# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1055165'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H19 Eu N6 O10'
_chemical_formula_weight         775.47

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.4550(11)
_cell_length_b                   17.5918(9)
_cell_length_c                   19.7955(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.960(7)
_cell_angle_gamma                90.00
_cell_volume                     5872.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00(13)
_cell_measurement_reflns_used    8867
_cell_measurement_theta_min      2.7760
_cell_measurement_theta_max      29.1820

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3072
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.00(13)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14157
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5163
_reflns_number_gt                4487
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL

_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)+(0.0733P)²+104.1585P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.988507(19) 0.042533(19) 0.619705(18) 0.01804(16) Uani 1 1 d . . .
N6 N 0.9818(3) -0.1217(3) 0.6353(3) 0.0223(13) Uani 1 1 d . . .
O4 O 0.9225(3) -0.0542(3) 0.4467(3) 0.0295(12) Uani 1 1 d . . .
O9 O 1.0282(3) -0.0925(3) 0.6042(3) 0.0316(12) Uani 1 1 d . . .
C30 C 0.8752(4) -0.0515(4) 0.4838(4) 0.0195(15) Uani 1 1 d . . .
O2 O 1.0906(3) 0.0359(3) 0.7187(3) 0.0258(11) Uani 1 1 d . . .
O3 O 0.8814(3) -0.0074(3) 0.5347(2) 0.0230(10) Uani 1 1 d . . .
O1 O 1.1111(3) 0.0767(3) 0.8276(3) 0.0279(11) Uani 1 1 d . . .
C15 C 1.1352(4) 0.0617(4) 0.7746(4) 0.0215(15) Uani 1 1 d . . .
N1 N 1.3051(4) -0.0323(3) 0.6239(3) 0.0279(14) Uani 1 1 d . . .
N5 N 0.9697(4) 0.2047(4) 0.6014(4) 0.0315(15) Uani 1 1 d . . .
C7 C 1.2478(4) 0.0432(4) 0.7243(4) 0.0195(15) Uani 1 1 d . . .
H7A H 1.2134 0.0138 0.6906 0.023 Uiso 1 1 calc R . .
N4 N 0.6818(3) -0.2117(3) 0.4174(3) 0.0221(12) Uani 1 1 d . . .
N2 N 1.3783(4) 0.0967(3) 0.7666(3) 0.0244(13) Uani 1 1 d . . .
N3 N 0.6684(4) -0.2968(3) 0.3057(3) 0.0266(14) Uani 1 1 d . . .
O8 O 0.9482(3) -0.0761(3) 0.6698(3) 0.0326(12) Uani 1 1 d . . .
O6 O 1.0252(3) 0.1763(3) 0.6507(3) 0.0282(11) Uani 1 1 d . . .
C10 C 1.2564(4) 0.1590(4) 0.8851(4) 0.0241(15) Uani 1 1 d . . .
H10A H 1.2062 0.1536 0.8926 0.029 Uiso 1 1 calc R . .
O5 O 0.9286(3) 0.1592(3) 0.5578(3) 0.0287(12) Uani 1 1 d . . .
C4 C 1.4289(5) 0.0356(4) 0.6525(4) 0.0259(16) Uani 1 1 d . . .
H4A H 1.4621 0.0705 0.6811 0.031 Uiso 1 1 calc R . .
C24 C 0.7444(4) -0.1124(4) 0.5011(4) 0.0203(14) Uani 1 1 d . . .
C22 C 0.8043(4) -0.1539(4) 0.4100(4) 0.0208(14) Uani 1 1 d . . .
H22A H 0.8450 -0.1521 0.3876 0.025 Uiso 1 1 calc R . .
C2 C 1.4008(5) -0.0503(4) 0.5571(4) 0.0306(18) Uani 1 1 d . . .
H2A H 1.4148 -0.0749 0.5205 0.037 Uiso 1 1 calc R . .
C21 C 0.7404(4) -0.2051(4) 0.3871(4) 0.0222(15) Uani 1 1 d . . .
C26 C 0.6764(4) -0.0803(4) 0.5892(4) 0.0286(16) Uani 1 1 d . . .
H26A H 0.6737 -0.0511 0.6277 0.034 Uiso 1 1 calc R . .
C9 C 1.2748(4) 0.1203(4) 0.8287(4) 0.0193(14) Uani 1 1 d . . .
C20 C 0.7359(4) -0.2542(4) 0.3258(4) 0.0233(15) Uani 1 1 d . . .
C27 C 0.6160(4) -0.1336(4) 0.5630(4) 0.0273(16) Uani 1 1 d . . .
H27A H 0.5748 -0.1403 0.5843 0.033 Uiso 1 1 calc R . .
C23 C 0.8058(4) -0.1070(4) 0.4657(3) 0.0198(14) Uani 1 1 d . . .
C12 C 1.3880(4) 0.2151(4) 0.9184(4) 0.0269(16) Uani 1 1 d . . .
H12A H 1.4242 0.2474 0.9474 0.032 Uiso 1 1 calc R . .
O10 O 0.9684(3) -0.1898(3) 0.6367(4) 0.0437(15) Uani 1 1 d . . .
C14 C 1.3523(4) 0.1298(4) 0.8192(4) 0.0223(15) Uani 1 1 d . . .
