# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2bBr-sr
_database_code_depnum_ccdc_archive 'CCDC 1049817'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H31 Br2 F6 I3 N6 O P'
_chemical_formula_weight         1141.07

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9697(14)
_cell_length_b                   14.1499(18)
_cell_length_c                   16.420(2)
_cell_angle_alpha                93.110(3)
_cell_angle_beta                 108.455(3)
_cell_angle_gamma                112.057(3)
_cell_volume                     2196.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1082
_exptl_absorpt_coefficient_mu    4.041
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3974
_exptl_absorpt_correction_T_max  0.6427
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25065
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7711
_reflns_number_gt                6138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Ortep 3v.2'

_refine_special_details          SQUEEZE
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.008 0.000 0.000 213 96 ' '
2 0.000 0.500 0.500 171 62 ' '
3 0.500 0.500 0.500 60 25 ' '
_platon_squeeze_details          
;
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1908P)²+44.2757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7711
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   0.609
_refine_ls_restrained_S_all      0.609
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C26A C 0.190(5) 0.676(4) 0.889(3) 0.101(12) Uiso 0.40 1 d P . .
C26B C 0.138(2) 0.6323(17) 0.8199(15) 0.069(5) Uiso 0.60 1 d P . .
I1 I 0.11561(5) 0.74834(4) 0.35304(4) 0.03046(17) Uani 1 1 d . . .
I2 I 1.34923(5) 1.03472(4) 0.75434(3) 0.03175(17) Uani 1 1 d . . .
I3 I 0.30490(5) 0.45627(4) 0.72166(4) 0.03661(18) Uani 1 1 d . . .
Br4 Br 0.59478(8) 0.01527(6) 0.71247(6) 0.0347(2) Uani 1 1 d . . .
Br5 Br 0.85698(8) 0.77409(6) 0.38051(6) 0.0368(2) Uani 1 1 d . . .
C2 C 0.7315(7) 0.8898(5) 0.5634(5) 0.0264(16) Uani 1 1 d . . .
C7 C 0.5881(8) 0.8303(6) 0.5461(5) 0.0274(16) Uani 1 1 d . . .
C6 C 0.5453(8) 0.7543(6) 0.5952(6) 0.0345(18) Uani 1 1 d . . .
C8 C 0.4762(8) 0.8479(7) 0.4747(6) 0.0361(19) Uani 1 1 d . . .
H8A H 0.4010 0.8450 0.4949 0.043 Uiso 1 1 calc R . .
H8B H 0.5172 0.9165 0.4621 0.043 Uiso 1 1 calc R . .
C3 C 0.8311(8) 0.8724(6) 0.6322(5) 0.0283(16) Uani 1 1 d . . .
C4 C 0.7895(8) 0.8013(6) 0.6832(6) 0.0331(18) Uani 1 1 d . . .
C1 C 0.7784(9) 0.9697(6) 0.5090(5) 0.0311(17) Uani 1 1 d . . .
H1A H 0.6988 0.9810 0.4734 0.047 Uiso 1 1 calc R . .
H1B H 0.8168 0.9447 0.4721 0.047 Uiso 1 1 calc R . .
H1C H 0.8492 1.0339 0.5472 0.047 Uiso 1 1 calc R . .
C5 C 0.6455(9) 0.7403(6) 0.6631(5) 0.0337(18) Uani 1 1 d . . .
C10 C 0.9874(8) 0.9370(6) 0.6523(5) 0.0316(18) Uani 1 1 d . . .
H10A H 1.0360 0.8915 0.6578 0.038 Uiso 1 1 calc R . .
H10B H 0.9987 0.9717 0.6041 0.038 Uiso 1 1 calc R . .
C9 C 0.5985(11) 0.6598(7) 0.7157(7) 0.045(2) Uani 1 1 d . . .
H9A H 0.5413 0.5924 0.6769 0.054 Uiso 1 1 calc R . .
H9B H 0.6808 0.6558 0.7576 0.054 Uiso 1 1 calc R . .
C15 C 0.1846(18) 0.6883(13) 0.1205(11) 0.105(6) Uani 1 1 d . . .
H15A H 0.2022 0.7575 0.1450 0.158 Uiso 1 1 calc R . .
H15B H 0.1033 0.6625 0.0672 0.158 Uiso 1 1 calc R . .
H15C H 0.2652 0.6896 0.1085 0.158 Uiso 1 1 calc R . .
C13 C 0.2839(8) 0.7290(6) 0.3368(5) 0.0272(16) Uani 1 1 d . . .
C12 C 0.4110(8) 0.6704(7) 0.2847(5) 0.0330(18) Uani 1 1 d . . .
H12 H 0.4357 0.6354 0.2475 0.040 Uiso 1 1 calc R . .
C11 C 0.4962(8) 0.7316(6) 0.3604(5) 0.0329(18) Uani 1 1 d . . .
H11 H 0.5919 0.7475 0.3869 0.040 Uiso 1 1 calc R . .
C14 C 0.1572(10) 0.6171(9) 0.1861(7) 0.058(3) Uani 1 1 d . . .
H14A H 0.0699 0.6089 0.1938 0.070 Uiso 1 1 calc R . .
H14B H 0.1497 0.5490 0.1650 0.070 Uiso 1 1 calc R . .
N2 N 0.4173(6) 0.7685(5) 0.3941(4) 0.0243(13) Uani 1 1 d . . .
N1 N 0.2776(7) 0.6668(5) 0.2696(5) 0.0328(15) Uani 1 1 d . . .
