# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'C. N. R. Rao'
'Amitava Choudhury'
'Manashi Nath'

_publ_contact_author_name        'Prof C. N. R. Rao'
_publ_contact_author_address     
;
CSIR-COE, CPMU
Jawaharlal Nehru Center for Advanced Scientific Research
Bangalore
Karnataka
560064
INDIA
;

_publ_contact_author_email       CNRRAO@JNCASR.AC.IN

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Chemical routes to GeS2 and GeSe2 nanowires
;

data_sad
_database_code_depnum_ccdc_archive 'CCDC 247374'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C12 H32 Ge N2 Se3'
_chemical_formula_weight         513.87
_chemical_melting_point          ?
_chemical_compound_source        ?

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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8528(8)
_cell_length_b                   18.3953(14)
_cell_length_c                   10.9941(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.42
_cell_angle_gamma                90.00
_cell_volume                     2134.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3525
_cell_measurement_theta_min      2
_cell_measurement_theta_max      23.5

_exptl_crystal_description       Chuncky
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    6.540
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.713924
_exptl_absorpt_correction_T_max  1.000000

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens CCD-diffractometer'
_diffrn_measurement_method       \W
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8642
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         23.37
_reflns_number_total             3051
_reflns_number_observed          2141
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       SMART(Siemens,1996)
_computing_cell_refinement       SAINT(Siemens,1996)
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'SHELXTL v5.0'
_computing_publication_material  'SHELXTL v5.0'

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
are based on F, with F set to zero for negative F^2^. The observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+4.6686P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3051
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_obs          0.0709
_refine_ls_wR_factor_all         0.1237
_refine_ls_wR_factor_obs         0.1128
_refine_ls_goodness_of_fit_all   1.169
_refine_ls_goodness_of_fit_obs   1.283
_refine_ls_restrained_S_all      1.169
_refine_ls_restrained_S_obs      1.283
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000

