# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full 'Chemical Science'
_journal_coden_cambridge 1475
_journal_coden_ASTM ?
_journal_coeditor_code ?
_journal_coeditor_name ?
_journal_coeditor_notes
;
?
;
_journal_date_accepted ?
_journal_date_from_coeditor ?
_journal_date_printers_final ?
_journal_date_printers_first ?
_journal_date_proofs_in ?
_journal_date_proofs_out ?
#=============================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
_journal_techeditor_code ?
_journal_techeditor_notes
;
?
;
_journal_volume ?
_journal_year ?
loop_
_publ_author_name
_publ_author_address
T.Fallon
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
A.C.Willis
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
A.D.Rae
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
M.N.Paddon-Row
;
School of Chemistry,
The University of New South Wales,
Sydney, N. S. W. 2052, Australia
;
M.S.Sherburn
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email sherburn@rsc.anu.edu.au
_publ_contact_author_fax ' 61 2 6125 8114 '
_publ_contact_author_phone ' 61 2 6125 4988 '
_publ_contact_author_name 'Michael S. Sherburn'
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_category ' fo '
_publ_requested_coeditor_name ?
#=============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
beta-Oligofurans
;
data_she0627
_database_code_depnum_ccdc_archive 'CCDC 860334'
_audit_creation_date 06-10-16
_audit_creation_method CRYSTALS_ver_12.18
_audit_update_record
;
2006-10-17 - Report on C8 H4 Br2 O2
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2006-10-17 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '10161641 she0627'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 17.3296(6)
_cell_length_b 3.8995(1)
_cell_length_c 13.8867(5)
_cell_angle_alpha 90
_cell_angle_beta 114.947(2)
_cell_angle_gamma 90
_cell_volume 850.86(5)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 1 2/c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C8 H4 Br2 O2
# Dc = 2.28 Fooo = 552.00 Mu = 94.77 M = 145.96
# Found Formula = C8 H4 Br2 O2
# Dc = 2.28 FOOO = 552.00 Mu = 94.77 M = 145.96
_chemical_formula_sum 'C8 H4 Br2 O2'
_chemical_formula_moiety 'C8 H4 Br2 O2'
_chemical_compound_source local
_chemical_formula_weight 291.93
_cell_measurement_reflns_used 5266
_cell_measurement_theta_min 3
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.04
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_max 0.26
_exptl_crystal_density_diffrn 2.279
_exptl_crystal_density_meas 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 552
_exptl_absorpt_coefficient_mu 9.477
# Sheldrick geometric approximatio 0.32 0.68
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.080
-1 0 0 0.040
0 1 0 0.120
0 -1 0 0.140
0 0 1 0.010
0 0 -1 0.035
-16 -1 0 0.050
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.241
_exptl_absorpt_correction_T_max 0.671
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.030
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 100 sec/frame,
crystal-detector distance 40mm,
multiple scan sets so over 95 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius BV, 1997)'
_computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement 'CRYSTALS (Watkin et al 2003)'
_computing_publication_material 'CRYSTALS (Watkin et al 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 6439
_reflns_number_total 968
_diffrn_reflns_av_R_equivalents 0.037
# Number of reflections with Friedels Law is 968
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 975
_diffrn_reflns_theta_min 4.821
_diffrn_reflns_theta_max 27.481
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 27.481
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 4
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_reflns_limit_h_min -22
_reflns_limit_h_max 20
_reflns_limit_k_min 0
_reflns_limit_k_max 5
_reflns_limit_l_min 0
_reflns_limit_l_max 18
_oxford_diffrn_Wilson_B_factor 2.58
_oxford_diffrn_Wilson_scale 3.63
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.33
_refine_diff_density_max 0.66
_refine_ls_number_reflns 835
_refine_ls_number_restraints 0
_refine_ls_number_parameters 62
#_refine_ls_R_factor_ref 0.0205
_refine_ls_wR_factor_ref 0.0225
_refine_ls_goodness_of_fit_ref 1.1356
#_reflns_number_all 968
_refine_ls_R_factor_all 0.0234
_refine_ls_wR_factor_all 0.0244
# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression I>3.0\s(I)
_reflns_number_gt 835
_refine_ls_R_factor_gt 0.0205
_refine_ls_wR_factor_gt 0.0225
_refine_ls_shift/su_max 0.001536
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial,
(Carruthers & Watkin, 1979, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
-0.522 4.42 -1.13 1.56
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~8~H~4~Br~2~O~2~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of
one half of the C~8~H~4~Br~2~O~2~ molecule.
The other half of the molecule is completed by a
crystallographic two-fold symmetry operation.
All H atoms were observed in a
difference electron density map prior to their inclusion.
They were included at
idealized positions and refined positionally.
The major peaks in the final difference electron density map
are located near the Br atom.
;
_publ_section_acknowledgements # Acknowledgments
;
?
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms were
included at idealized positions and refined positionally.
;
_publ_section_exptl_prep
;
The compound was prepared by TF and recrystallized from
petrol. The sample ID is tf-dibrbifur.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. 27, 435-435
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294
Nonius BV, COLLECT Software, 1997-2001)
Otwinowski, Z. & Minor, W. (1997), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Carruthers, J.R. & Watkin, D.J. (1979),
Acta Cryst. A35, 698-699.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976)
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.42469(11) 0.7346(5) 0.51642(13) 0.0413 1.0000 Uani . . . . . .
C2 C 0.49218(16) 0.7767(6) 0.61295(18) 0.0352 1.0000 Uani . . . . . .
C3 C 0.47216(13) 0.6801(5) 0.69310(16) 0.0273 1.0000 Uani . . . . . .
C4 C 0.38520(14) 0.5691(5) 0.64146(18) 0.0286 1.0000 Uani . . . . . .
C5 C 0.35941(15) 0.6049(6) 0.53598(19) 0.0356 1.0000 Uani . . . . . .
Br6 Br 0.318300(13) 0.39638(5) 0.706810(18) 0.0344 1.0000 Uani . . . . . .
H21 H 0.541(2) 0.868(7) 0.614(3) 0.0434 1.0000 Uiso . . . . . .
H51 H 0.308(2) 0.537(8) 0.470(2) 0.0423 1.0000 Uiso . . . . . .
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
O1 0.0396(9) 0.0563(11) 0.0309(8) 0.0026(8) 0.0177(7) -0.0019(8)
C2 0.0338(11) 0.0418(13) 0.0341(11) 0.0019(10) 0.0184(9) -0.0011(10)
C3 0.0295(10) 0.0250(9) 0.0313(11) -0.0007(8) 0.0164(9) 0.0006(8)
C4 0.0299(10) 0.0244(10) 0.0354(11) -0.0004(8) 0.0175(9) 0.0010(8)
C5 0.0326(10) 0.0397(13) 0.0343(11) -0.0023(9) 0.0138(9) -0.0016(10)
Br6 0.03328(15) 0.03114(15) 0.04490(17) 0.00044(8) 0.02243(11) -0.00263(9)
_refine_ls_extinction_coef 30(3)
_refine_ls_extinction_method 'Larson (1970), Equation 22'
_oxford_refine_ls_scale 0.7540(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.367(3) yes
O1 . C5 . 1.367(3) yes
C2 . C3 . 1.352(3) yes
C2 . H21 . 0.92(4) no
C3 . C3 5_656 1.464(4) yes
C3 . C4 . 1.435(3) yes
C4 . C5 . 1.346(3) yes
C4 . Br6 . 1.873(2) yes
C5 . H51 . 1.01(3) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C5 . 106.68(18) yes
O1 . C2 . C3 . 111.3(2) yes
O1 . C2 . H21 . 118(2) no
C3 . C2 . H21 . 131(2) no
C3 5_656 C3 . C2 . 127.4(2) yes
C3 5_656 C3 . C4 . 127.9(2) yes
C2 . C3 . C4 . 104.63(19) yes
C3 . C4 . C5 . 108.0(2) yes
C3 . C4 . Br6 . 126.88(17) yes
C5 . C4 . Br6 . 125.10(18) yes
O1 . C5 . C4 . 109.4(2) yes
O1 . C5 . H51 . 113.6(17) no
C4 . C5 . H51 . 136.6(17) no
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C2 3.334(4) . 2_676 no
O1 O1 3.372(4) . 2_666 no
O1 C2 3.385(4) . 2_666 no
O1 O1 3.509(4) . 2_676 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br6 C4 C3 C2 . . . . 179.1(2) no
Br6 C4 C3 C3 . . . 5_656 0.7(3) no
Br6 C4 C5 O1 . . . . -179.3(2) no
O1 C2 C3 C3 . . . 5_656 178.5(2) no
O1 C2 C3 C4 . . . . 0.1(3) no
O1 C5 C4 C3 . . . . -0.3(3) no
C2 O1 C5 C4 . . . . 0.4(3) no
C2 C3 C3 C2 . . 5_656 5_656 138.9(4) no
C2 C3 C3 C4 . . 5_656 5_656 -43.0(2) no
C2 C3 C4 C5 . . . . 0.1(2) no
C3 C2 O1 C5 . . . . -0.3(3) no
C3 C3 C4 C5 . 5_656 5_656 5_656 -178.3(2) no
C4 C3 C3 C4 . . 5_656 5_656 135.1(4) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd8_she0710.cif'
data_she0710
_database_code_depnum_ccdc_archive 'CCDC 860335'
_audit_creation_date 07-05-31
_audit_creation_method CRYSTALS_ver_12.18
_audit_update_record
;
2007-05-31 - Report on C16 H8 Br2 O4
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2007-05-31 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '5311504 she0710'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 13.2036(4)
_cell_length_b 7.7069(2)
_cell_length_c 14.7968(5)
_cell_angle_alpha 90
_cell_angle_beta 107.1542(15)
_cell_angle_gamma 90
_cell_volume 1438.72(8)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 1 2/c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C16 H8 Br2 O4
# Dc = 1.96 Fooo = 824.00 Mu = 56.49 M = 212.02
# Found Formula = C16 H8 Br2 O4
# Dc = 1.96 FOOO = 824.00 Mu = 56.49 M = 212.02
_chemical_formula_sum 'C16 H8 Br2 O4'
_chemical_formula_moiety 'C16 H8 Br2 O4'
_chemical_compound_source local
_chemical_formula_weight 424.05
_cell_measurement_reflns_used 9945
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.04
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_max 0.40
_exptl_crystal_density_diffrn 1.958
_exptl_crystal_density_meas ' not measured '
# Non-dispersive F(000):
_exptl_crystal_F_000 824
_exptl_absorpt_coefficient_mu 5.649
# Sheldrick geometric approximatio 0.29 0.80
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.120
-1 0 0 0.100
0 1 0 0.200
0 -1 0 0.200
0 0 1 0.030
0 0 -1 0.015
-4 -5 1 0.157
-6 1 2 0.110
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.256
_exptl_absorpt_correction_T_max 0.779
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.043
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 240 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 95 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius BV, 1997)'
_computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement 'CRYSTALS (Watkin et al 2003)'
_computing_publication_material 'CRYSTALS (Watkin et al 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 13994
_reflns_number_total 1642
_diffrn_reflns_av_R_equivalents 0.060
# Number of reflections with Friedels Law is 1642
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1655
_diffrn_reflns_theta_min 3.612
_diffrn_reflns_theta_max 27.517
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 27.5 # 26.966
_diffrn_measured_fraction_theta_full 0.995 # 0.996
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_reflns_limit_h_min -17
_reflns_limit_h_max 16
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 19
_oxford_diffrn_Wilson_B_factor 3.32
_oxford_diffrn_Wilson_scale 5.06
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.92
_refine_diff_density_max 0.33
_refine_ls_number_reflns 1200
_refine_ls_number_restraints 0
_refine_ls_number_parameters 112
#_refine_ls_R_factor_ref 0.0272
_refine_ls_wR_factor_ref 0.0310
_refine_ls_goodness_of_fit_ref 1.1093
#_reflns_number_all 1639
_refine_ls_R_factor_all 0.0367
_refine_ls_wR_factor_all 0.0393
# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression I>3.0\s(I)
_reflns_number_gt 1200
_refine_ls_R_factor_gt 0.0272
_refine_ls_wR_factor_gt 0.0310
_refine_ls_shift/su_max 0.000755
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial,
(Carruthers & Watkin, 1979, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.985 0.324 0.543
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~16~H~8~Br~2~O~4~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of
one half of the C~16~H~8~Br~2~O~4~ molecule.
The other half of the molecule is completed by a
crystallographic two-fold symmetry operation.
All H atoms were observed in a
difference electron density map prior to their inclusion.
They were included at
idealized positions and refined positionally.
The major peaks in the final difference electron density map
are located near the Br atom.
;
_publ_section_acknowledgements # Acknowledgments
;
?
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms were
included at idealized positions and refined positionally.
;
_publ_section_exptl_prep
;
The compound was prepared by TF and recrystallized from
petrol/dichloromethane. The sample ID is tf-Br~2~Fu~4~.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. 27, 435-435
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294
Nonius BV, COLLECT Software, 1997-2001)
Otwinowski, Z. & Minor, W. (1997), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Carruthers, J.R. & Watkin, D.J. (1979),
Acta Cryst. A35, 698-699.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976)
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.66689(2) 0.23747(3) 0.57511(2) 0.0490 1.0000 Uani . . . . . .
C2 C 0.53619(19) 0.2774(3) 0.59627(17) 0.0332 1.0000 Uani . . . . . .
C3 C 0.4576(2) 0.1596(3) 0.58174(19) 0.0391 1.0000 Uani . . . . . .
O4 O 0.37320(15) 0.2300(2) 0.60288(14) 0.0412 1.0000 Uani . . . . . .
C5 C 0.4009(2) 0.3968(3) 0.63204(19) 0.0376 1.0000 Uani . . . . . .
C6 C 0.50091(18) 0.4346(3) 0.63041(16) 0.0310 1.0000 Uani . . . . . .
C7 C 0.55903(17) 0.5962(3) 0.66012(16) 0.0308 1.0000 Uani . . . . . .
C8 C 0.6414(2) 0.6576(3) 0.63211(19) 0.0382 1.0000 Uani . . . . . .
O9 O 0.67463(14) 0.8144(2) 0.67289(14) 0.0417 1.0000 Uani . . . . . .
C10 C 0.61195(19) 0.8520(3) 0.72903(19) 0.0377 1.0000 Uani . . . . . .
C11 C 0.54018(18) 0.7246(3) 0.72454(17) 0.0307 1.0000 Uani . . . . . .
H31 H 0.452(2) 0.051(4) 0.559(2) 0.0466 1.0000 Uiso . . . . . .
H51 H 0.348(2) 0.470(4) 0.648(2) 0.0454 1.0000 Uiso . . . . . .
H81 H 0.673(2) 0.615(5) 0.590(2) 0.0467 1.0000 Uiso . . . . . .
H101 H 0.625(2) 0.956(4) 0.763(2) 0.0447 1.0000 Uiso . . . . . .
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
Br1 0.03539(16) 0.04366(17) 0.0735(2) -0.00708(13) 0.02436(13) 0.00172(10)
C2 0.0292(11) 0.0362(11) 0.0363(12) 0.0003(9) 0.0130(9) 0.0005(9)
C3 0.0406(13) 0.0341(12) 0.0441(13) -0.0063(10) 0.0149(11) -0.0051(9)
O4 0.0344(9) 0.0431(10) 0.0495(10) -0.0077(8) 0.0178(8) -0.0122(7)
C5 0.0312(11) 0.0364(12) 0.0479(13) -0.0074(10) 0.0159(10) -0.0069(9)
C6 0.0277(10) 0.0312(10) 0.0352(11) 0.0010(9) 0.0111(9) -0.0018(8)
C7 0.0268(10) 0.0290(10) 0.0373(11) 0.0030(9) 0.0106(9) -0.0007(8)
C8 0.0344(12) 0.0377(12) 0.0466(14) 0.0018(10) 0.0181(11) -0.0057(9)
O9 0.0369(9) 0.0362(9) 0.0566(11) 0.0023(8) 0.0208(8) -0.0097(7)
C10 0.0333(11) 0.0288(11) 0.0518(14) 0.0005(10) 0.0138(10) -0.0037(9)
C11 0.0263(10) 0.0268(10) 0.0384(11) 0.0026(9) 0.0089(9) 0.0007(8)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.5906(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.868(2) yes
C2 . C3 . 1.347(3) yes
C2 . C6 . 1.442(3) yes
C3 . O4 . 1.356(3) yes
C3 . H31 . 0.90(3) no
O4 . C5 . 1.371(3) yes
C5 . C6 . 1.360(3) yes
C5 . H51 . 0.98(3) no
C6 . C7 . 1.461(3) yes
C7 . C8 . 1.357(3) yes
C7 . C11 . 1.445(3) yes
C8 . O9 . 1.364(3) yes
C8 . H81 . 0.91(3) no
O9 . C10 . 1.366(3) yes
C10 . C11 . 1.353(3) yes
C10 . H101 . 0.93(3) no
C11 . C11 5_656 1.471(5) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 124.62(19) yes
Br1 . C2 . C6 . 127.39(17) yes
C3 . C2 . C6 . 108.0(2) yes
C2 . C3 . O4 . 109.9(2) yes
C2 . C3 . H31 . 131(2) no
O4 . C3 . H31 . 119(2) no
C3 . O4 . C5 . 106.65(19) yes
O4 . C5 . C6 . 111.4(2) yes
O4 . C5 . H51 . 118.0(18) no
C6 . C5 . H51 . 130.5(18) no
C2 . C6 . C5 . 104.0(2) yes
C2 . C6 . C7 . 128.8(2) yes
C5 . C6 . C7 . 127.1(2) yes
C6 . C7 . C8 . 127.0(2) yes
C6 . C7 . C11 . 127.2(2) yes
C8 . C7 . C11 . 105.8(2) yes
C7 . C8 . O9 . 110.8(2) yes
C7 . C8 . H81 . 131(2) no
O9 . C8 . H81 . 118(2) no
C8 . O9 . C10 . 106.47(18) yes
O9 . C10 . C11 . 110.9(2) yes
O9 . C10 . H101 . 117.4(19) no
C11 . C10 . H101 . 131.7(19) no
C11 5_656 C11 . C7 . 128.91(16) yes
C11 5_656 C11 . C10 . 125.12(18) yes
C7 . C11 . C10 . 106.0(2) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O9 3.556(2) . 1_545 no
Br1 Br1 3.5598(6) . 4_656 no
Br1 C10 3.566(2) . 7_646 no
O4 O9 3.158(3) . 3_445 no
O4 C8 3.263(4) . 3_445 no
O4 C8 3.533(4) . 2_666 no
O9 C5 3.280(4) . 3 no
C2 C8 3.535(3) . 2_666 no
C3 C8 3.356(4) . 2_666 no
C3 C10 3.450(3) . 1_545 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C2 C3 O4 . . . . -179.4(2) no
Br1 C2 C6 C5 . . . . 179.3(2) no
Br1 C2 C6 C7 . . . . -2.8(4) no
O4 C3 C2 C6 . . . . 0.8(3) no
O4 C5 C6 C2 . . . . 0.7(3) no
O4 C5 C6 C7 . . . . -177.3(2) no
O9 C8 C7 C6 . . . . 178.7(2) no
O9 C8 C7 C11 . . . . -0.7(2) no
O9 C10 C11 C7 . . . . -0.1(3) no
O9 C10 C11 C11 . . . 5_656 -179.3(2) no
C2 C3 O4 C5 . . . . -0.4(3) no
C2 C6 C7 C8 . . . . 25.5(4) no
C2 C6 C7 C11 . . . . -155.2(2) no
C3 O4 C5 C6 . . . . -0.2(3) no
C3 C2 C6 C5 . . . . -0.9(3) no
C3 C2 C6 C7 . . . . 177.1(2) no
C5 C6 C7 C8 . . . . -157.0(3) no
C5 C6 C7 C11 . . . . 22.3(4) no
C6 C7 C11 C10 . . . . -179.0(2) no
C6 C7 C11 C11 . . . 5_656 0.2(4) no
C7 C8 O9 C10 . . . . 0.6(2) no
C7 C11 C11 C7 . . 5_656 5_656 56.8(5) no
C7 C11 C11 C10 . . 5_656 5_656 -124.2(2) no
C8 O9 C10 C11 . . . . -0.3(3) no
C8 C7 C11 C10 . . . . 0.5(2) no
C8 C7 C11 C11 . . . 5_656 179.6(2) no
C10 C11 C11 C10 . . 5_656 5_656 54.8(5) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd9_she1001.cif'
data_she1001
_database_code_depnum_ccdc_archive 'CCDC 860336'
_audit_creation_date 10-01-20
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2010-01-21 - Report on C32 H16 Br2 O8
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2010-01-21 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '1201509 she1001'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 13.3084(3)
_cell_length_b 6.8541(2)
_cell_length_c 29.0760(8)
_cell_angle_alpha 90
_cell_angle_beta 93.4770(11)
_cell_angle_gamma 90
_cell_volume 2647.35(12)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 1 2/c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C32 H16 Br2 O8
# Dc = 1.73 Fooo = 1368.00 Mu = 31.18 M = 344.14
# Found Formula = C32 H16 Br2 O8
# Dc = 1.73 FOOO = 1368.00 Mu = 31.18 M = 344.14
_chemical_formula_sum 'C32 H16 Br2 O8'
_chemical_formula_moiety 'C32 H16 Br2 O8'
_chemical_compound_source local
_chemical_formula_weight 688.28
_cell_measurement_reflns_used 79153
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 200
_exptl_crystal_description lath
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.020
_exptl_crystal_size_mid 0.110
_exptl_crystal_size_max 0.300
_exptl_crystal_density_diffrn 1.727
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1368
_exptl_absorpt_coefficient_mu 3.118
# Sheldrick geometric approximatio 0.71 0.94
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.66 # 0.94*8.20/11.60 scale range # 0.71
_exptl_absorpt_correction_T_max 0.94
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 0.5 deg at rate 90 sec/frame,
crystal-detector distance 40mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 21480 # 2328
_reflns_number_total 2328
_diffrn_reflns_av_R_equivalents 0.058
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 2328
# Theoretical number of reflections is about 4664
_diffrn_reflns_theta_min 2.807
_diffrn_reflns_theta_max 25.003
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.003
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_limit_l_max 34
_reflns_limit_h_min -15
_reflns_limit_h_max 15
_reflns_limit_k_min 0
_reflns_limit_k_max 8
_reflns_limit_l_min 0
_reflns_limit_l_max 34
_oxford_diffrn_Wilson_B_factor 3.56
_oxford_diffrn_Wilson_scale 40.31
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -1.01
_refine_diff_density_max 0.92
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 2315
_refine_ls_number_restraints 0
_refine_ls_number_parameters 190
_oxford_refine_ls_R_factor_ref 0.0973
_refine_ls_wR_factor_ref 0.1756
_refine_ls_goodness_of_fit_ref 1.0211
_refine_ls_shift/su_max 0.0001207
_refine_ls_shift/su_mean 0.9270998
# The values computed from all data
_oxford_reflns_number_all 2315
_refine_ls_R_factor_all 0.0973
_refine_ls_wR_factor_all 0.1756
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1955
_refine_ls_R_factor_gt 0.0848
_refine_ls_wR_factor_gt 0.1725
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
34.7 49.9 25.0 6.75
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~32~H~16~Br~2~O~8~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one-half of a
molecule of C~32~H~16~Br~2~O~8~.
The other half of the molecule is generated by a crystallographic
twofold rotation symmetry operation.
The crystals supplied were very thin plates and generally intergrown.
One extremely thin plate was selected and used for this study.
Data are weak and long exposure times were used.
Intensity data were scaled by multi-scan inter-frame methods
(DENZO/SCALEPACK, Otwinowski & Minor, 1997) to
correct for any miscentring of
the crystal (G\"orbitz, 1999) as well as for absorption and decay.
The compound is clearly identified although the
precision of the bond lengths and angles is not particularly good.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
Hydrogen atoms were included at idealized positions and
were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98\%A) and with
U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom,
after which the positions were refined with riding constraints.
The largest peaks in the final difference electron density map
are located near the Br atom.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from chloroform.
The sample ID is tf715-Br~2~Fu~8~.
;
_refine_special_details
;
Hydrogen atoms were included at idealized positions and
were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98\%A) and with
U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom,
after which the positions were refined with riding constraints.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 0.88225(7) 0.03537(16) 0.46426(4) 0.0533 1.0000 Uani . . . . . . .
O13 O 0.5821(4) 0.0287(10) 0.4461(2) 0.0500 1.0000 Uani . . . . . . .
O23 O 0.8610(4) 0.6361(10) 0.3887(2) 0.0527 1.0000 Uani . . . . . . .
O33 O 0.4397(4) 0.6425(9) 0.3314(2) 0.0446 1.0000 Uani . . . . . . .
O43 O 0.7109(4) 0.0108(9) 0.2779(2) 0.0440 1.0000 Uani . . . . . . .
C11 C 0.7444(6) 0.0774(14) 0.4505(3) 0.0408 1.0000 Uani . . . . . . .
C12 C 0.6713(8) -0.0374(17) 0.4616(3) 0.0552 1.0000 Uani . . . . . . .
C14 C 0.5994(6) 0.2004(13) 0.4233(3) 0.0392 1.0000 Uani . . . . . . .
C15 C 0.6984(6) 0.2412(13) 0.4249(3) 0.0350 1.0000 Uani . . . . . . .
C21 C 0.7453(5) 0.4118(11) 0.4046(3) 0.0278 1.0000 Uani . . . . . . .
C22 C 0.8422(6) 0.4790(14) 0.4141(3) 0.0423 1.0000 Uani . . . . . . .
C24 C 0.7730(6) 0.6744(15) 0.3623(3) 0.0481 1.0000 Uani . . . . . . .
C25 C 0.7022(6) 0.5421(14) 0.3707(3) 0.0368 1.0000 Uani . . . . . . .
