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

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

data_mo_dabco_icl_0ma
_database_code_depnum_ccdc_archive 'CCDC 2183013'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2022-06-30 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'1,4-diazabicyclo[2,2,2]octane  iodine chloride'
_chemical_formula_moiety         'C6 H12 Cl0.953 I1.047 N2'
_chemical_formula_sum            'C6 H12 Cl0.95 I1.05 N2'
_chemical_formula_weight         278.87
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   21.6511(17)
_cell_length_b                   6.9602(6)
_cell_length_c                   5.9635(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     898.68(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5359
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.74
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   0.694
_shelx_estimated_absorpt_T_min   0.243
_exptl_absorpt_coefficient_mu    3.943
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.7016.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             535
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.276
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1481
_reflns_number_total             1858
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.155
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+0.9930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Rigid body (RIGU) restrains
 I2, I1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(I2)=0.5*(1-FVAR(2))
 Sof(Cl1)=0.5*FVAR(2)
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.76667(2) 0.250000 0.63638(3) 0.01344(8) Uani 1 2 d S T P . .
Cl1 Cl 0.88477(8) 0.250000 0.6729(3) 0.0192(3) Uani 0.9528(16) 2 d S T P . .
N1 N 0.66177(13) 0.250000 0.6004(4) 0.0131(5) Uani 1 2 d S T P . .
N2 N 0.54439(14) 0.250000 0.5566(5) 0.0180(6) Uani 1 2 d S T P . .
C1 C 0.64530(15) 0.250000 0.3578(5) 0.0147(6) Uani 1 2 d S T P . .
H1A H 0.662718 0.134696 0.283989 0.018 Uiso 0.5 1 calc R U P . .
H1B H 0.662718 0.365304 0.283989 0.018 Uiso 0.5 1 calc R U P . .
C2 C 0.57389(16) 0.250000 0.3351(5) 0.0175(7) Uani 1 2 d S T P . .
H2A H 0.560620 0.365117 0.250358 0.021 Uiso 0.5 1 calc R U P . .
H2B H 0.560620 0.134883 0.250358 0.021 Uiso 0.5 1 calc R U P . .
C3 C 0.63541(11) 0.4252(4) 0.7090(4) 0.0185(5) Uani 1 1 d . . . . .
H3A H 0.652730 0.542077 0.638266 0.022 Uiso 1 1 calc R U . . .
H3B H 0.646156 0.426974 0.870322 0.022 Uiso 1 1 calc R U . . .
C4 C 0.56419(11) 0.4219(4) 0.6801(4) 0.0195(5) Uani 1 1 d . . . . .
H4A H 0.544270 0.423433 0.829572 0.023 Uiso 1 1 calc R U . . .
H4B H 0.550833 0.538295 0.597947 0.023 Uiso 1 1 calc R U . . .
I2 I 0.9000(4) 0.250000 0.6735(16) 0.016(2) Uiso 0.0472(16) 2 d S . P . .


_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
I1 Cl1 2.5664(17) . ?
I1 N1 2.281(3) . ?
I1 I2 2.895(8) . ?
N1 C1 1.490(4) . ?
N1 C3 1.494(3) . ?
N1 C3 1.494(3) 7_565 ?
N2 C2 1.467(4) . ?
N2 C4 1.469(3) . ?
N2 C4 1.469(3) 7_565 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.552(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.552(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 I1 I2 0.5(2) . . ?
N1 I1 Cl1 179.47(8) . . ?
N1 I1 I2 179.0(2) . . ?
C1 N1 I1 109.24(19) . . ?
C1 N1 C3 109.22(17) . 7_565 ?
C1 N1 C3 109.22(17) . . ?
C3 N1 I1 109.86(15) 7_565 . ?
C3 N1 I1 109.86(15) . . ?
C3 N1 C3 109.4(3) . 7_565 ?
C2 N2 C4 108.93(18) . 7_565 ?
