# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxs
_database_code_depnum_ccdc_archive 'CCDC 1542481'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
7-(4-Chlorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine
_chemical_name_common            ?
_chemical_melting_point          430
_chemical_formula_moiety         'C13 H9 Cl I N3'
_chemical_formula_sum            'C13 H9 Cl I N3'
_chemical_formula_weight         369.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1315(6)
_cell_length_b                   12.4851(8)
_cell_length_c                   14.5014(7)
_cell_angle_alpha                105.748(5)
_cell_angle_beta                 105.605(6)
_cell_angle_gamma                99.832(6)
_cell_volume                     1316.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    18407
_cell_measurement_theta_min      3.302
_cell_measurement_theta_max      29.390

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    2.619
_shelx_estimated_absorpt_T_min   0.546
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.3072
_diffrn_reflns_number            58640
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         30.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7387
_reflns_number_gt                5196
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'

_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)+(0.0361P)²+0.8410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7387
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
I1 I 0.15729(3) 0.10268(2) 0.12219(2) 0.07369(11) Uani 1 1 d . . . . .
C2 C 0.3514(4) 0.2526(2) 0.2088(2) 0.0474(6) Uani 1 1 d . . . . .
C4 C 0.3914(4) 0.3477(3) 0.1791(2) 0.0467(6) Uani 1 1 d . . . . .
N5 N 0.5241(3) 0.4290(2) 0.26329(16) 0.0434(5) Uani 1 1 d . . . . .
N6 N 0.5674(3) 0.3897(2) 0.34312(17) 0.0477(6) Uani 1 1 d . . . . .
C7 C 0.4610(4) 0.2824(3) 0.3093(2) 0.0480(6) Uani 1 1 d . . . . .
C8 C 0.4659(5) 0.2113(3) 0.3763(3) 0.0710(10) Uani 1 1 d . . . . .
H8A H 0.3487 0.1842 0.3772 0.107 Uiso 1 1 calc R U . . .
H8B H 0.5423 0.2571 0.4439 0.107 Uiso 1 1 calc R U . . .
H8C H 0.5099 0.1466 0.3513 0.107 Uiso 1 1 calc R U . . .
C9 C 0.5914(4) 0.5377(2) 0.2629(2) 0.0456(6) Uani 1 1 d . . . . .
C10 C 0.7255(4) 0.6248(2) 0.3549(2) 0.0450(6) Uani 1 1 d . . . . .
C11 C 0.8604(4) 0.5994(2) 0.4196(2) 0.0487(6) Uani 1 1 d . . . . .
H11 H 0.8679 0.5235 0.4061 0.058 Uiso 1 1 calc R U . . .
C12 C 0.9846(4) 0.6851(3) 0.5043(2) 0.0544(7) Uani 1 1 d . . . . .
H12 H 1.0758 0.6675 0.5471 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9700(5) 0.7963(3) 0.5239(2) 0.0594(8) Uani 1 1 d . . . . .
Cl14 Cl 1.11753(18) 0.90326(9) 0.63355(8) 0.0972(4) Uani 1 1 d . . . . .
C15 C 0.8388(5) 0.8243(3) 0.4610(3) 0.0691(10) Uani 1 1 d . . . . .
H15 H 0.8313 0.9002 0.4757 0.083 Uiso 1 1 calc R U . . .
C16 C 0.7177(5) 0.7393(3) 0.3757(3) 0.0623(8) Uani 1 1 d . . . . .
H16 H 0.6303 0.7584 0.3317 0.075 Uiso 1 1 calc R U . . .
C17 C 0.5228(4) 0.5567(3) 0.1739(2) 0.0572(8) Uani 1 1 d . . . . .
H17 H 0.5637 0.6281 0.1683 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3914(5) 0.4701(3) 0.0907(2) 0.0624(9) Uani 1 1 d . . . . .
H18 H 0.3494 0.4868 0.0313 0.075 Uiso 1 1 calc R U . . .
N19 N 0.3243(4) 0.3672(2) 0.09140(19) 0.0583(7) Uani 1 1 d . . . . .
I20 I 0.31273(3) 0.89460(2) 0.38440(2) 0.06784(11) Uani 1 1 d . . . . .
C21 C 0.1531(4) 0.7344(2) 0.2908(2) 0.0479(6) Uani 1 1 d . . . . .
C22 C 0.0110(4) 0.7086(3) 0.2015(2) 0.0492(7) Uani 1 1 d . . . . .
N23 N -0.0638(3) 0.5950(2) 0.15907(18) 0.0482(6) Uani 1 1 d . . . . .
N24 N 0.0309(3) 0.5478(2) 0.22275(16) 0.0437(5) Uani 1 1 d . . . . .
