#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/48/4504810.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_4504810
loop_
_publ_author_name
'Morris, J. Jacob'
'Noll, Bruce C.'
'Henderson, Kenneth W.'
_publ_section_title
;
 Assembly of 63,66-Pillared Metal−Organic Bilayers and Diamondoid
 Lattices Using Molecular Li2O2Ring Dimers as Secondary Building Units
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1071
_journal_paper_doi               10.1021/cg0600187
_journal_volume                  6
_journal_year                    2006
_chemical_compound_source        Synthesized
_chemical_formula_moiety         'C22 H28 Br2 Li2 O6'
_chemical_formula_sum            'C22 H28 Br2 Li2 O6'
_chemical_formula_weight         562.14
_chemical_name_common            'Lithium 4-Br,2,6-Dimethylphenoxide Dioxolane'
_space_group_IT_number           122
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      122
_symmetry_space_group_name_Hall  'I -4 2bw'
_symmetry_space_group_name_H-M   'I -4 2 d'
_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            16
_cell_length_a                   18.4920(5)
_cell_length_b                   18.4920(5)
_cell_length_c                   28.562(1)
_cell_measurement_reflns_used    7506
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.56
_cell_volume                     9766.9(5)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       'ω  and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            58978
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.31
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_correction_T_min  0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, R.H. (1995) Acta Cryst. A51 33-38.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             4544
_exptl_crystal_recrystallization_method
'Recrystallized on standing in dioxolane and toluene.'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0213P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0472
_reflns_number_gt                5308
_reflns_number_total             6036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0600187si20060111_095533.cif
_cod_data_source_block           jjm35
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4504810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, -y, -z+3/4'
'-x+1/2, y, -z+3/4'
'-x, -y, z'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1, -y+1/2, -z+5/4'
'-x+1, y+1/2, -z+5/4'
'-x+1/2, -y+1/2, z+1/2'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'
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
Li1 Li 0.2500 0.7658(3) -0.1250 0.0192(11) Uani 1 2 d S
Li2 Li 0.2500 0.6238(3) -0.1250 0.0176(10) Uani 1 2 d S
Li3 Li 0.07030(19) 0.48540(17) 0.03594(12) 0.0194(7) Uani 1 1 d .
O1 O 0.30163(7) 0.69330(7) -0.09044(5) 0.0160(3) Uani 1 1 d .
O2 O 0.20190(7) 0.55389(7) -0.07871(5) 0.0175(3) Uani 1 1 d .
O3 O 0.15321(8) 0.51209(7) -0.01027(5) 0.0189(3) Uani 1 1 d .
O4 O 0.11995(7) 0.44161(7) 0.09478(5) 0.0206(3) Uani 1 1 d .
O5 O 0.16091(7) 0.33513(7) 0.12293(5) 0.0207(3) Uani 1 1 d .
O6 O 0.01610(7) 0.57108(7) 0.03592(5) 0.0170(3) Uani 1 1 d .
Br1 Br 0.363919(13) 0.620764(12) 0.110592(8) 0.03004(6) Uani 1 1 d .
Br2 Br 0.067136(11) 0.892244(10) 0.025963(8) 0.02094(5) Uani 1 1 d .
C1 C 0.31964(10) 0.68069(10) -0.04659(7) 0.0140(4) Uani 1 1 d .
C2 C 0.28558(11) 0.71922(11) -0.00928(8) 0.0180(5) Uani 1 1 d .
C3 C 0.30003(11) 0.70213(11) 0.03660(8) 0.0197(5) Uani 1 1 d .
H3 H 0.2768 0.7267 0.0607 0.024 Uiso 1 1 calc R
C4 C 0.34962(11) 0.64777(11) 0.04674(7) 0.0200(5) Uani 1 1 d .
C5 C 0.38702(11) 0.61315(11) 0.01177(7) 0.0191(4) Uani 1 1 d .
H5 H 0.4213 0.5783 0.0194 0.023 Uiso 1 1 calc R
C6 C 0.37404(10) 0.62970(10) -0.03507(7) 0.0164(4) Uani 1 1 d .
C7 C 0.23232(11) 0.77812(11) -0.02211(8) 0.0220(5) Uani 1 1 d .
