# Electronic Supplementary Material (ESI) for Reaction Chemistry & Engineering.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sl1409
_database_code_depnum_ccdc_archive 'CCDC 1430558'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2013

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Jian-Siang Poh'
_cambridge_user_crsid            jsp47
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'John Davies'
_cambridge_crystallographer_crsid jed2
_cambridge_sample_id             JSP-2-12-129frA
_cambridge_data_id               sl1409
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H24 Cl2 F6 N4 O4'
_chemical_formula_sum            'C29 H24 Cl2 F6 N4 O4'
_chemical_formula_weight         677.42

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   14.9981(3)
_cell_length_b                   14.2324(3)
_cell_length_c                   14.6364(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.9300(10)
_cell_angle_gamma                90
_cell_volume                     3032.39(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8477
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      30.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15189
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.005
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4351
_reflns_number_gt                3065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+0.8030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     233
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.046

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
N1 N 0.31489(9) 0.57909(9) 0.26522(9) 0.0393(3) Uani 1 1 d . . . . .
N2 N 0.35575(9) 0.52249(10) 0.21313(9) 0.0394(3) Uani 1 1 d . . . . .
O1 O 0.48370(8) 0.60783(9) 0.05594(9) 0.0515(3) Uani 1 1 d . . . . .
H1 H 0.5058 0.5821 0.0147 0.077 Uiso 1 1 calc R U . . .
O2 O 0.44535(9) 0.45923(9) 0.07988(9) 0.0526(3) Uani 1 1 d . . . . .
C1 C 0.12664(12) 0.39861(12) 0.50982(12) 0.0445(4) Uani 1 1 d D . . . .
F1 F 0.1135(11) 0.4512(7) 0.5767(8) 0.134(4) Uani 0.402(12) 1 d D . P A 1
F2 F 0.0495(7) 0.3668(8) 0.4668(7) 0.105(4) Uani 0.402(12) 1 d D . P A 1
F3 F 0.1729(5) 0.3262(7) 0.5549(7) 0.108(3) Uani 0.402(12) 1 d D . P A 1
F1' F 0.1430(4) 0.4354(4) 0.5926(3) 0.0828(17) Uani 0.598(12) 1 d D . P A 2
F2' F 0.0374(4) 0.4008(8) 0.4808(5) 0.115(3) Uani 0.598(12) 1 d D . P A 2
F3' F 0.1463(6) 0.3100(3) 0.5222(6) 0.106(2) Uani 0.598(12) 1 d D . P A 2
C2 C 0.17570(11) 0.44637(12) 0.44538(11) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.25633(11) 0.40839(11) 0.43129(11) 0.0397(3) Uani 1 1 d . . . . .
H3 H 0.2798 0.3515 0.4618 0.048 Uiso 1 1 calc R U . . .
C4 C 0.30281(10) 0.45328(11) 0.37264(10) 0.0383(3) Uani 1 1 d . . . . .
H4 H 0.3587 0.4281 0.3635 0.046 Uiso 1 1 calc R U . . .
C5 C 0.26681(10) 0.53556(11) 0.32727(10) 0.0382(3) Uani 1 1 d . . . . .
C6 C 0.18570(13) 0.57266(14) 0.33956(14) 0.0535(5) Uani 1 1 d . . . . .
H6 H 0.1610 0.6282 0.3071 0.064 Uiso 1 1 calc R U . . .
C7 C 0.14036(13) 0.52831(14) 0.39966(15) 0.0554(5) Uani 1 1 d . . . . .
H7 H 0.0850 0.5542 0.4095 0.067 Uiso 1 1 calc R U . . .
C8 C 0.34910(16) 0.83514(16) 0.33020(16) 0.0684(6) Uani 1 1 d . . . . .
H8A H 0.3202 0.8981 0.3225 0.082 Uiso 1 1 calc R U . . .
H8B H 0.4134 0.8334 0.3239 0.082 Uiso 1 1 calc R U . . .
C9 C 0.3225(2) 0.76850(19) 0.39917(17) 0.0862(8) Uani 1 1 d . . . . .
H9A H 0.3705 0.7259 0.4352 0.103 Uiso 1 1 calc R U . . .
H9B H 0.2773 0.7907 0.4338 0.103 Uiso 1 1 calc R U . . .
C10 C 0.28929(15) 0.75209(12) 0.29565(14) 0.0545(5) Uani 1 1 d . . . . .
H10 H 0.2230 0.7663 0.2681 0.065 Uiso 1 1 calc R U . . .
C11 C 0.32835(11) 0.67339(12) 0.25054(12) 0.0441(4) Uani 1 1 d . . . . .
C12 C 0.38149(11) 0.67618(12) 0.18640(11) 0.0448(4) Uani 1 1 d . . . . .
H12 H 0.4038 0.7306 0.1614 0.054 Uiso 1 1 calc R U . . .
C13 C 0.39623(10) 0.58225(12) 0.16522(11) 0.0400(3) Uani 1 1 d . . . . .
C14 C 0.44482(10) 0.54536(12) 0.09664(11) 0.0407(4) Uani 1 1 d . . . . .
Cl1 Cl 0.01988(4) 0.75038(3) 0.15761(3) 0.05779(17) Uani 1 1 d . . . . .
C15 C 0.0000 0.82032(16) 0.2500 0.0458(5) Uani 1 2 d S T P . .
H15 H -0.0567 0.8576 0.2267 0.055 Uiso 1 1 d R U . . .