N4 N 0.3719(10) 0.6639(6) 0.8297(6) 0.050(2) Uani 1 1 d . . .
N3 N 0.5171(8) 0.6832(5) 0.7624(5) 0.0361(16) Uani 1 1 d . . .
C16 C 0.4099(10) 0.6147(7) 0.7792(6) 0.040(2) Uani 1 1 d . . .
C21 C 1.4108(12) 1.2921(8) 0.8913(7) 0.055(3) Uani 1 1 d . . .
H21A H 1.4274 1.2761 0.8394 0.083 Uiso 1 1 calc R . .
H21B H 1.4991 1.3350 0.9372 0.083 Uiso 1 1 calc R . .
H21C H 1.3507 1.3284 0.8795 0.083 Uiso 1 1 calc R . .
C18 C 0.9791(8) 1.0567(6) 0.7690(5) 0.0279(16) Uani 1 1 d . . .
H18 H 0.8827 1.0395 0.7478 0.033 Uiso 1 1 calc R . .
C19 C 1.0763(9) 1.1261(7) 0.8397(6) 0.042(2) Uani 1 1 d . . .
H19 H 1.0596 1.1670 0.8775 0.050 Uiso 1 1 calc R . .
C17 C 1.1878(8) 1.0601(7) 0.7805(6) 0.0338(18) Uani 1 1 d . . .
C20 C 1.3413(9) 1.1941(7) 0.9191(6) 0.042(2) Uani 1 1 d . . .
H20A H 1.4023 1.1576 0.9321 0.050 Uiso 1 1 calc R . .
H20B H 1.3246 1.2099 0.9718 0.050 Uiso 1 1 calc R . .
N5 N 1.0512(6) 1.0146(5) 0.7330(4) 0.0283(14) Uani 1 1 d . . .
N6 N 1.2058(7) 1.1278(6) 0.8482(5) 0.0373(16) Uani 1 1 d . . .
C22 C 0.3901(9) 0.6909(8) 0.5743(7) 0.050(2) Uani 1 1 d . . .
H22A H 0.3756 0.6231 0.5874 0.075 Uiso 1 1 calc R . .
H22B H 0.3390 0.6843 0.5133 0.075 Uiso 1 1 calc R . .
H22C H 0.3568 0.7249 0.6089 0.075 Uiso 1 1 calc R . .
C23 C 0.8997(10) 0.7893(7) 0.7609(7) 0.050(2) Uani 1 1 d . . .
H23A H 0.8899 0.7187 0.7533 0.074 Uiso 1 1 calc R . .
H23B H 0.8862 0.8065 0.8138 0.074 Uiso 1 1 calc R . .
H23C H 0.9924 0.8351 0.7644 0.074 Uiso 1 1 calc R . .
C27 C 0.5474(11) 0.7801(7) 0.8043(6) 0.047(2) Uani 1 1 d . . .
H27 H 0.6175 0.8422 0.8035 0.056 Uiso 1 1 calc R . .
C24 C 0.4587(14) 0.7698(8) 0.8465(8) 0.060(3) Uani 1 1 d . . .
H24 H 0.4554 0.8229 0.8805 0.072 Uiso 1 1 calc R . .
C25 C 0.2609(18) 0.6170(11) 0.8653(12) 0.093(5) Uani 1 1 d . . .
P1 P 0.7729(3) 0.5952(2) 0.95774(17) 0.0484(6) Uani 1 1 d . . .
F3 F 0.6857(9) 0.5346(6) 0.8597(5) 0.092(3) Uani 1 1 d . . .
F1 F 0.9024(10) 0.6374(8) 0.9322(6) 0.116(3) Uani 1 1 d . . .
F2 F 0.7477(15) 0.6928(8) 0.9348(6) 0.139(5) Uani 1 1 d . . .
F5 F 0.8530(11) 0.6530(7) 1.0560(4) 0.102(3) Uani 1 1 d . . .
F4 F 0.8051(16) 0.5002(7) 0.9807(6) 0.142(5) Uani 1 1 d . . .
F6 F 0.6328(13) 0.5653(13) 0.9720(12) 0.223(10) Uani 1 1 d . . .
O1 O 0.1964(8) 0.4605(4) 0.3811(4) 0.0529(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C26A C25 1.45(5) . ?
C26B C25 1.42(3) . ?
I1 C13 2.059(7) . ?
I2 C17 2.095(8) . ?
I3 C16 2.095(9) . ?
C2 C7 1.400(10) . ?
C2 C3 1.408(11) . ?
C2 C1 1.517(11) . ?
C7 C6 1.408(12) . ?
C7 C8 1.514(11) . ?
C6 C5 1.379(12) . ?
C6 C22 1.507(11) . ?
C8 N2 1.477(10) . ?
C3 C4 1.382(12) . ?
C3 C10 1.522(10) . ?
C4 C5 1.401(11) . ?
C4 C23 1.522(12) . ?
C5 C9 1.503(12) . ?
C10 N5 1.459(10) . ?
C9 N3 1.457(12) . ?
C15 C14 1.54(2) . ?
C13 N1 1.340(10) . ?
C13 N2 1.341(10) . ?
C12 C11 1.307(12) . ?
C12 N1 1.385(10) . ?
C11 N2 1.393(9) . ?
C14 N1 1.473(12) . ?
N4 C16 1.311(13) . ?
N4 C24 1.395(14) . ?
N4 C25 1.466(14) . ?
