# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_yo_end
_database_code_depnum_ccdc_archive 'CCDC 2340566'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.19I0.81
_chemical_formula_moiety         'C6 H13 N2, 0.19(Br), 0.81(I)'
_chemical_formula_sum            'C6 H13 Br0.19 I0.81 N2'
_chemical_formula_weight         231.16
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.25I0.75
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   7.0554(4)
_cell_length_b                   7.0554(4)
_cell_length_c                   5.3478(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     230.54(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.0460
_cell_measurement_theta_min      3.3380
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.278
_exptl_absorpt_coefficient_mu    3.591
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             113
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -8 0.1551
-1 0 7 0.3168
-10 3 0 0.0392
0 0 8 0.3176
2 -9 0 0.0168
-4 10 0 0.0149
-1 9 0 0.0112
3 7 0 0.0112
10 -6 0 0.0205

_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2151 0.0446 -7.5328 0.0383 0.0240 0.9990
-1.1850 0.2647 7.4769 -0.1256 -0.0715 -0.9895
-9.7342 3.0948 0.0891 -0.8783 -0.4781 0.0090
0.1744 -0.0653 7.5344 0.0046 -0.0140 -0.9999
2.0366 -9.4513 -0.1890 -0.4781 0.8783 0.0090
-4.0197 9.8916 0.0824 0.2850 -0.9585 0.0091
-1.0123 9.0800 0.0352 0.5672 -0.8235 0.0091
3.0984 6.6422 -0.0426 0.8531 -0.5216 0.0092
9.8837 -5.8608 -0.2554 0.6876 0.7261 0.0092

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1334
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.195
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  63.00   0.25    1.00    --   16.26   2.00 -21.00  488
  2  ω     53.00  83.00   0.25    1.00    --   16.26-135.00 -62.00  120
  3  ω     -6.00  25.00   0.25    1.00    --  -15.63 -99.00 -60.00  124
  4  ω    -10.00  31.00   0.25    1.00    --  -15.63 -99.00-120.00  164
  5  ω     73.00  99.00   0.25    1.00    --   16.26-178.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1141223000
_diffrn_orient_matrix_UB_12      0.0751998000
_diffrn_orient_matrix_UB_13      -0.0013764000
_diffrn_orient_matrix_UB_21      0.0209957000
_diffrn_orient_matrix_UB_22      -0.0883412000
_diffrn_orient_matrix_UB_23      -0.0031104000
_diffrn_orient_matrix_UB_31      -0.0017136000
_diffrn_orient_matrix_UB_32      0.0013291000
_diffrn_orient_matrix_UB_33      -0.1326589000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                245
_reflns_number_total             245
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0141
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0353
_refine_ls_wR_factor_ref         0.0353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{Br1, I1}
3. Uiso/Uaniso restraints and constraints
Uiso(Br1) = Uiso(I1)
4. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) Br1(0.01583) I1(0.0675)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.666667 0.333333 0.7637(8) 0.0498(13) Uani 1 6 d S T P . .
H1 H 0.666666 0.333334 0.580442 0.060 Uiso 0.5 6 calc R U P . .
C1 C 0.7805(4) 0.5610(8) 0.8556(5) 0.0566(11) Uani 1 2 d S T P . .
H1A H 0.707093 0.636974 0.794254 0.068 Uiso 0.5 1 calc R U P . .
H1B H 0.929880 0.636976 0.794249 0.068 Uiso 0.5 1 calc R U P . .
Br1 Br 0.333333 0.666667 0.500000 0.05024(19) Uiso 0.19 12 d S . P A 3
I1 I 0.333333 0.666667 0.500000 0.05024(19) Uiso 0.81 12 d S . P B 4

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
N1 0.059(2) 0.059(2) 0.0313(17) 0.000 0.000 0.0295(11)
C1 0.065(2) 0.055(2) 0.0465(17) 0.0043(15) 0.0021(8) 0.0273(12)

_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 H1 0.9800 . ?
N1 C1 1.475(5) . ?
N1 C1 1.475(5) 3_665 ?
N1 C1 1.475(5) 2_655 ?
C1 C1 1.544(6) 4_557 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.5 3_665 . ?
C1 N1 H1 109.5 2_655 . ?
C1 N1 H1 109.5 . . ?
C1 N1 C1 109.5(2) 3_665 2_655 ?
C1 N1 C1 109.5(2) 2_655 . ?
C1 N1 C1 109.5(2) 3_665 . ?
N1 C1 C1 109.5(2) . 4_557 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4_557 . ?
C1 C1 H1B 109.8 4_557 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 -60.0(3) 3_665 . . 4_557 ?
C1 N1 C1 C1 60.0(3) 2_655 . . 4_557 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 12:51:34 on 28-Jul-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.030, Rweak 0.449, Alpha 0.003
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.115 ( 0.042 ) from 97 Parsons' quotients
REM Formula found by SHELXT: C10 I
CELL 0.71073 7.0554 7.0554 5.3478 90 90 120
ZERR 1 0.0004 0.0004 0.0003 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.19 0.81 2
EADP Br1 I1
EXYZ Br1 I1

L.S. 4
PLAN  5
SIZE 0.04 0.07 0.48
TEMP 24.85
CONF
BOND
list 4
fmap 2
ACTA
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.023200
FVAR       2.02883
N1    5    0.666667    0.333333    0.763695    10.16667    0.05910    0.05910 =
         0.03130    0.00000    0.00000    0.02955
AFIX  13
H1    2    0.666666    0.333334    0.580442    10.08333   -1.20000
AFIX   0
C1    1    0.780503    0.561005    0.855634    10.50000    0.06519    0.05462 =
         0.04649    0.00427    0.00214    0.02731
AFIX  23
H1A   2    0.707093    0.636974    0.794254    10.50000   -1.20000
H1B   2    0.929880    0.636976    0.794249    10.50000   -1.20000
AFIX   0

PART 3
BR1   3    0.333333    0.666667    0.500000    10.01583    0.05024

PART 4
I1    4    0.333333    0.666667    0.500000    10.06750    0.05024
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0353, GooF = S = 1.097, Restrained GooF = 1.097 for all data
REM R1 = 0.0141 for 245 Fo > 4sig(Fo) and 0.0141 for all 245 data
REM 11 parameters refined using 0 restraints

END

WGHT      0.0232      0.0000

REM Highest difference peak  0.267,  deepest hole -0.101,  1-sigma level  0.039
Q1    1   0.4019  0.8038  0.5000  10.25000  0.05    0.27
Q2    1   0.2662  0.5325  0.5000  10.25000  0.05    0.27
Q3    1   0.3333  0.6667  0.3342  10.16667  0.05    0.14
Q4    1   0.5280  0.4720  0.5000  10.25000  0.05    0.11
Q5    1   0.4847  0.2423  0.5000  10.25000  0.05    0.09
;
_shelx_res_checksum              74301
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.695
_oxdiff_exptl_absorpt_empirical_full_min 0.489
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_yo_end_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2340567'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.27I0.73
_chemical_formula_moiety         'C6 H13 N2, 0.27(Br), 0.73(I)'
_chemical_formula_sum            'C6 H13 Br0.27 I0.73 N2'
_chemical_formula_weight         227.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.27I0.73
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.9445(9)
_cell_length_b                   6.9445(9)
_cell_length_c                   5.3334(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     222.75(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    868
_cell_measurement_temperature    298
_cell_measurement_theta_max      36.6490
_cell_measurement_theta_min      3.3810
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.416
_exptl_absorpt_coefficient_mu    3.798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             111
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -4 0 0.0868
0 8 3 0.0367
-1 -7 -3 0.0095
1 -1 -7 0.0965
9 -7 1 0.0458
-9 7 -2 0.0059
0 0 1 0.1337

