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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1970627'
loop_
_audit_author_name
_audit_author_address
'Gao Zhang-Ran'
;Laboratory of Solid State Microstructures, Nanjing University, Nanjing, China
China
;
_audit_update_record             
;
2019-12-07 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H10 Br N'
_chemical_formula_weight         140.03

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.3884(4)
_cell_length_b                   8.0901(6)
_cell_length_c                   6.8757(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.324(7)
_cell_angle_gamma                90
_cell_volume                     287.65(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2640
_cell_measurement_theta_min      3.087
_cell_measurement_theta_max      30.725

_exptl_crystal_description       lamellar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    6.995
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2634
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         30.725
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.795
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.795
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             1299
_reflns_number_gt                1064
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.647
_reflns_Friedel_fraction_full    0.917

_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-2014/7 (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)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.39(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1299
_refine_ls_number_parameters     89
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.115
_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
Br1 Br 0.03771(11) 0.3280(17) 0.19929(9) 0.0324(2) Uani 1 1 d . . . . .
N1 N -0.4263(10) 0.321(2) 0.7802(9) 0.0284(14) Uani 1 1 d D U . . .
C1 C -0.604(11) 0.178(5) 0.777(8) 0.023(6) Uani 0.5 1 d D U P A 1
C1' C -0.583(10) 0.166(5) 0.728(7) 0.023(6) Uani 0.5 1 d D U P A 2
C2 C -0.584(4) 0.4749(11) 0.765(3) 0.031(4) Uani 1 1 d D U . . .
C3 C -0.2746(15) 0.322(5) 0.6279(13) 0.044(2) Uani 1 1 d D U . . .
H10 H -0.306(9) 0.307(14) 0.917(5) 0.011(18) Uiso 1 1 d D . . . .
H1 H -0.74(2) 0.178(18) 0.851(19) 0.08(5) Uiso 1 1 d D . . . .
H4 H -0.48(4) 0.579(17) 0.76(4) 0.08(9) Uiso 1 1 d D . . . .
H2 H -0.48(2) 0.084(15) 0.78(3) 0.03(5) Uiso 1 1 d D . . . .
H5 H -0.72(3) 0.46(3) 0.631(17) 0.05(6) Uiso 1 1 d D . . . .
H7 H -0.397(14) 0.35(2) 0.493(9) 0.07(4) Uiso 1 1 d D . . . .
H3 H -0.71(4) 0.17(2) 0.633(14) 0.05(6) Uiso 1 1 d D . . . .
H6 H -0.657(16) 0.464(11) 0.882(9) 0.01(2) Uiso 1 1 d D . . . .
H9 H -0.194(15) 0.209(7) 0.627(13) 0.01(2) Uiso 1 1 d D . . . .
H8 H -0.124(13) 0.399(10) 0.671(15) 0.04(3) Uiso 1 1 d D . . . .

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 0.0258(3) 0.0375(4) 0.0277(4) 0.0034(12) -0.0028(2) 0.0016(14)
N1 0.021(2) 0.036(4) 0.024(3) -0.006(7) -0.0014(19) 0.000(7)
C1 0.033(12) 0.028(6) 0.007(19) -0.003(9) 0.006(10) 0.000(9)
C1' 0.033(12) 0.028(6) 0.007(19) -0.003(9) 0.006(10) 0.000(9)
C2 0.030(9) 0.030(6) 0.033(10) 0.003(7) 0.006(8) -0.003(7)
C3 0.029(3) 0.064(6) 0.038(4) -0.011(12) 0.009(3) -0.016(11)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1' 1.50(2) . ?
N1 C1 1.49(2) . ?
N1 C2 1.496(16) . ?
N1 C3 1.499(9) . ?

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
C1' N1 C2 114(2) . . ?
C1 N1 C2 107(2) . . ?
C1' N1 C3 102(2) . . ?
C1 N1 C3 118(2) . . ?
C2 N1 C3 110.9(19) . . ?