H8A H 0.2149 0.8009 0.0059 0.033 Uiso 1 1 calc R
H8B H 0.1924 0.7574 -0.0389 0.033 Uiso 1 1 calc R
H8C H 0.2559 0.8134 -0.0415 0.033 Uiso 1 1 calc R
C8 C 0.41714(11) 0.59536(11) -0.07377(8) 0.0211(5) Uani 1 1 d .
H7A H 0.4493 0.5599 -0.0608 0.032 Uiso 1 1 calc R
H7B H 0.4448 0.6318 -0.0897 0.032 Uiso 1 1 calc R
H7C H 0.3849 0.5725 -0.0956 0.032 Uiso 1 1 calc R
C9 C 0.24351(11) 0.49233(11) -0.06332(7) 0.0179(4) Uani 1 1 d .
H9A H 0.2947 0.5001 -0.0686 0.021 Uiso 1 1 calc R
H9B H 0.2286 0.4488 -0.0796 0.021 Uiso 1 1 calc R
C10 C 0.22722(10) 0.48695(11) -0.01187(7) 0.0182(5) Uani 1 1 d .
H25A H 0.2313 0.4375 -0.0008 0.022 Uiso 1 1 calc R
H25B H 0.2589 0.5178 0.0064 0.022 Uiso 1 1 calc R
C11 C 0.15271(11) 0.57159(12) -0.04163(7) 0.0214(5) Uani 1 1 d .
H11A H 0.1682 0.6153 -0.0257 0.026 Uiso 1 1 calc R
H11B H 0.1044 0.5793 -0.0540 0.026 Uiso 1 1 calc R
C12 C 0.18367(11) 0.40372(11) 0.10620(8) 0.0234(5) Uani 1 1 d .
H22A H 0.2107 0.4293 0.1301 0.028 Uiso 1 1 calc R
H22B H 0.2142 0.3983 0.0788 0.028 Uiso 1 1 calc R
C13 C 0.08948(11) 0.34529(11) 0.14260(9) 0.0280(5) Uani 1 1 d .
H24A H 0.0895 0.3355 0.1760 0.034 Uiso 1 1 calc R
H24B H 0.0546 0.3138 0.1275 0.034 Uiso 1 1 calc R
C14 C 0.07238(12) 0.42414(11) 0.13300(8) 0.0230(5) Uani 1 1 d .
H21A H 0.0221 0.4304 0.1241 0.028 Uiso 1 1 calc R
H21B H 0.0825 0.4539 0.1602 0.028 Uiso 1 1 calc R
C15 C 0.02784(10) 0.64136(10) 0.03410(7) 0.0152(4) Uani 1 1 d .
C16 C 0.08458(10) 0.67354(11) 0.06025(7) 0.0155(4) Uani 1 1 d .
C17 C 0.09428(10) 0.74824(11) 0.05831(7) 0.0169(4) Uani 1 1 d .
H17 H 0.1305 0.7699 0.0761 0.020 Uiso 1 1 calc R
C18 C 0.05051(10) 0.79015(10) 0.03024(8) 0.0166(4) Uani 1 1 d .
C19 C -0.00418(11) 0.76002(11) 0.00399(7) 0.0165(4) Uani 1 1 d .
H15 H -0.0327 0.7891 -0.0151 0.020 Uiso 1 1 calc R
C20 C -0.01676(11) 0.68605(11) 0.00608(7) 0.0162(4) Uani 1 1 d .
C21 C 0.13376(11) 0.62697(11) 0.08950(7) 0.0200(4) Uani 1 1 d .
H20A H 0.1681 0.6570 0.1055 0.030 Uiso 1 1 calc R
H20B H 0.1590 0.5936 0.0696 0.030 Uiso 1 1 calc R
H20C H 0.1056 0.6006 0.1120 0.030 Uiso 1 1 calc R
C22 C -0.07734(12) 0.65231(11) -0.02102(8) 0.0239(5) Uani 1 1 d .
H19A H -0.1133 0.6345 0.0003 0.036 Uiso 1 1 calc R
H19B H -0.0589 0.6130 -0.0394 0.036 Uiso 1 1 calc R
H19C H -0.0986 0.6878 -0.0413 0.036 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'
Li Li -0.0003 0.0001 '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
O1 Li1 O1 91.4(2) 5_554 .