C25 C 0.1651(4) 0.6307(2) 0.3054(2) 0.0449(6) Uani 1 1 d . . . . .
N26 N 0.2699(3) 0.6041(2) 0.38102(18) 0.0521(6) Uani 1 1 d . . . . .
C27 C 0.2323(4) 0.4953(3) 0.3744(2) 0.0548(7) Uani 1 1 d . . . . .
H27 H 0.2989 0.4747 0.4265 0.066 Uiso 1 1 calc R U . . .
C28 C 0.0973(4) 0.4078(3) 0.2931(2) 0.0524(7) Uani 1 1 d . . . . .
H28 H 0.0770 0.3322 0.2930 0.063 Uiso 1 1 calc R U . . .
C29 C -0.0043(4) 0.4333(2) 0.2143(2) 0.0455(6) Uani 1 1 d . . . . .
C30 C -0.1431(4) 0.3475(2) 0.1238(2) 0.0467(6) Uani 1 1 d . . . . .
C31 C -0.2582(5) 0.2595(3) 0.1354(3) 0.0571(8) Uani 1 1 d . . . . .
H31 H -0.2490 0.2566 0.1999 0.069 Uiso 1 1 calc R U . . .
C32 C -0.3863(5) 0.1762(3) 0.0506(3) 0.0650(9) Uani 1 1 d . . . . .
H32 H -0.4648 0.1183 0.0582 0.078 Uiso 1 1 calc R U . . .
C33 C -0.3962(5) 0.1798(3) -0.0434(3) 0.0591(8) Uani 1 1 d . . . . .
Cl34 Cl -0.55660(15) 0.07548(10) -0.15033(9) 0.0901(3) Uani 1 1 d . . . . .
C35 C -0.2822(5) 0.2640(3) -0.0571(2) 0.0611(8) Uani 1 1 d . . . . .
H35 H -0.2899 0.2643 -0.1222 0.073 Uiso 1 1 calc R U . . .
C36 C -0.1559(5) 0.3481(3) 0.0269(2) 0.0568(8) Uani 1 1 d . . . . .
H36 H -0.0787 0.4057 0.0182 0.068 Uiso 1 1 calc R U . . .
C37 C -0.0618(5) 0.7908(3) 0.1561(3) 0.0676(9) Uani 1 1 d . . . . .
H37A H -0.1488 0.7490 0.0904 0.101 Uiso 1 1 calc R U . . .
H37B H 0.0321 0.8428 0.1493 0.101 Uiso 1 1 calc R U . . .
H37C H -0.1159 0.8339 0.1994 0.101 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 C2 2.054(3) . ?
C2 C4 1.386(4) . ?
C2 C7 1.397(4) . ?
C4 N19 1.347(4) . ?
C4 N5 1.389(3) . ?
N5 N6 1.361(3) . ?
N5 C9 1.375(4) . ?
N6 C7 1.343(4) . ?
C7 C8 1.480(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C17 1.363(4) . ?
C9 C10 1.475(4) . ?
C10 C11 1.383(4) . ?
C10 C16 1.394(4) . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(5) . ?
C12 H12 0.9300 . ?
C13 C15 1.366(5) . ?
C13 Cl14 1.739(3) . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.404(4) . ?
C17 H17 0.9300 . ?
C18 N19 1.312(4) . ?
C18 H18 0.9300 . ?
I20 C21 2.054(3) . ?
C21 C25 1.383(4) . ?
C21 C22 1.399(4) . ?
C22 N23 1.337(4) . ?
C22 C37 1.484(4) . ?
N23 N24 1.365(3) . ?
N24 C29 1.373(3) . ?
N24 C25 1.392(3) . ?
C25 N26 1.353(4) . ?
N26 C27 1.310(4) . ?
C27 C28 1.408(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.473(4) . ?
C30 C36 1.383(4) . ?
C30 C31 1.395(4) . ?
C31 C32 1.387(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.357(5) . ?
C32 H32 0.9300 . ?
C33 C35 1.373(5) . ?
C33 Cl34 1.743(3) . ?
C35 C36 1.380(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
C4 C2 C7 106.4(2) . . ?
C4 C2 I1 125.6(2) . . ?
C7 C2 I1 127.9(2) . . ?
N19 C4 C2 131.7(3) . . ?
N19 C4 N5 123.2(3) . . ?
C2 C4 N5 105.1(2) . . ?
N6 N5 C9 126.4(2) . . ?
N6 N5 C4 112.2(2) . . ?
C9 N5 C4 121.2(2) . . ?
C7 N6 N5 104.7(2) . . ?
N6 C7 C2 111.5(3) . . ?
N6 C7 C8 120.9(3) . . ?
