# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
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data_TTFCOONH3Ph
_database_code_depnum_ccdc_archive 'CCDC 906098'
#TrackingRef '14706_web_deposit_cif_file_0_YukaKobayashi_1350366734.TTFCOONH3Ph.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common 'Anilinium Tetrathiafulvalene-2-Carboxylate'
_chemical_formula_moiety 'C7 H3 O2 S4, C6 H8 N'
_chemical_formula_sum 'C13 H11 N O2 S4'
_chemical_formula_weight 341.47
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 8.82440(10)
_cell_length_b 6.26990(10)
_cell_length_c 26.3613(5)
_cell_angle_alpha 90
_cell_angle_beta 95.8516(7)
_cell_angle_gamma 90
_cell_volume 1450.92(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 90
_cell_measurement_reflns_used 40647
_cell_measurement_theta_min 1.55
_cell_measurement_theta_max 31.05
_exptl_crystal_description plate
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.563
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 704
_exptl_absorpt_coefficient_mu 0.653
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 90
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus rotating anode'
_diffrn_radiation_monochromator confocal
_diffrn_measurement_device_type 'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method \w-scan
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 38609
_diffrn_reflns_av_R_equivalents 0.0420
_diffrn_reflns_av_sigmaI/netI 0.0285
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -37
_diffrn_reflns_limit_l_max 37
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 31.05
_reflns_number_total 4607
_reflns_number_gt 3933
_reflns_threshold_expression I>2\s(I)
_computing_data_collection CrystalClear
_computing_cell_refinement HKL2000
_computing_data_reduction HKL2000
_computing_structure_solution SIR2004
_computing_structure_refinement SHELXL-97
_computing_molecular_graphics 'ORTEP-3 for Windows'
_computing_publication_material SHELXL-97
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness 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 threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.5479P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4607
_refine_ls_number_parameters 225
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0373
_refine_ls_R_factor_gt 0.0302
_refine_ls_wR_factor_ref 0.0819
_refine_ls_wR_factor_gt 0.0780
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_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_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
S1 S 0.06969(4) 0.70668(5) 0.428995(12) 0.01841(8) Uani 1 1 d . . .
S2 S 0.10585(4) 0.24746(5) 0.453834(12) 0.01880(8) Uani 1 1 d . . .
S3 S 0.35653(4) 0.37934(5) 0.551619(12) 0.02060(8) Uani 1 1 d . . .
S4 S 0.31116(4) 0.83212(5) 0.522838(13) 0.02134(8) Uani 1 1 d . . .
O1 O -0.19286(11) 0.49388(15) 0.31044(3) 0.02029(19) Uani 1 1 d . . .
O2 O -0.10841(11) 0.81497(15) 0.33716(4) 0.02002(19) Uani 1 1 d . . .
C1 C 0.15888(14) 0.5117(2) 0.46984(5) 0.0168(2) Uani 1 1 d . . .
C2 C -0.02257(14) 0.5220(2) 0.38633(4) 0.0154(2) Uani 1 1 d . . .
C3 C -0.00607(15) 0.3151(2) 0.39829(5) 0.0174(2) Uani 1 1 d . . .
H3 H -0.0532(18) 0.203(3) 0.3808(6) 0.017(4) Uiso 1 1 d . . .
C4 C 0.26047(14) 0.5648(2) 0.50964(5) 0.0173(2) Uani 1 1 d . . .
C5 C 0.49200(16) 0.5646(3) 0.57713(5) 0.0243(3) Uani 1 1 d . . .
H5 H 0.573(2) 0.509(3) 0.5986(7) 0.035(5) Uiso 1 1 d . . .
C6 C 0.47147(17) 0.7682(2) 0.56427(5) 0.0243(3) Uani 1 1 d . . .
H6 H 0.532(2) 0.879(3) 0.5771(7) 0.035(5) Uiso 1 1 d . . .
