# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_global
#TrackingRef '246trifphenol_5.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jan 29 15:14:15 2013'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
;
#===END
# Attachment 'phenol_1.cif'
# CIF-file generated for vabalt in Pccn
#==============================================================================
#===============================================================================
data_vabalt
#TrackingRef 'phenol_1.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
'hexa-2,4-diyne-1,6-diyl bis(phenylcarbonate)'
;
_chemical_name_common
"'hexa-2,4-diyne-1,6-diyl bis(phenylcarbonate)'"
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H14 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C20 H14 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 350.31
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall '-P 2ab 2ac'
_symmetry_space_group_name_H-M 'P c c n'
_symmetry_Int_Tables_number 56
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,z
3 1/2+x,-y,1/2-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,-z
7 1/2-x,y,1/2+z
8 x,1/2-y,1/2+z
_cell_length_a 9.5387(15)
_cell_length_b 23.208(4)
_cell_length_c 7.4056(12)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1639.4(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 15969
_cell_measurement_theta_min 1.75
_cell_measurement_theta_max 26.37
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.419
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 728
_exptl_absorpt_coefficient_mu 0.106
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9589
_exptl_absorpt_correction_T_max 0.9791
_exptl_absorpt_process_details 'Apex2 (Bruker)'
_exptl_crystal_density_meas_temp ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Brucker kappa apex2 CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_reflns_number 15969
_diffrn_reflns_av_R_equivalents 0.0397
_diffrn_reflns_av_sigmaI/netI 0.0237
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.75
_diffrn_reflns_theta_max 26.37
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 1674
# number of observed reflections (> n sig(I))
_reflns_number_gt 1284
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker kappa Apex2'
_computing_cell_refinement Apex2
_computing_data_reduction SAINT32
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.0089P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1674
_refine_ls_number_parameters 118
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0441
_refine_ls_R_factor_gt 0.0302
_refine_ls_wR_factor_ref 0.0811
_refine_ls_wR_factor_gt 0.0770
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_restrained_S_all 1.043
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.188
_refine_diff_density_min -0.189
_refine_diff_density_rms 0.036
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88082(8) 0.69193(3) 0.11025(10) 0.0228(2) Uani 1 1 d . . .
O3 O 0.88966(8) 0.65262(3) 0.37333(11) 0.0255(2) Uani 1 1 d . . .
O2 O 1.02020(8) 0.61388(3) 0.14774(11) 0.0292(2) Uani 1 1 d . . .
C2 C 1.06787(12) 0.71871(5) -0.09038(16) 0.0221(3) Uani 1 1 d . . .
C4 C 0.93999(11) 0.64889(5) 0.20391(16) 0.0208(3) Uani 1 1 d . . .
C5 C 0.94546(12) 0.61266(4) 0.49920(15) 0.0212(3) Uani 1 1 d . . .
C1 C 1.18329(11) 0.73853(4) -0.09781(15) 0.0213(3) Uani 1 1 d . . .
C3 C 0.92624(12) 0.69491(5) -0.07667(15) 0.0235(3) Uani 1 1 d . . .
H3A H 0.8618 0.7189 -0.1446 0.028 Uiso 1 1 calc R . .
H3B H 0.9247 0.6566 -0.1290 0.028 Uiso 1 1 calc R . .
C9 C 1.13153(12) 0.58107(5) 0.68857(17) 0.0265(3) Uani 1 1 d . . .
H9 H 1.2233 0.5844 0.7298 0.032 Uiso 1 1 calc R . .
C6 C 0.85737(12) 0.57123(5) 0.56684(16) 0.0250(3) Uani 1 1 d . . .
H6 H 0.7655 0.5682 0.5260 0.030 Uiso 1 1 calc R . .
C10 C 1.08196(12) 0.61844(5) 0.55698(16) 0.0238(3) Uani 1 1 d . . .
H10 H 1.1397 0.6468 0.5088 0.029 Uiso 1 1 calc R . .
C7 C 0.90853(13) 0.53384(5) 0.69766(17) 0.0284(3) Uani 1 1 d . . .
H7 H 0.8507 0.5052 0.7445 0.034 Uiso 1 1 calc R . .
C8 C 1.04482(13) 0.53897(5) 0.75843(17) 0.0278(3) Uani 1 1 d . . .
H8 H 1.0783 0.5140 0.8467 0.033 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0211(4) 0.0252(4) 0.0222(5) 0.0026(3) 0.0007(3) 0.0026(3)
O3 0.0254(5) 0.0304(5) 0.0207(5) 0.0022(3) 0.0034(3) 0.0075(3)
O2 0.0319(5) 0.0308(5) 0.0250(5) -0.0003(4) 0.0042(4) 0.0110(4)
C2 0.0248(6) 0.0211(6) 0.0205(7) 0.0015(5) -0.0012(5) 0.0008(5)
C4 0.0175(6) 0.0223(6) 0.0225(7) -0.0010(5) -0.0006(5) -0.0015(5)
C5 0.0239(6) 0.0215(6) 0.0181(6) -0.0011(5) 0.0031(5) 0.0044(5)
C1 0.0239(6) 0.0199(6) 0.0203(6) -0.0001(5) -0.0008(5) 0.0015(5)
C3 0.0206(6) 0.0283(6) 0.0216(7) 0.0033(5) -0.0019(5) -0.0019(5)
C9 0.0222(6) 0.0274(6) 0.0300(7) -0.0020(5) -0.0016(5) 0.0019(5)
C6 0.0192(6) 0.0297(6) 0.0261(7) -0.0051(5) 0.0016(5) -0.0026(5)
C10 0.0229(6) 0.0204(6) 0.0281(7) 0.0011(5) 0.0045(5) -0.0017(5)
C7 0.0291(7) 0.0239(6) 0.0323(8) 0.0018(5) 0.0085(6) -0.0047(5)
C8 0.0330(7) 0.0255(6) 0.0249(7) 0.0031(5) 0.0030(5) 0.0052(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.3406(13) . ?
O1 C3 1.4522(13) . ?
O3 C4 1.3461(14) . ?
O3 C5 1.4185(13) . ?
O2 C4 1.1911(13) . ?
