# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_19ML004
_database_code_depnum_ccdc_archive 'CCDC 2171667'
loop_
_audit_author_name
_audit_author_address
'Michal Andrzejewski'
;University of Bern
Switzerland
;
_audit_update_record             
;
2022-05-09 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
4,5-dibromo-1-methyl-2-(prop-2-yn-1-yl)-1,2-dihydropyridazine-3,6-dione
_chemical_formula_moiety         'C8 H6 Br2 N2 O2'
_chemical_formula_sum            'C8 H6 Br2 N2 O2'
_chemical_formula_weight         321.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         B8H6Br2N2O2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.57760(10)
_cell_length_b                   14.7143(2)
_cell_length_c                   17.7153(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1975.24(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7690
_cell_measurement_theta_min      2.2970
_shelx_estimated_absorpt_T_max   0.579
_shelx_estimated_absorpt_T_min   0.291
_exptl_absorpt_coefficient_mu    8.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.144
_diffrn_reflns_theta_min         2.299
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00 104.00   1.00   20.50    --   27.84  57.00-120.00  114
  2  ω    -20.00  83.00   1.00   20.50    --   27.84 -99.00-180.00  103
  3  ω    -28.00 109.00   1.00   20.50    --   27.84  38.00   0.00  137
  4  ω    -10.00  41.00   1.00   20.50    --   27.84  57.00 120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413370000
_diffrn_orient_matrix_UB_12      -0.0046871000
_diffrn_orient_matrix_UB_13      0.0357121000
_diffrn_orient_matrix_UB_21      0.0839860000
_diffrn_orient_matrix_UB_22      0.0028752000
_diffrn_orient_matrix_UB_23      -0.0175267000
_diffrn_orient_matrix_UB_31      -0.0009889000
_diffrn_orient_matrix_UB_32      0.0478857000
_diffrn_orient_matrix_UB_33      0.0045386000
_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                1949
_reflns_number_total             2255
_reflns_odcompleteness_completeness 99.91
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0207
_refine_ls_restrained_S_all      1.067
_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)+(0.0209P)²+0.8120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.61138(3) 0.49982(2) 0.31210(2) 0.02250(7) Uani 1 1 d . . . . .
Br2 Br 0.53000(3) 0.63537(2) 0.16148(2) 0.02367(7) Uani 1 1 d . . . . .
O1 O 0.5892(2) 0.61608(10) 0.45315(9) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.3512(2) 0.80554(10) 0.21716(9) 0.0276(4) Uani 1 1 d . . . . .
N3 N 0.4497(2) 0.73958(11) 0.40563(10) 0.0193(4) Uani 1 1 d . . . . .
N4 N 0.3910(2) 0.79090(12) 0.34328(11) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.5355(3) 0.61984(14) 0.32096(13) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.4949(3) 0.67265(14) 0.26160(12) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.5275(3) 0.65625(14) 0.39860(13) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.4102(3) 0.76211(14) 0.27061(13) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.5918(3) 0.85895(15) 0.48002(13) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.4585(3) 0.78627(15) 0.47895(13) 0.0216(5) Uani 1 1 d . . . . .
H8A H 0.4862 0.7423 0.5180 0.026 Uiso 1 1 calc R . . . .
H8B H 0.3438 0.8121 0.4904 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2720(3) 0.86747(14) 0.35965(14) 0.0278(5) Uani 1 1 d . . . . .
H7A H 0.2275 0.8919 0.3132 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.3357 0.9138 0.3864 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.1753 0.8466 0.3901 0.033 Uiso 1 1 calc GR . . . .
C10 C 0.6929(3) 0.91980(17) 0.48051(14) 0.0299(6) Uani 1 1 d . . . . .
H10 H 0.771(4) 0.9638(18) 0.4761(16) 0.040(8) 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
Br1 C1 1.864(2) . ?
Br2 C6 1.875(2) . ?
O1 C2 1.225(3) . ?
O2 C5 1.227(3) . ?
N3 N4 1.410(2) . ?
N3 C2 1.366(3) . ?
N3 C8 1.471(3) . ?
N4 C5 1.363(3) . ?
N4 C7 1.472(3) . ?
C1 C6 1.343(3) . ?
C1 C2 1.477(3) . ?
C6 C5 1.473(3) . ?
C9 C8 1.471(3) . ?
C9 C10 1.179(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10 0.88(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
N4 N3 C8 117.12(16) . . ?
C2 N3 N4 123.05(18) . . ?
C2 N3 C8 118.70(18) . . ?
N3 N4 C7 116.67(18) . . ?
C5 N4 N3 122.67(17) . . ?
C5 N4 C7 119.30(19) . . ?
C6 C1 Br1 123.56(17) . . ?
C6 C1 C2 120.64(19) . . ?
C2 C1 Br1 115.77(15) . . ?
C1 C6 Br2 122.60(16) . . ?
C1 C6 C5 122.1(2) . . ?
C5 C6 Br2 115.19(16) . . ?
O1 C2 N3 121.7(2) . . ?
O1 C2 C1 122.92(19) . . ?
N3 C2 C1 115.35(19) . . ?
O2 C5 N4 121.9(2) . . ?
O2 C5 C6 122.7(2) . . ?
N4 C5 C6 115.25(19) . . ?
C10 C9 C8 177.2(3) . . ?
N3 C8 C9 112.45(18) . . ?
N3 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10 174.2(19) . . ?

_olex2_date_sample_data_collection 2019-09-30
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.818
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/ hexane'
####################################################################### 
# 
# 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_19ml002
_database_code_depnum_ccdc_archive 'CCDC 2171686'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;University of Bern
Switzerland
;
_audit_update_record             
;
2022-05-09 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            Si-Xanthone
_chemical_name_systematic        
3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one
_chemical_formula_moiety         'C19 H24 N2 O Si'
_chemical_formula_sum            'C19 H24 N2 O Si'
_chemical_formula_weight         324.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   9.71112(9)
_cell_length_b                   15.04527(14)
_cell_length_c                   11.81596(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.7446(9)
_cell_angle_gamma                90
_cell_volume                     1726.24(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9699
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7550
_cell_measurement_theta_min      2.1760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1247
0 -1 0 0.1247
0 -3 -17 0.0679
0 1 5 0.1006
-1 0 -1 0.1473
1 0 1 0.1473
0 0 1 0.0942
-2 -1 5 0.1338

