# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dtbbp130
_database_code_depnum_ccdc_archive 'CCDC 1567116'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4,4'-di-tert-butyl-2,2'-bipyridyl
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 N2'
_chemical_formula_sum            'C18 H24 N2'
_chemical_formula_weight         268.39

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      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                   10.2682(3)
_cell_length_b                   6.2802(3)
_cell_length_c                   24.5507(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.492(3)
_cell_angle_gamma                90
_cell_volume                     1561.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1813
_cell_measurement_theta_min      2.8212
_cell_measurement_theta_max      30.7010

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7630
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         30.770
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4273
_reflns_number_gt                2606
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4273
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
N2 N 0.17434(14) 0.2993(2) 0.24083(6) 0.0208(3) Uani 1 1 d . . . . .
C21 C 0.21498(16) 0.4857(3) 0.26449(7) 0.0183(4) Uani 1 1 d . . . . .
C31 C 0.18834(17) 0.5468(3) 0.31628(7) 0.0202(4) Uani 1 1 d . . . . .
H31 H 0.2189(19) 0.684(3) 0.3302(8) 0.021(5) Uiso 1 1 d . . . . .
C41 C 0.11456(16) 0.4153(3) 0.34519(7) 0.0195(4) Uani 1 1 d . . . . .
C51 C 0.07353(17) 0.2206(3) 0.32022(8) 0.0218(4) Uani 1 1 d . . . . .
H51 H 0.018(2) 0.117(3) 0.3388(8) 0.027(5) Uiso 1 1 d . . . . .
C61 C 0.10619(17) 0.1704(3) 0.26938(8) 0.0213(4) Uani 1 1 d . . . . .
H61 H 0.0796(18) 0.032(3) 0.2510(8) 0.019(5) Uiso 1 1 d . . . . .
C71 C 0.07474(17) 0.4792(3) 0.40020(7) 0.0228(4) Uani 1 1 d . . . . .
C76 C 0.1051(3) 0.3008(4) 0.44214(10) 0.0589(8) Uani 1 1 d . . . . .
H761 H 0.1996 0.2674 0.4473 0.088 Uiso 1 1 calc R U . . .
H762 H 0.0540 0.1740 0.4287 0.088 Uiso 1 1 calc R U . . .
H763 H 0.0813 0.3458 0.4774 0.088 Uiso 1 1 calc R U . . .
C75 C 0.1467(3) 0.6782(4) 0.42458(11) 0.0583(8) Uani 1 1 d . . . . .
H751 H 0.1179 0.7136 0.4596 0.087 Uiso 1 1 calc R U . . .
H752 H 0.1265 0.7971 0.3987 0.087 Uiso 1 1 calc R U . . .
H753 H 0.2421 0.6520 0.4311 0.087 Uiso 1 1 calc R U . . .
C77 C -0.0733(2) 0.5236(5) 0.38994(10) 0.0544(8) Uani 1 1 d . . . . .
H771 H -0.1210 0.3944 0.3759 0.082 Uiso 1 1 calc R U . . .
H772 H -0.0929 0.6381 0.3627 0.082 Uiso 1 1 calc R U . . .
H773 H -0.1012 0.5668 0.4246 0.082 Uiso 1 1 calc R U . . .
N1 N 0.32847(14) 0.8154(2) 0.25595(6) 0.0210(3) Uani 1 1 d . . . . .
C12 C 0.28992(16) 0.6281(3) 0.23222(7) 0.0188(4) Uani 1 1 d . . . . .
C13 C 0.31741(17) 0.5667(3) 0.18072(8) 0.0201(4) Uani 1 1 d . . . . .
H13 H 0.2861(19) 0.425(3) 0.1661(8) 0.024(5) Uiso 1 1 d . . . . .
C14 C 0.38884(16) 0.7019(3) 0.15136(7) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.42900(17) 0.8957(3) 0.17648(8) 0.0222(4) Uani 1 1 d . . . . .
H15 H 0.477(2) 1.004(3) 0.1589(9) 0.036(6) Uiso 1 1 d . . . . .
C16 C 0.39615(17) 0.9449(3) 0.22761(8) 0.0227(4) Uani 1 1 d . . . . .
H16 H 0.4203(19) 1.087(3) 0.2462(8) 0.023(5) Uiso 1 1 d . . . . .
C17 C 0.42709(17) 0.6366(3) 0.09618(8) 0.0230(4) Uani 1 1 d . . . . .
C72 C 0.4391(3) 0.8300(4) 0.05956(10) 0.0507(7) Uani 1 1 d . . . . .
H721 H 0.4571 0.7823 0.0235 0.076 Uiso 1 1 calc R U . . .
H722 H 0.5116 0.9209 0.0771 0.076 Uiso 1 1 calc R U . . .
H723 H 0.3563 0.9108 0.0545 0.076 Uiso 1 1 calc R U . . .
C73 C 0.3259(2) 0.4852(4) 0.06443(9) 0.0486(7) Uani 1 1 d . . . . .
H731 H 0.3224 0.3540 0.0857 0.073 Uiso 1 1 calc R U . . .
H732 H 0.3515 0.4512 0.0287 0.073 Uiso 1 1 calc R U . . .
H733 H 0.2388 0.5532 0.0584 0.073 Uiso 1 1 calc R U . . .
C74 C 0.5608(2) 0.5244(4) 0.10819(10) 0.0484(7) Uani 1 1 d . . . . .
H741 H 0.5548 0.4023 0.1325 0.073 Uiso 1 1 calc R U . . .
H742 H 0.6277 0.6241 0.1263 0.073 Uiso 1 1 calc R U . . .
H743 H 0.5857 0.4749 0.0735 0.073 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
N2 C61 1.341(2) . ?
N2 C21 1.342(2) . ?
C21 C31 1.398(3) . ?
C21 C12 1.490(2) . ?
C31 C41 1.392(3) . ?
C41 C51 1.401(3) . ?
C41 C71 1.528(3) . ?
C51 C61 1.381(3) . ?
C71 C76 1.519(3) . ?
C71 C75 1.523(3) . ?
C71 C77 1.525(3) . ?
N1 C16 1.337(2) . ?
N1 C12 1.343(2) . ?
C12 C13 1.394(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.396(3) . ?
C14 C17 1.528(3) . ?
C15 C16 1.387(3) . ?
C17 C73 1.524(3) . ?
C17 C74 1.528(3) . ?
C17 C72 1.528(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C61 N2 C21 116.88(16) . . ?
N2 C21 C31 122.65(17) . . ?
N2 C21 C12 116.38(15) . . ?
C31 C21 C12 120.97(16) . . ?
C41 C31 C21 120.38(17) . . ?
C31 C41 C51 116.39(17) . . ?
C31 C41 C71 122.84(16) . . ?
C51 C41 C71 120.74(16) . . ?
C61 C51 C41 119.63(18) . . ?
N2 C61 C51 124.04(17) . . ?
C76 C71 C75 107.86(19) . . ?
C76 C71 C77 109.5(2) . . ?
C75 C71 C77 108.7(2) . . ?
C76 C71 C41 110.50(17) . . ?
C75 C71 C41 112.32(16) . . ?
C77 C71 C41 107.87(15) . . ?
C16 N1 C12 116.62(16) . . ?
N1 C12 C13 123.13(17) . . ?
N1 C12 C21 115.86(16) . . ?
C13 C12 C21 121.01(16) . . ?
C12 C13 C14 120.08(17) . . ?
C15 C14 C13 116.36(17) . . ?
C15 C14 C17 121.73(17) . . ?
C13 C14 C17 121.84(16) . . ?
C16 C15 C14 119.74(18) . . ?
N1 C16 C15 124.06(17) . . ?
C73 C17 C14 111.58(16) . . ?
C73 C17 C74 109.05(19) . . ?
C14 C17 C74 107.88(15) . . ?
C73 C17 C72 108.00(18) . . ?
C14 C17 C72 111.44(17) . . ?
C74 C17 C72 108.8(2) . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

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

data_dtbbp190
_database_code_depnum_ccdc_archive 'CCDC 1567117'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4,4'-di-tert-butyl-2,2'-bipyridyl
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 N2'
_chemical_formula_sum            'C18 H24 N2'
_chemical_formula_weight         268.39

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      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                   10.3157(5)
_cell_length_b                   6.3341(3)
_cell_length_c                   24.5593(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.775(5)
_cell_angle_gamma                90
_cell_volume                     1581.42(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3566
_cell_measurement_theta_min      2.9389
_cell_measurement_theta_max      28.7195

