# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_zhu2br1
_database_code_depnum_ccdc_archive 'CCDC 1534287'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        br-kz-br
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 Br2 N3'
_chemical_formula_weight         559.30

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0137(9)
_cell_length_b                   11.6967(13)
_cell_length_c                   13.9362(15)
_cell_angle_alpha                72.1240(10)
_cell_angle_beta                 81.6730(10)
_cell_angle_gamma                78.3640(10)
_cell_volume                     1212.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3967
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.22

_exptl_crystal_description       square
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5675
_exptl_absorpt_correction_T_max  0.5987
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8697
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4242
_reflns_number_gt                3427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0375P)²+1.1037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4242
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.13884(5) 0.24342(4) 0.44002(3) 0.06406(14) Uani 1 1 d . . .
Br2 Br -0.38437(6) 1.03454(4) 1.17150(4) 0.07913(16) Uani 1 1 d . . .
C1 C 0.2492(4) 0.5070(3) 0.5504(2) 0.0388(7) Uani 1 1 d . . .
C2 C 0.1981(4) 0.4027(3) 0.5448(2) 0.0412(7) Uani 1 1 d . . .
H2 H 0.1658 0.3442 0.6031 0.049 Uiso 1 1 calc R . .
C4 C 0.2410(4) 0.4751(3) 0.3621(2) 0.0505(8) Uani 1 1 d . . .
H4 H 0.2370 0.4626 0.2998 0.061 Uiso 1 1 calc R . .
C3 C 0.1964(4) 0.3883(3) 0.4509(2) 0.0457(7) Uani 1 1 d . . .
C6 C 0.2969(4) 0.5947(3) 0.4602(2) 0.0416(7) Uani 1 1 d . . .
C5 C 0.2910(4) 0.5796(3) 0.3660(2) 0.0494(8) Uani 1 1 d . . .
H5 H 0.3199 0.6384 0.3070 0.059 Uiso 1 1 calc R . .
C9 C 0.2848(5) 0.9110(3) 0.3976(3) 0.0555(9) Uani 1 1 d . . .
H9A H 0.2324 0.9202 0.4626 0.067 Uiso 1 1 calc R . .
H9B H 0.3438 0.9796 0.3647 0.067 Uiso 1 1 calc R . .
C8 C 0.1468(5) 0.9141(3) 0.3339(3) 0.0619(10) Uani 1 1 d . . .
H8A H 0.0945 0.8417 0.3630 0.074 Uiso 1 1 calc R . .
H8B H 0.1971 0.9137 0.2664 0.074 Uiso 1 1 calc R . .
C10 C 0.4158(4) 0.7933(3) 0.4151(3) 0.0528(8) Uani 1 1 d . . .
H10A H 0.4537 0.7766 0.3507 0.063 Uiso 1 1 calc R . .
H10B H 0.5145 0.8049 0.4417 0.063 Uiso 1 1 calc R . .
C7 C 0.0090(5) 1.0276(4) 0.3271(3) 0.0756(12) Uani 1 1 d . . .
H7A H -0.0488 1.0242 0.3930 0.113 Uiso 1 1 calc R . .
H7B H -0.0720 1.0303 0.2817 0.113 Uiso 1 1 calc R . .
H7C H 0.0615 1.0992 0.3023 0.113 Uiso 1 1 calc R . .
C15 C 0.2526(4) 0.5051(3) 0.7381(2) 0.0387(6) Uani 1 1 d . . .
H15 H 0.2143 0.4312 0.7680 0.046 Uiso 1 1 calc R . .
C14 C 0.2732(3) 0.5508(3) 0.6334(2) 0.0376(6) Uani 1 1 d . . .
C11 C 0.3339(3) 0.6627(3) 0.5889(2) 0.0393(7) Uani 1 1 d . . .
C12 C 0.3718(4) 0.7294(3) 0.6481(2) 0.0451(7) Uani 1 1 d . . .
H12 H 0.4123 0.8026 0.6186 0.054 Uiso 1 1 calc R . .
C16 C 0.2900(4) 0.5713(3) 0.7981(2) 0.0406(7) Uani 1 1 d . . .
C13 C 0.3472(4) 0.6830(3) 0.7518(2) 0.0450(7) Uani 1 1 d . . .
H13 H 0.3692 0.7272 0.7924 0.054 Uiso 1 1 calc R . .
C17 C 0.2721(4) 0.5246(3) 0.9100(2) 0.0416(7) Uani 1 1 d . . .
C20 C -0.0212(4) 0.7863(3) 0.9951(2) 0.0454(7) Uani 1 1 d . . .
C19 C 0.0791(4) 0.7076(3) 0.9362(2) 0.0479(8) Uani 1 1 d . . .
H19 H 0.0702 0.7341 0.8668 0.057 Uiso 1 1 calc R . .
C18 C 0.1819(4) 0.6021(3) 0.9713(2) 0.0497(8) Uani 1 1 d . . .
H18 H 0.1969 0.5763 1.0401 0.060 Uiso 1 1 calc R . .
C25 C -0.2311(4) 0.9359(3) 1.0997(3) 0.0518(8) Uani 1 1 d . . .
C24 C -0.2449(5) 0.9589(3) 0.9991(3) 0.0568(9) Uani 1 1 d . . .
H24 H -0.3231 1.0240 0.9657 0.068 Uiso 1 1 calc R . .
C22 C -0.1122(5) 0.8420(3) 1.1505(3) 0.0567(9) Uani 1 1 d . . .
H22 H -0.1030 0.8287 1.2190 0.068 Uiso 1 1 calc R . .
C21 C -0.0066(4) 0.7680(3) 1.0974(3) 0.0540(8) Uani 1 1 d . . .
H21 H 0.0751 0.7053 1.1305 0.065 Uiso 1 1 calc R . .
C23 C -0.1405(5) 0.8836(3) 0.9477(3) 0.0562(9) Uani 1 1 d . . .
H23 H -0.1503 0.8986 0.8791 0.067 Uiso 1 1 calc R . .
C27 C 0.3171(4) 0.3570(3) 1.0659(3) 0.0469(7) Uani 1 1 d . . .
C26 C 0.4505(4) 0.3263(3) 0.9068(2) 0.0478(8) Uani 1 1 d . . .
N1 N 0.3486(3) 0.6882(2) 0.48501(19) 0.0443(6) Uani 1 1 d . . .
N2 N 0.5404(4) 0.2593(3) 0.8695(2) 0.0688(9) Uani 1 1 d . . .
N3 N 0.2960(4) 0.3180(3) 1.1512(2) 0.0702(9) Uani 1 1 d . . .
C28 C 0.3436(4) 0.4072(3) 0.9577(2) 0.0431(7) Uani 1 1 d . . .


_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 C3 1.898(3) . ?
Br2 C25 1.903(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.417(4) . ?
C1 C14 1.452(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C4 C5 1.379(5) . ?
C4 C3 1.392(5) . ?
C4 H4 0.9300 . ?
C6 C5 1.386(4) . ?
C6 N1 1.394(4) . ?
C5 H5 0.9300 . ?
C9 C8 1.504(5) . ?
C9 C10 1.530(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C7 1.533(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 N1 1.459(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 C14 1.388(4) . ?
C15 C16 1.397(4) . ?
C15 H15 0.9300 . ?
C14 C11 1.416(4) . ?
C11 N1 1.379(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C16 C13 1.405(4) . ?
C16 C17 1.482(4) . ?
C13 H13 0.9300 . ?
C17 C28 1.374(4) . ?
C17 C18 1.451(4) . ?
C20 C23 1.389(4) . ?
C20 C21 1.393(5) . ?
C20 C19 1.463(4) . ?
C19 C18 1.333(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C25 C24 1.360(5) . ?
C25 C22 1.383(5) . ?
C24 C23 1.380(5) . ?
C24 H24 0.9300 . ?
C22 C21 1.390(5) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C27 N3 1.135(4) . ?
C27 C28 1.441(5) . ?
C26 N2 1.149(4) . ?
C26 C28 1.429(4) . ?