_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.168
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18724
_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         28.117
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_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     35.00 122.00   1.00    7.00    --   27.42 178.00 -60.00   87
  2  ω    -10.00 103.00   1.00    7.00    --   27.42  57.00 150.00  113
  3  ω    -57.00 114.00   1.00    7.00    --   27.42  19.00   0.00  171
  4  ω     35.00 122.00   1.00    7.00    --   27.42 178.00  30.00   87
  5  ω    -20.00  32.00   1.00    7.00    --  -23.50 -99.00   0.00   52
  6  ω    -10.00  94.00   1.00    7.00    --   27.42  57.00  60.00  104
  7  ω    -49.00  65.00   1.00    7.00    --   27.42 -57.00   0.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0128452000
_diffrn_orient_matrix_UB_12      0.0237162000
_diffrn_orient_matrix_UB_13      -0.0509394000
_diffrn_orient_matrix_UB_21      0.0043245000
_diffrn_orient_matrix_UB_22      0.0407058000
_diffrn_orient_matrix_UB_23      0.0300861000
_diffrn_orient_matrix_UB_31      0.0717920000
_diffrn_orient_matrix_UB_32      0.0017900000
_diffrn_orient_matrix_UB_33      -0.0101316000
_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                3413
_reflns_number_total             3938
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.043
_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)+(0.0526P)²+0.8213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
Si1 Si 0.39170(4) 0.59606(2) 0.23011(3) 0.02106(12) Uani 1 1 d . . . . .
O1 O 0.38255(12) 0.88722(7) 0.30305(11) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.89586(13) 0.67923(9) 0.11578(12) 0.0307(3) Uani 1 1 d . . . . .
N2 N -0.08772(13) 0.61431(9) 0.43022(12) 0.0316(3) Uani 1 1 d . . . . .
C1 C 0.53748(14) 0.67600(9) 0.22080(11) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.66251(14) 0.64800(10) 0.17721(12) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.672320 0.588689 0.156672 0.028 Uiso 1 1 calc R . . . .
C3AA C 0.25514(14) 0.65855(9) 0.30561(11) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.77521(14) 0.70610(10) 0.16289(12) 0.0243(3) Uani 1 1 d . . . . .
C4 C 0.75748(16) 0.79441(10) 0.20014(14) 0.0298(3) Uani 1 1 d . . . . .
H4 H 0.830364 0.834271 0.195364 0.036 Uiso 1 1 calc R . . . .
C5 C 0.63426(16) 0.82239(10) 0.24333(13) 0.0288(3) Uani 1 1 d . . . . .
H5 H 0.625932 0.881122 0.266816 0.035 Uiso 1 1 calc R . . . .
C6 C 0.52058(14) 0.76567(9) 0.25330(11) 0.0226(3) Uani 1 1 d . . . . .
C7 C 0.39029(15) 0.80535(9) 0.29472(12) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.26991(14) 0.75042(9) 0.32738(11) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.16215(15) 0.79343(10) 0.38312(13) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.169881 0.853928 0.398054 0.032 Uiso 1 1 calc R . . . .
C10 C 0.04561(15) 0.74946(10) 0.41646(12) 0.0282(3) Uani 1 1 d . . . . .
H10 H -0.022888 0.780550 0.453933 0.034 Uiso 1 1 calc R . . . .
C11 C 0.02803(15) 0.65801(10) 0.39485(12) 0.0248(3) Uani 1 1 d . . . . .
C12 C 0.13602(14) 0.61446(10) 0.33814(12) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.127199 0.554212 0.321988 0.029 Uiso 1 1 calc R . . . .
C13 C 0.92093(16) 0.58840(11) 0.08189(14) 0.0318(3) Uani 1 1 d . . . . .
H13A H 0.883722 0.548691 0.137257 0.048 Uiso 1 1 calc GR . . . .
H13B H 1.018285 0.578672 0.076115 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.877427 0.577512 0.009797 0.048 Uiso 1 1 calc GR . . . .
C14 C 1.00192(16) 0.74377(12) 0.08918(15) 0.0351(4) Uani 1 1 d . . . . .
H14A H 0.961725 0.792115 0.047271 0.053 Uiso 1 1 calc GR . . . .
H14B H 1.071640 0.715857 0.044589 0.053 Uiso 1 1 calc GR . . . .
H14C H 1.042477 0.765983 0.158095 0.053 Uiso 1 1 calc GR . . . .
C15 C -0.19941(16) 0.66342(12) 0.48192(14) 0.0354(4) Uani 1 1 d . . . . .
H15A H -0.164847 0.695134 0.546815 0.053 Uiso 1 1 calc GR . . . .
H15B H -0.269837 0.622728 0.504971 0.053 Uiso 1 1 calc GR . . . .
H15C H -0.237301 0.704829 0.428123 0.053 Uiso 1 1 calc GR . . . .
C16 C -0.12055(16) 0.52481(11) 0.39346(14) 0.0314(3) Uani 1 1 d . . . . .
H16A H -0.170211 0.527118 0.322737 0.047 Uiso 1 1 calc GR . . . .
H16B H -0.176253 0.496267 0.449300 0.047 Uiso 1 1 calc GR . . . .
H16C H -0.036944 0.491740 0.383985 0.047 Uiso 1 1 calc GR . . . .
C17 C 0.33004(16) 0.56346(11) 0.08585(13) 0.0308(3) Uani 1 1 d . . . . .
H17A H 0.299168 0.615348 0.045609 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.255200 0.522146 0.092184 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.404006 0.536116 0.045485 0.046 Uiso 1 1 calc GR . . . .
C18 C 0.44405(18) 0.49421(11) 0.30919(17) 0.0388(4) Uani 1 1 d . . . . .
H18A H 0.520433 0.466714 0.272128 0.058 Uiso 1 1 calc GR . . . .
H18B H 0.368122 0.453403 0.311096 0.058 Uiso 1 1 calc GR . . . .
H18C H 0.470584 0.510014 0.385105 0.058 Uiso 1 1 calc GR . . . .


_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
Si1 C1 1.8621(14) . ?
Si1 C3AA 1.8626(14) . ?
Si1 C17 1.8650(16) . ?
Si1 C18 1.8619(16) . ?
O1 C7 1.2381(18) . ?
N1 C3 1.3650(19) . ?
N1 C13 1.446(2) . ?
N1 C14 1.4529(19) . ?
N2 C11 1.3721(19) . ?
N2 C15 1.4536(19) . ?
N2 C16 1.449(2) . ?
C1 C2 1.3904(19) . ?
C1 C6 1.4128(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.413(2) . ?
C3AA C8 1.4129(19) . ?
C3AA C12 1.392(2) . ?
C3 C4 1.411(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(2) . ?
C6 C7 1.4876(19) . ?
C7 C8 1.4867(19) . ?
C8 C9 1.4020(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.409(2) . ?
C11 C12 1.4129(19) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C1 Si1 C3AA 104.41(6) . . ?
C1 Si1 C17 110.56(7) . . ?
C1 Si1 C18 111.00(7) . . ?
C3AA Si1 C17 110.39(7) . . ?
C18 Si1 C3AA 111.51(7) . . ?
C18 Si1 C17 108.94(8) . . ?
C3 N1 C13 122.79(13) . . ?
C3 N1 C14 120.33(13) . . ?
C13 N1 C14 116.71(12) . . ?
C11 N2 C15 120.20(13) . . ?
C11 N2 C16 122.14(13) . . ?
C16 N2 C15 115.84(13) . . ?
C2 C1 Si1 119.63(10) . . ?
C2 C1 C6 119.68(13) . . ?
C6 C1 Si1 120.64(10) . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.58(13) . . ?
C3 C2 H2 118.7 . . ?
C8 C3AA Si1 120.65(10) . . ?
C12 C3AA Si1 119.41(11) . . ?
C12 C3AA C8 119.92(13) . . ?
N1 C3 C2 122.42(13) . . ?
N1 C3 C4 121.00(13) . . ?
C4 C3 C2 116.58(13) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.01(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.39(14) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 125.10(12) . . ?
C5 C6 C1 117.66(13) . . ?
C5 C6 C7 117.23(13) . . ?
O1 C7 C6 118.57(13) . . ?
O1 C7 C8 118.93(13) . . ?
C8 C7 C6 122.50(12) . . ?
C3AA C8 C7 125.09(12) . . ?
C9 C8 C3AA 117.54(13) . . ?
C9 C8 C7 117.36(13) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.38(14) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.11(13) . . ?
C11 C10 H10 119.4 . . ?
N2 C11 C10 120.69(13) . . ?
N2 C11 C12 122.56(14) . . ?
C10 C11 C12 116.73(13) . . ?
C3AA C12 C11 122.31(13) . . ?
C3AA C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/ n-hexane/ cyclohexane'
####################################################################### 
# 
# 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_20ML001_PG01-079-01-03
_database_code_depnum_ccdc_archive 'CCDC 2171687'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina '
;University of Bern
Switzerland
;
_audit_update_record             
;
2022-05-09 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18 H24 Br2 N2 Si'
_chemical_formula_sum            'C18 H24 Br2 N2 Si'
_chemical_formula_weight         456.3

