#------------------------------------------------------------------------------
#$Date: 2026-05-13 00:54:56 +0200 (Wed, 13 May 2026) $
#$Revision: 305942 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/72/10/7721024.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_7721024
loop_
_publ_author_name
'Zhou, Jie'
'Tong, Binyi'
'Zhong, Zhirong'
'Duan, An'
'Ai, Yong'
'Zhou, Lin'
'Wei, Zhenhong'
'Cai, Hu'
_publ_section_title
;
 A novel 0D germanium-based organic--inorganic hybrid material
 (C12H28N)GeCl3 showing reversible phase transition, dielectric anomaly
 and SHG response
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D6DT00723F
_journal_year                    2026
_chemical_formula_moiety         'C12 H28 N, Cl3 Ge'
_chemical_formula_sum            'C12 H28 Cl3 Ge N'
_chemical_formula_weight         365.29
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2026-03-12
_audit_creation_method
;
Olex2 1.5-ac6-018
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_audit_update_record
;
2026-03-24 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   10.5973(4)
_cell_length_b                   10.5973(4)
_cell_length_c                   9.8138(7)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8560
_cell_measurement_theta_min      3.0360
_cell_volume                     954.46(9)
_computing_molecular_graphics    'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4767
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.764
_diffrn_reflns_theta_min         3.039
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_type   none
_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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_preparation       NONE
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         1483
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0449
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                1076
_reflns_number_total             1483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00723f2.cif
_cod_data_source_block           111
_cod_original_cell_volume        954.46(10)
_cod_database_code               7721024
_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   0.980
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 N003(H003), C004(H004)
1.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B)
1.c Idealised Me refined as rotating group:
 C006(H00C,H00D,H00E), C007(H00F,H00G,H00H)
;
_shelx_res_file
;
TITL 111_a.res in P6(3)
    111.res
    created by SHELXL-2018/3 at 16:00:42 on 01-Dec-2025
REM Old TITL 111 in P6(3)
REM SHELXT solution in P6(3): R1 0.137, Rweak 0.089, Alpha 0.002
REM <I/s> 0.143 for 5 systematic absences, Orientation as input
REM Flack x = 0.086 ( 0.013 ) from 372 Parsons' quotients
REM Formula found by SHELXT: C7 N6 Cl3 Ge
CELL 0.71073 10.5973 10.5973 9.8138 90 90 120
ZERR 2 0.0004 0.0004 0.0007 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -X,-Y,0.5+Z
SYMM +Y,-X+Y,0.5+Z
SYMM -Y+X,+X,0.5+Z
SFAC C H Cl Ge N
UNIT 24 56 6 2 2

L.S. 4
PLAN  5
SIZE 0.01 0.02 0.01
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\111.hkl">
REM </olex2.extras>

WGHT    0.100000
FVAR       0.75098
GE01  4    0.333333    0.666667    0.154463    10.33333    0.09364    0.09364 =
         0.07439    0.00000    0.00000    0.04682
CL02  3    0.315173    0.841484    0.273373    11.00000    0.08349    0.06394 =
         0.15205    0.02681    0.02908    0.04187
N003  5    0.333333    0.666667    0.686243    10.33333    0.03739    0.03739 =
         0.07180    0.00000    0.00000    0.01870
AFIX  13
H003  2    0.333333    0.666667    0.786102    10.33333   -1.20000
AFIX   0
C004  1    0.277113    0.873822    0.694806    11.00000    0.05331    0.04307 =
         0.10163    0.00182    0.00103    0.02785
AFIX  13
H004  2    0.374207    0.944808    0.661037    11.00000   -1.20000
AFIX   0
C005  1    0.236339    0.724596    0.638579    11.00000    0.04454    0.04658 =
         0.08899    0.00009   -0.00645    0.02560
AFIX  23
H00A  2    0.136761    0.656043    0.664793    11.00000   -1.20000
H00B  2    0.239641    0.729822    0.539863    11.00000   -1.20000
AFIX   0
C006  1    0.165608    0.911394    0.634847    11.00000    0.07205    0.06400 =
         0.18383    0.00385   -0.01213    0.04718
AFIX 137
H00C  2    0.161819    0.899585    0.537678    11.00000   -1.50000
H00D  2    0.194325    1.010497    0.656612    11.00000   -1.50000
H00E  2    0.071170    0.847522    0.672875    11.00000   -1.50000
AFIX   0
C007  1    0.279008    0.879381    0.844736    11.00000    0.12173    0.08807 =
         0.10582   -0.01604    0.00985    0.06664
AFIX 137
H00F  2    0.186275    0.806014    0.879356    11.00000   -1.50000
H00G  2    0.297944    0.973687    0.874111    11.00000   -1.50000
H00H  2    0.354039    0.862066    0.878501    11.00000   -1.50000
AFIX   0
HKLF 4




REM  111_a.res in P6(3)
REM wR2 = 0.1345, GooF = S = 0.912, Restrained GooF = 0.912 for all data
REM R1 = 0.0449 for 1076 Fo > 4sig(Fo) and 0.0671 for all 1483 data
REM 54 parameters refined using 1 restraints