N3 C16 1.332(12) . ?
N3 C27 1.369(11) . ?
C21 C20 1.485(14) . ?
C18 C19 1.325(12) . ?
C18 N5 1.393(10) . ?
C19 N6 1.374(11) . ?
C17 N5 1.323(10) . ?
C17 N6 1.341(11) . ?
C20 N6 1.477(11) . ?
C27 C24 1.333(15) . ?
P1 F1 1.522(9) . ?
P1 F6 1.531(11) . ?
P1 F2 1.550(9) . ?
P1 F4 1.550(8) . ?
P1 F5 1.570(7) . ?
P1 F3 1.581(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C2 C3 117.9(7) . . ?
C7 C2 C1 121.1(7) . . ?
C3 C2 C1 120.9(7) . . ?
C2 C7 C6 120.9(7) . . ?
C2 C7 C8 120.3(7) . . ?
C6 C7 C8 118.8(7) . . ?
C5 C6 C7 119.7(7) . . ?
C5 C6 C22 120.8(8) . . ?
C7 C6 C22 119.5(8) . . ?
N2 C8 C7 110.9(6) . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 C10 120.0(7) . . ?
C2 C3 C10 118.6(7) . . ?
C3 C4 C5 119.7(8) . . ?
C3 C4 C23 120.1(7) . . ?
C5 C4 C23 120.2(8) . . ?
C6 C5 C4 120.3(8) . . ?
C6 C5 C9 119.2(8) . . ?
C4 C5 C9 120.5(8) . . ?
N5 C10 C3 111.5(6) . . ?
N3 C9 C5 112.3(7) . . ?
N1 C13 N2 107.0(6) . . ?
N1 C13 I1 126.0(5) . . ?
N2 C13 I1 126.8(5) . . ?
C11 C12 N1 108.1(7) . . ?
C12 C11 N2 107.5(7) . . ?
N1 C14 C15 107.0(9) . . ?
C13 N2 C11 108.7(6) . . ?
C13 N2 C8 126.0(6) . . ?
C11 N2 C8 124.9(6) . . ?
C13 N1 C12 108.7(6) . . ?
C13 N1 C14 126.3(7) . . ?
C12 N1 C14 124.2(7) . . ?
C16 N4 C24 108.1(9) . . ?
C16 N4 C25 126.7(9) . . ?
C24 N4 C25 125.1(10) . . ?
C16 N3 C27 107.9(8) . . ?
C16 N3 C9 126.7(7) . . ?
C27 N3 C9 125.1(8) . . ?
N4 C16 N3 109.4(8) . . ?
N4 C16 I3 125.6(7) . . ?
N3 C16 I3 124.7(7) . . ?
C19 C18 N5 105.9(7) . . ?
C18 C19 N6 108.8(7) . . ?
N5 C17 N6 107.7(7) . . ?
N5 C17 I2 126.7(6) . . ?
N6 C17 I2 125.6(6) . . ?
N6 C20 C21 109.4(8) . . ?
C17 N5 C18 109.5(7) . . ?
C17 N5 C10 125.0(6) . . ?
C18 N5 C10 125.4(6) . . ?
C17 N6 C19 108.1(7) . . ?
C17 N6 C20 126.2(7) . . ?
C19 N6 C20 125.7(7) . . ?
C24 C27 N3 108.0(9) . . ?
C27 C24 N4 106.6(9) . . ?
C26B C25 C26A 45.7(19) . . ?
C26B C25 N4 111.3(14) . . ?
C26A C25 N4 121(2) . . ?
F1 P1 F6 169.2(10) . . ?
F1 P1 F2 87.8(7) . . ?
F6 P1 F2 82.3(10) . . ?
F1 P1 F4 89.7(7) . . ?
F6 P1 F4 100.3(10) . . ?
F2 P1 F4 177.4(8) . . ?
F1 P1 F5 95.2(6) . . ?
F6 P1 F5 89.1(7) . . ?
F2 P1 F5 88.8(5) . . ?
F4 P1 F5 90.7(5) . . ?
F1 P1 F3 87.5(5) . . ?
F6 P1 F3 88.4(7) . . ?
F2 P1 F3 91.4(5) . . ?
F4 P1 F3 89.2(5) . . ?
F5 P1 F3 177.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.368
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.184
####################################################################### 
# 
# 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_2bCl-sr
_database_code_depnum_ccdc_archive 'CCDC 1049818'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H33 Cl2 F6 I3 N6 O P'
_chemical_formula_weight         1054.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6955(13)
_cell_length_b                   13.5915(17)
_cell_length_c                   16.862(2)
_cell_angle_alpha                93.543(3)
_cell_angle_beta                 107.602(3)
_cell_angle_gamma                110.756(3)
_cell_volume                     2145.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      31.78

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1014
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5966
_exptl_absorpt_correction_T_max  0.7953
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7524
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7524
_reflns_number_gt                6604
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Ortep 3v.2'

_refine_special_details          SQUEEZE
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.081 0.500 0.500 308 94 ' '
2 0.500 1.000 1.000 134 48 ' '
_platon_squeeze_details          
;
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0873P)²+2.3217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7524
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_restrained_S_all      1.223
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C25A C 0.8663(18) 0.3579(14) 0.8622(10) 0.048(4) Uiso 0.53 1 d P A 1
C25B C 0.825(2) 0.3130(17) 0.8687(12) 0.055(5) Uiso 0.47 1 d P A 2
I1 I -0.35851(4) -0.02949(3) 0.24908(3) 0.03047(14) Uani 1 1 d . . .
