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#$Date: 2023-08-26 01:53:45 +0300 (Sat, 26 Aug 2023) $
#$Revision: 285880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/37/7713793.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_7713793
loop_
_publ_author_name
'Du, Xiaodi'
'Gao, Cong-Li'
'Zhang, Zhiqiang'
'Su, Bing'
'Li, Xi-Li'
_publ_section_title
;
 A pair of ionic 1D Cu(II) chain enantiomers simultaneously displaying
 large second- and third-harmonic generation responses
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01923C
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H29 Cu N5 O2, 2(Cl O4)'
_chemical_formula_sum            'C21 H29 Cl2 Cu N5 O10'
_chemical_formula_weight         645.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-08-06 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3721(2)
_cell_length_b                   12.2081(3)
_cell_length_c                   21.1481(5)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3137
_cell_measurement_theta_min      3.2112
_cell_volume                     2677.85(10)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7278
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.218
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5006
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0853P)²+0.5419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                3938
_reflns_number_total             5006
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01923c2.cif
_cod_data_source_block           D-1
_cod_database_code               7713793
_shelx_shelxl_version_number     2014/7
_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_min   0.97008
_shelx_estimated_absorpt_t_max   1.00000
loop_
_space_group_symop_operation_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_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
C1 C -0.1702(8) -0.3148(7) 0.9452(4) 0.044(2) Uani 1 1 d . . . . .
H1 H -0.1380 -0.3565 0.9119 0.052 Uiso 1 1 calc R U . . .
C2 C -0.2613(8) -0.3591(7) 0.9839(4) 0.0427(19) Uani 1 1 d . . . . .
H2 H -0.2865 -0.4314 0.9777 0.051 Uiso 1 1 calc R U . . .
C3 C -0.2708(7) -0.1999(7) 1.0381(4) 0.0408(19) Uani 1 1 d . . . . .
H3 H -0.3066 -0.1568 1.0699 0.049 Uiso 1 1 calc R U . . .
C4 C -0.1747(7) -0.1554(6) 1.0014(4) 0.0339(17) Uani 1 1 d . . . . .
C5 C -0.1200(6) -0.0467(6) 1.0116(4) 0.0333(17) Uani 1 1 d . . . . .
C6 C -0.1345(8) 0.0150(7) 1.0653(4) 0.044(2) Uani 1 1 d . . . . .
H6 H -0.1898 -0.0083 1.0972 0.053 Uiso 1 1 calc R U . . .
C7 C -0.0657(8) 0.1134(7) 1.0720(4) 0.0432(18) Uani 1 1 d . . . . .
C8 C 0.0069(8) 0.1497(5) 1.0222(3) 0.0373(16) Uani 1 1 d . . . . .
C9 C 0.0168(7) 0.0857(5) 0.9687(3) 0.0331(15) Uani 1 1 d . . . . .
H9 H 0.0666 0.1110 0.9352 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0689(10) 0.1802(8) 1.1329(4) 0.057(2) Uani 1 1 d . . . . .
H10A H -0.1551 0.2085 1.1398 0.069 Uiso 1 1 calc R U . . .
H10B H -0.0464 0.1339 1.1685 0.069 Uiso 1 1 calc R U . . .
C11 C 0.0263(10) 0.2745(8) 1.1278(4) 0.061(3) Uani 1 1 d . . . . .
H11 H 0.0354 0.3186 1.1663 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1555(9) 0.2352(10) 1.0983(5) 0.067(3) Uani 1 1 d . . . . .
H12A H 0.2276 0.2842 1.1055 0.081 Uiso 1 1 calc R U . . .
H12B H 0.1778 0.1600 1.1082 0.081 Uiso 1 1 calc R U . . .
C13 C 0.0886(7) 0.2503(7) 1.0333(4) 0.045(2) Uani 1 1 d . . . . .
H13 H 0.1430 0.2746 0.9981 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0058(9) 0.3404(6) 1.0673(4) 0.0470(19) Uani 1 1 d . . . . .
C15 C -0.1322(9) 0.3589(9) 1.0433(6) 0.067(3) Uani 1 1 d . . . . .
H15A H -0.1830 0.2946 1.0513 0.100 Uiso 1 1 calc R U . . .
H15B H -0.1304 0.3733 0.9987 0.100 Uiso 1 1 calc R U . . .
H15C H -0.1695 0.4203 1.0649 0.100 Uiso 1 1 calc R U . . .
C16 C 0.0768(11) 0.4518(8) 1.0665(6) 0.079(3) Uani 1 1 d . . . . .
H16A H 0.0397 0.4993 1.0978 0.118 Uiso 1 1 calc R U . . .
H16B H 0.0683 0.4846 1.0255 0.118 Uiso 1 1 calc R U . . .
H16C H 0.1664 0.4405 1.0758 0.118 Uiso 1 1 calc R U . . .
C17 C 0.0913(8) -0.2908(7) 0.7975(4) 0.044(2) Uani 1 1 d . . . . .
C18 C 0.1498(14) -0.3424(10) 0.7429(5) 0.085(4) Uani 1 1 d . . . . .
