# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1538804'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Gd2 N4 O14 S3'
_chemical_formula_weight         999.12

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'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.1145(8)
_cell_length_b                   12.2682(10)
_cell_length_c                   12.3933(9)
_cell_angle_alpha                72.208(2)
_cell_angle_beta                 75.931(2)
_cell_angle_gamma                83.695(2)
_cell_volume                     1419.32(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5731
_cell_measurement_theta_min      3.0135
_cell_measurement_theta_max      27.4685

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.934
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3839
_exptl_absorpt_correction_T_max  0.4386
_exptl_absorpt_process_details   CrystalClear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12388
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             6349
_reflns_number_gt                4788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
The reflection statistics indicate non-merohedral twinning, the probable twin law revealed by PLATON Twin Rot Matrix program (A. Speck, 2015)
(-1.000    0.000    0.000)   (h1)     (h2)               
( 0.000   -1.000    0.000) * (k1) = (k2)                   
(-0.520   -0.570    1.000)   (l1)      (l2)                     
Because of partial overlap of reflections, intensity correction was unsatisfactory, which resulted in high residual electron density
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0636P)²+12.5152P] 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_number_reflns         6349
_refine_ls_number_parameters     424
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.093
_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
C21 C 0.7689(11) 0.9426(9) 1.0307(9) 0.026(2) Uani 1 1 d . . . . .
H21 H 0.720303 0.878514 1.077740 0.031 Uiso 1 1 calc R U . . .
Gd1 Gd 0.51916(4) 0.83989(4) 0.62794(4) 0.01193(13) Uani 1 1 d D . . . .
Gd2 Gd 0.91589(4) 1.10054(4) 0.61769(4) 0.01145(13) Uani 1 1 d D . . . .
S2 S 0.8623(2) 0.79644(19) 0.66815(19) 0.0133(4) Uani 1 1 d . . . . .
S1 S 0.5531(2) 1.12359(19) 0.65551(19) 0.0129(4) Uani 1 1 d . . . . .
O10 O 0.1343(6) 1.0421(5) 0.6727(5) 0.0171(14) Uani 1 1 d . . . . .
C18 C 0.9145(11) 1.1974(10) 1.0522(9) 0.030(2) Uani 1 1 d . . . . .
H18 H 0.903343 1.182213 1.132080 0.036 Uiso 1 1 calc R U . . .
O2W O 0.8291(6) 1.2810(6) 0.4812(6) 0.0243(15) Uani 1 1 d D . . . .
H2A H 0.877827 1.308352 0.413524 0.029 Uiso 1 1 d DR U . . .
H2B H 0.748991 1.283591 0.470216 0.029 Uiso 1 1 d DR U . . .
O12 O 0.2707(6) 0.8674(5) 0.6828(5) 0.0185(14) Uani 1 1 d . . . . .
S3 S 0.2227(2) 0.97185(19) 0.60609(18) 0.0123(4) Uani 1 1 d . . . . .
O4 O 0.6811(6) 1.1379(6) 0.6868(5) 0.0197(15) Uani 1 1 d . . . . .
O5 O 0.8739(7) 0.9084(5) 0.6859(6) 0.0196(14) Uani 1 1 d . . . . .
O3 O 0.5296(7) 0.9994(6) 0.6882(5) 0.0190(14) Uani 1 1 d . . . . .
O7 O 0.7172(6) 0.7696(6) 0.7007(5) 0.0182(14) Uani 1 1 d . . . . .
O2 O 0.5747(6) 1.1744(5) 0.5271(5) 0.0165(13) Uani 1 1 d . . . . .
O6 O 0.9069(6) 0.8082(5) 0.5421(5) 0.0177(14) Uani 1 1 d . . . . .
O11 O 0.1423(7) 0.9454(5) 0.5342(5) 0.0186(14) Uani 1 1 d . . . . .
O8 O 0.9444(7) 0.7093(6) 0.7311(6) 0.0247(16) Uani 1 1 d . . . . .
O1 O 0.4373(7) 1.1824(6) 0.7122(6) 0.0261(16) Uani 1 1 d . . . . .