C29 C 0.6825(4) -0.1670(4) 0.4739(4) 0.0228(15) Uani 1 1 d . . .
C6 C 1.3276(4) 0.0537(4) 0.7207(4) 0.0224(15) Uani 1 1 d . . .
C8 C 1.2213(4) 0.0758(4) 0.7769(4) 0.0206(14) Uani 1 1 d . . .
C25 C 0.7386(4) -0.0695(4) 0.5606(4) 0.0247(15) Uani 1 1 d . . .
H25A H 0.7776 -0.0340 0.5800 0.030 Uiso 1 1 calc R . .
C5 C 1.3557(4) 0.0178(4) 0.6638(4) 0.0243(15) Uani 1 1 d . . .
O7 O 0.9570(4) 0.2740(3) 0.5983(4) 0.0497(17) Uani 1 1 d . . .
C28 C 0.6190(4) -0.1752(4) 0.5057(4) 0.0263(16) Uani 1 1 d . . .
H28A H 0.5786 -0.2096 0.4871 0.032 Uiso 1 1 calc R . .
C1 C 1.4517(5) 0.0011(5) 0.5984(4) 0.0330(18) Uani 1 1 d . . .
H1A H 1.5004 0.0121 0.5899 0.040 Uiso 1 1 calc R . .
C18 C 0.7774(5) -0.3055(4) 0.2292(4) 0.0334(18) Uani 1 1 d . . .
H18A H 0.8147 -0.3084 0.2032 0.040 Uiso 1 1 calc R . .
C11 C 1.3115(5) 0.2043(4) 0.9289(4) 0.0265(16) Uani 1 1 d . . .
H11A H 1.2984 0.2283 0.9663 0.032 Uiso 1 1 calc R . .
C17 C 0.7079(5) -0.3474(4) 0.2090(4) 0.0331(18) Uani 1 1 d . . .
H17A H 0.6975 -0.3778 0.1693 0.040 Uiso 1 1 calc R . .
C16 C 0.6548(5) -0.3428(4) 0.2492(4) 0.0314(18) Uani 1 1 d . . .
H16A H 0.6087 -0.3718 0.2375 0.038 Uiso 1 1 calc R . .
C3 C 1.3282(5) -0.0648(5) 0.5710(4) 0.0301(17) Uani 1 1 d . . .
H3A H 1.2939 -0.0988 0.5423 0.036 Uiso 1 1 calc R . .
C19 C 0.7916(5) -0.2592(4) 0.2880(4) 0.0263(16) Uani 1 1 d . . .
H19A H 0.8386 -0.2317 0.3017 0.032 Uiso 1 1 calc R . .
C13 C 1.4078(4) 0.1776(4) 0.8652(4) 0.0258(16) Uani 1 1 d . . .
H13A H 1.4584 0.1834 0.8588 0.031 Uiso 1 1 calc R . .


_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 O2 2.286(5) . ?
Eu1 O4 2.290(5) 5_756 ?
Eu1 O1 2.326(5) 2_756 ?
Eu1 O3 2.340(5) . ?
Eu1 O6 2.473(5) . ?
Eu1 O5 2.480(5) . ?
Eu1 O8 2.489(5) . ?
Eu1 O9 2.515(5) . ?
Eu1 N5 2.883(7) . ?
Eu1 N6 2.910(6) . ?
N6 O10 1.223(8) . ?
N6 O9 1.246(8) . ?
N6 O8 1.290(8) . ?
O4 C30 1.239(9) . ?
O4 Eu1 2.290(5) 5_756 ?
C30 O3 1.253(9) . ?
C30 C23 1.525(9) . ?
O2 C15 1.262(9) . ?
O1 C15 1.255(9) . ?
O1 Eu1 2.326(5) 2_756 ?
C15 C8 1.513(10) . ?
N1 C5 1.348(10) . ?
N1 C3 1.343(10) . ?
N5 O7 1.237(9) . ?
N5 O5 1.257(8) . ?
N5 O6 1.286(9) . ?
C7 C8 1.369(10) . ?
C7 C6 1.425(10) . ?
N4 C21 1.319(9) . ?
N4 C29 1.364(9) . ?
N2 C6 1.329(9) . ?
N2 C14 1.368(9) . ?
N3 C16 1.350(10) . ?
N3 C20 1.366(9) . ?
C10 C11 1.372(10) . ?
C10 C9 1.414(10) . ?
C4 C1 1.376(11) . ?
C4 C5 1.389(10) . ?
C24 C23 1.426(10) . ?
C24 C25 1.424(10) . ?
C24 C29 1.443(10) . ?
C22 C23 1.372(10) . ?
C22 C21 1.413(10) . ?
C2 C3 1.387(11) . ?
C2 C1 1.378(12) . ?
C21 C20 1.475(10) . ?
C26 C25 1.362(10) . ?
C26 C27 1.406(11) . ?
C9 C14 1.422(9) . ?
C9 C8 1.430(10) . ?
C20 C19 1.374(11) . ?
C27 C28 1.363(11) . ?
C12 C13 1.359(11) . ?
C12 C11 1.417(11) . ?
C14 C13 1.421(10) . ?
C29 C28 1.417(10) . ?
