Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006
data_global
_journal_name_full CrystEngComm
#===============================================================================
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
_journal_coden_Cambridge 1350
#==============================================================================
#===============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name 'Neil Winterton'
_publ_contact_author_address
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
_publ_contact_author_email n.winterton@liv.ac.uk
_publ_contact_author_fax +441517943583
_publ_contact_author_phone +441517943585
# Publication choise FI, CI or EI for Inorganic
# FM, CM or EM for Metal-organic
# FO, CO or EO for Organic
_publ_requested_category ?
_publ_requested_coeditor_name ?
_publ_contact_letter # Include date of submission
;
Date of submission ?
Please consider this CIF submission for publication as a
Regular Structural Paper in CRYSTENGCOMM.
;
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
#===============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
In situ crystallization of ionic liquids with melting points <-25 \%C
;
_publ_section_title_footnote
; ?
;
# The loop structure below should contain the names and adresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
#_publ_author_footnote
_publ_author_address
A.R.Choudhury
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
N.Winterton
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
A.Steiner
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
A.I.Cooper
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
K.A.Johnson
;
Liverpool Centre for Materials and Catalysis, Department of Chemistry,
University of Liverpool, Liverpool. L69 7ZD
;
#===============================================================================
# 4. TEXT
_publ_section_synopsis
;
?
;
_publ_section_abstract
;
?
;
# Insert blank lines between paragraphs
_publ_section_comment
; ?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
?
;
# Insert blank lines between references
_publ_section_references
;
?
;
_publ_section_acknowledgements
; ?
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
#===============================================================================
data_[emim]NTf2
_database_code_depnum_ccdc_archive 'CCDC 614037'
# 0. AUDIT DETAILS
_audit_creation_date 'Aug 04 13:39:26 2006'
_audit_creation_method 'PLATON
option'
_audit_update_record
; ?
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonlyl)imide
;
_chemical_name_common
;1-ethyl-3-methylimidazolium
bis(trifluoromethanesulfonlyl)imide
;
_chemical_melting_point 247.3
_chemical_formula_moiety 'C6 H11 N2, C2 F6 N O4 S2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C8 H11 F6 N3 O4 S2'
_chemical_formula_iupac ?
_chemical_formula_weight 391.34
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2ac'
_symmetry_space_group_name_H-M 'P c a 21'
_symmetry_Int_Tables_number 29
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+x,-y,z
_cell_length_a 18.499(9)
_cell_length_b 8.626(8)
_cell_length_c 19.255(9)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3073(4)
_cell_formula_units_Z 8
_cell_measurement_temperature 230
_cell_measurement_reflns_used 755
_cell_measurement_theta_min 2.61
_cell_measurement_theta_max 18.14
_cell_special_details
; ?
;
_exptl_crystal_description Rod
_exptl_crystal_colour Colorless
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.3
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.692
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1584
_exptl_absorpt_coefficient_mu 0.432
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type None
# Example: '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 230.0(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_type 'Bruker SMART CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
# number of measured reflections (redundant set)
_diffrn_reflns_number 25029
_diffrn_reflns_av_R_equivalents 0.1722
_diffrn_reflns_av_sigmaI/netI 0.1271
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.12
_diffrn_reflns_theta_max 25.35
_reflns_number_total 2947
_reflns_number_gt 1439
_reflns_threshold_expression >2sigma(I)
_diffrn_measured_fraction_theta_max 0.768
_diffrn_reflns_theta_full 25.35
_diffrn_measured_fraction_theta_full 0.768
_computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution 'SIR92 (Altomare, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
Ortep-32 for Windows (Farrugia, 1997), POV-Ray^TM^ for Windows
Version 3.6 (The POV-Ray Team, 2004) and CAMERON (Watkin et. al., 1993)
;
_computing_publication_material 'PLATON (Spek, 1990)'
#===============================================================================
# 8. REFINEMENT DATA
_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^)+(0.1293P)^2^+0.0000P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.5(3)
_refine_ls_number_reflns 2947
_refine_ls_number_parameters 413
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1465
_refine_ls_R_factor_gt 0.0823
_refine_ls_wR_factor_ref 0.2225
_refine_ls_wR_factor_gt 0.1936
_refine_ls_goodness_of_fit_ref 0.948
_refine_ls_restrained_S_all 0.948
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.411
_refine_diff_density_min -0.352
_refine_diff_density_rms 0.105
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.7828(3) -0.0827(4) -0.2483(2) 0.0452(14) Uani 1 1 d . . .
S2 S 0.7275(4) 0.2157(5) -0.2720(3) 0.0527(17) Uani 1 1 d . . .
F1 F 0.7987(15) -0.0187(16) -0.1165(6) 0.165(11) Uani 1 1 d . . .