C7 C -0.11505(14) 0.6159(2) 0.34156(4) 0.0157(2) Uani 1 1 d . . .
N1 N -0.19333(12) 0.59401(19) 0.21016(4) 0.0166(2) Uani 1 1 d . . .
H1A H -0.1999(19) 0.574(3) 0.2452(7) 0.026(4) Uiso 1 1 d . . .
H1B H -0.234(2) 0.716(3) 0.2000(7) 0.023(4) Uiso 1 1 d . . .
H1C H -0.253(2) 0.493(3) 0.1955(7) 0.033(5) Uiso 1 1 d . . .
C8 C -0.03480(14) 0.5733(2) 0.19942(5) 0.0172(2) Uani 1 1 d . . .
C9 C 0.01469(16) 0.3831(2) 0.17995(5) 0.0232(3) Uani 1 1 d . . .
H9 H -0.054(2) 0.269(3) 0.1742(7) 0.026(5) Uiso 1 1 d . . .
C10 C 0.16613(18) 0.3656(3) 0.17033(6) 0.0285(3) Uani 1 1 d . . .
H10 H 0.205(2) 0.235(3) 0.1564(8) 0.041(5) Uiso 1 1 d . . .
C11 C 0.26517(17) 0.5352(3) 0.18002(6) 0.0278(3) Uani 1 1 d . . .
H11 H 0.363(2) 0.525(3) 0.1730(7) 0.036(5) Uiso 1 1 d . . .
C12 C 0.21447(17) 0.7236(3) 0.19992(6) 0.0275(3) Uani 1 1 d . . .
H12 H 0.276(2) 0.834(3) 0.2068(7) 0.035(5) Uiso 1 1 d . . .
C13 C 0.06331(16) 0.7432(2) 0.20998(6) 0.0235(3) Uani 1 1 d . . .
H13 H 0.0257(19) 0.874(3) 0.2228(7) 0.028(5) Uiso 1 1 d . . .
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
S1 0.02375(16) 0.01226(15) 0.01739(14) 0.00045(10) -0.00681(11) -0.00096(11)
S2 0.02365(16) 0.01241(15) 0.01855(15) 0.00011(10) -0.00646(11) 0.00112(11)
S3 0.02372(16) 0.01766(16) 0.01872(15) 0.00073(11) -0.00600(11) 0.00262(12)
S4 0.02283(16) 0.01538(16) 0.02402(16) -0.00188(11) -0.00630(12) -0.00072(12)
O1 0.0264(5) 0.0183(5) 0.0146(4) 0.0006(3) -0.0054(3) -0.0046(4)
O2 0.0216(5) 0.0152(4) 0.0218(4) 0.0038(3) -0.0047(3) -0.0017(3)
C1 0.0201(6) 0.0127(5) 0.0167(5) 0.0000(4) -0.0034(4) 0.0005(4)
C2 0.0176(5) 0.0146(5) 0.0133(5) -0.0011(4) -0.0023(4) -0.0001(4)
C3 0.0199(6) 0.0158(6) 0.0156(5) -0.0017(4) -0.0033(4) 0.0002(5)
C4 0.0189(6) 0.0149(6) 0.0171(5) -0.0003(4) -0.0036(4) 0.0011(5)
C5 0.0221(6) 0.0287(7) 0.0203(6) -0.0008(5) -0.0071(5) 0.0005(6)
C6 0.0231(7) 0.0265(7) 0.0216(6) -0.0021(5) -0.0065(5) -0.0046(5)
C7 0.0165(5) 0.0166(6) 0.0136(5) 0.0010(4) -0.0005(4) -0.0006(4)
N1 0.0183(5) 0.0153(5) 0.0152(5) -0.0007(4) -0.0026(4) 0.0011(4)
C8 0.0182(6) 0.0187(6) 0.0142(5) 0.0018(4) -0.0012(4) 0.0014(5)
C9 0.0246(7) 0.0198(7) 0.0248(6) -0.0023(5) 0.0001(5) 0.0017(5)
C10 0.0277(7) 0.0276(8) 0.0307(7) -0.0022(6) 0.0048(6) 0.0057(6)
C11 0.0210(7) 0.0350(8) 0.0278(7) 0.0054(6) 0.0044(5) 0.0033(6)
C12 0.0227(7) 0.0273(8) 0.0319(7) 0.0033(6) 0.0001(5) -0.0048(6)
C13 0.0236(7) 0.0201(7) 0.0264(7) -0.0013(5) -0.0001(5) -0.0014(5)
_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
S1 C2 1.7554(12) . ?