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 C1 C6 119.6(3) . . ?
C2 C1 C14 134.0(3) . . ?
C6 C1 C14 106.4(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 122.3(3) . . ?
C2 C3 Br1 119.6(2) . . ?
C4 C3 Br1 118.1(2) . . ?
C5 C6 N1 129.6(3) . . ?
C5 C6 C1 121.2(3) . . ?
N1 C6 C1 109.1(3) . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C8 C9 C10 113.3(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C8 C7 111.5(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C10 C9 113.2(3) . . ?
N1 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C14 C11 119.7(3) . . ?
C15 C14 C1 133.9(3) . . ?
C11 C14 C1 106.4(3) . . ?
N1 C11 C12 129.1(3) . . ?
N1 C11 C14 109.6(3) . . ?
C12 C11 C14 121.4(3) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C15 C16 C13 119.6(3) . . ?
C15 C16 C17 121.0(3) . . ?
C13 C16 C17 119.4(3) . . ?
C12 C13 C16 122.2(3) . . ?
C12 C13 H13 118.9 . . ?
C16 C13 H13 118.9 . . ?
C28 C17 C18 118.8(3) . . ?
C28 C17 C16 120.3(3) . . ?
C18 C17 C16 120.9(3) . . ?
C23 C20 C21 117.6(3) . . ?
C23 C20 C19 118.6(3) . . ?
C21 C20 C19 123.7(3) . . ?
C18 C19 C20 127.0(3) . . ?
C18 C19 H19 116.5 . . ?
C20 C19 H19 116.5 . . ?
C19 C18 C17 124.7(3) . . ?
C19 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
C24 C25 C22 121.8(3) . . ?
C24 C25 Br2 118.4(3) . . ?
C22 C25 Br2 119.8(3) . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C25 C22 C21 118.8(3) . . ?
C25 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C24 C23 C20 122.1(3) . . ?
C24 C23 H23 119.0 . . ?
C20 C23 H23 119.0 . . ?
N3 C27 C28 179.7(4) . . ?
N2 C26 C28 177.1(3) . . ?
C11 N1 C6 108.5(2) . . ?
C11 N1 C10 124.4(3) . . ?
C6 N1 C10 127.0(3) . . ?
C17 C28 C26 124.1(3) . . ?
C17 C28 C27 121.2(3) . . ?
C26 C28 C27 114.6(3) . . ?

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
C6 C1 C2 C3 0.3(4) . . . . ?
C14 C1 C2 C3 -177.2(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 Br1 176.8(2) . . . . ?
C5 C4 C3 C2 0.8(5) . . . . ?
C5 C4 C3 Br1 -177.2(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C14 C1 C6 C5 179.2(3) . . . . ?
C2 C1 C6 N1 -177.9(2) . . . . ?
C14 C1 C6 N1 0.2(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
N1 C6 C5 C4 177.3(3) . . . . ?
C1 C6 C5 C4 -1.5(4) . . . . ?
C10 C9 C8 C7 174.3(3) . . . . ?
C8 C9 C10 N1 -72.5(4) . . . . ?
C16 C15 C14 C11 0.9(4) . . . . ?
C16 C15 C14 C1 179.1(3) . . . . ?
C2 C1 C14 C15 -0.6(6) . . . . ?
C6 C1 C14 C15 -178.3(3) . . . . ?
C2 C1 C14 C11 177.8(3) . . . . ?
C6 C1 C14 C11 0.1(3) . . . . ?
C15 C14 C11 N1 178.3(2) . . . . ?
C1 C14 C11 N1 -0.4(3) . . . . ?
C15 C14 C11 C12 -0.8(4) . . . . ?
C1 C14 C11 C12 -179.5(3) . . . . ?
N1 C11 C12 C13 -179.3(3) . . . . ?
C14 C11 C12 C13 -0.4(4) . . . . ?
C14 C15 C16 C13 0.2(4) . . . . ?
C14 C15 C16 C17 -179.1(3) . . . . ?
C11 C12 C13 C16 1.6(4) . . . . ?
C15 C16 C13 C12 -1.5(4) . . . . ?
C17 C16 C13 C12 177.8(3) . . . . ?
C15 C16 C17 C28 49.5(4) . . . . ?
C13 C16 C17 C28 -129.8(3) . . . . ?
C15 C16 C17 C18 -131.6(3) . . . . ?
C13 C16 C17 C18 49.1(4) . . . . ?
C23 C20 C19 C18 -170.6(4) . . . . ?
C21 C20 C19 C18 8.2(6) . . . . ?
C20 C19 C18 C17 176.8(3) . . . . ?
C28 C17 C18 C19 -166.0(3) . . . . ?
C16 C17 C18 C19 15.1(5) . . . . ?
C22 C25 C24 C23 2.1(5) . . . . ?
Br2 C25 C24 C23 -176.5(3) . . . . ?
C24 C25 C22 C21 -1.3(5) . . . . ?
Br2 C25 C22 C21 177.3(3) . . . . ?
C25 C22 C21 C20 -1.0(5) . . . . ?
C23 C20 C21 C22 2.3(5) . . . . ?
C19 C20 C21 C22 -176.4(3) . . . . ?
C25 C24 C23 C20 -0.6(6) . . . . ?
C21 C20 C23 C24 -1.6(5) . . . . ?
C19 C20 C23 C24 177.3(3) . . . . ?
C12 C11 N1 C6 179.5(3) . . . . ?
C14 C11 N1 C6 0.5(3) . . . . ?
C12 C11 N1 C10 2.3(5) . . . . ?
C14 C11 N1 C10 -176.7(3) . . . . ?
C5 C6 N1 C11 -179.3(3) . . . . ?
C1 C6 N1 C11 -0.5(3) . . . . ?
C5 C6 N1 C10 -2.2(5) . . . . ?
C1 C6 N1 C10 176.7(3) . . . . ?
C9 C10 N1 C11 -80.0(4) . . . . ?
C9 C10 N1 C6 103.3(4) . . . . ?
C18 C17 C28 C26 -173.1(3) . . . . ?
C16 C17 C28 C26 5.9(5) . . . . ?
C18 C17 C28 C27 5.7(5) . . . . ?
C16 C17 C28 C27 -175.3(3) . . . . ?
N2 C26 C28 C17 144(7) . . . . ?
N2 C26 C28 C27 -34(8) . . . . ?
N3 C27 C28 C17 -21(82) . . . . ?
N3 C27 C28 C26 158(100) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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 2015186'
loop_
_audit_author_name
_audit_author_address
'Pengfei Chen'
;ANHUI UNIVERSITY
China
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_audit_creation_date             2019-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C28 H20 Br3 N3)'
_chemical_formula_sum            'C56 H40 Br6 N6'
_chemical_formula_weight         1276.40
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3087(4)
_cell_length_b                   11.5980(7)
_cell_length_c                   14.7149(8)
_cell_angle_alpha                98.253(5)
_cell_angle_beta                 93.797(5)
_cell_angle_gamma                100.037(5)
_cell_volume                     1210.18(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   70.05
_shelx_estimated_absorpt_T_min   23.84
_exptl_absorpt_coefficient_mu    6.354
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block-shaped
_exptl_crystal_F_000             628
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10044
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.813
_diffrn_reflns_theta_min         3.920
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3381
_reflns_number_total             4366
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C14(H14A,H14B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C3(H3), C24(H24), C21(H21), C11(H11), C22(H22), C12(H12), C27(H27),
 C2(H2), C6(H6), C9(H9), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br3 Br 1.10668(6) 1.35663(4) 1.05817(3) 0.02487(13) Uani 1 1 d . . . . .
Br1 Br 0.20618(6) 0.11778(4) 0.40267(3) 0.02430(13) Uani 1 1 d . . . . .
Br2 Br 0.75503(6) 0.89380(4) 0.32472(3) 0.02994(14) Uani 1 1 d . . . . .
N3 N 0.2107(4) 0.6429(3) 0.4565(2) 0.0175(7) Uani 1 1 d . . . . .
C5 C 0.2670(5) 0.4747(3) 0.5074(3) 0.0153(8) Uani 1 1 d . . . . .
C23 C 0.7598(5) 0.9929(3) 0.9079(3) 0.0163(8) Uani 1 1 d . . . . .
C10 C 0.3749(5) 0.6861(3) 0.7367(3) 0.0166(8) Uani 1 1 d . . . . .
C25 C 0.8677(5) 1.1329(4) 1.0486(3) 0.0204(8) Uani 1 1 d . . . . .
H25 H 0.868661 1.153614 1.112054 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2086(5) 0.5218(3) 0.4303(3) 0.0169(8) Uani 1 1 d . . . . .
N1 N 0.4122(5) 0.6169(3) 1.0607(3) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.3047(5) 0.5705(3) 0.5851(3) 0.0146(8) Uani 1 1 d . . . . .
C3 C 0.1566(5) 0.4516(4) 0.3439(3) 0.0204(8) Uani 1 1 d . . . . .
H3 H 0.121527 0.484326 0.292787 0.024 Uiso 1 1 calc R . . . .
C24 C 0.7629(5) 1.0263(3) 1.0030(3) 0.0185(8) Uani 1 1 d . . . . .
H24 H 0.692847 0.975801 1.036744 0.022 Uiso 1 1 calc R . . . .
C21 C 0.5341(5) 0.8011(3) 0.8907(3) 0.0171(8) Uani 1 1 d . . . . .
H21 H 0.527496 0.812768 0.954133 0.021 Uiso 1 1 calc R . . . .
C17 C 0.4199(5) 0.6943(3) 0.8370(3) 0.0165(8) Uani 1 1 d . . . . .
C11 C 0.3311(5) 0.7852(3) 0.6999(3) 0.0176(8) Uani 1 1 d . . . . .
H11 H 0.337480 0.856180 0.739419 0.021 Uiso 1 1 calc R . . . .
C22 C 0.6480(5) 0.8841(3) 0.8556(3) 0.0177(8) Uani 1 1 d . . . . .
H22 H 0.656374 0.870938 0.792337 0.021 Uiso 1 1 calc R . . . .
C1 C 0.2143(5) 0.2844(3) 0.4142(3) 0.0178(8) Uani 1 1 d . . . . .
N2 N 0.1223(5) 0.4128(3) 0.8081(2) 0.0256(8) Uani 1 1 d . . . . .
C12 C 0.2792(5) 0.7801(3) 0.6074(3) 0.0168(8) Uani 1 1 d . . . . .
H12 H 0.253737 0.846706 0.584161 0.020 Uiso 1 1 calc R . . . .
C8 C 0.2662(5) 0.6719(4) 0.5498(3) 0.0177(8) Uani 1 1 d . . . . .
C26 C 0.9714(5) 1.2082(3) 0.9974(3) 0.0197(8) Uani 1 1 d . . . . .
C18 C 0.3501(5) 0.6047(3) 0.8840(3) 0.0168(8) Uani 1 1 d . . . . .
C20 C 0.3875(5) 0.6122(3) 0.9816(3) 0.0189(8) Uani 1 1 d . . . . .
C27 C 0.9744(6) 1.1778(4) 0.9039(3) 0.0227(9) Uani 1 1 d . . . . .
H27 H 1.044521 1.228950 0.870631 0.027 Uiso 1 1 calc R . . . .
C19 C 0.2254(5) 0.4982(4) 0.8408(3) 0.0186(8) Uani 1 1 d . . . . .
C13 C 0.1467(5) 0.7238(4) 0.3995(3) 0.0194(8) Uani 1 1 d . . . . .
H13A H 0.078147 0.774939 0.436154 0.023 Uiso 1 1 calc R . . . .
H13B H 0.061188 0.677842 0.348702 0.023 Uiso 1 1 calc R . . . .
C2 C 0.1591(5) 0.3330(4) 0.3372(3) 0.0185(8) Uani 1 1 d . . . . .
H2 H 0.123666 0.283929 0.280730 0.022 Uiso 1 1 calc R . . . .
C6 C 0.2678(5) 0.3532(3) 0.4995(3) 0.0189(8) Uani 1 1 d . . . . .
H6 H 0.303295 0.319860 0.550125 0.023 Uiso 1 1 calc R . . . .
C9 C 0.3620(5) 0.5786(3) 0.6770(3) 0.0153(8) Uani 1 1 d . . . . .
H9 H 0.392177 0.512804 0.699683 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3996(6) 0.7320(4) 0.2877(3) 0.0249(9) Uani 1 1 d . . . . .
H15A H 0.460949 0.676932 0.316539 0.030 Uiso 1 1 calc R . . . .
H15B H 0.304461 0.685571 0.241264 0.030 Uiso 1 1 calc R . . . .
C14 C 0.3048(6) 0.8010(4) 0.3605(3) 0.0209(8) Uani 1 1 d . . . . .
H14A H 0.254967 0.862020 0.333647 0.025 Uiso 1 1 calc R . . . .
H14B H 0.397491 0.840089 0.410695 0.025 Uiso 1 1 calc R . . . .
C28 C 0.8721(6) 1.0705(4) 0.8599(3) 0.0224(9) Uani 1 1 d . . . . .
H28 H 0.877554 1.048914 0.796893 0.027 Uiso 1 1 calc R . . . .
C16 C 0.5425(6) 0.8078(4) 0.2401(3) 0.0294(10) Uani 1 1 d . . . . .
H16A H 0.482814 0.864268 0.212148 0.035 Uiso 1 1 calc R . . . .
H16B H 0.586869 0.757448 0.191193 0.035 Uiso 1 1 calc R . . . .


