# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_sa4188
_database_code_depnum_ccdc_archive 'CCDC 1494891'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-11-03 downloaded from the CCDC.
;
_audit_creation_date             2015-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 F N O3'
_chemical_formula_sum            'C17 H16 F N O3'
_chemical_formula_weight         301.31
_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'
N N 0.0061 0.0033 '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                   11.931(4)
_cell_length_b                   10.515(3)
_cell_length_c                   12.710(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.644(4)
_cell_angle_gamma                90
_cell_volume                     1412.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4105
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4667
_cell_measurement_theta_min      1.8087
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.015
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9391
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0936
	          2theta: -19.7326
scan:
	Number of images: 270
	           Slice: -110.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0936
	          2theta: -19.7326
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3415
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0930
_diffrn_orient_matrix_UB_12      -0.0152
_diffrn_orient_matrix_UB_13      0.0081
_diffrn_orient_matrix_UB_21      -0.0173
_diffrn_orient_matrix_UB_22      0.0868
_diffrn_orient_matrix_UB_23      -0.0349
_diffrn_orient_matrix_UB_31      -0.0420
_diffrn_orient_matrix_UB_32      -0.0363
_diffrn_orient_matrix_UB_33      -0.0693
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3052
_reflns_number_total             3230
_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         0.235
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.176
_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)+(0.0440P)²+0.5703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 0.14592(9) 0.85738(11) 0.29920(10) 0.0444(3) Uani 1 1 d . . . . .
O1 O 0.23516(11) 0.60465(12) 0.04497(10) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.46336(10) 0.55636(11) 0.10128(9) 0.0304(3) Uani 1 1 d . . . . .
O3 O 0.68567(11) 0.49856(12) 0.15049(10) 0.0329(3) Uani 1 1 d . . . . .
N1 N 1.25641(12) 0.61132(13) 0.50799(12) 0.0301(3) Uani 1 1 d . . . . .
C1 C 0.23338(15) 0.80041(16) 0.27564(15) 0.0316(4) Uani 1 1 d . . . . .
C2 C 0.19190(15) 0.72776(16) 0.17504(15) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.1058 0.7165 0.1258 0.039 Uiso 1 1 calc R . . . .
C3 C 0.28071(14) 0.67080(15) 0.14753(13) 0.0275(3) Uani 1 1 d . . . . .
C4 C 0.41162(13) 0.68541(14) 0.22484(13) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.44743(14) 0.75983(14) 0.32729(13) 0.0259(3) Uani 1 1 d . . . . .
H5 H 0.5331 0.7698 0.3792 0.031 Uiso 1 1 calc R . . . .
C6 C 0.36002(15) 0.81874(15) 0.35370(14) 0.0302(3) Uani 1 1 d . . . . .
H6 H 0.3853 0.8687 0.4213 0.036 Uiso 1 1 calc R . . . .
C7 C 0.50535(14) 0.62396(14) 0.19549(12) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.63730(14) 0.63868(14) 0.26836(13) 0.0249(3) Uani 1 1 d . . . . .
H8 H 0.6661 0.6920 0.3342 0.030 Uiso 1 1 calc R . . . .
C9 C 0.72428(13) 0.57553(14) 0.24381(12) 0.0238(3) Uani 1 1 d . . . . .
C10 C 0.86083(13) 0.58614(14) 0.31345(12) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.91892(14) 0.66809(15) 0.41085(13) 0.0266(3) Uani 1 1 d . . . . .
H11 H 0.8686 0.7169 0.4333 0.032 Uiso 1 1 calc R . . . .
C12 C 1.04793(14) 0.67846(15) 0.47410(13) 0.0270(3) Uani 1 1 d . . . . .
H12 H 1.0833 0.7347 0.5377 0.032 Uiso 1 1 calc R . . . .
C13 C 1.12789(13) 0.60461(14) 0.44381(12) 0.0241(3) Uani 1 1 d . . . . .
C14 C 1.06962(14) 0.52392(15) 0.34457(13) 0.0269(3) Uani 1 1 d . . . . .
H14 H 1.1196 0.4755 0.3213 0.032 Uiso 1 1 calc R . . . .
C15 C 0.94009(14) 0.51543(15) 0.28140(13) 0.0265(3) Uani 1 1 d . . . . .
H15 H 0.9042 0.4616 0.2160 0.032 Uiso 1 1 calc R . . . .
C16 C 1.33701(15) 0.52929(16) 0.48072(15) 0.0319(4) Uani 1 1 d . . . . .
H16A H 1.3128 0.4422 0.4809 0.048 Uiso 1 1 calc GR . . . .
H16B H 1.4235 0.5407 0.5394 0.048 Uiso 1 1 calc GR . . . .
H16C H 1.3281 0.5505 0.4038 0.048 Uiso 1 1 calc GR . . . .
