# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_6gd
_database_code_depnum_ccdc_archive 'CCDC 1940040'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 Gd O9'
_chemical_formula_sum            'C15 H12 Br6 Gd O9'
_chemical_formula_weight         972.90
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.2230(11)
_cell_length_b                   10.5573(6)
_cell_length_c                   22.0212(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.884(2)
_cell_angle_gamma                90
_cell_volume                     4684.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    296
_cell_measurement_theta_max      31.034
_cell_measurement_theta_min      3.468
_shelx_estimated_absorpt_T_max   0.354
_shelx_estimated_absorpt_T_min   0.145
_exptl_absorpt_coefficient_mu    13.111
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1239 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.6916. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49336
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.806
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4065
_reflns_number_total             4590
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.000210(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0207
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0064P)²+17.4775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0417
_refine_ls_wR_factor_ref         0.0433
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.52433(2) 0.52164(2) 0.39288(2) 0.01460(5) Uani 1 1 d . . . . .
Br1 Br 0.75955(2) 0.49075(3) 0.31574(2) 0.03140(10) Uani 1 1 d . . . . .
Br2 Br 0.90437(2) 0.63323(3) 0.33842(2) 0.02944(10) Uani 1 1 d . . . . .
Br3 Br 0.77339(2) 1.10599(3) 0.35595(2) 0.03228(10) Uani 1 1 d . . . . .
Br4 Br 0.62859(2) 0.95886(4) 0.33115(2) 0.03526(11) Uani 1 1 d . . . . .
Br5 Br 0.64271(2) 0.14427(3) 0.49641(2) 0.03564(11) Uani 1 1 d . . . . .
Br6 Br 0.63586(2) -0.16959(3) 0.50333(2) 0.02811(9) Uani 1 1 d . . . . .
O1 O 0.60976(12) 0.6515(2) 0.36522(11) 0.0257(6) Uani 1 1 d . . . . .
O2 O 0.61877(14) 0.6378(3) 0.26551(12) 0.0428(8) Uani 1 1 d . . . . .
O3 O 0.90743(11) 0.9752(2) 0.41068(11) 0.0247(5) Uani 1 1 d . . . . .
O4 O 0.93585(11) 0.9244(2) 0.31990(11) 0.0231(5) Uani 1 1 d . . . . .
O5 O 0.51679(12) 0.3121(2) 0.43344(11) 0.0251(6) Uani 1 1 d . . . . .
O6 O 0.49892(12) 0.3439(2) 0.53014(12) 0.0264(6) Uani 1 1 d . . . . .
O7 O 0.58073(13) 0.4043(2) 0.32018(13) 0.0309(6) Uani 1 1 d D . . . .
O8 O 0.61712(12) 0.4948(3) 0.47025(12) 0.0281(6) Uani 1 1 d D . . . .
O9 O 0.46652(13) 0.6787(2) 0.33092(13) 0.0322(6) Uani 1 1 d D . . . .
C1 C 0.63824(16) 0.6705(3) 0.31735(16) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.70524(16) 0.7366(3) 0.32692(14) 0.0176(7) Uani 1 1 d . . . . .
C3 C 0.76428(16) 0.6686(3) 0.32722(15) 0.0183(7) Uani 1 1 d . . . . .
C4 C 0.82517(16) 0.7290(3) 0.33651(15) 0.0186(7) Uani 1 1 d . . . . .
C5 C 0.82839(16) 0.8588(3) 0.34625(15) 0.0192(7) Uani 1 1 d . . . . .
C6 C 0.89514(16) 0.9242(3) 0.35937(16) 0.0199(7) Uani 1 1 d . . . . .
C7 C 0.76976(17) 0.9282(3) 0.34559(15) 0.0200(7) Uani 1 1 d . . . . .
C8 C 0.70866(16) 0.8666(3) 0.33559(15) 0.0206(7) Uani 1 1 d . . . . .
C9 C 0.50648(15) 0.2749(3) 0.48508(16) 0.0175(7) Uani 1 1 d . . . . .
C10 C 0.50275(15) 0.1322(3) 0.49396(14) 0.0153(7) Uani 1 1 d . . . . .
C11 C 0.56062(16) 0.0593(3) 0.49675(15) 0.0175(7) Uani 1 1 d . . . . .
C12 C 0.55815(16) -0.0713(3) 0.50171(15) 0.0169(7) Uani 1 1 d . . . . .
C13 C 0.5928(3) 0.2739(4) 0.3152(2) 0.0631(16) Uani 1 1 d . . . . .
H13A H 0.636465 0.260909 0.302319 0.095 Uiso 1 1 calc GR . . . .
H13B H 0.560523 0.237420 0.285772 0.095 Uiso 1 1 calc GR . . . .
H13C H 0.589640 0.234161 0.354046 0.095 Uiso 1 1 calc GR . . . .
C14 C 0.6867(2) 0.4928(5) 0.4685(2) 0.0502(13) Uani 1 1 d . . . . .
H14A H 0.698383 0.433334 0.438193 0.075 Uiso 1 1 calc GR . . . .
H14B H 0.707167 0.468083 0.507624 0.075 Uiso 1 1 calc GR . . . .
H14C H 0.701963 0.575721 0.458408 0.075 Uiso 1 1 calc GR . . . .
C15 C 0.4567(3) 0.8097(4) 0.3401(2) 0.0519(13) Uani 1 1 d . . . . .
H15A H 0.457825 0.853644 0.302081 0.078 Uiso 1 1 calc GR . . . .
H15B H 0.491219 0.841519 0.368727 0.078 Uiso 1 1 calc GR . . . .
H15C H 0.414400 0.822828 0.355877 0.078 Uiso 1 1 calc GR . . . .
H8 H 0.611(3) 0.508(5) 0.5059(8) 0.060(17) Uiso 1 1 d D . . . .
H9 H 0.4404(16) 0.654(4) 0.3031(13) 0.038(13) Uiso 1 1 d D . . . .
H7 H 0.590(3) 0.443(4) 0.2898(14) 0.065(17) Uiso 1 1 d 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 2.327(2) . ?
Gd1 O3 2.478(2) 3_445 ?
Gd1 O4 2.520(2) 3_445 ?
Gd1 O5 2.396(2) . ?
Gd1 O6 2.291(2) 5_666 ?
Gd1 O7 2.389(3) . ?
Gd1 O8 2.441(2) . ?
Gd1 O9 2.389(2) . ?
Br1 C3 1.896(3) . ?
Br2 C4 1.892(3) . ?
Br3 C7 1.892(3) . ?
Br4 C8 1.885(3) . ?
Br5 C11 1.888(3) . ?
Br6 C12 1.881(3) . ?
O1 C1 1.260(4) . ?
O2 C1 1.225(4) . ?
O3 C6 1.257(4) . ?
O4 C6 1.247(4) . ?
O5 C9 1.237(4) . ?
O6 C9 1.250(4) . ?
O7 C13 1.404(5) . ?
O7 H7 0.816(10) . ?
O8 C14 1.412(5) . ?
O8 H8 0.817(10) . ?
O9 C15 1.415(5) . ?
O9 H9 0.817(10) . ?
C1 C2 1.522(4) . ?
C2 C3 1.393(5) . ?
C2 C8 1.387(5) . ?
C3 C4 1.386(4) . ?
C4 C5 1.388(5) . ?
C5 C6 1.522(4) . ?
C5 C7 1.392(5) . ?
C7 C8 1.397(5) . ?
C9 C10 1.522(4) . ?
C10 C11 1.398(4) . ?
C10 C12 1.400(4) 5_656 ?
C11 C12 1.385(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O3 153.84(8) . 3_445 ?
O1 Gd1 O4 125.16(8) . 3_445 ?
O1 Gd1 O5 135.57(8) . . ?
O1 Gd1 O7 73.91(9) . . ?
O1 Gd1 O8 72.99(9) . . ?
O1 Gd1 O9 77.28(9) . . ?
O3 Gd1 O4 52.05(8) 3_445 3_445 ?
O5 Gd1 O3 70.51(8) . 3_445 ?
O5 Gd1 O4 78.31(8) . 3_445 ?
O5 Gd1 O8 72.67(8) . . ?
O6 Gd1 O1 91.84(9) 5_666 . ?
O6 Gd1 O3 75.34(8) 5_666 3_445 ?
O6 Gd1 O4 123.04(8) 5_666 3_445 ?
O6 Gd1 O5 105.84(9) 5_666 . ?
O6 Gd1 O7 163.14(9) 5_666 . ?
O6 Gd1 O8 75.49(9) 5_666 . ?
O6 Gd1 O9 82.60(9) 5_666 . ?
O7 Gd1 O3 121.31(9) . 3_445 ?
O7 Gd1 O4 73.45(9) . 3_445 ?
O7 Gd1 O5 79.65(9) . . ?
O7 Gd1 O8 91.44(9) . . ?
O8 Gd1 O3 123.61(8) . 3_445 ?
O8 Gd1 O4 149.30(8) . 3_445 ?
O9 Gd1 O3 78.50(9) . 3_445 ?
O9 Gd1 O4 68.40(8) . 3_445 ?
O9 Gd1 O5 144.13(9) . . ?
O9 Gd1 O7 102.44(10) . . ?
O9 Gd1 O8 142.09(9) . . ?
C1 O1 Gd1 135.7(2) . . ?
C6 O3 Gd1 93.5(2) . 3 ?
C6 O4 Gd1 91.80(19) . 3 ?
C9 O5 Gd1 131.0(2) . . ?
C9 O6 Gd1 174.1(2) . 5_666 ?
Gd1 O7 H7 116(4) . . ?
C13 O7 Gd1 131.1(3) . . ?
C13 O7 H7 112(4) . . ?
Gd1 O8 H8 119(4) . . ?
C14 O8 Gd1 133.7(2) . . ?
C14 O8 H8 105(4) . . ?
Gd1 O9 H9 118(3) . . ?
C15 O9 Gd1 131.6(2) . . ?
C15 O9 H9 109(3) . . ?
O1 C1 C2 115.0(3) . . ?
O2 C1 O1 127.0(3) . . ?
O2 C1 C2 118.0(3) . . ?
C3 C2 C1 121.1(3) . . ?
C8 C2 C1 120.4(3) . . ?
C8 C2 C3 118.5(3) . . ?
C2 C3 Br1 118.4(2) . . ?
C4 C3 Br1 120.6(2) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 Br2 119.8(2) . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 Br2 119.7(2) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C7 119.3(3) . . ?
C7 C5 C6 120.3(3) . . ?
O3 C6 Gd1 60.35(17) . 3 ?
O3 C6 C5 118.0(3) . . ?
O4 C6 Gd1 62.23(17) . 3 ?
O4 C6 O3 122.3(3) . . ?
O4 C6 C5 119.7(3) . . ?
C5 C6 Gd1 173.2(2) . 3 ?
C5 C7 Br3 119.7(2) . . ?
C5 C7 C8 119.9(3) . . ?
C8 C7 Br3 120.4(3) . . ?
C2 C8 Br4 118.1(2) . . ?
C2 C8 C7 121.0(3) . . ?
C7 C8 Br4 120.8(3) . . ?
O5 C9 O6 125.9(3) . . ?
O5 C9 C10 116.5(3) . . ?
O6 C9 C10 117.6(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 C12 118.8(3) . 5_656 ?
C12 C10 C9 121.1(3) 5_656 . ?
C10 C11 Br5 118.1(2) . . ?
C12 C11 Br5 120.8(2) . . ?
C12 C11 C10 121.1(3) . . ?
C10 C12 Br6 118.9(2) 5_656 . ?
C11 C12 Br6 121.0(2) . . ?
C11 C12 C10 120.1(3) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O3 0.817(10) 1.913(12) 2.728(4) 175(5) 7_666 yes
O9 H9 O2 0.817(10) 1.853(14) 2.655(4) 167(4) 2_655 yes
O7 H7 O4 0.816(10) 2.43(4) 3.082(4) 137(5) 4_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7tb
_database_code_depnum_ccdc_archive 'CCDC 1940041'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 O9 Tb'
_chemical_formula_sum            'C15 H12 Br6 O9 Tb'
_chemical_formula_weight         974.58
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.1546(15)
_cell_length_b                   10.5416(8)
_cell_length_c                   22.0160(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.940(3)
_cell_angle_gamma                90
_cell_volume                     4660.2(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8368
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.430
_cell_measurement_theta_min      2.866
_shelx_estimated_absorpt_T_max   0.414
_shelx_estimated_absorpt_T_min   0.129
_exptl_absorpt_coefficient_mu    13.368
_exptl_absorpt_correction_T_max  0.4923
_exptl_absorpt_correction_T_min  0.3553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1187 before and 0.0624 after correction. The Ratio of minimum to maximum transmission is 0.7217. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3667
_reflns_number_total             4561
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.000163(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+10.8562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0518
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.52409(2) 0.52114(2) 0.39311(2) 0.01432(7) Uani 1 1 d . . . . .
Br1 Br 0.75942(3) 0.48933(4) 0.31592(3) 0.03035(14) Uani 1 1 d . . . . .
Br2 Br 0.90454(2) 0.63191(5) 0.33873(3) 0.02835(13) Uani 1 1 d . . . . .
Br3 Br 0.77316(2) 1.10538(5) 0.35567(3) 0.03138(14) Uani 1 1 d . . . . .
Br4 Br 0.62806(2) 0.95791(5) 0.33100(3) 0.03447(15) Uani 1 1 d . . . . .
Br5 Br 0.64299(2) 0.14463(5) 0.49649(3) 0.03488(15) Uani 1 1 d . . . . .
Br6 Br 0.63627(2) -0.16950(4) 0.50317(3) 0.02752(13) Uani 1 1 d . . . . .
O1 O 0.60918(15) 0.6507(3) 0.36575(15) 0.0249(8) Uani 1 1 d . . . . .
O2 O 0.61845(17) 0.6347(4) 0.26603(17) 0.0394(10) Uani 1 1 d . . . . .
O3 O 0.90780(15) 0.9753(3) 0.41088(15) 0.0247(8) Uani 1 1 d . . . . .
O4 O 0.93630(15) 0.9229(3) 0.32055(15) 0.0231(8) Uani 1 1 d . . . . .
O5 O 0.51637(15) 0.3131(3) 0.43360(15) 0.0229(8) Uani 1 1 d . . . . .
O6 O 0.49910(15) 0.3436(3) 0.53101(16) 0.0251(8) Uani 1 1 d . . . . .
O7 O 0.58100(17) 0.4043(3) 0.32158(18) 0.0297(9) Uani 1 1 d D . . . .
O8 O 0.61668(16) 0.4947(3) 0.46968(16) 0.0270(8) Uani 1 1 d D . . . .
O9 O 0.46645(18) 0.6767(3) 0.33118(18) 0.0299(9) Uani 1 1 d D . . . .
C1 C 0.6379(2) 0.6687(4) 0.3179(2) 0.0227(11) Uani 1 1 d . . . . .
C2 C 0.7050(2) 0.7355(4) 0.3273(2) 0.0160(10) Uani 1 1 d . . . . .
C3 C 0.7639(2) 0.6666(4) 0.3271(2) 0.0180(10) Uani 1 1 d . . . . .
C4 C 0.8254(2) 0.7278(4) 0.3366(2) 0.0159(10) Uani 1 1 d . . . . .
C5 C 0.8283(2) 0.8583(4) 0.3463(2) 0.0168(10) Uani 1 1 d . . . . .
C6 C 0.8952(2) 0.9240(4) 0.3600(2) 0.0184(11) Uani 1 1 d . . . . .
C7 C 0.7694(2) 0.9266(4) 0.3456(2) 0.0185(10) Uani 1 1 d . . . . .
C8 C 0.7085(2) 0.8652(4) 0.3354(2) 0.0191(11) Uani 1 1 d . . . . .
C9 C 0.5065(2) 0.2755(4) 0.4856(2) 0.0157(10) Uani 1 1 d . . . . .
C10 C 0.5027(2) 0.1332(4) 0.4941(2) 0.0162(10) Uani 1 1 d . . . . .
C11 C 0.5605(2) 0.0598(4) 0.4967(2) 0.0163(10) Uani 1 1 d . . . . .
C12 C 0.5579(2) -0.0716(4) 0.5017(2) 0.0184(10) Uani 1 1 d . . . . .
C13 C 0.5919(3) 0.2727(5) 0.3160(3) 0.057(2) Uani 1 1 d . . . . .
H13A H 0.636168 0.258361 0.304401 0.085 Uiso 1 1 calc GR . . . .
H13B H 0.560135 0.238184 0.285442 0.085 Uiso 1 1 calc GR . . . .
H13C H 0.586976 0.232015 0.354358 0.085 Uiso 1 1 calc GR . . . .
C14 C 0.6865(3) 0.4933(6) 0.4683(3) 0.0472(17) Uani 1 1 d . . . . .
H14A H 0.698467 0.435866 0.437247 0.071 Uiso 1 1 calc GR . . . .
H14B H 0.706803 0.466141 0.507203 0.071 Uiso 1 1 calc GR . . . .
H14C H 0.701826 0.577089 0.459614 0.071 Uiso 1 1 calc GR . . . .
C15 C 0.4563(3) 0.8080(5) 0.3406(3) 0.0508(17) Uani 1 1 d . . . . .
H15A H 0.454948 0.851666 0.302230 0.076 Uiso 1 1 calc GR . . . .
H15B H 0.492092 0.840965 0.367579 0.076 Uiso 1 1 calc GR . . . .
H15C H 0.414856 0.820311 0.358296 0.076 Uiso 1 1 calc GR . . . .
H8 H 0.611(3) 0.510(5) 0.5051(9) 0.037(18) Uiso 1 1 d D . . . .
H9 H 0.442(2) 0.655(5) 0.3011(15) 0.044(19) Uiso 1 1 d D . . . .
H7 H 0.587(3) 0.438(6) 0.2891(16) 0.07(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.312(3) . ?
Tb1 O3 2.457(3) 3_445 ?
Tb1 O4 2.504(3) 3_445 ?
Tb1 O5 2.378(3) . ?
Tb1 O6 2.275(3) 5_666 ?
Tb1 O7 2.372(3) . ?
Tb1 O8 2.421(3) . ?
Tb1 O9 2.371(3) . ?
Tb1 C6 2.829(4) 3_445 ?
Br1 C3 1.886(4) . ?
Br2 C4 1.886(4) . ?
Br3 C7 1.898(4) . ?
Br4 C8 1.888(4) . ?
Br5 C11 1.887(4) . ?
Br6 C12 1.884(4) . ?
O1 C1 1.258(6) . ?
O2 C1 1.229(6) . ?
O3 C6 1.251(6) . ?
O4 C6 1.250(5) . ?
O5 C9 1.243(5) . ?
O6 C9 1.250(5) . ?
O7 C13 1.412(6) . ?
O7 H7 0.817(10) . ?
O8 C14 1.411(6) . ?
O8 H8 0.815(10) . ?
O9 C15 1.417(6) . ?
O9 H9 0.818(10) . ?
C1 C2 1.523(6) . ?
C2 C3 1.392(6) . ?
C2 C8 1.380(6) . ?
C3 C4 1.396(6) . ?
C4 C5 1.393(6) . ?
C5 C6 1.523(6) . ?
C5 C7 1.387(6) . ?
C7 C8 1.389(6) . ?
C9 C10 1.515(6) . ?
C10 C11 1.395(6) . ?
C10 C12 1.395(6) 5_656 ?
C11 C12 1.391(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 Tb1 O3 153.71(11) . 3_445 ?
O1 Tb1 O4 125.26(11) . 3_445 ?
O1 Tb1 O5 135.76(11) . . ?
O1 Tb1 O7 73.85(12) . . ?
O1 Tb1 O8 72.83(12) . . ?
O1 Tb1 O9 77.26(12) . . ?
O1 Tb1 C6 146.29(13) . 3_445 ?
O3 Tb1 O4 52.34(10) 3_445 3_445 ?
O3 Tb1 C6 26.18(12) 3_445 3_445 ?
O4 Tb1 C6 26.22(11) 3_445 3_445 ?
O5 Tb1 O3 70.42(11) . 3_445 ?
O5 Tb1 O4 78.00(11) . 3_445 ?
O5 Tb1 O8 72.79(11) . . ?
O5 Tb1 C6 70.99(12) . 3_445 ?
O6 Tb1 O1 91.43(11) 5_666 . ?
O6 Tb1 O3 75.36(11) 5_666 3_445 ?
O6 Tb1 O4 123.32(11) 5_666 3_445 ?
O6 Tb1 O5 106.17(11) 5_666 . ?
O6 Tb1 O7 162.70(12) 5_666 . ?
O6 Tb1 O8 75.85(12) 5_666 . ?
O6 Tb1 O9 82.39(13) 5_666 . ?
O6 Tb1 C6 100.04(12) 5_666 3_445 ?
O7 Tb1 O3 121.74(12) . 3_445 ?
O7 Tb1 O4 73.56(11) . 3_445 ?
O7 Tb1 O5 79.67(12) . . ?
O7 Tb1 O8 90.84(13) . . ?
O7 Tb1 C6 97.27(13) . 3_445 ?
O8 Tb1 O3 123.72(11) . 3_445 ?
O8 Tb1 O4 148.94(11) . 3_445 ?
O8 Tb1 C6 140.67(12) . 3_445 ?
O9 Tb1 O3 78.50(12) . 3_445 ?
O9 Tb1 O4 68.59(11) . 3_445 ?
O9 Tb1 O5 143.97(11) . . ?
O9 Tb1 O7 102.61(13) . . ?
O9 Tb1 O8 142.20(12) . . ?
O9 Tb1 C6 73.06(12) . 3_445 ?
C1 O1 Tb1 135.4(3) . . ?
C6 O3 Tb1 93.7(3) . 3 ?
C6 O4 Tb1 91.5(3) . 3 ?
C9 O5 Tb1 131.3(3) . . ?
C9 O6 Tb1 173.3(3) . 5_666 ?
Tb1 O7 H7 118(5) . . ?
C13 O7 Tb1 131.0(3) . . ?
C13 O7 H7 108(5) . . ?
Tb1 O8 H8 119(4) . . ?
C14 O8 Tb1 134.2(3) . . ?
C14 O8 H8 104(4) . . ?
Tb1 O9 H9 120(4) . . ?
C15 O9 Tb1 131.4(3) . . ?
C15 O9 H9 108(4) . . ?
O1 C1 C2 115.1(4) . . ?
O2 C1 O1 126.9(4) . . ?
O2 C1 C2 117.9(4) . . ?
C3 C2 C1 120.4(4) . . ?
C8 C2 C1 120.7(4) . . ?
C8 C2 C3 118.9(4) . . ?
C2 C3 Br1 119.1(3) . . ?
C2 C3 C4 120.3(4) . . ?
C4 C3 Br1 120.6(3) . . ?
C3 C4 Br2 119.6(3) . . ?
C5 C4 Br2 120.1(3) . . ?
C5 C4 C3 120.3(4) . . ?
C4 C5 C6 120.3(4) . . ?
C7 C5 C4 119.1(4) . . ?
C7 C5 C6 120.6(4) . . ?
O3 C6 Tb1 60.1(2) . 3 ?
O3 C6 C5 118.8(4) . . ?
O4 C6 Tb1 62.2(2) . 3 ?
O4 C6 O3 122.1(4) . . ?
O4 C6 C5 119.1(4) . . ?
C5 C6 Tb1 173.5(3) . 3 ?
C5 C7 Br3 119.3(3) . . ?
C5 C7 C8 120.2(4) . . ?
C8 C7 Br3 120.5(3) . . ?
C2 C8 Br4 118.2(3) . . ?
C2 C8 C7 121.1(4) . . ?
C7 C8 Br4 120.7(3) . . ?
O5 C9 O6 126.4(4) . . ?
O5 C9 C10 116.3(4) . . ?
O6 C9 C10 117.3(4) . . ?
C11 C10 C9 120.2(4) . . ?
C12 C10 C9 121.5(4) 5_656 . ?
C12 C10 C11 118.3(4) 5_656 . ?
C10 C11 Br5 118.0(3) . . ?
C12 C11 Br5 120.7(3) . . ?
C12 C11 C10 121.2(4) . . ?
C10 C12 Br6 118.9(3) 5_656 . ?
C11 C12 Br6 120.7(3) . . ?
C11 C12 C10 120.5(4) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O3 0.815(10) 1.925(13) 2.735(5) 173(6) 7_666 yes
O9 H9 O2 0.818(10) 1.851(15) 2.660(5) 169(6) 2_655 yes
O7 H7 O4 0.817(10) 2.42(4) 3.125(5) 144(6) 4_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_16gd
_database_code_depnum_ccdc_archive 'CCDC 1940055'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H4 Br4 Gd N O8'
_chemical_formula_sum            'C9 H4 Br4 Gd N O8'
_chemical_formula_weight         730.98
_chemical_melting_point          ?
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'
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.165(2)
_cell_length_b                   9.216(2)
_cell_length_c                   10.039(2)
_cell_angle_alpha                104.271(8)
_cell_angle_beta                 93.426(8)
_cell_angle_gamma                99.634(9)
_cell_volume                     805.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8619
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.924
_cell_measurement_theta_min      2.926
_shelx_estimated_absorpt_T_max   0.283
_shelx_estimated_absorpt_T_min   0.121
_exptl_absorpt_coefficient_mu    14.072
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1333 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.5913. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15148
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2775
_reflns_number_total             3163
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.195
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.0034(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+1.0172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O8-H8
 0.85 with sigma of 0.01
 C9-H8
 1.898416 with sigma of 0.02
 Gd1-H8
 2.916163 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.47314(2) 0.21057(2) 0.97889(2) 0.01545(8) Uani 1 1 d D . . . .
Br1 Br 0.20394(6) 0.32597(7) 0.63007(5) 0.04448(16) Uani 1 1 d . . . . .
Br2 Br 0.20924(5) 0.07663(6) 0.32853(5) 0.04247(15) Uani 1 1 d . . . . .
Br3 Br 0.83448(5) 0.21782(6) 0.38877(5) 0.04225(15) Uani 1 1 d . . . . .
Br4 Br 0.82921(6) 0.47365(6) 0.68662(5) 0.04708(16) Uani 1 1 d . . . . .
O1 O 0.5329(4) 0.4019(3) 0.8745(3) 0.0292(7) Uani 1 1 d . . . . .
O2 O 0.5054(4) 0.6078(3) 0.8069(3) 0.0289(7) Uani 1 1 d . . . . .
O3 O 0.5494(4) -0.0815(3) 0.2686(3) 0.0309(8) Uani 1 1 d . . . . .
O4 O 0.4957(3) 0.0615(3) 0.1362(3) 0.0206(6) Uani 1 1 d . . . . .
O5 O 0.2330(4) 0.0426(3) 0.9432(4) 0.0369(8) Uani 1 1 d . . . . .
O6 O 0.2266(4) 0.2778(4) 0.9653(4) 0.0460(10) Uani 1 1 d . . . . .
O7 O 0.0222(4) 0.1098(5) 0.9066(5) 0.0626(12) Uani 1 1 d . . . . .
O8 O 0.7343(3) 0.2337(3) 1.0031(4) 0.0349(8) Uani 1 1 d D . . . .
H8 H 0.776(2) 0.1584(19) 1.006(6) 0.052 Uiso 1 1 d DR . . . .
N1 N 0.1555(4) 0.1427(4) 0.9377(4) 0.0323(9) Uani 1 1 d . . . . .
C1 C 0.5173(5) 0.4712(4) 0.7830(4) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.5174(5) 0.3785(4) 0.6357(4) 0.0176(9) Uani 1 1 d . . . . .
C3 C 0.3847(5) 0.2975(5) 0.5588(4) 0.0205(9) Uani 1 1 d . . . . .
C4 C 0.3873(5) 0.1930(4) 0.4335(4) 0.0201(9) Uani 1 1 d . . . . .
C5 C 0.5206(5) 0.1671(4) 0.3837(4) 0.0165(9) Uani 1 1 d . . . . .
C6 C 0.5228(5) 0.0418(4) 0.2564(4) 0.0172(9) Uani 1 1 d . . . . .
C7 C 0.6530(5) 0.2519(4) 0.4587(4) 0.0192(9) Uani 1 1 d . . . . .
C8 C 0.6508(5) 0.3570(4) 0.5829(4) 0.0210(9) Uani 1 1 d . . . . .
C9 C 0.8450(6) 0.3701(6) 1.0410(6) 0.0472(15) Uani 1 1 d D . . . .
H9A H 0.928025 0.355772 0.988580 0.071 Uiso 1 1 calc GR . . . .
H9B H 0.877774 0.393337 1.137854 0.071 Uiso 1 1 calc GR . . . .
H9C H 0.803424 0.452847 1.022198 0.071 Uiso 1 1 calc GR . . . .


_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 2.272(3) . ?
Gd1 O2 2.351(3) 2_667 ?
Gd1 O3 2.455(3) 2_656 ?
Gd1 O4 2.560(3) 2_656 ?
Gd1 O4 2.356(3) 1_556 ?
Gd1 O5 2.421(3) . ?
Gd1 O6 2.445(3) . ?
Gd1 O8 2.359(3) . ?
Br1 C3 1.876(4) . ?
Br2 C4 1.891(4) . ?
Br3 C7 1.888(4) . ?
Br4 C8 1.889(4) . ?
O1 C1 1.256(5) . ?
O2 C1 1.248(5) . ?
O3 C6 1.235(5) . ?
O4 C6 1.280(5) . ?
O5 N1 1.265(5) . ?
O6 N1 1.260(5) . ?
O7 N1 1.211(5) . ?
O8 H8 0.851(9) . ?
O8 C9 1.430(6) . ?
C1 C2 1.514(5) . ?
C2 C3 1.390(6) . ?
C2 C8 1.386(6) . ?
C3 C4 1.387(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.500(5) . ?
C5 C7 1.390(6) . ?
C7 C8 1.382(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 O2 89.65(10) . 2_667 ?
O1 Gd1 O3 75.42(10) . 2_656 ?
O1 Gd1 O4 121.01(10) . 2_656 ?
O1 Gd1 O4 158.46(11) . 1_556 ?
O1 Gd1 O5 124.78(12) . . ?
O1 Gd1 O6 82.87(12) . . ?
O1 Gd1 O8 81.44(11) . . ?
O2 Gd1 O3 164.57(9) 2_667 2_656 ?
O2 Gd1 O4 143.51(9) 2_667 2_656 ?
O2 Gd1 O4 77.94(10) 2_667 1_556 ?
O2 Gd1 O5 109.21(12) 2_667 . ?
O2 Gd1 O6 80.69(12) 2_667 . ?
O2 Gd1 O8 88.46(12) 2_667 . ?
O3 Gd1 O4 51.45(9) 2_656 2_656 ?
O4 Gd1 O3 117.46(9) 1_556 2_656 ?
O4 Gd1 O4 66.53(11) 1_556 2_656 ?
O4 Gd1 O5 76.34(11) 1_556 . ?
O4 Gd1 O6 111.88(12) 1_556 . ?
O4 Gd1 O8 80.70(11) 1_556 . ?
O5 Gd1 O3 77.26(12) . 2_656 ?
O5 Gd1 O4 71.08(10) . 2_656 ?
O5 Gd1 O6 52.04(10) . . ?
O6 Gd1 O3 93.40(12) . 2_656 ?
O6 Gd1 O4 119.46(10) . 2_656 ?
O8 Gd1 O3 93.04(12) . 2_656 ?
O8 Gd1 O4 78.21(10) . 2_656 ?
O8 Gd1 O5 147.02(10) . . ?
O8 Gd1 O6 160.94(11) . . ?
C1 O1 Gd1 154.7(3) . . ?
C1 O2 Gd1 128.8(3) . 2_667 ?
C6 O3 Gd1 97.3(2) . 2_656 ?
Gd1 O4 Gd1 113.47(11) 1_554 2_656 ?
C6 O4 Gd1 154.0(2) . 1_554 ?
C6 O4 Gd1 91.1(2) . 2_656 ?
N1 O5 Gd1 96.5(2) . . ?
N1 O6 Gd1 95.5(2) . . ?
Gd1 O8 H8 122.1(14) . . ?
C9 O8 Gd1 128.2(3) . . ?
C9 O8 H8 108.7(14) . . ?
O6 N1 O5 115.5(4) . . ?
O7 N1 O5 121.8(4) . . ?
O7 N1 O6 122.7(4) . . ?
O1 C1 C2 115.5(3) . . ?
O2 C1 O1 124.4(4) . . ?
O2 C1 C2 120.1(3) . . ?
C3 C2 C1 120.3(4) . . ?
C8 C2 C1 120.1(4) . . ?
C8 C2 C3 119.1(4) . . ?
C2 C3 Br1 119.2(3) . . ?
C4 C3 Br1 120.9(3) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 Br2 121.1(3) . . ?
C5 C4 Br2 117.9(3) . . ?
C5 C4 C3 121.0(4) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 C7 118.9(3) . . ?
C7 C5 C6 120.4(4) . . ?
O3 C6 Gd1 57.6(2) . 2_656 ?
O3 C6 O4 120.1(3) . . ?
O3 C6 C5 119.3(4) . . ?
O4 C6 Gd1 62.53(19) . 2_656 ?
O4 C6 C5 120.5(3) . . ?
C5 C6 Gd1 176.8(3) . 2_656 ?
C5 C7 Br3 118.7(3) . . ?
C8 C7 Br3 121.0(3) . . ?
C8 C7 C5 120.3(4) . . ?
C2 C8 Br4 118.2(3) . . ?
C7 C8 Br4 121.1(3) . . ?
C7 C8 C2 120.8(4) . . ?
O8 C9 H9A 109.5 . . ?
O8 C9 H9B 109.5 . . ?
O8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O5 0.851(9) 2.03(2) 2.789(4) 148(3) 2_657 yes
O8 H8 O7 0.851(9) 2.58(3) 3.158(5) 126(3) 1_655 yes
C9 H9A O7 0.96 2.53 3.191(7) 126.5 1_655 yes
C9 H9C O6 0.96 2.52 3.431(6) 159.2 2_667 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_13gd
_database_code_depnum_ccdc_archive 'CCDC 1940050'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26.7 H15.4 Br12 Gd2 O17'
_chemical_formula_sum            'C26.70 H15.40 Br12 Gd2 O17'
_chemical_formula_weight         1881.49
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.587(5)
_cell_length_b                   18.133(7)
_cell_length_c                   21.632(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.686(15)
_cell_angle_gamma                90
_cell_volume                     4504(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.025
_cell_measurement_theta_min      2.941
_shelx_estimated_absorpt_T_max   0.343
_shelx_estimated_absorpt_T_min   0.171
_exptl_absorpt_coefficient_mu    13.629
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1220 before and 0.0701 after correction. The Ratio of minimum to maximum transmission is 0.8762. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.775
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3438
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            64054
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.863
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6542
_reflns_number_total             8850
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.286
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.00025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8850
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+15.1813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O14-H14
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O13A-H13A
 0.85 with sigma of 0.01
 O13-H13
 0.85 with sigma of 0.01
 O15-H15A = O15-H15B
 0.85 with sigma of 0.02
 O16-H16A = O16-H16B
 0.85 with sigma of 0.02
 C26-H14
 1.915338 with sigma of 0.02
 Gd2-H14
 2.96379 with sigma of 0.02
 C27-H17
 1.91147 with sigma of 0.02
 Gd2-H17
 3.083201 with sigma of 0.02
 C25A-H13A
 2.001639 with sigma of 0.02
 Gd2-H13A
 2.970671 with sigma of 0.02
 C25-H13
 2.006304 with sigma of 0.02
 Gd2-H13
 2.996201 with sigma of 0.02
 H15A-H15B
 1.34 with sigma of 0.04
 H16A-H16B
 1.34 with sigma of 0.04
 Gd2-O15 \\sim Gd2-O18
 with sigma of 0.01
 Gd2-O14 \\sim Gd2-O17
 with sigma of 0.01
 O14-C26 \\sim O17-C27
 with sigma of 0.01
 Gd2-O13 \\sim Gd2-O13A
 with sigma of 0.02
 O13-C25 \\sim O13A-C25A
 with sigma of 0.02
 Gd2-C25 \\sim Gd2-C25A
 with sigma of 0.04
 Gd2-H15A \\sim Gd2-H15B
 with sigma of 0.02
 Gd2-H16A \\sim Gd2-H16B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O17) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O13) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O13A) \\sim Ueq, Uanis(C25A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Gd2, O17, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Gd2, O18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Gd2, O13, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Gd2, O13A, C25A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O13A)=Sof(H13A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(O13)=Sof(H13)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
 Fixed Sof: O17(0.7) H17(0.7) O18(0.3) H18A(0.3) H18B(0.3) C27(0.7) H27A(0.7)
 H27B(0.7) H27C(0.7)
6.a Rotating group:
 O18(H18A,H18B)
6.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.43781(2) 0.74826(2) 0.63079(2) 0.01574(7) Uani 1 1 d . . . . .
Gd2 Gd 0.49714(2) 0.24984(2) 0.87147(2) 0.01812(8) Uani 1 1 d D U . . .
Br1 Br 0.31398(7) 0.67352(3) 0.85054(3) 0.0451(2) Uani 1 1 d . . . . .
Br2 Br 0.31255(7) 0.51632(4) 0.93037(3) 0.0460(2) Uani 1 1 d . . . . .
Br3 Br 0.21435(7) 0.35679(4) 0.70552(3) 0.0482(2) Uani 1 1 d . . . . .
Br4 Br 0.21013(7) 0.51641(4) 0.62513(3) 0.04429(19) Uani 1 1 d . . . . .
Br5 Br 0.60383(7) 0.95022(4) 0.81302(3) 0.03847(17) Uani 1 1 d . . . . .
Br6 Br 0.64960(8) 0.94700(4) 0.96838(3) 0.0506(2) Uani 1 1 d . . . . .
Br7 Br 0.70379(8) 0.63678(4) 0.96362(3) 0.0547(2) Uani 1 1 d . . . . .
Br8 Br 0.67029(9) 0.64152(4) 0.80676(4) 0.0628(3) Uani 1 1 d . . . . .
Br9 Br 0.54800(8) 0.67042(4) 0.45827(4) 0.0563(2) Uani 1 1 d . . . . .
Br10 Br 0.43766(8) 0.54515(4) 0.35243(4) 0.0595(2) Uani 1 1 d . . . . .
Br11 Br 0.51349(7) 0.86383(4) 0.40155(3) 0.0487(2) Uani 1 1 d . . . . .
Br12 Br 0.41037(7) 1.02906(4) 0.35181(3) 0.04384(19) Uani 1 1 d . . . . .
O1 O 0.3312(4) 0.6825(2) 0.6934(2) 0.0372(11) Uani 1 1 d . . . . .
O2 O 0.1403(4) 0.6807(2) 0.6949(2) 0.0351(11) Uani 1 1 d . . . . .
O3 O 0.3626(4) 0.3456(2) 0.8565(2) 0.0345(11) Uani 1 1 d . . . . .
O4 O 0.1740(4) 0.3526(2) 0.8618(2) 0.0324(10) Uani 1 1 d . . . . .
O5 O 0.5495(4) 0.7841(2) 0.71981(19) 0.0384(11) Uani 1 1 d . . . . .
O6 O 0.7359(4) 0.8163(3) 0.7331(2) 0.0488(13) Uani 1 1 d . . . . .
O7 O 0.8049(3) 0.7912(2) 1.04821(18) 0.0342(11) Uani 1 1 d . . . . .
O8 O 0.6158(4) 0.7849(2) 1.05291(18) 0.0331(10) Uani 1 1 d . . . . .
O9 O 0.5463(4) 0.6481(2) 0.6179(2) 0.0359(11) Uani 1 1 d . . . . .
O10 O 0.7166(4) 0.6070(3) 0.5988(3) 0.0626(17) Uani 1 1 d . . . . .
O11 O 0.5366(4) 0.8123(2) 0.56630(19) 0.0323(10) Uani 1 1 d . . . . .
O12 O 0.7017(4) 0.8476(3) 0.5352(2) 0.0452(12) Uani 1 1 d . . . . .
O13 O 0.5992(9) 0.3680(4) 0.8908(6) 0.053(3) Uani 0.72(2) 1 d D U P A 1
H13 H 0.630(8) 0.380(2) 0.9275(14) 0.080 Uiso 0.72(2) 1 d DR . P A 1
O13A O 0.606(3) 0.3645(10) 0.8641(14) 0.063(9) Uani 0.28(2) 1 d D U P A 2
H13A H 0.653(11) 0.368(3) 0.837(6) 0.094 Uiso 0.28(2) 1 d DR . P A 2
O14 O 0.6249(5) 0.2468(4) 0.9710(2) 0.0756(19) Uani 1 1 d D . . . .
H14 H 0.690(3) 0.269(4) 0.9738(19) 0.113 Uiso 1 1 d DR . . . .
O15 O 0.6850(4) 0.2272(3) 0.8483(3) 0.074(2) Uani 1 1 d D . . . .
H15A H 0.733(4) 0.195(4) 0.865(4) 0.110 Uiso 1 1 d DR . . . .
H15B H 0.724(4) 0.254(4) 0.826(4) 0.110 Uiso 1 1 d DR . . . .
O16 O 0.5458(4) 0.1197(3) 0.8899(3) 0.0541(14) Uani 1 1 d D . . . .
H16A H 0.499(3) 0.0837(17) 0.892(4) 0.081 Uiso 1 1 d DR . . . .
H16B H 0.614(2) 0.100(2) 0.895(4) 0.081 Uiso 1 1 d DR . . . .
O17 O 0.5159(14) 0.3008(6) 0.7665(3) 0.040(3) Uani 0.7 1 d D U P A 2
H17 H 0.555(6) 0.339(2) 0.7595(12) 0.060 Uiso 0.7 1 d DR . P B 2
O18 O 0.512(4) 0.2789(15) 0.7667(7) 0.057(9) Uani 0.3 1 d D U P A 1
H18A H 0.448308 0.267813 0.741882 0.086 Uiso 0.3 1 d GR . P A 1
H18B H 0.565018 0.253932 0.751101 0.086 Uiso 0.3 1 d GR . P A 1
C1 C 0.2401(5) 0.6552(3) 0.7075(3) 0.0220(13) Uani 1 1 d . . . . .
C2 C 0.2514(5) 0.5832(3) 0.7446(3) 0.0209(13) Uani 1 1 d . . . . .
C3 C 0.2780(5) 0.5824(3) 0.8090(3) 0.0230(13) Uani 1 1 d . . . . .
C4 C 0.2811(5) 0.5164(3) 0.8422(3) 0.0219(13) Uani 1 1 d . . . . .
C5 C 0.2608(4) 0.4488(3) 0.8116(2) 0.0183(12) Uani 1 1 d . . . . .
C6 C 0.2384(5) 0.4489(3) 0.7466(3) 0.0232(13) Uani 1 1 d . . . . .
C7 C 0.2345(5) 0.5150(3) 0.7136(3) 0.0249(13) Uani 1 1 d . . . . .
C8 C 0.2652(5) 0.3758(3) 0.8464(3) 0.0212(13) Uani 1 1 d . . . . .
C9 C 0.6433(6) 0.7991(3) 0.7520(3) 0.0296(15) Uani 1 1 d . . . . .
C10 C 0.6468(5) 0.7965(3) 0.8230(2) 0.0208(13) Uani 1 1 d . . . . .
C11 C 0.6386(5) 0.8610(3) 0.8569(3) 0.0233(13) Uani 1 1 d . . . . .
C12 C 0.6567(5) 0.8587(3) 0.9220(3) 0.0213(13) Uani 1 1 d . . . . .
C13 C 0.6785(5) 0.7919(3) 0.9531(2) 0.0211(13) Uani 1 1 d . . . . .
C14 C 0.6802(5) 0.7269(3) 0.9190(3) 0.0255(14) Uani 1 1 d . . . . .
C15 C 0.6651(5) 0.7280(3) 0.8542(3) 0.0292(14) Uani 1 1 d . . . . .
C16 C 0.7018(5) 0.7894(3) 1.0247(3) 0.0224(13) Uani 1 1 d . . . . .
C17 C 0.6097(6) 0.6068(3) 0.5907(3) 0.0332(16) Uani 1 1 d . . . . .
C18 C 0.5501(5) 0.5518(3) 0.5439(3) 0.0321(15) Uani 1 1 d . . . . .
C19 C 0.5221(5) 0.5713(3) 0.4818(3) 0.0322(15) Uani 1 1 d . . . . .
C20 C 0.4740(6) 0.5202(3) 0.4378(3) 0.0357(16) Uani 1 1 d . . . . .
C21 C 0.5999(5) 0.8571(3) 0.5427(3) 0.0241(13) Uani 1 1 d . . . . .
C22 C 0.5461(5) 0.9311(3) 0.5206(3) 0.0209(13) Uani 1 1 d . . . . .
C23 C 0.5071(5) 0.9432(3) 0.4582(3) 0.0273(14) Uani 1 1 d . . . . .
C24 C 0.4617(5) 1.0116(3) 0.4371(3) 0.0240(13) Uani 1 1 d . . . . .
C25 C 0.5871(13) 0.4387(7) 0.8491(9) 0.080(5) Uani 0.72(2) 1 d D U P A 1
H25A H 0.628914 0.431849 0.814095 0.120 Uiso 0.72(2) 1 calc GR . P A 1
H25B H 0.618641 0.480244 0.873161 0.120 Uiso 0.72(2) 1 calc GR . P A 1
H25C H 0.506348 0.447393 0.834451 0.120 Uiso 0.72(2) 1 calc GR . P A 1
C25A C 0.578(3) 0.4429(13) 0.8874(17) 0.055(9) Uani 0.28(2) 1 d D U P A 2
H25D H 0.528997 0.468368 0.855157 0.083 Uiso 0.28(2) 1 calc GR . P A 2
H25E H 0.649763 0.469895 0.897581 0.083 Uiso 0.28(2) 1 calc GR . P A 2
H25F H 0.539747 0.438798 0.923786 0.083 Uiso 0.28(2) 1 calc GR . P A 2
C26 C 0.6280(8) 0.1948(6) 1.0235(4) 0.090(4) Uani 1 1 d D . . . .
H26A H 0.590779 0.149540 1.009075 0.134 Uiso 1 1 calc GR . . . .
H26B H 0.587902 0.215884 1.055310 0.134 Uiso 1 1 calc GR . . . .
H26C H 0.707509 0.185101 1.040323 0.134 Uiso 1 1 calc GR . . . .
C27 C 0.5061(12) 0.2563(7) 0.7103(5) 0.072(4) Uani 0.7 1 d D U P A 2
H27A H 0.528325 0.285151 0.676609 0.107 Uiso 0.7 1 calc GR . P A 2
H27B H 0.427033 0.239990 0.699810 0.107 Uiso 0.7 1 calc GR . P A 2
H27C H 0.556419 0.214170 0.717212 0.107 Uiso 0.7 1 calc GR . P A 2


_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 2.287(4) . ?
Gd1 O4 2.310(4) 2_556 ?
Gd1 O5 2.267(4) . ?
Gd1 O7 2.311(4) 4_575 ?
Gd1 O9 2.247(4) . ?
Gd1 O11 2.243(4) . ?
Gd2 O2 2.358(4) 2_546 ?
Gd2 O3 2.326(4) . ?
Gd2 O8 2.315(4) 3_667 ?
Gd2 O13 2.455(7) . ?
Gd2 O13A 2.449(15) . ?
Gd2 O14 2.445(5) . ?
Gd2 O15 2.334(5) . ?
Gd2 O16 2.447(5) . ?
Gd2 O17 2.487(7) . ?
Gd2 O18 2.356(11) . ?
Br1 C3 1.901(6) . ?
Br2 C4 1.893(6) . ?
Br3 C6 1.895(6) . ?
Br4 C7 1.897(6) . ?
Br5 C11 1.892(6) . ?
Br6 C12 1.897(5) . ?
Br7 C14 1.899(6) . ?
Br8 C15 1.880(6) . ?
Br9 C19 1.902(6) . ?
Br10 C20 1.893(7) . ?
Br11 C23 1.898(6) . ?
Br12 C24 1.888(6) . ?
O1 C1 1.240(7) . ?
O2 C1 1.241(7) . ?
O3 C8 1.248(7) . ?
O4 C8 1.224(7) . ?
O5 C9 1.240(7) . ?
O6 C9 1.238(8) . ?
O7 C16 1.235(7) . ?
O8 C16 1.239(7) . ?
O9 C17 1.252(7) . ?
O10 C17 1.227(7) . ?
O11 C21 1.248(7) . ?
O12 C21 1.224(7) . ?
O13 C25 1.563(13) . ?
O13A C25A 1.554(19) . ?
O14 C26 1.473(9) . ?
O17 C27 1.453(10) . ?
C1 C2 1.529(7) . ?
C2 C3 1.387(8) . ?
C2 C7 1.407(8) . ?
C3 C4 1.394(8) . ?
C4 C5 1.397(8) . ?
C5 C6 1.396(8) . ?
C5 C8 1.520(7) . ?
C6 C7 1.392(8) . ?
C9 C10 1.532(8) . ?
C10 C11 1.390(8) . ?
C10 C15 1.416(8) . ?
C11 C12 1.396(8) . ?
C12 C13 1.392(8) . ?
C13 C14 1.392(8) . ?
C13 C16 1.536(8) . ?
C14 C15 1.390(8) . ?
C17 C18 1.519(8) . ?
C18 C19 1.385(9) . ?
C18 C20 1.402(9) 3_666 ?
C19 C20 1.392(9) . ?
C21 C22 1.530(8) . ?
C22 C23 1.383(8) . ?
C22 C24 1.395(8) 3_676 ?
C23 C24 1.399(8) . ?

