . ?
N5 C44 C45 N6 179.2(12) . . . . ?
Eu1 O3 C7 N2 -172.8(5) . . . . ?
Eu1 O3 C7 C6 5.3(15) . . . . ?
C8 N2 C7 O3 -5.1(15) . . . . ?
C8 N2 C7 C6 176.9(11) . . . . ?
N1 C6 C7 O3 5.5(12) . . . . ?
C5 C6 C7 O3 -175.1(10) . . . . ?
N1 C6 C7 N2 -176.4(8) . . . . ?
C5 C6 C7 N2 3.0 . . . . ?
C98 C97 C96 O16 173.8(8) . . . . ?
N11 C97 C96 O16 2.9(11) . . . . ?
C98 C97 C96 O17 -13.5(12) . . . . ?
N11 C97 C96 O17 175.6(15) . . . . ?
N1 C2 C3 C4 1(3) . . . . ?
C1 C2 C3 C4 -176.1(15) . . . . ?
Eu1 O4 C20 O5 -166.3(12) . . . . ?
Eu1 O4 C20 C21 17.9(18) . . . . ?
O9 C45 N6 C46 0.6(8) . . . . ?
C44 C45 N6 C46 -173.8(10) . . . . ?
O15 C83 N10 C84 1.7(8) . . . . ?
C82 C83 N10 C84 -179.7 . . . . ?
O15 C83 C82 N9 -0.4(11) . . . . ?
N10 C83 C82 N9 -179.2(8) . . . . ?
O15 C83 C82 C81 -168.3(12) . . . . ?
N10 C83 C82 C81 12.9(10) . . . . ?
C57 C48 C49 C50 13.6(13) . . . . ?
C46 C48 C49 C50 -169.4 . . . . ?
C48 C49 C50 C51 174.4(15) . . . . ?
C48 C49 C50 C55 -15.6 . . . . ?
C45 N6 C46 C47 -163.7 . . . . ?
C45 N6 C46 C48 82.7 . . . . ?
C49 C48 C46 N6 -140.4 . . . . ?
C57 C48 C46 N6 36.1(15) . . . . ?
C49 C48 C46 C47 105.4 . . . . ?
C57 C48 C46 C47 -78.1(15) . . . . ?
O12 C64 C63 C62 -177.8(9) . . . . ?
N8 C64 C63 C62 4.6(10) . . . . ?
O12 C64 C63 N7 1.0(11) . . . . ?
N8 C64 C63 N7 -176.6(14) . . . . ?
C83 N10 C84 C85 -145.1(12) . . . . ?
C83 N10 C84 C86 83.5(12) . . . . ?
N7 C63 C62 C61 4.1(15) . . . . ?
C64 C63 C62 C61 -177.3(14) . . . . ?
C2 C3 C4 C5 1.6(11) . . . . ?
C6 C5 C4 C3 -2.0 . . . . ?
C51 C50 C55 C56 -179.5(15) . . . . ?
C49 C50 C55 C56 10.0 . . . . ?
C51 C50 C55 C54 -3(2) . . . . ?
C49 C50 C55 C54 -173.1(16) . . . . ?
C57 C56 C55 C50 -4.1(14) . . . . ?
C57 C56 C55 C54 179(2) . . . . ?
C88 C87 C86 C95 9(6) . . . . ?
C88 C87 C86 C84 177(3) . . . . ?
N10 C84 C86 C95 -150(2) . . . . ?
C85 C84 C86 C95 81(3) . . . . ?
N10 C84 C86 C87 42(3) . . . . ?
C85 C84 C86 C87 -87(3) . . . . ?
C87 C86 C95 C94 -7(5) . . . . ?
C84 C86 C95 C94 -176(2) . . . . ?
C86 C95 C94 C93 6(5) . . . . ?
C95 C94 C93 C88 -6(4) . . . . ?
C95 C94 C93 C92 178(2) . . . . ?
C94 C93 C88 C89 -177(3) . . . . ?
