# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012
data_New_Global_Publ_Block
_journal_name_full 'Dalton Trans.'
_journal_coden_cambridge 0222
#TrackingRef 'Ph2Se2Br2.cif'
_publ_section_related_literature ?
# Added by publCIF - use a unique identifier for each data block
#==============================================================================
# SUBMISSION DETAILS
_publ_contact_author_name
'Nicholas A Barnes' # Name of author for correspondence
_publ_contact_author_address # Address of author for correspondence
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
_publ_contact_author_email 'nick barnes28@hotmail.com'
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_contact_letter
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;
_publ_requested_category ?
#==============================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
;
Structural isomerism in (p-XC~6~H~4~)SeCl~3~ and
(p-XC~6~H~4~)SeBr~3~ (X = F, Cl) compounds. Co-crystallisation of
cis- and trans-dimeric forms of
(p-ClC~6~H~4~)SeCl~2~(\m-Cl)~2~(p-ClC~6~H~4~)SeCl~2~. A new
structural modification for the "PhSeBr" reagent, Ph~2~Se~2~Br~2~, containing
an elongated Se-Se bond
;
_publ_section_title_footnote # remove if not required
; ?
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
N.Barnes
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
. .
S.Godfrey
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
. .
R.T.Ollerenshaw
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
. .
R.Khan
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
. .
R.Pritchard
;
School of Chemistry,
The University of Manchester,
Oxford Road,
Manchester,
M13 9PL, UK
;
. .
#==============================================================================
# TEXT
_publ_section_synopsis
;
?
;
_publ_section_abstract
;
?
;
_publ_section_comment
;
?
;
_publ_section_acknowledgements # remove if not required
;
?
;
_publ_section_references
;
?
;
_publ_section_figure_captions
;
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
?
;
#==============================================================================
#\#CIF_1.1
# CIF produced by WinGX routine CIF_UPDATE
# Created on 2012-07-04 at 11:05:51
# Using CIFtbx version 2.6.2 16 Jun 1998
# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\archive.reqdat
# CIF files read : r dreduc sortav struct
data_r_Ph2Se2Br2
_database_code_depnum_ccdc_archive 'CCDC 892016'
#TrackingRef 'Ph2Se2Br2.cif'
_audit_update_record
;
2012-09-11 # Formatted by publCIF
;
_audit_creation_date 2012-07-04T11:05:51-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.4
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic ?
_chemical_formula_moiety 'C12 H10 Br2 Se2'
_chemical_formula_sum 'C12 H10 Br2 Se2'
_chemical_formula_weight 471.94
_chemical_compound_source 'synthesis as described'
_chemical_absolute_configuration ad
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 6.0108(5)
_cell_length_b 7.1843(7)
_cell_length_c 15.6165(18)
_cell_angle_alpha 90.000(4)
_cell_angle_beta 90.004(4)
_cell_angle_gamma 90.000(7)
_cell_volume 674.37(12)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1703
_cell_measurement_theta_min 2
_cell_measurement_theta_max 27
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description prism
_exptl_crystal_colour purple
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.05
_exptl_crystal_density_diffrn 2.324
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 440
_exptl_special_details ?
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 11.378
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.3422
_exptl_absorpt_correction_T_max 0.6
_exptl_absorpt_process_details
;
Blessing, R. H. (1995) Acta Cryst., A51, 33-38.
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 -0.142683
_diffrn_orient_matrix_ub_12 0.59124E-2
_diffrn_orient_matrix_ub_13 0.328272E-1
_diffrn_orient_matrix_ub_21 -0.854461E-1
_diffrn_orient_matrix_ub_22 -0.28603E-2
_diffrn_orient_matrix_ub_23 -0.549223E-1
_diffrn_orient_matrix_ub_31 -0.43096E-2
_diffrn_orient_matrix_ub_32 -0.139037
_diffrn_orient_matrix_ub_33 0.25258E-2
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents 0.158
_diffrn_reflns_av_unetI/netI 0.0983
_diffrn_reflns_number 5484
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 3.63
_diffrn_reflns_theta_max 25.6
_diffrn_reflns_theta_full 25.6
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total 2061
_reflns_number_gt 1646
_reflns_threshold_expression >2\s(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^ > 2\s(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.
A total of 85 restraints were applied. These comprise six ISOR restraints
on each of the twelve carbon atoms c(1) to C(12) and on atoms Se(1) and
Br(1). Additionally, one floating origin restraint was generated due to
the P21 (no. 4) space group.
;
_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^)+(0.1203P)^2^+28.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef 0.003(2)
_refine_ls_number_reflns 2061
_refine_ls_number_parameters 147
_refine_ls_number_restraints 85
_refine_ls_R_factor_all 0.1222
_refine_ls_R_factor_gt 0.0886
_refine_ls_wR_factor_ref 0.2544
_refine_ls_wR_factor_gt 0.213
_refine_ls_goodness_of_fit_ref 1.068
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.18(14)
_refine_diff_density_max 2.487
_refine_diff_density_min -2.202
_refine_diff_density_rms 0.364
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 C 0.780(5) 0.823(5) 0.3748(16) 0.024(6) Uani 1 1 d U . .
C2 C 0.599(5) 0.731(5) 0.4169(19) 0.021(7) Uani 1 1 d U . .
H2 H 0.4906 0.6655 0.3848 0.026 Uiso 1 1 calc R . .
C3 C 0.586(6) 0.741(6) 0.506(2) 0.030(8) Uani 1 1 d U . .
H3 H 0.469 0.6807 0.5368 0.036 Uiso 1 1 calc R . .
C4 C 0.748(6) 0.840(6) 0.548(2) 0.036(9) Uani 1 1 d U . .
H4 H 0.7396 0.8495 0.609 0.043 Uiso 1 1 calc R . .
C5 C 0.924(6) 0.927(6) 0.506(3) 0.031(8) Uani 1 1 d U . .
H5 H 1.0352 0.9925 0.537 0.038 Uiso 1 1 calc R . .
C6 C 0.934(5) 0.917(5) 0.418(2) 0.024(7) Uani 1 1 d U . .
H6 H 1.0509 0.9779 0.3877 0.028 Uiso 1 1 calc R . .
C7 C 0.339(5) 1.038(5) 0.1291(19) 0.025(7) Uani 1 1 d U . .
C8 C 0.137(5) 1.110(6) 0.103(2) 0.030(7) Uani 1 1 d U . .
H8 H 0.0357 1.1555 0.1447 0.037 Uiso 1 1 calc R . .
C9 C 0.082(6) 1.118(6) 0.020(2) 0.040(9) Uani 1 1 d U . .
H9 H -0.0518 1.1773 0.0032 0.048 Uiso 1 1 calc R . .
C10 C 0.229(7) 1.033(7) -0.044(3) 0.042(9) Uani 1 1 d U . .
H10 H 0.1835 1.018 -0.1018 0.05 Uiso 1 1 calc R . .
C11 C 0.437(8) 0.977(8) -0.016(3) 0.053(14) Uani 1 1 d U . .
H11 H 0.5449 0.9396 -0.0573 0.063 Uiso 1 1 calc R . .
C12 C 0.491(7) 0.974(5) 0.066(2) 0.032(8) Uani 1 1 d U . .
H12 H 0.6326 0.9291 0.0828 0.039 Uiso 1 1 calc R . .
Se1 Se 0.7985(5) 0.8043(5) 0.2498(3) 0.0324(7) Uani 1 1 d U . .
Se2 Se 0.4163(5) 1.0349(4) 0.2490(3) 0.0302(7) Uani 1 1 d . . .
Br1 Br 1.1478(5) 0.6290(4) 0.2455(4) 0.0347(8) Uani 1 1 d . . .
Br2 Br 0.6246(5) 1.3117(5) 0.2557(3) 0.0370(8) Uani 1 1 d U . .