F2 F 0.7182(10) -0.1824(18) -0.1366(7) 0.113(6) Uani 1 1 d . . .
F3 F 0.8278(9) -0.2473(14) -0.1451(7) 0.102(5) Uani 1 1 d . . .
F4 F 0.7040(10) 0.2728(14) -0.1425(7) 0.108(5) Uani 1 1 d . . .
F5 F 0.8131(10) 0.2953(15) -0.1733(7) 0.088(5) Uani 1 1 d . . .
F6 F 0.7385(9) 0.4649(13) -0.2007(9) 0.121(6) Uani 1 1 d . . .
O1 O 0.7620(9) -0.2211(12) -0.2818(7) 0.061(4) Uani 1 1 d . . .
O2 O 0.8521(11) -0.0235(14) -0.2615(7) 0.069(5) Uani 1 1 d . . .
O3 O 0.7866(9) 0.2531(12) -0.3159(7) 0.068(4) Uani 1 1 d . . .
O4 O 0.6578(9) 0.2691(12) -0.2903(8) 0.077(4) Uani 1 1 d . . .
N1 N 0.7301(11) -0.2964(16) -0.4390(6) 0.052(4) Uani 1 1 d . . .
N3 N 0.7822(12) -0.0759(15) -0.4448(7) 0.055(5) Uani 1 1 d . . .
N11 N 1.0213(9) 0.1967(13) -0.2839(7) 0.046(3) Uani 1 1 d . . .
C2 C 0.7932(11) -0.2285(16) -0.4423(8) 0.041(5) Uani 1 1 d . . .
H2 H 0.8379 -0.2780 -0.4429 0.050 Uiso 1 1 calc R . .
C4 C 0.7069(13) -0.054(2) -0.4445(8) 0.050(5) Uani 1 1 d . . .
H4 H 0.6827 0.0410 -0.4448 0.060 Uiso 1 1 calc R . .
C5 C 0.6773(13) -0.191(3) -0.4435(9) 0.066(6) Uani 1 1 d . . .
H5 H 0.6280 -0.2120 -0.4456 0.079 Uiso 1 1 calc R . .
C6 C 0.7218(13) -0.467(2) -0.4350(11) 0.060(6) Uani 1 1 d . . .
H6A H 0.6766 -0.4923 -0.4120 0.073 Uiso 1 1 calc R . .
H6B H 0.7609 -0.5105 -0.4075 0.073 Uiso 1 1 calc R . .
C7 C 0.7227(14) -0.543(2) -0.5101(11) 0.080(8) Uani 1 1 d . . .
H7A H 0.6879 -0.4921 -0.5391 0.120 Uiso 1 1 calc R . .
H7B H 0.7107 -0.6514 -0.5066 0.120 Uiso 1 1 calc R . .
H7C H 0.7699 -0.5326 -0.5301 0.120 Uiso 1 1 calc R . .
C8 C 0.8378(12) 0.039(2) -0.4574(13) 0.084(8) Uani 1 1 d . . .
H8A H 0.8845 -0.0088 -0.4553 0.126 Uiso 1 1 calc R . .
H8B H 0.8348 0.1191 -0.4227 0.126 Uiso 1 1 calc R . .
H8C H 0.8309 0.0844 -0.5025 0.126 Uiso 1 1 calc R . .
C9 C 0.7835(15) -0.132(3) -0.1615(11) 0.091(9) Uani 1 1 d . . .
C10 C 0.7474(17) 0.315(2) -0.1902(11) 0.078(8) Uani 1 1 d . . .
S3 S 0.9734(3) 0.2814(5) 0.0379(3) 0.0540(17) Uani 1 1 d . . .
S4 S 1.0279(3) 0.5830(4) 0.0237(2) 0.0479(15) Uani 1 1 d . . .
F7 F 0.9870(10) 0.0382(13) -0.0419(8) 0.120(6) Uani 1 1 d . . .
F8 F 1.0588(11) 0.2202(15) -0.0659(7) 0.109(6) Uani 1 1 d . . .
F9 F 0.9523(9) 0.2462(13) -0.0979(7) 0.103(5) Uani 1 1 d . . .
F10 F 1.0498(10) 0.5331(15) -0.1076(6) 0.107(6) Uani 1 1 d . . .
F11 F 0.9643(10) 0.6955(18) -0.0886(7) 0.113(5) Uani 1 1 d . . .
F12 F 1.0711(8) 0.7627(12) -0.0750(6) 0.085(4) Uani 1 1 d . . .
O5 O 1.0320(8) 0.2370(12) 0.0806(7) 0.058(4) Uani 1 1 d . . .
O6 O 0.9045(8) 0.2235(12) 0.0548(8) 0.078(5) Uani 1 1 d . . .
O7 O 1.1003(9) 0.5307(15) 0.0367(10) 0.081(5) Uani 1 1 d . . .