_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
Br3 C26 1.895(4) . ?
Br1 C1 1.905(4) . ?
Br2 C16 1.951(4) . ?
N3 C4 1.399(5) . ?
N3 C8 1.382(5) . ?
N3 C13 1.459(5) . ?
C5 C4 1.401(6) . ?
C5 C7 1.452(5) . ?
C5 C6 1.398(5) . ?
C23 C24 1.395(6) . ?
C23 C22 1.460(5) . ?
C23 C28 1.409(6) . ?
C10 C17 1.477(5) . ?
C10 C11 1.414(5) . ?
C10 C9 1.403(5) . ?
C25 C24 1.390(5) . ?
C25 C26 1.392(6) . ?
C4 C3 1.399(5) . ?
N1 C20 1.158(5) . ?
C7 C8 1.415(6) . ?
C7 C9 1.374(5) . ?
C3 C2 1.368(6) . ?
C21 C17 1.459(5) . ?
C21 C22 1.343(6) . ?
C17 C18 1.373(6) . ?
C11 C12 1.378(6) . ?
C1 C2 1.403(6) . ?
C1 C6 1.380(5) . ?
N2 C19 1.156(5) . ?
C12 C8 1.395(5) . ?
C26 C27 1.372(6) . ?
C18 C20 1.431(6) . ?
C18 C19 1.438(5) . ?
C27 C28 1.382(6) . ?
C13 C14 1.530(6) . ?
C15 C14 1.521(6) . ?
C15 C16 1.520(6) . ?

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
C4 N3 C13 127.0(3) . . ?
C8 N3 C4 108.1(3) . . ?
C8 N3 C13 124.6(3) . . ?
C4 C5 C7 107.3(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 C7 132.8(4) . . ?
C24 C23 C22 124.4(4) . . ?
C24 C23 C28 117.2(3) . . ?
C28 C23 C22 118.5(4) . . ?
C11 C10 C17 120.2(3) . . ?
C9 C10 C17 121.0(4) . . ?
C9 C10 C11 118.6(3) . . ?
C24 C25 C26 118.7(4) . . ?
N3 C4 C5 109.0(3) . . ?
N3 C4 C3 129.0(4) . . ?
C3 C4 C5 122.0(4) . . ?
C8 C7 C5 105.6(3) . . ?
C9 C7 C5 134.3(4) . . ?
C9 C7 C8 120.0(3) . . ?
C2 C3 C4 117.6(4) . . ?
C25 C24 C23 121.8(4) . . ?
C22 C21 C17 125.2(4) . . ?
C21 C17 C10 120.7(3) . . ?
C18 C17 C10 121.8(3) . . ?
C18 C17 C21 117.4(4) . . ?
C12 C11 C10 122.3(4) . . ?
C21 C22 C23 126.0(4) . . ?
C2 C1 Br1 119.4(3) . . ?
C6 C1 Br1 118.7(3) . . ?
C6 C1 C2 121.8(4) . . ?
C11 C12 C8 117.8(4) . . ?
N3 C8 C7 109.9(3) . . ?
N3 C8 C12 128.9(4) . . ?
C12 C8 C7 121.2(3) . . ?
C25 C26 Br3 119.0(3) . . ?
C27 C26 Br3 119.7(3) . . ?
C27 C26 C25 121.3(4) . . ?
C17 C18 C20 122.7(3) . . ?
C17 C18 C19 123.2(3) . . ?
C20 C18 C19 114.0(3) . . ?
N1 C20 C18 178.0(4) . . ?
C26 C27 C28 119.3(4) . . ?
N2 C19 C18 178.1(4) . . ?
N3 C13 C14 113.7(3) . . ?
C3 C2 C1 120.9(4) . . ?
C1 C6 C5 117.9(4) . . ?
C7 C9 C10 120.0(4) . . ?
C16 C15 C14 114.8(4) . . ?
C15 C14 C13 113.6(3) . . ?
C27 C28 C23 121.7(4) . . ?
C15 C16 Br2 112.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_brkznbr2
_database_code_depnum_ccdc_archive 'CCDC 1540851'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        brkznbr2
_chemical_name_common            zhu06
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H27 Br N4'
_chemical_formula_weight         523.47

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.509(9)
_cell_length_b                   12.679(7)
_cell_length_c                   12.592(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.956(7)
_cell_angle_gamma                90.00
_cell_volume                     2688(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6202
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.73

