# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1833552'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br2 N6 O12 Pr'
_chemical_formula_weight         938.27

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.4940(2)
_cell_length_b                   17.6204(4)
_cell_length_c                   12.3858(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.6680(10)
_cell_angle_gamma                90
_cell_volume                     1634.82(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    14808
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.52

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.006
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Crustalclear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15927
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3690
_reflns_number_gt                3457
_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       'Crustalclear, Rigaku MSC, 2005'
_computing_cell_refinement       'Crustalclear, Rigaku MSC, 2005'
_computing_data_reduction        'Crustalclear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+1.5245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.15555(2) 0.2500 1.10202(2) 0.01776(6) Uani 1 2 d S T P . .
O1 O 0.1444(2) 0.11597(9) 1.12534(13) 0.0272(4) Uani 1 1 d . . . . .
N1 N 0.2402(3) 0.01768(11) 0.97510(16) 0.0237(4) Uani 1 1 d . . . . .
Br1 Br 0.18329(5) -0.14091(2) 1.44541(2) 0.04153(9) Uani 1 1 d . . . . .
C1 C 0.1563(3) 0.06043(12) 1.19465(18) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.1263(4) 0.07151(13) 1.30588(19) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.1386(4) 0.01265(14) 1.3777(2) 0.0276(5) Uani 1 1 d . . . . .
C4 C 0.1798(4) -0.06080(13) 1.34310(19) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.2116(3) -0.07476(13) 1.23739(19) 0.0253(5) Uani 1 1 d . . . . .
C6 C 0.2017(3) -0.01481(13) 1.16129(18) 0.0229(5) Uani 1 1 d . . . . .
C7 C 0.2412(3) -0.03220(13) 1.05278(19) 0.0243(5) Uani 1 1 d . . . . .
C8 C 0.2846(3) 0.00541(13) 0.86542(18) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.3611(4) -0.06177(14) 0.8312(2) 0.0287(5) Uani 1 1 d . . . . .
C10 C 0.4037(4) -0.06909(16) 0.7234(2) 0.0326(6) Uani 1 1 d . . . . .
C11 C 0.3704(4) -0.01079(16) 0.6514(2) 0.0334(6) Uani 1 1 d . . . . .
C12 C 0.2920(4) 0.05537(16) 0.6859(2) 0.0347(6) Uani 1 1 d . . . . .
C13 C 0.2494(4) 0.06373(14) 0.7934(2) 0.0296(5) Uani 1 1 d . . . . .
N2 N -0.1469(4) 0.2500 1.2529(2) 0.0268(6) Uani 1 2 d S T P . .
O2 O 0.0135(3) 0.2500 1.28499(18) 0.0240(5) Uani 1 2 d S T P . .
O3 O -0.1797(3) 0.2500 1.1515(2) 0.0333(6) Uani 1 2 d S T P . .
O4 O -0.2689(4) 0.2500 1.3178(2) 0.0419(7) Uani 1 2 d S T P . .
N3 N 0.4911(4) 0.2500 0.9699(2) 0.0275(6) Uani 1 2 d S T P . .
O5 O 0.4197(3) 0.18951(11) 1.00137(18) 0.0430(5) Uani 1 1 d . . . . .
O6 O 0.6208(4) 0.2500 0.9129(2) 0.0466(8) Uani 1 2 d S T P . .
N4 N -0.0008(4) 0.2500 0.8801(2) 0.0265(6) Uani 1 2 d S T P . .
O7 O 0.0187(3) 0.18920(10) 0.93401(14) 0.0380(5) Uani 1 1 d . . . . .
O8 O -0.0361(5) 0.2500 0.7846(2) 0.0474(8) Uani 1 2 d S T P . .
O1W O 0.3782(4) 0.2500 1.2494(2) 0.0330(6) Uani 1 2 d S T P . .
N5 N 0.3480(7) 0.2500 0.4741(3) 0.0714(14) Uani 1 2 d S T P . .
C14 C 0.3812(7) 0.2500 0.5627(4) 0.0508(11) Uani 1 2 d S T P . .
C15 C 0.4247(11) 0.2500 0.6784(4) 0.0594(15) Uani 1 2 d S T P . .
H1WA H 0.366(7) 0.2500 1.310(4) 0.045(15) Uiso 1 2 d S . P . .
H1WB H 0.477(6) 0.2500 1.246(3) 0.025 Uiso 1 2 d S U P . .
H1N H 0.213(4) 0.0638(18) 0.994(2) 0.029(7) Uiso 1 1 d . . . . .
H2 H 0.103(4) 0.1198(16) 1.329(2) 0.023(6) Uiso 1 1 d . . . . .
H3 H 0.121(4) 0.0201(17) 1.450(2) 0.032(7) Uiso 1 1 d . . . . .
H5 H 0.240(4) -0.1224(17) 1.213(2) 0.024(7) Uiso 1 1 d . . . . .
H7 H 0.269(4) -0.0814(16) 1.037(2) 0.023(7) Uiso 1 1 d . . . . .
H9 H 0.387(4) -0.099(2) 0.877(3) 0.042(9) Uiso 1 1 d . . . . .
H10 H 0.451(4) -0.112(2) 0.697(3) 0.045(9) Uiso 1 1 d . . . . .
H11 H 0.404(4) -0.0161(17) 0.581(2) 0.038(8) Uiso 1 1 d . . . . .
H12 H 0.259(4) 0.0945(19) 0.635(3) 0.042(8) Uiso 1 1 d . . . . .
H13 H 0.198(4) 0.1084(18) 0.819(2) 0.035(8) Uiso 1 1 d . . . . .
H15A H 0.492(7) 0.294(3) 0.694(4) 0.091(16) Uiso 1 1 d . . . . .
H15B H 0.319(10) 0.2500 0.714(6) 0.09(2) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O1 2.3811(16) 4_565 ?
Pr1 O1 2.3811(16) . ?
Pr1 O1W 2.437(3) . ?
Pr1 O7 2.5310(18) 4_565 ?
Pr1 O7 2.5310(18) . ?
Pr1 O2 2.532(2) . ?
Pr1 O5 2.5986(19) . ?
Pr1 O5 2.5987(19) 4_565 ?
Pr1 O3 2.603(3) . ?
Pr1 N4 2.956(3) . ?
Pr1 N2 2.979(3) . ?
O1 C1 1.303(3) . ?
N1 C7 1.303(3) . ?
N1 C8 1.425(3) . ?
N1 H1N 0.87(3) . ?
Br1 C4 1.897(2) . ?
C1 C2 1.416(3) . ?
C1 C6 1.432(3) . ?
C2 C3 1.368(3) . ?
C2 H2 0.92(3) . ?
C3 C4 1.401(3) . ?
C3 H3 0.92(3) . ?
C4 C5 1.360(3) . ?
C5 C6 1.416(3) . ?
C5 H5 0.92(3) . ?
C6 C7 1.418(3) . ?
C7 H7 0.91(3) . ?
C8 C13 1.381(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.387(4) . ?
C9 H9 0.88(3) . ?
C10 C11 1.379(4) . ?
C10 H10 0.91(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.92(3) . ?
C12 C13 1.387(4) . ?
C12 H12 0.96(3) . ?
C13 H13 0.93(3) . ?
N2 O4 1.235(4) . ?
N2 O2 1.255(4) . ?
N2 O3 1.273(4) . ?
N3 O6 1.218(4) . ?
N3 O5 1.259(2) . ?
N3 O5 1.259(2) 4_565 ?
N4 O8 1.205(4) . ?
N4 O7 1.269(2) 4_565 ?
N4 O7 1.269(2) . ?
O1W H1WA 0.76(5) . ?
O1W H1WB 0.74(5) . ?
N5 C14 1.118(6) . ?
C14 C15 1.459(7) . ?
C15 H15A 0.95(5) . ?
C15 H15B 0.92(7) . ?