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.153
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9886
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.325
_diffrn_reflns_theta_max         28.783
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3847
_reflns_number_gt                2114
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1416P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3847
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2126
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
N2 N 0.17585(17) 0.2985(3) 0.24120(7) 0.0332(4) Uani 1 1 d . . . . .
C21 C 0.21472(19) 0.4843(3) 0.26443(8) 0.0290(5) Uani 1 1 d . . . . .
C31 C 0.1873(2) 0.5464(3) 0.31583(8) 0.0309(5) Uani 1 1 d . . . . .
H31 H 0.218(2) 0.693(4) 0.3287(9) 0.040(6) Uiso 1 1 d . . . . .
C41 C 0.11414(19) 0.4162(3) 0.34475(8) 0.0305(5) Uani 1 1 d . . . . .
C51 C 0.0750(2) 0.2237(4) 0.32033(9) 0.0344(5) Uani 1 1 d . . . . .
H51 H 0.032(3) 0.116(4) 0.3384(10) 0.049(7) Uiso 1 1 d . . . . .
C61 C 0.1079(2) 0.1721(4) 0.26978(9) 0.0347(5) Uani 1 1 d . . . . .
H61 H 0.088(2) 0.039(4) 0.2543(9) 0.035(6) Uiso 1 1 d . . . . .
C71 C 0.0744(2) 0.4808(4) 0.39949(9) 0.0359(5) Uani 1 1 d . . . . .
C76 C 0.1084(5) 0.3111(6) 0.44209(13) 0.1021(16) Uani 1 1 d . . . . .
H761 H 0.2017 0.2748 0.4453 0.153 Uiso 1 1 calc R U . . .
H762 H 0.0547 0.1856 0.4310 0.153 Uiso 1 1 calc R U . . .
H763 H 0.0909 0.3618 0.4778 0.153 Uiso 1 1 calc R U . . .
C75 C 0.1423(5) 0.6820(7) 0.42272(15) 0.1072(16) Uani 1 1 d . . . . .
H751 H 0.1115 0.7201 0.4570 0.161 Uiso 1 1 calc R U . . .
H752 H 0.1216 0.7964 0.3958 0.161 Uiso 1 1 calc R U . . .
H753 H 0.2377 0.6595 0.4303 0.161 Uiso 1 1 calc R U . . .
C77 C -0.0724(3) 0.5169(7) 0.38958(13) 0.0919(13) Uani 1 1 d . . . . .
H771 H -0.1178 0.3851 0.3772 0.138 Uiso 1 1 calc R U . . .
H772 H -0.0951 0.6256 0.3611 0.138 Uiso 1 1 calc R U . . .
H773 H -0.0997 0.5636 0.4240 0.138 Uiso 1 1 calc R U . . .
N1 N 0.32760(17) 0.8108(3) 0.25566(7) 0.0331(4) Uani 1 1 d . . . . .
C12 C 0.28961(19) 0.6245(3) 0.23233(8) 0.0298(5) Uani 1 1 d . . . . .
C13 C 0.3167(2) 0.5626(4) 0.18104(9) 0.0323(5) Uani 1 1 d . . . . .
H13 H 0.283(2) 0.427(4) 0.1668(9) 0.032(6) Uiso 1 1 d . . . . .
C14 C 0.3879(2) 0.6959(3) 0.15183(8) 0.0318(5) Uani 1 1 d . . . . .
C15 C 0.4284(2) 0.8885(4) 0.17654(9) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.474(2) 0.992(4) 0.1581(9) 0.036(6) Uiso 1 1 d . . . . .
C16 C 0.3957(2) 0.9387(4) 0.22740(9) 0.0349(5) Uani 1 1 d . . . . .
H16 H 0.424(2) 1.082(4) 0.2461(9) 0.043(6) Uiso 1 1 d . . . . .
C17 C 0.4262(2) 0.6306(4) 0.09675(9) 0.0376(5) Uani 1 1 d . . . . .
C72 C 0.4354(4) 0.8195(5) 0.05967(12) 0.0778(11) Uani 1 1 d . . . . .
H721 H 0.4545 0.7711 0.0240 0.117 Uiso 1 1 calc R U . . .
H722 H 0.5059 0.9133 0.0771 0.117 Uiso 1 1 calc R U . . .
H723 H 0.3516 0.8962 0.0540 0.117 Uiso 1 1 calc R U . . .
C73 C 0.3265(4) 0.4778(6) 0.06533(12) 0.0834(11) Uani 1 1 d . . . . .
H731 H 0.3291 0.3442 0.0856 0.125 Uiso 1 1 calc R U . . .
H732 H 0.3482 0.4519 0.0286 0.125 Uiso 1 1 calc R U . . .
H733 H 0.2382 0.5389 0.0616 0.125 Uiso 1 1 calc R U . . .
C74 C 0.5599(3) 0.5227(6) 0.10917(12) 0.0785(11) Uani 1 1 d . . . . .
H741 H 0.5551 0.4027 0.1340 0.118 Uiso 1 1 calc R U . . .
H742 H 0.6258 0.6235 0.1269 0.118 Uiso 1 1 calc R U . . .
H743 H 0.5847 0.4723 0.0746 0.118 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
N2 C21 1.339(3) . ?
N2 C61 1.339(3) . ?
C21 C31 1.396(3) . ?
C21 C12 1.488(3) . ?
C31 C41 1.392(3) . ?
C41 C51 1.388(3) . ?
C41 C71 1.526(3) . ?
C51 C61 1.381(3) . ?
C71 C76 1.499(4) . ?
C71 C77 1.511(4) . ?
C71 C75 1.518(4) . ?
N1 C12 1.341(3) . ?
N1 C16 1.341(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.395(3) . ?
C14 C17 1.529(3) . ?
C15 C16 1.385(3) . ?
C17 C72 1.516(4) . ?
C17 C74 1.523(3) . ?
C17 C73 1.523(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
C21 N2 C61 116.61(18) . . ?
N2 C21 C31 122.73(19) . . ?
N2 C21 C12 116.34(17) . . ?
C31 C21 C12 120.94(18) . . ?
C41 C31 C21 120.4(2) . . ?
C51 C41 C31 116.28(18) . . ?
C51 C41 C71 120.95(18) . . ?
C31 C41 C71 122.74(19) . . ?
C61 C51 C41 119.9(2) . . ?
N2 C61 C51 124.1(2) . . ?
C76 C71 C77 109.3(3) . . ?
C76 C71 C75 107.6(3) . . ?
C77 C71 C75 108.6(3) . . ?
C76 C71 C41 110.9(2) . . ?
C77 C71 C41 108.09(19) . . ?
C75 C71 C41 112.36(19) . . ?
C12 N1 C16 116.84(18) . . ?
N1 C12 C13 123.07(19) . . ?
N1 C12 C21 116.06(17) . . ?
C13 C12 C21 120.87(19) . . ?
C12 C13 C14 119.9(2) . . ?
C15 C14 C13 116.80(19) . . ?
C15 C14 C17 121.21(19) . . ?
C13 C14 C17 121.9(2) . . ?
C16 C15 C14 119.5(2) . . ?
N1 C16 C15 123.9(2) . . ?
C72 C17 C74 109.1(2) . . ?
C72 C17 C73 107.6(2) . . ?
C74 C17 C73 109.1(3) . . ?
C72 C17 C14 111.7(2) . . ?
C74 C17 C14 107.78(19) . . ?
C73 C17 C14 111.51(19) . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

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

data_dtbbpbra
_database_code_depnum_ccdc_archive 'CCDC 1567119'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_dtbbpbra            
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT112_dtbbpbra            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.      c/2        100 %Fit
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT113_dtbbpbra            
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Br2 N2 O4'
_chemical_formula_weight         566.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.951(3)
_cell_length_b                   11.491(5)
_cell_length_c                   11.910(3)
_cell_angle_alpha                98.84(3)
_cell_angle_beta                 104.58(6)
_cell_angle_gamma                93.42(4)
_cell_volume                     1165.3(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7802
_cell_measurement_theta_min      3.0867
_cell_measurement_theta_max      36.7423
_cell_measurement_temperature    150(2)