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
C1 0.027(10) 0.025(10) 0.019(9) 0.001(9) 0.006(8) -0.006(8)
C2 0.023(10) 0.019(10) 0.022(10) -0.001(8) 0.003(8) 0.004(8)
C3 0.025(11) 0.030(11) 0.036(11) -0.007(8) 0.000(9) 0.007(9)
C4 0.037(12) 0.038(12) 0.033(11) -0.001(9) 0.003(9) -0.003(9)
C5 0.031(11) 0.032(11) 0.031(10) -0.004(8) 0.004(9) -0.002(8)
C6 0.025(11) 0.022(10) 0.023(10) 0.005(8) 0.000(8) -0.005(8)
C7 0.026(10) 0.025(10) 0.025(10) -0.003(8) 0.001(8) 0.001(9)
C8 0.024(10) 0.034(11) 0.033(10) -0.001(9) 0.005(8) -0.003(9)
C9 0.037(12) 0.042(12) 0.041(12) 0.000(9) -0.003(8) 0.000(9)
C10 0.039(12) 0.042(12) 0.045(12) -0.003(9) -0.007(9) 0.001(9)
C11 0.052(16) 0.055(16) 0.052(15) 0.000(9) -0.003(9) 0.000(9)
C12 0.035(11) 0.026(11) 0.036(11) -0.007(8) -0.003(9) 0.000(8)
Se1 0.0330(14) 0.0352(15) 0.0290(14) 0.000(3) 0.000(3) -0.0063(13)
Se2 0.0289(13) 0.0337(15) 0.0280(15) -0.002(3) 0.001(3) -0.0007(12)
Br1 0.0325(15) 0.0323(15) 0.039(2) 0.000(3) -0.001(3) 0.0004(13)
Br2 0.0358(15) 0.0351(16) 0.0400(18) -0.003(3) 0.003(3) -0.0045(14)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.33(5) . ?
C1 C2 1.43(4) . ?
C1 Se1 1.96(3) . ?
C2 C3 1.40(4) . ?
C2 H2 0.95 . ?
C3 C4 1.37(5) . ?
C3 H3 0.95 . ?
C4 C5 1.40(5) . ?
C4 H4 0.95 . ?
C5 C6 1.38(5) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.38(5) . ?
C7 C12 1.42(5) . ?
C7 Se2 1.93(3) . ?
C8 C9 1.33(5) . ?
C8 H8 0.95 . ?
C9 C10 1.47(6) . ?
C9 H9 0.95 . ?
C10 C11 1.39(6) . ?
C10 H10 0.95 . ?
C11 C12 1.32(5) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
Se1 Br1 2.449(4) . ?
Se1 Se2 2.833(4) . ?
Se2 Br2 2.352(5) . ?
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
C6 C1 C2 122(3) . . ?
C6 C1 Se1 120(2) . . ?
C2 C1 Se1 118(2) . . ?
C3 C2 C1 119(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 117(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 123(3) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 119(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C1 C6 C5 120(3) . . ?
C1 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C8 C7 C12 119(3) . . ?
C8 C7 Se2 120(2) . . ?
C12 C7 Se2 121(3) . . ?
C9 C8 C7 121(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 117(4) . . ?
C11 C10 H10 121.7 . . ?
C9 C10 H10 121.7 . . ?
C12 C11 C10 122(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 121(4) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C1 Se1 Br1 96.5(10) . . ?
C1 Se1 Se2 85.2(10) . . ?
Br1 Se1 Se2 174.83(17) . . ?
C7 Se2 Br2 99.3(11) . . ?
C7 Se2 Se1 101.9(10) . . ?
Br2 Se2 Se1 93.60(14) . . ?
# END of CIF
# Attachment 'p-ClC6H4SeBr3.cif'
#==============================================================================
#\#CIF_1.1
# CIF produced by WinGX routine CIF_UPDATE
# Created on 2012-07-04 at 09:34:03
# Using CIFtbx version 2.6.2 16 Jun 1998
# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\archive.reqdat
# CIF files read : r dreduc sortav struct
data_r_p-ClC6H4SeBr3
_database_code_depnum_ccdc_archive 'CCDC 892017'
#TrackingRef 'p-ClC6H4SeBr3.cif'
_audit_update_record
;
2012-09-13 # Formatted by publCIF
;
_audit_creation_date 2012-07-04T09:34:03-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.4
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic ?
_chemical_formula_moiety 'C12 H8 Br6 Cl2 Se2'
_chemical_formula_sum 'C12 H8 Br6 Cl2 Se2'
_chemical_formula_weight 860.46
_chemical_compound_source 'synthesis as described'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 7.24800(10)
_cell_length_b 25.3497(5)
_cell_length_c 10.7265(3)
_cell_angle_alpha 90
_cell_angle_beta 96.9800(10)
_cell_angle_gamma 90
_cell_volume 1956.22(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 5993
_cell_measurement_theta_min 2
_cell_measurement_theta_max 27
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description plate
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.14
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.02
_exptl_crystal_density_diffrn 2.922
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1568
_exptl_special_details ?
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 16.301
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.1372
_exptl_absorpt_correction_T_max 0.7430
_exptl_absorpt_process_details
;
Blessing, R. H. (1995) Acta Cryst., A51, 33-38.
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 -0.101193
_diffrn_orient_matrix_ub_12 -0.166006E-1
_diffrn_orient_matrix_ub_13 -0.587652E-1
_diffrn_orient_matrix_ub_21 -0.935028E-1
_diffrn_orient_matrix_ub_22 0.112886E-1
_diffrn_orient_matrix_ub_23 0.559357E-1
_diffrn_orient_matrix_ub_31 -0.183859E-1
_diffrn_orient_matrix_ub_32 0.33958E-1
_diffrn_orient_matrix_ub_33 -0.473224E-1
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents 0.0696
_diffrn_reflns_av_unetI/netI 0.0744
_diffrn_reflns_number 21237
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -31
_diffrn_reflns_limit_k_max 31
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.94
_diffrn_reflns_theta_max 26
_diffrn_reflns_theta_full 26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total 3805
_reflns_number_gt 3084
_reflns_threshold_expression >2\s(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^ > 2\s(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.
Deepest hole -2.76 at 0.2243 0.3705 0.7582 [ 0.91 A from SE2 ]
;
_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^)+(0.0933P)^2^+15.1532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef 0.0007(3)
_refine_ls_number_reflns 3805
_refine_ls_number_parameters 200
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0821
_refine_ls_R_factor_gt 0.067
_refine_ls_wR_factor_ref 0.1756
_refine_ls_wR_factor_gt 0.166
_refine_ls_goodness_of_fit_ref 1.138
_refine_ls_restrained_S_all 1.138
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0
_refine_diff_density_max 1.881
_refine_diff_density_min -2.76
_refine_diff_density_rms 0.391
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 C 0.3021(14) 0.5963(5) 0.7272(10) 0.019(2) Uani 1 1 d . . .
C2 C 0.3148(17) 0.6467(4) 0.7807(11) 0.023(3) Uani 1 1 d . . .
H2 H 0.3357 0.6509 0.8693 0.028 Uiso 1 1 calc R . .
C3 C 0.2962(16) 0.6911(5) 0.7009(11) 0.026(3) Uani 1 1 d . . .
H3 H 0.3059 0.726 0.7336 0.032 Uiso 1 1 calc R . .
C4 C 0.2629(14) 0.6817(4) 0.5724(10) 0.018(2) Uani 1 1 d . . .
C5 C 0.2577(15) 0.6327(5) 0.5211(10) 0.019(2) Uani 1 1 d . . .
H5 H 0.2442 0.6287 0.4324 0.022 Uiso 1 1 calc R . .
C6 C 0.2723(16) 0.5881(5) 0.5982(9) 0.020(2) Uani 1 1 d . . .
H6 H 0.2621 0.5535 0.5638 0.024 Uiso 1 1 calc R . .
C7 C 0.2602(14) 0.3705(5) 0.5684(10) 0.019(2) Uani 1 1 d . . .
C8 C 0.2345(14) 0.4077(4) 0.4713(9) 0.017(2) Uani 1 1 d . . .
H8 H 0.2396 0.4445 0.4884 0.02 Uiso 1 1 calc R . .
C9 C 0.2009(17) 0.3885(5) 0.3477(11) 0.023(2) Uani 1 1 d . . .
H9 H 0.1772 0.4123 0.2793 0.028 Uiso 1 1 calc R . .