O9 O 0.3459(6) 1.0335(6) 0.5318(5) 0.0191(14) Uani 1 1 d . . . . .
O1W O 0.6762(7) 0.7275(6) 0.5020(6) 0.0256(16) Uani 1 1 d D . . . .
H1B H 0.756953 0.722040 0.511956 0.031 Uiso 1 1 d DR U . . .
H1A H 0.683777 0.763282 0.430353 0.031 Uiso 1 1 d DR U . . .
N4 N 0.8638(8) 1.0572(7) 0.8402(6) 0.0152(16) Uani 1 1 d . . . . .
N1 N 0.4531(8) 0.7654(7) 0.8541(7) 0.0205(18) Uani 1 1 d . . . . .
N2 N 0.4359(8) 0.6351(7) 0.7144(8) 0.029(2) Uani 1 1 d . . . . .
N3 N 0.9665(8) 1.2594(7) 0.6934(8) 0.025(2) Uani 1 1 d . . . . .
C17 C 0.9680(12) 1.2956(11) 0.9813(11) 0.038(3) Uani 1 1 d . . . . .
H17 H 0.995954 1.346829 1.012450 0.045 Uiso 1 1 calc R U . . .
C23 C 0.8973(9) 1.1356(8) 0.8871(8) 0.0169(19) Uani 1 1 d . . . . .
C11 C 0.3996(9) 0.6611(10) 0.9038(8) 0.027(2) Uani 1 1 d . . . . .
C24 C 0.9559(9) 1.2397(8) 0.8076(8) 0.019(2) Uani 1 1 d . . . . .
C16 C 0.9834(10) 1.3240(9) 0.8561(9) 0.026(2) Uani 1 1 d . . . . .
C20 C 0.8101(11) 1.0162(10) 1.0782(8) 0.030(3) Uani 1 1 d . . . . .
H20 H 0.794878 0.999207 1.158530 0.036 Uiso 1 1 calc R U . . .
C19 C 0.8751(10) 1.1170(9) 1.0076(9) 0.025(2) Uani 1 1 d . . . . .
C22 C 0.8012(10) 0.9655(9) 0.9099(8) 0.021(2) Uani 1 1 d . . . . .
H22 H 0.777217 0.913256 0.877781 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3594(11) 0.6137(10) 1.0258(10) 0.034(3) Uani 1 1 d . . . . .
C10 C 0.4723(11) 0.8241(11) 0.9211(9) 0.035(3) Uani 1 1 d . . . . .
H10 H 0.511343 0.895096 0.885715 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4371(12) 0.7861(13) 1.0442(9) 0.041(3) Uani 1 1 d . . . . .
H9 H 0.453647 0.829740 1.088697 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3893(10) 0.5931(9) 0.8345(9) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.3778(13) 0.6821(15) 1.0946(10) 0.057(5) Uani 1 1 d . . . . .
H8 H 0.349204 0.655939 1.175060 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3039(12) 0.5044(12) 1.0738(12) 0.048(3) Uani 1 1 d . U . . .
H6 H 0.276271 0.475476 1.154099 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2898(12) 0.4413(12) 1.0070(13) 0.055(4) Uani 1 1 d . . . . .
H5 H 0.248137 0.371347 1.041506 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4348(12) 0.5703(11) 0.6506(11) 0.040(3) Uani 1 1 d . U . . .
H1 H 0.471888 0.599519 0.571553 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3382(11) 0.4793(10) 0.8814(11) 0.038(3) Uani 1 1 d . U . . .
C3 C 0.3384(13) 0.4160(11) 0.8064(13) 0.046(3) Uani 1 1 d . U . . .
H3 H 0.307470 0.341713 0.834991 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3861(12) 0.4652(12) 0.6857(13) 0.048(3) Uani 1 1 d . U . . .
H2 H 0.383657 0.426095 0.632792 0.057 Uiso 1 1 calc R U . . .
C13 C 1.0233(10) 1.3697(9) 0.6201(9) 0.025(2) Uani 1 1 d . U . . .
H13 H 1.044587 1.385150 0.539686 0.029 Uiso 1 1 calc R U . . .
C15 C 1.0294(12) 1.4280(9) 0.7788(10) 0.031(3) Uani 1 1 d . . . . .
