# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# 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_[NC2C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120102'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H16 N6), Br'
_chemical_formula_sum            'C6 H8 Br N3'
_chemical_formula_weight         202.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 Br N3'
_chemical_oxdiff_usercomment     SK57_EtOH
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'
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.5333(6)
_cell_length_b                   6.3618(3)
_cell_length_c                   7.9158(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     782.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1679
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      27.8950
_cell_measurement_theta_min      3.1050
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.510
_exptl_absorpt_coefficient_mu    5.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.011
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  51.00   1.00    1.00    --  -13.33  77.00  30.00   89
  2  ω    -79.00  12.00   1.00    1.00    --  -13.33 -77.00 -90.00   91
  3  ω     -2.00  82.00   1.00    1.00    --   14.43  57.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0063109000
_diffrn_orient_matrix_UB_12      -0.0482126000
_diffrn_orient_matrix_UB_13      -0.0927195000
_diffrn_orient_matrix_UB_21      -0.0432595000
_diffrn_orient_matrix_UB_22      0.0154604000
_diffrn_orient_matrix_UB_23      -0.0300069000
_diffrn_orient_matrix_UB_31      0.0131618000
_diffrn_orient_matrix_UB_32      0.0739370000
_diffrn_orient_matrix_UB_33      -0.0541867000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                819
_reflns_number_total             951
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.0108(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H5A(0.5) H5B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.8439(2) 0.250000 0.3353(4) 0.0182(7) Uani 1 2 d S T P . .
C1 C 0.9381(3) 0.250000 0.3378(5) 0.0270(11) Uani 1 2 d S T P . .
H1A H 0.957968 0.220304 0.450149 0.041 Uiso 0.5 1 calc R U P A -1
H1B H 0.958985 0.385344 0.303099 0.041 Uiso 0.5 1 calc R U P A -1
H1C H 0.959271 0.144352 0.261765 0.041 Uiso 0.5 1 calc R U P A -1
N2 N 0.7124(2) 0.250000 0.4194(4) 0.0172(7) Uani 1 2 d S T P . .
C2 C 0.7943(2) 0.250000 0.4706(5) 0.0167(8) Uani 1 2 d S T P . .
H2 H 0.813103 0.250000 0.582174 0.020 Uiso 1 2 calc R U P . .
N3 N 0.6722(3) 0.250000 0.8438(4) 0.0279(9) Uani 1 2 d S T P . .
C3 C 0.7925(3) 0.250000 0.1930(5) 0.0209(9) Uani 1 2 d S T P . .
H3 H 0.811376 0.250000 0.081570 0.025 Uiso 1 2 calc R U P . .
C4 C 0.7103(3) 0.250000 0.2449(5) 0.0194(8) Uani 1 2 d S T P . .
H4 H 0.661455 0.250000 0.176841 0.023 Uiso 1 2 calc R U P . .
C5 C 0.6345(2) 0.250000 0.5231(5) 0.0187(8) Uani 1 2 d S T P . .
H5A H 0.600372 0.126677 0.496542 0.022 Uiso 0.5 1 calc R U P . .
H5B H 0.600372 0.373323 0.496542 0.022 Uiso 0.5 1 calc R U P . .
C6 C 0.6551(3) 0.250000 0.7038(5) 0.0186(8) Uani 1 2 d S T P . .
Br1 Br 0.93110(3) 0.250000 0.82442(5) 0.0209(2) Uani 1 2 d S T 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
N1 0.018(2) 0.0170(16) 0.0193(17) 0.000 0.0054(14) 0.000
C1 0.017(2) 0.033(3) 0.032(3) 0.000 0.0046(18) 0.000
N2 0.0207(19) 0.0179(16) 0.0130(16) 0.000 0.0015(13) 0.000
C2 0.019(2) 0.0165(18) 0.0147(17) 0.000 -0.0018(17) 0.000
N3 0.037(2) 0.028(2) 0.018(2) 0.000 -0.0001(16) 0.000
C3 0.030(3) 0.017(2) 0.0166(19) 0.000 0.0003(17) 0.000
C4 0.024(2) 0.022(2) 0.0129(18) 0.000 -0.0011(18) 0.000
C5 0.019(2) 0.0215(19) 0.0156(18) 0.000 0.0028(16) 0.000
C6 0.019(2) 0.0147(18) 0.022(2) 0.000 0.0046(17) 0.000
Br1 0.0178(3) 0.0273(3) 0.0177(3) 0.000 -0.00044(15) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.463(5) . ?
N1 C2 1.320(5) . ?
N1 C3 1.381(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.336(5) . ?
N2 C4 1.381(5) . ?
N2 C5 1.462(5) . ?
C2 H2 0.9300 . ?
N3 C6 1.140(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.341(6) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.466(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.0(3) . . ?
C2 N1 C3 108.9(4) . . ?
C3 N1 C1 126.2(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 109.1(3) . . ?
C2 N2 C5 128.2(3) . . ?
C4 N2 C5 122.8(3) . . ?
N1 C2 N2 108.1(3) . . ?
N1 C2 H2 126.0 . . ?
N2 C2 H2 126.0 . . ?
N1 C3 H3 126.2 . . ?
C4 C3 N1 107.6(3) . . ?
C4 C3 H3 126.2 . . ?
N2 C4 H4 126.8 . . ?
C3 C4 N2 106.4(3) . . ?
C3 C4 H4 126.8 . . ?
N2 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
N2 C5 C6 111.6(3) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N3 C6 C5 179.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 N2 0.000(0) . . . . ?
C1 N1 C2 N2 180.000(0) . . . . ?
C1 N1 C3 C4 180.000(0) . . . . ?
C2 N1 C3 C4 0.000(0) . . . . ?
C2 N2 C4 C3 0.000(0) . . . . ?
C2 N2 C5 C6 0.000(1) . . . . ?
C3 N1 C2 N2 0.000(0) . . . . ?
C4 N2 C2 N1 0.000(0) . . . . ?
C4 N2 C5 C6 180.000(1) . . . . ?
C5 N2 C2 N1 180.000(0) . . . . ?
C5 N2 C4 C3 180.000(0) . . . . ?

_shelx_res_file                  
;
TITL tw2009_a.res in Pnma
    tw2009.res
    created by SHELXL-2018/3 at 14:43:04 on 23-Jun-2021
REM Old TITL tw2009_a.res in Pnma
REM SHELXT solution in Pnma: R1 0.071, Rweak 0.002, Alpha 0.029
REM <I/s> 0.789 for 98 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N3 Br
CELL 0.71073 15.5333 6.3618 7.9158 90 90 90
ZERR 4 0.0006 0.0003 0.0003 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H Br N
UNIT 24 32 4 12

L.S. 10
PLAN  5
SIZE 0.15 0.1 0.02
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2009.hkl">
REM </olex2.extras>

WGHT    0.058400
EXTI    0.010780
FVAR       0.44993
N1    4    0.843938    0.250000    0.335281    10.50000    0.01839    0.01697 =
         0.01935    0.00000    0.00539    0.00000
C1    1    0.938143    0.250000    0.337789    10.50000    0.01677    0.03261 =
         0.03163    0.00000    0.00461    0.00000
PART -1
AFIX 137
H1A   2    0.957968    0.220304    0.450149    10.50000   -1.50000
H1B   2    0.958985    0.385344    0.303099    10.50000   -1.50000
H1C   2    0.959271    0.144352    0.261765    10.50000   -1.50000
AFIX   0
PART 0
N2    4    0.712389    0.250000    0.419374    10.50000    0.02066    0.01785 =
         0.01305    0.00000    0.00155    0.00000
C2    1    0.794312    0.250000    0.470624    10.50000    0.01886    0.01653 =
         0.01470    0.00000   -0.00181    0.00000
AFIX  43
H2    2    0.813103    0.250000    0.582174    10.50000   -1.20000
AFIX   0
N3    4    0.672237    0.250000    0.843821    10.50000    0.03695    0.02841 =
         0.01822    0.00000   -0.00012    0.00000
C3    1    0.792475    0.250000    0.193048    10.50000    0.02951    0.01658 =
         0.01657    0.00000    0.00027    0.00000
AFIX  43
H3    2    0.811376    0.250000    0.081570    10.50000   -1.20000
AFIX   0
C4    1    0.710256    0.250000    0.244905    10.50000    0.02364    0.02159 =
         0.01288    0.00000   -0.00109    0.00000
AFIX  43
H4    2    0.661455    0.250000    0.176841    10.50000   -1.20000
AFIX   0
C5    1    0.634511    0.250000    0.523092    10.50000    0.01915    0.02149 =
         0.01560    0.00000    0.00282    0.00000
AFIX  23
H5A   2    0.600372    0.126677    0.496542    10.50000   -1.20000
H5B   2    0.600372    0.373323    0.496542    10.50000   -1.20000
AFIX   0
C6    1    0.655095    0.250000    0.703842    10.50000    0.01929    0.01471 =
         0.02172    0.00000    0.00459    0.00000

BR1   3    0.931096    0.250000    0.824416    10.50000    0.01776    0.02732 =
         0.01768    0.00000   -0.00044    0.00000
HKLF 4




REM  tw2009_a.res in Pnma
REM wR2 = 0.0899, GooF = S = 1.048, Restrained GooF = 1.048 for all data
REM R1 = 0.0329 for 819 Fo > 4sig(Fo) and 0.0413 for all 951 data
REM 63 parameters refined using 0 restraints

END

WGHT      0.0580      0.0000

REM Highest difference peak  1.141,  deepest hole -0.797,  1-sigma level  0.119
Q1    1   0.9314  0.0844  0.8208  11.00000  0.05    1.14
Q2    1   0.8815  0.2500  0.8373  10.50000  0.05    0.61
Q3    1   0.9995  0.1302  0.8163  11.00000  0.05    0.45
Q4    1   0.9829  0.2500  0.8270  10.50000  0.05    0.45
Q5    1   0.8607  0.0917  0.8207  11.00000  0.05    0.43
;
_shelx_res_checksum              83102
_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 3.279
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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. 
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#######################################################################

data_[HCC2C1C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120103'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 N2, Br'
_chemical_formula_sum            'C8 H11 Br N2'
_chemical_formula_weight         215.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H9 Br N2'
_chemical_oxdiff_usercomment     SK86_EtOH
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4022(7)
_cell_length_b                   7.5130(5)
_cell_length_c                   11.8190(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.618(8)
_cell_angle_gamma                90
_cell_volume                     901.37(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.0710
_cell_measurement_theta_min      3.3130
_shelx_estimated_absorpt_T_max   0.614
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    4.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.945
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  52.00   1.00    1.00    --  -13.33  77.00 120.00   91
  2  ω    -80.00  12.00   1.00    1.00    --  -13.33 -77.00   0.00   92
  3  ω     -2.00  81.00   1.00    1.00    --   14.58  57.00 -90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0036360000
_diffrn_orient_matrix_UB_12      -0.0246032000
_diffrn_orient_matrix_UB_13      0.0571580000
_diffrn_orient_matrix_UB_21      0.0049758000
_diffrn_orient_matrix_UB_22      -0.0909471000
_diffrn_orient_matrix_UB_23      -0.0145084000
_diffrn_orient_matrix_UB_31      0.0696110000
_diffrn_orient_matrix_UB_32      0.0052161000
_diffrn_orient_matrix_UB_33      0.0176158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1622
_reflns_number_total             1890
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.117(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.067
_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)+(0.0212P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
2.d :
 C7(H7)
;
_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 0.52039(17) 0.3033(2) 0.93297(14) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.4051(2) 0.2247(3) 0.9656(2) 0.0284(5) Uani 1 1 d . . . . .
H1A H 0.334846 0.310204 0.953715 0.043 Uiso 1 1 calc R U . . .
H1B H 0.427306 0.190765 1.045807 0.043 Uiso 1 1 calc R U . . .
H1C H 0.377425 0.121519 0.918656 0.043 Uiso 1 1 calc R U . . .
N2 N 0.64417(17) 0.4302(2) 0.83266(15) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.5193(2) 0.3869(2) 0.83314(18) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.6486(2) 0.2933(3) 0.99688(19) 0.0274(5) Uani 1 1 d . . . . .
H3 H 0.675921 0.241869 1.069744 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7261(2) 0.3712(3) 0.9348(2) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.817148 0.383502 0.955874 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6864(2) 0.5226(3) 0.7375(2) 0.0229(5) Uani 1 1 d . . . . .
H5A H 0.642018 0.636656 0.724020 0.027 Uiso 1 1 calc R U . . .
H5B H 0.780450 0.544494 0.759037 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6561(2) 0.4169(3) 0.6306(2) 0.0228(5) Uani 1 1 d . . . . .
C7 C 0.6251(2) 0.3303(3) 0.5466(2) 0.0290(5) Uani 1 1 d . . . . .
H7 H 0.600492 0.261490 0.479991 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4022(2) 0.4246(3) 0.74020(19) 0.0234(5) Uani 1 1 d . . . . .
H8A H 0.398976 0.342130 0.677597 0.035 Uiso 1 1 calc R U . . .
H8B H 0.407495 0.543834 0.712403 0.035 Uiso 1 1 calc R U . . .
H8C H 0.324068 0.412256 0.770279 0.035 Uiso 1 1 calc R U . . .
Br1 Br 0.45629(2) -0.06844(3) 0.71839(2) 0.02436(11) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0252(9) 0.0176(9) 0.0179(9) -0.0020(7) 0.0052(7) 0.0021(8)
C1 0.0344(13) 0.0265(12) 0.0276(13) 0.0017(10) 0.0142(10) 0.0005(11)
N2 0.0162(9) 0.0196(9) 0.0203(9) -0.0036(7) 0.0027(7) 0.0002(7)
C2 0.0212(11) 0.0133(10) 0.0183(11) -0.0047(8) 0.0047(9) 0.0012(8)
C3 0.0313(12) 0.0265(12) 0.0202(12) -0.0006(9) -0.0038(10) 0.0084(11)
C4 0.0191(11) 0.0284(12) 0.0267(13) -0.0061(10) -0.0041(10) 0.0060(10)
C5 0.0207(11) 0.0190(11) 0.0306(13) -0.0020(9) 0.0092(10) -0.0033(9)
C6 0.0202(11) 0.0231(12) 0.0275(13) 0.0059(10) 0.0104(9) 0.0034(9)
C7 0.0292(12) 0.0323(13) 0.0263(13) 0.0022(11) 0.0074(10) 0.0040(11)
C8 0.0155(10) 0.0285(12) 0.0256(12) 0.0018(9) 0.0031(9) 0.0004(9)
Br1 0.02187(14) 0.02473(15) 0.02653(15) -0.00420(9) 0.00538(9) -0.00004(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.462(3) . ?
N1 C2 1.335(3) . ?
N1 C3 1.384(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.340(3) . ?
N2 C4 1.389(3) . ?
N2 C5 1.468(3) . ?
C2 C8 1.479(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.338(3) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.467(3) . ?
C6 C7 1.171(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.06(18) . . ?
C2 N1 C3 109.19(18) . . ?
C3 N1 C1 125.63(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 109.27(18) . . ?
C2 N2 C5 124.76(17) . . ?
C4 N2 C5 125.96(18) . . ?
N1 C2 N2 107.29(17) . . ?
N1 C2 C8 126.4(2) . . ?
N2 C2 C8 126.34(19) . . ?
N1 C3 H3 126.2 . . ?
C4 C3 N1 107.53(19) . . ?
C4 C3 H3 126.2 . . ?
N2 C4 H4 126.6 . . ?
C3 C4 N2 106.71(19) . . ?
C3 C4 H4 126.6 . . ?
N2 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 N2 111.11(17) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C7 C6 C5 176.1(2) . . ?
C6 C7 H7 180.0 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 N2 0.4(2) . . . . ?
C1 N1 C2 N2 -176.36(17) . . . . ?
C1 N1 C2 C8 3.5(3) . . . . ?
C1 N1 C3 C4 176.03(18) . . . . ?
C2 N1 C3 C4 -0.3(2) . . . . ?
C2 N2 C4 C3 -0.5(2) . . . . ?
C2 N2 C5 C6 -62.1(2) . . . . ?
C3 N1 C2 N2 -0.1(2) . . . . ?
C3 N1 C2 C8 179.85(19) . . . . ?
C4 N2 C2 N1 0.3(2) . . . . ?
C4 N2 C2 C8 -179.57(19) . . . . ?
C4 N2 C5 C6 116.7(2) . . . . ?
C5 N2 C2 N1 179.32(17) . . . . ?
C5 N2 C2 C8 -0.6(3) . . . . ?
C5 N2 C4 C3 -179.46(18) . . . . ?