C10 C 0.2025(15) 0.3352(5) 0.3264(11) 0.020(2) Uani 1 1 d . . .
C11 C 0.2279(16) 0.2987(5) 0.4238(11) 0.025(3) Uani 1 1 d . . .
H11 H 0.2244 0.2619 0.4067 0.029 Uiso 1 1 calc R . .
C12 C 0.2584(15) 0.3170(5) 0.5459(11) 0.021(2) Uani 1 1 d . . .
H12 H 0.278 0.2929 0.6139 0.025 Uiso 1 1 calc R . .
Se1 Se 0.32346(14) 0.53532(4) 0.83959(9) 0.0160(3) Uani 1 1 d . . .
Se2 Se 0.30640(14) 0.39606(4) 0.74114(9) 0.0160(3) Uani 1 1 d . . .
Br1 Br 0.13628(15) 0.56883(4) 0.98454(10) 0.0202(3) Uani 1 1 d . . .
Br2 Br 0.03951(15) 0.48416(4) 0.70702(10) 0.0200(3) Uani 1 1 d . . .
Br3 Br 0.62166(15) 0.56688(4) 0.95240(10) 0.0191(3) Uani 1 1 d . . .
Br4 Br 0.54217(16) 0.33430(5) 0.81032(10) 0.0232(3) Uani 1 1 d . . .
Br5 Br 0.05335(15) 0.34168(4) 0.81291(10) 0.0213(3) Uani 1 1 d . . .
Br6 Br 0.54972(15) 0.46727(5) 0.68256(10) 0.0208(3) Uani 1 1 d . . .
Cl1 Cl 0.2339(4) 0.73705(12) 0.4742(3) 0.0266(6) Uani 1 1 d . . .
Cl2 Cl 0.1640(4) 0.31292(12) 0.1716(2) 0.0248(6) 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
C1 0.008(5) 0.025(6) 0.026(6) 0.007(5) 0.004(4) 0.002(4)
C2 0.037(7) 0.006(5) 0.028(6) -0.001(5) 0.008(5) -0.002(5)
C3 0.019(6) 0.028(7) 0.030(6) -0.004(5) -0.005(5) 0.002(5)
C4 0.010(5) 0.015(6) 0.030(6) 0.007(5) 0.002(4) 0.002(4)
C5 0.020(6) 0.020(6) 0.016(5) 0.002(4) 0.001(4) 0.007(4)
C6 0.029(6) 0.020(6) 0.012(5) -0.003(4) 0.005(4) 0.005(5)
C7 0.007(5) 0.033(7) 0.017(5) 0.001(5) 0.001(4) 0.001(5)
C8 0.017(5) 0.013(6) 0.019(5) -0.006(4) -0.002(4) 0.009(4)
C9 0.030(6) 0.013(6) 0.027(6) 0.000(5) 0.004(5) 0.004(5)
C10 0.016(6) 0.020(6) 0.024(6) -0.010(5) -0.001(4) -0.003(4)
C11 0.019(6) 0.026(7) 0.029(6) -0.001(5) 0.006(5) -0.002(5)
C12 0.018(6) 0.014(6) 0.029(6) 0.002(5) -0.004(4) -0.002(4)
Se1 0.0169(6) 0.0130(6) 0.0182(5) 0.0005(4) 0.0026(4) 0.0000(4)
Se2 0.0159(6) 0.0138(6) 0.0180(5) -0.0004(4) 0.0014(4) 0.0002(4)
Br1 0.0201(6) 0.0208(6) 0.0203(5) -0.0002(4) 0.0054(4) 0.0007(4)
Br2 0.0172(6) 0.0167(6) 0.0255(6) 0.0009(4) 0.0005(4) 0.0003(4)
Br3 0.0183(6) 0.0189(6) 0.0197(5) 0.0007(4) 0.0010(4) -0.0019(4)
Br4 0.0230(6) 0.0190(6) 0.0264(6) -0.0009(5) -0.0025(4) 0.0063(4)
Br5 0.0227(6) 0.0181(6) 0.0239(6) 0.0023(4) 0.0058(4) -0.0010(4)
Br6 0.0191(6) 0.0198(6) 0.0240(6) -0.0044(4) 0.0049(4) -0.0032(4)
Cl1 0.0388(17) 0.0173(15) 0.0232(13) 0.0055(11) 0.0014(12) -0.0010(12)
Cl2 0.0318(16) 0.0228(15) 0.0192(13) -0.0057(11) 0.0009(11) 0.0007(12)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.390(15) . ?
C1 C2 1.397(17) . ?
C1 Se1 1.955(11) . ?
C2 C3 1.412(17) . ?
C2 H2 0.95 . ?
C3 C4 1.390(16) . ?
C3 H3 0.95 . ?
C4 C5 1.358(16) . ?
C4 Cl1 1.752(11) . ?
C5 C6 1.397(16) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.376(17) . ?
C7 C8 1.401(16) . ?
C7 Se2 1.954(11) . ?
C8 C9 1.406(16) . ?
C8 H8 0.95 . ?
C9 C10 1.369(16) . ?
C9 H9 0.95 . ?
C10 C11 1.392(17) . ?
C10 Cl2 1.745(11) . ?
C11 C12 1.382(17) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
Se1 Br1 2.3436(14) . ?
Se1 Br3 2.4779(15) . ?
Se1 Br2 2.6887(15) . ?
Se2 Br4 2.3694(15) . ?
Se2 Br5 2.4899(15) . ?
Se2 Br6 2.6520(15) . ?
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
C6 C1 C2 122.7(11) . . ?
C6 C1 Se1 119.1(9) . . ?
C2 C1 Se1 118.2(8) . . ?
C1 C2 C3 118.9(11) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 117.2(12) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C5 C4 C3 123.5(11) . . ?
C5 C4 Cl1 119.6(9) . . ?
C3 C4 Cl1 116.9(9) . . ?
C4 C5 C6 120.3(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.4(11) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C12 C7 C8 122.4(10) . . ?
C12 C7 Se2 119.3(8) . . ?
C8 C7 Se2 118.2(9) . . ?
C7 C8 C9 117.3(10) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 119.7(11) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 122.3(11) . . ?
C9 C10 Cl2 118.3(9) . . ?
C11 C10 Cl2 119.3(9) . . ?
C12 C11 C10 118.6(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C7 C12 C11 119.6(11) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C1 Se1 Br1 96.5(3) . . ?
C1 Se1 Br3 92.6(3) . . ?
Br1 Se1 Br3 95.73(5) . . ?
C1 Se1 Br2 93.3(3) . . ?
Br1 Se1 Br2 93.33(5) . . ?
Br3 Se1 Br2 168.58(6) . . ?
C7 Se2 Br4 96.4(3) . . ?
C7 Se2 Br5 93.5(3) . . ?
Br4 Se2 Br5 93.88(5) . . ?
C7 Se2 Br6 92.5(3) . . ?
Br4 Se2 Br6 92.80(5) . . ?
Br5 Se2 Br6 170.44(6) . . ?
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 0.2(17) . . . . ?
Se1 C1 C2 C3 -178.8(9) . . . . ?
C1 C2 C3 C4 1.0(17) . . . . ?
C2 C3 C4 C5 -3.6(17) . . . . ?
C2 C3 C4 Cl1 178.4(9) . . . . ?
C3 C4 C5 C6 4.9(17) . . . . ?
Cl1 C4 C5 C6 -177.1(9) . . . . ?
C2 C1 C6 C5 1.0(17) . . . . ?
Se1 C1 C6 C5 180.0(8) . . . . ?
C4 C5 C6 C1 -3.4(16) . . . . ?
C12 C7 C8 C9 1.8(16) . . . . ?
Se2 C7 C8 C9 -179.8(8) . . . . ?
C7 C8 C9 C10 -2.8(17) . . . . ?
C8 C9 C10 C11 3.1(18) . . . . ?
C8 C9 C10 Cl2 -179.0(9) . . . . ?
C9 C10 C11 C12 -2.1(17) . . . . ?
Cl2 C10 C11 C12 180.0(9) . . . . ?
C8 C7 C12 C11 -0.9(17) . . . . ?