C2 C7 C8 127.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C9 N5 115.1(3) . . ?
C17 C9 C10 124.4(3) . . ?
N5 C9 C10 120.4(2) . . ?
C11 C10 C16 118.6(3) . . ?
C11 C10 C9 123.5(3) . . ?
C16 C10 C9 117.9(3) . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C15 C13 C12 121.6(3) . . ?
C15 C13 Cl14 119.3(3) . . ?
C12 C13 Cl14 119.1(3) . . ?
C13 C15 C16 119.6(3) . . ?
C13 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C10 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C10 C16 H16 119.8 . . ?
C9 C17 C18 121.0(3) . . ?
C9 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
N19 C18 C17 124.1(3) . . ?
N19 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
C18 N19 C4 115.3(3) . . ?
C25 C21 C22 106.7(3) . . ?
C25 C21 I20 126.0(2) . . ?
C22 C21 I20 127.3(2) . . ?
N23 C22 C21 111.6(3) . . ?
N23 C22 C37 120.8(3) . . ?
C21 C22 C37 127.6(3) . . ?
C22 N23 N24 104.6(2) . . ?
N23 N24 C29 126.1(2) . . ?
N23 N24 C25 112.4(2) . . ?
C29 N24 C25 121.4(2) . . ?
N26 C25 C21 132.6(3) . . ?
N26 C25 N24 122.6(3) . . ?
C21 C25 N24 104.7(2) . . ?
C27 N26 C25 115.8(3) . . ?
N26 C27 C28 124.0(3) . . ?
N26 C27 H27 118.0 . . ?
C28 C27 H27 118.0 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 N24 115.6(3) . . ?
C28 C29 C30 124.6(3) . . ?
N24 C29 C30 119.8(2) . . ?
C36 C30 C31 118.9(3) . . ?
C36 C30 C29 121.6(3) . . ?
C31 C30 C29 119.4(3) . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C31 119.5(3) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C35 121.7(3) . . ?
C32 C33 Cl34 119.9(3) . . ?
C35 C33 Cl34 118.5(3) . . ?
C33 C35 C36 119.2(3) . . ?
C33 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C30 120.6(3) . . ?
C35 C36 H36 119.7 . . ?
C30 C36 H36 119.7 . . ?
C22 C37 H37A 109.5 . . ?
C22 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C22 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C4 N19 -178.7(3) . . . . ?
I1 C2 C4 N19 -2.0(5) . . . . ?
C7 C2 C4 N5 0.5(3) . . . . ?
I1 C2 C4 N5 177.2(2) . . . . ?
N19 C4 N5 N6 179.0(3) . . . . ?
C2 C4 N5 N6 -0.3(3) . . . . ?
N19 C4 N5 C9 2.3(4) . . . . ?
C2 C4 N5 C9 -176.9(3) . . . . ?
C9 N5 N6 C7 176.4(3) . . . . ?
C4 N5 N6 C7 -0.1(3) . . . . ?
N5 N6 C7 C2 0.4(4) . . . . ?
N5 N6 C7 C8 -178.5(3) . . . . ?
C4 C2 C7 N6 -0.6(4) . . . . ?
I1 C2 C7 N6 -177.1(2) . . . . ?
C4 C2 C7 C8 178.3(3) . . . . ?
I1 C2 C7 C8 1.7(5) . . . . ?
N6 N5 C9 C17 -178.3(3) . . . . ?
C4 N5 C9 C17 -2.2(4) . . . . ?
N6 N5 C9 C10 0.6(4) . . . . ?
C4 N5 C9 C10 176.8(3) . . . . ?
C17 C9 C10 C11 -143.0(3) . . . . ?
N5 C9 C10 C11 38.2(4) . . . . ?
C17 C9 C10 C16 35.3(5) . . . . ?
N5 C9 C10 C16 -143.5(3) . . . . ?
C16 C10 C11 C12 0.8(5) . . . . ?
C9 C10 C11 C12 179.1(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C15 -1.3(5) . . . . ?
C11 C12 C13 Cl14 176.5(2) . . . . ?
C12 C13 C15 C16 0.0(6) . . . . ?
Cl14 C13 C15 C16 -177.8(3) . . . . ?
C13 C15 C16 C10 1.8(6) . . . . ?
C11 C10 C16 C15 -2.1(5) . . . . ?
C9 C10 C16 C15 179.5(3) . . . . ?
N5 C9 C17 C18 0.8(5) . . . . ?
C10 C9 C17 C18 -178.1(3) . . . . ?
C9 C17 C18 N19 0.6(6) . . . . ?
C17 C18 N19 C4 -0.6(5) . . . . ?
C2 C4 N19 C18 178.2(4) . . . . ?