_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 N2 1.3530(18) . ?
N1 C11 1.382(2) . ?
N1 C5 1.4297(19) . ?
N2 C13 1.337(2) . ?
O1 C14 1.2855(19) . ?
O1 H1 0.8400 . ?
O2 C14 1.251(2) . ?
C1 F2 1.260(7) . ?
C1 F1 1.285(7) . ?
C1 F1' 1.288(4) . ?
C1 F3' 1.298(4) . ?
C1 F2' 1.303(5) . ?
C1 F3 1.326(6) . ?
C1 C2 1.492(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.385(3) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C10 1.496(3) . ?
C8 C9 1.507(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.495(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.490(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.371(2) . ?
C12 C13 1.402(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.472(2) . ?
Cl1 C15 1.7615(14) . ?
C15 Cl1 1.7615(14) 2 ?
C15 H15 0.9900 . ?

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
N2 N1 C11 112.81(13) . . ?
N2 N1 C5 117.79(13) . . ?
C11 N1 C5 129.39(13) . . ?
C13 N2 N1 103.96(13) . . ?
C14 O1 H1 109.5 . . ?
F2 C1 F1 107.4(7) . . ?
F1' C1 F3' 106.1(4) . . ?
F1' C1 F2' 104.2(4) . . ?
F3' C1 F2' 104.5(4) . . ?
F2 C1 F3 106.1(6) . . ?
F1 C1 F3 103.4(6) . . ?
F2 C1 C2 112.4(5) . . ?
F1 C1 C2 114.0(4) . . ?
F1' C1 C2 113.4(3) . . ?
F3' C1 C2 113.6(2) . . ?
F2' C1 C2 114.0(3) . . ?
F3 C1 C2 112.9(3) . . ?
C3 C2 C7 120.21(15) . . ?
C3 C2 C1 119.83(15) . . ?
C7 C2 C1 119.96(15) . . ?
C2 C3 C4 120.00(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.28(14) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.96(15) . . ?
C6 C5 N1 120.89(14) . . ?
C4 C5 N1 118.12(13) . . ?
C5 C6 C7 119.47(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 120.05(15) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C10 C8 C9 59.70(16) . . ?
C10 C8 H8A 117.8 . . ?
C9 C8 H8A 117.8 . . ?
C10 C8 H8B 117.8 . . ?
C9 C8 H8B 117.8 . . ?
H8A C8 H8B 114.9 . . ?
C10 C9 C8 59.79(14) . . ?
C10 C9 H9A 117.8 . . ?
C8 C9 H9A 117.8 . . ?
C10 C9 H9B 117.8 . . ?
C8 C9 H9B 117.8 . . ?
H9A C9 H9B 114.9 . . ?
C11 C10 C9 119.74(18) . . ?
C11 C10 C8 118.42(18) . . ?
C9 C10 C8 60.51(17) . . ?
C11 C10 H10 115.7 . . ?
C9 C10 H10 115.7 . . ?
C8 C10 H10 115.7 . . ?
C12 C11 N1 105.39(14) . . ?
C12 C11 C10 129.59(16) . . ?
N1 C11 C10 125.00(15) . . ?
C11 C12 C13 105.82(14) . . ?
C11 C12 H12 127.1 . . ?
C13 C12 H12 127.1 . . ?
N2 C13 C12 112.01(14) . . ?
N2 C13 C14 119.51(15) . . ?
C12 C13 C14 128.41(15) . . ?
O2 C14 O1 124.19(15) . . ?
O2 C14 C13 120.73(14) . . ?
O1 C14 C13 115.06(15) . . ?
Cl1 C15 Cl1 111.17(13) . 2 ?
Cl1 C15 H15 109.2 . . ?
Cl1 C15 H15 106.1 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
C11 N1 N2 C13 0.41(16) . . . . ?
C5 N1 N2 C13 -178.42(13) . . . . ?
F2 C1 C2 C3 -113.9(7) . . . . ?
F1 C1 C2 C3 123.6(9) . . . . ?
F1' C1 C2 C3 99.1(4) . . . . ?
F3' C1 C2 C3 -22.3(5) . . . . ?
F2' C1 C2 C3 -141.9(6) . . . . ?
F3 C1 C2 C3 6.0(6) . . . . ?
F2 C1 C2 C7 65.9(7) . . . . ?
F1 C1 C2 C7 -56.6(9) . . . . ?
F1' C1 C2 C7 -81.1(4) . . . . ?
F3' C1 C2 C7 157.5(5) . . . . ?
F2' C1 C2 C7 37.9(6) . . . . ?
F3 C1 C2 C7 -174.2(6) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C4 -179.02(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3 C4 C5 N1 -178.37(14) . . . . ?
N2 N1 C5 C6 -141.81(17) . . . . ?
C11 N1 C5 C6 39.6(3) . . . . ?
N2 N1 C5 C4 36.3(2) . . . . ?
C11 N1 C5 C4 -142.29(17) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
N1 C5 C6 C7 179.47(17) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 -179.82(17) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C8 C9 C10 C11 107.9(2) . . . . ?
C9 C8 C10 C11 -110.0(2) . . . . ?
N2 N1 C11 C12 -0.68(18) . . . . ?
C5 N1 C11 C12 177.98(15) . . . . ?
N2 N1 C11 C10 178.01(16) . . . . ?
C5 N1 C11 C10 -3.3(3) . . . . ?
C9 C10 C11 C12 -113.5(3) . . . . ?
C8 C10 C11 C12 -43.1(3) . . . . ?
C9 C10 C11 N1 68.1(3) . . . . ?
C8 C10 C11 N1 138.54(19) . . . . ?
N1 C11 C12 C13 0.64(18) . . . . ?
C10 C11 C12 C13 -177.97(17) . . . . ?
N1 N2 C13 C12 0.02(16) . . . . ?
N1 N2 C13 C14 -177.22(13) . . . . ?
C11 C12 C13 N2 -0.43(18) . . . . ?
C11 C12 C13 C14 176.51(15) . . . . ?
N2 C13 C14 O2 3.0(2) . . . . ?
C12 C13 C14 O2 -173.71(16) . . . . ?
N2 C13 C14 O1 -178.16(13) . . . . ?
C12 C13 C14 O1 5.1(2) . . . . ?