H15 H 1.049931 1.484917 0.806751 0.037 Uiso 1 1 calc R U . . .
C14 C 1.0440(13) 1.4465(11) 0.6670(11) 0.041(3) Uani 1 1 d . U . . .
H14 H 1.070700 1.518405 0.618106 0.049 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
C21 C20 1.365(15) . ?
C21 C22 1.397(13) . ?
Gd1 O3 2.318(7) . ?
Gd1 O9 2.339(6) 2_676 ?
Gd1 O7 2.365(6) . ?
Gd1 O2 2.398(6) 2_676 ?
Gd1 O12 2.452(6) . ?
Gd1 O1W 2.547(7) . ?
Gd1 N2 2.559(9) . ?
Gd1 N1 2.607(8) . ?
Gd1 O9 2.917(7) . ?
Gd1 S3 3.278(2) . ?
Gd2 O5 2.298(6) . ?
Gd2 O11 2.338(6) 2_676 ?
Gd2 O4 2.365(6) . ?
Gd2 O6 2.398(6) 2_776 ?
Gd2 O10 2.439(6) 1_655 ?
Gd2 N3 2.552(8) . ?
Gd2 O2W 2.557(7) . ?
Gd2 N4 2.573(7) . ?
Gd2 S3 3.315(2) 1_655 ?
S2 O8 1.432(7) . ?
S2 O7 1.470(6) . ?
S2 O5 1.477(6) . ?
S2 O6 1.482(7) . ?
S1 O1 1.453(7) . ?
S1 O4 1.481(6) . ?
S1 O3 1.483(7) . ?
S1 O2 1.491(7) . ?
O10 S3 1.460(6) . ?
C18 C17 1.334(17) . ?
C18 C19 1.402(15) . ?
O12 S3 1.458(6) . ?
S3 O11 1.466(6) . ?
S3 O9 1.482(6) . ?
N4 C22 1.308(12) . ?
N4 C23 1.374(11) . ?
N1 C10 1.312(14) . ?
N1 C11 1.349(13) . ?
N2 C1 1.285(15) . ?
N2 C12 1.395(14) . ?
N3 C24 1.339(13) . ?
N3 C13 1.467(13) . ?
C17 C16 1.455(16) . ?
C23 C19 1.405(13) . ?
C23 C24 1.437(14) . ?
C11 C12 1.394(16) . ?
C11 C7 1.416(14) . ?
C24 C16 1.427(13) . ?
C16 C15 1.389(16) . ?
C20 C19 1.401(16) . ?
C7 C6 1.409(18) . ?
C7 C8 1.42(2) . ?
C10 C9 1.417(15) . ?
C9 C8 1.37(2) . ?
C12 C4 1.440(14) . ?
C6 C5 1.33(2) . ?
C5 C4 1.454(19) . ?
C1 C2 1.336(18) . ?
C4 C3 1.381(19) . ?
C3 C2 1.412(19) . ?
C13 C14 1.306(16) . ?
C15 C14 1.307(16) . ?

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
C20 C21 C22 118.6(10) . . ?
O3 Gd1 O9 75.2(2) . 2_676 ?
O3 Gd1 O7 86.4(2) . . ?
O9 Gd1 O7 88.9(2) 2_676 . ?
O3 Gd1 O2 128.9(2) . 2_676 ?
O9 Gd1 O2 79.1(2) 2_676 2_676 ?
O7 Gd1 O2 136.5(2) . 2_676 ?
O3 Gd1 O12 85.8(2) . . ?
O9 Gd1 O12 122.4(2) 2_676 . ?
O7 Gd1 O12 144.2(2) . . ?
O2 Gd1 O12 72.0(2) 2_676 . ?
O3 Gd1 O1W 137.7(2) . . ?
O9 Gd1 O1W 70.4(2) 2_676 . ?
O7 Gd1 O1W 69.3(2) . . ?
O2 Gd1 O1W 67.3(2) 2_676 . ?
O12 Gd1 O1W 133.6(2) . . ?
O3 Gd1 N2 138.9(3) . . ?
O9 Gd1 N2 145.0(3) 2_676 . ?
