# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ms-a-d6py
_database_code_depnum_ccdc_archive 'CCDC 2219093'
loop_
_audit_author_name
_audit_author_address
'AMITA MAHAPATRA'
;National Institute of Science Education and Research
India
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C8 H17 N, H2 O'
_chemical_formula_sum            'C8 H19 Br N O'
_chemical_formula_weight         225.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H34 Br2 N4 O1 '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2705(3)
_cell_length_b                   8.3119(4)
_cell_length_c                   8.6304(4)
_cell_angle_alpha                81.434(4)
_cell_angle_beta                 78.227(4)
_cell_angle_gamma                66.545(4)
_cell_volume                     531.30(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12159
_cell_measurement_temperature    294.6(5)
_cell_measurement_theta_max      28.7450
_cell_measurement_theta_min      3.4780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19379
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         3.437
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  63.00   0.50    5.54    --   -0.01-144.00-162.00  100
  2  ω      3.00  52.00   0.50    5.54    --   -0.01-126.00   6.00   98
  3  ω     -3.00  66.00   0.50    5.54    --   -0.01  38.00-180.00  138
  4  ω    -68.00   9.00   0.50    5.54    --   -0.01 -14.00  26.90  154
  5  ω    -20.00  36.00   0.50    5.54    --   -0.01 -99.00 120.00  112
  6  ω    -64.00  23.00   0.50    5.54    --   -0.01 -77.00-120.00  174
  7  ω      0.00  49.00   0.50    5.54    --   -0.01-122.00 107.00   98
  8  ω     -6.00  69.00   0.50    5.54    --   -0.01  19.00-120.00  150
  9  ω    -69.00  15.00   0.50    5.54    --   -0.01  -9.00  60.26  168
 10  ω    -69.00  15.00   0.50    5.54    --   -0.01  -9.00 147.01  168
 11  ω    -68.00   9.00   0.50    5.54    --   -0.01 -13.00 -88.34  154
 12  ω    -68.00   9.00   0.50    5.54    --   -0.01 -13.00-150.60  154
 13  ω     -6.00  69.00   0.50    5.54    --   -0.01  19.00 -30.00  150
 14  ω    -69.00   6.00   0.50    5.54    --   -0.01 -19.00 120.00  150
 15  ω     -6.00  69.00   0.50    5.54    --   -0.01  19.00 120.00  150
 16  ω    -69.00  13.00   0.50    5.54    --   -0.01 -10.00 178.44  164
 17  ω    -23.00   2.00   0.50    5.54    --   -0.01  77.00 -90.00   50
 18  ω    -20.00  36.00   0.50    5.54    --   -0.01 -99.00   0.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358273000
_diffrn_orient_matrix_UB_12      0.0674267000
_diffrn_orient_matrix_UB_13      -0.0587102000
_diffrn_orient_matrix_UB_21      0.0484444000
_diffrn_orient_matrix_UB_22      -0.0589034000
_diffrn_orient_matrix_UB_23      -0.0600023000
_diffrn_orient_matrix_UB_31      -0.0730595000
_diffrn_orient_matrix_UB_32      -0.0262008000
_diffrn_orient_matrix_UB_33      0.0064171000
_diffrn_oxdiff_ac3_digest_frames 
;
01b20ea653cc2baa95b98b2259da183dd3000268fb8
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01064a51fd33fc58b8f373295bbf08fa8d3ee4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1959
_reflns_number_total             2191
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.06
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.060
_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)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C004(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F), C007(H00G,H00H), C008(H00I,
 H00J), C009(H00K,H00L), C00B(H00P,H00Q)
2.b Idealised Me refined as rotating group:
 C00A(H00M,H00N,H00O)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br01 Br 0.14391(3) 0.68257(3) 1.26400(3) 0.05077(14) Uani 1 1 d . . . . .
N002 N 0.2530(2) 0.7928(3) 0.7040(2) 0.0372(4) Uani 1 1 d . . . . .
O00 O 0.7619(3) 0.6850(4) 0.4960(5) 0.0935(10) Uani 1 1 d . . . . .
