# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2020250'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-10-08 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
#data_nitti1

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2,3-Dibromo-N,N-dimethyl-N,N-diphenylfumaramide '
_chemical_formula_moiety         'C18 H16 Br2 N2 O2'
_chemical_formula_sum            'C18 H16 Br2 N2 O2'
_chemical_formula_weight         452.15

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'
Br Br -0.2901 2.4595 '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                   6.4413(5)
_cell_length_b                   11.5184(10)
_cell_length_c                   12.4869(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.8517(13)
_cell_angle_gamma                90
_cell_volume                     903.24(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6933
_cell_measurement_theta_min      2.434
_cell_measurement_theta_max      29.193

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    4.500
_shelx_estimated_absorpt_T_min   0.237
_shelx_estimated_absorpt_T_max   0.515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            18004
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         31.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2979
_reflns_number_gt                2439
_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       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.5247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Br1 Br 0.74852(3) 0.51258(2) 0.39434(2) 0.04186(7) Uani 1 1 d . . . . .
O1 O 0.1759(3) 0.50253(12) 0.31722(13) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.2965(2) 0.68529(13) 0.35916(12) 0.0367(3) Uani 1 1 d . . . . .
C1 C 0.4995(3) 0.52165(15) 0.45074(14) 0.0325(3) Uani 1 1 d . . . . .
C2 C 0.3073(3) 0.56919(16) 0.37045(14) 0.0337(3) Uani 1 1 d . . . . .
C3 C 0.1199(3) 0.7360(2) 0.27835(19) 0.0530(5) Uani 1 1 d . . . . .
H3A H 0.093524 0.690169 0.212505 0.080 Uiso 1 1 calc R U . . .
H3B H 0.156005 0.813808 0.261710 0.080 Uiso 1 1 calc R U . . .
H3C H -0.005556 0.737326 0.307845 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4453(3) 0.76259(15) 0.42636(16) 0.0384(4) Uani 1 1 d . . . . .
C5 C 0.5909(4) 0.8223(2) 0.3803(2) 0.0616(6) Uani 1 1 d . . . . .
H5 H 0.593549 0.811891 0.306728 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7328(4) 0.8981(3) 0.4457(3) 0.0832(10) Uani 1 1 d . . . . .
H6 H 0.830664 0.938991 0.415678 0.100 Uiso 1 1 calc R U . . .
C7 C 0.7295(5) 0.9130(2) 0.5543(3) 0.0819(10) Uani 1 1 d . . . . .
H7 H 0.827155 0.962359 0.598139 0.098 Uiso 1 1 calc R U . . .
C8 C 0.5848(6) 0.8560(2) 0.5974(2) 0.0835(10) Uani 1 1 d . . . . .
H8 H 0.581773 0.867161 0.670834 0.100 Uiso 1 1 calc R U . . .
C9 C 0.4397(5) 0.7805(2) 0.53327(19) 0.0614(6) Uani 1 1 d . . . . .
H9 H 0.338978 0.742442 0.563518 0.074 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
Br1 C1 1.8925(18) . ?
O1 C2 1.224(2) . ?
N1 C2 1.345(2) . ?
N1 C4 1.434(2) . ?
N1 C3 1.464(2) . ?
C1 C1 1.326(4) 3_666 ?
C1 C2 1.512(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.359(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.346(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9300 . ?
C9 H9 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
C2 N1 C4 122.94(14) . . ?
C2 N1 C3 118.89(16) . . ?
C4 N1 C3 118.11(16) . . ?
C1 C1 C2 125.8(2) 3_666 . ?
C1 C1 Br1 119.67(18) 3_666 . ?
C2 C1 Br1 114.21(12) . . ?
O1 C2 N1 123.62(17) . . ?
O1 C2 C1 119.90(16) . . ?
N1 C2 C1 116.43(15) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 120.0(2) . . ?
C9 C4 N1 120.6(2) . . ?
C5 C4 N1 119.38(19) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 119.9(3) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 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
C4 N1 C2 O1 176.47(19) . . . . ?
C3 N1 C2 O1 -0.6(3) . . . . ?
C4 N1 C2 C1 -6.1(3) . . . . ?
C3 N1 C2 C1 176.79(17) . . . . ?
C1 C1 C2 O1 -76.5(3) 3_666 . . . ?
Br1 C1 C2 O1 97.26(19) . . . . ?
C1 C1 C2 N1 106.0(3) 3_666 . . . ?
Br1 C1 C2 N1 -80.24(18) . . . . ?
C2 N1 C4 C9 -72.6(3) . . . . ?
C3 N1 C4 C9 104.5(2) . . . . ?
C2 N1 C4 C5 109.7(2) . . . . ?
C3 N1 C4 C5 -73.2(3) . . . . ?
C9 C4 C5 C6 1.5(4) . . . . ?
N1 C4 C5 C6 179.3(2) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -1.6(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C5 C4 C9 C8 -2.1(4) . . . . ?
N1 C4 C9 C8 -179.9(2) . . . . ?
C7 C8 C9 C4 0.9(4) . . . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.062