_shelx_res_file                  
;
TITL tw2010_a.res in P2(1)/n
    tw2010.res
    created by SHELXL-2018/3 at 14:46:32 on 23-Jun-2021
REM Old TITL TW2010 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.128, Rweak 0.328, Alpha 0.024
REM <I/s> 0.670 for 142 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N3 Br
CELL 0.71073 10.4022 7.513 11.819 90 102.618 90
ZERR 4 0.0007 0.0005 0.0009 0 0.008 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Br N
UNIT 32 44 4 8

L.S. 10
PLAN  5
SIZE 0.17 0.15 0.12
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2010.hkl">
REM </olex2.extras>

WGHT    0.021200    0.151200
EXTI    0.117304
FVAR       0.94954
N1    4    0.520386    0.303262    0.932967    11.00000    0.02518    0.01759 =
         0.01785   -0.00205    0.00523    0.00208
C1    1    0.405094    0.224693    0.965586    11.00000    0.03439    0.02654 =
         0.02765    0.00167    0.01419    0.00055
AFIX 137
H1A   2    0.334846    0.310204    0.953715    11.00000   -1.50000
H1B   2    0.427306    0.190765    1.045807    11.00000   -1.50000
H1C   2    0.377425    0.121519    0.918656    11.00000   -1.50000
AFIX   0
N2    4    0.644174    0.430161    0.832665    11.00000    0.01624    0.01959 =
         0.02032   -0.00362    0.00275    0.00023
C2    1    0.519334    0.386896    0.833144    11.00000    0.02118    0.01335 =
         0.01828   -0.00466    0.00467    0.00122
C3    1    0.648598    0.293324    0.996881    11.00000    0.03126    0.02650 =
         0.02017   -0.00055   -0.00385    0.00839
AFIX  43
H3    2    0.675921    0.241869    1.069744    11.00000   -1.20000
AFIX   0
C4    1    0.726080    0.371207    0.934774    11.00000    0.01913    0.02843 =
         0.02666   -0.00612   -0.00407    0.00604
AFIX  43
H4    2    0.817148    0.383502    0.955874    11.00000   -1.20000
AFIX   0
C5    1    0.686369    0.522559    0.737477    11.00000    0.02074    0.01898 =
         0.03056   -0.00200    0.00917   -0.00326
AFIX  23
H5A   2    0.642018    0.636656    0.724020    11.00000   -1.20000
H5B   2    0.780450    0.544494    0.759037    11.00000   -1.20000
AFIX   0
C6    1    0.656138    0.416860    0.630579    11.00000    0.02024    0.02307 =
         0.02750    0.00593    0.01036    0.00335
C7    1    0.625121    0.330256    0.546641    11.00000    0.02917    0.03230 =
         0.02630    0.00216    0.00743    0.00405
AFIX 163
H7    2    0.600492    0.261490    0.479991    11.00000   -1.20000
AFIX   0
C8    1    0.402195    0.424584    0.740205    11.00000    0.01548    0.02845 =
         0.02558    0.00183    0.00308    0.00037
AFIX 137
H8A   2    0.398976    0.342130    0.677597    11.00000   -1.50000
H8B   2    0.407495    0.543834    0.712403    11.00000   -1.50000
H8C   2    0.324068    0.412256    0.770279    11.00000   -1.50000
AFIX   0

BR1   3    0.456295   -0.068443    0.718388    11.00000    0.02187    0.02473 =
         0.02653   -0.00420    0.00538   -0.00004
HKLF 4




REM  tw2010_a.res in P2(1)/n
REM wR2 = 0.0511, GooF = S = 1.067, Restrained GooF = 1.067 for all data
REM R1 = 0.0243 for 1622 Fo > 4sig(Fo) and 0.0333 for all 1890 data
REM 103 parameters refined using 0 restraints

END

WGHT      0.0212      0.1512

REM Highest difference peak  0.407,  deepest hole -0.359,  1-sigma level  0.064
Q1    1   0.3656 -0.0657  0.7225  11.00000  0.05    0.41
Q2    1   0.5430 -0.0528  0.7030  11.00000  0.05    0.38
Q3    1   0.4866  0.0292  0.6230  11.00000  0.05    0.26
Q4    1   0.6775  0.4038  0.8865  11.00000  0.05    0.26
Q5    1   0.5392 -0.0593  0.6144  11.00000  0.05    0.25
;
_shelx_res_checksum              33197
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_[NC2C1C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120105'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 N3, Br'
_chemical_formula_sum            'C7 H10 Br N3'
_chemical_formula_weight         216.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H9 Br N2'
_chemical_oxdiff_usercomment     SK86_EtOH
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'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.0482(3)
_cell_length_b                   11.4371(5)
_cell_length_c                   11.1712(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.909(5)
_cell_angle_gamma                90
_cell_volume                     897.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.0710
_cell_measurement_theta_min      3.3130
_shelx_estimated_absorpt_T_max   0.550
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    4.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5531
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  52.00   1.00    1.00    --  -13.33  77.00 120.00   91
  2  ω    -80.00  12.00   1.00    1.00    --  -13.33 -77.00   0.00   92
  3  ω     -2.00  81.00   1.00    1.00    --   14.58  57.00 -90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0036360000
_diffrn_orient_matrix_UB_12      -0.0246032000
_diffrn_orient_matrix_UB_13      0.0571580000
_diffrn_orient_matrix_UB_21      0.0049758000
_diffrn_orient_matrix_UB_22      -0.0909471000
_diffrn_orient_matrix_UB_23      -0.0145084000
_diffrn_orient_matrix_UB_31      0.0696110000
_diffrn_orient_matrix_UB_32      0.0052161000
_diffrn_orient_matrix_UB_33      0.0176158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                1782
_reflns_number_total             1904
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1904
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.042
_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)+(0.0322P)²+1.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_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 0.5437(7) 0.2853(4) 0.3261(4) 0.0270(11) Uani 1 1 d . . . . .
C1 C 0.4664(10) 0.1919(6) 0.2471(6) 0.0365(15) Uani 1 1 d . . . . .
H1A H 0.401384 0.136066 0.293073 0.055 Uiso 1 1 calc R U . . .
H1B H 0.568367 0.153785 0.210734 0.055 Uiso 1 1 calc R U . . .
H1C H 0.378557 0.224442 0.185537 0.055 Uiso 1 1 calc R U . . .
N2 N 0.5723(9) 0.4185(6) 0.4615(6) 0.0268(14) Uani 1 1 d . . . . .
C2 C 0.4502(8) 0.3471(5) 0.4020(5) 0.0266(12) Uani 1 1 d . . . . .
N3 N 0.4758(11) 0.4152(7) 0.7567(6) 0.0390(18) Uani 1 1 d . . . . .
C3 C 0.2446(9) 0.3401(6) 0.4148(6) 0.0332(14) Uani 1 1 d . . . . .
H3A H 0.175451 0.366099 0.341920 0.050 Uiso 1 1 calc R U . . .
H3B H 0.213567 0.388946 0.480256 0.050 Uiso 1 1 calc R U . . .
H3C H 0.210624 0.260657 0.430713 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7353(9) 0.3173(5) 0.3392(6) 0.0322(14) Uani 1 1 d . . . . .
H4 H 0.832186 0.286939 0.296923 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7530(11) 0.3991(6) 0.4232(6) 0.0320(14) Uani 1 1 d . . . . .
H5 H 0.864961 0.436766 0.451423 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5296(9) 0.5060(5) 0.5501(5) 0.0246(13) Uani 1 1 d . . . . .
H6A H 0.415877 0.548441 0.520689 0.030 Uiso 1 1 calc R U . . .
H6B H 0.633839 0.561503 0.559792 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5002(9) 0.4545(6) 0.6671(6) 0.0267(14) Uani 1 1 d . . . . .
Br1 Br 0.54439(6) 0.11494(4) 0.58843(5) 0.02900(17) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.027(3) 0.031(3) 0.023(2) -0.002(2) 0.006(2) 0.001(2)
C1 0.038(4) 0.037(4) 0.035(4) -0.010(3) 0.005(3) 0.001(3)
N2 0.025(3) 0.024(3) 0.033(4) 0.002(3) 0.008(3) 0.000(2)
C2 0.028(3) 0.027(3) 0.025(3) 0.005(2) 0.006(2) 0.004(3)
N3 0.049(5) 0.031(3) 0.038(4) -0.007(3) 0.011(3) -0.005(3)
C3 0.019(3) 0.045(4) 0.037(3) 0.004(3) 0.007(3) 0.005(3)
C4 0.023(3) 0.034(3) 0.042(4) -0.002(3) 0.016(3) 0.001(2)
C5 0.023(3) 0.039(4) 0.036(3) 0.000(3) 0.009(3) -0.002(3)
C6 0.022(3) 0.024(3) 0.029(3) -0.002(2) 0.011(3) 0.002(2)
C7 0.019(3) 0.027(4) 0.035(4) -0.010(3) 0.008(3) -0.002(3)
Br1 0.0289(3) 0.0295(3) 0.0294(3) -0.0017(4) 0.00686(19) 0.0013(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.461(8) . ?
N1 C2 1.323(7) . ?
N1 C4 1.395(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.324(9) . ?
N2 C5 1.395(9) . ?
N2 C6 1.457(8) . ?
C2 C3 1.470(8) . ?
N3 C7 1.124(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.324(9) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.464(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 126.7(5) . . ?
C2 N1 C4 108.8(5) . . ?
C4 N1 C1 124.3(5) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C5 108.6(6) . . ?
C2 N2 C6 127.0(6) . . ?
C5 N2 C6 124.4(6) . . ?
N1 C2 N2 108.3(5) . . ?
N1 C2 C3 125.6(6) . . ?
N2 C2 C3 126.1(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 126.5 . . ?
C5 C4 N1 107.0(6) . . ?
C5 C4 H4 126.5 . . ?
N2 C5 H5 126.4 . . ?
C4 C5 N2 107.3(6) . . ?
C4 C5 H5 126.4 . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
N2 C6 C7 112.5(5) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
N3 C7 C6 179.3(8) . . ?

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
N1 C4 C5 N2 -0.4(7) . . . . ?
C1 N1 C2 N2 176.6(6) . . . . ?
C1 N1 C2 C3 -5.2(9) . . . . ?
C1 N1 C4 C5 -176.1(6) . . . . ?
C2 N1 C4 C5 -0.3(7) . . . . ?
C2 N2 C5 C4 1.0(8) . . . . ?
C2 N2 C6 C7 77.1(9) . . . . ?
C4 N1 C2 N2 1.0(7) . . . . ?
C4 N1 C2 C3 179.2(6) . . . . ?
C5 N2 C2 N1 -1.3(7) . . . . ?
C5 N2 C2 C3 -179.5(6) . . . . ?
C5 N2 C6 C7 -105.0(7) . . . . ?
C6 N2 C2 N1 177.0(6) . . . . ?
C6 N2 C2 C3 -1.2(11) . . . . ?
C6 N2 C5 C4 -177.2(6) . . . . ?

_shelx_res_file                  
;
TITL tw2012_a.res in Cc
    tw2012.res
    created by SHELXL-2018/3 at 15:06:36 on 23-Jun-2021
REM Old TITL TW2012 in Cc
REM SHELXT solution in Cc: R1 0.056, Rweak 0.307, Alpha 0.023
REM <I/s> 1.426 for 48 systematic absences, Orientation as input
REM Flack x = -0.009 ( 0.013 ) from 795 Parsons' quotients
REM Formula found by SHELXT: C7 N3 Br
CELL 0.71073 7.0482 11.4371 11.1712 90 94.909 90
ZERR 4 0.0003 0.0005 0.0006 0 0.005 0
LATT -7
SYMM +X,-Y,0.5+Z
SFAC C H Br N
UNIT 28 40 4 12

L.S. 10
PLAN  5
SIZE 0.2 0.17 0.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2012.hkl">
REM </olex2.extras>

WGHT    0.032200    1.106500
FVAR       0.49159
N1    4    0.543653    0.285254    0.326060    11.00000    0.02731    0.03088 =
         0.02331   -0.00166    0.00558    0.00124
C1    1    0.466369    0.191888    0.247085    11.00000    0.03789    0.03676 =
         0.03519   -0.00961    0.00481    0.00064
AFIX 137
H1A   2    0.401384    0.136066    0.293073    11.00000   -1.50000
H1B   2    0.568367    0.153785    0.210734    11.00000   -1.50000
H1C   2    0.378557    0.224442    0.185537    11.00000   -1.50000
AFIX   0
N2    4    0.572348    0.418450    0.461550    11.00000    0.02466    0.02389 =
         0.03270    0.00152    0.00817   -0.00037
C2    1    0.450174    0.347114    0.401979    11.00000    0.02776    0.02726 =
         0.02540    0.00460    0.00585    0.00404
N3    4    0.475764    0.415183    0.756665    11.00000    0.04880    0.03141 =
         0.03821   -0.00682    0.01113   -0.00531
C3    1    0.244620    0.340095    0.414832    11.00000    0.01851    0.04506 =
         0.03681    0.00376    0.00699    0.00490
AFIX 137
H3A   2    0.175451    0.366099    0.341920    11.00000   -1.50000
H3B   2    0.213567    0.388946    0.480256    11.00000   -1.50000
H3C   2    0.210624    0.260657    0.430713    11.00000   -1.50000
AFIX   0
C4    1    0.735287    0.317295    0.339172    11.00000    0.02291    0.03391 =
         0.04210   -0.00241    0.01593    0.00114
AFIX  43
H4    2    0.832186    0.286939    0.296923    11.00000   -1.20000
AFIX   0
C5    1    0.752974    0.399146    0.423208    11.00000    0.02287    0.03863 =
         0.03555    0.00000    0.00889   -0.00213
AFIX  43
H5    2    0.864961    0.436766    0.451423    11.00000   -1.20000
AFIX   0
C6    1    0.529604    0.505996    0.550072    11.00000    0.02238    0.02403 =
         0.02892   -0.00248    0.01072    0.00161
AFIX  23
H6A   2    0.415877    0.548441    0.520689    11.00000   -1.20000
H6B   2    0.633839    0.561503    0.559792    11.00000   -1.20000
AFIX   0
C7    1    0.500155    0.454495    0.667062    11.00000    0.01858    0.02749 =
         0.03490   -0.00980    0.00770   -0.00204

BR1   3    0.544390    0.114945    0.588430    11.00000    0.02889    0.02947 =
         0.02939   -0.00170    0.00686    0.00128
HKLF 4




REM  tw2012_a.res in Cc
REM wR2 = 0.0720, GooF = S = 1.042, Restrained GooF = 1.042 for all data
REM R1 = 0.0330 for 1782 Fo > 4sig(Fo) and 0.0365 for all 1904 data
REM 102 parameters refined using 2 restraints