C92 C93 C88 C89 0.0 . . . . ?
C94 C93 C88 C87 7(3) . . . . ?
C92 C93 C88 C87 -177(3) . . . . ?
C86 C87 C88 C89 175(3) . . . . ?
C86 C87 C88 C93 -8(5) . . . . ?
C93 C88 C89 C90 0.0 . . . . ?
C87 C88 C89 C90 177(3) . . . . ?
C88 C89 C90 C91 0.0 . . . . ?
C89 C90 C91 C92 0.0 . . . . ?
C90 C91 C92 C93 0.0 . . . . ?
C94 C93 C92 C91 176(3) . . . . ?
C88 C93 C92 C91 0.0 . . . . ?
N9 C82 C81 C80 8.2(16) . . . . ?
C83 C82 C81 C80 175.4(9) . . . . ?
C55 C56 C57 C48 3(3) . . . . ?
C49 C48 C57 C56 -8(3) . . . . ?
C46 C48 C57 C56 175.2(16) . . . . ?
N5 C40 C41 C42 -1(4) . . . . ?
C39 C40 C41 C42 171(3) . . . . ?
C97 C98 C99 C100 0(2) . . . . ?
C101 C100 C99 C98 1(3) . . . . ?
N7 C59 C60 C61 0(3) . . . . ?
C58 C59 C60 C61 174(2) . . . . ?
C82 C81 C80 C79 3(2) . . . . ?
C54 C53 C52 C51 -4(6) . . . . ?
C59 C60 C61 C62 10(3) . . . . ?
C63 C62 C61 C60 -12(3) . . . . ?
C40 C41 C42 C43 0(4) . . . . ?
C44 C43 C42 C41 1(3) . . . . ?
C52 C53 C54 C55 10(6) . . . . ?
C50 C55 C54 C53 -6(3) . . . . ?
C56 C55 C54 C53 171(2) . . . . ?
Eu1 O7 C39 O8 175.2(16) . . . . ?
Eu1 O7 C39 C40 14(3) . . . . ?
C41 C40 C39 O7 170(3) . . . . ?
N5 C40 C39 O7 -17(3) . . . . ?
C41 C40 C39 O8 8(4) . . . . ?
N5 C40 C39 O8 -179(2) . . . . ?
O14 C77 C78 N9 174.5(19) . . . . ?
O13 C77 C78 N9 -12(3) . . . . ?
O14 C77 C78 C79 -5(4) . . . . ?
O13 C77 C78 C79 169(3) . . . . ?
O6 C26 N4 C27 -10(3) . . . . ?
C25 C26 N4 C27 171(2) . . . . ?
C29 C27 N4 C26 116(3) . . . . ?
C28 C27 N4 C26 -124(3) . . . . ?
C81 C80 C79 C78 -9(3) . . . . ?
C77 C78 C79 C80 -176(2) . . . . ?
N9 C78 C79 C80 5(4) . . . . ?
C7 N2 C8 C10 74(2) . . . . ?
C7 N2 C8 C9 -154.2(19) . . . . ?
C53 C52 C51 C50 -6(5) . . . . ?
C55 C50 C51 C52 9(3) . . . . ?
C49 C50 C51 C52 179(2) . . . . ?
N7 C59 C58 O10 -3(2) . . . . ?
C60 C59 C58 O10 -178.3(18) . . . . ?
N7 C59 C58 O11 -179.3(16) . . . . ?
C60 C59 C58 O11 6(3) . . . . ?
C99 C100 C101 N11 0(3) . . . . ?
C99 C100 C101 C102 176.9(16) . . . . ?
O18 C102 C101 N11 2(2) . . . . ?
N12 C102 C101 N11 -179.2(15) . . . . ?
O18 C102 C101 C100 -174.7(15) . . . . ?
N12 C102 C101 C100 4(3) . . . . ?
C60 C59 N7 C63 -8(2) . . . . ?
C58 C59 N7 C63 177.0(13) . . . . ?
C60 C59 N7 Eu2 -175.6(13) . . . . ?