H18A H 0.1725 -0.2873 0.7125 0.128 Uiso 1 1 calc R U . . .
H18B H 0.0897 -0.3928 0.7243 0.128 Uiso 1 1 calc R U . . .
H18C H 0.2259 -0.3812 0.7558 0.128 Uiso 1 1 calc R U . . .
C19 C 0.2011(10) -0.0360(12) 0.8235(5) 0.083(4) Uani 1 1 d . . . . .
H19 H 0.2398 -0.1034 0.8312 0.100 Uiso 1 1 calc R U . . .
C20 C 0.3803(12) -0.0104(14) 0.7522(8) 0.120(6) Uani 1 1 d . . . . .
H20A H 0.4014 -0.0834 0.7656 0.180 Uiso 1 1 calc R U . . .
H20B H 0.4503 0.0380 0.7623 0.180 Uiso 1 1 calc R U . . .
H20C H 0.3658 -0.0098 0.7074 0.180 Uiso 1 1 calc R U . . .
C21 C 0.2150(13) 0.1236(12) 0.7686(8) 0.101(4) Uani 1 1 d . . . . .
H21A H 0.1704 0.1178 0.7290 0.151 Uiso 1 1 calc R U . . .
H21B H 0.2823 0.1772 0.7651 0.151 Uiso 1 1 calc R U . . .
H21C H 0.1555 0.1455 0.8010 0.151 Uiso 1 1 calc R U . . .
Cl1 Cl 0.9782(2) 0.90219(19) 0.65244(10) 0.0573(6) Uani 1 1 d . . . . .
Cl2 Cl 0.0071(3) 0.7616(3) 0.15301(15) 0.0950(10) Uani 1 1 d . . . . .
Cu1 Cu -0.00340(9) -0.12657(7) 0.89939(4) 0.0371(3) Uani 1 1 d . . . . .
H22A H -0.151(8) -0.106(7) 0.7918(18) 0.04(2) Uiso 1 1 d D . . . .
H23A H -0.227(8) -0.138(6) 0.838(5) 0.07(3) Uiso 1 1 d D . . . .
N1 N -0.0423(5) -0.0112(5) 0.9631(3) 0.0294(13) Uani 1 1 d . . . . .
N2 N -0.1257(6) -0.2132(5) 0.9535(3) 0.0329(14) Uani 1 1 d . . . . .
N3 N -0.3153(6) -0.3019(6) 1.0305(3) 0.0412(16) Uani 1 1 d . . . . .
N4 N 0.0456(6) -0.2478(6) 0.8393(3) 0.0440(16) Uani 1 1 d . . . . .
N5 N 0.2670(9) 0.0252(9) 0.7838(5) 0.074(3) Uani 1 1 d . . . . .
O1 O -0.1750(7) -0.0869(6) 0.8285(4) 0.0577(17) Uani 1 1 d D . . . .
O2 O 1.0805(18) 0.9158(15) 0.6853(12) 0.306(15) Uani 1 1 d . . . . .
O3 O 0.8811(17) 0.9066(17) 0.6952(7) 0.223(9) Uani 1 1 d . . . . .
O4 O 0.9440(17) 0.9832(10) 0.6150(7) 0.181(6) Uani 1 1 d . . . . .
O5 O 0.9800(16) 0.8026(7) 0.6216(5) 0.143(5) Uani 1 1 d . . . . .
O6 O 0.0723(15) 0.8756(12) 0.1365(8) 0.180(6) Uani 1 1 d . . . . .
O7 O 0.0857(10) 0.7037(11) 0.1949(6) 0.140(4) Uani 1 1 d . . . . .
O8 O -0.0985(10) 0.7916(13) 0.1750(7) 0.169(6) Uani 1 1 d . . . . .
O9 O -0.003(2) 0.7130(12) 0.0967(6) 0.223(9) Uani 1 1 d . . . . .
O10 O 0.1059(6) -0.0244(5) 0.8509(3) 0.0520(15) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
N2 C1 C2 121.9(8) . . ?
N2 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N3 C2 C1 121.9(8) . . ?
N3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N3 C3 C4 123.3(8) . . ?
N3 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
N2 C4 C3 119.7(7) . . ?
N2 C4 C5 116.4(7) . . ?
C3 C4 C5 123.9(7) . . ?
C6 C5 N1 120.7(7) . . ?
C6 C5 C4 125.3(7) . . ?
N1 C5 C4 113.8(7) . . ?
C5 C6 C7 119.8(7) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 118.6(7) . . ?
C8 C7 C10 119.3(8) . . ?
C6 C7 C10 122.1(7) . . ?
C7 C8 C9 119.3(7) . . ?
C7 C8 C13 116.9(7) . . ?
C9 C8 C13 123.1(7) . . ?
N1 C9 C8 122.7(6) . . ?
N1 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C11 C10 C7 109.4(7) . . ?
C11 C10 H10A 109.8 . . ?
C7 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C7 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C14 111.5(8) . . ?
C10 C11 C12 110.7(8) . . ?