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6606(2)
_cell_length_b                   18.8553(2)
_cell_length_c                   12.7788(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.662(2)
_cell_angle_gamma                90
_cell_volume                     1988.39(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    5242
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      26.423

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'rect. Prism'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -1 0.1113
0 -1 -1 0.0263
0 1 1 0.0426
1 -1 -1 0.0869
-1 1 1 0.1473
-2 0 -1 0.1334
1 1 2 0.0905
0 1 2 0.0429
0 -1 -2 0.0214
1 -1 -2 0.065
-1 1 2 0.1123
1 0 -2 0.0706
0 -1 2 0.0386
1 1 -2 0.0726
0 -1 1 0.0374
1 1 -1 0.087
0 -2 1 0.041
0 2 -1 0.0426
1 2 -1 0.0742
-2 -1 1 0.143
0 -1 0 0.0418
0 1 0 0.0537

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
-0.9990 -0.9992 -0.9993 -0.0264 -0.0850 -0.0853
-0.0000 -0.9991 -0.9990 -0.0146 -0.0677 -0.0021
0.0000 0.9991 0.9990 0.0146 0.0677 0.0021
0.9989 -0.9989 -0.9987 -0.0028 -0.0504 0.0812
-0.9989 0.9989 0.9987 0.0028 0.0504 -0.0812
-1.9979 -0.0005 -0.9997 -0.0041 -0.0885 -0.1763
0.9990 0.9994 1.9984 0.0069 0.1389 0.0951
0.0000 0.9992 1.9981 -0.0049 0.1216 0.0118
-0.0000 -0.9992 -1.9981 0.0049 -0.1216 -0.0118
0.9989 -0.9990 -1.9978 0.0167 -0.1043 0.0714
-0.9989 0.9990 1.9978 -0.0167 0.1043 -0.0714
0.9990 -0.0001 -1.9979 0.0508 -0.0906 0.0637
-0.0000 -0.9987 1.9982 -0.0732 0.0942 0.0272
0.9990 0.9988 -1.9979 0.0850 -0.0769 0.0560
-0.0000 -0.9988 0.9991 -0.0536 0.0402 0.0175
0.9990 0.9990 -0.9988 0.0654 -0.0229 0.0658
-0.0000 -1.9977 0.9991 -0.0878 0.0265 0.0251
0.0000 1.9977 -0.9991 0.0878 -0.0265 -0.0251
0.9990 1.9979 -0.9988 0.0996 -0.0092 0.0581
-1.9979 -0.9992 0.9985 -0.0772 0.0056 -0.1491
-0.0000 -0.9989 0.0000 -0.0341 -0.0137 0.0077
0.0000 0.9989 -0.0000 0.0341 0.0137 -0.0077


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.138
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_T_max  1

_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 0.800

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0118079
_diffrn_orient_matrix_ub_12      0.0341651
_diffrn_orient_matrix_ub_13      -0.0195429
_diffrn_orient_matrix_ub_21      0.0172967
_diffrn_orient_matrix_ub_22      0.0137537
_diffrn_orient_matrix_ub_23      0.0539942
_diffrn_orient_matrix_ub_31      0.0833424
_diffrn_orient_matrix_ub_32      -0.0076992
_diffrn_orient_matrix_ub_33      0.0097697
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_number            16850
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             4068
_reflns_number_gt                3306
_reflns_threshold_expression     'I > 2σ(I)'

_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  72.00   1.00   10.00    --   29.02 -77.00-120.00  114
  2  ω     -9.00 105.00   1.00   10.00    --   29.02  57.00-180.00  114
  3  ω     39.00 123.00   1.00   10.00    --   29.02 178.00-180.00   84
  4  ω     -9.00 105.00   1.00   10.00    --   29.02  57.00 -90.00  114
  5  ω    -62.00  42.00   1.00   10.00    --   29.02   0.00 120.00  104
  6  ω    -14.00  42.00   1.00   10.00    --   29.02  77.00  30.00   56
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'

_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0184P)²+0.6312P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4068
_refine_ls_number_parameters     228
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.072
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C3A \\sim C3: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.02 within 1.7A
Uanis(N1) = Uanis(N1A)
3. Others
 Sof(H2BD)=Sof(H2BE)=Sof(H2BF)=Sof(N1A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 1-FVAR(1)
 Sof(N1)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=
 FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00J(H00K)
4.b Idealised Me refined as rotating group:
 C00G(H00B,H00F,H00G), C00I(H00H,H00I,H00J), C00K(H00L,H00M,H00N), C00L(H00O,
 H00P,H00Q), C2(H2AA,H2AB,H2AC), C2(H2BD,H2BE,H2BF), C3(H3A,H3B,H3C), C3A(H3AA,
 H3AB,H3AC)
;
_olex2_submission_special_instructions 'No special instructions were received'

