# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1559130'
_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2yn'
#Added by publCIF


_audit_creation_date             2017-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 Br4 N4'
_chemical_formula_sum            'C14 H6 Br4 N4'
_chemical_formula_weight         549.87
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4013(7)
_cell_length_b                   7.1404(6)
_cell_length_c                   26.687(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1330(10)
_cell_angle_gamma                90
_cell_volume                     1591.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.312
_shelx_estimated_absorpt_T_min   0.107
_exptl_absorpt_coefficient_mu    10.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1386 before and 0.0353 after correction. The Ratio of minimum to maximum transmission is 0.5862. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.682
_diffrn_reflns_theta_min         1.535
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3382
_reflns_number_total             3710
_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 V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      1.152
_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)+(0.0226P)²+2.0483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0554
_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:
 C13(H13), C11(H11), C12(H12), C4(H4), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br3 Br 0.13676(3) 0.15861(3) 0.58975(2) 0.02301(7) Uani 1 1 d . . . . .
Br2 Br 0.38343(3) 0.57371(3) 0.77799(2) 0.02266(7) Uani 1 1 d . . . . .
Br1 Br 0.61143(3) 1.06044(4) 0.63256(2) 0.02648(7) Uani 1 1 d . . . . .
Br4 Br 0.37526(3) 0.81118(4) 0.50223(2) 0.02795(7) Uani 1 1 d . . . . .
N1 N 0.2695(2) 0.7287(3) 0.65692(7) 0.0188(4) Uani 1 1 d . . . . .
N3 N 0.4648(2) 0.5153(3) 0.60525(8) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.2079(2) 0.6395(3) 0.61550(8) 0.0199(4) Uani 1 1 d . . . . .
N4 N 0.5258(2) 0.6029(3) 0.64686(8) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.4970(2) 0.8412(3) 0.71067(8) 0.0140(4) Uani 1 1 d . . . . .
C7 C 0.4282(3) 0.7172(3) 0.66902(8) 0.0141(4) Uani 1 1 d . . . . .
C8 C 0.3109(3) 0.5479(3) 0.58931(8) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.4771(3) 0.8036(3) 0.76084(8) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.2512(3) 0.4727(3) 0.53867(8) 0.0141(4) Uani 1 1 d . . . . .
C14 C 0.2749(3) 0.5736(3) 0.49518(9) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.2250(3) 0.5076(4) 0.44717(8) 0.0184(5) Uani 1 1 d . . . . .
H13 H 0.2411 0.5800 0.4183 0.022 Uiso 1 1 calc R . . . .
C1 C 0.5746(3) 1.0066(3) 0.70006(8) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.1741(3) 0.3005(3) 0.53210(8) 0.0161(4) Uani 1 1 d . . . . .
C11 C 0.1249(3) 0.2303(4) 0.48442(9) 0.0207(5) Uani 1 1 d . . . . .
H11 H 0.0734 0.1119 0.4807 0.025 Uiso 1 1 calc R . . . .
C12 C 0.1516(3) 0.3346(4) 0.44230(9) 0.0197(5) Uani 1 1 d . . . . .
H12 H 0.1190 0.2864 0.4096 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5285(3) 0.9287(3) 0.79912(9) 0.0186(5) Uani 1 1 d . . . . .
H4 H 0.5146 0.9005 0.8332 0.022 Uiso 1 1 calc R . . . .
C2 C 0.6252(3) 1.1349(4) 0.73755(9) 0.0205(5) Uani 1 1 d . . . . .
H2 H 0.6761 1.2481 0.7295 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6001(3) 1.0949(4) 0.78694(9) 0.0209(5) Uani 1 1 d . . . . .
H3 H 0.6325 1.1827 0.8128 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br3 C10 1.896(2) . ?
Br2 C5 1.897(2) . ?
Br1 C1 1.899(2) . ?
Br4 C14 1.895(2) . ?
N1 N2 1.331(3) . ?
N1 C7 1.340(3) . ?
N3 N4 1.329(3) . ?
N3 C8 1.337(3) . ?
N2 C8 1.340(3) . ?
N4 C7 1.338(3) . ?
C6 C7 1.488(3) . ?
C6 C5 1.393(3) . ?
C6 C1 1.393(3) . ?
C8 C9 1.490(3) . ?
C5 C4 1.390(3) . ?
C9 C14 1.398(3) . ?
C9 C10 1.393(3) . ?
C14 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.380(4) . ?
C1 C2 1.389(3) . ?
C10 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 117.35(19) . . ?
N4 N3 C8 117.21(19) . . ?
N1 N2 C8 116.80(19) . . ?
N3 N4 C7 117.17(19) . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 C1 117.7(2) . . ?
C1 C6 C7 120.3(2) . . ?
N1 C7 C6 116.11(19) . . ?
N4 C7 N1 124.8(2) . . ?
N4 C7 C6 119.06(19) . . ?
N3 C8 N2 125.1(2) . . ?
N3 C8 C9 116.49(19) . . ?
N2 C8 C9 118.37(19) . . ?
C6 C5 Br2 119.58(17) . . ?
C4 C5 Br2 118.86(17) . . ?
C4 C5 C6 121.5(2) . . ?
C14 C9 C8 120.2(2) . . ?
C10 C9 C8 122.63(19) . . ?
C10 C9 C14 117.1(2) . . ?
C9 C14 Br4 118.69(17) . . ?
C13 C14 Br4 118.89(18) . . ?
C13 C14 C9 122.4(2) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 H13 120.7 . . ?
C6 C1 Br1 119.45(17) . . ?
C2 C1 Br1 118.77(18) . . ?
C2 C1 C6 121.8(2) . . ?
C9 C10 Br3 119.00(16) . . ?
C11 C10 Br3 119.46(18) . . ?
C11 C10 C9 121.5(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_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_Compound_10
_database_code_depnum_ccdc_archive 'CCDC 1993888'
loop_
_audit_author_name
_audit_author_address
'HELENE CATTEY'
;University of Burgundy
France
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H34 N4 O4'
_chemical_formula_sum            'C42 H34 N4 O4'
_chemical_formula_weight         658.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.6114(8)
_cell_length_b                   7.0737(4)
_cell_length_c                   19.7448(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.356(2)
_cell_angle_gamma                90
_cell_volume                     1620.38(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0676 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.7756.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of dichloromethane and pentane  by slow evaporation'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30148
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_min         3.059
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3232
_reflns_number_total             3717
_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, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.40A (bruker, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.8001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13), C16(H16),
 C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07879(7) 0.74400(13) 0.29953(5) 0.0229(2) Uani 1 1 d . . . . .
O2 O 1.03517(7) 0.28050(13) 0.45446(4) 0.0212(2) Uani 1 1 d . . . . .
