#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:21:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180431 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/00/7210011.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7210011
loop_
_publ_author_name
'Dikundwar, Amol G.'
'Venkateswarlu, Ch.'
'Chandrakala, R. N.'
'Chandrasekaran, Srinivasan'
'Row, Tayur N. Guru'
_publ_section_title
;
 H/F isosteric substitution to attest different equi-energetic molecular
 conformations in crystals
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              5403
_journal_paper_doi               10.1039/c3ce40697k
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C20 H12 F2 O6'
_chemical_formula_sum            'C20 H12 F2 O6'
_chemical_formula_weight         386.30
_chemical_name_systematic
;
hexa-2,4-diyne-1,6-diyl bis(3-fluorophenylcarbonate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 110.433(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8305(12)
_cell_length_b                   3.9051(3)
_cell_length_c                   22.4954(12)
_cell_measurement_reflns_used    18137
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     1714.8(2)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18137
_diffrn_reflns_reduction_process
;

;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.3818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2552
_reflns_number_total             3031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40697k.txt
_cod_data_source_block           avebmfp_150
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7210011
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
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
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