_exptl_crystal_description       bulk
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_T_max  0.7781
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18523
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4735
_reflns_number_gt                3396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.1281P)²+2.8648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4735
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2285
_refine_ls_wR_factor_gt          0.2071
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.06563(4) 0.38966(6) 0.67213(6) 0.1013(4) Uani 1 1 d . . .
C2 C 0.9505(3) 0.4737(4) 0.7694(4) 0.0576(11) Uani 1 1 d . . .
H2 H 0.9397 0.5217 0.7114 0.069 Uiso 1 1 calc R . .
C1 C 0.9093(2) 0.4776(3) 0.8500(3) 0.0500(10) Uani 1 1 d . . .
C3 C 1.0074(3) 0.3970(4) 0.7782(5) 0.0684(14) Uani 1 1 d . . .
C6 C 0.9271(3) 0.4058(4) 0.9384(4) 0.0581(12) Uani 1 1 d . . .
C4 C 1.0246(3) 0.3231(5) 0.8662(6) 0.0823(17) Uani 1 1 d . . .
H4 H 1.0634 0.2721 0.8699 0.099 Uiso 1 1 calc R . .
C5 C 0.9848(3) 0.3261(4) 0.9459(5) 0.0770(16) Uani 1 1 d . . .
H5 H 0.9954 0.2771 1.0031 0.092 Uiso 1 1 calc R . .
C10 C 0.8787(4) 0.3685(4) 1.1072(4) 0.0739(15) Uani 1 1 d . . .
H10A H 0.8712 0.4171 1.1630 0.089 Uiso 1 1 calc R . .
H10B H 0.9293 0.3334 1.1367 0.089 Uiso 1 1 calc R . .
C8 C 0.7988(4) 0.2350(5) 1.1820(6) 0.098(2) Uani 1 1 d . . .
H8A H 0.7821 0.2880 1.2266 0.117 Uiso 1 1 calc R . .
H8B H 0.8486 0.2053 1.2260 0.117 Uiso 1 1 calc R . .
C9 C 0.8125(4) 0.2864(6) 1.0841(6) 0.097(2) Uani 1 1 d . . .
H9A H 0.7635 0.3201 1.0432 0.117 Uiso 1 1 calc R . .
H9B H 0.8248 0.2323 1.0369 0.117 Uiso 1 1 calc R . .
C7 C 0.7371(5) 0.1488(7) 1.1545(9) 0.144(4) Uani 1 1 d . . .
H7A H 0.6893 0.1757 1.1049 0.217 Uiso 1 1 calc R . .
H7B H 0.7262 0.1246 1.2211 0.217 Uiso 1 1 calc R . .
H7C H 0.7567 0.0911 1.1201 0.217 Uiso 1 1 calc R . .
C16 C 0.7529(2) 0.6853(3) 0.8510(3) 0.0432(9) Uani 1 1 d . . .
C11 C 0.8484(2) 0.5469(3) 0.8677(3) 0.0449(9) Uani 1 1 d . . .
C12 C 0.8076(2) 0.6321(3) 0.8090(3) 0.0431(9) Uani 1 1 d . . .
H12 H 0.8168 0.6530 0.7428 0.052 Uiso 1 1 calc R . .
C14 C 0.7781(3) 0.5672(4) 1.0097(4) 0.0566(11) Uani 1 1 d . . .
H14 H 0.7676 0.5457 1.0749 0.068 Uiso 1 1 calc R . .
C13 C 0.8336(3) 0.5132(3) 0.9671(3) 0.0503(10) Uani 1 1 d . . .
C15 C 0.7402(3) 0.6525(4) 0.9515(4) 0.0546(11) Uani 1 1 d . . .
H15 H 0.7046 0.6903 0.9797 0.066 Uiso 1 1 calc R . .
C18 C 0.7267(3) 0.8766(3) 0.8416(4) 0.0520(10) Uani 1 1 d . . .
C17 C 0.7112(2) 0.7798(3) 0.7926(3) 0.0443(9) Uani 1 1 d . . .
C19 C 0.6924(3) 0.9714(4) 0.7861(4) 0.0656(13) Uani 1 1 d . . .
C20 C 0.7812(3) 0.8898(4) 0.9491(5) 0.0631(12) Uani 1 1 d . . .
C21 C 0.6568(2) 0.7697(3) 0.6841(3) 0.0487(10) Uani 1 1 d . . .
H21 H 0.6348 0.8317 0.6493 0.058 Uiso 1 1 calc R . .
C22 C 0.6349(2) 0.6797(3) 0.6286(3) 0.0470(10) Uani 1 1 d . . .
H22 H 0.6560 0.6178 0.6644 0.056 Uiso 1 1 calc R . .
C23 C 0.5817(2) 0.6688(3) 0.5186(3) 0.0476(10) Uani 1 1 d . . .
C26 C 0.5720(3) 0.5712(4) 0.4642(4) 0.0539(11) Uani 1 1 d . . .
H26 H 0.5984 0.5127 0.5013 0.065 Uiso 1 1 calc R . .
C24 C 0.5383(3) 0.7533(4) 0.4592(4) 0.0558(11) Uani 1 1 d . . .
H24 H 0.5420 0.8190 0.4930 0.067 Uiso 1 1 calc R . .
C28 C 0.4839(3) 0.6444(4) 0.2984(4) 0.0564(11) Uani 1 1 d . . .
C25 C 0.4907(3) 0.7427(4) 0.3536(4) 0.0632(12) Uani 1 1 d . . .
H25 H 0.4626 0.8007 0.3177 0.076 Uiso 1 1 calc R . .
C27 C 0.5248(3) 0.5589(4) 0.3575(4) 0.0595(12) Uani 1 1 d . . .
H27 H 0.5200 0.4927 0.3245 0.071 Uiso 1 1 calc R . .
C30 C 0.4324(5) 0.5335(5) 0.1352(5) 0.102(2) Uani 1 1 d . . .
H30A H 0.4843 0.5060 0.1397 0.154 Uiso 1 1 calc R . .
H30B H 0.4032 0.5417 0.0591 0.154 Uiso 1 1 calc R . .
H30C H 0.4047 0.4854 0.1704 0.154 Uiso 1 1 calc R . .
C29 C 0.3986(4) 0.7248(6) 0.1300(5) 0.098(2) Uani 1 1 d . . .
H29A H 0.3590 0.7490 0.1642 0.147 Uiso 1 1 calc R . .
H29B H 0.3734 0.7044 0.0552 0.147 Uiso 1 1 calc R . .
H29C H 0.4358 0.7806 0.1306 0.147 Uiso 1 1 calc R . .
N1 N 0.8809(2) 0.4279(3) 1.0089(3) 0.0608(10) Uani 1 1 d . . .
N2 N 0.6655(4) 1.0456(4) 0.7369(5) 0.0971(16) Uani 1 1 d . . .
N4 N 0.4399(3) 0.6354(4) 0.1905(4) 0.0770(13) Uani 1 1 d . . .
N3 N 0.8251(4) 0.9009(4) 1.0342(4) 0.0898(16) Uani 1 1 d . . .