_exptl_crystal_preparation       Luminescent,Luminescent

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2020251'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-10-08 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_2                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Crystals are extremely thin laminae so as to prevent HR data collection
;
_vrf_PLAT020_2                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.284 Report
RESPONSE: Crystals are extremely thin laminae so as to prevent HR data collection
;
_vrf_PLAT026_2                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        39% Check
RESPONSE: Crystals are extremely thin laminae so as to prevent HR data collection
;
_vrf_PLAT340_2                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01104 Ang.
RESPONSE: Crystals are extremely thin laminae so as to prevent HR data collection
;
# Added during the CSD deposition process: Thursday 08 October 2020 10:06 AM
# end Validation Reply Form

#data_nitti3

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'N, N-dimethyl-N, N-diphenylfumaramide'
_chemical_formula_moiety         'C18 H18 N2 O2'
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34

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           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                   18.21(2)
_cell_length_b                   7.066(8)
_cell_length_c                   19.77(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.968(10)
_cell_angle_gamma                90
_cell_volume                     2375(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    551
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      18.15

_exptl_crystal_description       lamina
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            25862
_diffrn_reflns_av_unetI/netI     0.1959
_diffrn_reflns_av_R_equivalents  0.2842
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4084
_reflns_number_gt                1592
_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       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1014P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4084
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2210
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2795
_refine_ls_wR_factor_gt          0.2022
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0.002
_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
O1A O -0.0591(3) 0.6563(8) 0.5818(3) 0.0953(19) Uani 1 1 d . . . . .
O1B O 0.6038(3) 0.5698(6) 0.6213(2) 0.0499(11) Uani 1 1 d . . . . .
O1C O 0.5042(2) 0.0911(6) 0.6239(2) 0.0488(11) Uani 1 1 d . . . . .
N1A N 0.0289(3) 0.4620(8) 0.6596(3) 0.0619(16) Uani 1 1 d . . . . .
N1B N 0.4921(3) 0.6046(7) 0.6448(2) 0.0466(13) Uani 1 1 d . . . . .
N1C N 0.6325(3) 0.1016(7) 0.6381(2) 0.0463(13) Uani 1 1 d . . . . .
C1A C 0.0196(4) 0.4752(10) 0.5339(3) 0.0613(19) Uani 1 1 d . . . . .
H1A H 0.065726 0.400110 0.545587 0.074 Uiso 1 1 calc R U . . .
C2A C -0.0090(4) 0.5374(11) 0.5916(4) 0.062(2) Uani 1 1 d . . . . .
C3A C 0.0095(5) 0.5429(10) 0.7201(4) 0.078(2) Uani 1 1 d . . . . .