S1 C1 1.7607(13) . ?
S2 C3 1.7333(13) . ?
S2 C1 1.7613(13) . ?
S3 C5 1.7513(15) . ?
S3 C4 1.7616(13) . ?
S4 C6 1.7434(15) . ?
S4 C4 1.7605(13) . ?
O1 C7 1.2710(15) . ?
O2 C7 1.2552(16) . ?
C1 C4 1.3503(17) . ?
C2 C3 1.3397(18) . ?
C2 C7 1.4863(16) . ?
C3 H3 0.920(17) . ?
C5 C6 1.328(2) . ?
C5 H5 0.930(19) . ?
C6 H6 0.92(2) . ?
N1 C8 1.4611(17) . ?
N1 H1A 0.939(18) . ?
N1 H1B 0.876(19) . ?
N1 H1C 0.89(2) . ?
C8 C13 1.3832(19) . ?
C8 C9 1.3862(19) . ?
C9 C10 1.390(2) . ?
C9 H9 0.942(18) . ?
C10 C11 1.383(2) . ?
C10 H10 0.98(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.904(19) . ?
C12 C13 1.392(2) . ?
C12 H12 0.89(2) . ?
C13 H13 0.961(18) . ?
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
C2 S1 C1 94.77(6) . . ?
C3 S2 C1 94.98(6) . . ?
C5 S3 C4 93.97(7) . . ?
C6 S4 C4 94.50(7) . . ?
C4 C1 S1 121.61(10) . . ?
C4 C1 S2 123.85(10) . . ?
S1 C1 S2 114.54(7) . . ?
C3 C2 C7 127.46(11) . . ?
C3 C2 S1 117.12(9) . . ?
C7 C2 S1 115.38(9) . . ?
C2 C3 S2 118.33(10) . . ?
C2 C3 H3 126.3(10) . . ?
S2 C3 H3 115.3(10) . . ?
C1 C4 S4 121.55(10) . . ?
C1 C4 S3 124.36(10) . . ?
S4 C4 S3 114.08(7) . . ?
C6 C5 S3 118.00(11) . . ?
C6 C5 H5 126.2(12) . . ?
S3 C5 H5 115.8(12) . . ?
C5 C6 S4 117.49(11) . . ?
C5 C6 H6 125.0(12) . . ?
S4 C6 H6 117.4(12) . . ?
O2 C7 O1 124.49(11) . . ?
O2 C7 C2 116.12(11) . . ?
O1 C7 C2 119.39(11) . . ?
C8 N1 H1A 109.6(10) . . ?
C8 N1 H1B 113.0(11) . . ?
H1A N1 H1B 110.5(16) . . ?
C8 N1 H1C 112.9(12) . . ?
H1A N1 H1C 104.0(16) . . ?
H1B N1 H1C 106.5(16) . . ?
C13 C8 C9 121.52(13) . . ?
C13 C8 N1 118.97(12) . . ?
C9 C8 N1 119.50(12) . . ?
C8 C9 C10 118.72(14) . . ?
C8 C9 H9 119.5(11) . . ?
C10 C9 H9 121.7(11) . . ?
C11 C10 C9 120.46(14) . . ?
C11 C10 H10 118.2(12) . . ?