N1 N 0.43272(8) 0.45241(14) 0.44410(5) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.39988(8) 0.40175(14) 0.50526(5) 0.0161(2) Uani 1 1 d . . . . .
C1 C 0.53187(9) 0.54931(16) 0.44061(5) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.57046(9) 0.61038(16) 0.37272(5) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.50157(10) 0.73260(16) 0.33237(5) 0.0143(2) Uani 1 1 d . . . . .
C4 C 0.54172(10) 0.79582(17) 0.27055(6) 0.0163(2) Uani 1 1 d . . . . .
H4 H 0.494631 0.876617 0.242736 0.020 Uiso 1 1 calc R . . . .
C5 C 0.64934(10) 0.74233(17) 0.24918(6) 0.0172(2) Uani 1 1 d . . . . .
H5 H 0.676563 0.788820 0.207633 0.021 Uiso 1 1 calc R . . . .
C6 C 0.71680(10) 0.62054(17) 0.28895(6) 0.0162(2) Uani 1 1 d . . . . .
H6 H 0.790868 0.585157 0.274600 0.019 Uiso 1 1 calc R . . . .
C7 C 0.67757(10) 0.54905(16) 0.34978(5) 0.0142(2) Uani 1 1 d . . . . .
C8 C 0.38603(10) 0.79957(16) 0.35233(5) 0.0152(2) Uani 1 1 d . . . . .
C9 C 0.28821(10) 0.73214(16) 0.31615(6) 0.0160(2) Uani 1 1 d . . . . .
H9 H 0.295627 0.639784 0.281675 0.019 Uiso 1 1 calc R . . . .
C10 C 0.18007(10) 0.80156(17) 0.33113(6) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.16970(10) 0.93953(18) 0.38062(6) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.095818 0.987571 0.390424 0.024 Uiso 1 1 calc R . . . .
C12 C 0.26691(11) 1.00700(18) 0.41562(6) 0.0203(3) Uani 1 1 d . . . . .
H12 H 0.259500 1.102606 0.448951 0.024 Uiso 1 1 calc R . . . .
C13 C 0.37593(10) 0.93552(17) 0.40231(6) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.442330 0.979597 0.427226 0.021 Uiso 1 1 calc R . . . .
C14 C 0.08599(11) 0.6099(2) 0.24572(6) 0.0248(3) Uani 1 1 d . . . . .
H14A H 0.135738 0.659976 0.211046 0.037 Uiso 1 1 calc GR . . . .
H14B H 0.008763 0.586469 0.225568 0.037 Uiso 1 1 calc GR . . . .
H14C H 0.118403 0.491220 0.263640 0.037 Uiso 1 1 calc GR . . . .
C15 C 0.74363(10) 0.39411(16) 0.38402(5) 0.0152(2) Uani 1 1 d . . . . .
C16 C 0.86024(10) 0.41859(17) 0.40287(6) 0.0167(2) Uani 1 1 d . . . . .
H16 H 0.896760 0.536991 0.396331 0.020 Uiso 1 1 calc R . . . .
C17 C 0.92218(10) 0.26748(18) 0.43133(6) 0.0173(2) Uani 1 1 d . . . . .
C18 C 0.86969(10) 0.09194(17) 0.43907(6) 0.0190(3) Uani 1 1 d . . . . .
H18 H 0.912431 -0.010820 0.458236 0.023 Uiso 1 1 calc R . . . .
C19 C 0.75500(10) 0.06785(18) 0.41870(6) 0.0199(3) Uani 1 1 d . . . . .
H19 H 0.719710 -0.052435 0.423148 0.024 Uiso 1 1 calc R . . . .
C20 C 0.69112(10) 0.21860(18) 0.39179(6) 0.0182(2) Uani 1 1 d . . . . .
H20 H 0.612093 0.201987 0.378771 0.022 Uiso 1 1 calc R . . . .
C21 C 1.10162(11) 0.43444(19) 0.42936(6) 0.0222(3) Uani 1 1 d . . . . .
H21A H 1.100353 0.429700 0.379728 0.033 Uiso 1 1 calc GR . . . .
H21B H 1.181354 0.424291 0.447263 0.033 Uiso 1 1 calc GR . . . .
H21C H 1.068543 0.554474 0.443933 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.3703(14) . ?
O1 C14 1.4295(16) . ?
O2 C17 1.3744(14) . ?
O2 C21 1.4346(15) . ?
N1 N2 1.3306(13) . ?
N1 C1 1.3440(15) . ?
N2 C1 1.3492(14) 3_666 ?
C1 C2 1.4946(15) . ?
C2 C3 1.4034(15) . ?
C2 C7 1.4094(16) . ?
C3 C4 1.3980(16) . ?
C3 C8 1.4910(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3877(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3862(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3968(16) . ?
C7 C15 1.4846(16) . ?
C8 C9 1.4004(16) . ?
C8 C13 1.3863(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3913(17) . ?
C10 C11 1.3898(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3840(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3981(17) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.4002(16) . ?
C15 C20 1.3944(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3937(16) . ?
C17 C18 1.3944(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3857(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3918(17) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C10 O1 C14 117.41(10) . . ?
C17 O2 C21 117.11(9) . . ?
N2 N1 C1 117.51(9) . . ?
N1 N2 C1 117.96(10) . 3_666 ?
N1 C1 N2 124.53(10) . 3_666 ?
N1 C1 C2 118.84(9) . . ?
N2 C1 C2 116.64(10) 3_666 . ?
C3 C2 C1 120.15(10) . . ?
C3 C2 C7 119.81(10) . . ?
C7 C2 C1 120.02(10) . . ?
C2 C3 C8 122.94(10) . . ?
C4 C3 C2 119.34(10) . . ?
C4 C3 C8 117.72(10) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.00(11) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.49(11) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.02(11) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C15 121.82(10) . . ?
C6 C7 C2 119.22(10) . . ?
C6 C7 C15 118.56(10) . . ?
C9 C8 C3 118.47(10) . . ?
C13 C8 C3 120.79(10) . . ?
C13 C8 C9 120.58(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.45(11) . . ?
C10 C9 H9 120.3 . . ?
O1 C10 C9 124.30(11) . . ?
O1 C10 C11 115.55(11) . . ?
C11 C10 C9 120.15(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.05(11) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.50(11) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.24(11) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C7 120.38(10) . . ?
C20 C15 C7 119.17(10) . . ?
C20 C15 C16 120.22(11) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.32(11) . . ?
C17 C16 H16 120.3 . . ?
O2 C17 C16 123.53(11) . . ?
O2 C17 C18 116.03(10) . . ?
C16 C17 C18 120.43(11) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.80(11) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.48(12) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.71(11) . . ?