O7 Gd1 N2 86.8(2) . . ?
O2 Gd1 N2 80.4(3) 2_676 . ?
O12 Gd1 N2 76.6(2) . . ?
O1W Gd1 N2 75.6(3) . . ?
O3 Gd1 N1 75.6(2) . . ?
O9 Gd1 N1 145.1(2) 2_676 . ?
O7 Gd1 N1 70.4(2) . . ?
O2 Gd1 N1 135.1(2) 2_676 . ?
O12 Gd1 N1 73.8(2) . . ?
O1W Gd1 N1 123.3(2) . . ?
N2 Gd1 N1 63.9(3) . . ?
O3 Gd1 O9 66.4(2) . . ?
O9 Gd1 O9 71.6(2) 2_676 . ?
O7 Gd1 O9 149.5(2) . . ?
O2 Gd1 O9 63.83(19) 2_676 . ?
O12 Gd1 O9 51.16(18) . . ?
O1W Gd1 O9 122.08(19) . . ?
N2 Gd1 O9 122.6(2) . . ?
N1 Gd1 O9 113.0(2) . . ?
O3 Gd1 S3 77.22(17) . . ?
O9 Gd1 S3 98.00(17) 2_676 . ?
O7 Gd1 S3 159.86(16) . . ?
O2 Gd1 S3 63.58(15) 2_676 . ?
O12 Gd1 S3 24.45(15) . . ?
O1W Gd1 S3 130.83(15) . . ?
N2 Gd1 S3 97.82(19) . . ?
N1 Gd1 S3 93.95(17) . . ?
O9 Gd1 S3 26.87(12) . . ?
O5 Gd2 O11 74.3(2) . 2_676 ?
O5 Gd2 O4 88.2(2) . . ?
O11 Gd2 O4 88.0(2) 2_676 . ?
O5 Gd2 O6 126.8(2) . 2_776 ?
O11 Gd2 O6 79.5(2) 2_676 2_776 ?
O4 Gd2 O6 136.5(2) . 2_776 ?
O5 Gd2 O10 84.9(2) . 1_655 ?
O11 Gd2 O10 122.8(2) 2_676 1_655 ?
O4 Gd2 O10 144.9(2) . 1_655 ?
O6 Gd2 O10 71.7(2) 2_776 1_655 ?
O5 Gd2 N3 138.7(3) . . ?
O11 Gd2 N3 146.5(2) 2_676 . ?
O4 Gd2 N3 88.1(2) . . ?
O6 Gd2 N3 80.7(3) 2_776 . ?
O10 Gd2 N3 75.1(2) 1_655 . ?
O5 Gd2 O2W 138.0(2) . . ?
O11 Gd2 O2W 70.2(2) 2_676 . ?
O4 Gd2 O2W 69.0(2) . . ?
O6 Gd2 O2W 67.5(2) 2_776 . ?
O10 Gd2 O2W 133.5(2) 1_655 . ?
N3 Gd2 O2W 77.3(2) . . ?
O5 Gd2 N4 75.8(2) . . ?
O11 Gd2 N4 143.5(2) 2_676 . ?
O4 Gd2 N4 70.5(2) . . ?
O6 Gd2 N4 136.2(2) 2_776 . ?
O10 Gd2 N4 74.4(2) 1_655 . ?
N3 Gd2 N4 64.3(3) . . ?
O2W Gd2 N4 124.1(2) . . ?
O5 Gd2 S3 75.54(17) . 1_655 ?
O11 Gd2 S3 99.07(17) 2_676 1_655 ?
O4 Gd2 S3 159.65(16) . 1_655 ?
O6 Gd2 S3 63.88(15) 2_776 1_655 ?
O10 Gd2 S3 23.70(15) 1_655 1_655 ?
N3 Gd2 S3 96.07(18) . 1_655 ?
O2W Gd2 S3 131.31(15) . 1_655 ?
N4 Gd2 S3 93.29(17) . 1_655 ?
O8 S2 O7 112.8(4) . . ?
O8 S2 O5 111.2(4) . . ?
O7 S2 O5 108.3(4) . . ?
O8 S2 O6 109.9(4) . . ?
O7 S2 O6 106.1(4) . . ?
