# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_CPPN
_database_code_depnum_ccdc_archive 'CCDC 1990136'
loop_
_audit_author_name
_audit_author_address
'Harsh Bhatia'
;Shiv Nadar University
India
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CPPN
_chemical_name_common            
(3r,6r)-3,6-di(9H-carbazol-9-yl)-4,5-diphenoxyphthalonitrile
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H26 N4 O2'
_chemical_formula_sum            'C44 H26 N4 O2'
_chemical_formula_weight         642.69

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'

_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                   22.594(3)
_cell_length_b                   10.1874(16)
_cell_length_c                   14.501(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.669(7)
_cell_angle_gamma                90
_cell_volume                     3299.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3084
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.9

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.96
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20029
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3382
_reflns_number_gt                1896
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0635P)²+2.2969P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.000
_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
O1 O 0.55047(7) 0.11988(15) 0.71415(12) 0.0544(5) Uani 1 1 d . . . . .
N2 N 0.61265(8) 0.35656(19) 0.68983(14) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.55550(9) 0.3565(2) 0.71733(16) 0.0410(6) Uani 1 1 d . . . . .
C5 C 0.66352(10) 0.2936(2) 0.73858(17) 0.0426(6) Uani 1 1 d . . . . .
C1 C 0.52810(9) 0.4743(2) 0.73506(16) 0.0423(6) Uani 1 1 d . . . . .
C3 C 0.52622(10) 0.2382(2) 0.73038(16) 0.0432(6) Uani 1 1 d . . . . .
C10 C 0.71022(10) 0.3037(2) 0.68581(18) 0.0470(6) Uani 1 1 d . . . . .
C11 C 0.68685(11) 0.3708(2) 0.60049(18) 0.0479(6) Uani 1 1 d . . . . .
C16 C 0.62702(10) 0.4035(2) 0.60558(17) 0.0470(6) Uani 1 1 d . . . . .
C17 C 0.56756(11) 0.0981(2) 0.6259(2) 0.0524(7) Uani 1 1 d . . . . .
N1 N 0.57918(11) 0.6981(2) 0.7211(2) 0.0813(8) Uani 1 1 d . . . . .
C4 C 0.55747(10) 0.5982(3) 0.72619(19) 0.0531(7) Uani 1 1 d . . . . .
C6 C 0.67052(11) 0.2343(3) 0.82480(19) 0.0544(7) Uani 1 1 d . . . . .
H6 H 0.6388 0.2275 0.8586 0.065 Uiso 1 1 calc R U . . .
C15 C 0.59156(13) 0.4718(3) 0.53533(19) 0.0627(8) Uani 1 1 d . . . . .
H15 H 0.5521 0.4935 0.5397 0.075 Uiso 1 1 calc R U . . .
C9 C 0.76637(11) 0.2542(3) 0.7226(2) 0.0660(8) Uani 1 1 d . . . . .
H9 H 0.7984 0.2601 0.6893 0.079 Uiso 1 1 calc R U . . .
C12 C 0.71069(14) 0.4046(3) 0.5206(2) 0.0648(8) Uani 1 1 d . . . . .
H12 H 0.7498 0.3815 0.5147 0.078 Uiso 1 1 calc R U . . .
C22 C 0.53707(14) 0.1511(3) 0.5460(2) 0.0655(8) Uani 1 1 d . . . . .
H22 H 0.5042 0.2053 0.5486 0.079 Uiso 1 1 calc R U . . .
C7 C 0.72637(13) 0.1853(3) 0.8592(2) 0.0737(9) Uani 1 1 d . . . . .
H7 H 0.7325 0.1441 0.9171 0.088 Uiso 1 1 calc R U . . .
C18 C 0.61472(13) 0.0145(3) 0.6232(2) 0.0701(9) Uani 1 1 d . . . . .
H18 H 0.6346 -0.0231 0.6777 0.084 Uiso 1 1 calc R U . . .
C13 C 0.67582(16) 0.4725(3) 0.4506(2) 0.0756(9) Uani 1 1 d . . . . .
H13 H 0.6915 0.4962 0.3973 0.091 Uiso 1 1 calc R U . . .
