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

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

data_mo_scan_0m
_database_code_depnum_ccdc_archive 'CCDC 1991695'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        1-methyl-1H-imidazole-4,5-dicarbaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N2 O2'
_chemical_formula_weight         138.13

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   3.8712(16)
_cell_length_b                   6.840(3)
_cell_length_c                   23.770(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     629.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1648
_cell_measurement_theta_min      3.099
_cell_measurement_theta_max      28.195

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8519
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3988
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.713
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1563
_reflns_number_gt                1405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.0751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1563
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4397(6) 0.0308(3) 0.15393(8) 0.0561(5) Uani 1 1 d . . . . .
C1 C 0.9442(6) 0.6195(3) 0.17219(9) 0.0394(5) Uani 1 1 d . . . . .
H1 H 1.0504 0.7294 0.1874 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8540(5) 0.6041(2) 0.11775(7) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.5483(6) 0.4393(2) 0.01540(6) 0.0534(5) Uani 1 1 d . . . . .
C2 C 0.9147(7) 0.7545(3) 0.07469(10) 0.0422(5) Uani 1 1 d . . . . .
H2A H 1.0396 0.6983 0.0438 0.063 Uiso 1 1 calc R U . . .
H2B H 1.0469 0.8594 0.0906 0.063 Uiso 1 1 calc R U . . .
H2C H 0.6971 0.8039 0.0615 0.063 Uiso 1 1 calc R U . . .
N2 N 0.8663(5) 0.4622(3) 0.20181(8) 0.0411(5) Uani 1 1 d . . . . .
C3 C 0.7052(5) 0.4221(3) 0.11115(8) 0.0309(4) Uani 1 1 d . . . . .
C4 C 0.7144(5) 0.3381(3) 0.16432(8) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.5652(6) 0.3474(3) 0.05859(8) 0.0389(5) Uani 1 1 d . . . . .
H6 H 0.4830 0.2197 0.0583 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5857(7) 0.1477(3) 0.18296(9) 0.0423(5) Uani 1 1 d . . . . .
H5 H 0.6202 0.1147 0.2205 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.198(3) . ?
C1 N2 1.321(3) . ?
C1 N1 1.344(3) . ?
C1 H1 0.9300 . ?
N1 C3 1.381(3) . ?
N1 C2 1.470(3) . ?
O2 C6 1.206(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N2 C4 1.364(3) . ?
C3 C4 1.389(3) . ?
C3 C6 1.454(3) . ?
C4 C5 1.463(3) . ?
C6 H6 0.9300 . ?
C5 H5 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
N2 C1 N1 112.96(19) . . ?
N2 C1 H1 123.5 . . ?
N1 C1 H1 123.5 . . ?
C1 N1 C3 106.75(16) . . ?
C1 N1 C2 125.04(18) . . ?
C3 N1 C2 128.19(17) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C4 104.90(18) . . ?
N1 C3 C4 105.01(17) . . ?
N1 C3 C6 124.75(18) . . ?
C4 C3 C6 130.2(2) . . ?
N2 C4 C3 110.37(18) . . ?
N2 C4 C5 120.18(18) . . ?
C3 C4 C5 129.44(19) . . ?
O2 C6 C3 124.6(2) . . ?
O2 C6 H6 117.7 . . ?
C3 C6 H6 117.7 . . ?
O1 C5 C4 125.5(2) . . ?
O1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C3 0.0(3) . . . . ?
N2 C1 N1 C2 -178.8(2) . . . . ?
N1 C1 N2 C4 -0.4(3) . . . . ?
C1 N1 C3 C4 0.5(2) . . . . ?
C2 N1 C3 C4 179.1(2) . . . . ?
C1 N1 C3 C6 178.8(2) . . . . ?
C2 N1 C3 C6 -2.5(3) . . . . ?
C1 N2 C4 C3 0.7(3) . . . . ?
C1 N2 C4 C5 -178.6(2) . . . . ?
N1 C3 C4 N2 -0.7(2) . . . . ?
C6 C3 C4 N2 -179.0(2) . . . . ?
N1 C3 C4 C5 178.5(2) . . . . ?
C6 C3 C4 C5 0.2(4) . . . . ?
N1 C3 C6 O2 -3.7(4) . . . . ?
C4 C3 C6 O2 174.3(2) . . . . ?
N2 C4 C5 O1 177.7(2) . . . . ?
C3 C4 C5 O1 -1.5(4) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_mo_PBP_61-auto
_database_code_depnum_ccdc_archive 'CCDC 1991700'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N2'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.0018(5)
_cell_length_b                   8.6564(7)
_cell_length_c                   14.5956(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     758.30(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.791
_cell_measurement_theta_max      35.564
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22988
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.736
_diffrn_reflns_theta_max         34.860
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3301
_reflns_number_gt                3059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP 3 for Windows (Version 2014.1)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.0875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1235 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3301
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.55324(16) 0.48990(10) 0.50694(6) 0.01628(17) Uani 1 1 d . . . . .
C1 C 0.7296(2) 0.39222(13) 0.50969(8) 0.0197(2) Uani 1 1 d . . . . .
H1 H 0.752314 0.311313 0.466717 0.024 Uiso 1 1 calc R U . . .
N2 N 0.86640(18) 0.42123(11) 0.57824(7) 0.02031(19) Uani 1 1 d . . . . .
C2 C 0.77049(18) 0.54492(12) 0.62410(7) 0.01561(18) Uani 1 1 d . . . . .
C3 C 0.8764(2) 0.62539(12) 0.69906(8) 0.0190(2) Uani 1 1 d . . . . .
H3 H 1.032852 0.614244 0.706488 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7659(2) 0.71517(14) 0.75889(8) 0.0213(2) Uani 1 1 d . . . . .
H4 H 0.848843 0.776609 0.800669 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5150(2) 0.72186(14) 0.76209(8) 0.0228(2) Uani 1 1 d . . . . .
H5A H 0.455195 0.615989 0.769383 0.027 Uiso 1 1 calc R U . . .
H5AB H 0.467983 0.783226 0.815961 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4194(2) 0.79308(13) 0.67659(8) 0.0209(2) Uani 1 1 d . . . . .
H6 H 0.343269 0.889032 0.680917 0.025 Uiso 1 1 calc R U . . .
C7 C 0.43862(19) 0.72474(12) 0.59442(8) 0.01801(19) Uani 1 1 d . . . . .
H7 H 0.359514 0.766916 0.543896 0.022 Uiso 1 1 calc R U . . .
C8 C 0.57475(17) 0.58985(11) 0.57996(7) 0.01435(17) Uani 1 1 d . . . . .
C9 C 0.3764(2) 0.49275(14) 0.43861(8) 0.0215(2) Uani 1 1 d . . . . .
H9A H 0.390305 0.586281 0.401219 0.032 Uiso 1 1 calc R U . . .
H9B H 0.231323 0.492437 0.469414 0.032 Uiso 1 1 calc R U . . .
H9C H 0.388643 0.401442 0.399239 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3555(14) . ?
N1 C8 1.3788(13) . ?
N1 C9 1.4565(15) . ?
C1 N2 1.3183(16) . ?
C1 H1 0.9500 . ?
N2 C2 1.3877(14) . ?
C2 C8 1.3951(15) . ?
C2 C3 1.4445(16) . ?
C3 C4 1.3441(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.5076(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.5056(17) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.3422(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4407(15) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 107.18(9) . . ?
C1 N1 C9 126.86(10) . . ?
C8 N1 C9 125.94(9) . . ?
N2 C1 N1 112.95(10) . . ?
N2 C1 H1 123.5 . . ?
N1 C1 H1 123.5 . . ?
C1 N2 C2 104.76(9) . . ?
N2 C2 C8 109.98(9) . . ?
N2 C2 C3 123.70(10) . . ?
C8 C2 C3 125.87(10) . . ?
C4 C3 C2 123.62(11) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C3 C4 C5 122.36(11) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 111.77(10) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5AB 109.3 . . ?
C4 C5 H5AB 109.3 . . ?
H5A C5 H5AB 107.9 . . ?
C7 C6 C5 121.82(10) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 122.47(10) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
N1 C8 C2 105.12(9) . . ?
N1 C8 C7 124.66(9) . . ?
C2 C8 C7 129.48(10) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C8 N1 C1 N2 -0.65(13) . . . . ?
C9 N1 C1 N2 177.79(10) . . . . ?
N1 C1 N2 C2 0.95(13) . . . . ?
C1 N2 C2 C8 -0.89(12) . . . . ?
C1 N2 C2 C3 -173.56(10) . . . . ?
N2 C2 C3 C4 -161.50(11) . . . . ?
C8 C2 C3 C4 27.00(17) . . . . ?
C2 C3 C4 C5 9.36(18) . . . . ?
C3 C4 C5 C6 -66.55(15) . . . . ?
C4 C5 C6 C7 65.58(16) . . . . ?
C5 C6 C7 C8 -8.03(19) . . . . ?
C1 N1 C8 C2 0.06(11) . . . . ?
C9 N1 C8 C2 -178.40(10) . . . . ?
C1 N1 C8 C7 171.02(10) . . . . ?
C9 N1 C8 C7 -7.44(17) . . . . ?
N2 C2 C8 N1 0.51(12) . . . . ?
C3 C2 C8 N1 173.00(10) . . . . ?
N2 C2 C8 C7 -169.85(11) . . . . ?
C3 C2 C8 C7 2.64(18) . . . . ?
C6 C7 C8 N1 160.42(11) . . . . ?
C6 C7 C8 C2 -30.92(18) . . . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_mo_SA_458_2_3-auto
_database_code_depnum_ccdc_archive 'CCDC 1991698'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N2 Se,B F4'
_chemical_formula_sum            'C10 H11 B F4 N2 Se'
_chemical_formula_weight         324.98