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.7754 -4.4886 -0.0080 -0.3032 -0.9465 -0.1104
0.2832 7.6840 2.8916 -0.9088 0.2545 -0.3308
-0.8684 -7.3678 -2.8736 0.9214 -0.1961 0.3354
1.3419 -0.7856 -7.4448 0.0051 -0.2604 0.9655
9.3878 -6.9701 0.6634 0.0090 -0.9770 -0.2128
-9.2218 6.8713 -1.5280 -0.0084 0.9457 0.3248
0.0000 -0.0000 1.0000 -0.0037 0.0168 -0.1319

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            809
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         3.387
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  26.00   0.25    0.80    --  -32.68  12.00 176.00  244
  2  ω     15.00  78.00   0.25    0.80    --   33.31-117.00-119.00  252
  3  ω     70.00 112.00   0.25    0.80    --   33.31 178.00 -90.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0832801000
_diffrn_orient_matrix_UB_12      -0.1138103000
_diffrn_orient_matrix_UB_13      -0.0036840000
_diffrn_orient_matrix_UB_21      -0.0831081000
_diffrn_orient_matrix_UB_22      0.0298443000
_diffrn_orient_matrix_UB_23      0.0168435000
_diffrn_orient_matrix_UB_31      -0.0082315000
_diffrn_orient_matrix_UB_32      0.0068942000
_diffrn_orient_matrix_UB_33      -0.1318982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.514
_reflns_Friedel_fraction_full    0.631
_reflns_Friedel_fraction_max     0.655
_reflns_number_gt                218
_reflns_number_total             218
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 73 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.1096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0667
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{Br1, I1}
3. Uiso/Uaniso restraints and constraints
Uiso(Br1) = Uiso(I1)
4. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) Br1(0.0225) I1(0.06083)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.666667 0.333333 0.7641(15) 0.051(2) Uani 1 6 d S T P . .
H1 H 0.666667 0.333333 0.580328 0.061 Uiso 0.5 6 calc R U P . .
C1 C 0.7821(7) 0.5642(14) 0.8547(9) 0.0569(18) Uani 1 2 d S T P . .
H1A H 0.707427 0.641248 0.793000 0.068 Uiso 0.5 1 calc R U P . .
H1B H 0.933821 0.641248 0.793001 0.068 Uiso 0.5 1 calc R U P . .
Br1 Br 0.333333 0.666667 0.500000 0.0512(3) Uiso 0.27 12 d S . P A 3
I1 I 0.333333 0.666667 0.500000 0.0512(3) Uiso 0.73 12 d S . P B 4

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
N1 0.062(4) 0.062(4) 0.028(3) 0.000 0.000 0.0310(19)
C1 0.069(4) 0.054(4) 0.042(3) 0.005(3) 0.0025(13) 0.0272(18)

_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 H1 0.9800 . ?
N1 C1 1.470(8) 2_655 ?
N1 C1 1.470(8) 3_665 ?
N1 C1 1.470(9) . ?
C1 C1 1.550(10) 4_557 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.2 3_665 . ?
C1 N1 H1 109.2 . . ?
C1 N1 H1 109.2 2_655 . ?
C1 N1 C1 109.7(4) 3_665 . ?
C1 N1 C1 109.7(4) . 2_655 ?
C1 N1 C1 109.7(4) 3_665 2_655 ?
N1 C1 C1 109.2(4) . 4_557 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4_557 . ?
C1 C1 H1B 109.8 4_557 . ?
H1A C1 H1B 108.3 . . ?

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
C1 N1 C1 C1 -60.3(5) 3_665 . . 4_557 ?
C1 N1 C1 C1 60.3(5) 2_655 . . 4_557 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 17:55:19 on 31-Jul-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.042, Rweak 0.414, Alpha 0.002
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.171 ( 0.048 ) from 59 Parsons' quotients
REM Formula found by SHELXT: C8 N2 I
CELL 0.71073 6.9445 6.9445 5.3334 90 90 120
ZERR 1 0.0009 0.0009 0.0005 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.27 0.73 2
EADP Br1 I1
EXYZ Br1 I1

L.S. 4
PLAN  5
SIZE 0.05 0.07 0.28
TEMP 27
CONF
BOND
list 4
fmap 2
ACTA
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.043500    0.109600
FVAR       2.04858
N1    5    0.666667    0.333333    0.764076    10.16667    0.06209    0.06209 =
         0.02761    0.00000    0.00000    0.03104
AFIX  13
H1    2    0.666667    0.333333    0.580328    10.08333   -1.20000
AFIX   0
C1    1    0.782113    0.564226    0.854727    10.50000    0.06900    0.05439 =
         0.04244    0.00508    0.00254    0.02719
AFIX  23
H1A   2    0.707427    0.641248    0.793000    10.50000   -1.20000
H1B   2    0.933821    0.641248    0.793001    10.50000   -1.20000
AFIX   0

PART 3
BR1   3    0.333333    0.666667    0.500000    10.02250    0.05115
PART 4
I1    4    0.333333    0.666667    0.500000    10.06083    0.05115
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0667, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0263 for 218 Fo > 4sig(Fo) and 0.0263 for all 218 data
REM 11 parameters refined using 0 restraints

END

WGHT      0.0435      0.1106

REM Highest difference peak  0.725,  deepest hole -0.875,  1-sigma level  0.070
Q1    1   0.3811  0.7623  0.3392  10.50000  0.05    0.19
Q2    1   0.2884  0.5769  0.3396  10.50000  0.05    0.19
Q3    1   0.7216  0.4432  0.8128  10.50000  0.05    0.18
Q4    1   0.8335  0.6669  0.8450  10.50000  0.05    0.17
Q5    1   0.4506  0.9011  0.5000  10.25000  0.05    0.16
;
_shelx_res_checksum              80722
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.511
####################################################################### 
# 
# 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_yo_end_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2340568'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.64I0.36
_chemical_formula_moiety         'C6 H13 N2, 0.36(I), 0.64(Br)'
_chemical_formula_sum            'C6 H13 Br0.64 I0.36 N2'
_chemical_formula_weight         210.01
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.65I0.35
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.8337(5)
_cell_length_b                   6.8337(5)
_cell_length_c                   5.3349(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     215.76(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1051
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.4670
_cell_measurement_theta_min      3.4390
_shelx_estimated_absorpt_T_max   0.724
_shelx_estimated_absorpt_T_min   0.400
_exptl_absorpt_coefficient_mu    4.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             104
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1547
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         3.442
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -60.00   0.25    2.16    --  -12.77 157.00 126.00  100
  2  ω    -39.00 -13.00   0.25    2.16    --  -12.77 119.00 -28.00  104
  3  ω     17.00  42.00   0.25    2.16    --   13.32-119.00-113.00  100
  4  ω     61.00  88.00   0.25    2.16    --   13.32-157.00  91.00  108
  5  ω    -88.00  12.00   0.25    2.16    --  -12.77 -57.00-180.00  400
  6  ω    -16.00  58.00   0.25    2.16    --   13.32 -99.00  90.00  296
  7  ω     12.00  40.00   0.25    2.16    --   13.32 -57.00 150.00  112
  8  ω    -62.00 -25.00   0.25    2.16    --   13.32 -57.00 150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0897109000
_diffrn_orient_matrix_UB_12      0.1133015000
_diffrn_orient_matrix_UB_13      -0.0074417000
_diffrn_orient_matrix_UB_21      -0.0791490000
_diffrn_orient_matrix_UB_22      0.0368169000
_diffrn_orient_matrix_UB_23      -0.0203079000
_diffrn_orient_matrix_UB_31      -0.0068665000
_diffrn_orient_matrix_UB_32      0.0122971000
_diffrn_orient_matrix_UB_33      0.1312417000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                237
_reflns_number_total             240
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.805
_refine_diff_density_min         -1.055
_refine_diff_density_rms         0.151
_refine_ls_abs_structure_details 
;
 Flack x determined using 94 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.077
_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)+(0.1013P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(10)
 0(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Shared sites
{I1, Br1}
4. Uiso/Uaniso restraints and constraints
Uiso(I1) = Uiso(Br1)
5. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) I1(0.03) Br1(0.05333)
6.a Ternary CH refined with riding coordinates:
 N1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.666667 0.333333 0.762(3) 0.051(4) Uani 1 6 d S T P . .
H1 H 0.666667 0.333334 0.578490 0.061 Uiso 0.5 6 calc R U P . .
C1 C 0.7840(12) 0.568(2) 0.8550(17) 0.058(3) Uani 1 2 d S T P . .
H1A H 0.708282 0.646549 0.793550 0.070 Uiso 0.5 1 calc R U P . .
H1B H 0.938266 0.646549 0.793550 0.070 Uiso 0.5 1 calc R U P . .
I1 I 0.333333 0.666667 0.500000 0.0520(7) Uiso 0.36 12 d S . P A 3
Br1 Br 0.333333 0.666667 0.500000 0.0520(7) Uiso 0.64 12 d S . P B 4