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 O4 91.91(16) . 2_556 ?
O1 Gd1 O7 86.52(16) . 4_575 ?
O4 Gd1 O7 89.15(15) 2_556 4_575 ?
O5 Gd1 O1 86.49(16) . . ?
O5 Gd1 O4 88.19(16) . 2_556 ?
O5 Gd1 O7 172.43(16) . 4_575 ?
O9 Gd1 O1 90.42(17) . . ?
O9 Gd1 O4 176.83(15) . 2_556 ?
O9 Gd1 O5 94.11(16) . . ?
O9 Gd1 O7 88.85(15) . 4_575 ?
O11 Gd1 O1 177.73(15) . . ?
O11 Gd1 O4 87.53(15) . 2_556 ?
O11 Gd1 O5 95.69(16) . . ?
O11 Gd1 O7 91.27(16) . 4_575 ?
O11 Gd1 O9 90.06(16) . . ?
O2 Gd2 O13 146.9(3) 2_546 . ?
O2 Gd2 O13A 136.4(8) 2_546 . ?
O2 Gd2 O14 143.57(18) 2_546 . ?
O2 Gd2 O16 73.07(16) 2_546 . ?
O2 Gd2 O17 77.1(3) 2_546 . ?
O3 Gd2 O2 85.79(15) . 2_546 ?
O3 Gd2 O13 70.8(3) . . ?
O3 Gd2 O13A 72.5(7) . . ?
O3 Gd2 O14 117.0(2) . . ?
O3 Gd2 O15 136.73(17) . . ?
O3 Gd2 O16 151.38(15) . . ?
O3 Gd2 O17 74.6(4) . . ?
O3 Gd2 O18 80.4(11) . . ?
O8 Gd2 O2 83.44(15) 3_667 2_546 ?
O8 Gd2 O3 82.49(15) 3_667 . ?
O8 Gd2 O13 115.0(3) 3_667 . ?
O8 Gd2 O13A 128.4(6) 3_667 . ?
O8 Gd2 O14 72.82(17) 3_667 . ?
O8 Gd2 O15 137.34(17) 3_667 . ?
O8 Gd2 O16 76.24(18) 3_667 . ?
O8 Gd2 O17 150.8(4) 3_667 . ?
O8 Gd2 O18 149.5(12) 3_667 . ?
O13A Gd2 O17 61.1(8) . . ?
O14 Gd2 O13 69.4(3) . . ?
O14 Gd2 O13A 79.6(8) . . ?
O14 Gd2 O16 74.7(2) . . ?
O14 Gd2 O17 134.1(4) . . ?
O15 Gd2 O2 110.4(2) . 2_546 ?
O15 Gd2 O13 75.4(3) . . ?
O15 Gd2 O13A 68.4(7) . . ?
O15 Gd2 O14 73.3(2) . . ?
O15 Gd2 O16 70.37(18) . . ?
O15 Gd2 O17 70.8(4) . . ?
O15 Gd2 O18 69.1(13) . . ?
O16 Gd2 O13 135.9(3) . . ?
O16 Gd2 O13A 136.1(7) . . ?
O16 Gd2 O17 117.5(3) . . ?
O18 Gd2 O2 70.3(9) . 2_546 ?
O18 Gd2 O13 82.7(8) . . ?
O18 Gd2 O14 137.7(12) . . ?
O18 Gd2 O16 109.2(8) . . ?
C1 O1 Gd1 154.0(4) . . ?
C1 O2 Gd2 149.9(4) . 2_556 ?
C8 O3 Gd2 157.8(4) . . ?
C8 O4 Gd1 144.4(4) . 2_546 ?
C9 O5 Gd1 153.9(4) . . ?
C16 O7 Gd1 144.9(4) . 4_676 ?
C16 O8 Gd2 159.1(4) . 3_667 ?
C17 O9 Gd1 156.3(4) . . ?
C21 O11 Gd1 165.4(4) . . ?
C25 O13 Gd2 127.9(9) . . ?
C25A O13A Gd2 128.7(17) . . ?
C26 O14 Gd2 130.0(5) . . ?
C27 O17 Gd2 123.5(8) . . ?
O1 C1 O2 126.5(5) . . ?
O1 C1 C2 117.0(5) . . ?
O2 C1 C2 116.5(5) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 C7 117.9(5) . . ?
C7 C2 C1 120.2(5) . . ?
C2 C3 Br1 118.1(4) . . ?
C2 C3 C4 120.9(5) . . ?
C4 C3 Br1 120.9(4) . . ?
C3 C4 Br2 120.5(4) . . ?
C3 C4 C5 121.2(5) . . ?
C5 C4 Br2 118.3(4) . . ?
C4 C5 C8 122.5(5) . . ?
C6 C5 C4 118.2(5) . . ?
C6 C5 C8 119.3(5) . . ?
C5 C6 Br3 117.8(4) . . ?
C7 C6 Br3 121.7(4) . . ?
C7 C6 C5 120.4(5) . . ?
C2 C7 Br4 117.5(4) . . ?
C6 C7 Br4 121.2(4) . . ?
C6 C7 C2 121.3(5) . . ?
O3 C8 C5 116.1(5) . . ?
O4 C8 O3 126.4(5) . . ?
O4 C8 C5 117.5(5) . . ?
O5 C9 C10 117.4(6) . . ?
O6 C9 O5 127.1(6) . . ?
O6 C9 C10 115.5(5) . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 C15 120.2(5) . . ?
C15 C10 C9 119.1(5) . . ?
C10 C11 Br5 118.6(4) . . ?
C10 C11 C12 119.7(5) . . ?
C12 C11 Br5 121.7(4) . . ?
C11 C12 Br6 119.8(4) . . ?
C13 C12 Br6 119.8(4) . . ?
C13 C12 C11 120.5(5) . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 C16 120.6(5) . . ?
C14 C13 C16 119.7(5) . . ?
C13 C14 Br7 118.1(4) . . ?
C15 C14 Br7 121.0(5) . . ?
C15 C14 C13 120.9(5) . . ?
C10 C15 Br8 119.1(4) . . ?
C14 C15 Br8 122.0(5) . . ?
C14 C15 C10 118.9(5) . . ?
O7 C16 O8 126.6(5) . . ?
O7 C16 C13 116.4(5) . . ?
O8 C16 C13 117.0(5) . . ?
O9 C17 C18 117.6(5) . . ?
O10 C17 O9 125.1(6) . . ?
O10 C17 C18 117.3(6) . . ?
C19 C18 C17 120.3(6) . . ?
C19 C18 C20 118.8(6) . 3_666 ?
C20 C18 C17 120.8(6) 3_666 . ?
C18 C19 Br9 118.4(5) . . ?
C18 C19 C20 120.9(6) . . ?
C20 C19 Br9 120.6(5) . . ?
C18 C20 Br10 118.1(5) 3_666 . ?
C19 C20 Br10 121.6(5) . . ?
C19 C20 C18 120.2(6) . 3_666 ?
O11 C21 C22 117.5(5) . . ?
O12 C21 O11 126.3(6) . . ?
O12 C21 C22 116.2(5) . . ?
C23 C22 C21 120.7(5) . . ?
C23 C22 C24 118.7(5) . 3_676 ?
C24 C22 C21 120.6(5) 3_676 . ?
C22 C23 Br11 118.3(4) . . ?
C22 C23 C24 121.2(5) . . ?
C24 C23 Br11 120.4(4) . . ?
C22 C24 Br12 118.4(4) 3_676 . ?
C22 C24 C23 120.0(5) 3_676 . ?
C23 C24 Br12 121.6(5) . . ?

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
_geom_hbond_publ_flag
O13 H13 O12 0.854(10) 2.09(8) 2.653(11) 123(9) 2_646 yes
O13A H13A O6 0.852(10) 2.32(3) 3.09(3) 151(3) 2_646 yes
O14 H14 O12 0.854(10) 1.92(2) 2.732(7) 158(6) 2_646 yes
O15 H15A O10 0.85(2) 1.84(3) 2.647(7) 158(6) 2_646 yes
O15 H15B O6 0.85(2) 1.82(3) 2.643(7) 163(6) 2_646 yes
O16 H16B O10 0.86(2) 1.95(3) 2.740(7) 151(4) 2_646 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_18dy
_database_code_depnum_ccdc_archive 'CCDC 1940057'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H4 Br4 Dy N O8'
_chemical_formula_sum            'C9 H4 Br4 Dy N O8'
_chemical_formula_weight         736.23
_chemical_melting_point          ?
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'
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1555(7)
_cell_length_b                   9.1608(7)
_cell_length_c                   10.0141(8)
_cell_angle_alpha                104.319(2)
_cell_angle_beta                 93.375(3)
_cell_angle_gamma                99.769(3)
_cell_volume                     797.52(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.305
_cell_measurement_theta_min      2.933
_shelx_estimated_absorpt_T_max   0.320
_shelx_estimated_absorpt_T_min   0.140
_exptl_absorpt_coefficient_mu    14.742
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1352 before and 0.0750 after correction. The Ratio of minimum to maximum transmission is 0.5640. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19405
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2873
_reflns_number_total             3144
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.633
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.201
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+11.0950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O8-H8
 0.85 with sigma of 0.01
 C9-H8
 1.898416 with sigma of 0.02
 Dy1-H8
 2.916163 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O1, C1, O2, C2, C3, Br1, C4, Br2, C5, C7, Br3, C8, Br4, C6, O3, O4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.47379(4) 0.20947(4) 0.97843(3) 0.01500(13) Uani 1 1 d D . . . .
Br1 Br 0.20210(10) 0.32550(13) 0.63105(10) 0.0438(3) Uani 1 1 d . U . . .
Br2 Br 0.20767(10) 0.07634(12) 0.32820(9) 0.0419(3) Uani 1 1 d . U . . .
Br3 Br 0.83400(10) 0.21959(12) 0.38866(10) 0.0408(3) Uani 1 1 d . U . . .
Br4 Br 0.82862(11) 0.47515(13) 0.68815(10) 0.0462(3) Uani 1 1 d . U . . .
O1 O 0.5321(7) 0.3994(6) 0.8740(5) 0.0252(12) Uani 1 1 d . U . . .
O2 O 0.5037(7) 0.6077(6) 0.8110(5) 0.0260(12) Uani 1 1 d . U . . .
O3 O 0.5485(7) -0.0821(6) 0.2663(5) 0.0300(13) Uani 1 1 d . U . . .
O4 O 0.4971(6) 0.0632(5) 0.1354(5) 0.0178(10) Uani 1 1 d . U . . .
O5 O 0.2354(7) 0.0425(7) 0.9444(7) 0.0364(15) Uani 1 1 d . . . . .
O6 O 0.2300(7) 0.2786(7) 0.9642(8) 0.0454(18) Uani 1 1 d . . . . .
O7 O 0.0251(8) 0.1097(10) 0.9047(9) 0.061(2) Uani 1 1 d . . . . .
O8 O 0.7318(7) 0.2327(6) 1.0022(7) 0.0343(14) Uani 1 1 d D . . . .
H8 H 0.775(2) 0.157(2) 1.003(11) 0.051 Uiso 1 1 d DR . . . .
N1 N 0.1580(8) 0.1437(8) 0.9389(7) 0.0308(16) Uani 1 1 d . . . . .
C1 C 0.5159(9) 0.4704(8) 0.7856(7) 0.0191(13) Uani 1 1 d . U . . .
C2 C 0.5165(9) 0.3783(8) 0.6359(7) 0.0194(12) Uani 1 1 d . U . . .
C3 C 0.3834(9) 0.2978(8) 0.5582(7) 0.0192(13) Uani 1 1 d . U . . .
C4 C 0.3873(9) 0.1943(8) 0.4330(7) 0.0189(13) Uani 1 1 d . U . . .
C5 C 0.5201(8) 0.1685(8) 0.3838(7) 0.0160(12) Uani 1 1 d . U . . .
C6 C 0.5217(8) 0.0416(8) 0.2548(7) 0.0168(12) Uani 1 1 d . U . . .
C7 C 0.6528(9) 0.2525(8) 0.4578(7) 0.0187(13) Uani 1 1 d . U . . .
C8 C 0.6509(9) 0.3588(8) 0.5846(7) 0.0195(13) Uani 1 1 d . U . . .
C9 C 0.8423(11) 0.3692(10) 1.0397(12) 0.046(3) Uani 1 1 d D . . . .
H9A H 0.923895 0.355720 0.984898 0.070 Uiso 1 1 calc GR . . . .
H9B H 0.877544 0.390983 1.136109 0.070 Uiso 1 1 calc GR . . . .
H9C H 0.799925 0.453046 1.023590 0.070 Uiso 1 1 calc GR . . . .


_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 2.249(5) . ?
Dy1 O2 2.319(5) 2_667 ?
Dy1 O3 2.420(5) 2_656 ?
Dy1 O4 2.326(5) 1_556 ?
Dy1 O4 2.543(5) 2_656 ?
Dy1 O5 2.396(6) . ?
Dy1 O6 2.427(7) . ?
Dy1 O8 2.328(6) . ?
Br1 C3 1.883(8) . ?
Br2 C4 1.899(7) . ?
Br3 C7 1.878(8) . ?
Br4 C8 1.878(8) . ?
O1 C1 1.237(9) . ?
O2 C1 1.246(9) . ?
O3 C6 1.231(9) . ?
O4 C6 1.273(8) . ?
O5 N1 1.268(9) . ?
O6 N1 1.255(9) . ?
O7 N1 1.211(10) . ?
O8 H8 0.858(9) . ?
O8 C9 1.422(10) . ?
C1 C2 1.529(9) . ?
C2 C3 1.390(11) . ?
C2 C8 1.384(11) . ?
C3 C4 1.379(10) . ?
C4 C5 1.374(11) . ?
C5 C6 1.512(9) . ?
C5 C7 1.383(10) . ?
C7 C8 1.399(10) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 O2 89.13(18) . 2_667 ?
O1 Dy1 O3 75.01(18) . 2_656 ?
O1 Dy1 O4 121.28(17) . 2_656 ?
O1 Dy1 O4 158.3(2) . 1_556 ?
O1 Dy1 O5 124.6(2) . . ?
O1 Dy1 O6 82.1(2) . . ?
O1 Dy1 O8 81.7(2) . . ?
O2 Dy1 O3 163.69(18) 2_667 2_656 ?
O2 Dy1 O4 78.20(17) 2_667 1_556 ?
O2 Dy1 O4 143.92(17) 2_667 2_656 ?
O2 Dy1 O5 109.4(2) 2_667 . ?
O2 Dy1 O6 80.6(2) 2_667 . ?
O2 Dy1 O8 88.3(2) 2_667 . ?
O3 Dy1 O4 51.85(17) 2_656 2_656 ?
O3 Dy1 O6 93.3(2) 2_656 . ?
O4 Dy1 O3 118.06(17) 1_556 2_656 ?
O4 Dy1 O4 66.63(19) 1_556 2_656 ?
O4 Dy1 O5 76.6(2) 1_556 . ?
O4 Dy1 O6 112.5(2) 1_556 . ?
O4 Dy1 O8 80.5(2) 1_556 . ?
O5 Dy1 O3 77.7(2) . 2_656 ?
O5 Dy1 O4 70.95(19) . 2_656 ?
O5 Dy1 O6 52.5(2) . . ?
O6 Dy1 O4 119.59(19) . 2_656 ?
O8 Dy1 O3 93.0(2) . 2_656 ?
O8 Dy1 O4 78.49(19) . 2_656 ?
O8 Dy1 O5 147.1(2) . . ?
O8 Dy1 O6 160.4(2) . . ?
C1 O1 Dy1 155.4(5) . . ?
C1 O2 Dy1 130.0(5) . 2_667 ?
C6 O3 Dy1 97.4(4) . 2_656 ?
Dy1 O4 Dy1 113.37(19) 1_554 2_656 ?
C6 O4 Dy1 155.2(4) . 1_554 ?
C6 O4 Dy1 90.4(4) . 2_656 ?
N1 O5 Dy1 96.5(5) . . ?
N1 O6 Dy1 95.3(5) . . ?
Dy1 O8 H8 123.2(17) . . ?
C9 O8 Dy1 128.2(5) . . ?
C9 O8 H8 107.8(17) . . ?
O6 N1 O5 115.4(7) . . ?
O7 N1 O5 121.5(8) . . ?
O7 N1 O6 123.0(8) . . ?
O1 C1 O2 125.0(7) . . ?
O1 C1 C2 115.0(6) . . ?
O2 C1 C2 119.9(6) . . ?
C3 C2 C1 120.1(7) . . ?
C8 C2 C1 119.4(7) . . ?
C8 C2 C3 119.9(6) . . ?
C2 C3 Br1 119.0(5) . . ?
C4 C3 Br1 121.5(6) . . ?
C4 C3 C2 119.4(7) . . ?
C3 C4 Br2 120.4(6) . . ?
C5 C4 Br2 118.3(5) . . ?
C5 C4 C3 121.3(7) . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 C7 119.6(6) . . ?
C7 C5 C6 120.0(7) . . ?
O3 C6 Dy1 57.3(4) . 2_656 ?
O3 C6 O4 120.4(6) . . ?
O3 C6 C5 119.4(6) . . ?
O4 C6 Dy1 63.1(3) . 2_656 ?
O4 C6 C5 120.2(6) . . ?
C5 C6 Dy1 176.7(5) . 2_656 ?
C5 C7 Br3 119.5(5) . . ?
C5 C7 C8 119.8(7) . . ?
C8 C7 Br3 120.7(6) . . ?
C2 C8 Br4 119.0(5) . . ?
C2 C8 C7 119.9(7) . . ?
C7 C8 Br4 121.1(6) . . ?
O8 C9 H9A 109.5 . . ?
O8 C9 H9B 109.5 . . ?
O8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O5 0.858(9) 2.01(4) 2.763(8) 146(6) 2_657 yes
O8 H8 O7 0.858(9) 2.60(5) 3.197(10) 128(6) 1_655 yes
C9 H9A O7 0.96 2.55 3.210(13) 126.4 1_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_12sm
_database_code_depnum_ccdc_archive 'CCDC 1940091'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br8 N2 O18 Sm2'
_chemical_formula_sum            'C20 H16 Br8 N2 O18 Sm2'
_chemical_formula_weight         1512.27
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3577(5)
_cell_length_b                   12.6090(5)
_cell_length_c                   16.2094(8)
_cell_angle_alpha                77.356(2)
_cell_angle_beta                 72.911(2)
_cell_angle_gamma                68.745(2)
_cell_volume                     1870.78(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.256
_cell_measurement_theta_min      2.925
_shelx_estimated_absorpt_T_max   0.454
_shelx_estimated_absorpt_T_min   0.203
_exptl_absorpt_coefficient_mu    11.724
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1759 before and 0.0694 after correction. The Ratio of minimum to maximum transmission is 0.5009. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27416
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5574
_reflns_number_total             7334
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.905
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7334
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+5.4739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10
 0.85 with sigma of 0.01
 O11-H11
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O18-H18
 0.85 with sigma of 0.01
 C13-H10
 1.91069 with sigma of 0.02
 Sm1-H10
 3.026644 with sigma of 0.02
 C14-H11
 1.891164 with sigma of 0.02
 Sm1-H11
 3.009963 with sigma of 0.02
 C19-H17
 1.888197 with sigma of 0.02
 Sm2-H17
 2.985151 with sigma of 0.02
 C20-H18
 1.895701 with sigma of 0.02
 Sm2-H18
 3.02219 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Br7, Br8, O12, O13, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.00586(3) 0.69415(3) 0.28681(2) 0.01795(9) Uani 1 1 d D . . . .
Sm2 Sm 0.48819(3) 0.80980(3) 0.21073(2) 0.01818(9) Uani 1 1 d D . . . .
Br1 Br 0.61967(8) 0.72256(5) 0.55796(5) 0.03181(18) Uani 1 1 d . . . . .
Br2 Br 0.45479(9) 0.90245(6) 0.70727(4) 0.03397(19) Uani 1 1 d . . . . .
Br3 Br 0.80175(9) 0.39103(6) 0.17015(5) 0.0396(2) Uani 1 1 d . . . . .
Br4 Br 0.99230(9) 0.24210(6) 0.00652(5) 0.0374(2) Uani 1 1 d . . . . .
Br5 Br 1.26638(8) 0.76051(6) 0.50878(5) 0.0373(2) Uani 1 1 d . . . . .
Br6 Br 1.10798(9) 0.89842(7) 0.68057(5) 0.0465(2) Uani 1 1 d . . . . .
Br7 Br 0.42387(8) 0.40099(6) 0.20646(4) 0.03364(19) Uani 1 1 d . U . . .
Br8 Br 0.61118(8) 0.22242(5) 0.05830(5) 0.03140(18) Uani 1 1 d . U . . .
O1 O 0.7747(5) 0.7899(4) 0.3607(3) 0.0301(11) Uani 1 1 d . . . . .
O2 O 0.5695(5) 0.8298(4) 0.3244(3) 0.0297(11) Uani 1 1 d . . . . .
O3 O 0.9101(5) 0.6405(4) 0.1945(3) 0.0332(12) Uani 1 1 d . . . . .
O4 O 0.7069(5) 0.6709(4) 0.1587(3) 0.0317(12) Uani 1 1 d . . . . .
O5 O 1.0782(5) 0.8273(4) 0.3250(3) 0.0350(12) Uani 1 1 d . . . . .
O6 O 1.2672(5) 0.8788(4) 0.3105(3) 0.0347(12) Uani 1 1 d . . . . .
O7 O 1.0178(5) 0.6313(4) 0.4500(3) 0.0319(12) Uani 1 1 d . . . . .
O8 O 1.2168(5) 0.5812(4) 0.3532(3) 0.0337(12) Uani 1 1 d . . . . .
O9 O 1.2118(6) 0.5246(4) 0.4902(4) 0.0403(13) Uani 1 1 d . . . . .
O10 O 0.9308(5) 0.8690(4) 0.1873(3) 0.0329(12) Uani 1 1 d D . . . .
H10 H 0.847(3) 0.897(4) 0.179(4) 0.049 Uiso 1 1 d DR . . . .
O11 O 0.9787(7) 0.5034(5) 0.3468(4) 0.0502(16) Uani 1 1 d D . . . .
H11 H 0.937(9) 0.491(3) 0.4002(18) 0.075 Uiso 1 1 d DR . . . .
O12 O 0.3887(5) 0.7214(4) 0.1465(3) 0.0302(9) Uani 1 1 d . U . . .
O13 O 0.2080(5) 0.6548(4) 0.1682(3) 0.0266(9) Uani 1 1 d . U . . .
O14 O 0.6646(5) 0.9173(4) 0.1433(3) 0.0321(12) Uani 1 1 d . . . . .
O15 O 0.5892(5) 0.8756(4) 0.0472(3) 0.0329(12) Uani 1 1 d . . . . .
O16 O 0.7301(6) 0.9804(4) 0.0061(3) 0.0396(13) Uani 1 1 d . . . . .
O17 O 0.3481(7) 1.0027(5) 0.1516(4) 0.0554(17) Uani 1 1 d D . . . .
H17 H 0.340(9) 1.010(3) 0.099(2) 0.083 Uiso 1 1 d DR . . . .
O18 O 0.4769(5) 0.6349(4) 0.3112(3) 0.0350(12) Uani 1 1 d D . . . .
H18 H 0.405(4) 0.611(4) 0.322(4) 0.053 Uiso 1 1 d DR . . . .
N1 N 1.1501(6) 0.5776(5) 0.4328(4) 0.0288(14) Uani 1 1 d . . . . .
N2 N 0.6616(6) 0.9262(5) 0.0642(4) 0.0298(14) Uani 1 1 d . . . . .
C1 C 0.6437(7) 0.8412(5) 0.3679(4) 0.0175(14) Uani 1 1 d . . . . .
C2 C 0.5692(6) 0.9229(5) 0.4369(4) 0.0152(13) Uani 1 1 d . . . . .
C3 C 0.5507(7) 0.8827(5) 0.5254(4) 0.0213(14) Uani 1 1 d . . . . .
C4 C 0.4831(7) 0.9576(5) 0.5882(4) 0.0187(14) Uani 1 1 d . . . . .
C5 C 0.8394(7) 0.6302(5) 0.1480(4) 0.0200(15) Uani 1 1 d . . . . .
C6 C 0.9216(6) 0.5631(5) 0.0710(4) 0.0186(14) Uani 1 1 d . . . . .
C7 C 0.9165(7) 0.4541(5) 0.0725(4) 0.0186(14) Uani 1 1 d . . . . .
C8 C 0.9941(7) 0.3923(5) 0.0022(4) 0.0221(15) Uani 1 1 d . . . . .
C9 C 1.1439(7) 0.8765(5) 0.3478(4) 0.0173(14) Uani 1 1 d . . . . .
C10 C 1.0684(6) 0.9409(5) 0.4262(4) 0.0179(14) Uani 1 1 d . . . . .
C11 C 1.1145(7) 0.8992(5) 0.5028(4) 0.0219(14) Uani 1 1 d . . . . .
C12 C 1.0461(7) 0.9566(5) 0.5765(4) 0.0196(14) Uani 1 1 d . . . . .
C13 C 1.0113(9) 0.9415(7) 0.1322(5) 0.041(2) Uani 1 1 d D . . . .
H13A H 1.020749 0.936773 0.072322 0.061 Uiso 1 1 calc GR . . . .
H13B H 1.104178 0.916562 0.143892 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.962463 1.019474 0.143850 0.061 Uiso 1 1 calc GR . . . .
C14 C 1.0381(11) 0.3953(7) 0.3122(7) 0.063(3) Uani 1 1 d D . . . .
H14A H 1.082565 0.407065 0.251462 0.095 Uiso 1 1 calc GR . . . .
H14B H 0.963536 0.363600 0.319240 0.095 Uiso 1 1 calc GR . . . .
H14C H 1.107810 0.343276 0.342724 0.095 Uiso 1 1 calc GR . . . .
C15 C 0.3319(7) 0.6570(5) 0.1312(4) 0.0186(8) Uani 1 1 d . U . . .
C16 C 0.4181(7) 0.5764(5) 0.0632(4) 0.0201(7) Uani 1 1 d . U . . .
C17 C 0.4675(7) 0.4569(5) 0.0873(4) 0.0185(12) Uani 1 1 d . U . . .
C18 C 0.5461(6) 0.3827(5) 0.0248(4) 0.0167(11) Uani 1 1 d . U . . .
C19 C 0.2627(9) 1.1089(7) 0.1841(6) 0.049(2) Uani 1 1 d D . . . .
H19A H 0.304686 1.167393 0.153990 0.074 Uiso 1 1 calc GR . . . .
H19B H 0.257246 1.100988 0.245196 0.074 Uiso 1 1 calc GR . . . .
H19C H 0.168559 1.129900 0.175085 0.074 Uiso 1 1 calc GR . . . .
C20 C 0.5712(9) 0.5608(7) 0.3627(6) 0.048(2) Uani 1 1 d D . . . .
H20A H 0.658786 0.578599 0.345165 0.072 Uiso 1 1 calc GR . . . .
H20B H 0.590388 0.482768 0.354975 0.072 Uiso 1 1 calc GR . . . .
H20C H 0.528481 0.570886 0.422783 0.072 Uiso 1 1 calc GR . . . .


_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 2.340(4) . ?
Sm1 O3 2.342(5) . ?
Sm1 O5 2.324(5) . ?
Sm1 O7 2.617(5) . ?
Sm1 O8 2.534(5) . ?
Sm1 O10 2.450(5) . ?
Sm1 O11 2.473(5) . ?
Sm1 O13 2.372(4) 1_655 ?
Sm2 O2 2.331(5) . ?
Sm2 O4 2.357(4) . ?
Sm2 O6 2.368(5) 1_455 ?
Sm2 O12 2.315(5) . ?
Sm2 O14 2.518(5) . ?
Sm2 O15 2.617(5) . ?
Sm2 O17 2.486(5) . ?
Sm2 O18 2.456(5) . ?
Br1 C3 1.891(6) . ?
Br2 C4 1.876(6) . ?
Br3 C7 1.891(6) . ?
Br4 C8 1.887(6) . ?
Br5 C11 1.887(6) . ?
Br6 C12 1.883(6) . ?
Br7 C17 1.885(6) . ?
Br8 C18 1.892(6) . ?
O1 C1 1.256(8) . ?
O2 C1 1.246(8) . ?
O3 C5 1.248(8) . ?
O4 C5 1.251(8) . ?
O5 C9 1.241(8) . ?
O6 C9 1.250(8) . ?
O7 N1 1.265(7) . ?
O8 N1 1.271(7) . ?
O9 N1 1.221(7) . ?
O10 H10 0.856(9) . ?
O10 C13 1.444(8) . ?
O11 H11 0.855(9) . ?
O11 C14 1.441(10) . ?
O12 C15 1.260(7) . ?
O13 C15 1.255(7) . ?
O14 N2 1.270(7) . ?
O15 N2 1.262(7) . ?
O16 N2 1.238(7) . ?
O17 H17 0.857(9) . ?
O17 C19 1.424(9) . ?
O18 H18 0.859(9) . ?
O18 C20 1.413(9) . ?
C1 C2 1.526(8) . ?
C2 C3 1.394(9) . ?
C2 C4 1.414(8) 2_676 ?
C3 C4 1.393(9) . ?
C5 C6 1.521(8) . ?
C6 C7 1.390(8) . ?
C6 C8 1.393(9) 2_765 ?
C7 C8 1.396(9) . ?
C9 C10 1.515(8) . ?
C10 C11 1.388(9) . ?
C10 C12 1.404(9) 2_776 ?
C11 C12 1.402(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.517(8) . ?
C16 C17 1.409(8) . ?
C16 C18 1.395(8) 2_665 ?
C17 C18 1.393(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O3 89.47(17) . . ?
O1 Sm1 O7 77.43(16) . . ?
O1 Sm1 O8 126.74(16) . . ?
O1 Sm1 O10 76.38(17) . . ?
O1 Sm1 O11 92.54(19) . . ?
O1 Sm1 O13 157.19(17) . 1_655 ?
O3 Sm1 O7 133.91(16) . . ?
O3 Sm1 O8 129.92(17) . . ?
O3 Sm1 O10 75.69(17) . . ?
O3 Sm1 O11 71.17(19) . . ?
O3 Sm1 O13 80.78(16) . 1_655 ?
O5 Sm1 O1 87.09(17) . . ?
O5 Sm1 O3 150.65(18) . . ?
O5 Sm1 O7 73.48(17) . . ?
O5 Sm1 O8 73.30(17) . . ?
O5 Sm1 O10 75.17(17) . . ?
O5 Sm1 O11 138.09(19) . . ?
O5 Sm1 O13 91.38(17) . 1_655 ?
O8 Sm1 O7 49.76(15) . . ?
O10 Sm1 O7 139.74(17) . . ?
O10 Sm1 O8 139.03(16) . . ?
O10 Sm1 O11 145.11(19) . . ?
O11 Sm1 O7 65.62(17) . . ?
O11 Sm1 O8 73.65(19) . . ?
O13 Sm1 O7 123.85(16) 1_655 . ?
O13 Sm1 O8 74.10(16) 1_655 . ?
O13 Sm1 O10 81.22(16) 1_655 . ?
O13 Sm1 O11 103.57(18) 1_655 . ?
O2 Sm2 O4 91.57(17) . . ?
O2 Sm2 O6 80.31(17) . 1_455 ?
O2 Sm2 O14 73.67(16) . . ?
O2 Sm2 O15 123.25(16) . . ?
O2 Sm2 O17 108.72(19) . . ?
O2 Sm2 O18 77.88(17) . . ?
O4 Sm2 O6 154.56(17) . 1_455 ?
O4 Sm2 O14 74.09(16) . . ?
O4 Sm2 O15 71.00(16) . . ?
O4 Sm2 O17 135.51(18) . . ?
O4 Sm2 O18 76.17(17) . . ?
O6 Sm2 O14 125.27(17) 1_455 . ?
O6 Sm2 O15 133.30(17) 1_455 . ?
O6 Sm2 O17 69.67(19) 1_455 . ?
O6 Sm2 O18 78.56(17) 1_455 . ?
O12 Sm2 O2 153.34(17) . . ?
O12 Sm2 O4 85.78(16) . . ?
O12 Sm2 O6 90.81(17) . 1_455 ?
O12 Sm2 O14 130.28(16) . . ?
O12 Sm2 O15 80.85(16) . . ?
O12 Sm2 O17 91.3(2) . . ?
O12 Sm2 O18 75.73(17) . . ?
O14 Sm2 O15 49.79(15) . . ?
O17 Sm2 O14 74.5(2) . . ?
O17 Sm2 O15 64.72(17) . . ?
O18 Sm2 O14 137.75(16) . . ?
O18 Sm2 O15 140.71(17) . . ?
O18 Sm2 O17 145.49(19) . . ?
C1 O1 Sm1 154.6(4) . . ?
C1 O2 Sm2 163.5(4) . . ?
C5 O3 Sm1 168.6(5) . . ?
C5 O4 Sm2 150.5(4) . . ?
C9 O5 Sm1 165.2(5) . . ?
C9 O6 Sm2 151.0(4) . 1_655 ?
N1 O7 Sm1 94.4(4) . . ?
N1 O8 Sm1 98.2(4) . . ?
Sm1 O10 H10 123.0(15) . . ?
C13 O10 Sm1 129.9(4) . . ?
C13 O10 H10 107.1(15) . . ?
Sm1 O11 H11 119.7(15) . . ?
C14 O11 Sm1 132.1(5) . . ?
C14 O11 H11 107.6(15) . . ?
C15 O12 Sm2 164.6(4) . . ?
C15 O13 Sm1 149.9(4) . 1_455 ?
N2 O14 Sm2 98.5(4) . . ?
N2 O15 Sm2 94.0(4) . . ?
Sm2 O17 H17 116.1(15) . . ?
C19 O17 Sm2 136.6(5) . . ?
C19 O17 H17 107.1(15) . . ?
Sm2 O18 H18 121.1(15) . . ?
C20 O18 Sm2 130.7(5) . . ?
C20 O18 H18 108.0(15) . . ?
O7 N1 O8 117.5(6) . . ?
O9 N1 O7 121.4(6) . . ?
O9 N1 O8 121.1(6) . . ?
O15 N2 O14 117.4(5) . . ?
O16 N2 O14 121.0(6) . . ?
O16 N2 O15 121.6(6) . . ?
O1 C1 C2 116.9(6) . . ?
O2 C1 O1 125.6(6) . . ?
O2 C1 C2 117.5(5) . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 C4 118.3(5) . 2_676 ?
C4 C2 C1 120.2(5) 2_676 . ?
C2 C3 Br1 117.8(5) . . ?
C4 C3 Br1 120.8(5) . . ?
C4 C3 C2 121.4(6) . . ?
C2 C4 Br2 118.6(5) 2_676 . ?
C3 C4 Br2 121.1(5) . . ?
C3 C4 C2 120.3(6) . 2_676 ?
O3 C5 O4 125.8(6) . . ?
O3 C5 C6 117.1(6) . . ?
O4 C5 C6 117.1(6) . . ?
C7 C6 C5 120.6(6) . . ?
C7 C6 C8 118.0(6) . 2_765 ?
C8 C6 C5 121.4(5) 2_765 . ?
C6 C7 Br3 119.4(5) . . ?
C6 C7 C8 120.2(6) . . ?
C8 C7 Br3 120.4(5) . . ?
C6 C8 Br4 118.2(5) 2_765 . ?
C6 C8 C7 121.8(6) 2_765 . ?
C7 C8 Br4 120.0(5) . . ?
O5 C9 O6 125.3(6) . . ?
O5 C9 C10 117.7(6) . . ?
O6 C9 C10 117.0(6) . . ?
C11 C10 C9 119.4(6) . . ?
C11 C10 C12 118.7(6) . 2_776 ?
C12 C10 C9 121.9(6) 2_776 . ?
C10 C11 Br5 119.5(5) . . ?
C10 C11 C12 120.7(6) . . ?
C12 C11 Br5 119.7(5) . . ?
C10 C12 Br6 119.0(5) 2_776 . ?
C11 C12 Br6 120.4(5) . . ?
C11 C12 C10 120.6(6) . 2_776 ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O12 C15 C16 118.3(6) . . ?
O13 C15 O12 124.6(6) . . ?
O13 C15 C16 117.1(6) . . ?
C17 C16 C15 120.8(5) . . ?
C18 C16 C15 121.6(5) 2_665 . ?
C18 C16 C17 117.6(6) 2_665 . ?
C16 C17 Br7 117.9(5) . . ?
C18 C17 Br7 121.3(5) . . ?
C18 C17 C16 120.9(6) . . ?
C16 C18 Br8 118.1(4) 2_665 . ?
C17 C18 Br8 120.3(5) . . ?
C17 C18 C16 121.5(6) . 2_665 ?
O17 C19 H19A 109.5 . . ?
O17 C19 H19B 109.5 . . ?
O17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O18 C20 H20A 109.5 . . ?
O18 C20 H20B 109.5 . . ?
O18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_hbond_publ_flag
O10 H10 O14 0.856(9) 2.04(3) 2.870(7) 163(8) . yes
O11 H11 O9 0.855(9) 2.01(3) 2.833(8) 163(9) 2_766 yes
O17 H17 O15 0.857(9) 2.55(6) 3.237(7) 138(8) 2_675 yes
O17 H17 O16 0.857(9) 2.01(3) 2.844(8) 164(10) 2_675 yes
O18 H18 O8 0.859(9) 2.016(16) 2.867(7) 171(7) 1_455 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2pr
_database_code_depnum_ccdc_archive 'CCDC 1940036'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 O9 Pr'
_chemical_formula_sum            'C15 H12 Br6 O9 Pr'
_chemical_formula_weight         956.56
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.4250(15)
_cell_length_b                   10.6255(7)
_cell_length_c                   22.0706(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.676(3)
_cell_angle_gamma                90
_cell_volume                     4773.9(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.608
_cell_measurement_theta_min      3.457
_shelx_estimated_absorpt_T_max   0.444
_shelx_estimated_absorpt_T_min   0.219
_exptl_absorpt_coefficient_mu    12.128
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1469 before and 0.0759 after correction. The Ratio of minimum to maximum transmission is 0.5016. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3544
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            54192
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4020
_reflns_number_total             4677
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.000208(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+13.8179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.52642(2) 0.52345(2) 0.39187(2) 0.01662(6) Uani 1 1 d . . . . .
Br1 Br 0.76038(2) 0.49691(3) 0.31494(2) 0.03481(11) Uani 1 1 d . . . . .
Br2 Br 0.90407(2) 0.63854(4) 0.33703(2) 0.03425(11) Uani 1 1 d . . . . .
Br3 Br 0.77490(2) 1.10724(4) 0.35668(2) 0.03556(11) Uani 1 1 d . . . . .
Br4 Br 0.63138(2) 0.96164(4) 0.33222(2) 0.03909(11) Uani 1 1 d . . . . .
Br5 Br 0.64165(2) 0.14154(4) 0.49658(2) 0.03778(12) Uani 1 1 d . . . . .
Br6 Br 0.63386(2) -0.17003(3) 0.50427(2) 0.03179(10) Uani 1 1 d . . . . .
O1 O 0.61359(13) 0.6512(3) 0.36366(13) 0.0338(7) Uani 1 1 d . . . . .
O2 O 0.62036(15) 0.6525(3) 0.26375(13) 0.0509(9) Uani 1 1 d . . . . .
O3 O 0.90823(12) 0.9739(2) 0.40981(11) 0.0278(6) Uani 1 1 d . . . . .
O4 O 0.93392(12) 0.9300(2) 0.31731(11) 0.0251(6) Uani 1 1 d . . . . .
O5 O 0.51844(13) 0.3079(2) 0.43181(12) 0.0285(6) Uani 1 1 d . . . . .
O6 O 0.49973(13) 0.3427(2) 0.52807(12) 0.0295(6) Uani 1 1 d . . . . .
O7 O 0.58056(15) 0.4014(3) 0.31479(14) 0.0360(7) Uani 1 1 d D . . . .
H7 H 0.583(2) 0.426(4) 0.2801(9) 0.050(15) Uiso 1 1 d D . . . .
O8 O 0.62001(12) 0.4956(3) 0.47223(12) 0.0309(6) Uani 1 1 d D . . . .
H8 H 0.612(2) 0.504(4) 0.5079(8) 0.047(15) Uiso 1 1 d D . . . .
O9 O 0.46694(15) 0.6867(3) 0.33005(14) 0.0368(7) Uani 1 1 d D . . . .
H9 H 0.443(2) 0.662(5) 0.3010(15) 0.068(18) Uiso 1 1 d D . . . .
C1 C 0.64101(18) 0.6765(3) 0.31595(18) 0.0255(8) Uani 1 1 d . . . . .
C2 C 0.70736(17) 0.7411(3) 0.32585(15) 0.0192(7) Uani 1 1 d . . . . .
C3 C 0.76529(17) 0.6734(3) 0.32627(16) 0.0216(8) Uani 1 1 d . . . . .
C4 C 0.82596(17) 0.7332(3) 0.33554(16) 0.0210(8) Uani 1 1 d . . . . .
C5 C 0.82899(17) 0.8625(3) 0.34538(16) 0.0212(8) Uani 1 1 d . . . . .
C6 C 0.89477(17) 0.9273(3) 0.35799(16) 0.0210(8) Uani 1 1 d . . . . .
C7 C 0.77111(17) 0.9304(3) 0.34536(16) 0.0221(8) Uani 1 1 d . . . . .
C8 C 0.71066(17) 0.8708(3) 0.33519(16) 0.0218(8) Uani 1 1 d . . . . .
C9 C 0.50733(16) 0.2730(3) 0.48350(17) 0.0188(7) Uani 1 1 d . . . . .
C10 C 0.50345(16) 0.1311(3) 0.49324(15) 0.0172(7) Uani 1 1 d . . . . .
C11 C 0.55993(16) 0.0585(3) 0.49668(15) 0.0184(7) Uani 1 1 d . . . . .
C12 C 0.55707(17) -0.0721(3) 0.50263(16) 0.0192(7) Uani 1 1 d . . . . .
C13 C 0.5993(4) 0.2762(5) 0.3165(3) 0.083(2) Uani 1 1 d . . . . .
H13A H 0.639296 0.266595 0.296926 0.124 Uiso 1 1 calc GR . . . .
H13B H 0.565409 0.226026 0.295754 0.124 Uiso 1 1 calc GR . . . .
H13C H 0.606237 0.249086 0.358028 0.124 Uiso 1 1 calc GR . . . .
C14 C 0.6891(2) 0.4959(5) 0.4713(2) 0.0553(14) Uani 1 1 d . . . . .
H14A H 0.702330 0.426839 0.446993 0.083 Uiso 1 1 calc GR . . . .
H14B H 0.709038 0.487329 0.511988 0.083 Uiso 1 1 calc GR . . . .
H14C H 0.702943 0.573623 0.454190 0.083 Uiso 1 1 calc GR . . . .
C15 C 0.4588(3) 0.8176(4) 0.3404(3) 0.0623(16) Uani 1 1 d . . . . .
H15A H 0.459988 0.862266 0.302706 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.493686 0.846989 0.368692 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.417371 0.831862 0.356813 0.093 Uiso 1 1 calc GR . . . .