I2 I 0.88317(4) 0.24917(3) 0.64367(3) 0.03073(14) Uani 1 1 d . . .
I3 I 0.70542(4) 0.54506(3) 0.27725(3) 0.02973(14) Uani 1 1 d . . .
Cl5 Cl 0.14329(14) 0.22666(11) 0.62778(10) 0.0315(3) Uani 1 1 d . . .
P6 P 0.24131(18) 0.39477(14) 0.05242(10) 0.0365(4) Uani 1 1 d . . .
Cl4 Cl 0.39136(14) 0.97732(11) 0.28257(9) 0.0265(3) Uani 1 1 d . . .
C6 C 0.4607(6) 0.2330(5) 0.4113(4) 0.0278(13) Uani 1 1 d . . .
C1 C 0.2021(7) 0.0269(5) 0.4938(4) 0.0303(13) Uani 1 1 d . . .
H1A H 0.2752 0.0054 0.5264 0.045 Uiso 1 1 calc R . .
H1B H 0.1232 -0.0349 0.4568 0.045 Uiso 1 1 calc R . .
H1C H 0.1706 0.0603 0.5313 0.045 Uiso 1 1 calc R . .
C9 C 0.5154(6) 0.1403(4) 0.5335(4) 0.0261(12) Uani 1 1 d . . .
H9A H 0.4696 0.0727 0.5490 0.031 Uiso 1 1 calc R . .
H9B H 0.5923 0.1359 0.5162 0.031 Uiso 1 1 calc R . .
C7 C 0.4083(6) 0.1585(4) 0.4600(4) 0.0245(12) Uani 1 1 d . . .
C2 C 0.2613(5) 0.1060(4) 0.4414(3) 0.0222(12) Uani 1 1 d . . .
C3 C 0.1679(6) 0.1277(5) 0.3728(4) 0.0258(12) Uani 1 1 d . . .
C8 C 0.4238(7) 0.3440(5) 0.3015(4) 0.0344(14) Uani 1 1 d . . .
H8A H 0.3457 0.3611 0.2680 0.041 Uiso 1 1 calc R . .
H8B H 0.4923 0.4078 0.3428 0.041 Uiso 1 1 calc R . .
C5 C 0.3672(6) 0.2566(4) 0.3476(4) 0.0267(13) Uani 1 1 d . . .
C4 C 0.2208(6) 0.2046(5) 0.3261(4) 0.0296(13) Uani 1 1 d . . .
C12 C 0.7106(6) 0.2724(4) 0.6591(4) 0.0234(12) Uani 1 1 d . . .
C10 C 0.4942(6) 0.2682(4) 0.6378(4) 0.0251(12) Uani 1 1 d . . .
H10 H 0.3967 0.2506 0.6138 0.030 Uiso 1 1 calc R . .
C11 C 0.5840(6) 0.3393(5) 0.7095(4) 0.0286(13) Uani 1 1 d . . .
H11 H 0.5599 0.3791 0.7448 0.034 Uiso 1 1 calc R . .
N2 N 0.5739(5) 0.2263(4) 0.6065(3) 0.0211(9) Uani 1 1 d . . .
N1 N 0.7186(5) 0.3420(4) 0.7205(3) 0.0281(11) Uani 1 1 d . A .
N4 N 0.6181(6) 0.3263(4) 0.1655(3) 0.0354(12) Uani 1 1 d . . .
N3 N 0.4922(5) 0.3153(4) 0.2458(3) 0.0285(11) Uani 1 1 d . . .
C13 C 0.5949(6) 0.3833(5) 0.2231(4) 0.0288(13) Uani 1 1 d . . .
C14 C 0.4534(7) 0.2134(5) 0.2030(4) 0.0361(15) Uani 1 1 d . . .
H14 H 0.3854 0.1508 0.2079 0.043 Uiso 1 1 calc R . .
C15 C 0.5309(8) 0.2210(5) 0.1535(4) 0.0401(16) Uani 1 1 d . . .
H15 H 0.5266 0.1646 0.1172 0.048 Uiso 1 1 calc R . .
F2 F 0.3132(5) 0.4478(4) 0.1504(3) 0.0634(13) Uani 1 1 d . . .
F1 F 0.0904(5) 0.3690(4) 0.0618(3) 0.0651(13) Uani 1 1 d . . .
F3 F 0.1680(5) 0.3429(5) -0.0460(3) 0.0671(14) Uani 1 1 d . . .
F4 F 0.3945(5) 0.4185(5) 0.0476(3) 0.0747(15) Uani 1 1 d . . .
C17 C 0.0205(6) -0.0522(5) 0.2332(4) 0.0339(14) Uani 1 1 d . . .
H17 H 0.1179 -0.0362 0.2538 0.041 Uiso 1 1 calc R . .
C18 C -0.1906(6) -0.0542(5) 0.2223(4) 0.0277(13) Uani 1 1 d . . .
C16 C -0.0750(7) -0.1218(5) 0.1620(5) 0.0396(16) Uani 1 1 d . . .
H16 H -0.0564 -0.1628 0.1244 0.048 Uiso 1 1 calc R . .
C20 C -0.4135(8) -0.2897(6) 0.1134(5) 0.0451(17) Uani 1 1 d . . .
H20A H -0.3524 -0.3284 0.1245 0.068 Uiso 1 1 calc R . .
H20B H -0.5019 -0.3328 0.0692 0.068 Uiso 1 1 calc R . .