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
N1 0.060(6) 0.060(6) 0.032(6) 0.000 0.000 0.030(3)
C1 0.070(6) 0.055(5) 0.045(5) 0.006(5) 0.003(2) 0.027(3)

_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 H1 0.9800 . ?
N1 C1 1.475(14) 2_655 ?
N1 C1 1.475(14) 3_665 ?
N1 C1 1.475(14) . ?
C1 C1 1.547(18) 4_557 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.6 3_665 . ?
C1 N1 H1 109.6 . . ?
C1 N1 H1 109.6 2_655 . ?
C1 N1 C1 109.3(7) 3_665 . ?
C1 N1 C1 109.3(7) . 2_655 ?
C1 N1 C1 109.3(7) 3_665 2_655 ?
N1 C1 C1 109.6(7) . 4_557 ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C1 C1 H1A 109.7 4_557 . ?
C1 C1 H1B 109.7 4_557 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 -59.8(8) 3_665 . . 4_557 ?
C1 N1 C1 C1 59.8(8) 2_655 . . 4_557 ?

_shelx_res_file                  
;
TITL yo_end_c.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 12:52:17 on 01-Aug-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.083, Rweak 0.410, Alpha 0.018
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.262 ( 0.054 ) from 90 Parsons' quotients
REM Formula found by SHELXT: C10 I
CELL 0.71073 6.8337 6.8337 5.3349 90 90 120
ZERR 1 0.0005 0.0005 0.0003 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.64 0.36 2
EADP I1 Br1
EXYZ I1 Br1

L.S. 10
PLAN  5
SIZE 0.08 0.1 0.26
TEMP 24.85
CONF
BOND
LIST 6
fmap 2
ACTA
MORE -1
BOND $H
TWIN -1 0 0 1 1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.101300
BASF   0.11460
FVAR       2.17865
N1    5    0.666667    0.333333    0.762186    10.16667    0.06016    0.06016 =
         0.03161    0.00000    0.00000    0.03008
AFIX  13
H1    2    0.666667    0.333334    0.578490    10.08333   -1.20000
AFIX   0
C1    1    0.784011    0.568022    0.854982    10.50000    0.06964    0.05455 =
         0.04542    0.00605    0.00302    0.02727
AFIX  23
H1A   2    0.708282    0.646549    0.793550    10.50000   -1.20000
H1B   2    0.938266    0.646549    0.793550    10.50000   -1.20000
AFIX   0

PART 3
I1    4    0.333333    0.666667    0.500000    10.03000    0.05198

PART 4
BR1   3    0.333333    0.666667    0.500000    10.05333    0.05198
HKLF 4




REM  yo_end_c.res in P-6m2
REM wR2 = 0.1275, GooF = S = 1.077, Restrained GooF = 1.077 for all data
REM R1 = 0.0525 for 237 Fo > 4sig(Fo) and 0.0533 for all 240 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.1010      0.0000

REM Highest difference peak  1.805,  deepest hole -1.055,  1-sigma level  0.151
Q1    1   0.3868  0.7735  0.5000  10.25000  0.05    1.80
Q2    1   0.2818  0.5635  0.5000  10.25000  0.05    1.77
Q3    1   0.7193  0.4387  0.8112  10.50000  0.05    0.32
Q4    1   0.4809  0.9618  0.5000  10.25000  0.05    0.25
Q5    1   0.8299  0.6597  0.8520  10.50000  0.05    0.23
;
_shelx_res_checksum              15658
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.795
_oxdiff_exptl_absorpt_empirical_full_min 0.730
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(10)
2 0(10)

####################################################################### 
# 
# 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_yo_end_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2340569'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.74I0.26
_chemical_formula_moiety         'C6 H13 N2, 0.26(I), 0.74(Br1)'
_chemical_formula_sum            'C6 H13 Br0.74 I0.26 N2'
_chemical_formula_weight         205.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.7I0.3
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.8015(6)
_cell_length_b                   6.8015(6)
_cell_length_c                   5.3298(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     213.53(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    715
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.6690
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.312
_exptl_absorpt_coefficient_mu    4.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             103
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -7 0.1162
7 -9 -1 0.0526
0 -1 7 0.2312
-7 9 0 0.0149

_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.2567 0.6558 -7.4926 0.0019 0.0714 0.9974
6.5517 -9.2956 -0.6784 0.0100 -0.9952 0.0975
0.4722 -0.9616 7.4727 -0.0016 -0.1041 -0.9946
-6.5601 9.3386 -0.1220 -0.0098 0.9999 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            803
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.246
_diffrn_reflns_theta_min         3.459
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.25    0.80    --   -9.50   2.00 -68.00  240
  2  ω    -18.00  30.00   0.25    0.80    --   -9.50 -99.00-180.00  192
  3  ω     30.00  55.00   0.25    0.80    --    9.97-137.00 121.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1169026000
_diffrn_orient_matrix_UB_12      -0.0832126000
_diffrn_orient_matrix_UB_13      -0.0035336000
_diffrn_orient_matrix_UB_21      -0.0286819000
_diffrn_orient_matrix_UB_22      0.0869120000
_diffrn_orient_matrix_UB_23      -0.0009337000
_diffrn_orient_matrix_UB_31      0.0033074000
_diffrn_orient_matrix_UB_32      0.0015559000
_diffrn_orient_matrix_UB_33      -0.1331012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                224
_reflns_number_total             224
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.978
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 
;
 Flack x determined using 92 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.2711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{I1, Br1}
3. Uiso/Uaniso restraints and constraints
Uiso(I1) = Uiso(Br1)
4. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) I1(0.02167) Br1(0.06167)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.666667 0.333333 0.237(3) 0.052(4) Uani 1 6 d S T P . .
H1 H 0.666667 0.333334 0.421291 0.062 Uiso 0.5 6 calc R U P . .
C1 C 0.428(2) 0.2141(11) 0.1449(15) 0.058(3) Uani 1 2 d S T P . .
H1A H 0.349399 0.290262 0.206563 0.069 Uiso 0.5 1 calc R U P . .
H1B H 0.349400 0.059136 0.206559 0.069 Uiso 0.5 1 calc R U P . .
I1 I 0.333333 0.666667 0.500000 0.0505(7) Uiso 0.26 12 d S . P A 3
Br1 Br 0.333333 0.666667 0.500000 0.0505(7) Uiso 0.74 12 d S . P B 4

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
N1 0.062(6) 0.062(6) 0.030(6) 0.000 0.000 0.031(3)
C1 0.057(6) 0.068(6) 0.044(5) 0.002(2) 0.005(5) 0.028(3)

_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 H1 0.9800 . ?
N1 C1 1.489(13) . ?
N1 C1 1.489(13) 2_655 ?
N1 C1 1.489(13) 3_665 ?
C1 C1 1.544(16) 4 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.3 2_655 . ?
C1 N1 H1 109.3 3_665 . ?
C1 N1 H1 109.3 . . ?
C1 N1 C1 109.6(6) 2_655 3_665 ?
C1 N1 C1 109.6(6) 3_665 . ?
C1 N1 C1 109.6(6) 2_655 . ?
N1 C1 C1 109.3(6) . 4 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4 . ?
C1 C1 H1B 109.8 4 . ?
H1A C1 H1B 108.3 . . ?