C19 C20 H20 120.1 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'

#------------------ END ----------------------------------------------------#
####################################################################### 
# 
# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 1991440'
loop_
_audit_author_name
_audit_author_address
'HELENE CATTEY'
;University of Burgundy
France
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H58 N4, C H2 Cl2'
_chemical_formula_sum            'C55 H60 Cl2 N4'
_chemical_formula_weight         847.97
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4912(6)
_cell_length_b                   12.8803(8)
_cell_length_c                   17.1913(9)
_cell_angle_alpha                77.642(2)
_cell_angle_beta                 74.455(2)
_cell_angle_gamma                88.158(2)
_cell_volume                     2393.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9441
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0748 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.9079. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of ether and dichloromethane  by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            105384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8080
_reflns_number_total             11025
_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, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.40A (bruker, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         11025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+3.8275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1641
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=
 Sof(H26F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C19(H19),
 C20(H20), C22(H22), C23(H23), C31(H31), C32(H32), C33(H33), C36(H36), C37(H37),
  C39(H39), C40(H40), C46(H46), C47(H47), C49(H49), C50(H50)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C42(H42A,H42B,H42C), C43(H43A,
 H43B,H43C), C44(H44A,H44B,H44C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C), C27A(H27D,H27E,H27F), C26A(H26D,H26E,H26F), C25A(H25D,
 H25E,H25F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45789(18) 0.53908(16) 0.24947(12) 0.0106(4) Uani 1 1 d . . . . .
N1 N 0.39544(15) 0.53065(14) 0.32902(11) 0.0125(4) Uani 1 1 d . . . . .
C2 C 0.57860(18) 0.49121(16) 0.23044(12) 0.0115(4) Uani 1 1 d . . . . .
N2 N 0.29512(15) 0.58603(14) 0.34448(11) 0.0131(4) Uani 1 1 d . . . . .
C3 C 0.60759(19) 0.42528(16) 0.17233(13) 0.0129(4) Uani 1 1 d . . . . .
N3 N 0.41796(15) 0.58807(14) 0.18472(11) 0.0126(4) Uani 1 1 d . . . . .
C4 C 0.7263(2) 0.39196(18) 0.14911(14) 0.0178(4) Uani 1 1 d . . . . .
H4 H 0.747924 0.349847 0.108550 0.021 Uiso 1 1 calc R . . . .
N4 N 0.31653(15) 0.64096(14) 0.20006(11) 0.0124(4) Uani 1 1 d . . . . .
C5 C 0.8129(2) 0.4192(2) 0.18408(15) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.893428 0.396260 0.167253 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7823(2) 0.48000(19) 0.24376(15) 0.0192(5) Uani 1 1 d . . . . .
H6 H 0.841348 0.496112 0.269211 0.023 Uiso 1 1 calc R . . . .
C7 C 0.66582(19) 0.51772(17) 0.26681(13) 0.0137(4) Uani 1 1 d . . . . .
C8 C 0.51533(19) 0.38389(16) 0.13970(13) 0.0124(4) Uani 1 1 d . . . . .
C9 C 0.4103(2) 0.33183(17) 0.19264(13) 0.0152(4) Uani 1 1 d . . . . .
H9 H 0.394709 0.326851 0.250469 0.018 Uiso 1 1 calc R . . . .
C10 C 0.3285(2) 0.28737(17) 0.16256(13) 0.0157(4) Uani 1 1 d . . . . .
H10 H 0.259157 0.250037 0.200364 0.019 Uiso 1 1 calc R . . . .
C11 C 0.34514(19) 0.29584(17) 0.07758(13) 0.0140(4) Uani 1 1 d . . . . .
C12 C 0.4504(2) 0.34747(17) 0.02498(13) 0.0146(4) Uani 1 1 d . . . . .
H12 H 0.465017 0.354141 -0.032959 0.018 Uiso 1 1 calc R . . . .
C13 C 0.53505(19) 0.38967(17) 0.05541(13) 0.0143(4) Uani 1 1 d . . . . .
H13 H 0.607209 0.422852 0.018058 0.017 Uiso 1 1 calc R . . . .
C14 C 0.2514(2) 0.24652(19) 0.04642(14) 0.0183(5) Uani 1 1 d . . . . .
C15 C 0.1248(2) 0.2826(3) 0.08570(18) 0.0392(7) Uani 1 1 d . . . . .
H15A H 0.104296 0.256065 0.145699 0.059 Uiso 1 1 calc GR . . . .
H15B H 0.065694 0.254369 0.063177 0.059 Uiso 1 1 calc GR . . . .
H15C H 0.123489 0.360462 0.073312 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.2748(2) 0.28100(19) -0.04769(14) 0.0219(5) Uani 1 1 d . . . . .
H16A H 0.272426 0.358647 -0.063348 0.033 Uiso 1 1 calc GR . . . .
H16B H 0.212437 0.249098 -0.065219 0.033 Uiso 1 1 calc GR . . . .
H16C H 0.354401 0.257275 -0.074605 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.2569(3) 0.1253(2) 0.07022(17) 0.0331(6) Uani 1 1 d . . . . .
H17A H 0.337969 0.102876 0.044942 0.050 Uiso 1 1 calc GR . . . .
H17B H 0.197383 0.092881 0.050487 0.050 Uiso 1 1 calc GR . . . .
H17C H 0.238779 0.102637 0.130470 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.63972(18) 0.58668(17) 0.32862(13) 0.0132(4) Uani 1 1 d . . . . .
C19 C 0.6111(2) 0.69317(18) 0.30815(13) 0.0164(4) Uani 1 1 d . . . . .
H19 H 0.604963 0.722859 0.253881 0.020 Uiso 1 1 calc R . . . .
C20 C 0.5915(2) 0.75634(18) 0.36625(14) 0.0182(5) Uani 1 1 d . . . . .
H20 H 0.572179 0.828849 0.351116 0.022 Uiso 1 1 calc R . . . .
C21 C 0.59958(19) 0.71502(18) 0.44675(13) 0.0157(4) Uani 1 1 d . . . . .
C22 C 0.62685(19) 0.60822(18) 0.46688(13) 0.0161(4) Uani 1 1 d . . . . .
H22 H 0.631652 0.577988 0.521379 0.019 Uiso 1 1 calc R . . . .
C23 C 0.64714(19) 0.54516(18) 0.40871(14) 0.0156(4) Uani 1 1 d . . . . .
H23 H 0.666374 0.472635 0.423797 0.019 Uiso 1 1 calc R . . . .
