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#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/22/7052201.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7052201
loop_
_publ_author_name
'Albrecht, Markus'
'Schmid, Sören'
'Dehn, Sabrina'
'Wickleder, Claudia'
'Zhang, Shuang'
'Bassett, Andrew P.'
'Pikramenou, Zoe'
'Fröhlich, Roland'
_publ_section_title
;
 Diastereoselective formation of luminescent dinuclear lanthanide(iii)
 helicates with enantiomerically pure tartaric acid derived
 bis(β-diketonate) ligands
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1755
_journal_paper_doi               10.1039/b705090a
_journal_volume                  31
_journal_year                    2007
_chemical_formula_sum            'C23 H20 Br2 O6'
_chemical_formula_weight         552.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.691(1)
_cell_length_b                   9.359(1)
_cell_length_c                   41.058(1)
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_volume                     2186.8(5)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            11822
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.8960
_exptl_absorpt_correction_T_min  0.2561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0368P)²+1.4364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                3682
_reflns_number_total             5022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b705090a.txt
_cod_data_source_block           fro3869
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7052201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6888(6) 0.5255(4) -0.16939(9) 0.0335(9) Uani 1 1 d . . .
O1 O 0.6573(6) 0.4037(3) -0.15479(8) 0.0543(9) Uani 1 1 d . . .
H1 H 0.5480 0.4111 -0.1415 0.081 Uiso 1 1 calc R . .
C11 C 0.8852(7) 0.5272(4) -0.19294(9) 0.0336(9) Uani 1 1 d . . .
C12 C 0.9522(7) 0.6485(4) -0.20957(10) 0.0433(10) Uani 1 1 d . . .
H12 H 0.8744 0.7352 -0.2055 0.052 Uiso 1 1 calc R . .
C13 C 1.1315(7) 0.6446(5) -0.23214(11) 0.0465(11) Uani 1 1 d . . .
H13 H 1.1766 0.7281 -0.2432 0.056 Uiso 1 1 calc R . .
C14 C 1.2439(7) 0.5171(5) -0.23833(9) 0.0380(9) Uani 1 1 d . . .
C15 C 1.1858(8) 0.3960(5) -0.22166(12) 0.0509(12) Uani 1 1 d . . .
H15 H 1.2667 0.3100 -0.2255 0.061 Uiso 1 1 calc R . .
C16 C 1.0049(8) 0.4017(4) -0.19890(11) 0.0461(11) Uani 1 1 d . . .
H16 H 0.9635 0.3186 -0.1874 0.055 Uiso 1 1 calc R . .
Br1 Br 1.48061(8) 0.50647(6) -0.270731(12) 0.05654(15) Uani 1 1 d . . .
C2 C 0.5478(7) 0.6417(4) -0.16240(9) 0.0351(9) Uani 1 1 d . . .
H2 H 0.5755 0.7299 -0.1726 0.042 Uiso 1 1 calc R . .
C3 C 0.3632(7) 0.6276(4) -0.13997(9) 0.0357(9) Uani 1 1 d . . .
O3 O 0.3218(5) 0.5132(3) -0.12458(8) 0.0556(8) Uani 1 1 d . . .
C4 C 0.2023(7) 0.7493(4) -0.13158(9) 0.0336(9) Uani 1 1 d . . .
H4 H 0.0371 0.7163 -0.1317 0.040 Uiso 1 1 calc R . .
O4 O 0.2292(5) 0.8663(3) -0.15315(7) 0.0372(7) Uani 1 1 d . . .
C5 C 0.2615(6) 0.8174(4) -0.09823(9) 0.0303(8) Uani 1 1 d . . .
H5 H 0.4306 0.8038 -0.0935 0.036 Uiso 1 1 calc R . .
O5 O 0.2153(5) 0.9649(3) -0.10291(6) 0.0368(6) Uani 1 1 d . . .
C6 C 0.1176(6) 0.7568(4) -0.07067(9) 0.0304(8) Uani 1 1 d . . .
O6 O -0.1099(5) 0.7864(3) -0.07215(7) 0.0479(8) Uani 1 1 d . . .
C7 C 0.2102(6) 0.6745(4) -0.04693(9) 0.0304(8) Uani 1 1 d . . .
H7 H 0.3727 0.6563 -0.0468 0.036 Uiso 1 1 calc R . .
C8 C 0.0645(6) 0.6145(4) -0.02200(9) 0.0297(8) Uani 1 1 d . . .
O8 O -0.1517(4) 0.6458(3) -0.02094(7) 0.0413(7) Uani 1 1 d . . .
H8 H -0.1869 0.6940 -0.0372 0.062 Uiso 1 1 calc R . .
