# Electronic Supplementary Material (ESI) for Soft Matter.
# 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_qzr
_database_code_depnum_ccdc_archive 'CCDC 2047103'
loop_
_audit_author_name
_audit_author_address
Rany
;hangzhou normal university
China
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.50 H4.50 Br0.50 N0.25 O0.25'
_chemical_formula_weight         94.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   12.0433(19)
_cell_length_b                   9.2013(15)
_cell_length_c                   14.945(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.240(3)
_cell_angle_gamma                90.00
_cell_volume                     1624.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             187
_exptl_absorpt_coefficient_mu    1.245
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            10136
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3681
_reflns_number_gt                1932
_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)+(0.0866P)²+0.5715P] 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         3681
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.58052(5) 0.70538(7) 0.57887(4) 0.0763(3) Uani 1 1 d . . .
N1 N 0.4649(3) 0.5069(4) 0.7024(2) 0.0538(10) Uani 1 1 d . . .
Br2 Br 0.22142(6) 0.39237(10) 0.68390(5) 0.1051(3) Uani 1 1 d . . .
O2 O 0.4539(3) 0.7199(4) 0.7761(2) 0.0708(10) Uani 1 1 d . . .
C3 C 0.4938(4) 0.5967(6) 0.7745(3) 0.0571(13) Uani 1 1 d . . .
C4 C 0.3920(4) 0.5535(5) 0.6214(3) 0.0512(11) Uani 1 1 d . . .
C5 C 0.3563(5) 0.6895(7) 0.4776(3) 0.0725(16) Uani 1 1 d . . .
H5 H 0.3834 0.7505 0.4371 0.087 Uiso 1 1 calc R . .
C7 C 0.2794(4) 0.5112(6) 0.6009(3) 0.0657(14) Uani 1 1 d . . .
C8 C 0.4281(4) 0.6432(6) 0.5579(3) 0.0576(12) Uani 1 1 d . . .
C10 C 0.2079(5) 0.5520(8) 0.5213(4) 0.0835(18) Uani 1 1 d . . .
H10 H 0.1339 0.5177 0.5088 0.100 Uiso 1 1 calc R . .
C11 C 0.2451(5) 0.6435(8) 0.4593(4) 0.0806(17) Uani 1 1 d . . .
C15 C 0.1713(7) 0.6890(11) 0.3685(5) 0.125(3) Uani 1 1 d . . .
H15A H 0.0927 0.6903 0.3749 0.150 Uiso 1 1 calc R . .
H15B H 0.1917 0.7869 0.3539 0.150 Uiso 1 1 calc R . .
C16 C 0.1831(8) 0.5914(15) 0.2927(5) 0.166(5) Uani 1 1 d . . .
H16A H 0.1578 0.4945 0.3045 0.200 Uiso 1 1 calc R . .
H16B H 0.2620 0.5858 0.2874 0.200 Uiso 1 1 calc R . .
C18 C -0.0322(10) 0.6865(17) 0.0700(7) 0.180(5) Uani 1 1 d . . .
H18A H -0.0250 0.7916 0.0699 0.216 Uiso 1 1 calc R . .
H18B H 0.0003 0.6479 0.0204 0.216 Uiso 1 1 calc R . .
C19 C 0.0330(12) 0.623(3) 0.1645(9) 0.296(11) Uani 1 1 d . . .
H19A H -0.0193 0.6343 0.2059 0.356 Uiso 1 1 calc R . .
H19B H 0.0376 0.5190 0.1542 0.356 Uiso 1 1 calc R . .
C30 C 0.5772(5) 0.5351(7) 0.8524(3) 0.0828(18) Uani 1 1 d . . .
H30A H 0.6349 0.6059 0.8736 0.124 Uiso 1 1 calc R . .
H30B H 0.6112 0.4496 0.8326 0.124 Uiso 1 1 calc R . .
H30C H 0.5391 0.5102 0.9011 0.124 Uiso 1 1 calc R . .
C31 C 0.1109(15) 0.651(3) 0.2023(7) 0.337(15) Uani 1 1 d . . .
H31A H 0.1040 0.7536 0.2138 0.404 Uiso 1 1 calc R . .
H31B H 0.1613 0.6440 0.1591 0.404 Uiso 1 1 calc R . .
C40 C -0.1488(9) 0.6466(19) 0.0579(8) 0.204(7) Uani 1 1 d . . .
H40A H -0.1559 0.5431 0.0503 0.307 Uiso 1 1 calc R . .
H40B H -0.1908 0.6940 0.0047 0.307 Uiso 1 1 calc R . .
H40C H -0.1780 0.6756 0.1105 0.307 Uiso 1 1 calc R . .

