#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:13:17 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/86/7128698.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_7128698
loop_
_publ_author_name
'Yang, Shuo'
'Jiang, Wei-Tao'
'Xiao, Bin'
_publ_section_title
;
 Tertiary cyclopropyl carbagermatranes: synthesis and cross-coupling.
;
_journal_issue                   66
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8143
_journal_page_last               8146
_journal_paper_doi               10.1039/d1cc02930d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C24 H31 Ge N'
_chemical_formula_sum            'C24 H31 Ge N'
_chemical_formula_weight         406.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.508(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7360(11)
_cell_length_b                   10.2256(7)
_cell_length_c                   14.5955(11)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.956
_cell_measurement_theta_min      4.796
_cell_volume                     2083.0(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20026
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.931
_diffrn_reflns_theta_min         4.795
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1933 before and 0.0919 after correction. The Ratio of minimum to maximum transmission is 0.6742. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.776
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0747P)²+0.7049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3610
_reflns_number_total             3925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02930d2.cif
_cod_data_source_block           200917ys
_cod_depositor_comments
'Adding full bibliography for 7128698--7128699.cif.'
_cod_database_code               7128698
_shelx_shelxl_version_number     2016/6
_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   0.934
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
Ge1 Ge 0.80962(2) 0.59566(2) 0.70213(2) 0.02465(13) Uani 1 1 d . . . . .
N1 N 0.83113(13) 0.35309(17) 0.66437(14) 0.0324(4) Uani 1 1 d . . . . .
C1 C 0.78943(13) 0.78312(18) 0.72899(15) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.86018(15) 0.8487(2) 0.82717(17) 0.0321(5) Uani 1 1 d . . . . .
H2A H 0.871234 0.943600 0.824448 0.038 Uiso 1 1 calc R . . . .
H2B H 0.917439 0.798141 0.874344 0.038 Uiso 1 1 calc R . . . .
C3 C 0.76430(14) 0.80615(19) 0.81712(15) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.767531 0.725380 0.857236 0.032 Uiso 1 1 calc R . . . .
C4 C 0.69115(14) 0.90199(18) 0.81203(17) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.61891(15) 0.8589(2) 0.83424(17) 0.0326(5) Uani 1 1 d . . . . .
H5 H 0.617714 0.769777 0.852096 0.039 Uiso 1 1 calc R . . . .
C6 C 0.54867(16) 0.9432(3) 0.83087(19) 0.0406(5) Uani 1 1 d . . . . .
H6 H 0.499712 0.911431 0.845878 0.049 Uiso 1 1 calc R . . . .
C7 C 0.54953(17) 1.0734(2) 0.80573(19) 0.0411(6) Uani 1 1 d . . . . .
H7 H 0.501564 1.131458 0.803713 0.049 Uiso 1 1 calc R . . . .
C8 C 0.62046(19) 1.1180(2) 0.78369(19) 0.0399(5) Uani 1 1 d . . . . .
H8 H 0.621507 1.207322 0.766316 0.048 Uiso 1 1 calc R . . . .
C9 C 0.69072(15) 1.0330(2) 0.78669(17) 0.0341(5) Uani 1 1 d . . . . .
H9 H 0.739253 1.065157 0.771148 0.041 Uiso 1 1 calc R . . . .
C10 C 0.74329(15) 0.8645(2) 0.63274(16) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.64416(16) 0.8685(2) 0.57202(18) 0.0347(5) Uani 1 1 d . . . . .
H11 H 0.603980 0.823185 0.593870 0.042 Uiso 1 1 calc R . . . .
C12 C 0.6033(2) 0.9385(3) 0.47940(19) 0.0459(6) Uani 1 1 d . . . . .
H12 H 0.535620 0.941472 0.439251 0.055 Uiso 1 1 calc R . . . .
C13 C 0.6606(2) 1.0033(2) 0.4459(2) 0.0511(7) Uani 1 1 d . . . . .
H13 H 0.632727 1.049588 0.382281 0.061 Uiso 1 1 calc R . . . .
C14 C 0.7584(2) 1.0004(2) 0.50521(19) 0.0469(6) Uani 1 1 d . . . . .
H14 H 0.798175 1.045258 0.482565 0.056 Uiso 1 1 calc R . . . .
C15 C 0.79945(18) 0.9324(2) 0.59799(19) 0.0366(5) Uani 1 1 d . . . . .
H15 H 0.867142 0.932279 0.638508 0.044 Uiso 1 1 calc R . . . .
C16 C 0.91045(17) 0.5309(2) 0.83655(17) 0.0388(5) Uani 1 1 d . . . . .
H16A H 0.973775 0.556591 0.843361 0.047 Uiso 1 1 calc R . . . .
H16B H 0.902585 0.574648 0.892683 0.047 Uiso 1 1 calc R . . . .
C17 C 0.9098(2) 0.3828(2) 0.8513(2) 0.0483(7) Uani 1 1 d . . . . .
H17A H 0.966779 0.357595 0.916028 0.058 Uiso 1 1 calc R . . . .
H17B H 0.852058 0.358255 0.857871 0.058 Uiso 1 1 calc R . . . .
C18 C 0.91050(18) 0.3085(2) 0.76141(19) 0.0427(6) Uani 1 1 d . . . . .