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 Pr1 O1 165.37(8) 4_565 . ?
O1 Pr1 O1W 86.27(4) 4_565 . ?
O1 Pr1 O1W 86.27(4) . . ?
O1 Pr1 O7 70.43(6) 4_565 4_565 ?
O1 Pr1 O7 120.31(6) . 4_565 ?
O1W Pr1 O7 150.24(6) . 4_565 ?
O1 Pr1 O7 120.32(6) 4_565 . ?
O1 Pr1 O7 70.43(6) . . ?
O1W Pr1 O7 150.24(6) . . ?
O7 Pr1 O7 50.09(8) 4_565 . ?
O1 Pr1 O2 82.77(4) 4_565 . ?
O1 Pr1 O2 82.77(4) . . ?
O1W Pr1 O2 68.04(9) . . ?
O7 Pr1 O2 124.41(7) 4_565 . ?
O7 Pr1 O2 124.40(7) . . ?
O1 Pr1 O5 119.67(6) 4_565 . ?
O1 Pr1 O5 71.42(6) . . ?
O1W Pr1 O5 81.07(9) . . ?
O7 Pr1 O5 94.32(7) 4_565 . ?
O7 Pr1 O5 74.22(7) . . ?
O2 Pr1 O5 140.85(7) . . ?
O1 Pr1 O5 71.42(6) 4_565 4_565 ?
O1 Pr1 O5 119.67(6) . 4_565 ?
O1W Pr1 O5 81.07(9) . 4_565 ?
O7 Pr1 O5 74.22(7) 4_565 4_565 ?
O7 Pr1 O5 94.32(7) . 4_565 ?
O2 Pr1 O5 140.85(7) . 4_565 ?
O5 Pr1 O5 48.43(9) . 4_565 ?
O1 Pr1 O3 86.21(4) 4_565 . ?
O1 Pr1 O3 86.21(4) . . ?
O1W Pr1 O3 117.92(9) . . ?
O7 Pr1 O3 79.78(7) 4_565 . ?
O7 Pr1 O3 79.78(7) . . ?
O2 Pr1 O3 49.88(8) . . ?
O5 Pr1 O3 150.09(6) . . ?
O5 Pr1 O3 150.09(6) 4_565 . ?
O1 Pr1 N4 95.65(4) 4_565 . ?
O1 Pr1 N4 95.65(4) . . ?
O1W Pr1 N4 160.14(10) . . ?
O7 Pr1 N4 25.24(4) 4_565 . ?
O7 Pr1 N4 25.24(4) . . ?
O2 Pr1 N4 131.81(8) . . ?
O5 Pr1 N4 80.83(7) . . ?
O5 Pr1 N4 80.84(7) 4_565 . ?
O3 Pr1 N4 81.94(8) . . ?
O1 Pr1 N2 83.91(4) 4_565 . ?
O1 Pr1 N2 83.91(4) . . ?
O1W Pr1 N2 92.70(10) . . ?
O7 Pr1 N2 102.60(8) 4_565 . ?
O7 Pr1 N2 102.60(8) . . ?
O2 Pr1 N2 24.66(8) . . ?
O5 Pr1 N2 154.83(5) . . ?
O5 Pr1 N2 154.83(5) 4_565 . ?
O3 Pr1 N2 25.22(8) . . ?
N4 Pr1 N2 107.16(8) . . ?
C1 O1 Pr1 145.37(15) . . ?
C7 N1 C8 127.2(2) . . ?
C7 N1 H1N 114.9(18) . . ?
C8 N1 H1N 117.8(18) . . ?
O1 C1 C2 121.8(2) . . ?
O1 C1 C6 121.2(2) . . ?
C2 C1 C6 117.0(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 120.6(16) . . ?
C1 C2 H2 118.1(16) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 121.1(19) . . ?
C4 C3 H3 118.0(19) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 Br1 120.60(18) . . ?
C3 C4 Br1 118.83(18) . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 121.7(16) . . ?
C6 C5 H5 118.4(16) . . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 C1 120.4(2) . . ?
C7 C6 C1 122.1(2) . . ?
N1 C7 C6 123.8(2) . . ?
N1 C7 H7 118.5(16) . . ?
C6 C7 H7 117.7(16) . . ?
C13 C8 C9 120.7(2) . . ?
C13 C8 N1 117.2(2) . . ?
C9 C8 N1 122.1(2) . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 121(2) . . ?
C10 C9 H9 120(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 117(2) . . ?
C9 C10 H10 122(2) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 121(2) . . ?
C10 C11 H11 119(2) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.5(19) . . ?
C13 C12 H12 119.4(19) . . ?
C8 C13 C12 119.7(2) . . ?
C8 C13 H13 118.9(18) . . ?
C12 C13 H13 121.3(18) . . ?
O4 N2 O2 120.9(3) . . ?
O4 N2 O3 121.1(3) . . ?
O2 N2 O3 117.9(3) . . ?
O4 N2 Pr1 178.2(3) . . ?
O2 N2 Pr1 57.28(15) . . ?
O3 N2 Pr1 60.63(16) . . ?
N2 O2 Pr1 98.06(18) . . ?
N2 O3 Pr1 94.15(19) . . ?
O6 N3 O5 122.18(14) . . ?
O6 N3 O5 122.18(14) . 4_565 ?
O5 N3 O5 115.6(3) . 4_565 ?
N3 O5 Pr1 97.91(15) . . ?
O8 N4 O7 122.38(13) . 4_565 ?
O8 N4 O7 122.38(13) . . ?
O7 N4 O7 115.2(3) 4_565 . ?
O8 N4 Pr1 169.4(3) . . ?
O7 N4 Pr1 58.28(13) 4_565 . ?
O7 N4 Pr1 58.28(13) . . ?
N4 O7 Pr1 96.48(14) . . ?
Pr1 O1W H1WA 130(4) . . ?
Pr1 O1W H1WB 128(3) . . ?
H1WA O1W H1WB 102(5) . . ?
N5 C14 C15 180.0(6) . . ?
C14 C15 H15A 108(3) . . ?
C14 C15 H15B 107(5) . . ?
H15A C15 H15B 112(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA N5 0.76(5) 2.04(5) 2.799(5) 177(5) 1_556
O1W H1WB O4 0.74(5) 2.08(5) 2.753(4) 152(4) 1_655
N1 H1N O1 0.87(3) 1.95(3) 2.656(3) 138(2) .
C2 H2 O2 0.92(3) 2.45(3) 3.265(2) 149(2) .
C9 H9 O5 0.88(3) 2.61(3) 3.445(4) 159(3) 3_657
C13 H13 O7 0.93(3) 2.45(3) 3.329(3) 158(2) .

_refine_diff_density_max         1.216
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.086

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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data_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1833555'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br2 N6 O12 Sm'
_chemical_formula_weight         947.71

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.48050(10)
_cell_length_b                   17.5672(3)
_cell_length_c                   12.3748(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.7840(10)
_cell_angle_gamma                90
_cell_volume                     1625.40(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    13543
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.49