H20C H -0.4316 -0.2730 0.1639 0.068 Uiso 1 1 calc R . .
C19 C -0.3428(7) -0.1886(5) 0.0864(4) 0.0380(15) Uani 1 1 d . . .
H19A H -0.4051 -0.1500 0.0738 0.046 Uiso 1 1 calc R . .
H19B H -0.3239 -0.2050 0.0355 0.046 Uiso 1 1 calc R . .
N6 N -0.0520(5) -0.0088(4) 0.2701(3) 0.0254(10) Uani 1 1 d . . .
N5 N -0.2054(5) -0.1203(4) 0.1560(3) 0.0329(12) Uani 1 1 d . . .
C21 C 0.7194(9) 0.3686(7) 0.1214(6) 0.057(2) Uani 1 1 d . . .
H21A H 0.7464 0.4453 0.1260 0.068 Uiso 1 1 calc R . .
H21B H 0.6748 0.3357 0.0618 0.068 Uiso 1 1 calc R . .
F6 F 0.2337(7) 0.2828(4) 0.0746(4) 0.0816(17) Uani 1 1 d . . .
F5 F 0.2455(7) 0.5068(4) 0.0308(3) 0.0731(15) Uani 1 1 d . . .
C22 C 0.0086(6) 0.0699(5) 0.3487(4) 0.0336(14) Uani 1 1 d . . .
H22A H -0.0122 0.0340 0.3939 0.040 Uiso 1 1 calc R . .
H22B H -0.0355 0.1216 0.3416 0.040 Uiso 1 1 calc R . .
C23 C 0.8456(8) 0.4052(7) 0.7949(5) 0.064(3) Uani 1 1 d . . .
H23A H 0.9290 0.4228 0.7782 0.076 Uiso 1 1 calc R A 1
H23B H 0.8387 0.4720 0.8119 0.076 Uiso 1 1 calc R A 1
C24 C 0.8477(10) 0.3456(9) 0.1590(8) 0.087(3) Uani 1 1 d . . .
H24A H 0.8960 0.3831 0.2167 0.131 Uiso 1 1 calc R . .
H24B H 0.9104 0.3689 0.1273 0.131 Uiso 1 1 calc R . .
H24C H 0.8201 0.2700 0.1574 0.131 Uiso 1 1 calc R . .
C26 C 0.6186(7) 0.2842(6) 0.4289(4) 0.0397(16) Uani 1 1 d . . .
H26A H 0.6486 0.2339 0.4056 0.059 Uiso 1 1 calc R . .
H26B H 0.6684 0.3048 0.4890 0.059 Uiso 1 1 calc R . .
H26C H 0.6396 0.3464 0.4033 0.059 Uiso 1 1 calc R . .
C27 C 0.1200(7) 0.2261(5) 0.2531(4) 0.0380(15) Uani 1 1 d . . .
H27A H 0.1402 0.3014 0.2605 0.057 Uiso 1 1 calc R . .
H27B H 0.0239 0.1872 0.2503 0.057 Uiso 1 1 calc R . .
H27C H 0.1311 0.2035 0.2015 0.057 Uiso 1 1 calc R . .
O4 O 0.1406(5) 0.9889(4) 0.0295(4) 0.0511(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C25A C23 1.338(18) . ?
C25B C23 1.82(2) . ?
I1 C18 2.108(6) . ?
I2 C12 2.066(5) . ?
I3 C13 2.079(6) . ?
P6 F6 1.570(5) . ?
P6 F5 1.577(5) . ?
P6 F4 1.582(5) . ?
P6 F1 1.585(5) . ?
P6 F2 1.592(4) . ?
P6 F3 1.595(4) . ?
C6 C5 1.371(9) . ?
C6 C7 1.411(8) . ?
C6 C26 1.504(8) . ?
C1 C2 1.520(7) . ?
C9 N2 1.454(7) . ?
C9 C7 1.513(8) . ?
C7 C2 1.399(7) . ?
C2 C3 1.406(8) . ?
C3 C4 1.408(8) . ?
C3 C22 1.510(8) . ?
C8 N3 1.463(7) . ?
C8 C5 1.507(8) . ?
C5 C4 1.387(8) . ?
C4 C27 1.493(9) . ?
C12 N1 1.320(7) . ?
C12 N2 1.347(7) . ?
C10 C11 1.346(8) . ?
C10 N2 1.381(7) . ?
C11 N1 1.382(7) . ?
N1 C23 1.472(8) . ?
N4 C13 1.339(8) . ?
N4 C15 1.365(9) . ?
N4 C21 1.468(8) . ?
N3 C13 1.337(7) . ?
N3 C14 1.378(8) . ?
C14 C15 1.328(9) . ?
C17 C16 1.346(9) . ?
C17 N6 1.381(8) . ?
C18 N5 1.323(8) . ?
C18 N6 1.340(7) . ?
C16 N5 1.375(8) . ?
C20 C19 1.489(10) . ?
C19 N5 1.501(8) . ?
N6 C22 1.460(8) . ?
C21 C24 1.478(13) . ?

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
F6 P6 F5 178.5(3) . . ?
F6 P6 F4 89.2(3) . . ?
F5 P6 F4 92.3(3) . . ?
F6 P6 F1 88.8(3) . . ?
F5 P6 F1 89.8(3) . . ?
F4 P6 F1 177.0(3) . . ?
F6 P6 F2 90.3(3) . . ?
F5 P6 F2 89.4(3) . . ?