C2 C1 1.1944(15) . ?
C2 C3 1.4631(16) . ?
C5 C6 1.3717(16) . ?
C5 C10 1.3770(16) . ?
C1 C1 1.380(2) 2_765 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C8 1.3808(16) . ?
C9 C10 1.3877(16) . ?
C9 H9 0.9300 . ?
C6 C7 1.3890(16) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C7 C8 1.3808(18) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C3 113.77(9) . . ?
C4 O3 C5 115.89(8) . . ?
C1 C2 C3 178.59(13) . . ?
O2 C4 O1 126.73(11) . . ?
O2 C4 O3 126.76(11) . . ?
O1 C4 O3 106.51(9) . . ?
C6 C5 C10 122.28(11) . . ?
C6 C5 O3 117.93(10) . . ?
C10 C5 O3 119.68(10) . . ?
C2 C1 C1 177.36(8) . 2_765 ?
O1 C3 C2 111.08(9) . . ?
O1 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C8 C9 C10 120.09(11) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C6 C7 118.51(11) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C5 C10 C9 118.65(10) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C8 C7 C6 120.29(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.18(11) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
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
C3 O1 C4 O2 -1.81(15) . . . . ?
C3 O1 C4 O3 178.88(8) . . . . ?
C5 O3 C4 O2 4.20(16) . . . . ?
C5 O3 C4 O1 -176.49(8) . . . . ?
C4 O3 C5 C6 -112.89(11) . . . . ?
C4 O3 C5 C10 70.76(13) . . . . ?
C4 O1 C3 C2 -75.32(11) . . . . ?
C10 C5 C6 C7 -0.23(17) . . . . ?
O3 C5 C6 C7 -176.48(10) . . . . ?
C6 C5 C10 C9 -0.19(17) . . . . ?
O3 C5 C10 C9 176.00(10) . . . . ?
C8 C9 C10 C5 0.29(17) . . . . ?
C5 C6 C7 C8 0.55(18) . . . . ?
C10 C9 C8 C7 0.03(18) . . . . ?
C6 C7 C8 C9 -0.46(19) . . . . ?
#===END
_database_code_depnum_ccdc_archive 'CCDC 759062'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_global
#TrackingRef '246trifphenol_5.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jan 29 15:14:15 2013'
_audit_creation_method 'PLATON option'
_audit_update_record
;
;
#===============================================================================
data_aveb246tfp150k
#TrackingRef '246trifphenol_5.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
'hexa-2,4-diyne-1,6-diyl bis(2,4,6-trifluorophenylcarbonate)'
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H8 F6 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C20 H8 F6 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 458.26
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a 5.2422(3)
_cell_length_b 7.1560(4)
_cell_length_c 13.2155(7)
_cell_angle_alpha 93.426(4)
_cell_angle_beta 98.645(4)
_cell_angle_gamma 109.868(5)
_cell_volume 457.66(5)
_cell_formula_units_Z 1
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 9493
_cell_measurement_theta_min 3.0
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.663
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 230
_exptl_absorpt_coefficient_mu 0.161
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.9532
_exptl_absorpt_correction_T_max 0.9684
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 9493
_diffrn_reflns_av_R_equivalents 0.0276
_diffrn_reflns_av_sigmaI/netI 0.0157
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 3.05
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 1614
# number of observed reflections (> n sig(I))
_reflns_number_gt 1454
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.1619P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1614
_refine_ls_number_parameters 145
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0317
_refine_ls_R_factor_gt 0.0285
_refine_ls_wR_factor_ref 0.0747
_refine_ls_wR_factor_gt 0.0729
_refine_ls_goodness_of_fit_ref 1.028
_refine_ls_restrained_S_all 1.028
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.191
_refine_diff_density_min -0.201
_refine_diff_density_rms 0.034
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49204(18) 0.59217(14) 0.14538(7) 0.0252(2) Uani 1 1 d . . .
O3 O 0.37861(19) 0.39009(15) 0.25854(7) 0.0289(2) Uani 1 1 d . . .
F1 F 0.06428(18) 0.50106(12) 0.38261(7) 0.0370(2) Uani 1 1 d . . .
F3 F 0.29178(18) -0.00496(13) 0.22302(6) 0.0371(2) Uani 1 1 d . . .
F2 F -0.39410(18) -0.16715(13) 0.42595(7) 0.0442(3) Uani 1 1 d . . .
C5 C 0.1792(3) 0.2505(2) 0.30071(10) 0.0235(3) Uani 1 1 d . . .
C2 C 0.6736(3) 0.8264(2) 0.03497(10) 0.0252(3) Uani 1 1 d . . .
C4 C 0.2766(3) 0.47261(19) 0.17963(10) 0.0219(3) Uani 1 1 d . . .
O2 O 0.03961(19) 0.44189(15) 0.14882(8) 0.0322(3) Uani 1 1 d . . .
C6 C 0.0229(3) 0.30538(19) 0.36375(10) 0.0252(3) Uani 1 1 d . . .
C7 C -0.1702(3) 0.1685(2) 0.40723(11) 0.0277(3) Uani 1 1 d . . .
H7 H -0.2741 0.2076 0.4496 0.033 Uiso 1 1 calc R . .
C1 C 0.8798(3) 0.9361(2) 0.01254(10) 0.0253(3) Uani 1 1 d . . .
C10 C 0.1378(3) 0.0497(2) 0.28325(10) 0.0256(3) Uani 1 1 d . . .
C9 C -0.0521(3) -0.0941(2) 0.32436(11) 0.0286(3) Uani 1 1 d . . .
H9 H -0.0777 -0.2291 0.3117 0.034 Uiso 1 1 calc R . .
C8 C -0.2025(3) -0.0287(2) 0.38515(11) 0.0286(3) Uani 1 1 d . . .
C3 C 0.4172(3) 0.6943(2) 0.06037(10) 0.0241(3) Uani 1 1 d . . .
H3A H 0.3081 0.7711 0.0803 0.029 Uiso 1 1 calc R . .