C58 C59 N7 Eu2 9.6(15) . . . . ?
C62 C63 N7 C59 5.8(17) . . . . ?
C64 C63 N7 C59 -173.0(10) . . . . ?
C62 C63 N7 Eu2 173.1(4) . . . . ?
C64 C63 N7 Eu2 -5.7(11) . . . . ?
O12 C64 N8 C65 5(2) . . . . ?
C63 C64 N8 C65 -177.5(8) . . . . ?
C67 C65 N8 C64 75.8(15) . . . . ?
C66 C65 N8 C64 -153.6(12) . . . . ?
C81 C82 N9 C78 -13(2) . . . . ?
C83 C82 N9 C78 178.1(14) . . . . ?
C81 C82 N9 Eu2 165.6(10) . . . . ?
C83 C82 N9 Eu2 -3.4(12) . . . . ?
C77 C78 N9 C82 -172.7(17) . . . . ?
C79 C78 N9 C82 7(3) . . . . ?
C77 C78 N9 Eu2 9(2) . . . . ?
C79 C78 N9 Eu2 -172(2) . . . . ?
C98 C97 N11 C101 5.1(19) . . . . ?
C96 C97 N11 C101 176.0(13) . . . . ?
C98 C97 N11 Eu2 -173.5(4) . . . . ?
C96 C97 N11 Eu2 -2.6(12) . . . . ?
C100 C101 N11 C97 -3(2) . . . . ?
C102 C101 N11 C97 179.6(13) . . . . ?
C100 C101 N11 Eu2 175.2(11) . . . . ?
C102 C101 N11 Eu2 -2(2) . . . . ?
O18 C102 N12 C103 19(2) . . . . ?
C101 C102 N12 C103 -159.5(13) . . . . ?
C105 C103 N12 C102 -78(2) . . . . ?
C116 C103 N12 C102 16(3) . . . . ?
C115 C103 N12 C102 -156(2) . . . . ?
C104 C103 N12 C102 65(2) . . . . ?
N8 C64 O12 Eu2 -177.7(12) . . . . ?
C63 C64 O12 Eu2 5.0(16) . . . . ?
O14 C77 O13 Eu2 -176.6(13) . . . . ?
C78 C77 O13 Eu2 10(3) . . . . ?
N10 C83 O15 Eu2 -176.7(4) . . . . ?
C82 C83 O15 Eu2 4.6(12) . . . . ?
O11 C58 O10 Eu2 169.4(17) . . . . ?
C59 C58 O10 Eu2 -6(3) . . . . ?
O17 C96 O16 Eu2 -173.3(15) . . . . ?
C97 C96 O16 Eu2 -2.3(15) . . . . ?
N12 C102 O18 Eu2 -180.0(13) . . . . ?
C101 C102 O18 Eu2 -1.1(16) . . . . ?
C58 O10 Eu2 O16 84.0(18) . . . . ?
C58 O10 Eu2 O15 -63.9(18) . . . . ?
C58 O10 Eu2 O13 158.2(16) . . . . ?
C58 O10 Eu2 O18 -148.0(18) . . . . ?
C58 O10 Eu2 O12 10(2) . . . . ?
C58 O10 Eu2 N11 146.3(18) . . . . ?
C58 O10 Eu2 N9 -92.9(18) . . . . ?
C58 O10 Eu2 N7 7.8(17) . . . . ?
C96 O16 Eu2 O10 72.8(14) . . . . ?
C96 O16 Eu2 O15 139.5(12) . . . . ?
C96 O16 Eu2 O13 -72.5(14) . . . . ?
C96 O16 Eu2 O18 -1.1(17) . . . . ?
C96 O16 Eu2 O12 -160.9(15) . . . . ?
C96 O16 Eu2 N11 0.8(13) . . . . ?
C96 O16 Eu2 N9 -110.5(14) . . . . ?
C96 O16 Eu2 N7 136.0(15) . . . . ?