O8 O 1.0031(9) 0.7204(14) 0.0588(7) 0.064(4) Uani 1 1 d . . .
N13 N 0.9731(10) 0.4252(14) -0.2777(7) 0.046(3) Uani 1 1 d . . .
N14 N 0.7204(9) 0.0393(18) -0.2545(8) 0.050(5) Uani 1 1 d . . .
N15 N 0.9655(8) 0.4597(16) 0.0213(8) 0.044(4) Uani 1 1 d . . .
C12 C 0.9618(12) 0.2714(19) -0.2856(8) 0.054(5) Uani 1 1 d . . .
H12 H 0.9166 0.2260 -0.2914 0.065 Uiso 1 1 calc R . .
C14 C 1.0457(14) 0.442(2) -0.2750(10) 0.069(6) Uani 1 1 d . . .
H14 H 1.0705 0.5346 -0.2696 0.083 Uiso 1 1 calc R . .
C15 C 1.0751(12) 0.3031(19) -0.2812(9) 0.062(6) Uani 1 1 d . . .
H15 H 1.1244 0.2821 -0.2833 0.074 Uiso 1 1 calc R . .
C16 C 1.0305(14) 0.0279(18) -0.2875(14) 0.063(7) Uani 1 1 d . . .
H16A H 0.9927 -0.0154 -0.3165 0.075 Uiso 1 1 calc R . .
H16B H 1.0765 0.0048 -0.3093 0.075 Uiso 1 1 calc R . .
C17 C 1.0281(12) -0.046(2) -0.2199(12) 0.071(7) Uani 1 1 d . . .
H17A H 1.0752 -0.0428 -0.1991 0.107 Uiso 1 1 calc R . .
H17B H 1.0130 -0.1518 -0.2251 0.107 Uiso 1 1 calc R . .
H17C H 0.9943 0.0079 -0.1907 0.107 Uiso 1 1 calc R . .
C18 C 0.9198(13) 0.543(2) -0.2783(10) 0.075(8) Uani 1 1 d . . .
H18A H 0.9190 0.5943 -0.2341 0.113 Uiso 1 1 calc R . .
H18B H 0.8733 0.4980 -0.2874 0.113 Uiso 1 1 calc R . .
H18C H 0.9310 0.6172 -0.3140 0.113 Uiso 1 1 calc R . .
C19 C 0.9908(14) 0.194(2) -0.0442(11) 0.063(6) Uani 1 1 d . . .
C20 C 1.0249(14) 0.6405(18) -0.0678(10) 0.071(7) Uani 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 0.054(5) 0.035(2) 0.047(2) 0.0016(17) 0.001(2) -0.005(2)
S2 0.055(5) 0.035(2) 0.068(3) 0.003(2) -0.006(3) 0.000(3)
F1 0.37(3) 0.100(9) 0.029(7) -0.008(6) -0.035(11) 0.037(13)
F2 0.123(16) 0.133(12) 0.084(10) 0.061(9) 0.035(9) 0.016(10)
F3 0.103(13) 0.102(10) 0.102(11) 0.017(7) -0.026(8) 0.035(8)
F4 0.152(16) 0.085(8) 0.087(10) -0.033(7) 0.039(9) -0.014(9)
F5 0.100(15) 0.081(8) 0.084(9) -0.011(6) -0.024(9) -0.011(8)
F6 0.171(15) 0.041(5) 0.151(13) -0.040(8) -0.004(11) -0.006(8)
O1 0.077(13) 0.040(6) 0.066(9) -0.012(6) -0.011(8) 0.006(7)
O2 0.079(15) 0.048(7) 0.080(10) -0.006(6) 0.003(9) -0.027(8)
O3 0.091(14) 0.041(6) 0.072(9) 0.015(6) 0.022(8) 0.005(6)
O4 0.076(13) 0.045(6) 0.111(11) 0.010(7) -0.020(9) 0.006(7)
N1 0.069(16) 0.060(8) 0.027(7) 0.003(6) 0.013(7) -0.006(9)
N3 0.067(17) 0.057(9) 0.041(8) 0.001(6) 0.035(8) 0.016(9)
N11 0.037(10) 0.037(5) 0.064(6) 0.006(5) -0.007(6) -0.008(5)
C2 0.033(16) 0.034(8) 0.057(10) -0.012(7) 0.011(8) 0.009(9)
C4 0.05(2) 0.056(11) 0.043(10) -0.004(8) 0.020(9) 0.003(11)
C5 0.037(18) 0.104(16) 0.056(11) -0.011(10) -0.016(10) 0.031(14)
C6 0.057(18) 0.061(9) 0.063(13) 0.017(10) -0.005(11) -0.009(11)
C7 0.11(2) 0.063(11) 0.066(13) -0.028(11) 0.033(12) -0.038(13)
C8 0.07(2) 0.047(9) 0.14(2) 0.018(12) -0.018(15) -0.001(12)