C9 C10 H10 121.4(12) . . ?
C10 C11 C12 120.19(14) . . ?
C10 C11 H11 120.4(13) . . ?
C12 C11 H11 119.4(13) . . ?
C11 C12 C13 120.02(14) . . ?
C11 C12 H12 121.6(13) . . ?
C13 C12 H12 118.3(13) . . ?
C8 C13 C12 119.08(14) . . ?
C8 C13 H13 119.9(11) . . ?
C12 C13 H13 121.0(11) . . ?
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
C2 S1 C1 C4 174.32(12) . . . . ?
C2 S1 C1 S2 -5.04(8) . . . . ?
C3 S2 C1 C4 -174.63(12) . . . . ?
C3 S2 C1 S1 4.72(8) . . . . ?
C1 S1 C2 C3 3.57(11) . . . . ?
C1 S1 C2 C7 -178.40(10) . . . . ?
C7 C2 C3 S2 -178.59(10) . . . . ?
S1 C2 C3 S2 -0.84(15) . . . . ?
C1 S2 C3 C2 -2.38(12) . . . . ?
S1 C1 C4 S4 -0.52(17) . . . . ?
S2 C1 C4 S4 178.78(7) . . . . ?
S1 C1 C4 S3 -179.02(7) . . . . ?
S2 C1 C4 S3 0.28(18) . . . . ?
C6 S4 C4 C1 -165.12(12) . . . . ?
C6 S4 C4 S3 13.52(9) . . . . ?
C5 S3 C4 C1 165.07(13) . . . . ?
C5 S3 C4 S4 -13.53(9) . . . . ?
C4 S3 C5 C6 8.40(13) . . . . ?
S3 C5 C6 S4 -0.20(18) . . . . ?
C4 S4 C6 C5 -8.13(14) . . . . ?
C3 C2 C7 O2 -177.27(13) . . . . ?
S1 C2 C7 O2 4.94(15) . . . . ?
C3 C2 C7 O1 2.0(2) . . . . ?
S1 C2 C7 O1 -175.82(9) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
N1 C8 C9 C10 -179.50(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
N1 C8 C13 C12 179.81(12) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.939(18) 1.788(19) 2.7165(14) 169.5(17) .
N1 H1B O1 0.876(19) 1.868(19) 2.7346(15) 169.9(17) 2_455
N1 H1C O2 0.89(2) 1.81(2) 2.6895(14) 172.4(18) 2_445
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 31.05
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.437
_refine_diff_density_min -0.422
_refine_diff_density_rms 0.064
data_single_phase
_database_code_depnum_ccdc_archive 'CCDC 911426'
#TrackingRef 'CCDC911426.cif'
# 5. CHEMICAL DATA
_chemical_name_systematic
; Anilinium tetrathiafulvalene-2-carboxylate
;
_chemical_name_common 'Anilinium tetrathiafulvalene-2-carboxylate'
# Get _chemical_formula_moiety using checkCIF
_chemical_formula_moiety 'C6 H8 N, C7 H3 O2 S4'
_chemical_formula_structural ?
_chemical_formula_analytical 'C13 H11 N O2 S4'
_chemical_formula_sum 'C13 H11 N O2 S4'
_chemical_formula_weight 341.492
_chemical_melting_point ?
_chemical_compound_source ? # for minerals and
# natural products
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0120 0.0060 'International Tables for Crystallography, Vol. C'
H H 0.0000 0.0000 'International Tables for Crystallography, Vol. C'
N N 0.0210 0.0120 'International Tables for Crystallography, Vol. C'
O O 0.0340 0.0230 'International Tables for Crystallography, Vol. C'
S S 0.2690 0.4050 'International Tables for Crystallography, Vol. C'
#===============================================================================
# 6. POWDER SPECIMEN AND CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
_cell_length_a 8.9395(2)
_cell_length_b 6.3387(1)
_cell_length_c 26.9154(6)
_cell_angle_alpha 90
_cell_angle_beta 96.838(1)
_cell_angle_gamma 90
_cell_volume 1514.30(6)
# If checkCIF gives a different Z value, change both
# _chemical_formula_sum and _chemical_formula_weight.
_cell_formula_units_Z 4
_cell_measurement_temperature 300
_cell_special_details ?