_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 2.362(2) . ?
Pr1 O3 2.533(2) 3_445 ?
Pr1 O4 2.599(2) 3_445 ?
Pr1 O5 2.464(2) . ?
Pr1 O6 2.363(3) 5_666 ?
Pr1 O7 2.471(3) . ?
Pr1 O8 2.517(3) . ?
Pr1 O9 2.465(3) . ?
Pr1 C6 2.917(3) 3_445 ?
Br1 C3 1.893(3) . ?
Br2 C4 1.884(3) . ?
Br3 C7 1.896(3) . ?
Br4 C8 1.882(3) . ?
Br5 C11 1.888(3) . ?
Br6 C12 1.880(3) . ?
O1 C1 1.261(5) . ?
O2 C1 1.221(5) . ?
O3 C6 1.256(4) . ?
O4 C6 1.250(4) . ?
O5 C9 1.238(4) . ?
O6 C9 1.251(4) . ?
O7 H7 0.816(10) . ?
O7 C13 1.384(6) . ?
O8 H8 0.820(10) . ?
O8 C14 1.413(5) . ?
O9 H9 0.819(10) . ?
O9 C15 1.421(5) . ?
C1 C2 1.519(5) . ?
C2 C3 1.384(5) . ?
C2 C8 1.394(5) . ?
C3 C4 1.393(5) . ?
C4 C5 1.391(5) . ?
C5 C6 1.515(5) . ?
C5 C7 1.385(5) . ?
C7 C8 1.390(5) . ?
C9 C10 1.525(4) . ?
C10 C11 1.385(5) . ?
C10 C12 1.396(5) 5_656 ?
C11 C12 1.396(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O3 155.35(9) . 3_445 ?
O1 Pr1 O4 125.25(9) . 3_445 ?
O1 Pr1 O5 134.55(9) . . ?
O1 Pr1 O6 94.15(9) . 5_666 ?
O1 Pr1 O7 74.39(10) . . ?
O1 Pr1 O8 73.00(9) . . ?
O1 Pr1 O9 78.34(10) . . ?
O1 Pr1 C6 146.37(10) . 3_445 ?
O3 Pr1 O4 50.72(8) 3_445 3_445 ?
O3 Pr1 C6 25.43(9) 3_445 3_445 ?
O4 Pr1 C6 25.37(8) 3_445 3_445 ?
O5 Pr1 O3 70.08(8) . 3_445 ?
O5 Pr1 O4 78.79(8) . 3_445 ?
O5 Pr1 O7 78.75(9) . . ?
O5 Pr1 O8 72.99(9) . . ?
O5 Pr1 O9 143.90(9) . . ?
O5 Pr1 C6 71.32(9) . 3_445 ?
O6 Pr1 O3 74.45(8) 5_666 3_445 ?
O6 Pr1 O4 120.42(8) 5_666 3_445 ?
O6 Pr1 O5 105.46(9) 5_666 . ?
O6 Pr1 O7 166.37(10) 5_666 . ?
O6 Pr1 O8 75.46(9) 5_666 . ?
O6 Pr1 O9 81.90(10) 5_666 . ?
O6 Pr1 C6 98.21(9) 5_666 3_445 ?
O7 Pr1 O3 118.96(9) . 3_445 ?
O7 Pr1 O4 72.94(9) . 3_445 ?
O7 Pr1 O8 93.83(10) . . ?
O7 Pr1 C6 95.43(10) . 3_445 ?
O8 Pr1 O3 122.97(8) . 3_445 ?
O8 Pr1 O4 150.74(8) . 3_445 ?
O8 Pr1 C6 140.45(9) . 3_445 ?
O9 Pr1 O3 78.45(9) . 3_445 ?
O9 Pr1 O4 67.55(9) . 3_445 ?
O9 Pr1 O7 102.48(10) . . ?
O9 Pr1 O8 141.68(9) . . ?
O9 Pr1 C6 72.66(9) . 3_445 ?
C1 O1 Pr1 137.6(2) . . ?
C6 O3 Pr1 94.6(2) . 3 ?
C6 O4 Pr1 91.6(2) . 3 ?
C9 O5 Pr1 129.1(2) . . ?
C9 O6 Pr1 173.9(2) . 5_666 ?
Pr1 O7 H7 123(3) . . ?
C13 O7 Pr1 128.6(3) . . ?
C13 O7 H7 107(3) . . ?
Pr1 O8 H8 118(3) . . ?
C14 O8 Pr1 133.7(3) . . ?
C14 O8 H8 107(3) . . ?
Pr1 O9 H9 117(4) . . ?
C15 O9 Pr1 131.2(3) . . ?
C15 O9 H9 111(4) . . ?
O1 C1 C2 115.3(3) . . ?
O2 C1 O1 126.9(4) . . ?
O2 C1 C2 117.7(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 C8 118.8(3) . . ?
C8 C2 C1 120.0(3) . . ?
C2 C3 Br1 118.5(3) . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 Br1 120.6(3) . . ?
C3 C4 Br2 120.0(3) . . ?
C5 C4 Br2 119.8(3) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 120.3(3) . . ?
C7 C5 C4 119.2(3) . . ?
C7 C5 C6 120.5(3) . . ?
O3 C6 Pr1 59.97(17) . 3 ?
O3 C6 C5 118.1(3) . . ?
O4 C6 Pr1 62.99(18) . 3 ?
O4 C6 O3 122.6(3) . . ?
O4 C6 C5 119.2(3) . . ?
C5 C6 Pr1 172.5(2) . 3 ?
C5 C7 Br3 119.4(3) . . ?
C5 C7 C8 120.6(3) . . ?
C8 C7 Br3 120.0(3) . . ?
C2 C8 Br4 118.1(3) . . ?
C7 C8 Br4 121.5(3) . . ?
C7 C8 C2 120.4(3) . . ?
O5 C9 O6 126.2(3) . . ?
O5 C9 C10 116.2(3) . . ?
O6 C9 C10 117.6(3) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 C12 119.0(3) . 5_656 ?
C12 C10 C9 120.6(3) 5_656 . ?
C10 C11 Br5 118.2(2) . . ?
C10 C11 C12 121.2(3) . . ?
C12 C11 Br5 120.6(2) . . ?
C10 C12 Br6 119.5(2) 5_656 . ?
C10 C12 C11 119.8(3) 5_656 . ?
C11 C12 Br6 120.7(3) . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O7 H7 O4 0.816(10) 2.15(2) 2.922(4) 158(5) 4_645 yes
O8 H8 O3 0.820(10) 1.911(11) 2.731(4) 178(5) 7_666 yes
O9 H9 O2 0.819(10) 1.848(18) 2.645(4) 164(5) 2_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3tb_r
_database_code_depnum_ccdc_archive 'CCDC 2130102'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H32 Br12 O24 Tb2, 2(C2 H6 O2), 2(H2 O)'
_chemical_formula_sum            'C36 H48 Br12 O30 Tb2'
_chemical_formula_weight         2237.50
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.62280(10)
_cell_length_b                   22.3036(4)
_cell_length_c                   16.5045(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.9410(10)
_cell_angle_gamma                90
_cell_volume                     3157.09(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.297
_cell_measurement_theta_min      2.644
_shelx_estimated_absorpt_T_max   0.338
_shelx_estimated_absorpt_T_min   0.200
_exptl_absorpt_coefficient_mu    9.896
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.7681.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2108
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            63712
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         2.644
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6927
_reflns_number_total             7834
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         1.433
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     201
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+5.9439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0524
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O12-H12B = O12-H12A = O15-H15E = O15-H15F
 0.84 with sigma of 0.01
 O7-C13A \\sim O7-C13B \\sim O8-C14A \\sim O8-C14A
 with sigma of 0.02
 C14A-C13B \\sim C14A-C13A
 with sigma of 0.02
 O7-C14A \\sim O8-C13A
 with sigma of 0.02
 O7-C14B \\sim O8-C13B
 with sigma of 0.02
 C18B-C17 \\sim C18A-C17
 with sigma of 0.02
 O14A-C18A \\sim O14B-C18B
 with sigma of 0.02
 O14A-C17 \\sim O14B-C17
 with sigma of 0.02
 O13-C18A \\sim O13-C18B
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 O10-C16 \\sim O10-C16A
 with sigma of 0.02
 O9-C15 \\sim O9-C15A
 with sigma of 0.02
 O9-C16 \\sim O9-C16A
 with sigma of 0.04
 O10-C15 \\sim O10-C15A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(O8)
\\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C13B) \\sim Ueq, Uanis(C14B) \\sim Ueq,
Uanis(O8) \\sim Ueq, Uanis(O14B) \\sim Ueq, Uanis(C18B) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(O14A) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C15A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O7, C13A, C14A, O8, O7, C13B, C14B, O8, O14B, C18B, C17, O13, O14A, C18A, C17,
  O13, O10, C16, C15, O9, O10, C16A, C15A, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H7B)=Sof(H8B)=Sof(C13B)=Sof(H13A)=Sof(H13B)=Sof(C14B)=Sof(H14C)=Sof(H14D)=
 1-FVAR(1)
 Sof(H7A)=Sof(H8A)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 FVAR(1)
 Sof(O14B)=Sof(H14E)=Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=1-FVAR(2)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(O14A)=Sof(H14F)=FVAR(2)
 Sof(H9B)=Sof(H10A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C15A)=Sof(H15C)=
 Sof(H15D)=1-FVAR(3)
 Sof(H9A)=Sof(H10)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 FVAR(3)
6.a Rotating group:
 O11(H11A,H11B), O12(H12A,H12B)
6.b Secondary CH2 refined with riding coordinates:
 C13B(H13A,H13B), C14A(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C17(H17C,H17D), C18A(H18A,H18B), C13A(H13C,H13D), C14B(H14C,H14D),
 C18B(H18C,H18D), C16A(H16C,H16D), C15A(H15C,H15D)
6.c Tetrahedral OH refined with riding coordinates:
 O7(H7B), O7(H7A), O8(H8A), O8(H8B), O9(H9A), O9(H9B), O10(H10), O10(H10A)
6.d Idealised tetrahedral OH refined as rotating group:
 O13(H13), O14B(H14E), O14A(H14F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.89425(2) 0.64164(2) 0.19836(2) 0.02000(4) Uani 1 1 d . . . . .
Br1 Br 0.54842(5) 0.70473(2) 0.38840(2) 0.04872(10) Uani 1 1 d . . . . .
Br2 Br 0.42112(5) 0.82916(2) 0.47618(2) 0.04306(9) Uani 1 1 d . . . . .
Br3 Br 0.34947(6) 0.94195(2) 0.16947(2) 0.05951(13) Uani 1 1 d . . . . .
Br4 Br 0.44885(6) 0.81459(2) 0.08240(2) 0.05438(11) Uani 1 1 d . . . . .
Br5 Br 0.64982(4) 0.55746(2) 0.48008(2) 0.03753(8) Uani 1 1 d . . . . .
Br6 Br 0.73148(4) 0.43675(2) 0.59694(3) 0.04997(10) Uani 1 1 d . . . . .
O1 O 0.6899(2) 0.70958(9) 0.20335(14) 0.0300(5) Uani 1 1 d . . . . .
O2 O 0.4471(2) 0.67473(10) 0.17865(16) 0.0371(5) Uani 1 1 d . . . . .
O3 O 0.1775(3) 0.93330(10) 0.34779(17) 0.0433(6) Uani 1 1 d . . . . .
O4 O 0.4157(3) 0.96995(10) 0.38102(15) 0.0383(5) Uani 1 1 d . . . . .
O5 O 0.8973(3) 0.59832(10) 0.32496(13) 0.0334(5) Uani 1 1 d . . . . .
O6 O 0.9478(4) 0.65514(10) 0.43559(15) 0.0479(7) Uani 1 1 d . . . . .
O7 O 0.9601(2) 0.53949(9) 0.16543(16) 0.0376(5) Uani 1 1 d D U . . .
H7B H 0.907619 0.508831 0.165401 0.056 Uiso 0.427(13) 1 calc R U P A 2
H7A H 0.901600 0.510474 0.159719 0.056 Uiso 0.573(13) 1 calc R U P A 1
O8 O 1.1664(3) 0.62225(10) 0.18794(18) 0.0455(6) Uani 1 1 d D U . . .
H8A H 1.238137 0.646561 0.192034 0.068 Uiso 0.573(13) 1 calc R U P A 1
H8B H 1.235243 0.647601 0.187715 0.068 Uiso 0.427(13) 1 calc R U P A 2
O9 O 0.8424(4) 0.63393(12) 0.05392(15) 0.0516(7) Uani 1 1 d D . . . .
H9A H 0.796935 0.607072 0.027107 0.077 Uiso 0.823(13) 1 calc R U P B 1
H9B H 0.798562 0.605170 0.030593 0.077 Uiso 0.177(13) 1 calc R U P B 2
O10 O 0.9896(3) 0.72440(11) 0.12256(16) 0.0467(6) Uani 1 1 d D . . . .
H10 H 0.961660 0.759216 0.127664 0.070 Uiso 0.823(13) 1 calc R U P B 1
H10A H 0.979850 0.757290 0.143639 0.070 Uiso 0.177(13) 1 calc R U P B 2
O11 O 1.0165(3) 0.71212(10) 0.29425(15) 0.0417(6) Uani 1 1 d . . . . .
H11A H 0.993972 0.704003 0.343490 0.063 Uiso 1 1 d R U . . .
H11B H 0.977213 0.747973 0.285220 0.063 Uiso 1 1 d R U . . .
O12 O 0.6585(2) 0.58498(9) 0.18012(15) 0.0345(5) Uani 1 1 d D . . . .
H12A H 0.660157 0.560037 0.139612 0.052 Uiso 1 1 d DR U . . .
H12B H 0.579737 0.608467 0.164821 0.052 Uiso 1 1 d DR U . . .
O13 O 1.0028(3) 0.83349(11) 0.28957(18) 0.0531(7) Uani 1 1 d D U . . .
H13 H 1.055905 0.861491 0.309012 0.080 Uiso 1 1 calc R U . . .
O14B O 0.893(4) 0.8352(11) 0.1088(8) 0.056(6) Uani 0.28(5) 1 d D U P C 2
H14E H 0.909642 0.848532 0.064282 0.085 Uiso 0.28(5) 1 calc R U P C 2
O15 O 0.6947(4) 0.53896(15) -0.01607(19) 0.0523(7) Uani 1 1 d D . . . .
C1 C 0.5447(3) 0.71298(12) 0.20453(18) 0.0251(6) Uani 1 1 d . . . . .
C2 C 0.4863(3) 0.76980(12) 0.24265(17) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.4809(3) 0.77280(12) 0.32659(18) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.4310(3) 0.82454(12) 0.36241(17) 0.0249(6) Uani 1 1 d . . . . .
C5 C 0.3880(3) 0.87486(12) 0.31545(17) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.3966(4) 0.87216(12) 0.23189(18) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.4430(4) 0.81967(13) 0.19562(17) 0.0267(6) Uani 1 1 d . . . . .
C8 C 0.3222(4) 0.93059(13) 0.35198(18) 0.0287(6) Uani 1 1 d . . . . .
C9 C 0.9335(3) 0.60658(13) 0.39967(19) 0.0286(6) Uani 1 1 d . . . . .
C10 C 0.9659(3) 0.55060(12) 0.45122(17) 0.0239(5) Uani 1 1 d . . . . .
C11 C 0.8514(3) 0.52430(13) 0.49251(17) 0.0252(6) Uani 1 1 d . . . . .
C12 C 0.8850(3) 0.47405(13) 0.54088(17) 0.0258(6) Uani 1 1 d . . . . .
C13B C 1.0902(10) 0.5294(4) 0.1210(8) 0.042(3) Uani 0.427(13) 1 d D U P A 2
H13A H 1.072916 0.546442 0.066776 0.050 Uiso 0.427(13) 1 calc R U P A 2
H13B H 1.111752 0.486912 0.116703 0.050 Uiso 0.427(13) 1 calc R U P A 2
C14A C 1.2150(12) 0.5686(5) 0.1484(8) 0.041(3) Uani 0.573(13) 1 d D U P A 1
H14A H 1.325342 0.561196 0.162410 0.049 Uiso 0.573(13) 1 calc R U P A 1
H14B H 1.194334 0.571879 0.089703 0.049 Uiso 0.573(13) 1 calc R U P A 1
C15 C 0.8732(9) 0.6829(3) 0.0008(4) 0.0618(19) Uani 0.823(13) 1 d D U P B 1
H15A H 0.785498 0.710313 -0.005290 0.074 Uiso 0.823(13) 1 calc R U P B 1
H15B H 0.891612 0.667986 -0.052540 0.074 Uiso 0.823(13) 1 calc R U P B 1
C16 C 1.0154(8) 0.7138(3) 0.0403(3) 0.0535(16) Uani 0.823(13) 1 d D U P B 1
H16A H 1.106735 0.688743 0.037729 0.064 Uiso 0.823(13) 1 calc R U P B 1
H16B H 1.031864 0.751378 0.012924 0.064 Uiso 0.823(13) 1 calc R U P B 1
C17 C 0.8669(5) 0.85605(19) 0.2448(3) 0.0564(10) Uani 1 1 d D U . . .
H17A H 0.819204 0.885360 0.277877 0.068 Uiso 0.72(5) 1 calc R U P C 1
H17B H 0.793294 0.823449 0.233728 0.068 Uiso 0.72(5) 1 calc R U P C 1
H17C H 0.820527 0.885681 0.277935 0.068 Uiso 0.28(5) 1 calc R U P C 2
H17D H 0.792789 0.823463 0.235142 0.068 Uiso 0.28(5) 1 calc R U P C 2
C18A C 0.8962(19) 0.8843(5) 0.1667(5) 0.073(3) Uani 0.72(5) 1 d D U P C 1
H18A H 0.798466 0.897660 0.137979 0.088 Uiso 0.72(5) 1 calc R U P C 1
H18B H 0.963128 0.919050 0.177120 0.088 Uiso 0.72(5) 1 calc R U P C 1
C13A C 1.1179(7) 0.5192(3) 0.1808(7) 0.050(2) Uani 0.573(13) 1 d D U P A 1
H13C H 1.132404 0.481746 0.152721 0.060 Uiso 0.573(13) 1 calc R U P A 1
H13D H 1.146123 0.513331 0.238709 0.060 Uiso 0.573(13) 1 calc R U P A 1
C14B C 1.2311(15) 0.5635(7) 0.1752(9) 0.036(3) Uani 0.427(13) 1 d D U P A 2
H14C H 1.258241 0.543040 0.226616 0.043 Uiso 0.427(13) 1 calc R U P A 2
H14D H 1.323022 0.566265 0.146157 0.043 Uiso 0.427(13) 1 calc R U P A 2
C18B C 0.890(4) 0.8836(12) 0.1661(9) 0.065(7) Uani 0.28(5) 1 d D U P C 2
H18C H 0.806023 0.911113 0.149368 0.078 Uiso 0.28(5) 1 calc R U P C 2
H18D H 0.987996 0.905441 0.170030 0.078 Uiso 0.28(5) 1 calc R U P C 2
O14A O 0.969(3) 0.8418(4) 0.1180(6) 0.086(4) Uani 0.72(5) 1 d D U P C 1
H14F H 0.974404 0.855771 0.072328 0.129 Uiso 0.72(5) 1 calc R U P C 1
H15E H 0.678(7) 0.516(2) 0.022(2) 0.087(19) Uiso 1 1 d D . . . .
H15F H 0.623(6) 0.541(3) -0.054(3) 0.14(3) Uiso 1 1 d D . . . .
C16A C 0.926(4) 0.7269(9) 0.0355(10) 0.060(5) Uani 0.177(13) 1 d D U P B 2
H16C H 0.988784 0.753792 0.006251 0.072 Uiso 0.177(13) 1 calc R U P B 2
H16D H 0.820298 0.742310 0.031117 0.072 Uiso 0.177(13) 1 calc R U P B 2
C15A C 0.927(3) 0.6658(10) -0.0013(14) 0.052(6) Uani 0.177(13) 1 d D U P B 2
H15C H 0.873790 0.665230 -0.056100 0.062 Uiso 0.177(13) 1 calc R U P B 2
H15D H 1.031677 0.650385 -0.001927 0.062 Uiso 0.177(13) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.332(2) . ?
Tb1 O5 2.300(2) . ?
Tb1 O7 2.423(2) . ?
Tb1 O8 2.410(2) . ?
Tb1 O9 2.386(2) . ?
Tb1 O10 2.421(2) . ?
Tb1 O11 2.396(2) . ?
Tb1 O12 2.386(2) . ?
Br1 C3 1.887(3) . ?
Br2 C4 1.891(3) . ?
Br3 C6 1.887(3) . ?
Br4 C7 1.878(3) . ?
Br5 C11 1.881(3) . ?
Br6 C12 1.885(3) . ?
O1 C1 1.256(3) . ?
O2 C1 1.243(3) . ?
O3 C8 1.244(4) . ?
O4 C8 1.253(4) . ?
O5 C9 1.254(4) . ?
O6 C9 1.235(4) . ?
O7 H7B 0.8200 . ?
O7 H7A 0.8200 . ?
O7 C13B 1.420(7) . ?
O7 C13A 1.431(7) . ?
O8 H8A 0.8200 . ?
O8 H8B 0.8200 . ?
O8 C14A 1.445(11) . ?
O8 C14B 1.448(16) . ?
O9 H9A 0.8200 . ?
O9 H9B 0.8200 . ?
O9 C15 1.442(6) . ?
O9 C15A 1.414(17) . ?
O10 H10 0.8200 . ?
O10 H10A 0.8200 . ?
O10 C16 1.417(5) . ?
O10 C16A 1.484(17) . ?
O11 H11A 0.8738 . ?
O11 H11B 0.8751 . ?
O12 H12A 0.8710 . ?
O12 H12B 0.8742 . ?
O13 H13 0.8200 . ?
O13 C17 1.411(5) . ?
O14B H14E 0.8200 . ?
O14B C18B 1.437(17) . ?
O15 H15E 0.841(10) . ?
O15 H15F 0.839(10) . ?
C1 C2 1.524(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.385(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.390(4) . ?
C5 C8 1.517(4) . ?
C6 C7 1.392(4) . ?
C9 C10 1.520(4) . ?
C10 C11 1.386(4) . ?
C10 C12 1.392(4) 3_766 ?
C11 C12 1.389(4) . ?
C13B H13A 0.9700 . ?
C13B H13B 0.9700 . ?
C13B C14B 1.622(19) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14A C13A 1.514(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.496(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C17 C18A 1.480(9) . ?
C17 C18B 1.469(16) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A O14A 1.432(10) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
O14A H14F 0.8200 . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C16A C15A 1.492(18) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?

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 Tb1 O7 144.52(7) . . ?
O1 Tb1 O8 149.78(7) . . ?
O1 Tb1 O9 91.03(9) . . ?
O1 Tb1 O10 79.69(8) . . ?
O1 Tb1 O11 80.37(8) . . ?
O1 Tb1 O12 73.24(7) . . ?
O5 Tb1 O1 100.29(8) . . ?
O5 Tb1 O7 80.09(8) . . ?
O5 Tb1 O8 94.00(9) . . ?
O5 Tb1 O9 149.42(8) . . ?
O5 Tb1 O10 144.82(9) . . ?
O5 Tb1 O11 73.30(8) . . ?
O5 Tb1 O12 79.73(8) . . ?
O8 Tb1 O7 64.07(7) . . ?
O8 Tb1 O10 73.42(9) . . ?
O9 Tb1 O7 74.46(9) . . ?
O9 Tb1 O8 89.94(10) . . ?
O9 Tb1 O10 64.98(9) . . ?
O9 Tb1 O11 137.00(9) . . ?
O9 Tb1 O12 76.50(9) . . ?
O10 Tb1 O7 120.06(8) . . ?
O11 Tb1 O7 131.89(9) . . ?
O11 Tb1 O8 78.46(9) . . ?
O11 Tb1 O10 72.03(9) . . ?
O12 Tb1 O7 71.95(7) . . ?
O12 Tb1 O8 135.98(7) . . ?
O12 Tb1 O10 131.99(9) . . ?
O12 Tb1 O11 137.87(9) . . ?
C1 O1 Tb1 142.89(18) . . ?
C9 O5 Tb1 144.1(2) . . ?
Tb1 O7 H7B 129.9 . . ?
Tb1 O7 H7A 127.7 . . ?
C13B O7 Tb1 118.7(4) . . ?
C13B O7 H7B 109.5 . . ?
C13A O7 Tb1 119.9(3) . . ?
C13A O7 H7A 109.5 . . ?
Tb1 O8 H8A 127.4 . . ?
Tb1 O8 H8B 126.0 . . ?
C14A O8 Tb1 120.7(4) . . ?
C14A O8 H8A 109.5 . . ?
C14B O8 Tb1 124.4(5) . . ?
C14B O8 H8B 109.5 . . ?
Tb1 O9 H9A 128.4 . . ?
Tb1 O9 H9B 123.7 . . ?
C15 O9 Tb1 121.7(3) . . ?
C15 O9 H9A 109.5 . . ?
C15A O9 Tb1 123.5(11) . . ?
C15A O9 H9B 109.5 . . ?
Tb1 O10 H10 123.4 . . ?
Tb1 O10 H10A 114.1 . . ?
C16 O10 Tb1 117.6(2) . . ?
C16 O10 H10 109.5 . . ?
C16A O10 Tb1 114.7(10) . . ?
C16A O10 H10A 109.5 . . ?
Tb1 O11 H11A 110.7 . . ?
Tb1 O11 H11B 110.5 . . ?
H11A O11 H11B 103.2 . . ?
Tb1 O12 H12A 110.7 . . ?
Tb1 O12 H12B 110.2 . . ?
H12A O12 H12B 103.6 . . ?
C17 O13 H13 109.5 . . ?
C18B O14B H14E 109.5 . . ?
H15E O15 H15F 116(6) . . ?
O1 C1 C2 115.4(2) . . ?
O2 C1 O1 126.4(3) . . ?
O2 C1 C2 118.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
C7 C2 C1 121.2(3) . . ?
C7 C2 C3 118.9(2) . . ?
C2 C3 Br1 117.3(2) . . ?
C4 C3 Br1 122.1(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 Br2 121.1(2) . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 Br2 118.2(2) . . ?
C4 C5 C8 121.9(3) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 C8 119.4(2) . . ?
C5 C6 Br3 118.4(2) . . ?
C5 C6 C7 120.7(3) . . ?
C7 C6 Br3 120.9(2) . . ?
C2 C7 Br4 118.4(2) . . ?
C2 C7 C6 120.5(3) . . ?
C6 C7 Br4 121.1(2) . . ?
O3 C8 O4 126.1(3) . . ?
O3 C8 C5 115.6(3) . . ?
O4 C8 C5 118.3(3) . . ?
O5 C9 C10 116.2(3) . . ?
O6 C9 O5 127.1(3) . . ?
O6 C9 C10 116.6(3) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 C12 119.0(3) . 3_766 ?
C12 C10 C9 119.4(3) 3_766 . ?
C10 C11 Br5 118.5(2) . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 Br5 121.0(2) . . ?
C10 C12 Br6 117.9(2) 3_766 . ?
C11 C12 Br6 121.5(2) . . ?
C11 C12 C10 120.5(3) . 3_766 ?
O7 C13B H13A 111.1 . . ?
O7 C13B H13B 111.1 . . ?
O7 C13B C14B 103.2(8) . . ?
H13A C13B H13B 109.1 . . ?
C14B C13B H13A 111.1 . . ?
C14B C13B H13B 111.1 . . ?
O8 C14A H14A 110.9 . . ?
O8 C14A H14B 110.9 . . ?
O8 C14A C13A 104.3(8) . . ?
H14A C14A H14B 108.9 . . ?
C13A C14A H14A 110.9 . . ?
C13A C14A H14B 110.9 . . ?
O9 C15 H15A 110.5 . . ?
O9 C15 H15B 110.5 . . ?
O9 C15 C16 106.2(4) . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
O10 C16 C15 106.9(5) . . ?
O10 C16 H16A 110.3 . . ?
O10 C16 H16B 110.3 . . ?
C15 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
O13 C17 H17A 108.8 . . ?
O13 C17 H17B 108.8 . . ?
O13 C17 H17C 108.4 . . ?
O13 C17 H17D 108.4 . . ?
O13 C17 C18A 113.6(7) . . ?
O13 C17 C18B 115.4(14) . . ?
H17A C17 H17B 107.7 . . ?
H17C C17 H17D 107.5 . . ?
C18A C17 H17A 108.8 . . ?
C18A C17 H17B 108.8 . . ?
C18B C17 H17C 108.4 . . ?
C18B C17 H17D 108.4 . . ?
C17 C18A H18A 109.8 . . ?
C17 C18A H18B 109.8 . . ?
H18A C18A H18B 108.2 . . ?
O14A C18A C17 109.4(6) . . ?
O14A C18A H18A 109.8 . . ?
O14A C18A H18B 109.8 . . ?
O7 C13A C14A 104.9(7) . . ?
O7 C13A H13C 110.8 . . ?
O7 C13A H13D 110.8 . . ?
C14A C13A H13C 110.8 . . ?
C14A C13A H13D 110.8 . . ?
H13C C13A H13D 108.8 . . ?
O8 C14B C13B 103.1(9) . . ?
O8 C14B H14C 111.2 . . ?
O8 C14B H14D 111.2 . . ?
C13B C14B H14C 111.2 . . ?
C13B C14B H14D 111.2 . . ?
H14C C14B H14D 109.1 . . ?
O14B C18B C17 106.3(15) . . ?
O14B C18B H18C 110.5 . . ?
O14B C18B H18D 110.5 . . ?
C17 C18B H18C 110.5 . . ?
C17 C18B H18D 110.5 . . ?
H18C C18B H18D 108.7 . . ?
C18A O14A H14F 109.5 . . ?
O10 C16A H16C 109.6 . . ?
O10 C16A H16D 109.6 . . ?
O10 C16A C15A 110.1(18) . . ?
H16C C16A H16D 108.2 . . ?
C15A C16A H16C 109.6 . . ?
C15A C16A H16D 109.6 . . ?
O9 C15A C16A 100.0(15) . . ?
O9 C15A H15C 111.8 . . ?
O9 C15A H15D 111.8 . . ?
C16A C15A H15C 111.8 . . ?
C16A C15A H15D 111.8 . . ?
H15C C15A H15D 109.5 . . ?