C31 C 0.5984(5) 0.5451(12) 0.3491(3) 0.0296 1.0000 Uani . . . . . . .
C32 C 0.5280(6) 0.6814(13) 0.3565(3) 0.0388 1.0000 Uani . . . . . . .
C34 C 0.4568(6) 0.4746(13) 0.3069(3) 0.0344 1.0000 Uani . . . . . . .
C35 C 0.5508(5) 0.4095(11) 0.3159(3) 0.0269 1.0000 Uani . . . . . . .
C41 C 0.5974(5) 0.2388(12) 0.2953(3) 0.0290 1.0000 Uani . . . . . . .
C42 C 0.6919(6) 0.1767(13) 0.3038(3) 0.0364 1.0000 Uani . . . . . . .
C44 C 0.6235(5) -0.0231(14) 0.2522(3) 0.0407 1.0000 Uani . . . . . . .
C45 C 0.5514(6) 0.1071(12) 0.2612(3) 0.0340 1.0000 Uani . . . . . . .
H121 H 0.6801 -0.1529 0.4780 0.0659 1.0000 Uiso R . . . . . .
H141 H 0.5491 0.2784 0.4091 0.0471 1.0000 Uiso R . . . . . .
H221 H 0.8887 0.4235 0.4354 0.0510 1.0000 Uiso R . . . . . .
H241 H 0.7644 0.7782 0.3419 0.0580 1.0000 Uiso R . . . . . .
H321 H 0.5370 0.7892 0.3760 0.0472 1.0000 Uiso R . . . . . .
H341 H 0.4091 0.4158 0.2870 0.0410 1.0000 Uiso R . . . . . .
H421 H 0.7398 0.2348 0.3241 0.0440 1.0000 Uiso R . . . . . .
H441 H 0.6155 -0.1244 0.2312 0.0489 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0367(5) 0.0627(6) 0.0590(6) 0.0079(6) -0.0077(4) 0.0082(5)
O13 0.041(3) 0.052(4) 0.058(4) 0.019(3) 0.003(3) -0.014(3)
O23 0.031(3) 0.057(4) 0.068(4) 0.012(4) -0.007(3) -0.017(3)
O33 0.034(3) 0.055(4) 0.044(3) -0.005(3) -0.004(3) 0.013(3)
O43 0.033(3) 0.045(4) 0.052(3) -0.013(3) -0.013(2) 0.015(3)
C11 0.023(4) 0.054(6) 0.045(5) -0.005(4) -0.003(3) -0.004(4)
C12 0.070(6) 0.055(6) 0.039(5) 0.015(5) -0.016(4) -0.012(5)
C14 0.028(4) 0.047(5) 0.043(5) 0.008(4) -0.003(3) -0.006(4)
C15 0.032(4) 0.044(5) 0.028(4) 0.002(4) -0.004(3) 0.002(4)
C21 0.017(3) 0.035(5) 0.032(4) -0.007(3) 0.002(3) -0.003(3)
C22 0.033(4) 0.049(6) 0.044(5) 0.005(5) -0.002(4) -0.005(4)
C24 0.035(5) 0.048(6) 0.059(6) 0.010(5) -0.013(4) -0.010(4)
C25 0.032(4) 0.041(5) 0.036(4) -0.008(4) -0.003(3) -0.007(4)
C31 0.024(3) 0.033(4) 0.032(4) 0.000(4) 0.002(3) 0.001(3)
C32 0.034(4) 0.036(5) 0.045(5) -0.009(4) -0.010(4) 0.005(4)
C34 0.030(4) 0.040(5) 0.032(4) -0.006(4) -0.004(3) 0.009(4)
C35 0.019(3) 0.029(4) 0.033(4) 0.002(3) 0.004(3) -0.001(3)
C41 0.022(4) 0.034(5) 0.031(4) -0.003(4) 0.001(3) 0.001(3)
C42 0.023(4) 0.046(5) 0.039(5) -0.010(4) -0.006(3) 0.006(4)
C44 0.026(4) 0.050(5) 0.045(5) -0.008(4) -0.008(3) 0.008(4)
C45 0.031(4) 0.033(4) 0.037(4) -0.003(4) -0.005(3) -0.004(4)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.15877(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C11 . 1.876(8) yes
O13 . C12 . 1.325(11) yes
O13 . C14 . 1.376(10) yes
O23 . C22 . 1.339(11) yes
O23 . C24 . 1.384(10) yes
O33 . C32 . 1.370(9) yes
O33 . C34 . 1.380(10) yes
O43 . C42 . 1.395(10) yes
O43 . C44 . 1.363(9) yes
C11 . C12 . 1.307(13) yes
C11 . C15 . 1.460(12) yes
C12 . H121 . 0.927 no
C14 . C15 . 1.345(11) yes
C14 . H141 . 0.933 no
C15 . C21 . 1.467(11) yes
C21 . C22 . 1.381(10) yes
C21 . C25 . 1.423(11) yes
C22 . H221 . 0.931 no
C24 . C25 . 1.341(12) yes
C24 . H241 . 0.930 no
C25 . C31 . 1.483(10) yes
C31 . C32 . 1.350(11) yes
C31 . C35 . 1.457(11) yes
C32 . H321 . 0.935 no
C34 . C35 . 1.339(10) yes
C34 . H341 . 0.926 no
C35 . C41 . 1.469(11) yes
C41 . C42 . 1.337(10) yes
C41 . C45 . 1.448(11) yes
C42 . H421 . 0.932 no
C44 . C45 . 1.348(12) yes
C44 . H441 . 0.926 no
C45 . C45 5_655 1.481(14) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 . O13 . C14 . 106.5(7) yes
C22 . O23 . C24 . 106.2(6) yes
C32 . O33 . C34 . 105.9(6) yes
C42 . O43 . C44 . 105.0(6) yes
Br1 . C11 . C12 . 125.9(8) yes
Br1 . C11 . C15 . 127.0(6) yes
C12 . C11 . C15 . 107.1(7) yes
O13 . C12 . C11 . 112.0(9) yes
O13 . C12 . H121 . 123.3 no
C11 . C12 . H121 . 124.7 no
O13 . C14 . C15 . 110.7(7) yes
O13 . C14 . H141 . 124.5 no
C15 . C14 . H141 . 124.8 no
C11 . C15 . C14 . 103.7(7) yes
C11 . C15 . C21 . 130.0(7) yes
C14 . C15 . C21 . 126.3(7) yes
C15 . C21 . C22 . 126.8(7) yes
C15 . C21 . C25 . 128.0(6) yes
C22 . C21 . C25 . 105.2(7) yes
C21 . C22 . O23 . 111.1(7) yes
C21 . C22 . H221 . 125.0 no
O23 . C22 . H221 . 123.9 no
O23 . C24 . C25 . 110.5(8) yes
O23 . C24 . H241 . 124.5 no
C25 . C24 . H241 . 124.9 no
C21 . C25 . C24 . 107.0(7) yes
C21 . C25 . C31 . 128.9(7) yes
C24 . C25 . C31 . 124.1(8) yes
C25 . C31 . C32 . 125.5(8) yes
C25 . C31 . C35 . 128.9(7) yes
C32 . C31 . C35 . 105.5(6) yes
O33 . C32 . C31 . 111.3(7) yes
O33 . C32 . H321 . 123.5 no
C31 . C32 . H321 . 125.3 no
O33 . C34 . C35 . 111.0(7) yes
O33 . C34 . H341 . 123.9 no
C35 . C34 . H341 . 125.1 no
C31 . C35 . C34 . 106.3(7) yes
C31 . C35 . C41 . 127.0(6) yes
C34 . C35 . C41 . 126.7(7) yes
C35 . C41 . C42 . 126.4(7) yes
C35 . C41 . C45 . 127.2(6) yes
C42 . C41 . C45 . 106.3(7) yes
O43 . C42 . C41 . 111.1(7) yes
O43 . C42 . H421 . 123.5 no
C41 . C42 . H421 . 125.5 no
O43 . C44 . C45 . 111.9(7) yes
O43 . C44 . H441 . 123.3 no
C45 . C44 . H441 . 124.7 no
C45 5_655 C45 . C41 . 130.0(6) yes
C45 5_655 C45 . C44 . 124.3(7) yes
C41 . C45 . C44 . 105.7(7) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O23 3.510(7) . 1_545 no
O13 C22 3.289(9) . 3_445 no
O13 O23 3.375(8) . 3_445 no
O13 C32 3.57(1) . 1_545 no
O23 C14 3.299(9) . 3 no
O33 C42 3.355(9) . 3_455 no
O33 C44 3.41(1) . 5_665 no
O33 O43 3.454(8) . 3_455 no
O43 C34 3.339(9) . 3_545 no
O43 C24 3.43(1) . 1_545 no
O43 C42 3.60(1) . 7_645 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C11 C12 O13 . . . . -178.4(6) no
Br1 C11 C15 C14 . . . . 178.2(7) no
Br1 C11 C15 C21 . . . . -1(1) no
O13 C12 C11 C15 . . . . 1(1) no
O13 C14 C15 C11 . . . . 1(1) no
O13 C14 C15 C21 . . . . -179.8(8) no
O23 C22 C21 C15 . . . . 178.7(8) no
O23 C22 C21 C25 . . . . -1(1) no
O23 C24 C25 C21 . . . . 1(1) no
O23 C24 C25 C31 . . . . 178.1(8) no
O33 C32 C31 C25 . . . . -179.9(8) no
O33 C32 C31 C35 . . . . 1(1) no
O33 C34 C35 C31 . . . . 0(1) no
O33 C34 C35 C41 . . . . -177.9(8) no
O43 C42 C41 C35 . . . . -179.6(8) no
O43 C42 C41 C45 . . . . -1(1) no
O43 C44 C45 C41 . . . . 1(1) no
O43 C44 C45 C45 . . . 5_655 -179.8(9) no
C11 C12 O13 C14 . . . . -0(1) no
C11 C15 C21 C22 . . . . -16(2) no
C11 C15 C21 C25 . . . . 163.0(9) no
C12 O13 C14 C15 . . . . -0(1) no
C12 C11 C15 C14 . . . . -1(1) no
C12 C11 C15 C21 . . . . 179.7(9) no
C14 C15 C21 C22 . . . . 164.6(9) no
C14 C15 C21 C25 . . . . -16(2) no
C15 C21 C25 C24 . . . . -179.3(9) no
C15 C21 C25 C31 . . . . 3(2) no
C21 C22 O23 C24 . . . . 1(1) no
C21 C25 C31 C32 . . . . 110(1) no
C21 C25 C31 C35 . . . . -71(1) no
C22 O23 C24 C25 . . . . -1(1) no
C22 C21 C25 C24 . . . . -0(1) no
C22 C21 C25 C31 . . . . -177.4(9) no
C24 C25 C31 C32 . . . . -67(1) no
C24 C25 C31 C35 . . . . 112(1) no
C25 C31 C35 C34 . . . . -180.0(9) no
C25 C31 C35 C41 . . . . -2(1) no
C31 C32 O33 C34 . . . . -0.6(9) no
C31 C35 C41 C42 . . . . 1(1) no
C31 C35 C41 C45 . . . . -177.9(8) no
C32 O33 C34 C35 . . . . 0.1(9) no
C32 C31 C35 C34 . . . . -1(1) no
C32 C31 C35 C41 . . . . 177.6(8) no
C34 C35 C41 C42 . . . . 178.7(9) no
C34 C35 C41 C45 . . . . 0(1) no
C35 C41 C45 C44 . . . . 178.6(8) no
C35 C41 C45 C45 . . . 5_655 -0(2) no
C41 C42 O43 C44 . . . . 1.3(9) no
C41 C45 C45 C41 . . 5_655 5_655 71(2) no
C41 C45 C45 C44 . . 5_655 5_655 -107.8(6) no
C42 O43 C44 C45 . . . . -1(1) no
C42 C41 C45 C44 . . . . -0(1) no
C42 C41 C45 C45 . . . 5_655 -179(1) no
C44 C45 C45 C44 . . 5_655 5_655 73(2) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd17_she1005.cif'
data_she1005
_database_code_depnum_ccdc_archive 'CCDC 860337'
_audit_creation_date 10-02-19
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2010-02-22 - Report on C12 H6 I2 O3
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2010-02-22 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '2191417 she1005'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 8.6955(2)
_cell_length_b 11.3755(3)
_cell_length_c 13.3637(3)
_cell_angle_alpha 90
_cell_angle_beta 103.3546(11)
_cell_angle_gamma 90
_cell_volume 1286.13(5)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C12 H6 I2 O3
# Dc = 2.33 Fooo = 832.00 Mu = 48.83 M = 451.99
# Found Formula = C12 H6 I2 O3
# Dc = 2.33 FOOO = 832.00 Mu = 48.83 M = 451.99
_chemical_formula_sum 'C12 H6 I2 O3'
_chemical_formula_moiety 'C12 H6 I2 O3'
_chemical_compound_source local
_chemical_formula_weight 451.99
_cell_measurement_reflns_used 14691
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 30
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.070
_exptl_crystal_size_mid 0.310
_exptl_crystal_size_max 0.310
_exptl_crystal_density_diffrn 2.334
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 832
_exptl_absorpt_coefficient_mu 4.883
# Sheldrick geometric approximatio 0.22 0.71
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.040
-1 0 0 0.030
0 1 0 0.150
0 -1 0 0.160
0 0 1 0.140
0 0 -1 0.170
-1 -1 0 0.080
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.260
_exptl_absorpt_correction_T_max 0.727
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.029
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 160 sec/frame,
crystal-detector distance 40mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 28726
_reflns_number_total 3749
_diffrn_reflns_av_R_equivalents 0.029
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3749
# Theoretical number of reflections is about 7524
_diffrn_reflns_theta_min 3.001
_diffrn_reflns_theta_max 30.031
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 30.031
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_reflns_limit_h_min -12
_reflns_limit_h_max 11
_reflns_limit_k_min 0
_reflns_limit_k_max 16
_reflns_limit_l_min 0
_reflns_limit_l_max 18
_oxford_diffrn_Wilson_B_factor 2.83
_oxford_diffrn_Wilson_scale 1.32
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.98
_refine_diff_density_max 1.02
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 3749
_refine_ls_number_restraints 0
_refine_ls_number_parameters 173
_oxford_refine_ls_R_factor_ref 0.0222
_refine_ls_wR_factor_ref 0.0485
_refine_ls_goodness_of_fit_ref 1.0625
_refine_ls_shift/su_max 0.0048275
_refine_ls_shift/su_mean 0.3403080
# The values computed from all data
_oxford_reflns_number_all 3749
_refine_ls_R_factor_all 0.0222
_refine_ls_wR_factor_all 0.0485
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 3538
_refine_ls_R_factor_gt 0.0205
_refine_ls_wR_factor_gt 0.0477
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 1.71P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~12~H~6~I~2~O~3~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one
molecule of C~12~H~6~I~2~O~3~.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
The H atoms were all located in a difference map, but
were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98 \%A) and with
U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom,
after which the positions were refined without restraints
and the displacement parameters were held fixed.
The largest peaks in the final difference electron density map
are located close to the I atoms.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from hexane.
The sample ID is tf-I~2~Fu~3~.
;
_refine_special_details
;
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
I1 I 0.716058(19) 0.860937(13) 0.699765(13) 0.0368 1.0000 Uani . . . . . . .
I2 I 0.36097(2) 0.739440(15) 0.899742(12) 0.0395 1.0000 Uani . . . . . . .
O13 O 0.8998(2) 0.61091(16) 0.52310(12) 0.0359 1.0000 Uani . . . . . . .
O23 O 0.83119(19) 0.49118(16) 0.93148(12) 0.0373 1.0000 Uani . . . . . . .
O33 O 0.2966(2) 0.62237(17) 0.59371(12) 0.0405 1.0000 Uani . . . . . . .
C11 C 0.8013(2) 0.71983(18) 0.63159(16) 0.0265 1.0000 Uani . . . . . . .
C12 C 0.8458(3) 0.7200(2) 0.54123(18) 0.0333 1.0000 Uani . . . . . . .
C14 C 0.8872(3) 0.5420(2) 0.60440(17) 0.0314 1.0000 Uani . . . . . . .
C15 C 0.8273(2) 0.60316(18) 0.67378(15) 0.0258 1.0000 Uani . . . . . . .
C21 C 0.7956(2) 0.56126(18) 0.77087(15) 0.0257 1.0000 Uani . . . . . . .
C22 C 0.9026(3) 0.5200(2) 0.85361(17) 0.0343 1.0000 Uani . . . . . . .
C24 C 0.6748(3) 0.5167(2) 0.89640(16) 0.0322 1.0000 Uani . . . . . . .
C25 C 0.6451(2) 0.55996(18) 0.79939(14) 0.0250 1.0000 Uani . . . . . . .
C31 C 0.4929(2) 0.59589(18) 0.73446(14) 0.0249 1.0000 Uani . . . . . . .
C32 C 0.4398(3) 0.5712(2) 0.63311(16) 0.0342 1.0000 Uani . . . . . . .
C34 C 0.2566(3) 0.6810(2) 0.67330(18) 0.0349 1.0000 Uani . . . . . . .
C35 C 0.3703(2) 0.66741(18) 0.75944(15) 0.0261 1.0000 Uani . . . . . . .
H121 H 0.846(3) 0.775(3) 0.487(2) 0.0399 1.0000 Uiso . . . . . . .
H141 H 0.924(3) 0.467(3) 0.605(2) 0.0381 1.0000 Uiso . . . . . . .
H221 H 1.015(4) 0.511(3) 0.868(2) 0.0407 1.0000 Uiso . . . . . . .
H241 H 0.610(3) 0.503(3) 0.944(2) 0.0394 1.0000 Uiso . . . . . . .
H321 H 0.478(3) 0.530(3) 0.587(2) 0.0415 1.0000 Uiso . . . . . . .
H341 H 0.162(4) 0.722(3) 0.658(2) 0.0434 1.0000 Uiso . . . . . . .
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
I1 0.04081(9) 0.02607(8) 0.04843(10) -0.00255(6) 0.02046(7) 0.00281(5)
I2 0.04826(10) 0.04045(9) 0.03250(8) -0.00491(6) 0.01486(6) 0.00549(6)
O13 0.0416(9) 0.0398(9) 0.0313(8) 0.0003(7) 0.0185(7) 0.0054(7)
O23 0.0327(8) 0.0506(10) 0.0272(7) 0.0097(7) 0.0042(6) 0.0070(7)
O33 0.0357(8) 0.0568(11) 0.0255(7) 0.0007(7) -0.0002(6) 0.0023(8)
C11 0.0246(9) 0.0268(9) 0.0300(9) 0.0006(7) 0.0098(7) 0.0030(7)
C12 0.0343(11) 0.0344(11) 0.0335(10) 0.0061(9) 0.0128(9) 0.0048(9)
C14 0.0348(10) 0.0296(10) 0.0337(10) -0.0004(8) 0.0157(8) 0.0039(8)
C15 0.0241(8) 0.0282(9) 0.0262(9) 0.0000(7) 0.0078(7) 0.0018(7)
C21 0.0257(9) 0.0263(9) 0.0261(9) 0.0005(7) 0.0083(7) 0.0028(7)
C22 0.0296(10) 0.0429(12) 0.0309(10) 0.0041(9) 0.0077(8) 0.0078(9)
C24 0.0296(10) 0.0409(12) 0.0262(9) 0.0052(8) 0.0062(8) 0.0005(8)
C25 0.0256(9) 0.0273(9) 0.0225(8) 0.0008(7) 0.0066(7) -0.0003(7)
C31 0.0244(8) 0.0279(9) 0.0231(8) 0.0018(7) 0.0070(7) -0.0027(7)
C32 0.0361(11) 0.0431(12) 0.0232(9) -0.0016(9) 0.0063(8) 0.0019(9)
C34 0.0280(10) 0.0424(12) 0.0335(10) 0.0043(9) 0.0054(8) 0.0031(9)
C35 0.0265(9) 0.0279(9) 0.0250(8) 0.0013(7) 0.0081(7) -0.0016(7)
_refine_ls_extinction_coef 34.1(17)
_refine_ls_extinction_method 'Larson (1970), Equation 22'
_oxford_refine_ls_scale 0.9001(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . C11 . 2.066(2) yes
I2 . C35 . 2.065(2) yes
O13 . C12 . 1.368(3) yes
O13 . C14 . 1.365(3) yes
O23 . C22 . 1.369(3) yes
O23 . C24 . 1.363(3) yes
O33 . C32 . 1.365(3) yes
O33 . C34 . 1.367(3) yes
C11 . C12 . 1.351(3) yes
C11 . C15 . 1.439(3) yes
C12 . H121 . 0.95(3) no
C14 . C15 . 1.356(3) yes
C14 . H141 . 0.91(3) no
C15 . C21 . 1.467(3) yes
C21 . C22 . 1.354(3) yes
C21 . C25 . 1.445(3) yes
C22 . H221 . 0.96(3) no
C24 . C25 . 1.355(3) yes
C24 . H241 . 0.95(3) no
C25 . C31 . 1.463(3) yes
C31 . C32 . 1.356(3) yes
C31 . C35 . 1.440(3) yes
C32 . H321 . 0.90(3) no
C34 . C35 . 1.342(3) yes
C34 . H341 . 0.93(3) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 . O13 . C14 . 106.63(17) yes
C22 . O23 . C24 . 106.21(17) yes
C32 . O33 . C34 . 106.36(17) yes
I1 . C11 . C12 . 126.83(16) yes
I1 . C11 . C15 . 125.71(14) yes
C12 . C11 . C15 . 107.45(18) yes
O13 . C12 . C11 . 109.77(19) yes
O13 . C12 . H121 . 113.4(18) no
C11 . C12 . H121 . 136.8(18) no
O13 . C14 . C15 . 111.33(19) yes
O13 . C14 . H141 . 116.8(18) no
C15 . C14 . H141 . 131.7(18) no
C11 . C15 . C14 . 104.83(18) yes
C11 . C15 . C21 . 126.98(18) yes
C14 . C15 . C21 . 128.2(2) yes
C15 . C21 . C22 . 126.94(19) yes
C15 . C21 . C25 . 127.10(17) yes
C22 . C21 . C25 . 105.92(18) yes
O23 . C22 . C21 . 110.92(19) yes
O23 . C22 . H221 . 116.2(17) no
C21 . C22 . H221 . 132.8(17) no
O23 . C24 . C25 . 111.13(19) yes
O23 . C24 . H241 . 115.8(17) no
C25 . C24 . H241 . 133.1(17) no
C21 . C25 . C24 . 105.81(18) yes
C21 . C25 . C31 . 126.22(17) yes
C24 . C25 . C31 . 127.96(18) yes
C25 . C31 . C32 . 125.97(19) yes
C25 . C31 . C35 . 129.56(18) yes
C32 . C31 . C35 . 104.42(18) yes
O33 . C32 . C31 . 111.5(2) yes
O33 . C32 . H321 . 113.9(18) no
C31 . C32 . H321 . 134.5(18) no
O33 . C34 . C35 . 109.9(2) yes
O33 . C34 . H341 . 116.9(19) no
C35 . C34 . H341 . 133.1(19) no
C31 . C35 . I2 . 128.41(14) yes
C31 . C35 . C34 . 107.74(19) yes
I2 . C35 . C34 . 123.85(17) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
I1 C31 3.458(2) . 3_656 no
I2 O33 3.190(2) . 4_565 no
O13 O13 3.207(4) . 2_766 no
O13 C14 3.289(3) . 2_766 no
O13 O33 3.341(2) . 2_666 no
O13 O33 3.363(2) . 1_655 no
O13 C34 3.378(3) . 1_655 no
O23 O23 3.087(3) . 2_767 no
O23 C22 3.248(2) . 2_767 no
O23 C12 3.588(3) . 4_565 no
O33 C14 3.332(3) . 2_666 no
C14 C34 3.507(4) . 1_655 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
I1 C11 C12 O13 . . . . 178.3(1) no
I1 C11 C15 C14 . . . . -178.4(1) no
I1 C11 C15 C21 . . . . 1.5(2) no
I2 C35 C31 C25 . . . . -3.2(3) no
I2 C35 C31 C32 . . . . 179.3(2) no
I2 C35 C34 O33 . . . . -179.6(1) no
O13 C12 C11 C15 . . . . -0.4(2) no
O13 C14 C15 C11 . . . . -0.2(2) no
O13 C14 C15 C21 . . . . 180.0(2) no
O23 C22 C21 C15 . . . . 178.6(2) no
O23 C22 C21 C25 . . . . 0.9(2) no
O23 C24 C25 C21 . . . . 0.3(2) no
O23 C24 C25 C31 . . . . 179.0(2) no
O33 C32 C31 C25 . . . . -176.9(2) no
O33 C32 C31 C35 . . . . 0.7(3) no
O33 C34 C35 C31 . . . . 0.3(3) no
C11 C12 O13 C14 . . . . 0.3(2) no
C11 C15 C21 C22 . . . . -117.4(2) no
C11 C15 C21 C25 . . . . 59.9(3) no
C12 O13 C14 C15 . . . . -0.1(2) no
C12 C11 C15 C14 . . . . 0.4(2) no
C12 C11 C15 C21 . . . . -179.8(2) no
C14 C15 C21 C22 . . . . 62.4(3) no
C14 C15 C21 C25 . . . . -120.3(2) no
C15 C21 C25 C24 . . . . -178.4(2) no
C15 C21 C25 C31 . . . . 2.8(3) no
C21 C22 O23 C24 . . . . -0.7(2) no
C21 C25 C31 C32 . . . . 41.6(3) no
C21 C25 C31 C35 . . . . -135.4(2) no
C22 O23 C24 C25 . . . . 0.3(2) no
C22 C21 C25 C24 . . . . -0.7(2) no
C22 C21 C25 C31 . . . . -179.4(2) no
C24 C25 C31 C32 . . . . -136.8(3) no
C24 C25 C31 C35 . . . . 46.2(3) no
C25 C31 C35 C34 . . . . 176.9(2) no
C31 C32 O33 C34 . . . . -0.5(3) no
C32 O33 C34 C35 . . . . 0.1(3) no
C32 C31 C35 C34 . . . . -0.6(2) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd18_she0935.cif'
data_she0935
_database_code_depnum_ccdc_archive 'CCDC 860338'
_audit_creation_date 09-11-06
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2009-11-12 - Report on C20 H10 Br2 O5
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2009-11-12 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '11061620 she0935'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 8.1262(11)
_cell_length_b 15.991(2)
_cell_length_c 13.825(2)
_cell_angle_alpha 90
_cell_angle_beta 101.243(5)
_cell_angle_gamma 90
_cell_volume 1761.9(4)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 1 c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
x,-y,z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C20 H10 Br2 O5
# Dc = 1.85 Fooo = 960.00 Mu = 46.31 M = 490.10
# Found Formula = C20 H10 Br2 O5
# Dc = 1.85 FOOO = 960.00 Mu = 46.31 M = 490.10
_chemical_formula_sum 'C20 H10 Br2 O5'
_chemical_formula_moiety 'C20 H10 Br2 O5'
_chemical_compound_source local
_chemical_formula_weight 490.10
_cell_measurement_reflns_used 19338
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 25
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.030
_exptl_crystal_size_mid 0.140
_exptl_crystal_size_max 0.250
_exptl_crystal_density_diffrn 1.847
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 960
_exptl_absorpt_coefficient_mu 4.631
# Sheldrick geometric approximatio 0.52 0.87
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.150
-1 0 0 0.100
0 1 0 0.020
0 -1 0 0.120
1 -3 0 0.081
0 0 1 0.010
0 0 -1 0.020
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.436
_exptl_absorpt_correction_T_max 0.872
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.057
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 1.8 deg at rate 144 sec/frame,
crystal-detector distance 60mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more [assuming Friedel's Law].