C17 C 1.31472(15) 0.69731(18) 0.60878(15) 0.0354(4) Uani 1 1 d . . . . .
H17A H 1.2955 0.7836 0.5816 0.053 Uiso 1 1 calc GR . . . .
H17B H 1.4047 0.6852 0.6475 0.053 Uiso 1 1 calc GR . . . .
H17C H 1.2824 0.6799 0.6638 0.053 Uiso 1 1 calc GR . . . .
H1 H 0.309(3) 0.569(2) 0.040(2) 0.076(8) Uiso 1 1 d . . . . .
H3 H 0.597(2) 0.503(2) 0.113(2) 0.068(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 C1 1.3517(18) . ?
O1 C3 1.3494(19) . ?
O1 H1 0.98(3) . ?
O2 C7 1.2780(18) . ?
O3 C9 1.3293(18) . ?
O3 H3 0.94(3) . ?
N1 C13 1.3642(19) . ?
N1 C16 1.4485(19) . ?
N1 C17 1.455(2) . ?
C1 C2 1.370(2) . ?
C1 C6 1.383(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(2) . ?
C3 C4 1.416(2) . ?
C4 C5 1.405(2) . ?
C4 C7 1.481(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(2) . ?
C9 C10 1.453(2) . ?
C10 C11 1.400(2) . ?
C10 C15 1.404(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.415(2) . ?
C13 C14 1.407(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C3 O1 H1 106.9(15) . . ?
C9 O3 H3 104.9(15) . . ?
C13 N1 C16 120.87(13) . . ?
C13 N1 C17 120.28(12) . . ?
C16 N1 C17 118.79(13) . . ?
F1 C1 C2 118.18(15) . . ?
F1 C1 C6 118.56(15) . . ?
C2 C1 C6 123.27(15) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.06(15) . . ?
C3 C2 H2 120.5 . . ?
O1 C3 C2 116.80(14) . . ?
O1 C3 C4 123.13(14) . . ?
C2 C3 C4 120.06(15) . . ?
C3 C4 C7 119.77(14) . . ?
C5 C4 C3 117.83(13) . . ?
C5 C4 C7 122.40(13) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.38(14) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 H6 121.3 . . ?
C5 C6 C1 117.37(15) . . ?
C5 C6 H6 121.3 . . ?
O2 C7 C4 117.71(13) . . ?
O2 C7 C8 120.45(13) . . ?
C8 C7 C4 121.83(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.48(14) . . ?
C9 C8 H8 119.3 . . ?
O3 C9 C8 120.50(13) . . ?
O3 C9 C10 114.63(13) . . ?
C8 C9 C10 124.87(13) . . ?
C11 C10 C9 122.76(13) . . ?
C11 C10 C15 117.32(13) . . ?
C15 C10 C9 119.89(13) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.88(14) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.80(14) . . ?
C13 C12 H12 119.6 . . ?
N1 C13 C12 121.44(13) . . ?
N1 C13 C14 121.18(13) . . ?
C14 C13 C12 117.37(13) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.10(13) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.49(14) . . ?
C14 C15 H15 119.3 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 H1 O2 0.98(3) 1.64(3) 2.5250(18) 147(2) .
O1 H1 O3 0.98(3) 2.55(3) 3.2280(18) 126.1(19) 3_665
O3 H3 O2 0.94(3) 1.62(3) 2.5012(18) 153(2) .

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 C1 C2 C3 178.37(14) . . . . ?
F1 C1 C6 C5 -179.77(14) . . . . ?
O1 C3 C4 C5 178.07(14) . . . . ?
O1 C3 C4 C7 -1.4(2) . . . . ?
O2 C7 C8 C9 -3.5(2) . . . . ?
O3 C9 C10 C11 176.32(13) . . . . ?
O3 C9 C10 C15 -1.5(2) . . . . ?
N1 C13 C14 C15 178.72(15) . . . . ?
C1 C2 C3 O1 -177.28(15) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C7 179.58(14) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C7 O2 -1.7(2) . . . . ?
C3 C4 C7 C8 178.25(14) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C7 C8 C9 176.50(13) . . . . ?
C5 C4 C7 O2 178.84(13) . . . . ?
C5 C4 C7 C8 -1.2(2) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C7 C4 C5 C6 178.98(14) . . . . ?
C7 C8 C9 O3 -0.2(2) . . . . ?
C7 C8 C9 C10 179.55(13) . . . . ?
C8 C9 C10 C11 -3.4(2) . . . . ?
C8 C9 C10 C15 178.73(14) . . . . ?
C9 C10 C11 C12 -178.77(14) . . . . ?
C9 C10 C15 C14 179.42(14) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C10 C15 C14 1.4(2) . . . . ?
C11 C12 C13 N1 -178.14(15) . . . . ?