END

WGHT      0.0322      1.1064

REM Highest difference peak  0.487,  deepest hole -0.370,  1-sigma level  0.069
Q1    1   0.5342  0.0367  0.5861  11.00000  0.05    0.49
Q2    1   0.6735  0.1173  0.6146  11.00000  0.05    0.45
Q3    1   0.4164  0.1193  0.5550  11.00000  0.05    0.38
Q4    1   0.5492  0.1948  0.5906  11.00000  0.05    0.37
Q5    1   0.5652  0.1180  0.5632  11.00000  0.05    0.32
;
_shelx_res_checksum              32411
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_[HCC2C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120104'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H9 N2, Br'
_chemical_formula_sum            'C7 H9 Br N2'
_chemical_formula_weight         201.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H9 Br N2'
_chemical_oxdiff_usercomment     SK85_acetone
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'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.7092(3)
_cell_length_b                   15.2680(4)
_cell_length_c                   7.4616(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.339(4)
_cell_angle_gamma                90
_cell_volume                     846.96(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.5510
_cell_measurement_theta_min      2.6350
_shelx_estimated_absorpt_T_max   0.497
_shelx_estimated_absorpt_T_min   0.433
_exptl_absorpt_coefficient_mu    4.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5356
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.138
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  82.00   1.00    1.22    --   14.27  57.00   0.00   84
  2  ω    -19.00  54.00   1.00    1.22    --   14.27-101.00 117.00   73
  3  ω    -25.00  53.00   1.00    1.22    --   14.27 -99.00 -30.00   78
  4  ω    -50.00  33.00   1.00    1.22    --   14.27 -37.00 -30.00   83
  5  ω    -40.00  51.00   1.00    1.22    --  -13.18  77.00-150.00   91
  6  ω    -80.00  14.00   1.00    1.22    --  -13.18 -77.00  90.00   94
  7  ω    -80.00   3.00   1.00    1.22    --  -13.18 -57.00-150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148379000
_diffrn_orient_matrix_UB_12      -0.0435876000
_diffrn_orient_matrix_UB_13      0.0253341000
_diffrn_orient_matrix_UB_21      -0.0940122000
_diffrn_orient_matrix_UB_22      0.0078747000
_diffrn_orient_matrix_UB_23      -0.0239479000
_diffrn_orient_matrix_UB_31      -0.0066749000
_diffrn_orient_matrix_UB_32      -0.0140049000
_diffrn_orient_matrix_UB_33      -0.0922117000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                1685
_reflns_number_total             1757
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.033
_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)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d :
 C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4367(6) 0.2547(2) 0.2051(4) 0.0236(9) Uani 1 1 d . . . . .
C1 C 0.4454(7) 0.1633(3) 0.1523(7) 0.0388(11) Uani 1 1 d . . . . .
H1A H 0.335099 0.134438 0.153340 0.058 Uiso 1 1 calc R U . . .
H1B H 0.544009 0.135066 0.238947 0.058 Uiso 1 1 calc R U . . .
H1C H 0.462981 0.160207 0.029779 0.058 Uiso 1 1 calc R U . . .
N2 N 0.3331(5) 0.3795(3) 0.2576(5) 0.0235(9) Uani 1 1 d . . . . .
C2 C 0.2880(7) 0.2966(3) 0.2152(7) 0.0264(11) Uani 1 1 d . . . . .
H2 H 0.173956 0.272287 0.196142 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5789(7) 0.3133(4) 0.2415(7) 0.0303(13) Uani 1 1 d . . . . .
H3 H 0.697187 0.301134 0.241731 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5123(7) 0.3916(3) 0.2766(7) 0.0313(11) Uani 1 1 d . . . . .
H4 H 0.576330 0.443535 0.307672 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2096(5) 0.4457(3) 0.2998(6) 0.0280(9) Uani 1 1 d . . . . .
H5A H 0.204343 0.438846 0.427516 0.034 Uiso 1 1 calc R U . . .
H5B H 0.255344 0.503830 0.286586 0.034 Uiso 1 1 calc R U . . .
C6 C 0.0288(6) 0.4368(2) 0.1758(6) 0.0292(9) Uani 1 1 d . . . . .
C7 C -0.1166(6) 0.4273(3) 0.0761(6) 0.0373(10) Uani 1 1 d . . . . .
H7 H -0.231294 0.419823 -0.002606 0.045 Uiso 1 1 calc R U . . .
Br1 Br 0.45125(8) 0.35293(2) 0.74879(8) 0.02961(13) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0206(18) 0.0250(15) 0.024(2) 0.0001(11) 0.0033(19) -0.0016(15)
C1 0.030(3) 0.032(2) 0.053(3) -0.007(2) 0.009(2) 0.0046(19)
N2 0.022(2) 0.0226(19) 0.025(2) 0.0036(16) 0.0052(16) -0.0049(16)
C2 0.020(2) 0.024(2) 0.034(3) 0.0011(19) 0.004(2) -0.0029(18)
C3 0.015(2) 0.042(3) 0.035(3) -0.004(2) 0.007(2) 0.000(2)
C4 0.027(3) 0.029(3) 0.038(3) -0.006(2) 0.009(2) -0.0059(19)
C5 0.026(2) 0.025(2) 0.033(2) -0.0001(16) 0.0084(19) 0.0008(16)
C6 0.031(2) 0.022(2) 0.037(2) 0.0030(17) 0.013(2) -0.0027(17)
C7 0.028(3) 0.036(2) 0.046(3) 0.0024(19) 0.007(2) 0.0021(18)
Br1 0.02250(19) 0.02913(19) 0.0353(2) 0.0005(3) 0.00429(14) 0.0065(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 C1 1.457(5) . ?
N1 C2 1.331(7) . ?
N1 C3 1.384(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.328(6) . ?
N2 C4 1.364(6) . ?
N2 C5 1.479(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.354(8) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.461(6) . ?
C6 C7 1.179(6) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.2(4) . . ?
C2 N1 C3 109.2(4) . . ?
C3 N1 C1 125.5(4) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 110.4(5) . . ?
C2 N2 C5 124.0(4) . . ?
C4 N2 C5 125.2(4) . . ?
N1 C2 H2 126.4 . . ?
N2 C2 N1 107.2(5) . . ?
N2 C2 H2 126.4 . . ?
N1 C3 H3 126.7 . . ?
C4 C3 N1 106.7(5) . . ?
C4 C3 H3 126.7 . . ?
N2 C4 H4 126.7 . . ?
C3 C4 N2 106.6(5) . . ?
C3 C4 H4 126.7 . . ?
N2 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 N2 111.2(3) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C7 C6 C5 178.2(4) . . ?
C6 C7 H7 180.0 . . ?

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
N1 C3 C4 N2 -1.1(5) . . . . ?
C1 N1 C2 N2 -176.6(4) . . . . ?
C1 N1 C3 C4 177.2(4) . . . . ?
C2 N1 C3 C4 0.9(5) . . . . ?
C2 N2 C4 C3 1.0(5) . . . . ?
C2 N2 C5 C6 -40.6(5) . . . . ?
C3 N1 C2 N2 -0.3(5) . . . . ?
C4 N2 C2 N1 -0.5(5) . . . . ?
C4 N2 C5 C6 147.2(4) . . . . ?
C5 N2 C2 N1 -173.7(4) . . . . ?
C5 N2 C4 C3 174.2(4) . . . . ?

_shelx_res_file                  
;
TITL TW2011b in Cc #9
    tw2011b.res
    created by SHELXL-2018/3 at 15:36:14 on 23-Jun-2021
REM reset to Cc #9
CELL 0.71073 7.70916 15.26797 7.46157 90 105.3394 90
ZERR 4 0.00025 0.0004 0.00027 0 0.0036 0
LATT -7
SYMM +X,-Y,0.5+Z
SFAC C H Br N
UNIT 28 36 4 8

L.S. 10
PLAN  5
SIZE 0.17 0.18 0.21
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2011b.hkl">
REM </olex2.extras>

WGHT    0.027900
FVAR       4.44136
N1    4    0.436691    0.254740    0.205121    11.00000    0.02059    0.02497 =
         0.02383    0.00014    0.00330   -0.00160
C1    1    0.445441    0.163319    0.152293    11.00000    0.03033    0.03213 =
         0.05256   -0.00703    0.00855    0.00458
AFIX 137
H1A   2    0.335099    0.134438    0.153340    11.00000   -1.50000
H1B   2    0.544009    0.135066    0.238947    11.00000   -1.50000
H1C   2    0.462981    0.160207    0.029779    11.00000   -1.50000
AFIX   0
N2    4    0.333066    0.379462    0.257596    11.00000    0.02178    0.02258 =
         0.02543    0.00361    0.00518   -0.00494
C2    1    0.288031    0.296572    0.215211    11.00000    0.01969    0.02439 =
         0.03364    0.00115    0.00429   -0.00290
AFIX  43
H2    2    0.173956    0.272287    0.196142    11.00000   -1.20000
AFIX   0
C3    1    0.578906    0.313265    0.241486    11.00000    0.01470    0.04157 =
         0.03473   -0.00404    0.00692    0.00038
AFIX  43
H3    2    0.697187    0.301134    0.241731    11.00000   -1.20000
AFIX   0
C4    1    0.512344    0.391616    0.276635    11.00000    0.02711    0.02941 =
         0.03764   -0.00574    0.00905   -0.00594
AFIX  43
H4    2    0.576330    0.443535    0.307672    11.00000   -1.20000
AFIX   0
C5    1    0.209551    0.445684    0.299800    11.00000    0.02634    0.02497 =
         0.03315   -0.00013    0.00843    0.00084
AFIX  23
H5A   2    0.204343    0.438846    0.427516    11.00000   -1.20000
H5B   2    0.255344    0.503830    0.286586    11.00000   -1.20000
AFIX   0
C6    1    0.028819    0.436848    0.175793    11.00000    0.03052    0.02181 =
         0.03745    0.00303    0.01284   -0.00275
C7    1   -0.116598    0.427330    0.076059    11.00000    0.02821    0.03569 =
         0.04639    0.00236    0.00689    0.00207
AFIX 163
H7    2   -0.231294    0.419823   -0.002606    11.00000   -1.20000
AFIX   0

BR1   3    0.451250    0.352935    0.748790    11.00000    0.02250    0.02913 =
         0.03531    0.00054    0.00429    0.00648
HKLF 4




REM  TW2011b in Cc #9
REM wR2 = 0.0498, GooF = S = 1.034, Restrained GooF = 1.033 for all data
REM R1 = 0.0227 for 1685 Fo > 4sig(Fo) and 0.0249 for all 1757 data
REM 92 parameters refined using 2 restraints

END

WGHT      0.0279      0.0000

REM Highest difference peak  0.225,  deepest hole -0.301,  1-sigma level  0.053
Q1    1   0.3768  0.2830  0.2524  11.00000  0.05    0.22
Q2    1   0.3392  0.3853  0.6535  11.00000  0.05    0.21
Q3    1   0.5171  0.2841  0.2520  11.00000  0.05    0.21
Q4    1   0.5082  0.3909  0.7099  11.00000  0.05    0.20
Q5    1   0.5643  0.3885  0.8378  11.00000  0.05    0.19
;
_shelx_res_checksum              98727
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.834
####################################################################### 
# 
# 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_[NC2C1C1im]Cl
_database_code_depnum_ccdc_archive 'CCDC 2120108'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 N3, Cl'
_chemical_formula_sum            'C7 H10 Cl N3'
_chemical_formula_weight         171.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H10 Cl N3'
_chemical_oxdiff_usercomment     SK62_ISOP
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3329(3)
_cell_length_b                   9.3234(4)
_cell_length_c                   12.2867(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.240(3)
_cell_angle_gamma                90
_cell_volume                     840.00(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.5560
_cell_measurement_theta_min      5.9420
_shelx_estimated_absorpt_T_max   0.554
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3152
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.299
_diffrn_reflns_theta_min         5.958
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  93.00   1.00    1.00    --   42.36-125.00-180.00   89
  2  ω     36.00 102.00   1.00    1.00    --  105.13 -77.00-120.00   66
  3  ω     26.00  60.00   1.00    1.00    --   42.36-125.00  60.00   34
  4  ω     74.00 138.00   1.00    1.00    --  105.13 -77.00  60.00   64
  5  ω     92.00 176.00   1.00    1.00    --  105.13  61.00  60.00   84
  6  ω     19.00  45.00   1.00    1.00    --   42.23  57.00 -30.00   26
  7  ω     73.00  98.00   1.00    1.00    --   42.23-125.00-180.00   25
  8  ω     54.00 109.00   1.00    1.00    --   42.23  57.00 -30.00   55
  9  ω     71.00  97.00   1.00    1.00    --  105.13 -95.00-180.00   26
 10  ω     31.00 104.00   1.00    1.00    --  105.13 -30.00 -60.00   73
 11  ω     35.00  74.00   1.00    1.00    --  105.13 -45.00 -90.00   39
 12  ω     42.00  87.00   1.00    1.00    --  105.13 -30.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1852036000
_diffrn_orient_matrix_UB_12      0.0131060000
_diffrn_orient_matrix_UB_13      -0.0579043000
_diffrn_orient_matrix_UB_21      -0.0235513000
_diffrn_orient_matrix_UB_22      0.1525066000
_diffrn_orient_matrix_UB_23      0.0461467000
_diffrn_orient_matrix_UB_31      0.0963640000
_diffrn_orient_matrix_UB_32      0.0621793000
_diffrn_orient_matrix_UB_33      -0.1011768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1374
_reflns_number_total             1629
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.059
_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)+(0.0486P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0953
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_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 0.1985(2) 0.40809(18) 0.45967(12) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.2749(3) 0.3100(2) 0.54100(16) 0.0322(5) Uani 1 1 d . . . . .
H1A H 0.180954 0.246786 0.566536 0.048 Uiso 1 1 calc R U . . .
H1B H 0.322916 0.364176 0.601042 0.048 Uiso 1 1 calc R U . . .
H1C H 0.370889 0.254564 0.508742 0.048 Uiso 1 1 calc R U . . .
N2 N 0.0703(2) 0.49168(18) 0.31548(12) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.1005(2) 0.3714(2) 0.37281(15) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.1859(3) 0.4137(2) 0.05208(14) 0.0360(4) Uani 1 1 d . . . . .
C3 C 0.0304(3) 0.2270(2) 0.34559(17) 0.0306(4) Uani 1 1 d . . . . .
H3A H 0.093086 0.190921 0.282876 0.046 Uiso 1 1 calc R U . . .
H3B H -0.097874 0.232790 0.330165 0.046 Uiso 1 1 calc R U . . .
H3C H 0.050338 0.163669 0.406062 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2329(3) 0.5541(2) 0.45740(15) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.298974 0.606021 0.508765 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1531(2) 0.6069(2) 0.36728(15) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.153363 0.701913 0.344192 0.029 Uiso 1 1 calc R U . . .
C6 C -0.0234(3) 0.5006(2) 0.21021(14) 0.0252(4) Uani 1 1 d . . . . .
H6A H -0.059707 0.599045 0.196575 0.030 Uiso 1 1 calc R U . . .
H6B H -0.132718 0.442057 0.211926 0.030 Uiso 1 1 calc R U . . .
C7 C 0.0961(3) 0.4510(2) 0.12185(15) 0.0255(4) Uani 1 1 d . . . . .
Cl1 Cl 0.55446(6) 0.37168(5) 0.28871(4) 0.02751(16) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0232(8) 0.0294(9) 0.0198(7) 0.0026(6) 0.0018(6) 0.0052(7)
C1 0.0338(11) 0.0359(12) 0.0269(10) 0.0079(9) -0.0019(8) 0.0099(9)
N2 0.0223(7) 0.0232(8) 0.0213(7) 0.0007(6) -0.0002(6) 0.0005(6)
C2 0.0218(9) 0.0246(10) 0.0232(9) 0.0017(8) 0.0026(7) 0.0029(8)
N3 0.0424(10) 0.0388(11) 0.0267(9) -0.0004(8) -0.0021(8) 0.0067(9)
C3 0.0338(11) 0.0223(10) 0.0355(10) -0.0004(8) 0.0006(8) 0.0008(8)
C4 0.0228(9) 0.0287(11) 0.0256(9) -0.0045(8) 0.0007(7) -0.0009(8)
C5 0.0245(9) 0.0211(9) 0.0266(9) -0.0024(7) 0.0035(7) -0.0018(7)
C6 0.0264(9) 0.0247(10) 0.0243(9) -0.0005(8) -0.0054(7) 0.0007(8)
C7 0.0310(10) 0.0219(10) 0.0237(9) 0.0032(8) -0.0086(8) -0.0011(8)
Cl1 0.0275(3) 0.0273(3) 0.0277(2) -0.00489(18) -0.00048(17) -0.00122(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 C1 1.465(2) . ?
N1 C2 1.329(2) . ?
N1 C4 1.385(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.342(2) . ?
N2 C5 1.387(2) . ?
N2 C6 1.465(2) . ?
C2 C3 1.479(3) . ?
N3 C7 1.138(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.344(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.473(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 126.26(18) . . ?
C2 N1 C4 109.54(16) . . ?
C4 N1 C1 123.97(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C5 109.58(15) . . ?
C2 N2 C6 125.94(16) . . ?
C5 N2 C6 124.33(16) . . ?
N1 C2 N2 107.12(16) . . ?
N1 C2 C3 127.02(17) . . ?
N2 C2 C3 125.81(17) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 126.3 . . ?
C5 C4 N1 107.35(17) . . ?
C5 C4 H4 126.3 . . ?
N2 C5 H5 126.8 . . ?
C4 C5 N2 106.40(17) . . ?
C4 C5 H5 126.8 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 C7 110.77(15) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
N3 C7 C6 178.6(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
N1 C4 C5 N2 0.1(2) . . . . ?
C1 N1 C2 N2 -175.12(16) . . . . ?
C1 N1 C2 C3 7.2(3) . . . . ?
C1 N1 C4 C5 175.02(16) . . . . ?
C2 N1 C4 C5 0.3(2) . . . . ?
C2 N2 C5 C4 -0.4(2) . . . . ?
C2 N2 C6 C7 -76.2(2) . . . . ?
C4 N1 C2 N2 -0.5(2) . . . . ?
C4 N1 C2 C3 -178.18(18) . . . . ?
C5 N2 C2 N1 0.6(2) . . . . ?
C5 N2 C2 C3 178.27(18) . . . . ?
C5 N2 C6 C7 99.0(2) . . . . ?
C6 N2 C2 N1 176.34(16) . . . . ?
C6 N2 C2 C3 -6.0(3) . . . . ?
C6 N2 C5 C4 -176.26(16) . . . . ?