Se2 C7 C12 C11 -179.3(8) . . . . ?
C10 C11 C12 C7 0.9(17) . . . . ?
C6 C1 Se1 Br1 -136.2(8) . . . . ?
C2 C1 Se1 Br1 42.8(9) . . . . ?
C6 C1 Se1 Br3 127.7(8) . . . . ?
C2 C1 Se1 Br3 -53.3(9) . . . . ?
C6 C1 Se1 Br2 -42.5(8) . . . . ?
C2 C1 Se1 Br2 136.5(9) . . . . ?
C12 C7 Se2 Br4 40.4(9) . . . . ?
C8 C7 Se2 Br4 -138.0(8) . . . . ?
C12 C7 Se2 Br5 -53.9(9) . . . . ?
C8 C7 Se2 Br5 127.7(8) . . . . ?
C12 C7 Se2 Br6 133.5(8) . . . . ?
C8 C7 Se2 Br6 -44.9(8) . . . . ?
# END of CIF
# Attachment 'p-ClC6H4SeCl3.cif'
#==============================================================================
#==============================================================================
#\#CIF_1.1
# CIF produced by WinGX routine CIF_UPDATE
# Created on 2011-02-28 at 03:22:29
# Using CIFtbx version 2.6.2 16 Jun 1998
# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\archive.reqdat
# CIF files read : rob dreduc sortav struct
data_rob_p-ClC6H4SeCl3
_database_code_depnum_ccdc_archive 'CCDC 892018'
#TrackingRef 'p-ClC6H4SeCl3.cif'
_audit_update_record
;
2012-09-11 # Formatted by publCIF
;
_audit_creation_date 2011-02-28T03:22:29-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.4
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H12 Cl12 Se3'
_chemical_formula_sum 'C18 H12 Cl12 Se3'
_chemical_formula_weight 890.56
_chemical_compound_source 'synthesis as described'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 25.4102(7)
_cell_length_b 10.7139(3)
_cell_length_c 20.2732(6)
_cell_angle_alpha 90
_cell_angle_beta 92.780(2)
_cell_angle_gamma 90
_cell_volume 5512.7(3)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 6718
_cell_measurement_theta_min 2
_cell_measurement_theta_max 27
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.06
_exptl_crystal_density_diffrn 2.146
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 3408
_exptl_special_details ?
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 5.178
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min 0.5754
_exptl_absorpt_correction_T_max 0.7464
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 0.56157E-2
_diffrn_orient_matrix_ub_12 0.344312E-1
_diffrn_orient_matrix_ub_13 -0.449637E-1
_diffrn_orient_matrix_ub_21 -0.238887E-1
_diffrn_orient_matrix_ub_22 0.714976E-1
_diffrn_orient_matrix_ub_23 0.90825E-2
_diffrn_orient_matrix_ub_31 0.308254E-1
_diffrn_orient_matrix_ub_32 0.491359E-1
_diffrn_orient_matrix_ub_33 0.182917E-1
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents 0.081
_diffrn_reflns_av_unetI/netI 0.0667
_diffrn_reflns_number 20467
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 30
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 3.07
_diffrn_reflns_theta_max 25.5
_diffrn_reflns_theta_full 25.5
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total 5108
_reflns_number_gt 3605
_reflns_threshold_expression >2\s(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^ > 2\s(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^)+(0.0836P)^2^+28.3979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 5108
_refine_ls_number_parameters 298
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0902
_refine_ls_R_factor_gt 0.0567
_refine_ls_wR_factor_ref 0.1554
_refine_ls_wR_factor_gt 0.1326
_refine_ls_goodness_of_fit_ref 1.037
_refine_ls_restrained_S_all 1.037
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.001
_refine_diff_density_max 1.982
_refine_diff_density_min -1.103
_refine_diff_density_rms 0.199
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C1 C 0.3842(3) 0.7533(7) 0.3098(3) 0.0263(17) Uani 1 1 d . . .
C2 C 0.4372(3) 0.7595(7) 0.3278(4) 0.0293(18) Uani 1 1 d . . .
H2 H 0.4625 0.7655 0.295 0.035 Uiso 1 1 calc R . .
C3 C 0.4532(3) 0.7569(7) 0.3941(4) 0.0308(18) Uani 1 1 d . . .
H3 H 0.4896 0.76 0.4074 0.037 Uiso 1 1 calc R . .
C4 C 0.4149(3) 0.7497(7) 0.4409(4) 0.0285(17) Uani 1 1 d . . .
C5 C 0.3624(3) 0.7412(7) 0.4233(4) 0.0300(18) Uani 1 1 d . . .
H5 H 0.3373 0.7334 0.4563 0.036 Uiso 1 1 calc R . .
C6 C 0.3454(3) 0.7438(7) 0.3565(4) 0.0275(17) Uani 1 1 d . . .
H6 H 0.3091 0.7394 0.3434 0.033 Uiso 1 1 calc R . .
C7 C 0.3866(3) 0.3998(7) 0.3074(4) 0.0246(16) Uani 1 1 d . . .
C8 C 0.4383(3) 0.4257(6) 0.3308(4) 0.0267(17) Uani 1 1 d . . .
H8 H 0.465 0.4426 0.3009 0.032 Uiso 1 1 calc R . .
C9 C 0.4497(3) 0.4263(6) 0.3983(4) 0.0268(17) Uani 1 1 d . . .
H9 H 0.4844 0.4447 0.4153 0.032 Uiso 1 1 calc R . .
C10 C 0.4106(3) 0.4002(7) 0.4403(3) 0.0252(16) Uani 1 1 d . . .
C11 C 0.3596(3) 0.3740(7) 0.4179(3) 0.0261(17) Uani 1 1 d . . .
H11 H 0.3335 0.3548 0.4482 0.031 Uiso 1 1 calc R . .
C12 C 0.3469(3) 0.3761(7) 0.3500(3) 0.0237(16) Uani 1 1 d . . .
H12 H 0.3118 0.3616 0.3336 0.028 Uiso 1 1 calc R . .
C13 C 0.1756(3) 0.4349(6) 0.5417(3) 0.0232(16) Uani 1 1 d . . .
C14 C 0.1759(3) 0.4359(7) 0.6091(3) 0.0266(17) Uani 1 1 d . . .
H14 H 0.2082 0.4392 0.6346 0.032 Uiso 1 1 calc R . .
C15 C 0.1278(3) 0.4321(6) 0.6400(4) 0.0243(16) Uani 1 1 d . . .
H15 H 0.127 0.4332 0.6868 0.029 Uiso 1 1 calc R . .
C16 C 0.0816(3) 0.4268(6) 0.6012(4) 0.0273(17) Uani 1 1 d . . .
C17 C 0.0815(3) 0.4233(7) 0.5326(4) 0.0284(17) Uani 1 1 d . . .
H17 H 0.0492 0.4178 0.5071 0.034 Uiso 1 1 calc R . .
C18 C 0.1290(3) 0.4280(7) 0.5021(4) 0.0289(17) Uani 1 1 d . . .
H18 H 0.1299 0.4266 0.4554 0.035 Uiso 1 1 calc R . .
Cl1 Cl 0.42002(8) 0.90725(18) 0.18999(9) 0.0309(4) Uani 1 1 d . . .
Cl2 Cl 0.29815(7) 0.89788(17) 0.23258(9) 0.0270(4) Uani 1 1 d . . .
Cl3 Cl 0.29685(7) 0.57348(16) 0.23360(9) 0.0249(4) Uani 1 1 d . . .
Cl4 Cl 0.43435(10) 0.7512(2) 0.52419(9) 0.0423(6) Uani 1 1 d . . .
Cl5 Cl 0.43465(7) 0.58328(17) 0.19256(8) 0.0260(4) Uani 1 1 d . . .
Cl6 Cl 0.43703(7) 0.26813(17) 0.19287(9) 0.0287(4) Uani 1 1 d . . .
Cl7 Cl 0.31247(8) 0.24020(17) 0.21638(9) 0.0297(4) Uani 1 1 d . . .
Cl8 Cl 0.42425(8) 0.40017(18) 0.52584(8) 0.0317(4) Uani 1 1 d . . .