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.1299(18)
_cell_length_b                   6.2796(10)
_cell_length_c                   16.088(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.965(6)
_cell_angle_gamma                90
_cell_volume                     1220.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6921
_cell_measurement_theta_min      2.542
_cell_measurement_theta_max      26.5115

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.107
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12836
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         28.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2422
_reflns_number_gt                2021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+4.3211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.92751(4) 0.20892(8) 0.47186(4) 0.0386(2) Uani 1 1 d . . . . .
F1 F 0.5297(3) 0.3312(6) 0.2650(2) 0.0659(12) Uani 1 1 d . . . . .
F2 F 0.3669(3) 0.4964(7) 0.2709(2) 0.0627(11) Uani 1 1 d . . . . .
F3 F 0.5211(4) 0.6872(6) 0.2692(2) 0.0714(13) Uani 1 1 d . . . . .
F4 F 0.4931(3) 0.4945(5) 0.38256(18) 0.0538(9) Uani 1 1 d . . . . .
N1 N 0.8243(3) 0.5388(6) 0.5589(2) 0.0229(8) Uani 1 1 d . . . . .
N2 N 0.7944(3) 0.5676(6) 0.4228(2) 0.0230(8) Uani 1 1 d . . . . .
C1 C 0.8474(3) 0.4436(7) 0.4852(3) 0.0256(9) Uani 1 1 d . . . . .
C2 C 0.8002(4) 0.5250(9) 0.3333(3) 0.0388(12) Uani 1 1 d . . . . .
H2A H 0.7252 0.5157 0.3057 0.058 Uiso 1 1 calc R U . . .
H2B H 0.8390 0.3901 0.3264 0.058 Uiso 1 1 calc R U . . .
H2C H 0.8404 0.6407 0.3084 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8681(4) 0.4644(9) 0.6416(3) 0.0353(11) Uani 1 1 d . . . . .
H3A H 0.9090 0.3314 0.6359 0.053 Uiso 1 1 calc R U . . .
H3B H 0.8067 0.4395 0.6762 0.053 Uiso 1 1 calc R U . . .
H3C H 0.9178 0.5725 0.6680 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7619(3) 0.7181(7) 0.5437(3) 0.0214(9) Uani 1 1 d . . . . .
C5 C 0.7282(4) 0.8527(8) 0.6052(3) 0.0290(10) Uani 1 1 d . . . . .
H5 H 0.7489 0.8143 0.6616 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6676(4) 1.0364(8) 0.5920(3) 0.0365(12) Uani 1 1 d . . . . .
H6 H 0.6537 1.1118 0.6412 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6236(4) 1.1289(8) 0.5184(4) 0.0395(13) Uani 1 1 d . . . . .
H7 H 0.5835 1.2569 0.5248 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6293(4) 1.0628(8) 0.4371(4) 0.0365(12) Uani 1 1 d . . . . .
H8 H 0.5916 1.1501 0.3956 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6823(4) 0.8871(8) 0.4081(3) 0.0299(10) Uani 1 1 d . . . . .
H9 H 0.6773 0.8685 0.3492 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7420(3) 0.7349(7) 0.4550(3) 0.0220(9) Uani 1 1 d . . . . .
B1 B 0.4783(4) 0.5015(8) 0.2964(3) 0.0266(11) Uani 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
Se1 C1 1.788(5) . ?
F1 B1 1.358(6) . ?
F2 B1 1.378(6) . ?
F3 B1 1.364(6) . ?
F4 B1 1.382(6) . ?
N1 C4 1.367(6) . ?
N1 C1 1.379(6) . ?
N1 C3 1.466(6) . ?
N2 C10 1.354(6) . ?
N2 C1 1.384(6) . ?
N2 C2 1.471(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.390(6) . ?
C4 C10 1.431(6) . ?
C5 C6 1.374(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(7) . ?
C9 H9 0.9500 . ?