C6 C5 1.482(10) . ?
C18 C17 1.388(12) . ?
C18 C19 1.389(11) . ?
C17 C16 1.371(12) . ?

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
O2 Eu1 O4 90.15(19) . 5_756 ?
O2 Eu1 O1 97.85(18) . 2_756 ?
O4 Eu1 O1 158.6(2) 5_756 2_756 ?
O2 Eu1 O3 153.97(17) . . ?
O4 Eu1 O3 98.92(17) 5_756 . ?
O1 Eu1 O3 82.45(17) 2_756 . ?
O2 Eu1 O6 75.01(18) . . ?
O4 Eu1 O6 83.46(18) 5_756 . ?
O1 Eu1 O6 79.56(18) 2_756 . ?
O3 Eu1 O6 130.04(17) . . ?
O2 Eu1 O5 127.02(17) . . ?
O4 Eu1 O5 84.48(19) 5_756 . ?
O1 Eu1 O5 74.86(18) 2_756 . ?
O3 Eu1 O5 78.39(17) . . ?
O6 Eu1 O5 52.01(17) . . ?
O2 Eu1 O8 81.57(18) . . ?
O4 Eu1 O8 127.46(19) 5_756 . ?
O1 Eu1 O8 73.55(18) 2_756 . ?
O3 Eu1 O8 73.52(18) . . ?
O6 Eu1 O8 141.28(17) . . ?
O5 Eu1 O8 139.87(18) . . ?
O2 Eu1 O9 83.00(18) . . ?
O4 Eu1 O9 76.45(18) 5_756 . ?
O1 Eu1 O9 124.07(18) 2_756 . ?
O3 Eu1 O9 75.60(17) . . ?
O6 Eu1 O9 150.07(17) . . ?
O5 Eu1 O9 144.66(18) . . ?
O8 Eu1 O9 51.10(17) . . ?
O2 Eu1 N5 101.34(19) . . ?
O4 Eu1 N5 84.90(19) 5_756 . ?
O1 Eu1 N5 74.12(19) 2_756 . ?
O3 Eu1 N5 103.72(19) . . ?
O6 Eu1 N5 26.39(18) . . ?
O5 Eu1 N5 25.71(18) . . ?
O8 Eu1 N5 147.64(18) . . ?
O9 Eu1 N5 160.90(18) . . ?
O2 Eu1 N6 84.38(16) . . ?
O4 Eu1 N6 101.63(19) 5_756 . ?
O1 Eu1 N6 98.87(18) 2_756 . ?
O3 Eu1 N6 69.95(16) . . ?
O6 Eu1 N6 158.83(17) . . ?
O5 Eu1 N6 148.29(16) . . ?
O8 Eu1 N6 26.18(18) . . ?
O9 Eu1 N6 25.23(17) . . ?
N5 Eu1 N6 171.40(18) . . ?
O10 N6 O9 124.6(7) . . ?
O10 N6 O8 118.7(6) . . ?
O9 N6 O8 116.7(6) . . ?
O10 N6 Eu1 171.2(5) . . ?
O9 N6 Eu1 59.4(3) . . ?
O8 N6 Eu1 58.4(3) . . ?
C30 O4 Eu1 172.6(5) . 5_756 ?
N6 O9 Eu1 95.4(4) . . ?
O4 C30 O3 124.5(6) . . ?
O4 C30 C23 116.5(6) . . ?
O3 C30 C23 118.9(6) . . ?
C15 O2 Eu1 154.3(5) . . ?
C30 O3 Eu1 134.2(4) . . ?
C15 O1 Eu1 140.4(5) . 2_756 ?
O1 C15 O2 123.1(7) . . ?
O1 C15 C8 119.0(6) . . ?
O2 C15 C8 117.9(6) . . ?
C5 N1 C3 116.9(7) . . ?
O7 N5 O5 122.0(7) . . ?
O7 N5 O6 120.7(7) . . ?
O5 N5 O6 117.3(6) . . ?
O7 N5 Eu1 173.6(6) . . ?
O5 N5 Eu1 58.9(3) . . ?
O6 N5 Eu1 58.7(3) . . ?
C8 C7 C6 120.6(7) . . ?
C21 N4 C29 118.5(6) . . ?
C6 N2 C14 118.0(6) . . ?
C16 N3 C20 121.6(7) . . ?
N6 O8 Eu1 95.5(4) . . ?
N5 O6 Eu1 94.9(4) . . ?
C11 C10 C9 120.9(7) . . ?
N5 O5 Eu1 95.4(4) . . ?
C1 C4 C5 119.2(7) . . ?
C23 C24 C25 126.4(6) . . ?
C23 C24 C29 116.5(6) . . ?
C25 C24 C29 117.1(6) . . ?
C23 C22 C21 119.3(6) . . ?
C3 C2 C1 119.0(7) . . ?
N4 C21 C22 123.5(7) . . ?
N4 C21 C20 116.1(6) . . ?
C22 C21 C20 120.4(6) . . ?
C25 C26 C27 122.8(7) . . ?
C10 C9 C14 117.8(6) . . ?
C10 C9 C8 126.2(6) . . ?
C14 C9 C8 115.9(6) . . ?
N3 C20 C19 119.0(7) . . ?