C004 C 0.2563(3) 0.8848(3) 0.8416(3) 0.0387(5) Uani 1 1 d . . . . .
H00A H 0.166978 1.003534 0.836817 0.046 Uiso 1 1 calc R . . . .
H00B H 0.221510 0.824313 0.939659 0.046 Uiso 1 1 calc R . . . .
C005 C 0.4158(3) 0.9874(4) 0.9941(3) 0.0471(6) Uani 1 1 d . . . . .
H00C H 0.318576 1.101539 0.991152 0.057 Uiso 1 1 calc R . . . .
H00D H 0.385649 0.919058 1.088485 0.057 Uiso 1 1 calc R . . . .
C006 C 0.0661(3) 0.7962(4) 0.7160(3) 0.0479(6) Uani 1 1 d . . . . .
H00E H -0.023015 0.909139 0.747246 0.057 Uiso 1 1 calc R . . . .
H00F H 0.047250 0.773908 0.615237 0.057 Uiso 1 1 calc R . . . .
C007 C 0.4325(4) 0.8953(4) 0.8485(3) 0.0507(6) Uani 1 1 d . . . . .
H00G H 0.467438 0.959809 0.753361 0.061 Uiso 1 1 calc R . . . .
H00H H 0.523920 0.777729 0.853635 0.061 Uiso 1 1 calc R . . . .
C008 C 0.0566(4) 0.6508(4) 0.8419(4) 0.0583(7) Uani 1 1 d . . . . .
H00I H -0.017125 0.594855 0.817480 0.070 Uiso 1 1 calc R . . . .
H00J H 0.007243 0.697087 0.945408 0.070 Uiso 1 1 calc R . . . .
C009 C 0.3616(4) 0.5984(3) 0.7166(4) 0.0520(6) Uani 1 1 d . . . . .
H00K H 0.474360 0.575003 0.750183 0.062 Uiso 1 1 calc R . . . .
H00L H 0.385511 0.549529 0.615244 0.062 Uiso 1 1 calc R . . . .
C00A C 0.3086(5) 0.8789(5) 0.5492(3) 0.0569(7) Uani 1 1 d . . . . .
H00M H 0.236139 1.002369 0.544785 0.085 Uiso 1 1 calc GR . . . .
H00N H 0.293737 0.826991 0.463634 0.085 Uiso 1 1 calc GR . . . .
H00O H 0.431728 0.862735 0.539834 0.085 Uiso 1 1 calc GR . . . .
C00B C 0.2492(5) 0.5205(4) 0.8390(4) 0.0643(8) Uani 1 1 d . . . . .
H00P H 0.284500 0.505073 0.942386 0.077 Uiso 1 1 calc R . . . .
H00Q H 0.262338 0.407023 0.809998 0.077 Uiso 1 1 calc R . . . .
H00R H 0.848(5) 0.681(5) 0.425(5) 0.077(12) Uiso 1 1 d . . . . .
H00S H 0.788(6) 0.591(7) 0.554(6) 0.098(15) Uiso 1 1 d . . . . .


_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
N002 C004 1.515(3) . ?
N002 C006 1.517(3) . ?
N002 C009 1.504(3) . ?
N002 C00A 1.495(3) . ?
O00 H00R 0.83(4) . ?
O00 H00S 0.84(6) . ?
C004 H00A 0.9700 . ?
C004 H00B 0.9700 . ?
C004 C007 1.507(3) . ?
C005 C005 1.514(5) 2_677 ?
C005 H00C 0.9700 . ?
C005 H00D 0.9700 . ?
C005 C007 1.522(3) . ?
C006 H00E 0.9700 . ?
C006 H00F 0.9700 . ?
C006 C008 1.515(4) . ?
C007 H00G 0.9700 . ?
C007 H00H 0.9700 . ?
C008 H00I 0.9700 . ?
C008 H00J 0.9700 . ?
C008 C00B 1.526(5) . ?
C009 H00K 0.9700 . ?
C009 H00L 0.9700 . ?