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.48130(3) 0.61162(2) 0.45152(3) 0.03345(9) Uani 1 1 d . . . . .
Br02 Br 0.90469(4) 0.81937(2) 0.58812(3) 0.03783(10) Uani 1 1 d . . . . .
Si03 Si 0.67021(9) 0.70479(4) 0.69082(7) 0.02430(18) Uani 1 1 d . . . . .
N004 N 1.0624(3) 0.50457(12) 0.6407(2) 0.0364(7) Uani 1 1 d . . . . .
C005 C 0.9501(3) 0.72011(13) 0.6094(2) 0.0237(6) Uani 1 1 d . . . . .
C006 C 0.8490(3) 0.67529(13) 0.6473(2) 0.0210(6) Uani 1 1 d . . . . .
C007 C 0.4273(3) 0.70814(14) 0.4733(2) 0.0247(6) Uani 1 1 d . . . . .
C008 C 0.5061(3) 0.74289(14) 0.5713(2) 0.0239(6) Uani 1 1 d . . . . .
C009 C 0.8932(3) 0.60372(13) 0.6576(2) 0.0232(6) Uani 1 1 d . . . . .
H009 H 0.829267 0.572485 0.682752 0.028 Uiso 1 1 calc R U . . .
C00A C 1.0858(3) 0.69552(14) 0.5863(2) 0.0278(7) Uani 1 1 d . . . . .
H00A H 1.150848 0.726932 0.562492 0.033 Uiso 1 1 calc R U . . .
C00B C 1.0274(3) 0.57618(14) 0.6325(2) 0.0254(6) Uani 1 1 d . . . . .
C00C C 0.3088(3) 0.74009(15) 0.3894(2) 0.0296(7) Uani 1 1 d . . . . .
H00C H 0.259851 0.715082 0.32517 0.036 Uiso 1 1 calc R U . . .
C00D C 1.1255(3) 0.62484(15) 0.5981(2) 0.0280(7) Uani 1 1 d . . . . .
H00D H 1.218273 0.608914 0.58314 0.034 Uiso 1 1 calc R U . . .
C00E C 0.2623(3) 0.80907(15) 0.4003(2) 0.0322(7) Uani 1 1 d . . . . .
H00E H 0.182545 0.830461 0.343333 0.039 Uiso 1 1 calc R U . . .
C00G C 0.9611(4) 0.45564(14) 0.6766(3) 0.0353(7) Uani 1 1 d . . . . .
H00B H 0.972703 0.463799 0.752794 0.053 Uiso 1 1 calc R U . . .
H00F H 0.992953 0.407908 0.667081 0.053 Uiso 1 1 calc R U . . .
H00G H 0.850007 0.462607 0.633924 0.053 Uiso 1 1 calc R U . . .
C00H C 0.3349(4) 0.84665(15) 0.4966(3) 0.0340(7) Uani 1 1 d . . . . .
C00I C 0.5908(4) 0.62840(15) 0.7515(3) 0.0364(8) Uani 1 1 d . . . . .
H00H H 0.56139 0.59066 0.698756 0.055 Uiso 1 1 calc R U . . .
H00I H 0.497149 0.643125 0.771196 0.055 Uiso 1 1 calc R U . . .
H00J H 0.672873 0.612073 0.815852 0.055 Uiso 1 1 calc R U . . .
C00J C 0.4551(3) 0.81237(14) 0.5796(3) 0.0310(7) Uani 1 1 d . . . . .
H00K H 0.503876 0.83727 0.64403 0.037 Uiso 1 1 calc R U . . .
C00K C 0.7386(4) 0.77241(15) 0.8012(2) 0.0357(7) Uani 1 1 d . . . . .
H00L H 0.833185 0.755413 0.856487 0.054 Uiso 1 1 calc R U . . .
H00M H 0.653738 0.780987 0.833612 0.054 Uiso 1 1 calc R U . . .
H00N H 0.764072 0.815723 0.770591 0.054 Uiso 1 1 calc R U . . .
C00L C 1.2139(4) 0.47860(16) 0.6292(3) 0.0414(8) Uani 1 1 d . . . . .
H00O H 1.2256 0.494864 0.560788 0.062 Uiso 1 1 calc R U . . .
H00P H 1.214103 0.427693 0.630338 0.062 Uiso 1 1 calc R U . . .
H00Q H 1.302473 0.496048 0.688766 0.062 Uiso 1 1 calc R U . . .
N1 N 0.2768(15) 0.9141(5) 0.5156(9) 0.039(2) Uani 0.67(2) 1 d . . P A 1
C2 C 0.1648(5) 0.95013(19) 0.4279(3) 0.0715(13) Uani 1 1 d . . . . .
H2AA H 0.211837 0.957554 0.369739 0.107 Uiso 0.67(2) 1 calc R U P A 1
H2AB H 0.138323 0.995102 0.453246 0.107 Uiso 0.67(2) 1 calc R U P A 1
H2AC H 0.068154 0.922179 0.40115 0.107 Uiso 0.67(2) 1 calc R U P A 1
H2BD H 0.158393 0.945332 0.351905 0.107 Uiso 0.33(2) 1 calc R U P A 2
H2BE H 0.157777 0.999371 0.445008 0.107 Uiso 0.33(2) 1 calc R U P A 2
H2BF H 0.077011 0.924663 0.441743 0.107 Uiso 0.33(2) 1 calc R U P A 2
C3 C 0.3351(17) 0.9474(5) 0.6195(8) 0.068(3) Uani 0.67(2) 1 d . U P A 1
H3A H 0.323011 0.915794 0.67532 0.102 Uiso 0.67(2) 1 calc R U P A 1
H3B H 0.274189 0.98996 0.619674 0.102 Uiso 0.67(2) 1 calc R U P A 1
H3C H 0.447462 0.959143 0.633831 0.102 Uiso 0.67(2) 1 calc R U P A 1
N1A N 0.323(3) 0.9205(12) 0.498(2) 0.039(2) Uani 0.33(2) 1 d . . P A 2
C3A C 0.414(3) 0.9591(11) 0.592(2) 0.073(7) Uani 0.33(2) 1 d . U P A 2
H3AA H 0.393399 0.940135 0.656178 0.11 Uiso 0.33(2) 1 calc R U P A 2
H3AB H 0.381782 1.008097 0.583521 0.11 Uiso 0.33(2) 1 calc R U P A 2
H3AC H 0.526875 0.95529 0.599245 0.11 Uiso 0.33(2) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br01 C007 1.920(3) . ?
Br02 C005 1.915(3) . ?
Si03 C006 1.881(3) . ?
Si03 C008 1.884(3) . ?
Si03 C00I 1.864(3) . ?
Si03 C00K 1.860(3) . ?
N004 C00B 1.381(3) . ?
N004 C00G 1.441(3) . ?
N004 C00L 1.450(3) . ?
C005 C006 1.405(3) . ?
C005 C00A 1.376(4) . ?
C006 C009 1.398(3) . ?
C007 C008 1.395(4) . ?
C007 C00C 1.378(4) . ?
C008 C00J 1.397(4) . ?
C009 H009 0.93 . ?
C009 C00B 1.396(3) . ?
C00A H00A 0.93 . ?
C00A C00D 1.373(4) . ?
C00B C00D 1.408(4) . ?
C00C H00C 0.93 . ?
C00C C00E 1.381(4) . ?
C00D H00D 0.93 . ?
C00E H00E 0.93 . ?
C00E C00H 1.393(4) . ?
C00G H00B 0.96 . ?
C00G H00F 0.96 . ?
C00G H00G 0.96 . ?
C00H C00J 1.400(4) . ?
C00H N1 1.416(10) . ?
C00H N1A 1.40(2) . ?
C00I H00H 0.96 . ?
C00I H00I 0.96 . ?
C00I H00J 0.96 . ?
C00J H00K 0.93 . ?
C00K H00L 0.96 . ?
C00K H00M 0.96 . ?
C00K H00N 0.96 . ?
C00L H00O 0.96 . ?
C00L H00P 0.96 . ?
C00L H00Q 0.96 . ?
N1 C2 1.413(11) . ?
N1 C3 1.416(14) . ?
C2 H2AA 0.96 . ?
C2 H2AB 0.96 . ?
C2 H2AC 0.96 . ?
C2 H2BD 0.96 . ?
C2 H2BE 0.96 . ?
C2 H2BF 0.96 . ?
C2 N1A 1.50(2) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
N1A C3A 1.42(3) . ?
C3A H3AA 0.96 . ?
C3A H3AB 0.96 . ?
C3A H3AC 0.96 . ?