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 10901
_reflns_number_total 3030
_diffrn_reflns_av_R_equivalents 0.096
# Number of reflections without Friedels Law is 3030
# Number of reflections with Friedels Law is 1566
# Theoretical number of reflections is about 1560
_diffrn_reflns_theta_min 2.547
_diffrn_reflns_theta_max 25.047
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.047
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min 0
_reflns_limit_k_max 18
_reflns_limit_l_min -16
_reflns_limit_l_max 16
_oxford_diffrn_Wilson_B_factor 3.77
_oxford_diffrn_Wilson_scale 52.27
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.94
_refine_diff_density_max 1.03
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 3030
_refine_ls_number_restraints 2
_refine_ls_number_parameters 245
_oxford_refine_ls_R_factor_ref 0.0890
_refine_ls_wR_factor_ref 0.1237
_refine_ls_goodness_of_fit_ref 1.0073
_refine_ls_shift/su_max 0.0003437
_refine_ls_shift/su_mean 3.4989586
# The values computed from all data
_oxford_reflns_number_all 3030
_refine_ls_R_factor_all 0.0890
_refine_ls_wR_factor_all 0.1237
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 2175
_refine_ls_R_factor_gt 0.0576
_refine_ls_wR_factor_gt 0.1094
_refine_ls_abs_structure_Flack 0.206(19)
_refine_ls_abs_structure_details 'Flack (1983), 1461 Friedel-pairs'
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration ad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ +12.44P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~20~H~10~Br~2~O~5~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one
molecule of C~20~H~10~Br~2~O~5~.
The crystals supplied were very thin plates and generally intergrown.
During data collection, spots were observed that did not belong to the
major diffraction pattern suggesting that the crystal
was not single or
was split to some degree.
The crystal comes from a racemic solution but has a
noncentrosymmetric space group.
The Flack parameter (Flack, 1983)
was refined in an attempt to determine
the absolute structure of the crystal used in this experiment.
The final value of 0.21(2)
suggests that the crystal is partially inversion twinned
(Flack & Bernardinelli, 1999, 2000).
The space group is not enantiomorphic so
the compound is present as a racemate within the crystal structure
anyway.
Hydrogen atoms were included at idealized positions and
ride on the atoms to which they are bonded.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms were included at
calculated positions and ride on the atom to which they are bonded.
The largest peaks in the final difference electron density map
are located near the Br atoms.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from dichloromethane/hexane.
The sample ID is tf704-Bu~2~Fu~5~.
;
_refine_special_details
;
The crystal comes from a racemic solution but has a
noncentrosymmetric space group.
The Flack parameter (Flack, 1983)
was refined in an attempt to determine
the absolute structure of the crystal used in this experiment.
The final value of 0.21(2)
suggests that the crystal is partially inversion twinned
(Flack & Bernardinelli, 1999, 2000).
The space group is not enantiomorphic so
the compound is present as a racemate within the crystal structure
anyway.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Flack, H.D. (1983) Acta Cryst., A39, 876-881.
Flack, H.D. & Bernardinelli, G. (1999) Acta Cryst., A55, 908-915.
Flack, H.D. & Bernardinelli, G. (2000) J. Appl. Cryst., 33, 1143-1148.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 0.9955(2) 0.38150(7) 0.73400(13) 0.0570 1.0000 Uani . . . . . . .
Br2 Br 0.5861(2) 0.30251(7) 0.85867(13) 0.0609 1.0000 Uani . . . . . . .
C11 C 0.9551(11) 0.4289(7) 0.6086(7) 0.0502 1.0000 Uani . . . . . . .
C12 C 1.0144(12) 0.5046(6) 0.5845(8) 0.0481 1.0000 Uani . . . . . . .
O13 O 0.9582(9) 0.5184(4) 0.4857(6) 0.0568 1.0000 Uani . . . . . . .
C14 C 0.8686(11) 0.4506(6) 0.4474(8) 0.0469 1.0000 Uani . . . . . . .
C15 C 0.8618(11) 0.3921(6) 0.5206(7) 0.0382 1.0000 Uani . . . . . . .
C21 C 0.7706(11) 0.3134(5) 0.5097(7) 0.0347 1.0000 Uani . . . . . . .
C22 C 0.8311(11) 0.2389(6) 0.5457(7) 0.0465 1.0000 Uani . . . . . . .
O23 O 0.7140(8) 0.1772(4) 0.5201(5) 0.0472 1.0000 Uani . . . . . . .
C24 C 0.5792(13) 0.2131(6) 0.4646(7) 0.0454 1.0000 Uani . . . . . . .
C25 C 0.6048(11) 0.2970(5) 0.4555(7) 0.0347 1.0000 Uani . . . . . . .
C31 C 0.4797(10) 0.3577(5) 0.4067(7) 0.0307 1.0000 Uani . . . . . . .
C32 C 0.3854(12) 0.3543(6) 0.3154(7) 0.0451 1.0000 Uani . . . . . . .
O33 O 0.2754(9) 0.4202(5) 0.2994(5) 0.0610 1.0000 Uani . . . . . . .
C34 C 0.3058(12) 0.4652(7) 0.3826(8) 0.0514 1.0000 Uani . . . . . . .
C35 C 0.4270(11) 0.4333(6) 0.4515(6) 0.0353 1.0000 Uani . . . . . . .
C41 C 0.4873(11) 0.4644(6) 0.5515(7) 0.0424 1.0000 Uani . . . . . . .
C42 C 0.5653(13) 0.5399(6) 0.5760(8) 0.0486 1.0000 Uani . . . . . . .
O43 O 0.6071(10) 0.5481(4) 0.6758(5) 0.0587 1.0000 Uani . . . . . . .
C44 C 0.5531(12) 0.4767(6) 0.7148(8) 0.0497 1.0000 Uani . . . . . . .
C45 C 0.4809(11) 0.4244(5) 0.6446(7) 0.0352 1.0000 Uani . . . . . . .
C51 C 0.4067(11) 0.3409(6) 0.6562(7) 0.0419 1.0000 Uani . . . . . . .
C52 C 0.2947(12) 0.3007(7) 0.5893(7) 0.0474 1.0000 Uani . . . . . . .
O53 O 0.2535(9) 0.2252(5) 0.6215(6) 0.0592 1.0000 Uani . . . . . . .
C54 C 0.3453(14) 0.2169(6) 0.7153(8) 0.0560 1.0000 Uani . . . . . . .
C55 C 0.4442(12) 0.2855(5) 0.7387(7) 0.0423 1.0000 Uani . . . . . . .
H121 H 1.0831 0.5415 0.6288 0.0577 1.0000 Uiso R . . . . . .
H141 H 0.8176 0.4440 0.3800 0.0563 1.0000 Uiso R . . . . . .
H221 H 0.9404 0.2303 0.5837 0.0558 1.0000 Uiso R . . . . . .
H241 H 0.4796 0.1843 0.4355 0.0545 1.0000 Uiso R . . . . . .
H321 H 0.3937 0.3120 0.2684 0.0541 1.0000 Uiso R . . . . . .
H341 H 0.2467 0.5150 0.3915 0.0618 1.0000 Uiso R . . . . . .
H421 H 0.5868 0.5805 0.5298 0.0583 1.0000 Uiso R . . . . . .
H441 H 0.5657 0.4659 0.7835 0.0597 1.0000 Uiso R . . . . . .
H521 H 0.2489 0.3226 0.5259 0.0568 1.0000 Uiso R . . . . . .
H541 H 0.3406 0.1705 0.7575 0.0672 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0649(7) 0.0564(7) 0.0465(6) 0.0021(6) 0.0025(5) -0.0120(6)
Br2 0.0632(7) 0.0659(8) 0.0484(7) 0.0080(6) -0.0017(5) 0.0078(7)
C11 0.026(5) 0.084(9) 0.042(6) -0.013(6) 0.009(5) 0.001(5)
C12 0.045(6) 0.032(6) 0.064(8) -0.002(5) 0.005(5) -0.024(5)
O13 0.063(5) 0.035(4) 0.067(5) 0.016(4) -0.003(4) -0.010(4)
C14 0.029(5) 0.040(6) 0.071(8) -0.020(6) 0.008(5) -0.017(5)
C15 0.041(6) 0.026(5) 0.053(7) 0.004(5) 0.021(5) -0.001(4)
C21 0.038(5) 0.019(5) 0.050(6) 0.000(4) 0.014(5) 0.005(4)
C22 0.030(5) 0.049(7) 0.059(7) -0.004(5) 0.004(5) 0.000(5)
O23 0.044(4) 0.030(4) 0.069(5) 0.010(4) 0.014(4) 0.000(3)
C24 0.045(6) 0.037(6) 0.051(7) 0.001(5) 0.001(5) -0.007(5)
C25 0.033(5) 0.030(5) 0.044(6) -0.001(5) 0.013(4) 0.002(4)
C31 0.031(5) 0.025(5) 0.037(5) 0.002(4) 0.007(4) -0.003(4)
C32 0.056(6) 0.042(6) 0.034(6) -0.007(5) 0.003(5) 0.000(5)
O33 0.060(5) 0.064(5) 0.050(5) 0.012(4) -0.011(4) 0.005(4)
C34 0.044(6) 0.048(7) 0.063(8) -0.004(6) 0.012(6) 0.001(5)
C35 0.039(6) 0.034(6) 0.033(5) 0.012(4) 0.006(5) 0.007(4)
C41 0.038(6) 0.030(6) 0.060(7) 0.004(5) 0.012(5) 0.011(4)
C42 0.070(7) 0.021(5) 0.061(7) 0.009(5) 0.029(6) -0.003(5)
O43 0.082(5) 0.033(4) 0.063(5) -0.007(4) 0.020(5) -0.018(4)
C44 0.055(7) 0.043(7) 0.051(7) -0.004(5) 0.011(5) -0.014(5)
C45 0.037(5) 0.024(5) 0.045(6) 0.000(5) 0.008(5) 0.003(4)
C51 0.030(5) 0.043(6) 0.050(6) -0.006(5) 0.001(5) -0.008(5)
C52 0.053(7) 0.044(7) 0.043(6) 0.004(5) 0.004(5) -0.004(6)
O53 0.059(5) 0.038(4) 0.078(6) 0.012(4) 0.007(4) -0.010(4)
C54 0.067(7) 0.043(7) 0.055(7) 0.015(6) 0.005(6) -0.001(6)
C55 0.050(6) 0.032(6) 0.043(6) 0.003(5) 0.004(5) -0.001(5)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.15139(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C11 . 1.861(11) yes
Br2 . C55 . 1.846(10) yes
C11 . C12 . 1.368(14) yes
C11 . C15 . 1.430(14) yes
C12 . O13 . 1.370(13) yes
C12 . H121 . 0.950 no
O13 . C14 . 1.355(11) yes
C14 . C15 . 1.386(13) yes
C14 . H141 . 0.950 no
C15 . C21 . 1.453(12) yes
C21 . C22 . 1.347(13) yes
C21 . C25 . 1.432(12) yes
C22 . O23 . 1.368(11) yes
C22 . H221 . 0.950 no
O23 . C24 . 1.338(11) yes
C24 . C25 . 1.366(12) yes
C24 . H241 . 0.950 no
C25 . C31 . 1.471(12) yes
C31 . C32 . 1.344(12) yes
C31 . C35 . 1.461(12) yes
C32 . O33 . 1.372(12) yes
C32 . H321 . 0.950 no
O33 . C34 . 1.339(12) yes
C34 . C35 . 1.332(13) yes
C34 . H341 . 0.950 no
C35 . C41 . 1.461(13) yes
C41 . C42 . 1.375(13) yes
C41 . C45 . 1.447(12) yes
C42 . O43 . 1.362(12) yes
C42 . H421 . 0.950 no
O43 . C44 . 1.372(12) yes
C44 . C45 . 1.327(13) yes
C44 . H441 . 0.950 no
C45 . C51 . 1.487(13) yes
C51 . C52 . 1.330(13) yes
C51 . C55 . 1.429(13) yes
C52 . O53 . 1.351(12) yes
C52 . H521 . 0.950 no
O53 . C54 . 1.370(12) yes
C54 . C55 . 1.361(13) yes
C54 . H541 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C11 . C12 . 125.5(8) yes
Br1 . C11 . C15 . 126.4(8) yes
C12 . C11 . C15 . 108.1(9) yes
C11 . C12 . O13 . 108.7(8) yes
C11 . C12 . H121 . 125.6 no
O13 . C12 . H121 . 125.6 no
C12 . O13 . C14 . 108.0(8) yes
O13 . C14 . C15 . 110.5(9) yes
O13 . C14 . H141 . 124.8 no
C15 . C14 . H141 . 124.8 no
C11 . C15 . C14 . 104.7(8) yes
C11 . C15 . C21 . 128.3(9) yes
C14 . C15 . C21 . 126.9(9) yes
C15 . C21 . C22 . 125.8(9) yes
C15 . C21 . C25 . 128.5(8) yes
C22 . C21 . C25 . 105.6(8) yes
C21 . C22 . O23 . 110.9(8) yes
C21 . C22 . H221 . 124.6 no
O23 . C22 . H221 . 124.6 no
C22 . O23 . C24 . 106.8(7) yes
O23 . C24 . C25 . 110.6(9) yes
O23 . C24 . H241 . 124.7 no
C25 . C24 . H241 . 124.7 no
C21 . C25 . C24 . 106.1(8) yes
C21 . C25 . C31 . 127.9(8) yes
C24 . C25 . C31 . 125.8(8) yes
C25 . C31 . C32 . 128.4(9) yes
C25 . C31 . C35 . 125.8(8) yes
C32 . C31 . C35 . 105.7(8) yes
C31 . C32 . O33 . 110.8(8) yes
C31 . C32 . H321 . 124.6 no
O33 . C32 . H321 . 124.6 no
C32 . O33 . C34 . 105.6(8) yes
O33 . C34 . C35 . 113.3(9) yes
O33 . C34 . H341 . 123.4 no
C35 . C34 . H341 . 123.4 no
C31 . C35 . C34 . 104.5(8) yes
C31 . C35 . C41 . 127.7(8) yes
C34 . C35 . C41 . 127.7(9) yes
C35 . C41 . C42 . 125.8(9) yes
C35 . C41 . C45 . 128.9(8) yes
C42 . C41 . C45 . 105.3(9) yes
C41 . C42 . O43 . 110.2(9) yes
C41 . C42 . H421 . 124.9 no
O43 . C42 . H421 . 124.9 no
C42 . O43 . C44 . 106.4(7) yes
O43 . C44 . C45 . 111.5(9) yes
O43 . C44 . H441 . 124.3 no
C45 . C44 . H441 . 124.2 no
C41 . C45 . C44 . 106.6(8) yes
C41 . C45 . C51 . 125.3(8) yes
C44 . C45 . C51 . 128.1(9) yes
C45 . C51 . C52 . 126.6(9) yes
C45 . C51 . C55 . 127.9(8) yes
C52 . C51 . C55 . 105.4(9) yes
C51 . C52 . O53 . 112.5(9) yes
C51 . C52 . H521 . 123.8 no
O53 . C52 . H521 . 123.8 no
C52 . O53 . C54 . 105.9(8) yes
O53 . C54 . C55 . 109.6(9) yes
O53 . C54 . H541 . 125.2 no
C55 . C54 . H541 . 125.2 no
Br2 . C55 . C51 . 128.6(7) yes
Br2 . C55 . C54 . 124.7(8) yes
C51 . C55 . C54 . 106.5(9) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 C24 3.47(1) . 4 no
O13 O23 3.257(9) . 2 no
O13 C24 3.30(1) . 2 no
O13 C34 3.51(1) . 1_655 no
O23 C12 3.41(1) . 2_445 no
O23 C42 3.56(1) . 2_545 no
O33 C44 3.19(1) . 3_564 no
O33 O43 3.50(1) . 3_564 no
O33 C12 3.51(1) . 3_464 no
O43 O53 3.22(1) . 2 no
O43 C32 3.28(1) . 3_565 no
O43 C54 3.30(1) . 2 no
O53 C42 3.34(1) . 2_445 no
O53 C22 3.39(1) . 1_455 no
C11 C52 3.49(1) . 1_655 no
C32 C44 3.44(1) . 3_564 no
C34 C44 3.48(2) . 3_564 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C11 C12 O13 . . . . -179.8(7) no
Br1 C11 C15 C14 . . . . -179.4(7) no
Br1 C11 C15 C21 . . . . 4(2) no
Br2 C55 C51 C45 . . . . 4(2) no
Br2 C55 C51 C52 . . . . -178.3(8) no
Br2 C55 C54 O53 . . . . 178.7(7) no
O13 C12 C11 C15 . . . . 2(1) no
O13 C14 C15 C11 . . . . -0(1) no
O13 C14 C15 C21 . . . . 176.6(9) no
O23 C22 C21 C15 . . . . -178.5(9) no
O23 C22 C21 C25 . . . . -1(1) no
O23 C24 C25 C21 . . . . 0(1) no
O23 C24 C25 C31 . . . . -174.8(9) no
O33 C32 C31 C25 . . . . 175.9(9) no
O33 C32 C31 C35 . . . . -1(1) no
O33 C34 C35 C31 . . . . -1(1) no
O33 C34 C35 C41 . . . . -177.5(9) no
O43 C42 C41 C35 . . . . -179.0(9) no
O43 C42 C41 C45 . . . . 0(1) no
O43 C44 C45 C41 . . . . -0(1) no
O43 C44 C45 C51 . . . . 179.9(9) no
O53 C52 C51 C45 . . . . 179.1(9) no
O53 C52 C51 C55 . . . . 1(1) no
O53 C54 C55 C51 . . . . 2(1) no
C11 C12 O13 C14 . . . . -2(1) no
C11 C15 C21 C22 . . . . -50(2) no
C11 C15 C21 C25 . . . . 134(1) no
C12 O13 C14 C15 . . . . 1(1) no
C12 C11 C15 C14 . . . . -1(1) no
C12 C11 C15 C21 . . . . -178(1) no
C14 C15 C21 C22 . . . . 134(1) no
C14 C15 C21 C25 . . . . -42(2) no
C15 C21 C25 C24 . . . . 177(1) no
C15 C21 C25 C31 . . . . -7(2) no
C21 C22 O23 C24 . . . . 2(1) no
C21 C25 C31 C32 . . . . 133(1) no
C21 C25 C31 C35 . . . . -50(2) no
C22 O23 C24 C25 . . . . -1(1) no
C22 C21 C25 C24 . . . . 1(1) no
C22 C21 C25 C31 . . . . 176(1) no
C24 C25 C31 C32 . . . . -53(2) no
C24 C25 C31 C35 . . . . 124(1) no
C25 C31 C35 C34 . . . . -176.2(9) no
C25 C31 C35 C41 . . . . 1(2) no
C31 C32 O33 C34 . . . . 1(1) no
C31 C35 C41 C42 . . . . 119(1) no
C31 C35 C41 C45 . . . . -60(2) no
C32 O33 C34 C35 . . . . -0(1) no
C32 C31 C35 C34 . . . . 1(1) no
C32 C31 C35 C41 . . . . 178(1) no
C34 C35 C41 C42 . . . . -64(2) no
C34 C35 C41 C45 . . . . 116(1) no
C35 C41 C45 C44 . . . . 179.3(9) no
C35 C41 C45 C51 . . . . -1(2) no
C41 C42 O43 C44 . . . . -1(1) no
C41 C45 C51 C52 . . . . -21(2) no
C41 C45 C51 C55 . . . . 156(1) no
C42 O43 C44 C45 . . . . 0(1) no
C42 C41 C45 C44 . . . . -0(1) no
C42 C41 C45 C51 . . . . 179.8(9) no
C44 C45 C51 C52 . . . . 159(1) no
C44 C45 C51 C55 . . . . -24(2) no
C45 C51 C55 C54 . . . . -180(1) no
C51 C52 O53 C54 . . . . 0(1) no
C52 O53 C54 C55 . . . . -2(1) no
C52 C51 C55 C54 . . . . -2(1) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd20_she1012.cif'
data_she1012
_database_code_depnum_ccdc_archive 'CCDC 860339'
_audit_creation_date 10-04-01
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2010-04-01 - Report on C28 H14 Br2 O7
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2010-04-06 - passes checkcif tests with warnings
;
_oxford_structure_analysis_title '4011218 she1012'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 7.3671(14)
_cell_length_b 12.397(2)
_cell_length_c 13.127(3)
_cell_angle_alpha 92.975(11)
_cell_angle_beta 93.428(9)
_cell_angle_gamma 95.781(12)
_cell_volume 1188.7(4)
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M 'P -1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 2
# Given Formula = C28 H14 Br2 O7
# Dc = 1.74 Fooo = 616.00 Mu = 34.59 M = 622.22
# Found Formula = C28 H14 Br2 O7
# Dc = 1.74 FOOO = 616.00 Mu = 34.59 M = 622.22
_chemical_formula_sum 'C28 H14 Br2 O7'
_chemical_formula_moiety 'C28 H14 Br2 O7'
_chemical_compound_source local
_chemical_formula_weight 622.22
_cell_measurement_reflns_used 9077
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 25
_cell_measurement_temperature 200
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.020
_exptl_crystal_size_mid 0.020
_exptl_crystal_size_max 0.420
_exptl_crystal_density_diffrn 1.738
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 3.459
# Sheldrick geometric approximatio 0.93 0.93
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.73
_exptl_absorpt_correction_T_max 0.93
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 440 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 90 percent of data collected with 2-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 10999
_reflns_number_total 4175
_diffrn_reflns_av_R_equivalents 0.157
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 4175
# Theoretical number of reflections is about 8604
_diffrn_reflns_theta_min 2.785
_diffrn_reflns_theta_max 25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_reflns_limit_h_min -8
_reflns_limit_h_max 8
_reflns_limit_k_min -14
_reflns_limit_k_max 14
_reflns_limit_l_min 0
_reflns_limit_l_max 15
_oxford_diffrn_Wilson_B_factor 3.08
_oxford_diffrn_Wilson_scale 75.89
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -3.83
_refine_diff_density_max 2.28
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 4174
_refine_ls_number_restraints 0
_refine_ls_number_parameters 334
_oxford_refine_ls_R_factor_ref 0.2389
_refine_ls_wR_factor_ref 0.2490
_refine_ls_goodness_of_fit_ref 0.9873
_refine_ls_shift/su_max 0.0001468
_refine_ls_shift/su_mean .000007 # 0.0006977
# The values computed from all data
_oxford_reflns_number_all 4174
_refine_ls_R_factor_all 0.2389
_refine_ls_wR_factor_all 0.2490
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1664
_refine_ls_R_factor_gt 0.1017
_refine_ls_wR_factor_gt 0.1769
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.00P)^2^ +22.46P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~28~H~14~Br~2~O~7~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one
molecule of C~28~H~14~Br~2~O~7~.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
The crystals supplied were generally very small and intergrown.
One extremely thin lath was discovered, however, and was used for this study.
Even with long exposure times, the number of
reflections with intensities above background
is limited.
The observation:parameter ratio is therefore lower than we would like
but the identity of the compound is clearly established, nonetheless.
The precision of the bond lengths and angles is rather poor, however.
Hydrogen atoms were included at calculated position
and ride on the atoms to which they are bonded.
The peaks in the final difference electron density map
are distributed randomly through the structure.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from hexane/chloroform.
The sample ID is tf-Br~2~Fu~7~.
;
_refine_special_details
;
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Blessing, R. H. (1995). Acta Crystallogr., Section A, 51, 33-37.
Blessing, R. H. (1997). J. Appl. Crystallogr., 30, 421-426.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 0.1529(2) 0.54636(17) 0.90856(15) 0.0649 1.0000 Uani . . . . . . .
Br2 Br 0.8312(4) 0.1224(2) 0.08769(18) 0.1027 1.0000 Uani . . . . . . .
C11 C 0.388(2) 0.5590(12) 0.8615(12) 0.0456 1.0000 Uani . . . . . . .
C12 C 0.479(2) 0.6492(14) 0.8325(11) 0.0482 1.0000 Uani . . . . . . .
O13 O 0.6456(14) 0.6286(10) 0.8033(8) 0.0539 1.0000 Uani . . . . . . .