C24 C 0.5776(2) 0.7850(2) 0.51077(15) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.5972(5) 0.7392(4) 0.5883(3) 0.0276(13) Uani 0.518(5) 1 d . . P A 1
H25A H 0.542570 0.677287 0.614862 0.041 Uiso 0.518(5) 1 calc GR . P A 1
H25B H 0.581522 0.791628 0.623403 0.041 Uiso 0.518(5) 1 calc GR . P A 1
H25C H 0.681103 0.716780 0.580630 0.041 Uiso 0.518(5) 1 calc GR . P A 1
C26 C 0.4431(4) 0.8257(4) 0.5214(3) 0.0256(12) Uani 0.518(5) 1 d . . P A 1
H26A H 0.434310 0.865201 0.467884 0.038 Uiso 0.518(5) 1 calc GR . P A 1
H26B H 0.425868 0.872434 0.561008 0.038 Uiso 0.518(5) 1 calc GR . P A 1
H26C H 0.386240 0.764674 0.541772 0.038 Uiso 0.518(5) 1 calc GR . P A 1
C27 C 0.6591(5) 0.8934(4) 0.4704(3) 0.0219(11) Uani 0.518(5) 1 d . . P A 1
H27A H 0.744939 0.876322 0.459479 0.033 Uiso 0.518(5) 1 calc GR . P A 1
H27B H 0.640666 0.941677 0.508869 0.033 Uiso 0.518(5) 1 calc GR . P A 1
H27C H 0.641100 0.927855 0.418471 0.033 Uiso 0.518(5) 1 calc GR . P A 1
C28 C 0.26237(18) 0.64336(16) 0.27915(12) 0.0111(4) Uani 1 1 d . . . . .
C29 C 0.15385(18) 0.71071(17) 0.29402(12) 0.0118(4) Uani 1 1 d . . . . .
C30 C 0.03826(19) 0.66183(17) 0.32692(13) 0.0140(4) Uani 1 1 d . . . . .
C31 C -0.06242(19) 0.72639(18) 0.33905(14) 0.0183(5) Uani 1 1 d . . . . .
H31 H -0.141097 0.694605 0.361184 0.022 Uiso 1 1 calc R . . . .
C32 C -0.0487(2) 0.83620(19) 0.31914(15) 0.0222(5) Uani 1 1 d . . . . .
H32 H -0.117999 0.879042 0.326967 0.027 Uiso 1 1 calc R . . . .
C33 C 0.0653(2) 0.88377(19) 0.28792(15) 0.0209(5) Uani 1 1 d . . . . .
H33 H 0.073560 0.959114 0.275027 0.025 Uiso 1 1 calc R . . . .
C34 C 0.16883(19) 0.82240(17) 0.27507(13) 0.0144(4) Uani 1 1 d . . . . .
C35 C 0.01899(18) 0.54409(17) 0.34757(13) 0.0130(4) Uani 1 1 d . . . . .
C36 C 0.07225(18) 0.48018(17) 0.29205(13) 0.0141(4) Uani 1 1 d . . . . .
H36 H 0.125675 0.511567 0.240232 0.017 Uiso 1 1 calc R . . . .
C37 C 0.04806(19) 0.37164(18) 0.31167(13) 0.0155(4) Uani 1 1 d . . . . .
H37 H 0.085005 0.330101 0.272661 0.019 Uiso 1 1 calc R . . . .
C38 C -0.02943(19) 0.32141(18) 0.38750(13) 0.0162(4) Uani 1 1 d . . . . .
C39 C -0.08234(19) 0.38583(18) 0.44244(13) 0.0166(4) Uani 1 1 d . . . . .
H39 H -0.135542 0.354534 0.494374 0.020 Uiso 1 1 calc R . . . .
C40 C -0.05881(18) 0.49494(18) 0.42275(13) 0.0149(4) Uani 1 1 d . . . . .
H40 H -0.096581 0.536729 0.461376 0.018 Uiso 1 1 calc R . . . .
C41 C -0.0553(2) 0.20189(19) 0.40490(15) 0.0255(5) Uani 1 1 d . . . . .
C42 C 0.0630(3) 0.1413(2) 0.3969(2) 0.0444(8) Uani 1 1 d . . . . .
H42A H 0.115419 0.163919 0.340646 0.067 Uiso 1 1 calc GR . . . .
H42B H 0.045245 0.064819 0.408334 0.067 Uiso 1 1 calc GR . . . .
H42C H 0.104018 0.156626 0.436515 0.067 Uiso 1 1 calc GR . . . .
C43 C -0.1361(3) 0.1608(2) 0.49263(17) 0.0377(7) Uani 1 1 d . . . . .
H43A H -0.095735 0.174787 0.532986 0.057 Uiso 1 1 calc GR . . . .
H43B H -0.150939 0.084092 0.501539 0.057 Uiso 1 1 calc GR . . . .
H43C H -0.213207 0.197232 0.499378 0.057 Uiso 1 1 calc GR . . . .
C44 C -0.1186(3) 0.1775(2) 0.34255(17) 0.0358(7) Uani 1 1 d . . . . .
H44A H -0.193646 0.216843 0.346718 0.054 Uiso 1 1 calc GR . . . .
H44B H -0.137193 0.101076 0.354598 0.054 Uiso 1 1 calc GR . . . .
H44C H -0.065293 0.199028 0.286509 0.054 Uiso 1 1 calc GR . . . .
C45 C 0.28959(19) 0.87776(16) 0.24662(13) 0.0147(4) Uani 1 1 d . . . . .
C46 C 0.3195(2) 0.94155(18) 0.29492(14) 0.0177(4) Uani 1 1 d . . . . .
H46 H 0.263013 0.948203 0.345163 0.021 Uiso 1 1 calc R . . . .
C47 C 0.4303(2) 0.99548(18) 0.27091(14) 0.0183(5) Uani 1 1 d . . . . .
H47 H 0.447912 1.038399 0.305101 0.022 Uiso 1 1 calc R . . . .
C48 C 0.51615(19) 0.98818(17) 0.19790(14) 0.0163(4) Uani 1 1 d . . . . .
C49 C 0.4840(2) 0.92661(18) 0.14885(14) 0.0188(5) Uani 1 1 d . . . . .
H49 H 0.539737 0.921585 0.097891 0.023 Uiso 1 1 calc R . . . .
C50 C 0.3735(2) 0.87255(17) 0.17199(14) 0.0171(4) Uani 1 1 d . . . . .
H50 H 0.354820 0.831665 0.136815 0.021 Uiso 1 1 calc R . . . .
C51 C 0.6393(2) 1.04588(18) 0.16900(15) 0.0196(5) Uani 1 1 d . . . . .
C52 C 0.7401(2) 0.9649(2) 0.15829(19) 0.0291(6) Uani 1 1 d . . . . .
H52A H 0.733991 0.915493 0.211304 0.044 Uiso 1 1 calc GR . . . .
H52B H 0.818848 1.002244 0.139363 0.044 Uiso 1 1 calc GR . . . .