Cl9 Cl 0.27650(8) 0.59150(18) 0.56658(9) 0.0325(4) Uani 1 1 d . . .
Cl10 Cl 0.21648(8) 0.57334(17) 0.42041(9) 0.0317(4) Uani 1 1 d . . .
Cl11 Cl 0.21521(8) 0.25476(17) 0.42341(8) 0.0279(4) Uani 1 1 d . . .
Cl12 Cl 0.02216(8) 0.42494(18) 0.64005(10) 0.0365(5) Uani 1 1 d . . .
Se1 Se 0.36104(3) 0.76105(7) 0.21632(3) 0.0228(2) Uani 1 1 d . . .
Se2 Se 0.37116(3) 0.39571(7) 0.21232(3) 0.0237(2) Uani 1 1 d . . .
Se3 Se 0.24242(3) 0.44188(7) 0.49842(3) 0.0244(2) 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
C1 0.041(5) 0.024(4) 0.014(4) 0.000(3) -0.003(3) -0.001(3)
C2 0.026(4) 0.028(4) 0.034(4) -0.010(3) 0.001(3) 0.001(3)
C3 0.040(5) 0.032(4) 0.019(4) -0.005(3) -0.012(3) 0.001(4)
C4 0.038(5) 0.024(4) 0.022(4) 0.002(3) -0.003(3) 0.000(3)
C5 0.035(5) 0.027(4) 0.029(4) 0.002(3) 0.007(3) -0.002(3)
C6 0.024(4) 0.031(4) 0.027(4) -0.002(3) 0.001(3) -0.002(3)
C7 0.023(4) 0.022(4) 0.029(4) -0.001(3) -0.005(3) 0.002(3)
C8 0.029(4) 0.024(4) 0.028(4) 0.003(3) 0.004(3) -0.007(3)
C9 0.030(4) 0.026(4) 0.024(4) 0.004(3) -0.007(3) -0.003(3)
C10 0.031(4) 0.028(4) 0.016(4) -0.003(3) -0.001(3) 0.006(3)
C11 0.025(4) 0.027(4) 0.027(4) -0.002(3) 0.004(3) -0.001(3)
C12 0.023(4) 0.023(4) 0.026(4) 0.001(3) 0.001(3) 0.003(3)
C13 0.021(4) 0.024(4) 0.024(4) -0.004(3) 0.002(3) 0.000(3)
C14 0.023(4) 0.033(4) 0.024(4) 0.000(3) 0.002(3) -0.006(3)
C15 0.030(4) 0.022(4) 0.022(4) -0.001(3) 0.003(3) 0.001(3)
C16 0.036(5) 0.013(4) 0.034(4) -0.001(3) 0.012(3) 0.001(3)
C17 0.024(4) 0.029(4) 0.031(4) -0.007(3) -0.006(3) -0.005(3)
C18 0.037(5) 0.029(4) 0.020(4) -0.003(3) -0.001(3) 0.003(3)
Cl1 0.0320(11) 0.0308(10) 0.0301(10) 0.0048(8) 0.0047(8) -0.0065(8)
Cl2 0.0280(10) 0.0278(9) 0.0251(9) 0.0000(7) -0.0007(7) 0.0043(8)
Cl3 0.0230(9) 0.0264(10) 0.0252(9) -0.0014(7) -0.0001(7) -0.0003(7)
Cl4 0.0631(16) 0.0394(12) 0.0231(11) 0.0001(8) -0.0112(9) 0.0062(10)
Cl5 0.0242(10) 0.0312(10) 0.0226(9) 0.0001(7) 0.0015(7) -0.0007(8)
Cl6 0.0302(10) 0.0301(10) 0.0259(10) -0.0029(7) 0.0045(7) 0.0080(8)
Cl7 0.0312(11) 0.0290(10) 0.0284(10) 0.0002(7) -0.0044(8) -0.0052(8)
Cl8 0.0387(11) 0.0373(11) 0.0190(9) -0.0006(7) -0.0014(7) -0.0030(9)
Cl9 0.0359(11) 0.0312(10) 0.0304(10) -0.0041(8) 0.0024(8) -0.0065(8)
Cl10 0.0413(12) 0.0291(10) 0.0246(10) 0.0053(7) 0.0010(8) 0.0016(8)
Cl11 0.0328(11) 0.0300(10) 0.0207(9) -0.0003(7) -0.0001(7) 0.0006(8)
Cl12 0.0283(11) 0.0338(11) 0.0484(12) -0.0039(9) 0.0123(9) -0.0038(8)
Se1 0.0245(4) 0.0245(4) 0.0195(4) 0.0009(3) 0.0007(3) -0.0007(3)
Se2 0.0250(4) 0.0260(4) 0.0199(4) -0.0014(3) -0.0002(3) 0.0005(3)
Se3 0.0281(4) 0.0242(4) 0.0212(4) -0.0005(3) 0.0031(3) 0.0003(3)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.381(11) . ?
C1 C6 1.402(10) . ?
C1 Se1 1.959(7) . ?
C2 C3 1.385(11) . ?
C3 C4 1.395(11) . ?
C4 C5 1.368(11) . ?
C4 Cl4 1.737(7) . ?
C5 C6 1.400(10) . ?
C7 C12 1.382(10) . ?
C7 C8 1.403(10) . ?
C7 Se2 1.948(7) . ?
C8 C9 1.385(10) . ?
C9 C10 1.368(11) . ?
C10 C11 1.380(10) . ?
C10 Cl8 1.753(7) . ?
C11 C12 1.397(10) . ?
C13 C14 1.365(10) . ?
C13 C18 1.399(10) . ?
C13 Se3 1.951(7) . ?
C14 C15 1.401(10) . ?
C15 C16 1.382(11) . ?
C16 C17 1.391(11) . ?
C16 Cl12 1.736(8) . ?
C17 C18 1.383(11) . ?
Cl1 Se1 2.250(2) . ?
Cl2 Se1 2.205(2) . ?
Cl3 Se1 2.6225(19) . ?
Cl5 Se2 2.6201(19) . ?
Cl6 Se2 2.2112(19) . ?
Cl7 Se2 2.240(2) . ?
Cl9 Se3 2.261(2) . ?
Cl10 Se3 2.1949(19) . ?
Cl11 Se3 2.5899(19) . ?
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 C1 C6 122.3(7) . . ?
C2 C1 Se1 119.8(6) . . ?
C6 C1 Se1 118.0(6) . . ?
C1 C2 C3 119.5(7) . . ?
C2 C3 C4 118.6(8) . . ?
C5 C4 C3 122.1(7) . . ?
C5 C4 Cl4 118.9(6) . . ?
C3 C4 Cl4 119.0(6) . . ?
C4 C5 C6 120.1(7) . . ?
C1 C6 C5 117.5(7) . . ?
C12 C7 C8 121.5(7) . . ?
C12 C7 Se2 119.8(5) . . ?
C8 C7 Se2 118.7(6) . . ?
C9 C8 C7 119.0(7) . . ?
C10 C9 C8 119.2(7) . . ?
C9 C10 C11 122.4(7) . . ?
C9 C10 Cl8 120.0(6) . . ?
C11 C10 Cl8 117.6(6) . . ?
C10 C11 C12 119.2(7) . . ?
C7 C12 C11 118.6(7) . . ?
C14 C13 C18 122.5(7) . . ?
C14 C13 Se3 119.1(5) . . ?
C18 C13 Se3 118.4(5) . . ?
C13 C14 C15 119.0(7) . . ?
C16 C15 C14 118.8(7) . . ?
C15 C16 C17 122.0(7) . . ?
C15 C16 Cl12 118.5(6) . . ?
C17 C16 Cl12 119.6(6) . . ?
C18 C17 C16 119.1(7) . . ?
C17 C18 C13 118.6(7) . . ?
C1 Se1 Cl2 94.0(2) . . ?
C1 Se1 Cl1 95.0(2) . . ?
Cl2 Se1 Cl1 93.93(8) . . ?
C1 Se1 Cl3 89.8(2) . . ?
Cl2 Se1 Cl3 91.69(7) . . ?
