#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:53:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/99/1549945.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_1549945
loop_
_publ_author_name
'Rozatian, Neshat'
'Ashworth, Ian W.'
'Sandford, Graham'
'Hodgson, David R. W.'
_publ_section_title
;
 A quantitative reactivity scale for electrophilic fluorinating reagents.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              8692
_journal_page_last               8702
_journal_paper_doi               10.1039/c8sc03596b
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H15 F O4'
_chemical_formula_sum            'C17 H15 F O4'
_chemical_formula_weight         302.29
_chemical_name_systematic
;
2-fluoro-1,3-bis(4-methoxyphenyl)-1,3-propanedione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.944(2)
_cell_length_b                   7.0229(5)
_cell_length_c                   6.1827(5)
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.55
_cell_volume                     1387.02(17)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         2.550
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1094 before and 0.0558 after correction. 
The Ratio of minimum to maximum transmission is 0.7836. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²+0.3700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1661
_reflns_number_total             1880
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL 17srv344 in Cmc21 #36
REM reset to Cmc21 #36
CELL 0.71073 31.9439 7.0229 6.1827 90 90 90
ZERR 4 0.0024 0.0005 0.0005 0 0 0
LATT -7
SYMM -X,-Y,0.5+Z
SYMM -X,+Y,+Z
SYMM +X,-Y,0.5+Z
SFAC C H F O
UNIT 68 60 4 16
EQIV $1 1-X,+Y,+Z

L.S. 9 0 0
PLAN  5
SIZE 0.18 0.27 0.41
TEMP -153.15
HTAB O1 O1_$1
CONF O1 C2 C1 F1
CONF C2_$1 C1 C2 O1
CONF C3 C2 C1 F1
CONF C2_$1 C1 C2 C3
CONF C4 C3 C2 O1
CONF C1 C2 C3 C4
CONF C8 C3 C2 O1
CONF C1 C2 C3 C8
CONF C5 C6 O2 C9
CONF C7 C6 O2 C9
BOND $h
fmap 2 53
acta 
OMIT -2 58
WGHT 0.063 0.37
FVAR 0.2116
REM <olex2.extras>
REM <HklSrc "%.\\17srv344.hkl">
REM </olex2.extras>

F1    3     0.50000  0.73492  0.71293  10.50000  0.01594  0.05112  0.01560 =
 0.00142  0.00000  0.00000 
O1    4     0.53862  0.72008  0.17543  11.00000  0.01372  0.03344  0.01404 =
 -0.00210  0.00050  0.00017 
PART -1
AFIX 3 0.95
H1    2     0.50903  0.71313  0.16206  10.50000 -1.20000 
AFIX 0
PART 0
O2    4     0.70076  0.74275  0.73897  11.00000  0.01043  0.02545  0.01996 =
 -0.00162 -0.00075  0.00134 
C1    1     0.50000  0.73735  0.49323  10.50000  0.01227  0.02078  0.01421 =
 0.00155  0.00000 -0.00000 
C2    1     0.53853  0.73229  0.38406  11.00000  0.01391  0.01433  0.01474 =
 0.00037 -0.00050 -0.00023 
C3    1     0.57973  0.73739  0.49172  11.00000  0.01109  0.01284  0.01638 =
 0.00124  0.00091 -0.00041 
C4    1     0.61396  0.66102  0.37760  11.00000  0.01553  0.01579  0.01402 =
 -0.00155  0.00256 -0.00037 
C5    1     0.65358  0.66351  0.46552  11.00000  0.01315  0.01621  0.01750 =
 -0.00103  0.00357  0.00099 
C6    1     0.66025  0.74794  0.66667  11.00000  0.01193  0.01331  0.01854 =
 0.00360  0.00069  0.00001 
C7    1     0.62707  0.82788  0.78113  11.00000  0.01255  0.01767  0.01401 =
 -0.00104  0.00162  0.00017 
C8    1     0.58691  0.81960  0.69341  11.00000  0.01219  0.01743  0.01622 =
 -0.00090  0.00399  0.00132 
C9    1     0.71002  0.83691  0.93739  11.00000  0.01369  0.04229  0.02456 =
 -0.00666 -0.00370  0.00122 
H4    2     0.61009  0.60299  0.23530  11.00000  0.01344 
H5    2     0.67692  0.60461  0.39627  11.00000  0.01847 
H7    2     0.63151  0.89232  0.91834  11.00000  0.01240 
H8    2     0.56580  0.87883  0.76945  11.00000  0.02513 
H9a   2     0.73864  0.82218  0.95664  11.00000  0.02881 
H9b   2     0.70379  0.96815  0.93162  11.00000  0.03107 
H9c   2     0.69556  0.77981  1.05740  11.00000  0.03089 
HKLF 4