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
C006 Si03 C008 111.08(12) . . ?
C00I Si03 C006 109.58(12) . . ?
C00I Si03 C008 110.41(13) . . ?
C00K Si03 C006 109.01(13) . . ?
C00K Si03 C008 109.98(13) . . ?
C00K Si03 C00I 106.66(14) . . ?
C00B N004 C00G 120.6(2) . . ?
C00B N004 C00L 120.5(2) . . ?
C00G N004 C00L 118.3(2) . . ?
C006 C005 Br02 120.95(19) . . ?
C00A C005 Br02 116.78(19) . . ?
C00A C005 C006 122.3(2) . . ?
C005 C006 Si03 125.39(19) . . ?
C009 C006 Si03 119.00(19) . . ?
C009 C006 C005 115.5(2) . . ?
C008 C007 Br01 120.1(2) . . ?
C00C C007 Br01 117.3(2) . . ?
C00C C007 C008 122.6(3) . . ?
C007 C008 Si03 126.3(2) . . ?
C007 C008 C00J 115.4(3) . . ?
C00J C008 Si03 118.3(2) . . ?
C006 C009 H009 117.9 . . ?
C00B C009 C006 124.1(2) . . ?
C00B C009 H009 117.9 . . ?
C005 C00A H00A 119.8 . . ?
C00D C00A C005 120.3(3) . . ?
C00D C00A H00A 119.8 . . ?
N004 C00B C009 121.6(2) . . ?
N004 C00B C00D 121.4(2) . . ?
C009 C00B C00D 116.9(2) . . ?
C007 C00C H00C 119.8 . . ?
C007 C00C C00E 120.3(3) . . ?
C00E C00C H00C 119.8 . . ?
C00A C00D C00B 120.8(2) . . ?
C00A C00D H00D 119.6 . . ?
C00B C00D H00D 119.6 . . ?
C00C C00E H00E 120 . . ?
C00C C00E C00H 120.1(3) . . ?
C00H C00E H00E 120 . . ?
N004 C00G H00B 109.5 . . ?
N004 C00G H00F 109.5 . . ?
N004 C00G H00G 109.5 . . ?
H00B C00G H00F 109.5 . . ?
H00B C00G H00G 109.5 . . ?
H00F C00G H00G 109.5 . . ?
C00E C00H C00J 117.9(3) . . ?
C00E C00H N1 121.3(5) . . ?
C00E C00H N1A 120.3(11) . . ?
C00J C00H N1 120.4(5) . . ?
N1A C00H C00J 119.4(11) . . ?
Si03 C00I H00H 109.5 . . ?
Si03 C00I H00I 109.5 . . ?
Si03 C00I H00J 109.5 . . ?
H00H C00I H00I 109.5 . . ?
H00H C00I H00J 109.5 . . ?
H00I C00I H00J 109.5 . . ?
C008 C00J C00H 123.7(3) . . ?
C008 C00J H00K 118.1 . . ?
C00H C00J H00K 118.1 . . ?
Si03 C00K H00L 109.5 . . ?
Si03 C00K H00M 109.5 . . ?
Si03 C00K H00N 109.5 . . ?
H00L C00K H00M 109.5 . . ?
H00L C00K H00N 109.5 . . ?
H00M C00K H00N 109.5 . . ?
N004 C00L H00O 109.5 . . ?
N004 C00L H00P 109.5 . . ?
N004 C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C2 N1 C00H 119.3(8) . . ?
C2 N1 C3 119.6(8) . . ?
C3 N1 C00H 121.0(8) . . ?
N1 C2 H2AA 109.5 . . ?
N1 C2 H2AB 109.5 . . ?
N1 C2 H2AC 109.5 . . ?
H2AA C2 H2AB 109.5 . . ?
H2AA C2 H2AC 109.5 . . ?
H2AB C2 H2AC 109.5 . . ?
H2BD C2 H2BE 109.5 . . ?
H2BD C2 H2BF 109.5 . . ?
H2BE C2 H2BF 109.5 . . ?
N1A C2 H2BD 109.5 . . ?
N1A C2 H2BE 109.5 . . ?
N1A C2 H2BF 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C00H N1A C2 115.0(16) . . ?
C00H N1A C3A 119.9(19) . . ?
C3A N1A C2 119.1(17) . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 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
Br01 C007 C008 Si03 1.0(3) . . . . ?
Br01 C007 C008 C00J -178.6(2) . . . . ?
Br01 C007 C00C C00E 179.0(2) . . . . ?
Br02 C005 C006 Si03 -4.4(3) . . . . ?
Br02 C005 C006 C009 178.9(2) . . . . ?
Br02 C005 C00A C00D -179.1(2) . . . . ?
Si03 C006 C009 C00B -177.2(2) . . . . ?
Si03 C008 C00J C00H 179.8(2) . . . . ?
N004 C00B C00D C00A 177.5(3) . . . . ?
C005 C006 C009 C00B -0.2(4) . . . . ?
C005 C00A C00D C00B 0.9(4) . . . . ?
C006 Si03 C008 C007 58.3(3) . . . . ?
C006 Si03 C008 C00J -122.1(2) . . . . ?
C006 C005 C00A C00D 1.1(4) . . . . ?
C006 C009 C00B N004 -177.8(3) . . . . ?
C006 C009 C00B C00D 2.1(4) . . . . ?
C007 C008 C00J C00H -0.6(4) . . . . ?
C007 C00C C00E C00H -0.2(4) . . . . ?
C008 Si03 C006 C005 65.0(3) . . . . ?
C008 Si03 C006 C009 -118.4(2) . . . . ?
C008 C007 C00C C00E -0.4(4) . . . . ?
C009 C00B C00D C00A -2.4(4) . . . . ?
C00A C005 C006 Si03 175.3(2) . . . . ?
C00A C005 C006 C009 -1.4(4) . . . . ?
C00C C007 C008 Si03 -179.6(2) . . . . ?
C00C C007 C008 C00J 0.8(4) . . . . ?
C00C C00E C00H C00J 0.4(4) . . . . ?
C00C C00E C00H N1 -172.3(7) . . . . ?
C00C C00E C00H N1A 162.6(10) . . . . ?
C00E C00H C00J C008 0.0(5) . . . . ?
C00E C00H N1 C2 -12.4(14) . . . . ?
C00E C00H N1 C3 170.7(5) . . . . ?
C00E C00H N1A C2 35.5(18) . . . . ?
C00E C00H N1A C3A -172.0(13) . . . . ?
C00G N004 C00B C009 -0.4(4) . . . . ?
C00G N004 C00B C00D 179.7(3) . . . . ?
C00I Si03 C006 C005 -172.7(2) . . . . ?
C00I Si03 C006 C009 3.9(3) . . . . ?
C00I Si03 C008 C007 -63.5(3) . . . . ?
C00I Si03 C008 C00J 116.1(2) . . . . ?
C00J C00H N1 C2 175.0(7) . . . . ?
C00J C00H N1 C3 -1.9(9) . . . . ?
C00J C00H N1A C2 -162.6(9) . . . . ?
C00J C00H N1A C3A -10.1(17) . . . . ?
C00K Si03 C006 C005 -56.3(3) . . . . ?
C00K Si03 C006 C009 120.3(2) . . . . ?
C00K Si03 C008 C007 179.1(2) . . . . ?
C00K Si03 C008 C00J -1.3(3) . . . . ?
C00L N004 C00B C009 -171.3(3) . . . . ?
C00L N004 C00B C00D 8.8(4) . . . . ?
N1 C00H C00J C008 172.8(7) . . . . ?
N1A C00H C00J C008 -162.3(10) . . . . ?