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 0.84 1.81 2.6483(17) 173.0 5_665



####################################################################### 
# 
# 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_sl1408
_database_code_depnum_ccdc_archive 'CCDC 1430559'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2013

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Jian-Siang Poh'
_cambridge_user_crsid            jsp47
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'John Davies'
_cambridge_crystallographer_crsid jed2
_cambridge_sample_id             JSP-2-141
_cambridge_data_id               sl1408
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 F3 N3'
_chemical_formula_sum            'C11 H10 F3 N3'
_chemical_formula_weight         241.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.2750(8)
_cell_length_b                   7.2650(5)
_cell_length_c                   12.6939(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.016(2)
_cell_angle_gamma                90
_cell_volume                     1082.46(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3366
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      54.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.112
_shelx_estimated_absorpt_T_min   0.697
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4319
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.766
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.661
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.661
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.661
_reflns_number_total             1295
_reflns_number_gt                1152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+1.3872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1295
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056

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
N1 N 0.00537(17) 0.2568(3) 0.34545(16) 0.0257(6) Uani 1 1 d . . . . .
N2 N -0.06881(18) 0.2184(3) 0.40700(17) 0.0289(6) Uani 1 1 d . . . . .
N3 N 0.0074(2) 0.2817(4) 0.15853(19) 0.0356(7) Uani 1 1 d D . . . .
H3A H -0.033(2) 0.287(4) 0.0895(11) 0.046(9) Uiso 1 1 d D . . . .
H3B H 0.060(2) 0.367(3) 0.177(3) 0.048(10) Uiso 1 1 d D . . . .
C1 C 0.4763(3) 0.2819(5) 0.5815(3) 0.0464(9) Uani 1 1 d . . . . .
F1 F 0.49711(16) 0.1557(3) 0.66131(18) 0.0786(8) Uani 1 1 d . . . . .
F2 F 0.54690(15) 0.2407(4) 0.52267(18) 0.0768(8) Uani 1 1 d . . . . .
F3 F 0.51175(15) 0.4428(3) 0.62988(18) 0.0720(7) Uani 1 1 d . . . . .
C2 C 0.3536(2) 0.2864(4) 0.5147(2) 0.0342(7) Uani 1 1 d . . . . .
C3 C 0.2742(2) 0.3708(4) 0.5571(2) 0.0360(8) Uani 1 1 d . . . . .
H3 H 0.2989 0.4330 0.6258 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1594(2) 0.3654(4) 0.5002(2) 0.0302(7) Uani 1 1 d . . . . .
H4 H 0.1054 0.4251 0.5289 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1238(2) 0.2714(4) 0.4004(2) 0.0260(7) Uani 1 1 d . . . . .
C6 C 0.2029(2) 0.1877(4) 0.3575(2) 0.0316(7) Uani 1 1 d . . . . .
H6 H 0.1785 0.1246 0.2891 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3182(2) 0.1963(4) 0.4149(2) 0.0362(8) Uani 1 1 d . . . . .
H7 H 0.3726 0.1400 0.3852 0.043 Uiso 1 1 calc R U . . .
C8 C -0.0502(2) 0.2508(4) 0.2347(2) 0.0271(7) Uani 1 1 d . . . . .
C9 C -0.1607(2) 0.2046(4) 0.2246(2) 0.0295(7) Uani 1 1 d . . . . .
H9 H -0.2205 0.1881 0.1581 0.035 Uiso 1 1 calc R U . . .
C10 C -0.1681(2) 0.1866(4) 0.3324(2) 0.0276(7) Uani 1 1 d . . . . .
C11 C -0.2692(2) 0.1343(5) 0.3689(2) 0.0399(8) Uani 1 1 d . . . . .
H11A H -0.2466 0.1251 0.4494 0.060 Uiso 1 1 calc R U . . .
H11B H -0.2986 0.0153 0.3365 0.060 Uiso 1 1 calc R U . . .
H11C H -0.3285 0.2283 0.3445 0.060 Uiso 1 1 calc R U . . .