_shelx_res_file                  
;
TITL tw2103_a.res in P2(1)/n
    tw2103.res
    created by SHELXL-2018/3 at 15:27:25 on 23-Jun-2021
REM Old TITL TW2103 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.091, Rweak 0.270, Alpha 0.013
REM <I/s> 0.554 for 107 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N3 Cl
CELL 1.54184 7.3329 9.3234 12.2867 90 90.24 90
ZERR 4 0.0003 0.0004 0.0004 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Cl
UNIT 28 40 12 4

L.S. 4
PLAN  5
SIZE 0.26 0.2 0.19
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2103.hkl">
REM </olex2.extras>

WGHT    0.048600    0.280400
FVAR       1.25259
N1    3    0.198512    0.408088    0.459669    11.00000    0.02318    0.02943 =
         0.01981    0.00257    0.00178    0.00524
C1    1    0.274896    0.309952    0.541002    11.00000    0.03377    0.03588 =
         0.02687    0.00789   -0.00186    0.00991
AFIX 137
H1A   2    0.180954    0.246786    0.566536    11.00000   -1.50000
H1B   2    0.322916    0.364176    0.601042    11.00000   -1.50000
H1C   2    0.370889    0.254564    0.508742    11.00000   -1.50000
AFIX   0
N2    3    0.070340    0.491679    0.315480    11.00000    0.02226    0.02318 =
         0.02133    0.00070   -0.00019    0.00046
C2    1    0.100548    0.371449    0.372813    11.00000    0.02183    0.02462 =
         0.02325    0.00173    0.00260    0.00293
N3    3    0.185916    0.413689    0.052084    11.00000    0.04239    0.03881 =
         0.02674   -0.00042   -0.00213    0.00670
C3    1    0.030366    0.227034    0.345590    11.00000    0.03382    0.02233 =
         0.03554   -0.00040    0.00058    0.00080
AFIX 137
H3A   2    0.093086    0.190921    0.282876    11.00000   -1.50000
H3B   2   -0.097874    0.232790    0.330165    11.00000   -1.50000
H3C   2    0.050338    0.163669    0.406062    11.00000   -1.50000
AFIX   0
C4    1    0.232886    0.554106    0.457398    11.00000    0.02277    0.02867 =
         0.02555   -0.00448    0.00074   -0.00093
AFIX  43
H4    2    0.298974    0.606021    0.508765    11.00000   -1.20000
AFIX   0
C5    1    0.153125    0.606917    0.367278    11.00000    0.02450    0.02105 =
         0.02662   -0.00238    0.00345   -0.00181
AFIX  43
H5    2    0.153363    0.701913    0.344192    11.00000   -1.20000
AFIX   0
C6    1   -0.023417    0.500601    0.210206    11.00000    0.02640    0.02475 =
         0.02427   -0.00050   -0.00545    0.00069
AFIX  23
H6A   2   -0.059707    0.599045    0.196575    11.00000   -1.20000
H6B   2   -0.132718    0.442057    0.211926    11.00000   -1.20000
AFIX   0
C7    1    0.096088    0.450988    0.121854    11.00000    0.03098    0.02186 =
         0.02373    0.00316   -0.00864   -0.00112

CL1   4    0.554463    0.371679    0.288709    11.00000    0.02755    0.02732 =
         0.02766   -0.00489   -0.00048   -0.00122
HKLF 4




REM  tw2103_a.res in P2(1)/n
REM wR2 = 0.0953, GooF = S = 1.059, Restrained GooF = 1.059 for all data
REM R1 = 0.0353 for 1374 Fo > 4sig(Fo) and 0.0442 for all 1629 data
REM 102 parameters refined using 0 restraints

END

WGHT      0.0486      0.2803

REM Highest difference peak  0.228,  deepest hole -0.295,  1-sigma level  0.056
Q1    1   0.1366  0.1514  0.3539  11.00000  0.05    0.23
Q2    1   0.0421  0.4214  0.3422  11.00000  0.05    0.22
Q3    1  -0.1487  0.6716  0.0895  11.00000  0.05    0.20
Q4    1  -0.0189  0.1887  0.2561  11.00000  0.05    0.19
Q5    1   0.2535  0.5846  0.3975  11.00000  0.05    0.18
;
_shelx_res_checksum              84522
_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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_[NC2C1im][NTf2]
_database_code_depnum_ccdc_archive 'CCDC 2120106'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C2 F6 N O4 S2, C7 H10 N3'
_chemical_formula_sum            'C9 H10 F6 N4 O4 S2'
_chemical_formula_weight         416.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 Br N3'
_chemical_oxdiff_usercomment     SK57_EtOH
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0861(12)
_cell_length_b                   16.2425(13)
_cell_length_c                   15.1289(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.599(8)
_cell_angle_gamma                90
_cell_volume                     3215.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1679
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      27.8950
_cell_measurement_theta_min      3.1050
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20094
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  51.00   1.00    1.00    --  -13.33  77.00  30.00   89
  2  ω    -79.00  12.00   1.00    1.00    --  -13.33 -77.00 -90.00   91
  3  ω     -2.00  82.00   1.00    1.00    --   14.43  57.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0063109000
_diffrn_orient_matrix_UB_12      -0.0482126000
_diffrn_orient_matrix_UB_13      -0.0927195000
_diffrn_orient_matrix_UB_21      -0.0432595000
_diffrn_orient_matrix_UB_22      0.0154604000
_diffrn_orient_matrix_UB_23      -0.0300069000
_diffrn_orient_matrix_UB_31      0.0131618000
_diffrn_orient_matrix_UB_32      0.0739370000
_diffrn_orient_matrix_UB_33      -0.0541867000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5185
_reflns_number_total             6677
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6677
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0797
_refine_ls_restrained_S_all      1.036
_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)+(0.1487P)²+6.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2478
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.750(3)
 0.250(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C3(H3), C4(H4)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.72401(11) 0.12070(8) 0.61445(10) 0.0309(3) Uani 1 1 d . . . . .
F1 F 0.6097(5) 0.1146(4) 0.7511(4) 0.0873(17) Uani 1 1 d . . . . .
O1 O 0.7196(5) 0.0326(3) 0.6074(4) 0.0695(17) Uani 1 1 d . . . . .
S2 S 0.72157(12) 0.13206(10) 0.43020(11) 0.0361(4) Uani 1 1 d . . . . .
F2 F 0.5252(4) 0.1192(4) 0.6308(4) 0.0819(17) Uani 1 1 d . . . . .
O2 O 0.8022(4) 0.1559(4) 0.6670(4) 0.0652(16) Uani 1 1 d . . . . .
F3 F 0.6003(4) 0.2270(3) 0.6832(5) 0.0900(18) Uani 1 1 d . . . . .
O3 O 0.7805(3) 0.0610(3) 0.4191(4) 0.0562(14) Uani 1 1 d . . . . .
F4 F 0.5544(3) 0.0474(3) 0.4423(4) 0.0711(14) Uani 1 1 d . . . . .
O4 O 0.7445(5) 0.2022(3) 0.3767(4) 0.0668(16) Uani 1 1 d . . . . .
N4 N 0.7089(5) 0.1699(3) 0.5257(4) 0.0523(15) Uani 1 1 d . . . . .
F5 F 0.5302(4) 0.1687(3) 0.4005(4) 0.0792(16) Uani 1 1 d . . . . .
F6 F 0.5954(5) 0.0815(5) 0.3098(4) 0.0942(19) Uani 1 1 d . U . . .
C9 C 0.6057(5) 0.1488(4) 0.6688(5) 0.0450(16) Uani 1 1 d . . . . .
C10 C 0.5928(5) 0.1062(4) 0.3928(5) 0.0401(14) Uani 1 1 d . . . . .
S11 S 0.26220(11) 0.35938(8) 0.42806(10) 0.0307(3) Uani 1 1 d . . . . .
F11 F 0.4563(3) 0.3301(3) 0.4087(4) 0.0737(15) Uani 1 1 d . . . . .
O11 O 0.2437(4) 0.2875(3) 0.3742(3) 0.0542(13) Uani 1 1 d . . . . .
S12 S 0.25590(11) 0.38296(8) 0.61139(10) 0.0301(3) Uani 1 1 d . . . . .
F12 F 0.3896(4) 0.4112(4) 0.3116(3) 0.0736(14) Uani 1 1 d . . . . .
O12 O 0.2009(4) 0.4299(3) 0.4124(4) 0.0557(14) Uani 1 1 d . . . . .
F13 F 0.4237(4) 0.4529(3) 0.4437(3) 0.0665(13) Uani 1 1 d . . . . .
O13 O 0.2484(5) 0.4703(3) 0.5984(3) 0.0631(16) Uani 1 1 d . . . . .
F14 F 0.3893(4) 0.2859(3) 0.6890(4) 0.0744(14) Uani 1 1 d . . . . .
O14 O 0.1818(4) 0.3440(3) 0.6654(3) 0.0474(12) Uani 1 1 d . . . . .
N14 N 0.2738(4) 0.3291(3) 0.5256(3) 0.0359(11) Uani 1 1 d . . . . .
F15 F 0.3717(4) 0.4043(4) 0.7494(3) 0.0751(15) Uani 1 1 d . . . . .
F16 F 0.4556(4) 0.3929(4) 0.6299(4) 0.0803(16) Uani 1 1 d . . . . .
C19 C 0.3903(5) 0.3900(4) 0.3949(5) 0.0384(14) Uani 1 1 d . . . . .
C20 C 0.3761(6) 0.3656(5) 0.6723(5) 0.0499(18) Uani 1 1 d . . . . .
N11 N 0.1560(4) 0.6219(3) 0.4053(3) 0.0332(11) Uani 1 1 d . . . . .
C11 C 0.2061(6) 0.6179(4) 0.3203(4) 0.0463(16) Uani 1 1 d . . . . .
H11A H 0.204615 0.671193 0.292970 0.069 Uiso 1 1 calc R U . . .
H11B H 0.171205 0.578944 0.282987 0.069 Uiso 1 1 calc R U . . .
H11C H 0.275804 0.600774 0.328692 0.069 Uiso 1 1 calc R U . . .
N12 N 0.1273(4) 0.6279(3) 0.5449(3) 0.0298(11) Uani 1 1 d . . . . .
C12 C 0.2012(4) 0.6277(3) 0.4849(4) 0.0244(11) Uani 1 1 d . . . . .
N13 N 0.0233(5) 0.7433(4) 0.7064(4) 0.0530(15) Uani 1 1 d . . . . .
C13 C 0.0521(6) 0.6187(5) 0.4149(5) 0.0542(19) Uani 1 1 d . . . . .
H13 H 0.003364 0.615547 0.369852 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0342(5) 0.6209(5) 0.5023(5) 0.0516(19) Uani 1 1 d . . . . .
H14 H -0.029355 0.618235 0.529049 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1411(5) 0.6319(3) 0.6413(4) 0.0339(13) Uani 1 1 d . . . . .
H15A H 0.124266 0.579038 0.667208 0.041 Uiso 1 1 calc R U . . .
H15B H 0.211888 0.644152 0.655572 0.041 Uiso 1 1 calc R U . . .
C16 C 0.0756(5) 0.6952(3) 0.6778(4) 0.0357(13) Uani 1 1 d . . . . .
C18 C 0.3128(4) 0.6311(3) 0.5021(4) 0.0330(13) Uani 1 1 d . . . . .
H18A H 0.335031 0.580040 0.527962 0.050 Uiso 1 1 calc R U . . .
H18B H 0.327917 0.675489 0.541986 0.050 Uiso 1 1 calc R U . . .
H18C H 0.347892 0.639784 0.447460 0.050 Uiso 1 1 calc R U . . .
N1 N 0.1357(4) 0.1343(3) 0.5920(3) 0.0291(10) Uani 1 1 d . . . . .
C1 C 0.1793(6) 0.1353(4) 0.6813(4) 0.0445(16) Uani 1 1 d . . . . .
H1A H 0.200933 0.080805 0.697260 0.067 Uiso 1 1 calc R U . . .
H1B H 0.128731 0.154070 0.722110 0.067 Uiso 1 1 calc R U . . .
H1C H 0.237008 0.171842 0.683055 0.067 Uiso 1 1 calc R U . . .
N2 N 0.1200(4) 0.1234(3) 0.4505(3) 0.0260(10) Uani 1 1 d . . . . .
C2 C 0.1888(4) 0.1272(3) 0.5173(4) 0.0221(10) Uani 1 1 d . . . . .
N3 N 0.0240(5) 0.0122(3) 0.2770(3) 0.0469(14) Uani 1 1 d . . . . .
C3 C 0.0327(5) 0.1355(4) 0.5711(4) 0.0388(14) Uani 1 1 d . . . . .
H3 H -0.020229 0.140286 0.611239 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0221(4) 0.1288(4) 0.4843(4) 0.0377(14) Uani 1 1 d . . . . .
H4 H -0.038972 0.127976 0.452283 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1443(5) 0.1184(3) 0.3564(4) 0.0300(12) Uani 1 1 d . . . . .
H5A H 0.215020 0.101853 0.349599 0.036 Uiso 1 1 calc R U . . .
H5B H 0.135623 0.172081 0.329254 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0768(5) 0.0583(3) 0.3124(4) 0.0341(13) Uani 1 1 d . . . . .
C8 C 0.3006(4) 0.1254(3) 0.5111(5) 0.0319(13) Uani 1 1 d . . . . .
H8A H 0.328155 0.176611 0.532331 0.048 Uiso 1 1 calc R U . . .
H8B H 0.319769 0.117546 0.450625 0.048 Uiso 1 1 calc R U . . .
H8C H 0.327074 0.080991 0.546384 0.048 Uiso 1 1 calc R U . . .