C83 O15 Eu2 O10 -161.8(11) . . . . ?
C83 O15 Eu2 O16 128.5(11) . . . . ?
C83 O15 Eu2 O13 -11.0(13) . . . . ?
C83 O15 Eu2 O18 -82.4(11) . . . . ?
C83 O15 Eu2 O12 70.6(11) . . . . ?
C83 O15 Eu2 N11 -114.9(11) . . . . ?
C83 O15 Eu2 N9 -4.6(10) . . . . ?
C83 O15 Eu2 N7 132.2(12) . . . . ?
C77 O13 Eu2 O10 128.6(17) . . . . ?
C77 O13 Eu2 O16 -155.2(17) . . . . ?
C77 O13 Eu2 O15 2.9(18) . . . . ?
C77 O13 Eu2 O18 75.3(16) . . . . ?
C77 O13 Eu2 O12 -77.3(17) . . . . ?
C77 O13 Eu2 N11 140.6(17) . . . . ?
C77 O13 Eu2 N9 -3.4(16) . . . . ?
C77 O13 Eu2 N7 -101.5(18) . . . . ?
C102 O18 Eu2 O10 -76.9(12) . . . . ?
C102 O18 Eu2 O16 2.2(14) . . . . ?
C102 O18 Eu2 O15 -156.5(12) . . . . ?
C102 O18 Eu2 O13 74.4(12) . . . . ?
C102 O18 Eu2 O12 140.2(11) . . . . ?
C102 O18 Eu2 N11 0.2(10) . . . . ?
C102 O18 Eu2 N9 139.9(13) . . . . ?
C102 O18 Eu2 N7 -108.2(12) . . . . ?
C64 O12 Eu2 O10 -8.3(17) . . . . ?
C64 O12 Eu2 O16 -87.5(14) . . . . ?
C64 O12 Eu2 O15 63.0(14) . . . . ?
C64 O12 Eu2 O13 -170.1(14) . . . . ?
C64 O12 Eu2 O18 125.8(13) . . . . ?
C64 O12 Eu2 N11 -111.7(14) . . . . ?
C64 O12 Eu2 N9 126.0(15) . . . . ?
C64 O12 Eu2 N7 -5.7(13) . . . . ?
C97 N11 Eu2 O10 -95.7(12) . . . . ?
C101 N11 Eu2 O10 85.7(14) . . . . ?
C97 N11 Eu2 O16 1.3(10) . . . . ?
C101 N11 Eu2 O16 -177.3(16) . . . . ?
C97 N11 Eu2 O15 -144.0(10) . . . . ?
C101 N11 Eu2 O15 37.4(17) . . . . ?
C97 N11 Eu2 O13 91.6(12) . . . . ?
C101 N11 Eu2 O13 -87.0(14) . . . . ?
C97 N11 Eu2 O18 179.5(13) . . . . ?
C101 N11 Eu2 O18 0.9(13) . . . . ?
C97 N11 Eu2 O12 27.9(15) . . . . ?
C101 N11 Eu2 O12 -150.8(13) . . . . ?
C97 N11 Eu2 N9 130.9(11) . . . . ?
C101 N11 Eu2 N9 -47.7(16) . . . . ?
C97 N11 Eu2 N7 -52.0(13) . . . . ?
C101 N11 Eu2 N7 129.4(14) . . . . ?
C82 N9 Eu2 O10 36.3(15) . . . . ?
C78 N9 Eu2 O10 -145.2(13) . . . . ?
C82 N9 Eu2 O16 -139.1(10) . . . . ?
C78 N9 Eu2 O16 39.4(18) . . . . ?
C82 N9 Eu2 O15 3.9(10) . . . . ?
C78 N9 Eu2 O15 -177.5(16) . . . . ?
C82 N9 Eu2 O13 178.2(13) . . . . ?
C78 N9 Eu2 O13 -3.3(13) . . . . ?
C82 N9 Eu2 O18 92.3(12) . . . . ?
C78 N9 Eu2 O18 -89.2(15) . . . . ?