N5 C4 N19 C18 -0.8(5) . . . . ?
C25 C21 C22 N23 -1.0(4) . . . . ?
I20 C21 C22 N23 179.7(2) . . . . ?
C25 C21 C22 C37 176.4(3) . . . . ?
I20 C21 C22 C37 -2.8(5) . . . . ?
C21 C22 N23 N24 0.5(3) . . . . ?
C37 C22 N23 N24 -177.1(3) . . . . ?
C22 N23 N24 C29 175.4(3) . . . . ?
C22 N23 N24 C25 0.1(3) . . . . ?
C22 C21 C25 N26 -175.9(3) . . . . ?
I20 C21 C25 N26 3.3(5) . . . . ?
C22 C21 C25 N24 1.0(3) . . . . ?
I20 C21 C25 N24 -179.7(2) . . . . ?
N23 N24 C25 N26 176.6(3) . . . . ?
C29 N24 C25 N26 1.0(4) . . . . ?
N23 N24 C25 C21 -0.8(3) . . . . ?
C29 N24 C25 C21 -176.3(3) . . . . ?
C21 C25 N26 C27 173.4(3) . . . . ?
N24 C25 N26 C27 -3.1(4) . . . . ?
C25 N26 C27 C28 2.5(5) . . . . ?
N26 C27 C28 C29 0.2(5) . . . . ?
C27 C28 C29 N24 -2.3(4) . . . . ?
C27 C28 C29 C30 177.2(3) . . . . ?
N23 N24 C29 C28 -173.2(3) . . . . ?
C25 N24 C29 C28 1.7(4) . . . . ?
N23 N24 C29 C30 7.3(4) . . . . ?
C25 N24 C29 C30 -177.8(3) . . . . ?
C28 C29 C30 C36 -133.8(3) . . . . ?
N24 C29 C30 C36 45.6(4) . . . . ?
C28 C29 C30 C31 42.4(4) . . . . ?
N24 C29 C30 C31 -138.2(3) . . . . ?
C36 C30 C31 C32 -1.9(5) . . . . ?
C29 C30 C31 C32 -178.2(3) . . . . ?
C30 C31 C32 C33 1.4(5) . . . . ?
C31 C32 C33 C35 0.1(6) . . . . ?
C31 C32 C33 Cl34 179.9(3) . . . . ?
C32 C33 C35 C36 -1.0(5) . . . . ?
Cl34 C33 C35 C36 179.2(3) . . . . ?
C33 C35 C36 C30 0.4(5) . . . . ?
C31 C30 C36 C35 1.0(5) . . . . ?
C29 C30 C36 C35 177.2(3) . . . . ?

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
C8 H8B N26 0.96 2.53 3.486(4) 173.7 2_666
C37 H37A N19 0.96 2.51 3.454(4) 168.7 2_565

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_ar-sr
_database_code_depnum_ccdc_archive 'CCDC 1542479'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1,3,5-tris(2-(tert-Butyl)pyrazolo[1,5-a]pyrimidin-7-yl)benzene
_chemical_name_common            ?
_chemical_melting_point          '> 573'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C150 H162 N36'
_chemical_formula_weight         2469.15
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'

_symmetry_cell_setting           Hexagonal
_space_group_IT_number           148
_symmetry_space_group_name_H-M   R-3
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   14.6829(3)
_cell_length_b                   14.6829(3)
_cell_length_c                   57.9972(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10828.3(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23754
_cell_measurement_theta_min      2.3820
_cell_measurement_theta_max      34.5670

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             3942
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -93
_diffrn_reflns_limit_l_max       92
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         35.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10167
_reflns_number_gt                8956
_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       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0681P)²+32.3341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10167
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.190
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.086 77 22 ' '
2 0.000 0.000 0.500 294 92 ' '
3 0.000 0.000 0.914 77 22 ' '
4 0.333 0.667 0.167 296 92 ' '
5 0.333 0.667 0.580 77 22 ' '
6 0.333 0.667 0.753 77 22 ' '
7 0.667 0.333 0.833 296 92 ' '
8 0.667 0.333 0.247 77 22 ' '
9 0.667 0.333 0.420 77 22 ' '
_platon_squeeze_details          
;
SQUEEZE implemented in Platon: Spek, A.L. J. Appl. Cryst. 2003, 36, 7-13.
;

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
N1A N 0.88962(9) 0.71538(9) 0.12123(2) 0.0169(2) Uani 1 1 d . . . . .
N2A N 0.81762(9) 0.71075(8) 0.13632(2) 0.01415(19) Uani 1 1 d . . . . .
N3A N 0.64727(10) 0.58800(10) 0.15116(2) 0.0189(2) Uani 1 1 d . . . . .
