# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_TTEPY
_database_code_depnum_ccdc_archive 'CCDC 2024746'
loop_
_audit_author_name
_audit_author_address
'Shuai Ma'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 Br3 N6'
_chemical_formula_sum            'C24 H27 Br3 N6'
_chemical_formula_weight         639.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           160
_space_group_name_H-M_alt        'R 3 m :H'
_space_group_name_Hall           'R 3 -2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   16.647(3)
_cell_length_b                   16.647(3)
_cell_length_c                   7.749(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1859.6(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    299
_cell_measurement_theta_min      4.5660
_cell_measurement_theta_max      27.2440

_exptl_crystal_description       rod
_exptl_crystal_colour            Gold-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             954
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.906
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4159
_diffrn_reflns_number            1042
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.861
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_full        24.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.736
_diffrn_reflns_point_group_measured_fraction_full 0.738
_reflns_number_total             594
_reflns_number_gt                504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.478
_reflns_Friedel_fraction_max     0.481
_reflns_Friedel_fraction_full    0.482

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_computing_publication_material  'Windows Word 2019'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1901P)²+29.9483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dimap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         594
_refine_ls_number_parameters     56
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.2245
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_restrained_S_all      0.866
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.48026(7) 0.51974(7) 0.7699(11) 0.0507(10) Uani 1 2 d S T P . .
N1 N 0.5233(7) 0.4767(7) 0.299(4) 0.054(6) Uani 1 2 d DS T P . .
N2 N 0.4284(11) 0.7142(5) 0.234(2) 0.027(3) Uani 1 2 d S T P . .
C1 C 0.5833(14) 0.4167(14) 0.506(4) 0.079(5) Uani 1 2 d S TU P . .
H1A H 0.606210 0.475887 0.561016 0.118 Uiso 0.5 1 calc R U P . .
H1B H 0.625972 0.394733 0.524547 0.118 Uiso 0.5 1 calc R U P . .
H1C H 0.523923 0.373275 0.553671 0.118 Uiso 0.5 1 calc R U P . .
C2 C 0.573920 0.426080 0.327087 0.054 Uani 1 2 d S TU P . .
H2A H 0.540359 0.365225 0.274114 0.065 Uiso 0.5 1 calc R U P . .
H2B H 0.634775 0.459641 0.274114 0.065 Uiso 0.5 1 calc R U P . .
C3 C 0.5756(12) 0.5721(6) 0.2900(17) 0.043(5) Uani 1 1 d D U . . .
H3 H 0.639694 0.604478 0.302752 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5247(8) 0.6155(14) 0.2606(12) 0.029(4) Uani 1 1 d D U . . .
H4 H 0.557077 0.679686 0.247995 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4292(7) 0.5708(7) 0.249(3) 0.034(5) Uani 1 2 d DS T P . .
C6 C 0.3781(7) 0.6219(7) 0.238(3) 0.028(4) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0364(11) 0.0364(11) 0.0822(16) -0.0011(6) 0.0011(6) 0.0205(11)
N1 0.061(13) 0.061(13) 0.060(13) -0.002(5) 0.002(5) 0.046(13)
N2 0.016(9) 0.022(6) 0.041(8) 0.004(3) 0.009(7) 0.008(4)
C1 0.079(5) 0.079(5) 0.079(5) -0.0015(18) 0.0015(18) 0.040(3)
C2 0.054 0.054 0.054 0.000 0.000 0.027
C3 0.043(5) 0.043(5) 0.044(5) -0.0003(13) -0.0001(13) 0.022(3)
C4 0.029(4) 0.029(4) 0.030(4) 0.0002(13) 0.0000(13) 0.015(2)
C5 0.041(10) 0.041(10) 0.031(9) 0.001(4) -0.001(4) 0.029(11)
C6 0.027(8) 0.027(8) 0.032(8) 0.005(4) -0.005(4) 0.014(9)

_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 C3 1.3797(13) . ?
N1 C3 1.3797(13) 4_665 ?
N1 C2 1.47(2) . ?
N2 C6 1.333(12) 2_665 ?
N2 C6 1.333(12) . ?
C1 C2 1.41(3) . ?
C3 C4 1.3801(13) . ?
C4 C5 1.3802(13) . ?
C5 C6 1.47(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C3 126(3) . 4_665 ?
C3 N1 C2 117.0(13) . . ?
C3 N1 C2 117.0(13) 4_665 . ?
C6 N2 C6 114.1(19) 2_665 . ?
C1 C2 N1 109.6(19) . . ?
N1 C3 C4 114(2) . . ?
C3 C4 C5 125(2) . . ?
C4 C5 C4 115(3) . 4_665 ?
C4 C5 C6 122.2(13) . . ?
C4 C5 C6 122.2(13) 4_665 . ?
N2 C6 N2 125.8(19) . 3_565 ?
N2 C6 C5 117.1(10) . . ?
N2 C6 C5 117.1(10) 3_565 . ?