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
_geom_hbond_publ_flag
O11 H11A O6 0.87 1.94 2.774(4) 157.9 . yes
O11 H11B O13 0.88 1.92 2.710(3) 149.3 . yes
O12 H12A O4 0.87 2.13 2.806(3) 134.1 2_645 yes
O12 H12B O2 0.87 1.90 2.706(3) 153.2 . yes
O13 H13 O3 0.82 1.98 2.802(4) 175.1 1_655 yes
O14B H14E O6 0.82 2.18 2.954(16) 156.4 4_575 yes
O15 H15E O4 0.841(10) 2.125(18) 2.946(4) 165(5) 2_645 yes
O15 H15F O4 0.839(10) 2.00(3) 2.804(4) 161(7) 4_575 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb1 O1 C1 O2 -23.7(6) . . . . ?
Tb1 O1 C1 C2 155.6(2) . . . . ?
Tb1 O5 C9 O6 23.1(6) . . . . ?
Tb1 O5 C9 C10 -155.7(2) . . . . ?
Tb1 O7 C13B C14B 54.6(11) . . . . ?
Tb1 O7 C13A C14A -46.0(10) . . . . ?
Tb1 O8 C14A C13A -44.1(10) . . . . ?
Tb1 O8 C14B C13B 31.6(12) . . . . ?
Tb1 O9 C15 C16 34.3(8) . . . . ?
Tb1 O9 C15A C16A -47(3) . . . . ?
Tb1 O10 C16 C15 48.0(7) . . . . ?
Tb1 O10 C16A C15A -44(3) . . . . ?
Br1 C3 C4 Br2 -2.1(4) . . . . ?
Br1 C3 C4 C5 177.3(2) . . . . ?
Br2 C4 C5 C6 179.3(2) . . . . ?
Br2 C4 C5 C8 -5.0(4) . . . . ?
Br3 C6 C7 Br4 -3.8(4) . . . . ?
Br3 C6 C7 C2 176.1(2) . . . . ?
Br5 C11 C12 Br6 -0.3(4) . . . . ?
Br5 C11 C12 C10 179.1(2) . . . 3_766 ?
O1 C1 C2 C3 -85.7(3) . . . . ?
O1 C1 C2 C7 92.1(3) . . . . ?
O2 C1 C2 C3 93.7(4) . . . . ?
O2 C1 C2 C7 -88.5(4) . . . . ?
O5 C9 C10 C11 -95.4(4) . . . . ?
O5 C9 C10 C12 86.3(4) . . . 3_766 ?
O6 C9 C10 C11 85.6(4) . . . . ?
O6 C9 C10 C12 -92.6(4) . . . 3_766 ?
O7 C13B C14B O8 -50.3(12) . . . . ?
O8 C14A C13A O7 53.3(11) . . . . ?
O9 C15 C16 O10 -49.8(8) . . . . ?
O10 C16A C15A O9 54(3) . . . . ?
O13 C17 C18A O14A 57.5(17) . . . . ?
O13 C17 C18B O14B 83(2) . . . . ?
C1 C2 C3 Br1 0.1(4) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C7 Br4 2.9(4) . . . . ?
C1 C2 C7 C6 -177.1(3) . . . . ?
C2 C3 C4 Br2 179.4(2) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C2 C7 Br4 -179.3(2) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C8 175.6(3) . . . . ?
C4 C5 C6 Br3 -176.5(2) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C4 C5 C8 O3 -93.7(4) . . . . ?
C4 C5 C8 O4 88.3(4) . . . . ?
C5 C6 C7 Br4 178.0(2) . . . . ?
C5 C6 C7 C2 -2.0(5) . . . . ?
C6 C5 C8 O3 82.0(4) . . . . ?
C6 C5 C8 O4 -96.0(4) . . . . ?
C7 C2 C3 Br1 -177.7(2) . . . . ?
C7 C2 C3 C4 0.9(4) . . . . ?
C8 C5 C6 Br3 7.7(4) . . . . ?
C8 C5 C6 C7 -174.1(3) . . . . ?
C9 C10 C11 Br5 2.6(4) . . . . ?
C9 C10 C11 C12 -178.4(3) . . . . ?
C10 C11 C12 Br6 -179.4(2) . . . . ?
C10 C11 C12 C10 0.1(5) . . . 3_766 ?
C12 C10 C11 Br5 -179.2(2) 3_766 . . . ?
C12 C10 C11 C12 -0.1(5) 3_766 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_17tb_r
_database_code_depnum_ccdc_archive 'CCDC 1940056'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H4 Br4 N O8 Tb'
_chemical_formula_sum            'C9 H4 Br4 N O8 Tb'
_chemical_formula_weight         732.69
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1698(3)
_cell_length_b                   9.1909(3)
_cell_length_c                   10.0385(2)
_cell_angle_alpha                104.2990(10)
_cell_angle_beta                 93.4920(10)
_cell_angle_gamma                99.6490(10)
_cell_volume                     803.58(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.302
_cell_measurement_theta_min      2.701
_shelx_estimated_absorpt_T_max   0.238
_shelx_estimated_absorpt_T_min   0.130
_exptl_absorpt_coefficient_mu    14.382
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1133 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.6331.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.028
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37131
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3676
_reflns_number_total             4018
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0086P)²+2.3860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0487
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O8-H8
 0.85 with sigma of 0.01
 C9-H8
 1.898416 with sigma of 0.02
 Tb1-H8
 2.916163 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.47334(2) 0.20996(2) 0.97860(2) 0.01741(5) Uani 1 1 d D . . . .
Br1 Br 0.20334(5) 0.32585(7) 0.63017(5) 0.04763(13) Uani 1 1 d . . . . .
Br2 Br 0.20866(5) 0.07647(6) 0.32817(5) 0.04570(13) Uani 1 1 d . . . . .
Br3 Br 0.83440(5) 0.21869(6) 0.38876(5) 0.04491(13) Uani 1 1 d . . . . .
Br4 Br 0.82902(6) 0.47387(6) 0.68764(5) 0.05014(14) Uani 1 1 d . . . . .
O1 O 0.5323(4) 0.4006(3) 0.8755(3) 0.0318(7) Uani 1 1 d . . . . .
O2 O 0.5047(4) 0.6076(3) 0.8089(3) 0.0301(6) Uani 1 1 d . . . . .
O3 O 0.5497(4) -0.0816(3) 0.2675(3) 0.0333(7) Uani 1 1 d . . . . .
O4 O 0.4955(3) 0.0625(3) 0.1358(2) 0.0228(5) Uani 1 1 d . . . . .
O5 O 0.2351(3) 0.0427(3) 0.9449(4) 0.0396(7) Uani 1 1 d . . . . .
O6 O 0.2287(4) 0.2787(4) 0.9647(4) 0.0503(9) Uani 1 1 d . . . . .
O7 O 0.0242(4) 0.1105(5) 0.9058(5) 0.0678(12) Uani 1 1 d . . . . .
O8 O 0.7331(3) 0.2331(3) 1.0025(4) 0.0359(7) Uani 1 1 d D . . . .
H8 H 0.775(2) 0.1579(19) 1.007(5) 0.054 Uiso 1 1 d D U . . .
N1 N 0.1559(4) 0.1425(4) 0.9380(4) 0.0350(8) Uani 1 1 d . . . . .
C1 C 0.5174(4) 0.4710(4) 0.7855(3) 0.0208(7) Uani 1 1 d . . . . .
C2 C 0.5163(4) 0.3785(4) 0.6369(3) 0.0209(7) Uani 1 1 d . . . . .
C3 C 0.3848(4) 0.2981(4) 0.5589(4) 0.0218(7) Uani 1 1 d . . . . .
C4 C 0.3862(4) 0.1927(4) 0.4325(4) 0.0223(7) Uani 1 1 d . . . . .
C5 C 0.5205(4) 0.1679(4) 0.3839(3) 0.0200(7) Uani 1 1 d . . . . .
C6 C 0.5226(4) 0.0421(4) 0.2546(3) 0.0200(7) Uani 1 1 d . . . . .
C7 C 0.6531(4) 0.2521(4) 0.4585(4) 0.0228(7) Uani 1 1 d . . . . .
C8 C 0.6507(4) 0.3578(4) 0.5839(4) 0.0235(7) Uani 1 1 d . . . . .
C9 C 0.8429(5) 0.3693(5) 1.0408(6) 0.0493(13) Uani 1 1 d D . . . .
H9A H 0.932094 0.350346 0.999951 0.074 Uiso 1 1 calc R U . . .
H9B H 0.863947 0.401370 1.139666 0.074 Uiso 1 1 calc R U . . .
H9C H 0.806709 0.448163 1.008778 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.254(3) . ?
Tb1 O2 2.339(2) 2_667 ?
Tb1 O3 2.440(3) 2_656 ?
Tb1 O4 2.341(2) 1_556 ?
Tb1 O4 2.556(2) 2_656 ?
Tb1 O5 2.403(3) . ?
Tb1 O6 2.436(3) . ?
Tb1 O8 2.347(3) . ?
Br1 C3 1.882(4) . ?
Br2 C4 1.883(4) . ?
Br3 C7 1.885(4) . ?
Br4 C8 1.885(4) . ?
O1 C1 1.248(4) . ?
O2 C1 1.245(4) . ?
O3 C6 1.238(4) . ?
O4 C6 1.268(4) . ?
O5 N1 1.273(4) . ?
O6 N1 1.271(5) . ?
O7 N1 1.198(5) . ?
O8 H8 0.854(9) . ?
O8 C9 1.422(5) . ?
C1 C2 1.522(4) . ?
C2 C3 1.384(5) . ?
C2 C8 1.395(5) . ?
C3 C4 1.396(5) . ?
C4 C5 1.385(5) . ?
C5 C6 1.514(4) . ?
C5 C7 1.387(5) . ?
C7 C8 1.392(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 Tb1 O2 89.17(9) . 2_667 ?
O1 Tb1 O3 75.48(9) . 2_656 ?
O1 Tb1 O4 121.26(9) . 2_656 ?
O1 Tb1 O4 158.35(10) . 1_556 ?
O1 Tb1 O5 125.12(11) . . ?
O1 Tb1 O6 82.41(12) . . ?
O1 Tb1 O8 81.45(11) . . ?
O2 Tb1 O3 164.14(9) 2_667 2_656 ?
O2 Tb1 O4 77.99(8) 2_667 1_556 ?
O2 Tb1 O4 143.68(8) 2_667 2_656 ?
O2 Tb1 O5 109.05(11) 2_667 . ?
O2 Tb1 O6 80.54(12) 2_667 . ?
O2 Tb1 O8 88.46(11) 2_667 . ?
O3 Tb1 O4 51.68(8) 2_656 2_656 ?
O4 Tb1 O3 117.83(8) 1_556 2_656 ?
O4 Tb1 O4 66.69(9) 1_556 2_656 ?
O4 Tb1 O5 76.00(10) 1_556 . ?
O4 Tb1 O6 112.04(11) 1_556 . ?
O4 Tb1 O8 80.85(10) 1_556 . ?
O5 Tb1 O3 77.65(11) . 2_656 ?
O5 Tb1 O4 71.21(9) . 2_656 ?
O5 Tb1 O6 52.47(10) . . ?
O6 Tb1 O3 93.30(12) . 2_656 ?
O6 Tb1 O4 119.82(10) . 2_656 ?
O8 Tb1 O3 93.07(11) . 2_656 ?
O8 Tb1 O4 78.15(9) . 2_656 ?
O8 Tb1 O5 146.97(10) . . ?
O8 Tb1 O6 160.56(10) . . ?
C1 O1 Tb1 155.3(3) . . ?
C1 O2 Tb1 128.8(2) . 2_667 ?
C6 O3 Tb1 96.9(2) . 2_656 ?
Tb1 O4 Tb1 113.31(9) 1_554 2_656 ?
C6 O4 Tb1 90.62(19) . 2_656 ?
C6 O4 Tb1 154.7(2) . 1_554 ?
N1 O5 Tb1 97.1(2) . . ?
N1 O6 Tb1 95.6(2) . . ?
Tb1 O8 H8 122.0(14) . . ?
C9 O8 Tb1 128.0(3) . . ?
C9 O8 H8 108.6(14) . . ?
O6 N1 O5 114.4(3) . . ?
O7 N1 O5 122.9(4) . . ?
O7 N1 O6 122.7(4) . . ?
O1 C1 C2 115.4(3) . . ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 119.4(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 C8 118.8(3) . . ?
C8 C2 C1 119.6(3) . . ?
C2 C3 Br1 118.8(3) . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 Br1 120.3(3) . . ?
C3 C4 Br2 121.4(3) . . ?
C5 C4 Br2 118.6(3) . . ?
C5 C4 C3 119.9(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 C7 119.9(3) . . ?
C7 C5 C6 120.1(3) . . ?
O3 C6 Tb1 57.71(17) . 2_656 ?
O3 C6 O4 120.8(3) . . ?
O3 C6 C5 118.5(3) . . ?
O4 C6 Tb1 63.11(17) . 2_656 ?
O4 C6 C5 120.6(3) . . ?
C5 C6 Tb1 176.1(2) . 2_656 ?
C5 C7 Br3 119.1(3) . . ?
C5 C7 C8 119.8(3) . . ?
C8 C7 Br3 121.0(3) . . ?
C2 C8 Br4 118.5(3) . . ?
C7 C8 Br4 120.8(3) . . ?
C7 C8 C2 120.7(3) . . ?
O8 C9 H9A 109.5 . . ?
O8 C9 H9B 109.5 . . ?
O8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O5 0.854(9) 2.01(2) 2.772(4) 149(3) 2_657 yes
O8 H8 O7 0.854(9) 2.62(3) 3.182(5) 125(3) 1_655 yes
C9 H9A O7 0.96 2.48 3.205(7) 132.0 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb1 O1 C1 O2 124.9(5) . . . . ?
Tb1 O1 C1 C2 -55.5(8) . . . . ?
Tb1 O2 C1 O1 6.7(6) 2_667 . . . ?
Tb1 O2 C1 C2 -172.9(3) 2_667 . . . ?
Tb1 O3 C6 O4 -0.2(4) 2_656 . . . ?
Tb1 O3 C6 C5 179.0(3) 2_656 . . . ?
Tb1 O4 C6 Tb1 -161.3(6) 1_554 . . 2_656 ?
Tb1 O4 C6 O3 -161.2(4) 1_554 . . . ?
Tb1 O4 C6 O3 0.2(4) 2_656 . . . ?
Tb1 O4 C6 C5 19.6(8) 1_554 . . . ?
Tb1 O4 C6 C5 -179.0(3) 2_656 . . . ?
Tb1 O5 N1 O6 -6.8(4) . . . . ?
Tb1 O5 N1 O7 171.5(4) . . . . ?
Tb1 O6 N1 O5 6.7(4) . . . . ?
Tb1 O6 N1 O7 -171.6(4) . . . . ?
Br1 C3 C4 Br2 0.6(4) . . . . ?
Br1 C3 C4 C5 -177.0(3) . . . . ?
Br2 C4 C5 C6 -4.1(5) . . . . ?
Br2 C4 C5 C7 179.9(3) . . . . ?
Br3 C7 C8 Br4 0.9(5) . . . . ?
Br3 C7 C8 C2 -178.0(3) . . . . ?
O1 C1 C2 C3 90.5(4) . . . . ?
O1 C1 C2 C8 -81.1(4) . . . . ?
O2 C1 C2 C3 -89.9(5) . . . . ?
O2 C1 C2 C8 98.6(4) . . . . ?
C1 C2 C3 Br1 8.4(5) . . . . ?
C1 C2 C3 C4 -168.6(3) . . . . ?
C1 C2 C8 Br4 -10.7(4) . . . . ?
C1 C2 C8 C7 168.3(3) . . . . ?
C2 C3 C4 Br2 177.5(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C2 C8 Br4 177.5(3) . . . . ?
C3 C2 C8 C7 -3.5(5) . . . . ?
C3 C4 C5 C6 173.6(3) . . . . ?
C3 C4 C5 C7 -2.5(5) . . . . ?
C4 C5 C6 O3 -99.1(4) . . . . ?
C4 C5 C6 O4 80.2(5) . . . . ?
C4 C5 C7 Br3 -179.0(3) . . . . ?
C4 C5 C7 C8 2.0(5) . . . . ?
C5 C7 C8 Br4 -180.0(3) . . . . ?
C5 C7 C8 C2 1.0(6) . . . . ?
C6 C5 C7 Br3 5.0(5) . . . . ?
C6 C5 C7 C8 -174.1(3) . . . . ?
C7 C5 C6 O3 77.0(5) . . . . ?
C7 C5 C6 O4 -103.8(4) . . . . ?
C8 C2 C3 Br1 180.0(3) . . . . ?
C8 C2 C3 C4 3.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9ce_r
_database_code_depnum_ccdc_archive 'CCDC 1940063'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br8 Ce2 N2 O18'
_chemical_formula_sum            'C20 H16 Br8 Ce2 N2 O18'
_chemical_formula_weight         1491.87
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4200(10)
_cell_length_b                   12.6555(12)
_cell_length_c                   16.2502(18)
_cell_angle_alpha                77.141(4)
_cell_angle_beta                 72.822(3)
_cell_angle_gamma                68.507(3)
_cell_volume                     1889.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.341
_cell_measurement_theta_min      2.646
_shelx_estimated_absorpt_T_max   0.274
_shelx_estimated_absorpt_T_min   0.157
_exptl_absorpt_coefficient_mu    10.911
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1121 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.7071.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            75259
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6282
_reflns_number_total             7753
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.484
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7753
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+6.7196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10
 0.85 with sigma of 0.01
 O11-H11
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O18-H18
 0.85 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Ce1 Ce 1.00775(3) 0.69102(3) 0.28784(2) 0.02284(9) Uani 1 1 d . . . . .
Ce2 Ce 0.48792(3) 0.81421(3) 0.20917(2) 0.02317(9) Uani 1 1 d . . . . .
Br1 Br 0.61848(8) 0.72352(5) 0.55945(4) 0.03855(16) Uani 1 1 d . . . . .
Br2 Br 0.45464(8) 0.90323(6) 0.70710(4) 0.03991(17) Uani 1 1 d . . . . .
Br3 Br 0.80035(8) 0.39232(6) 0.16827(4) 0.04442(19) Uani 1 1 d . . . . .
Br4 Br 0.98889(9) 0.24477(6) 0.00508(4) 0.04372(18) Uani 1 1 d . . . . .
Br5 Br 1.26824(8) 0.76400(6) 0.50728(5) 0.04384(18) Uani 1 1 d . . . . .
Br6 Br 1.10864(9) 0.89873(7) 0.67974(5) 0.0515(2) Uani 1 1 d . . . . .
Br7 Br 0.42457(8) 0.40205(6) 0.20640(4) 0.03902(17) Uani 1 1 d . . . . .
Br8 Br 0.61032(8) 0.22352(5) 0.06012(4) 0.03806(16) Uani 1 1 d . . . . .
O1 O 0.7743(4) 0.7905(4) 0.3628(3) 0.0381(11) Uani 1 1 d . . . . .
O2 O 0.5713(5) 0.8296(4) 0.3265(3) 0.0359(10) Uani 1 1 d . . . . .
O3 O 0.9089(5) 0.6357(4) 0.1952(3) 0.0406(11) Uani 1 1 d . . . . .
O4 O 0.7099(5) 0.6716(4) 0.1556(3) 0.0389(11) Uani 1 1 d . . . . .
O5 O 1.0811(5) 0.8266(4) 0.3272(3) 0.0419(12) Uani 1 1 d . . . . .
O6 O 1.2622(5) 0.8870(4) 0.3082(3) 0.0427(12) Uani 1 1 d . . . . .
O7 O 1.0242(5) 0.6247(4) 0.4530(3) 0.0410(11) Uani 1 1 d . . . . .
O8 O 1.2231(5) 0.5774(4) 0.3569(3) 0.0407(11) Uani 1 1 d . . . . .
O9 O 1.2191(6) 0.5232(4) 0.4937(3) 0.0506(13) Uani 1 1 d . . . . .
O10 O 0.9320(5) 0.8710(4) 0.1866(3) 0.0380(11) Uani 1 1 d D . . . .
H10 H 0.854(5) 0.895(7) 0.171(5) 0.057 Uiso 1 1 d D U . . .
O11 O 0.9902(8) 0.4931(5) 0.3481(3) 0.0630(17) Uani 1 1 d D . . . .
H11 H 0.939(9) 0.491(9) 0.400(3) 0.094 Uiso 1 1 d D U . . .
O12 O 0.3911(5) 0.7209(4) 0.1434(3) 0.0377(11) Uani 1 1 d . . . . .
O13 O 0.2115(4) 0.6553(4) 0.1655(3) 0.0357(10) Uani 1 1 d . . . . .
O14 O 0.6721(5) 0.9205(4) 0.1413(3) 0.0396(11) Uani 1 1 d . . . . .
O15 O 0.5944(5) 0.8847(4) 0.0440(3) 0.0420(11) Uani 1 1 d . . . . .
O16 O 0.7410(6) 0.9819(4) 0.0045(3) 0.0517(14) Uani 1 1 d . . . . .
O17 O 0.3554(7) 1.0160(5) 0.1492(3) 0.0649(18) Uani 1 1 d D . . . .
H17 H 0.350(12) 1.033(9) 0.096(2) 0.097 Uiso 1 1 d D U . . .
O18 O 0.4768(5) 0.6344(4) 0.3122(3) 0.0404(11) Uani 1 1 d D . . . .
H18 H 0.399(5) 0.619(7) 0.330(5) 0.061 Uiso 1 1 d D U . . .
N1 N 1.1562(6) 0.5735(5) 0.4364(3) 0.0330(12) Uani 1 1 d . . . . .
N2 N 0.6707(6) 0.9299(4) 0.0618(4) 0.0355(13) Uani 1 1 d . . . . .
C1 C 0.6441(6) 0.8415(5) 0.3701(3) 0.0238(12) Uani 1 1 d . . . . .
C2 C 0.5694(6) 0.9237(5) 0.4376(3) 0.0212(11) Uani 1 1 d . . . . .
C3 C 0.5505(6) 0.8835(5) 0.5262(4) 0.0228(12) Uani 1 1 d . . . . .
C4 C 0.4821(6) 0.9592(5) 0.5879(3) 0.0233(12) Uani 1 1 d . . . . .
C5 C 0.8404(6) 0.6292(5) 0.1478(4) 0.0246(12) Uani 1 1 d . . . . .
C6 C 0.9230(6) 0.5616(5) 0.0709(4) 0.0240(12) Uani 1 1 d . . . . .
C7 C 0.9160(6) 0.4541(5) 0.0716(4) 0.0245(12) Uani 1 1 d . . . . .
C8 C 0.9924(6) 0.3931(5) 0.0017(4) 0.0243(12) Uani 1 1 d . . . . .
C9 C 1.1429(6) 0.8803(5) 0.3476(4) 0.0253(12) Uani 1 1 d . . . . .
C10 C 1.0688(6) 0.9419(5) 0.4267(4) 0.0231(12) Uani 1 1 d . . . . .
C11 C 1.1142(6) 0.9006(5) 0.5027(4) 0.0254(12) Uani 1 1 d . . . . .
C12 C 1.0453(6) 0.9579(5) 0.5762(4) 0.0277(13) Uani 1 1 d . . . . .
C13 C 1.0141(9) 0.9413(6) 0.1313(5) 0.0479(19) Uani 1 1 d . . . . .
H13A H 1.041345 0.923661 0.072806 0.072 Uiso 1 1 calc R U . . .
H13B H 1.097602 0.926434 0.151491 0.072 Uiso 1 1 calc R U . . .
H13C H 0.958093 1.020603 0.132691 0.072 Uiso 1 1 calc R U . . .
C14 C 1.0407(11) 0.3878(7) 0.3129(6) 0.067(3) Uani 1 1 d . . . . .
H14A H 1.110747 0.392080 0.259529 0.100 Uiso 1 1 calc R U . . .
H14B H 0.963037 0.373984 0.301892 0.100 Uiso 1 1 calc R U . . .
H14C H 1.082457 0.326498 0.353517 0.100 Uiso 1 1 calc R U . . .
C15 C 0.3328(6) 0.6573(5) 0.1298(3) 0.0238(12) Uani 1 1 d . . . . .
C16 C 0.4197(5) 0.5763(5) 0.0618(3) 0.0197(11) Uani 1 1 d . . . . .
C17 C 0.4669(6) 0.4586(5) 0.0871(3) 0.0236(12) Uani 1 1 d . . . . .
C18 C 0.5451(6) 0.3824(5) 0.0257(4) 0.0226(12) Uani 1 1 d . . . . .
C19 C 0.2592(9) 1.1189(7) 0.1823(6) 0.060(2) Uani 1 1 d . . . . .
H19A H 0.296425 1.180772 0.155885 0.090 Uiso 1 1 calc R U . . .
H19B H 0.247382 1.109601 0.244110 0.090 Uiso 1 1 calc R U . . .
H19C H 0.169133 1.135786 0.169368 0.090 Uiso 1 1 calc R U . . .
C20 C 0.5727(9) 0.5602(7) 0.3637(5) 0.056(2) Uani 1 1 d . . . . .
H20A H 0.667665 0.559077 0.334291 0.084 Uiso 1 1 calc R U . . .
H20B H 0.567342 0.484205 0.372766 0.084 Uiso 1 1 calc R U . . .
H20C H 0.547523 0.587488 0.418822 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O1 2.382(4) . ?
Ce1 O3 2.393(4) . ?
Ce1 O5 2.383(4) . ?
Ce1 O7 2.665(5) . ?
Ce1 O8 2.602(5) . ?
Ce1 O10 2.510(5) . ?
Ce1 O11 2.531(6) . ?
Ce1 O13 2.422(4) 1_655 ?
Ce2 O2 2.386(4) . ?
Ce2 O4 2.412(4) . ?
Ce2 O6 2.409(4) 1_455 ?
Ce2 O12 2.371(4) . ?
Ce2 O14 2.586(5) . ?
Ce2 O15 2.671(5) . ?
Ce2 O17 2.546(6) . ?
Ce2 O18 2.526(5) . ?
Br1 C3 1.893(6) . ?
Br2 C4 1.883(5) . ?
Br3 C7 1.886(6) . ?
Br4 C8 1.879(6) . ?
Br5 C11 1.885(6) . ?
Br6 C12 1.887(6) . ?
Br7 C17 1.890(5) . ?
Br8 C18 1.881(6) . ?
O1 C1 1.253(7) . ?
O2 C1 1.245(7) . ?
O3 C5 1.228(7) . ?
O4 C5 1.243(7) . ?
O5 C9 1.239(7) . ?
O6 C9 1.243(7) . ?
O7 N1 1.262(7) . ?
O8 N1 1.272(7) . ?
O9 N1 1.222(7) . ?
O10 H10 0.849(10) . ?
O10 C13 1.442(8) . ?
O11 H11 0.850(10) . ?
O11 C14 1.423(10) . ?
O12 C15 1.258(7) . ?
O13 C15 1.233(7) . ?
O14 N2 1.274(7) . ?
O15 N2 1.260(7) . ?
O16 N2 1.230(7) . ?
O17 H17 0.851(10) . ?
O17 C19 1.424(9) . ?
O18 H18 0.849(10) . ?
O18 C20 1.427(9) . ?
C1 C2 1.517(7) . ?
C2 C3 1.396(7) . ?
C2 C4 1.390(8) 2_676 ?
C3 C4 1.392(7) . ?
C5 C6 1.528(7) . ?
C6 C7 1.385(8) . ?
C6 C8 1.398(8) 2_765 ?
C7 C8 1.388(8) . ?
C9 C10 1.508(7) . ?
C10 C11 1.378(8) . ?
C10 C12 1.388(8) 2_776 ?
C11 C12 1.402(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.524(7) . ?
C16 C17 1.393(8) . ?
C16 C18 1.389(7) 2_665 ?
C17 C18 1.401(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 Ce1 O3 89.63(16) . . ?
O1 Ce1 O5 86.33(16) . . ?
O1 Ce1 O7 78.34(15) . . ?
O1 Ce1 O8 126.16(15) . . ?
O1 Ce1 O10 76.04(16) . . ?
O1 Ce1 O11 95.1(2) . . ?
O1 Ce1 O13 155.77(17) . 1_655 ?
O3 Ce1 O7 133.45(16) . . ?
O3 Ce1 O8 130.70(16) . . ?
O3 Ce1 O10 76.67(16) . . ?
O3 Ce1 O11 71.44(18) . . ?
O3 Ce1 O13 81.36(16) . 1_655 ?
O5 Ce1 O3 151.32(17) . . ?
O5 Ce1 O7 73.30(16) . . ?
O5 Ce1 O8 72.38(17) . . ?
O5 Ce1 O10 74.80(16) . . ?
O5 Ce1 O11 137.19(18) . . ?
O5 Ce1 O13 90.88(16) . 1_655 ?
O8 Ce1 O7 48.53(14) . . ?
O10 Ce1 O7 139.94(16) . . ?
O10 Ce1 O8 138.13(15) . . ?
O10 Ce1 O11 146.98(19) . . ?
O11 Ce1 O7 65.24(17) . . ?
O11 Ce1 O8 72.5(2) . . ?
O13 Ce1 O7 123.79(15) 1_655 . ?
O13 Ce1 O8 75.27(15) 1_655 . ?
O13 Ce1 O10 79.99(16) 1_655 . ?
O13 Ce1 O11 103.09(18) 1_655 . ?
O2 Ce2 O4 91.34(16) . . ?
O2 Ce2 O6 81.21(16) . 1_455 ?
O2 Ce2 O14 73.89(15) . . ?
O2 Ce2 O15 122.44(15) . . ?
O2 Ce2 O17 107.57(19) . . ?
O2 Ce2 O18 76.69(16) . . ?
O4 Ce2 O14 73.42(16) . . ?
O4 Ce2 O15 70.96(16) . . ?
O4 Ce2 O17 134.34(17) . . ?
O4 Ce2 O18 76.02(16) . . ?
O6 Ce2 O4 155.51(18) 1_455 . ?
O6 Ce2 O14 125.59(16) 1_455 . ?
O6 Ce2 O15 132.41(17) 1_455 . ?
O6 Ce2 O17 69.98(18) 1_455 . ?
O6 Ce2 O18 79.56(17) 1_455 . ?
O12 Ce2 O2 151.66(17) . . ?
O12 Ce2 O4 84.18(16) . . ?
O12 Ce2 O6 91.37(16) . 1_455 ?
O12 Ce2 O14 130.44(15) . . ?
O12 Ce2 O15 82.47(16) . . ?
O12 Ce2 O17 95.2(2) . . ?
O12 Ce2 O18 75.07(16) . . ?
O14 Ce2 O15 48.71(14) . . ?
O17 Ce2 O14 72.8(2) . . ?
O17 Ce2 O15 63.76(16) . . ?
O18 Ce2 O14 136.52(16) . . ?
O18 Ce2 O15 141.57(16) . . ?
O18 Ce2 O17 147.87(19) . . ?
C1 O1 Ce1 154.4(4) . . ?
C1 O2 Ce2 163.4(4) . . ?
C5 O3 Ce1 167.3(4) . . ?
C5 O4 Ce2 149.7(4) . . ?
C9 O5 Ce1 168.0(4) . . ?
C9 O6 Ce2 150.1(4) . 1_655 ?
N1 O7 Ce1 95.6(3) . . ?
N1 O8 Ce1 98.4(3) . . ?
Ce1 O10 H10 124(6) . . ?
C13 O10 Ce1 129.4(4) . . ?
C13 O10 H10 106(6) . . ?
Ce1 O11 H11 112(8) . . ?
C14 O11 Ce1 133.9(5) . . ?
C14 O11 H11 114(8) . . ?
C15 O12 Ce2 163.9(4) . . ?
C15 O13 Ce1 149.7(4) . 1_455 ?
N2 O14 Ce2 98.6(4) . . ?
N2 O15 Ce2 94.9(3) . . ?
Ce2 O17 H17 121(8) . . ?
C19 O17 Ce2 137.7(5) . . ?
C19 O17 H17 100(8) . . ?
Ce2 O18 H18 120(6) . . ?
C20 O18 Ce2 130.1(5) . . ?
C20 O18 H18 109(6) . . ?
O7 N1 O8 117.4(5) . . ?
O9 N1 O7 121.9(6) . . ?
O9 N1 O8 120.7(6) . . ?
O15 N2 O14 117.7(5) . . ?
O16 N2 O14 121.1(6) . . ?
O16 N2 O15 121.1(6) . . ?
O1 C1 C2 117.4(5) . . ?
O2 C1 O1 125.0(5) . . ?
O2 C1 C2 117.6(5) . . ?
C3 C2 C1 120.9(5) . . ?
C4 C2 C1 120.4(5) 2_676 . ?
C4 C2 C3 118.8(5) 2_676 . ?
C2 C3 Br1 118.1(4) . . ?
C4 C3 Br1 121.2(4) . . ?
C4 C3 C2 120.8(5) . . ?
C2 C4 Br2 119.3(4) 2_676 . ?
C2 C4 C3 120.5(5) 2_676 . ?
C3 C4 Br2 120.2(4) . . ?
O3 C5 O4 126.9(5) . . ?
O3 C5 C6 117.1(5) . . ?
O4 C5 C6 116.0(5) . . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 C8 118.5(5) . 2_765 ?
C8 C6 C5 120.5(5) 2_765 . ?
C6 C7 Br3 119.2(4) . . ?
C6 C7 C8 120.4(5) . . ?
C8 C7 Br3 120.4(4) . . ?
C6 C8 Br4 118.7(4) 2_765 . ?
C7 C8 Br4 120.2(4) . . ?
C7 C8 C6 121.0(5) . 2_765 ?
O5 C9 O6 125.0(6) . . ?
O5 C9 C10 117.8(5) . . ?
O6 C9 C10 117.2(5) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 C12 118.8(5) . 2_776 ?
C12 C10 C9 120.5(5) 2_776 . ?
C10 C11 Br5 119.0(4) . . ?
C10 C11 C12 120.7(5) . . ?
C12 C11 Br5 120.3(5) . . ?
C10 C12 Br6 119.7(4) 2_776 . ?
C10 C12 C11 120.5(5) 2_776 . ?
C11 C12 Br6 119.8(5) . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O12 C15 C16 116.9(5) . . ?
O13 C15 O12 126.2(5) . . ?
O13 C15 C16 117.0(5) . . ?
C17 C16 C15 120.0(5) . . ?
C18 C16 C15 121.2(5) 2_665 . ?
C18 C16 C17 118.8(5) 2_665 . ?
C16 C17 Br7 119.0(4) . . ?
C16 C17 C18 121.0(5) . . ?
C18 C17 Br7 120.0(4) . . ?
C16 C18 Br8 118.8(4) 2_665 . ?
C16 C18 C17 120.2(5) 2_665 . ?
C17 C18 Br8 120.9(4) . . ?
O17 C19 H19A 109.5 . . ?
O17 C19 H19B 109.5 . . ?
O17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O18 C20 H20A 109.5 . . ?
O18 C20 H20B 109.5 . . ?
O18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_hbond_publ_flag
O10 H10 O14 0.849(10) 1.99(2) 2.827(7) 169(8) . yes
O11 H11 O9 0.850(10) 2.04(3) 2.862(8) 164(10) 2_766 yes
O17 H17 O15 0.851(10) 2.29(5) 3.076(7) 155(10) 2_675 yes
O17 H17 O16 0.851(10) 2.19(6) 2.945(8) 148(10) 2_675 yes
O18 H18 O8 0.849(10) 1.996(16) 2.840(7) 173(8) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ce1 O1 C1 O2 23.3(14) . . . . ?
Ce1 O1 C1 C2 -156.8(7) . . . . ?
Ce1 O3 C5 O4 -40(2) . . . . ?
Ce1 O3 C5 C6 140.4(17) . . . . ?
Ce1 O5 C9 O6 51(2) . . . . ?
Ce1 O5 C9 C10 -128.2(19) . . . . ?
Ce1 O7 N1 O8 2.8(6) . . . . ?
Ce1 O7 N1 O9 -178.3(5) . . . . ?
Ce1 O8 N1 O7 -2.9(6) . . . . ?
Ce1 O8 N1 O9 178.2(5) . . . . ?
Ce1 O13 C15 O12 -23.8(13) 1_455 . . . ?
Ce1 O13 C15 C16 157.1(6) 1_455 . . . ?
Ce2 O2 C1 O1 -47.8(18) . . . . ?
Ce2 O2 C1 C2 132.4(13) . . . . ?
Ce2 O4 C5 O3 24.2(13) . . . . ?
Ce2 O4 C5 C6 -156.0(6) . . . . ?
Ce2 O6 C9 O5 -19.6(13) 1_655 . . . ?
Ce2 O6 C9 C10 159.9(6) 1_655 . . . ?
Ce2 O12 C15 O13 59.1(18) . . . . ?
Ce2 O12 C15 C16 -121.7(14) . . . . ?
Ce2 O14 N2 O15 -3.1(6) . . . . ?
Ce2 O14 N2 O16 176.6(5) . . . . ?
Ce2 O15 N2 O14 3.0(5) . . . . ?
Ce2 O15 N2 O16 -176.7(5) . . . . ?
Br1 C3 C4 Br2 -0.3(7) . . . . ?
Br1 C3 C4 C2 -178.9(4) . . . 2_676 ?
Br3 C7 C8 Br4 -3.2(7) . . . . ?
Br3 C7 C8 C6 179.1(4) . . . 2_765 ?
Br5 C11 C12 Br6 0.7(7) . . . . ?
Br5 C11 C12 C10 -179.6(4) . . . 2_776 ?
Br7 C17 C18 Br8 -0.4(7) . . . . ?
Br7 C17 C18 C16 -178.1(4) . . . 2_665 ?
O1 C1 C2 C3 -68.6(7) . . . . ?
O1 C1 C2 C4 111.7(7) . . . 2_676 ?
O2 C1 C2 C3 111.3(6) . . . . ?
O2 C1 C2 C4 -68.4(8) . . . 2_676 ?
O3 C5 C6 C7 106.2(7) . . . . ?
O3 C5 C6 C8 -73.6(8) . . . 2_765 ?
O4 C5 C6 C7 -73.6(8) . . . . ?
O4 C5 C6 C8 106.6(7) . . . 2_765 ?
O5 C9 C10 C11 106.9(7) . . . . ?
O5 C9 C10 C12 -74.0(8) . . . 2_776 ?
O6 C9 C10 C11 -72.7(8) . . . . ?
O6 C9 C10 C12 106.4(7) . . . 2_776 ?
O12 C15 C16 C17 111.4(6) . . . . ?
O12 C15 C16 C18 -67.8(7) . . . 2_665 ?
O13 C15 C16 C17 -69.4(7) . . . . ?
O13 C15 C16 C18 111.4(6) . . . 2_665 ?
C1 C2 C3 Br1 -0.8(7) . . . . ?
C1 C2 C3 C4 179.9(5) . . . . ?
C2 C3 C4 Br2 178.9(4) . . . . ?
C2 C3 C4 C2 0.4(10) . . . 2_676 ?
C4 C2 C3 Br1 178.9(4) 2_676 . . . ?
C4 C2 C3 C4 -0.4(9) 2_676 . . . ?
C5 C6 C7 Br3 1.0(8) . . . . ?
C5 C6 C7 C8 -179.5(6) . . . . ?
C6 C7 C8 Br4 177.3(4) . . . . ?
C6 C7 C8 C6 -0.3(10) . . . 2_765 ?
C8 C6 C7 Br3 -179.1(4) 2_765 . . . ?
C8 C6 C7 C8 0.3(10) 2_765 . . . ?
C9 C10 C11 Br5 -1.3(8) . . . . ?
C9 C10 C11 C12 180.0(5) . . . . ?
C10 C11 C12 Br6 179.5(4) . . . . ?
C10 C11 C12 C10 -0.9(10) . . . 2_776 ?
C12 C10 C11 Br5 179.6(4) 2_776 . . . ?
C12 C10 C11 C12 0.8(10) 2_776 . . . ?
C15 C16 C17 Br7 -1.2(7) . . . . ?
C15 C16 C17 C18 179.0(5) . . . . ?
C16 C17 C18 Br8 179.4(4) . . . . ?
C16 C17 C18 C16 1.8(9) . . . 2_665 ?
C18 C16 C17 Br7 178.1(4) 2_665 . . . ?
C18 C16 C17 C18 -1.7(9) 2_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_15dy
_database_code_depnum_ccdc_archive 'CCDC 1940054'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26.7 H15.4 Br12 Dy2 O17'
_chemical_formula_sum            'C26.70 H15.40 Br12 Dy2 O17'
_chemical_formula_weight         1891.99
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.550(4)
_cell_length_b                   17.970(5)
_cell_length_c                   21.577(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.910(10)
_cell_angle_gamma                90
_cell_volume                     4436(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.290
_cell_measurement_theta_min      3.154
_shelx_estimated_absorpt_T_max   0.396
_shelx_estimated_absorpt_T_min   0.184
_exptl_absorpt_coefficient_mu    14.218
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1183 before and 0.0780 after correction. The Ratio of minimum to maximum transmission is 0.7380. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3454
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            75522
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.883
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6548
_reflns_number_total             8699
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.386
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       0.000091(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8699
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+55.7176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O14-H14
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O13A-H13A
 0.85 with sigma of 0.01
 O13-H13
 0.85 with sigma of 0.01
 O15-H15A = O15-H15B
 0.85 with sigma of 0.02
 O16-H16A = O16-H16B
 0.85 with sigma of 0.02
 C26-H14
 1.915338 with sigma of 0.02
 Dy2-H14
 2.96379 with sigma of 0.02
 C27-H17
 1.91147 with sigma of 0.02
 Dy2-H17
 3.083201 with sigma of 0.02
 C25A-H13A
 2.001639 with sigma of 0.02
 Dy2-H13A
 2.970671 with sigma of 0.02
 C25-H13
 2.006304 with sigma of 0.02
 Dy2-H13
 2.996201 with sigma of 0.02
 H15A-H15B
 1.34 with sigma of 0.04
 H16A-H16B
 1.34 with sigma of 0.04
 Dy2-O15 \\sim Dy2-O18
 with sigma of 0.01
 Dy2-O14 \\sim Dy2-O17
 with sigma of 0.01
 O14-C26 \\sim O17-C27
 with sigma of 0.01
 Dy2-O13 \\sim Dy2-O13A
 with sigma of 0.02
 O13-C25 \\sim O13A-C25A
 with sigma of 0.02
 Dy2-C25 \\sim Dy2-C25A
 with sigma of 0.04
 Dy2-H15A \\sim Dy2-H15B
 with sigma of 0.02
 Dy2-H16A \\sim Dy2-H16B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O17) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O13) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O13A) \\sim Ueq, Uanis(C25A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Dy2, O17, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Dy2, O18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Dy2, O13, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Dy2, O13A, C25A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O13A)=Sof(H13A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(O13)=Sof(H13)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
 Fixed Sof: O17(0.7) H17(0.7) O18(0.3) H18A(0.3) H18B(0.3) C27(0.7) H27A(0.7)
 H27B(0.7) H27C(0.7)
6.a Rotating group:
 O18(H18A,H18B)
6.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.43693(3) 0.74796(2) 0.63078(2) 0.01358(9) Uani 1 1 d . . . . .
Dy2 Dy 0.49652(3) 0.24942(2) 0.87171(2) 0.01579(10) Uani 1 1 d D U . . .
Br1 Br 0.31522(10) 0.67308(5) 0.85030(5) 0.0422(3) Uani 1 1 d . . . . .
Br2 Br 0.31255(11) 0.51581(5) 0.93034(4) 0.0428(3) Uani 1 1 d . . . . .
Br3 Br 0.21434(10) 0.35571(5) 0.70484(5) 0.0430(3) Uani 1 1 d . . . . .
Br4 Br 0.21070(10) 0.51567(6) 0.62432(4) 0.0398(3) Uani 1 1 d . . . . .
Br5 Br 0.60338(9) 0.95028(5) 0.81285(4) 0.0352(2) Uani 1 1 d . . . . .
Br6 Br 0.65009(11) 0.94691(5) 0.96848(4) 0.0474(3) Uani 1 1 d . . . . .
Br7 Br 0.70287(11) 0.63574(6) 0.96336(5) 0.0508(3) Uani 1 1 d . . . . .
Br8 Br 0.66938(12) 0.64078(6) 0.80609(5) 0.0570(3) Uani 1 1 d . . . . .
Br9 Br 0.54690(10) 0.67093(6) 0.45798(5) 0.0488(3) Uani 1 1 d . . . . .
Br10 Br 0.43823(11) 0.54466(6) 0.35185(5) 0.0524(3) Uani 1 1 d . . . . .
Br11 Br 0.51330(10) 0.86297(5) 0.40182(5) 0.0450(3) Uani 1 1 d . . . . .
Br12 Br 0.41214(10) 1.02870(5) 0.35124(4) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.3317(5) 0.6822(3) 0.6926(3) 0.0339(15) Uani 1 1 d . . . . .
O2 O 0.1404(5) 0.6804(3) 0.6935(3) 0.0298(14) Uani 1 1 d . . . . .
O3 O 0.3626(5) 0.3442(3) 0.8565(3) 0.0290(14) Uani 1 1 d . . . . .
O4 O 0.1728(5) 0.3510(3) 0.8611(3) 0.0283(14) Uani 1 1 d . . . . .
O5 O 0.5476(5) 0.7835(3) 0.7187(3) 0.0320(15) Uani 1 1 d . . . . .
O6 O 0.7343(6) 0.8164(4) 0.7325(3) 0.0428(18) Uani 1 1 d . . . . .
O7 O 0.8052(5) 0.7909(4) 1.0486(3) 0.0308(15) Uani 1 1 d . . . . .
O8 O 0.6149(5) 0.7834(4) 1.0534(3) 0.0305(14) Uani 1 1 d . . . . .
O9 O 0.5443(5) 0.6491(3) 0.6180(3) 0.0310(15) Uani 1 1 d . . . . .
O10 O 0.7153(5) 0.6077(4) 0.5987(4) 0.056(2) Uani 1 1 d . . . . .
O11 O 0.5344(5) 0.8121(3) 0.5678(3) 0.0305(15) Uani 1 1 d . . . . .
O12 O 0.7001(5) 0.8469(4) 0.5363(3) 0.0431(18) Uani 1 1 d . . . . .
O13 O 0.5960(14) 0.3677(6) 0.8925(8) 0.052(5) Uani 0.67(3) 1 d D U P A 1
H13 H 0.636(12) 0.379(3) 0.928(3) 0.077 Uiso 0.67(3) 1 d DR . P A 1
O13A O 0.608(2) 0.3630(10) 0.8689(15) 0.036(7) Uani 0.33(3) 1 d D U P A 2
H13A H 0.676(10) 0.363(3) 0.858(12) 0.054 Uiso 0.33(3) 1 d DR . P A 2
O14 O 0.6258(6) 0.2455(5) 0.9702(3) 0.067(3) Uani 1 1 d D . . . .
H14 H 0.691(5) 0.269(5) 0.974(2) 0.100 Uiso 1 1 d DR . . . .
O15 O 0.6819(6) 0.2272(5) 0.8483(4) 0.062(3) Uani 1 1 d D . . . .
H15A H 0.740(4) 0.229(8) 0.877(2) 0.093 Uiso 1 1 d DR . . . .
H15B H 0.706(5) 0.248(6) 0.817(3) 0.093 Uiso 1 1 d DR . . . .
O16 O 0.5438(6) 0.1199(4) 0.8912(4) 0.049(2) Uani 1 1 d D . . . .
H16A H 0.493(3) 0.086(2) 0.891(6) 0.074 Uiso 1 1 d DR . . . .
H16B H 0.608(4) 0.100(2) 0.885(6) 0.074 Uiso 1 1 d DR . . . .
O17 O 0.5123(19) 0.2986(9) 0.7671(4) 0.036(3) Uani 0.7 1 d D U P A 2
H17 H 0.533(11) 0.343(2) 0.7580(15) 0.054 Uiso 0.7 1 d DR . P B 2
O18 O 0.512(7) 0.280(3) 0.7691(10) 0.076(17) Uani 0.3 1 d D U P A 1
H18A H 0.447669 0.269039 0.744213 0.115 Uiso 0.3 1 d GR . P A 1
H18B H 0.564696 0.254558 0.753191 0.115 Uiso 0.3 1 d GR . P A 1
C1 C 0.2403(7) 0.6550(4) 0.7069(4) 0.0218(19) Uani 1 1 d . . . . .
C2 C 0.2517(7) 0.5822(4) 0.7438(4) 0.0172(17) Uani 1 1 d . . . . .
C3 C 0.2788(7) 0.5825(4) 0.8085(4) 0.0224(18) Uani 1 1 d . . . . .
C4 C 0.2812(7) 0.5157(4) 0.8419(4) 0.0196(18) Uani 1 1 d . . . . .
C5 C 0.2612(6) 0.4485(4) 0.8114(3) 0.0143(16) Uani 1 1 d . . . . .
C6 C 0.2386(7) 0.4484(5) 0.7460(4) 0.0223(18) Uani 1 1 d . . . . .
C7 C 0.2341(7) 0.5145(4) 0.7128(4) 0.0198(18) Uani 1 1 d . . . . .
C8 C 0.2660(7) 0.3745(4) 0.8460(4) 0.0182(17) Uani 1 1 d . . . . .
C9 C 0.6425(8) 0.7990(5) 0.7519(4) 0.025(2) Uani 1 1 d . . . . .
C10 C 0.6455(7) 0.7955(4) 0.8224(4) 0.0183(17) Uani 1 1 d . . . . .
C11 C 0.6382(7) 0.8608(4) 0.8566(3) 0.0184(17) Uani 1 1 d . . . . .
C12 C 0.6574(7) 0.8585(4) 0.9221(3) 0.0177(17) Uani 1 1 d . . . . .
C13 C 0.6787(7) 0.7911(5) 0.9531(4) 0.0192(18) Uani 1 1 d . . . . .
C14 C 0.6797(8) 0.7264(5) 0.9191(4) 0.0244(19) Uani 1 1 d . . . . .
C15 C 0.6644(8) 0.7283(5) 0.8539(4) 0.026(2) Uani 1 1 d . . . . .
C16 C 0.7024(7) 0.7888(4) 1.0251(4) 0.0187(18) Uani 1 1 d . . . . .
C17 C 0.6083(7) 0.6071(4) 0.5905(4) 0.025(2) Uani 1 1 d . . . . .
C18 C 0.5493(7) 0.5524(5) 0.5441(5) 0.028(2) Uani 1 1 d . . . . .
C19 C 0.5212(8) 0.5716(5) 0.4818(5) 0.031(2) Uani 1 1 d . . . . .
C20 C 0.4740(8) 0.5200(5) 0.4371(4) 0.029(2) Uani 1 1 d . . . . .
C21 C 0.5982(7) 0.8567(4) 0.5436(4) 0.0204(18) Uani 1 1 d . . . . .
C22 C 0.5454(7) 0.9310(4) 0.5211(4) 0.0209(18) Uani 1 1 d . . . . .
C23 C 0.5062(7) 0.9422(5) 0.4583(4) 0.0237(19) Uani 1 1 d . . . . .
C24 C 0.4616(7) 1.0116(5) 0.4368(4) 0.0211(18) Uani 1 1 d . . . . .
C25 C 0.5875(17) 0.4367(9) 0.8487(11) 0.061(6) Uani 0.67(3) 1 d D U P A 1
H25A H 0.625705 0.426068 0.812953 0.091 Uiso 0.67(3) 1 calc GR . P A 1
H25B H 0.624676 0.478430 0.870986 0.091 Uiso 0.67(3) 1 calc GR . P A 1
H25C H 0.506753 0.448104 0.835245 0.091 Uiso 0.67(3) 1 calc GR . P A 1
C25A C 0.577(3) 0.4431(14) 0.887(2) 0.049(10) Uani 0.33(3) 1 d D U P A 2
H25D H 0.523856 0.464615 0.853440 0.074 Uiso 0.33(3) 1 calc GR . P A 2
H25E H 0.646427 0.472628 0.894265 0.074 Uiso 0.33(3) 1 calc GR . P A 2
H25F H 0.539936 0.441714 0.924210 0.074 Uiso 0.33(3) 1 calc GR . P A 2
C26 C 0.6267(11) 0.1962(8) 1.0230(5) 0.076(4) Uani 1 1 d D . . . .
H26A H 0.614761 0.145973 1.008378 0.114 Uiso 1 1 calc GR . . . .
H26B H 0.565268 0.210021 1.046504 0.114 Uiso 1 1 calc GR . . . .
H26C H 0.700677 0.199839 1.049222 0.114 Uiso 1 1 calc GR . . . .
C27 C 0.5074(16) 0.2547(10) 0.7111(7) 0.060(4) Uani 0.7 1 d D U P A 2
H27A H 0.545935 0.280849 0.680931 0.090 Uiso 0.7 1 calc GR . P A 2
H27B H 0.427223 0.246121 0.694113 0.090 Uiso 0.7 1 calc GR . P A 2
H27C H 0.545683 0.207927 0.720793 0.090 Uiso 0.7 1 calc GR . P A 2


_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 2.259(6) . ?
Dy1 O4 2.265(5) 2_556 ?
Dy1 O5 2.230(5) . ?
Dy1 O7 2.281(6) 4_575 ?
Dy1 O9 2.206(6) . ?
Dy1 O11 2.205(6) . ?
Dy2 O2 2.326(6) 2_546 ?
Dy2 O3 2.293(6) . ?
Dy2 O8 2.278(6) 3_667 ?
Dy2 O13 2.428(9) . ?
Dy2 O13A 2.420(14) . ?
Dy2 O14 2.425(7) . ?
Dy2 O15 2.301(7) . ?
Dy2 O16 2.415(7) . ?
Dy2 O17 2.454(8) . ?
Dy2 O18 2.310(12) . ?
Br1 C3 1.880(8) . ?
Br2 C4 1.892(8) . ?
Br3 C6 1.891(8) . ?
Br4 C7 1.892(8) . ?
Br5 C11 1.880(8) . ?
Br6 C12 1.885(8) . ?
Br7 C14 1.888(8) . ?
Br8 C15 1.885(8) . ?
Br9 C19 1.893(9) . ?
Br10 C20 1.883(9) . ?
Br11 C23 1.883(8) . ?
Br12 C24 1.882(8) . ?
O1 C1 1.240(10) . ?
O2 C1 1.236(10) . ?
O3 C8 1.234(9) . ?
O4 C8 1.240(9) . ?
O5 C9 1.255(10) . ?
O6 C9 1.233(10) . ?
O7 C16 1.225(9) . ?
O8 C16 1.254(9) . ?
O9 C17 1.260(10) . ?
O10 C17 1.223(10) . ?
O11 C21 1.251(9) . ?
O12 C21 1.221(10) . ?
O13 C25 1.554(16) . ?
O13A C25A 1.548(19) . ?
O14 C26 1.441(12) . ?
O17 C27 1.438(13) . ?
C1 C2 1.529(11) . ?
C2 C3 1.386(11) . ?
C2 C7 1.390(11) . ?
C3 C4 1.400(11) . ?
C4 C5 1.379(11) . ?
C5 C6 1.400(11) . ?
C5 C8 1.522(10) . ?
C6 C7 1.384(11) . ?
C9 C10 1.520(11) . ?
C10 C11 1.395(11) . ?
C10 C15 1.388(11) . ?
C11 C12 1.402(10) . ?
C12 C13 1.389(11) . ?
C13 C14 1.375(11) . ?
C13 C16 1.542(11) . ?
C14 C15 1.395(11) . ?
C17 C18 1.499(12) . ?
C18 C19 1.382(13) . ?
C18 C20 1.399(12) 3_666 ?
C19 C20 1.394(12) . ?
C21 C22 1.519(11) . ?
C22 C23 1.381(11) . ?
C22 C24 1.385(12) 3_676 ?
C23 C24 1.404(11) . ?