C14 C 0.659(2) 0.5208(14) 0.8163(11) 0.0484 1.0000 Uani . . . . . . .
C15 C 0.5100(17) 0.4721(13) 0.8521(11) 0.0391 1.0000 Uani . . . . . . .
C21 C 0.4739(19) 0.3563(13) 0.8722(11) 0.0435 1.0000 Uani . . . . . . .
C22 C 0.343(2) 0.3123(13) 0.9290(11) 0.0434 1.0000 Uani . . . . . . .
O23 O 0.3474(15) 0.2031(10) 0.9306(9) 0.0635 1.0000 Uani . . . . . . .
C24 C 0.491(2) 0.1780(14) 0.8736(12) 0.0525 1.0000 Uani . . . . . . .
C25 C 0.571(2) 0.2661(13) 0.8359(12) 0.0495 1.0000 Uani . . . . . . .
C31 C 0.732(2) 0.2701(13) 0.7738(11) 0.0421 1.0000 Uani . . . . . . .
C32 C 0.896(2) 0.2487(13) 0.8054(12) 0.0509 1.0000 Uani . . . . . . .
O33 O 1.0171(13) 0.2533(9) 0.7314(8) 0.0461 1.0000 Uani . . . . . . .
C34 C 0.918(2) 0.2814(12) 0.6480(12) 0.0440 1.0000 Uani . . . . . . .
C35 C 0.7417(19) 0.2914(12) 0.6650(12) 0.0407 1.0000 Uani . . . . . . .
C41 C 0.5994(18) 0.3177(10) 0.5924(11) 0.0323 1.0000 Uani . . . . . . .
C42 C 0.4233(19) 0.3264(12) 0.6128(12) 0.0410 1.0000 Uani . . . . . . .
O43 O 0.3219(13) 0.3514(9) 0.5275(8) 0.0487 1.0000 Uani . . . . . . .
C44 C 0.442(2) 0.3606(14) 0.4531(13) 0.0564 1.0000 Uani . . . . . . .
C45 C 0.613(2) 0.3413(13) 0.4887(13) 0.0468 1.0000 Uani . . . . . . .
C51 C 0.7753(18) 0.3460(13) 0.4251(10) 0.0335 1.0000 Uani . . . . . . .
C52 C 0.872(2) 0.4367(14) 0.4003(11) 0.0479 1.0000 Uani . . . . . . .
O53 O 1.0109(14) 0.4121(8) 0.3411(8) 0.0474 1.0000 Uani . . . . . . .
C54 C 0.999(2) 0.3014(14) 0.3324(11) 0.0493 1.0000 Uani . . . . . . .
C55 C 0.8563(19) 0.2571(12) 0.3806(11) 0.0390 1.0000 Uani . . . . . . .
C61 C 0.801(2) 0.1394(12) 0.3855(12) 0.0466 1.0000 Uani . . . . . . .
C62 C 0.664(2) 0.0937(13) 0.4374(14) 0.0650 1.0000 Uani . . . . . . .
O63 O 0.6498(17) -0.0170(9) 0.4266(10) 0.0805 1.0000 Uani . . . . . . .
C64 C 0.784(2) -0.0400(16) 0.3651(14) 0.0682 1.0000 Uani . . . . . . .
C65 C 0.873(2) 0.0484(13) 0.3348(13) 0.0523 1.0000 Uani . . . . . . .
C71 C 1.034(2) 0.0526(13) 0.2696(13) 0.0490 1.0000 Uani . . . . . . .
C72 C 1.205(3) 0.0345(15) 0.2977(17) 0.0751 1.0000 Uani . . . . . . .
O73 O 1.313(2) 0.0476(12) 0.2155(15) 0.0974 1.0000 Uani . . . . . . .
C74 C 1.200(3) 0.0788(16) 0.1352(18) 0.0903 1.0000 Uani . . . . . . .
C75 C 1.033(3) 0.0846(12) 0.1671(14) 0.0574 1.0000 Uani . . . . . . .
H121 H 0.4330 0.7182 0.8323 0.0578 1.0000 Uiso R . . . . . .
H141 H 0.7637 0.4852 0.8014 0.0581 1.0000 Uiso R . . . . . .
H221 H 0.2592 0.3521 0.9635 0.0520 1.0000 Uiso R . . . . . .
H241 H 0.5271 0.1071 0.8630 0.0630 1.0000 Uiso R . . . . . .
H321 H 0.9269 0.2317 0.8736 0.0611 1.0000 Uiso R . . . . . .
H341 H 0.9679 0.2928 0.5839 0.0528 1.0000 Uiso R . . . . . .
H421 H 0.3759 0.3165 0.6778 0.0492 1.0000 Uiso R . . . . . .
H441 H 0.4113 0.3783 0.3851 0.0677 1.0000 Uiso R . . . . . .
H521 H 0.8482 0.5083 0.4208 0.0575 1.0000 Uiso R . . . . . .
H541 H 1.0805 0.2609 0.2969 0.0592 1.0000 Uiso R . . . . . .
H621 H 0.5859 0.1335 0.4766 0.0780 1.0000 Uiso R . . . . . .
H641 H 0.8104 -0.1115 0.3461 0.0819 1.0000 Uiso R . . . . . .
H721 H 1.2464 0.0157 0.3637 0.0901 1.0000 Uiso R . . . . . .
H741 H 1.2367 0.0936 0.0688 0.1084 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0421(10) 0.0866(15) 0.0695(14) 0.0081(12) 0.0153(9) 0.0150(10)
Br2 0.151(3) 0.095(2) 0.0656(16) -0.0005(14) 0.0032(15) 0.0333(18)
C11 0.057(11) 0.037(10) 0.045(10) 0.014(8) 0.007(8) 0.006(9)
C12 0.041(10) 0.054(11) 0.047(10) 0.008(9) -0.008(8) -0.001(9)
O13 0.044(7) 0.071(9) 0.051(7) 0.016(6) 0.018(6) 0.007(6)
C14 0.053(11) 0.062(12) 0.037(9) 0.019(9) 0.015(8) 0.021(9)
C15 0.020(7) 0.060(11) 0.035(9) -0.012(8) 0.015(7) -0.007(7)
C21 0.033(8) 0.057(11) 0.042(9) -0.009(8) 0.004(7) 0.014(8)
C22 0.048(10) 0.040(10) 0.044(10) 0.010(8) 0.002(8) 0.010(8)
O23 0.058(8) 0.071(9) 0.064(8) 0.021(7) 0.033(6) -0.009(7)
C24 0.060(11) 0.053(12) 0.046(10) 0.013(9) 0.019(9) -0.002(9)
C25 0.054(11) 0.051(11) 0.049(10) 0.024(9) 0.011(8) 0.017(9)
C31 0.042(10) 0.050(11) 0.034(9) 0.000(8) 0.005(8) 0.003(8)
C32 0.050(10) 0.068(13) 0.040(10) 0.020(9) 0.010(8) 0.018(9)
O33 0.029(6) 0.073(8) 0.039(7) 0.008(6) 0.005(5) 0.013(6)
C34 0.047(10) 0.044(10) 0.042(10) -0.010(8) 0.013(8) 0.006(8)
C35 0.029(8) 0.049(10) 0.049(10) 0.013(8) 0.013(7) 0.019(7)
C41 0.028(8) 0.021(8) 0.048(9) -0.006(7) 0.005(7) 0.004(6)
C42 0.032(8) 0.050(10) 0.042(10) 0.004(8) 0.019(8) -0.004(7)
O43 0.035(6) 0.073(8) 0.042(7) 0.008(6) 0.012(5) 0.016(6)
C44 0.037(10) 0.083(14) 0.046(11) -0.005(10) -0.005(8) 0.002(9)
C45 0.039(9) 0.052(11) 0.053(11) -0.005(9) 0.013(8) 0.017(8)
C51 0.020(7) 0.054(10) 0.028(8) 0.004(8) -0.001(6) 0.009(7)
C52 0.056(11) 0.060(12) 0.031(9) 0.008(8) 0.016(8) 0.015(9)
O53 0.050(7) 0.038(7) 0.053(7) -0.005(6) 0.017(6) -0.004(5)
C54 0.044(10) 0.063(12) 0.042(10) -0.006(9) 0.019(8) 0.002(9)
C55 0.043(9) 0.032(9) 0.043(9) 0.002(7) 0.014(8) 0.002(7)
C61 0.055(10) 0.040(10) 0.046(10) 0.002(8) 0.023(8) -0.001(8)
C62 0.070(12) 0.025(10) 0.102(15) -0.006(10) 0.048(11) -0.009(8)
O63 0.096(10) 0.036(8) 0.113(11) -0.009(7) 0.073(9) -0.007(7)
C64 0.063(12) 0.071(14) 0.077(14) 0.008(11) 0.036(11) 0.015(11)
C65 0.057(11) 0.038(10) 0.067(12) 0.007(9) 0.042(10) 0.005(9)
C71 0.052(11) 0.039(10) 0.058(12) 0.009(9) 0.018(9) 0.000(9)
C72 0.070(14) 0.067(14) 0.096(17) 0.027(12) 0.020(13) 0.023(11)
O73 0.087(11) 0.072(11) 0.139(16) 0.003(11) 0.062(11) 0.008(9)
C74 0.12(2) 0.061(15) 0.098(19) -0.016(13) 0.085(17) 0.007(14)
C75 0.082(13) 0.026(9) 0.069(13) 0.003(9) 0.032(11) 0.011(9)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.15978(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C11 . 1.870(15) yes
Br2 . C75 . 1.874(19) yes
C11 . C12 . 1.33(2) yes
C11 . C15 . 1.47(2) yes
C12 . O13 . 1.354(17) yes
C12 . H121 . 0.950 no
O13 . C14 . 1.369(18) yes
C14 . C15 . 1.325(19) yes
C14 . H141 . 0.950 no
C15 . C21 . 1.47(2) yes
C21 . C22 . 1.343(19) yes
C21 . C25 . 1.46(2) yes
C22 . O23 . 1.358(17) yes
C22 . H221 . 0.950 no
O23 . C24 . 1.382(17) yes
C24 . C25 . 1.32(2) yes
C24 . H241 . 0.950 no
C25 . C31 . 1.480(19) yes
C31 . C32 . 1.308(19) yes
C31 . C35 . 1.47(2) yes
C32 . O33 . 1.358(16) yes
C32 . H321 . 0.950 no
O33 . C34 . 1.360(17) yes
C34 . C35 . 1.347(18) yes
C34 . H341 . 0.950 no
C35 . C41 . 1.447(19) yes
C41 . C42 . 1.354(17) yes
C41 . C45 . 1.41(2) yes
C42 . O43 . 1.375(17) yes
C42 . H421 . 0.950 no
O43 . C44 . 1.359(17) yes
C44 . C45 . 1.36(2) yes
C44 . H441 . 0.950 no
C45 . C51 . 1.496(18) yes
C51 . C52 . 1.34(2) yes
C51 . C55 . 1.420(18) yes
C52 . O53 . 1.369(16) yes
C52 . H521 . 0.950 no
O53 . C54 . 1.365(18) yes
C54 . C55 . 1.342(19) yes
C54 . H541 . 0.950 no
C55 . C61 . 1.481(19) yes
C61 . C62 . 1.35(2) yes
C61 . C65 . 1.44(2) yes
C62 . O63 . 1.365(17) yes
C62 . H621 . 0.950 no
O63 . C64 . 1.357(17) yes
C64 . C65 . 1.31(2) yes
C64 . H641 . 0.950 no
C65 . C71 . 1.50(2) yes
C71 . C72 . 1.34(2) yes
C71 . C75 . 1.42(2) yes
C72 . O73 . 1.38(2) yes
C72 . H721 . 0.950 no
O73 . C74 . 1.40(3) yes
C74 . C75 . 1.33(2) yes
C74 . H741 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C11 . C12 . 126.1(12) yes
Br1 . C11 . C15 . 126.7(11) yes
C12 . C11 . C15 . 107.2(14) yes
C11 . C12 . O13 . 110.1(14) yes
C11 . C12 . H121 . 124.9 no
O13 . C12 . H121 . 124.9 no
C12 . O13 . C14 . 106.7(12) yes
O13 . C14 . C15 . 112.1(14) yes
O13 . C14 . H141 . 124.0 no
C15 . C14 . H141 . 124.0 no
C11 . C15 . C14 . 103.9(15) yes
C11 . C15 . C21 . 129.0(12) yes
C14 . C15 . C21 . 127.1(14) yes
C15 . C21 . C22 . 126.3(13) yes
C15 . C21 . C25 . 128.0(13) yes
C22 . C21 . C25 . 105.7(15) yes
C21 . C22 . O23 . 110.8(14) yes
C21 . C22 . H221 . 124.6 no
O23 . C22 . H221 . 124.6 no
C22 . O23 . C24 . 106.5(12) yes
O23 . C24 . C25 . 110.8(15) yes
O23 . C24 . H241 . 124.6 no
C25 . C24 . H241 . 124.6 no
C21 . C25 . C24 . 106.2(14) yes
C21 . C25 . C31 . 128.1(15) yes
C24 . C25 . C31 . 125.6(15) yes
C25 . C31 . C32 . 125.5(15) yes
C25 . C31 . C35 . 128.3(14) yes
C32 . C31 . C35 . 106.1(13) yes
C31 . C32 . O33 . 113.5(14) yes
C31 . C32 . H321 . 123.3 no
O33 . C32 . H321 . 123.3 no
C32 . O33 . C34 . 103.8(11) yes
O33 . C34 . C35 . 113.5(13) yes
O33 . C34 . H341 . 123.3 no
C35 . C34 . H341 . 123.3 no
C31 . C35 . C34 . 103.1(13) yes
C31 . C35 . C41 . 129.5(12) yes
C34 . C35 . C41 . 127.4(14) yes
C35 . C41 . C42 . 125.4(14) yes
C35 . C41 . C45 . 128.5(12) yes
C42 . C41 . C45 . 106.1(13) yes
C41 . C42 . O43 . 111.3(12) yes
C41 . C42 . H421 . 124.3 no
O43 . C42 . H421 . 124.3 no
C42 . O43 . C44 . 105.1(11) yes
O43 . C44 . C45 . 111.3(15) yes
O43 . C44 . H441 . 124.4 no
C45 . C44 . H441 . 124.4 no
C41 . C45 . C44 . 106.2(13) yes
C41 . C45 . C51 . 129.9(14) yes
C44 . C45 . C51 . 123.9(15) yes
C45 . C51 . C52 . 125.4(14) yes
C45 . C51 . C55 . 127.4(14) yes
C52 . C51 . C55 . 107.1(12) yes
C51 . C52 . O53 . 110.4(13) yes
C51 . C52 . H521 . 124.8 no
O53 . C52 . H521 . 124.8 no
C52 . O53 . C54 . 105.5(11) yes
O53 . C54 . C55 . 111.2(13) yes
O53 . C54 . H541 . 124.4 no
C55 . C54 . H541 . 124.4 no
C51 . C55 . C54 . 105.7(14) yes
C51 . C55 . C61 . 128.5(13) yes
C54 . C55 . C61 . 125.8(14) yes
C55 . C61 . C62 . 126.6(14) yes
C55 . C61 . C65 . 129.2(13) yes
C62 . C61 . C65 . 104.2(14) yes
C61 . C62 . O63 . 111.7(14) yes
C61 . C62 . H621 . 124.2 no
O63 . C62 . H621 . 124.2 no
C62 . O63 . C64 . 105.1(13) yes
O63 . C64 . C65 . 111.8(15) yes
O63 . C64 . H641 . 124.1 no
C65 . C64 . H641 . 124.1 no
C61 . C65 . C64 . 107.0(13) yes
C61 . C65 . C71 . 126.9(14) yes
C64 . C65 . C71 . 125.7(14) yes
C65 . C71 . C72 . 127.3(18) yes
C65 . C71 . C75 . 125.3(16) yes
C72 . C71 . C75 . 107.4(16) yes
C71 . C72 . O73 . 109.4(19) yes
C71 . C72 . H721 . 125.3 no
O73 . C72 . H721 . 125.3 no
C72 . O73 . C74 . 106.4(16) yes
O73 . C74 . C75 . 109.0(18) yes
O73 . C74 . H741 . 125.5 no
C75 . C74 . H741 . 125.5 no
Br2 . C75 . C71 . 126.8(13) yes
Br2 . C75 . C74 . 125.4(18) yes
C71 . C75 . C74 . 107.7(19) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O53 3.51(1) . 2_666 no
Br1 Br1 3.546(4) . 2_567 no
O13 O53 3.31(2) . 2_766 no
O13 C54 3.32(2) . 2_766 no
O13 C44 3.40(2) . 2_666 no
O13 C22 3.55(2) . 2_667 no
O23 C74 3.35(3) . 1_456 no
O23 O33 3.59(2) . 1_455 no
O33 C64 3.38(2) . 2_756 no
O33 C22 3.43(2) . 1_655 no
O33 C42 3.52(2) . 1_655 no
O43 C52 3.24(2) . 2_666 no
O43 C54 3.38(2) . 1_455 no
O43 O53 3.42(1) . 1_455 no
O43 C34 3.51(2) . 1_455 no
O53 C14 3.35(2) . 2_766 no
O53 C44 3.55(2) . 1_655 no
O63 O63 3.06(3) . 2_656 no
O63 C62 3.11(2) . 2_656 no
O73 C24 3.46(2) . 2_756 no
C11 C22 3.51(2) . 2_667 no
C12 C22 3.31(2) . 2_667 no
C22 C32 3.58(2) . 1_455 no
C44 C54 3.53(2) . 1_455 no
C52 C52 3.36(3) . 2_766 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C11 C12 O13 . . . . 180(1) no
Br1 C11 C15 C14 . . . . -180(1) no
Br1 C11 C15 C21 . . . . 3(2) no
Br2 C75 C71 C65 . . . . -3(2) no
Br2 C75 C71 C72 . . . . -179(1) no
Br2 C75 C74 O73 . . . . -180(1) no
O13 C12 C11 C15 . . . . 1(2) no
O13 C14 C15 C11 . . . . 1(2) no
O13 C14 C15 C21 . . . . 178(1) no
O23 C22 C21 C15 . . . . 179(1) no
O23 C22 C21 C25 . . . . -1(2) no
O23 C24 C25 C21 . . . . 1(2) no
O23 C24 C25 C31 . . . . 178(1) no
O33 C32 C31 C25 . . . . 177(1) no
O33 C32 C31 C35 . . . . 0(2) no
O33 C34 C35 C31 . . . . 2(2) no
O33 C34 C35 C41 . . . . -178(1) no
O43 C42 C41 C35 . . . . -179(1) no
O43 C42 C41 C45 . . . . 2(2) no
O43 C44 C45 C41 . . . . 0(2) no
O43 C44 C45 C51 . . . . -180(1) no
O53 C52 C51 C45 . . . . -180(1) no
O53 C52 C51 C55 . . . . 1(2) no
O53 C54 C55 C51 . . . . -2(2) no
O53 C54 C55 C61 . . . . 179(1) no
O63 C62 C61 C55 . . . . -180(1) no
O63 C62 C61 C65 . . . . 2(2) no
O63 C64 C65 C61 . . . . 4(2) no
O63 C64 C65 C71 . . . . 177(1) no
O73 C72 C71 C65 . . . . -179(2) no
O73 C72 C71 C75 . . . . -3(2) no
O73 C74 C75 C71 . . . . -2(2) no
C11 C12 O13 C14 . . . . -1(2) no
C11 C15 C21 C22 . . . . -20(2) no
C11 C15 C21 C25 . . . . 161(2) no
C12 O13 C14 C15 . . . . 0(2) no
C12 C11 C15 C14 . . . . -1(2) no
C12 C11 C15 C21 . . . . -178(1) no
C14 C15 C21 C22 . . . . 164(2) no
C14 C15 C21 C25 . . . . -16(2) no
C15 C21 C25 C24 . . . . 180(1) no
C15 C21 C25 C31 . . . . 2(2) no
C21 C22 O23 C24 . . . . 1(2) no
C21 C25 C31 C32 . . . . 112(2) no
C21 C25 C31 C35 . . . . -72(2) no
C22 O23 C24 C25 . . . . -1(2) no
C22 C21 C25 C24 . . . . -0(2) no
C22 C21 C25 C31 . . . . -177(1) no
C24 C25 C31 C32 . . . . -64(2) no
C24 C25 C31 C35 . . . . 111(2) no
C25 C31 C35 C34 . . . . -178(2) no
C25 C31 C35 C41 . . . . 3(3) no
C31 C32 O33 C34 . . . . 1(2) no
C31 C35 C41 C42 . . . . -1(2) no
C31 C35 C41 C45 . . . . 178(2) no
C32 O33 C34 C35 . . . . -2(2) no
C32 C31 C35 C34 . . . . -1(2) no
C32 C31 C35 C41 . . . . 179(2) no
C34 C35 C41 C42 . . . . 180(2) no
C34 C35 C41 C45 . . . . -2(2) no
C35 C41 C45 C44 . . . . 180(1) no
C35 C41 C45 C51 . . . . -0(3) no
C41 C42 O43 C44 . . . . -1(2) no
C41 C45 C51 C52 . . . . -102(2) no
C41 C45 C51 C55 . . . . 77(2) no
C42 O43 C44 C45 . . . . 1(2) no
C42 C41 C45 C44 . . . . -1(2) no
C42 C41 C45 C51 . . . . 179(2) no
C44 C45 C51 C52 . . . . 78(2) no
C44 C45 C51 C55 . . . . -103(2) no
C45 C51 C55 C54 . . . . -179(1) no
C45 C51 C55 C61 . . . . 0(2) no
C51 C52 O53 C54 . . . . -2(2) no
C51 C55 C61 C62 . . . . -3(3) no
C51 C55 C61 C65 . . . . 175(2) no
C52 O53 C54 C55 . . . . 2(2) no
C52 C51 C55 C54 . . . . 1(2) no
C52 C51 C55 C61 . . . . 180(1) no
C54 C55 C61 C62 . . . . 177(2) no
C54 C55 C61 C65 . . . . -6(3) no
C55 C61 C65 C64 . . . . 178(2) no
C55 C61 C65 C71 . . . . 5(3) no
C61 C62 O63 C64 . . . . -0(2) no
C61 C65 C71 C72 . . . . 99(2) no
C61 C65 C71 C75 . . . . -77(2) no
C62 O63 C64 C65 . . . . -3(2) no
C62 C61 C65 C64 . . . . -4(2) no
C62 C61 C65 C71 . . . . -177(2) no
C64 C65 C71 C72 . . . . -73(2) no
C64 C65 C71 C75 . . . . 111(2) no
C65 C71 C75 C74 . . . . 180(2) no
C71 C72 O73 C74 . . . . 2(2) no
C72 O73 C74 C75 . . . . 0(2) no
C72 C71 C75 C74 . . . . 3(2) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd22_she0936.cif'
data_she0936
_database_code_depnum_ccdc_archive 'CCDC 860340'
_audit_creation_date 09-11-13
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2009-11-16 - Report on C24 H12 Br2 O6
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2009-11-16 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '11101646 she0936 numabs'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 6.9255(7)
_cell_length_b 7.3969(7)
_cell_length_c 11.6514(11)
_cell_angle_alpha 72.785(5)
_cell_angle_beta 78.030(6)
_cell_angle_gamma 63.603(5)
_cell_volume 508.68(9)
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M 'P -1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 1
# Given Formula = C24 H12 Br2 O6
# Dc = 1.82 Fooo = 274.00 Mu = 40.26 M = 278.08
# Found Formula = C24 H12 Br2 O6
# Dc = 1.82 FOOO = 274.00 Mu = 40.26 M = 278.08
_chemical_formula_sum 'C24 H12 Br2 O6'
_chemical_formula_moiety 'C24 H12 Br2 O6'
_chemical_compound_source local
_chemical_formula_weight 556.16
_cell_measurement_reflns_used 8413
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 25
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.01
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_max 0.40
_exptl_crystal_density_diffrn 1.815
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 274
_exptl_absorpt_coefficient_mu 4.026
# Sheldrick geometric approximatio 0.59 0.92
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.220
0 1 0 0.080
0 -1 0 0.050
0 0 1 0.005
0 0 -1 0.010
3 2 0 0.150
-1 -1 0 0.200
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.483
_exptl_absorpt_correction_T_max 0.942
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.049
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 240 sec/frame,
crystal-detector distance 32mm,
multiple scan sets so over 90 percent of data collected with 2-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 6643
_reflns_number_total 1759
_diffrn_reflns_av_R_equivalents 0.068
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 1759
# Theoretical number of reflections is about 3602
_diffrn_reflns_theta_min 3.161
_diffrn_reflns_theta_max 25.044
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full 25.044
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_reflns_limit_h_min -7
_reflns_limit_h_max 8
_reflns_limit_k_min -8
_reflns_limit_k_max 8
_reflns_limit_l_min 0
_reflns_limit_l_max 13
_oxford_diffrn_Wilson_B_factor 4.59
_oxford_diffrn_Wilson_scale 2.96
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -1.26
_refine_diff_density_max 0.83
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 1757
_refine_ls_number_restraints 0
_refine_ls_number_parameters 145
_oxford_refine_ls_R_factor_ref 0.0970
_refine_ls_wR_factor_ref 0.1586
_refine_ls_goodness_of_fit_ref 1.0534
_refine_ls_shift/su_max 0.0001925
_refine_ls_shift/su_mean 0.0000381
# The values computed from all data
_oxford_reflns_number_all 1757
_refine_ls_R_factor_all 0.0970
_refine_ls_wR_factor_all 0.1586
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1190
_refine_ls_R_factor_gt 0.0652
_refine_ls_wR_factor_gt 0.1409
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 2.12P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~24~H~12~Br~2~O~6~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one-half of a
molecule of C~24~H~12~Br~2~O~6~.
The other half of the molecule is generated by a crystallographic
inversion symmetry operation.
The crystals supplied were very thin plates and generally intergrown.
One extremely thin plate was selected and used for this study.