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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Ge1 Ge 0.43875(10) 0.07839(6) 0.02860(10) 0.0460(3) Uani 1 d . .
Se1 Se 0.56862(10) 0.17979(6) 0.07999(10) 0.0539(3) Uani 1 d . .
Se2 Se 0.47274(11) 0.02289(6) -0.15973(9) 0.0561(3) Uani 1 d . .
Se3 Se 0.23044(11) 0.09859(6) 0.02626(12) 0.0717(4) Uani 1 d . .
C1 C 0.3150(12) 0.2306(7) 0.2980(12) 0.086(4) Uani 1 d . .
H3 H 0.2831(12) 0.2445(7) 0.3700(12) 0.103 Uiso 1 calc R .
H4 H 0.2651(12) 0.1899(7) 0.2573(12) 0.103 Uiso 1 calc R .
C2 C 0.3036(13) 0.2936(8) 0.2083(13) 0.100(5) Uani 1 d . .
H5 H 0.3363(13) 0.2795(8) 0.1368(13) 0.120 Uiso 1 calc R .
H6 H 0.3539(13) 0.3341(8) 0.2494(13) 0.120 Uiso 1 calc R .
C3 C 0.1663(17) 0.3172(10) 0.1641(17) 0.171(7) Uiso 1 d . .
H7 H 0.1611(17) 0.3573(10) 0.1073(17) 0.256 Uiso 1 calc R .
H8 H 0.1344(17) 0.3319(10) 0.2348(17) 0.256 Uiso 1 calc R .
H9 H 0.1168(17) 0.2774(10) 0.1224(17) 0.256 Uiso 1 calc R .
N1 N 0.4501(10) 0.2090(5) 0.3387(9) 0.079(3) Uani 1 d . .
H1 H 0.4919(10) 0.2445(5) 0.3877(9) 0.095 Uiso 1 calc R .
H2 H 0.4824(10) 0.2063(5) 0.2705(9) 0.095 Uiso 1 calc R .
C4 C 0.4769(15) 0.1383(7) 0.4085(12) 0.101(5) Uani 1 d . .
H10 H 0.4370(15) 0.0985(7) 0.3559(12) 0.121 Uiso 1 calc R .
H11 H 0.4428(15) 0.1396(7) 0.4826(12) 0.121 Uiso 1 calc R .
C5 C 0.6218(16) 0.1267(8) 0.4462(14) 0.125(6) Uani 1 d . .
H12 H 0.6554(16) 0.1255(8) 0.3718(14) 0.150 Uiso 1 calc R .
H13 H 0.6613(16) 0.1669(8) 0.4980(14) 0.150 Uiso 1 calc R .
C6 C 0.6526(18) 0.0565(11) 0.5170(17) 0.173(8) Uiso 1 d . .
H14 H 0.7428(18) 0.0500(11) 0.5398(17) 0.259 Uiso 1 calc R .
H15 H 0.6144(18) 0.0168(11) 0.4652(17) 0.259 Uiso 1 calc R .
H16 H 0.6203(18) 0.0580(11) 0.5912(17) 0.259 Uiso 1 calc R .
C7 C 0.0798(13) -0.0888(8) -0.1342(16) 0.114(5) Uani 1 d . .
H19 H 0.0629(13) -0.1403(8) -0.1469(16) 0.137 Uiso 1 calc R .
H20 H 0.0053(13) -0.0663(8) -0.1159(16) 0.137 Uiso 1 calc R .
C8 C 0.1022(18) -0.0585(11) -0.2441(18) 0.155(7) Uiso 1 d . .
H21 H 0.1769(18) -0.0806(11) -0.2626(18) 0.186 Uiso 1 calc R .
H22 H 0.1176(18) -0.0068(11) -0.2325(18) 0.186 Uiso 1 calc R .
C9 C -0.0128(21) -0.0713(12) -0.3539(21) 0.219(10) Uiso 1 d . .
H23 H 0.0034(21) -0.0504(12) -0.4287(21) 0.328 Uiso 1 calc R .
H24 H -0.0864(21) -0.0489(12) -0.3358(21) 0.328 Uiso 1 calc R .
H25 H -0.0272(21) -0.1226(12) -0.3658(21) 0.328 Uiso 1 calc R .
N2 N 0.1878(8) -0.0787(5) -0.0272(10) 0.075(3) Uani 1 d . .
H17 H 0.2098(8) -0.0314(5) -0.0225(10) 0.090 Uiso 1 calc R .
H18 H 0.2540(8) -0.1042(5) -0.0409(10) 0.090 Uiso 1 calc R .
C10 C 0.1628(15) -0.1020(8) 0.0977(17) 0.127(6) Uani 1 d . .
H26 H 0.2314(15) -0.0852(8) 0.1650(17) 0.152 Uiso 1 calc R .
H27 H 0.0849(15) -0.0798(8) 0.1083(17) 0.152 Uiso 1 calc R .
C11 C 0.1523(23) -0.1819(13) 0.1044(22) 0.210(10) Uiso 1 d . .
H28 H 0.0768(23) -0.1988(13) 0.0456(22) 0.251 Uiso 1 calc R .
H29 H 0.2256(23) -0.2051(13) 0.0848(22) 0.251 Uiso 1 calc R .
C12 C 0.1456(23) -0.1980(14) 0.2266(24) 0.249(12) Uiso 1 d . .
H30 H 0.1386(23) -0.2497(14) 0.2356(24) 0.374 Uiso 1 calc R .
H31 H 0.0728(23) -0.1746(14) 0.2447(24) 0.374 Uiso 1 calc R .
H32 H 0.2208(23) -0.1809(14) 0.2837(24) 0.374 Uiso 1 calc R .