C2 N2 C4 108.93(18) . . ?
C4 N2 C4 109.1(3) . 7_565 ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 108.8(3) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
N2 C2 C1 110.8(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
N1 C3 C4 108.6(2) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
N2 C4 C3 110.9(2) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 N1 C1 C2 180.000(0) . . . . ?
I1 N1 C3 C4 179.56(16) . . . . ?
N1 C1 C2 N2 0.000(0) . . . . ?
N1 C3 C4 N2 0.0(3) . . . . ?
C1 N1 C3 C4 59.8(3) . . . . ?
C2 N2 C4 C3 -59.5(3) . . . . ?
C3 N1 C1 C2 59.82(17) 7_565 . . . ?
C3 N1 C1 C2 -59.82(17) . . . . ?
C3 N1 C3 C4 -59.8(3) 7_565 . . . ?
C4 N2 C2 C1 -59.44(18) 7_565 . . . ?
C4 N2 C2 C1 59.44(18) . . . . ?
C4 N2 C4 C3 59.3(3) 7_565 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dabco_ibr_0ma
_database_code_depnum_ccdc_archive 'CCDC 2183014'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2022-06-30 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '1,4-diazabicyclo[2,2,2]octane  iodine bromide'
_chemical_formula_moiety         'C6 H12 Br0.957 I0.983 N2'
_chemical_formula_sum            'C6 H12 Br0.96 I0.98 N2'
_chemical_formula_weight         313.37
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   21.6028(9)
_cell_length_b                   7.1603(3)
_cell_length_c                   5.9684(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     923.21(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5542
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      3.41
_shelx_estimated_absorpt_T_max   0.521
_shelx_estimated_absorpt_T_min   0.118
_exptl_absorpt_coefficient_mu    7.489
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.6483.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             590
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8758
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         1.885
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1232
_reflns_number_total             1307
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.00156(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0141
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0043P)²+0.6057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0284
_refine_ls_wR_factor_ref         0.0287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.76792(2) 0.250000 0.61823(2) 0.01142(6) Uani 0.983(3) 2 d S T . . .
Br1 Br 0.89259(2) 0.250000 0.65444(4) 0.01610(9) Uani 0.957(3) 2 d S T . . .
N1 N 0.66182(9) 0.250000 0.5857(3) 0.0115(4) Uani 1 2 d S T P . .
N2 N 0.54384(9) 0.250000 0.5492(3) 0.0141(4) Uani 1 2 d S T P . .
C1 C 0.64420(11) 0.250000 0.3438(4) 0.0142(5) Uani 1 2 d S T P . .
H1A H 0.661277 0.137897 0.268940 0.017 Uiso 0.5 1 calc R U P . .
H1B H 0.661277 0.362103 0.268940 0.017 Uiso 0.5 1 calc R U P . .
C4 C 0.63597(8) 0.4202(2) 0.6951(3) 0.0164(4) Uani 1 1 d . . . . .
H4A H 0.653080 0.533572 0.623184 0.020 Uiso 1 1 calc R U . . .
H4B H 0.647498 0.422053 0.855606 0.020 Uiso 1 1 calc R U . . .
C3 C 0.56431(8) 0.4176(2) 0.6708(3) 0.0162(4) Uani 1 1 d . . . . .
H3A H 0.545052 0.419707 0.821266 0.019 Uiso 1 1 calc R U . . .
H3B H 0.550635 0.530561 0.588899 0.019 Uiso 1 1 calc R U . . .
C2 C 0.57278(11) 0.250000 0.3264(4) 0.0148(5) Uani 1 2 d S T P . .
H2A H 0.559109 0.361852 0.242382 0.018 Uiso 0.5 1 calc R U P . .
H2B H 0.559109 0.138148 0.242382 0.018 Uiso 0.5 1 calc R U P . .


_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
I1 Br1 2.7018(3) . ?
I1 N1 2.3003(19) . ?
N1 C1 1.493(3) . ?