During data collection, spots were observed that did not belong to the
major diffraction pattern suggesting that the crystal
was not single or
was split to some degree.
The final structure shows that the displacement ellipsoids for almost all atoms
are elongated,
those within the rings containing atoms O23 and O33 largely in the c direction,
and those within the ring containing O13 generally in the a direction.
Use of intensity data scaled by multi-scan inter-frame methods
(DENZO/SCALEPACK, Otwinowski & Minor, 1997) made
no difference, though that should have corrected for any miscentering of
the crystal (G\"orbitz, 1999).
Splitting every atom over two sites appears excessively complicated
and has not been pursued,
nor has the possibility of a P1 space group with a pseudo centre of symmetry.
The compound is clearly identified although the
precision of the bond lengths and angles are not particularly good.
Hydrogen atoms were included at idealized positions and
ride on the atoms to which they are bonded.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms were included at
calculated positions and ride on the atom to which they are bonded.
The largest peaks in the final difference electron density map
are located near the Br atoms.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from dichloromethane/hexane.
The sample ID is tf710-Bu~2~Fu~6~.
;
_refine_special_details
;
The final structure shows that the displacement ellipsoids for almost all atoms
are elongated,
those within the rings containing atoms O23 and O33 largely in the c direction,
and those within the ring containing O13 generally in the a direction.
Use of intensity data scaled by multi-scan inter-frame methods
(DENZO/SCALEPACK, Otwinowski & Minor, 1997) made
no difference, though that should have corrected for any miscentering of
the crystal (G\"orbitz, 1999).
Splitting every atom over two sites appears excessively complicated
and has not been pursued,
nor has the possibility of a P1 space group with a pseudo centre of symmetry.
The compound is clearly identified although the
precision of the bond lengths and angles are not particularly good.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 0.41863(19) -0.23857(11) 0.90674(8) 0.1101 1.0000 Uani . . . . . . .
C11 C 0.3413(15) 0.0471(11) 0.8714(7) 0.0897 1.0000 Uani . . . . . . .
C12 C 0.1464(17) 0.1861(12) 0.9008(8) 0.1100 1.0000 Uani . . . . . . .
O13 O 0.1426(11) 0.3813(7) 0.8596(5) 0.1075 1.0000 Uani . . . . . . .
C14 C 0.3416(16) 0.3576(11) 0.8034(9) 0.1009 1.0000 Uani . . . . . . .
C15 C 0.4723(15) 0.1550(11) 0.8075(8) 0.0841 1.0000 Uani . . . . . . .
C21 C 0.6980(13) 0.0730(10) 0.7549(9) 0.0834 1.0000 Uani . . . . . . .
C22 C 0.8486(18) -0.1276(12) 0.7790(11) 0.1135 1.0000 Uani . . . . . . .
O23 O 1.0381(11) -0.1498(8) 0.7122(9) 0.1336 1.0000 Uani . . . . . . .
C24 C 1.0099(14) 0.0442(12) 0.6441(12) 0.1230 1.0000 Uani . . . . . . .
C25 C 0.8081(12) 0.1847(10) 0.6650(10) 0.0882 1.0000 Uani . . . . . . .
C31 C 0.7276(11) 0.4106(10) 0.6079(9) 0.0829 1.0000 Uani . . . . . . .
C32 C 0.8011(13) 0.5395(11) 0.6256(11) 0.1064 1.0000 Uani . . . . . . .
O33 O 0.6948(9) 0.7364(7) 0.5615(7) 0.1010 1.0000 Uani . . . . . . .
C34 C 0.5502(12) 0.7300(10) 0.5007(9) 0.0803 1.0000 Uani . . . . . . .
C35 C 0.5635(10) 0.5338(9) 0.5250(8) 0.0716 1.0000 Uani . . . . . . .
H121 H 0.0284 0.1545 0.9437 0.1315 1.0000 Uiso R . . . . . .
H141 H 0.3840 0.4688 0.7660 0.1208 1.0000 Uiso R . . . . . .
H221 H 0.8228 -0.2383 0.8361 0.1359 1.0000 Uiso R . . . . . .
H241 H 1.1187 0.0757 0.5889 0.1472 1.0000 Uiso R . . . . . .
H321 H 0.9123 0.4988 0.6758 0.1279 1.0000 Uiso R . . . . . .
H341 H 0.4538 0.8464 0.4487 0.0963 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1463(10) 0.0359(4) 0.0838(6) 0.0016(3) 0.0325(6) -0.0092(4)
C11 0.118(7) 0.036(4) 0.060(5) 0.001(3) 0.015(4) 0.000(4)
C12 0.131(8) 0.044(4) 0.083(6) 0.002(4) 0.041(5) -0.004(5)
O13 0.127(5) 0.034(3) 0.094(4) -0.005(3) 0.022(4) 0.006(3)
C14 0.092(7) 0.035(4) 0.131(8) -0.013(4) 0.007(6) 0.003(4)
C15 0.095(6) 0.036(4) 0.089(6) -0.013(4) -0.015(5) 0.004(4)
C21 0.075(6) 0.029(3) 0.132(8) -0.020(4) -0.026(5) 0.000(4)
C22 0.102(8) 0.031(4) 0.171(10) -0.022(5) -0.021(7) 0.008(4)
O23 0.072(4) 0.034(3) 0.262(10) -0.032(4) -0.021(5) 0.008(3)
C24 0.063(6) 0.036(4) 0.256(14) -0.032(6) -0.024(7) -0.006(4)
C25 0.049(4) 0.027(3) 0.181(9) -0.026(4) -0.026(5) -0.001(3)
C31 0.044(4) 0.032(3) 0.173(9) -0.032(4) -0.016(5) -0.009(3)
C32 0.064(5) 0.035(4) 0.224(12) -0.032(5) -0.050(6) -0.006(4)
O33 0.064(3) 0.035(3) 0.208(7) -0.032(3) -0.031(4) -0.013(2)
C34 0.046(4) 0.032(3) 0.157(8) -0.022(4) -0.009(5) -0.010(3)
C35 0.038(4) 0.029(3) 0.145(7) -0.029(4) -0.006(4) -0.007(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.818(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C11 . 1.869(7) yes
C11 . C12 . 1.334(11) yes
C11 . C15 . 1.423(12) yes
C12 . O13 . 1.370(10) yes
C12 . H121 . 0.950 no
O13 . C14 . 1.355(11) yes
C14 . C15 . 1.356(10) yes
C14 . H141 . 0.950 no
C15 . C21 . 1.472(12) yes
C21 . C22 . 1.367(10) yes
C21 . C25 . 1.442(12) yes
C22 . O23 . 1.347(13) yes
C22 . H221 . 0.950 no
O23 . C24 . 1.367(11) yes
C24 . C25 . 1.346(11) yes
C24 . H241 . 0.950 no
C25 . C31 . 1.487(10) yes
C31 . C32 . 1.343(10) yes
C31 . C35 . 1.439(11) yes
C32 . O33 . 1.361(10) yes
C32 . H321 . 0.950 no
O33 . C34 . 1.366(10) yes
C34 . C35 . 1.358(9) yes
C34 . H341 . 0.950 no
C35 . C35 2_666 1.462(14) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C11 . C12 . 124.3(8) yes
Br1 . C11 . C15 . 127.3(6) yes
C12 . C11 . C15 . 108.3(7) yes
C11 . C12 . O13 . 109.5(9) yes
C11 . C12 . H121 . 125.3 no
O13 . C12 . H121 . 125.3 no
C12 . O13 . C14 . 106.4(6) yes
O13 . C14 . C15 . 111.3(8) yes
O13 . C14 . H141 . 124.4 no
C15 . C14 . H141 . 124.3 no
C11 . C15 . C14 . 104.5(8) yes
C11 . C15 . C21 . 129.5(7) yes
C14 . C15 . C21 . 126.0(9) yes
C15 . C21 . C22 . 127.5(9) yes
C15 . C21 . C25 . 127.9(6) yes
C22 . C21 . C25 . 104.6(8) yes
C21 . C22 . O23 . 112.0(9) yes
C21 . C22 . H221 . 124.0 no
O23 . C22 . H221 . 124.0 no
C22 . O23 . C24 . 105.8(7) yes
O23 . C24 . C25 . 111.3(9) yes
O23 . C24 . H241 . 124.4 no
C25 . C24 . H241 . 124.3 no
C21 . C25 . C24 . 106.3(7) yes
C21 . C25 . C31 . 129.0(7) yes
C24 . C25 . C31 . 124.7(9) yes
C25 . C31 . C32 . 124.6(8) yes
C25 . C31 . C35 . 128.8(7) yes
C32 . C31 . C35 . 106.6(7) yes
C31 . C32 . O33 . 110.7(8) yes
C31 . C32 . H321 . 124.6 no
O33 . C32 . H321 . 124.6 no
C32 . O33 . C34 . 106.6(6) yes
O33 . C34 . C35 . 110.5(7) yes
O33 . C34 . H341 . 124.7 no
C35 . C34 . H341 . 124.8 no
C35 2_666 C35 . C31 . 128.2(7) yes
C35 2_666 C35 . C34 . 126.2(9) yes
C31 . C35 . C34 . 105.6(7) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O23 3.55(1) . 1_455 no
O13 O23 3.203(7) . 1_465 no
O13 C22 3.228(8) . 1_465 no
O13 C32 3.57(1) . 1_455 no
O23 C14 3.263(8) . 1_645 no
O33 C24 3.34(1) . 2_766 no
O33 C34 3.442(8) . 2_676 no
O33 C22 3.49(2) . 1_565 no
C22 C32 3.60(2) . 1_545 no
C32 C32 3.57(2) . 2_766 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C11 C12 O13 . . . . -178.8(7) no
Br1 C11 C15 C14 . . . . 178.6(8) no
Br1 C11 C15 C21 . . . . -1(2) no
O13 C12 C11 C15 . . . . -0(1) no
O13 C14 C15 C11 . . . . 0(1) no
O13 C14 C15 C21 . . . . 179(1) no
O23 C22 C21 C15 . . . . 178(1) no
O23 C22 C21 C25 . . . . -1(2) no
O23 C24 C25 C21 . . . . 1(2) no
O23 C24 C25 C31 . . . . 178(1) no
O33 C32 C31 C25 . . . . -179.7(8) no
O33 C32 C31 C35 . . . . 1(1) no
O33 C34 C35 C31 . . . . 0.5(9) no
O33 C34 C35 C35 . . . 2_666 -179.0(9) no
C11 C12 O13 C14 . . . . 0(1) no
C11 C15 C21 C22 . . . . -16(2) no
C11 C15 C21 C25 . . . . 162(1) no
C12 O13 C14 C15 . . . . -0(1) no
C12 C11 C15 C14 . . . . 0(1) no
C12 C11 C15 C21 . . . . -179(1) no
C14 C15 C21 C22 . . . . 164(1) no
C14 C15 C21 C25 . . . . -17(2) no
C15 C21 C25 C24 . . . . -179(1) no
C15 C21 C25 C31 . . . . 4(2) no
C21 C22 O23 C24 . . . . 1(2) no
C21 C25 C31 C32 . . . . 112(1) no
C21 C25 C31 C35 . . . . -69(2) no
C22 O23 C24 C25 . . . . -1(2) no
C22 C21 C25 C24 . . . . -0(1) no
C22 C21 C25 C31 . . . . -177(1) no
C24 C25 C31 C32 . . . . -65(2) no
C24 C25 C31 C35 . . . . 114(1) no
C25 C31 C35 C34 . . . . 179.7(9) no
C25 C31 C35 C35 . . . 2_666 -1(2) no
C31 C32 O33 C34 . . . . -0(1) no
C31 C35 C35 C31 . . 2_666 2_666 -180.0 no
C31 C35 C35 C34 . . 2_666 2_666 1(2) no
C32 O33 C34 C35 . . . . -0(1) no
C32 C31 C35 C34 . . . . -1(1) no
C32 C31 C35 C35 . . . 2_666 179(1) no
C34 C35 C35 C34 . . 2_666 2_666 180.0 no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd24_she1004.cif'
data_she1004
_database_code_depnum_ccdc_archive 'CCDC 860341'
_audit_creation_date 10-02-18
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2010-02-18 - Report on C24 H14 O6
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2010-02-18 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '2181415 she1004'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 5.9382(3)
_cell_length_b 22.9614(17)
_cell_length_c 6.7180(4)
_cell_angle_alpha 90
_cell_angle_beta 91.539(5)
_cell_angle_gamma 90
_cell_volume 915.66(10)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/a 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 2
# Given Formula = C24 H14 O6
# Dc = 1.44 Fooo = 412.00 Mu = 1.05 M = 199.19
# Found Formula = C24 H14 O6
# Dc = 1.44 FOOO = 412.00 Mu = 1.05 M = 199.19
_chemical_formula_sum 'C24 H14 O6'
_chemical_formula_moiety 'C24 H14 O6'
_chemical_compound_source local
_chemical_formula_weight 398.37
_cell_measurement_reflns_used 14368
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 25
_cell_measurement_temperature 200
_exptl_crystal_description lath
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.030
_exptl_crystal_size_mid 0.060
_exptl_crystal_size_max 0.170
_exptl_crystal_density_diffrn 1.445
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 412
_exptl_absorpt_coefficient_mu 0.105
# Sheldrick geometric approximatio 0.99 1.00
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.908 # range from scalepack 9.44/10.36
_exptl_absorpt_correction_T_max 0.997
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 1.0 deg at rate 540 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 9728
_reflns_number_total 1612
_diffrn_reflns_av_R_equivalents 0.095 # from scalepack
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 1612
# Theoretical number of reflections is about 3236
_diffrn_reflns_theta_min 3.033
_diffrn_reflns_theta_max 25.029
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.029
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_limit_l_max 7
_reflns_limit_h_min -7
_reflns_limit_h_max 7
_reflns_limit_k_min 0
_reflns_limit_k_max 27
_reflns_limit_l_min 0
_reflns_limit_l_max 7
_oxford_diffrn_Wilson_B_factor 2.64
_oxford_diffrn_Wilson_scale 6.38
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.50
_refine_diff_density_max 0.47
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 1609
_refine_ls_number_restraints 0
_refine_ls_number_parameters 158
_oxford_refine_ls_R_factor_ref 0.0980
_refine_ls_wR_factor_ref 0.1468
_refine_ls_goodness_of_fit_ref 0.9540
_refine_ls_shift/su_max 0.0024738
_refine_ls_shift/su_mean 0.0003 # 3.7045412
# The values computed from all data
_oxford_reflns_number_all 1609
_refine_ls_R_factor_all 0.0980
_refine_ls_wR_factor_all 0.1468
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1077
_refine_ls_R_factor_gt 0.0566
_refine_ls_wR_factor_gt 0.1277
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.90P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~24~H~14~O~6~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one-half of a
molecule of C~24~H~14~O~6~.
The other half of the molecule is generated by a crystallographic
inversion symmetry operation.
The crystals supplied were generally very small and intergrown.
One extremely thin lath was discovered, however, and was used for this study.
Very long exposure times were used for data collection
as the diffraction pattern was very weak.
Some spots were observed that did not belong to the
major cell, suggesting that the crystal
was not single or was split to some degree.
Intensity data were scaled by multi-scan inter-frame methods
(DENZO/SCALEPACK, Otwinowski & Minor, 1997) to correct
for absorption arising from the fibre used to mount the sample.
The compound is clearly identified although the
precision of the bond lengths and angles is not particularly good.
Hydrogen atoms were included at idealized positions and
then were allowed to refine positionally.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
Hydrogen atoms were included at idealized positions and
then were allowed to refine positionally.
The final difference electron density map is pretty flat
with peaks scattered randomly through the structure.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from chloroform/hexane.
The sample ID is tf-H~2~Fu~6~.
;
_refine_special_details
;
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C11 C 0.4161(6) 0.68930(15) 0.7696(5) 0.0507 1.0000 Uani . . . . . . .
C12 C 0.2314(6) 0.68000(16) 0.8767(6) 0.0528 1.0000 Uani . . . . . . .
O13 O 0.0844(4) 0.64495(11) 0.7735(4) 0.0579 1.0000 Uani . . . . . . .
C14 C 0.1837(6) 0.63231(17) 0.5967(5) 0.0529 1.0000 Uani . . . . . . .
C15 C 0.3870(5) 0.65823(13) 0.5866(5) 0.0379 1.0000 Uani . . . . . . .
C21 C 0.5445(5) 0.65468(13) 0.4229(5) 0.0395 1.0000 Uani . . . . . . .
C22 C 0.6953(6) 0.69561(16) 0.3723(5) 0.0471 1.0000 Uani . . . . . . .
O23 O 0.8162(4) 0.67814(10) 0.2130(3) 0.0521 1.0000 Uani . . . . . . .
C24 C 0.7370(6) 0.62395(15) 0.1643(5) 0.0439 1.0000 Uani . . . . . . .
C25 C 0.5722(5) 0.60740(13) 0.2840(4) 0.0383 1.0000 Uani . . . . . . .
C31 C 0.4416(5) 0.55279(13) 0.2705(4) 0.0375 1.0000 Uani . . . . . . .
C32 C 0.2970(6) 0.53893(15) 0.1174(5) 0.0453 1.0000 Uani . . . . . . .
O33 O 0.2000(4) 0.48594(10) 0.1468(3) 0.0478 1.0000 Uani . . . . . . .
C34 C 0.2883(5) 0.46557(15) 0.3242(5) 0.0429 1.0000 Uani . . . . . . .
C35 C 0.4358(5) 0.50385(13) 0.4061(4) 0.0368 1.0000 Uani . . . . . . .
H111 H 0.551(6) 0.7122(15) 0.821(5) 0.0609 1.0000 Uiso . . . . . . .
H121 H 0.178(6) 0.6932(16) 1.004(6) 0.0631 1.0000 Uiso . . . . . . .
H141 H 0.097(6) 0.6064(15) 0.502(5) 0.0647 1.0000 Uiso . . . . . . .
H221 H 0.723(6) 0.7334(15) 0.420(5) 0.0572 1.0000 Uiso . . . . . . .
H241 H 0.797(5) 0.6060(14) 0.056(5) 0.0519 1.0000 Uiso . . . . . . .
H321 H 0.252(6) 0.5597(14) 0.000(5) 0.0537 1.0000 Uiso . . . . . . .
H341 H 0.239(5) 0.4263(15) 0.362(5) 0.0518 1.0000 Uiso . . . . . . .
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
C11 0.054(2) 0.048(2) 0.050(2) -0.0035(17) 0.0016(17) -0.0025(17)
C12 0.060(2) 0.051(2) 0.047(2) -0.0033(18) 0.0109(18) 0.0049(18)
O13 0.0502(14) 0.0682(17) 0.0561(15) -0.0002(13) 0.0151(12) -0.0044(12)
C14 0.048(2) 0.064(2) 0.048(2) -0.0072(18) 0.0118(17) -0.0062(18)
C15 0.0392(17) 0.0366(17) 0.0377(17) 0.0032(13) 0.0001(13) 0.0005(13)
C21 0.0356(17) 0.0371(17) 0.0458(19) 0.0036(14) -0.0005(14) -0.0003(14)
C22 0.0465(19) 0.043(2) 0.052(2) -0.0036(16) 0.0120(16) -0.0060(16)
O23 0.0541(14) 0.0486(15) 0.0544(15) -0.0008(12) 0.0151(12) -0.0127(12)
C24 0.048(2) 0.044(2) 0.0392(18) -0.0056(15) 0.0069(16) -0.0081(16)
C25 0.0393(17) 0.0404(18) 0.0349(16) 0.0008(14) -0.0039(14) 0.0011(14)
C31 0.0388(17) 0.0355(17) 0.0381(17) 0.0002(13) 0.0009(13) -0.0012(13)
C32 0.053(2) 0.042(2) 0.0400(19) 0.0031(15) -0.0078(16) -0.0034(16)
O33 0.0520(13) 0.0439(14) 0.0466(13) 0.0024(10) -0.0169(11) -0.0071(11)
C34 0.0422(18) 0.0412(19) 0.0450(19) 0.0034(15) -0.0051(15) -0.0017(15)
C35 0.0347(16) 0.0358(16) 0.0396(17) -0.0027(13) -0.0030(13) -0.0037(13)
_refine_ls_extinction_coef 67(16)
_refine_ls_extinction_method 'Larson (1970), Equation 22'
_oxford_refine_ls_scale 0.4557(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 . C12 . 1.345(5) yes
C11 . C15 . 1.428(5) yes
C11 . H111 . 1.01(4) no
C12 . O13 . 1.363(4) yes
C12 . H121 . 0.97(4) no
O13 . C14 . 1.371(4) yes
C14 . C15 . 1.349(5) yes
C14 . H141 . 1.00(4) no
C15 . C21 . 1.465(5) yes
C21 . C22 . 1.348(4) yes
C21 . C25 . 1.444(4) yes
C22 . O23 . 1.365(4) yes
C22 . H221 . 0.94(3) no
O23 . C24 . 1.367(4) yes
C24 . C25 . 1.338(4) yes
C24 . H241 . 0.92(3) no
C25 . C31 . 1.476(4) yes
C31 . C32 . 1.360(4) yes
C31 . C35 . 1.447(4) yes
C32 . O33 . 1.363(4) yes
C32 . H321 . 0.96(4) no
O33 . C34 . 1.371(4) yes
C34 . C35 . 1.348(4) yes
C34 . H341 . 0.98(3) no
C35 . C35 2_666 1.468(6) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 . C11 . C15 . 107.5(3) yes
C12 . C11 . H111 . 123(2) no
C15 . C11 . H111 . 129(2) no
C11 . C12 . O13 . 110.0(3) yes
C11 . C12 . H121 . 136(2) no
O13 . C12 . H121 . 114(2) no
C12 . O13 . C14 . 106.3(3) yes
O13 . C14 . C15 . 110.9(3) yes
O13 . C14 . H141 . 117(2) no
C15 . C14 . H141 . 132(2) no
C11 . C15 . C14 . 105.4(3) yes
C11 . C15 . C21 . 127.5(3) yes
C14 . C15 . C21 . 127.1(3) yes
C15 . C21 . C22 . 126.3(3) yes
C15 . C21 . C25 . 127.8(3) yes
C22 . C21 . C25 . 105.8(3) yes
C21 . C22 . O23 . 111.1(3) yes
C21 . C22 . H221 . 132(2) no
O23 . C22 . H221 . 116(2) no
C22 . O23 . C24 . 105.7(3) yes
O23 . C24 . C25 . 111.6(3) yes
O23 . C24 . H241 . 117(2) no
C25 . C24 . H241 . 131(2) no
C21 . C25 . C24 . 105.8(3) yes
C21 . C25 . C31 . 127.6(3) yes
C24 . C25 . C31 . 126.6(3) yes
C25 . C31 . C32 . 124.4(3) yes
C25 . C31 . C35 . 130.0(3) yes
C32 . C31 . C35 . 105.6(3) yes
C31 . C32 . O33 . 111.1(3) yes
C31 . C32 . H321 . 132(2) no
O33 . C32 . H321 . 117(2) no
C32 . O33 . C34 . 106.1(2) yes
O33 . C34 . C35 . 111.2(3) yes
O33 . C34 . H341 . 115.3(19) no
C35 . C34 . H341 . 133.4(19) no
C35 2_666 C35 . C31 . 127.8(3) yes
C35 2_666 C35 . C34 . 126.1(4) yes
C31 . C35 . C34 . 106.0(3) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O13 C24 3.416(4) . 1_456 no
O13 C34 3.419(4) . 2_566 no
O13 O23 3.477(3) . 1_456 no
O13 O33 3.496(3) . 2_566 no
O13 C32 3.564(4) . 1_556 no
O23 C12 3.389(4) . 1_654 no
O23 C14 3.495(4) . 1_655 no
O33 O33 3.114(4) . 2_565 no
O33 C24 3.304(4) . 2_665 no
O33 C32 3.450(4) . 2_565 no
O33 C32 3.561(4) . 2_665 no
C11 C24 3.556(5) . 1_556 no
C11 C12 3.600(5) . 4_565 no
C14 C22 3.544(5) . 1_455 no
C32 C32 3.421(7) . 2_665 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O13 C12 C11 C15 . . . . -0.2(4) no
O13 C14 C15 C11 . . . . -0.2(4) no
O13 C14 C15 C21 . . . . 179.4(3) no
O23 C22 C21 C15 . . . . 179.7(3) no
O23 C22 C21 C25 . . . . -0.0(4) no
O23 C24 C25 C21 . . . . -0.6(4) no
O23 C24 C25 C31 . . . . 177.4(3) no
O33 C32 C31 C25 . . . . -179.6(3) no
O33 C32 C31 C35 . . . . 0.6(4) no
O33 C34 C35 C31 . . . . 0.3(3) no
O33 C34 C35 C35 . . . 2_666 -179.2(4) no
C11 C12 O13 C14 . . . . 0.1(4) no
C11 C15 C21 C22 . . . . -29.2(5) no
C11 C15 C21 C25 . . . . 150.5(3) no
C12 O13 C14 C15 . . . . 0.0(4) no
C12 C11 C15 C14 . . . . 0.2(4) no
C12 C11 C15 C21 . . . . -179.3(3) no
C14 C15 C21 C22 . . . . 151.4(4) no
C14 C15 C21 C25 . . . . -28.9(5) no
C15 C21 C25 C24 . . . . -179.3(3) no
C15 C21 C25 C31 . . . . 2.6(5) no
C21 C22 O23 C24 . . . . -0.3(4) no
C21 C25 C31 C32 . . . . 111.5(4) no
C21 C25 C31 C35 . . . . -68.8(5) no
C22 O23 C24 C25 . . . . 0.6(4) no
C22 C21 C25 C24 . . . . 0.4(4) no
C22 C21 C25 C31 . . . . -177.6(3) no
C24 C25 C31 C32 . . . . -66.1(5) no
C24 C25 C31 C35 . . . . 113.6(4) no
C25 C31 C35 C34 . . . . 179.7(3) no
C25 C31 C35 C35 . . . 2_666 -0.9(6) no
C31 C32 O33 C34 . . . . -0.5(4) no
C31 C35 C35 C31 . . 2_666 2_666 180.0 no
C31 C35 C35 C34 . . 2_666 2_666 0.7(7) no
C32 O33 C34 C35 . . . . 0.1(4) no
C32 C31 C35 C34 . . . . -0.5(3) no
C32 C31 C35 C35 . . . 2_666 178.9(4) no
C34 C35 C35 C34 . . 2_666 2_666 180.0 no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd25_she0620.cif'
data_she0620
_database_code_depnum_ccdc_archive 'CCDC 860342'
_audit_creation_date 06-08-28
_audit_creation_method CRYSTALS_ver_12.18
_audit_update_record
;
2006-08-28 - Report on C8 H6 O2
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2006-08-28 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '8281038 she0620scalepacked'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 8.9805(2)
_cell_length_b 7.2435(1)
_cell_length_c 15.1904(3)
_cell_angle_alpha 90
_cell_angle_beta 97.9427(12)
_cell_angle_gamma 90
_cell_volume 978.66(3)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 6
# Given Formula = C8 H6 O2
# Dc = 1.37 Fooo = 420.00 Mu = 0.99 M = 201.20
# Found Formula = C8 H6 O2
# Dc = 1.37 FOOO = 420.00 Mu = 0.99 M = 201.20
_chemical_formula_sum 'C8 H6 O2'
_chemical_formula_moiety 'C8 H6 O2'
_chemical_compound_source local
_chemical_formula_weight 134.13
_cell_measurement_reflns_used 2424
_cell_measurement_theta_min 3
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 200
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.10
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_max 0.34
_exptl_crystal_density_diffrn 1.365
_exptl_crystal_density_meas 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 420
_exptl_absorpt_coefficient_mu 0.099
# Sheldrick geometric approximatio 0.97 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.91
_exptl_absorpt_correction_T_max 0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 240 sec/frame
and 24 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 95 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius BV, 1997)'
_computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'Denzo/Scalepack '
_computing_structure_solution 'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement 'CRYSTALS (Watkin et al 2003)'
_computing_publication_material 'CRYSTALS '
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 35744
_reflns_number_total 2242
_diffrn_reflns_av_R_equivalents 0.051
# Number of reflections with Friedels Law is 2242
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2240
_diffrn_reflns_theta_min 2.708
_diffrn_reflns_theta_max 27.463
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.463
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_reflns_limit_h_min -11
_reflns_limit_h_max 11
_reflns_limit_k_min 0
_reflns_limit_k_max 9
_reflns_limit_l_min 0
_reflns_limit_l_max 19
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.19
_refine_diff_density_max 0.21
_refine_ls_number_reflns 1715
_refine_ls_number_restraints 0
_refine_ls_number_parameters 163
#_refine_ls_R_factor_ref 0.0354
_refine_ls_wR_factor_ref 0.0446
_refine_ls_goodness_of_fit_ref 1.0607
#_reflns_number_all 2235
_refine_ls_R_factor_all 0.0467
_refine_ls_wR_factor_all 0.0487
# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression I>3.0\s(I)
_reflns_number_gt 1715
_refine_ls_R_factor_gt 0.0354
_refine_ls_wR_factor_gt 0.0446
_refine_ls_shift/su_max 0.000530
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.88 1.99 1.32
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~8~H~6~O~2~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of
two C~8~H~6~O~2~ molecules,
one of which has a crystallographic inversion symmetry operation
relating its two halves.