O5 S2 O6 108.3(4) . . ?
O1 S1 O4 112.0(4) . . ?
O1 S1 O3 110.4(4) . . ?
O4 S1 O3 108.4(4) . . ?
O1 S1 O2 109.2(4) . . ?
O4 S1 O2 106.4(4) . . ?
O3 S1 O2 110.3(4) . . ?
S3 O10 Gd2 114.1(3) . 1_455 ?
C17 C18 C19 120.7(10) . . ?
S3 O12 Gd1 111.4(3) . . ?
O12 S3 O10 111.0(4) . . ?
O12 S3 O11 111.1(4) . . ?
O10 S3 O11 106.8(4) . . ?
O12 S3 O9 106.5(4) . . ?
O10 S3 O9 111.1(4) . . ?
O11 S3 O9 110.3(4) . . ?
O12 S3 Gd1 44.1(3) . . ?
O10 S3 Gd1 132.0(3) . . ?
O11 S3 Gd1 120.1(3) . . ?
O9 S3 Gd1 62.8(3) . . ?
O12 S3 Gd2 131.0(3) . 1_455 ?
O10 S3 Gd2 42.2(2) . 1_455 ?
O11 S3 Gd2 65.0(3) . 1_455 ?
O9 S3 Gd2 120.8(3) . 1_455 ?
Gd1 S3 Gd2 173.21(7) . 1_455 ?
S1 O4 Gd2 135.5(4) . . ?
S2 O5 Gd2 152.1(4) . . ?
S1 O3 Gd1 147.9(4) . . ?
S2 O7 Gd1 137.1(4) . . ?
S1 O2 Gd1 138.0(4) . 2_676 ?
S2 O6 Gd2 137.7(4) . 2_776 ?
S3 O11 Gd2 161.5(4) . 2_676 ?
S3 O9 Gd1 158.5(4) . 2_676 ?
S3 O9 Gd1 90.3(3) . . ?
Gd1 O9 Gd1 108.4(2) 2_676 . ?
C22 N4 C23 118.9(8) . . ?
C22 N4 Gd2 122.2(6) . . ?
C23 N4 Gd2 118.8(6) . . ?
C10 N1 C11 118.9(9) . . ?
C10 N1 Gd1 122.8(7) . . ?
C11 N1 Gd1 118.3(7) . . ?
C1 N2 C12 119.1(10) . . ?
C1 N2 Gd1 122.0(8) . . ?
C12 N2 Gd1 118.9(7) . . ?
C24 N3 C13 115.1(8) . . ?
C24 N3 Gd2 119.6(6) . . ?
C13 N3 Gd2 124.9(7) . . ?
C18 C17 C16 121.3(10) . . ?
N4 C23 C19 122.3(9) . . ?
N4 C23 C24 117.3(8) . . ?
C19 C23 C24 120.4(9) . . ?
N1 C11 C12 119.8(9) . . ?
N1 C11 C7 122.5(11) . . ?
C12 C11 C7 117.6(10) . . ?
N3 C24 C16 122.7(9) . . ?
N3 C24 C23 119.4(8) . . ?
C16 C24 C23 117.4(9) . . ?
C15 C16 C24 117.0(9) . . ?
C15 C16 C17 123.8(9) . . ?
C24 C16 C17 119.1(10) . . ?
C21 C20 C19 121.0(9) . . ?
C20 C19 C18 123.1(9) . . ?
C20 C19 C23 116.3(9) . . ?
C18 C19 C23 120.6(10) . . ?
N4 C22 C21 122.8(10) . . ?
C6 C7 C11 120.5(13) . . ?
C6 C7 C8 123.0(12) . . ?
C11 C7 C8 116.5(11) . . ?
N1 C10 C9 124.1(12) . . ?
C8 C9 C10 117.1(13) . . ?
N2 C12 C11 118.7(9) . . ?
N2 C12 C4 118.2(11) . . ?
C11 C12 C4 123.1(10) . . ?
C9 C8 C7 120.9(11) . . ?
C5 C6 C7 121.6(12) . . ?
C6 C5 C4 121.6(12) . . ?
N2 C1 C2 126.9(12) . . ?