C009 C00B 1.508(4) . ?
C00A H00M 0.9600 . ?
C00A H00N 0.9600 . ?
C00A H00O 0.9600 . ?
C00B H00P 0.9700 . ?
C00B H00Q 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
C004 N002 C006 108.38(18) . . ?
C009 N002 C004 112.77(19) . . ?
C009 N002 C006 101.56(19) . . ?
C00A N002 C004 110.70(19) . . ?
C00A N002 C006 111.4(2) . . ?
C00A N002 C009 111.7(2) . . ?
H00R O00 H00S 110(4) . . ?
N002 C004 H00A 108.3 . . ?
N002 C004 H00B 108.3 . . ?
H00A C004 H00B 107.4 . . ?
C007 C004 N002 115.86(19) . . ?
C007 C004 H00A 108.3 . . ?
C007 C004 H00B 108.3 . . ?
C005 C005 H00C 108.9 2_677 . ?
C005 C005 H00D 108.9 2_677 . ?
C005 C005 C007 113.4(3) 2_677 . ?
H00C C005 H00D 107.7 . . ?
C007 C005 H00C 108.9 . . ?
C007 C005 H00D 108.9 . . ?
N002 C006 H00E 110.8 . . ?
N002 C006 H00F 110.8 . . ?
H00E C006 H00F 108.9 . . ?
C008 C006 N002 104.7(2) . . ?
C008 C006 H00E 110.8 . . ?
C008 C006 H00F 110.8 . . ?
C004 C007 C005 109.7(2) . . ?
C004 C007 H00G 109.7 . . ?
C004 C007 H00H 109.7 . . ?
C005 C007 H00G 109.7 . . ?
C005 C007 H00H 109.7 . . ?
H00G C007 H00H 108.2 . . ?
C006 C008 H00I 110.7 . . ?
C006 C008 H00J 110.7 . . ?
C006 C008 C00B 105.2(2) . . ?
H00I C008 H00J 108.8 . . ?
C00B C008 H00I 110.7 . . ?
C00B C008 H00J 110.7 . . ?
N002 C009 H00K 110.7 . . ?
N002 C009 H00L 110.7 . . ?
N002 C009 C00B 105.4(2) . . ?
H00K C009 H00L 108.8 . . ?
C00B C009 H00K 110.7 . . ?
C00B C009 H00L 110.7 . . ?
N002 C00A H00M 109.5 . . ?
N002 C00A H00N 109.5 . . ?
N002 C00A H00O 109.5 . . ?
H00M C00A H00N 109.5 . . ?
H00M C00A H00O 109.5 . . ?
H00N C00A H00O 109.5 . . ?
C008 C00B H00P 110.5 . . ?
C008 C00B H00Q 110.5 . . ?
C009 C00B C008 106.0(2) . . ?
C009 C00B H00P 110.5 . . ?
C009 C00B H00Q 110.5 . . ?
H00P C00B H00Q 108.7 . . ?