C1A C 0.84942(11) 0.61606(10) 0.11376(2) 0.0169(2) Uani 1 1 d . . . . .
C2A C 0.75365(11) 0.54805(10) 0.12405(2) 0.0181(2) Uani 1 1 d . . . . .
H2A H 0.7127 0.4758 0.1218 0.022 Uiso 1 1 calc R U . . .
C3A C 0.73188(10) 0.60961(10) 0.13827(2) 0.0155(2) Uani 1 1 d . . . . .
C4A C 0.65064(11) 0.66796(11) 0.16197(3) 0.0191(2) Uani 1 1 d . . . . .
H4A H 0.5929 0.6554 0.1709 0.023 Uiso 1 1 calc R U . . .
C5A C 0.73551(10) 0.77132(10) 0.16098(2) 0.0175(2) Uani 1 1 d . . . . .
H5A H 0.7333 0.8245 0.1692 0.021 Uiso 1 1 calc R U . . .
C6A C 0.82131(10) 0.79332(10) 0.14786(2) 0.0147(2) Uani 1 1 d . . . . .
C7A C 0.90813(12) 0.59133(11) 0.09593(3) 0.0209(3) Uani 1 1 d . . . . .
C8A C 0.94696(16) 0.67383(15) 0.07684(3) 0.0319(4) Uani 1 1 d . . . . .
H8AA H 0.9846 0.6578 0.0655 0.048 Uiso 1 1 calc R U . . .
H8AB H 0.9928 0.7420 0.0833 0.048 Uiso 1 1 calc R U . . .
H8AC H 0.8879 0.6736 0.0697 0.048 Uiso 1 1 calc R U . . .
C9A C 1.00228(16) 0.59222(18) 0.10725(3) 0.0339(4) Uani 1 1 d . . . . .
H9AA H 1.0411 0.5783 0.0958 0.051 Uiso 1 1 calc R U . . .
H9AB H 0.9781 0.5390 0.1190 0.051 Uiso 1 1 calc R U . . .
H9AC H 1.0469 0.6599 0.1141 0.051 Uiso 1 1 calc R U . . .
C10A C 0.83535(16) 0.48408(14) 0.08546(3) 0.0323(4) Uani 1 1 d . . . . .
H10A H 0.7750 0.4836 0.0789 0.048 Uiso 1 1 calc R U . . .
H10B H 0.8130 0.4312 0.0972 0.048 Uiso 1 1 calc R U . . .
H10C H 0.8720 0.4697 0.0736 0.048 Uiso 1 1 calc R U . . .
C11A C 0.91384(10) 0.89869(10) 0.14634(2) 0.0149(2) Uani 1 1 d . . . . .
C12A C 0.89882(10) 0.98492(10) 0.14629(2) 0.0157(2) Uani 1 1 d . . . . .
H12A H 0.8310 0.9748 0.1462 0.019 Uiso 1 1 calc R U . . .
N1B N 0.45808(9) 0.04344(9) 0.04306(2) 0.0167(2) Uani 1 1 d . . . . .
N2B N 0.53254(9) 0.03751(9) 0.03053(2) 0.01480(19) Uani 1 1 d . . . . .
N3B N 0.57924(10) -0.08997(10) 0.01828(2) 0.0200(2) Uani 1 1 d . . . . .
C1B C 0.39272(11) -0.05557(11) 0.04991(2) 0.0181(2) Uani 1 1 d . . . . .
C2B C 0.42305(11) -0.12567(11) 0.04181(3) 0.0197(2) Uani 1 1 d . . . . .
H2B H 0.3892 -0.1979 0.0443 0.024 Uiso 1 1 calc R U . . .
C3B C 0.51402(11) -0.06541(10) 0.02936(2) 0.0169(2) Uani 1 1 d . . . . .
C4B C 0.66232(12) -0.01099(11) 0.00882(3) 0.0198(2) Uani 1 1 d . . . . .
H4B H 0.7089 -0.0255 0.0010 0.024 Uiso 1 1 calc R U . . .
C5B C 0.68559(11) 0.09371(11) 0.00972(2) 0.0177(2) Uani 1 1 d . . . . .
H5B H 0.7459 0.1459 0.0026 0.021 Uiso 1 1 calc R U . . .
C6B C 0.62020(10) 0.11973(10) 0.02106(2) 0.0146(2) Uani 1 1 d . . . . .
C7B C 0.29886(12) -0.07822(12) 0.06454(3) 0.0225(3) Uani 1 1 d . . . . .
C8B C 0.33328(13) 0.00043(14) 0.08427(3) 0.0275(3) Uani 1 1 d . . . . .