_exptl_crystal_description       blocks
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3952
_exptl_crystal_size_mid          0.2236
_exptl_crystal_size_min          0.1567
_exptl_absorpt_coefficient_mu    3.512
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
__diffrn_radiation_source        'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            17495
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.093
_diffrn_reflns_theta_max         36.830
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.745
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.745
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8710
_reflns_number_gt                4801
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0985P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8710
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_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
Br1 Br 0.76813(4) 0.07679(3) 0.49929(3) 0.02897(12) Uani 1 1 d . . . . .
Br2 Br 0.23078(4) -0.06277(3) -0.01479(3) 0.02576(12) Uani 1 1 d . . . . .
O2 O 0.5721(3) -0.1572(2) 0.3827(2) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.5258 -0.2220 0.3431 0.027 Uiso 1 1 calc R U . . .
O3 O 0.3662(3) -0.2139(2) 0.1767(2) 0.0232(5) Uani 1 1 d . . . . .
O5 O 0.4219(3) 0.1773(2) 0.1038(2) 0.0193(5) Uani 1 1 d . . . . .
O6 O 0.6337(3) 0.2318(2) 0.3123(2) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.6159(4) 0.0376(3) 0.3543(3) 0.0195(7) Uani 1 1 d . . . . .
C2 C 0.5420(4) -0.0723(3) 0.3188(3) 0.0194(7) Uani 1 1 d . . . . .
C3 C 0.4215(4) -0.1090(3) 0.2007(3) 0.0186(7) Uani 1 1 d . . . . .
C4 C 0.3833(4) -0.0200(3) 0.1303(3) 0.0182(7) Uani 1 1 d . . . . .
C5 C 0.4526(4) 0.0952(3) 0.1625(3) 0.0178(6) Uani 1 1 d . . . . .
C6 C 0.5763(4) 0.1289(3) 0.2832(3) 0.0182(7) Uani 1 1 d . . . . .
N1 N 0.5617(3) 0.3923(3) 0.1364(2) 0.0168(5) Uani 1 1 d . . . . .
H1 H 0.5040 0.3293 0.1406 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5588(3) 0.4957(3) 0.2073(3) 0.0141(6) Uani 1 1 d . . . . .
C13 C 0.6578(4) 0.5923(3) 0.2050(3) 0.0160(6) Uani 1 1 d . . . . .
H13 H 0.6576 0.6651 0.2550 0.019 Uiso 1 1 calc R U . . .
C14 C 0.7577(4) 0.5862(3) 0.1319(3) 0.0173(7) Uani 1 1 d . . . . .
C15 C 0.7476(4) 0.4783(3) 0.0548(3) 0.0198(7) Uani 1 1 d . . . . .
H15 H 0.8080 0.4712 -0.0006 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6495(4) 0.3826(3) 0.0599(3) 0.0187(7) Uani 1 1 d . . . . .
H16 H 0.6444 0.3095 0.0088 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8806(4) 0.6875(3) 0.1411(3) 0.0194(7) Uani 1 1 d . . . . .
C72 C 1.0314(4) 0.6580(4) 0.2208(3) 0.0279(8) Uani 1 1 d . . . . .
H721 H 1.0211 0.6627 0.3014 0.042 Uiso 1 1 calc R U . . .
H722 H 1.1175 0.7146 0.2205 0.042 Uiso 1 1 calc R U . . .
H723 H 1.0519 0.5777 0.1916 0.042 Uiso 1 1 calc R U . . .
C73 C 0.8393(5) 0.8067(3) 0.1954(4) 0.0317(9) Uani 1 1 d . . . . .
H731 H 0.7404 0.8244 0.1468 0.048 Uiso 1 1 calc R U . . .
H732 H 0.9210 0.8690 0.1992 0.048 Uiso 1 1 calc R U . . .
H733 H 0.8301 0.8032 0.2751 0.048 Uiso 1 1 calc R U . . .
C74 C 0.9042(4) 0.6980(3) 0.0194(3) 0.0266(8) Uani 1 1 d . . . . .
H741 H 0.9255 0.6212 -0.0184 0.040 Uiso 1 1 calc R U . . .
H742 H 0.9921 0.7571 0.0288 0.040 Uiso 1 1 calc R U . . .
H743 H 0.8101 0.7225 -0.0296 0.040 Uiso 1 1 calc R U . . .
N2 N 0.4633(3) 0.6074(3) 0.3551(3) 0.0185(6) Uani 1 1 d . . . . .
C21 C 0.4526(3) 0.5017(3) 0.2856(3) 0.0154(6) Uani 1 1 d . . . . .
C31 C 0.3511(4) 0.4047(3) 0.2862(3) 0.0167(6) Uani 1 1 d . . . . .
H31 H 0.3463 0.3323 0.2341 0.020 Uiso 1 1 calc R U . . .
C41 C 0.2560(3) 0.4147(3) 0.3642(3) 0.0167(6) Uani 1 1 d . . . . .
C51 C 0.2727(4) 0.5222(3) 0.4388(3) 0.0214(7) Uani 1 1 d . . . . .
H51 H 0.2138 0.5327 0.4951 0.026 Uiso 1 1 calc R U . . .
C61 C 0.3758(4) 0.6156(3) 0.4321(3) 0.0207(7) Uani 1 1 d . . . . .
H61 H 0.3843 0.6884 0.4844 0.025 Uiso 1 1 calc R U . . .
C71 C 0.1355(4) 0.3137(3) 0.3614(3) 0.0203(7) Uani 1 1 d . . . . .
C75 C 0.1797(5) 0.1921(4) 0.3148(4) 0.0371(10) Uani 1 1 d . . . . .
H751 H 0.1004 0.1302 0.3164 0.056 Uiso 1 1 calc R U . . .
H752 H 0.2802 0.1787 0.3645 0.056 Uiso 1 1 calc R U . . .
H753 H 0.1867 0.1896 0.2337 0.056 Uiso 1 1 calc R U . . .
C76 C -0.0187(4) 0.3356(4) 0.2800(3) 0.0288(9) Uani 1 1 d . . . . .
H761 H -0.0415 0.4167 0.3037 0.043 Uiso 1 1 calc R U . . .
H762 H -0.1021 0.2795 0.2859 0.043 Uiso 1 1 calc R U . . .
H763 H -0.0109 0.3247 0.1985 0.043 Uiso 1 1 calc R U . . .
C77 C 0.1137(4) 0.3121(4) 0.4845(3) 0.0304(9) Uani 1 1 d . . . . .
H771 H 0.0810 0.3880 0.5143 0.046 Uiso 1 1 calc R U . . .
H772 H 0.2120 0.2991 0.5376 0.046 Uiso 1 1 calc R U . . .
H773 H 0.0342 0.2480 0.4805 0.046 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
Br1 C1 1.883(4) . ?
Br2 C4 1.888(3) . ?
O2 C2 1.326(4) . ?
O2 H2 0.8400 . ?
O3 C3 1.238(4) . ?
O5 C5 1.261(4) . ?
O6 C6 1.222(4) . ?
C1 C2 1.344(5) . ?
C1 C6 1.453(4) . ?
C2 C3 1.523(5) . ?
C3 C4 1.423(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.555(5) . ?
N1 C16 1.341(4) . ?
N1 C12 1.354(4) . ?
N1 H1 0.8800 . ?
C12 C13 1.386(4) . ?
C12 C21 1.488(4) . ?
C13 C14 1.394(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(5) . ?
C14 C17 1.525(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C73 1.530(5) . ?
C17 C72 1.531(5) . ?
C17 C74 1.538(5) . ?
C72 H721 0.9800 . ?
C72 H722 0.9800 . ?
C72 H723 0.9800 . ?
C73 H731 0.9800 . ?
C73 H732 0.9800 . ?
C73 H733 0.9800 . ?
C74 H741 0.9800 . ?
C74 H742 0.9800 . ?
C74 H743 0.9800 . ?
N2 C21 1.344(5) . ?
N2 C61 1.344(4) . ?
C21 C31 1.398(4) . ?
C31 C41 1.407(4) . ?
C31 H31 0.9500 . ?
C41 C51 1.383(5) . ?
C41 C71 1.527(4) . ?
C51 C61 1.398(5) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
C71 C77 1.530(5) . ?
C71 C76 1.533(5) . ?
C71 C75 1.534(6) . ?
C75 H751 0.9800 . ?
C75 H752 0.9800 . ?
C75 H753 0.9800 . ?
C76 H761 0.9800 . ?
C76 H762 0.9800 . ?
C76 H763 0.9800 . ?
C77 H771 0.9800 . ?
C77 H772 0.9800 . ?
C77 H773 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
C2 O2 H2 109.5 . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 Br1 120.5(3) . . ?
C6 C1 Br1 118.9(2) . . ?
O2 C2 C1 122.3(3) . . ?
O2 C2 C3 115.4(3) . . ?
C1 C2 C3 122.3(3) . . ?
O3 C3 C4 126.9(3) . . ?
O3 C3 C2 115.8(3) . . ?
C4 C3 C2 117.2(3) . . ?
C5 C4 C3 123.4(3) . . ?
C5 C4 Br2 118.6(2) . . ?
C3 C4 Br2 117.9(2) . . ?
O5 C5 C4 125.8(3) . . ?
O5 C5 C6 116.4(3) . . ?
C4 C5 C6 117.8(3) . . ?
O6 C6 C1 124.1(3) . . ?
O6 C6 C5 117.3(3) . . ?
C1 C6 C5 118.6(3) . . ?
C16 N1 C12 122.3(3) . . ?
C16 N1 H1 118.8 . . ?
C12 N1 H1 118.8 . . ?
N1 C12 C13 118.1(3) . . ?
N1 C12 C21 119.5(3) . . ?
C13 C12 C21 122.4(3) . . ?
C12 C13 C14 122.3(3) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 116.7(3) . . ?
C13 C14 C17 121.8(3) . . ?
C15 C14 C17 121.3(3) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N1 C16 C15 120.5(3) . . ?
N1 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C14 C17 C73 112.4(3) . . ?
C14 C17 C72 106.4(3) . . ?
C73 C17 C72 109.1(3) . . ?
C14 C17 C74 111.1(3) . . ?
C73 C17 C74 108.4(3) . . ?
C72 C17 C74 109.6(3) . . ?
C17 C72 H721 109.5 . . ?
C17 C72 H722 109.5 . . ?
H721 C72 H722 109.5 . . ?
C17 C72 H723 109.5 . . ?
H721 C72 H723 109.5 . . ?
H722 C72 H723 109.5 . . ?
C17 C73 H731 109.5 . . ?
C17 C73 H732 109.5 . . ?
H731 C73 H732 109.5 . . ?
C17 C73 H733 109.5 . . ?
H731 C73 H733 109.5 . . ?
H732 C73 H733 109.5 . . ?
C17 C74 H741 109.5 . . ?
C17 C74 H742 109.5 . . ?
H741 C74 H742 109.5 . . ?
C17 C74 H743 109.5 . . ?
H741 C74 H743 109.5 . . ?
H742 C74 H743 109.5 . . ?
C21 N2 C61 116.7(3) . . ?
N2 C21 C31 123.4(3) . . ?
N2 C21 C12 114.4(3) . . ?
C31 C21 C12 122.2(3) . . ?
C21 C31 C41 119.7(3) . . ?
C21 C31 H31 120.1 . . ?
C41 C31 H31 120.1 . . ?
C51 C41 C31 116.4(3) . . ?
C51 C41 C71 122.3(3) . . ?
C31 C41 C71 121.2(3) . . ?
C41 C51 C61 120.5(3) . . ?
C41 C51 H51 119.8 . . ?
C61 C51 H51 119.8 . . ?
N2 C61 C51 123.2(4) . . ?
N2 C61 H61 118.4 . . ?
C51 C61 H61 118.4 . . ?
C41 C71 C77 110.7(3) . . ?
C41 C71 C76 107.4(3) . . ?
C77 C71 C76 108.7(3) . . ?
C41 C71 C75 112.5(3) . . ?
C77 C71 C75 108.4(3) . . ?
C76 C71 C75 109.0(3) . . ?
C71 C75 H751 109.5 . . ?
C71 C75 H752 109.5 . . ?
H751 C75 H752 109.5 . . ?
C71 C75 H753 109.5 . . ?
H751 C75 H753 109.5 . . ?
H752 C75 H753 109.5 . . ?
C71 C76 H761 109.5 . . ?
C71 C76 H762 109.5 . . ?
H761 C76 H762 109.5 . . ?
C71 C76 H763 109.5 . . ?
H761 C76 H763 109.5 . . ?
H762 C76 H763 109.5 . . ?
C71 C77 H771 109.5 . . ?
C71 C77 H772 109.5 . . ?
H771 C77 H772 109.5 . . ?
C71 C77 H773 109.5 . . ?
H771 C77 H773 109.5 . . ?
H772 C77 H773 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.88 1.80 2.630(4) 156.9 .
N1 H1 O6 0.88 2.54 2.976(4) 111.5 .
O2 H2 O3 0.84 2.15 2.632(4) 116.3 .
O2 H2 N2 0.84 2.04 2.761(4) 143.2 1_545
C13 H13 N2 0.95 2.46 2.787(4) 100.2 .
C13 H13 O3 0.95 3.04 3.517(4) 113.0 1_565
C16 H16 O5 0.95 2.98 3.215(4) 95.9 .
C31 H31 O5 0.95 2.42 3.331(5) 160.3 .
C16 H16 O3 0.95 2.29 3.132(5) 147.6 2_655
C72 H722 O3 0.98 2.53 3.454(4) 157.1 1_665
C74 H743 O5 0.98 2.47 3.423(5) 164.4 2_665
C61 H61 O6 0.95 2.50 3.296(5) 141.0 2_666
C76 H762 O6 0.98 2.50 3.399(4) 151.9 1_455