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 O4 91.7(2) . 2_556 ?
O1 Dy1 O7 86.7(2) . 4_575 ?
O4 Dy1 O7 89.4(2) 2_556 4_575 ?
O5 Dy1 O1 86.5(2) . . ?
O5 Dy1 O4 87.8(2) . 2_556 ?
O5 Dy1 O7 172.6(2) . 4_575 ?
O9 Dy1 O1 90.6(2) . . ?
O9 Dy1 O4 177.1(2) . 2_556 ?
O9 Dy1 O5 94.1(2) . . ?
O9 Dy1 O7 89.0(2) . 4_575 ?
O11 Dy1 O1 178.0(2) . . ?
O11 Dy1 O4 87.6(2) . 2_556 ?
O11 Dy1 O5 95.4(2) . . ?
O11 Dy1 O7 91.4(2) . 4_575 ?
O11 Dy1 O9 90.0(2) . . ?
O2 Dy2 O13 147.6(4) 2_546 . ?
O2 Dy2 O13A 139.1(8) 2_546 . ?
O2 Dy2 O14 143.2(3) 2_546 . ?
O2 Dy2 O16 73.1(2) 2_546 . ?
O2 Dy2 O17 76.5(5) 2_546 . ?
O3 Dy2 O2 85.5(2) . 2_546 ?
O3 Dy2 O13 70.7(4) . . ?
O3 Dy2 O13A 73.8(6) . . ?
O3 Dy2 O14 117.9(3) . . ?
O3 Dy2 O15 136.6(2) . . ?
O3 Dy2 O16 150.8(2) . . ?
O3 Dy2 O17 74.6(5) . . ?
O3 Dy2 O18 80.0(17) . . ?
O8 Dy2 O2 83.5(2) 3_667 2_546 ?
O8 Dy2 O3 81.8(2) 3_667 . ?
O8 Dy2 O13 113.2(5) 3_667 . ?
O8 Dy2 O13A 126.3(7) 3_667 . ?
O8 Dy2 O14 73.2(2) 3_667 . ?
O8 Dy2 O15 138.1(2) 3_667 . ?
O8 Dy2 O16 76.3(2) 3_667 . ?
O8 Dy2 O17 150.1(5) 3_667 . ?
O8 Dy2 O18 150.0(19) 3_667 . ?
O13A Dy2 O14 77.3(8) . . ?
O13A Dy2 O17 64.3(9) . . ?
O14 Dy2 O13 69.2(4) . . ?
O14 Dy2 O17 134.6(5) . . ?
O15 Dy2 O2 110.5(3) . 2_546 ?
O15 Dy2 O13 76.2(5) . . ?
O15 Dy2 O13A 68.0(6) . . ?
O15 Dy2 O14 73.0(3) . . ?
O15 Dy2 O16 71.1(3) . . ?
O15 Dy2 O17 70.8(5) . . ?
O15 Dy2 O18 68.6(19) . . ?
O16 Dy2 O13 136.2(4) . . ?
O16 Dy2 O13A 135.1(7) . . ?
O16 Dy2 O14 73.9(3) . . ?
O16 Dy2 O17 117.6(4) . . ?
O18 Dy2 O2 71.4(15) . 2_546 ?
O18 Dy2 O13 82.8(13) . . ?
O18 Dy2 O14 136.7(19) . . ?
O18 Dy2 O16 110.5(13) . . ?
C1 O1 Dy1 154.0(6) . . ?
C1 O2 Dy2 150.8(6) . 2_556 ?
C8 O3 Dy2 158.2(6) . . ?
C8 O4 Dy1 144.4(5) . 2_546 ?
C9 O5 Dy1 154.4(6) . . ?
C16 O7 Dy1 144.7(5) . 4_676 ?
C16 O8 Dy2 159.5(5) . 3_667 ?
C17 O9 Dy1 156.6(6) . . ?
C21 O11 Dy1 166.5(6) . . ?
C25 O13 Dy2 126.6(10) . . ?
C25A O13A Dy2 129.2(15) . . ?
C26 O14 Dy2 130.3(7) . . ?
C27 O17 Dy2 125.2(10) . . ?
O1 C1 C2 116.8(7) . . ?
O2 C1 O1 126.6(8) . . ?
O2 C1 C2 116.6(7) . . ?
C3 C2 C1 120.8(7) . . ?
C3 C2 C7 119.1(7) . . ?
C7 C2 C1 120.2(7) . . ?
C2 C3 Br1 119.4(6) . . ?
C2 C3 C4 120.1(8) . . ?
C4 C3 Br1 120.5(6) . . ?
C3 C4 Br2 120.5(6) . . ?
C5 C4 Br2 118.6(6) . . ?
C5 C4 C3 121.0(7) . . ?
C4 C5 C6 118.6(7) . . ?
C4 C5 C8 122.6(7) . . ?
C6 C5 C8 118.8(7) . . ?
C5 C6 Br3 118.0(6) . . ?
C7 C6 Br3 121.4(6) . . ?
C7 C6 C5 120.6(7) . . ?
C2 C7 Br4 117.9(6) . . ?
C6 C7 Br4 121.5(6) . . ?
C6 C7 C2 120.6(7) . . ?
O3 C8 O4 126.6(8) . . ?
O3 C8 C5 116.5(7) . . ?
O4 C8 C5 116.9(7) . . ?
O5 C9 C10 117.4(8) . . ?
O6 C9 O5 126.1(8) . . ?
O6 C9 C10 116.5(8) . . ?
C11 C10 C9 120.0(7) . . ?
C15 C10 C9 120.5(7) . . ?
C15 C10 C11 119.4(7) . . ?
C10 C11 Br5 118.6(6) . . ?
C10 C11 C12 119.7(7) . . ?
C12 C11 Br5 121.6(6) . . ?
C11 C12 Br6 119.9(6) . . ?
C13 C12 Br6 119.9(6) . . ?
C13 C12 C11 120.2(7) . . ?
C12 C13 C16 120.2(7) . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 C16 120.1(7) . . ?
C13 C14 Br7 118.1(6) . . ?
C13 C14 C15 120.5(7) . . ?
C15 C14 Br7 121.3(6) . . ?
C10 C15 Br8 118.2(6) . . ?
C10 C15 C14 120.3(7) . . ?
C14 C15 Br8 121.5(6) . . ?
O7 C16 O8 127.0(7) . . ?
O7 C16 C13 116.4(7) . . ?
O8 C16 C13 116.6(7) . . ?
O9 C17 C18 117.7(7) . . ?
O10 C17 O9 124.9(8) . . ?
O10 C17 C18 117.4(7) . . ?
C19 C18 C17 120.7(8) . . ?
C19 C18 C20 119.0(8) . 3_666 ?
C20 C18 C17 120.3(9) 3_666 . ?
C18 C19 Br9 118.4(7) . . ?
C18 C19 C20 121.6(8) . . ?
C20 C19 Br9 120.0(8) . . ?
C18 C20 Br10 118.5(7) 3_666 . ?
C19 C20 Br10 122.2(7) . . ?
C19 C20 C18 119.4(9) . 3_666 ?
O11 C21 C22 117.6(7) . . ?
O12 C21 O11 126.5(8) . . ?
O12 C21 C22 115.9(7) . . ?
C23 C22 C21 120.3(8) . . ?
C23 C22 C24 119.6(7) . 3_676 ?
C24 C22 C21 120.1(7) 3_676 . ?
C22 C23 Br11 119.1(6) . . ?
C22 C23 C24 120.6(8) . . ?
C24 C23 Br11 120.3(6) . . ?
C22 C24 Br12 119.0(6) 3_676 . ?
C22 C24 C23 119.8(7) 3_676 . ?
C23 C24 Br12 121.2(6) . . ?

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
_geom_hbond_publ_flag
O13 H13 O12 0.853(10) 2.03(13) 2.654(16) 129(14) 2_646 yes
O13A H13A O6 0.853(10) 2.47(15) 3.14(3) 136(19) 2_646 yes
O14 H14 O12 0.858(10) 1.91(3) 2.732(10) 159(7) 2_646 yes
O15 H15B O6 0.85(2) 1.83(5) 2.649(9) 163(13) 2_646 yes
O16 H16B O10 0.85(2) 2.03(5) 2.770(9) 145(8) 2_646 yes
C26 H26A O16 0.96 2.59 3.184(16) 120.2 . yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1ce
_database_code_depnum_ccdc_archive 'CCDC 1940034'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 Ce O9'
_chemical_formula_sum            'C15 H12 Br6 Ce O9'
_chemical_formula_weight         955.77
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.482(5)
_cell_length_b                   10.656(3)
_cell_length_c                   22.090(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.658(9)
_cell_angle_gamma                90
_cell_volume                     4806(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    296
_cell_measurement_theta_max      31.098
_cell_measurement_theta_min      2.894
_shelx_estimated_absorpt_T_max   0.535
_shelx_estimated_absorpt_T_min   0.223
_exptl_absorpt_coefficient_mu    11.915
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1324 before and 0.0709 after correction. The Ratio of minimum to maximum transmission is 0.6126. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.642
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47155
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.894
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4117
_reflns_number_total             4724
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.000297(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+13.6334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Ce1 Ce 0.52675(2) 0.52366(2) 0.39181(2) 0.01628(6) Uani 1 1 d . . . . .
Br1 Br 0.76047(2) 0.49788(3) 0.31512(2) 0.03475(10) Uani 1 1 d . . . . .
Br2 Br 0.90380(2) 0.63922(3) 0.33729(2) 0.03380(10) Uani 1 1 d . . . . .
Br3 Br 0.77507(2) 1.10678(3) 0.35642(2) 0.03540(10) Uani 1 1 d . . . . .
Br4 Br 0.63195(2) 0.96169(4) 0.33191(2) 0.03906(11) Uani 1 1 d . . . . .
Br5 Br 0.64132(2) 0.14064(3) 0.49632(2) 0.03816(11) Uani 1 1 d . . . . .
Br6 Br 0.63328(2) -0.17018(3) 0.50403(2) 0.03198(10) Uani 1 1 d . . . . .
O1 O 0.61437(12) 0.6520(2) 0.36321(12) 0.0357(6) Uani 1 1 d . . . . .
O2 O 0.62080(14) 0.6544(3) 0.26339(13) 0.0518(8) Uani 1 1 d . . . . .
O3 O 0.90812(11) 0.9731(2) 0.40965(11) 0.0271(5) Uani 1 1 d . . . . .
O4 O 0.93329(11) 0.9308(2) 0.31728(11) 0.0255(5) Uani 1 1 d . . . . .
O5 O 0.51875(12) 0.3070(2) 0.43199(11) 0.0284(6) Uani 1 1 d . . . . .
O6 O 0.49966(12) 0.3420(2) 0.52775(12) 0.0301(6) Uani 1 1 d . . . . .
O7 O 0.58024(14) 0.4009(2) 0.31383(13) 0.0358(6) Uani 1 1 d D . . . .
H7 H 0.582(2) 0.429(4) 0.2797(9) 0.045(13) Uiso 1 1 d D . . . .
O8 O 0.62064(12) 0.4957(3) 0.47287(12) 0.0317(6) Uani 1 1 d D . . . .
H8 H 0.613(2) 0.512(4) 0.5076(9) 0.053(15) Uiso 1 1 d D . . . .
O9 O 0.46704(14) 0.6876(2) 0.32964(13) 0.0380(7) Uani 1 1 d D . . . .
H9 H 0.4415(15) 0.666(4) 0.3012(12) 0.038(12) Uiso 1 1 d D . . . .
C1 C 0.64131(16) 0.6774(3) 0.31582(17) 0.0254(8) Uani 1 1 d . . . . .
C2 C 0.70766(15) 0.7418(3) 0.32603(14) 0.0194(7) Uani 1 1 d . . . . .
C3 C 0.76530(16) 0.6740(3) 0.32622(15) 0.0209(7) Uani 1 1 d . . . . .
C4 C 0.82589(15) 0.7338(3) 0.33560(15) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.82884(15) 0.8627(3) 0.34529(15) 0.0211(7) Uani 1 1 d . . . . .
C6 C 0.89437(15) 0.9273(3) 0.35776(16) 0.0210(7) Uani 1 1 d . . . . .
C7 C 0.77108(16) 0.9309(3) 0.34521(15) 0.0219(7) Uani 1 1 d . . . . .
C8 C 0.71120(15) 0.8709(3) 0.33495(15) 0.0217(7) Uani 1 1 d . . . . .
C9 C 0.50770(15) 0.2721(3) 0.48312(16) 0.0200(7) Uani 1 1 d . . . . .
C10 C 0.50345(15) 0.1310(3) 0.49353(14) 0.0166(7) Uani 1 1 d . . . . .
C11 C 0.55988(15) 0.0581(3) 0.49664(15) 0.0192(7) Uani 1 1 d . . . . .
C12 C 0.55646(15) -0.0720(3) 0.50225(14) 0.0186(7) Uani 1 1 d . . . . .
C13 C 0.6004(3) 0.2764(4) 0.3166(3) 0.0791(19) Uani 1 1 d . . . . .
H13A H 0.637885 0.266094 0.293644 0.119 Uiso 1 1 calc GR . . . .
H13B H 0.565455 0.223606 0.299845 0.119 Uiso 1 1 calc GR . . . .
H13C H 0.611727 0.253378 0.358115 0.119 Uiso 1 1 calc GR . . . .
C14 C 0.68941(19) 0.4966(5) 0.4714(2) 0.0565(13) Uani 1 1 d . . . . .
H14A H 0.702334 0.430919 0.445161 0.085 Uiso 1 1 calc GR . . . .
H14B H 0.709583 0.483285 0.511687 0.085 Uiso 1 1 calc GR . . . .
H14C H 0.703096 0.576159 0.456489 0.085 Uiso 1 1 calc GR . . . .
C15 C 0.4588(3) 0.8178(4) 0.3400(2) 0.0616(14) Uani 1 1 d . . . . .
H15A H 0.462195 0.862817 0.302690 0.092 Uiso 1 1 calc GR . . . .
H15B H 0.492197 0.846380 0.369793 0.092 Uiso 1 1 calc GR . . . .
H15C H 0.416486 0.832343 0.354347 0.092 Uiso 1 1 calc GR . . . .


_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
Ce1 O1 2.382(2) . ?
Ce1 O3 2.551(2) 3_445 ?
Ce1 O4 2.616(2) 3_445 ?
Ce1 O5 2.484(2) . ?
Ce1 O6 2.378(2) 5_666 ?
Ce1 O7 2.487(3) . ?
Ce1 O8 2.537(2) . ?
Ce1 O9 2.482(2) . ?
Ce1 C6 2.940(3) 3_445 ?
Br1 C3 1.894(3) . ?
Br2 C4 1.885(3) . ?
Br3 C7 1.891(3) . ?
Br4 C8 1.886(3) . ?
Br5 C11 1.886(3) . ?
Br6 C12 1.887(3) . ?
O1 C1 1.252(4) . ?
O2 C1 1.224(4) . ?
O3 C6 1.257(4) . ?
O4 C6 1.246(4) . ?
O5 C9 1.227(4) . ?
O6 C9 1.257(4) . ?
O7 H7 0.814(10) . ?
O7 C13 1.390(5) . ?
O8 H8 0.816(10) . ?
O8 C14 1.412(5) . ?
O9 H9 0.816(10) . ?
O9 C15 1.418(5) . ?
C1 C2 1.523(4) . ?
C2 C3 1.384(5) . ?
C2 C8 1.390(5) . ?
C3 C4 1.396(4) . ?
C4 C5 1.391(5) . ?
C5 C6 1.513(4) . ?
C5 C7 1.388(5) . ?
C7 C8 1.386(4) . ?
C9 C10 1.525(4) . ?
C10 C11 1.390(4) . ?
C10 C12 1.389(4) 5_656 ?
C11 C12 1.394(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 Ce1 O3 155.50(9) . 3_445 ?
O1 Ce1 O4 125.36(8) . 3_445 ?
O1 Ce1 O5 134.55(9) . . ?
O1 Ce1 O7 74.60(9) . . ?
O1 Ce1 O8 73.16(9) . . ?
O1 Ce1 O9 78.29(9) . . ?
O1 Ce1 C6 146.28(9) . 3_445 ?
O3 Ce1 O4 50.19(7) 3_445 3_445 ?
O3 Ce1 C6 25.21(8) 3_445 3_445 ?
O4 Ce1 C6 25.06(8) 3_445 3_445 ?
O5 Ce1 O3 69.94(8) . 3_445 ?
O5 Ce1 O4 78.88(8) . 3_445 ?
O5 Ce1 O7 78.71(8) . . ?
O5 Ce1 O8 72.95(8) . . ?
O5 Ce1 C6 71.36(8) . 3_445 ?
O6 Ce1 O1 94.27(9) 5_666 . ?
O6 Ce1 O3 74.61(8) 5_666 3_445 ?
O6 Ce1 O4 119.93(8) 5_666 3_445 ?
O6 Ce1 O5 105.49(8) 5_666 . ?
O6 Ce1 O7 166.86(9) 5_666 . ?
O6 Ce1 O8 75.44(9) 5_666 . ?
O6 Ce1 O9 81.84(9) 5_666 . ?
O6 Ce1 C6 98.08(9) 5_666 3_445 ?
O7 Ce1 O3 118.34(9) . 3_445 ?
O7 Ce1 O4 72.91(9) . 3_445 ?
O7 Ce1 O8 94.35(9) . . ?
O7 Ce1 C6 95.05(10) . 3_445 ?
O8 Ce1 O3 122.91(8) . 3_445 ?
O8 Ce1 O4 150.93(8) . 3_445 ?
O8 Ce1 C6 140.38(9) . 3_445 ?
O9 Ce1 O3 78.55(9) . 3_445 ?
O9 Ce1 O4 67.38(8) . 3_445 ?
O9 Ce1 O5 143.92(8) . . ?
O9 Ce1 O7 102.23(10) . . ?
O9 Ce1 O8 141.67(9) . . ?
O9 Ce1 C6 72.64(9) . 3_445 ?
C1 O1 Ce1 137.6(2) . . ?
C6 O3 Ce1 94.99(19) . 3 ?
C6 O4 Ce1 92.17(19) . 3 ?
C9 O5 Ce1 129.2(2) . . ?
C9 O6 Ce1 174.2(2) . 5_666 ?
Ce1 O7 H7 121(3) . . ?
C13 O7 Ce1 128.2(3) . . ?
C13 O7 H7 110(3) . . ?
Ce1 O8 H8 116(3) . . ?
C14 O8 Ce1 133.2(2) . . ?
C14 O8 H8 107(3) . . ?
Ce1 O9 H9 119(3) . . ?
C15 O9 Ce1 131.2(3) . . ?
C15 O9 H9 109(3) . . ?
O1 C1 C2 115.0(3) . . ?
O2 C1 O1 127.4(3) . . ?
O2 C1 C2 117.6(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 C8 118.8(3) . . ?
C8 C2 C1 120.2(3) . . ?
C2 C3 Br1 118.8(2) . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 Br1 120.5(2) . . ?
C3 C4 Br2 120.0(2) . . ?
C5 C4 Br2 119.9(2) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 120.2(3) . . ?
C7 C5 C4 119.4(3) . . ?
C7 C5 C6 120.3(3) . . ?
O3 C6 Ce1 59.81(16) . 3 ?
O3 C6 C5 118.2(3) . . ?
O4 C6 Ce1 62.77(16) . 3 ?
O4 C6 O3 122.3(3) . . ?
O4 C6 C5 119.5(3) . . ?
C5 C6 Ce1 172.5(2) . 3 ?
C5 C7 Br3 119.4(2) . . ?
C8 C7 Br3 120.5(2) . . ?
C8 C7 C5 120.1(3) . . ?
C2 C8 Br4 117.9(2) . . ?
C7 C8 Br4 121.1(2) . . ?
C7 C8 C2 121.0(3) . . ?
O5 C9 O6 126.0(3) . . ?
O5 C9 C10 117.0(3) . . ?
O6 C9 C10 116.9(3) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C10 C9 121.2(3) 5_656 . ?
C12 C10 C11 118.7(3) 5_656 . ?
C10 C11 Br5 118.2(2) . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 Br5 121.0(2) . . ?
C10 C12 Br6 119.1(2) 5_656 . ?
C10 C12 C11 120.5(3) 5_656 . ?
C11 C12 Br6 120.4(2) . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O7 H7 O4 0.814(10) 2.14(2) 2.904(4) 156(4) 4_645 yes
O8 H8 O3 0.816(10) 1.916(12) 2.728(4) 173(5) 7_666 yes
O9 H9 O2 0.816(10) 1.840(14) 2.643(4) 168(4) 2_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5eu
_database_code_depnum_ccdc_archive 'CCDC 1940039'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H12 Br6 Eu O9'
_chemical_formula_sum            'C15 H12 Br6 Eu O9'
_chemical_formula_weight         967.62
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.2349(12)
_cell_length_b                   10.5715(6)
_cell_length_c                   22.0267(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.846(2)
_cell_angle_gamma                90
_cell_volume                     4695.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.617
_cell_measurement_theta_min      2.857
_shelx_estimated_absorpt_T_max   0.424
_shelx_estimated_absorpt_T_min   0.163
_exptl_absorpt_coefficient_mu    12.928
_exptl_absorpt_correction_T_max  0.4923
_exptl_absorpt_correction_T_min  0.2471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1662 before and 0.0677 after correction. The Ratio of minimum to maximum transmission is 0.5019. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3922
_reflns_number_total             4601
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.000183(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²+15.1047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0496
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Eu1 Eu 0.52470(2) 0.52190(2) 0.39272(2) 0.01544(6) Uani 1 1 d . . . . .
Br1 Br 0.75969(2) 0.49159(4) 0.31572(2) 0.03195(11) Uani 1 1 d . . . . .
Br2 Br 0.90438(2) 0.63399(4) 0.33821(2) 0.03036(11) Uani 1 1 d . . . . .
Br3 Br 0.77367(2) 1.10602(4) 0.35597(2) 0.03301(12) Uani 1 1 d . . . . .
Br4 Br 0.62901(2) 0.95907(4) 0.33129(2) 0.03597(12) Uani 1 1 d . . . . .
Br5 Br 0.64260(2) 0.14370(4) 0.49641(2) 0.03616(13) Uani 1 1 d . . . . .
Br6 Br 0.63554(2) -0.16974(4) 0.50346(2) 0.02890(11) Uani 1 1 d . . . . .
O1 O 0.61073(13) 0.6512(3) 0.36515(14) 0.0283(7) Uani 1 1 d . . . . .
O2 O 0.61902(15) 0.6403(3) 0.26520(15) 0.0431(8) Uani 1 1 d . . . . .
O3 O 0.90789(13) 0.9750(3) 0.41065(13) 0.0266(7) Uani 1 1 d . . . . .
O4 O 0.93545(12) 0.9250(2) 0.31928(13) 0.0239(6) Uani 1 1 d . . . . .
O5 O 0.51701(13) 0.3113(2) 0.43297(13) 0.0249(6) Uani 1 1 d . . . . .
O6 O 0.49944(13) 0.3435(2) 0.52981(14) 0.0261(7) Uani 1 1 d . . . . .
O7 O 0.58082(15) 0.4036(3) 0.31927(16) 0.0321(7) Uani 1 1 d D . . . .
O8 O 0.61769(13) 0.4949(3) 0.47040(14) 0.0279(7) Uani 1 1 d D . . . .
O9 O 0.46650(15) 0.6800(3) 0.33068(15) 0.0331(7) Uani 1 1 d D . . . .
C1 C 0.63872(18) 0.6709(3) 0.31742(19) 0.0209(9) Uani 1 1 d . . . . .
C2 C 0.70580(17) 0.7375(3) 0.32686(17) 0.0181(8) Uani 1 1 d . . . . .
C3 C 0.76434(19) 0.6689(3) 0.32716(18) 0.0202(9) Uani 1 1 d . . . . .
C4 C 0.82526(17) 0.7297(3) 0.33644(19) 0.0199(9) Uani 1 1 d . . . . .
C5 C 0.82867(18) 0.8595(3) 0.34591(17) 0.0180(8) Uani 1 1 d . . . . .
C6 C 0.89513(18) 0.9252(3) 0.35914(19) 0.0208(9) Uani 1 1 d . . . . .
C7 C 0.76980(18) 0.9282(3) 0.34531(18) 0.0197(8) Uani 1 1 d . . . . .
C8 C 0.70894(18) 0.8678(4) 0.33525(18) 0.0201(9) Uani 1 1 d . . . . .
C9 C 0.50689(17) 0.2743(3) 0.48452(19) 0.0175(8) Uani 1 1 d . . . . .
C10 C 0.50302(17) 0.1320(3) 0.49381(17) 0.0161(8) Uani 1 1 d . . . . .
C11 C 0.56027(17) 0.0591(3) 0.49682(18) 0.0173(8) Uani 1 1 d . . . . .
C12 C 0.55747(17) -0.0717(3) 0.50186(17) 0.0168(8) Uani 1 1 d . . . . .
C13 C 0.5938(3) 0.2742(5) 0.3153(3) 0.0677(19) Uani 1 1 d . . . . .
H13A H 0.636211 0.261850 0.299730 0.102 Uiso 1 1 calc GR . . . .
H13B H 0.559971 0.234926 0.288512 0.102 Uiso 1 1 calc GR . . . .
H13C H 0.594130 0.236809 0.355092 0.102 Uiso 1 1 calc GR . . . .
C14 C 0.6871(2) 0.4936(6) 0.4693(3) 0.0514(15) Uani 1 1 d . . . . .
H14A H 0.699108 0.439121 0.437187 0.077 Uiso 1 1 calc GR . . . .
H14B H 0.706968 0.462992 0.507671 0.077 Uiso 1 1 calc GR . . . .
H14C H 0.702589 0.577800 0.462462 0.077 Uiso 1 1 calc GR . . . .
C15 C 0.4569(3) 0.8109(4) 0.3403(3) 0.0553(15) Uani 1 1 d . . . . .
H15A H 0.460686 0.855826 0.302877 0.083 Uiso 1 1 calc GR . . . .
H15B H 0.489838 0.841106 0.370739 0.083 Uiso 1 1 calc GR . . . .
H15C H 0.413527 0.824469 0.353764 0.083 Uiso 1 1 calc GR . . . .
H8 H 0.611(2) 0.501(4) 0.5064(8) 0.040(15) Uiso 1 1 d D . . . .
H9 H 0.438(2) 0.656(5) 0.3042(19) 0.07(2) Uiso 1 1 d D . . . .
H7 H 0.582(3) 0.435(5) 0.2856(12) 0.056(18) Uiso 1 1 d 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
Eu1 O1 2.334(3) . ?
Eu1 O3 2.479(3) 3_445 ?
Eu1 O4 2.537(3) 3_445 ?
Eu1 O5 2.406(3) . ?
Eu1 O6 2.306(3) 5_666 ?
Eu1 O7 2.404(3) . ?
Eu1 O8 2.451(3) . ?
Eu1 O9 2.403(3) . ?
Br1 C3 1.893(4) . ?
Br2 C4 1.892(4) . ?
Br3 C7 1.895(4) . ?
Br4 C8 1.879(4) . ?
Br5 C11 1.891(3) . ?
Br6 C12 1.887(3) . ?
O1 C1 1.253(5) . ?
O2 C1 1.228(5) . ?
O3 C6 1.258(5) . ?
O4 C6 1.248(5) . ?
O5 C9 1.234(5) . ?
O6 C9 1.256(5) . ?
O7 C13 1.397(6) . ?
O7 H7 0.816(10) . ?
O8 C14 1.407(5) . ?
O8 H8 0.820(10) . ?
O9 C15 1.416(5) . ?
O9 H9 0.822(10) . ?
C1 C2 1.528(5) . ?
C2 C3 1.388(5) . ?
C2 C8 1.391(5) . ?
C3 C4 1.390(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.520(5) . ?
C5 C7 1.395(5) . ?
C7 C8 1.388(5) . ?
C9 C10 1.522(5) . ?
C10 C11 1.388(5) . ?
C10 C12 1.390(5) 5_656 ?
C11 C12 1.389(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 Eu1 O3 154.27(9) . 3_445 ?
O1 Eu1 O4 125.25(10) . 3_445 ?
O1 Eu1 O5 135.29(9) . . ?
O1 Eu1 O7 74.01(10) . . ?
O1 Eu1 O8 72.80(10) . . ?
O1 Eu1 O9 77.61(10) . . ?
O3 Eu1 O4 51.96(9) 3_445 3_445 ?
O5 Eu1 O3 70.36(9) . 3_445 ?
O5 Eu1 O4 78.27(9) . 3_445 ?
O5 Eu1 O8 72.82(9) . . ?
O6 Eu1 O1 92.32(10) 5_666 . ?
O6 Eu1 O3 74.99(9) 5_666 3_445 ?
O6 Eu1 O4 122.50(9) 5_666 3_445 ?
O6 Eu1 O5 105.88(10) 5_666 . ?
O6 Eu1 O7 163.87(10) 5_666 . ?
O6 Eu1 O8 75.72(10) 5_666 . ?
O6 Eu1 O9 82.39(11) 5_666 . ?
O7 Eu1 O3 120.93(10) . 3_445 ?
O7 Eu1 O4 73.27(10) . 3_445 ?
O7 Eu1 O5 79.38(10) . . ?
O7 Eu1 O8 91.77(11) . . ?
O8 Eu1 O3 123.47(10) . 3_445 ?
O8 Eu1 O4 149.49(9) . 3_445 ?
O9 Eu1 O3 78.56(10) . 3_445 ?
O9 Eu1 O4 68.27(9) . 3_445 ?
O9 Eu1 O5 144.00(10) . . ?
O9 Eu1 O7 102.46(11) . . ?
O9 Eu1 O8 142.05(10) . . ?
C1 O1 Eu1 135.7(3) . . ?
C6 O3 Eu1 93.8(2) . 3 ?
C6 O4 Eu1 91.3(2) . 3 ?
C9 O5 Eu1 130.8(2) . . ?
C9 O6 Eu1 173.8(3) . 5_666 ?
Eu1 O7 H7 117(4) . . ?
C13 O7 Eu1 130.8(3) . . ?
C13 O7 H7 109(4) . . ?
Eu1 O8 H8 119(3) . . ?
C14 O8 Eu1 134.3(3) . . ?
C14 O8 H8 106(3) . . ?
Eu1 O9 H9 118(4) . . ?
C15 O9 Eu1 131.4(3) . . ?
C15 O9 H9 108(4) . . ?
O1 C1 C2 114.9(3) . . ?
O2 C1 O1 127.5(4) . . ?
O2 C1 C2 117.6(4) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 C8 119.1(3) . . ?
C8 C2 C1 120.3(3) . . ?
C2 C3 Br1 118.9(3) . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 Br1 120.7(3) . . ?
C3 C4 Br2 119.6(3) . . ?
C5 C4 Br2 119.6(3) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 C7 118.8(3) . . ?
C7 C5 C6 120.3(3) . . ?
O3 C6 Eu1 60.13(19) . 3 ?
O3 C6 C5 118.4(3) . . ?
O4 C6 Eu1 62.73(19) . 3 ?
O4 C6 O3 122.6(3) . . ?
O4 C6 C5 119.0(3) . . ?
C5 C6 Eu1 173.0(3) . 3 ?
C5 C7 Br3 119.3(3) . . ?
C8 C7 Br3 120.2(3) . . ?
C8 C7 C5 120.5(3) . . ?
C2 C8 Br4 118.2(3) . . ?
C7 C8 Br4 121.3(3) . . ?
C7 C8 C2 120.5(3) . . ?
O5 C9 O6 125.9(3) . . ?
O5 C9 C10 116.9(3) . . ?
O6 C9 C10 117.3(4) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 C12 118.6(3) . 5_656 ?
C12 C10 C9 121.2(3) 5_656 . ?
C10 C11 Br5 118.0(3) . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 Br5 120.9(3) . . ?
C10 C12 Br6 119.2(3) 5_656 . ?
C11 C12 Br6 120.6(3) . . ?
C11 C12 C10 120.2(3) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O3 0.820(10) 1.914(12) 2.732(4) 176(5) 7_666 yes
O9 H9 O2 0.822(10) 1.845(18) 2.648(4) 165(6) 2_655 yes
O7 H7 O4 0.816(10) 2.31(3) 3.050(4) 151(5) 4_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_14tb
_database_code_depnum_ccdc_archive 'CCDC 1940051'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26.7 H15.4 Br12 O17 Tb2'
_chemical_formula_sum            'C26.70 H15.40 Br12 O17 Tb2'
_chemical_formula_weight         1884.85
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.634(6)
_cell_length_b                   18.038(8)
_cell_length_c                   21.569(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.005(19)
_cell_angle_gamma                90
_cell_volume                     4482(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8064
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.566
_cell_measurement_theta_min      2.944
_shelx_estimated_absorpt_T_max   0.337
_shelx_estimated_absorpt_T_min   0.189
_exptl_absorpt_coefficient_mu    13.891
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1519 before and 0.0798 after correction. The Ratio of minimum to maximum transmission is 0.6992. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3446
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            98816
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.868
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7069
_reflns_number_total             8797
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.219
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       0.000170(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8797
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+24.6865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O14-H14
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O13A-H13A
 0.85 with sigma of 0.01
 O13-H13
 0.85 with sigma of 0.01
 O15-H15A = O15-H15B
 0.85 with sigma of 0.02
 O16-H16A = O16-H16B
 0.85 with sigma of 0.02
 C26-H14
 1.915338 with sigma of 0.02
 Tb2-H14
 2.96379 with sigma of 0.02
 C27-H17
 1.91147 with sigma of 0.02
 Tb2-H17
 3.083201 with sigma of 0.02
 C25A-H13A
 2.001639 with sigma of 0.02
 Tb2-H13A
 2.970671 with sigma of 0.02
 C25-H13
 2.006304 with sigma of 0.02
 Tb2-H13
 2.996201 with sigma of 0.02
 H15A-H15B
 1.34 with sigma of 0.04
 H16A-H16B
 1.34 with sigma of 0.04
 Tb2-O15 \\sim Tb2-O18
 with sigma of 0.01
 Tb2-O14 \\sim Tb2-O17
 with sigma of 0.01
 O14-C26 \\sim O17-C27
 with sigma of 0.01
 Tb2-O13 \\sim Tb2-O13A
 with sigma of 0.02
 O13-C25 \\sim O13A-C25A
 with sigma of 0.02
 Tb2-C25 \\sim Tb2-C25A
 with sigma of 0.04
 Tb2-H15A \\sim Tb2-H15B
 with sigma of 0.02
 Tb2-H16A \\sim Tb2-H16B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O17) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O13) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O13A) \\sim Ueq, Uanis(C25A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Tb2, O17, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Tb2, O18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Tb2, O13, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Tb2, O13A, C25A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O13A)=Sof(H13A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(O13)=Sof(H13)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
 Fixed Sof: O17(0.7) H17(0.7) O18(0.3) H18A(0.3) H18B(0.3) C27(0.7) H27A(0.7)
 H27B(0.7) H27C(0.7)
6.a Rotating group:
 O18(H18A,H18B)
6.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C25(H25A,H25B,H25C), C25A(H25D,H25E,
 H25F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.43748(2) 0.74803(2) 0.63077(2) 0.01360(7) Uani 1 1 d . . . . .
Tb2 Tb 0.49669(2) 0.24960(2) 0.87164(2) 0.01580(7) Uani 1 1 d D U . . .
Br1 Br 0.31499(7) 0.67321(3) 0.85025(3) 0.04200(19) Uani 1 1 d . . . . .
Br2 Br 0.31265(7) 0.51597(4) 0.93026(3) 0.04260(19) Uani 1 1 d . . . . .
Br3 Br 0.21395(7) 0.35606(3) 0.70506(3) 0.04415(19) Uani 1 1 d . . . . .
Br4 Br 0.21041(7) 0.51580(4) 0.62455(3) 0.04064(18) Uani 1 1 d . . . . .
Br5 Br 0.60348(6) 0.95034(3) 0.81292(3) 0.03519(16) Uani 1 1 d . . . . .
Br6 Br 0.64969(8) 0.94693(4) 0.96847(3) 0.0476(2) Uani 1 1 d . . . . .
Br7 Br 0.70397(8) 0.63628(4) 0.96339(3) 0.0514(2) Uani 1 1 d . . . . .
Br8 Br 0.67070(9) 0.64116(4) 0.80626(4) 0.0581(2) Uani 1 1 d . . . . .
Br9 Br 0.54730(7) 0.67080(4) 0.45815(4) 0.0500(2) Uani 1 1 d . . . . .
Br10 Br 0.43781(8) 0.54493(4) 0.35214(4) 0.0531(2) Uani 1 1 d . . . . .
Br11 Br 0.51424(7) 0.86332(4) 0.40179(3) 0.04505(19) Uani 1 1 d . . . . .
Br12 Br 0.41182(7) 1.02872(4) 0.35136(3) 0.04003(18) Uani 1 1 d . . . . .
O1 O 0.3312(4) 0.6821(2) 0.6928(2) 0.0343(11) Uani 1 1 d . . . . .
O2 O 0.1409(4) 0.6806(2) 0.69426(19) 0.0303(10) Uani 1 1 d . . . . .
O3 O 0.3625(3) 0.3443(2) 0.8565(2) 0.0309(10) Uani 1 1 d . . . . .
O4 O 0.1738(3) 0.3514(2) 0.8615(2) 0.0287(10) Uani 1 1 d . . . . .
O5 O 0.5489(4) 0.7836(2) 0.71926(19) 0.0349(11) Uani 1 1 d . . . . .
O6 O 0.7349(4) 0.8169(3) 0.7326(2) 0.0432(12) Uani 1 1 d . . . . .
O7 O 0.8051(3) 0.7908(2) 1.04858(19) 0.0316(10) Uani 1 1 d . . . . .
O8 O 0.6160(3) 0.7842(2) 1.05317(19) 0.0303(10) Uani 1 1 d . . . . .
O9 O 0.5453(4) 0.6487(2) 0.6180(2) 0.0303(10) Uani 1 1 d . . . . .
O10 O 0.7159(4) 0.6070(3) 0.5988(3) 0.0564(16) Uani 1 1 d . . . . .
O11 O 0.5357(4) 0.8121(2) 0.56725(19) 0.0288(10) Uani 1 1 d . . . . .
O12 O 0.7014(4) 0.8472(3) 0.5359(2) 0.0434(12) Uani 1 1 d . . . . .
O14 O 0.6254(4) 0.2465(4) 0.9706(2) 0.0624(16) Uani 1 1 d D . . . .
H14 H 0.692(3) 0.268(4) 0.9727(18) 0.094 Uiso 1 1 d DR . . . .
O15 O 0.6830(4) 0.2267(3) 0.8475(3) 0.0598(17) Uani 1 1 d D . . . .
H15A H 0.729(4) 0.193(3) 0.864(4) 0.090 Uiso 1 1 d DR . . . .
H15B H 0.725(4) 0.258(3) 0.832(4) 0.090 Uiso 1 1 d DR . . . .
O16 O 0.5443(4) 0.1197(2) 0.8907(3) 0.0468(13) Uani 1 1 d D . . . .
H16A H 0.498(3) 0.0837(17) 0.893(4) 0.070 Uiso 1 1 d DR . . . .
H16B H 0.612(2) 0.100(2) 0.896(4) 0.070 Uiso 1 1 d DR . . . .
O17 O 0.5164(16) 0.2995(7) 0.7671(3) 0.038(3) Uani 0.7 1 d D U P A 2
H17 H 0.516(9) 0.3451(9) 0.7562(13) 0.057 Uiso 0.7 1 d DR . P B 2
O18 O 0.507(5) 0.2825(18) 0.7672(7) 0.059(11) Uani 0.3 1 d D U P A 1
H18A H 0.453210 0.261084 0.741703 0.088 Uiso 0.3 1 d GR . P A 1
H18B H 0.570531 0.267170 0.755143 0.088 Uiso 0.3 1 d GR . P A 1
C1 C 0.2399(5) 0.6547(3) 0.7070(3) 0.0209(13) Uani 1 1 d . . . . .
C2 C 0.2515(5) 0.5829(3) 0.7441(3) 0.0180(12) Uani 1 1 d . . . . .
C3 C 0.2781(5) 0.5825(3) 0.8084(3) 0.0211(12) Uani 1 1 d . . . . .
C4 C 0.2809(5) 0.5157(3) 0.8423(3) 0.0190(12) Uani 1 1 d . . . . .
C5 C 0.2611(4) 0.4485(3) 0.8113(3) 0.0177(12) Uani 1 1 d . . . . .
C6 C 0.2388(5) 0.4482(3) 0.7463(3) 0.0222(13) Uani 1 1 d . . . . .
C7 C 0.2337(5) 0.5147(3) 0.7132(3) 0.0217(12) Uani 1 1 d . . . . .
C8 C 0.2659(5) 0.3751(3) 0.8463(3) 0.0195(12) Uani 1 1 d . . . . .
C9 C 0.6429(5) 0.7990(3) 0.7518(3) 0.0254(13) Uani 1 1 d . . . . .
C10 C 0.6465(5) 0.7961(3) 0.8226(2) 0.0192(12) Uani 1 1 d . . . . .
C11 C 0.6390(5) 0.8605(3) 0.8565(3) 0.0198(12) Uani 1 1 d . . . . .
C12 C 0.6570(5) 0.8586(3) 0.9219(3) 0.0199(12) Uani 1 1 d . . . . .
C13 C 0.6785(5) 0.7916(3) 0.9534(3) 0.0194(12) Uani 1 1 d . . . . .
C14 C 0.6807(5) 0.7271(3) 0.9195(3) 0.0238(13) Uani 1 1 d . . . . .
C15 C 0.6655(5) 0.7284(3) 0.8540(3) 0.0265(14) Uani 1 1 d . . . . .
C16 C 0.7014(5) 0.7893(3) 1.0247(3) 0.0205(12) Uani 1 1 d . . . . .
C17 C 0.6095(5) 0.6071(3) 0.5909(3) 0.0283(14) Uani 1 1 d . . . . .
C18 C 0.5498(5) 0.5521(3) 0.5434(3) 0.0263(14) Uani 1 1 d . . . . .
C19 C 0.5219(5) 0.5717(3) 0.4819(3) 0.0277(14) Uani 1 1 d . . . . .
C20 C 0.4735(5) 0.5199(3) 0.4376(3) 0.0313(15) Uani 1 1 d . . . . .
C21 C 0.5995(5) 0.8568(3) 0.5430(3) 0.0220(13) Uani 1 1 d . . . . .
C22 C 0.5455(5) 0.9317(3) 0.5208(3) 0.0218(13) Uani 1 1 d . . . . .
C23 C 0.5065(5) 0.9426(3) 0.4583(3) 0.0208(12) Uani 1 1 d . . . . .
C24 C 0.4620(5) 1.0114(3) 0.4370(3) 0.0208(12) Uani 1 1 d . . . . .
C26 C 0.6286(8) 0.1969(6) 1.0234(4) 0.073(3) Uani 1 1 d D . . . .
H26A H 0.605634 0.148134 1.008812 0.110 Uiso 1 1 calc GR . . . .
H26B H 0.576298 0.214476 1.050865 0.110 Uiso 1 1 calc GR . . . .
H26C H 0.705999 0.195216 1.045648 0.110 Uiso 1 1 calc GR . . . .
C27 C 0.5080(11) 0.2548(7) 0.7115(5) 0.062(3) Uani 0.7 1 d D U P A 2
H27A H 0.544607 0.279986 0.680322 0.093 Uiso 0.7 1 calc GR . P A 2
H27B H 0.427756 0.246272 0.695878 0.093 Uiso 0.7 1 calc GR . P A 2
H27C H 0.546043 0.208156 0.721335 0.093 Uiso 0.7 1 calc GR . P A 2
O13 O 0.5978(10) 0.3677(4) 0.8906(7) 0.046(3) Uani 0.70(2) 1 d D U P A 1
H13 H 0.660(5) 0.372(2) 0.917(3) 0.069 Uiso 0.70(2) 1 d DR . P A 1
C25 C 0.5863(12) 0.4387(6) 0.8491(9) 0.065(5) Uani 0.70(2) 1 d D U P A 1
H25A H 0.617448 0.429155 0.810914 0.098 Uiso 0.70(2) 1 calc GR . P A 1
H25B H 0.628475 0.478626 0.871207 0.098 Uiso 0.70(2) 1 calc GR . P A 1
H25C H 0.505935 0.452081 0.839514 0.098 Uiso 0.70(2) 1 calc GR . P A 1
O13A O 0.606(2) 0.3638(10) 0.8669(14) 0.056(8) Uani 0.30(2) 1 d D U P A 2
H13A H 0.666(12) 0.366(3) 0.848(10) 0.084 Uiso 0.30(2) 1 d DR . P A 2
C25A C 0.579(3) 0.4427(13) 0.8901(19) 0.061(9) Uani 0.30(2) 1 d D U P A 2
H25D H 0.522569 0.466161 0.859638 0.091 Uiso 0.30(2) 1 calc GR . P A 2
H25E H 0.648967 0.471705 0.895647 0.091 Uiso 0.30(2) 1 calc GR . P A 2
H25F H 0.549028 0.439054 0.929219 0.091 Uiso 0.30(2) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.279(4) . ?
Tb1 O4 2.289(4) 2_556 ?
Tb1 O5 2.246(4) . ?
Tb1 O7 2.290(4) 4_575 ?
Tb1 O9 2.227(4) . ?
Tb1 O11 2.226(4) . ?
Tb2 O2 2.344(4) 2_546 ?
Tb2 O3 2.307(4) . ?
Tb2 O8 2.305(4) 3_667 ?
Tb2 O14 2.431(5) . ?
Tb2 O15 2.335(5) . ?
Tb2 O16 2.429(5) . ?
Tb2 O17 2.469(7) . ?
Tb2 O18 2.350(11) . ?
Tb2 O13 2.441(7) . ?
Tb2 O13A 2.431(14) . ?
Br1 C3 1.889(6) . ?
Br2 C4 1.882(6) . ?
Br3 C6 1.888(6) . ?
Br4 C7 1.894(6) . ?
Br5 C11 1.890(5) . ?
Br6 C12 1.892(5) . ?
Br7 C14 1.892(5) . ?
Br8 C15 1.886(6) . ?
Br9 C19 1.894(6) . ?
Br10 C20 1.886(7) . ?
Br11 C23 1.890(6) . ?
Br12 C24 1.884(6) . ?
O1 C1 1.247(7) . ?
O2 C1 1.238(7) . ?
O3 C8 1.244(7) . ?
O4 C8 1.240(7) . ?
O5 C9 1.246(7) . ?
O6 C9 1.243(7) . ?
O7 C16 1.245(7) . ?
O8 C16 1.243(7) . ?
O9 C17 1.257(7) . ?
O10 C17 1.226(7) . ?
O11 C21 1.259(7) . ?
O12 C21 1.228(7) . ?
O14 C26 1.445(9) . ?
O17 C27 1.436(11) . ?
C1 C2 1.519(7) . ?
C2 C3 1.379(8) . ?
C2 C7 1.401(8) . ?
C3 C4 1.406(7) . ?
C4 C5 1.389(7) . ?
C5 C6 1.391(8) . ?
C5 C8 1.522(7) . ?
C6 C7 1.392(8) . ?
C9 C10 1.522(8) . ?
C10 C11 1.384(8) . ?
C10 C15 1.398(8) . ?
C11 C12 1.396(8) . ?
C12 C13 1.393(8) . ?
C13 C14 1.377(8) . ?
C13 C16 1.523(8) . ?
C14 C15 1.400(8) . ?
C17 C18 1.523(8) . ?
C18 C19 1.369(9) . ?
C18 C20 1.399(8) 3_666 ?
C19 C20 1.398(8) . ?
C21 C22 1.538(7) . ?
C22 C23 1.375(8) . ?
C22 C24 1.384(8) 3_676 ?
C23 C24 1.397(8) . ?
O13 C25 1.558(13) . ?
O13A C25A 1.555(17) . ?