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_F_000             926
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    4.337
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14599
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.139
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3663
_reflns_number_gt                3432
_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       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²+0.8544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3663
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0452
_refine_ls_wR_factor_gt          0.0444
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.15748(2) 0.2500 1.09955(2) 0.01430(5) Uani 1 2 d S T P . .
O1 O 0.14481(19) 0.11760(7) 1.12446(12) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.2402(2) 0.01860(9) 0.97368(15) 0.0202(3) Uani 1 1 d . . . . .
Br1 Br 0.18123(4) -0.14097(2) 1.44482(2) 0.03585(7) Uani 1 1 d . . . . .
C1 C 0.1565(2) 0.06183(10) 1.19414(17) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.1262(3) 0.07286(11) 1.30489(18) 0.0221(4) Uani 1 1 d . . . . .
C3 C 0.1373(3) 0.01381(11) 1.37720(19) 0.0228(4) Uani 1 1 d . . . . .
C4 C 0.1788(3) -0.06018(11) 1.34227(18) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.2110(3) -0.07408(11) 1.23690(18) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.2018(2) -0.01375(10) 1.16025(17) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.2408(3) -0.03117(11) 1.05234(17) 0.0202(4) Uani 1 1 d . . . . .
C8 C 0.2846(2) 0.00598(11) 0.86413(17) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.3618(3) -0.06170(12) 0.83048(19) 0.0250(4) Uani 1 1 d . . . . .
C10 C 0.4046(3) -0.06944(12) 0.7225(2) 0.0284(5) Uani 1 1 d . . . . .
C11 C 0.3710(3) -0.01130(13) 0.6497(2) 0.0290(5) Uani 1 1 d . . . . .
C12 C 0.2923(3) 0.05550(13) 0.6843(2) 0.0302(5) Uani 1 1 d . . . . .
C13 C 0.2499(3) 0.06439(12) 0.79126(19) 0.0257(5) Uani 1 1 d . . . . .
N2 N -0.1445(3) 0.2500 1.2450(2) 0.0223(5) Uani 1 2 d S T P . .
O2 O 0.0171(2) 0.2500 1.27860(17) 0.0193(4) Uani 1 2 d S T P . .
O3 O -0.1735(3) 0.2500 1.14343(19) 0.0280(5) Uani 1 2 d S T P . .
O4 O -0.2675(3) 0.2500 1.3086(2) 0.0355(5) Uani 1 2 d S T P . .
N3 N 0.4886(3) 0.2500 0.9694(2) 0.0224(5) Uani 1 2 d S T P . .
O5 O 0.4167(2) 0.18935(8) 1.00076(15) 0.0374(4) Uani 1 1 d . . . . .
O6 O 0.6177(3) 0.2500 0.9117(2) 0.0381(6) Uani 1 2 d S T P . .
N4 N 0.0009(3) 0.2500 0.8806(2) 0.0225(5) Uani 1 2 d S T P . .
O7 O 0.0225(2) 0.18914(8) 0.93492(13) 0.0328(4) Uani 1 1 d . . . . .
O8 O -0.0376(3) 0.2500 0.78481(19) 0.0387(6) Uani 1 2 d S T P . .
O1W O 0.3783(3) 0.2500 1.2435(2) 0.0271(5) Uani 1 2 d S T P . .
N5 N 0.3513(5) 0.2500 0.4695(3) 0.0595(10) Uani 1 2 d S T P . .
C14 C 0.3823(5) 0.2500 0.5588(3) 0.0422(9) Uani 1 2 d S T P . .
C15 C 0.4243(7) 0.2500 0.6748(3) 0.0483(10) Uani 1 2 d S T P . .
H1WA H 0.353(7) 0.2500 1.303(4) 0.066(17) Uiso 1 2 d S . P . .
H1WB H 0.475(5) 0.2500 1.245(3) 0.022(9) Uiso 1 2 d S . P . .
H1N H 0.211(3) 0.0644(15) 0.994(2) 0.033(7) Uiso 1 1 d . . . . .
H2 H 0.099(3) 0.1226(13) 1.3283(19) 0.025(6) Uiso 1 1 d . . . . .
H3 H 0.116(3) 0.0240(12) 1.447(2) 0.021(6) Uiso 1 1 d . . . . .
H5 H 0.239(3) -0.1218(13) 1.2122(19) 0.020(5) Uiso 1 1 d . . . . .
H7 H 0.271(3) -0.0821(13) 1.0362(19) 0.026(6) Uiso 1 1 d . . . . .
H9 H 0.387(3) -0.0987(16) 0.880(2) 0.040(7) Uiso 1 1 d . . . . .
H10 H 0.456(3) -0.1148(14) 0.697(2) 0.034(7) Uiso 1 1 d . . . . .
H11 H 0.399(3) -0.0186(14) 0.577(2) 0.037(7) Uiso 1 1 d . . . . .
H12 H 0.264(3) 0.0939(15) 0.634(2) 0.037(7) Uiso 1 1 d . . . . .
H13 H 0.200(3) 0.1066(14) 0.815(2) 0.027(6) Uiso 1 1 d . . . . .
H15A H 0.324(7) 0.2500 0.717(4) 0.074(16) Uiso 1 2 d S . P . .
H15B H 0.485(5) 0.298(2) 0.695(3) 0.085(12) Uiso 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
Sm1 O1 2.3486(13) . ?
Sm1 O1 2.3486(13) 4_565 ?
Sm1 O1W 2.391(2) . ?
Sm1 O2 2.481(2) . ?
Sm1 O7 2.4869(15) 4_565 ?
Sm1 O7 2.4869(15) . ?
Sm1 O3 2.551(2) . ?
Sm1 O5 2.5568(15) 4_565 ?
Sm1 O5 2.5568(15) . ?
Sm1 N4 2.918(3) . ?
Sm1 N2 2.932(2) . ?
Sm1 N3 2.996(2) . ?
O1 C1 1.306(2) . ?
N1 C7 1.308(3) . ?
N1 C8 1.423(3) . ?
N1 H1N 0.87(3) . ?
Br1 C4 1.904(2) . ?
C1 C2 1.410(3) . ?
C1 C6 1.436(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.95(2) . ?
C3 C4 1.407(3) . ?
C3 H3 0.91(2) . ?
C4 C5 1.356(3) . ?
C5 C6 1.423(3) . ?
C5 H5 0.92(2) . ?
C6 C7 1.409(3) . ?
C7 H7 0.94(2) . ?
C8 C13 1.385(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.91(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.94(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.94(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.94(3) . ?
C13 H13 0.89(2) . ?
N2 O4 1.229(3) . ?
N2 O2 1.266(3) . ?
N2 O3 1.269(3) . ?
N3 O6 1.219(3) . ?
N3 O5 1.260(2) 4_565 ?
N3 O5 1.260(2) . ?
N4 O8 1.211(3) . ?
N4 O7 1.270(2) 4_565 ?
N4 O7 1.271(2) . ?
O1W H1WA 0.76(5) . ?
O1W H1WB 0.72(4) . ?
N5 C14 1.122(5) . ?
C14 C15 1.461(6) . ?
C15 H15A 0.93(5) . ?
C15 H15B 0.98(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
O1 Sm1 O1 164.08(7) . 4_565 ?
O1 Sm1 O1W 86.10(4) . . ?
O1 Sm1 O1W 86.10(4) 4_565 . ?
O1 Sm1 O2 82.12(4) . . ?
O1 Sm1 O2 82.12(4) 4_565 . ?
O1W Sm1 O2 68.68(8) . . ?
O1 Sm1 O7 121.08(5) . 4_565 ?
O1 Sm1 O7 70.41(5) 4_565 4_565 ?
O1W Sm1 O7 149.73(5) . 4_565 ?
O2 Sm1 O7 124.01(5) . 4_565 ?
O1 Sm1 O7 70.41(5) . . ?
O1 Sm1 O7 121.08(5) 4_565 . ?
O1W Sm1 O7 149.73(5) . . ?
O2 Sm1 O7 124.01(6) . . ?
O7 Sm1 O7 50.93(7) 4_565 . ?
O1 Sm1 O3 85.91(4) . . ?
O1 Sm1 O3 85.91(4) 4_565 . ?
O1W Sm1 O3 119.59(9) . . ?
O2 Sm1 O3 50.91(7) . . ?
O7 Sm1 O3 78.61(6) 4_565 . ?
O7 Sm1 O3 78.61(6) . . ?
O1 Sm1 O5 120.65(5) . 4_565 ?
O1 Sm1 O5 71.60(5) 4_565 4_565 ?
O1W Sm1 O5 80.77(8) . 4_565 ?
O2 Sm1 O5 140.83(5) . 4_565 ?
O7 Sm1 O5 73.96(6) 4_565 4_565 ?
O7 Sm1 O5 94.70(6) . 4_565 ?
O3 Sm1 O5 149.01(5) . 4_565 ?
O1 Sm1 O5 71.60(5) . . ?
O1 Sm1 O5 120.65(5) 4_565 . ?
O1W Sm1 O5 80.77(8) . . ?
O2 Sm1 O5 140.83(5) . . ?
O7 Sm1 O5 94.70(6) 4_565 . ?
O7 Sm1 O5 73.96(6) . . ?
O3 Sm1 O5 149.01(5) . . ?
O5 Sm1 O5 49.25(7) 4_565 . ?
O1 Sm1 N4 96.04(4) . . ?
O1 Sm1 N4 96.04(4) 4_565 . ?
O1W Sm1 N4 160.00(8) . . ?
O2 Sm1 N4 131.32(6) . . ?
O7 Sm1 N4 25.63(3) 4_565 . ?
O7 Sm1 N4 25.63(3) . . ?
O3 Sm1 N4 80.41(7) . . ?
O5 Sm1 N4 81.06(6) 4_565 . ?
O5 Sm1 N4 81.06(6) . . ?
O1 Sm1 N2 83.36(4) . . ?
O1 Sm1 N2 83.36(4) 4_565 . ?
O1W Sm1 N2 94.01(9) . . ?
O2 Sm1 N2 25.34(6) . . ?
O7 Sm1 N2 101.67(6) 4_565 . ?
O7 Sm1 N2 101.67(6) . . ?
O3 Sm1 N2 25.58(7) . . ?
O5 Sm1 N2 154.67(4) 4_565 . ?
O5 Sm1 N2 154.67(4) . . ?
N4 Sm1 N2 105.99(7) . . ?
O1 Sm1 N3 96.20(4) . . ?
O1 Sm1 N3 96.20(4) 4_565 . ?
O1W Sm1 N3 80.62(8) . . ?
O2 Sm1 N3 149.30(6) . . ?
O7 Sm1 N3 83.16(6) 4_565 . ?
O7 Sm1 N3 83.16(6) . . ?
O3 Sm1 N3 159.78(7) . . ?
O5 Sm1 N3 24.64(3) 4_565 . ?
O5 Sm1 N3 24.64(3) . . ?
N4 Sm1 N3 79.38(7) . . ?
N2 Sm1 N3 174.64(7) . . ?
C1 O1 Sm1 145.82(13) . . ?
C7 N1 C8 127.52(17) . . ?
C7 N1 H1N 113.1(17) . . ?
C8 N1 H1N 119.4(17) . . ?
O1 C1 C2 121.95(17) . . ?
O1 C1 C6 120.81(19) . . ?
C2 C1 C6 117.23(17) . . ?
C3 C2 C1 121.49(18) . . ?
C3 C2 H2 120.6(15) . . ?
C1 C2 H2 117.9(15) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 117.9(14) . . ?
C4 C3 H3 121.6(14) . . ?
C5 C4 C3 120.62(18) . . ?
C5 C4 Br1 120.57(14) . . ?
C3 C4 Br1 118.78(17) . . ?
C4 C5 C6 120.06(18) . . ?
C4 C5 H5 122.3(14) . . ?
C6 C5 H5 117.7(15) . . ?
C7 C6 C5 117.58(17) . . ?
C7 C6 C1 122.35(18) . . ?
C5 C6 C1 120.07(19) . . ?
N1 C7 C6 124.32(18) . . ?
N1 C7 H7 118.1(15) . . ?
C6 C7 H7 117.6(15) . . ?
C13 C8 C9 120.6(2) . . ?
C13 C8 N1 117.39(17) . . ?
C9 C8 N1 121.99(19) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 122.2(18) . . ?
C8 C9 H9 119.0(18) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 118.6(16) . . ?
C9 C10 H10 120.6(16) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 118.8(16) . . ?
C12 C11 H11 121.4(16) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 120.2(16) . . ?
C11 C12 H12 119.4(16) . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H13 122.0(16) . . ?
C8 C13 H13 118.2(16) . . ?
O4 N2 O2 121.1(3) . . ?
O4 N2 O3 121.7(2) . . ?
O2 N2 O3 117.2(2) . . ?
O4 N2 Sm1 178.1(2) . . ?
O2 N2 Sm1 57.00(13) . . ?
O3 N2 Sm1 60.20(13) . . ?
N2 O2 Sm1 97.67(17) . . ?
N2 O3 Sm1 94.22(15) . . ?
O6 N3 O5 122.29(12) . 4_565 ?
O6 N3 O5 122.28(12) . . ?
O5 N3 O5 115.4(2) 4_565 . ?
O6 N3 Sm1 176.7(2) . . ?
O5 N3 Sm1 57.75(11) 4_565 . ?
O5 N3 Sm1 57.75(11) . . ?
N3 O5 Sm1 97.61(12) . . ?
O8 N4 O7 122.70(12) . 4_565 ?
O8 N4 O7 122.70(12) . . ?
O7 N4 O7 114.6(2) 4_565 . ?
O8 N4 Sm1 170.1(2) . . ?
O7 N4 Sm1 57.86(12) 4_565 . ?
O7 N4 Sm1 57.86(12) . . ?
N4 O7 Sm1 96.51(12) . . ?
Sm1 O1W H1WA 122(4) . . ?
Sm1 O1W H1WB 134(3) . . ?
H1WA O1W H1WB 104(4) . . ?
N5 C14 C15 179.5(5) . . ?
C14 C15 H15A 114(3) . . ?
C14 C15 H15B 109(2) . . ?
H15A C15 H15B 103(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA N5 0.76(5) 2.06(5) 2.810(5) 166(5) 1_556
O1W H1WB O4 0.72(4) 2.06(4) 2.746(3) 159(4) 1_655
N1 H1N O1 0.87(3) 1.94(3) 2.664(2) 139(2) .
C2 H2 O2 0.95(2) 2.39(2) 3.2308(19) 147(2) .
C9 H9 O5 0.91(3) 2.59(3) 3.453(3) 157(2) 3_657
C13 H13 O7 0.89(2) 2.48(3) 3.323(3) 158(2) .

