# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx4150
_audit_block_doi                 10.5517/cc1k95bc
_database_code_depnum_ccdc_archive 'CCDC 1438782'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_audit_creation_date             2015-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
1-(4-hydroxyphenyl)ethan-2-(4-fluorophenyl)-1-one
_chemical_formula_moiety         'C14 H11 F O2'
_chemical_formula_sum            'C14 H11 F O2'
_chemical_formula_weight         230.23
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.940(2)
_cell_length_b                   16.998(5)
_cell_length_c                   8.091(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.287(5)
_cell_angle_gamma                90
_cell_volume                     1092.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3919
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4801
_cell_measurement_theta_min      1.1980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9507
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0380
	          2theta: -19.9252
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0380
	          2theta: -19.9252
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2596
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0535
_diffrn_orient_matrix_UB_12      0.1041
_diffrn_orient_matrix_UB_13      -0.0466
_diffrn_orient_matrix_UB_21      -0.0531
_diffrn_orient_matrix_UB_22      -0.0210
_diffrn_orient_matrix_UB_23      0.0141
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      0.0544
_diffrn_orient_matrix_UB_33      0.1107
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2401
_reflns_number_total             2501
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.128
_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)+(0.0458P)²+0.4451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.30769(13) 0.74243(6) 0.97192(11) 0.0395(3) Uani 1 1 d . . . . .
O1 O 0.23595(16) 0.49718(7) 0.44945(13) 0.0390(3) Uani 1 1 d . . . . .
O2 O 0.12774(16) 0.40089(7) -0.30015(13) 0.0369(3) Uani 1 1 d . . . . .
C1 C 0.3363(2) 0.65141(9) 0.50104(17) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.47884(19) 0.65630(9) 0.60021(19) 0.0317(3) Uani 1 1 d . . . . .
H2A H 0.5814 0.6382 0.5603 0.038 Uiso 1 1 calc R . . . .
C3 C 0.47061(19) 0.68796(9) 0.75876(19) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.5663 0.6912 0.8251 0.038 Uiso 1 1 calc R . . . .
C4 C 0.3181(2) 0.71425(8) 0.81448(17) 0.0290(3) Uani 1 1 d . . . . .
C5 C 0.17388(19) 0.71184(9) 0.71947(19) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.0724 0.7312 0.7595 0.038 Uiso 1 1 calc R . . . .
C6 C 0.18438(19) 0.67962(9) 0.56195(19) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.0882 0.6769 0.4962 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3428(2) 0.61522(9) 0.33098(18) 0.0354(4) Uani 1 1 d . . . . .
H7A H 0.4591 0.6140 0.2947 0.042 Uiso 1 1 calc R . . . .
H7B H 0.2805 0.6485 0.2548 0.042 Uiso 1 1 calc R . . . .
C8 C 0.27142(19) 0.53232(9) 0.32243(17) 0.0281(3) Uani 1 1 d . . . . .
C9 C 0.24509(18) 0.49681(8) 0.15777(17) 0.0259(3) Uani 1 1 d . . . . .
C10 C 0.15602(19) 0.42618(9) 0.14359(17) 0.0302(3) Uani 1 1 d . . . . .
H10 H 0.1201 0.4005 0.2386 0.036 Uiso 1 1 calc R . . . .
C11 C 0.1205(2) 0.39390(9) -0.00927(18) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.0619 0.3467 -0.0169 0.038 Uiso 1 1 calc R . . . .
C12 C 0.17310(18) 0.43244(9) -0.15227(17) 0.0277(3) Uani 1 1 d . . . . .
C13 C 0.26640(19) 0.50138(9) -0.14085(17) 0.0292(3) Uani 1 1 d . . . . .
H13 H 0.3052 0.5261 -0.2359 0.035 Uiso 1 1 calc R . . . .
C14 C 0.30112(19) 0.53293(9) 0.01328(17) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.3632 0.5792 0.0207 0.034 Uiso 1 1 calc R . . . .
H2 H 0.162(3) 0.4346(15) -0.382(3) 0.061(7) Uiso 1 1 d . . . . .


_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
F1 C4 1.3639(16) . ?
O1 C8 1.2228(17) . ?
O2 C12 1.3582(17) . ?
O2 H2 0.92(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.390(2) . ?
C1 C7 1.508(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(2) . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.520(2) . ?
C8 C9 1.4766(19) . ?
C9 C10 1.398(2) . ?
C9 C14 1.3953(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(2) . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(2) . ?
C14 H14 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
C12 O2 H2 108.0(14) . . ?
C2 C1 C6 118.76(14) . . ?
C2 C1 C7 121.35(14) . . ?
C6 C1 C7 119.88(14) . . ?
C1 C2 H2A 119.5 . . ?
C1 C2 C3 120.94(14) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.36(14) . . ?
C4 C3 H3 120.8 . . ?
F1 C4 C3 118.68(13) . . ?
F1 C4 C5 118.56(13) . . ?
C3 C4 C5 122.75(14) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.05(14) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.13(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7A 108.8 . . ?
C1 C7 H7B 108.8 . . ?
C1 C7 C8 113.88(12) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
O1 C8 C7 120.13(13) . . ?
O1 C8 C9 121.77(14) . . ?
C9 C8 C7 118.10(12) . . ?
C10 C9 C8 119.63(12) . . ?
C14 C9 C8 122.13(13) . . ?
C14 C9 C10 118.19(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.04(13) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.71(14) . . ?
C12 C11 H11 120.1 . . ?
O2 C12 C11 117.78(13) . . ?
O2 C12 C13 122.04(13) . . ?
C13 C12 C11 120.17(13) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.37(13) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.45(14) . . ?
C13 C14 H14 119.3 . . ?

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
O2 H2 O1 0.92(2) 1.83(2) 2.7457(17) 177(2) 1_554

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
F1 C4 C5 C6 -177.06(13) . . . . ?
O1 C8 C9 C10 9.2(2) . . . . ?
O1 C8 C9 C14 -173.20(15) . . . . ?
O2 C12 C13 C14 176.57(14) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C7 C8 O1 -9.6(2) . . . . ?
C1 C7 C8 C9 169.75(14) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C7 C8 102.91(17) . . . . ?
C2 C3 C4 F1 177.43(13) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C1 C7 C8 -76.15(19) . . . . ?
C7 C1 C2 C3 -178.31(14) . . . . ?
C7 C1 C6 C5 178.72(14) . . . . ?
C7 C8 C9 C10 -170.09(14) . . . . ?
C7 C8 C9 C14 7.5(2) . . . . ?
C8 C9 C10 C11 176.09(14) . . . . ?
C8 C9 C14 C13 -175.93(14) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C9 C14 C13 1.7(2) . . . . ?
C10 C11 C12 O2 -176.51(14) . . . . ?
C10 C11 C12 C13 2.5(2) . . . . ?
C11 C12 C13 C14 -2.4(2) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C14 C9 C10 C11 -1.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour Deposition'