C14 C 0.61740(16) 0.5059(3) 0.4588(2) 0.0753(9) Uani 1 1 d . . . . .
H14 H 0.5949 0.5531 0.4109 0.090 Uiso 1 1 calc R U . . .
C8 C 0.77341(13) 0.1965(3) 0.8089(3) 0.0795(10) Uani 1 1 d . . . . .
H8 H 0.8108 0.1641 0.8343 0.095 Uiso 1 1 calc R U . . .
C21 C 0.55536(18) 0.1237(3) 0.4608(2) 0.0853(10) Uani 1 1 d . . . . .
H21 H 0.5354 0.1604 0.4061 0.102 Uiso 1 1 calc R U . . .
C19 C 0.63222(17) -0.0128(4) 0.5382(3) 0.0924(12) Uani 1 1 d . . . . .
H19 H 0.6642 -0.0692 0.5354 0.111 Uiso 1 1 calc R U . . .
C20 C 0.6032(2) 0.0420(4) 0.4584(3) 0.0968(12) Uani 1 1 d . . . . .
H20 H 0.6159 0.0237 0.4017 0.116 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
O1 C3 1.360(3) . ?
O1 C17 1.409(3) . ?
N2 C16 1.395(3) . ?
N2 C2 1.408(3) . ?
N2 C5 1.410(3) . ?
C2 C1 1.392(3) . ?
C2 C3 1.400(3) . ?
C5 C6 1.376(3) . ?
C5 C10 1.397(3) . ?
C1 C1 1.402(4) 2_656 ?
C1 C4 1.441(3) . ?
C3 C3 1.390(4) 2_656 ?
C10 C9 1.395(3) . ?
C10 C11 1.442(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.405(3) . ?
C16 C15 1.385(4) . ?
C17 C22 1.367(4) . ?
C17 C18 1.369(4) . ?
N1 C4 1.136(3) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C15 C14 1.374(4) . ?
C15 H15 0.9300 . ?
C9 C8 1.370(4) . ?
C9 H9 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C22 C21 1.389(4) . ?
C22 H22 0.9300 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?
C21 C20 1.369(5) . ?
C21 H21 0.9300 . ?
C19 C20 1.361(5) . ?
C19 H19 0.9300 . ?
C20 H20 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
C3 O1 C17 118.00(19) . . ?
C16 N2 C2 126.36(19) . . ?
C16 N2 C5 108.37(18) . . ?
C2 N2 C5 124.82(19) . . ?
C1 C2 C3 118.96(19) . . ?
C1 C2 N2 120.3(2) . . ?
C3 C2 N2 120.7(2) . . ?
C6 C5 C10 122.5(2) . . ?
C6 C5 N2 129.0(2) . . ?
C10 C5 N2 108.5(2) . . ?
C2 C1 C1 120.38(12) . 2_656 ?
C2 C1 C4 121.02(19) . . ?
C1 C1 C4 118.57(13) 2_656 . ?
O1 C3 C3 117.49(11) . 2_656 ?
O1 C3 C2 121.89(19) . . ?
C3 C3 C2 120.31(13) 2_656 . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C11 134.0(2) . . ?
C5 C10 C11 107.2(2) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C10 133.9(2) . . ?
C16 C11 C10 107.3(2) . . ?
C15 C16 N2 129.1(2) . . ?
C15 C16 C11 122.3(2) . . ?
N2 C16 C11 108.5(2) . . ?
C22 C17 C18 121.1(3) . . ?
C22 C17 O1 122.4(2) . . ?
C18 C17 O1 116.4(3) . . ?