H3B H 0.3097 0.5980 0.0013 0.029 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0222(5) 0.0275(5) 0.0253(5) 0.0096(4) 0.0049(4) 0.0067(4)
O3 0.0222(5) 0.0339(5) 0.0296(5) 0.0146(4) 0.0046(4) 0.0071(4)
F1 0.0459(5) 0.0214(4) 0.0445(5) 0.0025(4) 0.0112(4) 0.0120(4)
F3 0.0400(5) 0.0456(5) 0.0318(5) -0.0016(4) 0.0077(4) 0.0232(4)
F2 0.0363(5) 0.0366(5) 0.0527(6) 0.0175(4) 0.0144(4) -0.0009(4)
C5 0.0206(7) 0.0259(7) 0.0219(7) 0.0080(5) 0.0020(5) 0.0055(5)
C2 0.0301(7) 0.0248(7) 0.0233(7) 0.0065(5) 0.0069(6) 0.0116(6)
C4 0.0235(7) 0.0215(6) 0.0211(7) 0.0035(5) 0.0053(5) 0.0077(5)
O2 0.0218(5) 0.0421(6) 0.0326(6) 0.0150(5) 0.0055(4) 0.0092(4)
C6 0.0287(7) 0.0198(7) 0.0259(7) 0.0027(5) 0.0011(6) 0.0085(6)
C7 0.0263(7) 0.0319(8) 0.0254(7) 0.0042(6) 0.0069(6) 0.0098(6)
C1 0.0287(7) 0.0258(7) 0.0241(7) 0.0077(6) 0.0057(6) 0.0119(6)
C10 0.0280(7) 0.0317(7) 0.0192(7) 0.0014(6) 0.0007(5) 0.0150(6)
C9 0.0321(8) 0.0210(7) 0.0286(7) 0.0026(6) -0.0035(6) 0.0080(6)
C8 0.0240(7) 0.0272(7) 0.0286(7) 0.0099(6) 0.0024(6) 0.0013(6)
C3 0.0249(7) 0.0269(7) 0.0240(7) 0.0077(5) 0.0073(5) 0.0114(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.3249(16) . ?
O1 C3 1.4529(16) . ?
O3 C4 1.3573(16) . ?
O3 C5 1.3902(15) . ?
F1 C6 1.3437(15) . ?
F3 C10 1.3446(16) . ?
F2 C8 1.3534(16) . ?
C5 C10 1.3784(19) . ?
C5 C6 1.380(2) . ?
C2 C1 1.1917(19) . ?
C2 C3 1.4573(18) . ?
C4 O2 1.1872(16) . ?
C6 C7 1.3720(19) . ?
C7 C8 1.371(2) . ?
C7 H7 0.9300 . ?
C1 C1 1.383(3) 2_775 ?
C10 C9 1.371(2) . ?
C9 C8 1.372(2) . ?
C9 H9 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C3 113.43(10) . . ?
C4 O3 C5 114.57(10) . . ?
C10 C5 C6 117.37(12) . . ?
C10 C5 O3 120.25(12) . . ?
C6 C5 O3 122.35(12) . . ?
C1 C2 C3 178.46(14) . . ?
O2 C4 O1 127.69(12) . . ?
O2 C4 O3 125.76(12) . . ?
O1 C4 O3 106.55(10) . . ?
F1 C6 C7 119.52(12) . . ?
F1 C6 C5 117.92(12) . . ?
C7 C6 C5 122.56(13) . . ?
C8 C7 C6 116.71(13) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C2 C1 C1 179.48(19) . 2_775 ?
F3 C10 C9 119.42(13) . . ?
F3 C10 C5 117.80(12) . . ?
C9 C10 C5 122.79(13) . . ?
C10 C9 C8 116.58(13) . . ?
C10 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
F2 C8 C7 117.94(13) . . ?
F2 C8 C9 118.07(13) . . ?
C7 C8 C9 123.99(13) . . ?
O1 C3 C2 106.96(10) . . ?
O1 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
O1 C3 H3B 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O3 C5 C10 107.91(14) . . . . ?
C4 O3 C5 C6 -74.40(16) . . . . ?
C3 O1 C4 O2 0.24(19) . . . . ?
C3 O1 C4 O3 -179.55(10) . . . . ?
C5 O3 C4 O2 3.55(19) . . . . ?
C5 O3 C4 O1 -176.65(10) . . . . ?
C10 C5 C6 F1 179.02(11) . . . . ?
O3 C5 C6 F1 1.26(19) . . . . ?
C10 C5 C6 C7 -0.9(2) . . . . ?
O3 C5 C6 C7 -178.64(12) . . . . ?
F1 C6 C7 C8 -179.92(12) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C5 C10 F3 -179.14(11) . . . . ?
O3 C5 C10 F3 -1.33(18) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
O3 C5 C10 C9 178.77(11) . . . . ?
F3 C10 C9 C8 179.97(11) . . . . ?
C5 C10 C9 C8 -0.1(2) . . . . ?
C6 C7 C8 F2 -179.16(12) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C10 C9 C8 F2 179.23(12) . . . . ?
C10 C9 C8 C7 -0.9(2) . . . . ?
C4 O1 C3 C2 177.20(10) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 922272'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_global
#TrackingRef '246trifphenol_5.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jan 29 15:14:15 2013'
_audit_creation_method 'PLATON option'
_audit_update_record
;
;
#===END
# Attachment 'mfphenol_3.cif'
# CIF-file generated for avebmfp_150 in P2(1)/n
#==============================================================================
data_avebmfp_150
#TrackingRef 'mfphenol_3.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
'hexa-2,4-diyne-1,6-diyl bis(3-fluorophenylcarbonate)'
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H12 F2 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C20 H12 F2 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 386.30
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
_cell_length_a 20.8305(12)
_cell_length_b 3.9051(3)
_cell_length_c 22.4954(12)
_cell_angle_alpha 90
_cell_angle_beta 110.433(7)
_cell_angle_gamma 90
_cell_volume 1714.8(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 18137
_cell_measurement_theta_min 2.7
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.10
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.496
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 792
_exptl_absorpt_coefficient_mu 0.125
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.9517
_exptl_absorpt_correction_T_max 0.9876
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 18137
_diffrn_reflns_av_R_equivalents 0.0427
_diffrn_reflns_av_sigmaI/netI 0.0270
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_k_min -4
_diffrn_reflns_limit_k_max 4
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 2.72
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 3031
# number of observed reflections (> n sig(I))
_reflns_number_gt 2552
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.3818P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3031
_refine_ls_number_parameters 253
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0448
_refine_ls_R_factor_gt 0.0364
_refine_ls_wR_factor_ref 0.1032
_refine_ls_wR_factor_gt 0.0970
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_restrained_S_all 1.053
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.167
_refine_diff_density_min -0.225
_refine_diff_density_rms 0.043
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O 0.85464(5) 0.9941(3) 1.18908(5) 0.0262(3) Uani 1 1 d . . .
