# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 2153796'
loop_
_audit_author_name
_audit_author_address
'Youhei Takeda'
;Osaka University
Japan
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H19 Ge N'
_chemical_formula_moiety         'C24 H19 Ge N'
_chemical_formula_weight         394.01
_chemical_melting_point          '472 (dec.)'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.89970(13)
_cell_length_b                   8.57542(10)
_cell_length_c                   20.1183(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.5617(10)
_cell_angle_gamma                90.0000
_cell_volume                     1878.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7411
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      74.16
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808.00
_exptl_absorpt_coefficient_mu    2.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.799

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            9935
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_theta_max         74.442
_diffrn_reflns_theta_min         4.060
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3720
_reflns_number_gt                3439
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0915
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0573P)²+0.3898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Ge Ge -1.0885 0.8855
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.27157(2) 0.63044(2) 0.58394(2) 0.03561(10) Uani 1 1 d . . . . .
N1 N 0.31335(17) 0.8282(3) 0.71607(10) 0.0544(5) Uani 1 1 d . . . . .
H1 H 0.326873 0.894434 0.748329 0.065 Uiso 1 1 calc R U . . .
C1 C 0.41794(17) 0.6528(2) 0.64082(9) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.52855(18) 0.5797(2) 0.62598(10) 0.0403(4) Uani 1 1 d . . . . .
H2 H 0.529358 0.510216 0.589867 0.048 Uiso 1 1 calc R U . . .
C3 C 0.63598(19) 0.6068(3) 0.66277(11) 0.0459(5) Uani 1 1 d . . . . .
H3 H 0.709439 0.558396 0.651293 0.055 Uiso 1 1 calc R U . . .
C4 C 0.63438(18) 0.7065(3) 0.71692(11) 0.0493(5) Uani 1 1 d . . . . .
H4 H 0.707227 0.725573 0.742403 0.059 Uiso 1 1 calc R U . . .
C5 C 0.52690(19) 0.7778(3) 0.73370(10) 0.0505(5) Uani 1 1 d . . . . .
H5 H 0.526722 0.844280 0.770831 0.061 Uiso 1 1 calc R U . . .
C6 C 0.41768(17) 0.7518(3) 0.69582(9) 0.0417(4) Uani 1 1 d . . . . .
C7 C 0.15191(17) 0.7347(2) 0.63652(9) 0.0395(4) Uani 1 1 d . . . . .
C8 C 0.02614(19) 0.7322(3) 0.61870(11) 0.0493(5) Uani 1 1 d . . . . .
H8 H -0.001310 0.675816 0.580817 0.059 Uiso 1 1 calc R U . . .
C9 C -0.05846(19) 0.8104(3) 0.65540(12) 0.0563(6) Uani 1 1 d . . . . .
H9 H -0.142235 0.808610 0.642117 0.068 Uiso 1 1 calc R U . . .
C10 C -0.0191(2) 0.8914(3) 0.71180(12) 0.0539(6) Uani 1 1 d . . . . .
H10 H -0.076358 0.944535 0.737059 0.065 Uiso 1 1 calc R U . . .
C11 C 0.1040(2) 0.8945(3) 0.73117(12) 0.0521(5) Uani 1 1 d . . . . .
H11 H 0.129951 0.948864 0.769849 0.062 Uiso 1 1 calc R U . . .
C12 C 0.19056(18) 0.8172(3) 0.69368(10) 0.0431(4) Uani 1 1 d . . . . .
C13 C 0.22300(17) 0.4156(2) 0.56785(9) 0.0379(4) Uani 1 1 d . . . . .
C14 C 0.1476(3) 0.3372(3) 0.61056(13) 0.0648(7) Uani 1 1 d . . . . .
H14 H 0.118102 0.389133 0.647778 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1155(3) 0.1830(3) 0.59867(19) 0.0836(9) Uani 1 1 d . . . . .
H15 H 0.063568 0.131758 0.627666 0.100 Uiso 1 1 calc R U . . .
C16 C 0.1582(3) 0.1048(3) 0.54565(17) 0.0688(8) Uani 1 1 d . . . . .
H16 H 0.136750 -0.000186 0.538414 0.083 Uiso 1 1 calc R U . . .
C17 C 0.2318(3) 0.1791(3) 0.50324(14) 0.0638(6) Uani 1 1 d . . . . .
H17 H 0.261361 0.125445 0.466463 0.077 Uiso 1 1 calc R U . . .
C18 C 0.2637(2) 0.3340(3) 0.51399(11) 0.0502(5) Uani 1 1 d . . . . .
H18 H 0.314092 0.384427 0.483944 0.060 Uiso 1 1 calc R U . . .
C19 C 0.29984(18) 0.7280(2) 0.49805(9) 0.0399(4) Uani 1 1 d . . . . .
C20 C 0.4117(2) 0.7970(3) 0.48538(11) 0.0476(5) Uani 1 1 d . . . . .
H20 H 0.474398 0.798913 0.519027 0.057 Uiso 1 1 calc R U . . .
C21 C 0.4327(3) 0.8632(3) 0.42397(14) 0.0608(7) Uani 1 1 d . . . . .
H21 H 0.509494 0.907613 0.416031 0.073 Uiso 1 1 calc R U . . .
C22 C 0.3409(3) 0.8637(3) 0.37466(13) 0.0638(7) Uani 1 1 d . . . . .
H22 H 0.354454 0.909198 0.333122 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2293(3) 0.7971(3) 0.38664(12) 0.0642(7) Uani 1 1 d . . . . .
H23 H 0.166210 0.798584 0.353237 0.077 Uiso 1 1 calc R U . . .
C24 C 0.2088(2) 0.7280(3) 0.44724(11) 0.0519(5) Uani 1 1 d . . . . .
H24 H 0.132737 0.680513 0.454193 0.062 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.931(2) . ?
Ge1 C7 1.9346(19) . ?
Ge1 C13 1.940(2) . ?
Ge1 C19 1.9565(19) . ?
N1 C6 1.389(3) . ?
N1 C12 1.396(3) . ?
N1 H1 0.8700 . ?
C1 C6 1.395(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9400 . ?
C7 C12 1.399(3) . ?
C7 C8 1.402(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.400(3) . ?
C11 H11 0.9400 . ?
C13 C18 1.380(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.359(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.356(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.389(3) . ?
C19 C24 1.392(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?