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
S1 0.0275(7) 0.0306(6) 0.0344(7) -0.0031(6) -0.0032(6) 0.0067(5)
F1 0.072(4) 0.124(5) 0.067(3) 0.016(3) 0.018(3) -0.002(3)
O1 0.103(5) 0.038(3) 0.067(3) 0.005(2) -0.003(3) 0.016(3)
S2 0.0241(7) 0.0483(8) 0.0360(7) -0.0022(7) 0.0032(6) -0.0067(6)
F2 0.026(2) 0.122(5) 0.097(4) -0.029(3) 0.000(2) -0.017(3)
O2 0.031(3) 0.102(4) 0.063(3) -0.028(3) 0.002(2) -0.002(3)
F3 0.056(3) 0.075(3) 0.139(5) -0.045(3) 0.024(3) 0.014(3)
O3 0.028(2) 0.045(2) 0.095(4) -0.004(3) 0.005(3) 0.0099(19)
F4 0.041(2) 0.052(2) 0.120(4) 0.011(3) 0.007(3) -0.017(2)
O4 0.069(4) 0.042(3) 0.090(4) -0.003(3) 0.024(3) -0.026(3)
N4 0.064(4) 0.036(3) 0.057(4) 0.002(3) 0.003(3) 0.002(3)
F5 0.043(3) 0.057(3) 0.137(5) 0.005(3) -0.009(3) 0.020(2)
F6 0.063(3) 0.155(5) 0.065(3) -0.040(3) -0.010(3) -0.013(3)
C9 0.028(3) 0.054(4) 0.053(4) -0.007(3) 0.008(3) -0.006(3)
C10 0.030(3) 0.040(3) 0.050(4) 0.000(3) -0.004(3) 0.002(3)
S11 0.0231(7) 0.0331(6) 0.0359(7) 0.0053(6) -0.0007(6) -0.0035(5)
F11 0.035(2) 0.068(3) 0.118(4) -0.001(3) 0.010(3) 0.019(2)
O11 0.067(4) 0.049(3) 0.046(2) -0.002(2) -0.009(3) -0.022(2)
S12 0.0292(7) 0.0244(6) 0.0367(7) 0.0009(5) 0.0050(6) 0.0058(5)
F12 0.054(3) 0.114(4) 0.053(3) 0.014(3) 0.020(2) -0.017(3)
O12 0.040(3) 0.060(3) 0.068(3) 0.027(3) 0.012(2) 0.019(2)
F13 0.057(3) 0.056(2) 0.087(3) -0.010(2) 0.017(2) -0.031(2)
O13 0.101(4) 0.024(2) 0.065(3) 0.003(2) 0.015(3) 0.020(2)
F14 0.055(3) 0.080(3) 0.087(3) 0.014(3) -0.015(3) 0.026(3)
O14 0.031(2) 0.063(3) 0.048(3) 0.008(2) 0.006(2) -0.001(2)
N14 0.047(3) 0.020(2) 0.041(3) -0.003(2) 0.000(3) 0.005(2)
F15 0.045(3) 0.121(4) 0.059(3) -0.036(3) -0.007(2) -0.005(3)
F16 0.035(3) 0.130(4) 0.075(3) -0.013(3) 0.012(2) -0.031(3)
C19 0.027(3) 0.036(3) 0.052(4) -0.006(3) 0.008(3) -0.002(2)
C20 0.038(4) 0.068(5) 0.043(4) -0.007(3) 0.002(3) -0.001(3)
N11 0.033(3) 0.033(2) 0.033(3) 0.000(2) 0.003(2) 0.0067(19)
C11 0.054(4) 0.048(4) 0.037(3) -0.001(3) 0.012(3) 0.002(3)
N12 0.026(3) 0.034(2) 0.030(2) -0.0017(19) 0.0036(19) 0.0000(19)
C12 0.021(3) 0.020(2) 0.033(3) 0.005(2) 0.005(2) 0.0013(19)
N13 0.051(4) 0.051(3) 0.057(3) -0.006(3) 0.006(3) 0.013(3)
C13 0.025(3) 0.083(5) 0.054(4) -0.018(4) -0.006(3) 0.004(3)
C14 0.013(3) 0.078(5) 0.063(5) -0.014(4) -0.002(3) 0.000(3)
C15 0.035(3) 0.035(3) 0.032(3) 0.000(2) 0.003(3) 0.002(2)
C16 0.040(3) 0.032(3) 0.036(3) -0.003(2) 0.009(3) -0.005(3)
C18 0.019(3) 0.029(3) 0.051(4) 0.004(3) 0.003(2) -0.001(2)
N1 0.030(3) 0.027(2) 0.030(2) -0.0011(19) -0.004(2) 0.0010(18)
C1 0.054(4) 0.050(4) 0.029(3) -0.002(3) -0.005(3) -0.008(3)
N2 0.019(2) 0.029(2) 0.030(2) 0.0011(19) -0.0001(18) -0.0001(17)
C2 0.021(2) 0.013(2) 0.032(3) -0.001(2) -0.003(2) 0.0029(18)
N3 0.065(4) 0.036(3) 0.040(3) -0.001(2) 0.000(3) -0.006(3)
C3 0.028(3) 0.048(3) 0.041(3) -0.002(3) 0.010(3) -0.001(3)
C4 0.011(2) 0.058(4) 0.044(3) 0.003(3) -0.002(2) 0.000(2)
C5 0.026(3) 0.034(3) 0.030(3) 0.000(2) -0.001(2) 0.002(2)
C6 0.044(4) 0.028(3) 0.030(3) 0.002(2) 0.004(3) 0.004(3)
C8 0.021(3) 0.023(2) 0.051(3) -0.006(2) -0.004(3) 0.004(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
S1 O1 1.436(5) . ?
S1 O2 1.410(6) . ?
S1 N4 1.573(6) . ?
S1 C9 1.819(7) . ?
F1 C9 1.365(9) . ?
S2 O3 1.399(5) . ?
S2 O4 1.431(5) . ?
S2 N4 1.580(6) . ?
S2 C10 1.821(7) . ?
F2 C9 1.287(9) . ?
F3 C9 1.292(8) . ?
F4 C10 1.316(8) . ?
F5 C10 1.311(8) . ?
F6 C10 1.319(8) . ?
S11 O11 1.442(5) . ?
S11 O12 1.416(5) . ?
S11 N14 1.561(5) . ?
S11 C19 1.823(6) . ?
F11 C19 1.316(7) . ?
S12 O13 1.435(4) . ?
S12 O14 1.424(5) . ?
S12 N14 1.585(5) . ?
S12 C20 1.836(8) . ?
F12 C19 1.307(8) . ?
F13 C19 1.331(7) . ?
F14 C20 1.329(9) . ?
F15 C20 1.327(8) . ?
F16 C20 1.306(9) . ?
N11 C11 1.452(8) . ?
N11 C12 1.340(8) . ?
N11 C13 1.370(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N12 C12 1.333(7) . ?
N12 C14 1.377(8) . ?
N12 C15 1.469(8) . ?
C12 C18 1.482(8) . ?
N13 C16 1.127(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.345(11) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.452(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 C1 1.461(8) . ?
N1 C2 1.338(7) . ?
N1 C3 1.380(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.348(7) . ?
N2 C4 1.387(7) . ?
N2 C5 1.463(7) . ?
C2 C8 1.467(7) . ?
N3 C6 1.147(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.323(9) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.472(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N4 116.0(3) . . ?
O1 S1 C9 104.5(4) . . ?
O2 S1 O1 118.3(4) . . ?
O2 S1 N4 111.1(4) . . ?
O2 S1 C9 105.1(3) . . ?
N4 S1 C9 99.1(3) . . ?
O3 S2 O4 118.0(3) . . ?
O3 S2 N4 119.6(4) . . ?
O3 S2 C10 106.3(3) . . ?
O4 S2 N4 103.4(3) . . ?
O4 S2 C10 101.9(3) . . ?
N4 S2 C10 105.6(3) . . ?
S1 N4 S2 124.7(4) . . ?
F1 C9 S1 106.6(5) . . ?
F2 C9 S1 113.7(5) . . ?
F2 C9 F1 106.2(6) . . ?
F2 C9 F3 113.4(7) . . ?
F3 C9 S1 111.8(5) . . ?
F3 C9 F1 104.4(6) . . ?
F4 C10 S2 110.4(5) . . ?
F4 C10 F6 109.6(6) . . ?
F5 C10 S2 111.7(5) . . ?
F5 C10 F4 105.5(6) . . ?
F5 C10 F6 110.0(6) . . ?
F6 C10 S2 109.5(5) . . ?
O11 S11 N14 107.0(3) . . ?
O11 S11 C19 102.4(3) . . ?
O12 S11 O11 117.9(3) . . ?
O12 S11 N14 117.6(3) . . ?
O12 S11 C19 104.7(3) . . ?
N14 S11 C19 105.4(3) . . ?
O13 S12 N14 116.4(3) . . ?
O13 S12 C20 106.1(4) . . ?
O14 S12 O13 118.2(3) . . ?
O14 S12 N14 109.4(3) . . ?
O14 S12 C20 103.2(3) . . ?
N14 S12 C20 101.1(3) . . ?
S11 N14 S12 125.9(3) . . ?
F11 C19 S11 111.0(4) . . ?
F11 C19 F13 105.5(6) . . ?
F12 C19 S11 109.9(5) . . ?
F12 C19 F11 110.2(6) . . ?
F12 C19 F13 109.3(6) . . ?
F13 C19 S11 110.8(4) . . ?
F14 C20 S12 110.7(5) . . ?
F15 C20 S12 108.9(5) . . ?
F15 C20 F14 107.6(7) . . ?
F16 C20 S12 112.6(5) . . ?
F16 C20 F14 108.7(7) . . ?
F16 C20 F15 108.2(6) . . ?
C12 N11 C11 126.9(6) . . ?
C12 N11 C13 109.7(5) . . ?
C13 N11 C11 123.4(6) . . ?
N11 C11 H11A 109.5 . . ?
N11 C11 H11B 109.5 . . ?
N11 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N12 C14 109.0(5) . . ?
C12 N12 C15 126.5(5) . . ?
C14 N12 C15 124.5(6) . . ?
N11 C12 C18 125.8(5) . . ?
N12 C12 N11 107.2(5) . . ?
N12 C12 C18 126.9(6) . . ?
N11 C13 H13 126.7 . . ?
C14 C13 N11 106.6(6) . . ?
C14 C13 H13 126.7 . . ?
N12 C14 H14 126.3 . . ?
C13 C14 N12 107.5(6) . . ?
C13 C14 H14 126.3 . . ?
N12 C15 H15A 109.7 . . ?
N12 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 N12 110.0(5) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
N13 C16 C15 178.6(7) . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C1 125.5(5) . . ?
C2 N1 C3 108.8(5) . . ?
C3 N1 C1 125.6(6) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 109.5(5) . . ?
C2 N2 C5 125.5(5) . . ?
C4 N2 C5 125.0(5) . . ?
N1 C2 N2 106.7(4) . . ?
N1 C2 C8 125.6(5) . . ?
N2 C2 C8 127.6(6) . . ?
N1 C3 H3 125.7 . . ?
C4 C3 N1 108.6(5) . . ?
C4 C3 H3 125.7 . . ?
N2 C4 H4 126.8 . . ?
C3 C4 N2 106.4(5) . . ?
C3 C4 H4 126.8 . . ?
N2 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
N2 C5 C6 110.0(5) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N3 C6 C5 179.1(6) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N4 S2 -18.6(7) . . . . ?
O1 S1 C9 F1 63.9(6) . . . . ?
O1 S1 C9 F2 -52.7(7) . . . . ?
O1 S1 C9 F3 177.3(6) . . . . ?
O2 S1 N4 S2 120.2(5) . . . . ?
O2 S1 C9 F1 -61.3(6) . . . . ?
O2 S1 C9 F2 -177.9(6) . . . . ?
O2 S1 C9 F3 52.2(7) . . . . ?
O3 S2 N4 S1 -22.2(7) . . . . ?
O3 S2 C10 F4 62.7(6) . . . . ?
O3 S2 C10 F5 179.8(5) . . . . ?
O3 S2 C10 F6 -58.1(6) . . . . ?
O4 S2 N4 S1 -155.9(5) . . . . ?
O4 S2 C10 F4 -173.1(5) . . . . ?
O4 S2 C10 F5 -56.0(6) . . . . ?
O4 S2 C10 F6 66.1(6) . . . . ?
N4 S1 C9 F1 -176.1(5) . . . . ?
N4 S1 C9 F2 67.2(6) . . . . ?
N4 S1 C9 F3 -62.7(6) . . . . ?
N4 S2 C10 F4 -65.3(5) . . . . ?
N4 S2 C10 F5 51.8(6) . . . . ?
N4 S2 C10 F6 173.9(5) . . . . ?
C9 S1 N4 S2 -129.7(5) . . . . ?
C10 S2 N4 S1 97.4(5) . . . . ?
O11 S11 N14 S12 -156.8(4) . . . . ?
O11 S11 C19 F11 -58.3(6) . . . . ?
O11 S11 C19 F12 63.9(5) . . . . ?
O11 S11 C19 F13 -175.2(5) . . . . ?
O12 S11 N14 S12 -21.5(6) . . . . ?
O12 S11 C19 F11 178.1(5) . . . . ?
O12 S11 C19 F12 -59.7(5) . . . . ?
O12 S11 C19 F13 61.2(6) . . . . ?
O13 S12 N14 S11 -13.1(6) . . . . ?
O13 S12 C20 F14 179.0(5) . . . . ?
O13 S12 C20 F15 60.9(6) . . . . ?
O13 S12 C20 F16 -59.1(6) . . . . ?
O14 S12 N14 S11 124.0(4) . . . . ?
O14 S12 C20 F14 54.0(6) . . . . ?
O14 S12 C20 F15 -64.0(6) . . . . ?
O14 S12 C20 F16 176.0(5) . . . . ?
N14 S11 C19 F11 53.5(5) . . . . ?
N14 S11 C19 F12 175.7(4) . . . . ?
N14 S11 C19 F13 -63.4(5) . . . . ?
N14 S12 C20 F14 -59.2(6) . . . . ?
N14 S12 C20 F15 -177.2(5) . . . . ?
N14 S12 C20 F16 62.8(6) . . . . ?
C19 S11 N14 S12 94.7(4) . . . . ?
C20 S12 N14 S11 -127.5(5) . . . . ?
N11 C13 C14 N12 1.8(9) . . . . ?
C11 N11 C12 N12 -178.7(5) . . . . ?
C11 N11 C12 C18 -0.2(9) . . . . ?
C11 N11 C13 C14 177.8(6) . . . . ?
C12 N11 C13 C14 -1.3(8) . . . . ?
C12 N12 C14 C13 -1.7(8) . . . . ?
C12 N12 C15 C16 130.7(6) . . . . ?
C13 N11 C12 N12 0.2(7) . . . . ?
C13 N11 C12 C18 178.8(6) . . . . ?
C14 N12 C12 N11 0.9(6) . . . . ?
C14 N12 C12 C18 -177.7(6) . . . . ?
C14 N12 C15 C16 -51.7(8) . . . . ?
C15 N12 C12 N11 178.8(5) . . . . ?
C15 N12 C12 C18 0.3(9) . . . . ?
C15 N12 C14 C13 -179.6(6) . . . . ?
N1 C3 C4 N2 -0.1(7) . . . . ?
C1 N1 C2 N2 176.1(5) . . . . ?
C1 N1 C2 C8 -4.9(8) . . . . ?
C1 N1 C3 C4 -176.2(6) . . . . ?
C2 N1 C3 C4 0.3(7) . . . . ?
C2 N2 C4 C3 -0.2(7) . . . . ?
C2 N2 C5 C6 137.6(5) . . . . ?
C3 N1 C2 N2 -0.5(6) . . . . ?
C3 N1 C2 C8 178.6(5) . . . . ?
C4 N2 C2 N1 0.4(6) . . . . ?
C4 N2 C2 C8 -178.6(5) . . . . ?
C4 N2 C5 C6 -45.6(7) . . . . ?
C5 N2 C2 N1 177.7(4) . . . . ?
C5 N2 C2 C8 -1.3(8) . . . . ?
C5 N2 C4 C3 -177.5(5) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_file                  
;
TITL TW2101 in P21/c #14
    tw2101.res
    created by SHELXL-2018/3 at 15:57:15 on 23-Jun-2021
REM reset to P21/c #14
CELL 0.71073 13.086051 16.242498 15.128932 90 90.599 90
ZERR 8 0.001179 0.001256 0.00136 0 0.0079 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N O S
UNIT 72 80 48 32 32 16
ISOR 0.05 0.01 F6