C11 C12 C13 C14 2.0(2) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C15 C10 C11 C12 -0.9(2) . . . . ?
C16 N1 C13 C12 176.00(14) . . . . ?
C16 N1 C13 C14 -4.1(2) . . . . ?
C17 N1 C13 C12 -1.2(2) . . . . ?
C17 N1 C13 C14 178.72(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 
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data_b
_database_code_depnum_ccdc_archive 'CCDC 1494892'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-11-03 downloaded from the CCDC.
;
_audit_creation_date             2015-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 F N O2'
_chemical_formula_sum            'C17 H16 F N O2'
_chemical_formula_weight         285.31
_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'
N N 0.0061 0.0033 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   12.394(3)
_cell_length_b                   10.203(3)
_cell_length_c                   12.264(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.798(2)
_cell_angle_gamma                90
_cell_volume                     1396.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3986
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      1.8443
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10199
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0860
	          2theta: -20.0064
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0860
	          2theta: -20.0064
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3353
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0827
_diffrn_orient_matrix_UB_12      0.0102
_diffrn_orient_matrix_UB_13      0.0354
_diffrn_orient_matrix_UB_21      -0.0370
_diffrn_orient_matrix_UB_22      0.0584
_diffrn_orient_matrix_UB_23      0.0695
_diffrn_orient_matrix_UB_31      0.0233
_diffrn_orient_matrix_UB_32      -0.0598
_diffrn_orient_matrix_UB_33      0.0626
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3053
_reflns_number_total             3164
_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, 2015)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.120
_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)+(0.0401P)²+0.5055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.17246(8) 0.84473(10) 0.75341(8) 0.0477(2) Uani 1 1 d . . . . .
O1 O 0.15092(9) 0.58048(10) 0.99862(8) 0.0371(2) Uani 1 1 d . . . . .
H1 H 0.2152 0.5530 1.0039 0.056 Uiso 1 1 calc GR . . . .
O2 O 0.31975(8) 0.54875(10) 0.94175(8) 0.0328(2) Uani 1 1 d . . . . .
N1 N 0.71355(10) 0.61956(11) 0.53198(10) 0.0324(3) Uani 1 1 d . . . . .
C1 C -0.06675(12) 0.78788(14) 0.77421(12) 0.0332(3) Uani 1 1 d . . . . .
C2 C -0.01297(12) 0.70971(14) 0.87418(12) 0.0352(3) Uani 1 1 d . . . . .
H2 H -0.0494 0.6942 0.9251 0.042 Uiso 1 1 calc R . . . .
C3 C 0.09783(11) 0.65386(13) 0.89798(11) 0.0286(3) Uani 1 1 d . . . . .
C4 C 0.15127(11) 0.67467(12) 0.81815(10) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.08971(11) 0.75412(13) 0.71627(11) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.1229 0.7680 0.6623 0.034 Uiso 1 1 calc R . . . .
C6 C -0.01846(12) 0.81232(13) 0.69361(12) 0.0318(3) Uani 1 1 d . . . . .
H6 H -0.0575 0.8661 0.6265 0.038 Uiso 1 1 calc R . . . .
C7 C 0.26911(11) 0.61450(12) 0.84641(11) 0.0265(3) Uani 1 1 d . . . . .
C8 C 0.32539(11) 0.63288(12) 0.76555(11) 0.0285(3) Uani 1 1 d . . . . .
H8 H 0.2916 0.6909 0.7009 0.034 Uiso 1 1 calc R . . . .
C9 C 0.42593(11) 0.56723(12) 0.78261(11) 0.0278(3) Uani 1 1 d . . . . .
H9 H 0.4540 0.5069 0.8457 0.033 Uiso 1 1 calc R . . . .
C10 C 0.49485(11) 0.58020(12) 0.71384(10) 0.0260(3) Uani 1 1 d . . . . .
C11 C 0.59622(11) 0.50186(13) 0.74245(11) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.6154 0.4394 0.8033 0.035 Uiso 1 1 calc R . . . .
C12 C 0.66871(11) 0.51353(13) 0.68413(11) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.7352 0.4593 0.7061 0.036 Uiso 1 1 calc R . . . .
C13 C 0.64320(11) 0.60679(12) 0.59146(11) 0.0267(3) Uani 1 1 d . . . . .
C14 C 0.54124(11) 0.68732(13) 0.56227(11) 0.0290(3) Uani 1 1 d . . . . .
H14 H 0.5224 0.7507 0.5023 0.035 Uiso 1 1 calc R . . . .
C15 C 0.46987(11) 0.67317(12) 0.62125(11) 0.0282(3) Uani 1 1 d . . . . .
H15 H 0.4029 0.7267 0.5993 0.034 Uiso 1 1 calc R . . . .
C16 C 0.80872(12) 0.52665(14) 0.55171(13) 0.0364(3) Uani 1 1 d . . . . .