H52C H 0.731741 0.925066 0.117360 0.044 Uiso 1 1 calc GR . . . .
C53 C 0.6488(2) 1.12290(19) 0.08576(16) 0.0259(5) Uani 1 1 d . . . . .
H53A H 0.645235 1.082497 0.044164 0.039 Uiso 1 1 calc GR . . . .
H53B H 0.725658 1.163268 0.068313 0.039 Uiso 1 1 calc GR . . . .
H53C H 0.581727 1.172072 0.091692 0.039 Uiso 1 1 calc GR . . . .
C54 C 0.6574(2) 1.1102(2) 0.23053(17) 0.0270(5) Uani 1 1 d . . . . .
H54A H 0.595727 1.164458 0.236218 0.041 Uiso 1 1 calc GR . . . .
H54B H 0.737807 1.144673 0.210285 0.041 Uiso 1 1 calc GR . . . .
H54C H 0.650173 1.062520 0.284406 0.041 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.03294(8) 0.85781(10) 0.05529(7) 0.0678(3) Uani 1 1 d . . . . .
Cl2 Cl 0.07890(10) 0.63178(10) 0.06198(6) 0.0697(3) Uani 1 1 d . . . . .
C55 C 0.0630(6) 0.7345(6) 0.1120(3) 0.120(3) Uani 1 1 d . . . . .
H55A H 0.138125 0.742192 0.128300 0.144 Uiso 1 1 calc R . . . .
H55B H -0.003457 0.715735 0.163330 0.144 Uiso 1 1 calc R . . . .
C27A C 0.5587(9) 0.8908(5) 0.4838(4) 0.051(2) Uani 0.482(5) 1 d . . P A 2
H27D H 0.629416 0.922698 0.439808 0.077 Uiso 0.482(5) 1 calc GR . P A 2
H27E H 0.545966 0.927086 0.529935 0.077 Uiso 0.482(5) 1 calc GR . P A 2
H27F H 0.487211 0.898194 0.462451 0.077 Uiso 0.482(5) 1 calc GR . P A 2
C26A C 0.4685(5) 0.7284(5) 0.5874(3) 0.0263(13) Uani 0.482(5) 1 d . . P A 2
H26D H 0.395747 0.724960 0.568541 0.039 Uiso 0.482(5) 1 calc GR . P A 2
H26E H 0.452491 0.769648 0.630738 0.039 Uiso 0.482(5) 1 calc GR . P A 2
H26F H 0.491055 0.656310 0.609476 0.039 Uiso 0.482(5) 1 calc GR . P A 2
C25A C 0.6908(5) 0.7672(5) 0.5507(4) 0.0323(15) Uani 0.482(5) 1 d . . P A 2
H25D H 0.695871 0.691437 0.574427 0.048 Uiso 0.482(5) 1 calc GR . P A 2
H25E H 0.679787 0.807780 0.594162 0.048 Uiso 0.482(5) 1 calc GR . P A 2
H25F H 0.765587 0.791523 0.507670 0.048 Uiso 0.482(5) 1 calc GR . 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
C1 N1 1.346(3) . ?
C1 C2 1.483(3) . ?
C1 N3 1.343(3) . ?
N1 N2 1.331(2) . ?
C2 C3 1.413(3) . ?
C2 C7 1.401(3) . ?
N2 C28 1.342(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.485(3) . ?
N3 N4 1.324(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
N4 C28 1.342(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(3) . ?
C7 C18 1.491(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.402(3) . ?
C11 C12 1.390(3) . ?
C11 C14 1.533(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.534(3) . ?
C14 C16 1.534(3) . ?
C14 C17 1.530(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.393(3) . ?
C18 C23 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.399(3) . ?
C21 C22 1.392(3) . ?
C21 C24 1.533(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.412(5) . ?
C24 C26 1.592(5) . ?
C24 C27 1.622(5) . ?
C24 C27A 1.372(7) . ?
C24 C26A 1.612(6) . ?
C24 C25A 1.615(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.492(3) . ?
C29 C30 1.407(3) . ?
C29 C34 1.411(3) . ?
C30 C31 1.399(3) . ?
C30 C35 1.491(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.400(3) . ?
C34 C45 1.491(3) . ?
C35 C36 1.398(3) . ?
C35 C40 1.392(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.385(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.402(3) . ?
C38 C39 1.395(3) . ?
C38 C41 1.527(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.391(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.534(4) . ?
C41 C43 1.535(3) . ?
C41 C44 1.534(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.395(3) . ?
C45 C50 1.397(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.387(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.392(3) . ?
C48 C49 1.396(3) . ?
C48 C51 1.528(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.387(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.535(3) . ?
C51 C53 1.536(3) . ?
C51 C54 1.534(3) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
Cl1 C55 1.754(6) . ?
Cl2 C55 1.706(6) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 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
N1 C1 C2 119.01(18) . . ?
N3 C1 N1 124.28(18) . . ?
N3 C1 C2 116.71(17) . . ?
N2 N1 C1 117.58(17) . . ?
C3 C2 C1 120.35(18) . . ?
C7 C2 C1 119.05(18) . . ?
C7 C2 C3 120.48(19) . . ?
N1 N2 C28 117.19(17) . . ?
C2 C3 C8 122.67(18) . . ?
C4 C3 C2 118.44(19) . . ?
C4 C3 C8 118.74(19) . . ?
N4 N3 C1 117.69(17) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
N3 N4 C28 117.54(17) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C18 122.57(18) . . ?
C6 C7 C2 119.15(19) . . ?
C6 C7 C18 118.27(18) . . ?
C9 C8 C3 121.16(18) . . ?
C13 C8 C3 120.88(19) . . ?
C13 C8 C9 117.82(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.08(19) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.7(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C14 120.18(19) . . ?
C12 C11 C10 116.97(19) . . ?
C12 C11 C14 122.83(19) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.43(19) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 120.9(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C11 C14 C15 109.70(19) . . ?
C11 C14 C16 111.75(19) . . ?
C15 C14 C16 107.6(2) . . ?
C17 C14 C11 108.73(19) . . ?
C17 C14 C15 109.9(2) . . ?
C17 C14 C16 109.13(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C7 121.98(19) . . ?
C23 C18 C7 119.59(19) . . ?
C23 C18 C19 118.41(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C24 120.9(2) . . ?
C22 C21 C20 117.8(2) . . ?
C22 C21 C24 121.2(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C21 C24 C26 106.8(2) . . ?
C21 C24 C27 108.6(2) . . ?
C21 C24 C26A 106.5(3) . . ?
C21 C24 C25A 105.8(3) . . ?
C25 C24 C21 117.1(3) . . ?
C25 C24 C26 110.7(3) . . ?