H8BA H 0.3697 0.0706 0.0782 0.041 Uiso 1 1 calc R U . . .
H8BB H 0.3793 -0.0097 0.0944 0.041 Uiso 1 1 calc R U . . .
H8BC H 0.2726 -0.0100 0.0927 0.041 Uiso 1 1 calc R U . . .
C9B C 0.21800(15) -0.0687(2) 0.04981(3) 0.0402(5) Uani 1 1 d . . . . .
H9BA H 0.2490 0.0010 0.0436 0.060 Uiso 1 1 calc R U . . .
H9BB H 0.1585 -0.0824 0.0592 0.060 Uiso 1 1 calc R U . . .
H9BC H 0.1955 -0.1189 0.0375 0.060 Uiso 1 1 calc R U . . .
C10B C 0.2496(2) -0.18868(16) 0.07435(5) 0.0462(6) Uani 1 1 d . . . . .
H10D H 0.2234 -0.2388 0.0620 0.069 Uiso 1 1 calc R U . . .
H10E H 0.1926 -0.2009 0.0844 0.069 Uiso 1 1 calc R U . . .
H10F H 0.3015 -0.1961 0.0829 0.069 Uiso 1 1 calc R U . . .
C11B C 0.64165(10) 0.22850(10) 0.02274(2) 0.0141(2) Uani 1 1 d . . . . .
C12B C 0.56222(10) 0.25358(10) 0.02290(2) 0.0147(2) Uani 1 1 d . . . . .
H12B H 0.4922 0.2002 0.0231 0.018 Uiso 1 1 calc R U . . .
C1S C 0.9519(7) 0.0128(8) 0.01846(14) 0.082(2) Uani 0.5 1 d . . P . .
H1S H 0.9323 0.0309 0.0328 0.098 Uiso 0.5 1 d R U P . .
C2S C 0.9434(10) 0.0499(11) -0.0006(2) 0.103(3) Uani 0.5 1 d . . P . .
H2S H 0.8930 0.0727 -0.0026 0.123 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.3425(17) . ?
N1A N2A 1.3476(15) . ?
N2A C6A 1.3620(16) . ?
N2A C3A 1.3904(16) . ?
N3A C4A 1.3097(18) . ?
N3A C3A 1.3450(18) . ?
C1A C2A 1.3881(19) . ?
C1A C7A 1.502(2) . ?
C2A C3A 1.3739(19) . ?
C4A C5A 1.4029(19) . ?
C5A C6A 1.3648(18) . ?
C6A C11A 1.4646(18) . ?
C7A C10A 1.519(2) . ?
C7A C9A 1.525(3) . ?
C7A C8A 1.526(2) . ?
C11A C12A 1.3885(18) 2_765 ?
C11A C12A 1.3896(18) . ?
C12A C11A 1.3884(18) 3_675 ?
N1B C1B 1.3405(17) . ?
N1B N2B 1.3511(16) . ?
N2B C6B 1.3647(17) . ?
N2B C3B 1.3968(17) . ?
N3B C4B 1.311(2) . ?
N3B C3B 1.3437(19) . ?
C1B C2B 1.392(2) . ?
C1B C7B 1.507(2) . ?
C2B C3B 1.381(2) . ?
C4B C5B 1.3992(19) . ?
C5B C6B 1.3664(19) . ?
C6B C11B 1.4684(17) . ?
C7B C10B 1.518(3) . ?
C7B C8B 1.522(2) . ?
C7B C9B 1.524(3) . ?
C11B C12B 1.3876(18) . ?
C11B C12B 1.3931(18) 2_655 ?
C12B C11B 1.3931(18) 3_665 ?
C1S C2S 1.268(12) . ?
C1S C2S 1.403(15) 12_545 ?
C1S C1S 1.414(14) 3_765 ?
C1S C1S 1.414(14) 2_645 ?
C1S C2S 1.747(16) 11_665 ?
C2S C2S 1.357(10) 12_545 ?
C2S C2S 1.357(10) 11_665 ?
C2S C1S 1.403(15) 11_665 ?
C2S C1S 1.747(16) 12_545 ?

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
C1A N1A N2A 104.31(11) . . ?
N1A N2A C6A 126.38(11) . . ?
N1A N2A C3A 112.03(11) . . ?
C6A N2A C3A 121.51(11) . . ?
C4A N3A C3A 115.98(12) . . ?
N1A C1A C2A 112.31(12) . . ?
N1A C1A C7A 119.41(12) . . ?
C2A C1A C7A 128.28(12) . . ?
C3A C2A C1A 105.67(12) . . ?
N3A C3A C2A 132.04(12) . . ?
N3A C3A N2A 122.23(12) . . ?
C2A C3A N2A 105.65(11) . . ?
