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

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

data_dabcoBr_173_honnsoku_a
_database_code_depnum_ccdc_archive 'CCDC 1979316'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi university
Japan
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 Br3 N3'
_chemical_formula_weight         367.93

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

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   9.6026(5)
_cell_length_b                   9.6026(5)
_cell_length_c                   23.3261(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1862.7(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4327
_cell_measurement_theta_min      2.4597
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2

_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    9.707
_exptl_absorpt_correction_T_min  0.49185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 1.678
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Mercury (2x2 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16096
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         30.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3613
_reflns_number_gt                3008
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    1.000

_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       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    yadokari
_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)+(0.0526P)²+0.7562P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3613
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35552(9) -0.11125(9) 0.26023(3) 0.0335(2) Uani 1 1 d . . . . .
Br2 Br 0.96905(10) 0.17135(9) 0.57110(3) 0.0336(2) Uani 1 1 d . . . . .
Br3 Br 0.47568(9) 0.14607(9) 0.58327(3) 0.0340(2) Uani 1 1 d . . . . .
C1 C 0.3912(10) -0.4714(8) 0.2776(3) 0.0313(16) Uani 1 1 d . . . . .
H1 H 0.503262 -0.389101 0.268148 0.038 Uiso 1 1 calc R U . A 2
H2 H 0.348865 -0.425180 0.305898 0.038 Uiso 1 1 calc R U . A 2
C2 C 0.2890(9) -0.5209(9) 0.2241(4) 0.0335(17) Uani 1 1 d . . . . .
H3 H 0.336760 -0.435037 0.194764 0.040 Uiso 1 1 calc R U . B 2
H4 H 0.179046 -0.542619 0.232945 0.040 Uiso 1 1 calc R U . B 2
C3 C 0.219(2) -0.765(2) 0.3006(8) 0.029(4) Uani 0.5 1 d . . P C 2
H5 H 0.217193 -0.856446 0.320626 0.035 Uiso 0.5 1 calc R U P C 2
H6 H 0.141740 -0.740113 0.319714 0.035 Uiso 0.5 1 calc R U P C 2
C4 C 0.1738(18) -0.806(2) 0.2385(7) 0.030(3) Uani 0.5 1 d . . P C 2
H7 H 0.178099 -0.903869 0.228203 0.036 Uiso 0.5 1 calc R U P C 2
H8 H 0.062746 -0.827938 0.232015 0.036 Uiso 0.5 1 calc R U P C 2
C5 C 0.4959(19) -0.648(2) 0.2673(7) 0.028(3) Uiso 0.5 1 d . . P C 2
H9 H 0.487259 -0.751415 0.278564 0.033 Uiso 0.5 1 calc R U P C 2
H10 H 0.608068 -0.561349 0.274073 0.033 Uiso 0.5 1 calc R U P C 2
C6 C 0.456(2) -0.653(2) 0.2050(7) 0.028(4) Uiso 0.5 1 d . . P C 2
H11 H 0.456266 -0.744110 0.185770 0.034 Uiso 0.5 1 calc R U P C 2
H12 H 0.534453 -0.551776 0.185789 0.034 Uiso 0.5 1 calc R U P C 2
C7 C 0.079(2) -0.273(3) 0.1383(7) 0.052(6) Uani 0.5 1 d . . P D 1
H13 H 0.161197 -0.157026 0.139076 0.063 Uiso 0.5 1 calc R U P D 1
H14 H 0.061283 -0.314557 0.178016 0.063 Uiso 0.5 1 calc R U P D 1
C8 C 0.132(2) -0.363(2) 0.1011(10) 0.046(5) Uani 0.5 1 d . . P D 1
H15 H 0.248105 -0.294800 0.092386 0.055 Uiso 0.5 1 calc R U P D 1
H16 H 0.115894 -0.460481 0.121176 0.055 Uiso 0.5 1 calc R U P D 1
C9 C -0.050(2) -0.216(2) 0.0561(10) 0.036(4) Uani 0.5 1 d . . P D 1
H17 H -0.152644 -0.249618 0.035758 0.043 Uiso 0.5 1 calc R U P D 1
H18 H 0.005843 -0.097540 0.061104 0.043 Uiso 0.5 1 calc R U P D 1
C10 C 0.051(2) -0.261(2) 0.0222(7) 0.042(5) Uani 0.5 1 d . . P D 1
H19 H 0.163915 -0.171335 0.022102 0.050 Uiso 0.5 1 calc R U P D 1
H20 H 0.012526 -0.283531 -0.017922 0.050 Uiso 0.5 1 calc R U P D 1
N1 N 0.3409(9) 0.3409(9) 0.000000 0.044(3) Uani 1 2 d S T P . .
N2 N 0.3324(11) 0.3324(11) 0.500000 0.051(3) Uani 1 2 d S T P . .
N3 N 0.387(2) -0.6191(19) 0.3021(5) 0.025(3) Uani 0.5 1 d . . P C 2
H21 H 0.426195 -0.597393 0.342581 0.030 Uiso 0.5 1 calc R U P C 2
N4 N 0.2848(17) -0.6727(17) 0.2028(5) 0.025(3) Uani 0.5 1 d . . P C 2
H22 H 0.245381 -0.693592 0.162337 0.030 Uiso 0.5 1 calc R U P C 2
N5 N -0.0824(18) -0.2955(19) 0.1128(7) 0.035(3) Uani 0.5 1 d . . P D 1
H23 H -0.130679 -0.249363 0.139267 0.042 Uiso 0.5 1 calc R U P D 1
N6 N 0.0411(18) -0.407(2) 0.0488(6) 0.029(3) Uani 0.5 1 d . . P D 1
H24 H 0.089160 -0.451960 0.021743 0.034 Uiso 0.5 1 calc R U P D 1