_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 C3 1.892(6) . ?
C2 C3 1.374(7) . ?
C2 C1 1.398(6) . ?
C2 H2 0.9300 . ?
C1 C6 1.406(6) . ?
C1 C11 1.445(6) . ?
C3 C4 1.419(9) . ?
C6 N1 1.384(7) . ?
C6 C5 1.413(7) . ?
C4 C5 1.371(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C10 N1 1.459(6) . ?
C10 C9 1.525(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 C9 1.471(9) . ?
C8 C7 1.509(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C16 C12 1.390(5) . ?
C16 C15 1.407(6) . ?
C16 C17 1.487(6) . ?
C11 C12 1.390(6) . ?
C11 C13 1.414(6) . ?
C12 H12 0.9300 . ?
C14 C15 1.371(7) . ?
C14 C13 1.409(6) . ?
C14 H14 0.9300 . ?
C13 N1 1.376(6) . ?
C15 H15 0.9300 . ?
C18 C17 1.367(6) . ?
C18 C19 1.436(7) . ?
C18 C20 1.436(8) . ?
C17 C21 1.441(6) . ?
C19 N2 1.154(7) . ?
C20 N3 1.143(7) . ?
C21 C22 1.338(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.448(6) . ?
C22 H22 0.9300 . ?
C23 C26 1.402(6) . ?
C23 C24 1.404(6) . ?
C26 C27 1.379(6) . ?
C26 H26 0.9300 . ?
C24 C25 1.368(7) . ?
C24 H24 0.9300 . ?
C28 N4 1.370(6) . ?
C28 C27 1.396(7) . ?
C28 C25 1.417(7) . ?
C25 H25 0.9300 . ?
C27 H27 0.9300 . ?
C30 N4 1.457(8) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 N4 1.444(8) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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 C2 C1 118.3(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 C11 133.1(4) . . ?
C6 C1 C11 106.5(4) . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 Br1 119.8(5) . . ?
C4 C3 Br1 118.6(4) . . ?
N1 C6 C1 109.6(4) . . ?
N1 C6 C5 129.4(5) . . ?
C1 C6 C5 121.0(5) . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 117.9(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C10 C9 112.7(5) . . ?
N1 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C9 C8 C7 113.5(7) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 115.6(6) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C16 C15 119.7(4) . . ?
C12 C16 C17 119.9(3) . . ?
C15 C16 C17 120.3(4) . . ?
C12 C11 C13 120.8(4) . . ?
C12 C11 C1 133.1(4) . . ?
C13 C11 C1 106.0(4) . . ?
C11 C12 C16 118.9(4) . . ?
C11 C12 H12 120.6 . . ?
C16 C12 H12 120.6 . . ?
C15 C14 C13 117.6(4) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
N1 C13 C14 129.9(4) . . ?
N1 C13 C11 109.7(4) . . ?
C14 C13 C11 120.3(4) . . ?
C14 C15 C16 122.7(4) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C18 C19 121.9(4) . . ?
C17 C18 C20 121.9(4) . . ?
C19 C18 C20 116.2(4) . . ?
C18 C17 C21 120.3(4) . . ?
C18 C17 C16 119.4(4) . . ?
C21 C17 C16 120.3(4) . . ?
N2 C19 C18 176.7(6) . . ?
N3 C20 C18 179.4(6) . . ?
C22 C21 C17 126.2(4) . . ?
C22 C21 H21 116.9 . . ?
C17 C21 H21 116.9 . . ?
C21 C22 C23 126.7(4) . . ?
C21 C22 H22 116.6 . . ?
C23 C22 H22 116.6 . . ?
C26 C23 C24 116.0(4) . . ?
C26 C23 C22 120.8(4) . . ?
C24 C23 C22 123.2(4) . . ?
C27 C26 C23 122.4(4) . . ?
C27 C26 H26 118.8 . . ?
C23 C26 H26 118.8 . . ?
C25 C24 C23 122.6(4) . . ?
C25 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
N4 C28 C27 122.0(5) . . ?
N4 C28 C25 120.6(4) . . ?
C27 C28 C25 117.4(4) . . ?
C24 C25 C28 120.7(4) . . ?
C24 C25 H25 119.7 . . ?
C28 C25 H25 119.7 . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
N4 C30 H30A 109.5 . . ?
N4 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N4 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N4 C29 H29A 109.5 . . ?
N4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C13 N1 C6 108.1(4) . . ?
C13 N1 C10 125.2(5) . . ?
C6 N1 C10 126.6(4) . . ?
C28 N4 C29 121.4(5) . . ?
C28 N4 C30 120.0(5) . . ?
C29 N4 C30 118.6(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
C3 C2 C1 C6 1.1(6) . . . . ?
C3 C2 C1 C11 178.6(4) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C2 C3 Br1 -179.2(3) . . . . ?
C2 C1 C6 N1 177.7(4) . . . . ?
C11 C1 C6 N1 -0.4(5) . . . . ?
C2 C1 C6 C5 -2.2(7) . . . . ?
C11 C1 C6 C5 179.8(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
Br1 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
N1 C6 C5 C4 -177.8(5) . . . . ?
C1 C6 C5 C4 2.0(7) . . . . ?
C7 C8 C9 C10 -175.6(7) . . . . ?
N1 C10 C9 C8 -170.9(6) . . . . ?
C2 C1 C11 C12 2.3(8) . . . . ?
C6 C1 C11 C12 -179.9(4) . . . . ?
C2 C1 C11 C13 -177.1(5) . . . . ?
C6 C1 C11 C13 0.6(4) . . . . ?
C13 C11 C12 C16 1.4(6) . . . . ?
C1 C11 C12 C16 -178.0(4) . . . . ?
C15 C16 C12 C11 0.2(6) . . . . ?
C17 C16 C12 C11 177.2(4) . . . . ?
C15 C14 C13 N1 178.3(4) . . . . ?
C15 C14 C13 C11 -0.3(7) . . . . ?
C12 C11 C13 N1 179.8(4) . . . . ?
C1 C11 C13 N1 -0.7(5) . . . . ?
C12 C11 C13 C14 -1.4(6) . . . . ?
C1 C11 C13 C14 178.2(4) . . . . ?
C13 C14 C15 C16 1.9(7) . . . . ?
C12 C16 C15 C14 -1.9(7) . . . . ?
C17 C16 C15 C14 -178.8(4) . . . . ?
C19 C18 C17 C21 -2.6(6) . . . . ?
C20 C18 C17 C21 -179.3(4) . . . . ?
C19 C18 C17 C16 175.6(4) . . . . ?
C20 C18 C17 C16 -1.0(6) . . . . ?
C12 C16 C17 C18 -112.7(4) . . . . ?
C15 C16 C17 C18 64.2(5) . . . . ?
C12 C16 C17 C21 65.5(5) . . . . ?
C15 C16 C17 C21 -117.6(4) . . . . ?
C17 C18 C19 N2 -39(11) . . . . ?
C20 C18 C19 N2 138(10) . . . . ?
C17 C18 C20 N3 121(72) . . . . ?
C19 C18 C20 N3 -56(72) . . . . ?
C18 C17 C21 C22 -177.9(4) . . . . ?
C16 C17 C21 C22 3.9(6) . . . . ?
C17 C21 C22 C23 -178.5(4) . . . . ?
C21 C22 C23 C26 171.3(4) . . . . ?
C21 C22 C23 C24 -7.4(7) . . . . ?
C24 C23 C26 C27 1.9(6) . . . . ?
C22 C23 C26 C27 -176.9(4) . . . . ?
C26 C23 C24 C25 -1.5(7) . . . . ?
C22 C23 C24 C25 177.3(4) . . . . ?
C23 C24 C25 C28 -0.7(8) . . . . ?
N4 C28 C25 C24 -176.2(5) . . . . ?
C27 C28 C25 C24 2.6(7) . . . . ?
C23 C26 C27 C28 0.0(7) . . . . ?
N4 C28 C27 C26 176.5(5) . . . . ?
C25 C28 C27 C26 -2.2(7) . . . . ?
C14 C13 N1 C6 -178.2(5) . . . . ?
C11 C13 N1 C6 0.5(5) . . . . ?
C14 C13 N1 C10 4.9(8) . . . . ?
C11 C13 N1 C10 -176.4(4) . . . . ?
C1 C6 N1 C13 -0.1(5) . . . . ?
C5 C6 N1 C13 179.8(5) . . . . ?
C1 C6 N1 C10 176.8(4) . . . . ?
C5 C6 N1 C10 -3.4(8) . . . . ?
C9 C10 N1 C13 82.0(7) . . . . ?
C9 C10 N1 C6 -94.3(7) . . . . ?
C27 C28 N4 C29 -179.4(6) . . . . ?
C25 C28 N4 C29 -0.7(8) . . . . ?
C27 C28 N4 C30 2.2(8) . . . . ?
C25 C28 N4 C30 -179.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.227
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2015185'
loop_
_audit_author_name
_audit_author_address
'Pengfei Chen'
;ANHUI UNIVERSITY
China
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Br2 N4'
_chemical_formula_weight         602.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.292(4)
_cell_length_b                   13.172(3)
_cell_length_c                   12.572(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.655(2)
_cell_angle_gamma                90.00
_cell_volume                     2743.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5507
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.53