L.S. 4
PLAN  5
SIZE 0.05 0.13 0.15
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
TWIN 1 0 0.02 0 -1 0 0 0 -1 2
OMIT -5 1 2
OMIT 10 1 1
REM <olex2.extras>
REM <HklSrc "%.\\TW2101.hkl">
REM </olex2.extras>

WGHT    0.148700    6.352000
BASF   0.24984
FVAR       1.48408
S1    6    0.724012    0.120701    0.614447    11.00000    0.02748    0.03063 =
         0.03438   -0.00312   -0.00321    0.00674
F1    3    0.609724    0.114590    0.751116    11.00000    0.07186    0.12361 =
         0.06677    0.01557    0.01787   -0.00218
O1    5    0.719626    0.032630    0.607439    11.00000    0.10318    0.03849 =
         0.06673    0.00518   -0.00273    0.01584
S2    6    0.721574    0.132056    0.430204    11.00000    0.02415    0.04827 =
         0.03600   -0.00219    0.00319   -0.00675
F2    3    0.525232    0.119228    0.630816    11.00000    0.02649    0.12180 =
         0.09746   -0.02921   -0.00001   -0.01670
O2    5    0.802184    0.155885    0.666986    11.00000    0.03055    0.10180 =
         0.06327   -0.02843    0.00208   -0.00210
F3    3    0.600255    0.227030    0.683176    11.00000    0.05637    0.07516 =
         0.13892   -0.04491    0.02412    0.01429
O3    5    0.780451    0.060984    0.419076    11.00000    0.02819    0.04540 =
         0.09510   -0.00385    0.00489    0.00992
F4    3    0.554378    0.047449    0.442273    11.00000    0.04131    0.05209 =
         0.12006    0.01052    0.00711   -0.01749
O4    5    0.744486    0.202180    0.376722    11.00000    0.06942    0.04173 =
         0.08961   -0.00251    0.02370   -0.02584
N4    4    0.708943    0.169866    0.525710    11.00000    0.06371    0.03612 =
         0.05720    0.00157    0.00318    0.00193
F5    3    0.530226    0.168692    0.400478    11.00000    0.04306    0.05734 =
         0.13685    0.00498   -0.00930    0.01981
F6    3    0.595430    0.081505    0.309762    11.00000    0.06275    0.15466 =
         0.06488   -0.04022   -0.01017   -0.01291
C9    1    0.605672    0.148783    0.668757    11.00000    0.02823    0.05407 =
         0.05279   -0.00721    0.00787   -0.00632
C10   1    0.592836    0.106166    0.392764    11.00000    0.03002    0.03997 =
         0.05016   -0.00043   -0.00376    0.00170
S11   6    0.262201    0.359380    0.428056    11.00000    0.02314    0.03313 =
         0.03593    0.00529   -0.00069   -0.00346
F11   3    0.456268    0.330089    0.408727    11.00000    0.03509    0.06823 =
         0.11802   -0.00141    0.01012    0.01875
O11   5    0.243684    0.287521    0.374245    11.00000    0.06727    0.04938 =
         0.04576   -0.00154   -0.00914   -0.02156
S12   6    0.255904    0.382961    0.611389    11.00000    0.02920    0.02439 =
         0.03672    0.00095    0.00504    0.00581
F12   3    0.389604    0.411197    0.311609    11.00000    0.05366    0.11421 =
         0.05319    0.01396    0.01985   -0.01703
O12   5    0.200925    0.429867    0.412355    11.00000    0.03962    0.05966 =
         0.06797    0.02702    0.01207    0.01925
F13   3    0.423739    0.452867    0.443655    11.00000    0.05708    0.05593 =
         0.08672   -0.01036    0.01694   -0.03134
O13   5    0.248417    0.470309    0.598427    11.00000    0.10052    0.02359 =
         0.06538    0.00253    0.01539    0.02018
F14   3    0.389276    0.285895    0.688971    11.00000    0.05540    0.08044 =
         0.08698    0.01450   -0.01490    0.02607
O14   5    0.181750    0.343983    0.665401    11.00000    0.03137    0.06307 =
         0.04799    0.00757    0.00581   -0.00137
N14   4    0.273812    0.329086    0.525552    11.00000    0.04665    0.01996 =
         0.04122   -0.00337    0.00041    0.00491
F15   3    0.371711    0.404345    0.749365    11.00000    0.04491    0.12130 =
         0.05893   -0.03631   -0.00709   -0.00489
F16   3    0.455642    0.392868    0.629885    11.00000    0.03539    0.13041 =
         0.07530   -0.01304    0.01224   -0.03144
C19   1    0.390266    0.389973    0.394923    11.00000    0.02671    0.03624 =
         0.05250   -0.00620    0.00833   -0.00212
C20   1    0.376072    0.365570    0.672295    11.00000    0.03821    0.06828 =
         0.04328   -0.00675    0.00191   -0.00090
N11   4    0.155965    0.621868    0.405309    11.00000    0.03296    0.03332 =
         0.03339   -0.00034    0.00269    0.00674
C11   1    0.206147    0.617855    0.320290    11.00000    0.05411    0.04784 =
         0.03729   -0.00080    0.01227    0.00166
AFIX 137
H11A  2    0.204615    0.671193    0.292970    11.00000   -1.50000
H11B  2    0.171205    0.578944    0.282987    11.00000   -1.50000
H11C  2    0.275804    0.600774    0.328692    11.00000   -1.50000
AFIX   0
N12   4    0.127345    0.627941    0.544904    11.00000    0.02557    0.03438 =
         0.02954   -0.00173    0.00365   -0.00001
C12   1    0.201204    0.627722    0.484916    11.00000    0.02124    0.01966 =
         0.03252    0.00548    0.00453    0.00134
N13   4    0.023329    0.743255    0.706442    11.00000    0.05128    0.05087 =
         0.05697   -0.00618    0.00624    0.01281
C13   1    0.052069    0.618669    0.414935    11.00000    0.02541    0.08313 =
         0.05406   -0.01794   -0.00610    0.00408
AFIX  43
H13   2    0.003364    0.615547    0.369852    11.00000   -1.20000
AFIX   0
C14   1    0.034225    0.620923    0.502305    11.00000    0.01341    0.07822 =
         0.06306   -0.01350   -0.00157    0.00003
AFIX  43
H14   2   -0.029355    0.618235    0.529049    11.00000   -1.20000
AFIX   0
C15   1    0.141066    0.631900    0.641307    11.00000    0.03488    0.03528 =
         0.03163    0.00034    0.00289    0.00200
AFIX  23
H15A  2    0.124266    0.579038    0.667208    11.00000   -1.20000
H15B  2    0.211888    0.644152    0.655572    11.00000   -1.20000
AFIX   0
C16   1    0.075582    0.695233    0.677796    11.00000    0.03969    0.03155 =
         0.03612   -0.00255    0.00912   -0.00458
C18   1    0.312844    0.631052    0.502094    11.00000    0.01928    0.02851 =
         0.05136    0.00358    0.00330   -0.00120
AFIX 137
H18A  2    0.335031    0.580040    0.527962    11.00000   -1.50000
H18B  2    0.327917    0.675489    0.541986    11.00000   -1.50000
H18C  2    0.347892    0.639784    0.447460    11.00000   -1.50000
AFIX   0

N1    4    0.135666    0.134254    0.591963    11.00000    0.03031    0.02687 =
         0.03012   -0.00106   -0.00396    0.00101
C1    1    0.179330    0.135335    0.681256    11.00000    0.05450    0.04963 =
         0.02915   -0.00222   -0.00491   -0.00771
AFIX 137
H1A   2    0.200933    0.080805    0.697260    11.00000   -1.50000
H1B   2    0.128731    0.154070    0.722110    11.00000   -1.50000
H1C   2    0.237008    0.171842    0.683055    11.00000   -1.50000
AFIX   0
N2    4    0.119977    0.123405    0.450481    11.00000    0.01852    0.02908 =
         0.03040    0.00109   -0.00013   -0.00009
C2    1    0.188824    0.127159    0.517254    11.00000    0.02079    0.01334 =
         0.03209   -0.00055   -0.00296    0.00286
N3    4    0.024023    0.012160    0.277024    11.00000    0.06473    0.03647 =
         0.03959   -0.00083    0.00036   -0.00582
C3    1    0.032748    0.135529    0.571060    11.00000    0.02774    0.04797 =
         0.04091   -0.00179    0.01018   -0.00125
AFIX  43
H3    2   -0.020229    0.140286    0.611239    11.00000   -1.20000
AFIX   0
C4    1    0.022086    0.128848    0.484283    11.00000    0.01109    0.05821 =
         0.04389    0.00260   -0.00189   -0.00016
AFIX  43
H4    2   -0.038972    0.127976    0.452283    11.00000   -1.20000
AFIX   0
C5    1    0.144326    0.118416    0.356438    11.00000    0.02558    0.03391 =
         0.03035   -0.00035   -0.00133    0.00160
AFIX  23
H5A   2    0.215020    0.101853    0.349599    11.00000   -1.20000
H5B   2    0.135623    0.172081    0.329254    11.00000   -1.20000
AFIX   0
C6    1    0.076760    0.058299    0.312359    11.00000    0.04369    0.02845 =
         0.03012    0.00181    0.00394    0.00442
C8    1    0.300615    0.125427    0.511119    11.00000    0.02077    0.02339 =
         0.05138   -0.00560   -0.00406    0.00435
AFIX 137
H8A   2    0.328155    0.176611    0.532331    11.00000   -1.50000
H8B   2    0.319769    0.117546    0.450625    11.00000   -1.50000
H8C   2    0.327074    0.080991    0.546384    11.00000   -1.50000
AFIX   0
HKLF 4




REM  TW2101 in P21/c #14
REM wR2 = 0.2478, GooF = S = 1.031, Restrained GooF = 1.036 for all data
REM R1 = 0.0797 for 5185 Fo > 4sig(Fo) and 0.1023 for all 6677 data
REM 456 parameters refined using 6 restraints

END

WGHT      0.1487      6.3577

REM Highest difference peak  1.246,  deepest hole -0.539,  1-sigma level  0.120
Q1    1   0.7160  0.0782  0.5304  11.00000  0.05    1.25
Q2    1   0.5594  0.2135  0.5990  11.00000  0.05    1.12
Q3    1   0.7800  0.2026  0.6024  11.00000  0.05    1.04
Q4    1   0.7570  0.0701  0.6785  11.00000  0.05    1.02
Q5    1   0.5995  0.1425  0.3012  11.00000  0.05    0.95
;
_shelx_res_checksum              86705
_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 3.279
_oxdiff_exptl_absorpt_empirical_full_min 0.634
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.750(3)
2 0.250(3)

####################################################################### 
# 
# 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_[HOC2C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120109'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H11 N2 O, Br'
_chemical_formula_sum            'C6 H11 Br N2 O'
_chemical_formula_weight         207.08
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H11 Br N2 O'
_chemical_oxdiff_usercomment     SK72Cl_butanol
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.3302(3)
_cell_length_b                   7.1879(3)
_cell_length_c                   8.5495(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.076(5)
_cell_angle_gamma                90
_cell_volume                     425.73(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2388
_cell_measurement_temperature    173.2(7)
_cell_measurement_theta_max      27.8590
_cell_measurement_theta_min      2.4940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.767
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_correction_T_min  0.146
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'tabular needles'
_exptl_crystal_F_000             208
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0526
1 0 -1 0.0446
0 0 1 0.1060
0 0 -1 0.1390
0 1 0 0.3229
-3 -7 -6 0.2702
-1 0 0 0.1100
1 0 0 0.0930
6 0 7 0.1078
-6 0 -8 0.1410
2 -9 5 0.3435
-4 -9 1 0.3439
8 -6 -4 0.2534

_exptl_crystal_size_max          0.712
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.097
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
-0.9991 -0.0013 0.9987 0.0345 -0.0933 0.0488
0.9991 0.0013 -0.9987 -0.0345 0.0933 -0.0488
0.0000 -0.0008 0.9989 -0.0463 -0.0737 -0.0108
-0.0000 0.0008 -0.9989 0.0463 0.0737 0.0108
-0.0003 0.9985 0.0011 0.0536 -0.0218 -0.0799
-2.7915 -7.1447 -6.4016 0.1385 0.5732 0.8076
-0.9991 -0.0005 -0.0002 0.0808 -0.0196 0.0596
0.9991 0.0005 0.0002 -0.0808 0.0196 -0.0596
5.6557 0.0112 7.3772 -0.7980 -0.4337 -0.4185
-5.5235 0.3031 -7.5152 0.8105 0.4396 0.3870
1.8725 -8.5015 5.1196 -0.8444 -0.1560 0.5124
-4.4287 -9.1479 1.4373 -0.1993 0.0062 0.9799
7.9618 -6.3788 -4.2234 -0.7906 0.6068 0.0816