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 N1 C1 110.8(4) . . ?
C4 N1 C3 125.2(4) . . ?
C1 N1 C3 123.9(4) . . ?
C10 N2 C1 111.3(3) . . ?
C10 N2 C2 125.4(4) . . ?
C1 N2 C2 123.2(4) . . ?
N1 C1 N2 105.3(4) . . ?
N1 C1 Se1 127.8(3) . . ?
N2 C1 Se1 126.9(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 124.5(4) . . ?
N1 C4 C10 106.3(4) . . ?
C5 C4 C10 129.1(4) . . ?
C6 C5 C4 125.9(5) . . ?
C6 C5 H5 117.1 . . ?
C4 C5 H5 117.1 . . ?
C5 C6 C7 130.3(5) . . ?
C5 C6 H6 114.8 . . ?
C7 C6 H6 114.8 . . ?
C8 C7 C6 129.6(5) . . ?
C8 C7 H7 115.2 . . ?
C6 C7 H7 115.2 . . ?
C7 C8 C9 128.7(5) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
C8 C9 C10 127.2(5) . . ?
C8 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
N2 C10 C9 124.6(4) . . ?
N2 C10 C4 106.3(4) . . ?
C9 C10 C4 129.1(4) . . ?
F1 B1 F3 110.7(5) . . ?
F1 B1 F2 109.9(4) . . ?
F3 B1 F2 108.3(4) . . ?
F1 B1 F4 108.9(4) . . ?
F3 B1 F4 109.2(4) . . ?
F2 B1 F4 109.8(4) . . ?

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
C4 N1 C1 N2 -1.5(5) . . . . ?
C3 N1 C1 N2 -177.5(4) . . . . ?
C4 N1 C1 Se1 179.0(3) . . . . ?
C3 N1 C1 Se1 3.1(6) . . . . ?
C10 N2 C1 N1 1.1(5) . . . . ?
C2 N2 C1 N1 178.3(4) . . . . ?
C10 N2 C1 Se1 -179.4(3) . . . . ?
C2 N2 C1 Se1 -2.2(6) . . . . ?
C1 N1 C4 C5 -177.8(4) . . . . ?
C3 N1 C4 C5 -2.0(7) . . . . ?
C1 N1 C4 C10 1.4(5) . . . . ?
C3 N1 C4 C10 177.3(4) . . . . ?
N1 C4 C5 C6 178.5(4) . . . . ?
C10 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C7 1.9(8) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C9 -1.0(9) . . . . ?
C7 C8 C9 C10 0.4(8) . . . . ?
C1 N2 C10 C9 179.8(4) . . . . ?
C2 N2 C10 C9 2.6(7) . . . . ?
C1 N2 C10 C4 -0.3(5) . . . . ?
C2 N2 C10 C4 -177.4(4) . . . . ?
C8 C9 C10 N2 -178.6(4) . . . . ?
C8 C9 C10 C4 1.4(8) . . . . ?
N1 C4 C10 N2 -0.7(4) . . . . ?
C5 C4 C10 N2 178.5(4) . . . . ?
N1 C4 C10 C9 179.3(4) . . . . ?
C5 C4 C10 C9 -1.5(8) . . . . ?

_refine_diff_density_max         1.550
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.113



####################################################################### 
# 
# 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_SA-457
_database_code_depnum_ccdc_archive 'CCDC 1991697'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2 Se'
_chemical_formula_sum            'C10 H12 N2 Se'
_chemical_formula_weight         239.18

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.8033(8)
_cell_length_b                   10.5327(15)
_cell_length_c                   16.799(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1026.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7307
_cell_measurement_theta_min      2.2825
_cell_measurement_theta_max      24.664

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.612
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5454
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19341
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         29.964
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2955
_reflns_number_gt                2257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.4607P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se 0.79170(9) 0.49918(5) 0.46882(3) 0.0703(2) Uani 1 1 d . . . . .
N1 N 0.4357(6) 0.5179(3) 0.58606(18) 0.0450(7) Uani 1 1 d . . . . .
C1 C 0.6116(7) 0.4523(4) 0.5544(2) 0.0445(9) Uani 1 1 d . . . . .
C2 C 0.3560(11) 0.6404(4) 0.5574(3) 0.0643(13) Uani 1 1 d . . . . .
H2A H 0.3210 0.6942 0.6019 0.096 Uiso 1 1 calc R U . . .
H2B H 0.2200 0.6289 0.5256 0.096 Uiso 1 1 calc R U . . .
H2C H 0.4743 0.6791 0.5257 0.096 Uiso 1 1 calc R U . . .
C3 C 0.8075(9) 0.2465(4) 0.5853(3) 0.0658(12) Uani 1 1 d . . . . .
H3A H 0.7326 0.1664 0.5767 0.099 Uiso 1 1 calc R U . . .
H3B H 0.9064 0.2405 0.6309 0.099 Uiso 1 1 calc R U . . .
H3C H 0.8975 0.2680 0.5393 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4717(7) 0.3443(3) 0.6589(2) 0.0435(8) Uani 1 1 d . . . . .
C5 C 0.4248(9) 0.2387(4) 0.7106(3) 0.0576(11) Uani 1 1 d . . . . .
H5 H 0.4713 0.1577 0.6954 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3164(11) 0.2539(5) 0.7798(3) 0.0668(14) Uani 1 1 d . . . . .
H6 H 0.2708 0.1819 0.8078 0.080 Uiso 1 1 calc R U . . .
N2 N 0.6333(6) 0.3450(3) 0.5989(2) 0.0459(7) Uani 1 1 d . . . . .
C9 C 0.1381(9) 0.4882(5) 0.6918(3) 0.0641(11) Uani 1 1 d . . . . .
H9 H 0.0323 0.5397 0.6657 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2648(12) 0.3806(6) 0.8146(3) 0.0779(17) Uani 1 1 d . . . . .
H7A H 0.4055 0.4300 0.8177 0.093 Uiso 1 1 calc R U . . .
H7B H 0.2057 0.3701 0.8682 0.093 Uiso 1 1 calc R U . . .
C10 C 0.3445(7) 0.4531(4) 0.6515(2) 0.0445(8) Uani 1 1 d . . . . .
C8 C 0.0913(11) 0.4501(6) 0.7652(3) 0.0760(16) Uani 1 1 d . . . . .
H8 H -0.0532 0.4670 0.7866 0.091 Uiso 1 1 calc R U . . .