_exptl_crystal_description       lamellar
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    2.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_T_max  0.6160
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18768
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4828
_reflns_number_gt                3356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.1088P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4828
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1714
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44287(3) 0.62184(5) 0.33080(6) 0.0769(3) Uani 1 1 d . . .
Br2 Br 0.77577(5) 0.90392(5) -0.11214(7) 0.0939(3) Uani 1 1 d . . .
C20 C 0.6963(2) 0.3714(3) 0.1970(3) 0.0337(9) Uani 1 1 d . . .
H20 H 0.6895 0.3555 0.2658 0.040 Uiso 1 1 calc R . .
C12 C 0.7713(3) 0.1296(3) 0.1610(4) 0.0404(10) Uani 1 1 d . . .
C19 C 0.6551(2) 0.4527(3) 0.1356(3) 0.0320(9) Uani 1 1 d . . .
C24 C 0.4990(3) 0.6084(4) 0.2219(5) 0.0514(13) Uani 1 1 d . . .
C8 C 0.9219(2) 0.3202(3) 0.4916(4) 0.0375(10) Uani 1 1 d . . .
C11 C 0.7885(2) 0.2220(3) 0.2132(3) 0.0347(9) Uani 1 1 d . . .
C10 C 0.8427(2) 0.2289(3) 0.3226(4) 0.0391(10) Uani 1 1 d . . .
H10 H 0.8622 0.1679 0.3574 0.047 Uiso 1 1 calc R . .
C15 C 0.7479(2) 0.3142(3) 0.1541(3) 0.0334(9) Uani 1 1 d . . .
C9 C 0.8681(2) 0.3134(3) 0.3798(3) 0.0360(9) Uani 1 1 d . . .
H9 H 0.8494 0.3743 0.3444 0.043 Uiso 1 1 calc R . .
C18 C 0.6680(2) 0.4781(3) 0.0342(3) 0.0365(10) Uani 1 1 d . . .
C7 C 0.9577(3) 0.2351(3) 0.5546(4) 0.0445(10) Uani 1 1 d . . .
H7 H 0.9487 0.1711 0.5220 0.053 Uiso 1 1 calc R . .
C22 C 0.5953(2) 0.5223(3) 0.1522(4) 0.0362(9) Uani 1 1 d . . .
C21 C 0.5758(3) 0.5872(3) 0.0594(4) 0.0404(10) Uani 1 1 d . . .
C27 C 0.6190(3) 0.6090(4) -0.1166(4) 0.0505(12) Uani 1 1 d . . .
H27A H 0.5694 0.6474 -0.1438 0.061 Uiso 1 1 calc R . .
H27B H 0.6196 0.5570 -0.1709 0.061 Uiso 1 1 calc R . .
C23 C 0.5567(3) 0.5333(3) 0.2350(4) 0.0424(10) Uani 1 1 d . . .
H23 H 0.5695 0.4913 0.2971 0.051 Uiso 1 1 calc R . .
C3 C 1.0199(3) 0.3368(4) 0.7151(4) 0.0477(11) Uani 1 1 d . . .
C26 C 0.5180(3) 0.6651(3) 0.0494(5) 0.0542(13) Uani 1 1 d . . .
H26 H 0.5060 0.7092 -0.0109 0.065 Uiso 1 1 calc R . .
C17 C 0.7206(3) 0.4225(3) -0.0099(4) 0.0402(10) Uani 1 1 d . . .
H17 H 0.7296 0.4403 -0.0770 0.048 Uiso 1 1 calc R . .
C16 C 0.7584(2) 0.3403(3) 0.0505(4) 0.0387(10) Uani 1 1 d . . .
H16 H 0.7921 0.3004 0.0219 0.046 Uiso 1 1 calc R . .
C14 C 0.7135(3) 0.1206(3) 0.0533(5) 0.0502(12) Uani 1 1 d . . .
C28 C 0.6908(3) 0.6801(4) -0.1050(4) 0.0515(12) Uani 1 1 d . . .
H28A H 0.6906 0.7321 -0.0504 0.062 Uiso 1 1 calc R . .
H28B H 0.7406 0.6418 -0.0787 0.062 Uiso 1 1 calc R . .
C6 C 0.9391(3) 0.4122(3) 0.5445(4) 0.0439(11) Uani 1 1 d . . .
H6 H 0.9171 0.4704 0.5056 0.053 Uiso 1 1 calc R . .
C13 C 0.8060(3) 0.0374(4) 0.2137(4) 0.0512(12) Uani 1 1 d . . .
C29 C 0.6877(3) 0.7297(4) -0.2143(4) 0.0524(12) Uani 1 1 d . . .
H29A H 0.6405 0.7731 -0.2358 0.063 Uiso 1 1 calc R . .
H29B H 0.6810 0.6772 -0.2703 0.063 Uiso 1 1 calc R . .
C4 C 0.9870(3) 0.4228(4) 0.6518(4) 0.0524(12) Uani 1 1 d . . .
H4 H 0.9978 0.4871 0.6829 0.063 Uiso 1 1 calc R . .
C25 C 0.4799(3) 0.6739(4) 0.1309(5) 0.0580(14) Uani 1 1 d . . .
H25 H 0.4410 0.7239 0.1254 0.070 Uiso 1 1 calc R . .
C5 C 1.0052(3) 0.2430(4) 0.6619(4) 0.0500(11) Uani 1 1 d . . .
H5 H 1.0280 0.1847 0.7000 0.060 Uiso 1 1 calc R . .
C30 C 0.7615(3) 0.7926(5) -0.2139(5) 0.0704(16) Uani 1 1 d . . .
H30A H 0.7555 0.8185 -0.2881 0.084 Uiso 1 1 calc R . .
H30B H 0.8090 0.7497 -0.1934 0.084 Uiso 1 1 calc R . .
C1 C 1.0968(3) 0.2564(5) 0.8885(4) 0.0687(15) Uani 1 1 d . . .
H1A H 1.0539 0.2087 0.8838 0.103 Uiso 1 1 calc R . .
H1B H 1.1207 0.2751 0.9646 0.103 Uiso 1 1 calc R . .
H1C H 1.1370 0.2258 0.8596 0.103 Uiso 1 1 calc R . .
C2 C 1.0809(5) 0.4432(5) 0.8781(5) 0.104(3) Uani 1 1 d . . .
H2A H 1.1154 0.4817 0.8455 0.156 Uiso 1 1 calc R . .
H2B H 1.1069 0.4342 0.9560 0.156 Uiso 1 1 calc R . .
H2C H 1.0309 0.4788 0.8683 0.156 Uiso 1 1 calc R . .
N4 N 0.6201(2) 0.5605(3) -0.0116(3) 0.0422(9) Uani 1 1 d . . .
N3 N 0.6670(3) 0.1118(4) -0.0306(4) 0.0706(13) Uani 1 1 d . . .
N2 N 0.8328(3) -0.0354(3) 0.2579(4) 0.0777(14) Uani 1 1 d . . .
N1 N 1.0650(3) 0.3451(4) 0.8249(4) 0.0664(12) Uani 1 1 d . . .


_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 C24 1.900(5) . ?
Br2 C30 1.915(6) . ?
C20 C15 1.389(5) . ?
C20 C19 1.392(6) . ?
C20 H20 0.9300 . ?
C12 C11 1.375(6) . ?
C12 C13 1.430(7) . ?
C12 C14 1.439(8) . ?
C19 C18 1.397(6) . ?
C19 C22 1.440(5) . ?
C24 C23 1.381(6) . ?
C24 C25 1.394(8) . ?
C8 C6 1.374(6) . ?
C8 C7 1.410(6) . ?
C8 C9 1.449(6) . ?
C11 C10 1.427(6) . ?
C11 C15 1.490(6) . ?
C10 C9 1.330(6) . ?
C10 H10 0.9300 . ?
C15 C16 1.408(6) . ?
C9 H9 0.9300 . ?
C18 N4 1.386(5) . ?
C18 C17 1.401(6) . ?
C7 C5 1.368(6) . ?
C7 H7 0.9300 . ?
C22 C23 1.395(6) . ?
C22 C21 1.407(6) . ?
C21 N4 1.379(6) . ?
C21 C26 1.412(6) . ?
C27 N4 1.461(6) . ?
C27 C28 1.528(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C23 H23 0.9300 . ?
C3 N1 1.381(6) . ?
C3 C5 1.393(7) . ?
C3 C4 1.407(7) . ?
C26 C25 1.374(7) . ?
C26 H26 0.9300 . ?
C17 C16 1.375(6) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C14 N3 1.135(6) . ?
C28 C29 1.508(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C6 C4 1.373(7) . ?
C6 H6 0.9300 . ?
C13 N2 1.138(6) . ?
C29 C30 1.519(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C4 H4 0.9300 . ?
C25 H25 0.9300 . ?
C5 H5 0.9300 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C1 N1 1.434(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.445(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
C15 C20 C19 119.1(4) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C11 C12 C13 121.7(4) . . ?
C11 C12 C14 121.3(4) . . ?
C13 C12 C14 116.8(4) . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 C22 133.2(4) . . ?
C18 C19 C22 106.8(3) . . ?
C23 C24 C25 122.3(5) . . ?
C23 C24 Br1 118.8(4) . . ?
C25 C24 Br1 118.9(3) . . ?
C6 C8 C7 115.5(4) . . ?
C6 C8 C9 121.0(4) . . ?
C7 C8 C9 123.5(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 C15 118.5(4) . . ?
C10 C11 C15 121.0(4) . . ?
C9 C10 C11 126.7(4) . . ?
C9 C10 H10 116.7 . . ?
C11 C10 H10 116.7 . . ?
C20 C15 C16 119.6(4) . . ?
C20 C15 C11 120.7(3) . . ?
C16 C15 C11 119.6(3) . . ?
C10 C9 C8 126.7(4) . . ?
C10 C9 H9 116.6 . . ?
C8 C9 H9 116.6 . . ?
N4 C18 C19 109.6(4) . . ?
N4 C18 C17 128.6(4) . . ?
C19 C18 C17 121.9(4) . . ?
C5 C7 C8 122.5(4) . . ?
C5 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 C19 133.6(4) . . ?
C21 C22 C19 106.2(4) . . ?
N4 C21 C22 109.6(4) . . ?
N4 C21 C26 129.6(4) . . ?
C22 C21 C26 120.8(4) . . ?
N4 C27 C28 112.4(4) . . ?
N4 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
N4 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C24 C23 C22 118.0(4) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
N1 C3 C5 121.6(4) . . ?
N1 C3 C4 121.5(5) . . ?
C5 C3 C4 117.0(4) . . ?
C25 C26 C21 118.2(5) . . ?
C25 C26 H26 120.9 . . ?
C21 C26 H26 120.9 . . ?
C16 C17 C18 116.9(4) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C17 C16 C15 122.5(4) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
N3 C14 C12 178.4(5) . . ?
C29 C28 C27 111.3(4) . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C4 C6 C8 123.4(4) . . ?
C4 C6 H6 118.3 . . ?
C8 C6 H6 118.3 . . ?
N2 C13 C12 178.3(5) . . ?
C28 C29 C30 115.0(4) . . ?
C28 C29 H29A 108.5 . . ?
C30 C29 H29A 108.5 . . ?
C28 C29 H29B 108.5 . . ?
C30 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
C6 C4 C3 120.4(4) . . ?
C6 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C7 C5 C3 121.1(4) . . ?
C7 C5 H5 119.4 . . ?
C3 C5 H5 119.4 . . ?
C29 C30 Br2 111.6(4) . . ?
C29 C30 H30A 109.3 . . ?
Br2 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
Br2 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C21 N4 C18 107.9(3) . . ?
C21 N4 C27 127.4(4) . . ?
C18 N4 C27 124.7(4) . . ?
C3 N1 C1 120.6(5) . . ?
C3 N1 C2 120.8(5) . . ?
C1 N1 C2 118.6(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
C15 C20 C19 C18 -2.3(6) . . . . ?
C15 C20 C19 C22 176.1(4) . . . . ?
C13 C12 C11 C10 0.6(6) . . . . ?
C14 C12 C11 C10 176.5(4) . . . . ?
C13 C12 C11 C15 -178.1(4) . . . . ?
C14 C12 C11 C15 -2.1(6) . . . . ?
C12 C11 C10 C9 175.8(4) . . . . ?
C15 C11 C10 C9 -5.6(6) . . . . ?
C19 C20 C15 C16 0.9(6) . . . . ?
C19 C20 C15 C11 -175.5(4) . . . . ?
C12 C11 C15 C20 117.3(4) . . . . ?
C10 C11 C15 C20 -61.3(5) . . . . ?
C12 C11 C15 C16 -59.0(5) . . . . ?
C10 C11 C15 C16 122.4(4) . . . . ?
C11 C10 C9 C8 178.7(4) . . . . ?
C6 C8 C9 C10 -175.3(4) . . . . ?
C7 C8 C9 C10 2.5(6) . . . . ?
C20 C19 C18 N4 179.6(3) . . . . ?
C22 C19 C18 N4 0.7(4) . . . . ?
C20 C19 C18 C17 1.5(6) . . . . ?
C22 C19 C18 C17 -177.4(4) . . . . ?
C6 C8 C7 C5 1.2(6) . . . . ?
C9 C8 C7 C5 -176.8(4) . . . . ?
C20 C19 C22 C23 -0.5(8) . . . . ?
C18 C19 C22 C23 178.1(4) . . . . ?
C20 C19 C22 C21 -179.1(4) . . . . ?
C18 C19 C22 C21 -0.5(4) . . . . ?
C23 C22 C21 N4 -178.7(4) . . . . ?
C19 C22 C21 N4 0.1(4) . . . . ?
C23 C22 C21 C26 0.9(6) . . . . ?
C19 C22 C21 C26 179.7(4) . . . . ?
C25 C24 C23 C22 -1.4(7) . . . . ?
Br1 C24 C23 C22 177.8(3) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C19 C22 C23 C24 -177.7(4) . . . . ?
N4 C21 C26 C25 177.8(4) . . . . ?
C22 C21 C26 C25 -1.7(7) . . . . ?
N4 C18 C17 C16 -176.8(4) . . . . ?
C19 C18 C17 C16 0.9(6) . . . . ?
C18 C17 C16 C15 -2.4(6) . . . . ?
C20 C15 C16 C17 1.5(6) . . . . ?
C11 C15 C16 C17 177.9(4) . . . . ?
C11 C12 C14 N3 -123(20) . . . . ?
C13 C12 C14 N3 53(21) . . . . ?
N4 C27 C28 C29 -179.5(4) . . . . ?
C7 C8 C6 C4 -0.7(6) . . . . ?
C9 C8 C6 C4 177.4(4) . . . . ?
C11 C12 C13 N2 56(21) . . . . ?
C14 C12 C13 N2 -120(20) . . . . ?
C27 C28 C29 C30 -173.5(4) . . . . ?
C8 C6 C4 C3 -1.7(7) . . . . ?
N1 C3 C4 C6 -176.8(4) . . . . ?
C5 C3 C4 C6 3.4(7) . . . . ?
C21 C26 C25 C24 1.0(7) . . . . ?
C23 C24 C25 C26 0.6(7) . . . . ?
Br1 C24 C25 C26 -178.7(4) . . . . ?
C8 C7 C5 C3 0.6(7) . . . . ?
N1 C3 C5 C7 177.3(4) . . . . ?
C4 C3 C5 C7 -2.9(7) . . . . ?
C28 C29 C30 Br2 -62.0(5) . . . . ?
C22 C21 N4 C18 0.4(5) . . . . ?
C26 C21 N4 C18 -179.2(4) . . . . ?
C22 C21 N4 C27 -179.1(4) . . . . ?
C26 C21 N4 C27 1.3(7) . . . . ?
C19 C18 N4 C21 -0.7(4) . . . . ?
C17 C18 N4 C21 177.3(4) . . . . ?
C19 C18 N4 C27 178.8(4) . . . . ?
C17 C18 N4 C27 -3.2(7) . . . . ?
C28 C27 N4 C21 100.8(5) . . . . ?
C28 C27 N4 C18 -78.6(5) . . . . ?
C5 C3 N1 C1 -1.4(7) . . . . ?
C4 C3 N1 C1 178.8(5) . . . . ?
C5 C3 N1 C2 178.9(6) . . . . ?
C4 C3 N1 C2 -0.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_kzben
_database_code_depnum_ccdc_archive 'CCDC 1541386'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        kzben
_chemical_name_common            kzben
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 N3'
_chemical_formula_weight         401.49