END
;
_cod_data_source_file            c8sc03596b2.cif
_cod_data_source_block           2dE_17srv344
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549940--1549946.cif.
;
_cod_original_cell_volume        1387.02(18)
_cod_database_code               1549945
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.956
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Riding coordinates:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 0.7349(3) 0.7129(3) 0.0276(5) Uani 1 2 d S T P . .
O1 O 0.53862(4) 0.7201(2) 0.1754(3) 0.0204(4) Uani 1 1 d . . . . .
H1 H 0.509032 0.713124 0.162060 0.024 Uiso 0.5 1 d R . . A -1
O2 O 0.70077(5) 0.7427(2) 0.7390(3) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.500000 0.7373(4) 0.4932(5) 0.0158(6) Uani 1 2 d S T P . .
C2 C 0.53852(6) 0.7323(3) 0.3841(3) 0.0143(4) Uani 1 1 d . . . . .
C3 C 0.57973(6) 0.7374(3) 0.4917(4) 0.0134(4) Uani 1 1 d . . . . .
C4 C 0.61396(6) 0.6610(3) 0.3776(4) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.65358(6) 0.6635(3) 0.4655(4) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.66025(6) 0.7479(3) 0.6667(4) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.62707(6) 0.8279(3) 0.7811(4) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.58691(6) 0.8196(3) 0.6934(4) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.71002(7) 0.8369(4) 0.9374(4) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.6101(7) 0.603(3) 0.235(4) 0.013(6) Uiso 1 1 d . . . . .
H5 H 0.6769(7) 0.605(4) 0.396(5) 0.018(6) Uiso 1 1 d . . . . .
H7 H 0.6315(6) 0.892(3) 0.918(4) 0.012(6) Uiso 1 1 d . . . . .
H8 H 0.5658(8) 0.879(4) 0.769(5) 0.025(7) Uiso 1 1 d . . . . .
H9A H 0.7386(9) 0.822(4) 0.957(5) 0.029(8) Uiso 1 1 d . . . . .
H9B H 0.7038(7) 0.968(5) 0.932(5) 0.031(8) Uiso 1 1 d . . . . .
H9C H 0.6956(11) 0.780(4) 1.057(6) 0.031(8) Uiso 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
F1 0.0160(8) 0.0511(13) 0.0156(10) 0.0014(9) 0.000 0.000
O1 0.0137(7) 0.0335(8) 0.0141(8) -0.0021(8) 0.0005(6) 0.0002(6)
O2 0.0104(6) 0.0255(8) 0.0200(8) -0.0016(5) -0.0007(6) 0.0013(5)
C1 0.0123(12) 0.0208(15) 0.0142(15) 0.0016(11) 0.000 0.000
C2 0.0139(9) 0.0143(10) 0.0148(11) 0.0004(8) -0.0005(8) -0.0002(7)
C3 0.0111(9) 0.0128(9) 0.0164(11) 0.0012(8) 0.0009(7) -0.0004(7)
C4 0.0155(8) 0.0158(10) 0.0140(9) -0.0015(8) 0.0025(8) -0.0004(7)
C5 0.0132(8) 0.0162(9) 0.0175(10) -0.0010(8) 0.0036(8) 0.0010(7)
C6 0.0119(8) 0.0133(9) 0.0185(11) 0.0036(8) 0.0007(8) 0.0000(7)
C7 0.0126(8) 0.0177(9) 0.0140(9) -0.0010(8) 0.0016(8) 0.0002(6)
C8 0.0122(8) 0.0174(9) 0.0162(9) -0.0009(8) 0.0040(8) 0.0013(7)
C9 0.0137(10) 0.0423(16) 0.0246(12) -0.0067(11) -0.0037(9) 0.0012(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 H1 95.0 . .
C6 O2 C9 117.69(17) . .
F1 C1 C2 118.71(13) . 3_655
F1 C1 C2 118.71(13) . .
C2 C1 C2 122.4(3) 3_655 .
O1 C2 C1 118.91(19) . .
O1 C2 C3 116.72(18) . .
C1 C2 C3 124.36(19) . .
C4 C3 C2 117.24(19) . .
C8 C3 C2 124.11(18) . .
C8 C3 C4 118.59(18) . .
C3 C4 H4 120.8(14) . .
C5 C4 C3 120.7(2) . .
C5 C4 H4 118.5(14) . .
C4 C5 C6 119.85(19) . .
C4 C5 H5 122.4(16) . .
C6 C5 H5 117.7(16) . .
O2 C6 C5 115.10(18) . .
O2 C6 C7 124.3(2) . .
C7 C6 C5 120.56(18) . .
C6 C7 C8 119.07(19) . .
C6 C7 H7 121.3(12) . .
C8 C7 H7 119.6(12) . .
C3 C8 C7 121.14(18) . .
C3 C8 H8 121.5(19) . .
C7 C8 H8 117.2(19) . .
O2 C9 H9A 105(2) . .
O2 C9 H9B 112.2(19) . .
O2 C9 H9C 112(2) . .
H9A C9 H9B 109(2) . .
H9A C9 H9C 109(3) . .
H9B C9 H9C 110(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.358(4) .
O1 H1 0.9501 .
O1 C2 1.293(3) .
O2 C6 1.370(2) .
O2 C9 1.425(3) .
C1 C2 1.404(2) 3_655
C1 C2 1.404(2) .
C2 C3 1.475(3) .
C3 C4 1.408(3) .
C3 C8 1.393(3) .
C4 C5 1.377(3) .
C4 H4 0.98(3) .
C5 C6 1.394(3) .
C5 H5 0.95(2) .
C6 C7 1.393(3) .
C7 C8 1.394(3) .
C7 H7 0.97(3) .
C8 H8 0.92(3) .
C9 H9A 0.93(3) .
C9 H9B 0.94(3) .
C9 H9C 0.96(4) .
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
O1 H1 O1 0.95 1.53 2.467(3) 170.6 3_655 yes
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
O1 C2 C1 F1 174.8(2) .
C1 C2 C3 C4 156.5(2) .
C1 C2 C3 C8 -26.3(3) .
C2 C1 C2 O1 -0.9(5) 3_655
C2 C1 C2 C3 179.96(16) 3_655
C3 C2 C1 F1 -4.3(4) .
C4 C3 C2 O1 -22.6(3) .
C5 C6 O2 C9 176.3(2) .
C7 C6 O2 C9 -4.5(3) .
C8 C3 C2 O1 154.6(2) .