_refine_diff_density_max         1.059
_refine_diff_density_min         -1.720
_refine_diff_density_rms         0.219

_shelxl_version_number           2013-4

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

data_moskw2
_database_code_depnum_ccdc_archive 'CCDC 1567121'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_moskw2              
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT112_moskw2              
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.      c/2        100 %Fit
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT113_moskw2              
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 I2 N2 O4'
_chemical_formula_weight         660.27

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.8323(5)
_cell_length_b                   11.7934(6)
_cell_length_c                   12.0531(11)
_cell_angle_alpha                80.595(6)
_cell_angle_beta                 66.706(6)
_cell_angle_gamma                79.529(4)
_cell_volume                     1255.83(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    345(2)
_cell_measurement_reflns_used    2206
_cell_measurement_theta_min      3.7110
_cell_measurement_theta_max      29.6390

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3731
_exptl_crystal_size_mid          0.3117
_exptl_crystal_size_min          0.1586
_exptl_absorpt_coefficient_mu    2.536
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.78930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   analytical

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      345(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            10416
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         30.865
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             6397
_reflns_number_gt                4005
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6397
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_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
I2 I 0.2838(5) 0.4378(3) 0.3824(4) 0.0586(4) Uani 0.546(14) 1 d . . P A 1
I1 I -0.2716(4) 0.57066(19) 0.1266(3) 0.0607(4) Uani 0.546(14) 1 d . . P A 1
I1A I -0.2895(6) 0.5715(3) 0.1552(8) 0.0818(9) Uani 0.454(14) 1 d . . P A 2
I2A I 0.2984(7) 0.4398(4) 0.3567(8) 0.0730(10) Uani 0.454(14) 1 d . . P A 2
O2 O -0.0669(3) 0.33980(17) 0.1648(2) 0.0567(6) Uani 1 1 d . . . . .
H2 H -0.019(5) 0.273(4) 0.180(4) 0.125(18) Uiso 1 1 d . . . . .
O5 O 0.0809(2) 0.67424(16) 0.3437(2) 0.0538(6) Uani 1 1 d . . . . .
O3 O 0.1381(3) 0.28940(16) 0.2580(2) 0.0610(6) Uani 1 1 d . . . . .
O6 O -0.1314(3) 0.72289(16) 0.2506(2) 0.0608(6) Uani 1 1 d . . . . .
C5 C 0.0515(3) 0.5924(2) 0.3049(3) 0.0426(7) Uani 1 1 d . . . . .
C6 C -0.0732(3) 0.6234(2) 0.2529(3) 0.0442(7) Uani 1 1 d . . . . .
C1 C -0.1114(3) 0.5326(2) 0.2065(3) 0.0458(7) Uani 1 1 d . . . . .
C4 C 0.1215(3) 0.4801(2) 0.3047(3) 0.0445(7) Uani 1 1 d . . . . .
C2 C -0.0373(3) 0.4253(2) 0.2080(3) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.0824(3) 0.3919(2) 0.2594(3) 0.0432(7) Uani 1 1 d . . . . .
N1 N -0.0588(3) 0.88380(19) 0.3858(2) 0.0386(6) Uani 1 1 d . . . . .
N2 N 0.0403(3) 1.10260(19) 0.1293(2) 0.0457(6) Uani 1 1 d . . . . .
C12 C -0.0571(3) 0.9872(2) 0.3182(3) 0.0338(6) Uani 1 1 d . . . . .
C13 C -0.1530(3) 1.0809(2) 0.3727(3) 0.0373(6) Uani 1 1 d . . . . .
H13 H -0.1528 1.1524 0.3266 0.045 Uiso 1 1 calc R U . . .
C14 C -0.2494(3) 1.0726(2) 0.4931(3) 0.0373(6) Uani 1 1 d . . . . .
C15 C -0.2405(4) 0.9641(2) 0.5598(3) 0.0491(7) Uani 1 1 d . . . . .
H15 H -0.2985 0.9545 0.6423 0.059 Uiso 1 1 calc R U . . .
C16 C -0.1465(4) 0.8730(2) 0.5030(3) 0.0495(8) Uani 1 1 d . . . . .
H16 H -0.1436 0.8010 0.5475 0.059 Uiso 1 1 calc R U . . .
C17 C -0.3656(3) 1.1726(2) 0.5503(3) 0.0444(7) Uani 1 1 d . . . . .
C74 C -0.3747(5) 1.1815(4) 0.6775(3) 0.0776(12) Uani 1 1 d . . . . .
H741 H -0.4486 1.2447 0.7116 0.116 Uiso 1 1 calc R U . . .
H742 H -0.2793 1.1947 0.6737 0.116 Uiso 1 1 calc R U . . .
H743 H -0.4017 1.1106 0.7274 0.116 Uiso 1 1 calc R U . . .
C72 C -0.5149(4) 1.1504(4) 0.5548(4) 0.0795(12) Uani 1 1 d . . . . .
H721 H -0.5076 1.1440 0.4742 0.119 Uiso 1 1 calc R U . . .
H722 H -0.5898 1.2135 0.5880 0.119 Uiso 1 1 calc R U . . .
H723 H -0.5418 1.0796 0.6050 0.119 Uiso 1 1 calc R U . . .
C73 C -0.3303(5) 1.2905(3) 0.4748(4) 0.0834(13) Uani 1 1 d . . . . .
H731 H -0.3239 1.2871 0.3938 0.125 Uiso 1 1 calc R U . . .
H732 H -0.2368 1.3070 0.4719 0.125 Uiso 1 1 calc R U . . .
H733 H -0.4081 1.3504 0.5118 0.125 Uiso 1 1 calc R U . . .
C21 C 0.0481(3) 0.9957(2) 0.1896(3) 0.0348(6) Uani 1 1 d . . . . .
C31 C 0.1479(3) 0.9027(2) 0.1351(3) 0.0364(6) Uani 1 1 d . . . . .
H31 H 0.1495 0.8307 0.1799 0.044 Uiso 1 1 calc R U . . .
C41 C 0.2450(3) 0.9158(2) 0.0150(3) 0.0395(6) Uani 1 1 d . . . . .
C51 C 0.2318(4) 1.0255(3) -0.0472(3) 0.0524(8) Uani 1 1 d . . . . .
H51 H 0.2911 1.0392 -0.1289 0.063 Uiso 1 1 calc R U . . .
C61 C 0.1308(4) 1.1128(3) 0.0132(3) 0.0563(9) Uani 1 1 d . . . . .
H61 H 0.1253 1.1850 -0.0306 0.068 Uiso 1 1 calc R U . . .
C71 C 0.3634(3) 0.8188(3) -0.0466(3) 0.0490(7) Uani 1 1 d . . . . .