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'

_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                   14.9068(15)
_cell_length_b                   13.0177(13)
_cell_length_c                   12.5244(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.6110(10)
_cell_angle_gamma                90
_cell_volume                     2303.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6603
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.86

_exptl_crystal_description       bulk
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16109
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.441
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4068
_reflns_number_gt                3254
_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-2014 (Sheldrick, 2014)'
_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)+(0.0771P)²+0.5438P] 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
_refine_ls_extinction_coef       0.0036(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4068
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.08999(11) 0.54466(13) 0.19872(15) 0.0547(4) Uani 1 1 d . . . . .
C6 C 0.06679(12) 0.60675(13) 0.10191(16) 0.0598(5) Uani 1 1 d . . . . .
C2 C 0.04585(13) 0.56021(16) 0.28029(17) 0.0665(5) Uani 1 1 d . . . . .
H2 H 0.0604 0.5194 0.3445 0.080 Uiso 1 1 calc R U . . .
C5 C 0.00069(15) 0.68560(17) 0.0851(2) 0.0802(6) Uani 1 1 d . . . . .
H5 H -0.0144 0.7271 0.0214 0.096 Uiso 1 1 calc R U . . .
C4 C -0.04132(16) 0.69921(19) 0.1671(2) 0.0929(8) Uani 1 1 d . . . . .
H4 H -0.0857 0.7514 0.1581 0.111 Uiso 1 1 calc R U . . .
C3 C -0.02029(15) 0.63846(19) 0.2625(2) 0.0844(7) Uani 1 1 d . . . . .
H3 H -0.0509 0.6503 0.3154 0.101 Uiso 1 1 calc R U . . .
C10 C 0.11239(15) 0.61826(15) -0.07682(16) 0.0706(5) Uani 1 1 d . . . . .
H10A H 0.0526 0.6543 -0.1066 0.085 Uiso 1 1 calc R U . . .
H10B H 0.1123 0.5624 -0.1281 0.085 Uiso 1 1 calc R U . . .
C9 C 0.19093(17) 0.69098(17) -0.07537(19) 0.0823(6) Uani 1 1 d . . . . .
H9A H 0.2498 0.6527 -0.0547 0.099 Uiso 1 1 calc R U . . .
H9B H 0.1796 0.7169 -0.1512 0.099 Uiso 1 1 calc R U . . .
C7 C 0.2801(2) 0.8547(2) -0.0101(3) 0.1167(10) Uani 1 1 d . . . . .
H7A H 0.2802 0.9155 0.0333 0.175 Uiso 1 1 calc R U . . .
H7B H 0.2667 0.8729 -0.0879 0.175 Uiso 1 1 calc R U . . .
H7C H 0.3410 0.8221 0.0169 0.175 Uiso 1 1 calc R U . . .
C8 C 0.20298(17) 0.77943(18) 0.0018(2) 0.0866(7) Uani 1 1 d . . . . .
H8A H 0.2206 0.7548 0.0788 0.104 Uiso 1 1 calc R U . . .
H8B H 0.1433 0.8157 -0.0145 0.104 Uiso 1 1 calc R U . . .
C11 C 0.15865(11) 0.47069(12) 0.18709(13) 0.0478(4) Uani 1 1 d . . . . .
C12 C 0.20615(11) 0.38963(12) 0.25293(13) 0.0476(4) Uani 1 1 d . . . . .
H12 H 0.1990 0.3769 0.3228 0.057 Uiso 1 1 calc R U . . .
C13 C 0.17286(12) 0.49191(12) 0.08288(13) 0.0498(4) Uani 1 1 d . . . . .
C16 C 0.26473(11) 0.32742(12) 0.21327(13) 0.0478(4) Uani 1 1 d . . . . .
C15 C 0.27681(13) 0.34962(13) 0.10937(14) 0.0557(4) Uani 1 1 d . . . . .
H15 H 0.3156 0.3073 0.0833 0.067 Uiso 1 1 calc R U . . .
C14 C 0.23308(13) 0.43202(13) 0.04436(14) 0.0565(4) Uani 1 1 d . . . . .
H14 H 0.2436 0.4470 -0.0233 0.068 Uiso 1 1 calc R U . . .
C18 C 0.29197(13) 0.14066(13) 0.22898(15) 0.0566(4) Uani 1 1 d . . . . .
C19 C 0.22756(16) 0.12524(14) 0.11794(18) 0.0660(5) Uani 1 1 d . . . . .
C17 C 0.33192(15) 0.04878(14) 0.28833(17) 0.0668(5) Uani 1 1 d . . . . .
C20 C 0.31065(12) 0.23574(12) 0.27819(14) 0.0513(4) Uani 1 1 d . . . . .
C21 C 0.37400(12) 0.24472(13) 0.39249(14) 0.0546(4) Uani 1 1 d . . . . .
H21 H 0.3974 0.1840 0.4303 0.066 Uiso 1 1 calc R U . . .
C22 C 0.40188(12) 0.33241(13) 0.44841(14) 0.0531(4) Uani 1 1 d . . . . .
H22 H 0.3779 0.3929 0.4105 0.064 Uiso 1 1 calc R U . . .
C23 C 0.46627(12) 0.34271(13) 0.56311(15) 0.0554(4) Uani 1 1 d . . . . .
C28 C 0.47750(13) 0.43851(15) 0.61556(16) 0.0637(5) Uani 1 1 d . . . . .
H28 H 0.4441 0.4947 0.5766 0.076 Uiso 1 1 calc R U . . .
C27 C 0.53742(16) 0.45125(18) 0.72445(19) 0.0805(6) Uani 1 1 d . . . . .
H27 H 0.5442 0.5156 0.7585 0.097 Uiso 1 1 calc R U . . .
C24 C 0.51812(15) 0.26047(16) 0.62352(19) 0.0791(6) Uani 1 1 d . . . . .
H24 H 0.5123 0.1959 0.5902 0.095 Uiso 1 1 calc R U . . .
C26 C 0.5868(2) 0.3688(2) 0.7821(2) 0.1037(9) Uani 1 1 d . . . . .
H26 H 0.6266 0.3769 0.8557 0.124 Uiso 1 1 calc R U . . .
C25 C 0.5775(2) 0.2738(2) 0.7313(2) 0.1066(9) Uani 1 1 d . . . . .
H25 H 0.6118 0.2183 0.7705 0.128 Uiso 1 1 calc R U . . .
N1 N 0.11766(10) 0.57463(11) 0.03234(12) 0.0592(4) Uani 1 1 d . . . . .
N2 N 0.36218(17) -0.02391(14) 0.33754(19) 0.0956(6) Uani 1 1 d . . . . .
N3 N 0.17597(16) 0.10977(15) 0.02937(17) 0.0924(6) Uani 1 1 d . . . . .