O1 O 0.88027(6) 0.7534(3) 0.84995(5) 0.0287(3) Uani 1 1 d . . .
O3' O 0.75005(5) 0.9075(3) 1.17781(5) 0.0290(3) Uani 1 1 d . . .
F1 F 0.89910(6) 1.0826(3) 0.57163(5) 0.0451(3) Uani 1 1 d . . .
O2 O 0.92900(6) 0.5334(4) 0.78336(5) 0.0377(3) Uani 1 1 d . . .
F1' F 0.53525(5) 1.1293(3) 1.19380(5) 0.0487(3) Uani 1 1 d . . .
C1 C 0.91878(8) 0.7912(4) 1.00880(7) 0.0253(4) Uani 1 1 d . . .
C2 C 0.92291(8) 0.6892(4) 0.96015(7) 0.0255(4) Uani 1 1 d . . .
O2' O 0.77396(6) 1.2548(3) 1.10708(5) 0.0333(3) Uani 1 1 d . . .
C4' C 0.79045(8) 1.0734(4) 1.15222(7) 0.0244(4) Uani 1 1 d . . .
O3 O 0.83472(6) 0.8721(3) 0.75141(5) 0.0341(3) Uani 1 1 d . . .
C4 C 0.88617(8) 0.6995(4) 0.79335(7) 0.0238(4) Uani 1 1 d . . .
C1' C 0.91473(8) 0.9124(4) 1.06484(7) 0.0252(4) Uani 1 1 d . . .
C2' C 0.91204(8) 1.0240(4) 1.11329(7) 0.0256(4) Uani 1 1 d . . .
C3 C 0.92891(9) 0.5665(4) 0.90133(7) 0.0280(4) Uani 1 1 d . . .
H3A H 0.9750 0.6042 0.9016 0.034 Uiso 1 1 calc R . .
H3B H 0.9192 0.3231 0.8965 0.034 Uiso 1 1 calc R . .
C6 C 0.87152(8) 0.9727(4) 0.66206(7) 0.0277(4) Uani 1 1 d . . .
H6 H 0.9123 1.0725 0.6879 0.033 Uiso 1 1 calc R . .
C10' C 0.64720(9) 0.8051(5) 1.08636(7) 0.0294(4) Uani 1 1 d . . .
H10' H 0.6730 0.7308 1.0624 0.035 Uiso 1 1 calc R . .
C3' C 0.90770(8) 1.1610(4) 1.17215(7) 0.0271(4) Uani 1 1 d . . .
H3'1 H 0.9514 1.1300 1.2061 0.032 Uiso 1 1 calc R . .
H3'2 H 0.8983 1.4047 1.1673 0.032 Uiso 1 1 calc R . .
C5 C 0.82482(8) 0.8396(4) 0.68642(7) 0.0266(4) Uani 1 1 d . . .
C6' C 0.64233(8) 1.0373(4) 1.18430(7) 0.0269(4) Uani 1 1 d . . .
H6' H 0.6644 1.1190 1.2252 0.032 Uiso 1 1 calc R . .
C5' C 0.67828(8) 0.9249(4) 1.14732(7) 0.0252(4) Uani 1 1 d . . .
C8' C 0.53804(9) 0.9065(5) 1.09764(8) 0.0312(4) Uani 1 1 d . . .
H8' H 0.4904 0.8996 1.0812 0.037 Uiso 1 1 calc R . .
C7' C 0.57228(9) 1.0236(5) 1.15806(8) 0.0303(4) Uani 1 1 d . . .
C7 C 0.85459(9) 0.9501(5) 0.59735(8) 0.0298(4) Uani 1 1 d . . .
C10 C 0.76422(9) 0.6941(5) 0.64902(8) 0.0344(4) Uani 1 1 d . . .
H10 H 0.7334 0.6075 0.6668 0.041 Uiso 1 1 calc R . .
C9' C 0.57654(9) 0.7992(5) 1.06199(8) 0.0319(4) Uani 1 1 d . . .
H9' H 0.5544 0.7216 1.0208 0.038 Uiso 1 1 calc R . .
C8 C 0.79528(9) 0.8076(5) 0.55772(8) 0.0359(4) Uani 1 1 d . . .
H8 H 0.7858 0.7976 0.5142 0.043 Uiso 1 1 calc R . .
C9 C 0.74993(9) 0.6791(5) 0.58427(9) 0.0405(5) Uani 1 1 d . . .
