# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_cu_NCFO3M_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1550504'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32.42 H9 F12 N9.35 O1.38'
_chemical_formula_weight         779.57

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'
O O 0.0492 0.0322 '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                   19.1610(7)
_cell_length_b                   34.1885(15)
_cell_length_c                   7.1304(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.374(3)
_cell_angle_gamma                90
_cell_volume                     4378.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.999
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II DUO'
_diffrn_measurement_method       'narrow frame'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15731
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         68.444
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3937
_reflns_number_gt                3013
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1890P)²+4.8518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3937
_refine_ls_number_parameters     260
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2592
_refine_ls_wR_factor_gt          0.2396
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.88577(18) 0.77877(10) 0.7735(5) 0.0384(7) Uani 1 1 d . . . . .
H1 H 0.9038 0.7532 0.8170 0.046 Uiso 1 1 calc R U . . .
C2 C 0.81169(17) 0.79094(9) 0.7200(5) 0.0344(7) Uani 1 1 d . . . . .
C3 C 0.81344(18) 0.83042(9) 0.6695(6) 0.0415(8) Uani 1 1 d . . . . .
H3 H 0.7716 0.8474 0.6270 0.050 Uiso 1 1 calc R U . . .
C4 C 0.74737(16) 0.76746(9) 0.7179(5) 0.0327(7) Uani 1 1 d . . . . .
C5 C 0.75371(16) 0.72966(9) 0.7951(5) 0.0335(7) Uani 1 1 d . . . . .
C6 C 0.69347(17) 0.70760(8) 0.7966(5) 0.0330(7) Uani 1 1 d . . . . .
C7 C 0.62075(16) 0.72210(9) 0.7195(5) 0.0333(7) Uani 1 1 d . . . . .
C8 C 0.61358(16) 0.75933(9) 0.6358(5) 0.0377(7) Uani 1 1 d . . . . .
C9 C 0.67438(18) 0.78081(9) 0.6362(5) 0.0378(8) Uani 1 1 d . . . . .
C10 C 0.55613(16) 0.69974(9) 0.7325(5) 0.0333(7) Uani 1 1 d . . . . .
C11 C 0.5000 0.64284(12) 0.7500 0.0334(9) Uani 1 2 d S T P . .
C12 C 0.5000 0.59972(12) 0.7500 0.0337(9) Uani 1 2 d S T P . .
C13 C 0.43734(16) 0.57819(9) 0.6416(5) 0.0339(7) Uani 1 1 d . . . . .
C14 C 0.43806(16) 0.53791(9) 0.6413(5) 0.0340(7) Uani 1 1 d . . . . .
C15 C 0.5000 0.51592(12) 0.7500 0.0312(9) Uani 1 2 d S T P . .
C16 C 0.5000 0.47305(12) 0.7500 0.0335(9) Uani 1 2 d S T P . .
C17 C 0.43927(18) 0.44755(9) 0.6741(5) 0.0386(8) Uani 1 1 d . . . . .
H17 H 0.3889 0.4555 0.6117 0.046 Uiso 1 1 calc R U . . .
F1 F 0.82160(10) 0.71342(5) 0.8783(3) 0.0437(5) Uani 1 1 d . . . . .
F2 F 0.70790(10) 0.67268(5) 0.8845(3) 0.0403(5) Uani 1 1 d . . . . .
F3 F 0.54625(10) 0.77475(6) 0.5410(4) 0.0525(6) Uani 1 1 d . . . . .
F4 F 0.66068(10) 0.81624(6) 0.5471(4) 0.0524(6) Uani 1 1 d . . . . .
F5 F 0.37540(10) 0.59639(5) 0.5265(3) 0.0448(5) Uani 1 1 d . . . . .
F6 F 0.37566(10) 0.51960(5) 0.5249(3) 0.0448(5) Uani 1 1 d . . . . .
N1 N 0.92698(14) 0.80880(8) 0.7536(5) 0.0410(7) Uani 1 1 d . . . . .
H1A H 0.9753 0.8082 0.7778 0.049 Uiso 0.5 1 calc R U P . .
N2 N 0.88266(15) 0.84030(8) 0.6901(5) 0.0408(7) Uani 1 1 d . . . . .
H2A H 0.8973 0.8636 0.6664 0.049 Uiso 0.5 1 calc R U P . .
N3 N 0.46235(16) 0.41104(8) 0.7020(5) 0.0417(7) Uani 1 1 d . . . . .
H3A H 0.4340 0.3902 0.6650 0.050 Uiso 0.5 1 calc R U P . .
N4 N 0.55854(14) 0.66073(7) 0.7262(4) 0.0355(6) Uani 1 1 d . . . . .
N5 N 0.5000 0.72086(10) 0.7500 0.0346(8) Uani 1 2 d S T P . .
O1S O 0.7055(12) 0.9137(4) 0.563(2) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
C1S C 0.7143(8) 0.9451(3) 0.4909(16) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
C2S C 0.7086(16) 0.9844(4) 0.587(3) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
C3S C 0.7413(16) 0.9823(5) 0.222(3) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
C4S C 0.7359(15) 0.9100(5) 0.222(2) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
N1S N 0.7302(9) 0.9466(4) 0.3182(16) 0.151(4) Uiso 0.174(6) 1 d D . P A 1
O2S O 0.7599(7) 0.9231(4) 0.5040(18) 0.151(4) Uiso 0.515(12) 1 d D . P B 2
C5S C 0.7586(11) 0.9149(6) 0.2905(19) 0.151(4) Uiso 0.515(12) 1 d D . P B 2