#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#



# END of CIF
_chemical_name_systematic        
3,3'-(dimethylsilanediyl)bis(4-bromo-N,N-dimethylaniline)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Cyclohexane/ ethyl acetate'
####################################################################### 
# 
# 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_22ML008_PG01-080-02-02
_database_code_depnum_ccdc_archive 'CCDC 2177612'
loop_
_audit_author_name
_audit_author_address
'Lorraine Andrade Malaspina '
;University of Bern
Switzerland
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;

_audit_creation_date             2022-06-06T20:11:31-00:00

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C14 H19 N3 O5 S'
_chemical_formula_sum            'C14 H19 N3 O5 S'
_chemical_formula_weight         341.38
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.16670(4)
_cell_length_b                   7.62474(6)
_cell_length_c                   20.29901(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.9565(8)
_cell_angle_gamma                90
_cell_volume                     799.208(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    26371
_cell_measurement_theta_min      2.178
_cell_measurement_theta_max      79.792

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'light colourless'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0347
-1 0 0 0.0551
-1 0 -1 0.0499
-1 1 1 0.0974
-1 1 -1 0.0917
0 1 1 0.1045
0 1 0 0.1104
0 1 -1 0.1038
-1 -1 0 0.0705
-1 -1 1 0.0707
1 1 1 0.0871
0 0 -1 0.0196
0 0 1 0.0131
-3 -1 -7 0.0333
1 -5 -1 0.0999
-1 -4 -7 0.083

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 0.0009 -1.0019 -0.2595 0.0897 -0.1338
-1 -0.0007 0.0025 0.2272 -0.0473 0.1877
-1 -0.0006 -0.9969 0.1948 -0.0049 0.2417
-1 0.9996 1.0028 0.3533 0.074 0.0613
-1 0.9999 -0.996 0.2886 0.1588 0.1693
0 1.0003 1.0003 0.1261 0.1214 -0.1264
0 1.0004 0.0009 0.0938 0.1637 -0.0724
0 1.0006 -0.9985 0.0614 0.2061 -0.0184
-1 -1.0012 0.0016 0.1334 -0.2111 0.2601
-1 -1.0013 1.0009 0.1658 -0.2534 0.2062
1 1.001 0.9978 -0.101 0.1687 -0.3141
0 0.0002 -0.9994 -0.0324 0.0424 0.054
0 -0.0002 0.9994 0.0324 -0.0424 -0.054
-2.6776 -0.5235 -7.4366 0.3182 0.1033 0.9424
0.6198 -4.8571 -0.8108 -0.6222 -0.7316 0.2787
-1.074 -3.9241 -6.68 -0.3402 -0.4099 0.8463


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.87592
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.938
_oxdiff_exptl_absorpt_empirical_details 
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.029
_oxdiff_exptl_absorpt_empirical_full_min 0.77