H9 H 0.7091 0.5809 0.5583 0.049 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1' 0.0229(6) 0.0351(7) 0.0204(5) 0.0032(5) 0.0074(5) 0.0019(5)
O1 0.0314(6) 0.0351(7) 0.0205(6) 0.0021(5) 0.0102(5) 0.0084(5)
O3' 0.0220(6) 0.0428(8) 0.0210(6) 0.0062(5) 0.0060(5) 0.0022(5)
F1 0.0442(6) 0.0618(8) 0.0361(6) 0.0077(5) 0.0225(5) -0.0029(6)
O2 0.0365(7) 0.0507(9) 0.0250(6) -0.0019(6) 0.0097(5) 0.0152(6)
F1' 0.0342(6) 0.0801(9) 0.0367(6) -0.0058(6) 0.0185(5) 0.0076(6)
C1 0.0235(8) 0.0277(9) 0.0233(8) 0.0039(7) 0.0066(6) 0.0028(7)
C2 0.0266(8) 0.0247(9) 0.0247(8) 0.0021(7) 0.0085(7) 0.0005(7)
O2' 0.0348(6) 0.0358(7) 0.0280(6) 0.0106(6) 0.0091(5) 0.0073(6)
C4' 0.0262(8) 0.0257(9) 0.0208(8) -0.0022(7) 0.0074(7) 0.0033(7)
O3 0.0331(6) 0.0482(8) 0.0218(6) 0.0053(5) 0.0106(5) 0.0130(6)
C4 0.0243(8) 0.0249(9) 0.0223(8) -0.0015(7) 0.0084(6) -0.0029(7)
C1' 0.0251(8) 0.0264(9) 0.0240(8) 0.0034(7) 0.0084(7) 0.0021(7)
C2' 0.0248(8) 0.0266(9) 0.0253(8) 0.0039(7) 0.0085(7) 0.0020(7)
C3 0.0340(9) 0.0268(9) 0.0226(8) 0.0015(7) 0.0089(7) 0.0059(8)
C6 0.0237(8) 0.0319(10) 0.0252(8) -0.0009(7) 0.0058(7) 0.0002(7)
C10' 0.0320(9) 0.0321(10) 0.0235(8) -0.0015(7) 0.0090(7) 0.0056(8)
C3' 0.0280(8) 0.0295(10) 0.0252(8) -0.0020(7) 0.0111(7) -0.0031(7)
C5 0.0281(8) 0.0298(9) 0.0211(8) 0.0015(7) 0.0077(7) 0.0043(7)
C6' 0.0284(9) 0.0319(10) 0.0191(8) -0.0019(7) 0.0066(7) -0.0002(7)
C5' 0.0230(8) 0.0286(9) 0.0219(8) 0.0038(7) 0.0054(6) 0.0021(7)
C8' 0.0255(8) 0.0340(10) 0.0304(9) 0.0040(8) 0.0050(7) -0.0003(8)
C7' 0.0304(9) 0.0363(10) 0.0280(9) 0.0024(7) 0.0149(7) 0.0041(8)
C7 0.0309(9) 0.0341(10) 0.0269(8) 0.0044(7) 0.0131(7) 0.0027(8)
C10 0.0270(9) 0.0362(11) 0.0396(10) 0.0053(8) 0.0109(8) -0.0014(8)
C9' 0.0337(9) 0.0327(10) 0.0231(8) -0.0025(7) 0.0021(7) 0.0009(8)
C8 0.0404(10) 0.0382(11) 0.0231(8) -0.0008(8) 0.0037(7) 0.0020(9)
C9 0.0332(10) 0.0397(12) 0.0385(10) -0.0038(9) -0.0001(8) -0.0064(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' C4' 1.3406(19) . ?
O1' C3' 1.4441(19) . ?
O1 C4 1.3376(18) . ?
O1 C3 1.4414(19) . ?
O3' C4' 1.341(2) . ?
O3' C5' 1.4120(19) . ?
F1 C7 1.3552(19) . ?
O2 C4 1.1862(19) . ?
F1' C7' 1.3583(19) . ?
C1 C2 1.196(2) . ?
C1 C1' 1.376(2) . ?
C2 C3 1.453(2) . ?
O2' C4' 1.1861(19) . ?
O3 C4 1.337(2) . ?
O3 C5 1.4091(18) . ?
C1' C2' 1.193(2) . ?
C2' C3' 1.460(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C5 1.374(2) . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C10' C5' 1.378(2) . ?
C10' C9' 1.380(2) . ?
C10' H10' 0.9300 . ?
C3' H3'1 0.9700 . ?
C3' H3'2 0.9700 . ?
C5 C10 1.372(2) . ?
C6' C7' 1.371(2) . ?
C6' C5' 1.371(2) . ?
C6' H6' 0.9300 . ?
C8' C7' 1.374(2) . ?
C8' C9' 1.382(2) . ?
C8' H8' 0.9300 . ?
C7 C8 1.364(3) . ?
C10 C9 1.382(2) . ?
C10 H10 0.9300 . ?
C9' H9' 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4' O1' C3' 115.00(12) . . ?
C4 O1 C3 114.29(12) . . ?
C4' O3' C5' 119.02(12) . . ?
C2 C1 C1' 179.13(19) . . ?
C1 C2 C3 179.23(17) . . ?
O2' C4' O1' 126.56(15) . . ?
O2' C4' O3' 128.20(15) . . ?
O1' C4' O3' 105.24(13) . . ?
C4 O3 C5 118.53(12) . . ?
O2 C4 O3 127.78(14) . . ?
O2 C4 O1 126.25(15) . . ?
O3 C4 O1 105.97(13) . . ?
C2' C1' C1 178.49(19) . . ?
C1' C2' C3' 179.20(17) . . ?
O1 C3 C2 107.68(13) . . ?
O1 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
O1 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 C6 C7 116.23(15) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
C5' C10' C9' 117.80(15) . . ?
C5' C10' H10' 121.1 . . ?
C9' C10' H10' 121.1 . . ?
O1' C3' C2' 111.68(13) . . ?
O1' C3' H3'1 109.3 . . ?
C2' C3' H3'1 109.3 . . ?
O1' C3' H3'2 109.3 . . ?
C2' C3' H3'2 109.3 . . ?
H3'1 C3' H3'2 107.9 . . ?
C10 C5 C6 122.67(15) . . ?
C10 C5 O3 116.33(15) . . ?
C6 C5 O3 120.80(14) . . ?
C7' C6' C5' 116.81(15) . . ?
C7' C6' H6' 121.6 . . ?
C5' C6' H6' 121.6 . . ?
C6' C5' C10' 123.10(15) . . ?
C6' C5' O3' 115.50(13) . . ?
C10' C5' O3' 121.13(14) . . ?
C7' C8' C9' 117.96(15) . . ?
C7' C8' H8' 121.0 . . ?
C9' C8' H8' 121.0 . . ?
F1' C7' C6' 118.20(15) . . ?
F1' C7' C8' 118.73(15) . . ?
C6' C7' C8' 123.07(15) . . ?
F1 C7 C8 118.37(15) . . ?
F1 C7 C6 117.81(15) . . ?
C8 C7 C6 123.82(16) . . ?
C5 C10 C9 118.50(16) . . ?