_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
Se C1 1.845(4) . ?
N1 C1 1.343(5) . ?
N1 C10 1.398(5) . ?
N1 C2 1.453(5) . ?
C1 N2 1.361(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N2 1.467(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C10 1.369(5) . ?
C4 N2 1.377(5) . ?
C4 C5 1.437(6) . ?
C5 C6 1.331(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(8) . ?
C6 H6 0.9300 . ?
C9 C8 1.324(7) . ?
C9 C10 1.425(6) . ?
C9 H9 0.9300 . ?
C7 C8 1.496(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 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
C1 N1 C10 110.4(3) . . ?
C1 N1 C2 124.6(4) . . ?
C10 N1 C2 125.0(4) . . ?
N1 C1 N2 106.3(3) . . ?
N1 C1 Se 127.0(3) . . ?
N2 C1 Se 126.7(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C10 C4 N2 107.2(3) . . ?
C10 C4 C5 126.9(4) . . ?
N2 C4 C5 125.1(4) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 123.1(5) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C1 N2 C4 110.1(3) . . ?
C1 N2 C3 124.4(4) . . ?
C4 N2 C3 125.4(4) . . ?
C8 C9 C10 122.4(5) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C6 C7 C8 110.9(5) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C4 C10 N1 106.0(4) . . ?
C4 C10 C9 128.8(4) . . ?
N1 C10 C9 124.4(4) . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?

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
C10 N1 C1 N2 0.4(4) . . . . ?
C2 N1 C1 N2 178.9(4) . . . . ?
C10 N1 C1 Se -178.6(3) . . . . ?
C2 N1 C1 Se -0.2(6) . . . . ?
C10 C4 C5 C6 -29.8(7) . . . . ?
N2 C4 C5 C6 161.1(5) . . . . ?
C4 C5 C6 C7 -8.8(8) . . . . ?
N1 C1 N2 C4 -0.6(4) . . . . ?
Se C1 N2 C4 178.5(3) . . . . ?
N1 C1 N2 C3 -179.4(4) . . . . ?
Se C1 N2 C3 -0.3(6) . . . . ?
C10 C4 N2 C1 0.5(4) . . . . ?
C5 C4 N2 C1 171.4(4) . . . . ?
C10 C4 N2 C3 179.3(4) . . . . ?
C5 C4 N2 C3 -9.8(7) . . . . ?
C5 C6 C7 C8 67.3(8) . . . . ?
N2 C4 C10 N1 -0.2(4) . . . . ?
C5 C4 C10 N1 -171.0(4) . . . . ?
N2 C4 C10 C9 170.4(4) . . . . ?
C5 C4 C10 C9 -0.3(7) . . . . ?
C1 N1 C10 C4 -0.1(4) . . . . ?
C2 N1 C10 C4 -178.6(4) . . . . ?
C1 N1 C10 C9 -171.2(4) . . . . ?
C2 N1 C10 C9 10.3(6) . . . . ?
C8 C9 C10 C4 30.9(8) . . . . ?
C8 C9 C10 N1 -160.0(5) . . . . ?
C10 C9 C8 C7 7.6(9) . . . . ?
C6 C7 C8 C9 -66.0(8) . . . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_cu_scan_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1991696'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1,3-dimethylcyclohepta[d]imidazole-1,3-diium-trifluoromethanesulfonate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2, C2 F6 O6 S2'
_chemical_formula_sum            'C12 H12 F6 N2 O6 S2'
_chemical_formula_weight         458.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.8205(4)
_cell_length_b                   12.3993(7)
_cell_length_c                   21.2683(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.480(3)
_cell_angle_gamma                90
_cell_volume                     1798.58(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      4.127
_cell_measurement_theta_max      66.001