C9 0.12(3) 0.101(15) 0.053(13) -0.050(12) -0.039(15) 0.061(17)
C10 0.12(3) 0.053(12) 0.061(13) 0.029(9) 0.012(16) 0.022(13)
S3 0.044(5) 0.039(2) 0.079(3) 0.004(2) -0.008(3) -0.003(2)
S4 0.058(5) 0.037(2) 0.049(2) -0.0011(18) 0.004(3) -0.008(2)
F7 0.180(18) 0.046(6) 0.133(13) -0.016(8) 0.000(10) -0.012(9)
F8 0.164(19) 0.076(8) 0.088(9) -0.019(6) 0.036(11) 0.034(10)
F9 0.122(14) 0.084(8) 0.101(10) -0.027(7) -0.047(9) 0.010(8)
F10 0.181(17) 0.079(7) 0.060(8) -0.019(6) 0.048(9) -0.008(8)
F11 0.111(15) 0.131(11) 0.098(10) 0.043(9) -0.053(10) -0.008(10)
F12 0.117(13) 0.055(6) 0.082(8) 0.028(5) 0.036(8) 0.004(6)
O5 0.039(12) 0.045(6) 0.088(10) 0.013(6) -0.010(8) -0.013(6)
O6 0.028(11) 0.043(6) 0.164(14) -0.002(7) 0.025(9) -0.016(6)
O7 0.032(13) 0.062(7) 0.147(15) 0.022(8) -0.043(11) -0.011(7)
O8 0.079(13) 0.049(7) 0.063(9) -0.011(6) 0.015(7) 0.023(8)
N13 0.037(10) 0.037(5) 0.064(6) 0.006(5) -0.007(6) -0.008(5)
N14 0.043(14) 0.052(7) 0.056(9) -0.011(8) -0.001(8) 0.004(9)
N15 0.035(13) 0.051(7) 0.046(8) 0.000(7) 0.007(7) 0.004(8)
C12 0.051(17) 0.068(11) 0.045(10) -0.003(8) -0.011(9) 0.014(10)
C14 0.09(2) 0.049(11) 0.072(12) -0.002(10) -0.001(12) -0.032(12)
C15 0.069(19) 0.057(11) 0.059(11) -0.007(9) 0.005(11) -0.003(10)
C16 0.045(18) 0.041(8) 0.101(18) -0.002(11) 0.019(12) 0.015(9)
C17 0.055(19) 0.057(10) 0.101(17) 0.008(12) -0.032(12) -0.003(11)
C18 0.09(2) 0.071(11) 0.069(12) 0.035(11) 0.064(13) 0.039(14)
C19 0.05(2) 0.077(14) 0.064(13) -0.010(11) 0.003(13) -0.009(11)
C20 0.13(2) 0.031(8) 0.055(12) -0.002(8) 0.011(12) 0.013(11)
_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 O2 1.402(18) . ?
S1 O1 1.411(12) . ?
S1 N14 1.567(17) . ?
S1 C9 1.72(2) . ?
S2 O4 1.413(15) . ?
S2 O3 1.420(14) . ?
S2 N14 1.564(16) . ?
S2 C10 1.83(2) . ?
F1 C9 1.33(2) . ?
F2 C9 1.37(3) . ?
F3 C9 1.33(2) . ?
F4 C10 1.27(3) . ?
F5 C10 1.27(3) . ?
F6 C10 1.32(2) . ?
N1 C2 1.31(2) . ?
N1 C5 1.34(2) . ?
N1 C6 1.49(2) . ?
N3 C2 1.333(19) . ?
N3 C4 1.41(2) . ?
N3 C8 1.45(3) . ?
N11 C12 1.28(2) . ?
N11 C15 1.36(2) . ?
N11 C16 1.47(2) . ?
C2 H2 0.9300 . ?
C4 C5 1.31(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.59(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
S3 O6 1.407(14) . ?
S3 O5 1.413(14) . ?
S3 N15 1.578(15) . ?
S3 C19 1.78(2) . ?
S4 O7 1.436(16) . ?
S4 O8 1.440(12) . ?
S4 N15 1.570(15) . ?
S4 C20 1.830(19) . ?
F7 C19 1.35(2) . ?
F8 C19 1.34(2) . ?
F9 C19 1.33(2) . ?
F10 C20 1.288(19) . ?
F11 C20 1.28(3) . ?
F12 C20 1.36(2) . ?
N13 C12 1.35(2) . ?
N13 C14 1.35(2) . ?
N13 C18 1.42(2) . ?
C12 H12 0.9300 . ?
C14 C15 1.32(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.45(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
O2 S1 O1 118.4(9) . . ?