C5 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10' C9' C8' 121.25(16) . . ?
C10' C9' H9' 119.4 . . ?
C8' C9' H9' 119.4 . . ?
C7 C8 C9 117.86(16) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C8 C9 C10 120.92(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3' O1' C4' O2' 2.5(2) . . . . ?
C3' O1' C4' O3' -176.93(12) . . . . ?
C5' O3' C4' O2' 4.0(3) . . . . ?
C5' O3' C4' O1' -176.57(13) . . . . ?
C5 O3 C4 O2 5.5(3) . . . . ?
C5 O3 C4 O1 -175.01(13) . . . . ?
C3 O1 C4 O2 -4.6(2) . . . . ?
C3 O1 C4 O3 175.84(13) . . . . ?
C4 O1 C3 C2 171.67(14) . . . . ?
C4' O1' C3' C2' -71.41(18) . . . . ?
C7 C6 C5 C10 -0.6(3) . . . . ?
C7 C6 C5 O3 -175.26(15) . . . . ?
C4 O3 C5 C10 116.51(18) . . . . ?
C4 O3 C5 C6 -68.5(2) . . . . ?
C7' C6' C5' C10' 0.6(3) . . . . ?
C7' C6' C5' O3' -173.50(15) . . . . ?
C9' C10' C5' C6' -0.1(3) . . . . ?
C9' C10' C5' O3' 173.69(15) . . . . ?
C4' O3' C5' C6' -125.15(16) . . . . ?
C4' O3' C5' C10' 60.7(2) . . . . ?
C5' C6' C7' F1' 179.21(15) . . . . ?
C5' C6' C7' C8' -0.4(3) . . . . ?
C9' C8' C7' F1' -179.86(16) . . . . ?
C9' C8' C7' C6' -0.2(3) . . . . ?
C5 C6 C7 F1 179.21(15) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
O3 C5 C10 C9 175.39(16) . . . . ?
C5' C10' C9' C8' -0.6(3) . . . . ?
C7' C8' C9' C10' 0.8(3) . . . . ?
F1 C7 C8 C9 -178.90(17) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C5 C10 C9 C8 -0.1(3) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 922273'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_global
#TrackingRef '246trifphenol_5.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jan 29 15:14:15 2013'
_audit_creation_method 'PLATON option'
_audit_update_record
;
;
#===END
# Attachment 'ofphenol_2.cif'
# CIF-file generated for avebofp150k in Pccn
#==============================================================================
data_avebofp150k
#TrackingRef 'ofphenol_2.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
'hexa-2,4-diyne-1,6-diyl bis(2-fluorophenylcarbonate)'
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H12 F2 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C20 H12 F2 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 386.30
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall '-P 2ab 2ac'
_symmetry_space_group_name_H-M 'P c c n'
_symmetry_Int_Tables_number 56
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,z
3 1/2+x,-y,1/2-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,-z
7 1/2-x,y,1/2+z
8 x,1/2-y,1/2+z
_cell_length_a 22.665(5)
_cell_length_b 9.956(5)
_cell_length_c 7.442(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1679.3(15)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 9474
_cell_measurement_theta_min 3.4
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.528
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 792
_exptl_absorpt_coefficient_mu 0.128
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.9507
_exptl_absorpt_correction_T_max 0.9749
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 9474
_diffrn_reflns_av_R_equivalents 0.0489
_diffrn_reflns_av_sigmaI/netI 0.0337
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.39
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 1480
# number of observed reflections (> n sig(I))
_reflns_number_gt 1172
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.0496P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1480
_refine_ls_number_parameters 127
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0503
_refine_ls_R_factor_gt 0.0367
_refine_ls_wR_factor_ref 0.1004
_refine_ls_wR_factor_gt 0.0919
_refine_ls_goodness_of_fit_ref 1.061
_refine_ls_restrained_S_all 1.061
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.188
_refine_diff_density_min -0.189
_refine_diff_density_rms 0.043
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.19458(8) -0.06065(18) 1.0815(2) 0.0279(4) Uani 1 1 d . . .
H3A H 0.2191 -0.1226 1.1490 0.034 Uiso 1 1 calc R . .
H3B H 0.1552 -0.0627 1.1328 0.034 Uiso 1 1 calc R . .
F1 F 0.07030(5) -0.25122(10) 0.48232(14) 0.0368(3) Uani 1 1 d . . .
C8 C 0.03694(8) 0.05715(19) 0.2482(2) 0.0285(4) Uani 1 1 d . . .
H8 H 0.0113 0.0896 0.1608 0.034 Uiso 1 1 calc R . .
C7 C 0.03360(8) -0.07560(19) 0.3015(2) 0.0278(4) Uani 1 1 d . . .
H7 H 0.0058 -0.1330 0.2512 0.033 Uiso 1 1 calc R . .
O1 O 0.19194(5) -0.10340(12) 0.89478(15) 0.0262(3) Uani 1 1 d . . .
O2 O 0.11437(5) 0.03550(13) 0.85426(16) 0.0298(4) Uani 1 1 d . . .
O3 O 0.15287(5) -0.09285(12) 0.63193(15) 0.0281(3) Uani 1 1 d . . .
C5 C 0.11319(7) -0.03724(17) 0.5074(2) 0.0227(4) Uani 1 1 d . . .
C9 C 0.07822(8) 0.14162(18) 0.3241(2) 0.0288(4) Uani 1 1 d . . .
H9 H 0.0803 0.2308 0.2875 0.035 Uiso 1 1 calc R . .
C6 C 0.07216(7) -0.12110(17) 0.4301(2) 0.0237(4) Uani 1 1 d . . .
C2 C 0.21868(7) 0.07495(19) 1.0970(2) 0.0266(4) Uani 1 1 d . . .
C4 C 0.14910(8) -0.04436(17) 0.8013(2) 0.0234(4) Uani 1 1 d . . .
C10 C 0.11652(7) 0.09434(18) 0.4545(2) 0.0273(4) Uani 1 1 d . . .
H10 H 0.1443 0.1515 0.5058 0.033 Uiso 1 1 calc R . .