_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 C8 1.372(3) . ?
N1 N2 1.391(3) . ?
N1 C5 1.421(3) . ?
N2 C10 1.326(3) . ?
N3 C8 1.372(4) . ?
N3 H3A 0.871(10) . ?
N3 H3B 0.875(10) . ?
C1 F3 1.333(4) . ?
C1 F2 1.333(4) . ?
C1 F1 1.334(4) . ?
C1 C2 1.496(4) . ?
C2 C7 1.379(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.367(4) . ?
C9 C10 1.404(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.495(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C8 N1 N2 111.0(2) . . ?
C8 N1 C5 129.5(2) . . ?
N2 N1 C5 118.91(19) . . ?
C10 N2 N1 104.5(2) . . ?
C8 N3 H3A 117(2) . . ?
C8 N3 H3B 115(2) . . ?
H3A N3 H3B 113(3) . . ?
F3 C1 F2 106.1(3) . . ?
F3 C1 F1 106.8(3) . . ?
F2 C1 F1 105.0(3) . . ?
F3 C1 C2 112.4(3) . . ?
F2 C1 C2 113.5(3) . . ?
F1 C1 C2 112.5(2) . . ?
C7 C2 C3 119.8(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 119.7(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 N1 120.6(2) . . ?
C4 C5 N1 119.1(2) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 N1 106.6(2) . . ?
C9 C8 N3 132.5(2) . . ?
N1 C8 N3 120.9(2) . . ?
C8 C9 C10 106.1(2) . . ?
C8 C9 H9 127.0 . . ?
C10 C9 H9 127.0 . . ?
N2 C10 C9 111.8(2) . . ?
N2 C10 C11 119.7(2) . . ?
C9 C10 C11 128.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C8 N1 N2 C10 1.0(3) . . . . ?
C5 N1 N2 C10 -171.0(2) . . . . ?
F3 C1 C2 C7 141.0(3) . . . . ?
F2 C1 C2 C7 20.7(4) . . . . ?
F1 C1 C2 C7 -98.5(4) . . . . ?
F3 C1 C2 C3 -43.5(4) . . . . ?
F2 C1 C2 C3 -163.8(3) . . . . ?
F1 C1 C2 C3 77.0(4) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 -175.4(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 N1 176.3(2) . . . . ?
C8 N1 C5 C6 -34.9(4) . . . . ?
N2 N1 C5 C6 135.4(3) . . . . ?
C8 N1 C5 C4 147.4(3) . . . . ?
N2 N1 C5 C4 -42.3(3) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
N1 C5 C6 C7 -177.1(2) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C1 C2 C7 C6 174.6(3) . . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
N2 N1 C8 C9 -1.1(3) . . . . ?
C5 N1 C8 C9 169.8(3) . . . . ?
N2 N1 C8 N3 -179.0(2) . . . . ?
C5 N1 C8 N3 -8.1(4) . . . . ?
N1 C8 C9 C10 0.8(3) . . . . ?
N3 C8 C9 C10 178.3(3) . . . . ?
N1 N2 C10 C9 -0.5(3) . . . . ?
N1 N2 C10 C11 178.2(2) . . . . ?
C8 C9 C10 N2 -0.2(3) . . . . ?
C8 C9 C10 C11 -178.7(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
N3 H3A N2 0.871(10) 2.228(15) 3.053(3) 158(3) 4_565