N3 C20 C21 114.8(6) . . ?
C19 C20 C21 126.2(6) . . ?
C28 C27 C26 118.7(7) . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 C30 115.0(6) . . ?
C24 C23 C30 125.4(6) . . ?
C13 C12 C11 119.1(7) . . ?
N2 C14 C13 115.8(6) . . ?
N2 C14 C9 124.3(6) . . ?
C13 C14 C9 119.9(6) . . ?
N4 C29 C28 117.5(6) . . ?
N4 C29 C24 122.6(6) . . ?
C28 C29 C24 119.9(7) . . ?
N2 C6 C7 121.8(7) . . ?
N2 C6 C5 118.1(6) . . ?
C7 C6 C5 120.1(6) . . ?
C7 C8 C9 119.2(6) . . ?
C7 C8 C15 115.9(6) . . ?
C9 C8 C15 124.8(6) . . ?
C26 C25 C24 120.3(7) . . ?
N1 C5 C4 122.9(7) . . ?
N1 C5 C6 115.4(6) . . ?
C4 C5 C6 121.6(7) . . ?
C27 C28 C29 121.1(7) . . ?
C2 C1 C4 118.6(7) . . ?
C17 C18 C19 120.5(8) . . ?
C10 C11 C12 121.3(7) . . ?
C16 C17 C18 118.2(7) . . ?
N3 C16 C17 121.0(7) . . ?
N1 C3 C2 123.3(8) . . ?
C20 C19 C18 119.7(7) . . ?
C12 C13 C14 121.1(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         3.612
_refine_diff_density_min         -1.514
_refine_diff_density_rms         0.196
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1055166'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H19 N6 O10 Tb'
_chemical_formula_weight         782.43

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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.400(5)
_cell_length_b                   17.775(5)
_cell_length_c                   19.987(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.563(5)
_cell_angle_gamma                90.00
_cell_volume                     5983(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7354
_cell_measurement_theta_min      2.1075
_cell_measurement_theta_max      27.4740

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3088
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Sphere(Rigaku CryatalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 14.6306
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24758
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6842
_reflns_number_gt                6154
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0357P)²+203.5092P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6842
_refine_ls_number_parameters     424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.01070(2) 0.03698(2) 0.37891(2) 0.03357(13) Uani 1 1 d . . .
O1 O 0.1108(4) 0.0679(4) 0.3278(3) 0.0474(16) Uani 1 1 d . . .
N1 N -0.3287(5) 0.2943(4) 0.3078(4) 0.0479(19) Uani 1 1 d . . .
C1 C -0.3423(7) 0.3402(6) 0.2522(6) 0.061(3) Uani 1 1 d . . .
H1 H -0.3883 0.3692 0.2411 0.073 Uiso 1 1 calc R . .
O2 O -0.0788(4) 0.0490(4) 0.4427(4) 0.0531(19) Uani 1 1 d . . .
N2 N -0.3155(4) 0.2098(4) 0.4181(4) 0.0417(17) Uani 1 1 d . . .
C2 C -0.2898(8) 0.3448(6) 0.2122(6) 0.062(3) Uani 1 1 d . . .
H2 H -0.3003 0.3748 0.1728 0.075 Uiso 1 1 calc R . .
O3 O -0.0893(4) 0.0329(4) 0.2816(3) 0.0480(16) Uani 1 1 d . . .
C19 C -0.4282(6) 0.0359(7) 0.3467(6) 0.057(3) Uani 1 1 d D . .
H19 H -0.4607 0.0711 0.3188 0.069 Uiso 1 1 calc RD . .
C3 C -0.2210(8) 0.3041(6) 0.2315(6) 0.059(3) Uani 1 1 d . . .
H3 H -0.1834 0.3076 0.2058 0.071 Uiso 1 1 calc R . .
N4 N -0.3761(4) 0.0954(5) 0.2339(4) 0.0433(18) Uani 1 1 d . . .
O4 O 0.1139(4) -0.0108(4) 0.4652(3) 0.0457(16) Uani 1 1 d . . .
C4 C -0.2067(7) 0.2571(6) 0.2897(5) 0.052(2) Uani 1 1 d . . .
H4 H -0.1598 0.2297 0.3026 0.062 Uiso 1 1 calc R . .
C5 C -0.2618(6) 0.2519(5) 0.3274(5) 0.0405(19) Uani 1 1 d . . .
O5 O -0.0244(5) 0.1680(4) 0.3483(4) 0.0607(19) Uani 1 1 d . . .
N5 N 0.0275(6) 0.1961(5) 0.3989(5) 0.060(2) Uani 1 1 d . . .
N6 N 0.0161(4) -0.1227(4) 0.3631(4) 0.0420(18) Uani 1 1 d . . .
C6 C -0.2575(5) 0.2031(5) 0.3878(4) 0.0368(18) Uani 1 1 d . . .
O6 O 0.0697(5) 0.1506(5) 0.4419(4) 0.065(2) Uani 1 1 d . . .
C7 C -0.1944(5) 0.1521(5) 0.4107(4) 0.0356(18) Uani 1 1 d . . .
H7 H -0.1533 0.1505 0.3887 0.043 Uiso 1 1 calc R . .