C82 N9 Eu2 O12 -87.5(12) . . . . ?
C78 N9 Eu2 O12 91.0(15) . . . . ?
C82 N9 Eu2 N11 136.2(10) . . . . ?
C78 N9 Eu2 N11 -45.3(16) . . . . ?
C82 N9 Eu2 N7 -41.0(13) . . . . ?
C78 N9 Eu2 N7 137.5(14) . . . . ?
C59 N7 Eu2 O10 -9.0(10) . . . . ?
C63 N7 Eu2 O10 -176.7(13) . . . . ?
C59 N7 Eu2 O16 -103.9(12) . . . . ?
C63 N7 Eu2 O16 88.4(11) . . . . ?
C59 N7 Eu2 O15 78.2(11) . . . . ?
C63 N7 Eu2 O15 -89.5(11) . . . . ?
C59 N7 Eu2 O13 -158.9(9) . . . . ?
C63 N7 Eu2 O13 33.4(17) . . . . ?
C59 N7 Eu2 O18 25.6(15) . . . . ?
C63 N7 Eu2 O18 -142.2(9) . . . . ?
C59 N7 Eu2 O12 173.3(13) . . . . ?
C63 N7 Eu2 O12 5.6(10) . . . . ?
C59 N7 Eu2 N11 -56.7(12) . . . . ?
C63 N7 Eu2 N11 135.6(10) . . . . ?
C59 N7 Eu2 N9 120.6(11) . . . . ?
C63 N7 Eu2 N9 -47.1(12) . . . . ?
C22 C23 C24 C25 8(4) . . . . ?
C23 C24 C25 N3 -7(4) . . . . ?
C23 C24 C25 C26 179(2) . . . . ?
O6 C26 C25 N3 -1(2) . . . . ?
N4 C26 C25 N3 176.7(15) . . . . ?
O6 C26 C25 C24 174(2) . . . . ?
N4 C26 C25 C24 -8(3) . . . . ?
C24 C25 N3 C21 6(3) . . . . ?
C26 C25 N3 C21 -177.7(15) . . . . ?
C24 C25 N3 Eu1 179.4(16) . . . . ?
C26 C25 N3 Eu1 -5(2) . . . . ?
O4 Eu1 N3 C25 -173.9(16) . . . . ?
O1 Eu1 N3 C25 -135.3(15) . . . . ?
O6 Eu1 N3 C25 5.7(14) . . . . ?
O7 Eu1 N3 C25 44.1(17) . . . . ?
O3 Eu1 N3 C25 96.0(16) . . . . ?
O9 Eu1 N3 C25 -80.9(15) . . . . ?
N1 Eu1 N3 C25 142.0(15) . . . . ?
N5 Eu1 N3 C25 -37.5(17) . . . . ?
O4 Eu1 N3 C21 -0.3(12) . . . . ?
O1 Eu1 N3 C21 38.4(15) . . . . ?
O6 Eu1 N3 C21 179.4(14) . . . . ?
O7 Eu1 N3 C21 -142.2(12) . . . . ?
O3 Eu1 N3 C21 -90.4(14) . . . . ?
O9 Eu1 N3 C21 92.7(13) . . . . ?
N1 Eu1 N3 C21 -44.4(15) . . . . ?
N5 Eu1 N3 C21 136.1(13) . . . . ?
C25 N3 C21 C22 -8(3) . . . . ?
Eu1 N3 C21 C22 178.6(17) . . . . ?
C25 N3 C21 C20 -179.6(16) . . . . ?
Eu1 N3 C21 C20 6.9(19) . . . . ?
O4 C20 C21 C22 175(2) . . . . ?
O5 C20 C21 C22 -2(3) . . . . ?
O4 C20 C21 N3 -15(2) . . . . ?
O5 C20 C21 N3 168.3(14) . . . . ?
N3 C21 C22 C23 10(4) . . . . ?
C20 C21 C22 C23 179(2) . . . . ?
C24 C23 C22 C21 -10(5) . . . . ?