Cl1 Se1 Cl3 172.30(7) . . ?
C7 Se2 Cl6 94.2(2) . . ?
C7 Se2 Cl7 94.7(2) . . ?
Cl6 Se2 Cl7 93.32(8) . . ?
C7 Se2 Cl5 92.2(2) . . ?
Cl6 Se2 Cl5 88.27(7) . . ?
Cl7 Se2 Cl5 172.76(7) . . ?
C13 Se3 Cl10 96.4(2) . . ?
C13 Se3 Cl9 93.9(2) . . ?
Cl10 Se3 Cl9 94.48(8) . . ?
C13 Se3 Cl11 91.2(2) . . ?
Cl10 Se3 Cl11 90.65(7) . . ?
Cl9 Se3 Cl11 172.31(7) . . ?
# END of CIF
# Attachment 'p-FC6H4SeBr3.cif'
#==============================================================================
#==============================================================================
#\#CIF_1.1
# CIF produced by WinGX routine CIF_UPDATE
# Created on 2012-07-03 at 23:44:36
# Using CIFtbx version 2.6.2 16 Jun 1998
# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\archive.reqdat
# CIF files read : r dreduc sortav struct
data_r_p-FC6H4SeBr3
_database_code_depnum_ccdc_archive 'CCDC 892019'
#TrackingRef 'p-FC6H4SeBr3.cif'
_audit_update_record
;
2012-09-13 # Formatted by publCIF
;
_audit_creation_date 2012-07-03T23:44:36-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.4
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic ?
_chemical_formula_moiety 'C12 H8 Br6 F2 Se2'
_chemical_formula_sum 'C12 H8 Br6 F2 Se2'
_chemical_formula_weight 827.56
_chemical_compound_source 'synthesis as described'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 17.7188(6)
_cell_length_b 9.1035(3)
_cell_length_c 23.4934(11)
_cell_angle_alpha 90
_cell_angle_beta 97.2360(10)
_cell_angle_gamma 90
_cell_volume 3759.4(3)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 5686
_cell_measurement_theta_min 2
_cell_measurement_theta_max 27
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description needle
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.06
_exptl_crystal_size_min 0.04
_exptl_crystal_density_diffrn 2.924
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 3008
_exptl_special_details ?
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 16.698
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.286
_exptl_absorpt_correction_T_max 0.5548
_exptl_absorpt_process_details
;
Blessing, R. H. (1995) Acta Cryst., A51, 33-38.
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 0.380563E-1
_diffrn_orient_matrix_ub_12 0.162658E-1
_diffrn_orient_matrix_ub_13 -0.02739
_diffrn_orient_matrix_ub_21 -0.304174E-1
_diffrn_orient_matrix_ub_22 -0.642521E-1
_diffrn_orient_matrix_ub_23 -0.288507E-1
_diffrn_orient_matrix_ub_31 -0.293769E-1
_diffrn_orient_matrix_ub_32 0.875994E-1
_diffrn_orient_matrix_ub_33 -0.160754E-1
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents 0.1175
_diffrn_reflns_av_unetI/netI 0.128
_diffrn_reflns_number 19016
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 2.98
_diffrn_reflns_theta_max 25.7
_diffrn_reflns_theta_full 25.7
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total 3551
_reflns_number_gt 2249
_reflns_threshold_expression >2\s(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^ > 2\s(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.
Deepest hole -2.75 at 0.1921 0.7724 0.3292 [ 0.96 A from BR5 ]
A total of 72 restraints were generated. These comprised 6 ISOR restraints
being applied on each of the carbon atoms C(1) to C(12).
;
_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^)+(0.0607P)^2^+22.1793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 3551
_refine_ls_number_parameters 199
_refine_ls_number_restraints 72
_refine_ls_R_factor_all 0.1272
_refine_ls_R_factor_gt 0.0803
_refine_ls_wR_factor_ref 0.2001
_refine_ls_wR_factor_gt 0.1792
_refine_ls_goodness_of_fit_ref 1.272
_refine_ls_restrained_S_all 1.262
_refine_ls_shift/su_max 0.006
_refine_ls_shift/su_mean 0.001
_refine_diff_density_max 1.645
_refine_diff_density_min -2.752
_refine_diff_density_rms 0.381
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 C 0.0808(8) 0.5159(17) 0.3477(6) 0.020(3) Uani 1 1 d U . .
C2 C 0.0929(9) 0.5315(19) 0.2913(6) 0.029(4) Uani 1 1 d U . .
H2 H 0.0985 0.6274 0.2764 0.035 Uiso 1 1 calc R . .
C3 C 0.0973(9) 0.411(2) 0.2552(7) 0.033(4) Uani 1 1 d U . .
H3 H 0.1045 0.4204 0.216 0.039 Uiso 1 1 calc R . .
C4 C 0.0902(8) 0.2744(19) 0.2813(6) 0.026(4) Uani 1 1 d U . .
C5 C 0.0810(9) 0.2543(17) 0.3357(6) 0.023(3) Uani 1 1 d U . .
H5 H 0.076 0.1582 0.3506 0.028 Uiso 1 1 calc R . .
C6 C 0.0787(8) 0.3797(18) 0.3713(6) 0.024(3) Uani 1 1 d U . .
H6 H 0.0758 0.3687 0.4112 0.029 Uiso 1 1 calc R . .
C7 C 0.2976(8) 0.4387(18) 0.3941(6) 0.022(3) Uani 1 1 d U . .
C8 C 0.3070(8) 0.453(2) 0.3347(6) 0.027(4) Uani 1 1 d U . .
H8 H 0.3203 0.5443 0.3194 0.033 Uiso 1 1 calc R . .
C9 C 0.2965(8) 0.3312(18) 0.3003(6) 0.023(3) Uani 1 1 d U . .
H9 H 0.3016 0.3374 0.2606 0.028 Uiso 1 1 calc R . .
C10 C 0.2784(9) 0.1994(19) 0.3243(7) 0.027(4) Uani 1 1 d U . .
C11 C 0.2731(8) 0.1800(18) 0.3819(6) 0.022(3) Uani 1 1 d U . .
H11 H 0.263 0.0865 0.3971 0.027 Uiso 1 1 calc R . .
C12 C 0.2833(8) 0.3054(18) 0.4168(6) 0.025(3) Uani 1 1 d U . .
H12 H 0.2803 0.2972 0.4567 0.03 Uiso 1 1 calc R . .
Br1 Br 0.01470(10) 0.8458(2) 0.32653(8) 0.0388(5) Uani 1 1 d . . .
Br2 Br -0.03225(9) 0.6163(2) 0.43639(7) 0.0345(5) Uani 1 1 d . . .
Br3 Br 0.38846(9) 0.48322(19) 0.52298(7) 0.0318(4) Uani 1 1 d . . .
Br4 Br 0.42254(9) 0.7036(2) 0.40631(7) 0.0327(4) Uani 1 1 d . . .
Br5 Br 0.22448(9) 0.77643(18) 0.36506(6) 0.0278(4) Uani 1 1 d . . .
Br6 Br 0.17215(8) 0.54509(18) 0.48827(6) 0.0252(4) Uani 1 1 d . . .
F1 F 0.0926(5) 0.1533(11) 0.2470(4) 0.034(2) Uani 1 1 d . . .
F2 F 0.2670(5) 0.0849(10) 0.2886(4) 0.032(2) Uani 1 1 d . . .
Se1 Se 0.07995(9) 0.68587(18) 0.39770(6) 0.0258(4) Uani 1 1 d . . .