C3 C4 C12 119.0(11) . . ?
C3 C4 C5 125.6(12) . . ?
C12 C4 C5 115.4(13) . . ?
C4 C3 C2 119.3(11) . . ?
C1 C2 C3 117.4(11) . . ?
C14 C13 N3 120.4(10) . . ?
C14 C15 C16 120.4(10) . . ?
C13 C14 C15 123.8(12) . . ?

_refine_diff_density_max         6.216
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.282

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1538805'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H30 Gd2 O18'
_chemical_formula_weight         812.89

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'
Gd Gd -0.1653 3.9035 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.9630(9)
_cell_length_b                   14.9838(16)
_cell_length_c                   19.642(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.281(2)
_cell_angle_gamma                90
_cell_volume                     2337.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5731
_cell_measurement_theta_min      3.0135
_cell_measurement_theta_max      27.4685

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.310
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.712
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3839
_exptl_absorpt_correction_T_max  0.4386
_exptl_absorpt_process_details   'Sheldrick, G. M. 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23394
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.903
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2710
_reflns_number_gt                2583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0031P)²+16.0000P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00051(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0425
_refine_ls_wR_factor_gt          0.0420
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.228
_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
O6 O -0.0084(3) 0.54486(16) 0.56100(12) 0.0199(5) Uani 1 1 d . . . . .
O5 O -0.2655(3) 0.54760(18) 0.59271(13) 0.0271(6) Uani 1 1 d . . . . .
C8 C -0.1165(4) 0.5732(2) 0.60063(16) 0.0151(6) Uani 1 1 d . . . . .
O2W O 0.1107(13) 0.9077(4) 0.7007(3) 0.182(4) Uani 1 1 d . . . . .
H2WA H 0.109857 0.910325 0.657434 0.273 Uiso 1 1 d R U . . .
H2WB H 0.213717 0.918025 0.713934 0.273 Uiso 0.5 1 d R U P A 2
H2W H 0.042957 0.907735 0.732154 0.273 Uiso 0.5 1 d R U P B -1
O3W O 0.3745(13) 0.9293(6) 0.7833(5) 0.212(5) Uani 1 1 d . . . . .
H3WA H 0.375403 0.963763 0.819323 0.318 Uiso 1 1 d R U . . .
H3WB H 0.292834 0.922732 0.748843 0.318 Uiso 0.5 1 d R U P C 1
H3W H 0.461403 0.929343 0.760653 0.318 Uiso 0.5 1 d R U P D -1
O3 O -0.2672(3) 0.88554(16) 0.55826(14) 0.0244(5) Uani 1 1 d . . . . .
Gd1 Gd 0.24451(2) 0.96292(2) 0.48803(2) 0.01327(6) Uani 1 1 d . . . . .
O1 O 0.1670(3) 0.82267(16) 0.42806(12) 0.0220(5) Uani 1 1 d . . . . .
O4 O -0.0128(3) 0.92154(15) 0.53336(12) 0.0200(5) Uani 1 1 d . . . . .
O2 O 0.1487(3) 0.94643(15) 0.36857(12) 0.0241(5) Uani 1 1 d . . . . .
O1W O 0.3833(3) 0.85459(16) 0.56120(13) 0.0261(6) Uani 1 1 d . . . . .
H1WA H 0.488161 0.856031 0.573670 0.039 Uiso 1 1 d R U . . .
H1WB H 0.358521 0.799811 0.561800 0.039 Uiso 1 1 d R U . . .
C1 C 0.1308(4) 0.8629(2) 0.37155(17) 0.0164(6) Uani 1 1 d . . . . .
C7 C -0.0701(4) 0.6406(2) 0.65543(16) 0.0188(7) Uani 1 1 d . . . . .
H7A H 0.051523 0.643793 0.663103 0.023 Uiso 1 1 calc R U . . .
H7B H -0.115195 0.622036 0.697716 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0734(4) 0.8095(2) 0.30906(17) 0.0210(7) Uani 1 1 d . . . . .
H2A H -0.010905 0.766809 0.321231 0.025 Uiso 1 1 calc R U . . .
H2B H 0.168436 0.776122 0.294211 0.025 Uiso 1 1 calc R U . . .