C1 C 0.23840(8) 0.18588(18) 1.1051(2) 0.0261(4) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3 0.0322(11) 0.0271(10) 0.0244(9) 0.0025(8) -0.0027(8) -0.0016(8)
F1 0.0459(7) 0.0199(6) 0.0445(7) 0.0034(5) -0.0023(5) -0.0047(4)
C8 0.0270(10) 0.0325(11) 0.0259(10) 0.0004(8) -0.0019(7) 0.0050(8)
C7 0.0254(10) 0.0306(11) 0.0274(10) -0.0058(9) -0.0012(8) -0.0032(8)
O1 0.0268(7) 0.0276(7) 0.0241(6) -0.0001(6) -0.0030(5) 0.0034(5)
O2 0.0328(8) 0.0282(7) 0.0285(7) -0.0022(6) -0.0003(5) 0.0089(6)
O3 0.0315(7) 0.0283(7) 0.0246(6) -0.0034(5) -0.0044(5) 0.0072(6)
C5 0.0236(10) 0.0240(10) 0.0205(9) -0.0020(8) 0.0002(7) 0.0034(7)
C9 0.0313(11) 0.0207(10) 0.0344(10) 0.0031(8) 0.0017(8) 0.0011(8)
C6 0.0261(10) 0.0193(9) 0.0258(9) -0.0006(8) 0.0048(7) -0.0010(7)
C2 0.0232(10) 0.0339(11) 0.0228(9) 0.0016(8) -0.0023(7) 0.0016(8)
C4 0.0242(10) 0.0203(9) 0.0259(9) 0.0017(8) -0.0004(7) -0.0036(7)
C10 0.0261(10) 0.0256(10) 0.0303(10) -0.0043(8) -0.0014(7) -0.0036(8)
C1 0.0226(9) 0.0301(11) 0.0256(9) 0.0013(8) 0.0004(7) 0.0004(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 O1 1.454(2) . ?
C3 C2 1.461(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
F1 C6 1.353(2) . ?
C8 C9 1.379(3) . ?
C8 C7 1.382(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.373(2) . ?
C7 H7 0.9300 . ?
O1 C4 1.331(2) . ?
O2 C4 1.186(2) . ?
O3 C4 1.352(2) . ?
O3 C5 1.405(2) . ?
C5 C10 1.370(3) . ?
C5 C6 1.376(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C2 C1 1.193(3) . ?
C10 H10 0.9300 . ?
C1 C1 1.381(4) 2 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C3 C2 111.19(14) . . ?
O1 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C9 C8 C7 120.19(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 118.74(17) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C4 O1 C3 113.58(13) . . ?
C4 O3 C5 115.70(13) . . ?
C10 C5 C6 119.83(16) . . ?
C10 C5 O3 122.08(15) . . ?
C6 C5 O3 117.98(15) . . ?
C8 C9 C10 120.34(17) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
F1 C6 C7 119.75(15) . . ?
F1 C6 C5 118.82(15) . . ?
C7 C6 C5 121.43(17) . . ?
C1 C2 C3 178.35(19) . . ?
O2 C4 O1 127.32(16) . . ?
O2 C4 O3 126.23(16) . . ?
O1 C4 O3 106.46(14) . . ?
C5 C10 C9 119.47(16) . . ?
C5 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C2 C1 C1 177.09(13) . 2 ?
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
C9 C8 C7 C6 -0.3(3) . . . . ?
C2 C3 O1 C4 -73.79(18) . . . . ?
C4 O3 C5 C10 66.8(2) . . . . ?
C4 O3 C5 C6 -116.90(17) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C7 C6 F1 -178.96(15) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C10 C5 C6 F1 178.94(14) . . . . ?
O3 C5 C6 F1 2.6(2) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
O3 C5 C6 C7 -177.12(14) . . . . ?
C3 O1 C4 O2 -0.5(2) . . . . ?
C3 O1 C4 O3 179.27(13) . . . . ?
C5 O3 C4 O2 3.1(2) . . . . ?
C5 O3 C4 O1 -176.59(13) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
O3 C5 C10 C9 176.51(14) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 922274'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_global
#TrackingRef '246trifphenol_5.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jan 29 15:14:15 2013'
_audit_creation_method 'PLATON option'
_audit_update_record
;
;
#===END
# Attachment 'pfphenol_4.cif'
# CIF-file generated for vebpf_k150 in Pccn
#==============================================================================
#===============================================================================
data_vebpf_k150
#TrackingRef 'pfphenol_4.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
hexa-2,4-diyne-1,6-diyl bis(4-fluorophenylcarbonate)'
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H12 F2 O6'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C20 H12 F2 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 386.30
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall '-P 2ab 2ac'
_symmetry_space_group_name_H-M 'P c c n'
_symmetry_Int_Tables_number 56
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,z
3 1/2+x,-y,1/2-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,-z
7 1/2-x,y,1/2+z
8 x,1/2-y,1/2+z
_cell_length_a 9.6359(9)
_cell_length_b 23.748(2)
_cell_length_c 7.2680(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1663.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 6892
_cell_measurement_theta_min 1.7
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.543
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 792
_exptl_absorpt_coefficient_mu 0.129
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.9503
_exptl_absorpt_correction_T_max 0.9747
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 6892
_diffrn_reflns_av_R_equivalents 0.0335
_diffrn_reflns_av_sigmaI/netI 0.0263
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 1.72
_diffrn_reflns_theta_max 24.99
_diffrn_reflns_theta_full 24.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 1478
# number of observed reflections (> n sig(I))
_reflns_number_gt 1160
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1478
_refine_ls_number_parameters 127
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0508
_refine_ls_R_factor_gt 0.0371
_refine_ls_wR_factor_ref 0.1092
_refine_ls_wR_factor_gt 0.1015
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.238
_refine_diff_density_min -0.210
_refine_diff_density_rms 0.046
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.60855(13) 0.34810(5) 0.14882(17) 0.0263(3) Uani 1 1 d . . .
O1 O 0.61914(13) 0.30738(5) 0.41334(16) 0.0244(3) Uani 1 1 d . . .
O2 O 0.47445(14) 0.38168(6) 0.38138(17) 0.0317(4) Uani 1 1 d . . .