The major peaks in the final difference electron density map
have similar intensities and are located
between carbon atoms.
;
_publ_section_acknowledgements # Acknowledgments
;
?
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
All H atoms were observed in a
difference electron density map prior to their inclusion.
They were included at idealized positions and refined positionally.
;
_publ_section_exptl_prep
;
The compound was prepared by TF and recrystallized from
petrol. The sample ID is tf-bifuran.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. 27, 435-435
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius BV, COLLECT Software, 1997-2001)
Otwinowski, Z. & Minor, W. (1997), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994),
Acta Cryst, A50, 411-437
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976)
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.33771(8) 0.52530(10) 0.19798(5) 0.0492 1.0000 Uani . . . . . .
C2 C 0.48617(10) 0.57101(12) 0.22043(6) 0.0410 1.0000 Uani . . . . . .
C3 C 0.57104(9) 0.49432(9) 0.16295(5) 0.0330 1.0000 Uani . . . . . .
C4 C 0.46720(9) 0.39382(12) 0.10025(5) 0.0406 1.0000 Uani . . . . . .
C5 C 0.33078(10) 0.41635(13) 0.12415(6) 0.0456 1.0000 Uani . . . . . .
O6 O 0.96770(8) 0.47583(9) 0.13331(4) 0.0459 1.0000 Uani . . . . . .
C7 C 0.81790(10) 0.44551(12) 0.10551(6) 0.0399 1.0000 Uani . . . . . .
C8 C 0.73335(9) 0.50472(9) 0.16701(5) 0.0331 1.0000 Uani . . . . . .
C9 C 0.83928(10) 0.57552(10) 0.23890(5) 0.0380 1.0000 Uani . . . . . .
C10 C 0.97661(11) 0.55550(12) 0.21510(6) 0.0420 1.0000 Uani . . . . . .
O11 O 0.82059(7) 0.47871(9) 0.47860(4) 0.0440 1.0000 Uani . . . . . .
C12 C 0.67316(10) 0.43886(12) 0.44885(6) 0.0381 1.0000 Uani . . . . . .
C13 C 0.58146(9) 0.50669(9) 0.50483(5) 0.0315 1.0000 Uani . . . . . .
C14 C 0.68013(9) 0.59514(11) 0.57511(5) 0.0376 1.0000 Uani . . . . . .
C15 C 0.82060(10) 0.57463(12) 0.55604(6) 0.0417 1.0000 Uani . . . . . .
H21 H 0.5092(11) 0.6474(15) 0.2699(7) 0.0489 1.0000 Uiso . . . . . .
H41 H 0.4904(11) 0.3244(14) 0.0499(6) 0.0482 1.0000 Uiso . . . . . .
H51 H 0.2324(13) 0.3750(16) 0.1000(7) 0.0538 1.0000 Uiso . . . . . .
H71 H 0.7941(11) 0.3921(15) 0.0498(6) 0.0475 1.0000 Uiso . . . . . .
H91 H 0.8146(11) 0.6303(14) 0.2936(6) 0.0451 1.0000 Uiso . . . . . .
H101 H 1.0770(12) 0.5838(15) 0.2439(7) 0.0495 1.0000 Uiso . . . . . .
H121 H 0.6561(12) 0.3714(15) 0.3974(7) 0.0456 1.0000 Uiso . . . . . .
H141 H 0.6488(11) 0.6577(14) 0.6256(7) 0.0448 1.0000 Uiso . . . . . .
H151 H 0.9200(12) 0.6104(15) 0.5864(7) 0.0492 1.0000 Uiso . . . . . .
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
O1 0.0381(4) 0.0612(4) 0.0493(4) 0.0026(3) 0.0099(3) 0.0072(3)
C2 0.0373(5) 0.0443(4) 0.0412(4) -0.0018(3) 0.0052(3) 0.0046(3)
C3 0.0343(4) 0.0306(3) 0.0339(4) 0.0030(2) 0.0043(3) 0.0013(3)
C4 0.0363(5) 0.0441(4) 0.0407(4) -0.0013(3) 0.0027(3) -0.0018(3)
C5 0.0379(5) 0.0530(5) 0.0443(5) 0.0028(3) 0.0005(3) -0.0021(3)
O6 0.0363(4) 0.0548(4) 0.0473(4) -0.0018(3) 0.0087(2) -0.0003(3)
C7 0.0364(5) 0.0443(4) 0.0388(4) -0.0042(3) 0.0048(3) -0.0004(3)
C8 0.0355(5) 0.0281(3) 0.0355(4) 0.0014(3) 0.0044(3) -0.0008(3)
C9 0.0398(5) 0.0362(4) 0.0374(4) -0.0016(3) 0.0036(3) -0.0047(3)
C10 0.0390(5) 0.0428(4) 0.0428(4) 0.0004(3) 0.0010(3) -0.0063(3)
O11 0.0343(4) 0.0547(4) 0.0439(4) -0.0007(2) 0.0087(2) 0.0039(2)
C12 0.0333(5) 0.0430(4) 0.0381(4) -0.0035(3) 0.0058(3) 0.0023(3)
C13 0.0326(5) 0.0306(4) 0.0318(4) 0.0024(2) 0.0056(3) 0.0006(2)
C14 0.0381(4) 0.0407(4) 0.0340(4) -0.0009(3) 0.0050(3) -0.0031(3)
C15 0.0370(5) 0.0477(5) 0.0392(4) 0.0040(3) 0.0011(3) -0.0031(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 1.889(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.3703(11) yes
O1 . C5 . 1.3658(12) yes
C2 . C3 . 1.3549(12) yes
C2 . H21 . 0.933(11) no
C3 . C4 . 1.4357(11) yes
C3 . C8 . 1.4523(12) yes
C4 . C5 . 1.3350(13) yes
C4 . H41 . 0.961(10) no
C5 . H51 . 0.956(11) no
O6 . C7 . 1.3709(11) yes
O6 . C10 . 1.3622(11) yes
C7 . C8 . 1.3525(12) yes
C7 . H71 . 0.928(10) no
C8 . C9 . 1.4400(11) yes
C9 . C10 . 1.3401(13) yes
C9 . H91 . 0.973(10) no
C10 . H101 . 0.968(10) no
O11 . C12 . 1.3693(11) yes
O11 . C15 . 1.3663(11) yes
C12 . C13 . 1.3551(12) yes
C12 . H121 . 0.916(11) no
C13 . C13 2_666 1.4533(15) yes
C13 . C14 . 1.4401(10) yes
C14 . C15 . 1.3410(13) yes
C14 . H141 . 0.965(11) no
C15 . H151 . 0.981(10) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C5 . 106.04(7) yes
O1 . C2 . C3 . 110.80(8) yes
O1 . C2 . H21 . 116.3(6) no
C3 . C2 . H21 . 132.9(6) no
C2 . C3 . C4 . 105.29(8) yes
C2 . C3 . C8 . 127.01(8) yes
C4 . C3 . C8 . 127.63(8) yes
C3 . C4 . C5 . 107.10(8) yes
C3 . C4 . H41 . 126.9(6) no
C5 . C4 . H41 . 126.0(6) no
O1 . C5 . C4 . 110.76(8) yes
O1 . C5 . H51 . 115.5(7) no
C4 . C5 . H51 . 133.7(7) no
C7 . O6 . C10 . 106.28(7) yes
O6 . C7 . C8 . 110.92(7) yes
O6 . C7 . H71 . 116.1(6) no
C8 . C7 . H71 . 133.0(6) no
C3 . C8 . C7 . 127.60(8) yes
C3 . C8 . C9 . 127.21(8) yes
C7 . C8 . C9 . 105.17(7) yes
C8 . C9 . C10 . 107.04(7) yes
C8 . C9 . H91 . 126.0(6) no
C10 . C9 . H91 . 126.9(6) no
O6 . C10 . C9 . 110.59(7) yes
O6 . C10 . H101 . 115.8(7) no
C9 . C10 . H101 . 133.6(7) no
C12 . O11 . C15 . 106.04(7) yes
O11 . C12 . C13 . 111.11(7) yes
O11 . C12 . H121 . 115.7(7) no
C13 . C12 . H121 . 133.1(7) no
C13 2_666 C13 . C12 . 127.09(9) yes
C13 2_666 C13 . C14 . 127.76(9) yes
C12 . C13 . C14 . 105.15(7) yes
C13 . C14 . C15 . 106.95(7) yes
C13 . C14 . H141 . 125.5(6) no
C15 . C14 . H141 . 127.6(6) no
O11 . C15 . C14 . 110.74(7) yes
O11 . C15 . H151 . 115.5(6) no
C14 . C15 . H151 . 133.7(6) no
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C10 3.296(1) . 1_455 no
O1 O6 3.352(1) . 1_455 no
O1 C14 3.509(1) . 4_464 no
O1 C14 3.580(1) . 2_666 no
O6 C5 3.311(1) . 1_655 no
O11 O11 3.213(1) . 2_766 no
O11 C15 3.358(1) . 2_766 no
O11 C4 3.429(1) . 4 no
C3 C9 3.427(1) . 3_645 no
C4 C4 3.533(2) . 2_665 no
C8 C9 3.520(1) . 3_645 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 C4 . . . . 0.05(9) no
O1 C2 C3 C8 . . . . -177.20(7) no
O1 C5 C4 C3 . . . . 0.3(1) no
O6 C7 C8 C3 . . . . -178.92(7) no
O6 C7 C8 C9 . . . . -0.62(9) no
O6 C10 C9 C8 . . . . -0.39(9) no
O11 C12 C13 C13 . . . 2_666 179.45(9) no
O11 C12 C13 C14 . . . . -0.22(9) no
O11 C15 C14 C13 . . . . -0.20(9) no
C2 O1 C5 C4 . . . . -0.2(1) no
C2 C3 C4 C5 . . . . -0.18(9) no
C2 C3 C8 C7 . . . . -172.56(8) no
C2 C3 C8 C9 . . . . 9.5(1) no
C3 C2 O1 C5 . . . . 0.1(1) no
C3 C8 C9 C10 . . . . 178.93(7) no
C4 C3 C8 C7 . . . . 10.8(1) no
C4 C3 C8 C9 . . . . -167.15(7) no
C5 C4 C3 C8 . . . . 177.05(7) no
C7 O6 C10 C9 . . . . 0.02(9) no
C7 C8 C9 C10 . . . . 0.61(9) no
C8 C7 O6 C10 . . . . 0.39(9) no
C12 O11 C15 C14 . . . . 0.07(9) no
C12 C13 C13 C12 . . 2_666 2_666 180.0 no
C12 C13 C13 C14 . . 2_666 2_666 0.4(2) no
C12 C13 C14 C15 . . . . 0.25(9) no
C13 C12 O11 C15 . . . . 0.10(9) no
C13 C13 C14 C15 . 2_666 2_666 2_666 179.41(9) no
C14 C13 C13 C14 . . 2_666 2_666 180.0 no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd26_she0712a.cif'
data_she0712a
_database_code_depnum_ccdc_archive 'CCDC 860343'
_audit_creation_date 07-06-20
_audit_creation_method CRYSTALS_ver_12.18
_audit_update_record
;
2007-06-20 - Report on C12 H8 O3
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2007-06-20 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title 'tranformed axes for std space group'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 24.2219(9)
_cell_length_b 5.1953(2)
_cell_length_c 7.4212(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 933.88(6)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P c a 21 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y,z+1/2
x+1/2,-y,z
-x,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C12 H8 O3
# Dc = 1.42 Fooo = 416.00 Mu = 1.03 M = 200.19
# Found Formula = C12 H8 O3
# Dc = 1.42 FOOO = 416.00 Mu = 1.03 M = 200.19
_chemical_formula_sum 'C12 H8 O3'
_chemical_formula_moiety 'C12 H8 O3'
_chemical_compound_source local
_chemical_formula_weight 200.19
_cell_measurement_reflns_used 13108
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 30.0
_cell_measurement_temperature 150
_exptl_crystal_description plate
_exptl_crystal_colour yellow
_exptl_crystal_size_min 0.25
_exptl_crystal_size_mid 0.43
_exptl_crystal_size_max 0.50
_exptl_crystal_density_diffrn 1.424
_exptl_crystal_density_meas 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 416
_exptl_absorpt_coefficient_mu 0.103
# Sheldrick geometric approximatio 0.96 0.97
# Absorption correction
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.904 #0.933
_exptl_absorpt_correction_T_max 0.975 #1.006
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995, 1997)
;
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 1.1 deg at rate 44 sec/frame,
crystal-detector distance 55mm,
multiple scan sets so over 95 percent of data collected with 4-fold
redundancy or more [assuming Friedel's Law].
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius BV, 1997)'
_computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement 'CRYSTALS (Watkin et al 2003)'
_computing_publication_material 'CRYSTALS (Watkin et al 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 150
_diffrn_reflns_number 14543
_reflns_number_total 1449
_diffrn_reflns_av_R_equivalents 0.039
# Number of reflections with Friedels Law is 1449
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1370
_diffrn_reflns_theta_min 3.219
_diffrn_reflns_theta_max 30.061
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 29.460
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_h_max 34
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 10
_reflns_limit_h_min 0
_reflns_limit_h_max 34
_reflns_limit_k_min 0
_reflns_limit_k_max 7
_reflns_limit_l_min 0
_reflns_limit_l_max 10
_oxford_diffrn_Wilson_B_factor 2.26
_oxford_diffrn_Wilson_scale 0.26
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.14
_refine_diff_density_max 0.24
_refine_ls_number_reflns 1333
_refine_ls_number_restraints 1
_refine_ls_number_parameters 160
#_refine_ls_R_factor_ref 0.0271
_refine_ls_wR_factor_ref 0.0314
_refine_ls_goodness_of_fit_ref 1.1227
#_reflns_number_all 1446
_refine_ls_R_factor_all 0.0296
_refine_ls_wR_factor_all 0.0335
# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1333
_refine_ls_R_factor_gt 0.0271
_refine_ls_wR_factor_gt 0.0314
_refine_ls_shift/su_max 0.001044
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_abs_structure_details
;
The absolute structure of the crystal was not determined in this experiment.
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial,
(Carruthers & Watkin, 1979, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.20 0.149 0.967
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~12~H~8~O~3~
is reported.
;
_publ_section_comment #Text of the paper
;
The space group is noncentrosymmetric but
the anomolous dispersion terms are very small
for all elements in the structure,
so the
absolute structure of the crystal can not be determined in this experiment.
Consequently Friedel-pair reflections have been averaged and
the Flack parameter has not been refined.
The space group is not enantiomorphic
so there are both atropisomers of the molecule in the crystal.
The crystallographic asymmetric unit consists of
one molecule of C~12~H~8~O~3~.
All H atoms were observed in a
difference electron density map prior to their inclusion.
They were included at
idealized positions and refined positionally.
The major peaks in the final difference electron density map
are located along C---C bonds.
;
_publ_section_acknowledgements # Acknowledgments
;
We wish to acknowledge the kind assistance of Dr J\"org Wagler in mounting
this crystal. The compound has a melting point of ca. 253K so had
to be recrystallised below this temperature and then kept cold until mounted
in the cold nitrogen stream of a Cryostream cooling device mounted
on our KappaCCD diffractometer.
A single, very large crystal of C~12~H~8~O~3~ was prepared by slowly cooling
a solution of the compound in petrol/dichloromethane
in a cryobath to a final temperature of ca. 243K.
A slurry of isopropanol and dry-ice (ca. 195K)
was prepared in a short dewar and a petrie
dish was placed on top of the liquid. A small amount of silicone oil
was placed on the dish and allowed to cool, but remained liquid.
The crystal was transferred into the oil using a cooled spatula
and then was cleaved with a scalpel.
A suitably sized fragment was picked up on a glass fibre
smeared with vacuum grease, and then mounted on the diffractometer.
The Cryostream was set at 150K, freezing the grease.
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms were refined positionally.
;
_publ_section_exptl_prep
;
The compound was prepared by TF and recrystallized from
petrol/dichloromethane. The sample ID is tf-trifuran.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. 27, 435-435
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995).
Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997).
Nonius BV, COLLECT Software, 1997-2001)
Otwinowski, Z. & Minor, W. (1997), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Carruthers, J.R. & Watkin, D.J. (1979),
Acta Cryst. A35, 698-699.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976)
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O2 O 0.30119(4) -0.09713(17) 0.45356(18) 0.0330 1.0000 Uani . . . . . .
O8 O 0.31280(4) 0.56671(17) 1.07447(18) 0.0311 1.0000 Uani . . . . . .
O13 O 0.53435(3) 0.27893(16) 0.88937(17) 0.0299 1.0000 Uani . . . . . .
C1 C 0.29732(5) -0.0270(2) 0.6313(2) 0.0294 1.0000 Uani . . . . . .
C3 C 0.33672(5) 0.0726(2) 0.3745(2) 0.0297 1.0000 Uani . . . . . .
C4 C 0.35563(5) 0.2443(2) 0.4967(2) 0.0270 1.0000 Uani . . . . . .
C5 C 0.32993(4) 0.1806(2) 0.66576(19) 0.0228 1.0000 Uani . . . . . .
C6 C 0.33513(4) 0.32155(19) 0.83582(19) 0.0225 1.0000 Uani . . . . . .
C7 C 0.29307(5) 0.4341(2) 0.9285(2) 0.0272 1.0000 Uani . . . . . .
C9 C 0.36891(5) 0.5355(2) 1.0736(2) 0.0275 1.0000 Uani . . . . . .
C10 C 0.38521(4) 0.38788(19) 0.93102(18) 0.0222 1.0000 Uani . . . . . .
C11 C 0.44150(4) 0.30445(18) 0.89130(18) 0.0220 1.0000 Uani . . . . . .
C12 C 0.48932(4) 0.4197(2) 0.9437(2) 0.0263 1.0000 Uani . . . . . .
C14 C 0.51386(5) 0.0684(2) 0.8005(2) 0.0279 1.0000 Uani . . . . . .
C15 C 0.45793(5) 0.07433(19) 0.7972(2) 0.0256 1.0000 Uani . . . . . .
H11 H 0.2734(8) -0.122(4) 0.704(3) 0.0355 1.0000 Uiso . . . . . .
H31 H 0.3418(8) 0.057(4) 0.246(3) 0.0357 1.0000 Uiso . . . . . .
H41 H 0.3824(7) 0.390(4) 0.475(3) 0.0326 1.0000 Uiso . . . . . .
H71 H 0.2541(9) 0.446(3) 0.913(3) 0.0328 1.0000 Uiso . . . . . .
H91 H 0.3876(8) 0.605(3) 1.175(3) 0.0331 1.0000 Uiso . . . . . .
H121 H 0.4969(8) 0.580(3) 1.008(3) 0.0318 1.0000 Uiso . . . . . .
H141 H 0.5393(9) -0.052(4) 0.759(3) 0.0336 1.0000 Uiso . . . . . .
H151 H 0.4345(8) -0.051(3) 0.750(3) 0.0308 1.0000 Uiso . . . . . .
