# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1423187'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Gd N3 O6'
_chemical_formula_weight         433.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   7.7512(12)
_cell_length_b                   8.0176(13)
_cell_length_c                   18.399(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.125(2)
_cell_angle_gamma                90.00
_cell_volume                     1136.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    5.870
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_T_max  0.285
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5647
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2021
_reflns_number_gt                1667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0187P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0526
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.2197(6) -0.3630(6) 0.1094(3) 0.0156(11) Uani 1 1 d . . .
C2 C 0.2060(6) -0.4090(6) 0.0301(3) 0.0166(11) Uani 1 1 d . . .
C3 C 0.1143(6) -0.3032(6) -0.0199(3) 0.0200(12) Uani 1 1 d . . .
H3 H 0.0703 -0.2030 -0.0043 0.024 Uiso 1 1 calc R . .
C4 C 0.0888(6) -0.3476(6) -0.0930(3) 0.0190(12) Uani 1 1 d . . .
C5 C 0.1618(6) -0.4948(6) -0.1166(3) 0.0204(12) Uani 1 1 d . . .
H5 H 0.1485 -0.5230 -0.1659 0.025 Uiso 1 1 calc R . .
C6 C 0.2526(6) -0.5968(6) -0.0670(3) 0.0179(11) Uani 1 1 d . . .
C7 C 0.2762(6) -0.5563(6) 0.0070(3) 0.0228(12) Uani 1 1 d . . .
H7 H 0.3380 -0.6270 0.0403 0.027 Uiso 1 1 calc R . .
C8 C 0.3425(8) -0.8973(7) -0.0572(3) 0.0371(16) Uani 1 1 d . . .
H9 H 0.2941 -0.9243 -0.0146 0.045 Uiso 1 1 calc R . .
C9 C 0.4101(6) -0.7656(7) -0.1507(3) 0.0240(13) Uani 1 1 d . . .
H10 H 0.4165 -0.6835 -0.1860 0.029 Uiso 1 1 calc R . .
C10 C -0.0299(7) -0.2435(6) -0.1453(3) 0.0196(12) Uani 1 1 d . . .
C11 C -0.0491(7) -0.2076(7) 0.2679(3) 0.0269(13) Uani 1 1 d . . .
H12 H -0.1422 -0.2581 0.2872 0.032 Uiso 1 1 calc R . .
N1 N 0.3274(5) -0.7478(5) -0.0907(2) 0.0210(10) Uani 1 1 d . . .
N2 N 0.4354(7) -0.9997(5) -0.0930(3) 0.0370(13) Uani 1 1 d . . .
N3 N 0.4807(5) -0.9141(5) -0.1532(2) 0.0245(11) Uani 1 1 d . . .
O1 O 0.1749(5) -0.2183(4) 0.12436(18) 0.0258(9) Uani 1 1 d . . .
O2 O 0.2748(4) -0.4716(4) 0.15582(17) 0.0201(8) Uani 1 1 d . . .
O3 O -0.1014(5) -0.1200(5) -0.12001(19) 0.0305(9) Uani 1 1 d . . .
O4 O -0.0527(4) -0.2848(4) -0.21220(17) 0.0227(8) Uani 1 1 d . . .
O5 O -0.0674(4) -0.0660(4) 0.2423(2) 0.0292(9) Uani 1 1 d . . .
O6 O 0.4080(4) 0.2137(4) 0.23122(19) 0.0253(9) Uani 1 1 d . . .
Gd Gd 0.24627(3) -0.03316(3) 0.219856(13) 0.01578(9) 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
C1 O1 1.250(6) . ?
C1 O2 1.263(6) . ?
C1 C2 1.497(7) . ?
C2 C7 1.387(7) . ?
C2 C3 1.389(7) . ?
C3 C4 1.385(7) . ?
C4 C5 1.398(7) . ?
C4 C10 1.510(7) . ?
C5 C6 1.365(7) . ?
C6 C7 1.391(7) . ?
C6 N1 1.430(6) . ?
C8 N2 1.315(7) . ?
C8 N1 1.348(7) . ?
C9 N3 1.313(6) . ?
C9 N1 1.342(6) . ?
C10 O3 1.248(6) . ?
C10 O4 1.269(6) . ?
C10 Gd 3.020(5) 3 ?
C11 O5 1.231(6) . ?
C11 O6 1.262(6) 2_545 ?
C11 Gd 2.900(6) . ?
N2 N3 1.379(6) . ?
N3 Gd 2.592(4) 3_645 ?
O1 Gd 2.322(3) . ?
O2 Gd 2.363(3) 2_545 ?
O3 Gd 2.388(3) 3 ?
O4 Gd 2.389(3) 4 ?
O5 Gd 2.524(4) . ?
O6 C11 1.262(6) 2 ?
O6 Gd 2.340(3) . ?
O6 Gd 2.567(3) 2 ?
Gd O2 2.363(3) 2 ?
Gd O3 2.388(3) 3 ?