O7 O 0.0383(8) 0.2641(5) 0.4061(7) 0.120(4) Uani 1 1 d . . .
O8 O 0.0506(5) -0.0795(5) 0.3297(4) 0.065(2) Uani 1 1 d . . .
C8 C -0.1930(5) 0.1051(5) 0.4646(4) 0.0323(16) Uani 1 1 d . . .
C9 C -0.2538(5) 0.1111(5) 0.5005(4) 0.0352(17) Uani 1 1 d . . .
O9 O -0.0298(5) -0.0956(5) 0.3929(4) 0.068(2) Uani 1 1 d . . .
C10 C -0.2601(5) 0.0677(6) 0.5581(5) 0.044(2) Uani 1 1 d . . .
H10 H -0.2216 0.0318 0.5759 0.053 Uiso 1 1 calc R . .
O10 O 0.0285(6) -0.1912(5) 0.3615(6) 0.096(3) Uani 1 1 d . . .
C11 C -0.3219(6) 0.0777(6) 0.5881(5) 0.051(2) Uani 1 1 d . . .
H11 H -0.3248 0.0486 0.6261 0.061 Uiso 1 1 calc R . .
C12 C -0.3812(6) 0.1317(6) 0.5620(5) 0.049(2) Uani 1 1 d . . .
H12 H -0.4228 0.1382 0.5829 0.059 Uiso 1 1 calc R . .
C13 C -0.3777(5) 0.1742(6) 0.5065(5) 0.047(2) Uani 1 1 d . . .
H13 H -0.4169 0.2100 0.4900 0.057 Uiso 1 1 calc R . .
C14 C -0.3153(5) 0.1649(5) 0.4734(4) 0.0364(18) Uani 1 1 d . . .
C15 C -0.1227(5) 0.0509(5) 0.4834(4) 0.0347(18) Uani 1 1 d . . .
C18 C -0.4518(8) 0.0011(8) 0.4008(7) 0.075(4) Uani 1 1 d . . .
H18 H -0.5003 0.0131 0.4097 0.090 Uiso 1 1 calc R . .
C17 C -0.4025(8) -0.0511(7) 0.4408(7) 0.073(4) Uani 1 1 d . . .
H17 H -0.4173 -0.0755 0.4768 0.087 Uiso 1 1 calc R . .
C16 C -0.3305(8) -0.0665(7) 0.4261(7) 0.072(4) Uani 1 1 d . . .
H16 H -0.2968 -0.1010 0.4540 0.086 Uiso 1 1 calc R . .
N3 N -0.3068(6) -0.0347(5) 0.3744(5) 0.057(2) Uani 1 1 d . . .
C20 C -0.3555(6) 0.0168(5) 0.3354(5) 0.043(2) Uani 1 1 d . . .
C21 C -0.3258(5) 0.0524(5) 0.2795(5) 0.0382(19) Uani 1 1 d . . .
C22 C -0.2466(5) 0.0412(5) 0.2765(4) 0.0367(18) Uani 1 1 d . . .
H22 H -0.2127 0.0126 0.3105 0.044 Uiso 1 1 calc R . .
C23 C -0.2190(5) 0.0720(5) 0.2244(4) 0.0341(17) Uani 1 1 d . . .
C24 C -0.2718(5) 0.1176(5) 0.1735(4) 0.0362(18) Uani 1 1 d . . .
C25 C -0.2526(6) 0.1552(6) 0.1167(5) 0.045(2) Uani 1 1 d . . .
H25 H -0.2029 0.1483 0.1083 0.054 Uiso 1 1 calc R . .
C26 C -0.3067(7) 0.2010(6) 0.0747(5) 0.055(3) Uani 1 1 d . . .
H26 H -0.2927 0.2257 0.0384 0.066 Uiso 1 1 calc R . .
C27 C -0.3831(6) 0.2119(7) 0.0847(6) 0.058(3) Uani 1 1 d . . .
H27 H -0.4189 0.2436 0.0555 0.070 Uiso 1 1 calc R . .
C28 C -0.4038(6) 0.1759(6) 0.1369(5) 0.052(2) Uani 1 1 d . . .
H28 H -0.4546 0.1825 0.1431 0.062 Uiso 1 1 calc R . .
C29 C -0.3497(5) 0.1283(5) 0.1823(5) 0.0389(19) Uani 1 1 d . . .
C30 C -0.1337(5) 0.0570(5) 0.2251(4) 0.0362(18) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O2 2.257(6) . ?
Tb1 O3 2.262(6) . ?
Tb1 O1 2.297(6) . ?
Tb1 O4 2.315(6) . ?
Tb1 O5 2.446(7) . ?
Tb1 O6 2.464(8) . ?
Tb1 O8 2.466(8) . ?
Tb1 O9 2.496(8) . ?
Tb1 N6 2.861(7) . ?
Tb1 N5 2.861(10) . ?
O1 C30 1.236(10) 2 ?
N1 C5 1.359(12) . ?
N1 C1 1.352(13) . ?
C1 C2 1.359(17) . ?
O2 C15 1.249(10) . ?
N2 C6 1.306(11) . ?
N2 C14 1.363(11) . ?
C2 C3 1.369(16) . ?
O3 C30 1.270(10) . ?
C19 C20 1.383(14) . ?