F4 P6 F2 89.5(3) . . ?
F1 P6 F2 88.3(3) . . ?
F6 P6 F3 90.4(3) . . ?
F5 P6 F3 89.8(3) . . ?
F4 P6 F3 91.1(3) . . ?
F1 P6 F3 91.2(3) . . ?
F2 P6 F3 179.1(3) . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 C26 120.7(5) . . ?
C7 C6 C26 119.7(6) . . ?
N2 C9 C7 111.4(4) . . ?
C2 C7 C6 120.2(5) . . ?
C2 C7 C9 121.8(5) . . ?
C6 C7 C9 118.0(5) . . ?
C7 C2 C3 118.7(5) . . ?
C7 C2 C1 121.3(5) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 C22 120.4(5) . . ?
C4 C3 C22 118.8(6) . . ?
N3 C8 C5 113.5(5) . . ?
C6 C5 C4 121.7(5) . . ?
C6 C5 C8 119.6(5) . . ?
C4 C5 C8 118.7(6) . . ?
C5 C4 C3 118.7(6) . . ?
C5 C4 C27 121.2(5) . . ?
C3 C4 C27 120.1(5) . . ?
N1 C12 N2 108.2(5) . . ?
N1 C12 I2 124.8(4) . . ?
N2 C12 I2 126.9(4) . . ?
C11 C10 N2 107.3(5) . . ?
C10 C11 N1 107.0(5) . . ?
C12 N2 C10 108.3(4) . . ?
C12 N2 C9 126.7(5) . . ?
C10 N2 C9 124.8(5) . . ?
C12 N1 C11 109.2(5) . . ?
C12 N1 C23 126.7(5) . . ?
C11 N1 C23 123.8(5) . . ?
C13 N4 C15 108.8(5) . . ?
C13 N4 C21 126.4(6) . . ?
C15 N4 C21 124.9(6) . . ?
C13 N3 C14 108.5(5) . . ?
C13 N3 C8 126.3(5) . . ?
C14 N3 C8 125.1(5) . . ?
N3 C13 N4 107.5(5) . . ?
N3 C13 I3 124.4(4) . . ?
N4 C13 I3 127.9(4) . . ?
C15 C14 N3 107.4(6) . . ?
C14 C15 N4 107.9(6) . . ?
C16 C17 N6 107.8(5) . . ?
N5 C18 N6 108.3(5) . . ?
N5 C18 I1 125.4(4) . . ?
N6 C18 I1 126.3(4) . . ?
C17 C16 N5 106.5(6) . . ?
C20 C19 N5 109.6(5) . . ?
C18 N6 C17 107.8(5) . . ?
C18 N6 C22 125.3(5) . . ?
C17 N6 C22 126.9(5) . . ?
C18 N5 C16 109.5(5) . . ?
C18 N5 C19 126.3(5) . . ?
C16 N5 C19 124.2(5) . . ?
N4 C21 C24 110.0(7) . . ?
N6 C22 C3 111.4(5) . . ?
C25A C23 N1 115.7(10) . . ?
C25A C23 C25B 16.0(10) . . ?
N1 C23 C25B 99.8(8) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.387
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.151
####################################################################### 
# 
# 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_2bClmix-sr
_database_code_depnum_ccdc_archive 'CCDC 1049819'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H72 Cl3 I6 N12'
_chemical_formula_weight         1756.99

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.993(3)
_cell_length_b                   12.6135(12)
_cell_length_c                   21.963(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.059(2)
_cell_angle_gamma                90.00
_cell_volume                     7853.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.75

_exptl_crystal_description       Needle
_exptl_crystal_colour            COlorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3396
_exptl_absorpt_coefficient_mu    2.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4735
_exptl_absorpt_correction_T_max  0.7873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6916
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6916
_reflns_number_gt                5796
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Ortep 3v.2'

_refine_special_details          SQUEEZE
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.250 -0.005 0.235 1033 369 ' '
2 0.750 -0.032 0.012 1033 369 ' '
_platon_squeeze_details          
;
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1834P)²+312.9927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6916
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   0.592
_refine_ls_restrained_S_all      0.592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.073953(16) 0.98226(3) 0.57140(2) 0.03016(15) Uani 1 1 d . . .
I2 I 0.036783(16) 0.08928(4) 0.37622(2) 0.03376(16) Uani 1 1 d . . .
I3 I 0.064963(17) 0.44404(4) 0.73748(2) 0.03911(17) Uani 1 1 d . . .
C4 C 0.0964(2) 0.3827(5) 0.5522(3) 0.0267(13) Uani 1 1 d . . .
C6 C 0.0657(2) 0.4227(5) 0.4953(3) 0.0288(14) Uani 1 1 d . . .
C3 C 0.1161(2) 0.4496(5) 0.6055(3) 0.0283(14) Uani 1 1 d . . .
C5 C 0.1091(3) 0.2660(6) 0.5574(4) 0.0413(18) Uani 1 1 d . . .
H5A H 0.1000 0.2353 0.5151 0.062 Uiso 1 1 calc R . .
H5B H 0.0929 0.2305 0.5826 0.062 Uiso 1 1 calc R . .
H5C H 0.1425 0.2582 0.5777 0.062 Uiso 1 1 calc R . .
C7 C 0.0573(2) 0.5331(5) 0.4877(3) 0.0262(13) Uani 1 1 d . . .
C8 C 0.0266(3) 0.5772(6) 0.4224(4) 0.0391(17) Uani 1 1 d . . .