C25 C24 C27 109.6(3) . . ?
C26 C24 C27 103.1(3) . . ?
C27A C24 C21 117.0(3) . . ?
C27A C24 C26A 112.5(5) . . ?
C27A C24 C25A 112.1(5) . . ?
C26A C24 C25A 101.6(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 C29 118.77(18) . . ?
N4 C28 N2 124.79(19) . . ?
N4 C28 C29 116.35(18) . . ?
C30 C29 C28 119.48(18) . . ?
C30 C29 C34 121.04(19) . . ?
C34 C29 C28 119.48(18) . . ?
C29 C30 C35 122.51(19) . . ?
C31 C30 C29 118.6(2) . . ?
C31 C30 C35 118.88(19) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 C30 120.8(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 120.9(2) . . ?
C34 C33 H33 119.5 . . ?
C29 C34 C45 123.07(18) . . ?
C33 C34 C29 118.3(2) . . ?
C33 C34 C45 118.53(19) . . ?
C36 C35 C30 122.24(19) . . ?
C40 C35 C30 119.93(19) . . ?
C40 C35 C36 117.8(2) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C36 C37 H37 119.1 . . ?
C36 C37 C38 121.8(2) . . ?
C38 C37 H37 119.1 . . ?
C37 C38 C41 119.5(2) . . ?
C39 C38 C37 117.0(2) . . ?
C39 C38 C41 123.4(2) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 C38 121.4(2) . . ?
C40 C39 H39 119.3 . . ?
C35 C40 H40 119.4 . . ?
C39 C40 C35 121.3(2) . . ?
C39 C40 H40 119.4 . . ?
C38 C41 C42 110.2(2) . . ?
C38 C41 C43 111.7(2) . . ?
C38 C41 C44 109.4(2) . . ?
C42 C41 C43 107.5(2) . . ?
C44 C41 C42 109.0(2) . . ?
C44 C41 C43 108.9(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 C34 118.92(19) . . ?
C46 C45 C50 117.7(2) . . ?
C50 C45 C34 123.4(2) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.2(2) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 119.2 . . ?
C46 C47 C48 121.6(2) . . ?
C48 C47 H47 119.2 . . ?
C47 C48 C49 116.8(2) . . ?
C47 C48 C51 123.5(2) . . ?
C49 C48 C51 119.7(2) . . ?
C48 C49 H49 118.9 . . ?
C50 C49 C48 122.2(2) . . ?
C50 C49 H49 118.9 . . ?
C45 C50 H50 119.8 . . ?
C49 C50 C45 120.5(2) . . ?
C49 C50 H50 119.8 . . ?
C48 C51 C52 109.75(18) . . ?
C48 C51 C53 108.93(19) . . ?
C48 C51 C54 112.07(19) . . ?
C52 C51 C53 109.3(2) . . ?
C54 C51 C52 108.5(2) . . ?
C54 C51 C53 108.24(19) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
Cl1 C55 H55A 108.4 . . ?
Cl1 C55 H55B 108.4 . . ?
Cl2 C55 Cl1 115.5(2) . . ?
Cl2 C55 H55A 108.4 . . ?
Cl2 C55 H55B 108.4 . . ?
H55A C55 H55B 107.5 . . ?
C24 C27A H27D 109.5 . . ?
C24 C27A H27E 109.5 . . ?
C24 C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C24 C26A H26D 109.5 . . ?
C24 C26A H26E 109.5 . . ?
C24 C26A H26F 109.5 . . ?
H26D C26A H26E 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C24 C25A H25D 109.5 . . ?
C24 C25A H25E 109.5 . . ?
C24 C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'


#------------------ END ----------------------------------------------------#
####################################################################### 
# 
# 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_Compound_4_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1559131'
_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2ybc'
#Added by publCIF



_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br N4'
_chemical_formula_sum            'C14 H9 Br N4'
_chemical_formula_weight         313.16
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5112(10)
_cell_length_b                   7.3614(6)
_cell_length_c                   14.0920(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.653(2)
_cell_angle_gamma                90
_cell_volume                     1236.76(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7396
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0554 before and 0.0394 after correction. The Ratio of minimum to maximum transmission is 0.8472. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21740
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_min         2.997
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2454
_reflns_number_total             2850
_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 V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.8899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0732
_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), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.89181(2) 0.62930(3) 0.54467(2) 0.02478(9) Uani 1 1 d . . . . .
C1 C 0.88475(17) 0.5669(3) 0.67303(15) 0.0159(4) Uani 1 1 d . . . . .
N1 N 0.73199(14) 0.3053(2) 0.52831(13) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.96788(18) 0.6403(3) 0.75333(17) 0.0201(4) Uani 1 1 d . . . . .
H2 H 1.0272 0.7092 0.7424 0.024 Uiso 1 1 calc R . . . .
N2 N 0.64834(14) 0.2363(2) 0.45510(12) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.96352(19) 0.6122(3) 0.84922(16) 0.0226(5) Uani 1 1 d . . . . .
H3 H 1.0203 0.6614 0.9042 0.027 Uiso 1 1 calc R . . . .
N3 N 0.60459(15) 0.3767(2) 0.61834(13) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.87629(18) 0.5124(3) 0.86528(16) 0.0214(4) Uani 1 1 d . . . . .
H4 H 0.8733 0.4938 0.9311 0.026 Uiso 1 1 calc R . . . .
N4 N 0.52142(14) 0.3064(2) 0.54602(13) 0.0171(4) Uani 1 1 d . . . . .
C5 C 0.79396(17) 0.4404(3) 0.78532(15) 0.0178(4) Uani 1 1 d . . . . .
H5 H 0.7341 0.3736 0.7969 0.021 Uiso 1 1 calc R . . . .
C6 C 0.79702(16) 0.4640(3) 0.68724(14) 0.0141(4) Uani 1 1 d . . . . .
C7 C 0.70683(16) 0.3806(3) 0.60560(14) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.54456(16) 0.2440(3) 0.46446(14) 0.0136(4) Uani 1 1 d . . . . .
C9 C 0.44977(17) 0.1747(3) 0.38233(15) 0.0147(4) Uani 1 1 d . . . . .
C10 C 0.35003(17) 0.1245(3) 0.40074(15) 0.0164(4) Uani 1 1 d . . . . .
H10 H 0.3433 0.1356 0.4658 0.020 Uiso 1 1 calc R . . . .
C11 C 0.26088(17) 0.0585(3) 0.32341(16) 0.0191(4) Uani 1 1 d . . . . .
H11 H 0.1936 0.0222 0.3360 0.023 Uiso 1 1 calc R . . . .
C12 C 0.26975(18) 0.0456(3) 0.22803(16) 0.0211(4) Uani 1 1 d . . . . .