O1 Li1 O5 93.67(5) 5_554 7_564
O1 Li1 O5 147.89(6) . 7_564
O1 Li1 O5 147.89(6) 5_554 2_565
O1 Li1 O5 93.67(5) . 2_565
O5 Li1 O5 98.6(2) 7_564 2_565
O1 Li2 O1 93.8(2) . 5_554
O1 Li2 O2 123.27(6) . 5_554
O1 Li2 O2 108.20(6) 5_554 5_554
O1 Li2 O2 108.20(6) . .
O1 Li2 O2 123.27(6) 5_554 .
O2 Li2 O2 101.9(2) 5_554 .
O1 Li2 C1 113.4(2) . 5_554
O1 Li2 C1 24.01(6) 5_554 5_554
O2 Li2 C1 85.44(6) 5_554 5_554
O2 Li2 C1 123.70(7) . 5_554
O6 Li3 O6 90.85(16) . 6_565
O6 Li3 O4 124.44(19) . .
O6 Li3 O4 99.02(15) 6_565 .
O6 Li3 O3 101.14(16) . .
O6 Li3 O3 138.2(2) 6_565 .
O4 Li3 O3 106.23(16) . .
O6 Li3 Li3 45.95(11) . 6_565
O6 Li3 Li3 44.90(11) 6_565 6_565
O4 Li3 Li3 120.77(12) . 6_565
O3 Li3 Li3 132.28(14) . 6_565
C1 O1 Li2 120.43(15) . .
C1 O1 Li1 137.61(15) . .
Li2 O1 Li1 87.44(15) . .
C11 O2 C9 107.06(14) . .
C11 O2 Li2 127.40(15) . .
C9 O2 Li2 117.52(14) . .
C11 O3 C10 103.63(14) . .
C11 O3 Li3 125.39(15) . .
C10 O3 Li3 129.84(15) . .
C12 O4 C14 102.95(15) . .
C12 O4 Li3 138.58(16) . .
C14 O4 Li3 115.51(15) . .
C12 O5 C13 106.58(14) . .
C12 O5 Li1 119.57(15) . 3_655
C13 O5 Li1 133.01(14) . 3_655
C15 O6 Li3 138.15(16) . .
C15 O6 Li3 132.62(15) . 6_565
Li3 O6 Li3 89.15(16) . 6_565
O1 C1 C6 121.21(18) . .
O1 C1 C2 120.66(18) . .
C6 C1 C2 118.13(18) . .
C3 C2 C1 120.73(19) . .
C3 C2 C7 121.5(2) . .
C1 C2 C7 117.73(19) . .
C2 C3 C4 119.5(2) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
C5 C4 C3 121.15(19) . .
C5 C4 Br1 120.20(15) . .
C3 C4 Br1 118.64(16) . .
C4 C5 C6 120.62(18) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C5 C6 C1 119.43(19) . .
C5 C6 C8 121.47(18) . .
C1 C6 C8 119.10(18) . .
C2 C7 H8A 109.5 . .
C2 C7 H8B 109.5 . .
H8A C7 H8B 109.5 . .
C2 C7 H8C 109.5 . .
H8A C7 H8C 109.5 . .
H8B C7 H8C 109.5 . .
C6 C8 H7A 109.5 . .
C6 C8 H7B 109.5 . .
H7A C8 H7B 109.5 . .
C6 C8 H7C 109.5 . .
H7A C8 H7C 109.5 . .
H7B C8 H7C 109.5 . .
O2 C9 C10 104.08(16) . .
O2 C9 H9A 110.9 . .
C10 C9 H9A 110.9 . .
O2 C9 H9B 110.9 . .
C10 C9 H9B 110.9 . .
H9A C9 H9B 109.0 . .
O3 C10 C9 101.49(16) . .
O3 C10 H25A 111.5 . .
C9 C10 H25A 111.5 . .
O3 C10 H25B 111.5 . .
C9 C10 H25B 111.5 . .
H25A C10 H25B 109.3 . .
O3 C11 O2 106.56(16) . .
O3 C11 H11A 110.4 . .
O2 C11 H11A 110.4 . .
O3 C11 H11B 110.4 . .
O2 C11 H11B 110.4 . .
H11A C11 H11B 108.6 . .
O4 C12 O5 105.92(15) . .
O4 C12 H22A 110.6 . .
O5 C12 H22A 110.6 . .
O4 C12 H22B 110.6 . .
O5 C12 H22B 110.6 . .