C76 C 0.5134(4) 0.8427(4) -0.0542(4) 0.0905(14) Uani 1 1 d . . . . .
H763 H 0.5091 0.8473 0.0259 0.136 Uiso 1 1 calc R U . . .
H761 H 0.5370 0.9148 -0.1028 0.136 Uiso 1 1 calc R U . . .
H762 H 0.5891 0.7812 -0.0905 0.136 Uiso 1 1 calc R U . . .
C77 C 0.3696(5) 0.8127(4) -0.1735(4) 0.0915(14) Uani 1 1 d . . . . .
H771 H 0.4448 0.7512 -0.2103 0.137 Uiso 1 1 calc R U . . .
H772 H 0.3936 0.8850 -0.2217 0.137 Uiso 1 1 calc R U . . .
H773 H 0.2743 0.7983 -0.1687 0.137 Uiso 1 1 calc R U . . .
C75 C 0.3347(6) 0.6995(3) 0.0254(4) 0.1049(17) Uani 1 1 d . . . . .
H751 H 0.3310 0.7012 0.1059 0.157 Uiso 1 1 calc R U . . .
H752 H 0.4139 0.6417 -0.0147 0.157 Uiso 1 1 calc R U . . .
H753 H 0.2413 0.6811 0.0299 0.157 Uiso 1 1 calc R U . . .
H1 H -0.010(3) 0.814(3) 0.356(3) 0.059(9) 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
I2 C4 2.102(5) . ?
I1 C1 2.101(4) . ?
I1A C1 2.032(5) . ?
I2A C4 2.027(6) . ?
O2 C2 1.330(3) . ?
O2 H2 0.87(4) . ?
O5 C5 1.261(3) . ?
O3 C3 1.233(3) . ?
O6 C6 1.210(3) . ?
C5 C4 1.377(3) . ?
C5 C6 1.549(4) . ?
C6 C1 1.452(4) . ?
C1 C2 1.342(4) . ?
C4 C3 1.422(4) . ?
C2 C3 1.501(4) . ?
N1 C16 1.332(4) . ?
N1 C12 1.351(3) . ?
N1 H1 0.93(3) . ?
N2 C61 1.328(4) . ?
N2 C21 1.355(3) . ?
C12 C13 1.382(4) . ?
C12 C21 1.483(4) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(4) . ?
C14 C17 1.525(4) . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C72 1.516(4) . ?
C17 C74 1.520(4) . ?
C17 C73 1.547(5) . ?
C74 H741 0.9600 . ?
C74 H742 0.9600 . ?
C74 H743 0.9600 . ?
C72 H721 0.9600 . ?
C72 H722 0.9600 . ?
C72 H723 0.9600 . ?
C73 H731 0.9600 . ?
C73 H732 0.9600 . ?
C73 H733 0.9600 . ?
C21 C31 1.389(4) . ?
C31 C41 1.385(4) . ?
C31 H31 0.9300 . ?
C41 C51 1.397(4) . ?
C41 C71 1.525(4) . ?
C51 C61 1.370(4) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C71 C76 1.517(4) . ?
C71 C77 1.519(5) . ?
C71 C75 1.537(5) . ?
C76 H763 0.9600 . ?
C76 H761 0.9600 . ?
C76 H762 0.9600 . ?
C77 H771 0.9600 . ?
C77 H772 0.9600 . ?
C77 H773 0.9600 . ?
C75 H751 0.9600 . ?
C75 H752 0.9600 . ?
C75 H753 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H2 112(3) . . ?
O5 C5 C4 125.3(3) . . ?
O5 C5 C6 116.1(2) . . ?
C4 C5 C6 118.5(3) . . ?
O6 C6 C1 123.4(3) . . ?
O6 C6 C5 118.0(3) . . ?
C1 C6 C5 118.5(2) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 I1A 122.5(2) . . ?
C6 C1 I1A 117.6(2) . . ?
C2 C1 I1 119.8(2) . . ?
C6 C1 I1 120.4(2) . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 I2A 119.6(3) . . ?
C3 C4 I2A 117.8(2) . . ?
C5 C4 I2 118.1(2) . . ?
C3 C4 I2 119.6(2) . . ?
O2 C2 C1 121.8(3) . . ?
O2 C2 C3 115.1(2) . . ?
C1 C2 C3 123.2(3) . . ?
O3 C3 C4 126.0(3) . . ?
O3 C3 C2 116.2(3) . . ?
C4 C3 C2 117.8(2) . . ?
C16 N1 C12 121.0(3) . . ?
C16 N1 H1 113.6(19) . . ?
C12 N1 H1 125.1(19) . . ?
C61 N2 C21 116.0(3) . . ?
N1 C12 C13 118.2(3) . . ?
N1 C12 C21 118.8(3) . . ?
C13 C12 C21 123.0(2) . . ?
C12 C13 C14 122.5(2) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 116.3(3) . . ?
C13 C14 C17 122.7(2) . . ?
C15 C14 C17 120.9(3) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N1 C16 C15 122.1(3) . . ?
N1 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C72 C17 C74 110.2(3) . . ?
C72 C17 C14 107.7(2) . . ?
C74 C17 C14 111.0(3) . . ?
C72 C17 C73 108.0(3) . . ?
C74 C17 C73 107.8(3) . . ?
C14 C17 C73 112.1(3) . . ?
C17 C74 H741 109.5 . . ?
C17 C74 H742 109.5 . . ?
H741 C74 H742 109.5 . . ?
C17 C74 H743 109.5 . . ?
H741 C74 H743 109.5 . . ?
H742 C74 H743 109.5 . . ?
C17 C72 H721 109.5 . . ?
C17 C72 H722 109.5 . . ?
H721 C72 H722 109.5 . . ?
C17 C72 H723 109.5 . . ?
H721 C72 H723 109.5 . . ?
H722 C72 H723 109.5 . . ?
C17 C73 H731 109.5 . . ?
C17 C73 H732 109.5 . . ?
H731 C73 H732 109.5 . . ?
C17 C73 H733 109.5 . . ?
H731 C73 H733 109.5 . . ?
H732 C73 H733 109.5 . . ?
N2 C21 C31 122.4(3) . . ?
N2 C21 C12 114.3(3) . . ?
C31 C21 C12 123.3(2) . . ?
C41 C31 C21 120.9(2) . . ?
C41 C31 H31 119.5 . . ?
C21 C31 H31 119.5 . . ?
C31 C41 C51 116.0(3) . . ?
C31 C41 C71 122.9(2) . . ?
C51 C41 C71 121.0(3) . . ?
C61 C51 C41 119.5(3) . . ?
C61 C51 H51 120.2 . . ?
C41 C51 H51 120.2 . . ?
N2 C61 C51 125.2(3) . . ?
N2 C61 H61 117.4 . . ?
C51 C61 H61 117.4 . . ?
C76 C71 C77 109.5(3) . . ?
C76 C71 C41 108.2(3) . . ?
C77 C71 C41 111.1(3) . . ?
C76 C71 C75 107.7(3) . . ?
C77 C71 C75 108.0(3) . . ?
C41 C71 C75 112.3(3) . . ?
C71 C76 H763 109.5 . . ?
C71 C76 H761 109.5 . . ?
H763 C76 H761 109.5 . . ?
C71 C76 H762 109.5 . . ?
H763 C76 H762 109.5 . . ?
H761 C76 H762 109.5 . . ?
C71 C77 H771 109.5 . . ?
C71 C77 H772 109.5 . . ?
H771 C77 H772 109.5 . . ?
C71 C77 H773 109.5 . . ?
H771 C77 H773 109.5 . . ?
H772 C77 H773 109.5 . . ?
C71 C75 H751 109.5 . . ?
C71 C75 H752 109.5 . . ?
H751 C75 H752 109.5 . . ?
C71 C75 H753 109.5 . . ?
H751 C75 H753 109.5 . . ?
H752 C75 H753 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.93(3) 1.72(3) 2.622(3) 163(3) .
N1 H1 O6 0.93(3) 2.51(3) 3.031(3) 116(2) .
O2 H2 O3 0.87(4) 2.15(4) 2.611(3) 113(3) .
O2 H2 N2 0.87(4) 2.11(4) 2.843(3) 141(4) 1_545
C13 H13 N2 0.93 2.47 2.794(4) 100.8 .
C16 H16 O5 0.93 2.98 3.218(4) 96.6 .
C31 H31 O5 0.93 2.44 3.337(3) 161.4 .