_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
C1 N1 1.333(4) . ?
C1 C2 1.399(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(5) . ?
C2 C4 1.467(4) . ?
C3 N2 1.326(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.391(5) . ?
C4 C5 1.393(5) . ?
C5 F1 1.347(4) . ?
C5 C6 1.382(4) . ?
C6 F2 1.332(4) . ?
C6 C7 1.399(4) . ?
C7 C8 1.392(4) . ?
C7 C10 1.485(4) . ?
C8 F3 1.339(4) . ?
C8 C9 1.376(4) . ?
C9 F4 1.350(4) . ?
C10 N4 1.336(4) . ?
C10 N5 1.337(3) . ?
C11 N4 1.339(3) . ?
C11 N4 1.339(3) 2_656 ?
C11 C12 1.474(6) . ?
C12 C13 1.391(4) 2_656 ?
C12 C13 1.391(4) . ?
C13 F5 1.338(3) . ?
C13 C14 1.377(4) . ?
C14 F6 1.349(3) . ?
C14 C15 1.391(4) . ?
C15 C14 1.391(4) 2_656 ?
C15 C16 1.466(6) . ?
C16 C17 1.403(4) 2_656 ?
C16 C17 1.403(4) . ?
C17 N3 1.316(4) . ?
C17 H17 0.9500 . ?
N1 N2 1.348(4) . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
N3 N3 1.365(6) 2_656 ?
N3 H3A 0.8800 . ?
N5 C10 1.337(3) 2_656 ?
O1S C1S 1.2278(9) . ?
C1S N1S 1.3689(9) . ?
C1S C2S 1.5267(8) . ?
C2S C3S 1.48(2) 6_576 ?
C3S N1S 1.4499(10) . ?
C3S C2S 1.48(2) 6_575 ?
C4S N1S 1.4510(10) . ?
O2S C5S 1.5400(10) . ?

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
N1 C1 C2 108.9(3) . . ?
N1 C1 H1 125.5 . . ?
C2 C1 H1 125.5 . . ?
C1 C2 C3 104.1(3) . . ?
C1 C2 C4 127.6(3) . . ?
C3 C2 C4 128.3(3) . . ?
N2 C3 C2 109.2(3) . . ?
N2 C3 H3 125.4 . . ?
C2 C3 H3 125.4 . . ?
C9 C4 C5 114.0(3) . . ?
C9 C4 C2 122.9(3) . . ?
C5 C4 C2 123.1(3) . . ?
F1 C5 C6 116.9(3) . . ?
F1 C5 C4 119.6(3) . . ?
C6 C5 C4 123.4(3) . . ?
F2 C6 C5 117.1(3) . . ?
F2 C6 C7 121.2(3) . . ?
C5 C6 C7 121.6(3) . . ?
C8 C7 C6 115.4(3) . . ?
C8 C7 C10 122.5(3) . . ?
C6 C7 C10 122.1(3) . . ?
F3 C8 C9 117.2(3) . . ?
F3 C8 C7 120.7(3) . . ?
C9 C8 C7 122.0(3) . . ?
F4 C9 C8 116.9(3) . . ?
F4 C9 C4 119.6(3) . . ?
C8 C9 C4 123.5(3) . . ?
N4 C10 N5 125.5(3) . . ?
N4 C10 C7 118.2(3) . . ?
N5 C10 C7 116.3(3) . . ?
N4 C11 N4 125.7(4) . 2_656 ?
N4 C11 C12 117.17(19) . . ?
N4 C11 C12 117.17(19) 2_656 . ?
C13 C12 C13 116.1(4) 2_656 . ?
C13 C12 C11 121.95(19) 2_656 . ?
C13 C12 C11 121.95(19) . . ?
F5 C13 C14 118.1(3) . . ?
F5 C13 C12 120.3(3) . . ?
C14 C13 C12 121.5(3) . . ?
F6 C14 C13 117.2(3) . . ?
F6 C14 C15 119.6(3) . . ?
C13 C14 C15 123.1(3) . . ?
C14 C15 C14 114.5(4) . 2_656 ?
C14 C15 C16 122.72(19) . . ?
C14 C15 C16 122.73(19) 2_656 . ?
C17 C16 C17 103.2(4) 2_656 . ?
C17 C16 C15 128.42(19) 2_656 . ?
C17 C16 C15 128.42(19) . . ?
N3 C17 C16 109.9(3) . . ?
N3 C17 H17 125.0 . . ?
C16 C17 H17 125.0 . . ?
C1 N1 N2 108.9(3) . . ?
C1 N1 H1A 125.6 . . ?
N2 N1 H1A 125.6 . . ?
C3 N2 N1 108.8(3) . . ?
C3 N2 H2A 125.6 . . ?
N1 N2 H2A 125.6 . . ?
C17 N3 N3 108.47(19) . 2_656 ?
C17 N3 H3A 125.8 . . ?
N3 N3 H3A 125.8 2_656 . ?
C10 N4 C11 114.3(3) . . ?
C10 N5 C10 114.6(4) . 2_656 ?
O1S C1S N1S 120.90(8) . . ?
O1S C1S C2S 122.75(9) . . ?
N1S C1S C2S 116.35(9) . . ?
C3S C2S C1S 152.4(16) 6_576 . ?
N1S C3S C2S 148.8(15) . 6_575 ?
C1S N1S C3S 124.95(14) . . ?
C1S N1S C4S 118.04(8) . . ?
C3S N1S C4S 117.01(17) . . ?

_refine_diff_density_max         0.617
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.165

_shelxl_version_number           2013-4


_exptl_crystal_preparation       ', Luminescent'