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
C1 Ge1 C7 100.92(8) . . ?
C1 Ge1 C13 113.89(8) . . ?
C7 Ge1 C13 110.15(8) . . ?
C1 Ge1 C19 108.81(8) . . ?
C7 Ge1 C19 114.96(8) . . ?
C13 Ge1 C19 108.14(8) . . ?
C6 N1 C12 131.23(18) . . ?
C6 N1 H1 114.4 . . ?
C12 N1 H1 114.4 . . ?
C6 C1 C2 118.24(18) . . ?
C6 C1 Ge1 119.96(14) . . ?
C2 C1 Ge1 121.66(14) . . ?
C3 C2 C1 121.90(19) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.13(19) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.49(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N1 C6 C1 123.40(18) . . ?
N1 C6 C5 116.89(18) . . ?
C1 C6 C5 119.72(18) . . ?
C12 C7 C8 118.24(18) . . ?
C12 C7 Ge1 119.84(14) . . ?
C8 C7 Ge1 121.91(15) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N1 C12 C7 123.26(18) . . ?
N1 C12 C11 116.96(19) . . ?
C7 C12 C11 119.77(19) . . ?
C18 C13 C14 117.4(2) . . ?
C18 C13 Ge1 121.16(15) . . ?
C14 C13 Ge1 121.39(17) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 121.4(2) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C24 117.89(19) . . ?
C20 C19 Ge1 121.22(15) . . ?
C24 C19 Ge1 120.88(16) . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?

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
C6 C1 C2 C3 -1.9(3) . . . . ?
Ge1 C1 C2 C3 173.75(16) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C12 N1 C6 C1 6.4(4) . . . . ?
C12 N1 C6 C5 -173.4(2) . . . . ?
C2 C1 C6 N1 -178.8(2) . . . . ?
Ge1 C1 C6 N1 5.5(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
Ge1 C1 C6 C5 -174.66(16) . . . . ?
C4 C5 C6 N1 -180.0(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
Ge1 C7 C8 C9 -178.17(18) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C6 N1 C12 C7 -9.3(4) . . . . ?
C6 N1 C12 C11 171.0(2) . . . . ?
C8 C7 C12 N1 -179.8(2) . . . . ?
Ge1 C7 C12 N1 -0.6(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
Ge1 C7 C12 C11 179.11(17) . . . . ?
C10 C11 C12 N1 179.0(2) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C18 C13 C14 C15 0.0(4) . . . . ?
Ge1 C13 C14 C15 -179.0(2) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
Ge1 C13 C18 C17 178.30(19) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C24 C19 C20 C21 -0.3(3) . . . . ?
Ge1 C19 C20 C21 178.56(17) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C23 C24 C19 1.7(4) . . . . ?
C20 C19 C24 C23 -1.1(3) . . . . ?
Ge1 C19 C24 C23 180.00(19) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azagermine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/n-hexane'
_exptl_crystal_preparation       Luminescent