H3A1 H 0.016388 0.680545 0.721115 0.117 Uiso 1 1 calc R U . . .
H3A2 H 0.044357 0.488664 0.765984 0.117 Uiso 1 1 calc R U . . .
H3A3 H -0.045301 0.513125 0.713362 0.117 Uiso 1 1 calc R U . . .
C4A C 0.0794(4) 0.3043(10) 0.6729(3) 0.0516(17) Uani 1 1 d . . . . .
C5A C 0.1541(4) 0.3116(12) 0.7255(3) 0.064(2) Uani 1 1 d . . . . .
H5A H 0.171171 0.423966 0.753038 0.077 Uiso 1 1 calc R U . . .
C6A C 0.2027(5) 0.1625(17) 0.7380(4) 0.095(3) Uani 1 1 d . . . . .
H6A H 0.253638 0.170609 0.774412 0.114 Uiso 1 1 calc R U . . .
C7A C 0.1803(7) 0.0001(16) 0.6995(6) 0.103(4) Uani 1 1 d . . . . .
H7A H 0.216041 -0.102843 0.707632 0.123 Uiso 1 1 calc R U . . .
C8A C 0.1048(7) -0.0151(12) 0.6479(5) 0.086(3) Uani 1 1 d . . . . .
H8A H 0.087814 -0.129354 0.621615 0.103 Uiso 1 1 calc R U . . .
C9A C 0.0561(5) 0.1350(11) 0.6359(4) 0.066(2) Uani 1 1 d . . . . .
H9A H 0.004289 0.124607 0.601160 0.079 Uiso 1 1 calc R U . . .
C1B C 0.4837(4) 0.5208(8) 0.5237(3) 0.0476(16) Uani 1 1 d . . . . .
H1B H 0.428004 0.521530 0.508757 0.057 Uiso 1 1 calc R U . . .
C2B C 0.5316(4) 0.5669(8) 0.6005(3) 0.0435(15) Uani 1 1 d . . . . .
C4B C 0.4082(4) 0.6010(10) 0.6247(3) 0.0432(16) Uani 1 1 d . . . . .
C5B C 0.3669(4) 0.7675(10) 0.6157(3) 0.0502(17) Uani 1 1 d . . . . .
H5B H 0.393676 0.885448 0.622652 0.060 Uiso 1 1 calc R U . . .
C6B C 0.2865(4) 0.7623(11) 0.5966(3) 0.0541(18) Uani 1 1 d . . . . .
H6B H 0.257815 0.877465 0.589988 0.065 Uiso 1 1 calc R U . . .
C7B C 0.2475(4) 0.5953(13) 0.5871(3) 0.061(2) Uani 1 1 d . . . . .
H7B H 0.191965 0.594209 0.574280 0.074 Uiso 1 1 calc R U . . .
C8B C 0.2885(4) 0.4255(11) 0.5960(3) 0.0595(19) Uani 1 1 d . . . . .
H8B H 0.261275 0.308294 0.589169 0.071 Uiso 1 1 calc R U . . .
C9B C 0.3703(4) 0.4286(9) 0.6150(3) 0.0500(16) Uani 1 1 d . . . . .
H9B H 0.399252 0.314019 0.621141 0.060 Uiso 1 1 calc R U . . .
C1C C 0.5356(3) 0.0246(8) 0.5193(3) 0.0423(15) Uani 1 1 d . . . . .
H1C H 0.574785 0.029788 0.498023 0.051 Uiso 1 1 calc R U . . .
C2C C 0.5561(4) 0.0740(8) 0.5984(3) 0.0419(15) Uani 1 1 d . . . . .
C3C C 0.6514(4) 0.1613(9) 0.7134(3) 0.0545(18) Uani 1 1 d . . . . .
H3C1 H 0.652748 0.299805 0.716027 0.082 Uiso 1 1 calc R U . . .
H3C2 H 0.702931 0.110546 0.743281 0.082 Uiso 1 1 calc R U . . .
H3C3 H 0.611235 0.113429 0.731349 0.082 Uiso 1 1 calc R U . . .
C4C C 0.6969(4) 0.0808(10) 0.6133(3) 0.0468(16) Uani 1 1 d . . . . .
C5C C 0.7432(4) 0.2347(10) 0.6145(3) 0.0519(17) Uani 1 1 d . . . . .
H5C H 0.730123 0.355319 0.628265 0.062 Uiso 1 1 calc R U . . .
C6C C 0.8092(4) 0.2136(12) 0.5956(3) 0.064(2) Uani 1 1 d . . . . .
H6C H 0.842106 0.319041 0.596893 0.077 Uiso 1 1 calc R U . . .
C7C C 0.8265(4) 0.0372(13) 0.5749(3) 0.067(2) Uani 1 1 d . . . . .
H7C H 0.871546 0.022590 0.561673 0.081 Uiso 1 1 calc R U . . .
C8C C 0.7806(4) -0.1156(11) 0.5729(3) 0.0590(19) Uani 1 1 d . . . . .
H8C H 0.793421 -0.235557 0.558484 0.071 Uiso 1 1 calc R U . . .
C9C C 0.7150(4) -0.0959(10) 0.5921(3) 0.0508(17) Uani 1 1 d . . . . .
H9C H 0.682528 -0.202044 0.590909 0.061 Uiso 1 1 calc R U . . .
C3B C 0.5376(4) 0.6670(9) 0.7195(3) 0.0554(18) Uani 1 1 d . . . . .
