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#$Date: 2023-05-18 02:05:53 +0300 (Thu, 18 May 2023) $
#$Revision: 283841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/30/7713068.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_7713068
loop_
_publ_author_name
'Ghosh, Kowsik'
'Ovchinnikov, Alexander'
'Baitinger, Michael'
'Krnel, Mitja'
'Burkhardt, Ulrich'
'Grin, Yuri'
'Bobev, Svilen'
_publ_section_title
;
 Lithium metal atoms fill vacancies in the germanium network of a type-I
 clathrate: Synthesis and structural characterization of Ba8Li5Ge41
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01168B
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 N2 O'
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_formula_weight         316.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                92.371(2)
_cell_angle_beta                 100.401(2)
_cell_angle_gamma                114.782(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7993(2)
_cell_length_b                   9.5600(3)
_cell_length_c                   11.0330(4)
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.37
_cell_volume                     821.64(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20523
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.893
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0529 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.8878.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.869
_exptl_crystal_size_mid          0.623
_exptl_crystal_size_min          0.525
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0436
_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)+(0.0493P)²+0.4217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3047
_reflns_number_total             3792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01168b2.cif
_cod_data_source_block           compound_L5H
_cod_database_code               7713068
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6'),
 C8'(H8'), C9'(H9'), C10'(H10')
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
O1 O 0.15487(14) 0.26186(12) 0.06138(10) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.200615 0.358616 0.061356 0.049 Uiso 1 1 calc R U . . .
N1 N 0.40138(14) 0.49755(13) 0.22910(11) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.59358(14) 0.74230(13) 0.21466(11) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.36117(16) 0.34442(15) 0.25474(13) 0.0233(3) Uani 1 1 d . . . . .
C1' C 0.70203(16) 0.54863(14) 0.22694(12) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.22846(17) 0.22557(16) 0.16853(13) 0.0246(3) Uani 1 1 d . . . . .
C2' C 0.84993(16) 0.60977(14) 0.32604(12) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.17036(18) 0.07163(17) 0.18859(15) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.082773 -0.007973 0.127787 0.036 Uiso 1 1 calc R U . . .
C3' C 0.86317(17) 0.70271(16) 0.43454(13) 0.0242(3) Uani 1 1 d . . . . .
H3' H 0.771873 0.728652 0.441900 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2409(2) 0.03442(18) 0.29803(16) 0.0344(4) Uani 1 1 d . . . . .
H4 H 0.200075 -0.070871 0.313143 0.041 Uiso 1 1 calc R U . . .
C4' C 1.0063(2) 0.75531(17) 0.52868(14) 0.0317(3) Uani 1 1 d . . . . .
H4' H 1.012952 0.816816 0.601092 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3703(2) 0.15009(19) 0.38509(16) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.418145 0.124124 0.460116 0.041 Uiso 1 1 calc R U . . .
C5' C 1.14384(19) 0.71929(18) 0.51945(15) 0.0327(3) Uani 1 1 d . . . . .
H5' H 1.242581 0.756543 0.585428 0.039 Uiso 1 1 calc R U . . .
C6 C 0.43125(18) 0.30467(17) 0.36355(14) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.521251 0.383468 0.423585 0.034 Uiso 1 1 calc R U . . .
C6' C 1.13542(17) 0.63124(17) 0.41616(14) 0.0279(3) Uani 1 1 d . . . . .
H6' H 1.229150 0.608231 0.410387 0.033 Uiso 1 1 calc R U . . .
C7 C 0.55719(16) 0.59303(15) 0.22602(12) 0.0205(3) Uani 1 1 d . . . . .
C7' C 0.98888(16) 0.57337(15) 0.31709(12) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.46346(18) 0.80150(16) 0.20934(14) 0.0269(3) Uani 1 1 d . . . . .
H8A H 0.421473 0.792372 0.287402 0.032 Uiso 1 1 calc R U . . .
H8B H 0.364929 0.744666 0.138720 0.032 Uiso 1 1 calc R U . . .
C8' C 0.97634(18) 0.47708(17) 0.21183(13) 0.0269(3) Uani 1 1 d . . . . .
H8' H 1.069813 0.454098 0.205097 0.032 Uiso 1 1 calc R U . . .