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
C1 N1 C1 C1 -60.2(8) 2_655 . . 4 ?
C1 N1 C1 C1 60.2(8) 3_665 . . 4 ?

_shelx_res_file                  
;
TITL yo_end_b.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 15:42:35 on 31-Jul-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.064, Rweak 0.380, Alpha 0.001
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.378 ( 0.119 ) from 84 Parsons' quotients
REM Formula found by SHELXT: C10 I1
CELL 0.71073 6.8015 6.8015 5.3298 90 90 120
ZERR 1 0.0006 0.0006 0.0004 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.74 0.26 2
EADP I1 Br1
EXYZ I1 Br1

L.S. 10
PLAN  5
SIZE 0.08 0.07 0.34
TEMP 24.85
CONF
BOND
LIST 6
fmap 2
ACTA
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.059700    0.271100
FVAR       2.26382
N1    5    0.666667    0.333333    0.237419    10.16667    0.06205    0.06205 =
         0.03045    0.00000    0.00000    0.03103
AFIX  13
H1    2    0.666667    0.333334    0.421291    10.08333   -1.20000
AFIX   0
C1    1    0.428129    0.214065    0.144888    10.50000    0.05678    0.06831 =
         0.04400    0.00232    0.00464    0.02839
AFIX  23
H1A   2    0.349399    0.290262    0.206563    10.50000   -1.20000
H1B   2    0.349400    0.059136    0.206559    10.50000   -1.20000
AFIX   0

PART 3
I1    4    0.333333    0.666667    0.500000    10.02167    0.05046

PART 4
BR1   3    0.333333    0.666667    0.500000    10.06167    0.05046
HKLF 4




REM  yo_end_b.res in P-6m2
REM wR2 = 0.1136, GooF = S = 1.206, Restrained GooF = 1.206 for all data
REM R1 = 0.0436 for 224 Fo > 4sig(Fo) and 0.0436 for all 224 data
REM 11 parameters refined using 0 restraints

END

WGHT      0.0594      0.2764

REM Highest difference peak  0.978,  deepest hole -1.134,  1-sigma level  0.103
Q1    1   0.2827  0.5655  0.5000  10.25000  0.05    0.98
Q2    1   0.3854  0.7707  0.5000  10.25000  0.05    0.98
Q3    1   0.3333  0.6667  0.3044  10.16667  0.05    0.51
Q4    1   0.3826  0.9171  0.5000  10.50000  0.05    0.33
Q5    1   0.5430  0.2715  0.1878  10.50000  0.05    0.21
;
_shelx_res_checksum              16238
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.410
####################################################################### 
# 
# 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_yo_end_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2340571'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.80I0.20_112K
_chemical_formula_moiety         'C6 H13 N2, 0.2(I1), 0.8(Br)'
_chemical_formula_sum            'C6 H13 Br0.80 I0.20 N2'
_chemical_formula_weight         202.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.8I0.2
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.7014(5)
_cell_length_b                   6.7014(5)
_cell_length_c                   5.3164(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     206.77(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1061
_cell_measurement_temperature    112
_cell_measurement_theta_max      29.2440
_cell_measurement_theta_min      3.4900
_shelx_estimated_absorpt_T_max   0.767
_shelx_estimated_absorpt_T_min   0.325
_exptl_absorpt_coefficient_mu    4.673
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             102
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 7 0 0.0131
1 -2 7 0.1701
-1 -7 0 0.0430
-2 1 -7 0.1308
3 6 0 0.0249
-9 6 1 0.0075
-1 -8 0 0.0467
8 -8 -1 0.0744

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.4796 7.3475 0.0569 0.0091 -0.0024 1.0000
1.2721 -2.1462 7.2940 0.8416 -0.5150 -0.1626
-1.4796 -7.3475 -0.0569 -0.0091 0.0024 -1.0000
-1.5592 0.8188 -7.3892 -0.8531 0.5214 -0.0196
3.3999 5.9350 -0.2505 0.1148 0.1829 0.9764
-9.2221 5.7700 1.2199 -0.5216 -0.8531 -0.0091
-0.9914 -7.6472 -0.0732 0.0234 0.0433 -0.9988
8.3842 -7.7374 -1.1707 0.4981 0.8163 -0.2924

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1173
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.243
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  43.00   0.25    0.11    --  -15.47  77.00 120.00  388
  2  ω    -91.00  19.00   0.25    0.11    --  -15.47 -67.00 162.00  440
  3  ω   -105.00 -41.00   0.25    0.11    --  -15.47-178.00-180.00  256
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0623402000
_diffrn_orient_matrix_UB_12      -0.0121032000
_diffrn_orient_matrix_UB_13      0.1009511000
_diffrn_orient_matrix_UB_21      0.0720917000
_diffrn_orient_matrix_UB_22      -0.0141671000
_diffrn_orient_matrix_UB_23      -0.0873502000
_diffrn_orient_matrix_UB_31      0.0764893000
_diffrn_orient_matrix_UB_32      0.1206929000
_diffrn_orient_matrix_UB_33      -0.0001155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                229
_reflns_number_total             229
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     13
_refine_ls_number_reflns         229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0715
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.59(8)
 0.41(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Shared sites
{I1, Br1}
4. Uiso/Uaniso restraints and constraints
Uanis(I1) = Uanis(Br1)
5. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) I1(0.01667) Br1(0.06667)
6.a Ternary CH refined with riding coordinates:
 N1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.666667 0.333333 0.2387(18) 0.022(2) Uani 1 6 d S T P . .
H1 H 0.666667 0.333334 0.426748 0.027 Uiso 0.5 6 calc R U P . .
C1 C 0.4252(14) 0.2126(7) 0.1469(9) 0.0239(17) Uani 1 2 d S T P . .
H1A H 0.343784 0.291615 0.210118 0.029 Uiso 0.5 1 calc R U P . .
H1B H 0.343782 0.052170 0.210122 0.029 Uiso 0.5 1 calc R U P . .
I1 I 0.333333 0.666667 0.500000 0.0195(4) Uani 0.2 12 d S T P A 5
Br1 Br 0.333333 0.666667 0.500000 0.0195(4) Uani 0.8 12 d S T P B 6

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
N1 0.025(4) 0.025(4) 0.016(4) 0.000 0.000 0.0124(18)
C1 0.020(3) 0.028(3) 0.021(3) 0.0001(11) 0.000(2) 0.0099(16)
I1 0.0210(5) 0.0210(5) 0.0166(5) 0.000 0.000 0.0105(2)
Br1 0.0210(5) 0.0210(5) 0.0166(5) 0.000 0.000 0.0105(2)

_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 H1 1.0000 . ?
N1 C1 1.484(8) 3_665 ?
N1 C1 1.484(8) 2_655 ?
N1 C1 1.484(8) . ?
C1 C1 1.562(9) 4 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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 H1 109.2 2_655 . ?
C1 N1 H1 109.2 . . ?
C1 N1 H1 109.2 3_665 . ?
C1 N1 C1 109.8(4) 2_655 . ?
C1 N1 C1 109.7(4) . 3_665 ?
C1 N1 C1 109.7(4) 2_655 3_665 ?
N1 C1 C1 109.2(4) . 4 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4 . ?
C1 C1 H1B 109.8 4 . ?
H1A C1 H1B 108.3 . . ?