Se2 Se 0.31319(9) 0.61190(18) 0.44342(6) 0.0240(4) 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
C1 0.009(5) 0.026(7) 0.024(6) 0.000(6) 0.000(5) 0.001(5)
C2 0.044(7) 0.024(7) 0.020(6) -0.005(6) 0.001(6) -0.005(6)
C3 0.031(7) 0.039(8) 0.028(7) 0.007(6) 0.002(6) 0.000(7)
C4 0.019(6) 0.030(7) 0.028(7) -0.011(6) 0.000(5) 0.002(6)
C5 0.030(7) 0.014(6) 0.025(6) 0.004(5) -0.001(5) 0.007(6)
C6 0.024(6) 0.030(7) 0.018(6) -0.008(6) 0.001(5) -0.006(6)
C7 0.022(6) 0.021(7) 0.021(6) -0.002(6) -0.005(5) 0.003(6)
C8 0.029(7) 0.030(7) 0.022(6) -0.008(6) -0.001(5) 0.008(6)
C9 0.020(6) 0.028(7) 0.022(6) -0.003(6) 0.001(5) -0.001(6)
C10 0.027(7) 0.030(8) 0.024(6) 0.002(6) -0.002(5) -0.003(6)
C11 0.022(6) 0.024(7) 0.021(6) -0.002(6) 0.000(5) -0.001(6)
C12 0.025(6) 0.029(7) 0.021(6) 0.006(6) 0.002(5) 0.008(6)
Br1 0.0441(10) 0.0311(10) 0.0369(10) 0.0021(8) -0.0112(7) 0.0071(9)
Br2 0.0276(9) 0.0367(11) 0.0389(9) -0.0055(8) 0.0033(7) -0.0013(8)
Br3 0.0361(9) 0.0324(10) 0.0245(8) -0.0026(7) -0.0053(6) 0.0051(8)
Br4 0.0274(9) 0.0329(10) 0.0378(9) -0.0033(8) 0.0039(7) -0.0062(8)
Br5 0.0363(9) 0.0226(9) 0.0237(8) 0.0028(7) 0.0009(6) -0.0032(7)
Br6 0.0269(8) 0.0251(9) 0.0229(8) 0.0001(7) 0.0002(6) -0.0010(7)
F1 0.041(5) 0.023(5) 0.036(5) -0.015(4) 0.004(4) -0.001(5)
F2 0.047(6) 0.023(5) 0.024(5) -0.008(4) -0.002(4) -0.003(5)
Se1 0.0283(8) 0.0247(9) 0.0231(8) -0.0019(7) -0.0019(6) -0.0002(8)
Se2 0.0262(8) 0.0234(9) 0.0217(8) -0.0016(7) 0.0005(6) -0.0019(7)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.36(2) . ?
C1 C2 1.38(2) . ?
C1 Se1 1.944(15) . ?
C2 C3 1.40(2) . ?
C2 H2 0.95 . ?
C3 C4 1.40(2) . ?
C3 H3 0.95 . ?
C4 C5 1.32(2) . ?
C4 F1 1.370(17) . ?
C5 C6 1.42(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.36(2) . ?
C7 C8 1.43(2) . ?
C7 Se2 1.956(15) . ?
C8 C9 1.37(2) . ?
C8 H8 0.95 . ?
C9 C10 1.38(2) . ?
C9 H9 0.95 . ?
C10 F2 1.337(18) . ?
C10 C11 1.38(2) . ?
C11 C12 1.40(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
Br1 Se1 2.401(2) . ?
Br2 Se1 2.374(2) . ?
Br3 Se2 2.453(2) . ?
Br4 Se2 2.374(2) . ?
Br5 Se2 2.716(2) . ?
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
C6 C1 C2 120.1(14) . . ?
C6 C1 Se1 118.4(11) . . ?
C2 C1 Se1 120.9(12) . . ?
C1 C2 C3 122.0(16) . . ?
C1 C2 H2 119 . . ?
C3 C2 H2 119 . . ?
C4 C3 C2 114.7(14) . . ?
C4 C3 H3 122.6 . . ?
C2 C3 H3 122.7 . . ?
C5 C4 F1 118.3(15) . . ?
C5 C4 C3 125.3(15) . . ?
F1 C4 C3 116.4(14) . . ?
C4 C5 C6 118.3(15) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.3(13) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C12 C7 C8 120.7(14) . . ?
C12 C7 Se2 120.3(11) . . ?
C8 C7 Se2 118.8(12) . . ?
C9 C8 C7 118.8(16) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 118.8(14) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
F2 C10 C11 119.5(14) . . ?
F2 C10 C9 116.5(13) . . ?
C11 C10 C9 124.1(15) . . ?
C10 C11 C12 116.7(15) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C7 C12 C11 120.8(14) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C1 Se1 Br2 95.1(4) . . ?
C1 Se1 Br1 95.8(4) . . ?
Br2 Se1 Br1 94.32(8) . . ?
C7 Se2 Br4 97.3(4) . . ?
C7 Se2 Br3 95.1(4) . . ?
Br4 Se2 Br3 93.28(8) . . ?
C7 Se2 Br5 90.9(4) . . ?
Br4 Se2 Br5 89.23(7) . . ?
Br3 Se2 Br5 173.09(8) . . ?
# END of CIF
# Attachment 'p-FC6H4SeCl3.cif'
#==============================================================================
#==============================================================================
#\#CIF_1.1
# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-07-24 at 14:17:20
# Using CIFtbx version 2.6.2 16 Jun 1998
# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : shelxl dreduc sortav struct
data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 892020'
#TrackingRef 'p-FC6H4SeCl3.cif'
_audit_update_record
;
2012-09-11 # Formatted by publCIF
;
_audit_creation_date 2009-07-24T14:17:20-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.3
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic ?
_chemical_formula_moiety 'C12 H8 Cl6 F2 Se2'
_chemical_formula_sum 'C12 H8 Cl6 F2 Se2'
_chemical_formula_weight 560.8
_chemical_compound_source 'synthesis as described'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 17.4590(6)
_cell_length_b 8.7778(3)
_cell_length_c 23.2622(9)
_cell_angle_alpha 90
_cell_angle_beta 100.7710(10)
_cell_angle_gamma 90
_cell_volume 3502.2(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 3446
_cell_measurement_theta_min 2
_cell_measurement_theta_max 27
_cell_measurement_wavelength 0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.05
_exptl_crystal_density_diffrn 2.127
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2144
_exptl_special_details ?
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu 5.147
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min 0.5771
_exptl_absorpt_correction_T_max 0.7829
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source 'Enraf Nonius FR590'
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11 -0.500778E-1
_diffrn_orient_matrix_ub_12 -0.520789E-1
_diffrn_orient_matrix_ub_13 0.29013E-2
_diffrn_orient_matrix_ub_21 0.298595E-1
_diffrn_orient_matrix_ub_22 -0.875593E-1
_diffrn_orient_matrix_ub_23 0.206706E-1
_diffrn_orient_matrix_ub_31 0.1271E-3
_diffrn_orient_matrix_ub_32 0.509881E-1
_diffrn_orient_matrix_ub_33 0.03846
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type KappaCCD
_diffrn_measurement_method 'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents 0.088
_diffrn_reflns_av_unetI/netI 0.0635
_diffrn_reflns_number 12163
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 3.23
_diffrn_reflns_theta_max 26
_diffrn_reflns_theta_full 26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total 3423
_reflns_number_gt 2260
_reflns_threshold_expression >2sigma(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection 'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^)+(0.0612P)^2^+39.9270P] 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_number_reflns 3423
_refine_ls_number_parameters 199
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1067
_refine_ls_R_factor_gt 0.0664
_refine_ls_wR_factor_ref 0.1773
_refine_ls_wR_factor_gt 0.1543
_refine_ls_goodness_of_fit_ref 1.276
_refine_ls_restrained_S_all 1.276
_refine_ls_shift/su_max 0
_refine_ls_shift/su_mean 0
_refine_diff_density_max 1.469
_refine_diff_density_min -0.934
_refine_diff_density_rms 0.233
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 C 0.1965(5) 0.4406(10) 0.6056(3) 0.028(2) Uani 1 1 d . . .
C2 C 0.2102(5) 0.3022(9) 0.5814(4) 0.028(2) Uani 1 1 d . . .
H2 H 0.2144 0.2941 0.5414 0.034 Uiso 1 1 calc R . .
C3 C 0.2176(6) 0.1752(10) 0.6174(4) 0.037(2) Uani 1 1 d . . .
H3 H 0.2274 0.0779 0.6023 0.044 Uiso 1 1 calc R . .
C4 C 0.2108(5) 0.1907(10) 0.6744(4) 0.028(2) Uani 1 1 d . . .
