# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1498096'
_audit_update_record             
;
2016-08-07 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H17 N'
_chemical_formula_sum            'C23 H17 N'
_chemical_formula_weight         307.38
_chemical_absolute_configuration unk
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   7.521(4)
_cell_length_b                   19.628(9)
_cell_length_c                   11.313(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1670.0(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.71
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17049
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3020
_reflns_number_total             3392
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.157
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.2430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(4) 0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Rigid bond restraints
 C10, C15
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.2512(2) 0.38865(8) 0.21421(14) 0.0492(3) Uani 1 d . . . .
C1 C 0.4103(3) 0.38308(9) -0.02295(18) 0.0546(5) Uani 1 d . . . .
H1 H 0.4529 0.4179 0.0252 0.065 Uiso 1 calc . . R .
C2 C 0.4464(3) 0.38429(11) -0.1428(2) 0.0664(6) Uani 1 d . . . .
H2 H 0.5139 0.4196 -0.1744 0.080 Uiso 1 calc . . R .
C3 C 0.3833(3) 0.33369(11) -0.2155(2) 0.0677(6) Uani 1 d . . . .
H3 H 0.4091 0.3343 -0.2959 0.081 Uiso 1 calc . . R .
C4 C 0.2819(3) 0.28225(12) -0.1684(2) 0.0686(6) Uani 1 d . . . .
H4 H 0.2356 0.2488 -0.2177 0.082 Uiso 1 calc . . R .
C5 C 0.2477(3) 0.27967(10) -0.04800(17) 0.0554(5) Uani 1 d . . . .
H5 H 0.1821 0.2437 -0.0169 0.067 Uiso 1 calc . . R .
C6 C 0.3110(2) 0.33055(8) 0.02655(17) 0.0440(4) Uani 1 d . . . .
C7 C 0.2768(2) 0.32877(8) 0.15601(16) 0.0439(4) Uani 1 d . . . .
C8 C 0.2762(2) 0.26692(8) 0.21625(16) 0.0449(4) Uani 1 d . . . .
H8 H 0.2957 0.2265 0.1754 0.054 Uiso 1 calc . . R .
C9 C 0.2466(2) 0.26568(9) 0.33723(17) 0.0449(4) Uani 1 d . . . .
C10 C 0.2446(2) 0.20017(9) 0.40366(17) 0.0480(4) Uani 1 d . . . U
C11 C 0.1877(3) 0.14021(10) 0.3510(2) 0.0585(5) Uani 1 d . . . .
H11 H 0.1499 0.1407 0.2727 0.070 Uiso 1 calc . . R .
C12 C 0.1866(3) 0.07941(10) 0.4136(2) 0.0697(6) Uani 1 d . . . .
H12 H 0.1476 0.0397 0.3771 0.084 Uiso 1 calc . . R .
C13 C 0.2421(3) 0.07754(11) 0.5283(2) 0.0715(6) Uani 1 d . . . .
H13 H 0.2415 0.0366 0.5698 0.086 Uiso 1 calc . . R .
C14 C 0.2986(4) 0.13600(12) 0.5822(2) 0.0795(7) Uani 1 d . . . .
H14 H 0.3357 0.1348 0.6606 0.095 Uiso 1 calc . . R .
C15 C 0.3009(3) 0.19710(11) 0.52072(19) 0.0672(5) Uani 1 d . . . U
H15 H 0.3405 0.2365 0.5581 0.081 Uiso 1 calc . . R .
C16 C 0.2204(2) 0.32642(8) 0.39470(16) 0.0437(4) Uani 1 d . . . .
H16 H 0.2012 0.3268 0.4759 0.052 Uiso 1 calc . . R .
C17 C 0.2223(2) 0.38710(8) 0.33270(16) 0.0439(4) Uani 1 d . . . .
C18 C 0.2366(3) 0.46074(11) 0.51348(18) 0.0603(5) Uani 1 d . . . .
H18 H 0.2944 0.4256 0.5531 0.072 Uiso 1 calc . . R .
C19 C 0.1987(3) 0.52110(13) 0.5725(2) 0.0729(6) Uani 1 d . . . .
H19 H 0.2331 0.5264 0.6509 0.087 Uiso 1 calc . . R .
C20 C 0.1108(3) 0.57297(11) 0.5156(2) 0.0739(7) Uani 1 d . . . .
H20 H 0.0834 0.6129 0.5559 0.089 Uiso 1 calc . . R .
C21 C 0.0636(3) 0.56564(10) 0.3996(2) 0.0698(6) Uani 1 d . . . .
H21 H 0.0048 0.6008 0.3608 0.084 Uiso 1 calc . . R .
C22 C 0.1030(2) 0.50610(9) 0.33939(19) 0.0560(4) Uani 1 d . . . .
H22 H 0.0717 0.5020 0.2602 0.067 Uiso 1 calc . . R .
C23 C 0.1888(2) 0.45232(8) 0.39577(16) 0.0466(4) Uani 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
N1 C7 1.361(2) . ?
N1 C17 1.358(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.391(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.487(3) . ?
C7 C8 1.392(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 C10 1.490(2) . ?
C9 C16 1.372(2) . ?
C10 C11 1.387(3) . ?
C10 C15 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.382(2) . ?
C17 C23 1.487(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C18 C23 1.389(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(3) . ?