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    3.599
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4470
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13229
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.127
_diffrn_reflns_theta_max         59.971
_diffrn_reflns_theta_full        59.971
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2602
_reflns_number_gt                2452
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1191P)²+2.7926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2602
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.28186(15) 0.43917(8) 0.33593(6) 0.0590(4) Uani 1 1 d . . . . .
S2 S 0.3079(2) 0.11758(13) 0.59879(8) 0.0857(5) Uani 1 1 d . . . . .
F1 F 0.3772(11) 0.4268(5) 0.4529(2) 0.190(3) Uani 1 1 d . . . . .
F2 F 0.0881(12) 0.4917(6) 0.4341(3) 0.200(3) Uani 1 1 d . . . . .
F3 F 0.3424(11) 0.5881(4) 0.4185(2) 0.172(2) Uani 1 1 d . . . . .
F4 F 0.2003(10) 0.3144(5) 0.6166(4) 0.212(4) Uani 1 1 d . . . . .
F5 F -0.0355(5) 0.2087(5) 0.5937(2) 0.1376(17) Uani 1 1 d . . . . .
F6 F 0.1658(7) 0.2622(4) 0.5248(2) 0.1399(17) Uani 1 1 d . . . . .
O1 O 0.4853(5) 0.4303(3) 0.3237(2) 0.0895(12) Uani 1 1 d . . . . .
O2 O 0.1869(6) 0.3376(3) 0.3397(3) 0.1138(16) Uani 1 1 d . . . . .
O3 O 0.1834(6) 0.5201(3) 0.29999(19) 0.0944(12) Uani 1 1 d . . . . .
O4 O 0.2253(9) 0.0407(5) 0.5624(4) 0.168(3) Uani 1 1 d . . . . .
O5 O 0.4909(7) 0.1491(5) 0.5825(4) 0.167(3) Uani 1 1 d . . . . .
O6 O 0.2756(11) 0.0931(9) 0.6597(3) 0.230(5) Uani 1 1 d . . . . .
N1 N 0.6935(5) 0.2320(3) 0.28914(18) 0.0587(9) Uani 1 1 d . . . . .
N2 N 0.6770(5) 0.2157(3) 0.39070(18) 0.0620(10) Uani 1 1 d . . . . .
C1 C 0.7776(7) 0.2554(4) 0.3438(3) 0.0669(13) Uani 1 1 d . . . . .
C2 C 0.7305(10) 0.2266(6) 0.4578(3) 0.101(2) Uani 1 1 d . . . . .
H2A H 0.6213 0.2555 0.4805 0.152 Uiso 1 1 calc R U . . .
H2B H 0.8407 0.2743 0.4620 0.152 Uiso 1 1 calc R U . . .
H2C H 0.7642 0.1571 0.4746 0.152 Uiso 1 1 calc R U . . .
C3 C 0.7625(13) 0.2713(6) 0.2284(3) 0.0888(18) Uani 1 1 d . . . . .
C4 C 0.5260(6) 0.1740(3) 0.30104(19) 0.0514(10) Uani 1 1 d . . . . .
C5 C 0.4012(7) 0.1376(4) 0.2547(2) 0.0636(12) Uani 1 1 d . . . . .
C6 C 0.2284(8) 0.0830(4) 0.2636(3) 0.0725(13) Uani 1 1 d . . . . .
C7 C 0.1452(8) 0.0512(4) 0.3187(3) 0.0793(17) Uani 1 1 d . . . . .
C8 C 0.2096(8) 0.0618(4) 0.3810(3) 0.0762(15) Uani 1 1 d . . . . .
C9 C 0.3775(7) 0.1113(4) 0.4028(2) 0.0646(12) Uani 1 1 d . . . . .
C10 C 0.5146(6) 0.1628(3) 0.36642(19) 0.0510(10) Uani 1 1 d . . . . .
C11 C 0.2738(14) 0.4907(6) 0.4151(3) 0.110(2) Uani 1 1 d . . . . .
C12 C 0.1551(9) 0.2314(6) 0.5833(3) 0.0929(18) Uani 1 1 d . . . . .
H1 H 0.876(8) 0.299(4) 0.348(2) 0.077(15) Uiso 1 1 d . . . . .
H3A H 0.865(9) 0.306(5) 0.235(3) 0.085(19) Uiso 1 1 d . . . . .
H3B H 0.669(10) 0.330(6) 0.215(3) 0.11(2) Uiso 1 1 d . . . . .
H3C H 0.771(9) 0.204(6) 0.203(3) 0.10(2) Uiso 1 1 d . . . . .
H5 H 0.450(8) 0.157(4) 0.214(3) 0.079(15) Uiso 1 1 d . . . . .
H6 H 0.157(8) 0.061(4) 0.221(2) 0.075(14) Uiso 1 1 d . . . . .
H7 H 0.028(10) 0.014(5) 0.318(3) 0.103(19) Uiso 1 1 d . . . . .
H8 H 0.133(10) 0.015(6) 0.424(3) 0.12(2) Uiso 1 1 d . . . . .
H9 H 0.404(6) 0.108(3) 0.444(2) 0.048(11) 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
S1 O1 1.418(4) . ?
S1 O2 1.418(4) . ?
S1 O3 1.427(4) . ?
S1 C11 1.803(7) . ?
S2 O4 1.349(6) . ?
S2 O6 1.351(6) . ?
S2 O5 1.356(5) . ?
S2 C12 1.783(7) . ?
F1 C11 1.327(8) . ?
F2 C11 1.332(10) . ?
F3 C11 1.297(9) . ?
F4 C12 1.286(7) . ?
F5 C12 1.350(7) . ?
F6 C12 1.304(7) . ?
N1 C1 1.325(6) . ?
N1 C4 1.376(5) . ?
N1 C3 1.463(7) . ?
N2 C1 1.310(6) . ?
N2 C10 1.383(5) . ?
N2 C2 1.477(6) . ?
C1 H1 0.86(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.83(6) . ?
C3 H3B 1.01(7) . ?
C3 H3C 0.99(7) . ?
C4 C5 1.373(6) . ?
C4 C10 1.400(6) . ?
C5 C6 1.374(7) . ?
C5 H5 0.95(6) . ?
C6 C7 1.364(9) . ?
C6 H6 1.06(5) . ?
C7 C8 1.398(9) . ?
C7 H7 0.93(7) . ?
C8 C9 1.376(8) . ?
C8 H8 1.20(7) . ?
C9 C10 1.376(6) . ?
C9 H9 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 112.9(2) . . ?
O1 S1 O3 114.4(3) . . ?
O2 S1 O3 116.2(3) . . ?
O1 S1 C11 103.7(4) . . ?
O2 S1 C11 104.1(4) . . ?
O3 S1 C11 103.5(3) . . ?
O4 S2 O6 108.7(6) . . ?
O4 S2 O5 116.0(5) . . ?
O6 S2 O5 117.9(5) . . ?
O4 S2 C12 102.3(3) . . ?
O6 S2 C12 104.8(5) . . ?
O5 S2 C12 105.2(3) . . ?
C1 N1 C4 107.9(4) . . ?
C1 N1 C3 124.3(5) . . ?
C4 N1 C3 127.6(5) . . ?
C1 N2 C10 108.5(4) . . ?
C1 N2 C2 125.0(4) . . ?
C10 N2 C2 126.5(4) . . ?
N2 C1 N1 111.1(4) . . ?
N2 C1 H1 124(4) . . ?
N1 C1 H1 124(4) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 107(4) . . ?
N1 C3 H3B 106(4) . . ?
H3A C3 H3B 102(6) . . ?
N1 C3 H3C 103(4) . . ?
H3A C3 H3C 118(6) . . ?
H3B C3 H3C 119(5) . . ?
C5 C4 N1 123.4(4) . . ?
C5 C4 C10 129.9(4) . . ?
N1 C4 C10 106.7(3) . . ?
C4 C5 C6 126.1(5) . . ?
C4 C5 H5 110(3) . . ?
C6 C5 H5 124(3) . . ?
C7 C6 C5 128.7(5) . . ?
C7 C6 H6 118(3) . . ?
C5 C6 H6 113(3) . . ?
C6 C7 C8 131.0(5) . . ?
C6 C7 H7 120(4) . . ?
C8 C7 H7 109(4) . . ?
C9 C8 C7 127.9(5) . . ?
C9 C8 H8 109(3) . . ?
C7 C8 H8 122(3) . . ?
C10 C9 C8 125.8(5) . . ?
C10 C9 H9 116(3) . . ?
C8 C9 H9 118(3) . . ?
C9 C10 N2 123.8(4) . . ?
C9 C10 C4 130.4(4) . . ?
N2 C10 C4 105.9(4) . . ?
F3 C11 F1 109.5(8) . . ?
F3 C11 F2 108.6(7) . . ?
F1 C11 F2 108.9(7) . . ?
F3 C11 S1 111.6(5) . . ?
F1 C11 S1 109.5(6) . . ?
F2 C11 S1 108.8(6) . . ?
F4 C12 F6 106.0(7) . . ?
F4 C12 F5 107.6(6) . . ?
F6 C12 F5 106.3(5) . . ?
F4 C12 S2 113.2(5) . . ?
F6 C12 S2 111.8(4) . . ?
F5 C12 S2 111.5(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
C10 N2 C1 N1 -0.3(5) . . . . ?
C2 N2 C1 N1 179.7(5) . . . . ?
C4 N1 C1 N2 0.5(5) . . . . ?
C3 N1 C1 N2 175.5(5) . . . . ?
C1 N1 C4 C5 179.2(4) . . . . ?
C3 N1 C4 C5 4.4(7) . . . . ?
C1 N1 C4 C10 -0.5(4) . . . . ?
C3 N1 C4 C10 -175.2(5) . . . . ?
N1 C4 C5 C6 -177.3(4) . . . . ?
C10 C4 C5 C6 2.3(8) . . . . ?
C4 C5 C6 C7 -1.6(9) . . . . ?
C5 C6 C7 C8 -1.5(10) . . . . ?
C6 C7 C8 C9 1.8(9) . . . . ?
C7 C8 C9 C10 1.5(8) . . . . ?
C8 C9 C10 N2 177.0(4) . . . . ?
C8 C9 C10 C4 -3.4(8) . . . . ?
C1 N2 C10 C9 179.7(4) . . . . ?
C2 N2 C10 C9 -0.3(7) . . . . ?
C1 N2 C10 C4 0.0(5) . . . . ?
C2 N2 C10 C4 180.0(5) . . . . ?
C5 C4 C10 C9 1.0(7) . . . . ?
N1 C4 C10 C9 -179.4(4) . . . . ?
C5 C4 C10 N2 -179.4(4) . . . . ?
N1 C4 C10 N2 0.3(4) . . . . ?
O1 S1 C11 F3 66.6(7) . . . . ?
O2 S1 C11 F3 -175.0(6) . . . . ?
O3 S1 C11 F3 -53.1(7) . . . . ?
O1 S1 C11 F1 -54.7(7) . . . . ?
O2 S1 C11 F1 63.7(7) . . . . ?
O3 S1 C11 F1 -174.4(6) . . . . ?
O1 S1 C11 F2 -173.6(5) . . . . ?
O2 S1 C11 F2 -55.2(6) . . . . ?
O3 S1 C11 F2 66.7(6) . . . . ?
O4 S2 C12 F4 176.0(7) . . . . ?
O6 S2 C12 F4 62.6(8) . . . . ?
O5 S2 C12 F4 -62.4(8) . . . . ?
O4 S2 C12 F6 -64.4(6) . . . . ?
O6 S2 C12 F6 -177.7(6) . . . . ?
O5 S2 C12 F6 57.3(6) . . . . ?
O4 S2 C12 F5 54.4(6) . . . . ?
O6 S2 C12 F5 -58.9(6) . . . . ?
O5 S2 C12 F5 176.1(5) . . . . ?