_refine_diff_density_max         1.047
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.118

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7


TITL 1 in P2(1)
CELL 0.71073   5.38841   8.09007   6.87569  90.0000 106.3239  90.0000
ZERR    4.00   0.00035   0.00062   0.00050   0.0000   0.0071   0.0000
LATT -1
SYMM -X, 0.5+Y, -Z
SFAC C H N BR
UNIT 12 40 4 4

DFIX 1.0 0.02 N1 H10 C1 H1 C2 H4 C2 H5 C1 H2 C1 H3 C3 H7 C3 H8 C3 H9 C2 H6
DFIX 1.5 0.02 N1 C1 N1 C2 N1 C3 N1 C1'
EADP C1 C1'
L.S. 800
SIMU
DELU
BOND
FMAP 2
PLAN 20
ACTA

WGHT    0.030000
FVAR       0.68232
BR1   4    0.037712    0.327981    0.199291    11.00000    0.02577    0.03747 =
         0.02772    0.00336   -0.00278    0.00163
N1    3   -0.426257    0.320593    0.780214    11.00000    0.02051    0.03618 =
         0.02373   -0.00562   -0.00141   -0.00041
PART 1
C1    1   -0.603775    0.178487    0.777038    10.50000    0.03314    0.02841 =
         0.00727   -0.00303    0.00614   -0.00047
PART 2
C1'   1   -0.582692    0.165730    0.727556    10.50000    0.03314    0.02841 =
         0.00727   -0.00303    0.00614   -0.00047
PART 0
C2    1   -0.583630    0.474889    0.765121    11.00000    0.02988    0.02967 =
         0.03295    0.00337    0.00559   -0.00292
C3    1   -0.274645    0.321590    0.627854    11.00000    0.02923    0.06361 =
         0.03803   -0.01101    0.00932   -0.01573
H10   2   -0.306311    0.307078    0.917476    11.00000    0.01076
H1    2   -0.739864    0.177508    0.850793    11.00000    0.07561
H4    2   -0.483904    0.579253    0.760493    11.00000    0.08408
H2    2   -0.481284    0.083862    0.780985    11.00000    0.03033
H5    2   -0.717178    0.462710    0.630776    11.00000    0.05258
H7    2   -0.396650    0.347883    0.493422    11.00000    0.06929
H3    2   -0.713549    0.169630    0.632925    11.00000    0.04741
H6    2   -0.657403    0.463802    0.882347    11.00000    0.00692
H9    2   -0.194022    0.208986    0.626971    11.00000    0.00945
H8    2   -0.124228    0.399367    0.670821    11.00000    0.04372

HKLF 4

REM  1 in P2(1)
REM R1 =  0.0416 for    1064 Fo > 4sig(Fo)  and  0.0511 for all    1299 data
REM     89 parameters refined using     54 restraints

END

WGHT      0.0495      0.0000

REM Highest difference peak  1.047,  deepest hole -0.693,  1-sigma level  0.118
Q1    1  -0.1055  0.3285  0.0945  11.00000  0.05    1.05
Q2    1   0.1877  0.3265  0.3000  11.00000  0.05    0.99
Q3    1   0.0414  0.3300  0.0272  11.00000  0.05    0.48
Q4    1   0.0336  0.4265  0.1028  11.00000  0.05    0.46
Q5    1   0.0325  0.2274  0.1017  11.00000  0.05    0.45
Q6    1  -0.2220  0.3269  0.2194  11.00000  0.05    0.45
Q7    1   0.3018  0.3277  0.1779  11.00000  0.05    0.44
Q8    1   0.1898  0.2035  0.2389  11.00000  0.05    0.44
Q9    1  -0.2117  0.3266  0.9836  11.00000  0.05    0.42
Q10   1   0.0340  0.4415  0.2958  11.00000  0.05    0.41
Q11   1  -0.6653  0.5211  0.4860  11.00000  0.05    0.40
Q12   1   0.1848  0.4512  0.2376  11.00000  0.05    0.40
Q13   1  -0.6643  0.1347  0.4866  11.00000  0.05    0.39
Q14   1   0.0288  0.2146  0.2992  11.00000  0.05    0.39
Q15   1  -0.1148  0.4548  0.1579  11.00000  0.05    0.39
Q16   1  -0.7079  0.3273  0.4002  11.00000  0.05    0.35
Q17   1  -0.0801  0.3291  0.2898  11.00000  0.05    0.35
Q18   1  -0.1135  0.2157  0.1405  11.00000  0.05    0.35
Q19   1   0.0015  0.3268  0.3382  11.00000  0.05    0.34
Q20   1  -0.0197  0.1238  0.7866  11.00000  0.05    0.33
;
_shelx_res_checksum              9281

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_chemical_properties_physical    Moisture-sensitive,Hygroscopic