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
C17 N1 C7 118.74(16) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.87(19) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.37(19) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.16(18) . . ?
C1 C6 C7 120.45(16) . . ?
C5 C6 C7 121.39(16) . . ?
N1 C7 C6 118.73(15) . . ?
N1 C7 C8 121.05(17) . . ?
C8 C7 C6 120.19(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.92(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.97(15) . . ?
C16 C9 C8 118.40(16) . . ?
C16 C9 C10 120.63(16) . . ?
C11 C10 C9 121.27(17) . . ?
C11 C10 C15 117.77(18) . . ?
C15 C10 C9 120.95(17) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C9 C16 H16 119.8 . . ?
C9 C16 C17 120.44(17) . . ?
C17 C16 H16 119.8 . . ?
N1 C17 C16 121.45(16) . . ?
N1 C17 C23 118.77(15) . . ?
C16 C17 C23 119.77(15) . . ?
C19 C18 H18 119.7 . . ?
C23 C18 H18 119.7 . . ?
C23 C18 C19 120.6(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 120.9(2) . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C17 121.24(17) . . ?
C18 C23 C22 117.96(17) . . ?
C22 C23 C17 120.76(17) . . ?

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
N1 C7 C8 C9 0.9(3) . . . . ?
N1 C17 C23 C18 -150.52(18) . . . . ?
N1 C17 C23 C22 31.7(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 N1 35.8(2) . . . . ?
C1 C6 C7 C8 -142.43(18) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 178.42(18) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 -179.73(19) . . . . ?
C5 C6 C7 N1 -145.17(18) . . . . ?
C5 C6 C7 C8 36.6(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C7 C8 C9 179.13(16) . . . . ?
C7 N1 C17 C16 0.7(3) . . . . ?
C7 N1 C17 C23 -178.17(15) . . . . ?
C7 C8 C9 C10 179.76(16) . . . . ?
C7 C8 C9 C16 -0.7(3) . . . . ?
C8 C9 C10 C11 -31.2(3) . . . . ?
C8 C9 C10 C15 148.41(19) . . . . ?
C8 C9 C16 C17 0.5(3) . . . . ?
C9 C10 C11 C12 179.93(19) . . . . ?
C9 C10 C15 C14 179.9(2) . . . . ?
C9 C16 C17 N1 -0.5(3) . . . . ?
C9 C16 C17 C23 178.38(15) . . . . ?
C10 C9 C16 C17 -179.98(16) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C16 C9 C10 C11 149.25(18) . . . . ?
C16 C9 C10 C15 -31.1(3) . . . . ?
C16 C17 C23 C18 30.6(3) . . . . ?
C16 C17 C23 C22 -147.23(18) . . . . ?
C17 N1 C7 C6 -179.15(15) . . . . ?
C17 N1 C7 C8 -0.9(3) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C19 C18 C23 C17 -177.67(17) . . . . ?
C19 C18 C23 C22 0.2(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C17 176.71(17) . . . . ?
C21 C22 C23 C18 -1.2(3) . . . . ?
C23 C18 C19 C20 1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(4)
2 0(4)