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
C1 N1 C1 C1 -60.3(5) 2_655 . . 4 ?
C1 N1 C1 C1 60.3(5) 3_665 . . 4 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 09:34:13 on 05-Feb-2024
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.051, Rweak 0.364, Alpha 0.022
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.139 ( 0.126 ) from 85 Parsons' quotients
REM Formula found by SHELXT: C10 I
CELL 0.71073 6.7014 6.7014 5.3164 90 90 120
ZERR 1 0.0005 0.0005 0.0003 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.8 0.2 2
EADP I1 Br1
EXYZ I1 Br1

L.S. 4
PLAN  5
SIZE 0.06 0.09 0.31
TEMP -161.15
CONF
CONN 12 0.2 Br1
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.042200
BASF   0.40519
FVAR       1.91614
N1    5    0.666667    0.333333    0.238650    10.16667    0.02490    0.02490 =
         0.01648    0.00000    0.00000    0.01245
AFIX  13
H1    2    0.666667    0.333334    0.426748    10.08333   -1.20000
AFIX   0
C1    1    0.425241    0.212621    0.146916    10.50000    0.01981    0.02810 =
         0.02102    0.00011    0.00023    0.00990
AFIX  23
H1A   2    0.343784    0.291615    0.210118    10.50000   -1.20000
H1B   2    0.343782    0.052170    0.210122    10.50000   -1.20000
AFIX   0

PART 5
I1    4    0.333333    0.666667    0.500000    10.01667    0.02095    0.02095 =
         0.01658    0.00000    0.00000    0.01048
PART 6
BR1   3    0.333333    0.666667    0.500000    10.06667    0.02095    0.02095 =
         0.01658    0.00000    0.00000    0.01048
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0715, GooF = S = 1.141, Restrained GooF = 1.141 for all data
REM R1 = 0.0313 for 229 Fo > 4sig(Fo) and 0.0313 for all 229 data
REM 13 parameters refined using 0 restraints

END

WGHT      0.0422      0.0000

REM Highest difference peak  0.998,  deepest hole -0.354,  1-sigma level  0.109
Q1    1   0.3333  0.6667  0.3362  10.16667  0.05    1.00
Q2    1   0.2642  0.5283  0.5000  10.25000  0.05    0.67
Q3    1   0.4034  0.8069  0.5000  10.25000  0.05    0.66
Q4    1   0.3333  0.6667  0.0000  10.08333  0.05    0.41
Q5    1   0.4320  0.2160  0.0000  10.25000  0.05    0.40
;
_shelx_res_checksum              98832
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.095
_oxdiff_exptl_absorpt_empirical_full_min 0.363
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.59(8)
2 0.41(8)

####################################################################### 
# 
# 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_yo_end_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2340574'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-12-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHCl0.03Br0.97
_chemical_formula_moiety         '0.03(Cl), 0.97(Br), C6 H13 N2'
_chemical_formula_sum            'C6 H13 Br0.97 Cl0.03 N2'
_chemical_formula_weight         191.76
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.97Cl0.03
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.6645(5)
_cell_length_b                   6.6645(5)
_cell_length_c                   5.3238(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     204.78(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    914
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.9500
_cell_measurement_theta_min      3.5140
_shelx_estimated_absorpt_T_max   0.432
_shelx_estimated_absorpt_T_min   0.152
_exptl_absorpt_coefficient_mu    4.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.214
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             97
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -3 7 0.2056
9 -7 0 0.0953
-9 7 0 0.1158
0 0 7 0.2562
-3 -6 0 0.1121
0 0 -8 0.3625
3 6 0 0.1289

_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.6233 -3.0945 6.8245 0.0963 0.4151 0.9047
8.7117 -7.3764 0.1606 0.2323 0.9726 0.0106
-8.7124 7.3768 -0.1345 -0.2323 -0.9726 -0.0071
-0.2682 -0.2913 7.4928 0.0519 -0.0095 0.9986
-3.4892 -5.8187 -0.1089 0.9726 -0.2324 -0.0089
0.0437 -0.0833 -7.5054 0.0107 -0.0055 -0.9999
3.4872 5.8176 0.2177 -0.9723 0.2324 0.0234

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.109
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  95.00   0.25    0.06    --   13.59   1.00  16.00  360
  2  ω     52.00  78.00   0.25    0.06    --   13.59-136.00-163.00  104
  3  ω    -11.00  24.00   0.25    0.06    --  -12.66  19.00   0.00  140
  4  ω    -15.00  15.00   0.25    0.06    --  -12.66 -99.00-120.00  120
  5  ω    -14.00  32.00   0.25    0.06    --  -12.66 -99.00 -60.00  184
  6  ω    -73.00 -21.00   0.25    0.06    --  -12.66 134.00  82.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0761673000
_diffrn_orient_matrix_UB_12      -0.1214633000
_diffrn_orient_matrix_UB_13      -0.0005204000
_diffrn_orient_matrix_UB_21      0.0964391000
_diffrn_orient_matrix_UB_22      -0.0179206000
_diffrn_orient_matrix_UB_23      0.0014933000
_diffrn_orient_matrix_UB_31      -0.0013631000
_diffrn_orient_matrix_UB_32      -0.0001411000
_diffrn_orient_matrix_UB_33      0.1332218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                231
_reflns_number_total             236
_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       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 96 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{Cl1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Br1)
4. Others
 Fixed Sof: Cl1(0.0025) Br1(0.08083) H1(0.083333) H1A(0.5) H1B(0.5)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
Cl1 Cl 0.333333 0.666667 0.500000 0.0438(5) Uani 0.03 12 d S T P A 3
Br1 Br 0.333333 0.666667 0.500000 0.0438(5) Uani 0.97 12 d S T P B 4
N1 N 0.666667 0.333333 0.2390(16) 0.0420(19) Uani 1 6 d S T P . .
H1 H 0.666667 0.333334 0.423100 0.050 Uiso 0.5 6 calc R U P . .
C1 C 0.4253(13) 0.2126(6) 0.1452(8) 0.0466(15) Uani 1 2 d S T P . .
H1A H 0.344708 0.290257 0.206693 0.056 Uiso 0.5 1 calc R U P . .
H1B H 0.344706 0.054453 0.206699 0.056 Uiso 0.5 1 calc R U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0454(6) 0.0454(6) 0.0407(6) 0.000 0.000 0.0227(3)
Br1 0.0454(6) 0.0454(6) 0.0407(6) 0.000 0.000 0.0227(3)
N1 0.047(3) 0.047(3) 0.032(4) 0.000 0.000 0.0235(15)
C1 0.041(3) 0.051(3) 0.045(3) 0.0019(12) 0.004(2) 0.0204(14)

_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 H1 0.9800 . ?
N1 C1 1.480(8) . ?
N1 C1 1.480(8) 2_655 ?
N1 C1 1.480(8) 3_665 ?
C1 C1 1.546(9) 4 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.7 2_655 . ?
C1 N1 H1 109.7 3_665 . ?
C1 N1 H1 109.7 . . ?
C1 N1 C1 109.2(4) 2_655 3_665 ?
C1 N1 C1 109.2(4) 3_665 . ?
C1 N1 C1 109.2(4) 2_655 . ?
N1 C1 C1 109.7(4) . 4 ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C1 C1 H1A 109.7 4 . ?
C1 C1 H1B 109.7 4 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 -59.7(5) 2_655 . . 4 ?
C1 N1 C1 C1 59.7(5) 3_665 . . 4 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 15:36:10 on 10-Dec-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.074, Rweak 0.312, Alpha 0.026
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.004 ( 0.027 ) from 85 Parsons' quotients
REM Formula found by SHELXT: C8 Br
CELL 0.71073 6.6645 6.6645 5.3238 90 90 120
ZERR 1 0.0005 0.0005 0.0004 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br Cl N
UNIT 6 13 0.97 0.03 2
EADP Cl1 Br1
EXYZ Cl1 Br1

L.S. 4 0 0
PLAN  5
SIZE 0.21 0.25 0.63
TEMP 24.85
CONF
list 4
fmap 2 53
acta
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.055600    0.021300
FVAR       2.53121
PART 3
CL1   4    0.333333    0.666667    0.500000    10.00250    0.04537    0.04537 =
         0.04066    0.00000    0.00000    0.02269