_refine_diff_density_max         1.056
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.229

_shelx_res_file                  
;
TITL 123_a.res in R3m
    123.res
    created by SHELXL-2016/6 at 14:50:41 on 24-Sep-2020
CELL  0.71073  16.6468  16.6468   7.7488   90.000   90.000  120.000
ZERR   3.000   0.0030   0.0030   0.0025    0.000    0.000    0.000
LATT -3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SYMM -Y, -X, Z
SYMM -X+Y, Y, Z
SYMM X, X-Y, Z
SFAC C  H  N  Br
UNIT 72  81  18  9
OMIT 0 50
L.S. 60
ACTA
BOND
FMAP 2
PLAN 20
FREE C2   C3
DFIX 1.38 0.001 C3 C4 C4 C5 N1 C3
ISOR 0.001 C1
ISOR 0.001 C2
ISOR 0.001 C3
ISOR 0.001 C4
WGHT    0.190100   29.948290
FVAR       0.31286
BR1   4    0.480265    0.519735    0.769866    10.50000    0.03641    0.03641 =
         0.08221   -0.00114    0.00114    0.02046
N1    3    0.523335    0.476665    0.298711    10.50000    0.06112    0.06112 =
         0.05991   -0.00195    0.00195    0.04624
N2    3    0.428420    0.714210    0.234156    10.50000    0.01582    0.02186 =
         0.04082    0.00440    0.00880    0.00791
C1    1    0.583252    0.416748    0.505872    10.50000    0.07905    0.07905 =
         0.07923   -0.00145    0.00145    0.04009
AFIX 137
H1A   2    0.606210    0.475887    0.561016    10.50000   -1.50000
H1B   2    0.625972    0.394733    0.524547    10.50000   -1.50000
H1C   2    0.523923    0.373275    0.553671    10.50000   -1.50000
AFIX   1
C2    1    0.573920    0.426080    0.327087    10.50000    0.05386    0.05386 =
         0.05402    0.00020   -0.00020    0.02687
AFIX  23
H2A   2    0.540359    0.365225    0.274114    10.50000   -1.20000
H2B   2    0.634775    0.459641    0.274114    10.50000   -1.20000
AFIX   0
C3    1    0.575553    0.572109    0.289957    11.00000    0.04275    0.04344 =
         0.04374   -0.00033   -0.00006    0.02182
AFIX  43
H3    2    0.639694    0.604478    0.302752    11.00000   -1.20000
AFIX   0
C4    1    0.524658    0.615537    0.260629    11.00000    0.02941    0.02891 =
         0.02977    0.00020    0.00005    0.01465
AFIX  43
H4    2    0.557077    0.679686    0.247995    11.00000   -1.20000
AFIX   0
C5    1    0.429202    0.570798    0.248664    10.50000    0.04137    0.04137 =
         0.03083    0.00071   -0.00071    0.02871
C6    1    0.378139    0.621861    0.237577    10.50000    0.02676    0.02676 =
         0.03224    0.00450   -0.00450    0.01365
HKLF 4




REM  123_a.res in R3m
REM R1 =  0.0518 for     504 Fo > 4sig(Fo)  and  0.0752 for all     594 data
REM     56 parameters refined using     28 restraints

END

WGHT      0.1611      0.0000

REM Highest difference peak  1.056,  deepest hole -0.944,  1-sigma level  0.229
Q1    1   0.5636  0.4364  0.4206  10.50000  0.05    1.06
Q2    1   0.6023  0.3977  0.2768  10.50000  0.05    1.05
Q3    1   0.6653  0.5473  0.3640  11.00000  0.05    1.01
Q4    1   0.7354  0.4709  0.4880  10.50000  0.05    0.99
Q5    1   0.6012  0.3988  0.1797  10.50000  0.05    0.92
Q6    1   0.6349  0.3651  0.5120  10.50000  0.05    0.92
Q7    1   0.5656  0.5455  0.3440  11.00000  0.05    0.88
Q8    1   0.4996  0.5004  0.6763  10.50000  0.05    0.81
Q9    1   0.6245  0.3755  0.4479  10.50000  0.05    0.77
Q10   1   0.4491  0.4696  0.8289  11.00000  0.05    0.74
Q11   1   0.4632  0.5368  0.3960  10.50000  0.05    0.69
Q12   1   0.6379  0.7138  0.1702  11.00000  0.05    0.68
Q13   1   0.5914  0.4086  0.6521  10.50000  0.05    0.67
Q14   1   0.5477  0.6180  0.3346  11.00000  0.05    0.62
Q15   1   0.7327  0.6436  0.2461  11.00000  0.05    0.61
Q16   1   0.4989  0.3624  0.1434  11.00000  0.05    0.59
Q17   1   0.6986  0.3973  0.2554  10.50000  0.05    0.59
Q18   1   0.7297  0.6567  0.3571  11.00000  0.05    0.57
Q19   1   0.5462  0.4538  0.6987  10.50000  0.05    0.56
Q20   1   0.5423  0.3353  0.3702  11.00000  0.05    0.53
;
_shelx_res_checksum              21854