H22A C12 H22B 108.7 . .
O5 C13 C14 104.16(17) . .
O5 C13 H24A 110.9 . .
C14 C13 H24A 110.9 . .
O5 C13 H24B 110.9 . .
C14 C13 H24B 110.9 . .
H24A C13 H24B 108.9 . .
O4 C14 C13 103.03(17) . .
O4 C14 H21A 111.2 . .
C13 C14 H21A 111.2 . .
O4 C14 H21B 111.2 . .
C13 C14 H21B 111.2 . .
H21A C14 H21B 109.1 . .
O6 C15 C20 120.12(18) . .
O6 C15 C16 120.95(18) . .
C20 C15 C16 118.93(17) . .
C17 C16 C15 119.33(18) . .
C17 C16 C21 120.74(18) . .
C15 C16 C21 119.93(17) . .
C18 C17 C16 120.32(19) . .
C18 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
C19 C18 C17 121.39(18) . .
C19 C18 Br2 118.80(15) . .
C17 C18 Br2 119.79(15) . .
C18 C19 C20 119.88(19) . .
C18 C19 H15 120.1 . .
C20 C19 H15 120.1 . .
C19 C20 C15 120.12(19) . .
C19 C20 C22 120.88(18) . .
C15 C20 C22 118.99(18) . .
C16 C21 H20A 109.5 . .
C16 C21 H20B 109.5 . .
H20A C21 H20B 109.5 . .
C16 C21 H20C 109.5 . .
H20A C21 H20C 109.5 . .
H20B C21 H20C 109.5 . .
C20 C22 H19A 109.5 . .
C20 C22 H19B 109.5 . .
H19A C22 H19B 109.5 . .
C20 C22 H19C 109.5 . .
H19A C22 H19C 109.5 . .
H19B C22 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 O1 1.920(4) 5_554
Li1 O1 1.920(4) .
Li1 O5 2.078(3) 7_564
Li1 O5 2.078(3) 2_565
Li2 O1 1.881(3) .
Li2 O1 1.881(3) 5_554
Li2 O2 2.052(3) 5_554
Li2 O2 2.052(3) .
Li2 C1 2.790(3) 5_554
Li3 O6 1.875(4) .
Li3 O6 1.909(4) 6_565
Li3 O4 2.079(4) .
Li3 O3 2.082(4) .
Li3 Li3 2.656(7) 6_565
O1 C1 1.317(2) .
O2 C11 1.434(2) .
O2 C9 1.443(2) .
O3 C11 1.419(2) .
O3 C10 1.446(2) .
O4 C12 1.409(2) .
O4 C14 1.438(2) .
O5 C12 1.419(2) .
O5 C13 1.448(2) .
O5 Li1 2.078(3) 3_655
O6 C15 1.319(2) .
O6 Li3 1.909(4) 6_565
Br1 C4 1.909(2) .
Br2 C18 1.9167(19) .
C1 C6 1.418(3) .
C1 C2 1.428(3) .
C2 C3 1.374(3) .
C2 C7 1.513(3) .
C3 C4 1.391(3) .
C3 H3 0.9300 .
C4 C5 1.373(3) .
C5 C6 1.393(3) .
C5 H5 0.9300 .
C6 C8 1.503(3) .
C7 H8A 0.9600 .
C7 H8B 0.9600 .
C7 H8C 0.9600 .
C8 H7A 0.9600 .
C8 H7B 0.9600 .
C8 H7C 0.9600 .
C9 C10 1.503(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H25A 0.9700 .
C10 H25B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H22A 0.9700 .
C12 H22B 0.9700 .
C13 C14 1.517(3) .
C13 H24A 0.9700 .
C13 H24B 0.9700 .
C14 H21A 0.9700 .
C14 H21B 0.9700 .
C15 C20 1.415(3) .
C15 C16 1.419(3) .
C16 C17 1.394(3) .
C16 C21 1.506(3) .
C17 C18 1.378(3) .
C17 H17 0.9300 .
C18 C19 1.377(3) .
C19 C20 1.389(3) .
C19 H15 0.9300 .
C20 C22 1.498(3) .
C21 H20A 0.9600 .
C21 H20B 0.9600 .
C21 H20C 0.9600 .
C22 H19A 0.9600 .
C22 H19B 0.9600 .
C22 H19C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145631