H16A H 0.8688 0.5331 0.6339 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.8440 0.5458 0.4976 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.7764 0.4394 0.5367 0.055 Uiso 1 1 calc GR . . . .
C17 C 0.68469(13) 0.71661(14) 0.43697(13) 0.0364(3) Uani 1 1 d . . . . .
H17A H 0.6086 0.6960 0.3713 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.7455 0.7163 0.4083 0.055 Uiso 1 1 calc GR . . . .
H17C H 0.6809 0.8018 0.4684 0.055 Uiso 1 1 calc GR . . . .


_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 C1 1.3517(15) . ?
O1 H1 0.8200 . ?
O1 C3 1.3454(15) . ?
O2 C7 1.2540(15) . ?
N1 C13 1.3650(16) . ?
N1 C16 1.4492(17) . ?
N1 C17 1.4504(17) . ?
C1 C2 1.3683(19) . ?
C1 C6 1.3830(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.3953(18) . ?
C3 C4 1.4167(16) . ?
C4 C5 1.4038(17) . ?
C4 C7 1.4797(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3795(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.4518(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3484(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.4443(17) . ?
C10 C11 1.3989(17) . ?
C10 C15 1.4069(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3757(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.4087(17) . ?
C13 C14 1.4165(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3724(18) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C3 O1 H1 109.5 . . ?
C13 N1 C16 120.74(11) . . ?
C13 N1 C17 120.20(11) . . ?
C16 N1 C17 118.62(11) . . ?
F1 C1 C2 118.27(12) . . ?
F1 C1 C6 118.24(12) . . ?
C2 C1 C6 123.49(12) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.49(12) . . ?
C3 C2 H2 120.8 . . ?
O1 C3 C2 117.59(11) . . ?
O1 C3 C4 121.89(11) . . ?
C2 C3 C4 120.51(11) . . ?
C3 C4 C7 119.12(11) . . ?
C5 C4 C3 117.72(11) . . ?
C5 C4 C7 123.15(11) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.14(11) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.61(12) . . ?
C5 C6 H6 121.2 . . ?
O2 C7 C4 118.87(11) . . ?
O2 C7 C8 120.78(11) . . ?
C8 C7 C4 120.34(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.07(12) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 116.4 . . ?
C8 C9 C10 127.25(12) . . ?
C10 C9 H9 116.4 . . ?
C11 C10 C9 119.74(11) . . ?
C11 C10 C15 116.48(11) . . ?
C15 C10 C9 123.70(11) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.59(12) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.65(11) . . ?
C13 C12 H12 119.7 . . ?
N1 C13 C12 121.62(11) . . ?
N1 C13 C14 121.11(11) . . ?
C12 C13 C14 117.27(11) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.97(11) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 122.03(11) . . ?
C14 C15 H15 119.0 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 H1 O2 0.82 1.77 2.4980(14) 147.6 .

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 C1 C2 C3 -178.17(12) . . . . ?
F1 C1 C6 C5 179.72(12) . . . . ?
O1 C3 C4 C5 -179.19(12) . . . . ?
O1 C3 C4 C7 -0.27(18) . . . . ?
O2 C7 C8 C9 8.17(19) . . . . ?
N1 C13 C14 C15 179.21(12) . . . . ?
C1 C2 C3 O1 178.07(12) . . . . ?
C1 C2 C3 C4 -1.9(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C3 C4 C5 0.79(18) . . . . ?
C2 C3 C4 C7 179.72(12) . . . . ?
C3 C4 C5 C6 0.81(19) . . . . ?
C3 C4 C7 O2 -1.43(17) . . . . ?
C3 C4 C7 C8 179.29(11) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C4 C7 C8 C9 -172.56(11) . . . . ?
C5 C4 C7 O2 177.43(12) . . . . ?
C5 C4 C7 C8 -1.85(18) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C7 C4 C5 C6 -178.07(12) . . . . ?
C7 C8 C9 C10 -176.63(11) . . . . ?
C8 C9 C10 C11 -178.65(12) . . . . ?
C8 C9 C10 C15 4.6(2) . . . . ?
C9 C10 C11 C12 -176.99(12) . . . . ?
C9 C10 C15 C14 176.41(12) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C10 C15 C14 -0.40(18) . . . . ?
C11 C12 C13 N1 -179.64(12) . . . . ?
C11 C12 C13 C14 0.40(19) . . . . ?
C12 C13 C14 C15 -0.83(19) . . . . ?
C13 C14 C15 C10 0.86(19) . . . . ?
C15 C10 C11 C12 -0.05(19) . . . . ?
C16 N1 C13 C12 7.69(19) . . . . ?
C16 N1 C13 C14 -172.36(12) . . . . ?
C17 N1 C13 C12 179.99(12) . . . . ?
C17 N1 C13 C14 -0.06(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