_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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.638
####################################################################### 
# 
# 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_ms_01072019
_database_code_depnum_ccdc_archive 'CCDC 2219101'
loop_
_audit_author_name
_audit_author_address
'AMITA MAHAPATRA'
;NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH
India
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C19 H29 N2'
_chemical_formula_sum            'C19 H29 Br2 N2'
_chemical_formula_weight         445.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H32 N32 O32 Br32 '
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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.6157(17)
_cell_length_b                   13.7323(16)
_cell_length_c                   10.4556(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2242.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9410
_cell_measurement_theta_min      3.5810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         3.550
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  45.00   0.50   35.00    --    5.13-115.00 -19.00   52
  2  ω     13.00  59.00   0.50   35.00    --    5.13  57.00 -60.00   92
  3  ω      3.00  64.00   0.50   35.00    --    5.13  38.00 -90.00  122
  4  ω     -4.00  39.00   0.50   35.00    --    5.13 -99.00-180.00   86
  5  ω    -10.00  16.00   0.50   35.00    --   -5.59 -99.00 -30.00   52
  6  ω    -13.00  30.00   0.50   35.00    --   -5.59 -99.00  90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405158000
_diffrn_orient_matrix_UB_12      -0.0162012000
_diffrn_orient_matrix_UB_13      0.0220738000
_diffrn_orient_matrix_UB_21      0.0191381000
_diffrn_orient_matrix_UB_22      0.0430310000
_diffrn_orient_matrix_UB_23      -0.0242939000
_diffrn_orient_matrix_UB_31      -0.0072335000
_diffrn_orient_matrix_UB_32      0.0236143000
_diffrn_orient_matrix_UB_33      0.0593710000
_diffrn_oxdiff_ac3_digest_frames 
;
01ab1de49cd8466e84613d6f904d3c4161000253487
;
_diffrn_oxdiff_ac3_digest_hkl    
;
017cd296d1079b12fe77ffdfa5899aa60a4a53
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1500
_reflns_number_total             2472
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         1.541
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.063
_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)+(0.1246P)²+4.0133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2168
_refine_ls_wR_factor_ref         0.2478
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C004(H00D,H00E), C005(H00F,H00G), C006(H00H,H00I)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00D(H00J), C5(H5), C3(H3)
3.c Idealised Me refined as rotating group:
 C003(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br01 Br 0.63467(5) 0.81710(6) 0.54739(7) 0.0797(4) Uani 1 1 d . U . . .
N002 N 0.8423(5) 0.6235(5) 0.4461(6) 0.0933(18) Uani 1 1 d . U . . .
C003 C 0.9110(4) 0.5661(5) 0.3801(8) 0.0819(18) Uani 1 1 d . U . . .
H00A H 0.901396 0.567309 0.289380 0.123 Uiso 1 1 calc GR . . . .
H00B H 0.909723 0.499954 0.409797 0.123 Uiso 1 1 calc GR . . . .
H00C H 0.965885 0.594201 0.398726 0.123 Uiso 1 1 calc GR . . . .
C004 C 0.8590(6) 0.7314(6) 0.4289(9) 0.096(2) Uani 1 1 d . U . . .
H00D H 0.898754 0.742346 0.359082 0.115 Uiso 1 1 calc R . . . .
H00E H 0.806065 0.765618 0.410350 0.115 Uiso 1 1 calc R . . . .
C005 C 0.8935(8) 0.6693(12) 0.6311(12) 0.174(6) Uani 1 1 d . U . . .
H00F H 0.948397 0.636234 0.627703 0.208 Uiso 1 1 calc R . . . .
H00G H 0.880183 0.684535 0.719426 0.208 Uiso 1 1 calc R . . . .
C006 C 0.8945(9) 0.7645(10) 0.5461(10) 0.132(4) Uani 1 1 d . U . . .
H00H H 0.859607 0.815464 0.583790 0.158 Uiso 1 1 calc R . . . .
H00I H 0.952313 0.788661 0.534231 0.158 Uiso 1 1 calc R . . . .
C007 C 0.7479(7) 0.6016(9) 0.3558(10) 0.125(3) Uani 1 1 d . U . . .
H007 H 0.724470 0.649279 0.303260 0.149 Uiso 1 1 calc R . . . .
C008 C 0.8255(10) 0.6090(11) 0.5729(10) 0.150(4) Uani 1 1 d . U . . .
H008 H 0.783106 0.571740 0.611694 0.180 Uiso 1 1 calc R . . . .
C009 C 0.5719(8) 0.5084(11) 0.2895(11) 0.173(6) Uani 1 1 d . U . . .
H009 H 0.556535 0.571618 0.311835 0.208 Uiso 1 1 calc R . . . .
C00D C 0.7159(11) 0.5234(13) 0.3655(15) 0.190(7) Uani 1 1 d . U . . .
H00J H 0.743045 0.475321 0.413277 0.228 Uiso 1 1 calc R . . . .
C5 C 0.500000 0.4681(17) 0.250000 0.283(18) Uani 1 2 d S TU P . .
H5 H 0.500001 0.400339 0.249998 0.340 Uiso 1 2 calc RS T P . .
