#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:53:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/99/1549941.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_1549941
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_formula_moiety         'C17 H15 F O2'
_chemical_formula_sum            'C17 H15 F O2'
_chemical_formula_weight         270.29
_chemical_name_systematic
;
2-fluoro-1,3-bis(4-methylphenyl)-1,3-propandione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.3180(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1604(8)
_cell_length_b                   11.7655(8)
_cell_length_c                   10.8190(8)
_cell_measurement_reflns_used    2799
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.24
_cell_measurement_theta_min      2.65
_cell_volume                     1294.57(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Bruker Monocap'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0677 before and 0.0518 after correction. 
The Ratio of minimum to maximum transmission is 0.7702. 
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1500P)²+0.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1358
_reflns_number_total             1646
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL 17srv145 in C2/c #15
REM reset to C2/c #15
CELL 0.71073 11.1604 11.7655 10.819 90 114.318 90
ZERR 4 0.0008 0.0008 0.0008 0 0.0017 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H F O
UNIT 68 60 4 8

L.S. 9
PLAN  5
SIZE 0.2 0.26 0.38
TEMP -153.15
CONF O1 C2 C1 F1
CONF C2 C1 C2 O1
CONF C3 C2 C1 F1
CONF C2 C1 C2 C3
CONF C4 C3 C2 O1
CONF C1 C2 C3 C4
CONF C8 C3 C2 O1
CONF C1 C2 C3 C8
BOND $h
fmap 2
acta 
OMIT -2 57
WGHT 0.15 0.77
FVAR 0.09874
REM <olex2.extras>
REM <HklSrc "%.\\17srv145.hkl">
REM </olex2.extras>

F1    3     0.50000  0.39159  0.25000  10.50000  0.07068  0.02522  0.03643 =
 0.00000  0.00567  0.00000 
O1    4     0.58007  0.67509  0.36775  11.00000  0.03083  0.01897  0.02213 =
 -0.00048  0.00639 -0.00199 
C1    1     0.50000  0.50728  0.25000  10.50000  0.02482  0.01760  0.02096 =
 0.00000  0.00764  0.00000 
C2    1     0.57967  0.56506  0.36990  11.00000  0.01998  0.02083  0.01837 =
 0.00013  0.00806 -0.00042 
C3    1     0.66422  0.51018  0.49905  11.00000  0.01979  0.02156  0.01972 =
 -0.00009  0.00809 -0.00131 
C4    1     0.66516  0.39344  0.52485  11.00000  0.02656  0.02076  0.02391 =
 -0.00184  0.00748 -0.00321 
AFIX 43
H4    2     0.60857  0.34410  0.45608  11.00000 -1.20000 
AFIX 0
C5    1     0.74786  0.34922  0.64973  11.00000  0.02893  0.02081  0.02720 =
 0.00296  0.01182  0.00061 
AFIX 43
H5    2     0.74640  0.26983  0.66508  11.00000 -1.20000 
AFIX 0
C6    1     0.83293  0.41806  0.75316  11.00000  0.02149  0.02764  0.02143 =
 0.00251  0.01078  0.00427 
C7    1     0.83153  0.53489  0.72794  11.00000  0.02488  0.02603  0.02071 =
 -0.00245  0.00628 -0.00073 
AFIX 43
H7    2     0.88800  0.58393  0.79717  11.00000 -1.20000 
AFIX 0
C8    1     0.74909  0.58009  0.60360  11.00000  0.02766  0.01917  0.02243 =
 -0.00207  0.00883 -0.00192 
AFIX 43
H8    2     0.75001  0.65963  0.58887  11.00000 -1.20000 
AFIX 0
C9    1     0.92480  0.36909  0.88719  11.00000  0.02817  0.03586  0.02504 =
 0.00777  0.00997  0.00631 
AFIX 137
H9a   2     1.01512  0.39242  0.90677  11.00000 -1.50000 
H9b   2     0.91891  0.28596  0.88322  11.00000 -1.50000 
H9c   2     0.90023  0.39698  0.95892  11.00000 -1.50000 
AFIX 0
H1    2     0.50000  0.69832  0.25000  10.50000  10.05000 
HKLF 4