O2 S1 N14 114.5(9) . . ?
O1 S1 N14 109.4(9) . . ?
O2 S1 C9 105.0(12) . . ?
O1 S1 C9 103.8(10) . . ?
N14 S1 C9 104.1(9) . . ?
O4 S2 O3 118.7(9) . . ?
O4 S2 N14 107.1(9) . . ?
O3 S2 N14 114.5(8) . . ?
O4 S2 C10 104.2(11) . . ?
O3 S2 C10 104.5(11) . . ?
N14 S2 C10 106.6(8) . . ?
C2 N1 C5 110.2(17) . . ?
C2 N1 C6 122.6(17) . . ?
C5 N1 C6 127(2) . . ?
C2 N3 C4 106.6(17) . . ?
C2 N3 C8 125(2) . . ?
C4 N3 C8 127.5(16) . . ?
C12 N11 C15 107.0(16) . . ?
C12 N11 C16 126.8(17) . . ?
C15 N11 C16 126.1(17) . . ?
N1 C2 N3 107.9(17) . . ?
N1 C2 H2 126.0 . . ?
N3 C2 H2 126.0 . . ?
C5 C4 N3 106.9(19) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N1 108(2) . . ?
C4 C5 H5 125.9 . . ?
N1 C5 H5 125.9 . . ?
N1 C6 C7 111.1(15) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F3 C9 F1 105.2(17) . . ?
F3 C9 F2 103(2) . . ?
F1 C9 F2 101(2) . . ?
F3 C9 S1 114.8(16) . . ?
F1 C9 S1 117(2) . . ?
F2 C9 S1 114.3(15) . . ?
F5 C10 F4 112(2) . . ?
F5 C10 F6 107(2) . . ?
F4 C10 F6 108(2) . . ?
F5 C10 S2 110.5(16) . . ?
F4 C10 S2 111(2) . . ?
F6 C10 S2 107.5(14) . . ?
O6 S3 O5 117.7(9) . . ?
O6 S3 N15 108.0(8) . . ?
O5 S3 N15 116.9(8) . . ?
O6 S3 C19 102.6(10) . . ?
O5 S3 C19 105.2(11) . . ?
N15 S3 C19 104.4(9) . . ?
O7 S4 O8 118.3(10) . . ?
O7 S4 N15 118.6(8) . . ?
O8 S4 N15 109.7(10) . . ?
O7 S4 C20 106.3(11) . . ?
O8 S4 C20 102.7(8) . . ?
N15 S4 C20 97.7(9) . . ?
C12 N13 C14 105.1(15) . . ?
C12 N13 C18 127(2) . . ?
C14 N13 C18 128.1(18) . . ?
S2 N14 S1 127.5(12) . . ?
S4 N15 S3 125.9(11) . . ?
N11 C12 N13 111.1(18) . . ?
N11 C12 H12 124.4 . . ?
N13 C12 H12 124.4 . . ?
C15 C14 N13 108.2(17) . . ?
C15 C14 H14 125.9 . . ?
N13 C14 H14 125.9 . . ?
C14 C15 N11 108(2) . . ?
C14 C15 H15 125.9 . . ?
N11 C15 H15 125.9 . . ?
C17 C16 N11 112.9(19) . . ?
C17 C16 H16A 109.0 . . ?
N11 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
N11 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N13 C18 H18A 109.5 . . ?
N13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F9 C19 F8 101.7(19) . . ?
F9 C19 F7 109.7(18) . . ?
F8 C19 F7 103.1(19) . . ?
F9 C19 S3 116.6(17) . . ?
F8 C19 S3 111.9(15) . . ?
F7 C19 S3 112.5(15) . . ?
F11 C20 F10 113(2) . . ?
F11 C20 F12 103.3(15) . . ?
F10 C20 F12 105.8(18) . . ?
F11 C20 S4 115.3(16) . . ?
F10 C20 S4 111.6(13) . . ?
F12 C20 S4 106.8(14) . . ?
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
C5 N1 C2 N3 3.8(17) . . . . ?
C6 N1 C2 N3 -179.4(15) . . . . ?
C4 N3 C2 N1 -1.4(17) . . . . ?
C8 N3 C2 N1 -171.9(16) . . . . ?
C2 N3 C4 C5 -1.4(18) . . . . ?
C8 N3 C4 C5 168.7(18) . . . . ?
N3 C4 C5 N1 3.6(18) . . . . ?
C2 N1 C5 C4 -4.7(18) . . . . ?
C6 N1 C5 C4 178.6(16) . . . . ?
C2 N1 C6 C7 -85(2) . . . . ?
C5 N1 C6 C7 91(2) . . . . ?
O2 S1 C9 F3 -66(2) . . . . ?
O1 S1 C9 F3 59(2) . . . . ?