C3 C 0.6433(8) 0.5044(14) 0.310(2) 0.273(14) Uani 1 1 d . U . . .
H3 H 0.660627 0.459774 0.248108 0.327 Uiso 1 1 calc R . . . .


_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
N002 C003 1.500(10) . ?
N002 C004 1.515(12) . ?
N002 C007 1.776(13) . ?
N002 C008 1.366(11) . ?
C003 H00A 0.9600 . ?
C003 H00B 0.9600 . ?
C003 H00C 0.9600 . ?
C004 H00D 0.9700 . ?
C004 H00E 0.9700 . ?
C004 C006 1.419(13) . ?
C005 H00F 0.9700 . ?
C005 H00G 0.9700 . ?
C005 C006 1.582(16) . ?
C005 C008 1.478(17) . ?
C006 H00H 0.9700 . ?
C006 H00I 0.9700 . ?
C007 H007 0.9300 . ?
C007 C00D 1.189(17) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C009 C5 1.318(15) . ?
C009 C3 1.136(15) . ?
C00D H00J 0.9300 . ?
C00D C3 1.302(18) . ?
C5 C009 1.318(15) 3_655 ?
C5 H5 0.9300 . ?
C3 H3 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
C003 N002 C004 109.7(6) . . ?
C003 N002 C007 105.1(6) . . ?
C004 N002 C007 104.2(7) . . ?
C008 N002 C003 120.5(9) . . ?
C008 N002 C004 106.9(8) . . ?
C008 N002 C007 109.4(9) . . ?
N002 C003 H00A 109.5 . . ?
N002 C003 H00B 109.5 . . ?
N002 C003 H00C 109.5 . . ?
H00A C003 H00B 109.5 . . ?
H00A C003 H00C 109.5 . . ?
H00B C003 H00C 109.5 . . ?
N002 C004 H00D 110.5 . . ?
N002 C004 H00E 110.5 . . ?
H00D C004 H00E 108.7 . . ?
C006 C004 N002 106.1(8) . . ?
C006 C004 H00D 110.5 . . ?
C006 C004 H00E 110.5 . . ?
H00F C005 H00G 109.0 . . ?
C006 C005 H00F 111.0 . . ?
C006 C005 H00G 111.0 . . ?
C008 C005 H00F 111.0 . . ?
C008 C005 H00G 111.0 . . ?
C008 C005 C006 103.8(8) . . ?
C004 C006 C005 102.5(9) . . ?
C004 C006 H00H 111.3 . . ?
C004 C006 H00I 111.3 . . ?
C005 C006 H00H 111.3 . . ?
C005 C006 H00I 111.3 . . ?
H00H C006 H00I 109.2 . . ?
N002 C007 H007 121.4 . . ?
C00D C007 N002 117.2(11) . . ?
C00D C007 H007 121.4 . . ?
N002 C008 C005 100.4(10) . . ?
N002 C008 H008 129.8 . . ?
C005 C008 H008 129.8 . . ?
C5 C009 H009 104.6 . . ?
C3 C009 H009 104.6 . . ?
C3 C009 C5 151(2) . . ?
C007 C00D H00J 119.7 . . ?
C007 C00D C3 120.6(18) . . ?
C3 C00D H00J 119.7 . . ?
C009 C5 C009 130(2) 3_655 . ?
C009 C5 H5 114.9 . . ?
C009 C5 H5 114.9 3_655 . ?
C009 C3 C00D 158(3) . . ?
C009 C3 H3 100.9 . . ?
C00D C3 H3 100.9 . . ?