END

WGHT      0.0718      0.0146

REM Highest difference peak  0.233,  deepest hole -0.246,  1-sigma level  0.070
Q1    1   0.3385  0.6086  0.1980  11.00000  0.05    0.23
Q2    1   0.3596  0.8864  0.3585  11.00000  0.05    0.19
Q3    1   0.3902  0.8948  0.9455  11.00000  0.05    0.16
Q4    1   0.3970  0.9037  0.4548  11.00000  0.05    0.16
Q5    1   0.0000  1.0000  0.5051  10.33333  0.05    0.16
;
_shelx_res_checksum              56720
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
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
Ge01 Ge 0.333333 0.666667 0.15446(10) 0.0872(4) Uani 1 3 d S T P . .
Cl02 Cl 0.31517(15) 0.84148(14) 0.2734(2) 0.0976(6) Uani 1 1 d . . . . .
N003 N 0.333333 0.666667 0.6862(6) 0.0489(17) Uani 1 3 d S T P . .
H003 H 0.333333 0.666667 0.786102 0.059 Uiso 1 3 calc R U P . .
C004 C 0.2771(5) 0.8738(4) 0.6948(5) 0.0643(14) Uani 1 1 d . . . . .
H004 H 0.374207 0.944808 0.661037 0.077 Uiso 1 1 calc R U . . .
C005 C 0.2363(4) 0.7246(4) 0.6386(6) 0.0588(10) Uani 1 1 d . . . . .
H00A H 0.136761 0.656043 0.664793 0.071 Uiso 1 1 calc R U . . .
H00B H 0.239641 0.729822 0.539863 0.071 Uiso 1 1 calc R U . . .
C006 C 0.1656(6) 0.9114(5) 0.6348(11) 0.101(2) Uani 1 1 d . . . . .
H00C H 0.161819 0.899585 0.537678 0.151 Uiso 1 1 calc R U . . .
H00D H 0.194325 1.010497 0.656612 0.151 Uiso 1 1 calc R U . . .
H00E H 0.071170 0.847522 0.672875 0.151 Uiso 1 1 calc R U . . .
C007 C 0.2790(9) 0.8794(8) 0.8447(8) 0.0989(18) Uani 1 1 d . . . . .
H00F H 0.186275 0.806014 0.879356 0.148 Uiso 1 1 calc R U . . .
H00G H 0.297944 0.973687 0.874111 0.148 Uiso 1 1 calc R U . . .
H00H H 0.354039 0.862066 0.878501 0.148 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ge01 0.0936(5) 0.0936(5) 0.0744(6) 0.000 0.000 0.0468(3)
Cl02 0.0835(8) 0.0639(7) 0.1520(16) 0.0268(8) 0.0291(9) 0.0419(6)
N003 0.0374(15) 0.0374(15) 0.072(5) 0.000 0.000 0.0187(7)
C004 0.053(2) 0.0431(18) 0.102(4) 0.0018(19) 0.0010(19) 0.0279(17)
C005 0.0445(17) 0.0466(19) 0.089(3) 0.000(2) -0.006(2) 0.0256(15)
C006 0.072(3) 0.064(3) 0.184(7) 0.004(4) -0.012(4) 0.047(2)
C007 0.122(5) 0.088(4) 0.106(5) -0.016(3) 0.010(4) 0.067(4)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 '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'
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
Cl02 Ge01 Cl02 96.10(7) . 2_665 ?
Cl02 Ge01 Cl02 96.10(7) . 3_565 ?
Cl02 Ge01 Cl02 96.10(7) 2_665 3_565 ?
C005 N003 H003 108.0 2_665 . ?
C005 N003 H003 108.0 3_565 . ?
C005 N003 H003 108.0 . . ?
C005 N003 C005 110.9(3) . 3_565 ?
C005 N003 C005 110.9(3) 3_565 2_665 ?
C005 N003 C005 110.9(3) . 2_665 ?
C005 C004 H004 108.6 . . ?
C005 C004 C006 105.9(4) . . ?
C006 C004 H004 108.6 . . ?
C007 C004 H004 108.6 . . ?
C007 C004 C005 113.3(5) . . ?
C007 C004 C006 111.6(6) . . ?
N003 C005 C004 114.4(4) . . ?
N003 C005 H00A 108.7 . . ?
N003 C005 H00B 108.7 . . ?
C004 C005 H00A 108.7 . . ?
C004 C005 H00B 108.7 . . ?
H00A C005 H00B 107.6 . . ?
C004 C006 H00C 109.5 . . ?
C004 C006 H00D 109.5 . . ?
C004 C006 H00E 109.5 . . ?
H00C C006 H00D 109.5 . . ?
H00C C006 H00E 109.5 . . ?
H00D C006 H00E 109.5 . . ?
C004 C007 H00F 109.5 . . ?
C004 C007 H00G 109.5 . . ?
C004 C007 H00H 109.5 . . ?
H00F C007 H00G 109.5 . . ?
H00F C007 H00H 109.5 . . ?
H00G C007 H00H 109.5 . . ?
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
Ge01 Cl02 2.2776(17) . ?
Ge01 Cl02 2.2776(17) 2_665 ?
Ge01 Cl02 2.2776(17) 3_565 ?
N003 H003 0.9800 . ?
N003 C005 1.511(4) 3_565 ?
N003 C005 1.511(4) 2_665 ?
N003 C005 1.511(4) . ?
C004 H004 0.9800 . ?
C004 C005 1.519(6) . ?
C004 C006 1.540(7) . ?
C004 C007 1.472(9) . ?
C005 H00A 0.9700 . ?
C005 H00B 0.9700 . ?
C006 H00C 0.9600 . ?
C006 H00D 0.9600 . ?
C006 H00E 0.9600 . ?
C007 H00F 0.9600 . ?
C007 H00G 0.9600 . ?
C007 H00H 0.9600 . ?
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
C005 N003 C005 C004 -62.7(7) 3_565 . . . ?
C005 N003 C005 C004 173.6(3) 2_665 . . . ?
C006 C004 C005 N003 -179.7(5) . . . . ?
C007 C004 C005 N003 -57.0(7) . . . . ?