N14 S1 C9 F3 173.3(19) . . . . ?
O2 S1 C9 F1 58(2) . . . . ?
O1 S1 C9 F1 -177(2) . . . . ?
N14 S1 C9 F1 -63(2) . . . . ?
O2 S1 C9 F2 175.5(15) . . . . ?
O1 S1 C9 F2 -59.6(17) . . . . ?
N14 S1 C9 F2 54.9(17) . . . . ?
O4 S2 C10 F5 -170.0(14) . . . . ?
O3 S2 C10 F5 -44.7(16) . . . . ?
N14 S2 C10 F5 76.9(17) . . . . ?
O4 S2 C10 F4 64.3(17) . . . . ?
O3 S2 C10 F4 -170.4(16) . . . . ?
N14 S2 C10 F4 -49(2) . . . . ?
O4 S2 C10 F6 -54(2) . . . . ?
O3 S2 C10 F6 71(2) . . . . ?
N14 S2 C10 F6 -167.0(19) . . . . ?
O4 S2 N14 S1 164.4(12) . . . . ?
O3 S2 N14 S1 30.6(15) . . . . ?
C10 S2 N14 S1 -84.5(15) . . . . ?
O2 S1 N14 S2 -1.1(15) . . . . ?
O1 S1 N14 S2 -136.7(12) . . . . ?
C9 S1 N14 S2 112.9(14) . . . . ?
O7 S4 N15 S3 5.2(16) . . . . ?
O8 S4 N15 S3 -135.0(12) . . . . ?
C20 S4 N15 S3 118.5(13) . . . . ?
O6 S3 N15 S4 158.9(12) . . . . ?
O5 S3 N15 S4 23.4(16) . . . . ?
C19 S3 N15 S4 -92.4(14) . . . . ?
C15 N11 C12 N13 -5.6(19) . . . . ?
C16 N11 C12 N13 177.0(18) . . . . ?
C14 N13 C12 N11 3.4(19) . . . . ?
C18 N13 C12 N11 178.7(15) . . . . ?
C12 N13 C14 C15 0.2(19) . . . . ?
C18 N13 C14 C15 -175.0(17) . . . . ?
N13 C14 C15 N11 -3(2) . . . . ?
C12 N11 C15 C14 6(2) . . . . ?
C16 N11 C15 C14 -177.0(19) . . . . ?
C12 N11 C16 C17 -89(2) . . . . ?
C15 N11 C16 C17 94(2) . . . . ?
O6 S3 C19 F9 71.1(17) . . . . ?
O5 S3 C19 F9 -165.2(15) . . . . ?
N15 S3 C19 F9 -42(2) . . . . ?
O6 S3 C19 F8 -172.5(15) . . . . ?
O5 S3 C19 F8 -48.8(17) . . . . ?
N15 S3 C19 F8 74.9(17) . . . . ?
O6 S3 C19 F7 -57(2) . . . . ?
O5 S3 C19 F7 67(2) . . . . ?
N15 S3 C19 F7 -169.5(17) . . . . ?
O7 S4 C20 F11 -178.0(15) . . . . ?
O8 S4 C20 F11 -53.1(18) . . . . ?
N15 S4 C20 F11 59.2(16) . . . . ?
O7 S4 C20 F10 51(2) . . . . ?
O8 S4 C20 F10 176.2(18) . . . . ?
N15 S4 C20 F10 -71.6(19) . . . . ?
O7 S4 C20 F12 -63.9(14) . . . . ?
O8 S4 C20 F12 61.0(16) . . . . ?
N15 S4 C20 F12 173.3(13) . . . . ?
#===END
# Attachment 'CrystEngComm B609598D [emim]OTf.cif'
# CIF-file generated for il12_150 in P b c a
#===============================================================================
data_il12_150
_database_code_depnum_ccdc_archive 'CCDC 614038'
# 0. AUDIT DETAILS
_audit_creation_date 'Aug 04 14:01:15 2006'
_audit_creation_method 'PLATON option'
_audit_update_record
; ?
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
1-ethyl-3-methylimidazolium trifluoromethanesulfonate
;
_chemical_name_common
'1-ethyl-3-methylimidazolium trifluoromethanesulfonate'
_chemical_melting_point ?
_chemical_formula_moiety 'C6 H11 N2, C F3 O3 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C7 H11 F3 N2 O3 S'
_chemical_formula_iupac ?
_chemical_formula_weight 260.25
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_Int_Tables_number 61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
_cell_length_a 10.183(5)
_cell_length_b 12.384(7)
_cell_length_c 18.294(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2307(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 150
_cell_measurement_reflns_used 739
_cell_measurement_theta_min 2.19
_cell_measurement_theta_max 17.83
_cell_special_details
; ?