C6 C -0.1400(5) 0.7332(2) 0.6348(2) 0.0258(8) Uani 1 1 d . . . . .
H6A H -0.258973 0.727843 0.620743 0.031 Uiso 1 1 calc R U . . .
H6B H -0.128895 0.772424 0.674175 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0503(5) 0.7744(2) 0.5774(2) 0.0262(8) Uani 1 1 d . . . . .
H5A H 0.068736 0.778954 0.591568 0.031 Uiso 1 1 calc R U . . .
H5B H -0.061734 0.734845 0.538217 0.031 Uiso 1 1 calc R U . . .
C3 C 0.000000 0.8662(3) 0.250000 0.0239(10) Uani 1 2 d S T P . .
H3A H 0.087550 0.904249 0.234172 0.029 Uiso 0.5 1 calc R U P . .
H3B H -0.087551 0.904249 0.265827 0.029 Uiso 0.5 1 calc R U P . .
C4 C -0.1144(4) 0.8652(2) 0.55599(16) 0.0156(6) 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
O6 C8 1.276(4) . ?
O6 Gd1 2.379(2) 7_566 ?
O6 Gd1 2.648(2) 3_445 ?
O5 C8 1.246(4) . ?
O5 Gd1 2.422(2) 3_445 ?
C8 C7 1.502(4) . ?
C8 Gd1 2.912(3) 3_445 ?
O3 C4 1.258(4) . ?
O3 Gd1 2.458(2) 5_576 ?
Gd1 O4 2.377(2) . ?
Gd1 O1W 2.384(2) . ?
Gd1 O2 2.425(2) . ?
Gd1 O1 2.465(2) . ?
Gd1 O4 2.542(2) 5_576 ?
Gd1 C1 2.827(3) . ?
Gd1 C4 2.885(3) 5_576 ?
O1 C1 1.277(4) . ?
O4 C4 1.273(4) . ?
O2 C1 1.261(4) . ?
C1 C2 1.507(4) . ?
C7 C6 1.538(5) . ?
C2 C3 1.519(4) . ?
C6 C5 1.511(5) . ?
C5 C4 1.502(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O6 Gd1 156.9(2) . 7_566 ?
C8 O6 Gd1 88.66(18) . 3_445 ?
Gd1 O6 Gd1 113.66(9) 7_566 3_445 ?
C8 O5 Gd1 100.1(2) . 3_445 ?
O5 C8 O6 120.1(3) . . ?
O5 C8 C7 118.5(3) . . ?
O6 C8 C7 121.3(3) . . ?
O5 C8 Gd1 54.97(16) . 3_445 ?
O6 C8 Gd1 65.37(17) . 3_445 ?
C7 C8 Gd1 170.1(2) . 3_445 ?
C4 O3 Gd1 96.51(19) . 5_576 ?
O4 Gd1 O6 162.04(8) . 7_566 ?
O4 Gd1 O1W 88.30(8) . . ?
O6 Gd1 O1W 80.04(9) 7_566 . ?
O4 Gd1 O5 74.62(8) . 3 ?
O6 Gd1 O5 117.09(8) 7_566 3 ?
O1W Gd1 O5 83.57(9) . 3 ?
O4 Gd1 O2 96.78(9) . . ?
O6 Gd1 O2 80.03(8) 7_566 . ?
O1W Gd1 O2 127.74(8) . . ?
O5 Gd1 O2 147.85(9) 3 . ?
O4 Gd1 O3 117.96(8) . 5_576 ?
O6 Gd1 O3 78.70(8) 7_566 5_576 ?
O1W Gd1 O3 143.96(8) . 5_576 ?
O5 Gd1 O3 80.68(9) 3 5_576 ?
O2 Gd1 O3 76.27(8) . 5_576 ?
O4 Gd1 O1 76.38(8) . . ?
O6 Gd1 O1 87.82(8) 7_566 . ?
O1W Gd1 O1 78.22(8) . . ?
O5 Gd1 O1 146.02(8) 3 . ?
O2 Gd1 O1 53.22(8) . . ?
O3 Gd1 O1 129.31(8) 5_576 . ?