PART 4
BR1   3    0.333333    0.666667    0.500000    10.08083    0.04537    0.04537 =
         0.04066    0.00000    0.00000    0.02269

PART 0
N1    5    0.666667    0.333333    0.239021    10.16667    0.04706    0.04706 =
         0.03177    0.00000    0.00000    0.02353
AFIX  13
H1    2    0.666667    0.333334    0.423100    10.08333   -1.20000
AFIX   0
C1    1    0.425294    0.212647    0.145208    10.50000    0.04085    0.05051 =
         0.04509    0.00190    0.00379    0.02042
AFIX  23
H1A   2    0.344708    0.290257    0.206693    10.50000   -1.20000
H1B   2    0.344706    0.054453    0.206699    10.50000   -1.20000
AFIX   0
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0846, GooF = S = 1.161, Restrained GooF = 1.161 for all data
REM R1 = 0.0333 for 231 Fo > 4sig(Fo) and 0.0351 for all 236 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.0556      0.0213

REM Highest difference peak  0.714,  deepest hole -0.331,  1-sigma level  0.080
Q1    1   0.4077  0.8154  0.5000  10.25000  0.05    0.71
Q2    1   0.2600  0.5201  0.5000  10.25000  0.05    0.69
Q3    1   0.7220  0.4440  0.1815  10.50000  0.05    0.28
Q4    1   0.4898  0.9797  0.5000  10.25000  0.05    0.23
Q5    1   0.1734  0.3468  0.5000  10.25000  0.05    0.21
;
_shelx_res_checksum              89048
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.773
####################################################################### 
# 
# 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_yo_end_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2340570'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.80I0.20
_chemical_formula_moiety         '0.2(I1), C6 H13 N2, 0.8(Br)'
_chemical_formula_sum            'C6 H13 Br0.80 I0.20 N2'
_chemical_formula_weight         202.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.8I0.2
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.7541(6)
_cell_length_b                   6.7541(6)
_cell_length_c                   5.3383(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     210.90(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    941
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.5370
_cell_measurement_theta_min      3.4680
_shelx_estimated_absorpt_T_max   0.803
_shelx_estimated_absorpt_T_min   0.305
_exptl_absorpt_coefficient_mu    4.582
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             102
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 9 0 0.0337
-2 -3 -7 0.1277
2 3 7 0.1606
7 -9 0 0.0112
-6 -2 3 0.0660
-7 9 0 0.0374
-8 2 3 0.0711
7 -9 0 0.0093
5 3 -3 0.1084
2 1 1 0.1084
-2 -1 -1 0.0486
6 4 1 0.0803
5 5 0 0.0550
-6 -3 0 0.0093

_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.4961 8.8080 -0.4369 -0.0635 0.0123 0.9979
-1.9587 -2.5136 -6.6385 -0.9665 0.2313 -0.1115
1.5828 2.9382 6.5936 0.9599 -0.2298 0.1603
7.2746 -8.9553 0.0649 0.0007 -0.0095 -1.0000
-6.4524 -1.5503 3.4127 -0.2302 -0.9615 0.1504
-7.0814 9.0496 -0.1383 0.0120 0.0391 0.9992
-8.3040 1.8397 3.0130 -0.2012 -0.8476 0.4911
7.3576 -8.9105 -0.0344 -0.0004 0.0095 -1.0000
5.4719 2.8534 -3.4570 0.2324 0.9726 -0.0081
2.0000 1.0000 1.0000 0.3100 0.1558 -0.0067
-2.0000 -1.0000 -1.0000 -0.3100 -0.1558 0.0067
5.7807 3.5531 1.1296 0.7594 0.6498 0.0324
4.6741 4.8399 -0.4329 0.5985 0.7809 0.1789
-6.1466 -3.2141 0.4406 -0.6079 -0.7940 0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.024
_diffrn_reflns_theta_min         3.483
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  43.00   0.25    0.11    --  -15.47  77.00 120.00  388
  2  ω    -91.00  19.00   0.25    0.11    --  -15.47 -67.00 162.00  440
  3  ω   -105.00 -41.00   0.25    0.11    --  -15.47-178.00-180.00  256
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0742373000
_diffrn_orient_matrix_UB_12      0.0609597000
_diffrn_orient_matrix_UB_13      0.1006019000
_diffrn_orient_matrix_UB_21      0.0861316000
_diffrn_orient_matrix_UB_22      0.0703935000
_diffrn_orient_matrix_UB_23      -0.0869027000
_diffrn_orient_matrix_UB_31      -0.0420159000
_diffrn_orient_matrix_UB_32      0.0775291000
_diffrn_orient_matrix_UB_33      -0.0001575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                229
_reflns_number_total             231
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -1.303
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.3092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.59(10)
 0.41(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Shared sites
{Br1, I1}
4. Uiso/Uaniso restraints and constraints
Uiso(Br1) = Uiso(I1)
5. Others
 Fixed Sof: I1(0.01667) H1(0.083333) H1A(0.5) H1B(0.5) Br1(0.06667)
6.a Ternary CH refined with riding coordinates:
 N1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
I1 I 0.666667 0.333333 0.500000 0.0479(6) Uiso 0.2 12 d S . P A 4
N1 N 0.333333 0.666667 0.763(2) 0.046(3) Uani 1 6 d S T P . .
H1 H 0.333333 0.666666 0.579534 0.055 Uiso 0.5 6 calc R U P . .
C1 C 0.5710(16) 0.7855(8) 0.8549(12) 0.051(2) Uani 1 2 d S T P . .
H1A H 0.650304 0.941518 0.793431 0.061 Uiso 0.5 1 calc R U P . .
H1B H 0.650305 0.708787 0.793427 0.061 Uiso 0.5 1 calc R U P . .
Br1 Br 0.666667 0.333333 0.500000 0.0479(6) Uiso 0.8 12 d S . P B 3

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
N1 0.057(5) 0.057(5) 0.023(5) 0.000 0.000 0.029(2)
C1 0.047(4) 0.061(5) 0.039(4) 0.0025(18) 0.005(4) 0.024(2)

_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 H1 0.9800 . ?
N1 C1 1.474(10) . ?
N1 C1 1.474(10) 2_665 ?
N1 C1 1.474(10) 3_565 ?
C1 C1 1.549(13) 4_557 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.4 2_665 . ?
C1 N1 H1 109.4 3_565 . ?
C1 N1 H1 109.4 . . ?
C1 N1 C1 109.5(5) 2_665 3_565 ?
C1 N1 C1 109.5(5) 3_565 . ?
C1 N1 C1 109.5(5) 2_665 . ?
N1 C1 C1 109.4(5) . 4_557 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4_557 . ?
C1 C1 H1B 109.8 4_557 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 60.1(6) 2_665 . . 4_557 ?
C1 N1 C1 C1 -60.1(6) 3_565 . . 4_557 ?