N1 C4 1.4908(19) . ?
N1 C4 1.4908(19) 7_565 ?
N2 C3 1.470(2) . ?
N2 C3 1.470(2) 7_565 ?
N2 C2 1.470(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.546(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.555(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 Br1 179.75(5) . . ?
C1 N1 I1 109.61(14) . . ?
C4 N1 I1 109.64(10) . . ?
C4 N1 I1 109.64(10) 7_565 . ?
C4 N1 C1 109.15(12) . . ?
C4 N1 C1 109.15(12) 7_565 . ?
C4 N1 C4 109.63(18) 7_565 . ?
C3 N2 C3 109.42(18) 7_565 . ?
C2 N2 C3 108.57(12) . 7_565 ?
C2 N2 C3 108.57(12) . . ?
N1 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
N1 C1 C2 108.62(18) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
N1 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
N1 C4 C3 108.81(14) . . ?
H4A C4 H4B 108.3 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
N2 C3 C4 110.79(14) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C2 C1 111.32(18) . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 N1 C1 C2 180.000(0) . . . . ?
I1 N1 C4 C3 179.88(11) . . . . ?
N1 C1 C2 N2 0.000(0) . . . . ?
N1 C4 C3 N2 0.14(19) . . . . ?
C1 N1 C4 C3 59.81(18) . . . . ?
C4 N1 C1 C2 -59.90(12) . . . . ?
C4 N1 C1 C2 59.90(12) 7_565 . . . ?
C4 N1 C4 C3 -59.7(2) 7_565 . . . ?
C3 N2 C3 C4 59.0(2) 7_565 . . . ?
C3 N2 C2 C1 -59.44(12) 7_565 . . . ?
C3 N2 C2 C1 59.44(12) . . . . ?
C2 N2 C3 C4 -59.32(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_phz_icl_0m
_database_code_depnum_ccdc_archive 'CCDC 2236196'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev'
;Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2023-01-14 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'phenazine iodine bromide'
_chemical_formula_moiety         'Br I, C12 H8 N2'
_chemical_formula_sum            'C12 H8 Br I N2'
_chemical_formula_weight         387.01
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.742(3)
_cell_length_b                   4.0442(4)
_cell_length_c                   21.075(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.857(3)
_cell_angle_gamma                90
_cell_volume                     2300.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3059
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.369
_exptl_absorpt_coefficient_mu    6.230
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1722 before and 0.0777 after correction.
The Ratio of minimum to maximum transmission is 0.6763.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2367
_reflns_number_total             3066
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.934
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.218
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.60311(2) 0.48432(8) 0.66083(2) 0.01307(9) Uani 1 1 d . . . . .
Br1 Br 0.56460(2) 0.69115(13) 0.74257(3) 0.01599(13) Uani 1 1 d . . . . .
N1 N 0.64047(15) 0.2682(9) 0.5804(2) 0.0136(9) Uani 1 1 d . . . . .
N2 N 0.68277(15) -0.0563(11) 0.4995(2) 0.0146(9) Uani 1 1 d . . . . .
C1 C 0.69045(18) 0.2581(12) 0.6025(3) 0.0125(10) Uani 1 1 d . . . . .
C2 C 0.72236(18) 0.4141(13) 0.6655(3) 0.0152(11) Uani 1 1 d . . . . .
H2 H 0.709111 0.523685 0.693723 0.018 Uiso 1 1 calc R . . . .
C3 C 0.77238(19) 0.4057(13) 0.6854(3) 0.0163(11) Uani 1 1 d . . . . .
H3 H 0.793714 0.513594 0.727307 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7933(2) 0.2383(13) 0.6446(3) 0.0182(11) Uani 1 1 d . . . . .
H4 H 0.828191 0.235562 0.659524 0.022 Uiso 1 1 calc R . . . .
C5 C 0.76350(18) 0.0831(13) 0.5844(3) 0.0165(11) Uani 1 1 d . . . . .