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
Ge1 0.0469(6) 0.0413(6) 0.0532(7) -0.0042(5) 0.0187(5) -0.0005(5)
Se1 0.0578(7) 0.0439(7) 0.0628(8) -0.0046(5) 0.0196(6) -0.0054(5)
Se2 0.0753(8) 0.0498(7) 0.0463(7) -0.0005(5) 0.0201(6) 0.0041(6)
Se3 0.0512(7) 0.0619(8) 0.1076(11) -0.0168(7) 0.0299(7) 0.0024(6)
C1 0.075(10) 0.097(11) 0.092(11) -0.015(9) 0.035(8) -0.008(8)
C2 0.103(11) 0.089(11) 0.098(11) -0.015(9) 0.001(9) 0.031(9)
N1 0.110(9) 0.055(7) 0.081(8) -0.009(5) 0.036(7) -0.002(6)
C4 0.168(16) 0.068(10) 0.071(10) 0.002(8) 0.034(10) 0.009(10)
C5 0.167(17) 0.097(13) 0.101(13) 0.020(9) 0.013(12) 0.038(12)
C7 0.078(10) 0.118(14) 0.148(16) -0.007(11) 0.026(11) -0.009(9)
N2 0.053(6) 0.052(6) 0.121(9) -0.007(6) 0.023(7) 0.003(5)
C10 0.111(12) 0.094(12) 0.200(19) 0.020(11) 0.088(12) -0.007(10)

_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 Se3 2.2854(15) . ?
Ge1 Se1 2.3270(14) . ?
Ge1 Se2 2.4125(14) . ?
Ge1 Se2 2.4143(15) 3_655 ?
Se2 Ge1 2.4144(15) 3_655 ?
C1 N1 1.484(14) . ?
C1 C2 1.51(2) . ?
C1 H3 0.97 . ?
C1 H4 0.97 . ?
C2 C3 1.52(2) . ?
C2 H5 0.97 . ?
C2 H6 0.97 . ?
C3 H7 0.96 . ?
C3 H8 0.96 . ?
C3 H9 0.96 . ?
N1 C4 1.503(14) . ?
N1 H1 0.90 . ?
N1 H2 0.90 . ?
C4 C5 1.55(2) . ?
C4 H10 0.97 . ?
C4 H11 0.97 . ?
C5 C6 1.50(2) . ?
C5 H12 0.97 . ?
C5 H13 0.97 . ?
C6 H14 0.96 . ?
C6 H15 0.96 . ?
C6 H16 0.96 . ?
C7 C8 1.40(2) . ?
C7 N2 1.47(2) . ?
C7 H19 0.97 . ?
C7 H20 0.97 . ?
C8 C9 1.54(2) . ?
C8 H21 0.97 . ?
C8 H22 0.97 . ?
C9 H23 0.96 . ?
C9 H24 0.96 . ?
C9 H25 0.96 . ?
N2 C10 1.52(2) . ?
N2 H17 0.90 . ?
N2 H18 0.90 . ?
C10 C11 1.48(2) . ?
C10 H26 0.97 . ?
C10 H27 0.97 . ?
C11 C12 1.39(3) . ?
C11 H28 0.97 . ?
C11 H29 0.97 . ?
C12 H30 0.96 . ?
C12 H31 0.96 . ?
C12 H32 0.96 . ?