C14 C11 C12 86.9(7) . . ?
C10 C11 H11 114.9 . . ?
C14 C11 H11 114.9 . . ?
C12 C11 H11 114.9 . . ?
C13 C12 C11 86.3(6) . . ?
C13 C12 H12A 114.3 . . ?
C11 C12 H12A 114.3 . . ?
C13 C12 H12B 114.3 . . ?
C11 C12 H12B 114.3 . . ?
H12A C12 H12B 111.4 . . ?
C8 C13 C12 106.9(8) . . ?
C8 C13 C14 109.5(6) . . ?
C12 C13 C14 85.5(6) . . ?
C8 C13 H13 116.8 . . ?
C12 C13 H13 116.8 . . ?
C14 C13 H13 116.8 . . ?
C11 C14 C15 119.0(8) . . ?
C11 C14 C16 113.9(8) . . ?
C15 C14 C16 108.1(8) . . ?
C11 C14 C13 86.5(7) . . ?
C15 C14 C13 117.5(7) . . ?
C16 C14 C13 110.5(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 178.1(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O10 C19 N5 134.1(15) . . ?
O10 C19 H19 113.0 . . ?
N5 C19 H19 113.0 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 H21A 109.5 . . ?
N5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 Cl1 O4 116.9(13) . . ?
O2 Cl1 O3 104.4(14) . . ?
O4 Cl1 O3 99.9(12) . . ?
O2 Cl1 O5 111.1(10) . . ?
O4 Cl1 O5 112.5(8) . . ?
O3 Cl1 O5 111.2(10) . . ?
O8 Cl2 O9 113.1(12) . . ?
O8 Cl2 O7 115.2(9) . . ?
O9 Cl2 O7 112.9(9) . . ?
O8 Cl2 O6 101.5(10) . . ?
O9 Cl2 O6 103.1(10) . . ?
O7 Cl2 O6 109.6(8) . . ?
O10 Cu1 N1 91.2(2) . . ?
O10 Cu1 N2 172.6(3) . . ?
N1 Cu1 N2 81.9(2) . . ?
O10 Cu1 N4 89.5(3) . . ?
N1 Cu1 N4 175.8(3) . . ?
N2 Cu1 N4 97.6(3) . . ?
O10 Cu1 O1 88.5(3) . . ?
N1 Cu1 O1 97.5(2) . . ?
N2 Cu1 O1 89.7(2) . . ?
N4 Cu1 O1 86.6(3) . . ?
C9 N1 C5 118.7(6) . . ?
C9 N1 Cu1 126.4(5) . . ?
C5 N1 Cu1 113.7(5) . . ?
C4 N2 C1 117.4(7) . . ?
C4 N2 Cu1 113.2(5) . . ?
C1 N2 Cu1 129.2(6) . . ?
C2 N3 C3 115.6(7) . . ?
C17 N4 Cu1 159.8(7) . . ?
C19 N5 C21 116.6(11) . . ?
C19 N5 C20 123.9(12) . . ?
C21 N5 C20 119.2(12) . . ?
Cu1 O1 H22A 107(6) . . ?
Cu1 O1 H23A 100(7) . . ?
H22A O1 H23A 102(10) . . ?
C19 O10 Cu1 132.5(9) . . ?
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 N2 1.334(10) . ?
C1 C2 1.363(11) . ?
C1 H1 0.9300 . ?
C2 N3 1.331(10) . ?
C2 H2 0.9300 . ?
C3 N3 1.338(10) . ?
C3 C4 1.375(11) . ?
C3 H3 0.9300 . ?
C4 N2 1.335(10) . ?
C4 C5 1.460(11) . ?
C5 C6 1.371(11) . ?
C5 N1 1.374(9) . ?
C6 C7 1.405(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(11) . ?
C7 C10 1.524(11) . ?
C8 C9 1.379(9) . ?
C8 C13 1.511(11) . ?
C9 N1 1.339(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.521(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.526(13) . ?
C11 C12 1.554(14) . ?
C11 H11 0.9800 . ?
C12 C13 1.550(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.570(11) . ?
C13 H13 0.9800 . ?
C14 C15 1.535(13) . ?
C14 C16 1.547(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N4 1.132(10) . ?
C17 C18 1.449(12) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O10 1.153(10) . ?
C19 N5 1.314(14) . ?
C19 H19 0.9300 . ?
C20 N5 1.420(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N5 1.356(16) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl1 O2 1.279(13) . ?
Cl1 O4 1.315(11) . ?
Cl1 O3 1.355(12) . ?
Cl1 O5 1.379(9) . ?
Cl2 O8 1.245(10) . ?
Cl2 O9 1.336(12) . ?
Cl2 O7 1.395(10) . ?
Cl2 O6 1.586(14) . ?
Cu1 O10 1.974(6) . ?
Cu1 N1 1.990(6) . ?
Cu1 N2 2.010(6) . ?
Cu1 N4 2.016(7) . ?
Cu1 O1 2.377(7) . ?
O1 H22A 0.848(14) . ?
O1 H23A 0.848(14) . ?