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

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

data_dtbbpialt
_database_code_depnum_ccdc_archive 'CCDC 1567120'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_dtbbpialt           
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT112_dtbbpialt           
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.      c/2        100 %Fit
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;
_vrf_PLAT113_dtbbpialt           
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check
RESPONSE: The problem has been verified. The suggested pseudo symmetry has its reflection in the diffraction pattern  along the c* axis: every second reflection layers have weaker intensities than the other ones. The weaker reflections are, however, observable so that they cannot be omitted. Moreover the hydrogen and nitrogen  atoms positions do not exhibit pseudo symmetry.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 I2 N2 O4'
_chemical_formula_weight         660.27

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.261(3)
_cell_length_b                   11.779(3)
_cell_length_c                   11.997(4)
_cell_angle_alpha                99.09(4)
_cell_angle_beta                 103.48(5)
_cell_angle_gamma                94.58(4)
_cell_volume                     1247.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4701
_cell_measurement_theta_min      2.7016
_cell_measurement_theta_max      30.0973

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2835
_exptl_crystal_size_mid          0.1635
_exptl_crystal_size_min          0.1221
_exptl_absorpt_coefficient_mu    2.553
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_type   analytical

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            9785
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.707
_diffrn_reflns_theta_max         30.164
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6360
_reflns_number_gt                4927
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6360
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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
I1 I 0.7753(4) 0.0731(2) 0.5092(3) 0.0510(4) Uani 0.554(17) 1 d . . P A 1
I2 I 0.2178(4) -0.0611(3) -0.0282(3) 0.0457(3) Uani 0.554(17) 1 d . . P A 1
I11 I 0.7904(6) 0.0734(3) 0.4921(6) 0.0640(8) Uani 0.446(17) 1 d . . P A 2
I21 I 0.2082(6) -0.0583(4) -0.0137(6) 0.0578(8) Uani 0.446(17) 1 d . . P A 2
O2 O 0.5683(2) -0.15777(14) 0.36981(16) 0.0467(4) Uani 1 1 d . . . . .
H2 H 0.5230 -0.2192 0.3305 0.056 Uiso 1 1 calc R U . . .
O3 O 0.3635(2) -0.20850(14) 0.17217(16) 0.0488(5) Uani 1 1 d . . . . .
O5 O 0.42098(19) 0.17739(13) 0.11241(16) 0.0421(4) Uani 1 1 d . . . . .
O6 O 0.6312(2) 0.22679(14) 0.31461(17) 0.0486(5) Uani 1 1 d . . . . .
C1 C 0.6133(3) 0.03528(19) 0.3491(2) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.5387(3) -0.07261(18) 0.3104(2) 0.0352(5) Uani 1 1 d . . . . .
C3 C 0.4186(3) -0.10555(19) 0.1977(2) 0.0353(5) Uani 1 1 d . . . . .
C4 C 0.3811(3) -0.01791(19) 0.1318(2) 0.0346(5) Uani 1 1 d . . . . .
C5 C 0.4508(3) 0.09577(18) 0.1670(2) 0.0339(5) Uani 1 1 d . . . . .
C6 C 0.5735(3) 0.12644(18) 0.2821(2) 0.0350(5) Uani 1 1 d . . . . .
N1 N 0.5619(2) 0.38761(15) 0.14114(16) 0.0324(4) Uani 1 1 d . . . . .
H1 H 0.5058 0.3278 0.1461 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5580(2) 0.49024(18) 0.20795(19) 0.0279(4) Uani 1 1 d . . . . .
C13 C 0.6555(2) 0.58508(18) 0.2038(2) 0.0314(5) Uani 1 1 d . . . . .
H13 H 0.6546 0.6562 0.2499 0.038 Uiso 1 1 calc R U . . .
C14 C 0.7545(2) 0.57570(19) 0.1319(2) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.7457(3) 0.4686(2) 0.0605(2) 0.0403(6) Uani 1 1 d . . . . .
H15 H 0.8050 0.4599 0.0077 0.048 Uiso 1 1 calc R U . . .
C16 C 0.6506(3) 0.3761(2) 0.0673(2) 0.0395(6) Uani 1 1 d . . . . .
H16 H 0.6475 0.3047 0.0202 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8739(3) 0.6760(2) 0.1363(2) 0.0382(5) Uani 1 1 d . . . . .
C72 C 1.0236(3) 0.6480(3) 0.2055(3) 0.0578(8) Uani 1 1 d . . . . .
H721 H 1.0163 0.6397 0.2824 0.087 Uiso 1 1 calc R U . . .
H722 H 1.1006 0.7098 0.2109 0.087 Uiso 1 1 calc R U . . .
H723 H 1.0478 0.5771 0.1666 0.087 Uiso 1 1 calc R U . . .
C73 C 0.8401(4) 0.7927(2) 0.1962(3) 0.0625(9) Uani 1 1 d . . . . .
H731 H 0.7448 0.8098 0.1547 0.094 Uiso 1 1 calc R U . . .
H732 H 0.9166 0.8528 0.1964 0.094 Uiso 1 1 calc R U . . .
H733 H 0.8377 0.7885 0.2751 0.094 Uiso 1 1 calc R U . . .
C74 C 0.8844(3) 0.6866(3) 0.0123(2) 0.0559(7) Uani 1 1 d . . . . .
H741 H 0.9123 0.6161 -0.0243 0.084 Uiso 1 1 calc R U . . .
H742 H 0.9584 0.7500 0.0160 0.084 Uiso 1 1 calc R U . . .
H743 H 0.7891 0.7004 -0.0323 0.084 Uiso 1 1 calc R U . . .
N2 N 0.4613(2) 0.60498(16) 0.34997(17) 0.0359(4) Uani 1 1 d . . . . .
C21 C 0.4530(2) 0.49886(18) 0.28563(19) 0.0290(4) Uani 1 1 d . . . . .
C31 C 0.3541(2) 0.40548(18) 0.28963(19) 0.0307(5) Uani 1 1 d . . . . .
H31 H 0.3516 0.3342 0.2427 0.037 Uiso 1 1 calc R U . . .
C41 C 0.2581(2) 0.4181(2) 0.3639(2) 0.0329(5) Uani 1 1 d . . . . .
C51 C 0.2723(3) 0.5264(2) 0.4329(2) 0.0421(6) Uani 1 1 d . . . . .
H51 H 0.2138 0.5393 0.4859 0.051 Uiso 1 1 calc R U . . .
C61 C 0.3731(3) 0.6157(2) 0.4236(2) 0.0429(6) Uani 1 1 d . . . . .