C5 C 0.1974(5) 0.3279(9) 0.6989(4) 0.030(2) Uani 1 1 d . . .
H5 H 0.1936 0.3344 0.739 0.036 Uiso 1 1 calc R . .
C6 C 0.1893(5) 0.4582(10) 0.6636(3) 0.028(2) Uani 1 1 d . . .
H6 H 0.1793 0.555 0.6788 0.033 Uiso 1 1 calc R . .
C7 C 0.4184(5) 0.4898(10) 0.6502(4) 0.028(2) Uani 1 1 d . . .
C8 C 0.4255(5) 0.3484(9) 0.6245(4) 0.029(2) Uani 1 1 d . . .
H8 H 0.4325 0.3419 0.585 0.035 Uiso 1 1 calc R . .
C9 C 0.4223(5) 0.2177(10) 0.6571(4) 0.032(2) Uani 1 1 d . . .
H9 H 0.4284 0.12 0.641 0.039 Uiso 1 1 calc R . .
C10 C 0.4100(6) 0.2332(10) 0.7134(4) 0.032(2) Uani 1 1 d . . .
C11 C 0.4005(6) 0.3719(10) 0.7394(4) 0.033(2) Uani 1 1 d . . .
H11 H 0.3919 0.3772 0.7785 0.04 Uiso 1 1 calc R . .
C12 C 0.4041(5) 0.5049(10) 0.7062(4) 0.031(2) Uani 1 1 d . . .
H12 H 0.3968 0.6025 0.722 0.037 Uiso 1 1 calc R . .
F4 F 0.2186(3) 0.0648(6) 0.7092(2) 0.0398(13) Uani 1 1 d . . .
F10 F 0.4072(3) 0.1056(6) 0.7458(2) 0.0425(14) Uani 1 1 d . . .
Se1 Se 0.18799(5) 0.62293(9) 0.55607(4) 0.0282(3) Uani 1 1 d . . .
Se2 Se 0.41802(5) 0.67313(10) 0.60251(4) 0.0288(3) Uani 1 1 d . . .
Cl1 Cl 0.28126(14) 0.7654(2) 0.63586(9) 0.0320(5) Uani 1 1 d . . .
Cl2 Cl 0.08870(15) 0.7202(3) 0.58949(11) 0.0400(6) Uani 1 1 d . . .
Cl3 Cl 0.11056(15) 0.5040(3) 0.47960(10) 0.0376(6) Uani 1 1 d . . .
Cl4 Cl 0.32168(13) 0.5401(2) 0.51614(9) 0.0284(5) Uani 1 1 d . . .
Cl5 Cl 0.51909(14) 0.6086(3) 0.56466(10) 0.0371(6) Uani 1 1 d . . .
Cl6 Cl 0.48765(15) 0.8100(3) 0.67467(10) 0.0398(6) 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
C1 0.032(5) 0.033(5) 0.018(4) 0.008(3) 0.000(4) 0.002(4)
C2 0.022(5) 0.033(5) 0.028(5) -0.006(4) 0.000(4) -0.003(4)
C3 0.058(7) 0.029(5) 0.020(5) -0.003(4) -0.002(4) -0.002(5)
C4 0.023(5) 0.034(5) 0.026(5) 0.007(4) -0.001(4) -0.007(4)
C5 0.035(5) 0.028(4) 0.026(5) 0.006(4) 0.007(4) 0.002(4)
C6 0.029(5) 0.028(4) 0.025(5) 0.002(3) 0.001(4) 0.011(4)
C7 0.031(5) 0.034(5) 0.017(4) 0.004(3) -0.002(4) 0.006(4)
C8 0.036(5) 0.027(4) 0.025(5) 0.003(4) 0.006(4) -0.001(4)
C9 0.032(5) 0.023(4) 0.041(6) 0.000(4) 0.002(4) -0.003(4)
C10 0.032(5) 0.027(4) 0.037(5) 0.007(4) 0.003(4) 0.000(4)
C11 0.040(6) 0.036(5) 0.024(5) 0.007(4) 0.006(4) 0.004(4)
C12 0.019(5) 0.037(5) 0.036(5) 0.006(4) 0.002(4) 0.008(4)
F4 0.056(4) 0.032(3) 0.031(3) 0.005(2) 0.010(3) 0.001(3)
F10 0.046(4) 0.036(3) 0.046(3) 0.016(2) 0.011(3) 0.007(3)
Se1 0.0317(5) 0.0277(5) 0.0242(5) 0.0027(3) 0.0025(4) 0.0038(4)
Se2 0.0309(5) 0.0273(5) 0.0263(5) 0.0012(3) 0.0007(4) 0.0015(4)
Cl1 0.0431(14) 0.0270(10) 0.0245(11) -0.0020(8) 0.0028(10) 0.0034(10)
Cl2 0.0377(14) 0.0426(13) 0.0411(14) 0.0042(10) 0.0108(11) 0.0123(11)
Cl3 0.0430(15) 0.0351(12) 0.0295(12) 0.0013(9) -0.0064(10) -0.0048(10)
Cl4 0.0335(13) 0.0272(10) 0.0239(11) 0.0002(8) 0.0040(9) 0.0035(9)
Cl5 0.0321(13) 0.0437(13) 0.0362(13) 0.0052(10) 0.0079(10) 0.0018(10)
Cl6 0.0461(15) 0.0344(12) 0.0336(13) -0.0027(9) -0.0063(11) -0.0067(11)
#----------------------------------------------------------------------------#
# 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
C1 C2 1.378(12) . ?
C1 C6 1.386(11) . ?
C1 Se1 1.962(8) . ?
C2 C3 1.385(12) . ?
C2 H2 0.95 . ?
C3 C4 1.361(12) . ?
C3 H3 0.95 . ?
C4 F4 1.362(9) . ?
C4 C5 1.370(12) . ?
C5 C6 1.400(11) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.377(12) . ?
C7 C8 1.394(12) . ?
C7 Se2 1.954(8) . ?
C8 C9 1.382(12) . ?
C8 H8 0.95 . ?
C9 C10 1.371(13) . ?
C9 H9 0.95 . ?
C10 F10 1.357(10) . ?
C10 C11 1.383(13) . ?
C11 C12 1.407(12) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
Se1 Cl2 2.201(3) . ?
Se1 Cl3 2.277(2) . ?
Se1 Cl1 2.556(2) . ?
Se2 Cl5 2.189(3) . ?
Se2 Cl6 2.231(2) . ?
Se2 Cl4 2.639(2) . ?
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 C1 C6 123.3(8) . . ?
C2 C1 Se1 118.6(6) . . ?
C6 C1 Se1 118.0(6) . . ?
C1 C2 C3 117.8(8) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.5(8) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 F4 118.7(8) . . ?
C3 C4 C5 123.1(8) . . ?
F4 C4 C5 118.2(8) . . ?
C4 C5 C6 118.7(8) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 117.5(8) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C12 C7 C8 122.5(8) . . ?
C12 C7 Se2 118.5(6) . . ?
C8 C7 Se2 118.7(6) . . ?
C9 C8 C7 119.1(8) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 118.1(8) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
F10 C10 C9 118.5(8) . . ?
F10 C10 C11 117.6(8) . . ?
C9 C10 C11 123.9(8) . . ?
C10 C11 C12 117.9(8) . . ?
C10 C11 H11 121 . . ?
C12 C11 H11 121 . . ?
C7 C12 C11 118.3(8) . . ?
C7 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C1 Se1 Cl2 95.0(3) . . ?
C1 Se1 Cl3 93.1(3) . . ?
Cl2 Se1 Cl3 93.55(10) . . ?
C1 Se1 Cl1 90.3(3) . . ?
Cl2 Se1 Cl1 89.46(9) . . ?
Cl3 Se1 Cl1 175.28(9) . . ?
C7 Se2 Cl5 95.6(3) . . ?
C7 Se2 Cl6 94.2(3) . . ?
Cl5 Se2 Cl6 94.31(10) . . ?
C7 Se2 Cl4 90.1(3) . . ?
Cl5 Se2 Cl4 91.50(8) . . ?
Cl6 Se2 Cl4 172.40(9) . . ?