_exptl_crystal_density_diffrn 1.4979
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 704.00
# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.
_pd_spec_size_axial ? # perpendicular to
# equatorial plane
_pd_spec_size_equat ? # parallel to
# scattering vector
# in transmission
_pd_spec_size_thick ? # parallel to
# scattering vector
# in reflection
# The next five fields are character fields that describe the specimen.
_pd_spec_mounting
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode transmission
_pd_spec_shape cylinder
_pd_char_particle_morphology ?
_pd_char_colour orange
# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min. The pressure at which the sample was
# prepared is in kPa. The temperature of preparation is in K.
_pd_prep_cool_rate ?
_pd_prep_pressure ?
_pd_prep_temperature ?
_exptl_absorpt_coefficient_mu ?
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_correction_type ? # include if applicable
_exptl_absorpt_process_details ? # include if applicable
_exptl_absorpt_correction_T_min ? # include if applicable
_exptl_absorpt_correction_T_max ? # include if applicable
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
; ?
;
# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.
_pd_instr_location
; ?
;
_pd_calibration_special_details
# description of the method used
# to calibrate the instrument
; ?
;
_diffrn_ambient_temperature 300
_diffrn_source synchrotron
_diffrn_source_target ?
_diffrn_source_type 'BL02B2 SPring-8'
_diffrn_measurement_device_type 'large Debye-Scherrer camera'
_diffrn_detector 'imaging plate'
_diffrn_detector_type ?
_pd_meas_scan_method step # options are 'step', 'cont',
#' 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details
; ?
;
_diffrn_radiation_wavelength 1.303800
_diffrn_radiation_monochromator Si(111)
# The following four items give details of the measured (not processed)
# powder pattern. Angles are in degrees.
_pd_meas_number_of_points 7898
_pd_meas_2theta_range_min 0.0100
_pd_meas_2theta_range_max 78.9800
_pd_meas_2theta_range_inc 0.0100
# The following three items are used for time-of-flight measurements only.
_pd_instr_dist_src/spec ?
_pd_instr_dist_spec/detc ?
_pd_meas_2theta_fixed ?
#===============================================================================
# 8. REFINEMENT DATA
# Use the next field to give any special details about the fitting of the
# powder pattern.
_pd_proc_ls_special_details
; ?
;
# The next three items are given as text.
_pd_calc_method 'Rietveld Refinement'
_pd_proc_ls_profile_function 'split pseudo-Voigt function'
_pd_proc_ls_background_function 'Legendre polynomials'
_pd_proc_ls_pref_orient_corr
; ?
;
# Replace '; ?' with the following four lines for the March-Dollase function:
#; $P_k = \sum_{j=1}^{m_k} \frac{1}{m_k}
#\left( r^2 \cos^2 \alpha_j +r^{-1}\ sin^2 \alpha_j \right)^{-3/2}$
#with a preferred-orientation vector, (hkl),
#and r = 1.0(0)
_pd_proc_ls_prof_R_factor 0.03722
_pd_proc_ls_prof_wR_factor 0.05045
_pd_proc_ls_prof_wR_expected 0.02496
_refine_ls_R_I_factor 0.05539
_refine_ls_R_Fsqd_factor 0.05248
_refine_ls_R_factor_all 0.05219
_refine_special_details
; ?
;
_refine_ls_matrix_type full
_refine_ls_weighting_scheme sigma
_refine_ls_weighting_details 1/y~i~
# The following line must be commented out in the absence of H atoms.
_refine_ls_hydrogen_treatment ?