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
O2 0.0397(5) 0.0298(4) 0.0296(4) -0.0059(3) -0.0018(4) -0.0053(3)
O8 0.0287(4) 0.0360(4) 0.0285(4) -0.0089(4) 0.0028(3) 0.0031(3)
O13 0.0224(3) 0.0317(4) 0.0354(4) 0.0002(3) 0.0002(3) -0.0015(3)
C1 0.0321(5) 0.0280(5) 0.0281(5) -0.0025(4) 0.0002(4) -0.0048(4)
C3 0.0291(5) 0.0348(5) 0.0251(5) -0.0044(4) -0.0001(4) 0.0016(4)
C4 0.0236(4) 0.0332(5) 0.0243(5) -0.0015(4) 0.0019(4) -0.0021(4)
C5 0.0207(4) 0.0250(4) 0.0229(4) 0.0001(3) -0.0007(3) 0.0014(3)
C6 0.0213(4) 0.0234(4) 0.0228(4) -0.0006(4) 0.0004(3) -0.0002(3)
C7 0.0245(5) 0.0304(5) 0.0267(5) -0.0037(4) 0.0010(4) 0.0019(4)
C9 0.0262(5) 0.0310(4) 0.0252(5) -0.0052(4) 0.0001(4) 0.0009(4)
C10 0.0231(4) 0.0231(4) 0.0205(4) 0.0007(3) 0.0000(3) -0.0006(3)
C11 0.0228(4) 0.0226(4) 0.0204(4) 0.0009(3) -0.0005(3) 0.0002(3)
C12 0.0239(5) 0.0256(4) 0.0295(5) -0.0008(4) 0.0005(4) -0.0014(3)
C14 0.0251(5) 0.0278(5) 0.0309(5) -0.0007(5) 0.0006(4) 0.0032(4)
C15 0.0259(5) 0.0236(4) 0.0273(5) -0.0014(4) -0.0013(4) 0.0007(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 1.955(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . C1 . 1.3720(16) yes
O2 . C3 . 1.3648(16) yes
O8 . C7 . 1.3701(14) yes
O8 . C9 . 1.3688(14) yes
O13 . C12 . 1.3738(13) yes
O13 . C14 . 1.3704(14) yes
C1 . C5 . 1.3612(15) yes
C1 . H11 . 0.93(2) no
C3 . C4 . 1.3524(17) yes
C3 . H31 . 0.96(2) no
C4 . C5 . 1.4390(14) yes
C4 . H41 . 1.012(18) no
C5 . C6 . 1.4644(14) yes
C6 . C7 . 1.3610(15) yes
C6 . C10 . 1.4454(14) yes
C7 . H71 . 0.95(2) no
C9 . C10 . 1.3651(15) yes
C9 . H91 . 0.95(2) no
C10 . C11 . 1.4608(14) yes
C11 . C12 . 1.3607(14) yes
C11 . C15 . 1.4408(14) yes
C12 . H121 . 0.975(18) no
C14 . C15 . 1.3553(15) yes
C14 . H141 . 0.93(2) no
C15 . H151 . 0.932(19) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O2 . C3 . 106.57(9) yes
C7 . O8 . C9 . 106.44(8) yes
C12 . O13 . C14 . 106.18(9) yes
O2 . C1 . C5 . 110.56(11) yes
O2 . C1 . H11 . 117.4(12) no
C5 . C1 . H11 . 132.0(12) no
O2 . C3 . C4 . 110.57(11) yes
O2 . C3 . H31 . 116.8(12) no
C4 . C3 . H31 . 132.5(12) no
C3 . C4 . C5 . 106.65(10) yes
C3 . C4 . H41 . 127.2(12) no
C5 . C4 . H41 . 126.1(12) no
C4 . C5 . C1 . 105.65(10) yes
C4 . C5 . C6 . 126.80(9) yes
C1 . C5 . C6 . 127.43(11) yes
C5 . C6 . C7 . 125.85(10) yes
C5 . C6 . C10 . 127.78(10) yes
C7 . C6 . C10 . 106.19(9) yes
O8 . C7 . C6 . 110.76(10) yes
O8 . C7 . H71 . 113.9(11) no
C6 . C7 . H71 . 135.3(12) no
O8 . C9 . C10 . 110.94(10) yes
O8 . C9 . H91 . 115.2(11) no
C10 . C9 . H91 . 133.6(11) no
C6 . C10 . C9 . 105.68(9) yes
C6 . C10 . C11 . 127.87(9) yes
C9 . C10 . C11 . 126.37(10) yes
C10 . C11 . C12 . 127.33(10) yes
C10 . C11 . C15 . 127.01(9) yes
C12 . C11 . C15 . 105.58(9) yes
O13 . C12 . C11 . 110.96(10) yes
O13 . C12 . H121 . 116.6(12) no
C11 . C12 . H121 . 132.4(12) no
O13 . C14 . C15 . 110.64(9) yes
O13 . C14 . H141 . 117.2(12) no
C15 . C14 . H141 . 132.2(12) no
C11 . C15 . C14 . 106.64(9) yes
C11 . C15 . H151 . 126.4(11) no
C14 . C15 . H151 . 126.8(11) no
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O2 O8 3.323(2) . 1_544 no
O2 C7 3.343(2) . 2_544 no
O2 O8 3.388(1) . 2_544 no
O2 C1 3.398(2) . 2_554 no
O2 C7 3.587(1) . 2_554 no
O8 C1 3.428(2) . 2_565 no
O8 C3 3.447(2) . 1_556 no
O8 C3 3.493(2) . 1_566 no
O13 C9 3.451(2) . 4_664 no
O13 C15 3.545(2) . 4_655 no
C1 C7 3.566(2) . 1_545 no
C1 C7 3.577(2) . 2_554 no
C3 C9 3.373(2) . 1_554 no
C4 C9 3.500(2) . 1_554 no
C12 C14 3.583(2) . 1_565 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C5 C4 . . . . 0.3(1) no
O2 C1 C5 C6 . . . . 176.6(1) no
O2 C3 C4 C5 . . . . -0.5(1) no
O8 C7 C6 C5 . . . . -175.3(1) no
O8 C7 C6 C10 . . . . 0.1(1) no
O8 C9 C10 C6 . . . . -0.1(1) no
O8 C9 C10 C11 . . . . -177.0(1) no
O13 C12 C11 C10 . . . . 176.8(1) no
O13 C12 C11 C15 . . . . 0.0(2) no
O13 C14 C15 C11 . . . . -0.3(2) no
C1 O2 C3 C4 . . . . 0.7(1) no
C1 C5 C4 C3 . . . . 0.1(1) no
C1 C5 C6 C7 . . . . -56.5(2) no
C1 C5 C6 C10 . . . . 129.0(1) no
C3 O2 C1 C5 . . . . -0.6(1) no
C3 C4 C5 C6 . . . . -176.2(1) no
C4 C5 C6 C7 . . . . 119.0(1) no
C4 C5 C6 C10 . . . . -55.5(2) no
C5 C6 C10 C9 . . . . 175.3(1) no
C5 C6 C10 C11 . . . . -7.9(2) no
C6 C7 O8 C9 . . . . -0.2(1) no
C6 C10 C11 C12 . . . . 159.2(1) no
C6 C10 C11 C15 . . . . -24.7(2) no
C7 O8 C9 C10 . . . . 0.2(1) no
C7 C6 C10 C9 . . . . -0.0(1) no
C7 C6 C10 C11 . . . . 176.8(1) no
C9 C10 C11 C12 . . . . -24.6(2) no
C9 C10 C11 C15 . . . . 151.5(1) no
C10 C11 C15 C14 . . . . -176.6(1) no
C11 C12 O13 C14 . . . . -0.2(2) no
C12 O13 C14 C15 . . . . 0.3(2) no
C12 C11 C15 C14 . . . . 0.1(2) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd27_she0938.cif'
data_she0938
_database_code_depnum_ccdc_archive 'CCDC 860344'
_audit_creation_date 09-12-15
_audit_creation_method CRYSTALS_ver_12.87
_audit_update_record
;
2009-12-17 - Report on C12 H6 O3
by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2009-12-17 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title '12151651 she0938'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 15.1850(7)
_cell_length_b 8.7609(4)
_cell_length_c 7.1418(3)
_cell_angle_alpha 90
_cell_angle_beta 116.501(2)
_cell_angle_gamma 90
_cell_volume 850.27(7)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 1 2/c 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C12 H6 O3
# Dc = 1.55 Fooo = 408.00 Mu = 1.13 M = 99.09
# Found Formula = C12 H6 O3
# Dc = 1.55 FOOO = 408.00 Mu = 1.13 M = 99.09
_chemical_formula_sum 'C12 H6 O3'
_chemical_formula_moiety 'C12 H6 O3'
_chemical_compound_source local
_chemical_formula_weight 198.18
_cell_measurement_reflns_used 7920
_cell_measurement_theta_min 2.7
_cell_measurement_theta_max 27.5
_cell_measurement_temperature 200
_exptl_crystal_description plate
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_size_min 0.030
_exptl_crystal_size_mid 0.100
_exptl_crystal_size_max 0.460
_exptl_crystal_density_diffrn 1.548
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 408
_exptl_absorpt_coefficient_mu 0.113
# Sheldrick geometric approximatio 0.99 1.00
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.030
-1 0 0 0.001
0 1 0 0.100
0 -1 0 0.040
0 0 1 0.250
0 0 -1 0.210
1 7 -1 0.068
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.968
_exptl_absorpt_correction_T_max 0.997
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents 0.048
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 240 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 8871
_reflns_number_total 978
_diffrn_reflns_av_R_equivalents 0.055
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 978
# Theoretical number of reflections is about 1958
_diffrn_reflns_theta_min 2.766
_diffrn_reflns_theta_max 27.523
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 26.972
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 8
_reflns_limit_h_min -19
_reflns_limit_h_max 17
_reflns_limit_k_min 0
_reflns_limit_k_max 11
_reflns_limit_l_min 0
_reflns_limit_l_max 9
_oxford_diffrn_Wilson_B_factor 2.89
_oxford_diffrn_Wilson_scale 0.99
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.26
_refine_diff_density_max 0.21
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 978
_refine_ls_number_restraints 0
_refine_ls_number_parameters 78
_oxford_refine_ls_R_factor_ref 0.0483
_refine_ls_wR_factor_ref 0.1030
_refine_ls_goodness_of_fit_ref 1.0426
_refine_ls_shift/su_max 0.0123451
_refine_ls_shift/su_mean 0.4220141
# The values computed from all data
_oxford_reflns_number_all 978
_refine_ls_R_factor_all 0.0483
_refine_ls_wR_factor_all 0.1030
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 828
_refine_ls_R_factor_gt 0.0395
_refine_ls_wR_factor_gt 0.0987
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.42P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~12~H~6~O~3~
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one-half of a
molecule of C~12~H~6~O~3~.
The other half of the molecule is generated by a crystallographic
2-fold rotation symmetry operation.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
The H atoms were all located in a difference map, but
were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98 \%A) and with
U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom,
after which the positions were refined without restraints
and the displacement parameters were held fixed.
The largest peaks in the final difference electron density map
are located between C atoms.
;
_publ_section_exptl_prep
;
The compound was prepared by TF
and was crystallised from chloroform/hexane.
The sample ID is tf729_cycloFu~3~.
;
_refine_special_details
;
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(2000). maXus Computer Program for the Solution and Refinement of
Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The
University of Glasgow.
Coppens, P. (1970). The Evaluation of Absorption and Extinction in
Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed,
S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270.
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.55048(9) 0.50454(15) 0.26441(18) 0.0316 1.0000 Uani . . . . . . .
C2 C 0.61526(10) 0.39315(17) 0.2833(2) 0.0396 1.0000 Uani . . . . . . .
O3 O 0.70309(7) 0.45528(12) 0.30840(16) 0.0441 1.0000 Uani . . . . . . .
C4 C 0.69190(10) 0.61090(18) 0.3041(2) 0.0388 1.0000 Uani . . . . . . .
C5 C 0.60050(9) 0.64734(15) 0.27798(18) 0.0318 1.0000 Uani . . . . . . .
C6 C 0.55025(9) 0.79099(15) 0.26362(18) 0.0333 1.0000 Uani . . . . . . .
C7 C 0.57628(11) 0.93912(17) 0.2704(2) 0.0423 1.0000 Uani . . . . . . .
O8 O 0.5000 1.03312(16) 0.2500 0.0477 1.0000 Uani S T . . . . .
H21 H 0.6109(12) 0.277(2) 0.282(2) 0.0480 1.0000 Uiso . . . . . . .
H41 H 0.7527(12) 0.6704(19) 0.323(2) 0.0473 1.0000 Uiso . . . . . . .
H71 H 0.6379(13) 0.992(2) 0.284(3) 0.0526 1.0000 Uiso . . . . . . .
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 0.0297(7) 0.0363(7) 0.0298(6) -0.0015(5) 0.0141(5) 0.0001(5)
C2 0.0336(7) 0.0398(8) 0.0464(8) -0.0041(6) 0.0188(6) 0.0015(6)
O3 0.0310(5) 0.0489(6) 0.0542(6) -0.0078(4) 0.0207(4) 0.0030(4)
C4 0.0308(7) 0.0445(8) 0.0433(7) -0.0059(6) 0.0185(5) -0.0023(6)
C5 0.0288(6) 0.0378(7) 0.0294(6) -0.0018(4) 0.0136(5) -0.0017(5)
C6 0.0313(7) 0.0369(7) 0.0305(6) 0.0010(5) 0.0128(5) -0.0011(5)
C7 0.0374(8) 0.0396(8) 0.0466(8) 0.0009(6) 0.0157(6) -0.0034(6)
O8 0.0434(8) 0.0341(8) 0.0578(9) 0.0000 0.0155(7) 0.0000
_refine_ls_extinction_method None
_oxford_refine_ls_scale 1.075(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C1 5_655 1.453(2) yes
C1 . C2 . 1.3489(19) yes
C1 . C5 . 1.4443(17) yes
C2 . O3 . 1.3762(17) yes
C2 . H21 . 1.019(17) no
O3 . C4 . 1.3725(19) yes
C4 . C5 . 1.3536(18) yes
C4 . H41 . 1.016(17) no
C5 . C6 . 1.4515(18) yes
C6 . C6 5_655 1.450(2) yes
C6 . C7 . 1.3512(19) yes
C7 . O8 . 1.3749(17) yes
C7 . H71 . 1.011(19) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 5_655 C1 . C2 . 133.66(8) yes
C1 5_655 C1 . C5 . 119.97(7) yes
C2 . C1 . C5 . 106.36(12) yes
C1 . C2 . O3 . 110.36(13) yes
C1 . C2 . H21 . 132.7(9) no
O3 . C2 . H21 . 116.9(9) no
C2 . O3 . C4 . 106.68(10) yes
O3 . C4 . C5 . 110.27(12) yes
O3 . C4 . H41 . 114.2(9) no
C5 . C4 . H41 . 135.5(9) no
C1 . C5 . C4 . 106.33(12) yes
C1 . C5 . C6 . 120.14(12) yes
C4 . C5 . C6 . 133.53(13) yes
C5 . C6 . C6 5_655 119.88(7) yes
C5 . C6 . C7 . 133.95(12) yes
C6 5_655 C6 . C7 . 106.16(8) yes
C6 . C7 . O8 . 110.63(13) yes
C6 . C7 . H71 . 133.6(10) no
O8 . C7 . H71 . 115.7(10) no
C7 . O8 . C7 5_655 106.41(15) yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O3 C7 3.484(2) . 4_666 no
O3 C5 3.510(2) . 6_564 no
O3 C1 3.543(1) . 6_564 no
O3 C4 3.576(2) . 6_564 no
O8 C7 3.372(1) . 2_675 no
O8 C7 3.372(1) . 6_575 no
O8 C2 3.563(2) . 1_565 no
O8 C2 3.563(2) . 5_665 no
C1 C1 3.384(2) . 2_665 no
C1 C2 3.500(2) . 6_565 no
C1 C1 3.572(2) . 6_565 no
C1 C1 3.572(2) . 6_564 no
C2 C4 3.366(2) . 6_565 no
C2 C5 3.533(2) . 6_564 no
C4 C7 3.503(2) . 4_666 no
C4 C4 3.532(3) . 4_666 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C2 C1 C1 . . . 5_655 -179.9(2) no
O3 C2 C1 C5 . . . . 0.1(1) no
O3 C4 C5 C1 . . . . -0.1(1) no
O3 C4 C5 C6 . . . . 179.7(1) no
O8 C7 C6 C5 . . . . -179.7(1) no
O8 C7 C6 C6 . . . 5_655 0.1(2) no
O8 C7 C6 C5 . 5_655 5_655 5_655 -179.7(1) no
O8 C7 C6 C6 . 5_655 5_655 . 0.1(2) no
C1 C1 C5 C4 . 5_655 5_655 5_655 -180.0(1) no
C1 C1 C5 C6 . 5_655 5_655 5_655 0.2(2) no
C1 C2 O3 C4 . . . . -0.2(2) no
C1 C5 C6 C6 . . . 5_655 0.2(2) no
C1 C5 C6 C7 . . . . -180.0(1) no
C2 O3 C4 C5 . . . . 0.2(2) no
C2 C1 C1 C2 . . 5_655 5_655 -0.3(4) no
C2 C1 C1 C5 . . 5_655 5_655 179.6(1) no
C2 C1 C5 C4 . . . . -0.0(1) no
C2 C1 C5 C6 . . . . -179.8(1) no
C4 C5 C6 C6 . . . 5_655 -179.5(2) no
C4 C5 C6 C7 . . . . 0.3(3) no
C5 C1 C1 C5 . . 5_655 5_655 -0.4(3) no
C5 C6 C6 C5 . . 5_655 5_655 -0.5(2) no
C5 C6 C6 C7 . . 5_655 5_655 179.69(9) no
C6 C7 O8 C7 . . . 5_655 -0.06(7) no
C7 C6 C6 C7 . . 5_655 5_655 -0.2(2) no
#------------------------------------------------------------------------------
#===END
# Attachment 'Cpd28_she0711raeC.cif'
# CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98)
data_she0711_rae
_database_code_depnum_ccdc_archive 'CCDC 860345'
_audit_creation_method maXus
_audit_update_record
;
2010-04-07 - Report on C16 H8 O4
by A. David Rae
edited by Anthony C. Willis
for Thomas Fallon and Mick Sherburn
2010-04-08 - passes checkcif tests with warnings
2010-04-07 # Formatted by publCIF
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'
_symmetry_space_group_name_H-M 'A b a 2 '
_symmetry_cell_setting orthorhombic
_cell_length_a 8.8594(3)
_cell_length_b 8.8592(2)
_cell_length_c 46.7607(14)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3670.1(2)
_cell_formula_units_Z 12
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 'Waasmaier & Kirfel, 1995'
'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995'
'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995'
_chemical_compound_source 'Local laboratory'
_chemical_formula_moiety 'C16 H8 O4 '
_chemical_formula_sum 'C16 H8 O4 '
_chemical_name_systematic
;
;
_chemical_formula_weight 264.236
_cell_measurement_temperature 200
_cell_measurement_reflns_used 12599
_cell_measurement_theta_min 2.546
_cell_measurement_theta_max 25.028
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.04
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_max 0.40
_exptl_crystal_density_diffrn 1.435
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1632
_exptl_special_details
;
;
# Absorption correction
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.035
0 0 -1 0.001
-1 1 0 0.200
1 -1 0 0.200
2 1 0 0.110
-2 -1 0 0.093
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.974
_exptl_absorpt_correction_T_max 0.996
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_absorpt_coefficient_mu 0.104
_diffrn_measurement_device KappaCCD
#_diffrn_measurement_method 'CCD'
_diffrn_radiation_source 'fine-focus sealed tube'
loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_wavelength_id all
_diffrn_radiation_type ' MoK\a'
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 1.5 deg at rate 195 sec/frame,
crystal-detector distance 40mm,
multiple scan sets so over 90 percent of data collected with 4-fold
redundancy or more.
;
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement 'RAELS06 (Rae, 2006) '
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material 'maXus(Mackay et al., 1999)'
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -55
_diffrn_reflns_limit_l_max 55
_diffrn_orient_matrix_type X=UH
_diffrn_orient_matrix_UB_11 -0.10947
_diffrn_orient_matrix_UB_12 -0.02070
_diffrn_orient_matrix_UB_13 -0.01813
_diffrn_orient_matrix_UB_21 -0.02612
_diffrn_orient_matrix_UB_22 0.10155
_diffrn_orient_matrix_UB_23 0.04180
_diffrn_orient_matrix_UB_31 0.00164
_diffrn_orient_matrix_UB_32 0.00848
_diffrn_orient_matrix_UB_33 -0.01957
_diffrn_ambient_temperature 200
_diffrn_reflns_number 22876
_diffrn_reflns_theta_max 25.02
_diffrn_reflns_theta_min 2.61
_diffrn_reflns_theta_full 25.02
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_av_R_equivalents 0.036
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
# Refinement statistics
_reflns_d_resolution_low 1.97
_reflns_d_resolution_high 0.65
_reflns_limit_h_max 10
_reflns_limit_h_min 0
_reflns_limit_k_max 10
_reflns_limit_k_min 0
_reflns_limit_l_max 55
_reflns_limit_l_min 0
_refine_ls_matrix_type full
_refine_ls_shift/su_max 3.765
_refine_ls_shift/su_mean 0.874
_reflns_number_total 1648
_refine_ls_R_factor_all 0.081
_refine_ls_wR_factor_all 0.089
_refine_ls_goodness_of_fit_all 1.89
_reflns_number_gt 1060
_reflns_threshold_expression 'I> 3.00 sigma(I)'
_refine_ls_R_factor_gt 0.048
_refine_ls_wR_factor_gt 0.072
_refine_ls_goodness_of_fit_gt 1.91
_refine_ls_number_reflns 995
_refine_ls_number_parameters 115
_refine_ls_number_restraints 0
_refine_ls_number_constraints 69 # 27 + 42
_refine_ls_wR_factor_ref 0.072
_refine_ls_goodness_of_fit_ref 1.91
_refine_ls_abs_structure_details
;
;
_refine_ls_hydrogen_treatment refxyz
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme sigma
_refine_ls_weighting_details
; w = 1 / ( \s^2^(Fo) + 0.00090 * Fo^2^)
;
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_diff_density_max .396
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.10
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of C~16~H~8~O~4~ is reported.
Some classes of reflection are systematically weak which initially appeared to
suggest that the diffraction pattern was twinned. It has been found that this
actually arises from pseudo-symmetry relationships between the molecules.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of three one-half molecules of
C~16~H~8~O~4~. The other half of each molecule is generated by an appropriate
crystallographic twofold symmetry operator.
Each molecule has the same approximate local -42m symmetry with the -4 axis
perpendicular to the crystallographic c axis and approximately parallel to
either the a + b or -a + b directions. Each molecule contains a 2 fold
rotation axis coincident with a crystallographic 2 fold rotation axis parallel
to c.
A strange pseudo absence condition corresponding to 3h+l = 6n+-2 comes about
because of the pseudo translational relationship between the 3 half molecules
in the asymmetric unit of Aba2. The structure consists of pseudo equivalent
layers perpendicular to c, each of ba2 symmetry. If we describe layers at z =
1/6, 1/3 and 1/2 as having structure factors F1, F2, F3 relative to pseudo
equivalent origins at 0,0,1/6; 0,1/2,1/3; 1/2,1/2,1/2 then when k + l is even
(-1)^h^ F(hkl)/2 = [(-1)^h+l^ \w^2l^ F1 + (-1)^h+l^ \w^l^ F2 + F3] = F3 +
(-1)^h+l^ [(\w^2l^ + \w^l^) (F1 + F2)/2 + (\w^2l^ - \w^l^) (F1 - F2)/2] where
\w^l^ = exp(2\pil/3)
so that for
INDEX1 3h+l = 6n F(hkl) = 2 (-1)^h^ (F1 + F2 + F3),
INDEX2 3h+l = 6n+-1 F(hkl) = (-1)^h^ [(F1 + F2) +- iSQRT3(F1 - F2) + 2 F3],
INDEX3 3h+l = 6n+-2 F(hkl) = (-1)^h^ [- (F1 + F2) +- iSQRT3(F1 - F2) + 2 F3],
INDEX4 3h+l = 6n+3 F(hkl) = 2 (-1)^h^ [- (F1 + F2) + F3].
(SQRT3 = 1.73205)
If the pseudo translation is exact then F1 = F2 = F3 and mean intensities for
reflections of index 1, 2, 3, 4 will have values in the ratio 9 : 4 : 0 : 1.
Reflection data were analyzed using these 4 index conditions. It can
reasonably be assumed that the parameter combinations defining (F1 + F2) and
F3 are well determined but (F1 - F2) is not necessarily well determined,
suggesting constrained refinement would be a sensible approach for describing
the difference between the layers at z = 1/6 and 1/3, and for avoiding the
possibility of false minima, see (Rae et al., 2005).
The structure consists of two interpenetrating hydrogen bond networks. A single
network only connects molecules related by pseudo translation. The second
network is glide related to the first. Every furan ring is involved in the
hydrogen bonding, either as a donor using the H nearest a crystallographic
two-fold axis or as an acceptor using the O atom, but never as both. The furan
rings defining F1 have their O atoms acting as acceptors, the rings defining
F2 are donors, whereas the rings defining F3 are of each type. A sensible
constraint is to define common refinable local orthonormal coordinates for
rings of the same type. A hierarchical constrained refinement approach was
used to assess the extent to which meaningful detail of the pseudo-symmetric
structure could be reliably obtained. This used the program RAELS06, based on
papers by Rae (1975).
The origins of the furan rings were centered on the O atom. In refinements 1,
2, 3 the difference in z coordinates for O atoms in the same tetrafuran were
constrained to be equal for all tetrafurans and the thus defined layers that
were constrained to be 1/6 c apart. Only reflections with Icalc > 3\s(Iobs)
and INDEX \\neq 3 were used in the first 3 refinements.
Refinement 1
F1 = F2 = F3, 32 independent variables. Each ring is flat and identical and
each tetrafuran is described by the same 9 parameter TLX model restricted by
the 2-fold site symmetry. This gave R1(F) = 0.054, 0.085, 1.0, 0.168 for the
307, 408, 168, 177 reflections with Iobs > 3\s(Iobs) and INDEX 1, 2, 3, 4
respectively.
Refinement 2
F1 = F2 \\neq F3, 52 independent variables. Each ring is flat and identical and
the axial systems and TLX model for the third tetrafuran is now different to
those for the other two. R1(F) = 0.056, 0.081, 0.385, 0.068 for the same
choice of reflections with INDEX 1, 2, 3, 4 respectively.
Refinement 3
F1 \\neq F2 \\neq F3, 63 independent variables. Each ring is flat and
identical. Now the axial systems are independent for all furan rings but the
TLX model for the first and second tetrafurans remain the same. R1(F) = 0.056,
0.063, 0.285, 0.069 for the same choice of reflections with INDEX 1, 2, 3, 4
respectively.
Refinement 4
65 independent variables. Same as refinement 3 except that now the z coordinate
spacing for the furan rings was no longer constrained and all reflections with
Icalc > 3\s(Iobs) were now included in the refinement. R1(F) = 0.056, 0.063,
0.244, 0.075 for the same choice of reflections with INDEX 1, 2, 3, 4
respectively.
Refinement 5
74 independent variables. Same as refinement 4 except that the TLX parameters
are now independent for each tetrafuran. R1(F) = 0.055, 0.059, 0.209, 0.074
for the same choice of reflections with INDEX 1, 2, 3, 4 respectively.
Refinement 6
85 independent variables. Same as refinement 5 except that now the planar furan
rings are separated into two types, those with a donor C-H and those with a
receptor O. R1(F) = 0.055, 0.059, 0.204, 0.075 for the same choice of
reflections with INDEX 1, 2, 3, 4 respectively.
Refinement 7
115 independent variables. Same as refinement 6 except that now the atoms in
the tetrafuran ring are allowed additional atom displacement parameters
relative to there local axial systems so as to obey a pseudo -42m symmetry
common to each tetrafuran. Hydrogen atoms were allowed the same increment as
the atom to which they were attached. The TLX parameter changes were now
restrained to stay near their present values. R1(F) = 0.036, 0.045, 0.211,
0.055 for the same choice of reflections with INDEX 1, 2, 3, 4 respectively.
If we consider only those reflections for which both Icalc and Iobs are greater
than 3\s(Iobs) then R1(F) = 0.035, 0.044, 0.111, 0.054 (overall 0.042) for the
resulting 300, 403, 121, 171 reflections with INDEX 1, 2, 3, 4 respectively
(overall 995 out of 1648 reflections). The 653 reflections not used for
refinement had R1(F) = 0.451 and a goodness of fit 2.26 and had an average
value for |Fcalc|^2^ that was 0.52 of the average value of |Fobs|^2^. For all
1648 reflections R1(F) = 0.081.
An uncorrelated 3% error in F was included along with the counting statistics
estimate of the error in Fobs to estimate errors for the refinement on F using
weights w = 1/(var(Fobs) + 0.0009Fobs^2^). A goodness of fit of 1.46, 1.59,
1.97, 1.57 was obtained for the reflections of INDEX 1, 2, 3, 4 respectively
that were used in the refinement (Overall value 1.60)
One can conclude that there was no determinable effect of the hydrogen bonding
on the geometry of the furan rings but there were detectable zero order atom
displacement parameters in addition to those obtained from simple TLX models.
RAELS06, Rae, A.D. (2006) The Australian National University, Canberra.