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.074

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Compound9
_database_code_depnum_ccdc_archive 'CCDC 1833554'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br2 Er N6 O12'
_chemical_formula_weight         964.62

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.45790(10)
_cell_length_b                   17.4427(3)
_cell_length_c                   12.3564(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.8460(10)
_cell_angle_gamma                90
_cell_volume                     1606.56(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    14669
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.48

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_F_000             938
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    5.172
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15700
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3621
_reflns_number_gt                3441
_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       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0133P)²+1.2592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3621
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0409
_refine_ls_wR_factor_gt          0.0403
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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
Er1 Er 0.15995(2) 0.2500 1.09664(2) 0.01464(4) Uani 1 2 d S T P . .
O1 O 0.1458(2) 0.12060(8) 1.12308(11) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.2403(2) 0.02058(11) 0.97168(14) 0.0204(4) Uani 1 1 d . . . . .
Br1 Br 0.17686(4) -0.14064(2) 1.44242(2) 0.03699(7) Uani 1 1 d . . . . .
C1 C 0.1566(3) 0.06457(11) 1.19282(16) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.1264(3) 0.07539(12) 1.30393(17) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.1361(3) 0.01539(12) 1.37573(17) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.1762(3) -0.05899(12) 1.34043(17) 0.0235(4) Uani 1 1 d . . . . .
C5 C 0.2092(3) -0.07269(12) 1.23481(17) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.2008(3) -0.01155(12) 1.15883(16) 0.0197(4) Uani 1 1 d . . . . .
C7 C 0.2398(3) -0.02942(12) 1.05038(17) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.2851(3) 0.00692(12) 0.86194(16) 0.0202(4) Uani 1 1 d . . . . .
C9 C 0.3614(3) -0.06139(13) 0.82962(18) 0.0265(5) Uani 1 1 d . . . . .
C10 C 0.4039(3) -0.07042(14) 0.72177(19) 0.0300(5) Uani 1 1 d . . . . .
C11 C 0.3719(3) -0.01214(14) 0.64793(18) 0.0299(5) Uani 1 1 d . . . . .
C12 C 0.2938(4) 0.05540(14) 0.68120(18) 0.0315(5) Uani 1 1 d . . . . .
C13 C 0.2512(3) 0.06571(13) 0.78862(18) 0.0276(5) Uani 1 1 d . . . . .
N2 N -0.1401(3) 0.2500 1.2331(2) 0.0231(5) Uani 1 2 d S T P . .
O2 O 0.0201(3) 0.2500 1.26930(16) 0.0196(4) Uani 1 2 d S T P . .
O3 O -0.1628(3) 0.2500 1.13089(17) 0.0281(5) Uani 1 2 d S T P . .
O4 O -0.2660(3) 0.2500 1.29415(19) 0.0370(6) Uani 1 2 d S T P . .
N3 N 0.4830(3) 0.2500 0.96901(19) 0.0230(5) Uani 1 2 d S T P . .
O5 O 0.4120(3) 0.18934(10) 1.00155(15) 0.0406(4) Uani 1 1 d . . . . .
O6 O 0.6111(3) 0.2500 0.90936(19) 0.0373(6) Uani 1 2 d S T P . .
N4 N 0.0052(3) 0.2500 0.88315(19) 0.0224(5) Uani 1 2 d S T P . .
O7 O 0.0287(3) 0.18897(9) 0.93671(13) 0.0366(4) Uani 1 1 d . . . . .
O8 O -0.0377(4) 0.2500 0.78727(18) 0.0388(6) Uani 1 2 d S T P . .
O1W O 0.3767(3) 0.2500 1.23416(19) 0.0252(5) Uani 1 2 d S T P . .
N5 N 0.3560(5) 0.2500 0.4614(3) 0.0560(10) Uani 1 2 d S T P . .
C14 C 0.3851(6) 0.2500 0.5515(3) 0.0416(9) Uani 1 2 d S T P . .
C15 C 0.4222(8) 0.2500 0.6682(3) 0.0485(11) Uani 1 2 d S T P . .
H1WA H 0.355(7) 0.2500 1.290(4) 0.065(18) Uiso 1 2 d S . P . .
H1WB H 0.480(6) 0.2500 1.232(3) 0.025 Uiso 1 2 d S U P . .
H1N H 0.211(4) 0.0643(17) 0.989(2) 0.034(7) Uiso 1 1 d . . . . .
H2 H 0.099(3) 0.1237(15) 1.3278(19) 0.027(6) Uiso 1 1 d . . . . .
H3 H 0.115(3) 0.0254(14) 1.4488(19) 0.023(6) Uiso 1 1 d . . . . .
H5 H 0.233(3) -0.1214(15) 1.2104(18) 0.024(6) Uiso 1 1 d . . . . .
H7 H 0.268(3) -0.0810(16) 1.0350(19) 0.030(7) Uiso 1 1 d . . . . .
H9 H 0.385(4) -0.0993(17) 0.877(2) 0.034(7) Uiso 1 1 d . . . . .
H10 H 0.455(4) -0.1144(18) 0.699(2) 0.043(8) Uiso 1 1 d . . . . .
H11 H 0.402(4) -0.0196(16) 0.574(2) 0.037(7) Uiso 1 1 d . . . . .
H12 H 0.263(4) 0.0931(16) 0.631(2) 0.037(7) Uiso 1 1 d . . . . .
H13 H 0.193(4) 0.1094(17) 0.811(2) 0.037(7) Uiso 1 1 d . . . . .
H15A H 0.484(5) 0.296(2) 0.684(3) 0.076(12) Uiso 1 1 d . . . . .
H15B H 0.303(8) 0.2500 0.697(4) 0.070(16) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O1 2.2835(14) . ?
Er1 O1 2.2836(14) 4_565 ?
Er1 O1W 2.307(2) . ?
Er1 O2 2.405(2) . ?
Er1 O7 2.4231(15) . ?
Er1 O7 2.4231(15) 4_565 ?
Er1 O3 2.457(2) . ?
Er1 O5 2.4853(18) 4_565 ?
Er1 O5 2.4854(18) . ?
Er1 N2 2.845(3) . ?
Er1 N4 2.845(2) . ?
Er1 N3 2.922(3) . ?
O1 C1 1.304(2) . ?
N1 C7 1.306(3) . ?
N1 C8 1.427(3) . ?
N1 H1N 0.82(3) . ?
Br1 C4 1.902(2) . ?
C1 C2 1.411(3) . ?
C1 C6 1.434(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.92(3) . ?
C3 C4 1.404(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.357(3) . ?
C5 C6 1.421(3) . ?
C5 H5 0.92(3) . ?
C6 C7 1.415(3) . ?
C7 H7 0.94(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.386(3) . ?
C9 C10 1.389(3) . ?
C9 H9 0.90(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.91(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.96(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.93(3) . ?
C13 H13 0.92(3) . ?
N2 O4 1.223(3) . ?
N2 O2 1.262(3) . ?
N2 O3 1.269(3) . ?
N3 O6 1.225(3) . ?
N3 O5 1.255(2) 4_565 ?
N3 O5 1.255(2) . ?
N4 O8 1.217(3) . ?
N4 O7 1.263(2) . ?
N4 O7 1.263(2) 4_565 ?
O1W H1WA 0.71(5) . ?
O1W H1WB 0.77(4) . ?
N5 C14 1.127(5) . ?
C14 C15 1.459(5) . ?
C15 H15A 0.94(4) . ?
C15 H15B 0.97(6) . ?