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      173.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.2271555
_diffrn_orient_matrix_ub_12      0.0936967
_diffrn_orient_matrix_ub_13      0.0324073
_diffrn_orient_matrix_ub_21      0.0471026
_diffrn_orient_matrix_ub_22      0.1637106
_diffrn_orient_matrix_ub_23      -0.04238
_diffrn_orient_matrix_ub_31      -0.1878063
_diffrn_orient_matrix_ub_32      -0.0723315
_diffrn_orient_matrix_ub_33      -0.0540082
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_number            31548
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         77.681
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.99
_reflns_Friedel_coverage         0.849
_reflns_number_total             3405
_reflns_number_gt                3357
_reflns_threshold_expression     'I > 2σ(I)'
_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  50.00   0.50    0.20    --  -23.00  59.00  17.00  178
  2  ω    -94.00  -7.00   0.50    0.20    --  -23.00 -59.00-122.00  174
  3  ω    -23.00  64.00   0.50    0.20    --   47.92 -59.00-122.00  174
  4  ω     32.00 120.00   0.50    0.20    --   47.92  59.00  17.00  176
  5  ω     98.00 177.00   0.50    1.25    --  113.25  59.00  17.00  158
  6  ω    -95.00   0.00   0.50    0.20    --  -23.00 -77.00  60.00  190
  7  ω    -70.00 -12.00   0.50    0.20    --  -23.00 125.00  60.00  116
  8  ω    -70.00 -12.00   0.50    0.20    --  -23.00 125.00 120.00  116
  9  ω      9.00  42.00   0.50    0.20    --   38.00  91.00  57.42   66
 10  ω     25.00 121.00   0.50    0.20    --   47.92  77.00-150.00  192
 11  ω     -1.00  81.00   0.50    0.20    --   47.92 -99.00  90.00  164
 12  ω     32.00 126.00   0.50    0.20    --   54.00  76.00 158.38  188
 13  ω     32.00 126.00   0.50    0.20    --   54.00  76.00 -75.77  188
 14  ω     35.00 131.00   0.50    0.20    --   58.00  77.00 -31.53  192
 15  ω     40.00 135.00   0.50    0.20    --   62.00  75.00-169.79  190
 16  ω     40.00 135.00   0.50    0.20    --   62.00  76.00  -1.96  190
 17  ω     39.00 135.00   0.50    0.20    --   62.00  77.00 107.23  192
 18  ω     39.00 135.00   0.50    0.20    --   62.00  77.00  46.82  192
 19  ω     39.00 135.00   0.50    0.20    --   62.00  77.00-150.36  192
 20  ω     40.00 135.00   0.50    0.20    --   62.00  75.00 -72.71  190
 21  ω     44.00 139.00   0.50    0.20    --   66.00  76.00 151.70  190
 22  ω     44.00 139.00   0.50    0.20    --   66.00  75.00  65.99  190
 23  ω     48.00 143.00   0.50    0.20    --   70.00  75.00-132.36  190
 24  ω     55.00 143.00   0.50    0.20    --   70.00  56.00-177.14  176
 25  ω     58.00 151.00   0.50    0.20    --   78.00  70.00-130.22  186
 26  ω     71.00 162.00   0.50    1.25    --   90.00  68.00  94.53  182
 27  ω     97.00 177.00   0.50    1.25    --  113.25  61.00 -60.00  160
 28  ω     97.00 177.00   0.50    1.25    --  113.25  61.00 150.00  160
 29  ω     97.00 177.00   0.50    1.25    --  113.25  61.00   0.00  160
 30  ω     97.00 177.00   0.50    1.25    --  113.25  61.00 -30.00  160
 31  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00  90.00  128
 32  ω     97.00 177.00   0.50    1.25    --  113.25  61.00-180.00  160
 33  ω     91.00 177.00   0.50    1.25    --  113.25  77.00 -30.00  172
 34  ω     97.00 177.00   0.50    1.25    --  113.25  61.00-120.00  160
 35  ω     42.00  68.00   0.50    1.25    --  113.25 -61.00-120.00   52
 36  ω     91.00 177.00   0.50    1.25    --  113.25  77.00  90.00  172
 37  ω     91.00 177.00   0.50    1.25    --  113.25  77.00-150.00  172
 38  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00 -90.00  128
 39  ω     91.00 177.00   0.50    1.25    --  113.25  77.00  30.00  172
 40  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00 -30.00  128
 41  ω     97.00 177.00   0.50    1.25    --  113.25  61.00 -90.00  160
 42  ω     97.00 177.00   0.50    1.25    --  113.25  61.00  90.00  160
 43  ω     91.00 177.00   0.50    1.25    --  113.25  77.00-120.00  172
 44  ω     91.00 177.00   0.50    1.25    --  113.25  77.00 120.00  172
 45  ω    101.00 177.00   0.50    1.25    --  113.25  45.00 -60.00  152
 46  ω     97.00 177.00   0.50    1.25    --  113.25  61.00-150.00  160
 47  ω     97.00 177.00   0.50    1.25    --  113.25  61.00  30.00  160
 48  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00-150.00  128
 49  ω     42.00 102.00   0.50    1.25    --  113.25 -77.00  30.00  120
 50  ω     42.00  68.00   0.50    1.25    --  113.25 -61.00  90.00   52
 51  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00  60.00  128
 52  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00 150.00  128
 53  ω     91.00 177.00   0.50    1.25    --  113.25  77.00   0.00  172
 54  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00 120.00  128
 55  ω     97.00 177.00   0.50    1.25    --  113.25  61.00 120.00  160
 56  ω     42.00 102.00   0.50    1.25    --  113.25 -77.00-180.00  120
 57  ω     97.00 177.00   0.50    1.25    --  113.25  61.00  60.00  160
 58  ω     91.00 177.00   0.50    1.25    --  113.25  77.00 150.00  172
 59  ω     42.00 102.00   0.50    1.25    --  113.25 -77.00 -30.00  120
 60  ω     42.00 102.00   0.50    1.25    --  113.25 -77.00-120.00  120
 61  ω     42.00 102.00   0.50    1.25    --  113.25 -77.00  60.00  120
 62  ω     91.00 177.00   0.50    1.25    --  113.25  77.00-180.00  172
 63  ω     42.00  68.00   0.50    1.25    --  113.25 -61.00 150.00   52
 64  ω     42.00  68.00   0.50    1.25    --  113.25 -61.00 120.00   52
 65  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00 -60.00  128
 66  ω     42.00 106.00   0.50    1.25    --  113.25 -94.00   0.00  128
 67  ω     25.00 121.00   0.50    0.20    --   47.92  77.00 -30.00  192
 68  ω     27.00 122.00   0.50    0.20    --   50.00  77.00 143.38  190
 69  ω     31.00 126.00   0.50    0.20    --   54.00  77.00  47.29  190
 70  ω     32.00 126.00   0.50    0.20    --   54.00  76.00  96.18  188
 71  ω     44.00 115.00   0.50    0.20    --   62.00  66.00 -28.76  142
 72  ω     45.00 139.00   0.50    0.20    --   66.00  72.00 -34.13  188
 73  ω     58.00 142.00   0.50    0.20    --   70.00  42.00 108.41  168
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.1359P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_number_reflns         3405
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_olex2_refinement_description    
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
        2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2A), C5(H5)
        2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C9(H9A,H9B), C6(H6A,H6B), C4(H4A,
 H4B), C12(H12A,H12B)
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.37475(11) -0.02228(6) 0.69266(3) 0.03534(15) Uani 1 1 d . . . . .
O3 O 0.7974(3) 0.8189(2) 0.89223(7) 0.0328(3) Uani 1 1 d . . . . .
O1 O 0.5425(3) 0.0385(2) 0.47756(8) 0.0363(4) Uani 1 1 d . . . . .
N2 N 0.2706(4) 0.1796(2) 0.54830(8) 0.0303(4) Uani 1 1 d . . . . .
O4 O 0.9121(4) 1.1457(3) 0.83455(9) 0.0477(4) Uani 1 1 d . . . . .
O5 O 1.1547(4) 0.7547(3) 0.99426(10) 0.0513(5) Uani 1 1 d . . . . .
O2 O 1.0668(3) 0.7181(3) 0.81513(10) 0.0483(5) Uani 1 1 d . . . . .
N3 N 1.0003(3) 0.9297(2) 0.91040(9) 0.0303(4) Uani 1 1 d . . . . .
N1 N 0.2316(4) -0.1054(2) 0.53645(10) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.3646(4) 0.0374(3) 0.51778(10) 0.0296(4) Uani 1 1 d . . . . .
C3 C 0.0525(4) -0.0671(3) 0.58841(10) 0.0291(4) Uani 1 1 d . . . . .
H3 H -0.129244 -0.096733 0.573976 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0855(4) 0.1355(3) 0.59793(9) 0.0273(4) Uani 1 1 d . . . . .
H2A H -0.082633 0.197436 0.588975 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1873(4) 0.1714(3) 0.66874(9) 0.0266(4) Uani 1 1 d . . . . .
H5 H 0.035377 0.179206 0.697815 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8660(4) 0.7043(3) 0.84139(11) 0.0326(4) Uani 1 1 d . . . . .
C7 C 0.4246(4) 0.3743(3) 0.74923(10) 0.0309(4) Uani 1 1 d . . . . .
H7A H 0.267129 0.398215 0.774173 0.037 Uiso 1 1 calc R U . . .
H7B H 0.508077 0.268162 0.768323 0.037 Uiso 1 1 calc R U . . .
C14 C 1.1674(4) 0.8875(3) 0.96253(10) 0.0320(4) Uani 1 1 d . . . . .
C8 C 0.6093(5) 0.5282(3) 0.75772(11) 0.0337(4) Uani 1 1 d . . . . .
H8A H 0.535357 0.631925 0.734533 0.04 Uiso 1 1 calc R U . . .
H8B H 0.775908 0.499247 0.737642 0.04 Uiso 1 1 calc R U . . .
C13 C 1.3514(4) 1.0387(3) 0.96975(11) 0.0336(4) Uani 1 1 d . . . . .
H13A H 1.532956 0.997079 0.96994 0.04 Uiso 1 1 calc R U . . .
H13B H 1.323343 1.102689 1.011338 0.04 Uiso 1 1 calc R U . . .
C11 C 1.0477(4) 1.0870(3) 0.87820(11) 0.0332(4) Uani 1 1 d . . . . .
C9 C 0.6572(4) 0.5720(3) 0.83040(11) 0.0354(5) Uani 1 1 d . . . . .
H9A H 0.494953 0.617343 0.848624 0.042 Uiso 1 1 calc R U . . .
H9B H 0.704788 0.463349 0.854605 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3456(5) 0.3380(3) 0.67749(10) 0.0314(4) Uani 1 1 d . . . . .
H6A H 0.243175 0.43834 0.659946 0.038 Uiso 1 1 calc R U . . .
H6B H 0.50348 0.328275 0.651426 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1264(5) -0.1576(3) 0.65310(12) 0.0373(5) Uani 1 1 d . . . . .
H4A H 0.193761 -0.27693 0.644869 0.045 Uiso 1 1 calc R U . . .
H4B H -0.025738 -0.167194 0.68123 0.045 Uiso 1 1 calc R U . . .
C12 C 1.2937(4) 1.1573(3) 0.91025(12) 0.0382(5) Uani 1 1 d . . . . .
H12A H 1.269994 1.280246 0.924485 0.046 Uiso 1 1 calc R U . . .
H12B H 1.43722 1.152779 0.879205 0.046 Uiso 1 1 calc R U . . .
H2 H 0.327(5) 0.277(4) 0.5402(14) 0.035(7) Uiso 1 1 d . . . . .
H1 H 0.291(7) -0.216(5) 0.5317(17) 0.056(9) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 1.823(2) . ?
S1 C4 1.813(2) . ?
O3 N3 1.386(2) . ?
O3 C10 1.407(3) . ?
O1 C1 1.250(3) . ?
N2 C1 1.348(3) . ?
N2 C2 1.452(3) . ?
N2 H2 0.82(3) . ?
O4 C11 1.197(3) . ?
O5 C14 1.203(3) . ?
O2 C10 1.187(3) . ?
N3 C14 1.381(3) . ?
N3 C11 1.392(3) . ?
N1 C1 1.349(3) . ?
N1 C3 1.456(3) . ?
N1 H1 0.91(4) . ?
C3 H3 1 . ?
C3 C2 1.566(3) . ?
C3 C4 1.521(3) . ?
C2 H2A 1 . ?
C2 C5 1.538(3) . ?
C5 H5 1 . ?
C5 C6 1.518(3) . ?
C10 C9 1.488(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C7 C8 1.518(3) . ?
C7 C6 1.524(3) . ?
C14 C13 1.498(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C8 C9 1.525(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C12 1.530(3) . ?
C11 C12 1.507(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?