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_parameters 132
_refine_ls_number_restraints 0
_refine_ls_number_constraints 26
# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all 2.0215
_refine_ls_restrained_S_all ?
# The following item can be obtained by setting NPRINT at 2 in *.ins.
_refine_ls_shift/su_max 0.0
_refine_ls_shift/su_mean 0.0
# _refine_diff_density_max 0.0
# _refine_diff_density_min 0.0
# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.
_pd_proc_2theta_range_min 4.0100
_pd_proc_2theta_range_max 75.0000
_pd_proc_2theta_range_inc 0.0100
_pd_proc_wavelength ?
# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting
# of one data block containing a single powder profile. The value of
# _pd_block_diffractogram_id is used to associate each refinement with
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.
_pd_block_diffractogram_id ?
# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions ?
_pd_proc_info_data_reduction ?
# The following items are used to identify the programs used.
_computing_data_collection ?
_computing_cell_refinement 'RIETAN-FP (Izumi and Momma, 2007)'
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'RIETAN-FP (Izumi and Momma, 2007)'
_computing_molecular_graphics 'VESTA (Momma and Izumi, 2008)'
_computing_publication_material ?
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_type_symbol
S1 0.0657(8) 0.706(1) 0.4299(3) 1 4 e Uiso 0.058(1) S
S2 0.1037(8) 0.251(1) 0.4572(3) 1 4 e Uiso 0.058(1) S
S3 0.3561(7) 0.378(1) 0.5495(3) 1 4 e Uiso 0.058(1) S
S4 0.3122(8) 0.831(1) 0.5195(3) 1 4 e Uiso 0.058(1) S
O1 -0.187(2) 0.474(2) 0.3117(6) 1 4 e Uiso 0.068(5) O
O2 -0.109(1) 0.794(2) 0.3396(6) 1 4 e Uiso 0.068(5) O
C1 0.162(2) 0.514(4) 0.4692(8) 1 4 e Uiso 0.055(7) C
C2 -0.023(3) 0.520(5) 0.388(1) 1 4 e Uiso 0.118(6) C
C3 -0.004(3) 0.313(4) 0.401(1) 1 4 e Uiso 0.118(6) C
C4 0.265(2) 0.567(4) 0.5065(8) 1 4 e Uiso 0.055(7) C
C5 0.466(3) 0.564(4) 0.583(1) 1 4 e Uiso 0.118(6) C
C6 0.447(3) 0.769(4) 0.570(1) 1 4 e Uiso 0.118(6) C
C7 -0.119(3) 0.591(5) 0.347(1) 1 4 e Uiso 0.118(6) C
N1 -0.183(2) 0.591(3) 0.2115(8) 1 4 e Uiso 0.086(4) N
C8 -0.036(3) 0.580(6) 0.199(1) 1 4 e Uiso 0.086(4) C
C9 0.023(3) 0.387(5) 0.182(1) 1 4 e Uiso 0.086(4) C
C10 0.170(4) 0.381(4) 0.169(1) 1 4 e Uiso 0.086(4) C
C11 0.262(3) 0.560(6) 0.177(1) 1 4 e Uiso 0.086(4) C
C12 0.210(3) 0.741(4) 0.1967(9) 1 4 e Uiso 0.086(4) C
C13 0.063(4) 0.753(4) 0.210(1) 1 4 e Uiso 0.086(4) C
H3 -0.05014 0.20451 0.37988 1 4 e Uiso 0.142(6) H
H5 0.53927 0.52394 0.61065 1 4 e Uiso 0.142(6) H
H6 0.50596 0.87862 0.58727 1 4 e Uiso 0.142(6) H
H1A -0.19447 0.50178 0.23644 1 4 e Uiso 0.129(4) H
H1B -0.20398 0.72358 0.22046 1 4 e Uiso 0.129(4) H
H1C -0.24933 0.55497 0.1843 1 4 e Uiso 0.129(4) H
H9 -0.03762 0.26153 0.17984 1 4 e Uiso 0.103(4) H
H10 0.20984 0.25397 0.15711 1 4 e Uiso 0.103(4) H
H11 0.36484 0.55569 0.16919 1 4 e Uiso 0.103(4) H
H12 0.27424 0.86374 0.20168 1 4 e Uiso 0.103(4) H
H13 0.02775 0.87783 0.22533 1 4 e Uiso 0.103(4) H
#===============================================================================
#10. GEOMETRICAL PARAMETERS
_geom_special_details ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.75(3) . 1_555 ?