;
_exptl_crystal_description Rod
_exptl_crystal_colour Colorless
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.3
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.499
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1072
_exptl_absorpt_coefficient_mu 0.316
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type None
# Example: '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 150.0(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_type 'Bruker SMART CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
# number of measured reflections (redundant set)
_diffrn_reflns_number 10196
_diffrn_reflns_av_R_equivalents 0.0404
_diffrn_reflns_av_sigmaI/netI 0.0363
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.23
_diffrn_reflns_theta_max 25.34
_reflns_number_total 2028
_reflns_number_gt 1535
_reflns_threshold_expression >2sigma(I)
_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full 25.34
_diffrn_measured_fraction_theta_full 0.959
_computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution 'SIR92 (Altomare, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
Ortep-32 for Windows (Farrugia, 1997), POV-Ray^TM^ for Windows
Version 3.6 (The POV-Ray Team, 2004) and CAMERON (Watkin et. al., 1993)
;
_computing_publication_material 'PLATON (Spek, 1990)'
#===============================================================================
# 8. REFINEMENT DATA
_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^)+(0.0358P)^2^+4.3360P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2028
_refine_ls_number_parameters 147
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0738
_refine_ls_R_factor_gt 0.0519
_refine_ls_wR_factor_ref 0.1341
_refine_ls_wR_factor_gt 0.1249
_refine_ls_goodness_of_fit_ref 1.139
_refine_ls_restrained_S_all 1.139
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.350
_refine_diff_density_min -0.286
_refine_diff_density_rms 0.066
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.02018(9) 0.30651(7) 0.15056(5) 0.0308(3) Uani 1 1 d . . .
F3 F 0.1410(3) 0.2493(2) 0.03140(13) 0.0742(9) Uani 1 1 d . . .
F2 F -0.0624(3) 0.2826(3) 0.01643(14) 0.0827(10) Uani 1 1 d . . .
F1 F 0.0735(3) 0.4117(2) 0.03107(14) 0.0759(9) Uani 1 1 d . . .
O1 O -0.0832(2) 0.3828(2) 0.16363(15) 0.0444(7) Uani 1 1 d . . .
O2 O -0.0129(3) 0.1967(2) 0.16358(14) 0.0450(7) Uani 1 1 d . . .
O3 O 0.1456(2) 0.3398(2) 0.17835(14) 0.0400(7) Uani 1 1 d . . .
N1 N 0.5597(3) 0.3207(2) 0.15552(16) 0.0361(7) Uani 1 1 d . . .
C2 C 0.4388(4) 0.2849(3) 0.16102(18) 0.0310(8) Uani 1 1 d . . .
H2 H 0.3642 0.3278 0.1650 0.037 Uiso 1 1 calc R . .
N3 N 0.4401(3) 0.1779(2) 0.15994(16) 0.0363(7) Uani 1 1 d . . .
C4 C 0.5670(3) 0.1444(3) 0.15449(19) 0.0342(8) Uani 1 1 d . . .
H4 H 0.5961 0.0733 0.1528 0.041 Uiso 1 1 calc R . .
C5 C 0.6422(4) 0.2335(3) 0.1520(2) 0.0379(9) Uani 1 1 d . . .
H5 H 0.7333 0.2355 0.1486 0.045 Uiso 1 1 calc R . .
C6 C 0.5976(4) 0.4351(3) 0.1538(2) 0.0425(10) Uani 1 1 d . . .
H6A H 0.6698 0.4467 0.1875 0.051 Uiso 1 1 calc R . .
H6B H 0.5241 0.4788 0.1700 0.051 Uiso 1 1 calc R . .
C7 C 0.6384(5) 0.4706(3) 0.0786(2) 0.0552(12) Uani 1 1 d . . .
H7A H 0.7123 0.4286 0.0628 0.083 Uiso 1 1 calc R . .
H7B H 0.6622 0.5456 0.0797 0.083 Uiso 1 1 calc R . .
H7C H 0.5667 0.4604 0.0452 0.083 Uiso 1 1 calc R . .
C8 C 0.3255(4) 0.1083(3) 0.1644(3) 0.0513(11) Uani 1 1 d . . .
H8A H 0.2547 0.1467 0.1873 0.077 Uiso 1 1 calc R . .
H8B H 0.3465 0.0454 0.1927 0.077 Uiso 1 1 calc R . .
H8C H 0.2997 0.0868 0.1160 0.077 Uiso 1 1 calc R . .