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
C4 S1 C5 88.95(11) . . ?
N3 O3 C10 111.51(15) . . ?
C1 N2 C2 112.90(18) . . ?
C1 N2 H2 120(2) . . ?
C2 N2 H2 127(2) . . ?
O3 N3 C11 122.94(18) . . ?
C14 N3 O3 120.63(18) . . ?
C14 N3 C11 116.44(18) . . ?
C1 N1 C3 112.58(18) . . ?
C1 N1 H1 123(2) . . ?
C3 N1 H1 119(2) . . ?
O1 C1 N2 125.4(2) . . ?
O1 C1 N1 125.6(2) . . ?
N2 C1 N1 108.98(18) . . ?
N1 C3 H3 110.9 . . ?
N1 C3 C2 102.60(16) . . ?
N1 C3 C4 112.80(19) . . ?
C2 C3 H3 110.9 . . ?
C4 C3 H3 110.9 . . ?
C4 C3 C2 108.55(17) . . ?
N2 C2 C3 102.37(16) . . ?
N2 C2 H2A 110.7 . . ?
N2 C2 C5 113.27(17) . . ?
C3 C2 H2A 110.7 . . ?
C5 C2 C3 108.86(16) . . ?
C5 C2 H2A 110.7 . . ?
S1 C5 H5 108.2 . . ?
C2 C5 S1 105.46(13) . . ?
C2 C5 H5 108.2 . . ?
C6 C5 S1 111.56(15) . . ?
C6 C5 C2 115.08(16) . . ?
C6 C5 H5 108.2 . . ?
O3 C10 C9 109.36(18) . . ?
O2 C10 O3 121.3(2) . . ?
O2 C10 C9 129.3(2) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C8 C7 C6 113.32(17) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
O5 C14 N3 124.2(2) . . ?
O5 C14 C13 129.9(2) . . ?
N3 C14 C13 105.91(18) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.08(17) . . ?
H8A C8 H8B 108 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C14 C13 C12 105.75(18) . . ?
H13A C13 H13B 108.7 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
O4 C11 N3 124.2(2) . . ?
O4 C11 C12 130.6(2) . . ?
N3 C11 C12 105.25(19) . . ?
C10 C9 C8 112.73(19) . . ?
C10 C9 H9A 109 . . ?
C10 C9 H9B 109 . . ?
C8 C9 H9A 109 . . ?
C8 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
C5 C6 C7 112.95(17) . . ?
C5 C6 H6A 109 . . ?
C5 C6 H6B 109 . . ?
C7 C6 H6A 109 . . ?
C7 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
S1 C4 H4A 110.5 . . ?
S1 C4 H4B 110.5 . . ?
C3 C4 S1 106.09(15) . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C13 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
C11 C12 C13 105.64(19) . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?

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
S1 C5 C6 C7 -64.2(2) . . . . ?
O3 N3 C14 O5 1.6(3) . . . . ?
O3 N3 C14 C13 -177.47(16) . . . . ?
O3 N3 C11 O4 4.0(3) . . . . ?
O3 N3 C11 C12 -175.97(17) . . . . ?
O3 C10 C9 C8 141.52(19) . . . . ?
N2 C2 C5 S1 -84.21(18) . . . . ?
N2 C2 C5 C6 39.2(2) . . . . ?
O4 C11 C12 C13 171.3(2) . . . . ?
O5 C14 C13 C12 173.1(2) . . . . ?
O2 C10 C9 C8 -40.3(3) . . . . ?
N3 O3 C10 O2 -6.4(3) . . . . ?
N3 O3 C10 C9 171.91(17) . . . . ?
N3 C14 C13 C12 -7.8(2) . . . . ?
N3 C11 C12 C13 -8.7(2) . . . . ?
N1 C3 C2 N2 1.9(2) . . . . ?
N1 C3 C2 C5 -118.21(18) . . . . ?
N1 C3 C4 S1 81.57(19) . . . . ?
C1 N2 C2 C3 -6.1(2) . . . . ?
C1 N2 C2 C5 110.9(2) . . . . ?
C1 N1 C3 C2 2.7(2) . . . . ?
C1 N1 C3 C4 -113.9(2) . . . . ?
C3 N1 C1 O1 174.8(2) . . . . ?
C3 N1 C1 N2 -6.7(3) . . . . ?
C3 C2 C5 S1 28.95(18) . . . . ?
C3 C2 C5 C6 152.35(18) . . . . ?
C2 N2 C1 O1 -173.3(2) . . . . ?
C2 N2 C1 N1 8.2(3) . . . . ?
C2 C3 C4 S1 -31.4(2) . . . . ?
C2 C5 C6 C7 175.71(17) . . . . ?
C5 S1 C4 C3 42.51(16) . . . . ?
C10 O3 N3 C14 -94.6(2) . . . . ?
C10 O3 N3 C11 85.5(2) . . . . ?
C7 C8 C9 C10 171.55(18) . . . . ?
C14 N3 C11 O4 -175.9(2) . . . . ?
C14 N3 C11 C12 4.1(2) . . . . ?
C14 C13 C12 C11 10.1(2) . . . . ?
C8 C7 C6 C5 173.15(18) . . . . ?
C11 N3 C14 O5 -178.4(2) . . . . ?
C11 N3 C14 C13 2.4(2) . . . . ?
C6 C7 C8 C9 173.45(19) . . . . ?
C4 S1 C5 C2 -41.24(14) . . . . ?
C4 S1 C5 C6 -166.85(16) . . . . ?
C4 C3 C2 N2 121.53(18) . . . . ?
C4 C3 C2 C5 1.4(2) . . . . ?


#----------------------------------------------------------------------------#
#                       SHELX RES FILE                                       #
#----------------------------------------------------------------------------#


# END of CIF
_chemical_name_systematic        
'2,5-dioxopyrrolidin-1-yl 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate'
_chemical_name_common            Biotin-NHS
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