_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 N3 1.510(16) . ?
C1 C2 1.510(11) . ?
C1 N6 1.525(16) 4_545 ?
C2 N4 1.521(16) . ?
C2 N5 1.537(17) 4_545 ?
C3 C4 1.51(2) . ?
C3 N3 1.52(3) . ?
C4 N4 1.450(19) . ?
C5 N3 1.46(2) . ?
C5 C6 1.50(2) . ?
C6 N4 1.55(2) . ?
C7 C8 1.49(3) . ?
C7 N5 1.57(2) . ?
C8 N6 1.44(2) . ?
C9 C10 1.47(2) . ?
C9 N5 1.48(2) . ?
C10 N6 1.49(2) . ?

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
N3 C1 C2 108.0(7) . . ?
N3 C1 N6 24.9(6) . 4_545 ?
C2 C1 N6 105.8(7) . 4_545 ?
C1 C2 N4 105.8(6) . . ?
C1 C2 N5 105.4(7) . 4_545 ?
C4 C3 N3 107.3(12) . . ?
N4 C4 C3 109.3(13) . . ?
N3 C5 C6 110.2(13) . . ?
C5 C6 N4 106.1(13) . . ?
C8 C7 N5 107.4(12) . . ?
N6 C8 C7 109.3(13) . . ?
C10 C9 N5 109.0(15) . . ?
C9 C10 N6 108.1(14) . . ?
C5 N3 C1 106.4(11) . . ?
C5 N3 C3 110.2(13) . . ?
C1 N3 C3 112.0(13) . . ?
C4 N4 C2 108.4(12) . . ?
C4 N4 C6 110.8(12) . . ?
C2 N4 C6 110.5(11) . . ?
C9 N5 C2 113.1(13) . 4_445 ?
C9 N5 C7 109.3(14) . . ?
C2 N5 C7 103.5(13) 4_445 . ?
C8 N6 C10 109.4(14) . . ?
C8 N6 C1 114.9(13) . 4_445 ?
C10 N6 C1 106.5(12) . 4_445 ?

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
N3 C1 C2 N4 -24.1(13) . . . . ?
N6 C1 C2 N5 30.4(13) 4_545 . . 4_545 ?
N3 C3 C4 N4 -14(2) . . . . ?
N3 C5 C6 N4 -15.5(18) . . . . ?
N5 C7 C8 N6 13(2) . . . . ?
N5 C9 C10 N6 18(2) . . . . ?
C6 C5 N3 C1 -52.3(16) . . . . ?
C6 C5 N3 C3 69.4(17) . . . . ?
C2 C1 N3 C5 78.0(13) . . . . ?
C2 C1 N3 C3 -42.5(13) . . . . ?
C4 C3 N3 C5 -52.2(18) . . . . ?
C4 C3 N3 C1 66.0(16) . . . . ?
C3 C4 N4 C2 -53.2(15) . . . . ?
C3 C4 N4 C6 68.1(17) . . . . ?
C1 C2 N4 C4 77.0(11) . . . . ?
C1 C2 N4 C6 -44.6(13) . . . . ?
C5 C6 N4 C4 -51.2(17) . . . . ?
C5 C6 N4 C2 68.9(15) . . . . ?
C10 C9 N5 C2 -67.9(19) . . . 4_445 ?
C10 C9 N5 C7 47(2) . . . . ?
C8 C7 N5 C9 -66(2) . . . . ?
C8 C7 N5 C2 54.6(18) . . . 4_445 ?
C7 C8 N6 C10 53(2) . . . . ?
C7 C8 N6 C1 -67(2) . . . 4_445 ?
C9 C10 N6 C8 -73.7(19) . . . . ?
C9 C10 N6 C1 51.1(17) . . . 4_445 ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -2.731
_refine_diff_density_rms         0.359