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 0.0798(4) 0.0762(5) 0.0738(4) 0.0036(3) 0.0174(3) -0.0125(3)
N1 0.076(2) 0.039(2) 0.0435(18) -0.0038(17) 0.0045(18) -0.001(2)
Br2 0.1016(5) 0.1231(7) 0.0988(5) 0.0117(4) 0.0396(4) -0.0243(4)
O2 0.108(3) 0.039(2) 0.065(2) -0.0061(17) 0.0148(19) 0.004(2)
C3 0.076(3) 0.050(3) 0.046(2) -0.005(2) 0.013(2) -0.017(3)
C4 0.070(3) 0.041(3) 0.043(2) -0.005(2) 0.010(2) 0.007(2)
C5 0.089(4) 0.076(4) 0.051(3) 0.008(3) 0.009(3) 0.001(3)
C7 0.072(3) 0.067(4) 0.059(3) -0.006(3) 0.014(2) -0.005(3)
C8 0.068(3) 0.052(3) 0.053(2) -0.004(2) 0.011(2) -0.005(3)
C10 0.063(3) 0.105(5) 0.078(4) -0.009(4) 0.004(3) 0.011(3)
C11 0.075(4) 0.101(5) 0.060(3) -0.004(3) -0.001(3) 0.023(4)
C15 0.112(6) 0.155(9) 0.093(5) 0.028(5) -0.020(4) 0.036(5)
C16 0.144(7) 0.272(15) 0.062(4) -0.007(6) -0.031(4) -0.027(8)
C18 0.149(9) 0.234(16) 0.130(8) 0.024(8) -0.038(7) 0.046(9)
C19 0.212(14) 0.45(3) 0.168(12) 0.068(15) -0.097(11) 0.116(18)
C30 0.118(5) 0.072(4) 0.051(3) -0.009(3) -0.002(3) -0.002(4)
C31 0.30(2) 0.54(4) 0.109(8) 0.083(14) -0.127(11) -0.06(2)
C40 0.111(7) 0.34(2) 0.148(9) 0.094(11) 0.003(6) 0.032(10)

_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 C8 1.890(5) . ?
N1 C3 1.350(6) . ?
N1 C4 1.416(5) . ?
Br2 C7 1.887(5) . ?
O2 C3 1.233(6) . ?
C3 C30 1.493(7) . ?
C4 C7 1.386(7) . ?
C4 C8 1.390(7) . ?
C5 C11 1.380(8) . ?
C5 C8 1.401(7) . ?
C5 H5 0.9300 . ?
C7 C10 1.378(7) . ?
C10 C11 1.389(9) . ?
C10 H10 0.9300 . ?
C11 C15 1.529(8) . ?
C15 C16 1.474(13) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C31 1.555(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C40 1.429(15) . ?
C18 C19 1.588(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C31 1.030(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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 N1 C4 121.2(4) . . ?
O2 C3 N1 122.5(5) . . ?
O2 C3 C30 122.7(5) . . ?
N1 C3 C30 114.8(5) . . ?
C7 C4 C8 116.0(4) . . ?
C7 C4 N1 121.4(4) . . ?
C8 C4 N1 122.6(4) . . ?
C11 C5 C8 119.3(5) . . ?
C11 C5 H5 120.4 . . ?
C8 C5 H5 120.4 . . ?
C10 C7 C4 122.3(5) . . ?
C10 C7 Br2 118.4(4) . . ?
C4 C7 Br2 119.3(4) . . ?
C4 C8 C5 122.8(5) . . ?
C4 C8 Br1 119.3(3) . . ?
C5 C8 Br1 117.8(4) . . ?
C7 C10 C11 120.8(5) . . ?
C7 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C5 C11 C10 118.7(5) . . ?
C5 C11 C15 117.8(6) . . ?
C10 C11 C15 123.4(6) . . ?
C16 C15 C11 112.9(7) . . ?
C16 C15 H15A 109.0 . . ?
C11 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C11 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C31 109.5(13) . . ?
C15 C16 H16A 109.8 . . ?
C31 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C31 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C40 C18 C19 108.7(12) . . ?
C40 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
C40 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.3 . . ?
C31 C19 C18 129(2) . . ?
C31 C19 H19A 104.9 . . ?
C18 C19 H19A 104.9 . . ?
C31 C19 H19B 104.9 . . ?
C18 C19 H19B 104.9 . . ?
H19A C19 H19B 105.8 . . ?
C3 C30 H30A 109.5 . . ?
C3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C19 C31 C16 133(2) . . ?
C19 C31 H31A 103.9 . . ?
C16 C31 H31A 103.9 . . ?
C19 C31 H31B 103.9 . . ?
C16 C31 H31B 103.9 . . ?
H31A C31 H31B 105.4 . . ?
C18 C40 H40A 109.5 . . ?
C18 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C18 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.087
