#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:53:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/99/1549942.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_1549942
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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_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                 102.4067(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5592(5)
_cell_length_b                   12.9739(8)
_cell_length_c                   12.3376(8)
_cell_measurement_reflns_used    6831
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.28
_cell_measurement_theta_min      2.31
_cell_volume                     1338.05(14)
_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_method       ω-scan
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22309
_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         28.997
_diffrn_reflns_theta_min         2.307
_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    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0788 before and 0.0687 after correction. 
The Ratio of minimum to maximum transmission is 0.8465. 
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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0580
_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)+(0.1100P)²+0.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc03596b2.cif
_cod_data_source_block           2cK_17srv144
_cod_depositor_comments
'Adding full bibliography for 1549940--1549946.cif.'
_cod_database_code               1549942
_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   0.975
_shelx_estimated_absorpt_t_min   0.966
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.18465(12) 0.63983(6) 0.22345(8) 0.0346(3) Uani 1 1 d
O1 O -0.01022(12) 0.42458(9) 0.12253(8) 0.0330(3) Uani 1 1 d
O2 O 0.46823(12) 0.55954(8) 0.25314(8) 0.0318(3) Uani 1 1 d
C1 C 0.08542(15) 0.46745(11) 0.19617(11) 0.0247(3) Uani 1 1 d
C2 C 0.19371(17) 0.55104(10) 0.16211(11) 0.0263(3) Uani 1 1 d
C3 C 0.37076(16) 0.51849(10) 0.18010(10) 0.0238(3) Uani 1 1 d
C4 C 0.41327(15) 0.43759(10) 0.10748(10) 0.0219(3) Uani 1 1 d
C5 C 0.57059(16) 0.40018(11) 0.13074(11) 0.0254(3) Uani 1 1 d
C6 C 0.61587(17) 0.32457(11) 0.06438(12) 0.0281(3) Uani 1 1 d
C7 C 0.50784(16) 0.28444(10) -0.02675(11) 0.0253(3) Uani 1 1 d
C8 C 0.35113(16) 0.32228(11) -0.04974(11) 0.0260(3) Uani 1 1 d
C9 C 0.30442(15) 0.39752(11) 0.01618(11) 0.0255(3) Uani 1 1 d
C10 C 0.5567(2) 0.20435(12) -0.10070(14) 0.0347(4) Uani 1 1 d
C11 C 0.10220(15) 0.43970(10) 0.31492(11) 0.0224(3) Uani 1 1 d
C12 C 0.00160(16) 0.36272(10) 0.34097(11) 0.0247(3) Uani 1 1 d
C13 C 0.01790(17) 0.32931(11) 0.44935(12) 0.0263(3) Uani 1 1 d
C14 C 0.13377(17) 0.37133(10) 0.53460(11) 0.0246(3) Uani 1 1 d
C15 C 0.23266(17) 0.44875(11) 0.50876(11) 0.0263(3) Uani 1 1 d
C16 C 0.21713(17) 0.48320(10) 0.40013(11) 0.0257(3) Uani 1 1 d
C17 C 0.1565(2) 0.33270(13) 0.65201(12) 0.0315(3) Uani 1 1 d
H2 H 0.1490(16) 0.5852(10) 0.0837(11) 0.005(3) Uiso 1 1 d
H5 H 0.648(2) 0.4273(15) 0.1967(16) 0.037(5) Uiso 1 1 d