S1 C1 1.77(2) . 1_555 ?
S2 C3 1.73(3) . 1_555 ?
S2 C1 1.77(2) . 1_555 ?
S3 C5 1.72(2) . 1_555 ?
S3 C4 1.79(2) . 1_555 ?
S4 C6 1.74(2) . 1_555 ?
S4 C4 1.75(2) . 1_555 ?
O1 C7 1.30(3) . 1_555 ?
O2 C7 1.31(3) . 1_555 ?
C1 C4 1.32(2) . 1_555 ?
C1 S2 1.77(2) . 1_555 ?
C1 S1 1.77(2) . 1_555 ?
C2 C3 1.36(3) . 1_555 ?
C2 C7 1.39(4) . 1_555 ?
C2 S1 1.75(3) . 1_555 ?
C3 H3 0.96(3) . 1_555 ?
C3 C2 1.36(3) . 1_555 ?
C3 S2 1.73(3) . 1_555 ?
C4 C1 1.32(2) . 1_555 ?
C4 S4 1.75(2) . 1_555 ?
C4 S3 1.79(2) . 1_555 ?
C5 H5 0.96(3) . 1_555 ?
C5 C6 1.35(3) . 1_555 ?
C5 S3 1.72(2) . 1_555 ?
C6 H6 0.96(2) . 1_555 ?
C6 C5 1.35(3) . 1_555 ?
C6 S4 1.74(2) . 1_555 ?
C7 O1 1.30(3) . 1_555 ?
C7 O2 1.31(3) . 1_555 ?
C7 C2 1.39(4) . 1_555 ?
N1 H1A 0.89(2) . 1_555 ?
N1 H1B 0.90(2) . 1_555 ?
N1 H1C 0.92(2) . 1_555 ?
N1 C8 1.40(2) . 1_555 ?
C8 N1 1.40(2) . 1_555 ?
C8 C13 1.42(2) . 1_555 ?
C8 C9 1.42(3) . 1_555 ?
C9 H9 0.96(2) . 1_555 ?
C9 C10 1.40(3) . 1_555 ?
C9 C8 1.42(3) . 1_555 ?
C10 H10 0.96(2) . 1_555 ?
C10 C11 1.40(2) . 1_555 ?
C10 C9 1.40(3) . 1_555 ?
C11 H11 0.97(2) . 1_555 ?
C11 C12 1.37(3) . 1_555 ?
C11 C10 1.40(2) . 1_555 ?
C12 H12 0.97(2) . 1_555 ?
C12 C11 1.37(3) . 1_555 ?
C12 C13 1.40(3) . 1_555 ?
C13 H13 0.96(2) . 1_555 ?
C13 C12 1.40(3) . 1_555 ?
C13 C8 1.42(2) . 1_555 ?
H3 C3 0.96(3) . 1_555 ?
H5 C5 0.96(3) . 1_555 ?
H6 C6 0.96(2) . 1_555 ?
H1A N1 0.89(2) . 1_555 ?
H1B N1 0.90(2) . 1_555 ?
H1C N1 0.92(2) . 1_555 ?
H9 C9 0.96(2) . 1_555 ?
H10 C10 0.96(2) . 1_555 ?
H11 C11 0.97(2) . 1_555 ?