C1 C 0.31644(19) 0.26070(7) 0.6217(2) 0.0219(4) Uani 1 1 d . . .
C10 C 0.63387(18) 0.42558(8) -0.0563(2) 0.0218(4) Uani 1 1 d . . .
H10 H 0.7265 0.4282 -0.0214 0.026 Uiso 1 1 calc R . .
C2 C 0.4316(2) 0.27933(7) 0.6155(2) 0.0224(4) Uani 1 1 d . . .
C4 C 0.55794(18) 0.34894(7) 0.3233(3) 0.0212(4) Uani 1 1 d . . .
C3 C 0.57304(19) 0.30222(8) 0.6037(2) 0.0242(4) Uani 1 1 d . . .
H3A H 0.5756 0.3390 0.6619 0.029 Uiso 1 1 calc R . .
H3B H 0.6362 0.2777 0.6699 0.029 Uiso 1 1 calc R . .
C7 C 0.35492(19) 0.41738(8) -0.1572(2) 0.0233(4) Uani 1 1 d . . .
H7 H 0.2618 0.4153 -0.1902 0.028 Uiso 1 1 calc R . .
C8 C 0.4417(2) 0.45612(8) -0.2370(2) 0.0250(5) Uani 1 1 d . . .
C9 C 0.5792(2) 0.46161(8) -0.1903(3) 0.0263(5) Uani 1 1 d . . .
H9 H 0.6347 0.4887 -0.2464 0.032 Uiso 1 1 calc R . .
C6 C 0.41040(19) 0.38142(8) -0.0254(3) 0.0256(4) Uani 1 1 d . . .
H6 H 0.3549 0.3542 0.0300 0.031 Uiso 1 1 calc R . .
C5 C 0.54811(19) 0.38638(8) 0.0225(2) 0.0223(4) Uani 1 1 d . . .
F1 F 0.38767(12) 0.49139(5) -0.36589(16) 0.0371(4) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0272(7) 0.0307(7) 0.0209(7) 0.0036(6) 0.0035(5) 0.0056(6)
O1 0.0221(7) 0.0308(8) 0.0202(7) 0.0010(6) 0.0018(5) 0.0004(5)
O2 0.0361(8) 0.0335(8) 0.0256(8) -0.0010(6) 0.0033(6) 0.0096(6)
C1 0.0256(10) 0.0216(9) 0.0186(9) 0.0001(8) -0.0006(7) 0.0016(8)
C10 0.0171(9) 0.0267(10) 0.0218(10) -0.0040(8) 0.0012(8) -0.0008(7)
C2 0.0281(10) 0.0219(9) 0.0174(9) 0.0020(8) -0.0014(8) 0.0009(8)
C4 0.0189(9) 0.0229(10) 0.0216(10) -0.0034(8) 0.0018(8) -0.0026(8)
C3 0.0233(10) 0.0303(10) 0.0191(10) 0.0024(8) -0.0011(8) -0.0026(8)
C7 0.0190(9) 0.0286(10) 0.0223(10) -0.0023(8) -0.0017(8) -0.0011(8)
C8 0.0306(11) 0.0263(10) 0.0182(9) 0.0005(8) 0.0002(8) 0.0058(8)
C9 0.0279(10) 0.0249(10) 0.0262(10) -0.0004(8) 0.0069(8) -0.0043(8)
C6 0.0272(10) 0.0251(10) 0.0244(10) 0.0001(8) 0.0055(8) -0.0042(8)
C5 0.0277(10) 0.0230(9) 0.0162(9) -0.0008(8) 0.0011(8) 0.0031(8)
F1 0.0341(7) 0.0416(7) 0.0354(7) 0.0138(6) 0.0002(5) 0.0059(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C4 1.359(2) . ?
O3 C5 1.417(2) . ?
O1 C4 1.323(2) . ?
O1 C3 1.458(2) . ?
O2 C4 1.196(2) . ?
C1 C2 1.196(3) . ?
C1 C1 1.378(4) 2 ?
C10 C5 1.370(3) . ?
C10 C9 1.399(3) . ?
C10 H10 0.9300 . ?
C2 C3 1.470(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 C8 1.372(3) . ?
C7 C6 1.390(3) . ?
C7 H7 0.9300 . ?
C8 F1 1.361(2) . ?
C8 C9 1.374(3) . ?
C9 H9 0.9300 . ?
C6 C5 1.377(3) . ?
C6 H6 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C5 116.61(14) . . ?
C4 O1 C3 113.34(14) . . ?
C2 C1 C1 177.83(12) . 2 ?
C5 C10 C9 118.63(17) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C1 C2 C3 178.83(18) . . ?
O2 C4 O1 127.63(17) . . ?
O2 C4 O3 125.48(17) . . ?
O1 C4 O3 106.90(15) . . ?
O1 C3 C2 111.64(14) . . ?
O1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C8 C7 C6 117.94(17) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
F1 C8 C7 118.05(17) . . ?
F1 C8 C9 118.76(17) . . ?
C7 C8 C9 123.18(18) . . ?
C8 C9 C10 118.49(17) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C5 C6 C7 119.49(17) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C10 C5 C6 122.27(17) . . ?
C10 C5 O3 117.29(16) . . ?
C6 C5 O3 120.33(16) . . ?
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
C3 O1 C4 O2 1.4(3) . . . . ?
C3 O1 C4 O3 -178.93(14) . . . . ?
C5 O3 C4 O2 -5.6(3) . . . . ?
C5 O3 C4 O1 174.78(14) . . . . ?
C4 O1 C3 C2 72.63(19) . . . . ?
C6 C7 C8 F1 -179.96(16) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
F1 C8 C9 C10 179.38(16) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C5 C10 C9 C8 0.0(3) . . . . ?
C8 C7 C6 C5 1.1(3) . . . . ?
C9 C10 C5 C6 -0.2(3) . . . . ?
C9 C10 C5 O3 175.98(16) . . . . ?
C7 C6 C5 C10 -0.4(3) . . . . ?
C7 C6 C5 O3 -176.45(15) . . . . ?
C4 O3 C5 C10 119.47(17) . . . . ?
C4 O3 C5 C6 -64.3(2) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 922275'