O4 Gd1 O4 66.68(9) . 5_576 ?
O6 Gd1 O4 128.21(8) 7_566 5_576 ?
O1W Gd1 O4 149.46(8) . 5_576 ?
O5 Gd1 O4 73.39(8) 3 5_576 ?
O2 Gd1 O4 74.78(8) . 5_576 ?
O3 Gd1 O4 51.83(7) 5_576 5_576 ?
O1 Gd1 O4 110.42(8) . 5_576 ?
O4 Gd1 O6 123.01(8) . 3 ?
O6 Gd1 O6 66.34(9) 7_566 3 ?
O1W Gd1 O6 72.37(8) . 3 ?
O5 Gd1 O6 50.80(7) 3 3 ?
O2 Gd1 O6 137.59(8) . 3 ?
O3 Gd1 O6 72.53(8) 5_576 3 ?
O1 Gd1 O6 143.45(8) . 3 ?
O4 Gd1 O6 105.93(7) 5_576 3 ?
O4 Gd1 C1 86.09(9) . . ?
O6 Gd1 C1 83.43(8) 7_566 . ?
O1W Gd1 C1 103.48(9) . . ?
O5 Gd1 C1 159.35(8) 3 . ?
O2 Gd1 C1 26.39(9) . . ?
O3 Gd1 C1 102.60(9) 5_576 . ?
O1 Gd1 C1 26.83(8) . . ?
O4 Gd1 C1 92.43(8) 5_576 . ?
O6 Gd1 C1 149.78(8) 3 . ?
O4 Gd1 C4 92.58(8) . 5_576 ?
O6 Gd1 C4 103.33(9) 7_566 5_576 ?
O1W Gd1 C4 158.20(9) . 5_576 ?
O5 Gd1 C4 75.69(9) 3 5_576 ?
O2 Gd1 C4 73.80(8) . 5_576 ?
O3 Gd1 C4 25.67(8) 5_576 5_576 ?
O1 Gd1 C4 123.13(8) . 5_576 ?
O4 Gd1 C4 26.16(8) 5_576 5_576 ?
O6 Gd1 C4 89.08(8) 3 5_576 ?
C1 Gd1 C4 98.31(9) . 5_576 ?
O4 Gd1 C8 98.80(9) . 3 ?
O6 Gd1 C8 92.18(8) 7_566 3 ?
O1W Gd1 C8 78.21(9) . 3 ?
O5 Gd1 C8 24.90(8) 3 3 ?
O2 Gd1 C8 150.10(8) . 3 ?
O3 Gd1 C8 73.90(9) 5_576 3 ?
O1 Gd1 C8 156.06(8) . 3 ?
O4 Gd1 C8 88.24(8) 5_576 3 ?
O6 Gd1 C8 25.97(8) 3 3 ?
C1 Gd1 C8 174.91(9) . 3 ?
C4 Gd1 C8 80.14(9) 5_576 3 ?
C1 O1 Gd1 92.58(19) . . ?
C4 O4 Gd1 153.2(2) . . ?
C4 O4 Gd1 92.14(18) . 5_576 ?
Gd1 O4 Gd1 113.32(9) . 5_576 ?
C1 O2 Gd1 94.9(2) . . ?
O2 C1 O1 119.3(3) . . ?
O2 C1 C2 121.2(3) . . ?
O1 C1 C2 119.5(3) . . ?
O2 C1 Gd1 58.75(17) . . ?
O1 C1 Gd1 60.59(16) . . ?
C2 C1 Gd1 178.9(2) . . ?
C8 C7 C6 110.7(3) . . ?
C1 C2 C3 113.6(3) . . ?
C5 C6 C7 112.5(3) . . ?
C4 C5 C6 114.1(3) . . ?
C2 C3 C2 112.0(4) . 2 ?
O3 C4 O4 119.5(3) . . ?
O3 C4 C5 121.3(3) . . ?
O4 C4 C5 119.1(3) . . ?
O3 C4 Gd1 57.82(16) . 5_576 ?
O4 C4 Gd1 61.70(16) . 5_576 ?
C5 C4 Gd1 178.3(2) . 5_576 ?

_refine_diff_density_max         0.945
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.101