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 Tb1 O4 91.39(16) . 2_556 ?
O1 Tb1 O7 86.18(16) . 4_575 ?
O4 Tb1 O7 88.81(15) 2_556 4_575 ?
O5 Tb1 O1 86.93(17) . . ?
O5 Tb1 O4 88.33(16) . 2_556 ?
O5 Tb1 O7 172.48(16) . 4_575 ?
O9 Tb1 O1 90.78(16) . . ?
O9 Tb1 O4 177.00(15) . 2_556 ?
O9 Tb1 O5 93.85(16) . . ?
O9 Tb1 O7 89.27(16) . 4_575 ?
O11 Tb1 O1 177.82(16) . . ?
O11 Tb1 O4 88.02(15) . 2_556 ?
O11 Tb1 O5 95.15(17) . . ?
O11 Tb1 O7 91.70(16) . 4_575 ?
O11 Tb1 O9 89.74(16) . . ?
O2 Tb2 O14 143.62(18) 2_546 . ?
O2 Tb2 O16 73.21(16) 2_546 . ?
O2 Tb2 O17 77.4(4) 2_546 . ?
O2 Tb2 O18 71.0(11) 2_546 . ?
O2 Tb2 O13 146.9(3) 2_546 . ?
O2 Tb2 O13A 137.9(8) 2_546 . ?
O3 Tb2 O2 85.18(15) . 2_546 ?
O3 Tb2 O14 117.6(2) . . ?
O3 Tb2 O15 136.93(16) . . ?
O3 Tb2 O16 150.70(15) . . ?
O3 Tb2 O17 75.4(4) . . ?
O3 Tb2 O18 78.6(12) . . ?
O3 Tb2 O13 71.2(3) . . ?
O3 Tb2 O13A 73.4(7) . . ?
O8 Tb2 O2 83.06(16) 3_667 2_546 ?
O8 Tb2 O3 81.67(15) 3_667 . ?
O8 Tb2 O14 73.58(17) 3_667 . ?
O8 Tb2 O15 138.27(16) 3_667 . ?
O8 Tb2 O16 76.38(17) 3_667 . ?
O8 Tb2 O17 150.9(4) 3_667 . ?
O8 Tb2 O18 148.4(14) 3_667 . ?
O8 Tb2 O13 114.9(4) 3_667 . ?
O8 Tb2 O13A 127.3(6) 3_667 . ?
O14 Tb2 O17 133.3(4) . . ?
O14 Tb2 O13 69.4(3) . . ?
O14 Tb2 O13A 78.1(8) . . ?
O15 Tb2 O2 110.4(2) . 2_546 ?
O15 Tb2 O14 73.4(2) . . ?
O15 Tb2 O16 70.75(17) . . ?
O15 Tb2 O17 69.7(4) . . ?
O15 Tb2 O18 70.0(14) . . ?
O15 Tb2 O13 75.6(4) . . ?
O15 Tb2 O13A 68.5(6) . . ?
O16 Tb2 O14 74.4(2) . . ?
O16 Tb2 O17 117.3(3) . . ?
O16 Tb2 O13 136.1(3) . . ?
O16 Tb2 O13A 135.7(7) . . ?
O18 Tb2 O14 137.7(13) . . ?
O18 Tb2 O16 111.4(9) . . ?
O18 Tb2 O13 81.5(9) . . ?
O13A Tb2 O17 62.4(8) . . ?
C1 O1 Tb1 154.2(4) . . ?
C1 O2 Tb2 150.5(4) . 2_556 ?
C8 O3 Tb2 158.7(4) . . ?
C8 O4 Tb1 144.9(4) . 2_546 ?
C9 O5 Tb1 154.1(4) . . ?
C16 O7 Tb1 145.3(4) . 4_676 ?
C16 O8 Tb2 160.1(4) . 3_667 ?
C17 O9 Tb1 156.7(4) . . ?
C21 O11 Tb1 166.4(4) . . ?
C26 O14 Tb2 130.7(5) . . ?
C27 O17 Tb2 123.5(8) . . ?
O1 C1 C2 116.8(5) . . ?
O2 C1 O1 126.5(5) . . ?
O2 C1 C2 116.8(5) . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 C7 118.1(5) . . ?
C7 C2 C1 120.2(5) . . ?
C2 C3 Br1 118.7(4) . . ?
C2 C3 C4 120.9(5) . . ?
C4 C3 Br1 120.4(4) . . ?
C3 C4 Br2 120.6(4) . . ?
C5 C4 Br2 118.9(4) . . ?
C5 C4 C3 120.5(5) . . ?
C4 C5 C6 118.9(5) . . ?
C4 C5 C8 122.0(5) . . ?
C6 C5 C8 119.1(5) . . ?
C5 C6 Br3 118.2(4) . . ?
C5 C6 C7 120.2(5) . . ?
C7 C6 Br3 121.6(4) . . ?
C2 C7 Br4 117.5(4) . . ?
C6 C7 Br4 121.1(4) . . ?
C6 C7 C2 121.3(5) . . ?
O3 C8 C5 116.4(5) . . ?
O4 C8 O3 126.3(5) . . ?
O4 C8 C5 117.2(5) . . ?
O5 C9 C10 117.2(5) . . ?
O6 C9 O5 126.8(6) . . ?
O6 C9 C10 116.0(5) . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 C15 119.6(5) . . ?
C15 C10 C9 119.8(5) . . ?
C10 C11 Br5 118.9(4) . . ?
C10 C11 C12 120.1(5) . . ?
C12 C11 Br5 121.0(4) . . ?
C11 C12 Br6 120.3(4) . . ?
C13 C12 Br6 119.3(4) . . ?
C13 C12 C11 120.4(5) . . ?
C12 C13 C16 120.7(5) . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 C16 120.0(5) . . ?
C13 C14 Br7 118.5(4) . . ?
C13 C14 C15 120.9(5) . . ?
C15 C14 Br7 120.6(4) . . ?
C10 C15 Br8 118.6(4) . . ?
C10 C15 C14 119.6(5) . . ?
C14 C15 Br8 121.8(4) . . ?
O7 C16 C13 116.1(5) . . ?
O8 C16 O7 126.3(5) . . ?
O8 C16 C13 117.5(5) . . ?
O9 C17 C18 117.1(5) . . ?
O10 C17 O9 126.2(6) . . ?
O10 C17 C18 116.7(5) . . ?
C19 C18 C17 120.6(5) . . ?
C19 C18 C20 119.7(6) . 3_666 ?
C20 C18 C17 119.7(6) 3_666 . ?
C18 C19 Br9 118.8(4) . . ?
C18 C19 C20 120.6(6) . . ?
C20 C19 Br9 120.7(5) . . ?
C18 C20 Br10 118.9(5) 3_666 . ?
C19 C20 Br10 121.3(5) . . ?
C19 C20 C18 119.7(6) . 3_666 ?
O11 C21 C22 116.9(5) . . ?
O12 C21 O11 126.7(5) . . ?
O12 C21 C22 116.4(5) . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 C24 119.7(5) . 3_676 ?
C24 C22 C21 120.5(5) 3_676 . ?
C22 C23 Br11 119.0(4) . . ?
C22 C23 C24 120.4(5) . . ?
C24 C23 Br11 120.6(4) . . ?
C22 C24 Br12 118.9(4) 3_676 . ?
C22 C24 C23 119.8(5) 3_676 . ?
C23 C24 Br12 121.3(4) . . ?
C25 O13 Tb2 128.3(9) . . ?
C25A O13A Tb2 129.2(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O14 H14 O12 0.860(10) 1.92(2) 2.731(7) 157(6) 2_646 yes
O15 H15A O10 0.85(2) 1.83(3) 2.647(7) 162(5) 2_646 yes
O15 H15B O6 0.85(2) 1.86(4) 2.647(7) 154(9) 2_646 yes
O16 H16B O10 0.86(2) 1.99(3) 2.777(6) 151(4) 2_646 yes
O18 H18B O6 0.86 2.41 3.07(5) 132.7 2_646 yes
O13 H13 O12 0.856(10) 1.84(3) 2.660(11) 160(7) 2_646 yes
O13A H13A O6 0.852(10) 2.39(8) 3.14(2) 147(11) 2_646 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3tb'
_database_code_depnum_ccdc_archive 'CCDC 2130103'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C20 H44.04 Br4 O20.04 Tb2, 2(Br4 C8 O4), 4(H2 O)'
_chemical_formula_sum            'C36 H52.04 Br12 O32.04 Tb2'
_chemical_formula_weight         2274.21
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4965(3)
_cell_length_b                   12.3708(3)
_cell_length_c                   12.7873(3)
_cell_angle_alpha                78.8140(10)
_cell_angle_beta                 82.6170(10)
_cell_angle_gamma                82.6250(10)
_cell_volume                     1606.23(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.39
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   0.593
_shelx_estimated_absorpt_T_min   0.273
_exptl_absorpt_coefficient_mu    9.730
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0976 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.7635.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1074
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            68573
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.506
_diffrn_reflns_theta_min         3.128
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9004
_reflns_number_total             10691
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.00151(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         10691
_refine_ls_number_restraints     159
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+1.7549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0586
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3
 0.85 with sigma of 0.01
 O5-H5
 0.85 with sigma of 0.01
 O6-H6
 0.85 with sigma of 0.01
 O7B-H7B
 0.85 with sigma of 0.01
 O4-H4
 0.82 with sigma of 0.02
 O7A-H7A
 0.85 with sigma of 0.01
 C5-H3
 1.893693 with sigma of 0.02
 Tb1-H3
 3.073972 with sigma of 0.02
 C7-H5
 1.894238 with sigma of 0.02
 Tb1-H5
 3.078564 with sigma of 0.02
 C8-H6
 1.900962 with sigma of 0.02
 Tb1-H6
 3.051202 with sigma of 0.02
 C9B-H7B
 1.906142 with sigma of 0.02
 Tb1-H7B
 2.790684 with sigma of 0.02
 C9A-H7A
 1.888504 with sigma of 0.02
 Tb1-H7A
 2.922925 with sigma of 0.02
 O7A-C9A \\sim O7B-C9B \\sim O8A-C10A \\sim O8B-C10B
 with sigma of 0.02
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 O4-C6B \\sim O3-C5
 with sigma of 0.02
 O4-C6A \\sim O3-C5
 with sigma of 0.02
 C6B-C5 \\sim C6A-C5
 with sigma of 0.02
 O4-C6B \\sim C5-O3
 with sigma of 0.02
 O4-C6A \\sim C5-O3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O7A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(O8A)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(O8B) \\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(O7B)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(O4) \\sim Ueq, Uanis(C6B) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(O3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(O4) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(O3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O7A, O8A, C9A, C10A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O7B, O8B, C9B, C10B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O3, O4, C5, C6B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O3, O4, C5, C6A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5. Others
 Fixed Sof: O7A(0.02) H7A(0.02) O8A(0.2) H8A(0.2) O8B(0.8) H8B(0.8) C6A(0.75)
 H6AA(0.75) H6AB(0.75) C6B(0.25) H6BA(0.25) H6BB(0.25) C9A(0.2) H9AA(0.2)
 H9AB(0.2) C9B(0.8) H9BA(0.8) H9BB(0.8) C10A(0.2) H10C(0.2) H10D(0.2) C10B(0.8)
 H10E(0.8) H10F(0.8)
6.a Free rotating group:
 O15(H15A,H15B), O16(H16A,H16B)
6.b Rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
6.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6A(H6AA,H6AB), C6B(H6BA,H6BB), C7(H7C,H7D), C8(H8C,H8D),
 C9A(H9AA,H9AB), C9B(H9BA,H9BB), C10A(H10C,H10D), C10B(H10E,H10F)
6.d Idealised tetrahedral OH refined as rotating group:
 O8A(H8A), O8B(H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.59088(2) 0.61791(2) 0.70728(2) 0.02073(4) Uani 1 1 d D . . . .
Br1 Br 0.93275(4) 0.30514(3) 0.88241(3) 0.04959(9) Uani 1 1 d . . . . .
Br2 Br 1.05437(4) 0.24213(3) 1.11941(3) 0.05136(9) Uani 1 1 d . . . . .
Br3 Br 0.78988(3) 0.06646(3) 1.00572(3) 0.04826(9) Uani 1 1 d . . . . .
Br4 Br 0.71091(3) -0.18367(3) 1.12154(3) 0.04518(8) Uani 1 1 d . . . . .
Br5 Br 0.10392(3) 0.99587(3) 0.73136(2) 0.04197(8) Uani 1 1 d . . . . .
Br6 Br -0.18295(3) 1.12944(3) 0.67474(3) 0.04230(8) Uani 1 1 d . . . . .
O1 O 0.76146(18) 0.57127(19) 0.81118(16) 0.0373(5) Uani 1 1 d . . . . .
O2 O 0.9537(2) 0.5568(2) 0.71421(17) 0.0464(6) Uani 1 1 d . . . . .
O3 O 0.49457(19) 0.50734(16) 0.87042(16) 0.0329(4) Uani 1 1 d D U . . .
H3 H 0.5284(17) 0.4473(17) 0.906(2) 0.049 Uiso 1 1 d D U . . .
O4 O 0.3649(2) 0.6417(2) 0.73310(18) 0.0430(5) Uani 1 1 d D U . . .
H4 H 0.322(3) 0.690(2) 0.695(3) 0.053(11) Uiso 1 1 d D . . . .
O5 O 0.5536(2) 0.80591(16) 0.61714(15) 0.0307(4) Uani 1 1 d D . . . .
H5 H 0.489(2) 0.8382(15) 0.584(2) 0.046 Uiso 1 1 d D U . . .
O6 O 0.5627(2) 0.75093(17) 0.82636(15) 0.0388(5) Uani 1 1 d D . . . .
H6 H 0.534(3) 0.7396(16) 0.8928(9) 0.058 Uiso 1 1 d D U . . .
O7A O 0.787(8) 0.686(11) 0.609(3) 0.045(8) Uani 0.02 1 d D U P A 1
H7A H 0.85(3) 0.70(5) 0.645(5) 0.067 Uiso 0.02 1 d D U P B 1
O7B O 0.7796(2) 0.6482(2) 0.58415(17) 0.0406(5) Uani 1 1 d D U . C 2
H7B H 0.8470(12) 0.620(3) 0.6139(18) 0.061 Uiso 1 1 d D U . D 2
O8A O 0.9377(14) 0.5878(13) 0.4203(11) 0.060(3) Uani 0.2 1 d D U P A 1
H8A H 0.966587 0.565869 0.364485 0.090 Uiso 0.2 1 calc R U P A 1
O8B O 0.8525(4) 0.5940(4) 0.3668(3) 0.0709(10) Uani 0.8 1 d D U P C 2
H8B H 0.774201 0.611041 0.368383 0.106 Uiso 0.8 1 calc R U P C 2
O9 O 0.6446(3) 0.43572(17) 0.68277(17) 0.0463(6) Uani 1 1 d . . . . .
H9A H 0.678842 0.397018 0.737563 0.069 Uiso 1 1 d R U . . .
H9B H 0.704762 0.433338 0.630983 0.069 Uiso 1 1 d R U . . .
O10 O 0.5193(2) 0.61241(19) 0.53769(17) 0.0423(5) Uani 1 1 d . . . . .
H10A H 0.520463 0.676117 0.498222 0.063 Uiso 1 1 d R U . . .
H10B H 0.440121 0.600908 0.547002 0.063 Uiso 1 1 d R U . . .
O11 O 0.6062(2) 0.24265(17) 0.80943(16) 0.0399(5) Uani 1 1 d . . . . .
O12 O 0.5441(2) 0.29232(15) 0.96807(15) 0.0352(5) Uani 1 1 d . . . . .
O13 O 0.2191(2) 0.77104(18) 0.60712(19) 0.0439(5) Uani 1 1 d . . . . .
O14 O 0.3433(2) 0.9056(2) 0.5354(2) 0.0468(6) Uani 1 1 d . . . . .
O15 O 0.7464(4) 0.4145(3) 0.4865(3) 0.0762(9) Uani 1 1 d G . . . .
H15A H 0.819151 0.394121 0.510540 0.114 Uiso 1 1 d G U . . .
H15B H 0.758383 0.472627 0.440355 0.114 Uiso 1 1 d G U . . .
O16 O 0.5110(4) 0.7905(3) 0.3751(2) 0.0742(9) Uani 1 1 d G . . . .
H16A H 0.458145 0.800966 0.328158 0.111 Uiso 1 1 d G U . . .
H16B H 0.569628 0.738932 0.362888 0.111 Uiso 1 1 d G U . . .
C1 C 0.8829(3) 0.5534(2) 0.8000(2) 0.0315(6) Uani 1 1 d . . . . .
C2 C 0.9451(2) 0.5257(2) 0.9035(2) 0.0272(5) Uani 1 1 d . . . . .
C3 C 0.9727(3) 0.4160(2) 0.9514(2) 0.0295(5) Uani 1 1 d . . . . .
C4 C 1.0269(2) 0.3898(2) 1.0481(2) 0.0289(5) Uani 1 1 d . . . . .
C5 C 0.3579(3) 0.5072(3) 0.8875(3) 0.0482(7) Uani 1 1 d D U . . .
H5A H 0.330220 0.495253 0.963820 0.058 Uiso 1 1 calc R U . E 1
H5B H 0.332883 0.447229 0.858409 0.058 Uiso 1 1 calc R U . E 1
C6A C 0.2961(4) 0.6109(4) 0.8367(4) 0.0455(8) Uani 0.75 1 d D U P F 1
H6AA H 0.206887 0.603430 0.829503 0.055 Uiso 0.75 1 calc R U P F 1
H6AB H 0.297096 0.667338 0.879573 0.055 Uiso 0.75 1 calc R U P F 1
C6B C 0.2947(12) 0.5555(13) 0.7968(11) 0.0509(16) Uani 0.25 1 d D U P F 2
H6BA H 0.207806 0.586012 0.819026 0.061 Uiso 0.25 1 calc R U P F 2
H6BB H 0.288405 0.499529 0.754618 0.061 Uiso 0.25 1 calc R U P F 2
C7 C 0.5947(4) 0.8843(3) 0.6710(3) 0.0466(8) Uani 1 1 d D . . . .
H7C H 0.568062 0.959052 0.635723 0.056 Uiso 1 1 calc R U . . .
H7D H 0.688187 0.875222 0.668371 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5367(4) 0.8667(3) 0.7838(2) 0.0484(9) Uani 1 1 d D . . . .
H8C H 0.574573 0.910638 0.824390 0.058 Uiso 1 1 calc R U . . .
H8D H 0.444326 0.888199 0.787603 0.058 Uiso 1 1 calc R U . . .
C9A C 0.824(4) 0.725(3) 0.498(2) 0.043(3) Uani 0.2 1 d D U P A 1
H9AA H 0.908455 0.749879 0.497753 0.052 Uiso 0.2 1 calc R U P A 1
H9AB H 0.766513 0.792370 0.481622 0.052 Uiso 0.2 1 calc R U P A 1
C9B C 0.8166(12) 0.7247(8) 0.4880(5) 0.0484(11) Uani 0.8 1 d D U P C 2
H9BA H 0.856085 0.783882 0.507200 0.058 Uiso 0.8 1 calc R U P C 2
H9BB H 0.739843 0.757583 0.454049 0.058 Uiso 0.8 1 calc R U P C 2
C10A C 0.8381(17) 0.6787(14) 0.3981(14) 0.047(2) Uani 0.2 1 d D U P A 1
H10C H 0.758292 0.652872 0.387114 0.056 Uiso 0.2 1 calc R U P A 1
H10D H 0.865268 0.732513 0.335892 0.056 Uiso 0.2 1 calc R U P A 1
C10B C 0.9085(5) 0.6712(4) 0.4102(4) 0.0519(8) Uani 0.8 1 d D U P C 2
H10E H 0.939387 0.727895 0.352334 0.062 Uiso 0.8 1 calc R U P C 2
H10F H 0.982403 0.633502 0.445788 0.062 Uiso 0.8 1 calc R U P C 2
C11 C 0.5652(3) 0.2242(2) 0.9056(2) 0.0274(5) Uani 1 1 d . . . . .
C12 C 0.5333(3) 0.1068(2) 0.95315(19) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.6233(3) 0.0275(2) 1.0024(2) 0.0267(5) Uani 1 1 d . . . . .
C14 C 0.5905(3) -0.0780(2) 1.0500(2) 0.0262(5) Uani 1 1 d . . . . .
C15 C 0.2389(3) 0.8666(2) 0.5587(2) 0.0322(6) Uani 1 1 d . . . . .
C16 C 0.1174(3) 0.9393(2) 0.5257(2) 0.0271(5) Uani 1 1 d . . . . .
C17 C 0.0413(3) 0.9970(2) 0.5989(2) 0.0277(5) Uani 1 1 d . . . . .
C18 C -0.0751(3) 1.0562(2) 0.5737(2) 0.0278(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.3136(19) . ?
Tb1 O3 2.4394(19) . ?
Tb1 O4 2.341(2) . ?
Tb1 O5 2.3944(19) . ?
Tb1 O6 2.418(2) . ?
Tb1 O7A 2.43(4) . ?
Tb1 O7B 2.388(2) . ?
Tb1 O9 2.323(2) . ?
Tb1 O10 2.400(2) . ?
Br1 C3 1.883(3) . ?
Br2 C4 1.881(3) . ?
Br3 C13 1.880(3) . ?
Br4 C14 1.885(3) . ?
Br5 C17 1.891(3) . ?
Br6 C18 1.894(3) . ?
O1 C1 1.260(3) . ?
O2 C1 1.240(3) . ?
O3 H3 0.852(9) . ?
O3 C5 1.423(4) . ?
O4 H4 0.819(18) . ?
O4 C6A 1.432(4) . ?
O4 C6B 1.434(11) . ?
O5 H5 0.862(9) . ?
O5 C7 1.430(4) . ?
O6 H6 0.854(9) . ?
O6 C8 1.434(4) . ?
O7A H7A 0.850(10) . ?
O7A C9A 1.433(18) . ?
O7B H7B 0.849(9) . ?
O7B C9B 1.442(9) . ?
O8A H8A 0.8200 . ?
O8A C10A 1.445(14) . ?
O8B H8B 0.8200 . ?
O8B C10B 1.414(6) . ?
O9 H9A 0.8601 . ?
O9 H9B 0.8566 . ?
O10 H10A 0.8501 . ?
O10 H10B 0.8503 . ?
O11 C11 1.237(3) . ?
O12 C11 1.252(3) . ?
O13 C15 1.253(4) . ?
O14 C15 1.233(4) . ?
O15 H15A 0.8499 . ?
O15 H15B 0.8491 . ?
O16 H16A 0.8496 . ?
O16 H16B 0.8504 . ?
C1 C2 1.512(4) . ?
C2 C3 1.387(4) . ?
C2 C4 1.393(4) 2_767 ?
C3 C4 1.391(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6A 1.435(5) . ?
C5 C6B 1.403(11) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7 H7C 0.9700 . ?
C7 H7D 0.9700 . ?
C7 C8 1.478(4) . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.480(18) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C9B C10B 1.484(9) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10B H10E 0.9700 . ?
C10B H10F 0.9700 . ?
C11 C12 1.524(3) . ?
C12 C13 1.388(4) . ?
C12 C14 1.397(4) 2_657 ?
C13 C14 1.395(4) . ?
C15 C16 1.519(4) . ?
C16 C17 1.395(4) . ?
C16 C18 1.388(4) 2_576 ?
C17 C18 1.383(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 Tb1 O3 77.38(7) . . ?
O1 Tb1 O4 138.01(7) . . ?
O1 Tb1 O5 118.15(8) . . ?
O1 Tb1 O6 74.47(8) . . ?
O1 Tb1 O7A 69.2(16) . . ?
O1 Tb1 O7B 75.03(7) . . ?
O1 Tb1 O9 81.31(9) . . ?
O1 Tb1 O10 145.01(8) . . ?
O4 Tb1 O3 64.99(7) . . ?
O4 Tb1 O5 80.47(7) . . ?
O4 Tb1 O6 80.92(9) . . ?
O4 Tb1 O7A 147(3) . . ?
O4 Tb1 O7B 146.27(8) . . ?
O4 Tb1 O10 74.10(8) . . ?
O5 Tb1 O3 135.02(7) . . ?
O5 Tb1 O6 66.56(7) . . ?
O5 Tb1 O7A 68(3) . . ?
O5 Tb1 O10 73.09(7) . . ?
O6 Tb1 O3 79.76(7) . . ?
O6 Tb1 O7A 94(3) . . ?
O7A Tb1 O3 146.3(19) . . ?
O7B Tb1 O3 147.09(7) . . ?
O7B Tb1 O5 75.05(7) . . ?
O7B Tb1 O6 109.30(8) . . ?
O7B Tb1 O10 76.79(8) . . ?
O9 Tb1 O3 75.54(7) . . ?
O9 Tb1 O4 105.36(9) . . ?
O9 Tb1 O5 144.43(7) . . ?
O9 Tb1 O6 148.54(7) . . ?
O9 Tb1 O7A 96(3) . . ?
O9 Tb1 O7B 82.83(8) . . ?
O9 Tb1 O10 74.96(8) . . ?
O10 Tb1 O3 119.71(8) . . ?
O10 Tb1 O6 135.30(8) . . ?
O10 Tb1 O7A 87.7(11) . . ?
C1 O1 Tb1 139.55(18) . . ?
Tb1 O3 H3 127.1(14) . . ?
C5 O3 Tb1 119.09(17) . . ?
C5 O3 H3 108.1(14) . . ?
Tb1 O4 H4 122(3) . . ?
C6A O4 Tb1 121.3(2) . . ?
C6A O4 H4 111(3) . . ?
C6B O4 Tb1 120.4(5) . . ?
C6B O4 H4 115(3) . . ?
Tb1 O5 H5 129.1(15) . . ?
C7 O5 Tb1 113.56(17) . . ?
C7 O5 H5 107.5(14) . . ?
Tb1 O6 H6 126.6(14) . . ?
C8 O6 Tb1 119.60(17) . . ?
C8 O6 H6 108.6(14) . . ?
Tb1 O7A H7A 118(4) . . ?
C9A O7A Tb1 133(3) . . ?
C9A O7A H7A 109(3) . . ?
Tb1 O7B H7B 110.4(13) . . ?
C9B O7B Tb1 137.8(5) . . ?
C9B O7B H7B 108.7(13) . . ?
C10A O8A H8A 109.5 . . ?
C10B O8B H8B 109.5 . . ?
Tb1 O9 H9A 110.0 . . ?
Tb1 O9 H9B 109.5 . . ?
H9A O9 H9B 104.1 . . ?
Tb1 O10 H10A 109.3 . . ?
Tb1 O10 H10B 109.3 . . ?
H10A O10 H10B 104.5 . . ?
H15A O15 H15B 104.5 . . ?
H16A O16 H16B 109.5 . . ?
O1 C1 C2 114.9(2) . . ?
O2 C1 O1 126.7(3) . . ?
O2 C1 C2 118.4(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 C4 119.8(2) . 2_767 ?
C4 C2 C1 120.1(2) 2_767 . ?
C2 C3 Br1 118.0(2) . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 Br1 121.6(2) . . ?
C2 C4 Br2 118.9(2) 2_767 . ?
C3 C4 Br2 121.2(2) . . ?
C3 C4 C2 119.7(2) . 2_767 ?
O3 C5 H5A 109.6 . . ?
O3 C5 H5B 109.6 . . ?
O3 C5 C6A 110.3(3) . . ?
H5A C5 H5B 108.1 . . ?
C6A C5 H5A 109.6 . . ?
C6A C5 H5B 109.6 . . ?
C6B C5 O3 113.9(5) . . ?
O4 C6A C5 108.2(3) . . ?
O4 C6A H6AA 110.1 . . ?
O4 C6A H6AB 110.1 . . ?
C5 C6A H6AA 110.1 . . ?
C5 C6A H6AB 110.1 . . ?
H6AA C6A H6AB 108.4 . . ?
O4 C6B H6BA 109.7 . . ?
O4 C6B H6BB 109.7 . . ?
C5 C6B O4 109.9(8) . . ?
C5 C6B H6BA 109.7 . . ?
C5 C6B H6BB 109.7 . . ?
H6BA C6B H6BB 108.2 . . ?
O5 C7 H7C 109.8 . . ?
O5 C7 H7D 109.8 . . ?
O5 C7 C8 109.3(3) . . ?
H7C C7 H7D 108.3 . . ?
C8 C7 H7C 109.8 . . ?
C8 C7 H7D 109.8 . . ?
O6 C8 C7 107.0(3) . . ?
O6 C8 H8C 110.3 . . ?
O6 C8 H8D 110.3 . . ?
C7 C8 H8C 110.3 . . ?
C7 C8 H8D 110.3 . . ?
H8C C8 H8D 108.6 . . ?
O7A C9A H9AA 103.2 . . ?
O7A C9A H9AB 103.2 . . ?
O7A C9A C10A 136(6) . . ?
H9AA C9A H9AB 105.2 . . ?
C10A C9A H9AA 103.2 . . ?
C10A C9A H9AB 103.2 . . ?
O7B C9B H9BA 109.0 . . ?
O7B C9B H9BB 109.0 . . ?
O7B C9B C10B 112.7(7) . . ?
H9BA C9B H9BB 107.8 . . ?
C10B C9B H9BA 109.0 . . ?
C10B C9B H9BB 109.0 . . ?
O8A C10A C9A 101(2) . . ?
O8A C10A H10C 111.5 . . ?
O8A C10A H10D 111.5 . . ?
C9A C10A H10C 111.5 . . ?
C9A C10A H10D 111.5 . . ?
H10C C10A H10D 109.3 . . ?
O8B C10B C9B 112.7(6) . . ?
O8B C10B H10E 109.0 . . ?
O8B C10B H10F 109.0 . . ?
C9B C10B H10E 109.0 . . ?
C9B C10B H10F 109.0 . . ?
H10E C10B H10F 107.8 . . ?
O11 C11 O12 127.0(2) . . ?
O11 C11 C12 117.0(2) . . ?
O12 C11 C12 116.0(2) . . ?
C13 C12 C11 121.7(2) . . ?
C13 C12 C14 118.6(2) . 2_657 ?
C14 C12 C11 119.7(2) 2_657 . ?
C12 C13 Br3 118.40(19) . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 Br3 120.7(2) . . ?
C12 C14 Br4 118.74(18) 2_657 . ?
C13 C14 Br4 120.8(2) . . ?
C13 C14 C12 120.5(2) . 2_657 ?
O13 C15 C16 114.0(3) . . ?
O14 C15 O13 127.5(3) . . ?
O14 C15 C16 118.5(3) . . ?
C17 C16 C15 119.7(2) . . ?
C18 C16 C15 121.4(2) 2_576 . ?
C18 C16 C17 118.7(2) 2_576 . ?
C16 C17 Br5 118.28(19) . . ?
C18 C17 Br5 121.0(2) . . ?
C18 C17 C16 120.7(2) . . ?
C16 C18 Br6 118.29(19) 2_576 . ?
C17 C18 Br6 121.1(2) . . ?
C17 C18 C16 120.6(2) . 2_576 ?