N1 C4 C1 177.4(3) . . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C14 C15 C16 116.9(3) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C8 C9 C10 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C17 C22 C21 119.7(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 122.3(3) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_CPPNF
_database_code_depnum_ccdc_archive 'CCDC 1990137'
loop_
_audit_author_name
_audit_author_address
'Harsh Bhatia'
;Shiv Nadar University
India
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CPPNF
_chemical_name_common            
(3r,6r)-3,6-di(9H-carbazol-9-yl)-4,5-bis(2,6-difluorophenoxy)phthalonitrile
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H22 F4 N4 O2'
_chemical_formula_sum            'C44 H22 F4 N4 O2'
_chemical_formula_weight         714.65

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'

_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                   22.6154(7)
_cell_length_b                   10.4744(3)
_cell_length_c                   14.3547(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.9530(10)
_cell_angle_gamma                90
_cell_volume                     3349.20(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7629
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.01

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.499
_exptl_crystal_size_min          0.367
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.94
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28307
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3430
_reflns_number_gt                2486
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0359P)²+5.3302P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3430
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_restrained_S_all      0.822
_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
O1 O 0.54853(5) 0.12719(11) 0.71316(9) 0.0519(3) Uani 1 1 d . . . . .
F1 F 0.64381(6) -0.01832(13) 0.70873(11) 0.0885(4) Uani 1 1 d . . . . .
F2 F 0.48840(6) 0.22627(14) 0.54131(10) 0.0898(4) Uani 1 1 d . . . . .
N2 N 0.61310(5) 0.35658(13) 0.69368(10) 0.0419(3) Uani 1 1 d . . . . .
C1 C 0.52826(7) 0.47311(16) 0.73580(12) 0.0411(4) Uani 1 1 d . . . . .
C5 C 0.66324(7) 0.29428(15) 0.74578(12) 0.0403(4) Uani 1 1 d . . . . .
C2 C 0.55565(7) 0.35815(16) 0.71876(11) 0.0399(4) Uani 1 1 d . . . . .
C16 C 0.62833(7) 0.39999(16) 0.60845(12) 0.0431(4) Uani 1 1 d . . . . .
C10 C 0.71036(7) 0.29975(16) 0.69411(12) 0.0437(4) Uani 1 1 d . . . . .
C3 C 0.52636(7) 0.24444(15) 0.73096(12) 0.0420(4) Uani 1 1 d . . . . .
C6 C 0.66950(8) 0.23896(17) 0.83427(13) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.6376 0.2354 0.8674 0.060 Uiso 1 1 calc R U . . .
C4 C 0.55707(7) 0.59333(18) 0.72612(14) 0.0501(4) Uani 1 1 d . . . . .
C11 C 0.68799(7) 0.36506(16) 0.60656(12) 0.0441(4) Uani 1 1 d . . . . .
C17 C 0.56689(8) 0.10720(17) 0.62694(14) 0.0510(4) Uani 1 1 d . . . . .
N1 N 0.57836(8) 0.69056(18) 0.71945(16) 0.0795(6) Uani 1 1 d . . . . .
C9 C 0.76575(8) 0.24875(18) 0.73352(16) 0.0576(5) Uani 1 1 d . . . . .
H9 H 0.7978 0.2518 0.7007 0.069 Uiso 1 1 calc R U . . .
C12 C 0.71300(9) 0.39686(19) 0.52763(14) 0.0593(5) Uani 1 1 d . . . . .
H12 H 0.7522 0.3736 0.5242 0.071 Uiso 1 1 calc R U . . .
C15 C 0.59372(8) 0.4663(2) 0.53559(13) 0.0573(5) Uani 1 1 d . . . . .
H15 H 0.5542 0.4885 0.5379 0.069 Uiso 1 1 calc R U . . .
C7 C 0.72497(9) 0.1893(2) 0.87130(15) 0.0612(5) Uani 1 1 d . . . . .
H7 H 0.7307 0.1519 0.9309 0.073 Uiso 1 1 calc R U . . .
C8 C 0.77260(9) 0.1938(2) 0.82163(17) 0.0669(6) Uani 1 1 d . . . . .
H8 H 0.8095 0.1591 0.8484 0.080 Uiso 1 1 calc R U . . .
C13 C 0.67895(11) 0.4631(2) 0.45497(15) 0.0695(6) Uani 1 1 d . . . . .
H13 H 0.6954 0.4847 0.4020 0.083 Uiso 1 1 calc R U . . .
C22 C 0.53726(10) 0.1515(2) 0.54167(16) 0.0650(5) Uani 1 1 d . . . . .
C18 C 0.61577(9) 0.0285(2) 0.62595(17) 0.0642(6) Uani 1 1 d . . . . .
