#------------------------------------------------------------------------------
#$Date: 2025-08-20 23:21:57 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301837 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/93/4319326.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_4319326
loop_
_publ_author_name
'Ashley E. Ayers'
'Thomas M. Klapötke'
'H. V. Rasika Dias'
_publ_section_title
;
 Azido Derivatives of Germanium(II) and Tin(II): Syntheses and
 Characterization of [(Mes)2DAP]GeN3, [(Mes)2DAP]SnN3, and the
 Corresponding Chloro Analogues Featuring Heterocyclic Six-π-Electron
 Ring Systems (where [(Mes)2DAP] = {N(Mes)C(Me)}2CH)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1000
_journal_page_last               1005
_journal_paper_doi               10.1021/ic001078j
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C23 H29 Cl Ge N2'
_chemical_formula_weight         441.52
_chemical_name_common            '[(Mes)2DAP]GeCl'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 114.144(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.967(4)
_cell_length_b                   12.369(4)
_cell_length_c                   14.5548(13)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      12.47
_cell_measurement_theta_min      5.27
_cell_volume                     4430.1(16)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3376
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.84
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  0.9216
_exptl_absorpt_correction_T_min  0.7519
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelpipeds
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+5.9208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                2582
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic001078j_1.cif
_cod_data_source_block           rd254
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        4430.2(17)
_cod_database_code               4319326
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge Ge 0.155802(11) 0.23460(2) 0.11081(2) 0.02761(14) Uani 1 1 d . . .
Cl Cl 0.12368(3) 0.07615(7) 0.01929(6) 0.0444(2) Uani 1 1 d . . .
N1 N 0.21857(9) 0.16876(18) 0.21930(16) 0.0273(5) Uani 1 1 d . . .
C2 C 0.21417(12) 0.0925(2) 0.2816(2) 0.0304(7) Uani 1 1 d . . .
C3 C 0.16746(12) 0.0767(2) 0.2972(2) 0.0313(7) Uani 1 1 d . . .
H3A H 0.1663 0.0156 0.3335 0.038 Uiso 1 1 calc R . .
C4 C 0.12169(11) 0.1438(2) 0.2636(2) 0.0300(7) Uani 1 1 d . . .
N5 N 0.11167(9) 0.21521(18) 0.18988(17) 0.0278(5) Uani 1 1 d . . .
C6 C 0.26273(13) 0.0228(3) 0.3394(2) 0.0437(8) Uani 1 1 d . . .
H6A H 0.2842 0.0142 0.3011 0.066 Uiso 1 1 calc R . .
H6B H 0.2507 -0.0468 0.3513 0.066 Uiso 1 1 calc R . .
H6C H 0.2843 0.0565 0.4027 0.066 Uiso 1 1 calc R . .
C7 C 0.08379(13) 0.1369(3) 0.3155(2) 0.0414(8) Uani 1 1 d . . .
H7A H 0.0809 0.2066 0.3417 0.062 Uiso 1 1 calc R . .
H7B H 0.0977 0.0857 0.3697 0.062 Uiso 1 1 calc R . .
H7C H 0.0486 0.1139 0.2682 0.062 Uiso 1 1 calc R . .
C8 C 0.27156(11) 0.2067(2) 0.2315(2) 0.0278(7) Uani 1 1 d . . .
C9 C 0.30127(12) 0.2726(2) 0.3147(2) 0.0330(7) Uani 1 1 d . . .
C10 C 0.35113(12) 0.3128(3) 0.3232(2) 0.0391(8) Uani 1 1 d . . .
H10A H 0.3710 0.3563 0.3781 0.047 Uiso 1 1 calc R . .
C11 C 0.37214(12) 0.2906(3) 0.2532(2) 0.0372(7) Uani 1 1 d . . .
C12 C 0.34168(12) 0.2266(2) 0.1720(2) 0.0360(7) Uani 1 1 d . . .
H12A H 0.3552 0.2114 0.1240 0.043 Uiso 1 1 calc R . .
C13 C 0.29141(12) 0.1838(2) 0.1592(2) 0.0295(7) Uani 1 1 d . . .
C14 C 0.28059(13) 0.3008(3) 0.3934(2) 0.0469(8) Uani 1 1 d . . .
H14A H 0.3010 0.3606 0.4328 0.070 Uiso 1 1 calc R . .
H14B H 0.2847 0.2395 0.4363 0.070 Uiso 1 1 calc R . .
H14C H 0.2429 0.3202 0.3611 0.070 Uiso 1 1 calc R . .
C15 C 0.42689(13) 0.3342(3) 0.2652(3) 0.0570(10) Uani 1 1 d . . .
H15A H 0.4348 0.3991 0.3047 0.086 Uiso 1 1 calc R . .
H15B H 0.4261 0.3498 0.2000 0.086 Uiso 1 1 calc R . .
H15C H 0.4545 0.2812 0.2983 0.086 Uiso 1 1 calc R . .
C16 C 0.26143(13) 0.1127(3) 0.0699(2) 0.0410(8) Uani 1 1 d . . .
H16A H 0.2859 0.0890 0.0411 0.061 Uiso 1 1 calc R . .
H16B H 0.2321 0.1526 0.0205 0.061 Uiso 1 1 calc R . .
H16C H 0.2472 0.0509 0.0909 0.061 Uiso 1 1 calc R . .