_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 1.757
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_ms_29072019
_database_code_depnum_ccdc_archive 'CCDC 2219098'
loop_
_audit_author_name
_audit_author_address
'AMITA MAHAPATRA'
;NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH
India
;
_audit_update_record             
;
2022-11-11 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C9 H19 N, H2 O'
_chemical_formula_sum            'C9 H21 Br N O'
_chemical_formula_weight         239.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H34 Br2 N4 O2 '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7747(6)
_cell_length_b                   8.8458(6)
_cell_length_c                   8.9862(5)
_cell_angle_alpha                94.525(5)
_cell_angle_beta                 105.831(5)
_cell_angle_gamma                117.457(7)
_cell_volume                     578.09(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2670
_cell_measurement_theta_min      3.8170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22871
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.723
_diffrn_reflns_theta_min         3.420
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  53.00   0.50    7.50    --    3.67-122.00 -58.00  106
  2  ω     16.00  72.00   0.50    7.50    --    3.67-151.00 139.00  112
  3  ω     16.00  64.00   0.50    7.50    --   -3.98-151.00 139.00   96
  4  ω    -20.00  40.00   0.50    7.50    --    3.67 -99.00-180.00  120
  5  ω    -59.00  15.00   0.50    7.50    --    3.67 -57.00  30.00  148
  6  ω    -19.00  68.00   0.50    7.50    --    3.67  77.00-180.00  174
  7  ω    -66.00   9.00   0.50    7.50    --    3.67 -19.00  60.00  150
  8  ω    -66.00   9.00   0.50    7.50    --    3.67 -19.00 150.00  150
  9  ω      0.00  70.00   0.50    7.50    --    3.67  38.00 120.00  140
 10  ω    -57.00 -26.00   0.50    7.50    --   -3.98 128.00 171.81   62
 11  ω    -10.00  66.00   0.50    7.50    --   -3.98  19.00   0.00  152
 12  ω    -56.00 -24.00   0.50    7.50    --   -3.98 126.00  74.31   64
 13  ω    -68.00  19.00   0.50    7.50    --   -3.98 -77.00   0.00  174
 14  ω    -56.00 -24.00   0.50    7.50    --   -3.98 126.00 -11.41   64
 15  ω    -55.00 -23.00   0.50    7.50    --   -3.98 125.00 135.60   64
 16  ω    -67.00   8.00   0.50    7.50    --   -3.98 -57.00-120.00  150
 17  ω    -59.00 -27.00   0.50    7.50    --   -3.98 131.00-158.65   64
 18  ω    -62.00 -31.00   0.50    7.50    --   -3.98 137.00-109.45   62
 19  ω    -59.00 -27.00   0.50    7.50    --   -3.98 131.00 -47.23   64
 20  ω     -2.00  52.00   0.50    7.50    --    3.67-120.00  14.51  108
 21  ω    -20.00  40.00   0.50    7.50    --    3.67 -99.00-150.00  120
 22  ω     -2.00  52.00   0.50    7.50    --    3.67-120.00-172.17  108
 23  ω    -71.00 -36.00   0.50    7.50    --   -3.98 150.00-148.35   70
 24  ω    -70.00  -1.00   0.50    7.50    --   -3.98 -38.00  90.00  138
 25  ω    -20.00  32.00   0.50    7.50    --   -3.98 -99.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0117967000
_diffrn_orient_matrix_UB_12      0.0017723000
_diffrn_orient_matrix_UB_13      0.0815319000
_diffrn_orient_matrix_UB_21      -0.0951406000
_diffrn_orient_matrix_UB_22      -0.0597830000
_diffrn_orient_matrix_UB_23      -0.0212124000
_diffrn_orient_matrix_UB_31      0.0161965000
_diffrn_orient_matrix_UB_32      -0.0713187000
_diffrn_orient_matrix_UB_33      -0.0066343000
_diffrn_oxdiff_ac3_digest_frames 
;
01a353dd1e6b445ba9390ae3b322e76ea7000264de2
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01e48a57c1f8a251daf7ae1b4e62572dafc34b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1736
_reflns_number_total             2438
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.029
_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)+(0.0930P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1491
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C004(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F), C007(H00G,H00H), C009(H00L,
 H00M), C00A(H00N,H00O), C00B(H00P,H00Q), C00C(H00R,H00S)
2.b Idealised Me refined as rotating group:
 C008(H00I,H00J,H00K)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br01 Br 0.68229(5) 0.83841(5) 0.26108(5) 0.0735(2) Uani 1 1 d . . . . .