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.075



####################################################################### 
# 
# 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_mo_Duo_Appel_SA_452_2-auto
_database_code_depnum_ccdc_archive 'CCDC 1991699'
loop_
_audit_author_name
_audit_author_address
'Christian Ganter'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 Cl N2 Rh, B F4'
_chemical_formula_sum            'C18 H23 B Cl F4 N2 Rh'
_chemical_formula_weight         492.55

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.0887(4)
_cell_length_b                   20.7670(10)
_cell_length_c                   11.8752(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.634(2)
_cell_angle_gamma                90
_cell_volume                     1911.30(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9716
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      41.6615

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.076
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_T_max  0.7482
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83649
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.961
_diffrn_reflns_theta_max         41.920
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12052
_reflns_number_gt                10881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+0.7443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12052
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh Rh 0.30963(2) 0.66696(2) 0.34904(2) 0.01377(2) Uani 1 1 d . . . . .
Cl Cl 0.03457(3) 0.70355(2) 0.23205(2) 0.02516(4) Uani 1 1 d . . . . .
B B 0.66907(13) 0.46900(5) 0.26305(9) 0.01993(16) Uani 1 1 d . . . . .
F1 F 0.58316(11) 0.43880(5) 0.15804(7) 0.03943(18) Uani 1 1 d . . . . .
F2 F 0.75066(11) 0.52381(4) 0.23713(7) 0.03544(16) Uani 1 1 d . . . . .
F3 F 0.55185(9) 0.48630(4) 0.32377(6) 0.02765(13) Uani 1 1 d . . . . .
F4 F 0.79223(8) 0.42781(4) 0.33231(6) 0.02721(12) Uani 1 1 d . . . . .
N1 N 0.28754(9) 0.56567(3) 0.16052(6) 0.01338(10) Uani 1 1 d . . . . .
N2 N 0.19020(9) 0.53094(3) 0.30177(6) 0.01427(10) Uani 1 1 d . . . . .
C1 C 0.26573(10) 0.58303(4) 0.26661(7) 0.01391(11) Uani 1 1 d . . . . .
C2 C 0.37410(13) 0.60626(4) 0.09472(8) 0.01985(14) Uani 1 1 d . . . . .
C3 C 0.14593(13) 0.52843(5) 0.41288(8) 0.02101(15) Uani 1 1 d . . . . .
C4 C 0.16338(9) 0.48207(4) 0.22140(7) 0.01313(10) Uani 1 1 d . . . . .
C5 C 0.09255(11) 0.42280(4) 0.23512(8) 0.01717(12) Uani 1 1 d . . . . .
C6 C 0.05590(12) 0.37291(4) 0.15375(8) 0.01982(14) Uani 1 1 d . . . . .
C7 C 0.07811(12) 0.37085(4) 0.04173(8) 0.01934(14) Uani 1 1 d . . . . .
C8 C 0.15150(11) 0.41613(4) -0.01639(7) 0.01726(12) Uani 1 1 d . . . . .
C9 C 0.22227(10) 0.47592(4) 0.02207(7) 0.01509(11) Uani 1 1 d . . . . .
C10 C 0.22552(9) 0.50517(3) 0.12784(6) 0.01241(10) Uani 1 1 d . . . . .
C11 C 0.58158(12) 0.65483(5) 0.39901(9) 0.02191(15) Uani 1 1 d . . . . .
C12 C 0.51833(12) 0.63127(4) 0.48991(8) 0.02028(14) Uani 1 1 d . . . . .
C13 C 0.53784(14) 0.66705(5) 0.60491(9) 0.02353(16) Uani 1 1 d . . . . .
C14 C 0.37959(14) 0.70871(4) 0.60139(8) 0.02209(15) Uani 1 1 d . . . . .
C15 C 0.29846(12) 0.73874(4) 0.48313(7) 0.01765(13) Uani 1 1 d . . . . .
C16 C 0.38408(12) 0.76698(4) 0.41085(8) 0.01845(13) Uani 1 1 d . . . . .
C17 C 0.57757(14) 0.77572(5) 0.44144(10) 0.02509(17) Uani 1 1 d . . . . .
C18 C 0.67043(14) 0.71923(6) 0.40134(11) 0.02760(18) Uani 1 1 d . . . . .
H2A H 0.393(3) 0.6451(10) 0.1289(18) 0.045(5) Uiso 1 1 d . . . . .
H2B H 0.311(2) 0.6086(9) 0.0174(16) 0.037(5) Uiso 1 1 d . . . . .
H2C H 0.486(3) 0.5892(9) 0.1001(17) 0.040(5) Uiso 1 1 d . . . . .
H3A H 0.172(2) 0.5668(9) 0.4476(16) 0.036(4) Uiso 1 1 d . . . . .
H3B H 0.029(2) 0.5200(8) 0.3997(16) 0.034(4) Uiso 1 1 d . . . . .
H3C H 0.219(2) 0.4972(9) 0.4619(17) 0.040(5) Uiso 1 1 d . . . . .
H5 H 0.0645(19) 0.4163(7) 0.3061(13) 0.019(3) Uiso 1 1 d . . . . .
H6 H 0.007(2) 0.3341(7) 0.1789(16) 0.028(4) Uiso 1 1 d . . . . .
H7 H 0.041(2) 0.3347(7) 0.0000(15) 0.025(4) Uiso 1 1 d . . . . .
H8 H 0.1530(19) 0.4040(7) -0.0908(13) 0.018(3) Uiso 1 1 d . . . . .
H9 H 0.2677(18) 0.4990(7) -0.0252(13) 0.017(3) Uiso 1 1 d . . . . .
H11 H 0.611(2) 0.6247(8) 0.3515(14) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.506(2) 0.5865(8) 0.4942(14) 0.023(4) Uiso 1 1 d . . . . .
H13A H 0.554(2) 0.6361(8) 0.6650(14) 0.027(4) Uiso 1 1 d . . . . .
H13B H 0.634(2) 0.6926(9) 0.6203(16) 0.031(4) Uiso 1 1 d . . . . .
H15 H 0.1768(19) 0.7460(7) 0.4636(13) 0.019(3) Uiso 1 1 d . . . . .
H14A H 0.410(2) 0.7417(9) 0.6628(16) 0.034(4) Uiso 1 1 d . . . . .