H5 H 0.777665 -0.031060 0.557872 0.020 Uiso 1 1 calc R . . . .
C6 C 0.71103(18) 0.0908(12) 0.5610(2) 0.0120(10) Uani 1 1 d . . . . .
C7 C 0.63360(18) -0.0326(12) 0.4776(3) 0.0140(10) Uani 1 1 d . . . . .
C8 C 0.60243(19) -0.1724(14) 0.4115(3) 0.0180(11) Uani 1 1 d . . . . .
H8 H 0.616637 -0.279523 0.384132 0.022 Uiso 1 1 calc R . . . .
C9 C 0.55225(19) -0.1518(13) 0.3876(3) 0.0171(11) Uani 1 1 d . . . . .
H9 H 0.531616 -0.244740 0.343437 0.021 Uiso 1 1 calc R . . . .
C10 C 0.53048(19) 0.0065(13) 0.4277(3) 0.0179(11) Uani 1 1 d . . . . .
H10 H 0.495399 0.017779 0.410058 0.021 Uiso 1 1 calc R . . . .
C11 C 0.55874(18) 0.1423(13) 0.4910(3) 0.0150(11) Uani 1 1 d . . . . .
H11 H 0.543430 0.246387 0.517259 0.018 Uiso 1 1 calc R . . . .
C12 C 0.61132(18) 0.1287(13) 0.5179(3) 0.0135(10) 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
I1 Br1 2.5766(6) . ?
N1 C1 1.359(6) . ?
N1 C12 1.358(6) . ?
N2 C6 1.350(6) . ?
N2 C7 1.339(6) . ?
C1 C2 1.414(7) . ?
C1 C6 1.432(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.366(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.426(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.357(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.425(7) . ?
C7 C8 1.427(7) . ?
C7 C12 1.435(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.362(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.417(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.358(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.423(7) . ?

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
C12 N1 C1 118.7(4) . . ?
C7 N2 C6 116.7(4) . . ?
N1 C1 C2 120.9(4) . . ?
N1 C1 C6 119.5(5) . . ?
C2 C1 C6 119.6(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
N2 C6 C1 122.8(4) . . ?
N2 C6 C5 118.2(4) . . ?
C5 C6 C1 119.0(5) . . ?
N2 C7 C8 118.4(5) . . ?
N2 C7 C12 122.5(5) . . ?
C8 C7 C12 119.1(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(5) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(5) . . ?
C12 C11 H11 120.0 . . ?
N1 C12 C7 119.9(4) . . ?
N1 C12 C11 121.1(5) . . ?
C11 C12 C7 119.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.5(5) . . . . ?
N1 C1 C6 N2 0.8(7) . . . . ?
N1 C1 C6 C5 179.7(4) . . . . ?
N2 C7 C8 C9 -179.8(5) . . . . ?
N2 C7 C12 N1 0.9(8) . . . . ?
N2 C7 C12 C11 -179.8(5) . . . . ?
C1 N1 C12 C7 1.5(7) . . . . ?
C1 N1 C12 C11 -177.7(4) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
C2 C1 C6 N2 -178.3(5) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 1.1(8) . . . . ?
C4 C5 C6 N2 177.5(5) . . . . ?
C4 C5 C6 C1 -1.4(7) . . . . ?
C6 N2 C7 C8 177.3(5) . . . . ?
C6 N2 C7 C12 -2.4(7) . . . . ?
C6 C1 C2 C3 0.7(7) . . . . ?
C7 N2 C6 C1 1.6(7) . . . . ?
C7 N2 C6 C5 -177.3(4) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C8 C7 C12 N1 -178.8(5) . . . . ?
C8 C7 C12 C11 0.5(7) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 N1 178.7(5) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C12 N1 C1 C2 176.8(5) . . . . ?
C12 N1 C1 C6 -2.3(7) . . . . ?
C12 C7 C8 C9 -0.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