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
_geom_hbond_publ_flag
O3 H3 O12 0.852(9) 1.923(15) 2.725(3) 156(3) . yes
O4 H4 O13 0.819(18) 1.74(2) 2.550(3) 169(4) . yes
O5 H5 O14 0.862(9) 1.767(11) 2.623(3) 172(3) . yes
O6 H6 O12 0.854(9) 1.853(11) 2.703(3) 173(3) 2_667 yes
O7B H7B O2 0.849(9) 1.808(12) 2.627(3) 162(2) . yes
O8A H8A O2 0.82 2.02 2.760(14) 150.7 2_766 yes
O9 H9B O15 0.86 1.90 2.647(4) 145.6 . yes
O15 H15B O8A 0.85 2.46 3.052(18) 127.2 . yes
O15 H15B O8B 0.85 1.93 2.719(5) 155.0 . yes
O16 H16A O11 0.85 2.15 2.916(4) 150.3 2_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb1 O1 C1 O2 -0.4(6) . . . . ?
Tb1 O1 C1 C2 179.4(2) . . . . ?
Tb1 O3 C5 C6A -29.6(4) . . . . ?
Tb1 O3 C5 C6B 11.7(9) . . . . ?
Tb1 O4 C6A C5 -41.2(5) . . . . ?
Tb1 O4 C6B C5 40.6(15) . . . . ?
Tb1 O5 C7 C8 -52.7(3) . . . . ?
Tb1 O6 C8 C7 -27.5(4) . . . . ?
Tb1 O7A C9A C10A -60(15) . . . . ?
Tb1 O7B C9B C10B -143.8(5) . . . . ?
Br1 C3 C4 Br2 -3.6(3) . . . . ?
Br1 C3 C4 C2 -179.95(19) . . . 2_767 ?
Br3 C13 C14 Br4 1.3(3) . . . . ?
Br3 C13 C14 C12 -179.65(19) . . . 2_657 ?
Br5 C17 C18 Br6 -4.8(3) . . . . ?
Br5 C17 C18 C16 177.0(2) . . . 2_576 ?
O1 C1 C2 C3 93.7(3) . . . . ?
O1 C1 C2 C4 -85.3(3) . . . 2_767 ?
O2 C1 C2 C3 -86.5(4) . . . . ?
O2 C1 C2 C4 94.5(3) . . . 2_767 ?
O3 C5 C6A O4 42.7(5) . . . . ?
O3 C5 C6B O4 -31.4(14) . . . . ?
O5 C7 C8 O6 50.6(4) . . . . ?
O7A C9A C10A O8A -62(7) . . . . ?
O7B C9B C10B O8B 66.8(9) . . . . ?
O11 C11 C12 C13 92.8(3) . . . . ?
O11 C11 C12 C14 -88.9(3) . . . 2_657 ?
O12 C11 C12 C13 -88.8(3) . . . . ?
O12 C11 C12 C14 89.5(3) . . . 2_657 ?
O13 C15 C16 C17 84.3(3) . . . . ?
O13 C15 C16 C18 -91.2(3) . . . 2_576 ?
O14 C15 C16 C17 -96.3(3) . . . . ?
O14 C15 C16 C18 88.3(4) . . . 2_576 ?
C1 C2 C3 Br1 1.0(3) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C2 C3 C4 Br2 175.67(19) . . . . ?
C2 C3 C4 C2 -0.7(4) . . . 2_767 ?
C4 C2 C3 Br1 179.98(19) 2_767 . . . ?
C4 C2 C3 C4 0.7(4) 2_767 . . . ?
C11 C12 C13 Br3 -2.0(3) . . . . ?
C11 C12 C13 C14 176.9(2) . . . . ?
C12 C13 C14 Br4 -177.62(19) . . . . ?
C12 C13 C14 C12 1.4(4) . . . 2_657 ?
C14 C12 C13 Br3 179.65(19) 2_657 . . . ?
C14 C12 C13 C14 -1.4(4) 2_657 . . . ?
C15 C16 C17 Br5 7.3(4) . . . . ?
C15 C16 C17 C18 -174.6(3) . . . . ?
C16 C17 C18 Br6 177.1(2) . . . . ?
C16 C17 C18 C16 -1.0(5) . . . 2_576 ?
C18 C16 C17 Br5 -177.1(2) 2_576 . . . ?
C18 C16 C17 C18 1.0(5) 2_576 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_8dy
_database_code_depnum_ccdc_archive 'CCDC 2130091'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-30
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 Dy O9'
_chemical_formula_sum            'C15 H12 Br6 Dy O9'
_chemical_formula_weight         978.15
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.140(3)
_cell_length_b                   10.5370(11)
_cell_length_c                   21.997(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.896(5)
_cell_angle_gamma                90
_cell_volume                     4650.9(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9619
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.497
_shelx_estimated_absorpt_T_min   0.220
_exptl_absorpt_coefficient_mu    13.567
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0891 after correction.
The Ratio of minimum to maximum transmission is 0.6377.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3600
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            69165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.815
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5354
_reflns_number_total             6056
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.000249(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0146P)²+15.7983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.52392(2) 0.52090(2) 0.39319(2) 0.01664(5) Uani 1 1 d . . . . .
Br1 Br 0.75950(2) 0.48849(3) 0.31586(2) 0.03282(9) Uani 1 1 d . . . . .
Br2 Br 0.90476(2) 0.63132(3) 0.33864(2) 0.03031(9) Uani 1 1 d . . . . .
Br3 Br 0.77313(2) 1.10549(3) 0.35590(2) 0.03376(10) Uani 1 1 d . . . . .
Br4 Br 0.62777(2) 0.95780(4) 0.33121(2) 0.03646(10) Uani 1 1 d . . . . .
Br5 Br 0.64318(2) 0.14528(3) 0.49670(2) 0.03723(10) Uani 1 1 d . . . . .
Br6 Br 0.63666(2) -0.16948(3) 0.50323(2) 0.02942(9) Uani 1 1 d . . . . .
O1 O 0.60882(12) 0.6506(2) 0.36589(12) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.61842(14) 0.6334(3) 0.26630(13) 0.0427(7) Uani 1 1 d . . . . .
O3 O 0.90779(12) 0.9759(2) 0.41071(12) 0.0270(5) Uani 1 1 d . . . . .
O4 O 0.93670(11) 0.9223(2) 0.32040(11) 0.0255(5) Uani 1 1 d . . . . .
O5 O 0.51635(12) 0.3143(2) 0.43391(12) 0.0263(5) Uani 1 1 d . . . . .
O6 O 0.49879(12) 0.3443(2) 0.53133(12) 0.0273(5) Uani 1 1 d . . . . .
O7 O 0.58103(14) 0.4049(2) 0.32216(14) 0.0321(6) Uani 1 1 d D . . . .
H7 H 0.590(3) 0.437(5) 0.2898(14) 0.070(19) Uiso 1 1 d D . . . .
O8 O 0.61611(12) 0.4944(3) 0.46978(12) 0.0292(6) Uani 1 1 d D . . . .
H8 H 0.611(2) 0.505(4) 0.5060(7) 0.036(13) Uiso 1 1 d D . . . .
O9 O 0.46691(14) 0.6757(2) 0.33084(13) 0.0338(6) Uani 1 1 d D . . . .
H9 H 0.4455(18) 0.647(4) 0.3008(12) 0.028(11) Uiso 1 1 d D . . . .
C1 C 0.63759(16) 0.6679(3) 0.31784(16) 0.0223(7) Uani 1 1 d . . . . .
C2 C 0.70483(15) 0.7347(3) 0.32733(15) 0.0193(6) Uani 1 1 d . . . . .
C3 C 0.76377(16) 0.6662(3) 0.32734(15) 0.0205(6) Uani 1 1 d . . . . .
C4 C 0.82554(16) 0.7277(3) 0.33673(15) 0.0209(6) Uani 1 1 d . . . . .
C5 C 0.82839(16) 0.8583(3) 0.34648(16) 0.0210(6) Uani 1 1 d . . . . .
C6 C 0.89536(16) 0.9231(3) 0.35972(16) 0.0220(7) Uani 1 1 d . . . . .
C7 C 0.76965(16) 0.9268(3) 0.34603(16) 0.0227(7) Uani 1 1 d . . . . .
C8 C 0.70823(15) 0.8659(3) 0.33585(16) 0.0209(6) Uani 1 1 d . . . . .
C9 C 0.50599(15) 0.2758(3) 0.48570(15) 0.0185(6) Uani 1 1 d . . . . .
C10 C 0.50250(15) 0.1325(3) 0.49431(14) 0.0169(6) Uani 1 1 d . . . . .
C11 C 0.56092(15) 0.0601(3) 0.49708(15) 0.0187(6) Uani 1 1 d . . . . .
C12 C 0.55842(15) -0.0715(3) 0.50197(15) 0.0190(6) Uani 1 1 d . . . . .
C13 C 0.5915(3) 0.2730(4) 0.3156(3) 0.0603(15) Uani 1 1 d . . . . .
H13A H 0.634114 0.258836 0.300343 0.091 Uiso 1 1 calc R U . . .
H13B H 0.557094 0.238400 0.287473 0.091 Uiso 1 1 calc R U . . .
H13C H 0.590280 0.232222 0.354517 0.091 Uiso 1 1 calc R U . . .
C14 C 0.6860(2) 0.4926(5) 0.4680(2) 0.0500(12) Uani 1 1 d . . . . .
H14A H 0.697897 0.430171 0.439042 0.075 Uiso 1 1 calc R U . . .
H14B H 0.706653 0.471644 0.507702 0.075 Uiso 1 1 calc R U . . .
H14C H 0.701053 0.574632 0.456086 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4561(3) 0.8073(4) 0.3400(2) 0.0524(13) Uani 1 1 d . . . . .
H15A H 0.458591 0.851818 0.302205 0.079 Uiso 1 1 calc R U . . .
H15B H 0.489632 0.839395 0.369761 0.079 Uiso 1 1 calc R U . . .
H15C H 0.412882 0.819731 0.354350 0.079 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O1 2.308(2) . ?
Dy1 O3 2.449(2) 3_445 ?
Dy1 O4 2.500(2) 3_445 ?
Dy1 O5 2.364(2) . ?
Dy1 O6 2.261(2) 5_666 ?
Dy1 O7 2.359(3) . ?
Dy1 O8 2.414(3) . ?
Dy1 O9 2.364(3) . ?
Br1 C3 1.890(3) . ?
Br2 C4 1.889(3) . ?
Br3 C7 1.896(3) . ?
Br4 C8 1.883(3) . ?
Br5 C11 1.885(3) . ?
Br6 C12 1.882(3) . ?
O1 C1 1.261(4) . ?
O2 C1 1.222(4) . ?
O3 C6 1.258(4) . ?
O4 C6 1.251(4) . ?
O5 C9 1.244(4) . ?
O6 C9 1.255(4) . ?
O7 H7 0.818(10) . ?
O7 C13 1.415(5) . ?
O8 H8 0.820(10) . ?
O8 C14 1.412(5) . ?
O9 H9 0.818(10) . ?
O9 C15 1.422(5) . ?
C1 C2 1.525(4) . ?
C2 C3 1.389(5) . ?
C2 C8 1.396(4) . ?
C3 C4 1.402(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.517(4) . ?
C5 C7 1.385(5) . ?
C7 C8 1.395(4) . ?
C9 C10 1.524(4) . ?
C10 C11 1.399(4) . ?
C10 C12 1.394(4) 5_656 ?
C11 C12 1.393(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O3 153.40(9) . 3_445 ?
O1 Dy1 O4 125.12(9) . 3_445 ?
O1 Dy1 O5 135.82(9) . . ?
O1 Dy1 O7 73.78(9) . . ?
O1 Dy1 O8 72.98(9) . . ?
O1 Dy1 O9 76.97(9) . . ?
O3 Dy1 O4 52.55(8) 3_445 3_445 ?
O5 Dy1 O3 70.66(9) . 3_445 ?
O5 Dy1 O4 78.18(8) . 3_445 ?
O5 Dy1 O8 72.53(9) . . ?
O5 Dy1 O9 144.21(9) . . ?
O6 Dy1 O1 91.14(9) 5_666 . ?
O6 Dy1 O3 75.53(8) 5_666 3_445 ?
O6 Dy1 O4 123.80(8) 5_666 3_445 ?
O6 Dy1 O5 106.05(9) 5_666 . ?
O6 Dy1 O7 162.26(10) 5_666 . ?
O6 Dy1 O8 75.63(9) 5_666 . ?
O6 Dy1 O9 82.77(10) 5_666 . ?
O7 Dy1 O3 122.02(9) . 3_445 ?
O7 Dy1 O4 73.50(9) . 3_445 ?
O7 Dy1 O5 79.91(9) . . ?
O7 Dy1 O8 90.75(10) . . ?
O7 Dy1 O9 102.31(10) . . ?
O8 Dy1 O3 123.76(9) . 3_445 ?
O8 Dy1 O4 148.80(9) . 3_445 ?
O9 Dy1 O3 78.56(10) . 3_445 ?
O9 Dy1 O4 68.62(9) . 3_445 ?
O9 Dy1 O8 142.27(9) . . ?
C1 O1 Dy1 135.0(2) . . ?
C6 O3 Dy1 93.7(2) . 3 ?
C6 O4 Dy1 91.56(19) . 3 ?
C9 O5 Dy1 132.0(2) . . ?
C9 O6 Dy1 173.3(2) . 5_666 ?
Dy1 O7 H7 121(4) . . ?
C13 O7 Dy1 131.4(3) . . ?
C13 O7 H7 106(4) . . ?
Dy1 O8 H8 121(3) . . ?
C14 O8 Dy1 133.8(3) . . ?
C14 O8 H8 103(3) . . ?
Dy1 O9 H9 114(3) . . ?
C15 O9 Dy1 131.5(3) . . ?
C15 O9 H9 114(3) . . ?
O1 C1 C2 114.7(3) . . ?
O2 C1 O1 127.1(3) . . ?
O2 C1 C2 118.1(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 C8 118.8(3) . . ?
C8 C2 C1 120.6(3) . . ?
C2 C3 Br1 119.0(2) . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 Br1 120.5(2) . . ?
C3 C4 Br2 119.5(2) . . ?
C5 C4 Br2 120.3(2) . . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C6 119.9(3) . . ?
C7 C5 C4 119.3(3) . . ?
C7 C5 C6 120.8(3) . . ?
O3 C6 Dy1 59.87(17) . 3 ?
O3 C6 C5 118.4(3) . . ?
O4 C6 Dy1 62.18(17) . 3 ?
O4 C6 O3 121.7(3) . . ?
O4 C6 C5 119.8(3) . . ?
C5 C6 Dy1 173.6(2) . 3 ?
C5 C7 Br3 119.5(2) . . ?
C5 C7 C8 120.5(3) . . ?
C8 C7 Br3 119.9(2) . . ?
C2 C8 Br4 118.0(2) . . ?
C7 C8 Br4 121.3(2) . . ?
C7 C8 C2 120.7(3) . . ?
O5 C9 O6 125.8(3) . . ?
O5 C9 C10 116.7(3) . . ?
O6 C9 C10 117.5(3) . . ?
C11 C10 C9 119.9(3) . . ?
C12 C10 C9 121.0(3) 5_656 . ?
C12 C10 C11 119.2(3) 5_656 . ?
C10 C11 Br5 118.5(2) . . ?
C12 C11 Br5 120.8(2) . . ?
C12 C11 C10 120.7(3) . . ?
C10 C12 Br6 119.1(2) 5_656 . ?
C11 C12 Br6 120.8(2) . . ?
C11 C12 C10 120.1(3) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O7 H7 O2 0.818(10) 2.22(5) 2.834(4) 131(5) . yes
O7 H7 O4 0.818(10) 2.44(4) 3.131(4) 143(5) 4_645 yes
O8 H8 O3 0.820(10) 1.913(12) 2.731(4) 175(5) 7_666 yes
O9 H9 O2 0.818(10) 1.878(17) 2.663(4) 160(4) 2_655 yes
C13 H13C O5 0.96 2.54 3.150(6) 121.4 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Dy1 O1 C1 O2 15.3(6) . . . . ?
Dy1 O1 C1 C2 -162.1(2) . . . . ?
Dy1 O3 C6 O4 -6.6(3) 3 . . . ?
Dy1 O3 C6 C5 173.0(3) 3 . . . ?
Dy1 O4 C6 O3 6.5(3) 3 . . . ?
Dy1 O4 C6 C5 -173.1(3) 3 . . . ?
Dy1 O5 C9 O6 -2.5(5) . . . . ?
Dy1 O5 C9 C10 178.19(19) . . . . ?
Br1 C3 C4 Br2 -0.6(4) . . . . ?
Br1 C3 C4 C5 -178.6(3) . . . . ?
Br2 C4 C5 C6 -1.0(4) . . . . ?
Br2 C4 C5 C7 -178.8(3) . . . . ?
Br3 C7 C8 Br4 0.3(4) . . . . ?
Br3 C7 C8 C2 178.8(3) . . . . ?
Br5 C11 C12 Br6 -4.0(4) . . . . ?
Br5 C11 C12 C10 176.3(2) . . . 5_656 ?
O1 C1 C2 C3 102.2(4) . . . . ?
O1 C1 C2 C8 -78.1(4) . . . . ?
O2 C1 C2 C3 -75.4(4) . . . . ?
O2 C1 C2 C8 104.3(4) . . . . ?
O5 C9 C10 C11 74.1(4) . . . . ?
O5 C9 C10 C12 -104.4(4) . . . 5_656 ?
O6 C9 C10 C11 -105.3(4) . . . . ?
O6 C9 C10 C12 76.2(4) . . . 5_656 ?
C1 C2 C3 Br1 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C8 Br4 -3.1(4) . . . . ?
C1 C2 C8 C7 178.4(3) . . . . ?
C2 C3 C4 Br2 178.3(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C2 C8 Br4 176.6(2) . . . . ?
C3 C2 C8 C7 -1.9(5) . . . . ?
C3 C4 C5 C6 177.0(3) . . . . ?
C3 C4 C5 C7 -0.8(5) . . . . ?
C4 C5 C6 O3 -116.5(4) . . . . ?
C4 C5 C6 O4 63.2(5) . . . . ?
C4 C5 C7 Br3 -177.4(3) . . . . ?
C4 C5 C7 C8 -0.1(5) . . . . ?
C5 C7 C8 Br4 -177.0(3) . . . . ?
C5 C7 C8 C2 1.5(5) . . . . ?
C6 C5 C7 Br3 4.8(5) . . . . ?
C6 C5 C7 C8 -177.8(3) . . . . ?
C7 C5 C6 O3 61.3(5) . . . . ?
C7 C5 C6 O4 -119.1(4) . . . . ?
C8 C2 C3 Br1 180.0(3) . . . . ?
C8 C2 C3 C4 1.0(5) . . . . ?
C9 C10 C11 Br5 5.1(4) . . . . ?
C9 C10 C11 C12 -176.9(3) . . . . ?
C10 C11 C12 Br6 178.1(2) . . . . ?
C10 C11 C12 C10 -1.6(5) . . . 5_656 ?
C12 C10 C11 Br5 -176.4(2) 5_656 . . . ?
C12 C10 C11 C12 1.6(5) 5_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10pr_r
_database_code_depnum_ccdc_archive 'CCDC 1940047'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br8 N2 O18 Pr2'
_chemical_formula_sum            'C20 H16 Br8 N2 O18 Pr2'
_chemical_formula_weight         1493.45
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3657(7)
_cell_length_b                   12.6197(8)
_cell_length_c                   16.2172(9)
_cell_angle_alpha                77.345(2)
_cell_angle_beta                 72.943(2)
_cell_angle_gamma                68.733(2)
_cell_volume                     1874.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9649
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.143
_cell_measurement_theta_min      2.649
_shelx_estimated_absorpt_T_max   0.304
_shelx_estimated_absorpt_T_min   0.159
_exptl_absorpt_coefficient_mu    11.165
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.7960.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            85992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.649
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7607
_reflns_number_total             9356
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         9356
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²+4.8868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10
 0.85 with sigma of 0.01
 O11-H11
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O18-H18
 0.85 with sigma of 0.01
 C13-H10
 1.91069 with sigma of 0.02
 Pr1-H10
 3.026644 with sigma of 0.02
 C14-H11
 1.891164 with sigma of 0.02
 Pr1-H11
 3.009963 with sigma of 0.02
 C19-H17
 1.888197 with sigma of 0.02
 Pr2-H17
 2.985151 with sigma of 0.02
 C20-H18
 1.895701 with sigma of 0.02
 Pr2-H18
 3.02219 with sigma of 0.02
3. Restrained planarity
 Br1, Br1_$4, Br2, Br2_$4, C1, C1_$4, C2_$4, C2, C3_$4, C3, C4_$4, C4
 with sigma of 0.1
 Br3, Br3_$5, Br4, Br4_$5, C5, C5_$5, C6_$5, C6, C7_$5, C7, C8_$5, C8
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(Br2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(Br3) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(Br4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(Br7) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(Br8) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Rigid body (RIGU) restrains
 Br1, Br2, C2, C3, C4
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 Br3, Br4, C6, C7, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br7, Br8, C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.00703(2) 0.69219(2) 0.28730(2) 0.02140(5) Uani 1 1 d D . . . .
Pr2 Pr 0.48796(2) 0.81294(2) 0.20967(2) 0.02200(5) Uani 1 1 d D . . . .
Br1 Br 0.61909(5) 0.72327(4) 0.55890(3) 0.03644(11) Uani 1 1 d . U . . .
Br2 Br 0.45434(5) 0.90299(4) 0.70710(3) 0.03800(11) Uani 1 1 d . U . . .
Br3 Br 0.80074(6) 0.39150(4) 0.16848(3) 0.04265(12) Uani 1 1 d . U . . .
Br4 Br 0.99089(6) 0.24337(4) 0.00546(3) 0.04153(12) Uani 1 1 d . U . . .
Br5 Br 1.26761(5) 0.76335(4) 0.50784(3) 0.04179(12) Uani 1 1 d . . . . .
Br6 Br 1.10769(6) 0.89868(5) 0.68021(3) 0.04950(14) Uani 1 1 d . . . . .
Br7 Br 0.42410(5) 0.40161(4) 0.20627(3) 0.03710(11) Uani 1 1 d . U . . .
Br8 Br 0.61109(5) 0.22325(4) 0.05944(3) 0.03601(11) Uani 1 1 d . U . . .
O1 O 0.7752(3) 0.7907(3) 0.3624(2) 0.0362(7) Uani 1 1 d . . . . .
O2 O 0.5713(3) 0.8296(3) 0.32578(19) 0.0343(7) Uani 1 1 d . . . . .
O3 O 0.9082(3) 0.6372(3) 0.19491(19) 0.0373(7) Uani 1 1 d . . . . .
O4 O 0.7081(3) 0.6717(3) 0.1558(2) 0.0370(7) Uani 1 1 d . . . . .
O5 O 1.0812(4) 0.8264(3) 0.3267(2) 0.0404(8) Uani 1 1 d . . . . .
O6 O 1.2647(3) 0.8857(3) 0.3089(2) 0.0401(8) Uani 1 1 d . . . . .
O7 O 1.0224(3) 0.6272(3) 0.45177(19) 0.0387(8) Uani 1 1 d . . . . .
O8 O 1.2207(3) 0.5785(3) 0.35590(19) 0.0386(8) Uani 1 1 d . . . . .
O9 O 1.2160(4) 0.5229(3) 0.4928(2) 0.0461(9) Uani 1 1 d . . . . .
O10 O 0.9316(3) 0.8710(3) 0.1867(2) 0.0348(7) Uani 1 1 d D . . . .
H10 H 0.852(3) 0.890(3) 0.173(3) 0.052 Uiso 1 1 d D U . . .
O11 O 0.9846(5) 0.4968(3) 0.3476(2) 0.0577(11) Uani 1 1 d D . . . .
H11 H 0.937(6) 0.488(2) 0.3997(17) 0.087 Uiso 1 1 d D U . . .
O12 O 0.3893(3) 0.7214(3) 0.1444(2) 0.0358(7) Uani 1 1 d . . . . .
O13 O 0.2095(3) 0.6548(3) 0.16610(19) 0.0326(7) Uani 1 1 d . . . . .
O14 O 0.6703(4) 0.9192(3) 0.1416(2) 0.0383(7) Uani 1 1 d . . . . .
O15 O 0.5923(4) 0.8823(3) 0.0450(2) 0.0386(8) Uani 1 1 d . . . . .
O16 O 0.7377(4) 0.9814(3) 0.0053(2) 0.0481(9) Uani 1 1 d . . . . .
O17 O 0.3526(4) 1.0128(4) 0.1500(2) 0.0647(13) Uani 1 1 d D . . . .
H17 H 0.363(7) 1.022(3) 0.0951(9) 0.097 Uiso 1 1 d D U . . .
O18 O 0.4763(3) 0.6345(3) 0.3117(2) 0.0377(7) Uani 1 1 d D . . . .
H18 H 0.399(2) 0.618(3) 0.327(3) 0.057 Uiso 1 1 d D U . . .
N1 N 1.1535(4) 0.5753(3) 0.4354(2) 0.0323(8) Uani 1 1 d . . . . .
N2 N 0.6682(4) 0.9287(3) 0.0622(2) 0.0329(8) Uani 1 1 d . . . . .
C1 C 0.6451(3) 0.8415(3) 0.3691(2) 0.0221(8) Uani 1 1 d . . . . .
C2 C 0.5699(3) 0.9237(3) 0.4371(2) 0.0194(7) Uani 1 1 d . U . . .
C3 C 0.5508(3) 0.8826(3) 0.5257(2) 0.0222(7) Uani 1 1 d . U . . .
C4 C 0.4819(3) 0.9586(3) 0.5870(2) 0.0214(7) Uani 1 1 d . U . . .
C5 C 0.8348(3) 0.6314(3) 0.1459(2) 0.0238(8) Uani 1 1 d . . . . .
C6 C 0.9202(3) 0.5631(3) 0.0702(2) 0.0211(7) Uani 1 1 d . U . . .
C7 C 0.9157(3) 0.4538(3) 0.0718(2) 0.0220(7) Uani 1 1 d . U . . .
C8 C 0.9951(3) 0.3915(3) 0.0021(2) 0.0226(8) Uani 1 1 d . U . . .
C9 C 1.1434(4) 0.8793(3) 0.3473(2) 0.0232(8) Uani 1 1 d . . . . .
C10 C 1.0693(4) 0.9419(3) 0.4264(2) 0.0226(8) Uani 1 1 d . . . . .
C11 C 1.1145(4) 0.9005(3) 0.5028(3) 0.0242(8) Uani 1 1 d . . . . .
C12 C 1.0452(4) 0.9572(3) 0.5765(2) 0.0240(8) Uani 1 1 d . . . . .
C13 C 1.0140(6) 0.9414(5) 0.1321(3) 0.0486(13) Uani 1 1 d D . . . .
H13A H 1.046240 0.920805 0.074150 0.073 Uiso 1 1 calc R U . . .
H13B H 1.094667 0.929804 0.154601 0.073 Uiso 1 1 calc R U . . .
H13C H 0.956062 1.020500 0.131048 0.073 Uiso 1 1 calc R U . . .
C14 C 1.0387(8) 0.3905(5) 0.3122(5) 0.0683(18) Uani 1 1 d D . . . .
H14A H 1.077523 0.403391 0.250740 0.102 Uiso 1 1 calc R U . . .
H14B H 0.962988 0.359116 0.322314 0.102 Uiso 1 1 calc R U . . .
H14C H 1.112057 0.337666 0.339630 0.102 Uiso 1 1 calc R U . . .
C15 C 0.3314(4) 0.6571(3) 0.1306(2) 0.0220(8) Uani 1 1 d . . . . .
C16 C 0.4198(4) 0.5759(3) 0.0622(2) 0.0198(7) Uani 1 1 d . U . . .
C17 C 0.4664(4) 0.4584(3) 0.0866(2) 0.0216(7) Uani 1 1 d . U . . .
C18 C 0.5459(4) 0.3825(3) 0.0259(2) 0.0217(7) Uani 1 1 d . U . . .
C19 C 0.2605(6) 1.1158(5) 0.1836(4) 0.0592(16) Uani 1 1 d D . . . .
H19A H 0.302449 1.175612 0.159238 0.089 Uiso 1 1 calc R U . . .
H19B H 0.246087 1.104711 0.245720 0.089 Uiso 1 1 calc R U . . .
H19C H 0.170667 1.136864 0.168678 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5710(6) 0.5608(5) 0.3636(4) 0.0543(14) Uani 1 1 d D . . . .
H20A H 0.664370 0.567424 0.338591 0.081 Uiso 1 1 calc R U . . .
H20B H 0.574944 0.483047 0.365993 0.081 Uiso 1 1 calc R U . . .
H20C H 0.537709 0.582169 0.421333 0.081 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O1 2.363(3) . ?
Pr1 O3 2.376(3) . ?
Pr1 O5 2.361(3) . ?
Pr1 O7 2.647(3) . ?
Pr1 O8 2.578(3) . ?
Pr1 O10 2.494(3) . ?
Pr1 O11 2.514(4) . ?
Pr1 O13 2.400(3) 1_655 ?
Pr2 O2 2.365(3) . ?
Pr2 O4 2.389(3) . ?
Pr2 O6 2.389(3) 1_455 ?
Pr2 O12 2.351(3) . ?
Pr2 O14 2.560(3) . ?
Pr2 O15 2.653(3) . ?
Pr2 O17 2.535(4) . ?
Pr2 O18 2.504(3) . ?
Br1 C3 1.884(4) . ?
Br2 C4 1.893(4) . ?
Br3 C7 1.882(4) . ?
Br4 C8 1.874(4) . ?
Br5 C11 1.883(4) . ?
Br6 C12 1.881(4) . ?
Br7 C17 1.895(4) . ?
Br8 C18 1.882(4) . ?
O1 C1 1.248(4) . ?
O2 C1 1.244(4) . ?
O3 C5 1.280(4) . ?
O4 C5 1.199(4) . ?
O5 C9 1.229(5) . ?
O6 C9 1.252(5) . ?
O7 N1 1.252(5) . ?
O8 N1 1.273(4) . ?
O9 N1 1.222(5) . ?
O10 H10 0.853(9) . ?
O10 C13 1.437(5) . ?
O11 H11 0.851(9) . ?
O11 C14 1.431(7) . ?
O12 C15 1.257(5) . ?
O13 C15 1.233(5) . ?
O14 N2 1.273(5) . ?
O15 N2 1.255(5) . ?
O16 N2 1.225(5) . ?
O17 H17 0.850(9) . ?
O17 C19 1.415(6) . ?
O18 H18 0.853(9) . ?
O18 C20 1.420(6) . ?
C1 C2 1.520(5) . ?
C2 C3 1.398(5) . ?
C2 C4 1.392(5) 2_676 ?
C3 C4 1.388(5) . ?
C5 C6 1.518(5) . ?
C6 C7 1.391(5) . ?
C6 C8 1.393(5) 2_765 ?
C7 C8 1.396(5) . ?
C9 C10 1.512(5) . ?
C10 C11 1.380(5) . ?
C10 C12 1.394(5) 2_776 ?
C11 C12 1.399(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.530(5) . ?
C16 C17 1.388(5) . ?
C16 C18 1.398(5) 2_665 ?
C17 C18 1.390(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O3 89.83(11) . . ?
O1 Pr1 O7 77.85(10) . . ?
O1 Pr1 O8 125.97(10) . . ?
O1 Pr1 O10 76.19(11) . . ?
O1 Pr1 O11 94.18(13) . . ?
O1 Pr1 O13 156.31(11) . 1_655 ?
O3 Pr1 O7 133.54(11) . . ?
O3 Pr1 O8 130.40(11) . . ?
O3 Pr1 O10 76.53(11) . . ?
O3 Pr1 O11 71.15(12) . . ?
O3 Pr1 O13 81.01(11) . 1_655 ?
O5 Pr1 O1 86.36(11) . . ?
O5 Pr1 O3 151.39(12) . . ?
O5 Pr1 O7 73.14(11) . . ?
O5 Pr1 O8 72.58(12) . . ?
O5 Pr1 O10 75.02(11) . . ?
O5 Pr1 O11 137.38(12) . . ?
O5 Pr1 O13 91.30(11) . 1_655 ?
O8 Pr1 O7 48.73(9) . . ?
O10 Pr1 O7 139.76(10) . . ?
O10 Pr1 O8 138.55(11) . . ?
O10 Pr1 O11 146.31(13) . . ?
O11 Pr1 O7 65.44(11) . . ?
O11 Pr1 O8 72.93(13) . . ?
O13 Pr1 O7 123.92(10) 1_655 . ?
O13 Pr1 O8 75.20(10) 1_655 . ?
O13 Pr1 O10 80.43(11) 1_655 . ?
O13 Pr1 O11 103.30(12) 1_655 . ?
O2 Pr2 O4 91.72(11) . . ?
O2 Pr2 O6 80.66(11) . 1_455 ?
O2 Pr2 O14 74.02(10) . . ?
O2 Pr2 O15 122.77(11) . . ?
O2 Pr2 O17 107.93(13) . . ?
O2 Pr2 O18 77.09(11) . . ?
O4 Pr2 O14 73.62(11) . . ?
O4 Pr2 O15 70.87(11) . . ?
O4 Pr2 O17 134.57(12) . . ?
O4 Pr2 O18 76.16(11) . . ?
O6 Pr2 O4 155.63(12) 1_455 . ?
O6 Pr2 O14 125.17(11) 1_455 . ?
O6 Pr2 O15 132.44(11) 1_455 . ?
O6 Pr2 O17 69.61(12) 1_455 . ?
O6 Pr2 O18 79.57(11) 1_455 . ?
O12 Pr2 O2 152.15(11) . . ?
O12 Pr2 O4 84.45(11) . . ?
O12 Pr2 O6 91.55(11) . 1_455 ?
O12 Pr2 O14 130.26(10) . . ?
O12 Pr2 O15 81.97(11) . . ?
O12 Pr2 O17 93.98(14) . . ?
O12 Pr2 O18 75.21(11) . . ?
O14 Pr2 O15 48.91(10) . . ?
O17 Pr2 O14 73.28(14) . . ?
O17 Pr2 O15 63.99(11) . . ?
O18 Pr2 O14 137.00(11) . . ?
O18 Pr2 O15 141.35(11) . . ?
O18 Pr2 O17 147.11(13) . . ?
C1 O1 Pr1 153.8(3) . . ?
C1 O2 Pr2 163.2(3) . . ?
C5 O3 Pr1 166.6(3) . . ?
C5 O4 Pr2 150.4(3) . . ?
C9 O5 Pr1 167.9(3) . . ?
C9 O6 Pr2 149.2(3) . 1_655 ?
N1 O7 Pr1 95.6(2) . . ?
N1 O8 Pr1 98.3(2) . . ?
Pr1 O10 H10 119.8(14) . . ?
C13 O10 Pr1 129.2(3) . . ?
C13 O10 H10 109.9(14) . . ?
Pr1 O11 H11 117.7(14) . . ?
C14 O11 Pr1 132.9(4) . . ?
C14 O11 H11 109.3(14) . . ?
C15 O12 Pr2 163.8(3) . . ?
C15 O13 Pr1 149.1(3) . 1_455 ?
N2 O14 Pr2 98.8(2) . . ?
N2 O15 Pr2 94.8(2) . . ?
Pr2 O17 H17 113.7(13) . . ?
C19 O17 Pr2 137.1(3) . . ?
C19 O17 H17 109.2(14) . . ?
Pr2 O18 H18 118.9(14) . . ?
C20 O18 Pr2 130.3(3) . . ?
C20 O18 H18 109.8(14) . . ?
O7 N1 O8 117.3(4) . . ?
O9 N1 O7 122.1(4) . . ?
O9 N1 O8 120.6(4) . . ?
O15 N2 O14 117.3(4) . . ?
O16 N2 O14 120.9(4) . . ?
O16 N2 O15 121.8(4) . . ?
O1 C1 C2 117.2(3) . . ?
O2 C1 O1 125.6(4) . . ?
O2 C1 C2 117.1(3) . . ?
C3 C2 C1 120.5(3) . . ?
C4 C2 C1 121.1(3) 2_676 . ?
C4 C2 C3 118.4(3) 2_676 . ?
C2 C3 Br1 118.7(3) . . ?
C4 C3 Br1 121.4(3) . . ?
C4 C3 C2 119.9(3) . . ?
C2 C4 Br2 118.3(3) 2_676 . ?
C3 C4 Br2 120.1(3) . . ?
C3 C4 C2 121.7(3) . 2_676 ?
O3 C5 C6 114.9(3) . . ?
O4 C5 O3 126.3(4) . . ?
O4 C5 C6 118.8(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 C8 118.7(3) . 2_765 ?
C8 C6 C5 120.7(3) 2_765 . ?
C6 C7 Br3 119.3(3) . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 Br3 120.4(3) . . ?
C6 C8 Br4 118.9(3) 2_765 . ?
C6 C8 C7 121.1(3) 2_765 . ?
C7 C8 Br4 120.0(3) . . ?
O5 C9 O6 125.8(4) . . ?
O5 C9 C10 118.0(4) . . ?
O6 C9 C10 116.2(4) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 C12 118.8(3) . 2_776 ?
C12 C10 C9 120.7(3) 2_776 . ?
C10 C11 Br5 119.1(3) . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 Br5 120.0(3) . . ?
C10 C12 Br6 119.5(3) 2_776 . ?
C10 C12 C11 120.4(3) 2_776 . ?
C11 C12 Br6 120.2(3) . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O12 C15 C16 116.7(3) . . ?
O13 C15 O12 126.1(4) . . ?
O13 C15 C16 117.2(3) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 C18 118.4(3) . 2_665 ?
C18 C16 C15 121.2(3) 2_665 . ?
C16 C17 Br7 118.6(3) . . ?
C16 C17 C18 121.6(3) . . ?
C18 C17 Br7 119.7(3) . . ?
C16 C18 Br8 118.6(3) 2_665 . ?
C17 C18 Br8 121.5(3) . . ?
C17 C18 C16 120.0(3) . 2_665 ?
O17 C19 H19A 109.5 . . ?
O17 C19 H19B 109.5 . . ?
O17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O18 C20 H20A 109.5 . . ?
O18 C20 H20B 109.5 . . ?
O18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_hbond_publ_flag
O10 H10 O14 0.853(9) 1.980(11) 2.830(5) 175(4) . yes
O11 H11 O9 0.851(9) 2.00(2) 2.832(5) 165(7) 2_766 yes
O17 H17 O15 0.850(9) 2.33(3) 3.120(5) 155(5) 2_675 yes
O17 H17 O16 0.850(9) 2.19(5) 2.911(6) 142(7) 2_675 yes
O18 H18 O8 0.853(9) 1.986(10) 2.838(5) 177(5) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pr1 O1 C1 O2 24.0(9) . . . . ?
Pr1 O1 C1 C2 -156.9(5) . . . . ?
Pr1 O3 C5 O4 -39.5(15) . . . . ?
Pr1 O3 C5 C6 142.5(10) . . . . ?
Pr1 O5 C9 O6 51.3(16) . . . . ?
Pr1 O5 C9 C10 -128.0(13) . . . . ?
Pr1 O7 N1 O8 2.9(4) . . . . ?
Pr1 O7 N1 O9 -176.9(4) . . . . ?
Pr1 O8 N1 O7 -3.0(4) . . . . ?
Pr1 O8 N1 O9 176.8(3) . . . . ?
Pr1 O13 C15 O12 -23.2(8) 1_455 . . . ?
Pr1 O13 C15 C16 158.0(4) 1_455 . . . ?
Pr2 O2 C1 O1 -46.9(12) . . . . ?
Pr2 O2 C1 C2 134.1(8) . . . . ?
Pr2 O4 C5 O3 27.5(9) . . . . ?
Pr2 O4 C5 C6 -154.5(4) . . . . ?
Pr2 O6 C9 O5 -17.2(9) 1_655 . . . ?
Pr2 O6 C9 C10 162.2(4) 1_655 . . . ?
Pr2 O12 C15 O13 62.6(12) . . . . ?
Pr2 O12 C15 C16 -118.6(9) . . . . ?
Pr2 O14 N2 O15 -3.6(4) . . . . ?
Pr2 O14 N2 O16 176.2(3) . . . . ?
Pr2 O15 N2 O14 3.5(4) . . . . ?
Pr2 O15 N2 O16 -176.4(3) . . . . ?
Br1 C3 C4 Br2 -0.2(3) . . . . ?
Br1 C3 C4 C2 -179.5(2) . . . 2_676 ?
Br3 C7 C8 Br4 -1.4(3) . . . . ?
Br3 C7 C8 C6 179.5(2) . . . 2_765 ?
Br5 C11 C12 Br6 1.6(5) . . . . ?
Br5 C11 C12 C10 -179.3(3) . . . 2_776 ?
Br7 C17 C18 Br8 0.8(5) . . . . ?
Br7 C17 C18 C16 -178.5(3) . . . 2_665 ?
O1 C1 C2 C3 -68.4(4) . . . . ?
O1 C1 C2 C4 111.7(4) . . . 2_676 ?
O2 C1 C2 C3 110.7(4) . . . . ?
O2 C1 C2 C4 -69.1(4) . . . 2_676 ?
O3 C5 C6 C7 105.1(4) . . . . ?
O3 C5 C6 C8 -74.8(4) . . . 2_765 ?
O4 C5 C6 C7 -73.1(4) . . . . ?
O4 C5 C6 C8 107.0(4) . . . 2_765 ?
O5 C9 C10 C11 106.9(5) . . . . ?
O5 C9 C10 C12 -73.5(5) . . . 2_776 ?
O6 C9 C10 C11 -72.5(5) . . . . ?
O6 C9 C10 C12 107.2(5) . . . 2_776 ?
O12 C15 C16 C17 112.3(4) . . . . ?
O12 C15 C16 C18 -68.4(5) . . . 2_665 ?
O13 C15 C16 C17 -68.8(5) . . . . ?
O13 C15 C16 C18 110.5(4) . . . 2_665 ?
C1 C2 C3 Br1 -0.4(4) . . . . ?
C1 C2 C3 C4 180.0(3) . . . . ?
C2 C3 C4 Br2 179.4(2) . . . . ?
C2 C3 C4 C2 0.2(5) . . . 2_676 ?
C4 C2 C3 Br1 179.5(2) 2_676 . . . ?
C4 C2 C3 C4 -0.2(5) 2_676 . . . ?
C5 C6 C7 Br3 0.6(4) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C6 C7 C8 Br4 179.0(2) . . . . ?
C6 C7 C8 C6 -0.2(5) . . . 2_765 ?
C8 C6 C7 Br3 -179.5(2) 2_765 . . . ?
C8 C6 C7 C8 0.2(5) 2_765 . . . ?
C9 C10 C11 Br5 -1.1(5) . . . . ?
C9 C10 C11 C12 -179.1(4) . . . . ?
C10 C11 C12 Br6 179.6(3) . . . . ?
C10 C11 C12 C10 -1.3(7) . . . 2_776 ?
C12 C10 C11 Br5 179.2(3) 2_776 . . . ?
C12 C10 C11 C12 1.2(7) 2_776 . . . ?
C15 C16 C17 Br7 -2.2(5) . . . . ?
C15 C16 C17 C18 179.5(4) . . . . ?
C16 C17 C18 Br8 179.1(3) . . . . ?
C16 C17 C18 C16 -0.2(7) . . . 2_665 ?
C18 C16 C17 Br7 178.5(3) 2_665 . . . ?
C18 C16 C17 C18 0.2(7) 2_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4sm
_database_code_depnum_ccdc_archive 'CCDC 1940038'
loop_
_audit_author_name
_audit_author_address
'Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 O9 Sm'
_chemical_formula_sum            'C15 H12 Br6 O9 Sm'
_chemical_formula_weight         966.01
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.281(3)
_cell_length_b                   10.5811(16)
_cell_length_c                   22.039(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.821(5)
_cell_angle_gamma                90
_cell_volume                     4712.7(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9450
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.516
_shelx_estimated_absorpt_T_min   0.208
_exptl_absorpt_coefficient_mu    12.710
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1369 before and 0.0744 after correction. The Ratio of minimum to maximum transmission is 0.6789. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             3568
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            53918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3893
_reflns_number_total             4619
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.000064(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0175P)²+21.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.52500(2) 0.52230(2) 0.39251(2) 0.01627(7) Uani 1 1 d . . . . .
Br1 Br 0.75980(2) 0.49274(4) 0.31564(2) 0.03327(12) Uani 1 1 d . . . . .
Br2 Br 0.90425(2) 0.63495(4) 0.33803(2) 0.03155(12) Uani 1 1 d . . . . .
Br3 Br 0.77394(2) 1.10627(4) 0.35606(2) 0.03404(13) Uani 1 1 d . . . . .
Br4 Br 0.62951(2) 0.95957(5) 0.33142(3) 0.03736(14) Uani 1 1 d . . . . .
Br5 Br 0.64236(2) 0.14326(4) 0.49638(3) 0.03720(14) Uani 1 1 d . . . . .
Br6 Br 0.63515(2) -0.16980(4) 0.50361(2) 0.03008(12) Uani 1 1 d . . . . .
O1 O 0.61107(14) 0.6512(3) 0.36478(14) 0.0280(7) Uani 1 1 d . . . . .
O2 O 0.61930(17) 0.6429(4) 0.26476(16) 0.0465(10) Uani 1 1 d . . . . .
O3 O 0.90795(14) 0.9746(3) 0.41024(14) 0.0266(7) Uani 1 1 d . . . . .
O4 O 0.93525(14) 0.9258(3) 0.31889(14) 0.0254(7) Uani 1 1 d . . . . .
O5 O 0.51726(14) 0.3106(3) 0.43283(14) 0.0255(7) Uani 1 1 d . . . . .
O6 O 0.49933(14) 0.3433(3) 0.52943(15) 0.0282(7) Uani 1 1 d . . . . .
O7 O 0.58077(16) 0.4035(3) 0.31829(17) 0.0337(8) Uani 1 1 d D . . . .
O8 O 0.61816(14) 0.4951(3) 0.47083(15) 0.0291(7) Uani 1 1 d D . . . .
O9 O 0.46644(17) 0.6812(3) 0.33081(16) 0.0347(8) Uani 1 1 d D . . . .
C1 C 0.6393(2) 0.6718(4) 0.3170(2) 0.0231(10) Uani 1 1 d . . . . .
C2 C 0.70585(19) 0.7381(4) 0.32646(19) 0.0186(9) Uani 1 1 d . . . . .
C3 C 0.7643(2) 0.6695(4) 0.32676(19) 0.0208(9) Uani 1 1 d . . . . .
C4 C 0.82568(19) 0.7302(4) 0.33625(19) 0.0195(9) Uani 1 1 d . . . . .
C5 C 0.8285(2) 0.8601(4) 0.3457(2) 0.0217(10) Uani 1 1 d . . . . .
C6 C 0.8952(2) 0.9251(4) 0.3589(2) 0.0220(10) Uani 1 1 d . . . . .
C7 C 0.7699(2) 0.9290(4) 0.3451(2) 0.0216(9) Uani 1 1 d . . . . .
C8 C 0.70928(19) 0.8684(4) 0.3352(2) 0.0213(9) Uani 1 1 d . . . . .