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 Er1 O1 162.54(7) . 4_565 ?
O1 Er1 O1W 85.94(4) . . ?
O1 Er1 O1W 85.94(4) 4_565 . ?
O1 Er1 O2 81.35(4) . . ?
O1 Er1 O2 81.35(4) 4_565 . ?
O1W Er1 O2 70.14(8) . . ?
O1 Er1 O7 70.32(5) . . ?
O1 Er1 O7 122.11(5) 4_565 . ?
O1W Er1 O7 148.82(5) . . ?
O2 Er1 O7 123.24(6) . . ?
O1 Er1 O7 122.11(5) . 4_565 ?
O1 Er1 O7 70.32(5) 4_565 4_565 ?
O1W Er1 O7 148.82(5) . 4_565 ?
O2 Er1 O7 123.24(6) . 4_565 ?
O7 Er1 O7 52.12(7) . 4_565 ?
O1 Er1 O3 85.72(4) . . ?
O1 Er1 O3 85.72(4) 4_565 . ?
O1W Er1 O3 122.69(8) . . ?
O2 Er1 O3 52.55(7) . . ?
O7 Er1 O3 76.61(6) . . ?
O7 Er1 O3 76.61(6) 4_565 . ?
O1 Er1 O5 121.84(5) . 4_565 ?
O1 Er1 O5 71.70(6) 4_565 4_565 ?
O1W Er1 O5 79.95(7) . 4_565 ?
O2 Er1 O5 140.87(6) . 4_565 ?
O7 Er1 O5 95.35(7) . 4_565 ?
O7 Er1 O5 73.69(6) 4_565 4_565 ?
O3 Er1 O5 147.30(5) . 4_565 ?
O1 Er1 O5 71.70(6) . . ?
O1 Er1 O5 121.84(5) 4_565 . ?
O1W Er1 O5 79.95(7) . . ?
O2 Er1 O5 140.88(6) . . ?
O7 Er1 O5 73.69(6) . . ?
O7 Er1 O5 95.35(7) 4_565 . ?
O3 Er1 O5 147.30(5) . . ?
O5 Er1 O5 50.40(8) 4_565 . ?
O1 Er1 N2 82.78(4) . . ?
O1 Er1 N2 82.78(4) 4_565 . ?
O1W Er1 N2 96.27(8) . . ?
O2 Er1 N2 26.13(7) . . ?
O7 Er1 N2 100.29(7) . . ?
O7 Er1 N2 100.29(7) 4_565 . ?
O3 Er1 N2 26.42(7) . . ?
O5 Er1 N2 154.37(4) 4_565 . ?
O5 Er1 N2 154.37(4) . . ?
O1 Er1 N4 96.51(4) . . ?
O1 Er1 N4 96.51(4) 4_565 . ?
O1W Er1 N4 159.48(8) . . ?
O2 Er1 N4 130.38(7) . . ?
O7 Er1 N4 26.20(4) . . ?
O7 Er1 N4 26.20(4) 4_565 . ?
O3 Er1 N4 77.83(7) . . ?
O5 Er1 N4 81.50(7) 4_565 . ?
O5 Er1 N4 81.50(7) . . ?
N2 Er1 N4 104.25(7) . . ?
O1 Er1 N3 96.89(4) . . ?
O1 Er1 N3 96.89(4) 4_565 . ?
O1W Er1 N3 80.05(8) . . ?
O2 Er1 N3 150.19(7) . . ?
O7 Er1 N3 83.00(6) . . ?
O7 Er1 N3 83.00(6) 4_565 . ?
O3 Er1 N3 157.26(7) . . ?
O5 Er1 N3 25.22(4) 4_565 . ?
O5 Er1 N3 25.22(4) . . ?
N2 Er1 N3 176.32(7) . . ?
N4 Er1 N3 79.43(7) . . ?
C1 O1 Er1 146.44(13) . . ?
C7 N1 C8 127.03(19) . . ?
C7 N1 H1N 115.1(19) . . ?
C8 N1 H1N 117.9(19) . . ?
O1 C1 C2 122.30(19) . . ?
O1 C1 C6 120.69(18) . . ?
C2 C1 C6 117.01(18) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 120.0(15) . . ?
C1 C2 H2 118.6(15) . . ?
C2 C3 C4 120.74(19) . . ?
C2 C3 H3 118.2(15) . . ?
C4 C3 H3 121.0(15) . . ?
C5 C4 C3 120.57(19) . . ?
C5 C4 Br1 120.58(16) . . ?
C3 C4 Br1 118.82(15) . . ?
C4 C5 C6 119.85(19) . . ?
C4 C5 H5 121.4(15) . . ?
C6 C5 H5 118.7(15) . . ?
C7 C6 C5 117.03(19) . . ?
C7 C6 C1 122.50(18) . . ?
C5 C6 C1 120.47(18) . . ?
N1 C7 C6 124.3(2) . . ?
N1 C7 H7 118.6(15) . . ?
C6 C7 H7 117.1(15) . . ?
C9 C8 C13 121.07(19) . . ?
C9 C8 N1 121.92(19) . . ?
C13 C8 N1 117.00(19) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 121.3(18) . . ?
C10 C9 H9 119.8(18) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 118.7(18) . . ?
C9 C10 H10 120.6(18) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 119.3(17) . . ?
C12 C11 H11 120.9(17) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 120.0(17) . . ?
C13 C12 H12 119.5(17) . . ?
C8 C13 C12 119.1(2) . . ?
C8 C13 H13 119.5(17) . . ?
C12 C13 H13 121.2(17) . . ?
O4 N2 O2 121.2(3) . . ?
O4 N2 O3 122.2(3) . . ?
O2 N2 O3 116.6(2) . . ?
O4 N2 Er1 178.3(2) . . ?
O2 N2 Er1 57.07(13) . . ?
O3 N2 Er1 59.49(14) . . ?
N2 O2 Er1 96.80(16) . . ?
N2 O3 Er1 94.10(16) . . ?
O6 N3 O5 122.54(13) . 4_565 ?
O6 N3 O5 122.53(13) . . ?
O5 N3 O5 114.9(3) 4_565 . ?
O6 N3 Er1 175.7(2) . . ?
O5 N3 Er1 57.55(13) 4_565 . ?
O5 N3 Er1 57.55(13) . . ?
N3 O5 Er1 97.23(14) . . ?
O8 N4 O7 122.54(11) . . ?
O8 N4 O7 122.54(11) . 4_565 ?
O7 N4 O7 114.9(2) . 4_565 ?
O8 N4 Er1 171.3(2) . . ?
O7 N4 Er1 57.90(11) . . ?
O7 N4 Er1 57.90(11) 4_565 . ?
N4 O7 Er1 95.90(12) . . ?
Er1 O1W H1WA 122(5) . . ?
Er1 O1W H1WB 130(3) . . ?
H1WA O1W H1WB 108(5) . . ?
N5 C14 C15 179.8(5) . . ?
C14 C15 H15A 106(2) . . ?
C14 C15 H15B 102(3) . . ?
H15A C15 H15B 112(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA N5 0.71(5) 2.12(5) 2.817(4) 166(6) 1_556
O1W H1WB O4 0.77(4) 2.02(4) 2.743(3) 155(4) 1_655
N1 H1N O1 0.82(3) 2.00(3) 2.669(2) 138(2) .
C2 H2 O2 0.92(3) 2.39(3) 3.173(2) 144(2) .
C9 H9 O5 0.90(3) 2.62(3) 3.458(3) 156(2) 3_657
C13 H13 O7 0.92(3) 2.44(3) 3.304(3) 155(2) .
N1 H1N O5 0.82(3) 2.65(3) 3.227(2) 129(2) .
N1 H1N O7 0.82(3) 2.63(3) 3.355(2) 147(2) .

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.072

_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT232_Compound9           
;
PROBLEM: Hirshfeld Test Diff (M-X) Er1--O5   12.3 s.u. 
  
RESPONSE:  The atoms have been assigned correctly and
the data are not affected from any systematic error
based on the good results for all other parameters.
;
# end Validation Reply Form






####################################################################### 
# 
# 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_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1833556'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br2 Dy N6 O12'
_chemical_formula_weight         959.86

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.46760(10)
_cell_length_b                   17.4621(3)
_cell_length_c                   12.3690(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.8210(10)
_cell_angle_gamma                90
_cell_volume                     1612.10(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    15638
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.49