C116 C103 C105 C106 136(4) . . . . ?
N12 C103 C105 C106 -101(4) . . . . ?
C115 C103 C105 C106 3(4) . . . . ?
C104 C103 C105 C106 125(4) . . . . ?
C116 C103 C105 C114 -17(3) . . . . ?
N12 C103 C105 C114 106(3) . . . . ?
C115 C103 C105 C114 -150(4) . . . . ?
C104 C103 C105 C114 -28(4) . . . . ?
C9 C8 C10 C19 75(4) . . . . ?
N2 C8 C10 C19 -161.1(13) . . . . ?
C9 C8 C10 C11 -88(4) . . . . ?
N2 C8 C10 C11 36(3) . . . . ?
C8 C10 C19 C18 -165(2) . . . . ?
C11 C10 C19 C18 0.0 . . . . ?
C10 C19 C18 C17 0.0 . . . . ?
C19 C18 C17 C12 0.0 . . . . ?
C19 C18 C17 C16 -171(4) . . . . ?
C18 C17 C12 C11 0.0 . . . . ?
C16 C17 C12 C11 173(4) . . . . ?
C18 C17 C12 C13 174(4) . . . . ?
C16 C17 C12 C13 -13(4) . . . . ?
C14 C13 C12 C11 -175(4) . . . . ?
C14 C13 C12 C17 11(8) . . . . ?
C17 C12 C11 C10 0.0 . . . . ?
C13 C12 C11 C10 -175(4) . . . . ?
C8 C10 C11 C12 161(3) . . . . ?
C19 C10 C11 C12 0.0 . . . . ?
C28 C27 C29 C30 17(6) . . . . ?
N4 C27 C29 C30 109(2) . . . . ?
C28 C27 C29 C38 -170(4) . . . . ?
N4 C27 C29 C38 -77(3) . . . . ?
C31 C30 C29 C27 173(3) . . . . ?
C31 C30 C29 C38 0.0 . . . . ?
C27 C29 C38 C37 -174(3) . . . . ?
C30 C29 C38 C37 0.0 . . . . ?
C29 C38 C37 C36 0.0 . . . . ?
C38 C37 C36 C31 0.0 . . . . ?
C38 C37 C36 C35 180.0 . . . . ?
C37 C36 C31 C32 180.0 . . . . ?
C35 C36 C31 C32 0.0 . . . . ?
C37 C36 C31 C30 0.0 . . . . ?
C35 C36 C31 C30 180.0 . . . . ?
C29 C30 C31 C32 180.0 . . . . ?
C29 C30 C31 C36 0.0 . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C30 C31 C32 C33 180.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C31 C36 C35 C34 0.0 . . . . ?
C37 C36 C35 C34 180.0 . . . . ?
C16 C15 C14 C13 -1(3) . . . . ?
C12 C13 C14 C15 -2(7) . . . . ?
C103 C105 C114 C113 171(4) . . . . ?
C106 C105 C114 C113 17(6) . . . . ?
C107 C112 C111 C110 0.0 . . . . ?
C113 C112 C111 C110 -176(3) . . . . ?
C112 C111 C110 C109 0.0 . . . . ?
C111 C110 C109 C108 0.0 . . . . ?
C110 C109 C108 C107 0.0 . . . . ?
C109 C108 C107 C112 0.0 . . . . ?
C109 C108 C107 C106 178(3) . . . . ?
C111 C112 C107 C108 0.0 . . . . ?
C113 C112 C107 C108 176(3) . . . . ?
C111 C112 C107 C106 -179(3) . . . . ?
C113 C112 C107 C106 -3(4) . . . . ?
N4 C26 O6 Eu1 -171.1(11) . . . . ?
C25 C26 O6 Eu1 7.0(18) . . . . ?
O4 Eu1 O6 C26 -5.8(14) . . . . ?
O1 Eu1 O6 C26 128.4(11) . . . . ?
O7 Eu1 O6 C26 -161.5(12) . . . . ?