C81 C 0.1561(6) 0.5137(4) 0.00228(9) 0.0296(8) Uani 1 1 d . . .
C82 C 0.3727(6) 0.4470(4) -0.00101(10) 0.0338(9) Uani 1 1 d . . .
H82 H 0.4699 0.4710 -0.0187 0.041 Uiso 1 1 calc R . .
C83 C 0.4481(6) 0.3457(4) 0.02123(9) 0.0344(9) Uani 1 1 d . . .
H83 H 0.5946 0.3006 0.0187 0.041 Uiso 1 1 calc R . .
C84 C 0.3046(7) 0.3122(4) 0.04721(9) 0.0330(9) Uani 1 1 d . . .
C85 C 0.0897(7) 0.3776(4) 0.05152(9) 0.0360(9) Uani 1 1 d . . .
H85 H -0.0052 0.3546 0.0695 0.043 Uiso 1 1 calc R . .
C86 C 0.0168(6) 0.4772(4) 0.02900(9) 0.0321(8) Uani 1 1 d . . .
H86 H -0.1301 0.5216 0.0317 0.039 Uiso 1 1 calc R . .
Br2 Br 0.40733(9) 0.17058(5) 0.077002(10) 0.05216(14) Uani 1 1 d . . .
C9 C 0.1465(6) 0.9892(5) -0.13597(9) 0.0331(8) Uani 1 1 d . . .
C91 C -0.1189(7) 1.0021(6) -0.13809(11) 0.0499(11) Uani 1 1 d . . .
H91A H -0.1909 0.9166 -0.1292 0.075 Uiso 1 1 calc R . .
H91B H -0.1651 1.0131 -0.1607 0.075 Uiso 1 1 calc R . .
H91C H -0.1702 1.0847 -0.1257 0.075 Uiso 1 1 calc R . .
C92 C 0.2716(8) 1.1197(5) -0.14828(12) 0.0510(12) Uani 1 1 d . . .
H92A H 0.2184 1.2029 -0.1362 0.077 Uiso 1 1 calc R . .
H92B H 0.2376 1.1326 -0.1712 0.077 Uiso 1 1 calc R . .
H92C H 0.4396 1.1081 -0.1453 0.077 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.0(3) . . ?
O1 C1 C11 114.5(3) . . ?
C2 C1 C11 124.5(4) . . ?
C12 C11 C16 118.5(4) . . ?
C12 C11 C1 122.8(4) . . ?
C16 C11 C1 118.7(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C13 C12 119.4(4) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 Br1 118.7(3) . . ?
C13 C14 Br1 120.3(3) . . ?
C14 C15 C16 119.0(4) . . ?
C11 C16 C15 121.1(4) . . ?
C1 C2 C3 119.8(4) . . ?
O3 C3 C2 123.1(4) . . ?
O3 C3 C4 114.5(3) . . ?
C2 C3 C4 122.4(3) . . ?
O4 C4 C3 112.1(3) . . ?
O4 C4 C5 102.2(3) . . ?
C3 C4 C5 112.5(3) . . ?
C4 O4 C9 106.1(3) . . ?
O5 C5 C6 111.5(3) . . ?
O5 C5 C4 103.9(3) . . ?
C6 C5 C4 113.0(3) . . ?
C5 O5 C9 109.5(3) . . ?
O6 C6 C7 122.3(3) . . ?
O6 C6 C5 114.7(3) . . ?
C7 C6 C5 123.0(3) . . ?
C6 C7 C8 120.9(3) . . ?
O8 C8 C7 119.8(3) . . ?
O8 C8 C81 118.1(3) . . ?
C7 C8 C81 122.1(3) . . ?
C82 C81 C86 118.1(3) . . ?
C82 C81 C8 122.6(3) . . ?
C86 C81 C8 119.3(3) . . ?
C83 C82 C81 121.3(3) . . ?
C84 C83 C82 118.8(3) . . ?
C85 C84 C83 121.5(3) . . ?
C85 C84 Br2 120.1(3) . . ?
C83 C84 Br2 118.4(3) . . ?
C86 C85 C84 118.8(3) . . ?
C85 C86 C81 121.5(3) . . ?
O4 C9 O5 104.5(3) . . ?
O4 C9 C92 109.4(3) . . ?
O5 C9 C92 108.6(3) . . ?
O4 C9 C91 111.3(4) . . ?
O5 C9 C91 109.8(3) . . ?
C92 C9 C91 112.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.300(5) . ?
C1 C2 1.381(5) . ?
C1 C11 1.478(5) . ?
C11 C12 1.378(5) . ?
C11 C16 1.379(5) . ?
C12 C13 1.379(6) . ?