_shelx_res_file                  
;
TITL yo_end_c.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 17:53:36 on 24-Jul-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.080, Rweak 0.361, Alpha 0.031
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.362 ( 0.062 ) from 86 Parsons' quotients
REM Formula found by SHELXT: C2 N6 I
CELL 0.71073 6.7541 6.7541 5.3383 90 90 120
ZERR 1 0.0006 0.0006 0.0004 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.8 0.2 2
EADP Br1 I1
EXYZ Br1 I1

L.S. 10
PLAN  5
SIZE 0.05 0.07 0.34
TEMP 24.85
CONF
BOND
LIST 6
fmap 2
ACTA
MORE -1
BOND $H
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.046000    0.309200
BASF   0.40707
FVAR       2.28800
PART 4
I1    4    0.666667    0.333333    0.500000    10.01667    0.04788

PART 0
N1    5    0.333333    0.666667    0.763113    10.16667    0.05706    0.05706 =
         0.02323    0.00000    0.00000    0.02853
AFIX  13
H1    2    0.333333    0.666666    0.579534    10.08333   -1.20000
AFIX   0
C1    1    0.570969    0.785484    0.854946    10.50000    0.04744    0.06131 =
         0.03863    0.00246    0.00491    0.02372
AFIX  23
H1A   2    0.650304    0.941518    0.793431    10.50000   -1.20000
H1B   2    0.650305    0.708787    0.793427    10.50000   -1.20000
AFIX   0

PART 3
BR1   3    0.666667    0.333333    0.500000    10.06667    0.04788
HKLF 4




REM  yo_end_c.res in P-6m2
REM wR2 = 0.0933, GooF = S = 1.114, Restrained GooF = 1.114 for all data
REM R1 = 0.0389 for 229 Fo > 4sig(Fo) and 0.0394 for all 231 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.0460      0.3093

REM Highest difference peak  0.938,  deepest hole -1.303,  1-sigma level  0.082
Q1    1   0.7005  0.4011  0.3030  10.50000  0.05    0.31
Q2    1   0.6667  0.3333  0.1338  10.16667  0.05    0.24
Q3    1   0.2152  0.4304  0.5000  10.25000  0.05    0.19
Q4    1   1.0000  1.0000  0.8438  10.16667  0.05    0.18
Q5    1   0.6659  0.9511  0.5542  11.00000  0.05    0.18
;
_shelx_res_checksum              7728
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.947
_oxdiff_exptl_absorpt_empirical_full_min 0.359
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.59(10)
2 0.41(10)

####################################################################### 
# 
# 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_yo_end_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2340573'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.95I0.05
_chemical_formula_moiety         'C6 H13 N2, 0.05(I), 0.95(Br)'
_chemical_formula_sum            'C6 H13 Br0.95 I0.05 N2'
_chemical_formula_weight         195.44
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.9I0.1
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.6793(6)
_cell_length_b                   6.6793(6)
_cell_length_c                   5.3178(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     205.46(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1001
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.5190
_cell_measurement_theta_min      3.5020
_shelx_estimated_absorpt_T_max   0.697
_shelx_estimated_absorpt_T_min   0.388
_exptl_absorpt_coefficient_mu    4.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             99
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -5 -2 0.0399
4 5 2 0.0378
1 0 7 0.0927
9 -7 0 0.0440
-1 0 -7 0.0898
-9 7 -1 0.0396

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.2288 -4.8414 -1.9972 -0.9231 0.1871 -0.3360
3.9111 5.1552 1.9457 0.9293 -0.1483 0.3382
1.4248 -0.2049 7.3971 0.0057 -0.3308 0.9437
8.8036 -7.2901 -0.0346 0.0090 -0.9752 -0.2213
-1.1398 -0.0342 -7.4219 -0.0054 0.2998 -0.9540
-8.8114 7.2258 -0.5026 -0.0093 0.9886 0.1504

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1234
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.066
_diffrn_reflns_theta_min         3.522
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  70.00   0.25    0.20    --   -5.68  19.00 146.00  364
  2  ω    -17.00  28.00   0.25    0.20    --   -5.68 -99.00-120.00  180
  3  ω    -67.00 -29.00   0.25    0.20    --    6.15 -38.00 -30.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0950291000
_diffrn_orient_matrix_UB_12      0.1135968000
_diffrn_orient_matrix_UB_13      -0.0143861000
_diffrn_orient_matrix_UB_21      -0.0772203000
_diffrn_orient_matrix_UB_22      0.0406500000
_diffrn_orient_matrix_UB_23      -0.0287205000
_diffrn_orient_matrix_UB_31      -0.0066046000
_diffrn_orient_matrix_UB_32      0.0217635000
_diffrn_orient_matrix_UB_33      0.1294504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                222
_reflns_number_total             225
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 92 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{I1, Br1}
3. Uiso/Uaniso restraints and constraints
Uiso(I1) = Uiso(Br1)
4. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) I1(0.00417) Br1(0.07917)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.666667 0.333333 0.7612(14) 0.0399(18) Uani 1 6 d S T P . .
H1 H 0.666666 0.333332 0.576950 0.048 Uiso 0.5 6 calc R U P . .
C1 C 0.7875(6) 0.5751(11) 0.8545(8) 0.0450(15) Uani 1 2 d S T P . .
H1A H 0.710030 0.655379 0.792835 0.054 Uiso 0.5 1 calc R U P . .
H1B H 0.945348 0.655380 0.792832 0.054 Uiso 0.5 1 calc R U P . .
I1 I 0.333333 0.666667 0.500000 0.0445(4) Uiso 0.05 12 d S . P A 3
Br1 Br 0.333333 0.666667 0.500000 0.0445(4) Uiso 0.95 12 d S . P B 4

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
N1 0.045(3) 0.045(3) 0.030(4) 0.000 0.000 0.0225(14)
C1 0.046(3) 0.041(3) 0.046(3) 0.006(2) 0.0028(11) 0.0204(14)

_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 H1 0.9800 . ?
N1 C1 1.484(7) . ?
N1 C1 1.484(7) 3_665 ?
N1 C1 1.484(7) 2_655 ?
C1 C1 1.547(8) 4_557 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.5 3_665 . ?
C1 N1 H1 109.5 2_655 . ?
C1 N1 H1 109.5 . . ?
C1 N1 C1 109.4(3) 3_665 2_655 ?
C1 N1 C1 109.4(3) 2_655 . ?
C1 N1 C1 109.4(3) 3_665 . ?
N1 C1 C1 109.5(3) . 4_557 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4_557 . ?
C1 C1 H1B 109.8 4_557 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 -59.9(4) 3_665 . . 4_557 ?
C1 N1 C1 C1 59.9(4) 2_655 . . 4_557 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 10:08:12 on 01-Aug-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.046, Rweak 0.323, Alpha 0.028
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.534 ( 0.061 ) from 83 Parsons' quotients
REM Formula found by SHELXT: C2 N8 I
CELL 0.71073 6.6793 6.6793 5.3178 90 90 120
ZERR 1 0.0006 0.0006 0.0005 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.95 0.05 2
EADP I1 Br1
EXYZ I1 Br1

L.S. 4
PLAN  5
SIZE 0.08 0.1 0.24
TEMP 24.85
CONF
BOND
list 4
fmap 2
ACTA
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.049400
FVAR       2.30693
N1    5    0.666667    0.333333    0.761237    10.16667    0.04493    0.04493 =
         0.02993    0.00000    0.00000    0.02247
AFIX  13
H1    2    0.666666    0.333332    0.576950    10.08333   -1.20000
AFIX   0
C1    1    0.787546    0.575091    0.854519    10.50000    0.04629    0.04081 =
         0.04595    0.00564    0.00282    0.02040
AFIX  23
H1A   2    0.710030    0.655379    0.792835    10.50000   -1.20000
H1B   2    0.945348    0.655380    0.792832    10.50000   -1.20000
AFIX   0

PART 3
I1    4    0.333333    0.666667    0.500000    10.00417    0.04448
PART 4
BR1   3    0.333333    0.666667    0.500000    10.07917    0.04448
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0723, GooF = S = 1.080, Restrained GooF = 1.080 for all data
REM R1 = 0.0314 for 222 Fo > 4sig(Fo) and 0.0327 for all 225 data
REM 11 parameters refined using 0 restraints