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5312
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.104
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.2(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  82.00   1.00    1.00    --   14.43  57.00 -60.00   82
  2  ω      3.00  82.00   1.00    1.00    --   14.43  77.00 -30.00   79
  3  ω     42.00  82.00   1.00    1.00    --   14.43  77.00  90.00   40
  4  ω      3.00  72.00   1.00    1.00    --   14.43  57.00  90.00   69
  5  ω    -25.00  53.00   1.00    1.00    --   14.43 -99.00  60.00   78
  6  ω    -23.00  54.00   1.00    1.00    --   14.43-100.00 -63.87   77
  7  ω    -25.00  52.00   1.00    1.00    --   14.43 -99.00-180.00   77
  8  ω     -2.00  82.00   1.00    1.00    --   14.43  57.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0808526000
_diffrn_orient_matrix_UB_12      0.0536601000
_diffrn_orient_matrix_UB_13      -0.0462650000
_diffrn_orient_matrix_UB_21      0.0196278000
_diffrn_orient_matrix_UB_22      -0.0217729000
_diffrn_orient_matrix_UB_23      -0.0737987000
_diffrn_orient_matrix_UB_31      -0.0596113000
_diffrn_orient_matrix_UB_32      -0.0799745000
_diffrn_orient_matrix_UB_33      -0.0109089000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                1666
_reflns_number_total             1808
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Flack x determined using 698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.092
_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)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0582
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9986(4)
 0.0014(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O -0.0211(5) 0.2678(5) 0.8324(4) 0.0359(8) Uani 1 1 d . . . . .
H1 H 0.032563 0.189392 0.792979 0.054 Uiso 1 1 calc R U . . .
N1 N 0.3695(5) 0.4123(4) 0.5870(4) 0.0226(8) Uani 1 1 d . . . . .
C1 C 0.3352(7) 0.3683(8) 0.4129(6) 0.0391(12) Uani 1 1 d . . . . .
H1A H 0.312265 0.237227 0.395515 0.059 Uiso 1 1 calc R U . . .
H1B H 0.446174 0.402828 0.383395 0.059 Uiso 1 1 calc R U . . .
H1C H 0.224500 0.435950 0.345412 0.059 Uiso 1 1 calc R U . . .
N2 N 0.3142(4) 0.4741(14) 0.8128(3) 0.0268(7) Uani 1 1 d . . . . .
C2 C 0.2337(5) 0.4613(12) 0.6491(4) 0.0231(7) Uani 1 1 d . . . . .
H2 H 0.104698 0.483053 0.589195 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5405(6) 0.3940(6) 0.7144(7) 0.0335(11) Uani 1 1 d . . . . .
H3 H 0.658981 0.360522 0.704992 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5048(6) 0.4335(7) 0.8554(6) 0.0345(14) Uani 1 1 d . . . . .
H4 H 0.593836 0.432986 0.961707 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2067(8) 0.5223(6) 0.9259(6) 0.0366(12) Uani 1 1 d . . . . .
H5A H 0.107181 0.612464 0.873197 0.044 Uiso 1 1 calc R U . . .
H5B H 0.293933 0.578387 1.025603 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1143(8) 0.3491(7) 0.9716(6) 0.0334(11) Uani 1 1 d . . . . .
H6A H 0.214266 0.258988 1.023626 0.040 Uiso 1 1 calc R U . . .
H6B H 0.050995 0.382669 1.051037 0.040 Uiso 1 1 calc R U . . .
Br1 Br 0.78404(5) 0.46621(12) 1.30570(4) 0.02615(13) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0257(17) 0.044(2) 0.0391(19) -0.0115(16) 0.0125(15) 0.0005(15)
N1 0.0200(17) 0.023(2) 0.0256(18) 0.0014(13) 0.0084(15) 0.0011(12)
C1 0.041(3) 0.051(3) 0.032(3) -0.006(2) 0.022(2) 0.002(2)
N2 0.0329(17) 0.0218(18) 0.0231(15) 0.004(3) 0.0057(14) -0.001(3)
C2 0.0203(17) 0.0235(18) 0.0236(17) 0.002(4) 0.0048(14) 0.000(3)
C3 0.013(2) 0.031(2) 0.051(3) 0.010(2) 0.002(2) 0.0000(17)
C4 0.030(2) 0.029(4) 0.031(2) 0.005(2) -0.0079(19) -0.008(2)
C5 0.060(3) 0.025(3) 0.028(2) -0.0042(17) 0.019(2) -0.003(2)
C6 0.043(3) 0.032(3) 0.026(2) -0.001(2) 0.012(2) -0.001(2)
Br1 0.0240(2) 0.0254(2) 0.0271(2) 0.0005(3) 0.00580(14) -0.0006(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
O1 H1 0.8200 . ?
O1 C6 1.404(6) . ?
N1 C1 1.461(6) . ?
N1 C2 1.320(5) . ?
N1 C3 1.372(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.333(5) . ?
N2 C4 1.356(6) . ?
N2 C5 1.474(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.344(7) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.528(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 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
C6 O1 H1 109.5 . . ?
C2 N1 C1 124.5(4) . . ?
C2 N1 C3 108.6(4) . . ?
C3 N1 C1 126.6(4) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 109.3(4) . . ?
C2 N2 C5 123.9(4) . . ?
C4 N2 C5 126.8(4) . . ?
N1 C2 N2 107.9(4) . . ?
N1 C2 H2 126.0 . . ?
N2 C2 H2 126.0 . . ?
N1 C3 H3 126.4 . . ?
C4 C3 N1 107.3(4) . . ?
C4 C3 H3 126.4 . . ?
N2 C4 H4 126.6 . . ?
C3 C4 N2 106.9(4) . . ?
C3 C4 H4 126.6 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 C6 110.6(5) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O1 C6 C5 111.9(4) . . ?
O1 C6 H6A 109.2 . . ?
O1 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?

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
N1 C3 C4 N2 0.3(6) . . . . ?
C1 N1 C2 N2 174.5(6) . . . . ?
C1 N1 C3 C4 -174.6(5) . . . . ?
N2 C5 C6 O1 -62.3(5) . . . . ?
C2 N1 C3 C4 -0.1(6) . . . . ?
C2 N2 C4 C3 -0.4(9) . . . . ?
C2 N2 C5 C6 85.2(10) . . . . ?
C3 N1 C2 N2 -0.2(8) . . . . ?
C4 N2 C2 N1 0.4(10) . . . . ?
C4 N2 C5 C6 -93.7(9) . . . . ?
C5 N2 C2 N1 -178.7(7) . . . . ?
C5 N2 C4 C3 178.7(7) . . . . ?

_shelx_res_file                  
;
TITL TW2112 in P21 #4
    tw2112.res
    created by SHELXL-2018/3 at 16:05:05 on 23-Jun-2021
REM reset to P21 #4
CELL 0.71073 7.33024 7.18794 8.54949 90 109.0756 90
ZERR 2 0.00034 0.00028 0.00037 0 0.005 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Br N O
UNIT 12 22 2 4 2

L.S. 4
PLAN  5
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0.76 0 1 2
OMIT 1 0 1
REM <olex2.extras>
REM <HklSrc "%.\\TW2112.hkl">
REM </olex2.extras>

WGHT    0.030400
BASF   0.00145
FVAR      10.18114
O1    5   -0.021085    0.267782    0.832406    11.00000    0.02570    0.04431 =
         0.03910   -0.01153    0.01251    0.00054
AFIX 147
H1    2    0.032563    0.189392    0.792979    11.00000   -1.50000
AFIX   0
N1    4    0.369515    0.412264    0.587041    11.00000    0.02002    0.02282 =
         0.02560    0.00138    0.00840    0.00106
C1    1    0.335169    0.368299    0.412913    11.00000    0.04122    0.05125 =
         0.03238   -0.00592    0.02229    0.00171
AFIX 137
H1A   2    0.312265    0.237227    0.395515    11.00000   -1.50000
H1B   2    0.446174    0.402828    0.383395    11.00000   -1.50000
H1C   2    0.224500    0.435950    0.345412    11.00000   -1.50000
AFIX   0
N2    4    0.314160    0.474084    0.812832    11.00000    0.03287    0.02178 =
         0.02313    0.00360    0.00569   -0.00105
C2    1    0.233734    0.461285    0.649125    11.00000    0.02031    0.02353 =
         0.02365    0.00199    0.00481   -0.00004
AFIX  43
H2    2    0.104698    0.483053    0.589195    11.00000   -1.20000
AFIX   0
C3    1    0.540452    0.393990    0.714399    11.00000    0.01327    0.03059 =
         0.05065    0.01038    0.00242    0.00003
AFIX  43
H3    2    0.658981    0.360522    0.704992    11.00000   -1.20000
AFIX   0
C4    1    0.504780    0.433460    0.855358    11.00000    0.03024    0.02904 =
         0.03117    0.00504   -0.00785   -0.00780
AFIX  43
H4    2    0.593836    0.432986    0.961707    11.00000   -1.20000
AFIX   0
C5    1    0.206750    0.522308    0.925949    11.00000    0.06028    0.02496 =
         0.02764   -0.00423    0.01866   -0.00291
AFIX  23
H5A   2    0.107181    0.612464    0.873197    11.00000   -1.20000
H5B   2    0.293933    0.578387    1.025603    11.00000   -1.20000
AFIX   0
C6    1    0.114317    0.349077    0.971610    11.00000    0.04338    0.03219 =
         0.02554   -0.00098    0.01232   -0.00104
AFIX  23
H6A   2    0.214266    0.258988    1.023626    11.00000   -1.20000
H6B   2    0.050995    0.382669    1.051037    11.00000   -1.20000
AFIX   0

BR1   3    0.784040    0.466210    1.305695    11.00000    0.02401    0.02544 =
         0.02712    0.00047    0.00580   -0.00064
HKLF 4




REM  TW2112 in P21 #4
REM wR2 = 0.0582, GooF = S = 1.092, Restrained GooF = 1.092 for all data
REM R1 = 0.0255 for 1666 Fo > 4sig(Fo) and 0.0299 for all 1808 data
REM 94 parameters refined using 1 restraints

END

WGHT      0.0304      0.0000

REM Highest difference peak  0.273,  deepest hole -0.403,  1-sigma level  0.084
Q1    1  -0.0382  0.5378  1.0181  11.00000  0.05    0.27
Q2    1   0.0840  0.0464  0.8764  11.00000  0.05    0.24
Q3    1   0.2617  0.1572  0.8972  11.00000  0.05    0.24
Q4    1   0.6359  0.2505  0.4065  11.00000  0.05    0.22
Q5    1  -0.1239  0.4019  1.0691  11.00000  0.05    0.21
;
_shelx_res_checksum              77771
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.864
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9986(4)
2 0.0014(4)

####################################################################### 
# 
# 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_[C2C1C1im]Br
_database_code_depnum_ccdc_archive 'CCDC 2120110'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H13 N2, Br'
_chemical_formula_sum            'C7 H13 Br N2'
_chemical_formula_weight         205.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H13 Br N2'
_chemical_oxdiff_usercomment     SKS3_BuOH
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8182(2)
_cell_length_b                   17.0994(6)
_cell_length_c                   8.0181(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.298(3)
_cell_angle_gamma                90
_cell_volume                     913.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    172.95(10)
_cell_measurement_theta_max      25.9350
_cell_measurement_theta_min      2.8710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.435
_exptl_absorpt_correction_T_max  0.544
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -24 1 0.0839
-1 24 -1 0.0673
-9 8 3 0.1219
-8 6 -3 0.1264
8 6 4 0.1105
9 6 1 0.1082
-3 0 11 0.2409
3 0 -11 0.2032
-4 3 -9 0.1832
8 7 -7 0.1559
-8 -13 2 0.1256
-2 16 8 0.1659
1 13 -9 0.1696
-7 -8 -4 0.1570
-4 -22 2 0.1165

_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.151
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
1.2164 -23.8482 0.5488 0.3821 -0.9224 0.0565
-1.2134 23.8470 -0.5619 -0.3821 0.9223 -0.0577
-8.9802 8.4675 2.9388 -0.9470 0.1250 0.2958
-8.0832 6.4631 -3.1715 -0.9699 0.0252 -0.2421
7.9673 5.5812 3.6304 0.8447 0.4589 0.2755
8.9743 5.8979 0.6426 0.8788 0.4771 0.0090
-2.6133 -0.2665 11.2795 -0.0158 -0.0003 0.9999
2.6248 0.2613 -11.2786 0.0170 0.0004 -0.9999
-4.4458 3.0524 -8.5793 -0.6803 -0.0542 -0.7309
8.2996 6.6373 -6.7413 0.6375 0.4373 -0.6343
-8.2132 -12.5059 2.3391 -0.6663 -0.7017 0.2522
-2.0730 16.0837 8.3929 -0.1919 0.6506 0.7348
0.7343 13.4453 -9.3125 -0.2693 0.4942 -0.8266
-7.4479 -7.7638 -4.1434 -0.7802 -0.5365 -0.3216
-3.8980 -21.8588 2.2658 -0.1273 -0.9647 0.2305

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.860
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  53.00   1.00    1.49    --  -13.18  37.00 -30.00   84
  2  ω     16.00  69.00   1.00    1.49    --   14.43  57.00  30.00   53
  3  ω      4.00  81.00   1.00    1.49    --   14.43  57.00  90.00   77
  4  ω     -2.00  82.00   1.00    1.49    --   14.43  57.00 -30.00   84
  5  ω     -2.00  82.00   1.00    1.49    --   14.43  57.00-150.00   84
  6  ω    -52.00  40.00   1.00    1.49    --   14.43 -77.00  60.00   92
  7  ω    -62.00  11.00   1.00    1.49    --  -13.18 116.00  82.32   73
  8  ω    -63.00   9.00   1.00    1.49    --  -13.18 118.00-176.16   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1030699000
_diffrn_orient_matrix_UB_12      -0.0102523000
_diffrn_orient_matrix_UB_13      0.0222386000
_diffrn_orient_matrix_UB_21      0.0262562000
_diffrn_orient_matrix_UB_22      0.0401784000
_diffrn_orient_matrix_UB_23      0.0070081000
_diffrn_orient_matrix_UB_31      -0.0048690000
_diffrn_orient_matrix_UB_32      -0.0006053000
_diffrn_orient_matrix_UB_33      0.0875031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1570
_reflns_number_total             2055
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+0.6456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0647
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.5745(3) 0.54781(13) 0.7321(3) 0.0297(5) Uani 1 1 d . . . . .
N2 N 0.5054(3) 0.64926(12) 0.5699(3) 0.0279(5) Uani 1 1 d . . . . .
C1 C 0.6822(5) 0.49026(17) 0.8534(4) 0.0420(7) Uani 1 1 d . . . . .
H1A H 0.795380 0.470721 0.812631 0.063 Uiso 1 1 calc R U . . .
H1B H 0.593791 0.447754 0.864299 0.063 Uiso 1 1 calc R U . . .
H1C H 0.727855 0.514629 0.962610 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6521(4) 0.61311(16) 0.6812(3) 0.0295(6) Uani 1 1 d . . . . .
C3 C 0.3751(4) 0.54174(16) 0.6495(4) 0.0327(6) Uani 1 1 d . . . . .
H3 H 0.287085 0.501610 0.661464 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3332(4) 0.60477(16) 0.5490(3) 0.0314(6) Uani 1 1 d . . . . .
H4 H 0.210111 0.616439 0.477983 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5254(4) 0.72251(17) 0.4785(4) 0.0372(7) Uani 1 1 d . . . . .
H5A H 0.551858 0.710198 0.367242 0.045 Uiso 1 1 calc R U . . .
H5B H 0.639184 0.751784 0.541564 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3402(5) 0.77241(17) 0.4558(4) 0.0431(8) Uani 1 1 d . . . . .
H6A H 0.229500 0.745444 0.385101 0.065 Uiso 1 1 calc R U . . .
H6B H 0.362889 0.820909 0.402648 0.065 Uiso 1 1 calc R U . . .
H6C H 0.309862 0.782764 0.565290 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8630(4) 0.63910(19) 0.7380(4) 0.0431(8) Uani 1 1 d . . . . .
H8A H 0.909898 0.626401 0.856406 0.065 Uiso 1 1 calc R U . . .
H8B H 0.870649 0.694627 0.722832 0.065 Uiso 1 1 calc R U . . .
H8C H 0.945129 0.613136 0.671553 0.065 Uiso 1 1 calc R U . . .
Br1 Br 0.87082(4) 0.62967(2) 0.22649(4) 0.03606(11) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0272(12) 0.0313(12) 0.0285(12) -0.0063(10) 0.0016(10) 0.0038(10)
N2 0.0222(11) 0.0338(12) 0.0262(11) -0.0026(9) 0.0016(9) -0.0015(9)
C1 0.0439(18) 0.0416(17) 0.0361(17) -0.0009(14) -0.0015(14) 0.0124(14)
C2 0.0234(14) 0.0396(16) 0.0248(13) -0.0074(12) 0.0037(11) 0.0011(12)
C3 0.0272(15) 0.0326(15) 0.0367(15) -0.0085(13) 0.0033(12) -0.0048(12)
C4 0.0237(14) 0.0358(15) 0.0322(15) -0.0053(12) 0.0003(12) 0.0004(12)
C5 0.0351(16) 0.0425(17) 0.0338(16) 0.0022(13) 0.0067(13) -0.0061(14)
C6 0.0446(18) 0.0388(17) 0.0446(18) 0.0067(14) 0.0067(15) 0.0034(14)
C8 0.0229(14) 0.059(2) 0.0447(17) -0.0018(15) 0.0009(13) -0.0017(14)
Br1 0.02933(16) 0.03488(17) 0.03939(17) -0.00345(13) -0.00292(11) 0.00159(13)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.466(3) . ?
N1 C2 1.336(3) . ?
N1 C3 1.383(3) . ?
N2 C2 1.341(3) . ?
N2 C4 1.379(3) . ?
N2 C5 1.472(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C8 1.481(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.340(4) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.503(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 126.0(2) . . ?
C2 N1 C3 109.2(2) . . ?
C3 N1 C1 124.7(2) . . ?
C2 N2 C4 108.8(2) . . ?
C2 N2 C5 126.0(2) . . ?
C4 N2 C5 125.1(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 N2 107.5(2) . . ?
N1 C2 C8 125.4(3) . . ?
N2 C2 C8 127.1(3) . . ?
N1 C3 H3 126.6 . . ?
C4 C3 N1 106.8(2) . . ?
C4 C3 H3 126.6 . . ?
N2 C4 H4 126.2 . . ?
C3 C4 N2 107.7(2) . . ?
C3 C4 H4 126.2 . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
N2 C5 C6 112.3(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 N2 -0.1(3) . . . . ?
C1 N1 C2 N2 179.8(2) . . . . ?
C1 N1 C2 C8 0.3(4) . . . . ?
C1 N1 C3 C4 -179.4(2) . . . . ?
C2 N1 C3 C4 -0.5(3) . . . . ?
C2 N2 C4 C3 0.6(3) . . . . ?
C2 N2 C5 C6 -144.3(3) . . . . ?
C3 N1 C2 N2 0.9(3) . . . . ?
C3 N1 C2 C8 -178.5(3) . . . . ?
C4 N2 C2 N1 -0.9(3) . . . . ?
C4 N2 C2 C8 178.5(3) . . . . ?
C4 N2 C5 C6 38.6(4) . . . . ?
C5 N2 C2 N1 -178.4(2) . . . . ?
C5 N2 C2 C8 1.0(4) . . . . ?
C5 N2 C4 C3 178.2(2) . . . . ?