C13 C14 1.377(6) . ?
C14 C15 1.365(6) . ?
C14 Br1 1.896(4) . ?
C15 C16 1.391(6) . ?
C2 C3 1.403(5) . ?
C3 O3 1.266(5) . ?
C3 C4 1.502(5) . ?
C4 O4 1.416(5) . ?
C4 C5 1.547(5) . ?
O4 C9 1.429(5) . ?
C5 O5 1.418(4) . ?
C5 C6 1.507(5) . ?
O5 C9 1.431(4) . ?
C6 O6 1.326(5) . ?
C6 C7 1.350(5) . ?
C7 C8 1.432(5) . ?
C8 O8 1.266(4) . ?
C8 C81 1.468(5) . ?
C81 C82 1.388(5) . ?
C81 C86 1.396(5) . ?
C82 C83 1.384(5) . ?
C83 C84 1.380(5) . ?
C84 C85 1.379(6) . ?
C84 Br2 1.896(4) . ?
C85 C86 1.377(5) . ?
C9 C92 1.502(6) . ?
C9 C91 1.518(5) . ?
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
O1 C1 C11 C12 -176.8(4) . . . . ?
C2 C1 C11 C12 2.4(6) . . . . ?
O1 C1 C11 C16 4.1(5) . . . . ?
C2 C1 C11 C16 -176.7(4) . . . . ?
C16 C11 C12 C13 1.3(6) . . . . ?
C1 C11 C12 C13 -177.9(4) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C12 C13 C14 C15 -2.3(7) . . . . ?
C12 C13 C14 Br1 176.9(3) . . . . ?
C13 C14 C15 C16 2.1(7) . . . . ?
Br1 C14 C15 C16 -177.1(4) . . . . ?
C12 C11 C16 C15 -1.4(6) . . . . ?
C1 C11 C16 C15 177.7(4) . . . . ?
C14 C15 C16 C11 -0.2(7) . . . . ?
O1 C1 C2 C3 -1.9(6) . . . . ?
C11 C1 C2 C3 178.9(4) . . . . ?
C1 C2 C3 O3 2.4(6) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
O3 C3 C4 O4 -170.0(3) . . . . ?
C2 C3 C4 O4 11.7(5) . . . . ?
O3 C3 C4 C5 75.5(5) . . . . ?
C2 C3 C4 C5 -102.9(4) . . . . ?
C3 C4 O4 C9 -157.2(3) . . . . ?
C5 C4 O4 C9 -36.4(3) . . . . ?
O4 C4 C5 O5 23.8(4) . . . . ?
C3 C4 C5 O5 144.3(3) . . . . ?
O4 C4 C5 C6 144.9(3) . . . . ?
C3 C4 C5 C6 -94.6(4) . . . . ?
C6 C5 O5 C9 -124.8(3) . . . . ?
C4 C5 O5 C9 -2.8(4) . . . . ?
O5 C5 C6 O6 49.9(4) . . . . ?
C4 C5 C6 O6 -66.7(4) . . . . ?
O5 C5 C6 C7 -132.4(4) . . . . ?
C4 C5 C6 C7 111.0(4) . . . . ?
O6 C6 C7 C8 0.2(6) . . . . ?
C5 C6 C7 C8 -177.4(3) . . . . ?
C6 C7 C8 O8 -4.4(6) . . . . ?
C6 C7 C8 C81 174.1(3) . . . . ?
O8 C8 C81 C82 164.7(4) . . . . ?
C7 C8 C81 C82 -13.8(5) . . . . ?
O8 C8 C81 C86 -11.9(5) . . . . ?
C7 C8 C81 C86 169.6(3) . . . . ?
C86 C81 C82 C83 0.8(5) . . . . ?
C8 C81 C82 C83 -175.9(3) . . . . ?
C81 C82 C83 C84 -0.5(6) . . . . ?
C82 C83 C84 C85 -0.3(6) . . . . ?
C82 C83 C84 Br2 178.7(3) . . . . ?
C83 C84 C85 C86 0.8(6) . . . . ?
Br2 C84 C85 C86 -178.2(3) . . . . ?
C84 C85 C86 C81 -0.5(6) . . . . ?
C82 C81 C86 C85 -0.3(6) . . . . ?
C8 C81 C86 C85 176.6(3) . . . . ?
C4 O4 C9 O5 35.6(3) . . . . ?
C4 O4 C9 C92 151.8(3) . . . . ?
C4 O4 C9 C91 -82.9(4) . . . . ?
C5 O5 C9 O4 -19.3(4) . . . . ?
C5 O5 C9 C92 -136.1(3) . . . . ?
C5 O5 C9 C91 100.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189102
2 PubChem 102188651