C9 C 0.75575(17) 0.86026(15) 0.19356(14) 0.0260(3) Uani 1 1 d . . . . .
H9A H 0.805857 0.814535 0.139224 0.031 Uiso 1 1 calc R U . . .
H9B H 0.840047 0.910180 0.273002 0.031 Uiso 1 1 calc R U . . .
C9' C 0.83191(19) 0.41678(17) 0.11987(13) 0.0283(3) Uani 1 1 d . . . . .
H9' H 0.824394 0.350467 0.050255 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5590(2) 0.97077(19) 0.19162(19) 0.0410(4) Uani 1 1 d . . . . .
H10A H 0.482234 1.005387 0.137490 0.049 Uiso 1 1 calc R U . . .
H10B H 0.606239 1.038360 0.272523 0.049 Uiso 1 1 calc R U . . .
C10' C 0.69281(17) 0.45217(15) 0.12722(13) 0.0232(3) Uani 1 1 d . . . . .
H10' H 0.592206 0.408929 0.062712 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7021(2) 0.9747(2) 0.13063(17) 0.0389(4) Uani 1 1 d . . . . .
H11A H 0.659965 0.941924 0.039916 0.047 Uiso 1 1 calc R U . . .
H11B H 0.798412 1.080092 0.145686 0.047 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 O1 H1 109.5 . . ?
C7 N1 C1 120.92(11) . . ?
C7 N2 C8 121.89(11) . . ?
C7 N2 C9 125.92(11) . . ?
C9 N2 C8 111.90(11) . . ?
C2 C1 N1 116.43(12) . . ?
C6 C1 N1 124.95(13) . . ?
C6 C1 C2 118.30(13) . . ?
C2' C1' C7 121.17(11) . . ?
C10' C1' C2' 120.12(11) . . ?
C10' C1' C7 118.66(11) . . ?
O1 C2 C1 119.51(12) . . ?
O1 C2 C3 119.15(13) . . ?
C3 C2 C1 121.34(14) . . ?
C3' C2' C1' 122.79(11) . . ?
C3' C2' C7' 118.57(12) . . ?
C7' C2' C1' 118.63(11) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.49(14) . . ?
C4 C3 H3 120.3 . . ?
C2' C3' H3' 119.7 . . ?
C4' C3' C2' 120.58(13) . . ?
C4' C3' H3' 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.09(14) . . ?
C5 C4 H4 120.0 . . ?
C3' C4' H4' 119.6 . . ?
C3' C4' C5' 120.73(14) . . ?
C5' C4' H4' 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.34(15) . . ?
C6 C5 H5 119.8 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' C4' 120.08(13) . . ?
C6' C5' H5' 120.0 . . ?
C1 C6 C5 120.41(14) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5' C6' H6' 119.5 . . ?
C5' C6' C7' 120.93(13) . . ?
C7' C6' H6' 119.5 . . ?
N1 C7 N2 118.95(12) . . ?
N1 C7 C1' 125.09(12) . . ?
N2 C7 C1' 115.86(11) . . ?
C6' C7' C2' 119.12(13) . . ?
C8' C7' C2' 119.57(12) . . ?
C8' C7' C6' 121.29(12) . . ?
N2 C8 H8A 111.1 . . ?
N2 C8 H8B 111.1 . . ?
N2 C8 C10 103.47(11) . . ?
H8A C8 H8B 109.0 . . ?
C10 C8 H8A 111.1 . . ?
C10 C8 H8B 111.1 . . ?
C7' C8' H8' 119.6 . . ?
C9' C8' C7' 120.71(12) . . ?
C9' C8' H8' 119.6 . . ?
N2 C9 H9A 111.2 . . ?
N2 C9 H9B 111.2 . . ?
N2 C9 C11 102.83(11) . . ?
H9A C9 H9B 109.1 . . ?
C11 C9 H9A 111.2 . . ?
C11 C9 H9B 111.2 . . ?
C8' C9' H9' 119.8 . . ?
C8' C9' C10' 120.41(13) . . ?
C10' C9' H9' 119.8 . . ?
C8 C10 H10A 110.9 . . ?
C8 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 C8 104.44(12) . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C1' C10' C9' 120.52(12) . . ?