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_F_000             934
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    4.869
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Crustalclear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16632
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3637
_reflns_number_gt                3440
_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       'Crustalclear, Rigaku MSC, 2005'
_computing_cell_refinement       'Crustalclear, Rigaku MSC, 2005'
_computing_data_reduction        'Crustalclear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0085P)²+1.6758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3637
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0415
_refine_ls_wR_factor_gt          0.0408
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.15874(2) 0.2500 1.09790(2) 0.01490(5) Uani 1 2 d S T P . .
O1 O 0.1454(2) 0.12002(8) 1.12372(12) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.2399(3) 0.01993(10) 0.97222(14) 0.0202(4) Uani 1 1 d . . . . .
Br1 Br 0.17856(4) -0.14092(2) 1.44326(2) 0.03641(8) Uani 1 1 d . . . . .
C1 C 0.1568(3) 0.06392(11) 1.19331(17) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.1264(3) 0.07458(12) 1.30456(18) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.1366(3) 0.01485(12) 1.37641(18) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.1774(3) -0.05948(12) 1.34130(18) 0.0231(5) Uani 1 1 d . . . . .
C5 C 0.2097(3) -0.07302(12) 1.23551(18) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.2013(3) -0.01223(12) 1.15919(17) 0.0200(4) Uani 1 1 d . . . . .
C7 C 0.2401(3) -0.02991(12) 1.05100(18) 0.0212(4) Uani 1 1 d . . . . .
C8 C 0.2848(3) 0.00686(12) 0.86270(17) 0.0201(4) Uani 1 1 d . . . . .
C9 C 0.3616(3) -0.06136(13) 0.82961(19) 0.0261(5) Uani 1 1 d . . . . .
C10 C 0.4044(3) -0.06989(14) 0.7219(2) 0.0292(5) Uani 1 1 d . . . . .
C11 C 0.3711(3) -0.01167(14) 0.64823(19) 0.0294(5) Uani 1 1 d . . . . .
C12 C 0.2930(4) 0.05569(14) 0.68184(19) 0.0309(5) Uani 1 1 d . . . . .
C13 C 0.2504(3) 0.06550(13) 0.78946(19) 0.0265(5) Uani 1 1 d . . . . .
N2 N -0.1427(4) 0.2500 1.2374(2) 0.0230(6) Uani 1 2 d S T P . .
O2 O 0.0184(3) 0.2500 1.27279(17) 0.0200(4) Uani 1 2 d S T P . .
O3 O -0.1674(3) 0.2500 1.13553(18) 0.0282(5) Uani 1 2 d S T P . .
O4 O -0.2675(3) 0.2500 1.2997(2) 0.0359(6) Uani 1 2 d S T P . .
N3 N 0.4842(4) 0.2500 0.9690(2) 0.0219(5) Uani 1 2 d S T P . .
O5 O 0.4136(3) 0.18902(9) 1.00125(16) 0.0391(4) Uani 1 1 d . . . . .
O6 O 0.6131(3) 0.2500 0.9102(2) 0.0369(6) Uani 1 2 d S T P . .
N4 N 0.0045(4) 0.2500 0.8832(2) 0.0221(6) Uani 1 2 d S T P . .
O7 O 0.0257(3) 0.18880(9) 0.93658(13) 0.0361(5) Uani 1 1 d . . . . .
O8 O -0.0377(4) 0.2500 0.78672(19) 0.0396(6) Uani 1 2 d S T P . .
O1W O 0.3770(3) 0.2500 1.2373(2) 0.0252(5) Uani 1 2 d S T P . .
N5 N 0.3541(5) 0.2500 0.4640(3) 0.0559(10) Uani 1 2 d S T P . .
C14 C 0.3847(6) 0.2500 0.5537(3) 0.0404(9) Uani 1 2 d S T P . .
C15 C 0.4233(8) 0.2500 0.6709(3) 0.0470(11) Uani 1 2 d S T P . .
H1WA H 0.355(7) 0.2500 1.301(4) 0.053(15) Uiso 1 2 d S . P . .
H1WB H 0.482(6) 0.2500 1.237(3) 0.025 Uiso 1 2 d S U P . .
H1N H 0.212(4) 0.0634(16) 0.989(2) 0.029(7) Uiso 1 1 d . . . . .
H2 H 0.097(3) 0.1236(14) 1.3270(18) 0.019(6) Uiso 1 1 d . . . . .
H3 H 0.115(3) 0.0249(14) 1.448(2) 0.025(6) Uiso 1 1 d . . . . .
H5 H 0.235(4) -0.1204(15) 1.213(2) 0.029(7) Uiso 1 1 d . . . . .
H7 H 0.267(3) -0.0810(15) 1.0357(19) 0.026(6) Uiso 1 1 d . . . . .
H9 H 0.387(4) -0.0975(16) 0.877(2) 0.035(7) Uiso 1 1 d . . . . .
H10 H 0.452(4) -0.1146(16) 0.701(2) 0.035(7) Uiso 1 1 d . . . . .
H11 H 0.401(4) -0.0195(14) 0.576(2) 0.030(7) Uiso 1 1 d . . . . .
H12 H 0.260(4) 0.0937(16) 0.633(2) 0.039(8) Uiso 1 1 d . . . . .
H13 H 0.196(4) 0.1090(16) 0.812(2) 0.036(7) Uiso 1 1 d . . . . .
H15A H 0.486(5) 0.296(2) 0.689(3) 0.071(11) Uiso 1 1 d . . . . .
H15B H 0.310(8) 0.2500 0.698(4) 0.071(18) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O1 2.2947(14) . ?
Dy1 O1 2.2947(14) 4_565 ?
Dy1 O1W 2.335(2) . ?
Dy1 O2 2.433(2) . ?
Dy1 O7 2.4462(15) 4_565 ?
Dy1 O7 2.4462(15) . ?
Dy1 O3 2.494(2) . ?
Dy1 O5 2.5160(18) 4_565 ?
Dy1 O5 2.5160(18) . ?
Dy1 N4 2.861(2) . ?
Dy1 N2 2.879(3) . ?
Dy1 N3 2.949(3) . ?
O1 C1 1.305(2) . ?
N1 C7 1.306(3) . ?
N1 C8 1.424(3) . ?
N1 H1N 0.82(3) . ?
Br1 C4 1.901(2) . ?
C1 C2 1.414(3) . ?
C1 C6 1.437(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.93(2) . ?
C3 C4 1.405(3) . ?
C3 H3 0.92(2) . ?
C4 C5 1.359(3) . ?
C5 C6 1.421(3) . ?
C5 H5 0.90(3) . ?
C6 C7 1.412(3) . ?
C7 H7 0.94(3) . ?
C8 C13 1.386(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.88(3) . ?
C10 C11 1.382(4) . ?
C10 H10 0.90(3) . ?
C11 C12 1.382(4) . ?
C11 H11 0.94(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.93(3) . ?
C13 H13 0.91(3) . ?
N2 O4 1.228(4) . ?
N2 O2 1.267(3) . ?
N2 O3 1.268(3) . ?
N3 O6 1.225(4) . ?
N3 O5 1.259(2) 4_565 ?
N3 O5 1.259(2) . ?
N4 O8 1.224(3) . ?
N4 O7 1.264(2) 4_565 ?
N4 O7 1.264(2) . ?
O1W H1WA 0.81(5) . ?
O1W H1WB 0.78(4) . ?
N5 C14 1.127(5) . ?
C14 C15 1.468(6) . ?
C15 H15A 0.95(4) . ?
C15 H15B 0.92(6) . ?

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 Dy1 O1 163.08(8) . 4_565 ?
O1 Dy1 O1W 85.96(4) . . ?
O1 Dy1 O1W 85.96(4) 4_565 . ?
O1 Dy1 O2 81.63(4) . . ?
O1 Dy1 O2 81.63(4) 4_565 . ?
O1W Dy1 O2 69.74(8) . . ?
O1 Dy1 O7 121.82(5) . 4_565 ?
O1 Dy1 O7 70.31(5) 4_565 4_565 ?
O1W Dy1 O7 149.12(5) . 4_565 ?
O2 Dy1 O7 123.36(6) . 4_565 ?
O1 Dy1 O7 70.31(5) . . ?
O1 Dy1 O7 121.82(5) 4_565 . ?
O1W Dy1 O7 149.12(5) . . ?
O2 Dy1 O7 123.36(6) . . ?
O7 Dy1 O7 51.81(7) 4_565 . ?
O1 Dy1 O3 85.82(4) . . ?
O1 Dy1 O3 85.82(4) 4_565 . ?
O1W Dy1 O3 121.67(8) . . ?
O2 Dy1 O3 51.94(7) . . ?
O7 Dy1 O3 77.21(7) 4_565 . ?
O7 Dy1 O3 77.21(7) . . ?
O1 Dy1 O5 121.44(6) . 4_565 ?
O1 Dy1 O5 71.60(6) 4_565 4_565 ?
O1W Dy1 O5 80.21(8) . 4_565 ?
O2 Dy1 O5 140.90(6) . 4_565 ?
O7 Dy1 O5 73.82(6) 4_565 4_565 ?
O7 Dy1 O5 95.22(7) . 4_565 ?
O3 Dy1 O5 147.85(5) . 4_565 ?
O1 Dy1 O5 71.60(6) . . ?
O1 Dy1 O5 121.44(6) 4_565 . ?
O1W Dy1 O5 80.21(8) . . ?
O2 Dy1 O5 140.90(6) . . ?
O7 Dy1 O5 95.22(7) 4_565 . ?
O7 Dy1 O5 73.82(6) . . ?
O3 Dy1 O5 147.85(5) . . ?
O5 Dy1 O5 50.08(8) 4_565 . ?
O1 Dy1 N4 96.38(4) . . ?
O1 Dy1 N4 96.38(4) 4_565 . ?
O1W Dy1 N4 159.48(9) . . ?
O2 Dy1 N4 130.78(7) . . ?
O7 Dy1 N4 26.07(4) 4_565 . ?
O7 Dy1 N4 26.07(4) . . ?
O3 Dy1 N4 78.84(8) . . ?
O5 Dy1 N4 81.22(7) 4_565 . ?
O5 Dy1 N4 81.22(7) . . ?
O1 Dy1 N2 83.01(4) . . ?
O1 Dy1 N2 83.01(4) 4_565 . ?
O1W Dy1 N2 95.62(9) . . ?
O2 Dy1 N2 25.88(7) . . ?
O7 Dy1 N2 100.60(7) 4_565 . ?
O7 Dy1 N2 100.60(7) . . ?
O3 Dy1 N2 26.05(7) . . ?
O5 Dy1 N2 154.46(4) 4_565 . ?
O5 Dy1 N2 154.46(4) . . ?
N4 Dy1 N2 104.89(8) . . ?
O1 Dy1 N3 96.63(4) . . ?
O1 Dy1 N3 96.63(4) 4_565 . ?
O1W Dy1 N3 80.29(8) . . ?
O2 Dy1 N3 150.03(7) . . ?
O7 Dy1 N3 83.06(7) 4_565 . ?
O7 Dy1 N3 83.06(6) . . ?
O3 Dy1 N3 158.04(7) . . ?
O5 Dy1 N3 25.06(4) 4_565 . ?
O5 Dy1 N3 25.06(4) . . ?
N4 Dy1 N3 79.19(7) . . ?
N2 Dy1 N3 175.91(7) . . ?
C1 O1 Dy1 146.31(13) . . ?
C7 N1 C8 127.44(19) . . ?
C7 N1 H1N 114.9(19) . . ?
C8 N1 H1N 117.6(19) . . ?
O1 C1 C2 122.27(19) . . ?
O1 C1 C6 120.78(19) . . ?
C2 C1 C6 116.96(18) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 121.1(15) . . ?
C1 C2 H2 117.3(14) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 118.1(15) . . ?
C4 C3 H3 121.2(15) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 Br1 120.77(16) . . ?
C3 C4 Br1 118.86(17) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 120.6(17) . . ?
C6 C5 H5 119.1(16) . . ?
C7 C6 C5 117.41(19) . . ?
C7 C6 C1 122.46(19) . . ?
C5 C6 C1 120.13(19) . . ?
N1 C7 C6 124.5(2) . . ?
N1 C7 H7 118.7(15) . . ?
C6 C7 H7 116.8(15) . . ?
C13 C8 C9 120.7(2) . . ?
C13 C8 N1 117.32(19) . . ?
C9 C8 N1 122.0(2) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 121.0(19) . . ?
C8 C9 H9 120.0(19) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 120.8(17) . . ?
C9 C10 H10 118.4(17) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 118.6(16) . . ?
C12 C11 H11 121.7(16) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 121.5(18) . . ?
C13 C12 H12 118.0(18) . . ?
C8 C13 C12 119.5(2) . . ?
C8 C13 H13 119.6(18) . . ?
C12 C13 H13 120.9(17) . . ?
O4 N2 O2 121.0(3) . . ?
O4 N2 O3 122.3(3) . . ?
O2 N2 O3 116.7(3) . . ?
O4 N2 Dy1 178.0(2) . . ?
O2 N2 Dy1 56.99(15) . . ?
O3 N2 Dy1 59.76(16) . . ?
N2 O2 Dy1 97.13(17) . . ?
N2 O3 Dy1 94.19(17) . . ?
O6 N3 O5 122.21(14) . 4_565 ?
O6 N3 O5 122.21(14) . . ?
O5 N3 O5 115.6(3) 4_565 . ?
O6 N3 Dy1 176.3(2) . . ?
O5 N3 Dy1 57.87(14) 4_565 . ?
O5 N3 Dy1 57.87(14) . . ?
N3 O5 Dy1 97.07(14) . . ?
O8 N4 O7 122.26(11) . 4_565 ?
O8 N4 O7 122.26(11) . . ?
O7 N4 O7 115.5(2) 4_565 . ?
O8 N4 Dy1 171.2(2) . . ?
O7 N4 Dy1 58.29(11) 4_565 . ?
O7 N4 Dy1 58.29(11) . . ?
N4 O7 Dy1 95.63(12) . . ?
Dy1 O1W H1WA 124(4) . . ?
Dy1 O1W H1WB 132(3) . . ?
H1WA O1W H1WB 104(4) . . ?
N5 C14 C15 179.6(5) . . ?
C14 C15 H15A 108(2) . . ?
C14 C15 H15B 102(3) . . ?
H15A C15 H15B 112(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA N5 0.81(5) 2.02(5) 2.814(4) 168(5) 1_556
C2 H2 O2 0.93(2) 2.37(2) 3.189(2) 146.2(19) .
C13 H13 O7 0.91(3) 2.46(3) 3.310(3) 155(2) .
O1W H1WB O4 0.78(4) 2.00(4) 2.740(3) 157(4) 1_655
N1 H1N O1 0.82(3) 2.01(3) 2.674(2) 138(2) .
C9 H9 O5 0.88(3) 2.63(3) 3.455(3) 158(3) 3_657