H61 H 0.3796 0.6872 0.4713 0.051 Uiso 1 1 calc R U . . .
C71 C 0.1396(3) 0.3190(2) 0.3664(2) 0.0390(5) Uani 1 1 d . . . . .
C75 C 0.1710(4) 0.2011(3) 0.3092(4) 0.0809(12) Uani 1 1 d . . . . .
H751 H 0.0926 0.1427 0.3093 0.121 Uiso 1 1 calc R U . . .
H752 H 0.2649 0.1831 0.3521 0.121 Uiso 1 1 calc R U . . .
H753 H 0.1751 0.2035 0.2304 0.121 Uiso 1 1 calc R U . . .
C76 C -0.0120(3) 0.3428(3) 0.2981(3) 0.0704(9) Uani 1 1 d . . . . .
H761 H -0.0356 0.4155 0.3337 0.106 Uiso 1 1 calc R U . . .
H762 H -0.0873 0.2820 0.2983 0.106 Uiso 1 1 calc R U . . .
H763 H -0.0086 0.3458 0.2192 0.106 Uiso 1 1 calc R U . . .
C77 C 0.1355(4) 0.3147(3) 0.4919(3) 0.0733(10) Uani 1 1 d . . . . .
H771 H 0.0990 0.3833 0.5241 0.110 Uiso 1 1 calc R U . . .
H772 H 0.2345 0.3104 0.5371 0.110 Uiso 1 1 calc R U . . .
H773 H 0.0703 0.2477 0.4935 0.110 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
I1 C1 2.102(4) . ?
I2 C4 2.109(5) . ?
I11 C1 2.040(5) . ?
I21 C4 2.037(6) . ?
O2 C2 1.330(3) . ?
O2 H2 0.8200 . ?
O3 C3 1.239(3) . ?
O5 C5 1.260(3) . ?
O6 C6 1.221(3) . ?
C1 C2 1.354(3) . ?
C1 C6 1.461(3) . ?
C2 C3 1.510(4) . ?
C3 C4 1.413(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.540(4) . ?
N1 C16 1.341(3) . ?
N1 C12 1.349(3) . ?
N1 H1 0.8600 . ?
C12 C13 1.394(3) . ?
C12 C21 1.494(3) . ?
C13 C14 1.397(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(3) . ?
C14 C17 1.538(3) . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C72 1.531(4) . ?
C17 C74 1.537(3) . ?
C17 C73 1.539(4) . ?
C72 H721 0.9600 . ?
C72 H722 0.9600 . ?
C72 H723 0.9600 . ?
C73 H731 0.9600 . ?
C73 H732 0.9600 . ?
C73 H733 0.9600 . ?
C74 H741 0.9600 . ?
C74 H742 0.9600 . ?
C74 H743 0.9600 . ?
N2 C61 1.335(3) . ?
N2 C21 1.348(3) . ?
C21 C31 1.388(3) . ?
C31 C41 1.399(3) . ?
C31 H31 0.9300 . ?
C41 C51 1.385(3) . ?
C41 C71 1.545(3) . ?
C51 C61 1.385(3) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C71 C76 1.523(4) . ?
C71 C77 1.524(4) . ?
C71 C75 1.530(4) . ?
C75 H751 0.9600 . ?
C75 H752 0.9600 . ?
C75 H753 0.9600 . ?
C76 H761 0.9600 . ?
C76 H762 0.9600 . ?
C76 H763 0.9600 . ?
C77 H771 0.9600 . ?
C77 H772 0.9600 . ?
C77 H773 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H2 109.5 . . ?
C2 C1 C6 119.2(2) . . ?
C2 C1 I11 122.4(2) . . ?
C6 C1 I11 118.2(2) . . ?
C2 C1 I1 120.1(2) . . ?
C6 C1 I1 120.52(18) . . ?
O2 C2 C1 121.5(2) . . ?
O2 C2 C3 115.33(19) . . ?
C1 C2 C3 123.2(2) . . ?
O3 C3 C4 126.6(2) . . ?
O3 C3 C2 115.7(2) . . ?
C4 C3 C2 117.7(2) . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 I21 119.3(2) . . ?
C3 C4 I21 118.0(2) . . ?
C5 C4 I2 118.5(2) . . ?
C3 C4 I2 119.0(2) . . ?
O5 C5 C4 125.2(2) . . ?
O5 C5 C6 116.3(2) . . ?
C4 C5 C6 118.5(2) . . ?
O6 C6 C1 122.7(2) . . ?
O6 C6 C5 118.4(2) . . ?
C1 C6 C5 118.83(19) . . ?
C16 N1 C12 121.98(19) . . ?
C16 N1 H1 119.0 . . ?
C12 N1 H1 119.0 . . ?
N1 C12 C13 118.35(19) . . ?
N1 C12 C21 119.7(2) . . ?
C13 C12 C21 122.0(2) . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 116.7(2) . . ?
C15 C14 C17 121.3(2) . . ?
C13 C14 C17 121.9(2) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C15 120.6(2) . . ?
N1 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C72 C17 C74 109.5(2) . . ?
C72 C17 C14 107.3(2) . . ?
C74 C17 C14 110.2(2) . . ?
C72 C17 C73 109.0(3) . . ?
C74 C17 C73 108.6(2) . . ?
C14 C17 C73 112.3(2) . . ?
C17 C72 H721 109.5 . . ?
C17 C72 H722 109.5 . . ?
H721 C72 H722 109.5 . . ?
C17 C72 H723 109.5 . . ?
H721 C72 H723 109.5 . . ?
H722 C72 H723 109.5 . . ?
C17 C73 H731 109.5 . . ?
C17 C73 H732 109.5 . . ?
H731 C73 H732 109.5 . . ?
C17 C73 H733 109.5 . . ?
H731 C73 H733 109.5 . . ?
H732 C73 H733 109.5 . . ?
C17 C74 H741 109.5 . . ?
C17 C74 H742 109.5 . . ?
H741 C74 H742 109.5 . . ?
C17 C74 H743 109.5 . . ?
H741 C74 H743 109.5 . . ?
H742 C74 H743 109.5 . . ?
C61 N2 C21 116.4(2) . . ?
N2 C21 C31 123.1(2) . . ?
N2 C21 C12 114.3(2) . . ?
C31 C21 C12 122.6(2) . . ?
C21 C31 C41 120.3(2) . . ?
C21 C31 H31 119.8 . . ?
C41 C31 H31 119.8 . . ?
C51 C41 C31 115.8(2) . . ?
C51 C41 C71 121.8(2) . . ?
C31 C41 C71 122.3(2) . . ?
C61 C51 C41 120.5(2) . . ?
C61 C51 H51 119.7 . . ?
C41 C51 H51 119.7 . . ?
N2 C61 C51 123.8(2) . . ?
N2 C61 H61 118.1 . . ?
C51 C61 H61 118.1 . . ?
C76 C71 C77 109.8(3) . . ?
C76 C71 C75 107.9(3) . . ?
C77 C71 C75 109.0(3) . . ?
C76 C71 C41 108.1(2) . . ?
C77 C71 C41 109.9(2) . . ?
C75 C71 C41 112.1(2) . . ?
C71 C75 H751 109.5 . . ?
C71 C75 H752 109.5 . . ?
H751 C75 H752 109.5 . . ?
C71 C75 H753 109.5 . . ?
H751 C75 H753 109.5 . . ?
H752 C75 H753 109.5 . . ?
C71 C76 H761 109.5 . . ?
C71 C76 H762 109.5 . . ?
H761 C76 H762 109.5 . . ?
C71 C76 H763 109.5 . . ?
H761 C76 H763 109.5 . . ?
H762 C76 H763 109.5 . . ?
C71 C77 H771 109.5 . . ?
C71 C77 H772 109.5 . . ?
H771 C77 H772 109.5 . . ?
C71 C77 H773 109.5 . . ?
H771 C77 H773 109.5 . . ?
H772 C77 H773 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.86 1.82 2.638(3) 157.6 .
N1 H1 O6 0.86 2.60 3.025(3) 112.0 .
O2 H2 O3 0.82 2.15 2.617(3) 116.6 .
O2 H2 N2 0.82 2.17 2.843(3) 139.8 1_545
C13 H13 N2 0.93 2.46 2.788(3) 100.6 .
C16 H16 O5 0.93 3.00 3.230(3) 96.1 .
C31 H31 O5 0.93 2.45 3.346(3) 161.4 .
C16 H16 O3 0.93 2.38 3.187(3) 145.0 2_655
C72 H722 O3 0.96 2.71 3.588(4) 151.6 1_665
C74 H743 O5 0.96 2.61 3.509(4) 156.7 2_665
C61 H61 O6 0.93 2.64 3.397(3) 139.5 2_666
C76 H762 O6 0.96 2.70 3.535(4) 146.4 1_455