END
;
_cod_data_source_file            c8sc03596b2.cif
_cod_data_source_block           2cE_17srv145
_cod_depositor_comments
'Adding full bibliography for 1549940--1549946.cif.'
_cod_database_code               1549941
_shelx_shelxl_version_number     2014/7
_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   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Uiso: H1(0.05)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
F1 F 0.5000 0.39159(14) 0.2500 0.0495(6) Uani 1 2 d S T P
O1 O 0.58007(11) 0.67509(10) 0.36775(11) 0.0255(4) Uani 1 1 d . . .
C1 C 0.5000 0.50728(19) 0.2500 0.0217(5) Uani 1 2 d S T P
C2 C 0.57967(14) 0.56506(15) 0.36990(14) 0.0197(4) Uani 1 1 d . . .
C3 C 0.66422(13) 0.51018(14) 0.49905(14) 0.0204(4) Uani 1 1 d . . .
C4 C 0.66516(16) 0.39344(14) 0.52485(17) 0.0247(4) Uani 1 1 d . . .
H4 H 0.6086 0.3441 0.4561 0.030 Uiso 1 1 calc R . .
C5 C 0.74786(16) 0.34922(14) 0.64973(16) 0.0256(4) Uani 1 1 d . . .
H5 H 0.7464 0.2698 0.6651 0.031 Uiso 1 1 calc R . .
C6 C 0.83293(15) 0.41806(14) 0.75316(16) 0.0229(4) Uani 1 1 d . . .
C7 C 0.83153(15) 0.53489(14) 0.72793(16) 0.0249(4) Uani 1 1 d . . .
H7 H 0.8880 0.5839 0.7972 0.030 Uiso 1 1 calc R . .
C8 C 0.74909(16) 0.58009(14) 0.60360(16) 0.0236(4) Uani 1 1 d . . .
H8 H 0.7500 0.6596 0.5889 0.028 Uiso 1 1 calc R . .
C9 C 0.92479(17) 0.36909(17) 0.88719(18) 0.0300(5) Uani 1 1 d . . .
H9A H 1.0151 0.3924 0.9068 0.045 Uiso 1 1 calc GR . .
H9B H 0.9189 0.2860 0.8832 0.045 Uiso 1 1 calc GR . .
H9C H 0.9002 0.3970 0.9589 0.045 Uiso 1 1 calc GR . .
H1 H 0.5000 0.698(3) 0.2500 0.050 Uiso 1 2 d S T P
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 0.0707(13) 0.0252(9) 0.0364(10) 0.000 0.0057(9) 0.000
O1 0.0308(7) 0.0190(7) 0.0221(6) -0.0005(4) 0.0064(5) -0.0020(4)
C1 0.0248(10) 0.0176(10) 0.0210(10) 0.000 0.0076(8) 0.000
C2 0.0200(7) 0.0208(8) 0.0184(8) 0.0001(5) 0.0081(6) -0.0004(5)
C3 0.0198(8) 0.0216(8) 0.0197(8) -0.0001(6) 0.0081(6) -0.0013(6)
C4 0.0266(8) 0.0208(8) 0.0239(8) -0.0018(6) 0.0075(6) -0.0032(6)
C5 0.0289(9) 0.0208(8) 0.0272(9) 0.0030(6) 0.0118(7) 0.0006(6)
C6 0.0215(8) 0.0276(9) 0.0214(8) 0.0025(6) 0.0108(6) 0.0043(6)
C7 0.0249(8) 0.0260(9) 0.0207(8) -0.0025(6) 0.0063(6) -0.0007(6)
C8 0.0277(8) 0.0192(8) 0.0224(8) -0.0021(6) 0.0088(6) -0.0019(6)
C9 0.0282(9) 0.0359(10) 0.0250(9) 0.0078(7) 0.0100(7) 0.0063(7)
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_3
C2 O1 H1 103.4(16) .
F1 C1 C2 118.85(10) .
F1 C1 C2 118.85(10) 2_655
C2 C1 C2 122.3(2) 2_655
O1 C2 C1 118.12(14) .
O1 C2 C3 116.70(13) .
C1 C2 C3 125.18(16) .
C4 C3 C2 124.58(14) .
C4 C3 C8 117.82(14) .
C8 C3 C2 117.59(15) .
C3 C4 H4 119.7 .
C5 C4 C3 120.64(15) .
C5 C4 H4 119.7 .
C4 C5 H5 119.1 .
C4 C5 C6 121.71(15) .
C6 C5 H5 119.1 .
C5 C6 C7 117.75(14) .
C5 C6 C9 121.41(16) .
C7 C6 C9 120.83(15) .
C6 C7 H7 119.5 .
C8 C7 C6 121.05(14) .
C8 C7 H7 119.5 .
C3 C8 H8 119.5 .
C7 C8 C3 121.02(15) .
C7 C8 H8 119.5 .
C6 C9 H9A 109.5 .
C6 C9 H9B 109.5 .
C6 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.361(3) .
O1 C2 1.2948(19) .
O1 H1 1.248(8) .
C1 C2 1.4091(18) 2_655
C1 C2 1.4091(18) .
C2 C3 1.474(2) .
C3 C4 1.401(2) .
C3 C8 1.404(2) .
C4 H4 0.9500 .
C4 C5 1.386(2) .
C5 H5 0.9500 .
C5 C6 1.391(2) .
C6 C7 1.400(2) .
C6 C9 1.504(2) .
C7 H7 0.9500 .
C7 C8 1.385(2) .
C8 H8 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
O1 C2 C1 F1 179.02(9)
C1 C2 C3 C4 -7.9(2)
C1 C2 C3 C8 172.49(12)
C2 C1 C2 O1 0(82)
C2 C1 C2 C3 0(59)
C3 C2 C1 F1 -0.65(15)
C4 C3 C2 O1 172.44(15)
C8 C3 C2 O1 -7.18(19)