H3B1 H 0.589793 0.608089 0.735819 0.083 Uiso 1 1 calc R U . . .
H3B2 H 0.509950 0.629259 0.751718 0.083 Uiso 1 1 calc R U . . .
H3B3 H 0.543277 0.804991 0.720433 0.083 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
O1A C2A 1.204(7) . ?
O1B C2B 1.228(7) . ?
O1C C2C 1.225(6) . ?
N1A C2A 1.379(8) . ?
N1A C4A 1.408(8) . ?
N1A C3A 1.479(8) . ?
N1B C2B 1.345(7) . ?
N1B C4B 1.434(7) . ?
N1B C3B 1.478(7) . ?
N1C C2C 1.344(7) . ?
N1C C4C 1.433(7) . ?
N1C C3C 1.464(7) . ?
C1A C1A 1.321(12) 3_566 ?
C1A C2A 1.479(9) . ?
C1A H1A 0.9500 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C4A C5A 1.386(9) . ?
C4A C9A 1.387(9) . ?
C5A C6A 1.341(10) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.357(13) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.393(13) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.348(10) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C1B C1B 1.308(10) 3_666 ?
C1B C2B 1.491(8) . ?
C1B H1B 0.9500 . ?
C4B C5B 1.373(8) . ?
C4B C9B 1.379(8) . ?
C5B C6B 1.376(8) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.355(9) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.392(9) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.399(9) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C1C C1C 1.293(10) 3_656 ?
C1C C2C 1.513(8) . ?
C1C H1C 0.9500 . ?
C3C H3C1 0.9800 . ?
C3C H3C2 0.9800 . ?
C3C H3C3 0.9800 . ?
C4C C5C 1.371(8) . ?
C4C C9C 1.393(8) . ?
C5C C6C 1.390(9) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.384(10) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.358(9) . ?
C7C H7C 0.9500 . ?
C8C C9C 1.383(8) . ?
C8C H8C 0.9500 . ?
C9C H9C 0.9500 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 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
C2A N1A C4A 123.6(5) . . ?
C2A N1A C3A 117.2(6) . . ?
C4A N1A C3A 118.9(5) . . ?
C2B N1B C4B 125.5(5) . . ?
C2B N1B C3B 118.0(5) . . ?
C4B N1B C3B 116.3(4) . . ?
C2C N1C C4C 126.0(5) . . ?
C2C N1C C3C 117.0(5) . . ?
C4C N1C C3C 117.0(5) . . ?
C1A C1A C2A 119.6(8) 3_566 . ?
C1A C1A H1A 120.2 3_566 . ?
C2A C1A H1A 120.2 . . ?
O1A C2A N1A 120.8(6) . . ?
O1A C2A C1A 122.6(6) . . ?
N1A C2A C1A 116.4(6) . . ?
N1A C3A H3A1 109.5 . . ?
N1A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
N1A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C5A C4A C9A 117.4(7) . . ?
C5A C4A N1A 120.7(7) . . ?
C9A C4A N1A 121.8(7) . . ?
C6A C5A C4A 121.0(8) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C5A C6A C7A 121.0(9) . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A H6A 119.5 . . ?
C6A C7A C8A 119.7(8) . . ?
C6A C7A H7A 120.1 . . ?
C8A C7A H7A 120.1 . . ?
C9A C8A C7A 118.9(9) . . ?
C9A C8A H8A 120.5 . . ?
C7A C8A H8A 120.5 . . ?
C8A C9A C4A 121.8(8) . . ?
C8A C9A H9A 119.1 . . ?
C4A C9A H9A 119.1 . . ?
C1B C1B C2B 121.9(8) 3_666 . ?
C1B C1B H1B 119.1 3_666 . ?
C2B C1B H1B 119.1 . . ?
O1B C2B N1B 122.4(5) . . ?
O1B C2B C1B 120.7(5) . . ?
N1B C2B C1B 116.9(6) . . ?
C5B C4B C9B 121.1(6) . . ?
C5B C4B N1B 120.0(6) . . ?
C9B C4B N1B 118.9(6) . . ?
C4B C5B C6B 119.5(7) . . ?
C4B C5B H5B 120.3 . . ?
C6B C5B H5B 120.3 . . ?
C7B C6B C5B 121.0(7) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C6B C7B C8B 120.2(7) . . ?