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

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

data_250
_database_code_depnum_ccdc_archive 'CCDC 1567118'
_audit_update_record             
;
2017-08-07 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4,4'-di-tert-butyl-2,2'-bipyridyl
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 N2'
_chemical_formula_sum            'C18 H24 N2'
_chemical_formula_weight         268.39

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      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                   12.3193(7)
_cell_length_b                   6.5863(3)
_cell_length_c                   10.3445(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.039(5)
_cell_angle_gamma                90
_cell_volume                     820.88(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    1197
_cell_measurement_theta_min      2.8807
_cell_measurement_theta_max      28.6447

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.172
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4348
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         28.708
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1886
_reflns_number_gt                1178
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0899P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1886
_refine_ls_number_parameters     132
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1929
_refine_ls_wR_factor_gt          0.1610
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.005
_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
C12 C 0.03264(15) 0.0650(3) 0.55263(16) 0.0443(5) Uani 1 1 d . . . . .
N1 N -0.00837(13) 0.2505(3) 0.56690(15) 0.0517(5) Uani 1 1 d . . . . .
C13 C 0.13183(15) -0.0039(3) 0.63212(17) 0.0479(5) Uani 1 1 d . . . . .
C15 C 0.14672(16) 0.3076(3) 0.74664(19) 0.0530(6) Uani 1 1 d . . . . .
C17 C 0.29778(16) 0.0454(3) 0.8243(2) 0.0581(6) Uani 1 1 d . . . . .
C14 C 0.19081(14) 0.1172(3) 0.73226(18) 0.0480(5) Uani 1 1 d . . . . .
C16 C 0.04919(17) 0.3682(3) 0.66269(19) 0.0548(6) Uani 1 1 d . . . . .
H16 H 0.0201(16) 0.509(3) 0.6696(18) 0.050(5) Uiso 1 1 d . . . . .
H15 H 0.1832(17) 0.402(3) 0.815(2) 0.060(6) Uiso 1 1 d . . . . .
H13 H 0.1568(16) -0.136(3) 0.6157(18) 0.048(5) Uiso 1 1 d . . . . .
C721 C 0.3287(6) -0.1715(12) 0.7951(8) 0.153(5) Uani 0.688(10) 1 d . U P A 1
H21A H 0.2669 -0.2612 0.7981 0.229 Uiso 0.688(10) 1 calc R U P A 1
H21B H 0.3930 -0.2140 0.8607 0.229 Uiso 0.688(10) 1 calc R U P A 1
H21C H 0.3461 -0.1773 0.7079 0.229 Uiso 0.688(10) 1 calc R U P A 1
C731 C 0.2767(4) 0.0437(13) 0.9647(4) 0.097(2) Uani 0.688(10) 1 d . U P A 1
H31A H 0.2157 -0.0475 0.9689 0.145 Uiso 0.688(10) 1 calc R U P A 1
H31B H 0.2580 0.1797 0.9887 0.145 Uiso 0.688(10) 1 calc R U P A 1
H31C H 0.3430 -0.0021 1.0257 0.145 Uiso 0.688(10) 1 calc R U P A 1
C741 C 0.3902(3) 0.1862(13) 0.8180(8) 0.131(4) Uani 0.688(10) 1 d . U P A 1
H41A H 0.4574 0.1386 0.8766 0.196 Uiso 0.688(10) 1 calc R U P A 1
H41B H 0.3720 0.3208 0.8452 0.196 Uiso 0.688(10) 1 calc R U P A 1
H41C H 0.4019 0.1917 0.7282 0.196 Uiso 0.688(10) 1 calc R U P A 1
C722 C 0.3797(9) 0.006(3) 0.7389(12) 0.119(6) Uani 0.312(10) 1 d . U P A 2
H22A H 0.3789 0.1190 0.6783 0.178 Uiso 0.312(10) 1 calc R U P A 2
H22B H 0.3599 -0.1178 0.6891 0.178 Uiso 0.312(10) 1 calc R U P A 2
H22C H 0.4533 -0.0074 0.7940 0.178 Uiso 0.312(10) 1 calc R U P A 2
C732 C 0.3493(13) 0.213(3) 0.9194(18) 0.152(10) Uani 0.312(10) 1 d . U P A 2
H32A H 0.3723 0.3246 0.8697 0.229 Uiso 0.312(10) 1 calc R U P A 2
H32B H 0.4133 0.1603 0.9810 0.229 Uiso 0.312(10) 1 calc R U P A 2
H32C H 0.2950 0.2620 0.9679 0.229 Uiso 0.312(10) 1 calc R U P A 2
C742 C 0.2768(11) -0.139(4) 0.885(3) 0.192(14) Uani 0.312(10) 1 d . U P A 2
H42A H 0.3444 -0.1857 0.9430 0.288 Uiso 0.312(10) 1 calc R U P A 2
H42B H 0.2513 -0.2405 0.8175 0.288 Uiso 0.312(10) 1 calc R U P A 2
H42C H 0.2201 -0.1171 0.9361 0.288 Uiso 0.312(10) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 N1 1.342(2) . ?
C12 C13 1.399(2) . ?
C12 C12 1.484(4) 3_556 ?
N1 C16 1.339(2) . ?
C13 C14 1.387(3) . ?
C15 C14 1.387(3) . ?
C15 C16 1.386(3) . ?
C17 C722 1.495(11) . ?
C17 C742 1.416(13) . ?
C17 C741 1.481(5) . ?
C17 C14 1.531(3) . ?
C17 C721 1.525(6) . ?
C17 C731 1.529(5) . ?
C17 C732 1.528(12) . ?

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 C12 C13 122.26(17) . . ?
N1 C12 C12 116.59(19) . 3_556 ?
C13 C12 C12 121.2(2) . 3_556 ?
C16 N1 C12 117.06(16) . . ?
C12 C13 C14 120.66(19) . . ?
C14 C15 C16 120.03(19) . . ?
C722 C17 C742 108.9(13) . . ?
C722 C17 C14 106.6(4) . . ?
C742 C17 C14 109.1(5) . . ?
C741 C17 C14 110.5(2) . . ?
C741 C17 C721 110.6(4) . . ?
C14 C17 C721 112.6(2) . . ?
C741 C17 C731 109.3(4) . . ?
C14 C17 C731 107.3(2) . . ?
C721 C17 C731 106.3(4) . . ?
C722 C17 C732 105.3(10) . . ?
C742 C17 C732 115.2(13) . . ?
C14 C17 C732 111.4(5) . . ?
C15 C14 C13 116.37(17) . . ?
C15 C14 C17 121.22(18) . . ?
C13 C14 C17 122.40(18) . . ?
N1 C16 C15 123.6(2) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