Gd O4 2.389(3) 4_656 ?
Gd O6 2.567(3) 2_545 ?
Gd N3 2.592(4) 3_645 ?
Gd C10 3.020(5) 3 ?

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
O1 C1 O2 124.9(5) . . ?
O1 C1 C2 116.8(4) . . ?
O2 C1 C2 118.2(4) . . ?
C7 C2 C3 120.4(5) . . ?
C7 C2 C1 121.3(4) . . ?
C3 C2 C1 118.2(4) . . ?
C4 C3 C2 119.8(5) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 C10 119.4(5) . . ?
C5 C4 C10 120.6(5) . . ?
C6 C5 C4 119.7(5) . . ?
C5 C6 C7 121.3(5) . . ?
C5 C6 N1 120.0(5) . . ?
C7 C6 N1 118.8(4) . . ?
C2 C7 C6 119.0(5) . . ?
N2 C8 N1 110.6(5) . . ?
N3 C9 N1 111.2(5) . . ?
O3 C10 O4 123.2(5) . . ?
O3 C10 C4 117.7(4) . . ?
O4 C10 C4 119.1(5) . . ?
O3 C10 Gd 48.7(2) . 3 ?
O4 C10 Gd 74.8(3) . 3 ?
C4 C10 Gd 165.1(4) . 3 ?
O5 C11 O6 122.1(5) . 2_545 ?
O5 C11 Gd 60.1(3) . . ?
O6 C11 Gd 62.2(3) 2_545 . ?
C9 N1 C8 104.8(4) . . ?
C9 N1 C6 125.9(4) . . ?
C8 N1 C6 129.1(4) . . ?
C8 N2 N3 107.0(5) . . ?
C9 N3 N2 106.3(4) . . ?
C9 N3 Gd 121.9(3) . 3_645 ?
N2 N3 Gd 126.1(3) . 3_645 ?
C1 O1 Gd 135.3(3) . . ?
C1 O2 Gd 138.2(3) . 2_545 ?
C10 O3 Gd 108.2(3) . 3 ?
C10 O4 Gd 133.1(3) . 4 ?
C11 O5 Gd 94.9(3) . . ?
C11 O6 Gd 151.6(3) 2 . ?
C11 O6 Gd 92.0(3) 2 2 ?
Gd O6 Gd 115.79(13) . 2 ?
O1 Gd O6 133.67(12) . . ?
O1 Gd O2 146.18(12) . 2 ?
O6 Gd O2 80.13(11) . 2 ?
O1 Gd O3 72.07(12) . 3 ?
O6 Gd O3 80.63(12) . 3 ?
O2 Gd O3 124.18(12) 2 3 ?
O1 Gd O4 95.44(12) . 4_656 ?
O6 Gd O4 99.02(12) . 4_656 ?
O2 Gd O4 74.32(11) 2 4_656 ?
O3 Gd O4 160.68(12) 3 4_656 ?
O1 Gd O5 84.34(12) . . ?
O6 Gd O5 126.15(12) . . ?
O2 Gd O5 72.28(12) 2 . ?
O3 Gd O5 78.32(13) 3 . ?
O4 Gd O5 115.90(12) 4_656 . ?
O1 Gd O6 71.18(12) . 2_545 ?
O6 Gd O6 154.49(3) . 2_545 ?
O2 Gd O6 75.09(11) 2 2_545 ?
O3 Gd O6 118.56(12) 3 2_545 ?
O4 Gd O6 68.63(12) 4_656 2_545 ?
O5 Gd O6 50.73(11) . 2_545 ?
O1 Gd N3 71.21(13) . 3_645 ?
O6 Gd N3 73.96(13) . 3_645 ?
O2 Gd N3 129.56(12) 2 3_645 ?
O3 Gd N3 93.46(13) 3 3_645 ?
O4 Gd N3 68.16(13) 4_656 3_645 ?
O5 Gd N3 155.55(13) . 3_645 ?
O6 Gd N3 118.12(12) 2_545 3_645 ?
O1 Gd C11 77.89(14) . . ?
O6 Gd C11 144.42(13) . . ?
O2 Gd C11 70.56(13) 2 . ?
O3 Gd C11 99.26(14) 3 . ?
O4 Gd C11 92.18(14) 4_656 . ?
O5 Gd C11 25.03(13) . . ?
O6 Gd C11 25.77(12) 2_545 . ?
N3 Gd C11 140.96(15) 3_645 . ?
O1 Gd C10 92.86(13) . 3 ?
O6 Gd C10 71.68(13) . 3 ?
O2 Gd C10 101.18(13) 2 3 ?
O3 Gd C10 23.12(12) 3 3 ?
O4 Gd C10 170.41(12) 4_656 3 ?
O5 Gd C10 69.69(12) . 3 ?
O6 Gd C10 118.89(12) 2_545 3 ?
N3 Gd C10 110.29(14) 3_645 3 ?
C11 Gd C10 94.26(15) . 3 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.141