####################################################################### 
# 
# 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_aaaaa
_database_code_depnum_ccdc_archive 'CCDC 1498097'
_audit_update_record             
;
2016-08-07 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H15 Cl F N'
_chemical_formula_sum            'C23 H15 Cl F N'
_chemical_formula_weight         359.81
_chemical_absolute_configuration ad
_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 0.0030 0.0020 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+1/2, x+1/2, z+3/4'
3 '-x, -y, z+1/2'
4 'y+1/2, -x+1/2, z+1/4'
5 'x+1/2, -y+1/2, -z+1/4'
6 'y, x, -z'
7 '-x+1/2, y+1/2, -z+3/4'
8 '-y, -x, -z+1/2'

_cell_length_a                   12.115(12)
_cell_length_b                   12.115(12)
_cell_length_c                   12.641(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1855(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4063
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7488
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1531
_reflns_number_total             1699
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.086
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.24(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.1863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F1, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3. Others
 Fixed Sof: Cl1(0.5) F1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl -0.7913(2) -0.56539(19) -0.1372(2) 0.0805(4) Uani 0.50 d A 2 1 . . .
F1 F -0.7807(7) -0.5657(8) -0.1267(7) 0.154(3) Uani 0.50 d A 1 1 . U .
N1 N -0.42265(10) -0.42265(10) 0.0000 0.0432(4) Uani 1 d . . 2 S T P
C1 C -0.27479(14) -0.42247(15) -0.18146(12) 0.0535(4) Uani 1 d . . 1 . . .
H1 H -0.3137 -0.3568 -0.1737 0.064 Uiso 1 calc . . 1 R . .
C2 C -0.17935(15) -0.42508(18) -0.24413(14) 0.0669(5) Uani 1 d . . 1 . . .
H2 H -0.1553 -0.3615 -0.2784 0.080 Uiso 1 calc . . 1 R . .
C3 C -0.12051(16) -0.5236(2) -0.25488(16) 0.0754(6) Uani 1 d . . 1 . . .
H3 H -0.0566 -0.5255 -0.2956 0.090 Uiso 1 calc . . 1 R . .
C4 C -0.15727(19) -0.6178(2) -0.20519(18) 0.0793(6) Uani 1 d . . 1 . . .
H4 H -0.1180 -0.6833 -0.2126 0.095 Uiso 1 calc . . 1 R . .
C5 C -0.25279(16) -0.61570(16) -0.14389(15) 0.0653(5) Uani 1 d . . 1 . . .
H5 H -0.2774 -0.6801 -0.1116 0.078 Uiso 1 calc . . 1 R . .
C6 C -0.31185(12) -0.51801(13) -0.13050(12) 0.0463(4) Uani 1 d . . 1 . . .
C7 C -0.41312(12) -0.51390(12) -0.06203(11) 0.0435(4) Uani 1 d . . 1 . . .
C8 C -0.49245(13) -0.59800(13) -0.06279(12) 0.0500(4) Uani 1 d . . 1 . . .
H8 H -0.4823 -0.6604 -0.1046 0.060 Uiso 1 calc . . 1 R . .
C9 C -0.58741(12) -0.58741(12) 0.0000 0.0503(5) Uani 1 d . . 2 S T P
C10 C -0.67554(14) -0.67554(14) 0.0000 0.0601(5) Uani 1 d A . 2 S TU P
C11 C -0.77038(18) -0.6681(2) -0.06104(19) 0.0826(6) Uani 1 d . . 1 . U .
C12 C -0.8520(2) -0.7501(3) -0.0620(3) 0.1286(12) Uani 1 d A . 1 . U .
H12 H -0.9137 -0.7424 -0.1050 0.154 Uiso 1 calc . . 1 R . .
C13 C -0.8405(2) -0.8405(2) 0.0000 0.1510(19) Uani 1 d . . 2 S TU P
H13 H -0.8948 -0.8948 0.0000 0.181 Uiso 1 calc A . 2 RS T P