C19 C18 1.394(15) . ?
C3 C4 1.402(14) . ?
N4 C21 1.333(11) . ?
N4 C29 1.361(11) . ?
O4 C15 1.228(10) 5_556 ?
C4 C5 1.363(14) . ?
C5 C6 1.473(12) . ?
O5 N5 1.275(12) . ?
N5 O7 1.226(13) . ?
N5 O6 1.270(12) . ?
N6 O9 1.210(11) . ?
N6 O10 1.238(11) . ?
N6 O8 1.263(11) . ?
C6 C7 1.409(12) . ?
C7 C8 1.358(11) . ?
C8 C9 1.423(11) . ?
C8 C15 1.527(11) . ?
C9 C10 1.412(12) . ?
C9 C14 1.436(12) . ?
C10 C11 1.368(12) . ?
C11 C12 1.411(14) . ?
C12 C13 1.355(14) . ?
C13 C14 1.417(12) . ?
C15 O4 1.228(10) 5_556 ?
C18 C17 1.375(19) . ?
C17 C16 1.384(17) . ?
C16 N3 1.333(13) . ?
N3 C20 1.353(13) . ?
C20 C21 1.485(12) . ?
C21 C22 1.409(12) . ?
C22 C23 1.367(12) . ?
C23 C24 1.437(12) . ?
C23 C30 1.504(11) . ?
C24 C29 1.424(12) . ?
C24 C25 1.428(12) . ?
C25 C26 1.362(13) . ?
C26 C27 1.406(15) . ?
C27 C28 1.348(15) . ?
C28 C29 1.413(13) . ?
C30 O1 1.236(10) 2 ?

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
O2 Tb1 O3 89.9(3) . . ?
O2 Tb1 O1 159.5(3) . . ?
O3 Tb1 O1 97.5(2) . . ?
O2 Tb1 O4 97.5(2) . . ?
O3 Tb1 O4 156.0(3) . . ?
O1 Tb1 O4 83.5(2) . . ?
O2 Tb1 O5 83.5(2) . . ?
O3 Tb1 O5 74.1(3) . . ?
O1 Tb1 O5 80.2(3) . . ?
O4 Tb1 O5 129.3(3) . . ?
O2 Tb1 O6 83.8(3) . . ?
O3 Tb1 O6 126.7(3) . . ?
O1 Tb1 O6 76.5(3) . . ?
O4 Tb1 O6 77.0(3) . . ?
O5 Tb1 O6 52.6(3) . . ?
O2 Tb1 O8 127.4(3) . . ?
O3 Tb1 O8 82.1(3) . . ?
O1 Tb1 O8 72.7(3) . . ?
O4 Tb1 O8 75.3(3) . . ?
O5 Tb1 O8 141.0(3) . . ?
O6 Tb1 O8 140.3(3) . . ?
O2 Tb1 O9 76.8(3) . . ?
O3 Tb1 O9 83.6(3) . . ?
O1 Tb1 O9 122.9(3) . . ?
O4 Tb1 O9 76.0(3) . . ?
O5 Tb1 O9 150.2(3) . . ?
O6 Tb1 O9 144.1(3) . . ?
O8 Tb1 O9 50.7(3) . . ?
O2 Tb1 N6 101.7(3) . . ?
O3 Tb1 N6 85.0(2) . . ?
O1 Tb1 N6 98.0(3) . . ?
O4 Tb1 N6 71.2(2) . . ?
O5 Tb1 N6 158.5(3) . . ?
O6 Tb1 N6 148.1(2) . . ?
O8 Tb1 N6 26.1(2) . . ?
O9 Tb1 N6 24.9(2) . . ?
O2 Tb1 N5 83.6(3) . . ?
O3 Tb1 N5 100.4(3) . . ?
O1 Tb1 N5 76.3(3) . . ?
O4 Tb1 N5 103.0(3) . . ?
O5 Tb1 N5 26.3(3) . . ?
O6 Tb1 N5 26.3(3) . . ?
O8 Tb1 N5 148.9(3) . . ?
O9 Tb1 N5 160.0(3) . . ?
N6 Tb1 N5 172.5(3) . . ?
C30 O1 Tb1 141.9(6) 2 . ?
C5 N1 C1 122.2(9) . . ?
N1 C1 C2 121.0(11) . . ?
C15 O2 Tb1 173.0(6) . . ?
C6 N2 C14 118.5(7) . . ?
C1 C2 C3 118.2(10) . . ?
C30 O3 Tb1 156.6(6) . . ?
C20 C19 C18 118.6(11) . . ?
C2 C3 C4 120.6(11) . . ?
C21 N4 C29 118.4(8) . . ?
C15 O4 Tb1 138.3(6) 5_556 . ?
C5 C4 C3 119.8(10) . . ?
N1 C5 C4 118.2(9) . . ?
N1 C5 C6 115.2(8) . . ?
C4 C5 C6 126.6(9) . . ?
N5 O5 Tb1 95.3(6) . . ?
O7 N5 O6 120.2(12) . . ?
O7 N5 O5 122.4(11) . . ?
O6 N5 O5 117.4(9) . . ?
O7 N5 Tb1 176.5(10) . . ?
O6 N5 Tb1 59.1(5) . . ?