C6B C7B H7B 119.9 . . ?
C8B C7B H7B 119.9 . . ?
C7B C8B C9B 119.5(7) . . ?
C7B C8B H8B 120.3 . . ?
C9B C8B H8B 120.3 . . ?
C4B C9B C8B 118.8(6) . . ?
C4B C9B H9B 120.6 . . ?
C8B C9B H9B 120.6 . . ?
C1C C1C C2C 119.7(6) 3_656 . ?
C1C C1C H1C 120.1 3_656 . ?
C2C C1C H1C 120.1 . . ?
O1C C2C N1C 122.3(5) . . ?
O1C C2C C1C 120.4(5) . . ?
N1C C2C C1C 117.3(5) . . ?
N1C C3C H3C1 109.5 . . ?
N1C C3C H3C2 109.5 . . ?
H3C1 C3C H3C2 109.5 . . ?
N1C C3C H3C3 109.5 . . ?
H3C1 C3C H3C3 109.5 . . ?
H3C2 C3C H3C3 109.5 . . ?
C5C C4C C9C 120.5(6) . . ?
C5C C4C N1C 119.0(6) . . ?
C9C C4C N1C 120.4(6) . . ?
C4C C5C C6C 119.7(7) . . ?
C4C C5C H5C 120.1 . . ?
C6C C5C H5C 120.1 . . ?
C7C C6C C5C 119.2(7) . . ?
C7C C6C H6C 120.4 . . ?
C5C C6C H6C 120.4 . . ?
C8C C7C C6C 121.4(7) . . ?
C8C C7C H7C 119.3 . . ?
C6C C7C H7C 119.3 . . ?
C7C C8C C9C 119.7(7) . . ?
C7C C8C H8C 120.1 . . ?
C9C C8C H8C 120.1 . . ?
C8C C9C C4C 119.5(6) . . ?
C8C C9C H9C 120.2 . . ?
C4C C9C H9C 120.2 . . ?
N1B C3B H3B1 109.5 . . ?
N1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
N1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 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
C4A N1A C2A O1A 170.4(7) . . . . ?
C3A N1A C2A O1A -4.3(11) . . . . ?
C4A N1A C2A C1A -14.2(10) . . . . ?
C3A N1A C2A C1A 171.2(6) . . . . ?
C1A C1A C2A O1A -12.2(13) 3_566 . . . ?
C1A C1A C2A N1A 172.4(8) 3_566 . . . ?
C2A N1A C4A C5A 128.7(7) . . . . ?
C3A N1A C4A C5A -56.7(8) . . . . ?
C2A N1A C4A C9A -53.1(9) . . . . ?
C3A N1A C4A C9A 121.4(7) . . . . ?
C9A C4A C5A C6A 2.4(9) . . . . ?
N1A C4A C5A C6A -179.4(6) . . . . ?
C4A C5A C6A C7A 0.2(12) . . . . ?
C5A C6A C7A C8A -2.4(13) . . . . ?
C6A C7A C8A C9A 1.9(12) . . . . ?
C7A C8A C9A C4A 0.7(11) . . . . ?
C5A C4A C9A C8A -2.8(9) . . . . ?
N1A C4A C9A C8A 179.0(6) . . . . ?
C4B N1B C2B O1B -178.9(6) . . . . ?
C3B N1B C2B O1B 5.2(9) . . . . ?
C4B N1B C2B C1B 1.1(9) . . . . ?
C3B N1B C2B C1B -174.8(5) . . . . ?
C1B C1B C2B O1B 1.0(11) 3_666 . . . ?
C1B C1B C2B N1B -179.0(7) 3_666 . . . ?
C2B N1B C4B C5B -105.7(7) . . . . ?
C3B N1B C4B C5B 70.2(7) . . . . ?
C2B N1B C4B C9B 74.6(7) . . . . ?
C3B N1B C4B C9B -109.5(6) . . . . ?
C9B C4B C5B C6B -0.1(8) . . . . ?
N1B C4B C5B C6B -179.8(5) . . . . ?
C4B C5B C6B C7B 0.5(8) . . . . ?
C5B C6B C7B C8B -0.5(9) . . . . ?
C6B C7B C8B C9B 0.2(9) . . . . ?
C5B C4B C9B C8B -0.2(8) . . . . ?
N1B C4B C9B C8B 179.5(5) . . . . ?
C7B C8B C9B C4B 0.2(8) . . . . ?
C4C N1C C2C O1C 178.5(6) . . . . ?
C3C N1C C2C O1C -2.5(8) . . . . ?
C4C N1C C2C C1C -2.8(9) . . . . ?
C3C N1C C2C C1C 176.2(5) . . . . ?
C1C C1C C2C O1C -9.3(10) 3_656 . . . ?
C1C C1C C2C N1C 172.0(7) 3_656 . . . ?
C2C N1C C4C C5C 118.8(7) . . . . ?
C3C N1C C4C C5C -60.2(7) . . . . ?
C2C N1C C4C C9C -64.9(8) . . . . ?
C3C N1C C4C C9C 116.1(6) . . . . ?
C9C C4C C5C C6C -1.0(9) . . . . ?
N1C C4C C5C C6C 175.3(5) . . . . ?
C4C C5C C6C C7C 0.8(9) . . . . ?
C5C C6C C7C C8C -0.3(10) . . . . ?
C6C C7C C8C C9C -0.1(10) . . . . ?
C7C C8C C9C C4C 0.0(9) . . . . ?
C5C C4C C9C C8C 0.6(9) . . . . ?
N1C C4C C9C C8C -175.7(5) . . . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