N3A C4A C5A 124.41(13) . . ?
C6A C5A C4A 119.63(12) . . ?
N2A C6A C5A 116.23(12) . . ?
N2A C6A C11A 120.91(11) . . ?
C5A C6A C11A 122.85(12) . . ?
C1A C7A C10A 109.54(13) . . ?
C1A C7A C9A 109.20(13) . . ?
C10A C7A C9A 110.23(15) . . ?
C1A C7A C8A 109.85(12) . . ?
C10A C7A C8A 108.84(14) . . ?
C9A C7A C8A 109.17(15) . . ?
C12A C11A C12A 119.89(13) 2_765 . ?
C12A C11A C6A 121.54(11) 2_765 . ?
C12A C11A C6A 118.46(11) . . ?
C11A C12A C11A 120.11(13) 3_675 . ?
C1B N1B N2B 104.66(11) . . ?
N1B N2B C6B 126.52(11) . . ?
N1B N2B C3B 111.70(11) . . ?
C6B N2B C3B 121.65(12) . . ?
C4B N3B C3B 115.82(12) . . ?
N1B C1B C2B 112.43(13) . . ?
N1B C1B C7B 119.08(13) . . ?
C2B C1B C7B 128.48(13) . . ?
C3B C2B C1B 105.50(12) . . ?
N3B C3B C2B 131.98(13) . . ?
N3B C3B N2B 122.30(13) . . ?
C2B C3B N2B 105.70(12) . . ?
N3B C4B C5B 124.33(13) . . ?
C6B C5B C4B 120.38(13) . . ?
N2B C6B C5B 115.48(12) . . ?
N2B C6B C11B 122.00(11) . . ?
C5B C6B C11B 122.52(12) . . ?
C1B C7B C10B 109.97(15) . . ?
C1B C7B C8B 109.62(12) . . ?
C10B C7B C8B 109.20(16) . . ?
C1B C7B C9B 109.42(13) . . ?
C10B C7B C9B 109.30(17) . . ?
C8B C7B C9B 109.30(16) . . ?
C12B C11B C12B 119.70(12) . 2_655 ?
C12B C11B C6B 122.51(11) . . ?
C12B C11B C6B 117.70(11) 2_655 . ?
C11B C12B C11B 120.29(12) . 3_665 ?
C2S C1S C2S 60.8(5) . 12_545 ?
C2S C1S C1S 100.3(9) . 3_765 ?
C2S C1S C1S 115.8(6) 12_545 3_765 ?
C2S C1S C1S 118.8(7) . 2_645 ?
C2S C1S C1S 76.7(9) 12_545 2_645 ?
C1S C1S C1S 59.996(1) 3_765 2_645 ?
C2S C1S C2S 50.5(5) . 11_665 ?
C2S C1S C2S 95.7(9) 12_545 11_665 ?
C1S C1S C2S 51.4(7) 3_765 11_665 ?
C1S C1S C2S 97.5(7) 2_645 11_665 ?
C1S C2S C2S 64.5(8) . 12_545 ?
C1S C2S C2S 83.4(10) . 11_665 ?
C2S C2S C2S 119.7(2) 12_545 11_665 ?
C1S C2S C1S 118.1(11) . 11_665 ?
C2S C2S C1S 96.6(10) 12_545 11_665 ?
C2S C2S C1S 54.7(8) 11_665 11_665 ?
C1S C2S C1S 97.7(10) . 12_545 ?
C2S C2S C1S 46.1(7) 12_545 12_545 ?
C2S C2S C1S 95.3(8) 11_665 12_545 ?
C1S C2S C1S 52.0(8) 11_665 12_545 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A N1A N2A C6A -177.26(13) . . . . ?
C1A N1A N2A C3A -0.58(15) . . . . ?
N2A N1A C1A C2A -0.76(16) . . . . ?
N2A N1A C1A C7A 178.40(12) . . . . ?
N1A C1A C2A C3A 1.78(17) . . . . ?
C7A C1A C2A C3A -177.29(14) . . . . ?
C4A N3A C3A C2A -176.69(15) . . . . ?
C4A N3A C3A N2A -0.5(2) . . . . ?
C1A C2A C3A N3A 174.67(15) . . . . ?
C1A C2A C3A N2A -1.99(15) . . . . ?
N1A N2A C3A N3A -175.40(13) . . . . ?
C6A N2A C3A N3A 1.5(2) . . . . ?
N1A N2A C3A C2A 1.66(15) . . . . ?
C6A N2A C3A C2A 178.53(12) . . . . ?
C3A N3A C4A C5A -0.6(2) . . . . ?
N3A C4A C5A C6A 0.7(2) . . . . ?