H6 H 0.723(2) 0.2975(15) 0.0808(15) 0.033(5) Uiso 1 1 d
H8 H 0.273(2) 0.2952(14) -0.1086(16) 0.031(4) Uiso 1 1 d
H9 H 0.193(2) 0.4238(14) -0.0040(15) 0.031(4) Uiso 1 1 d
H10A H 0.486(4) 0.145(3) -0.112(2) 0.087(9) Uiso 1 1 d
H10B H 0.568(3) 0.236(2) -0.176(2) 0.064(7) Uiso 1 1 d
H10C H 0.665(3) 0.177(2) -0.073(2) 0.064(7) Uiso 1 1 d
H12 H -0.080(2) 0.3329(14) 0.2816(15) 0.027(4) Uiso 1 1 d
H13 H -0.048(2) 0.2787(15) 0.4705(16) 0.033(5) Uiso 1 1 d
H15 H 0.315(2) 0.4791(15) 0.5651(14) 0.028(4) Uiso 1 1 d
H16 H 0.287(2) 0.5371(15) 0.3838(15) 0.032(4) Uiso 1 1 d
H17A H 0.239(3) 0.282(2) 0.671(2) 0.076(8) Uiso 1 1 d
H17B H 0.186(4) 0.388(3) 0.701(3) 0.088(9) Uiso 1 1 d
H17C H 0.062(3) 0.308(2) 0.670(2) 0.069(7) Uiso 1 1 d
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
O1 C1 C2 117.68(12)
O1 C1 C11 122.12(13)
C11 C1 C2 120.18(12)
F1 C2 C1 109.11(11)
F1 C2 C3 108.46(11)
F1 C2 H2 95.7(7)
C1 C2 C3 113.43(10)
C1 C2 H2 115.0(7)
C3 C2 H2 113.4(7)
O2 C3 C2 118.99(12)
O2 C3 C4 122.96(12)
C4 C3 C2 118.05(11)
C5 C4 C3 118.25(12)
C9 C4 C3 123.02(11)
C9 C4 C5 118.72(12)
C4 C5 H5 118.9(11)
C6 C5 C4 120.17(13)
C6 C5 H5 120.9(11)
C5 C6 C7 121.31(13)
C5 C6 H6 120.6(11)
C7 C6 H6 118.1(11)
C6 C7 C8 118.25(13)
C6 C7 C10 121.74(13)
C8 C7 C10 119.99(13)
C7 C8 H8 120.9(11)
C9 C8 C7 120.93(12)
C9 C8 H8 118.1(11)
C4 C9 H9 120.8(10)
C8 C9 C4 120.60(12)
C8 C9 H9 118.6(10)
C7 C10 H10A 113.1(18)
C7 C10 H10B 111.4(15)
C7 C10 H10C 114.0(16)
H10A C10 H10B 111(2)
H10A C10 H10C 106(3)
H10B C10 H10C 101(2)
C12 C11 C1 117.73(12)
C16 C11 C1 123.24(12)
C16 C11 C12 118.97(12)
C11 C12 H12 119.0(10)
C13 C12 C11 120.38(12)
C13 C12 H12 120.6(10)
C12 C13 C14 120.99(13)
C12 C13 H13 123.2(12)
C14 C13 H13 115.8(11)
C13 C14 C15 118.57(12)
C13 C14 C17 121.36(13)
C15 C14 C17 120.04(13)
C14 C15 H15 121.1(11)
C16 C15 C14 120.97(13)
C16 C15 H15 118.0(11)
C11 C16 H16 120.2(10)
C15 C16 C11 120.11(12)
C15 C16 H16 119.7(10)
C14 C17 H17A 114.0(17)
C14 C17 H17B 108.9(19)
C14 C17 H17C 113.4(17)
H17A C17 H17B 107(3)
H17A C17 H17C 109(2)
H17B C17 H17C 104(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.3896(16)
O1 C1 1.2188(17)
O2 C3 1.2118(16)
C1 C2 1.5424(19)
C1 C11 1.4854(18)
C2 C3 1.5426(19)
C2 H2 1.058(13)
C3 C4 1.4755(18)
C4 C5 1.4017(18)
C4 C9 1.3986(18)
C5 C6 1.385(2)
C5 H5 1.00(2)
C6 C7 1.394(2)
C6 H6 0.958(19)
C7 C8 1.3990(19)
C7 C10 1.500(2)
C8 C9 1.383(2)
C8 H8 0.941(19)
C9 H9 0.997(17)
C10 H10A 0.97(3)
C10 H10B 1.04(3)
C10 H10C 0.98(3)
C11 C12 1.4004(18)
C11 C16 1.3953(19)
C12 C13 1.3839(19)
C12 H12 0.976(18)
C13 C14 1.392(2)
C13 H13 0.94(2)
C14 C15 1.3939(19)
C14 C17 1.5054(19)
C15 C16 1.3918(19)
C15 H15 0.960(17)
C16 H16 0.972(19)
C17 H17A 0.96(3)
C17 H17B 0.93(3)
C17 H17C 0.94(3)
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 C1 C2 F1 128.87(13)
O2 C3 C2 F1 11.60(16)
C1 C2 C3 O2 -109.78(14)
C1 C2 C3 C4 69.72(15)
C2 C1 C11 C12 -179.52(11)
C2 C1 C11 C16 -2.40(19)
C2 C3 C4 C5 -173.50(11)
C2 C3 C4 C9 7.17(18)
C3 C2 C1 O1 -110.11(14)
C3 C2 C1 C11 68.40(15)
C4 C3 C2 F1 -168.90(10)
C5 C4 C3 O2 5.98(19)
C9 C4 C3 O2 -173.34(12)
C11 C1 C2 F1 -52.62(15)
C12 C11 C1 O1 -1.07(19)
C16 C11 C1 O1 176.05(12)