Rae, A.D. (1975) Acta Cryst. A31, 560-570, 570-574.
Rae, A.D., Mossin, S. & S\/orensen, H.O. (2005) Acta Cryst. B61, 407-417.
;
_publ_section_acknowledgements # Acknowledgments
;
(type here to add acknowledgements)
;
_publ_section_figure_captions #Captions to figures
;
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
;
_publ_section_exptl_prep
;
The compound was prepared by TF and was crystallized from petroleum
spirits/dichloromethane. The sample ID is tf-cycFu~4~.
;
_refine_special_details
;
See Comments section for details of the refinement.
;
_publ_section_references
;
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999).
maXus Computer Program for the Solution and Refinement of Crystal
Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University
of Glasgow.
Johnson, C. K. (1976). ORTEPII. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.
Otwinowski, Z. & Minor, W. (1997). In Methods in Enzymology, 276, edited
by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,
Guagliardi, A., Moliterni, A. G. G. & Spagna, R. (1999). J. Appl.
Cryst. 32, 115--119.
Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416--431.
Nonius (1997--2001). COLLECT. Nonius BV, Delft, The Netherlands.
Molecular Structure Corporation. (1992--1997). TEXSAN. Single Crystal
Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The
Woodlands, TX 77381, USA.
Johnson, C. K. (1976). ORTEPII, A Fortran Thermal-Ellipsoid Plot
Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.
RAELS06, Rae, A.D. (2006). The Australian National University, Canberra.
Rae, A. D. (1975). Acta Cryst. A31, 560-570, 570-574.
Rae, A. D., Mossin, S. & S\/orensen, H. O. (2005). Acta Cryst. B61, 407-417.
;
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_calc_attached_atom
O12 O 0.0649(3) 0.3141(3) 0.21817(9) 0.0677(9) 1.000 1 d . . .
O17 O 0.3141(3) 0.0661(4) 0.11573(7) 0.0674(7) 1.000 1 d . . .
C10 C 0.0239(4) 0.0787(3) 0.20249(9) 0.0367(6) 1.000 1 d . . .
C11 C 0.0031(4) 0.1767(4) 0.22440(8) 0.0504(7) 1.000 1 d . . .
C13 C 0.1260(4) 0.3008(4) 0.19155(9) 0.0601(8) 1.000 1 d . . .
C14 C 0.1052(3) 0.1606(3) 0.18076(8) 0.0413(6) 1.000 1 d . . .
C15 C 0.1599(4) 0.1054(3) 0.15307(8) 0.0412(6) 1.000 1 d . . .
C16 C 0.3000(4) 0.1272(4) 0.14234(9) 0.0596(7) 1.000 1 d . . .
C18 C 0.1773(4) 0.0033(4) 0.10945(9) 0.0507(7) 1.000 1 d . . .
C19 C 0.0789(3) 0.0235(3) 0.13131(8) 0.0370(6) 1.000 1 d . . .
O22 O 0.0751(4) 0.8121(3) 0.38539(6) 0.0629(8) 1.000 1 d . . .
O27 O 0.3121(3) 0.5754(3) 0.28204(8) 0.0620(7) 1.000 1 d . . .
C20 C 0.0257(3) 0.5786(3) 0.36977(8) 0.0350(5) 1.000 1 d . . .
C21 C 0.0106(4) 0.6757(4) 0.39197(8) 0.0504(7) 1.000 1 d . . .
C23 C 0.1314(4) 0.7987(3) 0.35836(8) 0.0506(7) 1.000 1 d . . .
C24 C 0.1050(3) 0.6589(3) 0.34764(8) 0.0355(5) 1.000 1 d . . .
C25 C 0.1589(3) 0.6055(3) 0.31979(8) 0.0353(5) 1.000 1 d . . .
C26 C 0.2987(3) 0.6318(3) 0.30907(8) 0.0503(7) 1.000 1 d . . .
C28 C 0.1756(4) 0.5111(4) 0.27547(8) 0.0493(7) 1.000 1 d . . .
C29 C 0.0785(3) 0.5263(3) 0.29767(9) 0.0342(5) 1.000 1 d . . .
O32 O 0.5807(3) 0.8106(3) 0.55156(4) 0.0678(6) 1.000 1 d . . .
O37 O 0.8155(3) 0.5589(3) 0.44844(4) 0.0698(7) 1.000 1 d . . .
C30 C 0.5271(4) 0.5781(3) 0.53591(8) 0.0388(5) 1.000 1 d . . .
C31 C 0.5134(4) 0.6755(4) 0.55809(8) 0.0539(6) 1.000 1 d . . .
C33 C 0.6376(4) 0.7960(3) 0.52459(7) 0.0569(7) 1.000 1 d . . .
C34 C 0.6086(4) 0.6566(3) 0.51386(7) 0.0407(5) 1.000 1 d . . .
C35 C 0.6632(4) 0.6008(3) 0.48595(7) 0.0412(5) 1.000 1 d . . .
C36 C 0.8036(3) 0.6194(3) 0.47514(7) 0.0584(8) 1.000 1 d . . .
C38 C 0.6771(4) 0.4998(4) 0.44219(7) 0.0550(6) 1.000 1 d . . .
C39 C 0.5796(3) 0.5217(4) 0.46416(8) 0.0393(5) 1.000 1 d . . .
H11 H -0.0448(16) 0.1690(28) 0.2427(5) 0.0564(8) 1.000 1 d . . .
H13 H 0.1747(18) 0.3924(28) 0.1844(6) 0.0803(12) 1.000 1 d . . .
H16 H 0.3912(28) 0.1765(18) 0.1495(6) 0.0794(8) 1.000 1 d . . .
H18 H 0.1701(28) -0.0446(17) 0.0911(5) 0.0569(7) 1.000 1 d . . .
H21 H -0.0341(16) 0.6766(26) 0.4119(5) 0.0613(8) 1.000 1 d . . .
H23 H 0.1852(16) 0.8935(27) 0.3498(6) 0.0654(10) 1.000 1 d . . .
H26 H 0.3936(27) 0.6855(16) 0.3176(6) 0.0655(8) 1.000 1 d . . .
H28 H 0.1765(26) 0.4663(16) 0.2556(5) 0.0596(7) 1.000 1 d . . .
H31 H 0.4680(16) 0.6775(26) 0.5779(5) 0.0639(7) 1.000 1 d . . .
H33 H 0.6935(16) 0.8896(27) 0.5161(6) 0.0740(10) 1.000 1 d . . .
H36 H 0.8962(28) 0.6661(17) 0.4823(6) 0.0751(11) 1.000 1 d . . .
H38 H 0.6682(28) 0.4527(16) 0.4238(5) 0.0639(7) 1.000 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O12 0.1018(17) 0.0475(11) 0.0540(13) -0.0141(9) -0.0208(9) -0.0133(9)
O17 0.0483(12) 0.1025(16) 0.0515(13) -0.0137(9) 0.0115(10) 0.0217(9)
C10 0.0409(12) 0.0366(12) 0.0326(11) -0.0040(8) -0.0077(6) -0.0025(7)
C11 0.0651(16) 0.0482(13) 0.0380(12) -0.0037(9) -0.0132(9) -0.0069(9)
C13 0.0784(17) 0.0465(12) 0.0554(15) -0.0250(10) -0.0204(10) 0.0016(10)
C14 0.0437(11) 0.0413(11) 0.0389(11) -0.0147(8) -0.0134(7) 0.0046(6)
C15 0.0432(11) 0.0420(11) 0.0384(11) -0.0145(8) -0.0046(6) 0.0139(7)
C16 0.0484(13) 0.0771(16) 0.0534(15) -0.0248(10) -0.0022(10) 0.0213(10)
C18 0.0485(14) 0.0665(15) 0.0372(12) -0.0029(9) 0.0057(10) 0.0134(9)
C19 0.0380(13) 0.0405(11) 0.0324(11) -0.0035(8) 0.0022(7) 0.0079(6)
O22 0.0904(15) 0.0442(11) 0.0541(13) -0.0199(9) -0.0028(8) -0.0113(9)
O27 0.0427(11) 0.0885(15) 0.0549(13) -0.0193(9) 0.0112(9) 0.0028(8)
C20 0.0341(11) 0.0313(12) 0.0394(11) -0.0009(7) -0.0045(6) -0.0020(7)
C21 0.0602(16) 0.0455(13) 0.0457(12) -0.0145(9) -0.0011(9) -0.0078(10)
C23 0.0634(15) 0.0398(12) 0.0487(15) -0.0151(10) -0.0123(9) 0.0042(10)
C24 0.0326(11) 0.0338(11) 0.0402(11) -0.0029(8) -0.0110(7) 0.0059(6)
C25 0.0330(11) 0.0325(11) 0.0403(11) -0.0028(8) -0.0061(6) 0.0108(7)
C26 0.0387(12) 0.0629(15) 0.0493(15) -0.0149(10) -0.0046(10) 0.0121(9)
C28 0.0439(14) 0.0578(14) 0.0460(12) -0.0137(9) 0.0078(10) 0.0013(9)
C29 0.0300(12) 0.0331(11) 0.0395(11) -0.0004(7) 0.0019(7) 0.0045(6)
O32 0.0995(15) 0.0480(10) 0.0558(12) -0.0184(9) -0.0093(9) -0.0103(9)
O37 0.0511(11) 0.0986(15) 0.0598(13) -0.0151(9) 0.0153(10) 0.0076(9)
C30 0.0411(11) 0.0355(11) 0.0398(11) -0.0007(7) -0.0056(6) -0.0017(7)
C31 0.0677(15) 0.0483(12) 0.0456(11) -0.0102(9) -0.0051(9) -0.0065(9)
C33 0.0721(16) 0.0459(11) 0.0529(14) -0.0180(10) -0.0151(10) 0.0047(10)
C34 0.0400(10) 0.0396(10) 0.0423(10) -0.0055(8) -0.0117(7) 0.0061(6)
C35 0.0408(10) 0.0402(10) 0.0426(10) -0.0059(8) -0.0046(6) 0.0120(7)
C36 0.0462(12) 0.0734(16) 0.0556(15) -0.0166(10) -0.0014(10) 0.0149(10)
C38 0.0533(13) 0.0650(15) 0.0468(11) -0.0091(9) 0.0097(10) 0.0044(9)
C39 0.0387(12) 0.0393(10) 0.0398(11) -0.0005(7) 0.0028(7) 0.0054(6)
H11 0.0733(19) 0.0606(16) 0.0353(12) 0.0110(11) -0.0127(9) -0.0064(10)
H13 0.1104(21) 0.0527(12) 0.0778(18) -0.0423(12) -0.0198(10) 0.0022(10)
H16 0.0550(13) 0.1086(21) 0.0745(18) -0.0423(12) -0.0026(10) 0.0209(10)
H18 0.0593(18) 0.0769(18) 0.0346(12) 0.0121(12) 0.0047(10) 0.0124(9)
H21 0.0758(19) 0.0608(17) 0.0472(12) -0.0168(12) 0.0039(10) -0.0128(10)
H23 0.0912(19) 0.0456(12) 0.0595(17) -0.0296(11) -0.0125(9) 0.0050(10)
H26 0.0447(12) 0.0911(19) 0.0606(17) -0.0295(11) -0.0057(10) 0.0122(9)
H28 0.0592(17) 0.0722(17) 0.0474(12) -0.0158(11) 0.0128(11) -0.0034(10)
H31 0.0842(19) 0.0616(15) 0.0460(12) -0.0069(13) -0.0013(10) -0.0100(10)
H33 0.1011(20) 0.0532(12) 0.0675(17) -0.0347(12) -0.0148(10) 0.0056(10)
H36 0.0507(12) 0.1032(20) 0.0716(19) -0.0309(11) -0.0020(10) 0.0149(10)
H38 0.0694(17) 0.0756(17) 0.0467(12) -0.0058(13) 0.0128(10) 0.0010(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O12 C11 1.365(3) . . .
O12 C13 1.363(3) . . .
O17 C16 1.363(3) . . .
O17 C18 1.365(3) . . .
C10 C10 1.458(5) . 2_555 .
C10 C11 1.356(3) . . .
C10 C14 1.441(3) . . .
C13 C14 1.353(3) . . .
C14 C15 1.467(5) . . .
C15 C16 1.353(3) . . .
C15 C19 1.441(3) . . .
C18 C19 1.356(3) . . .
C19 C19 1.458(5) . 2_555 .
O22 C21 1.371(3) . . .
O22 C23 1.364(3) . . .
O27 C26 1.364(3) . . .
O27 C28 1.371(3) . . .
C20 C20 1.465(5) . 2_565 .
C20 C21 1.355(3) . . .
C20 C24 1.439(3) . . .
C23 C24 1.357(3) . . .
C24 C25 1.466(5) . . .
C25 C26 1.357(3) . . .
C25 C29 1.439(3) . . .
C28 C29 1.355(3) . . .
C29 C29 1.467(5) . 2_565 .
O32 C31 1.371(3) . . .
O32 C33 1.364(3) . . .
O37 C36 1.363(3) . . .
O37 C38 1.365(3) . . .
C30 C30 1.464(5) . 2_665 .
C30 C31 1.355(3) . . .
C30 C34 1.439(3) . . .
C33 C34 1.357(3) . . .
C34 C35 1.477(4) . . .
C35 C36 1.353(3) . . .
C35 C39 1.441(3) . . .
C38 C39 1.356(3) . . .
C39 C39 1.463(5) . 2_665 .
C11 H11 0.96(3) . . .
C13 H13 0.98(3) . . .
C16 H16 0.98(3) . . .
C18 H18 0.96(3) . . .
C21 H21 1.01(3) . . .
C23 H23 1.05(3) . . .
C26 H26 1.05(3) . . .
C28 H28 1.01(3) . . .
C31 H31 1.01(3) . . .
C33 H33 1.05(3) . . .
C36 H36 0.98(3) . . .
C38 H38 0.96(3) . . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O12 C28 3.345(4) . . .
O17 C31 3.365(4) . 5_544 .
C10 C19 3.567(5) . 2_555 .
C11 O27 3.279(4) . 4_545 .
C14 C14 3.403(6) . 2_555 .
C14 C15 3.571(4) . 2_555 .
C18 C18 3.142(7) . 2_555 .
C18 O32 3.283(4) . 7_454 .
O22 C38 3.263(4) . 3_465 .
C21 O37 3.321(4) . 1_455 .
C24 C24 3.374(6) . 2_565 .
C24 C25 3.556(4) . 2_565 .
C28 C28 3.118(7) . 2_565 .
C34 C34 3.377(6) . 2_665 .
C34 C35 3.564(4) . 2_665 .
C38 C38 3.137(7) . 2_665 .
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O12 C13 106.1(2) . . . .
C16 O17 C18 106.1(2) . . . .
C10 C10 C11 125.0(2) 2_555 . . .
C10 C10 C14 128.8(2) 2_555 . . .
C11 C10 C14 106.2(2) . . . .
O12 C11 C10 110.8(2) . . . .
O12 C13 C14 111.5(2) . . . .
C10 C14 C13 105.5(2) . . . .
C10 C14 C15 128.3(2) . . . .
C13 C14 C15 126.2(3) . . . .
C14 C15 C16 125.7(3) . . . .
C14 C15 C19 128.8(3) . . . .
C16 C15 C19 105.5(2) . . . .
O17 C16 C15 111.5(2) . . . .
O17 C18 C19 110.8(2) . . . .
C15 C19 C18 106.2(2) . . . .
C15 C19 C19 128.4(2) . . 2_555 .
C18 C19 C19 125.4(2) . . 2_555 .
C21 O22 C23 106.5(2) . . . .
C26 O27 C28 106.5(2) . . . .
C20 C20 C21 124.9(2) 2_565 . . .
C20 C20 C24 128.4(2) 2_565 . . .
C21 C20 C24 106.6(2) . . . .
O22 C21 C20 110.3(2) . . . .
O22 C23 C24 111.0(2) . . . .
C20 C24 C23 105.7(2) . . . .
C20 C24 C25 129.7(2) . . . .
C23 C24 C25 124.5(2) . . . .
C24 C25 C26 124.8(3) . . . .
C24 C25 C29 129.4(2) . . . .
C26 C25 C29 105.7(2) . . . .
O27 C26 C25 111.0(2) . . . .
O27 C28 C29 110.3(2) . . . .
C25 C29 C28 106.6(2) . . . .
C25 C29 C29 128.6(2) . . 2_565 .
C28 C29 C29 124.8(2) . . 2_565 .
C31 O32 C33 106.5(2) . . . .
C36 O37 C38 106.1(2) . . . .
C30 C30 C31 124.9(2) 2_665 . . .
C30 C30 C34 128.4(2) 2_665 . . .
C31 C30 C34 106.6(2) . . . .
O32 C31 C30 110.3(2) . . . .
O32 C33 C34 111.0(2) . . . .
C30 C34 C33 105.7(2) . . . .
C30 C34 C35 129.5(2) . . . .
C33 C34 C35 124.7(3) . . . .
C34 C35 C36 126.2(3) . . . .
C34 C35 C39 128.2(3) . . . .
C36 C35 C39 105.5(2) . . . .
O37 C36 C35 111.5(2) . . . .
O37 C38 C39 110.8(2) . . . .
C35 C39 C38 106.2(2) . . . .
C35 C39 C39 128.6(2) . . 2_665 .
C38 C39 C39 125.2(2) . . 2_665 .
O12 C11 H11 115.6(16) . . . .
C10 C11 H11 133.6(16) . . . .
O12 C13 H13 114.6(18) . . . .
C14 C13 H13 133.9(18) . . . .
O17 C16 H16 114.6(18) . . . .
C15 C16 H16 133.9(18) . . . .
O17 C18 H18 115.6(16) . . . .
C19 C18 H18 133.6(16) . . . .
O22 C21 H21 111.3(14) . . . .
C20 C21 H21 138.5(14) . . . .
O22 C23 H23 116.8(16) . . . .
C24 C23 H23 132.2(16) . . . .
O27 C26 H26 116.8(16) . . . .
C25 C26 H26 132.2(16) . . . .
O27 C28 H28 111.3(14) . . . .
C29 C28 H28 138.5(14) . . . .
O32 C31 H31 111.3(14) . . . .
C30 C31 H31 138.5(14) . . . .
O32 C33 H33 116.8(16) . . . .
C34 C33 H33 132.2(16) . . . .
O37 C36 H36 114.6(18) . . . .
C35 C36 H36 133.9(18) . . . .
O37 C38 H38 115.6(16) . . . .
C39 C38 H38 133.6(16) . . . .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21 O37 1.01(3) 2.41(3) 3.321(4) 150.2(19) 1_455 .
C28 H28 O12 1.01(3) 2.42(3) 3.345(4) 151.7(18) . .
C31 H31 O17 1.01(3) 2.44(3) 3.365(4) 151.6(19) 5_555 .
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
C13 O12 C11 C10 0.0 . . . . .
C11 O12 C13 C14 -0.0 . . . . .
C18 O17 C16 C15 0.0 . . . . .
C16 O17 C18 C19 0.0 . . . . .
C11 C10 C10 C11 -45.5(5) . . 2_555 2_555 .
C11 C10 C10 C14 132.1(2) . . 2_555 2_555 .
C14 C10 C10 C11 132.1(2) . . 2_555 2_555 .
C14 C10 C10 C14 -50.4(6) . . 2_555 2_555 .
C10 C10 C11 O12 178.0(4) 2_555 . . . .
C14 C10 C11 O12 -0.0 . . . . .
C10 C10 C14 C13 -177.9(4) 2_555 . . . .
C10 C10 C14 C15 0.1(5) 2_555 . . . .
C11 C10 C14 C13 0.0 . . . . .
C11 C10 C14 C15 178.0(3) . . . . .
O12 C13 C14 C10 -0.0 . . . . .
O12 C13 C14 C15 -178.1(3) . . . . .
C10 C14 C15 C16 -132.5(2) . . . . .
C10 C14 C15 C19 50.0(4) . . . . .
C13 C14 C15 C16 45.2(3) . . . . .
C13 C14 C15 C19 -132.3(2) . . . . .
C14 C15 C16 O17 -178.0(3) . . . . .
C19 C15 C16 O17 -0.0 . . . . .
C14 C15 C19 C18 177.9(3) . . . . .
C14 C15 C19 C19 0.7(4) . . . 2_555 .
C16 C15 C19 C18 0.0 . . . . .
C16 C15 C19 C19 -177.1(4) . . . 2_555 .
O17 C18 C19 C15 -0.0 . . . . .
O17 C18 C19 C19 177.3(4) . . . 2_555 .
C15 C19 C19 C15 -51.4(5) . . 2_555 2_555 .
C15 C19 C19 C18 131.9(2) . . 2_555 2_555 .
C18 C19 C19 C15 131.9(2) . . 2_555 2_555 .
C18 C19 C19 C18 -44.7(5) . . 2_555 2_555 .
C23 O22 C21 C20 0.0 . . . . .
C21 O22 C23 C24 0.0 . . . . .
C28 O27 C26 C25 -0.0 . . . . .
C26 O27 C28 C29 0.0 . . . . .
C21 C20 C20 C21 -41.6(5) . . 2_565 2_565 .
C21 C20 C20 C24 135.9(2) . . 2_565 2_565 .
C24 C20 C20 C21 135.9(2) . . 2_565 2_565 .
C24 C20 C20 C24 -46.6(6) . . 2_565 2_565 .
C20 C20 C21 O22 177.9(4) 2_565 . . . .
C24 C20 C21 O22 -0.0 . . . . .
C20 C20 C24 C23 -177.8(4) 2_565 . . . .
C20 C20 C24 C25 -1.8(5) 2_565 . . . .
C21 C20 C24 C23 0.0 . . . . .
C21 C20 C24 C25 176.0(3) . . . . .
O22 C23 C24 C20 -0.0 . . . . .
O22 C23 C24 C25 -176.3(3) . . . . .
C20 C24 C25 C26 -133.1(2) . . . . .
C20 C24 C25 C29 51.3(4) . . . . .
C23 C24 C25 C26 42.2(3) . . . . .
C23 C24 C25 C29 -133.3(2) . . . . .
C24 C25 C26 O27 -176.4(3) . . . . .
C29 C25 C26 O27 0.0 . . . . .
C24 C25 C29 C28 176.2(3) . . . . .
C24 C25 C29 C29 -2.1(5) . . . 2_565 .
C26 C25 C29 C28 0.0 . . . . .
C26 C25 C29 C29 -178.3(4) . . . 2_565 .
O27 C28 C29 C25 -0.0 . . . . .
O27 C28 C29 C29 178.4(4) . . . 2_565 .
C25 C29 C29 C25 -46.1(6) . . 2_565 2_565 .
C25 C29 C29 C28 135.9(2) . . 2_565 2_565 .
C28 C29 C29 C25 135.9(2) . . 2_565 2_565 .
C28 C29 C29 C28 -42.2(4) . . 2_565 2_565 .
C33 O32 C31 C30 -0.0 . . . . .
C31 O32 C33 C34 0.0 . . . . .
C38 O37 C36 C35 0.0 . . . . .
C36 O37 C38 C39 -0.0 . . . . .
C31 C30 C30 C31 -42.0(5) . . 2_665 2_665 .
C31 C30 C30 C34 135.2(2) . . 2_665 2_665 .
C34 C30 C30 C31 135.2(2) . . 2_665 2_665 .
C34 C30 C30 C34 -47.5(6) . . 2_665 2_665 .
C30 C30 C31 O32 177.7(4) 2_665 . . . .
C34 C30 C31 O32 0.0 . . . . .
C30 C30 C34 C33 -177.6(4) 2_665 . . . .
C30 C30 C34 C35 -2.1(5) 2_665 . . . .
C31 C30 C34 C33 -0.0 . . . . .
C31 C30 C34 C35 175.6(3) . . . . .
O32 C33 C34 C30 -0.0 . . . . .
O32 C33 C34 C35 -175.9(3) . . . . .
C30 C34 C35 C36 -131.5(3) . . . . .
C30 C34 C35 C39 51.2(4) . . . . .
C33 C34 C35 C36 43.3(3) . . . . .
C33 C34 C35 C39 -134.0(2) . . . . .
C34 C35 C36 O37 -177.8(3) . . . . .
C39 C35 C36 O37 -0.0 . . . . .
C34 C35 C39 C38 177.7(3) . . . . .
C34 C35 C39 C39 0.5(5) . . . 2_665 .
C36 C35 C39 C38 0.0 . . . . .
C36 C35 C39 C39 -177.2(4) . . . 2_665 .
O37 C38 C39 C35 0.0 . . . . .
O37 C38 C39 C39 177.4(4) . . . 2_665 .
C35 C39 C39 C35 -50.5(6) . . 2_665 2_665 .
C35 C39 C39 C38 132.8(2) . . 2_665 2_665 .
C38 C39 C39 C35 132.8(2) . . 2_665 2_665 .
C38 C39 C39 C38 -44.0(5) . . 2_665 2_665 .
_geom_special_details
;
All standard uncertainties (except dihedral angles between
l.s. planes) are estimated using the full covariance matrix.
The standard uncertainties in cell dimensions are not used in
calculating the standard uncertainties of bond distances,
angles and torsion angles.
;
#===================================================
# start Validation Reply Form
_vrf_SHFSU01_she0711_rae
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: ...This is an artifact caused by looking at errors one at
a time. High parameter correlation caused by pseudo symmetry, disorder,
rigid body thermal motion, corefinement of local coordinates and axial
systems can cause such events. Refinement did converge as did shifts in
isolated atom parameters derived from the parameterisation.
;
_vrf_PLAT080_she0711_rae
;
PROBLEM: Maximum Shift/Error ............................ 3.77
RESPONSE: ...This is an artifact caused by looking at errors one at
a time. High parameter correlation caused by pseudo symmetry, disorder,
rigid body thermal motion, corefinement of local coordinates and axial
systems can cause such events. Refinement did converge as did shifts in
isolated atom parameters derived from the parameterisation.
;
# end Validation Reply Form
#===END