O5 N5 Tb1 58.4(5) . . ?
O9 N6 O10 123.0(10) . . ?
O9 N6 O8 118.5(8) . . ?
O10 N6 O8 118.4(9) . . ?
O9 N6 Tb1 60.4(5) . . ?
O10 N6 Tb1 171.7(7) . . ?
O8 N6 Tb1 59.2(4) . . ?
N2 C6 C7 122.6(8) . . ?
N2 C6 C5 116.1(8) . . ?
C7 C6 C5 121.3(8) . . ?
N5 O6 Tb1 94.6(6) . . ?
C8 C7 C6 120.7(8) . . ?
N6 O8 Tb1 94.7(5) . . ?
C7 C8 C9 119.1(8) . . ?
C7 C8 C15 115.9(7) . . ?
C9 C8 C15 125.0(7) . . ?
C10 C9 C8 126.2(8) . . ?
C10 C9 C14 117.8(8) . . ?
C8 C9 C14 116.0(8) . . ?
N6 O9 Tb1 94.7(6) . . ?
C11 C10 C9 121.2(9) . . ?
C10 C11 C12 120.5(10) . . ?
C13 C12 C11 120.2(9) . . ?
C12 C13 C14 120.9(9) . . ?
N2 C14 C13 117.7(8) . . ?
N2 C14 C9 123.0(8) . . ?
C13 C14 C9 119.2(8) . . ?
O4 C15 O2 124.1(8) 5_556 . ?
O4 C15 C8 119.8(7) 5_556 . ?
O2 C15 C8 116.1(7) . . ?
C17 C18 C19 119.2(12) . . ?
C18 C17 C16 118.4(11) . . ?
N3 C16 C17 123.6(12) . . ?
C16 N3 C20 117.7(10) . . ?
N3 C20 C19 122.5(9) . . ?
N3 C20 C21 115.8(8) . . ?
C19 C20 C21 121.7(9) . . ?
N4 C21 C22 122.2(8) . . ?
N4 C21 C20 117.7(8) . . ?
C22 C21 C20 120.0(8) . . ?
C23 C22 C21 120.7(8) . . ?
C22 C23 C24 118.7(8) . . ?
C22 C23 C30 117.2(8) . . ?
C24 C23 C30 124.1(8) . . ?
C29 C24 C23 116.6(8) . . ?
C29 C24 C25 117.2(8) . . ?
C23 C24 C25 126.2(8) . . ?
C26 C25 C24 120.4(9) . . ?
C25 C26 C27 121.7(10) . . ?
C28 C27 C26 119.4(9) . . ?
C27 C28 C29 121.1(9) . . ?
N4 C29 C28 116.6(8) . . ?
N4 C29 C24 123.3(8) . . ?
C28 C29 C24 120.1(8) . . ?
O1 C30 O3 123.9(8) 2 . ?
O1 C30 C23 119.6(8) 2 . ?
O3 C30 C23 116.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.813
_refine_diff_density_min         -2.045
_refine_diff_density_rms         0.166
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zj001
_database_code_depnum_ccdc_archive 'CCDC 1055167'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cl N2 O3'
_chemical_formula_weight         304.72

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'
Cl Cl 0.3639 0.7018 '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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4489(7)
_cell_length_b                   8.9646(7)
_cell_length_c                   9.2306(5)
_cell_angle_alpha                91.897(5)
_cell_angle_beta                 97.303(5)
_cell_angle_gamma                95.599(6)
_cell_volume                     689.42(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.98(18)
_cell_measurement_reflns_used    1987
_cell_measurement_theta_min      4.8050
_cell_measurement_theta_max      73.4820

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    2.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;  
 ? 
;

_diffrn_ambient_temperature      99.98(18)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_standards_number         4525
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4490
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.84
_diffrn_reflns_theta_max         74.79
_reflns_number_total             2721
_reflns_number_gt                2305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL

_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)+(0.0625P)²+0.1457P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2721
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.78773(6) 0.58122(6) 0.83184(5) 0.03359(16) Uani 1 1 d . . .
O19 O 0.18466(18) -0.05212(16) 0.23362(14) 0.0300(3) Uani 1 1 d . . .
H19 H 0.1334 -0.1245 0.1871 0.045 Uiso 1 1 calc R . .
O18 O 0.11346(18) -0.17734(16) 0.42481(15) 0.0318(3) Uani 1 1 d . . .
O1W O 0.9294(2) 0.28715(16) 0.92974(16) 0.0358(4) Uani 1 1 d G . .
H1WA H 1.0108 0.3114 0.9932 0.054 Uiso 1 1 d G . .
H1WB H 0.8877 0.3657 0.9021 0.054 Uiso 1 1 d G . .
N1 N 0.71262(19) 0.45770(18) 0.50848(18) 0.0237(3) Uani 1 1 d . . .
H1 H 0.705(3) 0.453(3) 0.599(3) 0.041(7) Uiso 1 1 d . . .
N16 N 0.5166(2) 0.26676(18) 0.62795(17) 0.0251(3) Uani 1 1 d . . .
C17 C 0.1859(2) -0.0714(2) 0.3748(2) 0.0250(4) Uani 1 1 d . . .
C9 C 0.2919(2) 0.0497(2) 0.46762(19) 0.0226(4) Uani 1 1 d . . .