_refine_diff_density_max         0.778
_refine_diff_density_min         -1.051
_refine_diff_density_rms         0.078

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1833553'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Br2 Gd N6 O12'
_chemical_formula_weight         954.61

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.47120(10)
_cell_length_b                   17.5324(4)
_cell_length_c                   12.3673(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8170(10)
_cell_angle_gamma                90
_cell_volume                     1619.15(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    14768
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.50

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             930
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    4.588
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.450
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15643
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3646
_reflns_number_gt                3421
_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       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'CrystalClear, Rigaku MSC, 2005'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0112P)²+1.3866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.15867(2) 0.2500 1.09834(2) 0.01472(6) Uani 1 2 d S T P . .
O1 O 0.1453(2) 0.11839(9) 1.12396(14) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.2400(3) 0.01912(11) 0.97330(17) 0.0203(4) Uani 1 1 d . . . . .
Br1 Br 0.17981(4) -0.14085(2) 1.44428(2) 0.03652(9) Uani 1 1 d . . . . .
C1 C 0.1566(3) 0.06272(13) 1.1942(2) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.1258(3) 0.07361(14) 1.3048(2) 0.0233(5) Uani 1 1 d . . . . .
C3 C 0.1374(3) 0.01418(14) 1.3771(2) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.1779(3) -0.05986(13) 1.3417(2) 0.0231(5) Uani 1 1 d . . . . .
C5 C 0.2104(3) -0.07358(13) 1.2367(2) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.2012(3) -0.01310(13) 1.1601(2) 0.0193(5) Uani 1 1 d . . . . .
C7 C 0.2401(3) -0.03074(13) 1.0518(2) 0.0214(5) Uani 1 1 d . . . . .
C8 C 0.2850(3) 0.00626(13) 0.8636(2) 0.0206(5) Uani 1 1 d . . . . .
C9 C 0.3614(3) -0.06176(15) 0.8301(2) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.4048(3) -0.06960(15) 0.7223(2) 0.0289(6) Uani 1 1 d . . . . .
C11 C 0.3716(4) -0.01149(16) 0.6494(2) 0.0298(6) Uani 1 1 d . . . . .
C12 C 0.2927(4) 0.05566(16) 0.6833(2) 0.0310(6) Uani 1 1 d . . . . .
C13 C 0.2499(4) 0.06463(14) 0.7904(2) 0.0264(5) Uani 1 1 d . . . . .
N2 N -0.1426(4) 0.2500 1.2403(3) 0.0221(6) Uani 1 2 d S T P . .
O2 O 0.0187(3) 0.2500 1.2754(2) 0.0197(5) Uani 1 2 d S T P . .
O3 O -0.1691(3) 0.2500 1.1392(2) 0.0285(6) Uani 1 2 d S T P . .
O4 O -0.2663(3) 0.2500 1.3036(2) 0.0358(7) Uani 1 2 d S T P . .
N3 N 0.4866(4) 0.2500 0.9692(2) 0.0216(6) Uani 1 2 d S T P . .
O5 O 0.4150(3) 0.18927(10) 1.00099(19) 0.0387(5) Uani 1 1 d . . . . .
O6 O 0.6155(3) 0.2500 0.9110(2) 0.0374(7) Uani 1 2 d S T P . .
N4 N 0.0018(4) 0.2500 0.8814(2) 0.0236(6) Uani 1 2 d S T P . .
O7 O 0.0244(3) 0.18911(10) 0.93520(16) 0.0340(4) Uani 1 1 d . . . . .
O8 O -0.0383(4) 0.2500 0.7853(2) 0.0384(7) Uani 1 2 d S T P . .
O1W O 0.3787(4) 0.2500 1.2395(2) 0.0252(5) Uani 1 2 d S T P . .
N5 N 0.3538(6) 0.2500 0.4667(3) 0.0588(12) Uani 1 2 d S T P . .
C14 C 0.3849(6) 0.2500 0.5557(4) 0.0419(10) Uani 1 2 d S T P . .
C15 C 0.4223(9) 0.2500 0.6723(4) 0.0488(12) Uani 1 2 d S T P . .
H1WA H 0.356(7) 0.2500 1.303(5) 0.046(15) Uiso 1 2 d S . P . .
H1WB H 0.482(7) 0.2500 1.242(4) 0.041(14) Uiso 1 2 d S . P . .
H1N H 0.214(4) 0.0655(18) 0.991(2) 0.031(8) Uiso 1 1 d . . . . .
H2 H 0.097(3) 0.1229(16) 1.325(2) 0.023(7) Uiso 1 1 d . . . . .
H3 H 0.115(4) 0.0249(17) 1.449(3) 0.032(8) Uiso 1 1 d . . . . .
H5 H 0.239(3) -0.1220(16) 1.219(2) 0.022 Uiso 1 1 d . U . . .
H7 H 0.266(3) -0.0820(16) 1.034(2) 0.023(7) Uiso 1 1 d . . . . .
H9 H 0.388(4) -0.098(2) 0.878(3) 0.039(9) Uiso 1 1 d . . . . .
H10 H 0.457(4) -0.1162(18) 0.701(3) 0.036(8) Uiso 1 1 d . . . . .
H11 H 0.404(4) -0.0184(17) 0.575(3) 0.034(8) Uiso 1 1 d . . . . .
H12 H 0.258(4) 0.092(2) 0.629(3) 0.043(9) Uiso 1 1 d . . . . .
H13 H 0.199(4) 0.110(2) 0.814(3) 0.044(9) Uiso 1 1 d . . . . .
H15A H 0.311(9) 0.2500 0.696(6) 0.08(2) Uiso 1 2 d S . P . .
H15B H 0.491(6) 0.293(3) 0.695(4) 0.086(15) Uiso 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
Gd1 O1 2.3317(16) . ?
Gd1 O1 2.3317(16) 4_565 ?
Gd1 O1W 2.360(3) . ?
Gd1 O2 2.456(2) . ?
Gd1 O7 2.4675(19) . ?
Gd1 O7 2.4675(19) 4_565 ?
Gd1 O3 2.516(2) . ?
Gd1 O5 2.5291(18) . ?
Gd1 O5 2.5292(18) 4_565 ?
Gd1 N4 2.894(3) . ?
Gd1 N2 2.898(3) . ?
Gd1 N3 2.967(3) . ?
O1 C1 1.308(3) . ?
N1 C7 1.306(3) . ?
N1 C8 1.426(3) . ?
N1 H1N 0.87(3) . ?
Br1 C4 1.904(2) . ?
C1 C2 1.406(3) . ?
C1 C6 1.437(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.92(3) . ?
C3 C4 1.406(3) . ?
C3 H3 0.94(3) . ?
C4 C5 1.350(4) . ?
C5 C6 1.422(3) . ?
C5 H5 0.90(3) . ?
C6 C7 1.415(3) . ?
C7 H7 0.95(3) . ?
C8 C13 1.386(4) . ?
C8 C9 1.391(3) . ?
C9 C10 1.389(4) . ?
C9 H9 0.89(3) . ?
C10 C11 1.378(4) . ?
C10 H10 0.95(3) . ?
C11 C12 1.388(4) . ?
C11 H11 0.97(3) . ?
C12 C13 1.381(4) . ?