N002 N 0.5018(4) 0.2315(4) 0.3247(4) 0.0537(7) Uani 1 1 d . . . . .
O003 O 0.9610(7) 0.7565(6) 0.5341(7) 0.1209(16) Uani 1 1 d . . . . .
C004 C 0.4114(6) 0.3390(5) 0.3020(6) 0.0653(10) Uani 1 1 d . . . . .
H00A H 0.392484 0.370206 0.398688 0.078 Uiso 1 1 calc R . . . .
H00B H 0.485641 0.445850 0.273917 0.078 Uiso 1 1 calc R . . . .
C005 C 0.7408(6) 0.3897(5) 0.2029(6) 0.0679(10) Uani 1 1 d . . . . .
H00C H 0.837686 0.430347 0.305578 0.081 Uiso 1 1 calc R . . . .
H00D H 0.706898 0.478981 0.188708 0.081 Uiso 1 1 calc R . . . .
C006 C 0.5793(5) 0.2223(5) 0.1970(5) 0.0591(9) Uani 1 1 d . . . . .
H00E H 0.614283 0.133215 0.204846 0.071 Uiso 1 1 calc R . . . .
H00F H 0.483693 0.185074 0.094086 0.071 Uiso 1 1 calc R . . . .
C007 C 0.3430(7) 0.0548(5) 0.3047(7) 0.0765(13) Uani 1 1 d . . . . .
H00G H 0.369055 -0.036607 0.276248 0.092 Uiso 1 1 calc R . . . .
H00H H 0.316693 0.045026 0.402692 0.092 Uiso 1 1 calc R . . . .
C008 C 0.6452(7) 0.2962(7) 0.4853(6) 0.0774(12) Uani 1 1 d . . . . .
H00I H 0.737007 0.415460 0.497906 0.116 Uiso 1 1 calc GR . . . .
H00J H 0.700788 0.224353 0.496414 0.116 Uiso 1 1 calc GR . . . .
H00K H 0.590519 0.290769 0.565262 0.116 Uiso 1 1 calc GR . . . .
C009 C 0.8067(6) 0.3581(6) 0.0725(6) 0.0711(11) Uani 1 1 d . . . . .
H00L H 0.834394 0.264647 0.085633 0.085 Uiso 1 1 calc R . . . .
H00M H 0.708625 0.318627 -0.029215 0.085 Uiso 1 1 calc R . . . .
C00A C 0.9710(6) 0.5146(6) 0.0689(6) 0.0742(11) Uani 1 1 d . . . . .
H00N H 1.071637 0.549219 0.167641 0.089 Uiso 1 1 calc R . . . .
H00O H 0.946230 0.610469 0.062997 0.089 Uiso 1 1 calc R . . . .
C00B C 0.2338(7) 0.2273(7) 0.1709(8) 0.0856(14) Uani 1 1 d . . . . .
H00P H 0.244653 0.249878 0.069339 0.103 Uiso 1 1 calc R . . . .
H00Q H 0.140356 0.249372 0.187312 0.103 Uiso 1 1 calc R . . . .
C00C C 0.1858(7) 0.0389(6) 0.1752(8) 0.0891(16) Uani 1 1 d . . . . .
H00R H 0.073400 -0.022296 0.197713 0.107 Uiso 1 1 calc R . . . .
H00S H 0.170608 -0.024488 0.074176 0.107 Uiso 1 1 calc R . . . .
H00T H 1.017(5) 0.788(5) 0.464(4) 0.028(8) Uiso 1 1 d . . . . .
H00U H 1.058(9) 0.865(9) 0.553(9) 0.12(2) Uiso 1 1 d . . . . .


_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
N002 C004 1.488(5) . ?
N002 C006 1.499(5) . ?
N002 C007 1.492(5) . ?
N002 C008 1.486(6) . ?
O003 H00T 0.89(3) . ?
O003 H00U 0.90(7) . ?
C004 H00A 0.9700 . ?
C004 H00B 0.9700 . ?