C17 C 0.06608(11) 0.2883(2) 0.1607(2) 0.0298(7) Uani 1 1 d . . .
C18 C 0.07527(12) 0.3937(2) 0.1993(2) 0.0348(7) Uani 1 1 d . . .
C19 C 0.03252(14) 0.4667(3) 0.1643(3) 0.0464(9) Uani 1 1 d . . .
H19A H 0.0383 0.5370 0.1891 0.056 Uiso 1 1 calc R . .
C20 C -0.01852(14) 0.4384(3) 0.0935(3) 0.0486(9) Uani 1 1 d . . .
C21 C -0.02653(13) 0.3333(3) 0.0583(2) 0.0466(9) Uani 1 1 d . . .
H21A H -0.0608 0.3132 0.0113 0.056 Uiso 1 1 calc R . .
C22 C 0.01490(13) 0.2565(3) 0.0906(2) 0.0386(8) Uani 1 1 d . . .
C23 C 0.13022(13) 0.4262(3) 0.2767(3) 0.0491(9) Uani 1 1 d . . .
H23A H 0.1305 0.5026 0.2889 0.074 Uiso 1 1 calc R . .
H23B H 0.1575 0.4093 0.2523 0.074 Uiso 1 1 calc R . .
H23C H 0.1378 0.3877 0.3382 0.074 Uiso 1 1 calc R . .
C24 C -0.06344(16) 0.5220(4) 0.0563(3) 0.0723(13) Uani 1 1 d . . .
H24A H -0.0958 0.4897 0.0072 0.108 Uiso 1 1 calc R . .
H24B H -0.0525 0.5811 0.0262 0.108 Uiso 1 1 calc R . .
H24C H -0.0705 0.5480 0.1118 0.108 Uiso 1 1 calc R . .
C25 C 0.00405(13) 0.1425(3) 0.0501(3) 0.0508(9) Uani 1 1 d . . .
H25A H 0.0184 0.0921 0.1050 0.076 Uiso 1 1 calc R . .
H25B H 0.0213 0.1311 0.0048 0.076 Uiso 1 1 calc R . .
H25C H -0.0344 0.1316 0.0149 0.076 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'
N N 0.0061 0.0033 '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'
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
N1 Ge N5 90.44(9) . . ?
N1 Ge Cl 96.19(7) . . ?
N5 Ge Cl 93.39(7) . . ?
C2 N1 C8 120.0(2) . . ?
C2 N1 Ge 123.30(19) . . ?
C8 N1 Ge 116.71(17) . . ?
N1 C2 C3 123.1(3) . . ?
N1 C2 C6 118.8(3) . . ?
C3 C2 C6 118.1(3) . . ?
C2 C3 C4 126.3(3) . . ?
N5 C4 C3 122.4(3) . . ?
N5 C4 C7 119.2(3) . . ?
C3 C4 C7 118.4(2) . . ?
C4 N5 C17 121.5(2) . . ?
C4 N5 Ge 125.27(19) . . ?
C17 N5 Ge 113.27(17) . . ?
C13 C8 C9 120.6(3) . . ?
C13 C8 N1 120.6(2) . . ?
C9 C8 N1 118.7(2) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C14 119.6(3) . . ?
C8 C9 C14 122.1(3) . . ?
C11 C10 C9 122.4(3) . . ?
C12 C11 C10 117.8(3) . . ?
C12 C11 C15 120.9(3) . . ?
C10 C11 C15 121.3(3) . . ?
C11 C12 C13 122.6(3) . . ?
C8 C13 C12 118.3(3) . . ?
C8 C13 C16 122.4(3) . . ?
C12 C13 C16 119.2(3) . . ?
C22 C17 C18 121.1(3) . . ?
C22 C17 N5 120.4(3) . . ?
C18 C17 N5 118.4(3) . . ?
C19 C18 C17 118.3(3) . . ?
C19 C18 C23 121.1(3) . . ?
C17 C18 C23 120.6(3) . . ?
C20 C19 C18 122.2(3) . . ?
C21 C20 C19 118.1(3) . . ?
C21 C20 C24 121.9(4) . . ?
C19 C20 C24 120.0(4) . . ?
C20 C21 C22 122.3(3) . . ?
C21 C22 C17 118.0(3) . . ?
C21 C22 C25 120.3(3) . . ?
C17 C22 C25 121.6(3) . . ?
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
Ge N1 1.958(2) . ?
Ge N5 1.980(2) . ?
Ge Cl 2.3285(10) . ?
N1 C2 1.348(4) . ?
N1 C8 1.444(4) . ?
C2 C3 1.382(4) . ?
C2 C6 1.505(4) . ?
C3 C4 1.399(4) . ?
C4 N5 1.330(4) . ?
C4 C7 1.501(4) . ?
N5 C17 1.443(4) . ?
C8 C13 1.391(4) . ?
C8 C9 1.406(4) . ?
C9 C10 1.391(4) . ?
C9 C14 1.506(4) . ?
C10 C11 1.381(5) . ?
C11 C12 1.380(5) . ?
C11 C15 1.513(4) . ?
C12 C13 1.395(4) . ?
C13 C16 1.502(4) . ?
C17 C22 1.396(4) . ?
C17 C18 1.400(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.504(4) . ?
C19 C20 1.385(5) . ?
C20 C21 1.381(5) . ?
C20 C24 1.514(5) . ?
C21 C22 1.394(5) . ?
C22 C25 1.510(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139133521