C9 C 0.50673(19) 0.2739(4) 0.4845(2) 0.0186(9) Uani 1 1 d . . . . .
C10 C 0.50294(19) 0.1322(4) 0.49363(18) 0.0157(9) Uani 1 1 d . . . . .
C11 C 0.56032(19) 0.0588(4) 0.49687(19) 0.0184(9) Uani 1 1 d . . . . .
C12 C 0.55771(19) -0.0712(4) 0.50218(19) 0.0188(9) Uani 1 1 d . . . . .
C13 C 0.5947(4) 0.2739(5) 0.3159(3) 0.073(2) Uani 1 1 d . . . . .
H13A H 0.633480 0.260978 0.294563 0.109 Uiso 1 1 calc GR . . . .
H13B H 0.557870 0.230624 0.295058 0.109 Uiso 1 1 calc GR . . . .
H13C H 0.602276 0.241365 0.356589 0.109 Uiso 1 1 calc GR . . . .
C14 C 0.6878(2) 0.4935(6) 0.4694(3) 0.0543(17) Uani 1 1 d . . . . .
H14A H 0.699973 0.428803 0.441929 0.081 Uiso 1 1 calc GR . . . .
H14B H 0.708080 0.476613 0.509472 0.081 Uiso 1 1 calc GR . . . .
H14C H 0.702457 0.574143 0.455739 0.081 Uiso 1 1 calc GR . . . .
C15 C 0.4572(3) 0.8131(5) 0.3408(3) 0.0585(18) Uani 1 1 d . . . . .
H15A H 0.457078 0.857325 0.302713 0.088 Uiso 1 1 calc GR . . . .
H15B H 0.492557 0.844325 0.368405 0.088 Uiso 1 1 calc GR . . . .
H15C H 0.415728 0.826305 0.357826 0.088 Uiso 1 1 calc GR . . . .
H8 H 0.611(3) 0.513(6) 0.5057(11) 0.07(2) Uiso 1 1 d D . . . .
H9 H 0.443(2) 0.659(5) 0.3006(16) 0.055(19) Uiso 1 1 d D . . . .
H7 H 0.582(3) 0.429(5) 0.2835(10) 0.039(17) Uiso 1 1 d 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 2.337(3) . ?
Sm1 O3 2.490(3) 3_445 ?
Sm1 O4 2.548(3) 3_445 ?
Sm1 O5 2.420(3) . ?
Sm1 O6 2.317(3) 5_666 ?
Sm1 O7 2.418(3) . ?
Sm1 O8 2.466(3) . ?
Sm1 O9 2.412(3) . ?
Br1 C3 1.888(4) . ?
Br2 C4 1.884(4) . ?
Br3 C7 1.892(4) . ?
Br4 C8 1.879(4) . ?
Br5 C11 1.889(4) . ?
Br6 C12 1.883(4) . ?
O1 C1 1.259(5) . ?
O2 C1 1.227(5) . ?
O3 C6 1.255(5) . ?
O4 C6 1.247(5) . ?
O5 C9 1.238(5) . ?
O6 C9 1.252(5) . ?
O7 C13 1.402(6) . ?
O7 H7 0.814(10) . ?
O8 C14 1.415(6) . ?
O8 H8 0.819(10) . ?
O9 C15 1.427(6) . ?
O9 H9 0.820(10) . ?
C1 C2 1.520(5) . ?
C2 C3 1.390(6) . ?
C2 C8 1.393(6) . ?
C3 C4 1.400(5) . ?
C4 C5 1.390(6) . ?
C5 C6 1.524(6) . ?
C5 C7 1.394(6) . ?
C7 C8 1.387(6) . ?
C9 C10 1.516(5) . ?
C10 C11 1.396(5) . ?
C10 C12 1.399(5) 5_656 ?
C11 C12 1.383(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O3 154.47(10) . 3_445 ?
O1 Sm1 O4 125.22(10) . 3_445 ?
O1 Sm1 O5 135.18(10) . . ?
O1 Sm1 O7 73.99(11) . . ?
O1 Sm1 O8 72.90(11) . . ?
O1 Sm1 O9 77.81(11) . . ?
O3 Sm1 O4 51.62(10) 3_445 3_445 ?
O5 Sm1 O3 70.29(10) . 3_445 ?
O5 Sm1 O4 78.34(10) . 3_445 ?
O5 Sm1 O8 72.82(10) . . ?
O6 Sm1 O1 92.66(11) 5_666 . ?
O6 Sm1 O3 75.07(10) 5_666 3_445 ?
O6 Sm1 O4 122.24(10) 5_666 3_445 ?
O6 Sm1 O5 105.73(11) 5_666 . ?
O6 Sm1 O7 164.23(11) 5_666 . ?
O6 Sm1 O8 75.55(11) 5_666 . ?
O6 Sm1 O9 82.25(12) 5_666 . ?
O7 Sm1 O3 120.49(11) . 3_445 ?
O7 Sm1 O4 73.18(11) . 3_445 ?
O7 Sm1 O5 79.38(11) . . ?
O7 Sm1 O8 92.20(12) . . ?
O8 Sm1 O3 123.43(10) . 3_445 ?
O8 Sm1 O4 149.66(10) . 3_445 ?
O9 Sm1 O3 78.39(11) . 3_445 ?
O9 Sm1 O4 68.21(10) . 3_445 ?
O9 Sm1 O5 143.94(11) . . ?
O9 Sm1 O7 102.54(12) . . ?
O9 Sm1 O8 141.99(11) . . ?
C1 O1 Sm1 136.2(3) . . ?
C6 O3 Sm1 94.0(2) . 3 ?
C6 O4 Sm1 91.4(2) . 3 ?
C9 O5 Sm1 130.5(3) . . ?
C9 O6 Sm1 174.0(3) . 5_666 ?
Sm1 O7 H7 122(4) . . ?
C13 O7 Sm1 129.8(3) . . ?
C13 O7 H7 105(4) . . ?
Sm1 O8 H8 116(5) . . ?
C14 O8 Sm1 133.8(3) . . ?
C14 O8 H8 107(5) . . ?
Sm1 O9 H9 119(4) . . ?
C15 O9 Sm1 131.3(3) . . ?
C15 O9 H9 109(4) . . ?
O1 C1 C2 115.2(4) . . ?
O2 C1 O1 127.2(4) . . ?
O2 C1 C2 117.6(4) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 C8 118.9(4) . . ?
C8 C2 C1 120.6(4) . . ?
C2 C3 Br1 119.0(3) . . ?
C2 C3 C4 120.5(4) . . ?
C4 C3 Br1 120.5(3) . . ?
C3 C4 Br2 119.8(3) . . ?
C5 C4 Br2 120.1(3) . . ?
C5 C4 C3 120.0(4) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 C7 119.5(4) . . ?
C7 C5 C6 120.6(4) . . ?
O3 C6 Sm1 60.1(2) . 3 ?
O3 C6 C5 118.2(4) . . ?
O4 C6 Sm1 62.8(2) . 3 ?
O4 C6 O3 122.6(4) . . ?
O4 C6 C5 119.2(4) . . ?
C5 C6 Sm1 173.3(3) . 3 ?
C5 C7 Br3 119.3(3) . . ?
C8 C7 Br3 120.5(3) . . ?
C8 C7 C5 120.2(4) . . ?
C2 C8 Br4 118.0(3) . . ?
C7 C8 Br4 121.2(3) . . ?
C7 C8 C2 120.8(4) . . ?
O5 C9 O6 125.8(4) . . ?
O5 C9 C10 116.5(4) . . ?
O6 C9 C10 117.6(4) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 C12 118.3(4) . 5_656 ?
C12 C10 C9 121.3(3) 5_656 . ?
C10 C11 Br5 117.9(3) . . ?
C12 C11 Br5 120.7(3) . . ?
C12 C11 C10 121.3(4) . . ?
C10 C12 Br6 118.7(3) 5_656 . ?
C11 C12 Br6 121.0(3) . . ?
C11 C12 C10 120.3(4) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O8 H8 O3 0.819(10) 1.925(15) 2.736(5) 171(6) 7_666 yes
O9 H9 O2 0.820(10) 1.842(17) 2.647(5) 167(6) 2_655 yes
O7 H7 O4 0.814(10) 2.26(2) 3.022(5) 157(5) 4_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11nd_r
_database_code_depnum_ccdc_archive 'CCDC 1940048'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br8 N2 Nd2 O18'
_chemical_formula_sum            'C20 H16 Br8 N2 Nd2 O18'
_chemical_formula_weight         1500.11
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Nd Nd -0.1943 3.0179 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3427(12)
_cell_length_b                   12.6185(16)
_cell_length_c                   16.2191(18)
_cell_angle_alpha                77.419(4)
_cell_angle_beta                 72.879(4)
_cell_angle_gamma                68.729(5)
_cell_volume                     1870.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.649
_shelx_estimated_absorpt_T_max   0.428
_shelx_estimated_absorpt_T_min   0.189
_exptl_absorpt_coefficient_mu    11.363
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1547 before and 0.0829 after correction.
The Ratio of minimum to maximum transmission is 0.3827.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light violet'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            92694
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.649
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7712
_reflns_number_total             9277
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.605
_refine_diff_density_min         -1.764
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         9277
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+7.7831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10
 0.85 with sigma of 0.01
 O11-H11
 0.85 with sigma of 0.01
 O17-H17
 0.85 with sigma of 0.01
 O18-H18
 0.85 with sigma of 0.01
 C13-H10
 1.91069 with sigma of 0.02
 Nd1-H10
 3.026644 with sigma of 0.02
 C14-H11
 1.891164 with sigma of 0.02
 Nd1-H11
 3.009963 with sigma of 0.02
 C19-H17
 1.888197 with sigma of 0.02
 Nd2-H17
 2.985151 with sigma of 0.02
 C20-H18
 1.895701 with sigma of 0.02
 Nd2-H18
 3.02219 with sigma of 0.02
3. Restrained planarity
 Br1, Br1_$4, Br2_$4, Br2, C1, C1_$4, C2_$4, C2, C3, C3_$4, C4_$4, C4
 with sigma of 0.1
 Br3, Br3_$5, Br4_$5, Br4, C5, C5_$5, C6_$5, C6, C7, C7_$5, C8_$5, C8
 with sigma of 0.1
 Br7, Br7_$6, Br8, Br8_$6, C15, C15_$6, C16_$6, C16, C17, C17_$6, C18_$6, C18
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(Br2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(Br3) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(Br4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(Br7) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(Br8) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Rigid body (RIGU) restrains
 Br1, Br2, C2, C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br3, Br4, C6, C7, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Br7, Br8, C16, C17, C18
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
6.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Nd1 Nd 1.00705(3) 0.69286(2) 0.28718(2) 0.02140(7) Uani 1 1 d D . . . .
Nd2 Nd 0.48841(3) 0.81196(2) 0.21004(2) 0.02187(7) Uani 1 1 d D . . . .
Br1 Br 0.61941(7) 0.72310(5) 0.55843(4) 0.03643(13) Uani 1 1 d . U . . .
Br2 Br 0.45427(7) 0.90272(5) 0.70715(3) 0.03840(14) Uani 1 1 d . U . . .
Br3 Br 0.80146(7) 0.39124(6) 0.16909(4) 0.04359(16) Uani 1 1 d . U . . .
Br4 Br 0.99099(7) 0.24293(5) 0.00578(4) 0.04203(15) Uani 1 1 d . U . . .
Br5 Br 1.26716(7) 0.76235(5) 0.50824(4) 0.04205(15) Uani 1 1 d . . . . .
Br6 Br 1.10735(8) 0.89855(6) 0.68036(4) 0.05060(18) Uani 1 1 d . . . . .
Br7 Br 0.42426(7) 0.40139(5) 0.20621(3) 0.03748(14) Uani 1 1 d . U . . .
Br8 Br 0.61099(7) 0.22299(5) 0.05896(4) 0.03606(13) Uani 1 1 d . U . . .
O1 O 0.7757(4) 0.7901(4) 0.3619(3) 0.0366(9) Uani 1 1 d . . . . .
O2 O 0.5711(4) 0.8294(4) 0.3252(3) 0.0357(9) Uani 1 1 d . . . . .
O3 O 0.9087(5) 0.6384(4) 0.1945(3) 0.0391(9) Uani 1 1 d . . . . .
O4 O 0.7082(4) 0.6717(4) 0.1571(3) 0.0384(9) Uani 1 1 d . . . . .
O5 O 1.0806(5) 0.8266(4) 0.3261(3) 0.0416(10) Uani 1 1 d . . . . .
O6 O 1.2656(4) 0.8839(4) 0.3097(3) 0.0407(10) Uani 1 1 d . . . . .
O7 O 1.0203(4) 0.6294(4) 0.4506(3) 0.0391(9) Uani 1 1 d . . . . .
O8 O 1.2197(4) 0.5786(4) 0.3549(3) 0.0386(9) Uani 1 1 d . . . . .
O9 O 1.2150(5) 0.5235(4) 0.4916(3) 0.0465(11) Uani 1 1 d . . . . .
O10 O 0.9311(4) 0.8708(4) 0.1866(3) 0.0362(9) Uani 1 1 d D . . . .
H10 H 0.851(3) 0.890(4) 0.173(4) 0.054 Uiso 1 1 d D U . . .
O11 O 0.9836(7) 0.4987(5) 0.3472(3) 0.0571(14) Uani 1 1 d D . . . .
H11 H 0.939(9) 0.489(3) 0.400(2) 0.086 Uiso 1 1 d D U . . .
O12 O 0.3899(4) 0.7216(4) 0.1447(3) 0.0356(9) Uani 1 1 d . . . . .
O13 O 0.2092(4) 0.6548(3) 0.1664(2) 0.0328(8) Uani 1 1 d . . . . .
O14 O 0.6688(4) 0.9188(4) 0.1423(3) 0.0369(9) Uani 1 1 d . . . . .
O15 O 0.5908(4) 0.8800(4) 0.0462(3) 0.0379(9) Uani 1 1 d . . . . .
O16 O 0.7344(5) 0.9810(4) 0.0054(3) 0.0479(11) Uani 1 1 d . . . . .
O17 O 0.3511(6) 1.0097(5) 0.1506(3) 0.0618(15) Uani 1 1 d D . . . .
H17 H 0.355(9) 1.017(3) 0.0963(15) 0.093 Uiso 1 1 d D U . . .
O18 O 0.4765(4) 0.6354(4) 0.3117(3) 0.0380(9) Uani 1 1 d D . . . .
H18 H 0.399(3) 0.618(4) 0.328(4) 0.057 Uiso 1 1 d D U . . .
N1 N 1.1522(5) 0.5759(4) 0.4346(3) 0.0311(10) Uani 1 1 d . . . . .
N2 N 0.6663(5) 0.9280(4) 0.0627(3) 0.0324(10) Uani 1 1 d . . . . .
C1 C 0.6456(4) 0.8413(4) 0.3685(3) 0.0229(9) Uani 1 1 d . . . . .
C2 C 0.5700(4) 0.9231(4) 0.4372(3) 0.0198(8) Uani 1 1 d . U . . .
C3 C 0.5501(4) 0.8833(4) 0.5259(3) 0.0222(9) Uani 1 1 d . U . . .
C4 C 0.4819(4) 0.9585(4) 0.5871(3) 0.0222(9) Uani 1 1 d . U . . .
C5 C 0.8345(4) 0.6323(4) 0.1460(3) 0.0235(10) Uani 1 1 d . . . . .
C6 C 0.9202(4) 0.5637(4) 0.0702(3) 0.0213(9) Uani 1 1 d . U . . .
C7 C 0.9158(4) 0.4544(4) 0.0720(3) 0.0219(9) Uani 1 1 d . U . . .
C8 C 0.9950(4) 0.3914(4) 0.0024(3) 0.0238(9) Uani 1 1 d . U . . .
C9 C 1.1443(5) 0.8784(4) 0.3474(3) 0.0244(10) Uani 1 1 d . . . . .
C10 C 1.0691(5) 0.9416(4) 0.4262(3) 0.0227(9) Uani 1 1 d . . . . .
C11 C 1.1144(5) 0.8999(4) 0.5028(3) 0.0236(9) Uani 1 1 d . . . . .
C12 C 1.0450(5) 0.9570(4) 0.5767(3) 0.0242(10) Uani 1 1 d . . . . .
C13 C 1.0112(9) 0.9414(6) 0.1325(4) 0.0492(17) Uani 1 1 d D . . . .
H13A H 1.038885 0.924068 0.073837 0.074 Uiso 1 1 calc R U . . .
H13B H 1.094959 0.927502 0.152788 0.074 Uiso 1 1 calc R U . . .
H13C H 0.953772 1.020497 0.134489 0.074 Uiso 1 1 calc R U . . .
C14 C 1.0393(10) 0.3928(7) 0.3121(6) 0.067(2) Uani 1 1 d D . . . .
H14A H 1.080406 0.405328 0.250924 0.100 Uiso 1 1 calc R U . . .
H14B H 0.963717 0.361450 0.320983 0.100 Uiso 1 1 calc R U . . .
H14C H 1.111387 0.340146 0.340621 0.100 Uiso 1 1 calc R U . . .
C15 C 0.3334(4) 0.6575(4) 0.1311(3) 0.0226(9) Uani 1 1 d . . . . .
C16 C 0.4196(4) 0.5766(4) 0.0626(3) 0.0201(8) Uani 1 1 d . U . . .
C17 C 0.4680(4) 0.4577(4) 0.0869(3) 0.0220(8) Uani 1 1 d . U . . .
C18 C 0.5462(4) 0.3830(4) 0.0258(3) 0.0225(8) Uani 1 1 d . U . . .
C19 C 0.2610(9) 1.1141(7) 0.1831(6) 0.062(2) Uani 1 1 d D . . . .
H19A H 0.306186 1.172033 0.159371 0.093 Uiso 1 1 calc R U . . .
H19B H 0.243662 1.103563 0.245311 0.093 Uiso 1 1 calc R U . . .
H19C H 0.171884 1.137394 0.166516 0.093 Uiso 1 1 calc R U . . .
C20 C 0.5720(8) 0.5606(6) 0.3626(5) 0.0521(17) Uani 1 1 d D . . . .
H20A H 0.665868 0.566514 0.336958 0.078 Uiso 1 1 calc R U . . .
H20B H 0.574760 0.483224 0.364866 0.078 Uiso 1 1 calc R U . . .
H20C H 0.540088 0.581638 0.420445 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.347(4) . ?
Nd1 O3 2.372(4) . ?
Nd1 O5 2.347(4) . ?
Nd1 O7 2.626(4) . ?
Nd1 O8 2.561(4) . ?
Nd1 O10 2.490(4) . ?
Nd1 O11 2.503(5) . ?
Nd1 O13 2.390(3) 1_655 ?
Nd2 O2 2.351(4) . ?
Nd2 O4 2.373(4) . ?
Nd2 O6 2.382(4) 1_455 ?
Nd2 O12 2.338(4) . ?
Nd2 O14 2.546(4) . ?
Nd2 O15 2.632(4) . ?
Nd2 O17 2.522(5) . ?
Nd2 O18 2.486(4) . ?
Br1 C3 1.893(5) . ?
Br2 C4 1.895(4) . ?
Br3 C7 1.885(5) . ?
Br4 C8 1.878(5) . ?
Br5 C11 1.882(5) . ?
Br6 C12 1.882(5) . ?
Br7 C17 1.890(5) . ?
Br8 C18 1.890(5) . ?
O1 C1 1.247(5) . ?
O2 C1 1.248(5) . ?
O3 C5 1.281(5) . ?
O4 C5 1.189(5) . ?
O5 C9 1.234(6) . ?
O6 C9 1.243(6) . ?
O7 N1 1.258(6) . ?
O8 N1 1.275(6) . ?
O9 N1 1.220(6) . ?
O10 H10 0.856(9) . ?
O10 C13 1.420(7) . ?
O11 H11 0.852(9) . ?
O11 C14 1.421(9) . ?
O12 C15 1.241(5) . ?
O13 C15 1.252(5) . ?
O14 N2 1.278(6) . ?
O15 N2 1.259(6) . ?
O16 N2 1.223(6) . ?
O17 H17 0.854(9) . ?
O17 C19 1.416(9) . ?
O18 H18 0.855(9) . ?
O18 C20 1.419(8) . ?
C1 C2 1.523(6) . ?
C2 C3 1.396(6) . ?
C2 C4 1.401(7) 2_676 ?
C3 C4 1.377(7) . ?
C5 C6 1.519(6) . ?
C6 C7 1.391(7) . ?
C6 C8 1.392(7) 2_765 ?
C7 C8 1.396(6) . ?
C9 C10 1.512(6) . ?
C10 C11 1.385(7) . ?
C10 C12 1.394(7) 2_776 ?
C11 C12 1.401(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.524(6) . ?
C16 C17 1.404(7) . ?
C16 C18 1.398(6) 2_665 ?
C17 C18 1.381(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 Nd1 O3 89.74(15) . . ?
O1 Nd1 O7 77.47(14) . . ?
O1 Nd1 O8 126.15(13) . . ?
O1 Nd1 O10 76.30(15) . . ?
O1 Nd1 O11 93.79(18) . . ?
O1 Nd1 O13 156.49(15) . 1_655 ?
O3 Nd1 O7 133.67(15) . . ?
O3 Nd1 O8 130.07(15) . . ?
O3 Nd1 O10 76.09(15) . . ?
O3 Nd1 O11 71.26(16) . . ?
O3 Nd1 O13 80.73(14) . 1_655 ?
O5 Nd1 O1 86.54(15) . . ?
O5 Nd1 O3 151.05(16) . . ?
O5 Nd1 O7 73.28(15) . . ?
O5 Nd1 O8 73.14(15) . . ?
O5 Nd1 O10 75.13(15) . . ?
O5 Nd1 O11 137.62(16) . . ?
O5 Nd1 O13 91.47(15) . 1_655 ?
O8 Nd1 O7 49.19(12) . . ?
O10 Nd1 O7 139.72(14) . . ?
O10 Nd1 O8 139.06(14) . . ?
O10 Nd1 O11 145.90(16) . . ?
O11 Nd1 O7 65.53(15) . . ?
O11 Nd1 O8 72.75(17) . . ?
O13 Nd1 O7 124.29(13) 1_655 . ?
O13 Nd1 O8 75.13(13) 1_655 . ?
O13 Nd1 O10 80.55(14) 1_655 . ?
O13 Nd1 O11 103.26(16) 1_655 . ?
O2 Nd2 O4 91.49(15) . . ?
O2 Nd2 O6 80.42(15) . 1_455 ?
O2 Nd2 O14 73.94(14) . . ?
O2 Nd2 O15 123.15(14) . . ?
O2 Nd2 O17 108.29(17) . . ?
O2 Nd2 O18 77.13(14) . . ?
O4 Nd2 O6 155.24(16) . 1_455 ?
O4 Nd2 O14 73.89(15) . . ?
O4 Nd2 O15 71.16(15) . . ?
O4 Nd2 O17 134.95(16) . . ?
O4 Nd2 O18 76.23(15) . . ?
O6 Nd2 O14 124.95(15) 1_455 . ?
O6 Nd2 O15 132.57(15) 1_455 . ?
O6 Nd2 O17 69.63(16) 1_455 . ?
O6 Nd2 O18 79.16(15) 1_455 . ?
O12 Nd2 O2 152.59(15) . . ?
O12 Nd2 O4 84.87(15) . . ?
O12 Nd2 O6 91.62(15) . 1_455 ?
O12 Nd2 O14 130.15(14) . . ?
O12 Nd2 O15 81.30(14) . . ?
O12 Nd2 O17 93.06(18) . . ?
O12 Nd2 O18 75.62(15) . . ?
O14 Nd2 O15 49.38(13) . . ?
O17 Nd2 O14 73.56(18) . . ?
O17 Nd2 O15 64.08(15) . . ?
O18 Nd2 O14 137.32(14) . . ?
O18 Nd2 O15 141.36(14) . . ?
O18 Nd2 O17 146.52(17) . . ?
C1 O1 Nd1 153.8(3) . . ?
C1 O2 Nd2 163.1(3) . . ?
C5 O3 Nd1 166.7(4) . . ?
C5 O4 Nd2 150.9(4) . . ?
C9 O5 Nd1 166.9(4) . . ?
C9 O6 Nd2 149.3(4) . 1_655 ?
N1 O7 Nd1 95.6(3) . . ?
N1 O8 Nd1 98.2(3) . . ?
Nd1 O10 H10 119.9(15) . . ?
C13 O10 Nd1 129.8(4) . . ?
C13 O10 H10 109.4(15) . . ?
Nd1 O11 H11 118.1(15) . . ?
C14 O11 Nd1 132.7(5) . . ?
C14 O11 H11 109.1(15) . . ?
C15 O12 Nd2 163.5(4) . . ?
C15 O13 Nd1 148.3(3) . 1_455 ?
N2 O14 Nd2 98.5(3) . . ?
N2 O15 Nd2 94.9(3) . . ?
Nd2 O17 H17 113.8(14) . . ?
C19 O17 Nd2 137.6(5) . . ?
C19 O17 H17 108.5(14) . . ?
Nd2 O18 H18 120.2(15) . . ?
C20 O18 Nd2 130.6(4) . . ?
C20 O18 H18 108.3(15) . . ?
O7 N1 O8 116.9(4) . . ?
O9 N1 O7 122.7(5) . . ?
O9 N1 O8 120.4(5) . . ?
O15 N2 O14 117.1(4) . . ?
O16 N2 O14 121.2(5) . . ?
O16 N2 O15 121.7(5) . . ?
O1 C1 O2 125.7(5) . . ?
O1 C1 C2 117.1(4) . . ?
O2 C1 C2 117.1(4) . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 C4 117.8(4) . 2_676 ?
C4 C2 C1 120.6(4) 2_676 . ?
C2 C3 Br1 117.7(4) . . ?
C4 C3 Br1 121.5(3) . . ?
C4 C3 C2 120.8(4) . . ?
C2 C4 Br2 118.4(3) 2_676 . ?
C3 C4 Br2 120.2(4) . . ?
C3 C4 C2 121.4(4) . 2_676 ?
O3 C5 C6 114.6(4) . . ?
O4 C5 O3 125.9(5) . . ?
O4 C5 C6 119.4(4) . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 C8 118.4(4) . 2_765 ?
C8 C6 C5 121.0(4) 2_765 . ?
C6 C7 Br3 119.6(3) . . ?
C6 C7 C8 120.5(4) . . ?
C8 C7 Br3 119.9(4) . . ?
C6 C8 Br4 118.5(4) 2_765 . ?
C6 C8 C7 121.1(4) 2_765 . ?
C7 C8 Br4 120.4(4) . . ?
O5 C9 O6 126.0(5) . . ?
O5 C9 C10 117.7(5) . . ?
O6 C9 C10 116.3(4) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 C12 118.7(4) . 2_776 ?
C12 C10 C9 121.2(4) 2_776 . ?
C10 C11 Br5 119.3(4) . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 Br5 119.9(4) . . ?
C10 C12 Br6 119.4(4) 2_776 . ?
C10 C12 C11 120.5(4) 2_776 . ?
C11 C12 Br6 120.1(4) . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O12 C15 O13 126.4(5) . . ?
O12 C15 C16 117.8(3) . . ?
O13 C15 C16 115.8(4) . . ?
C17 C16 C15 120.5(4) . . ?
C18 C16 C15 121.9(4) 2_665 . ?
C18 C16 C17 117.6(4) 2_665 . ?
C16 C17 Br7 118.3(3) . . ?
C18 C17 Br7 120.4(4) . . ?
C18 C17 C16 121.3(4) . . ?
C16 C18 Br8 117.8(4) 2_665 . ?
C17 C18 Br8 121.1(3) . . ?
C17 C18 C16 121.1(4) . 2_665 ?
O17 C19 H19A 109.5 . . ?
O17 C19 H19B 109.5 . . ?
O17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O18 C20 H20A 109.5 . . ?
O18 C20 H20B 109.5 . . ?
O18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_hbond_publ_flag
O10 H10 O14 0.856(9) 1.976(13) 2.830(6) 175(5) . yes
O11 H11 O9 0.852(9) 2.01(3) 2.841(7) 163(9) 2_766 yes
O17 H17 O15 0.854(9) 2.41(5) 3.167(6) 148(8) 2_675 yes
O17 H17 O16 0.854(9) 2.11(5) 2.882(7) 150(9) 2_675 yes
O18 H18 O8 0.855(9) 1.998(11) 2.850(6) 175(6) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Nd1 O1 C1 O2 25.4(12) . . . . ?
Nd1 O1 C1 C2 -156.5(6) . . . . ?
Nd1 O3 C5 O4 -37.3(19) . . . . ?
Nd1 O3 C5 C6 145.1(14) . . . . ?
Nd1 O5 C9 O6 54(2) . . . . ?
Nd1 O5 C9 C10 -126.6(15) . . . . ?
Nd1 O7 N1 O8 3.1(5) . . . . ?
Nd1 O7 N1 O9 -177.1(5) . . . . ?
Nd1 O8 N1 O7 -3.2(5) . . . . ?
Nd1 O8 N1 O9 177.0(4) . . . . ?
Nd1 O13 C15 O12 -23.7(10) 1_455 . . . ?
Nd1 O13 C15 C16 158.7(5) 1_455 . . . ?
Nd2 O2 C1 O1 -46.4(16) . . . . ?
Nd2 O2 C1 C2 135.5(11) . . . . ?
Nd2 O4 C5 O3 29.4(11) . . . . ?
Nd2 O4 C5 C6 -153.1(6) . . . . ?
Nd2 O6 C9 O5 -16.4(12) 1_655 . . . ?
Nd2 O6 C9 C10 163.8(5) 1_655 . . . ?
Nd2 O12 C15 O13 64.9(14) . . . . ?
Nd2 O12 C15 C16 -117.6(11) . . . . ?
Nd2 O14 N2 O15 -4.0(5) . . . . ?
Nd2 O14 N2 O16 176.1(4) . . . . ?
Nd2 O15 N2 O14 3.8(5) . . . . ?
Nd2 O15 N2 O16 -176.2(4) . . . . ?
Br1 C3 C4 Br2 -0.4(4) . . . . ?
Br1 C3 C4 C2 -179.6(2) . . . 2_676 ?
Br3 C7 C8 Br4 -1.1(4) . . . . ?
Br3 C7 C8 C6 179.7(2) . . . 2_765 ?
Br5 C11 C12 Br6 1.5(6) . . . . ?
Br5 C11 C12 C10 -179.4(4) . . . 2_776 ?
Br7 C17 C18 Br8 0.3(4) . . . . ?
Br7 C17 C18 C16 -179.5(2) . . . 2_665 ?
O1 C1 C2 C3 -67.9(5) . . . . ?
O1 C1 C2 C4 112.2(5) . . . 2_676 ?
O2 C1 C2 C3 110.4(5) . . . . ?
O2 C1 C2 C4 -69.6(5) . . . 2_676 ?
O3 C5 C6 C7 105.3(5) . . . . ?
O3 C5 C6 C8 -74.7(5) . . . 2_765 ?
O4 C5 C6 C7 -72.5(5) . . . . ?
O4 C5 C6 C8 107.5(5) . . . 2_765 ?
O5 C9 C10 C11 108.1(6) . . . . ?
O5 C9 C10 C12 -72.8(7) . . . 2_776 ?
O6 C9 C10 C11 -72.1(7) . . . . ?
O6 C9 C10 C12 107.0(6) . . . 2_776 ?
O12 C15 C16 C17 111.9(5) . . . . ?
O12 C15 C16 C18 -67.9(5) . . . 2_665 ?
O13 C15 C16 C17 -70.3(5) . . . . ?
O13 C15 C16 C18 109.9(5) . . . 2_665 ?
C1 C2 C3 Br1 -0.4(4) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 Br2 179.4(2) . . . . ?
C2 C3 C4 C2 0.2(5) . . . 2_676 ?
C4 C2 C3 Br1 179.6(2) 2_676 . . . ?
C4 C2 C3 C4 -0.2(5) 2_676 . . . ?
C5 C6 C7 Br3 0.3(4) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C6 C7 C8 Br4 179.0(2) . . . . ?
C6 C7 C8 C6 -0.2(5) . . . 2_765 ?
C8 C6 C7 Br3 -179.7(2) 2_765 . . . ?
C8 C6 C7 C8 0.2(5) 2_765 . . . ?
C9 C10 C11 Br5 -1.5(6) . . . . ?
C9 C10 C11 C12 -179.5(5) . . . . ?
C10 C11 C12 Br6 179.6(4) . . . . ?
C10 C11 C12 C10 -1.4(8) . . . 2_776 ?
C12 C10 C11 Br5 179.4(4) 2_776 . . . ?
C12 C10 C11 C12 1.3(8) 2_776 . . . ?
C15 C16 C17 Br7 -0.4(4) . . . . ?
C15 C16 C17 C18 180.0(3) . . . . ?
C16 C17 C18 Br8 180.0(2) . . . . ?
C16 C17 C18 C16 0.2(5) . . . 2_665 ?
C18 C16 C17 Br7 179.5(2) 2_665 . . . ?
C18 C16 C17 C18 -0.2(5) 2_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3nd_re
_database_code_depnum_ccdc_archive 'CCDC 1940037'
loop_
_audit_author_name
_audit_author_address
'Dr. Kittipong Chainok'
;Thammasat University
Thailand
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br6 Nd O9'
_chemical_formula_sum            'C15 H12 Br6 Nd O9'
_chemical_formula_weight         959.95
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3900(4)
_cell_length_b                   10.6244(2)
_cell_length_c                   22.1112(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.8930(10)
_cell_angle_gamma                90
_cell_volume                     4772.53(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9737
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      28.715
_cell_measurement_theta_min      2.609
_shelx_estimated_absorpt_T_max   0.216
_shelx_estimated_absorpt_T_min   0.125
_exptl_absorpt_coefficient_mu    12.266
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.7490.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            108982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.747
_diffrn_reflns_theta_min         2.609
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5642
_reflns_number_total             6193
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6193
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+11.5214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O9-H9 = O8-H8
 0.82 with sigma of 0.01
 O7-H7
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Nd1 Nd 0.52564(2) 0.52288(2) 0.39231(2) 0.01763(4) Uani 1 1 d . . . . .
Br1 Br 0.76007(2) 0.49470(3) 0.31563(2) 0.03531(7) Uani 1 1 d . . . . .
Br2 Br 0.90406(2) 0.63663(3) 0.33814(2) 0.03366(7) Uani 1 1 d . . . . .
Br3 Br 0.77423(2) 1.10608(3) 0.35593(2) 0.03619(7) Uani 1 1 d . . . . .
Br4 Br 0.63043(2) 0.96002(3) 0.33124(2) 0.03964(8) Uani 1 1 d . . . . .
Br5 Br 0.64196(2) 0.14170(3) 0.49602(2) 0.03958(8) Uani 1 1 d . . . . .
Br6 Br 0.63422(2) -0.17019(3) 0.50354(2) 0.03243(7) Uani 1 1 d . . . . .
O1 O 0.61250(10) 0.6514(2) 0.36409(10) 0.0338(5) Uani 1 1 d . . . . .
O2 O 0.61971(12) 0.6469(3) 0.26435(10) 0.0506(6) Uani 1 1 d . . . . .
O3 O 0.90783(9) 0.97373(19) 0.41017(9) 0.0292(4) Uani 1 1 d . . . . .
O4 O 0.93418(9) 0.92817(18) 0.31823(9) 0.0274(4) Uani 1 1 d . . . . .
O5 O 0.51797(10) 0.30884(17) 0.43249(9) 0.0298(4) Uani 1 1 d . . . . .
O6 O 0.49968(10) 0.34265(17) 0.52851(9) 0.0306(4) Uani 1 1 d . . . . .
O7 O 0.58045(11) 0.4024(2) 0.31621(10) 0.0360(5) Uani 1 1 d D . . . .
H7 H 0.584(2) 0.438(4) 0.2840(11) 0.069(14) Uiso 1 1 d D . . . .
O8 O 0.61908(10) 0.4958(2) 0.47200(10) 0.0325(5) Uani 1 1 d D . . . .
H8 H 0.612(2) 0.509(4) 0.5073(7) 0.056(13) Uiso 1 1 d D . . . .
O9 O 0.46642(11) 0.6840(2) 0.33033(11) 0.0384(5) Uani 1 1 d D . . . .
H9 H 0.4420(16) 0.663(4) 0.3010(11) 0.052(12) Uiso 1 1 d D . . . .
C1 C 0.64018(12) 0.6740(3) 0.31645(12) 0.0254(5) Uani 1 1 d . . . . .
C2 C 0.70655(12) 0.7395(2) 0.32623(11) 0.0207(5) Uani 1 1 d . . . . .
C3 C 0.76470(13) 0.6709(2) 0.32657(11) 0.0222(5) Uani 1 1 d . . . . .
C4 C 0.82562(12) 0.7313(2) 0.33593(11) 0.0222(5) Uani 1 1 d . . . . .
C5 C 0.82867(12) 0.8612(2) 0.34572(11) 0.0218(5) Uani 1 1 d . . . . .
C6 C 0.89476(12) 0.9259(2) 0.35834(12) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.77026(12) 0.9296(2) 0.34490(12) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.70990(12) 0.8689(2) 0.33506(12) 0.0231(5) Uani 1 1 d . . . . .
C9 C 0.50732(12) 0.2727(2) 0.48411(12) 0.0208(5) Uani 1 1 d . . . . .
C10 C 0.50323(12) 0.1314(2) 0.49338(11) 0.0183(5) Uani 1 1 d . . . . .
C11 C 0.56026(12) 0.0586(2) 0.49644(12) 0.0211(5) Uani 1 1 d . . . . .
C12 C 0.55732(12) -0.0719(2) 0.50219(11) 0.0201(5) Uani 1 1 d . . . . .
C13 C 0.5966(3) 0.2755(4) 0.3158(2) 0.0760(15) Uani 1 1 d . . . . .
H13A H 0.632554 0.262786 0.291141 0.114 Uiso 1 1 calc R U . . .
H13B H 0.559175 0.227861 0.299497 0.114 Uiso 1 1 calc R U . . .
H13C H 0.609220 0.248109 0.356517 0.114 Uiso 1 1 calc R U . . .
C14 C 0.68826(16) 0.4944(4) 0.47059(18) 0.0557(11) Uani 1 1 d . . . . .
H14A H 0.700860 0.423724 0.447127 0.084 Uiso 1 1 calc R U . . .
H14B H 0.708650 0.487709 0.511224 0.084 Uiso 1 1 calc R U . . .
H14C H 0.702258 0.570855 0.452445 0.084 Uiso 1 1 calc R U . . .
C15 C 0.4578(2) 0.8149(3) 0.3408(2) 0.0588(11) Uani 1 1 d . . . . .
H15A H 0.455915 0.859180 0.302826 0.088 Uiso 1 1 calc R U . . .
H15B H 0.494182 0.845822 0.367067 0.088 Uiso 1 1 calc R U . . .
H15C H 0.417599 0.828010 0.359503 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.3619(18) . ?
Nd1 O3 2.5222(19) 3_445 ?
Nd1 O4 2.5792(18) 3_445 ?
Nd1 O5 2.4513(18) . ?
Nd1 O6 2.3509(19) 5_666 ?
Nd1 O7 2.457(2) . ?
Nd1 O8 2.499(2) . ?
Nd1 O9 2.446(2) . ?
Nd1 C6 2.899(2) 3_445 ?
Br1 C3 1.889(3) . ?
Br2 C4 1.887(3) . ?
Br3 C7 1.892(3) . ?
Br4 C8 1.883(3) . ?
Br5 C11 1.886(2) . ?
Br6 C12 1.882(2) . ?
O1 C1 1.260(3) . ?
O2 C1 1.226(3) . ?
O3 C6 1.261(3) . ?
O4 C6 1.247(3) . ?
O5 C9 1.241(3) . ?
O6 C9 1.252(3) . ?
O7 H7 0.813(10) . ?
O7 C13 1.388(4) . ?
O8 H8 0.817(10) . ?
O8 C14 1.414(4) . ?
O9 H9 0.815(10) . ?
O9 C15 1.423(4) . ?
C1 C2 1.520(3) . ?
C2 C3 1.391(4) . ?
C2 C8 1.390(4) . ?
C3 C4 1.398(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.518(3) . ?
C5 C7 1.394(4) . ?
C7 C8 1.390(3) . ?
C9 C10 1.518(3) . ?
C10 C11 1.394(3) . ?
C10 C12 1.398(3) 5_656 ?
C11 C12 1.394(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 Nd1 O3 155.05(7) . 3_445 ?
O1 Nd1 O4 125.14(7) . 3_445 ?
O1 Nd1 O5 134.79(7) . . ?
O1 Nd1 O7 74.04(7) . . ?
O1 Nd1 O8 73.10(7) . . ?
O1 Nd1 O9 78.05(8) . . ?
O1 Nd1 C6 146.23(7) . 3_445 ?
O3 Nd1 O4 51.09(6) 3_445 3_445 ?
O3 Nd1 C6 25.71(7) 3_445 3_445 ?
O4 Nd1 C6 25.46(6) 3_445 3_445 ?
O5 Nd1 O3 70.13(7) . 3_445 ?
O5 Nd1 O4 78.65(6) . 3_445 ?
O5 Nd1 O7 79.16(7) . . ?
O5 Nd1 O8 72.90(7) . . ?
O5 Nd1 C6 71.25(7) . 3_445 ?
O6 Nd1 O1 93.60(7) 5_666 . ?
O6 Nd1 O3 74.73(6) 5_666 3_445 ?
O6 Nd1 O4 121.15(6) 5_666 3_445 ?
O6 Nd1 O5 105.60(7) 5_666 . ?
O6 Nd1 O7 165.46(7) 5_666 . ?
O6 Nd1 O8 75.38(7) 5_666 . ?
O6 Nd1 O9 82.11(8) 5_666 . ?
O6 Nd1 C6 98.81(7) 5_666 3_445 ?
O7 Nd1 O3 119.62(7) . 3_445 ?
O7 Nd1 O4 73.04(7) . 3_445 ?
O7 Nd1 O8 93.37(7) . . ?
O7 Nd1 C6 95.73(8) . 3_445 ?
O8 Nd1 O3 123.01(7) . 3_445 ?
O8 Nd1 O4 150.37(7) . 3_445 ?
O8 Nd1 C6 140.47(7) . 3_445 ?
O9 Nd1 O3 78.54(7) . 3_445 ?
O9 Nd1 O4 67.77(7) . 3_445 ?
O9 Nd1 O5 143.95(7) . . ?
O9 Nd1 O7 102.26(8) . . ?
O9 Nd1 O8 141.81(7) . . ?
O9 Nd1 C6 72.78(7) . 3_445 ?
C1 O1 Nd1 136.95(18) . . ?
C6 O3 Nd1 94.09(15) . 3 ?
C6 O4 Nd1 91.76(15) . 3 ?
C9 O5 Nd1 129.96(17) . . ?
C9 O6 Nd1 174.22(18) . 5_666 ?
Nd1 O7 H7 116(3) . . ?
C13 O7 Nd1 129.2(2) . . ?
C13 O7 H7 114(3) . . ?
Nd1 O8 H8 118(3) . . ?
C14 O8 Nd1 133.5(2) . . ?
C14 O8 H8 106(3) . . ?
Nd1 O9 H9 119(3) . . ?
C15 O9 Nd1 130.9(2) . . ?
C15 O9 H9 109(3) . . ?
O1 C1 C2 115.2(2) . . ?
O2 C1 O1 126.8(2) . . ?
O2 C1 C2 118.0(2) . . ?
C3 C2 C1 120.6(2) . . ?
C8 C2 C1 120.3(2) . . ?
C8 C2 C3 119.1(2) . . ?
C2 C3 Br1 119.02(18) . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 Br1 120.54(19) . . ?
C3 C4 Br2 119.99(19) . . ?
C5 C4 Br2 119.74(18) . . ?
C5 C4 C3 120.2(2) . . ?
C4 C5 C6 120.2(2) . . ?
C7 C5 C4 119.1(2) . . ?
C7 C5 C6 120.7(2) . . ?
O3 C6 Nd1 60.20(13) . 3 ?
O3 C6 C5 117.7(2) . . ?
O4 C6 Nd1 62.78(13) . 3 ?
O4 C6 O3 122.7(2) . . ?
O4 C6 C5 119.6(2) . . ?
C5 C6 Nd1 172.77(18) . 3 ?
C5 C7 Br3 119.19(18) . . ?
C8 C7 Br3 120.5(2) . . ?
C8 C7 C5 120.3(2) . . ?
C2 C8 Br4 118.06(18) . . ?
C7 C8 Br4 121.1(2) . . ?
C7 C8 C2 120.9(2) . . ?
O5 C9 O6 125.5(2) . . ?
O5 C9 C10 116.5(2) . . ?
O6 C9 C10 118.0(2) . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 C12 118.9(2) . 5_656 ?
C12 C10 C9 121.0(2) 5_656 . ?
C10 C11 Br5 118.28(18) . . ?
C10 C11 C12 120.9(2) . . ?
C12 C11 Br5 120.72(18) . . ?
C10 C12 Br6 119.18(17) 5_656 . ?
C11 C12 Br6 120.72(18) . . ?
C11 C12 C10 120.1(2) . 5_656 ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O7 H7 O2 0.813(10) 2.39(4) 2.976(3) 129(4) . yes
O7 H7 O4 0.813(10) 2.26(3) 2.975(3) 147(4) 4_645 yes
O8 H8 O3 0.817(10) 1.913(11) 2.727(3) 175(4) 7_666 yes
O9 H9 O2 0.815(10) 1.841(13) 2.645(3) 168(4) 2_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Nd1 O1 C1 O2 14.4(5) . . . . ?
Nd1 O1 C1 C2 -164.17(19) . . . . ?
Nd1 O3 C6 O4 -6.6(3) 3 . . . ?
Nd1 O3 C6 C5 172.10(19) 3 . . . ?
Nd1 O4 C6 O3 6.4(3) 3 . . . ?
Nd1 O4 C6 C5 -172.2(2) 3 . . . ?
Nd1 O5 C9 O6 -2.0(4) . . . . ?
Nd1 O5 C9 C10 177.83(15) . . . . ?
Br1 C3 C4 Br2 -0.3(3) . . . . ?
Br1 C3 C4 C5 -178.17(19) . . . . ?
Br2 C4 C5 C6 -0.2(3) . . . . ?
Br2 C4 C5 C7 -178.99(19) . . . . ?
Br3 C7 C8 Br4 0.9(3) . . . . ?
Br3 C7 C8 C2 179.26(19) . . . . ?
Br5 C11 C12 Br6 -4.8(3) . . . . ?
Br5 C11 C12 C10 175.60(19) . . . 5_656 ?
O1 C1 C2 C3 99.0(3) . . . . ?
O1 C1 C2 C8 -80.9(3) . . . . ?
O2 C1 C2 C3 -79.7(3) . . . . ?
O2 C1 C2 C8 100.4(3) . . . . ?
O5 C9 C10 C11 73.7(3) . . . . ?
O5 C9 C10 C12 -105.1(3) . . . 5_656 ?
O6 C9 C10 C11 -106.4(3) . . . . ?
O6 C9 C10 C12 74.8(3) . . . 5_656 ?
C1 C2 C3 Br1 -0.7(3) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C8 Br4 -2.5(3) . . . . ?
C1 C2 C8 C7 179.1(2) . . . . ?
C2 C3 C4 Br2 178.54(19) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C2 C8 Br4 177.59(18) . . . . ?
C3 C2 C8 C7 -0.8(4) . . . . ?
C3 C4 C5 C6 177.6(2) . . . . ?
C3 C4 C5 C7 -1.2(4) . . . . ?
C4 C5 C6 O3 -113.7(3) . . . . ?
C4 C5 C6 O4 65.0(3) . . . . ?
C4 C5 C7 Br3 -178.28(19) . . . . ?
C4 C5 C7 C8 0.6(4) . . . . ?
C5 C7 C8 Br4 -178.0(2) . . . . ?
C5 C7 C8 C2 0.4(4) . . . . ?
C6 C5 C7 Br3 3.0(3) . . . . ?
C6 C5 C7 C8 -178.1(2) . . . . ?
C7 C5 C6 O3 65.0(3) . . . . ?
C7 C5 C6 O4 -116.3(3) . . . . ?
C8 C2 C3 Br1 179.17(19) . . . . ?
C8 C2 C3 C4 0.3(4) . . . . ?
C9 C10 C11 Br5 5.5(3) . . . . ?
C9 C10 C11 C12 -177.1(2) . . . . ?
C10 C11 C12 Br6 177.84(19) . . . . ?
C10 C11 C12 C10 -1.7(4) . . . 5_656 ?
C12 C10 C11 Br5 -175.69(18) 5_656 . . . ?
C12 C10 C11 C12 1.7(4) 5_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