C1' C10' H10' 119.7 . . ?
C9' C10' H10' 119.7 . . ?
C9 C11 C10 103.21(13) . . ?
C9 C11 H11A 111.1 . . ?
C9 C11 H11B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
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
O1 H1 0.8400 . ?
O1 C2 1.3723(18) . ?
N1 C1 1.4087(17) . ?
N1 C7 1.2978(17) . ?
N2 C7 1.3419(17) . ?
N2 C8 1.4684(16) . ?
N2 C9 1.4680(17) . ?
C1 C2 1.399(2) . ?
C1 C6 1.390(2) . ?
C1' C2' 1.4235(18) . ?
C1' C7 1.5013(17) . ?
C1' C10' 1.3743(18) . ?
C2 C3 1.383(2) . ?
C2' C3' 1.4180(18) . ?
C2' C7' 1.4224(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.368(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(2) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.409(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.360(2) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C7' 1.4165(19) . ?
C7' C8' 1.4101(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C10 1.519(2) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.360(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C11 1.510(2) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.4142(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(2) . ?
C10' H10' 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
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
O1 H1 N1 0.84 2.23 2.7045(15) 116.2 . 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
O1 C2 C3 C4 -178.30(12) . . . . ?
N1 C1 C2 O1 4.93(18) . . . . ?
N1 C1 C2 C3 -175.52(12) . . . . ?
N1 C1 C6 C5 173.53(13) . . . . ?
N2 C8 C10 C11 25.23(17) . . . . ?
N2 C9 C11 C10 34.25(16) . . . . ?
C1 N1 C7 N2 -172.87(12) . . . . ?
C1 N1 C7 C1' 10.8(2) . . . . ?
C1 C2 C3 C4 2.1(2) . . . . ?
C1' C2' C3' C4' 178.25(13) . . . . ?
C1' C2' C7' C6' -178.86(12) . . . . ?
C1' C2' C7' C8' -0.66(18) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2' C1' C7 N1 -117.34(15) . . . . ?
C2' C1' C7 N2 66.23(17) . . . . ?
C2' C1' C10' C9' -2.1(2) . . . . ?
C2' C3' C4' C5' 0.5(2) . . . . ?
C2' C7' C8' C9' -1.0(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3' C2' C7' C6' -0.20(18) . . . . ?
C3' C2' C7' C8' 178.00(12) . . . . ?
C3' C4' C5' C6' 0.0(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4' C5' C6' C7' -0.5(2) . . . . ?
C5' C6' C7' C2' 0.6(2) . . . . ?
C5' C6' C7' C8' -177.53(13) . . . . ?
C6 C1 C2 O1 178.82(12) . . . . ?
C6 C1 C2 C3 -1.63(19) . . . . ?
C6' C7' C8' C9' 177.11(13) . . . . ?
C7 N1 C1 C2 -126.45(14) . . . . ?
C7 N1 C1 C6 60.12(19) . . . . ?
C7 N2 C8 C10 -177.89(13) . . . . ?
C7 N2 C9 C11 154.58(14) . . . . ?
C7 C1' C2' C3' 6.34(19) . . . . ?
C7 C1' C2' C7' -175.05(11) . . . . ?
C7 C1' C10' C9' 175.23(12) . . . . ?
C7' C2' C3' C4' -0.4(2) . . . . ?
C7' C8' C9' C10' 1.2(2) . . . . ?
C8 N2 C7 N1 1.8(2) . . . . ?
C8 N2 C7 C1' 178.50(12) . . . . ?
C8 N2 C9 C11 -19.39(16) . . . . ?
C8 C10 C11 C9 -37.36(18) . . . . ?
C8' C9' C10' C1' 0.4(2) . . . . ?
C9 N2 C7 N1 -171.57(13) . . . . ?
C9 N2 C7 C1' 5.09(19) . . . . ?
C9 N2 C8 C10 -3.64(16) . . . . ?
C10' C1' C2' C3' -176.38(12) . . . . ?
C10' C1' C2' C7' 2.23(18) . . . . ?
C10' C1' C7 N1 65.34(18) . . . . ?
C10' C1' C7 N2 -111.09(14) . . . . ?