H8A H 0.0304 0.5339 0.3884 0.059 Uiso 1 1 calc R . .
H8B H 0.0361 0.6485 0.4176 0.059 Uiso 1 1 calc R . .
H8C H -0.0059 0.5766 0.4202 0.059 Uiso 1 1 calc R . .
C2 C 0.1064(3) 0.5583(5) 0.5996(3) 0.0317(15) Uani 1 1 d . . .
C1 C 0.0762(3) 0.5993(5) 0.5398(4) 0.0310(15) Uani 1 1 d . . .
C9 C 0.0680(3) 0.7179(5) 0.5336(4) 0.0335(15) Uani 1 1 d . . .
H9A H 0.0417 0.7325 0.4949 0.040 Uiso 1 1 calc R . .
H9B H 0.0595 0.7430 0.5701 0.040 Uiso 1 1 calc R . .
C10 C 0.0431(2) 0.3471(5) 0.4393(3) 0.0317(15) Uani 1 1 d . . .
H10A H 0.0326 0.2837 0.4555 0.038 Uiso 1 1 calc R . .
H10B H 0.0158 0.3809 0.4090 0.038 Uiso 1 1 calc R . .
C12 C 0.1477(3) 0.7315(6) 0.5168(4) 0.0411(17) Uani 1 1 d . . .
H12 H 0.1511 0.6612 0.5063 0.049 Uiso 1 1 calc R . .
C13 C 0.1183(2) 0.8796(5) 0.5441(3) 0.0309(14) Uani 1 1 d . . .
C11 C 0.1788(3) 0.8120(7) 0.5214(5) 0.050(2) Uani 1 1 d . . .
H11 H 0.2076 0.8069 0.5140 0.060 Uiso 1 1 calc R . .
C14 C 0.0775(2) 0.2235(6) 0.3762(3) 0.0301(14) Uani 1 1 d . . .
C16 C 0.0938(5) 0.1430(9) 0.2452(5) 0.081(4) Uani 1 1 d . . .
H16A H 0.0616 0.1378 0.2442 0.122 Uiso 1 1 calc R . .
H16B H 0.1012 0.0836 0.2229 0.122 Uiso 1 1 calc R . .
H16C H 0.0980 0.2075 0.2246 0.122 Uiso 1 1 calc R . .
C17 C 0.1260(3) 0.1431(7) 0.3142(4) 0.053(2) Uani 1 1 d . . .
H17A H 0.1244 0.0750 0.3339 0.064 Uiso 1 1 calc R . .
H17B H 0.1583 0.1547 0.3156 0.064 Uiso 1 1 calc R . .
C15 C 0.1326(3) 0.3275(7) 0.3621(4) 0.047(2) Uani 1 1 d . . .
H15 H 0.1571 0.3515 0.3485 0.056 Uiso 1 1 calc R . .
N2 N 0.1115(2) 0.2280(5) 0.3501(3) 0.0407(15) Uani 1 1 d . . .
N1 N 0.07665(19) 0.3175(4) 0.4059(3) 0.0261(11) Uani 1 1 d . . .
N4 N 0.1095(2) 0.7756(4) 0.5309(3) 0.0317(12) Uani 1 1 d . . .
N3 N 0.1605(2) 0.9019(5) 0.5389(3) 0.0374(14) Uani 1 1 d . . .
C19 C 0.1841(3) 1.0085(6) 0.5476(5) 0.047(2) Uani 1 1 d . . .
H19A H 0.1728 1.0516 0.5762 0.056 Uiso 1 1 calc R . .
H19B H 0.2179 0.9998 0.5672 0.056 Uiso 1 1 calc R . .
C20 C 0.1736(3) 1.0628(7) 0.4840(5) 0.057(2) Uani 1 1 d . . .
H20A H 0.1863 1.0219 0.4567 0.086 Uiso 1 1 calc R . .
H20B H 0.1876 1.1320 0.4903 0.086 Uiso 1 1 calc R . .
H20C H 0.1401 1.0693 0.4641 0.086 Uiso 1 1 calc R . .
C18 C 0.1297(4) 0.6335(6) 0.6540(4) 0.058(3) Uani 1 1 d . . .
H18A H 0.1248 0.6089 0.6927 0.087 Uiso 1 1 calc R . .
H18B H 0.1163 0.7029 0.6436 0.087 Uiso 1 1 calc R . .
H18C H 0.1630 0.6365 0.6605 0.087 Uiso 1 1 calc R . .
C21 C 0.1529(3) 0.4062(6) 0.6655(4) 0.0383(17) Uani 1 1 d . . .
H21A H 0.1800 0.3839 0.6539 0.046 Uiso 1 1 calc R . .
H21B H 0.1631 0.4638 0.6962 0.046 Uiso 1 1 calc R . .
N5 N 0.1387(2) 0.3182(5) 0.6978(3) 0.0385(14) Uani 1 1 d . . .
C23 C 0.1421(3) 0.1567(6) 0.7362(4) 0.054(3) Uani 1 1 d . . .
H23 H 0.1501 0.0862 0.7467 0.065 Uiso 1 1 calc R . .
N8 N 0.1047(2) 0.2198(5) 0.7512(3) 0.0440(16) Uani 1 1 d . . .
C22 C 0.1600(3) 0.2164(7) 0.7074(4) 0.047(2) Uani 1 1 d . . .
H22 H 0.1849 0.1975 0.6931 0.056 Uiso 1 1 calc R . .