H12 H 0.2083 0.0012 0.1754 0.025 Uiso 1 1 calc R . . . .
C13 C 0.3679(2) 0.0971(3) 0.20914(16) 0.0234(5) Uani 1 1 d . . . . .
H13 H 0.3734 0.0890 0.1435 0.028 Uiso 1 1 calc R . . . .
C14 C 0.45823(18) 0.1607(3) 0.28598(16) 0.0198(4) Uani 1 1 d . . . . .
H14 H 0.5258 0.1946 0.2731 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br C1 1.894(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.397(3) . ?
N1 N2 1.328(2) . ?
N1 C7 1.342(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
N2 C8 1.345(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
N3 N4 1.321(2) . ?
N3 C7 1.345(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
N4 C8 1.348(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(3) . ?
C6 C7 1.479(3) . ?
C8 C9 1.474(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br 116.25(16) . . ?
C2 C1 C6 121.28(19) . . ?
C6 C1 Br 122.31(15) . . ?
N2 N1 C7 117.72(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
N1 N2 C8 117.67(17) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
N4 N3 C7 117.65(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
N3 N4 C8 117.94(17) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.71(18) . . ?
C1 C6 C7 124.11(18) . . ?
C5 C6 C7 118.17(18) . . ?
N1 C7 N3 124.48(18) . . ?
N1 C7 C6 119.44(17) . . ?
N3 C7 C6 115.95(17) . . ?
N2 C8 N4 124.12(18) . . ?
N2 C8 C9 118.61(18) . . ?
N4 C8 C9 117.23(17) . . ?
C10 C9 C8 119.74(18) . . ?
C14 C9 C8 120.56(18) . . ?
C14 C9 C10 119.70(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.72(19) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.25(19) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.26(19) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with oil'
_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_Compound_5a
_database_code_depnum_ccdc_archive 'CCDC 1559132'
_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
#Added by publCIF




_symmetry_space_group_name_hall  '-C 2yc'
#Added by publCIF



_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H13 N2)'
_chemical_formula_sum            'C38 H26 N4'
_chemical_formula_weight         538.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   36.798(3)
_cell_length_b                   14.1747(11)
_cell_length_c                   10.8322(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.909(3)
_cell_angle_gamma                90
_cell_volume                     5642.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.838
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0591 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.9341. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            63449
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.874
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'κ-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5331
_reflns_number_total             6444
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+14.7264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1549
_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:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46508(5) 0.74981(13) 0.74476(17) 0.0128(4) Uani 1 1 d . . . . .
N1 N 0.48198(4) 0.66572(11) 0.74818(15) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.42463(5) 0.74862(14) 0.73811(18) 0.0139(4) Uani 1 1 d . . . . .
N2 N 0.48189(4) 0.83384(12) 0.74650(16) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.40528(5) 0.79917(14) 0.82513(18) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.36730(5) 0.79485(15) 0.81832(19) 0.0186(4) Uani 1 1 d . . . . .
H4 H 0.3539 0.8296 0.8756 0.022 Uiso 1 1 calc R . . . .
C5 C 0.34894(6) 0.74041(15) 0.7289(2) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.3231 0.7368 0.7264 0.025 Uiso 1 1 calc R . . . .
C6 C 0.36828(5) 0.69129(15) 0.64329(19) 0.0182(4) Uani 1 1 d . . . . .
H6 H 0.3555 0.6545 0.5819 0.022 Uiso 1 1 calc R . . . .
C7 C 0.40621(5) 0.69503(14) 0.64577(17) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.44989(6) 0.81116(16) 1.0076(2) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.4553 0.7461 0.9986 0.026 Uiso 1 1 calc R . . . .
C9 C 0.46768(7) 0.86296(18) 1.1004(2) 0.0288(5) Uani 1 1 d . . . . .
H9 H 0.4856 0.8335 1.1536 0.035 Uiso 1 1 calc R . . . .
C10 C 0.45955(7) 0.95774(18) 1.1166(2) 0.0343(6) Uani 1 1 d . . . . .
H10 H 0.4716 0.9931 1.1809 0.041 Uiso 1 1 calc R . . . .
C11 C 0.43347(7) 1.00036(17) 1.0374(2) 0.0310(5) Uani 1 1 d . . . . .
H11 H 0.4277 1.0652 1.0475 0.037 Uiso 1 1 calc R . . . .
C12 C 0.41583(6) 0.94846(16) 0.9438(2) 0.0236(5) Uani 1 1 d . . . . .
H12 H 0.3979 0.9779 0.8905 0.028 Uiso 1 1 calc R . . . .
C13 C 0.42409(5) 0.85373(14) 0.92710(18) 0.0169(4) Uani 1 1 d . . . . .
C14 C 0.42544(5) 0.64415(14) 0.54788(18) 0.0155(4) Uani 1 1 d . . . . .
C15 C 0.41818(6) 0.54882(15) 0.5266(2) 0.0210(4) Uani 1 1 d . . . . .
H15 H 0.4014 0.5168 0.5757 0.025 Uiso 1 1 calc R . . . .
C16 C 0.43520(6) 0.50028(17) 0.4344(2) 0.0273(5) Uani 1 1 d . . . . .
H16 H 0.4301 0.4353 0.4207 0.033 Uiso 1 1 calc R . . . .
C17 C 0.45957(7) 0.54667(18) 0.3623(2) 0.0317(6) Uani 1 1 d . . . . .
H17 H 0.4713 0.5137 0.2992 0.038 Uiso 1 1 calc R . . . .
C18 C 0.46674(7) 0.64239(18) 0.3833(2) 0.0301(5) Uani 1 1 d . . . . .
H18 H 0.4835 0.6745 0.3341 0.036 Uiso 1 1 calc R . . . .
C19 C 0.44969(6) 0.69055(16) 0.4749(2) 0.0219(4) Uani 1 1 d . . . . .
H19 H 0.4546 0.7557 0.4880 0.026 Uiso 1 1 calc R . . . .
N3 N 0.23809(5) 0.22210(12) 0.61118(16) 0.0198(4) Uani 1 1 d . . . . .
N4 N 0.23777(5) 0.31322(12) 0.58244(16) 0.0202(4) Uani 1 1 d . . . . .
C20 C 0.24963(5) 0.33843(14) 0.47234(17) 0.0141(4) Uani 1 1 d . . . . .
C21 C 0.25055(5) 0.44136(14) 0.44421(18) 0.0150(4) Uani 1 1 d . . . . .
C22 C 0.27770(5) 0.49769(14) 0.50303(18) 0.0154(4) Uani 1 1 d . . . . .
C23 C 0.27739(6) 0.59464(14) 0.48080(19) 0.0185(4) Uani 1 1 d . . . . .