H14B H 0.299(2) 0.6838(9) 0.6208(16) 0.035(4) Uiso 1 1 d . . . . .
H16 H 0.3163(18) 0.7921(8) 0.3461(13) 0.022(4) Uiso 1 1 d . . . . .
H17A H 0.621(2) 0.7813(8) 0.5207(15) 0.029(4) Uiso 1 1 d . . . . .
H17B H 0.601(2) 0.8126(9) 0.4063(16) 0.033(4) Uiso 1 1 d . . . . .
H18A H 0.680(2) 0.7267(8) 0.3230(16) 0.033(4) Uiso 1 1 d . . . . .
H18B H 0.790(3) 0.7151(9) 0.4504(18) 0.045(5) 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
Rh C1 1.9808(7) . ?
Rh C11 2.1230(9) . ?
Rh C12 2.1402(9) . ?
Rh C15 2.2018(8) . ?
Rh C16 2.2278(8) . ?
Rh Cl 2.3849(3) . ?
B F4 1.3898(12) . ?
B F1 1.3912(12) . ?
B F3 1.3926(12) . ?
B F2 1.3936(13) . ?
N1 C10 1.3672(10) . ?
N1 C1 1.3696(10) . ?
N1 C2 1.4575(11) . ?
N2 C1 1.3652(10) . ?
N2 C4 1.3672(10) . ?
N2 C3 1.4637(11) . ?
C2 H2A 0.90(2) . ?
C2 H2B 0.916(18) . ?
C2 H2C 0.96(2) . ?
C3 H3A 0.893(19) . ?
C3 H3B 0.927(18) . ?
C3 H3C 0.955(19) . ?
C4 C5 1.3868(11) . ?
C4 C10 1.4272(11) . ?
C5 C6 1.3896(12) . ?
C5 H5 0.943(15) . ?
C6 C7 1.3930(13) . ?
C6 H6 0.980(17) . ?
C7 C8 1.3954(13) . ?
C7 H7 0.903(16) . ?
C8 C9 1.3887(11) . ?
C8 H8 0.922(15) . ?
C9 C10 1.3887(10) . ?
C9 H9 0.894(15) . ?
C11 C12 1.4080(14) . ?
C11 C18 1.5148(15) . ?
C11 H11 0.917(16) . ?
C12 C13 1.5227(14) . ?
C12 H12 0.938(16) . ?
C13 C14 1.5356(15) . ?
C13 H13A 0.941(17) . ?
C13 H13B 0.917(18) . ?
C14 C15 1.5048(13) . ?
C14 H14A 0.979(18) . ?
C14 H14B 0.913(19) . ?
C15 C16 1.3786(13) . ?
C15 H15 0.956(15) . ?
C16 C17 1.5129(14) . ?
C16 H16 0.960(15) . ?
C17 C18 1.5400(16) . ?
C17 H17A 0.912(17) . ?
C17 H17B 0.917(19) . ?
C18 H18A 0.967(18) . ?
C18 H18B 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Rh C11 93.36(3) . . ?
C1 Rh C12 94.08(3) . . ?
C11 Rh C12 38.57(4) . . ?
C1 Rh C15 156.13(3) . . ?
C11 Rh C15 97.58(4) . . ?
C12 Rh C15 81.70(3) . . ?
C1 Rh C16 167.59(3) . . ?
C11 Rh C16 81.82(4) . . ?
C12 Rh C16 89.26(3) . . ?
C15 Rh C16 36.26(3) . . ?
C1 Rh Cl 89.26(2) . . ?
C11 Rh Cl 156.90(3) . . ?
C12 Rh Cl 163.99(3) . . ?
C15 Rh Cl 88.91(2) . . ?
C16 Rh Cl 90.80(2) . . ?
F4 B F1 110.03(9) . . ?
F4 B F3 109.35(8) . . ?
F1 B F3 109.94(8) . . ?
F4 B F2 109.20(8) . . ?
F1 B F2 108.47(9) . . ?
F3 B F2 109.84(9) . . ?
C10 N1 C1 111.69(6) . . ?
C10 N1 C2 124.95(7) . . ?
C1 N1 C2 123.30(7) . . ?
C1 N2 C4 111.73(6) . . ?
C1 N2 C3 123.38(7) . . ?
C4 N2 C3 124.89(7) . . ?
N2 C1 N1 105.04(6) . . ?
N2 C1 Rh 125.36(5) . . ?
N1 C1 Rh 129.36(6) . . ?
N1 C2 H2A 108.9(13) . . ?
N1 C2 H2B 110.6(12) . . ?
H2A C2 H2B 112.4(17) . . ?
N1 C2 H2C 109.9(12) . . ?
H2A C2 H2C 105.4(17) . . ?
H2B C2 H2C 109.5(16) . . ?
N2 C3 H3A 107.4(12) . . ?
N2 C3 H3B 110.7(11) . . ?
H3A C3 H3B 109.7(16) . . ?
N2 C3 H3C 107.7(12) . . ?
H3A C3 H3C 107.6(16) . . ?
H3B C3 H3C 113.5(16) . . ?
N2 C4 C5 124.42(7) . . ?
N2 C4 C10 105.84(6) . . ?
C5 C4 C10 129.73(7) . . ?
C4 C5 C6 126.38(8) . . ?
C4 C5 H5 116.5(9) . . ?
C6 C5 H5 117.1(9) . . ?
C5 C6 C7 128.80(8) . . ?
C5 C6 H6 115.2(10) . . ?
C7 C6 H6 116.0(10) . . ?
C6 C7 C8 129.88(8) . . ?
C6 C7 H7 115.8(11) . . ?
C8 C7 H7 114.4(11) . . ?
C9 C8 C7 129.31(8) . . ?
C9 C8 H8 116.3(9) . . ?
C7 C8 H8 114.4(9) . . ?
C10 C9 C8 126.00(8) . . ?
C10 C9 H9 115.4(9) . . ?
C8 C9 H9 118.6(9) . . ?
N1 C10 C9 124.68(7) . . ?
N1 C10 C4 105.68(6) . . ?
C9 C10 C4 129.60(7) . . ?
C12 C11 C18 124.58(9) . . ?
C12 C11 Rh 71.38(5) . . ?
C18 C11 Rh 110.40(7) . . ?
C12 C11 H11 116.6(10) . . ?
C18 C11 H11 114.2(10) . . ?
Rh C11 H11 109.6(10) . . ?
C11 C12 C13 123.43(9) . . ?
C11 C12 Rh 70.05(5) . . ?
C13 C12 Rh 112.84(6) . . ?
C11 C12 H12 116.9(10) . . ?
C13 C12 H12 114.9(10) . . ?
Rh C12 H12 108.3(10) . . ?
C12 C13 C14 112.26(8) . . ?
C12 C13 H13A 107.6(10) . . ?
C14 C13 H13A 109.9(10) . . ?
C12 C13 H13B 109.0(11) . . ?
C14 C13 H13B 109.5(11) . . ?
H13A C13 H13B 108.5(15) . . ?
C15 C14 C13 113.35(8) . . ?
C15 C14 H14A 110.7(10) . . ?
C13 C14 H14A 110.0(10) . . ?
C15 C14 H14B 108.6(12) . . ?
C13 C14 H14B 108.9(12) . . ?
H14A C14 H14B 104.9(16) . . ?
C16 C15 C14 126.50(9) . . ?
C16 C15 Rh 72.89(5) . . ?
C14 C15 Rh 107.28(5) . . ?
C16 C15 H15 116.6(9) . . ?
C14 C15 H15 115.8(9) . . ?
Rh C15 H15 100.6(9) . . ?
C15 C16 C17 124.82(8) . . ?
C15 C16 Rh 70.84(5) . . ?
C17 C16 Rh 110.76(6) . . ?
C15 C16 H16 117.1(9) . . ?
C17 C16 H16 116.2(9) . . ?
Rh C16 H16 101.8(10) . . ?
C16 C17 C18 113.39(8) . . ?
C16 C17 H17A 109.2(11) . . ?
C18 C17 H17A 109.7(11) . . ?
C16 C17 H17B 108.9(11) . . ?
C18 C17 H17B 108.2(12) . . ?
H17A C17 H17B 107.1(15) . . ?
C11 C18 C17 114.03(8) . . ?
C11 C18 H18A 106.9(10) . . ?
C17 C18 H18A 110.8(10) . . ?
C11 C18 H18B 108.5(12) . . ?
C17 C18 H18B 111.7(12) . . ?
H18A C18 H18B 104.3(16) . . ?