C24 C 0.1058(2) 0.3165(6) 0.7269(4) 0.0353(16) Uani 1 1 d . . .
C25 C 0.0751(3) 0.1814(7) 0.7890(4) 0.048(2) Uani 1 1 d . . .
H25A H 0.0662 0.1082 0.7780 0.058 Uiso 1 1 calc R . .
H25B H 0.0465 0.2234 0.7788 0.058 Uiso 1 1 calc R . .
C26 C 0.1023(4) 0.1900(9) 0.8607(4) 0.061(3) Uani 1 1 d . . .
H26A H 0.1287 0.1424 0.8715 0.092 Uiso 1 1 calc R . .
H26B H 0.0819 0.1717 0.8849 0.092 Uiso 1 1 calc R . .
H26C H 0.1134 0.2613 0.8707 0.092 Uiso 1 1 calc R . .
C27 C 0.1109(3) 0.3832(6) 0.3971(4) 0.0403(17) Uani 1 1 d . . .
H27 H 0.1177 0.4521 0.4123 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.0000 0.62793(13) 0.7500 0.0129(3) Uani 1 2 d S . .
Cl2 Cl 0.01198(6) 0.12368(12) 0.61798(8) 0.0309(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C13 2.079(7) . ?
I2 C14 2.087(7) . ?
I3 C24 2.079(7) . ?
C4 C6 1.383(10) . ?
C4 C3 1.407(9) . ?
C4 C5 1.516(9) . ?
C6 C7 1.415(9) . ?
C6 C10 1.528(9) . ?
C3 C2 1.399(9) . ?
C3 C21 1.519(10) . ?
C7 C1 1.381(10) . ?
C7 C8 1.533(10) . ?
C2 C1 1.426(11) . ?
C2 C18 1.507(10) . ?
C1 C9 1.514(9) . ?
C9 N4 1.460(9) . ?
C10 N1 1.474(8) . ?
C12 C11 1.362(12) . ?
C12 N4 1.396(9) . ?
C13 N3 1.338(9) . ?
C13 N4 1.351(9) . ?
C11 N3 1.369(10) . ?
C14 N2 1.325(9) . ?
C14 N1 1.358(9) . ?
C16 C17 1.508(15) . ?
C17 N2 1.477(10) . ?
C15 C27 1.355(11) . ?
C15 N2 1.391(10) . ?
N1 C27 1.381(9) . ?
N3 C19 1.502(10) . ?
C19 C20 1.494(13) . ?
C21 N5 1.454(10) . ?
N5 C24 1.340(10) . ?
N5 C22 1.419(10) . ?
C23 C22 1.214(12) . ?
C23 N8 1.500(12) . ?
N8 C24 1.336(10) . ?
N8 C25 1.481(10) . ?
C25 C26 1.521(13) . ?

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
C6 C4 C3 120.5(6) . . ?
C6 C4 C5 119.9(6) . . ?
C3 C4 C5 119.6(6) . . ?
C4 C6 C7 120.4(6) . . ?
C4 C6 C10 119.3(6) . . ?
C7 C6 C10 120.2(6) . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 C21 120.2(6) . . ?
C4 C3 C21 119.7(6) . . ?
C1 C7 C6 119.2(6) . . ?
C1 C7 C8 121.0(6) . . ?
C6 C7 C8 119.8(6) . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 C18 121.0(7) . . ?
C1 C2 C18 119.6(6) . . ?
C7 C1 C2 120.6(6) . . ?
C7 C1 C9 120.8(7) . . ?
C2 C1 C9 118.5(6) . . ?
N4 C9 C1 112.3(6) . . ?
N1 C10 C6 111.3(5) . . ?
C11 C12 N4 106.2(7) . . ?
N3 C13 N4 108.1(6) . . ?
N3 C13 I1 127.2(5) . . ?
N4 C13 I1 124.6(5) . . ?
C12 C11 N3 108.0(7) . . ?
N2 C14 N1 107.9(6) . . ?
N2 C14 I2 124.6(5) . . ?
N1 C14 I2 127.3(5) . . ?
N2 C17 C16 109.5(8) . . ?
C27 C15 N2 107.6(7) . . ?
C14 N2 C15 108.9(6) . . ?
C14 N2 C17 127.0(7) . . ?
C15 N2 C17 124.1(6) . . ?
C14 N1 C27 109.0(6) . . ?
C14 N1 C10 125.7(5) . . ?
C27 N1 C10 125.2(6) . . ?
C13 N4 C12 108.5(6) . . ?
C13 N4 C9 125.8(6) . . ?
C12 N4 C9 125.6(6) . . ?
C13 N3 C11 109.1(6) . . ?
C13 N3 C19 126.7(6) . . ?
C11 N3 C19 124.2(6) . . ?
C20 C19 N3 110.1(7) . . ?
N5 C21 C3 117.0(6) . . ?
C24 N5 C22 106.4(7) . . ?
C24 N5 C21 128.5(6) . . ?
C22 N5 C21 125.0(7) . . ?
C22 C23 N8 105.9(7) . . ?
C24 N8 C25 128.3(7) . . ?
C24 N8 C23 106.2(6) . . ?
C25 N8 C23 125.4(6) . . ?
C23 C22 N5 112.6(8) . . ?
N8 C24 N5 108.8(7) . . ?
N8 C24 I3 124.7(6) . . ?
N5 C24 I3 126.4(5) . . ?
N8 C25 C26 109.9(7) . . ?
C15 C27 N1 106.6(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         5.003
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.180