O3 Eu1 O6 C26 -80.0(12) . . . . ?
O9 Eu1 O6 C26 70.3(11) . . . . ?
N1 Eu1 O6 C26 -107.7(12) . . . . ?
N3 Eu1 O6 C26 -6.1(10) . . . . ?
N5 Eu1 O6 C26 135.4(13) . . . . ?
C103 C105 C106 C107 -168(3) . . . . ?
C114 C105 C106 C107 -13(6) . . . . ?
C108 C107 C106 C105 -172(4) . . . . ?
C112 C107 C106 C105 6(6) . . . . ?
C105 C114 C113 C112 -16(7) . . . . ?
C111 C112 C113 C114 -175(4) . . . . ?
C107 C112 C113 C114 9(6) . . . . ?
C14 C15 C16 C17 -3(7) . . . . ?
C12 C17 C16 C15 10(7) . . . . ?
C18 C17 C16 C15 -178(4) . . . . ?
C123 C124 C125 C116 0.0 . . . . ?
C124 C125 C116 C117 0.0 . . . . ?
C124 C125 C116 C103 -160(2) . . . . ?
C105 C103 C116 C125 -8(3) . . . . ?
N12 C103 C116 C125 -119(2) . . . . ?
C115 C103 C116 C125 52(3) . . . . ?
C104 C103 C116 C125 161(4) . . . . ?
C105 C103 C116 C117 -169.9(19) . . . . ?
N12 C103 C116 C117 79.2(14) . . . . ?
C115 C103 C116 C117 -110(2) . . . . ?
C104 C103 C116 C117 -1(3) . . . . ?
C125 C116 C117 C118 0.0 . . . . ?
C103 C116 C117 C118 165.8(18) . . . . ?
C116 C117 C118 C123 0.0 . . . . ?
C116 C117 C118 C119 180.0 . . . . ?
C117 C118 C123 C122 180.0 . . . . ?
C119 C118 C123 C122 0.0 . . . . ?
C117 C118 C123 C124 0.0 . . . . ?
C119 C118 C123 C124 180.0 . . . . ?
C125 C124 C123 C122 180.0 . . . . ?
C125 C124 C123 C118 0.0 . . . . ?
C118 C123 C122 C121 0.0 . . . . ?
C124 C123 C122 C121 180.0 . . . . ?
C123 C122 C121 C120 0.0 . . . . ?
C122 C121 C120 C119 0.0 . . . . ?
C121 C120 C119 C118 0.0 . . . . ?
C117 C118 C119 C120 180.0 . . . . ?
C123 C118 C119 C120 0.0 . . . . ?

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
N2 H2 O16 0.88 2.16 3.031(14) 172.0 8_456
N4 H4A O23 0.88 2.06 2.88(3) 155.1 .
N6 H6 O10 0.88 2.34 3.140(12) 152.0 3_656
N8 H8 O20 0.88 1.96 2.78(2) 155.3 .
N10 H10 O19 0.88 2.14 2.981(17) 161.0 .
N12 H12 O1 0.88 1.97 2.83(2) 164.8 3_656
O19 H19A O5 0.828 1.951(18) 2.78(2) 178.2(13) .
O19 H19B O17 0.833 2.145(17) 2.98(2) 178.6(13) 8_456
O20 H20A O8 0.829 1.969(15) 2.80(2) 177.4(14) 8_556
O22 H22A O8 0.78 3.240(17) 4.00(6) 167(4) 6_554
O23 H23A O2 0.837 1.798(19) 2.64(3) 178(2) 7_556
O23 H23B O24 0.865 1.94(2) 2.80(3) 177(2) .
O24 H24A O13 0.85 2.352(12) 2.93(2) 125.6(15) 5_455
O24 H24B O14 0.83 2.457(9) 2.87(3) 111.3(15) 5_455

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        50.55
_diffrn_measured_fraction_theta_full 0.896
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.134
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_database_code_depnum_ccdc_archive 'CCDC 1026036'