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
C4 N2 C1 N1 -0.33(9) . . . . ?
C3 N2 C1 N1 179.09(8) . . . . ?
C4 N2 C1 Rh 174.51(6) . . . . ?
C3 N2 C1 Rh -6.08(11) . . . . ?
C10 N1 C1 N2 1.05(9) . . . . ?
C2 N1 C1 N2 -176.21(7) . . . . ?
C10 N1 C1 Rh -173.50(6) . . . . ?
C2 N1 C1 Rh 9.23(12) . . . . ?
C1 N2 C4 C5 178.40(8) . . . . ?
C3 N2 C4 C5 -1.01(13) . . . . ?
C1 N2 C4 C10 -0.46(9) . . . . ?
C3 N2 C4 C10 -179.86(8) . . . . ?
N2 C4 C5 C6 176.92(8) . . . . ?
C10 C4 C5 C6 -4.50(15) . . . . ?
C4 C5 C6 C7 -1.13(16) . . . . ?
C5 C6 C7 C8 4.16(17) . . . . ?
C6 C7 C8 C9 -0.17(16) . . . . ?
C7 C8 C9 C10 -3.95(15) . . . . ?
C1 N1 C10 C9 176.74(7) . . . . ?
C2 N1 C10 C9 -6.05(12) . . . . ?
C1 N1 C10 C4 -1.33(8) . . . . ?
C2 N1 C10 C4 175.88(8) . . . . ?
C8 C9 C10 N1 -176.15(8) . . . . ?
C8 C9 C10 C4 1.44(14) . . . . ?
N2 C4 C10 N1 1.06(8) . . . . ?
C5 C4 C10 N1 -177.72(8) . . . . ?
N2 C4 C10 C9 -176.89(8) . . . . ?
C5 C4 C10 C9 4.34(14) . . . . ?
C18 C11 C12 C13 -2.40(15) . . . . ?
Rh C11 C12 C13 -104.78(9) . . . . ?
C18 C11 C12 Rh 102.39(10) . . . . ?
C11 C12 C13 C14 94.28(11) . . . . ?
Rh C12 C13 C14 13.81(10) . . . . ?
C12 C13 C14 C15 -35.64(12) . . . . ?
C13 C14 C15 C16 -42.68(12) . . . . ?
C13 C14 C15 Rh 38.52(9) . . . . ?
C14 C15 C16 C17 -3.29(13) . . . . ?
Rh C15 C16 C17 -102.44(8) . . . . ?
C14 C15 C16 Rh 99.15(8) . . . . ?
C15 C16 C17 C18 91.38(11) . . . . ?
Rh C16 C17 C18 10.81(11) . . . . ?
C12 C11 C18 C17 -46.26(14) . . . . ?
Rh C11 C18 C17 34.68(11) . . . . ?
C16 C17 C18 C11 -30.17(13) . . . . ?

_refine_diff_density_max         1.019
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.080