N1A N2A C6A C5A 175.12(13) . . . . ?
C3A N2A C6A C5A -1.27(19) . . . . ?
N1A N2A C6A C11A -6.0(2) . . . . ?
C3A N2A C6A C11A 177.65(12) . . . . ?
C4A C5A C6A N2A 0.2(2) . . . . ?
C4A C5A C6A C11A -178.65(13) . . . . ?
N1A C1A C7A C10A -164.29(15) . . . . ?
C2A C1A C7A C10A 14.7(2) . . . . ?
N1A C1A C7A C9A 74.91(18) . . . . ?
C2A C1A C7A C9A -106.08(18) . . . . ?
N1A C1A C7A C8A -44.8(2) . . . . ?
C2A C1A C7A C8A 134.23(17) . . . . ?
N2A C6A C11A C12A -39.55(19) . . . 2_765 ?
C5A C6A C11A C12A 139.29(14) . . . 2_765 ?
N2A C6A C11A C12A 144.14(13) . . . . ?
C5A C6A C11A C12A -37.0(2) . . . . ?
C12A C11A C12A C11A -0.4(3) 2_765 . . 3_675 ?
C6A C11A C12A C11A 175.92(9) . . . 3_675 ?
C1B N1B N2B C6B -175.68(12) . . . . ?
C1B N1B N2B C3B 0.30(14) . . . . ?
N2B N1B C1B C2B -0.66(16) . . . . ?
N2B N1B C1B C7B 179.93(12) . . . . ?
N1B C1B C2B C3B 0.77(16) . . . . ?
C7B C1B C2B C3B -179.88(14) . . . . ?
C4B N3B C3B C2B -177.32(15) . . . . ?
C4B N3B C3B N2B 0.7(2) . . . . ?
C1B C2B C3B N3B 177.74(15) . . . . ?
C1B C2B C3B N2B -0.54(15) . . . . ?
N1B N2B C3B N3B -178.32(12) . . . . ?
C6B N2B C3B N3B -2.1(2) . . . . ?
N1B N2B C3B C2B 0.16(15) . . . . ?
C6B N2B C3B C2B 176.37(12) . . . . ?
C3B N3B C4B C5B 0.2(2) . . . . ?
N3B C4B C5B C6B 0.2(2) . . . . ?
N1B N2B C6B C5B 177.98(12) . . . . ?
C3B N2B C6B C5B 2.36(18) . . . . ?
N1B N2B C6B C11B -2.7(2) . . . . ?
C3B N2B C6B C11B -178.36(12) . . . . ?
C4B C5B C6B N2B -1.45(19) . . . . ?
C4B C5B C6B C11B 179.28(13) . . . . ?
N1B C1B C7B C10B -168.22(16) . . . . ?
C2B C1B C7B C10B 12.5(2) . . . . ?
N1B C1B C7B C8B -48.15(19) . . . . ?
C2B C1B C7B C8B 132.54(16) . . . . ?
N1B C1B C7B C9B 71.71(18) . . . . ?
C2B C1B C7B C9B -107.60(19) . . . . ?
N2B C6B C11B C12B -33.16(19) . . . . ?
C5B C6B C11B C12B 146.07(14) . . . . ?
N2B C6B C11B C12B 150.41(12) . . . 2_655 ?
C5B C6B C11B C12B -30.37(19) . . . 2_655 ?
C12B C11B C12B C11B 1.3(3) 2_655 . . 3_665 ?
C6B C11B C12B C11B -175.05(8) . . . 3_665 ?
C1S C1S C2S C2S 113.9(9) 3_765 . . 12_545 ?
C1S C1S C2S C2S 52.5(12) 2_645 . . 12_545 ?
C2S C1S C2S C2S 127.5(7) 11_665 . . 12_545 ?
C2S C1S C2S C2S -127.5(7) 12_545 . . 11_665 ?
C1S C1S C2S C2S -13.6(11) 3_765 . . 11_665 ?
C1S C1S C2S C2S -74.9(15) 2_645 . . 11_665 ?
C2S C1S C2S C1S -83.7(10) 12_545 . . 11_665 ?
C1S C1S C2S C1S 30.2(17) 3_765 . . 11_665 ?
C1S C1S C2S C1S -31(2) 2_645 . . 11_665 ?
C2S C1S C2S C1S 43.8(7) 11_665 . . 11_665 ?
C2S C1S C2S C1S -33.0(6) 12_545 . . 12_545 ?
C1S C1S C2S C1S 80.9(9) 3_765 . . 12_545 ?
C1S C1S C2S C1S 19.6(13) 2_645 . . 12_545 ?
C2S C1S C2S C1S 94.5(7) 11_665 . . 12_545 ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.095
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       ', Luminescent'