C9 C 0.0437(5) 0.3128(4) 0.0526(2) 0.0491(11) Uani 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 0.0296(5) 0.0326(5) 0.0303(4) 0.0000(4) 0.0000(4) 0.0030(4)
F1 0.114(2) 0.0643(19) 0.0492(15) 0.0215(13) 0.0132(15) 0.0005(17)
F2 0.085(2) 0.119(3) 0.0445(15) -0.0093(15) -0.0278(14) -0.0042(19)
F3 0.093(2) 0.082(2) 0.0476(14) -0.0086(13) 0.0239(15) 0.0267(17)
O1 0.0341(15) 0.0446(16) 0.0545(17) -0.0027(13) 0.0050(13) 0.0107(12)
O2 0.0488(17) 0.0379(15) 0.0482(15) 0.0007(13) 0.0025(13) -0.0086(13)
O3 0.0327(15) 0.0420(16) 0.0453(15) -0.0029(12) -0.0039(12) -0.0018(12)
N1 0.0325(18) 0.0387(19) 0.0372(16) -0.0072(14) -0.0047(14) 0.0047(14)
C2 0.030(2) 0.027(2) 0.0357(19) -0.0015(15) 0.0000(15) 0.0044(15)
N3 0.0346(18) 0.039(2) 0.0357(16) 0.0026(14) -0.0018(13) -0.0013(14)
C4 0.032(2) 0.033(2) 0.0376(19) -0.0026(16) 0.0007(16) 0.0086(16)
C5 0.030(2) 0.040(2) 0.043(2) -0.0030(18) -0.0027(18) 0.0071(17)
C6 0.041(2) 0.031(2) 0.056(2) -0.0088(18) -0.003(2) 0.0002(17)
C7 0.070(3) 0.040(2) 0.055(3) 0.005(2) -0.017(2) -0.001(2)
C8 0.040(2) 0.040(2) 0.075(3) 0.009(2) 0.004(2) 0.0001(19)
C9 0.062(3) 0.051(3) 0.0339(19) 0.0000(19) -0.004(2) 0.009(2)
_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 O2 1.421(3) . ?
S1 O1 1.434(3) . ?
S1 O3 1.435(3) . ?
S1 C9 1.809(4) . ?
N3 C2 1.325(5) . ?
N3 C4 1.361(5) . ?
N3 C8 1.454(5) . ?
C2 N1 1.312(5) . ?
C2 H2 0.9300 . ?
N1 C5 1.370(5) . ?
N1 C6 1.468(5) . ?
C4 C5 1.343(5) . ?
C4 H4 0.9300 . ?
F3 C9 1.322(5) . ?
F2 C9 1.321(5) . ?
F1 C9 1.322(5) . ?
C6 C7 1.503(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
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
O2 S1 O1 115.39(17) . . ?
O2 S1 O3 115.25(16) . . ?
O1 S1 O3 113.85(16) . . ?
O2 S1 C9 103.79(18) . . ?
O1 S1 C9 103.54(18) . . ?
O3 S1 C9 102.74(19) . . ?
C2 N3 C4 108.4(3) . . ?
C2 N3 C8 125.8(3) . . ?
C4 N3 C8 125.8(3) . . ?
N1 C2 N3 109.1(3) . . ?
N1 C2 H2 125.4 . . ?
N3 C2 H2 125.4 . . ?
C2 N1 C5 108.2(3) . . ?
C2 N1 C6 125.1(3) . . ?
C5 N1 C6 126.7(3) . . ?
C5 C4 N3 107.1(3) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
N1 C6 C7 112.0(3) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C4 C5 N1 107.2(3) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
F2 C9 F1 107.5(4) . . ?
F2 C9 F3 107.3(3) . . ?
F1 C9 F3 106.9(4) . . ?
F2 C9 S1 112.1(3) . . ?
F1 C9 S1 111.4(3) . . ?
F3 C9 S1 111.4(3) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
C4 N3 C2 N1 0.8(4) . . . . ?
C8 N3 C2 N1 -179.6(3) . . . . ?
N3 C2 N1 C5 -1.1(4) . . . . ?
N3 C2 N1 C6 179.2(3) . . . . ?
C2 N3 C4 C5 -0.2(4) . . . . ?
C8 N3 C4 C5 -179.8(4) . . . . ?
C2 N1 C6 C7 -106.3(4) . . . . ?
C5 N1 C6 C7 74.0(5) . . . . ?
N3 C4 C5 N1 -0.4(4) . . . . ?
C2 N1 C5 C4 0.9(4) . . . . ?
C6 N1 C5 C4 -179.3(3) . . . . ?
O2 S1 C9 F2 58.5(3) . . . . ?
O1 S1 C9 F2 -62.4(3) . . . . ?
O3 S1 C9 F2 178.9(3) . . . . ?
O2 S1 C9 F1 179.0(3) . . . . ?
O1 S1 C9 F1 58.1(4) . . . . ?
O3 S1 C9 F1 -60.6(3) . . . . ?
O2 S1 C9 F3 -61.7(3) . . . . ?
O1 S1 C9 F3 177.4(3) . . . . ?
O3 S1 C9 F3 58.7(3) . . . . ?
#===END