H18A H 0.972041 0.323465 0.759986 0.051 Uiso 1 1 calc R . . . .
H18B H 0.904101 0.213606 0.770107 0.051 Uiso 1 1 calc R . . . .
C19 C 0.73821(18) 0.2962(2) 0.6408(2) 0.0408(6) Uani 1 1 d . . . . .
H19A H 0.738803 0.264235 0.705087 0.049 Uiso 1 1 calc R . . . .
H19B H 0.725017 0.221034 0.593386 0.049 Uiso 1 1 calc R . . . .
C20 C 0.66042(17) 0.3991(2) 0.5906(2) 0.0388(6) Uani 1 1 d . . . . .
H20A H 0.597884 0.361660 0.577737 0.047 Uiso 1 1 calc R . . . .
H20B H 0.656157 0.424757 0.523172 0.047 Uiso 1 1 calc R . . . .
C21 C 0.68128(15) 0.5198(2) 0.65897(19) 0.0351(5) Uani 1 1 d . . . . .
H21A H 0.675229 0.496051 0.721459 0.042 Uiso 1 1 calc R . . . .
H21B H 0.632350 0.587192 0.621153 0.042 Uiso 1 1 calc R . . . .
C22 C 0.85266(17) 0.3625(2) 0.57787(18) 0.0371(5) Uani 1 1 d . . . . .
H22A H 0.792490 0.359604 0.512046 0.044 Uiso 1 1 calc R . . . .
H22B H 0.893061 0.287580 0.579087 0.044 Uiso 1 1 calc R . . . .
C23 C 0.90526(16) 0.4903(2) 0.58526(19) 0.0371(5) Uani 1 1 d . . . . .
H23A H 0.915404 0.499885 0.523515 0.045 Uiso 1 1 calc R . . . .
H23B H 0.968890 0.487867 0.646878 0.045 Uiso 1 1 calc R . . . .
C24 C 0.84885(16) 0.60763(19) 0.59285(18) 0.0311(5) Uani 1 1 d . . . . .
H24A H 0.790759 0.618417 0.525738 0.037 Uiso 1 1 calc R . . . .
H24B H 0.888491 0.687132 0.604757 0.037 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 0.0148 0.0070 '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'
Ge Ge -1.5487 0.7176 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 '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
C16 Ge1 C1 104.58(9) . . ?
C21 Ge1 C1 101.91(8) . . ?
C21 Ge1 C16 114.69(10) . . ?
C24 Ge1 C1 103.67(8) . . ?
C24 Ge1 C16 114.63(10) . . ?
C24 Ge1 C21 115.11(10) . . ?
C19 N1 C18 114.8(2) . . ?
C22 N1 C18 115.10(18) . . ?
C22 N1 C19 115.55(19) . . ?
C2 C1 Ge1 119.73(14) . . ?
C2 C1 C3 59.71(13) . . ?
C3 C1 Ge1 115.88(13) . . ?
C10 C1 Ge1 113.43(14) . . ?
C10 C1 C2 118.00(17) . . ?
C10 C1 C3 120.09(16) . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C1 C2 C3 60.87(13) . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C3 H3 113.7 . . ?
C2 C3 C1 59.42(13) . . ?
C2 C3 H3 113.7 . . ?
C4 C3 C1 123.68(17) . . ?
C4 C3 C2 122.02(17) . . ?
C4 C3 H3 113.7 . . ?
C5 C4 C3 118.47(18) . . ?
C9 C4 C3 123.88(19) . . ?
C9 C4 C5 117.66(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 121.1(2) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C1 121.81(19) . . ?
C15 C10 C1 120.28(19) . . ?
C15 C10 C11 117.8(2) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
Ge1 C16 H16A 108.6 . . ?
Ge1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 Ge1 114.54(17) . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 111.7(2) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N1 C18 C17 109.68(19) . . ?
N1 C18 H18A 109.7 . . ?
N1 C18 H18B 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 H19A 109.8 . . ?
N1 C19 H19B 109.8 . . ?
N1 C19 C20 109.50(19) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C19 C20 C21 111.3(2) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
Ge1 C21 H21A 108.8 . . ?
Ge1 C21 H21B 108.8 . . ?
C20 C21 Ge1 113.95(15) . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
N1 C22 H22A 109.8 . . ?
N1 C22 H22B 109.8 . . ?
N1 C22 C23 109.38(18) . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 H22A 109.8 . . ?
C23 C22 H22B 109.8 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C22 C23 C24 111.36(18) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
Ge1 C24 H24A 108.5 . . ?
Ge1 C24 H24B 108.5 . . ?
C23 C24 Ge1 114.94(15) . . ?
C23 C24 H24A 108.5 . . ?
C23 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
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
Ge1 C1 2.0110(19) . ?
Ge1 C16 1.982(2) . ?
Ge1 C21 1.975(2) . ?
Ge1 C24 1.962(2) . ?
N1 C18 1.463(3) . ?
N1 C19 1.459(3) . ?
N1 C22 1.454(3) . ?
C1 C2 1.506(3) . ?
C1 C3 1.528(3) . ?
C1 C10 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.487(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.520(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.527(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