_shelx_res_file                  
;
TITL
    tw2114.res
    created by SHELXL-2018/3 at 16:14:34 on 02-Sep-2021
CELL 0.71073 6.818238 17.099397 8.01805 90 102.2975 90
ZERR 4 0.000242 0.000568 0.000284 0 0.0034 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N
UNIT 28 52 4 8

L.S. 4
PLAN  4
CONF
fmap 2
MORE -1
ACTA
BOND $H
OMIT 0 2 0
REM <olex2.extras>
REM <HklSrc "%.\\TW2114.hkl">
REM </olex2.extras>

WGHT    0.022700    0.645600
FVAR       8.22828
N1    4    0.574473    0.547808    0.732074    11.00000    0.02717    0.03134 =
         0.02852   -0.00626    0.00158    0.00382
N2    4    0.505439    0.649256    0.569874    11.00000    0.02222    0.03382 =
         0.02617   -0.00264    0.00157   -0.00149
C1    1    0.682167    0.490263    0.853370    11.00000    0.04390    0.04159 =
         0.03613   -0.00090   -0.00146    0.01242
AFIX 137
H1A   2    0.795380    0.470721    0.812631    11.00000   -1.50000
H1B   2    0.593791    0.447754    0.864299    11.00000   -1.50000
H1C   2    0.727855    0.514629    0.962610    11.00000   -1.50000
AFIX   0
C2    1    0.652145    0.613107    0.681188    11.00000    0.02344    0.03962 =
         0.02484   -0.00739    0.00367    0.00114
C3    1    0.375118    0.541742    0.649508    11.00000    0.02723    0.03264 =
         0.03669   -0.00853    0.00334   -0.00482
AFIX  43
H3    2    0.287085    0.501610    0.661464    11.00000   -1.20000
AFIX   0
C4    1    0.333198    0.604775    0.549019    11.00000    0.02370    0.03583 =
         0.03224   -0.00534    0.00027    0.00040
AFIX  43
H4    2    0.210111    0.616439    0.477983    11.00000   -1.20000
AFIX   0
C5    1    0.525422    0.722509    0.478486    11.00000    0.03515    0.04247 =
         0.03379    0.00222    0.00673   -0.00615
AFIX  23
H5A   2    0.551858    0.710198    0.367242    11.00000   -1.20000
H5B   2    0.639184    0.751784    0.541564    11.00000   -1.20000
AFIX   0
C6    1    0.340192    0.772413    0.455836    11.00000    0.04461    0.03885 =
         0.04460    0.00668    0.00669    0.00336
AFIX 137
H6A   2    0.229500    0.745444    0.385101    11.00000   -1.50000
H6B   2    0.362889    0.820909    0.402648    11.00000   -1.50000
H6C   2    0.309862    0.782764    0.565290    11.00000   -1.50000
AFIX   0
C8    1    0.862995    0.639104    0.737989    11.00000    0.02289    0.05885 =
         0.04466   -0.00178    0.00093   -0.00168
AFIX 137
H8A   2    0.909898    0.626401    0.856406    11.00000   -1.50000
H8B   2    0.870649    0.694627    0.722832    11.00000   -1.50000
H8C   2    0.945129    0.613136    0.671553    11.00000   -1.50000
AFIX   0

BR1   3    0.870817    0.629669    0.226489    11.00000    0.02933    0.03488 =
         0.03939   -0.00345   -0.00292    0.00159
HKLF 4




REM
REM wR2 = 0.0647, GooF = S = 1.016, Restrained GooF = 1.016 for all data
REM R1 = 0.0318 for 1570 Fo > 4sig(Fo) and 0.0528 for all 2055 data
REM 94 parameters refined using 0 restraints

END

WGHT      0.0227      0.6465

REM Highest difference peak  0.340,  deepest hole -0.291,  1-sigma level  0.073
Q1    1   0.7929  0.5693  0.2550  11.00000  0.05    0.34
Q2    1   0.9058  0.6671  0.6614  11.00000  0.05    0.33
Q3    1   0.8811  0.6475  0.3718  11.00000  0.05    0.32
Q4    1   0.2645  0.7890  0.3518  11.00000  0.05    0.30
;
_shelx_res_checksum              45583
_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.806
####################################################################### 
# 
# 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_[NC2C1im]Cl
_database_code_depnum_ccdc_archive 'CCDC 2120107'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H16 N6), Cl'
_chemical_formula_sum            'C6 H8 Cl N3'
_chemical_formula_weight         157.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 Cl N3'
_chemical_oxdiff_usercomment     SK56_EtOH
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'
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   14.9547(5)
_cell_length_b                   6.2734(2)
_cell_length_c                   7.8292(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     734.51(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      28.0540
_cell_measurement_theta_min      2.9350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9241
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.724
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  51.00   1.00    3.33    --  -13.18  77.00  60.00   88
  2  ω    -30.00  56.00   1.00    3.33    --  -13.18  37.00-120.00   86
  3  ω     13.00  82.00   1.00    3.33    --   14.27  57.00-150.00   69
  4  ω    -25.00  26.00   1.00    3.33    --  -13.18 -99.00   0.00   51
  5  ω     -2.00  67.00   1.00    3.33    --   14.27-123.00  15.00   69
  6  ω    -80.00   6.00   1.00    3.33    --  -13.18 -77.00 -60.00   86
  7  ω    -82.00   4.00   1.00    3.33    --  -13.18 -37.00  60.00   86
  8  ω    -67.00   3.00   1.00    3.33    --  -13.18 125.00 142.09   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0263948000
_diffrn_orient_matrix_UB_12      -0.0939026000
_diffrn_orient_matrix_UB_13      0.0000890000
_diffrn_orient_matrix_UB_21      0.0391871000
_diffrn_orient_matrix_UB_22      0.0625065000
_diffrn_orient_matrix_UB_23      0.0100748000
_diffrn_orient_matrix_UB_31      -0.0043972000
_diffrn_orient_matrix_UB_32      -0.0068795000
_diffrn_orient_matrix_UB_33      0.0900347000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                790
_reflns_number_total             926
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.082
_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     62
_refine_ls_number_reflns         926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.081
_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)+(0.0331P)²+0.2641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H6A(0.5) H6B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.14726(11) 0.750000 0.3475(2) 0.0178(3) Uani 1 2 d S T P . .
C1 C 0.04918(13) 0.750000 0.3553(3) 0.0261(5) Uani 1 2 d S T P . .
H1A H 0.026876 0.615527 0.315219 0.039 Uiso 0.5 1 calc R U P A -1
H1B H 0.026204 0.862505 0.284756 0.039 Uiso 0.5 1 calc R U P A -1
H1C H 0.030316 0.771969 0.471222 0.039 Uiso 0.5 1 calc R U P A -1
N2 N 0.28535(10) 0.750000 0.42569(18) 0.0162(3) Uani 1 2 d S T P . .
C2 C 0.20100(12) 0.750000 0.4825(2) 0.0164(4) Uani 1 2 d S T P . .
H2 H 0.183158 0.750000 0.596272 0.020 Uiso 1 2 calc R U P . .
N3 N 0.33526(12) 0.750000 0.8523(2) 0.0257(4) Uani 1 2 d S T P . .
C4 C 0.19818(13) 0.750000 0.2011(2) 0.0209(4) Uani 1 2 d S T P . .
H4 H 0.176955 0.750000 0.089452 0.025 Uiso 1 2 calc R U P . .
C5 C 0.28462(13) 0.750000 0.2500(2) 0.0196(4) Uani 1 2 d S T P . .
H5 H 0.334297 0.750000 0.178512 0.024 Uiso 1 2 calc R U P . .
C6 C 0.36835(12) 0.750000 0.5258(2) 0.0185(4) Uani 1 2 d S T P . .
H6A H 0.403355 0.624910 0.496970 0.022 Uiso 0.5 1 calc R U P . .
H6B H 0.403355 0.875090 0.496971 0.022 Uiso 0.5 1 calc R U P . .
C7 C 0.34966(13) 0.750000 0.7095(3) 0.0187(4) Uani 1 2 d S T P . .
Cl1 Cl 0.57081(3) 0.750000 0.66768(6) 0.02157(16) Uani 1 2 d S T 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
N1 0.0181(8) 0.0167(8) 0.0187(8) 0.000 -0.0031(6) 0.000
C1 0.0179(10) 0.0290(11) 0.0313(11) 0.000 -0.0061(8) 0.000
N2 0.0174(8) 0.0196(8) 0.0117(7) 0.000 -0.0017(6) 0.000
C2 0.0185(9) 0.0165(9) 0.0141(9) 0.000 0.0004(7) 0.000
N3 0.0329(10) 0.0264(9) 0.0178(9) 0.000 0.0004(7) 0.000
C4 0.0297(11) 0.0196(10) 0.0135(9) 0.000 -0.0034(8) 0.000
C5 0.0252(11) 0.0217(10) 0.0119(9) 0.000 0.0023(7) 0.000
C6 0.0161(9) 0.0241(10) 0.0151(9) 0.000 -0.0019(7) 0.000
C7 0.0177(10) 0.0172(9) 0.0213(10) 0.000 -0.0042(7) 0.000
Cl1 0.0180(3) 0.0296(3) 0.0170(3) 0.000 -0.00040(18) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.468(2) . ?
N1 C2 1.328(2) . ?
N1 C4 1.376(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.337(2) . ?
N2 C5 1.376(2) . ?
N2 C6 1.468(2) . ?
C2 H2 0.9300 . ?
N3 C7 1.138(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.465(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 124.83(16) . . ?
C2 N1 C4 109.15(16) . . ?
C4 N1 C1 126.02(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C5 108.96(16) . . ?
C2 N2 C6 128.31(15) . . ?
C5 N2 C6 122.73(15) . . ?
N1 C2 N2 107.83(16) . . ?
N1 C2 H2 126.1 . . ?
N2 C2 H2 126.1 . . ?
N1 C4 H4 126.4 . . ?
C5 C4 N1 107.12(16) . . ?
C5 C4 H4 126.4 . . ?
N2 C5 H5 126.5 . . ?
C4 C5 N2 106.94(17) . . ?
C4 C5 H5 126.5 . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 N2 111.28(15) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N3 C7 C6 179.9(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
N1 C4 C5 N2 0.000(0) . . . . ?
C1 N1 C2 N2 180.000(0) . . . . ?
C1 N1 C4 C5 180.000(0) . . . . ?
C2 N1 C4 C5 0.000(0) . . . . ?
C2 N2 C5 C4 0.000(0) . . . . ?
C2 N2 C6 C7 0.000(0) . . . . ?
C4 N1 C2 N2 0.000(0) . . . . ?
C5 N2 C2 N1 0.000(0) . . . . ?
C5 N2 C6 C7 180.000(0) . . . . ?
C6 N2 C2 N1 180.000(0) . . . . ?
C6 N2 C5 C4 180.000(0) . . . . ?

_shelx_res_file                  
;
TITL CF solution in Pnma
    tw2102.res
    created by SHELXL-2018/3 at 15:25:06 on 23-Jun-2021
CELL 0.71073 14.95469 6.2734 7.82916 90 90 90
ZERR 4 0.0005 0.00024 0.00025 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C H Cl N
UNIT 24 32 4 12

L.S. 10
PLAN  5
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2102.hkl">
REM </olex2.extras>

WGHT    0.033100    0.264100
FVAR       4.96629
N1    4    0.147259    0.750000    0.347455    10.50000    0.01807    0.01665 =
         0.01875    0.00000   -0.00311    0.00000
C1    1    0.049178    0.750000    0.355346    10.50000    0.01786    0.02902 =
         0.03129    0.00000   -0.00614    0.00000
PART -1
AFIX 137
H1A   2    0.026876    0.615527    0.315219    10.50000   -1.50000
H1B   2    0.026204    0.862505    0.284756    10.50000   -1.50000
H1C   2    0.030316    0.771969    0.471222    10.50000   -1.50000
AFIX   0
PART 0
N2    4    0.285349    0.750000    0.425691    10.50000    0.01736    0.01965 =
         0.01168    0.00000   -0.00169    0.00000
C2    1    0.200998    0.750000    0.482478    10.50000    0.01851    0.01648 =
         0.01410    0.00000    0.00036    0.00000
AFIX  43
H2    2    0.183158    0.750000    0.596272    10.50000   -1.20000
AFIX   0
N3    4    0.335262    0.750000    0.852270    10.50000    0.03286    0.02641 =
         0.01783    0.00000    0.00045    0.00000
C4    1    0.198177    0.750000    0.201107    10.50000    0.02969    0.01956 =
         0.01354    0.00000   -0.00340    0.00000
AFIX  43
H4    2    0.176955    0.750000    0.089452    10.50000   -1.20000
AFIX   0
C5    1    0.284621    0.750000    0.249973    10.50000    0.02517    0.02175 =
         0.01187    0.00000    0.00232    0.00000
AFIX  43
H5    2    0.334297    0.750000    0.178512    10.50000   -1.20000
AFIX   0
C6    1    0.368355    0.750000    0.525845    10.50000    0.01610    0.02414 =
         0.01515    0.00000   -0.00189    0.00000
AFIX  23
H6A   2    0.403355    0.624910    0.496970    10.50000   -1.20000
H6B   2    0.403355    0.875090    0.496971    10.50000   -1.20000
AFIX   0
C7    1    0.349660    0.750000    0.709531    10.50000    0.01765    0.01717 =
         0.02130    0.00000   -0.00419    0.00000

CL1   3    0.570815    0.750000    0.667678    10.50000    0.01804    0.02965 =
         0.01704    0.00000   -0.00040    0.00000
HKLF 4




REM  CF solution in Pnma
REM wR2 = 0.0741, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0310 for 790 Fo > 4sig(Fo) and 0.0386 for all 926 data
REM 62 parameters refined using 0 restraints

END

WGHT      0.0331      0.2641

REM Highest difference peak  0.191,  deepest hole -0.333,  1-sigma level  0.082
Q1    1   0.3547  1.0349  0.4160  11.00000  0.05    0.19
Q2    1   0.3978  0.9626  0.3490  11.00000  0.05    0.18
Q3    1   0.2859  0.7758  0.3388  11.00000  0.05    0.17
Q4    1   0.1360  0.9649  0.6628  11.00000  0.05    0.17
Q5    1   0.0105  1.0120  0.2177  11.00000  0.05    0.17
;
_shelx_res_checksum              66130
_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.960