H12 C12 0.97(2) . 1_555 ?
H13 C13 0.96(2) . 1_555 ?
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 94(1) 1_555 . 1_555 ?
C3 S2 C1 94(1) 1_555 . 1_555 ?
C5 S3 C4 94(1) 1_555 . 1_555 ?
C6 S4 C4 94(1) 1_555 . 1_555 ?
C4 C1 S2 123(2) 1_555 . 1_555 ?
C4 C1 S1 122(2) 1_555 . 1_555 ?
S2 C1 S1 115(1) 1_555 . 1_555 ?
C3 C2 C7 124(4) 1_555 . 1_555 ?
C3 C2 S1 117(2) 1_555 . 1_555 ?
C7 C2 S1 119(3) 1_555 . 1_555 ?
H3 C3 C2 121(4) 1_555 . 1_555 ?
H3 C3 S2 121(3) 1_555 . 1_555 ?
C2 C3 S2 119(3) 1_555 . 1_555 ?
C1 C4 S4 122(2) 1_555 . 1_555 ?
C1 C4 S3 123(2) 1_555 . 1_555 ?
S4 C4 S3 116(1) 1_555 . 1_555 ?
H5 C5 C6 121(3) 1_555 . 1_555 ?
H5 C5 S3 121(2) 1_555 . 1_555 ?
C6 C5 S3 118(2) 1_555 . 1_555 ?
H6 C6 C5 121(3) 1_555 . 1_555 ?
H6 C6 S4 121(2) 1_555 . 1_555 ?
C5 C6 S4 119(2) 1_555 . 1_555 ?
O1 C7 O2 119(3) 1_555 . 1_555 ?
O1 C7 C2 126(3) 1_555 . 1_555 ?
O2 C7 C2 113(3) 1_555 . 1_555 ?
H1A N1 H1B 110(2) 1_555 . 1_555 ?
H1A N1 H1C 109(2) 1_555 . 1_555 ?
H1A N1 C8 111(2) 1_555 . 1_555 ?
H1B N1 H1C 108(2) 1_555 . 1_555 ?
H1B N1 C8 110(3) 1_555 . 1_555 ?
H1C N1 C8 109(2) 1_555 . 1_555 ?
N1 C8 C13 119(4) 1_555 . 1_555 ?
N1 C8 C9 121(4) 1_555 . 1_555 ?
C13 C8 C9 119(3) 1_555 . 1_555 ?
C13 C8 H1C 134(3) 1_555 . 1_555 ?
C13 C8 H1A 125(3) 1_555 . 1_555 ?
C13 C8 H1B 93(3) 1_555 . 1_555 ?
C9 C8 H1C 105(3) 1_555 . 1_555 ?
C9 C8 H1A 105(3) 1_555 . 1_555 ?
C9 C8 H1B 147(3) 1_555 . 1_555 ?
H9 C9 C10 120(4) 1_555 . 1_555 ?
H9 C9 C8 121(4) 1_555 . 1_555 ?
C10 C9 C8 119(2) 1_555 . 1_555 ?
H10 C10 C11 120(4) 1_555 . 1_555 ?
H10 C10 C9 120(4) 1_555 . 1_555 ?
C11 C10 C9 120(2) 1_555 . 1_555 ?
H11 C11 C12 119(4) 1_555 . 1_555 ?
H11 C11 C10 120(4) 1_555 . 1_555 ?
C12 C11 C10 121(2) 1_555 . 1_555 ?
H12 C12 C11 120(4) 1_555 . 1_555 ?
H12 C12 C13 119(4) 1_555 . 1_555 ?
C11 C12 C13 121(2) 1_555 . 1_555 ?
H13 C13 C12 121(4) 1_555 . 1_555 ?
H13 C13 C8 120(4) 1_555 . 1_555 ?
C12 C13 C8 119(3) 1_555 . 1_555 ?