END

WGHT      0.0494      0.0000

REM Highest difference peak  0.800,  deepest hole -0.559,  1-sigma level  0.074
Q1    1   0.3333  0.6667  0.3869  10.16667  0.05    0.80
Q2    1   0.7785  0.5569  1.0000  10.25000  0.05    0.28
Q3    1   0.6667  0.3333  0.8931  10.16667  0.05    0.19
Q4    1   0.2355  0.4710  0.5000  10.25000  0.05    0.15
Q5    1   0.8222  0.6444  0.7337  10.50000  0.05    0.14
;
_shelx_res_checksum              80202
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.479
####################################################################### 
# 
# 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_yo_end_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2340572'
loop_
_audit_author_name
_audit_author_address
'Yuki Ohishi'
;Yamaguchi University
Japan
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        dabcoHBr0.90I0.10
_chemical_formula_moiety         'C6 H13 N2, 0.9(Br), 0.1(I)'
_chemical_formula_sum            'C6 H13 Br0.90 I0.10 N2'
_chemical_formula_weight         197.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H13N2Br0.85I0.15
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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      hexagonal
_space_group_IT_number           187
_space_group_name_H-M_alt        'P -6 m 2'
_space_group_name_Hall           'P -6 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z'
'-y, x-y, -z'
'-x+y, -x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   6.6949(4)
_cell_length_b                   6.6949(4)
_cell_length_c                   5.3265(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     206.76(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    722
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.7430
_cell_measurement_theta_min      3.5220
_shelx_estimated_absorpt_T_max   0.731
_shelx_estimated_absorpt_T_min   0.271
_exptl_absorpt_coefficient_mu    4.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             100
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 8 -1 0.0149
1 -1 -7 0.1744
5 4 0 0.0507
0 1 7 0.1847
-5 -4 1 0.0322
1 8 0 0.0281
8 -8 0 0.0468
7 -9 0 0.0318

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.7545 8.4811 -0.6381 -0.2324 -0.9726 0.0090
0.6540 -0.6275 -7.4821 -0.0740 0.0205 0.9970
5.3410 4.0766 -0.1206 0.9677 -0.2309 0.1015
-0.4080 0.8154 7.4772 0.1186 -0.0311 -0.9925
-5.3634 -4.0216 0.5989 -0.9594 0.2288 -0.1650
0.7484 7.7753 -0.2965 0.7239 -0.6858 0.0757
8.3321 -7.9989 -0.0303 0.3317 0.9392 0.0888
6.5575 -9.1555 -0.0810 0.0252 0.9974 0.0678

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0091
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            778
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.257
_diffrn_reflns_theta_min         3.514
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -24.00   0.25    1.00    --  -12.85 146.00  -2.00  240
  2  ω    -57.00   0.00   0.25    1.00    --  -12.85   9.00 111.00  228
  3  ω     59.00  84.00   0.25    1.00    --   13.32-146.00 -53.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1187524000
_diffrn_orient_matrix_UB_12      0.0821799000
_diffrn_orient_matrix_UB_13      0.0133842000
_diffrn_orient_matrix_UB_21      0.0259384000
_diffrn_orient_matrix_UB_22      -0.0904232000
_diffrn_orient_matrix_UB_23      0.0071149000
_diffrn_orient_matrix_UB_31      0.0134328000
_diffrn_orient_matrix_UB_32      0.0033895000
_diffrn_orient_matrix_UB_33      -0.1323671000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.618
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                212
_reflns_number_total             212
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 81 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0155
_refine_ls_R_factor_gt           0.0155
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²+0.0413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0427
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Shared sites
{Br1, I1}
3. Uiso/Uaniso restraints and constraints
Uiso(Br1) = Uiso(I1)
4. Others
 Fixed Sof: H1(0.083333) H1A(0.5) H1B(0.5) Br1(0.075) I1(0.00833)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.333333 0.666667 0.2374(9) 0.0382(11) Uani 1 6 d S T P . .
H1 H 0.333334 0.666666 0.421393 0.046 Uiso 0.5 6 calc R U P . .
C1 C 0.2132(4) 0.4265(7) 0.1451(5) 0.0444(9) Uani 1 2 d S T P . .
H1A H 0.055816 0.346416 0.206786 0.053 Uiso 0.5 1 calc R U P . .
H1B H 0.290604 0.346418 0.206781 0.053 Uiso 0.5 1 calc R U P . .
Br1 Br 0.666667 0.333333 0.500000 0.0422(2) Uiso 0.9 12 d S . P A 3
I1 I 0.666667 0.333333 0.500000 0.0422(2) Uiso 0.1 12 d S . P B 4

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
N1 0.0434(18) 0.0434(18) 0.028(2) 0.000 0.000 0.0217(9)
C1 0.0493(17) 0.0394(17) 0.0414(17) 0.0037(14) 0.0019(7) 0.0197(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.9800 . ?
N1 C1 1.477(4) . ?
N1 C1 1.477(4) 3_565 ?
N1 C1 1.477(4) 2_665 ?
C1 C1 1.546(5) 4 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 H1 109.4 3_565 . ?
C1 N1 H1 109.4 2_665 . ?
C1 N1 H1 109.4 . . ?
C1 N1 C1 109.5(2) 3_565 2_665 ?
C1 N1 C1 109.5(2) 2_665 . ?
C1 N1 C1 109.5(2) 3_565 . ?
N1 C1 C1 109.4(2) . 4 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 4 . ?
C1 C1 H1B 109.8 4 . ?
H1A C1 H1B 108.2 . . ?

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
C1 N1 C1 C1 60.0(3) 3_565 . . 4 ?
C1 N1 C1 C1 -60.0(3) 2_665 . . 4 ?

_shelx_res_file                  
;
TITL yo_end_a.res in P-6m2
    yo_end.res
    created by SHELXL-2018/3 at 16:13:50 on 28-Jul-2023
REM Old TITL YO_end in P-6m2
REM SHELXT solution in P-6m2: R1 0.061, Rweak 0.351, Alpha 0.027
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = -0.507 ( 0.058 ) from 70 Parsons' quotients
REM Formula found by SHELXT: C4 N6 I1
CELL 0.71073 6.6949 6.6949 5.3265 90 90 120
ZERR 1 0.0004 0.0004 0.0004 0 0 0
LATT -1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +X,+Y,-Z
SYMM -Y,+X-Y,-Z
SYMM +Y-X,-X,-Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SYMM -Y,-X,-Z
SYMM +Y-X,+Y,-Z
SYMM +X,+X-Y,-Z
SFAC C H Br I N
UNIT 6 13 0.9 0.1 2
EADP Br1 I1
EXYZ Br1 I1

L.S. 10 0 0
PLAN  5
SIZE 0.07 0.1 0.37
TEMP 24.85
CONF
BOND
list 4
fmap 2 53
ACTA
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\YO_end.hkl">
REM </olex2.extras>

WGHT    0.022300    0.041300
FVAR       2.42298
N1    5    0.333333    0.666667    0.237408    10.16667    0.04344    0.04344 =
         0.02769    0.00000    0.00000    0.02172
AFIX  13
H1    2    0.333334    0.666666    0.421393    10.08333   -1.20000
AFIX   0
C1    1    0.213230    0.426461    0.145137    10.50000    0.04929    0.03935 =
         0.04137    0.00373    0.00186    0.01968
AFIX  23
H1A   2    0.055816    0.346416    0.206786    10.50000   -1.20000
H1B   2    0.290604    0.346418    0.206781    10.50000   -1.20000
AFIX   0

PART 3
BR1   3    0.666667    0.333333    0.500000    10.07500    0.04217

PART 4
I1    4    0.666667    0.333333    0.500000    10.00833    0.04217
HKLF 4




REM  yo_end_a.res in P-6m2
REM wR2 = 0.0427, GooF = S = 1.240, Restrained GooF = 1.240 for all data
REM R1 = 0.0155 for 212 Fo > 4sig(Fo) and 0.0155 for all 212 data
REM 11 parameters refined using 0 restraints

END

WGHT      0.0223      0.0413

REM Highest difference peak  0.188,  deepest hole -0.166,  1-sigma level  0.034
Q1    1   0.5197  0.3349  0.5913  11.00000  0.05    0.19
Q2    1   0.7184  0.4368  0.3736  10.50000  0.05    0.15
Q3    1   0.8846  0.5123  0.5000  10.50000  0.05    0.14
Q4    1   0.6204  0.2408  0.6324  10.50000  0.05    0.14
Q5    1   0.0131  0.4241  0.5000  10.50000  0.05    0.11
;
_shelx_res_checksum              38896
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.695