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
Se3 Ge1 Se1 114.47(6) . . ?
Se3 Ge1 Se2 114.02(6) . . ?
Se1 Ge1 Se2 110.06(5) . . ?
Se3 Ge1 Se2 112.80(6) . 3_655 ?
Se1 Ge1 Se2 109.82(6) . 3_655 ?
Se2 Ge1 Se2 93.84(5) . 3_655 ?
Ge1 Se2 Ge1 86.16(5) . 3_655 ?
N1 C1 C2 109.1(10) . . ?
N1 C1 H3 109.9(6) . . ?
C2 C1 H3 109.9(7) . . ?
N1 C1 H4 109.9(6) . . ?
C2 C1 H4 109.9(8) . . ?
H3 C1 H4 108.3 . . ?
C1 C2 C3 110.7(13) . . ?
C1 C2 H5 109.5(7) . . ?
C3 C2 H5 109.5(9) . . ?
C1 C2 H6 109.5(7) . . ?
C3 C2 H6 109.5(9) . . ?
H5 C2 H6 108.1 . . ?
C2 C3 H7 109.5(9) . . ?
C2 C3 H8 109.5(9) . . ?
H7 C3 H8 109.5 . . ?
C2 C3 H9 109.5(9) . . ?
H7 C3 H9 109.5 . . ?
H8 C3 H9 109.5 . . ?
C1 N1 C4 116.5(11) . . ?
C1 N1 H1 108.2(6) . . ?
C4 N1 H1 108.2(7) . . ?
C1 N1 H2 108.2(6) . . ?
C4 N1 H2 108.2(6) . . ?
H1 N1 H2 107.3 . . ?
N1 C4 C5 108.7(12) . . ?
N1 C4 H10 109.9(7) . . ?
C5 C4 H10 109.9(8) . . ?
N1 C4 H11 109.9(6) . . ?
C5 C4 H11 109.9(8) . . ?
H10 C4 H11 108.3 . . ?
C6 C5 C4 110.3(14) . . ?
C6 C5 H12 109.6(10) . . ?
C4 C5 H12 109.6(8) . . ?
C6 C5 H13 109.6(10) . . ?
C4 C5 H13 109.6(8) . . ?
H12 C5 H13 108.1 . . ?
C5 C6 H14 109.5(10) . . ?
C5 C6 H15 109.5(10) . . ?
H14 C6 H15 109.5 . . ?
C5 C6 H16 109.5(10) . . ?
H14 C6 H16 109.5 . . ?
H15 C6 H16 109.5 . . ?
C8 C7 N2 112.0(14) . . ?
C8 C7 H19 109.2(11) . . ?
N2 C7 H19 109.2(7) . . ?
C8 C7 H20 109.2(11) . . ?
N2 C7 H20 109.2(7) . . ?
H19 C7 H20 107.9 . . ?
C7 C8 C9 110.1(17) . . ?
C7 C8 H21 109.6(11) . . ?
C9 C8 H21 109.6(12) . . ?
C7 C8 H22 109.6(11) . . ?
C9 C8 H22 109.6(12) . . ?
H21 C8 H22 108.1 . . ?
C8 C9 H23 109.5(12) . . ?
C8 C9 H24 109.5(12) . . ?
H23 C9 H24 109.5 . . ?
C8 C9 H25 109.5(12) . . ?
H23 C9 H25 109.5 . . ?
H24 C9 H25 109.5 . . ?
C7 N2 C10 114.3(11) . . ?
C7 N2 H17 108.7(7) . . ?
C10 N2 H17 108.7(7) . . ?
C7 N2 H18 108.7(7) . . ?
C10 N2 H18 108.7(7) . . ?
H17 N2 H18 107.6 . . ?
C11 C10 N2 111.0(15) . . ?
C11 C10 H26 109.4(13) . . ?
N2 C10 H26 109.4(7) . . ?
C11 C10 H27 109.4(11) . . ?
N2 C10 H27 109.4(7) . . ?
H26 C10 H27 108.0 . . ?
C12 C11 C10 106.4(21) . . ?
C12 C11 H28 110.4(16) . . ?
C10 C11 H28 110.4(13) . . ?
C12 C11 H29 110.4(15) . . ?
C10 C11 H29 110.4(11) . . ?
H28 C11 H29 108.6 . . ?
C11 C12 H30 109.5(16) . . ?
C11 C12 H31 109.5(15) . . ?
H30 C12 H31 109.5 . . ?
C11 C12 H32 109.5(16) . . ?
H30 C12 H32 109.5 . . ?
H31 C12 H32 109.5 . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.104