_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 C2 1.395(3) . ?
C1 C6 1.406(3) . ?
C1 C11 1.446(2) . ?
C6 N1 1.389(2) . ?
C6 C5 1.392(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.374(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.383(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C10 N1 1.459(2) . ?
C10 C9 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 C8 1.477(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C8 1.553(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C12 1.386(2) . ?
C11 C13 1.415(2) . ?
C12 C16 1.394(2) . ?
C12 H12 0.9300 . ?
C13 N1 1.380(2) . ?
C13 C14 1.387(2) . ?
C16 C15 1.400(2) . ?
C16 C20 1.483(2) . ?
C15 C14 1.378(2) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C18 C20 1.371(2) . ?
C18 C19 1.430(3) . ?
C18 C17 1.434(2) . ?
C19 N3 1.148(3) . ?
C17 N2 1.141(2) . ?
C20 C21 1.446(2) . ?
C21 C22 1.334(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.457(2) . ?
C22 H22 0.9300 . ?
C23 C28 1.394(3) . ?
C23 C24 1.394(3) . ?
C28 C27 1.381(3) . ?
C28 H28 0.9300 . ?
C27 C26 1.370(3) . ?
C27 H27 0.9300 . ?
C24 C25 1.368(3) . ?
C24 H24 0.9300 . ?
C26 C25 1.377(4) . ?
C26 H26 0.9300 . ?
C25 H25 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 C1 C6 120.30(16) . . ?
C2 C1 C11 133.22(17) . . ?
C6 C1 C11 106.45(15) . . ?
N1 C6 C5 128.97(19) . . ?
N1 C6 C1 109.55(14) . . ?
C5 C6 C1 121.47(19) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C5 C6 116.8(2) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
N1 C10 C9 115.18(16) . . ?
N1 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C8 C9 C10 115.5(2) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C12 C11 C13 119.93(14) . . ?
C12 C11 C1 133.66(16) . . ?
C13 C11 C1 106.39(14) . . ?
C11 C12 C16 119.30(15) . . ?
C11 C12 H12 120.3 . . ?
C16 C12 H12 120.3 . . ?
N1 C13 C14 129.54(16) . . ?
N1 C13 C11 109.42(15) . . ?
C14 C13 C11 121.03(15) . . ?
C12 C16 C15 119.52(15) . . ?
C12 C16 C20 120.29(14) . . ?
C15 C16 C20 120.14(14) . . ?
C14 C15 C16 122.21(15) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C14 C13 117.95(15) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C20 C18 C19 122.75(16) . . ?
C20 C18 C17 121.93(16) . . ?
C19 C18 C17 115.23(16) . . ?
N3 C19 C18 178.0(2) . . ?
N2 C17 C18 178.0(2) . . ?
C18 C20 C21 119.52(15) . . ?
C18 C20 C16 119.21(15) . . ?
C21 C20 C16 121.27(14) . . ?
C22 C21 C20 125.75(15) . . ?
C22 C21 H21 117.1 . . ?
C20 C21 H21 117.1 . . ?
C21 C22 C23 126.37(15) . . ?
C21 C22 H22 116.8 . . ?
C23 C22 H22 116.8 . . ?
C28 C23 C24 117.96(17) . . ?
C28 C23 C22 119.27(16) . . ?
C24 C23 C22 122.77(17) . . ?
C27 C28 C23 121.00(19) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C26 C27 C28 119.7(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C13 N1 C6 108.19(14) . . ?
C13 N1 C10 125.40(16) . . ?
C6 N1 C10 126.40(15) . . ?

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
C2 C1 C6 N1 -178.26(15) . . . . ?
C11 C1 C6 N1 -0.08(18) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C11 C1 C6 C5 178.95(16) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C11 C1 C2 C3 -177.95(18) . . . . ?
N1 C6 C5 C4 178.28(19) . . . . ?
C1 C6 C5 C4 -0.5(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
N1 C10 C9 C8 -56.4(3) . . . . ?
C10 C9 C8 C7 -175.24(19) . . . . ?
C2 C1 C11 C12 -0.9(3) . . . . ?
C6 C1 C11 C12 -178.75(17) . . . . ?
C2 C1 C11 C13 177.50(18) . . . . ?
C6 C1 C11 C13 -0.33(17) . . . . ?
C13 C11 C12 C16 -2.5(2) . . . . ?
C1 C11 C12 C16 175.77(16) . . . . ?
C12 C11 C13 N1 179.32(14) . . . . ?
C1 C11 C13 N1 0.64(17) . . . . ?
C12 C11 C13 C14 0.7(2) . . . . ?
C1 C11 C13 C14 -177.95(15) . . . . ?
C11 C12 C16 C15 1.9(2) . . . . ?
C11 C12 C16 C20 -175.46(14) . . . . ?
C12 C16 C15 C14 0.5(3) . . . . ?
C20 C16 C15 C14 177.86(16) . . . . ?
C16 C15 C14 C13 -2.2(3) . . . . ?
N1 C13 C14 C15 -176.67(16) . . . . ?
C11 C13 C14 C15 1.6(3) . . . . ?
C19 C18 C20 C21 177.68(16) . . . . ?
C17 C18 C20 C21 1.3(3) . . . . ?
C19 C18 C20 C16 -1.8(3) . . . . ?
C17 C18 C20 C16 -178.16(16) . . . . ?
C12 C16 C20 C18 120.12(18) . . . . ?
C15 C16 C20 C18 -57.2(2) . . . . ?
C12 C16 C20 C21 -59.4(2) . . . . ?
C15 C16 C20 C21 123.30(18) . . . . ?
C18 C20 C21 C22 176.51(17) . . . . ?
C16 C20 C21 C22 -4.0(3) . . . . ?
C20 C21 C22 C23 -179.41(15) . . . . ?
C21 C22 C23 C28 -170.53(17) . . . . ?
C21 C22 C23 C24 9.7(3) . . . . ?
C24 C23 C28 C27 -0.7(3) . . . . ?
C22 C23 C28 C27 179.60(17) . . . . ?
C23 C28 C27 C26 0.0(3) . . . . ?
C28 C23 C24 C25 0.5(3) . . . . ?
C22 C23 C24 C25 -179.7(2) . . . . ?
C28 C27 C26 C25 0.7(4) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C27 C26 C25 C24 -0.8(5) . . . . ?
C14 C13 N1 C6 177.73(17) . . . . ?
C11 C13 N1 C6 -0.70(18) . . . . ?
C14 C13 N1 C10 -0.7(3) . . . . ?
C11 C13 N1 C10 -179.18(16) . . . . ?
C5 C6 N1 C13 -178.46(18) . . . . ?
C1 C6 N1 C13 0.48(19) . . . . ?
C5 C6 N1 C10 0.0(3) . . . . ?
C1 C6 N1 C10 178.94(16) . . . . ?
C9 C10 N1 C13 -81.5(2) . . . . ?
C9 C10 N1 C6 100.3(2) . . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3