H23 H 0.2952 0.6335 0.5218 0.022 Uiso 1 1 calc R . . . .
C24 C 0.25143(6) 0.63523(15) 0.39980(19) 0.0199(4) Uani 1 1 d . . . . .
H24 H 0.2517 0.7012 0.3845 0.024 Uiso 1 1 calc R . . . .
C25 C 0.22505(6) 0.57867(15) 0.34155(19) 0.0193(4) Uani 1 1 d . . . . .
H25 H 0.2073 0.6064 0.2860 0.023 Uiso 1 1 calc R . . . .
C26 C 0.22410(5) 0.48160(14) 0.36312(18) 0.0163(4) Uani 1 1 d . . . . .
C27 C 0.30769(5) 0.45624(14) 0.58371(18) 0.0160(4) Uani 1 1 d . . . . .
C28 C 0.32998(6) 0.38510(15) 0.53860(19) 0.0187(4) Uani 1 1 d . . . . .
H28 H 0.3250 0.3606 0.4579 0.022 Uiso 1 1 calc R . . . .
C29 C 0.35925(6) 0.35017(15) 0.6108(2) 0.0226(5) Uani 1 1 d . . . . .
H29 H 0.3741 0.3018 0.5795 0.027 Uiso 1 1 calc R . . . .
C30 C 0.36673(6) 0.38598(15) 0.7286(2) 0.0224(5) Uani 1 1 d . . . . .
H30 H 0.3868 0.3624 0.7781 0.027 Uiso 1 1 calc R . . . .
C31 C 0.34490(6) 0.45615(16) 0.7738(2) 0.0219(4) Uani 1 1 d . . . . .
H31 H 0.3500 0.4806 0.8545 0.026 Uiso 1 1 calc R . . . .
C32 C 0.31550(6) 0.49128(15) 0.70208(19) 0.0187(4) Uani 1 1 d . . . . .
H32 H 0.3007 0.5394 0.7341 0.022 Uiso 1 1 calc R . . . .
C33 C 0.19448(5) 0.42654(14) 0.29687(18) 0.0165(4) Uani 1 1 d . . . . .
C34 C 0.19992(7) 0.3879(2) 0.1823(2) 0.0354(6) Uani 1 1 d . . . . .
H34 H 0.2234 0.3910 0.1496 0.042 Uiso 1 1 calc R . . . .
C35 C 0.17159(7) 0.3444(2) 0.1142(2) 0.0370(6) Uani 1 1 d . . . . .
H35 H 0.1757 0.3184 0.0353 0.044 Uiso 1 1 calc R . . . .
C36 C 0.13749(6) 0.33918(16) 0.1612(2) 0.0247(5) Uani 1 1 d . . . . .
H36 H 0.1180 0.3097 0.1149 0.030 Uiso 1 1 calc R . . . .
C37 C 0.13182(6) 0.37701(18) 0.2758(2) 0.0297(5) Uani 1 1 d . . . . .
H37 H 0.1085 0.3729 0.3089 0.036 Uiso 1 1 calc R . . . .
C38 C 0.16014(6) 0.42125(18) 0.3431(2) 0.0274(5) Uani 1 1 d . . . . .
H38 H 0.1559 0.4481 0.4214 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(2) . ?
C1 C2 1.487(3) . ?
C1 N2 1.342(2) . ?
N1 N1 1.325(3) 2_656 ?
C2 C3 1.406(3) . ?
C2 C7 1.403(3) . ?
N2 N2 1.332(3) 2_656 ?
C3 C4 1.397(3) . ?
C3 C13 1.490(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 C14 1.490(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(3) . ?
C14 C15 1.394(3) . ?
C14 C19 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
N3 N4 1.328(2) . ?
N3 C20 1.342(3) 7_556 ?
N4 C20 1.339(3) . ?
C20 N3 1.342(3) 7_556 ?
C20 C21 1.491(3) . ?
C21 C22 1.406(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.395(3) . ?
C22 C27 1.493(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(3) . ?
C26 C33 1.494(3) . ?
C27 C28 1.403(3) . ?
C27 C32 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.384(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(3) . ?
C33 C38 1.385(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.391(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.380(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.377(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.391(3) . ?
C38 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 116.88(17) . . ?
N2 C1 N1 125.07(17) . . ?
N2 C1 C2 118.06(17) . . ?
N1 N1 C1 117.51(11) 2_656 . ?
C3 C2 C1 120.10(17) . . ?
C7 C2 C1 119.13(17) . . ?
C7 C2 C3 120.75(18) . . ?
N2 N2 C1 117.40(11) 2_656 . ?
C2 C3 C13 121.98(17) . . ?
C4 C3 C2 118.78(18) . . ?
C4 C3 C13 119.19(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.78(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.90(19) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.03(19) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C14 122.67(17) . . ?
C6 C7 C2 118.73(18) . . ?
C6 C7 C14 118.58(17) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C13 120.5(2) . . ?
C13 C8 H8 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C3 121.02(18) . . ?
C12 C13 C3 120.08(19) . . ?
C12 C13 C8 118.90(19) . . ?
C15 C14 C7 119.53(18) . . ?
C19 C14 C7 121.21(18) . . ?
C19 C14 C15 119.23(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
N4 N3 C20 117.58(17) . 7_556 ?
N3 N4 C20 117.95(17) . . ?
N3 C20 C21 118.42(17) 7_556 . ?
N4 C20 N3 124.47(18) . 7_556 ?
N4 C20 C21 117.05(17) . . ?
C22 C21 C20 119.07(17) . . ?
C26 C21 C20 120.33(18) . . ?
C26 C21 C22 120.57(18) . . ?
C21 C22 C27 121.94(18) . . ?
C23 C22 C21 118.80(18) . . ?
C23 C22 C27 119.20(18) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.09(19) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.44(19) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.10(19) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C33 123.76(18) . . ?
C25 C26 C21 118.98(18) . . ?
C25 C26 C33 117.26(18) . . ?
C28 C27 C22 120.45(18) . . ?
C32 C27 C22 120.72(18) . . ?
C32 C27 C28 118.71(18) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.68(19) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.79(19) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.5(2) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 120.3(2) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C26 120.23(19) . . ?
C34 C33 C38 118.7(2) . . ?
C38 C33 C26 120.76(19) . . ?
C33 C34 H34 119.5 . . ?
C33 C34 C35 120.9(2) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 119.9(2) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.2 . . ?
C37 C36 C35 119.6(2) . . ?
C37 C36 H36 120.2 . . ?
C36 C37 H37 119.9 . . ?
C36 C37 C38 120.3(2) . . ?
C38 C37 H37 119.9 . . ?
C33 C38 C37 120.5(2) . . ?
C33 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