_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
Cl1 C11 1.594(4) . ?
F1 C11 1.497(9) . ?
N1 C7 1.3602(19) 6 ?
N1 C7 1.3602(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.402(3) . ?
C1 C6 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.502(2) . ?
C7 C8 1.401(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.404(2) . ?
C9 C8 1.404(2) 6 ?
C9 C10 1.510(3) . ?
C10 C11 1.387(3) 6 ?
C10 C11 1.387(3) . ?
C11 C12 1.402(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(4) . ?
C13 C12 1.354(4) 6 ?
C13 H13 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
C7 N1 C7 118.06(18) 6 . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.42(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.68(19) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.94(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.47(19) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.66(19) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.01(14) . . ?
C5 C6 C1 118.82(15) . . ?
C5 C6 C7 121.17(15) . . ?
N1 C7 C6 115.37(14) . . ?
N1 C7 C8 122.47(14) . . ?
C8 C7 C6 122.16(13) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.47(15) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C8 118.0(2) . 6 ?
C8 C9 C10 120.99(10) . . ?
C8 C9 C10 120.99(10) 6 . ?
C11 C10 C9 122.67(13) . . ?
C11 C10 C9 122.67(13) 6 . ?
C11 C10 C11 114.7(3) . 6 ?
F1 C11 Cl1 5.9(4) . . ?
C10 C11 Cl1 121.24(19) . . ?
C10 C11 F1 115.6(4) . . ?
C10 C11 C12 122.9(3) . . ?
C12 C11 Cl1 115.9(3) . . ?
C12 C11 F1 121.6(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C12 120.0(4) . 6 ?
C12 C13 H13 120.0 6 . ?
C12 C13 H13 120.0 . . ?

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
Cl1 C11 C12 C13 179.7(2) . . . . ?
F1 C11 C12 C13 -178.8(5) . . . . ?
N1 C7 C8 C9 1.9(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C6 C7 N1 -40.61(19) . . . . ?
C1 C6 C7 C8 138.94(17) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 178.95(14) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -178.20(16) . . . . ?
C5 C6 C7 N1 138.86(15) . . . . ?
C5 C6 C7 C8 -41.6(2) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C7 C8 C9 -177.58(12) . . . . ?
C7 N1 C7 C6 178.57(14) 6 . . . ?
C7 N1 C7 C8 -0.98(11) 6 . . . ?
C7 C8 C9 C8 -0.92(10) . . . 6 ?
C7 C8 C9 C10 179.08(10) . . . . ?
C8 C9 C10 C11 82.65(15) 6 . . . ?
C8 C9 C10 C11 -97.35(15) . . . . ?
C8 C9 C10 C11 82.65(15) . . . 6 ?
C8 C9 C10 C11 -97.35(15) 6 . . 6 ?
C9 C10 C11 Cl1 1.0(2) . . . . ?
C9 C10 C11 F1 -0.7(4) . . . . ?
C9 C10 C11 C12 179.44(18) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C10 C11 Cl1 -179.0(2) 6 . . . ?
C11 C10 C11 F1 179.3(4) 6 . . . ?
C11 C10 C11 C12 -0.56(18) 6 . . . ?
C11 C12 C13 C12 -0.53(17) . . . 6 ?

_olex2_submission_special_instructions 'No special instructions were received'