C6 C 0.6137(2) 0.3603(2) 0.4160(2) 0.0233(4) Uani 1 1 d . . .
C7 C 0.5019(2) 0.2540(2) 0.48386(19) 0.0228(4) Uani 1 1 d . . .
C8 C 0.3921(2) 0.1476(2) 0.39923(19) 0.0229(4) Uani 1 1 d . . .
H8 H 0.3869 0.1430 0.2979 0.027 Uiso 1 1 calc R . .
C15 C 0.4171(2) 0.1738(2) 0.6979(2) 0.0245(4) Uani 1 1 d . . .
C10 C 0.3004(2) 0.0625(2) 0.6232(2) 0.0235(4) Uani 1 1 d . . .
C5 C 0.6227(2) 0.3672(2) 0.2674(2) 0.0274(4) Uani 1 1 d . . .
H5 H 0.5545 0.3027 0.2009 0.033 Uiso 1 1 calc R . .
C2 C 0.8208(2) 0.5603(2) 0.4641(2) 0.0267(4) Uani 1 1 d . . .
H2 H 0.8859 0.6257 0.5322 0.032 Uiso 1 1 calc R . .
C11 C 0.2004(2) -0.0255(2) 0.7080(2) 0.0280(4) Uani 1 1 d . . .
H11 H 0.1233 -0.0989 0.6621 0.034 Uiso 1 1 calc R . .
C14 C 0.4329(3) 0.1939(2) 0.8527(2) 0.0330(5) Uani 1 1 d . . .
H14 H 0.5105 0.2653 0.9013 0.040 Uiso 1 1 calc R . .
C3 C 0.8351(2) 0.5683(2) 0.3178(2) 0.0292(4) Uani 1 1 d . . .
H3 H 0.9109 0.6376 0.2859 0.035 Uiso 1 1 calc R . .
C4 C 0.7345(3) 0.4713(2) 0.2188(2) 0.0308(4) Uani 1 1 d . . .
H4 H 0.7418 0.4760 0.1193 0.037 Uiso 1 1 calc R . .
C12 C 0.2175(3) -0.0023(2) 0.8575(2) 0.0344(5) Uani 1 1 d . . .
H12 H 0.1513 -0.0603 0.9117 0.041 Uiso 1 1 calc R . .
C13 C 0.3336(3) 0.1077(3) 0.9297(2) 0.0380(5) Uani 1 1 d . . .
H13 H 0.3428 0.1219 1.0308 0.046 Uiso 1 1 calc R . .


_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
O19 C17 1.319(2) . ?
O19 H19 0.8200 . ?
O18 C17 1.215(2) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8499 . ?
N1 C2 1.344(3) . ?
N1 C6 1.348(2) . ?
N1 H1 0.85(3) . ?
N16 C7 1.320(2) . ?
N16 C15 1.362(2) . ?
C17 C9 1.506(3) . ?
C9 C8 1.383(2) . ?
C9 C10 1.429(3) . ?
C6 C5 1.387(3) . ?
C6 C7 1.486(2) . ?
C7 C8 1.405(3) . ?
C8 H8 0.9300 . ?
C15 C14 1.422(3) . ?
C15 C10 1.426(3) . ?
C10 C11 1.424(3) . ?
C5 C4 1.389(3) . ?
C5 H5 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C14 C13 1.367(3) . ?
C14 H14 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C12 C13 1.408(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
C17 O19 H19 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
C2 N1 C6 123.34(17) . . ?
C2 N1 H1 119.4(19) . . ?
C6 N1 H1 117.3(19) . . ?
C7 N16 C15 118.03(16) . . ?
O18 C17 O19 123.90(17) . . ?
O18 C17 C9 123.57(17) . . ?
O19 C17 C9 112.50(15) . . ?
C8 C9 C10 118.68(17) . . ?
C8 C9 C17 118.11(16) . . ?
C10 C9 C17 123.10(16) . . ?
N1 C6 C5 118.40(16) . . ?
N1 C6 C7 116.22(16) . . ?
C5 C6 C7 125.38(17) . . ?
N16 C7 C8 123.63(16) . . ?
N16 C7 C6 114.65(16) . . ?
C8 C7 C6 121.70(16) . . ?
C9 C8 C7 119.55(16) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N16 C15 C14 116.47(17) . . ?
N16 C15 C10 123.15(16) . . ?
C14 C15 C10 120.37(17) . . ?
C11 C10 C15 118.00(17) . . ?
C11 C10 C9 125.09(17) . . ?
C15 C10 C9 116.91(16) . . ?
C4 C5 C6 119.42(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N1 C2 C3 119.78(17) . . ?
N1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C12 C11 C10 120.28(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C14 C15 119.67(19) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C2 C3 C4 118.78(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.27(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C11 C12 C13 121.05(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.62(19) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O19 H19 O1W 0.82 1.78 2.5818(19) 165.2 2_656
O1W H1WA Cl1 0.85 2.30 3.1445(15) 169.5 2_767
O1W H1WB Cl1 0.85 2.26 3.1141(17) 177.4 .
N1 H1 Cl1 0.85(3) 2.39(3) 3.1146(17) 143(2) .

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        74.79
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