C14 C 0.62027(10) 0.4982(2) 0.45951(14) 0.0684(6) Uani 1 1 d . . . . .
H14 H 0.5984 0.5444 0.4099 0.082 Uiso 1 1 calc R U . . .
C19 C 0.63495(13) -0.0027(3) 0.5438(2) 0.0933(9) Uani 1 1 d . . . . .
H19 H 0.6679 -0.0563 0.5448 0.112 Uiso 1 1 calc R U . . .
C20 C 0.60558(16) 0.0451(3) 0.4604(2) 0.1036(10) Uani 1 1 d . . . . .
H20 H 0.6189 0.0250 0.4045 0.124 Uiso 1 1 calc R U . . .
C21 C 0.55607(14) 0.1235(3) 0.45784(18) 0.0915(8) Uani 1 1 d . . . . .
H21 H 0.5360 0.1563 0.4009 0.110 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
O1 C3 1.3672(19) . ?
O1 C17 1.388(2) . ?
F1 C18 1.339(3) . ?
F2 C22 1.354(2) . ?
N2 C5 1.406(2) . ?
N2 C16 1.403(2) . ?
N2 C2 1.4068(18) . ?
C1 C2 1.395(2) . ?
C1 C1 1.407(3) 2_656 ?
C1 C4 1.436(2) . ?
C5 C6 1.381(2) . ?
C5 C10 1.401(2) . ?
C2 C3 1.389(2) . ?
C16 C15 1.381(2) . ?
C16 C11 1.403(2) . ?
C10 C9 1.389(2) . ?
C10 C11 1.443(2) . ?
C3 C3 1.395(3) 2_656 ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C4 N1 1.138(2) . ?
C11 C12 1.391(2) . ?
C17 C22 1.371(3) . ?
C17 C18 1.381(3) . ?
C9 C8 1.374(3) . ?
C9 H9 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C15 C14 1.375(3) . ?
C15 H15 0.9300 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C22 C21 1.376(3) . ?
C18 C19 1.365(3) . ?
C14 H14 0.9300 . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 H21 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
C3 O1 C17 118.57(13) . . ?
C5 N2 C16 108.49(12) . . ?
C5 N2 C2 124.38(13) . . ?
C16 N2 C2 126.60(13) . . ?
C2 C1 C1 120.26(9) . 2_656 ?
C2 C1 C4 121.16(14) . . ?
C1 C1 C4 118.57(9) 2_656 . ?
C6 C5 C10 122.54(15) . . ?
C6 C5 N2 128.96(14) . . ?
C10 C5 N2 108.46(14) . . ?
C3 C2 C1 118.83(13) . . ?
C3 C2 N2 120.27(14) . . ?
C1 C2 N2 120.84(14) . . ?
C15 C16 C11 122.54(16) . . ?
C15 C16 N2 129.13(16) . . ?
C11 C16 N2 108.32(14) . . ?
C9 C10 C5 118.92(17) . . ?
C9 C10 C11 133.82(16) . . ?
C5 C10 C11 107.23(14) . . ?
O1 C3 C2 123.26(13) . . ?
O1 C3 C3 116.05(8) . 2_656 ?
C2 C3 C3 120.54(9) . 2_656 ?
C7 C6 C5 117.07(17) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N1 C4 C1 177.7(2) . . ?
C12 C11 C16 118.75(17) . . ?
C12 C11 C10 133.78(17) . . ?
C16 C11 C10 107.47(14) . . ?
C22 C17 C18 117.50(19) . . ?
C22 C17 O1 124.73(17) . . ?
C18 C17 O1 117.56(18) . . ?
C8 C9 C10 119.11(17) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C13 C12 C11 119.09(19) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C16 C15 C14 117.09(19) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C6 C7 C8 121.59(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 120.76(18) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C12 C13 C14 120.86(19) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
F2 C22 C17 118.17(18) . . ?
F2 C22 C21 119.7(2) . . ?
C17 C22 C21 122.1(2) . . ?
F1 C18 C19 120.4(2) . . ?
F1 C18 C17 117.81(18) . . ?
C19 C18 C17 121.8(3) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 118.3(3) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031