C004 C00B 1.479(7) . ?
C005 H00C 0.9700 . ?
C005 H00D 0.9700 . ?
C005 C006 1.488(6) . ?
C005 C009 1.501(6) . ?
C006 H00E 0.9700 . ?
C006 H00F 0.9700 . ?
C007 H00G 0.9700 . ?
C007 H00H 0.9700 . ?
C007 C00C 1.482(8) . ?
C008 H00I 0.9600 . ?
C008 H00J 0.9600 . ?
C008 H00K 0.9600 . ?
C009 H00L 0.9700 . ?
C009 H00M 0.9700 . ?
C009 C00A 1.479(6) . ?
C00A C00A 1.507(9) 2_765 ?
C00A H00N 0.9700 . ?
C00A H00O 0.9700 . ?
C00B H00P 0.9700 . ?
C00B H00Q 0.9700 . ?
C00B C00C 1.526(7) . ?
C00C H00R 0.9700 . ?
C00C H00S 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
C004 N002 C006 112.0(3) . . ?
C004 N002 C007 101.3(3) . . ?
C007 N002 C006 108.8(3) . . ?
C008 N002 C004 111.4(3) . . ?
C008 N002 C006 110.8(3) . . ?
C008 N002 C007 112.2(4) . . ?
H00T O003 H00U 58(4) . . ?
N002 C004 H00A 110.6 . . ?
N002 C004 H00B 110.6 . . ?
H00A C004 H00B 108.8 . . ?
C00B C004 N002 105.5(3) . . ?
C00B C004 H00A 110.6 . . ?
C00B C004 H00B 110.6 . . ?
H00C C005 H00D 108.3 . . ?
C006 C005 H00C 110.0 . . ?
C006 C005 H00D 110.0 . . ?
C006 C005 C009 108.6(3) . . ?
C009 C005 H00C 110.0 . . ?
C009 C005 H00D 110.0 . . ?
N002 C006 H00E 108.5 . . ?
N002 C006 H00F 108.5 . . ?
C005 C006 N002 114.9(3) . . ?
C005 C006 H00E 108.5 . . ?
C005 C006 H00F 108.5 . . ?
H00E C006 H00F 107.5 . . ?
N002 C007 H00G 110.5 . . ?
N002 C007 H00H 110.5 . . ?
H00G C007 H00H 108.7 . . ?
C00C C007 N002 106.0(4) . . ?
C00C C007 H00G 110.5 . . ?
C00C C007 H00H 110.5 . . ?
N002 C008 H00I 109.5 . . ?
N002 C008 H00J 109.5 . . ?
N002 C008 H00K 109.5 . . ?
H00I C008 H00J 109.5 . . ?
H00I C008 H00K 109.5 . . ?
H00J C008 H00K 109.5 . . ?
C005 C009 H00L 108.8 . . ?
C005 C009 H00M 108.8 . . ?
H00L C009 H00M 107.7 . . ?
C00A C009 C005 113.8(4) . . ?
C00A C009 H00L 108.8 . . ?
C00A C009 H00M 108.8 . . ?
C009 C00A C00A 113.5(5) . 2_765 ?
C009 C00A H00N 108.9 . . ?
C009 C00A H00O 108.9 . . ?
C00A C00A H00N 108.9 2_765 . ?
C00A C00A H00O 108.9 2_765 . ?
H00N C00A H00O 107.7 . . ?
C004 C00B H00P 110.7 . . ?
C004 C00B H00Q 110.7 . . ?
C004 C00B C00C 105.4(4) . . ?
H00P C00B H00Q 108.8 . . ?
C00C C00B H00P 110.7 . . ?
C00C C00B H00Q 110.7 . . ?
C007 C00C C00B 105.1(4) . . ?
C007 C00C H00R 110.7 . . ?
C007 C00C H00S 110.7 . . ?
C00B C00C H00R 110.7 . . ?
C00B C00C H00S 110.7 . . ?
H00R C00C H00S 108.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.096
_oxdiff_exptl_absorpt_empirical_full_min 0.470