C12 H12 0.95(3) . ?
C13 H13 0.93(3) . ?
N2 O4 1.230(4) . ?
N2 O3 1.260(4) . ?
N2 O2 1.268(4) . ?
N3 O6 1.221(4) . ?
N3 O5 1.260(2) . ?
N3 O5 1.260(2) 4_565 ?
N4 O8 1.217(4) . ?
N4 O7 1.266(2) 4_565 ?
N4 O7 1.266(2) . ?
O1W H1WA 0.81(6) . ?
O1W H1WB 0.77(5) . ?
N5 C14 1.118(6) . ?
C14 C15 1.460(7) . ?
C15 H15A 0.89(7) . ?
C15 H15B 0.95(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
O1 Gd1 O1 163.47(9) . 4_565 ?
O1 Gd1 O1W 86.05(5) . . ?
O1 Gd1 O1W 86.05(5) 4_565 . ?
O1 Gd1 O2 81.81(4) . . ?
O1 Gd1 O2 81.81(4) 4_565 . ?
O1W Gd1 O2 69.31(9) . . ?
O1 Gd1 O7 70.43(6) . . ?
O1 Gd1 O7 121.42(6) 4_565 . ?
O1W Gd1 O7 149.39(6) . . ?
O2 Gd1 O7 123.73(7) . . ?
O1 Gd1 O7 121.42(6) . 4_565 ?
O1 Gd1 O7 70.43(6) 4_565 4_565 ?
O1W Gd1 O7 149.39(6) . 4_565 ?
O2 Gd1 O7 123.73(7) . 4_565 ?
O7 Gd1 O7 51.27(8) . 4_565 ?
O1 Gd1 O3 85.79(4) . . ?
O1 Gd1 O3 85.79(4) 4_565 . ?
O1W Gd1 O3 120.73(9) . . ?
O2 Gd1 O3 51.42(8) . . ?
O7 Gd1 O3 77.94(7) . . ?
O7 Gd1 O3 77.94(7) 4_565 . ?
O1 Gd1 O5 71.60(6) . . ?
O1 Gd1 O5 121.17(6) 4_565 . ?
O1W Gd1 O5 80.33(9) . . ?
O2 Gd1 O5 140.76(7) . . ?
O7 Gd1 O5 73.92(7) . . ?
O7 Gd1 O5 95.01(7) 4_565 . ?
O3 Gd1 O5 148.43(6) . . ?
O1 Gd1 O5 121.17(6) . 4_565 ?
O1 Gd1 O5 71.60(6) 4_565 4_565 ?
O1W Gd1 O5 80.33(9) . 4_565 ?
O2 Gd1 O5 140.76(7) . 4_565 ?
O7 Gd1 O5 95.01(7) . 4_565 ?
O7 Gd1 O5 73.92(7) 4_565 4_565 ?
O3 Gd1 O5 148.43(6) . 4_565 ?
O5 Gd1 O5 49.80(8) . 4_565 ?
O1 Gd1 N4 96.21(5) . . ?
O1 Gd1 N4 96.21(5) 4_565 . ?
O1W Gd1 N4 159.76(9) . . ?
O2 Gd1 N4 130.93(8) . . ?
O7 Gd1 N4 25.79(4) . . ?
O7 Gd1 N4 25.79(4) 4_565 . ?
O3 Gd1 N4 79.51(8) . . ?
O5 Gd1 N4 81.32(7) . . ?
O5 Gd1 N4 81.32(7) 4_565 . ?
O1 Gd1 N2 83.12(4) . . ?
O1 Gd1 N2 83.13(4) 4_565 . ?
O1W Gd1 N2 95.04(9) . . ?
O2 Gd1 N2 25.73(8) . . ?
O7 Gd1 N2 101.06(8) . . ?
O7 Gd1 N2 101.06(7) 4_565 . ?
O3 Gd1 N2 25.69(8) . . ?
O5 Gd1 N2 154.51(5) . . ?
O5 Gd1 N2 154.51(5) 4_565 . ?
N4 Gd1 N2 105.20(8) . . ?
O1 Gd1 N3 96.47(4) . . ?
O1 Gd1 N3 96.47(4) 4_565 . ?
O1W Gd1 N3 80.24(9) . . ?
O2 Gd1 N3 149.55(8) . . ?
O7 Gd1 N3 83.18(7) . . ?
O7 Gd1 N3 83.18(7) 4_565 . ?
O3 Gd1 N3 159.03(8) . . ?
O5 Gd1 N3 24.91(4) . . ?
O5 Gd1 N3 24.92(4) 4_565 . ?
N4 Gd1 N3 79.51(8) . . ?
N2 Gd1 N3 175.29(8) . . ?
C1 O1 Gd1 145.76(16) . . ?
C7 N1 C8 127.3(2) . . ?
C7 N1 H1N 115(2) . . ?
C8 N1 H1N 117(2) . . ?
O1 C1 C2 122.4(2) . . ?
O1 C1 C6 120.4(2) . . ?
C2 C1 C6 117.2(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 123.2(18) . . ?
C1 C2 H2 115.5(18) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 117.5(19) . . ?
C4 C3 H3 122.0(19) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 Br1 120.67(18) . . ?
C3 C4 Br1 118.59(19) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 116.7(18) . . ?
C6 C5 H5 123.2(18) . . ?
C7 C6 C5 117.5(2) . . ?
C7 C6 C1 122.5(2) . . ?
C5 C6 C1 120.1(2) . . ?
N1 C7 C6 124.2(2) . . ?
N1 C7 H7 117.1(17) . . ?
C6 C7 H7 118.7(17) . . ?
C13 C8 C9 120.6(2) . . ?
C13 C8 N1 117.4(2) . . ?
C9 C8 N1 122.0(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 121(2) . . ?
C8 C9 H9 120(2) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 121.7(19) . . ?
C9 C10 H10 117.5(19) . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 119.0(18) . . ?
C12 C11 H11 121.1(18) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 122(2) . . ?
C11 C12 H12 118(2) . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 121(2) . . ?
C8 C13 H13 120(2) . . ?
O4 N2 O3 122.3(3) . . ?
O4 N2 O2 120.5(3) . . ?
O3 N2 O2 117.2(3) . . ?
O4 N2 Gd1 177.8(2) . . ?
O3 N2 Gd1 59.96(15) . . ?
O2 N2 Gd1 57.27(15) . . ?
N2 O2 Gd1 97.00(19) . . ?
N2 O3 Gd1 94.36(17) . . ?
O6 N3 O5 122.34(13) . . ?
O6 N3 O5 122.34(13) . 4_565 ?
O5 N3 O5 115.3(3) . 4_565 ?
O6 N3 Gd1 176.4(2) . . ?
O5 N3 Gd1 57.71(13) . . ?
O5 N3 Gd1 57.71(13) 4_565 . ?
N3 O5 Gd1 97.38(14) . . ?
O8 N4 O7 122.55(15) . 4_565 ?
O8 N4 O7 122.55(15) . . ?
O7 N4 O7 114.9(3) 4_565 . ?
O8 N4 Gd1 170.4(2) . . ?
O7 N4 Gd1 57.96(15) 4_565 . ?
O7 N4 Gd1 57.96(15) . . ?
N4 O7 Gd1 96.25(16) . . ?
Gd1 O1W H1WA 124(4) . . ?
Gd1 O1W H1WB 135(4) . . ?
H1WA O1W H1WB 101(5) . . ?
N5 C14 C15 179.1(5) . . ?
C14 C15 H15A 100(5) . . ?
C14 C15 H15B 112(3) . . ?
H15A C15 H15B 114(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA N5 0.81(6) 2.03(6) 2.822(5) 169(5) 1_556
O1W H1WB O4 0.77(5) 2.01(5) 2.744(4) 160(5) 1_655
N1 H1N O1 0.87(3) 1.96(3) 2.662(3) 136(3) .
C2 H2 O2 0.92(3) 2.38(3) 3.212(2) 150(2) .
N1 H1N O5 0.87(3) 2.64(3) 3.271(3) 131(2) .
C9 H9 O5 0.89(3) 2.61(3) 3.454(4) 158(3) 3_657
C13 H13 O7 0.93(3) 2.45(3) 3.317(3) 155(3) .

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.094

_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT390_Compound5           
;
PROBLEM: Deviating Methyl C15 X-C-H Bond Angle ....100 Degree.
  
RESPONSE:  The hydrogen causing this problem is located on 
a mirror plane and the other available choice for 
refinement is to refine all the hydrogen atoms of this
 methyl group as disordered in two half occupied 
positions. We have attempted such a refinement with 
acceptable behavior, but we have considered this 
disorder model as overparameterized and so 
we have decided to keep the original one.
;

# end Validation Reply Form

