# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_H2BPTP
_database_code_depnum_ccdc_archive 'CCDC 1016314'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H50 Br2 Cl6 N8 O27'
_chemical_formula_sum            'C54 H50 Br2 Cl6 N8 O27'
_chemical_formula_weight         1615.54

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'
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'
O O 0.0106 0.0060 '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                   25.816(7)
_cell_length_b                   12.486(3)
_cell_length_c                   20.898(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.361(4)
_cell_angle_gamma                90.00
_cell_volume                     6315(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7258
_cell_measurement_theta_min      2.0789
_cell_measurement_theta_max      27.5049

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'light green'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3272
_exptl_absorpt_coefficient_mu    1.631
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5939
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  MicroMax-007
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1.0
_diffrn_reflns_number            25090
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7103
_reflns_number_gt                5831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1546P)²+32.9473P] 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         7103
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0910
_refine_ls_wR_factor_ref         0.2934
_refine_ls_wR_factor_gt          0.2483
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.17545(3) 0.27380(5) 0.08656(4) 0.0247(2) Uani 1 1 d . . .
Cl1 Cl 0.10831(8) 0.42429(14) 0.18236(10) 0.0287(4) Uani 1 1 d . . .
Cl2 Cl 0.29874(7) 0.39549(13) 0.35737(9) 0.0243(4) Uani 1 1 d . . .
Cl3 Cl 0.44571(8) 0.26570(14) 0.10231(11) 0.0304(4) Uani 1 1 d . . .
O1 O 0.0656(3) 0.5018(6) 0.1700(4) 0.064(2) Uani 1 1 d . . .
O2 O 0.1589(3) 0.4742(7) 0.1888(4) 0.071(2) Uani 1 1 d . . .
O1W O 0.0738(4) 0.6841(7) 0.2471(5) 0.0208(19) Uani 0.50 1 d P . .
O3 O 0.0919(3) 0.3512(6) 0.1252(3) 0.0507(17) Uani 1 1 d . . .
O2W O 0.1107(2) 0.5230(4) 0.3448(3) 0.0311(12) Uani 1 1 d . . .
O4 O 0.1142(3) 0.3660(5) 0.2441(3) 0.0482(17) Uani 1 1 d . . .
O5 O 0.2788(2) 0.4060(5) 0.4129(3) 0.0324(12) Uani 1 1 d . . .
O6 O 0.2771(3) 0.4803(5) 0.3093(3) 0.0496(17) Uani 1 1 d . . .
O7 O 0.3584(2) 0.3996(5) 0.3834(3) 0.0361(13) Uani 1 1 d . . .
O8 O 0.2807(2) 0.2939(4) 0.3231(3) 0.0355(13) Uani 1 1 d . . .
O9 O 0.3890(2) 0.2620(5) 0.0996(3) 0.0396(14) Uani 1 1 d . . .
O10 O 0.4761(3) 0.3266(6) 0.1627(4) 0.065(2) Uani 1 1 d . . .
O11 O 0.4494(3) 0.3174(6) 0.0446(4) 0.064(2) Uani 1 1 d . . .
O12 O 0.4665(3) 0.1600(5) 0.1072(4) 0.055(2) Uani 1 1 d . . .
N1 N 0.0885(2) 0.0507(4) 0.1872(3) 0.0192(11) Uani 1 1 d . . .
N2 N 0.3007(2) -0.0261(4) 0.5044(3) 0.0226(12) Uani 1 1 d . . .
N3 N 0.3793(3) 0.1472(6) 0.4287(4) 0.0374(16) Uani 1 1 d . . .
H1 H 0.3547 0.1697 0.3902 0.045 Uiso 1 1 calc R . .
N4 N 0.2005(4) -0.1942(7) 0.5481(4) 0.0459(19) Uani 1 1 d . . .
H4 H 0.1714 -0.1954 0.5104 0.055 Uiso 1 1 calc R . .
C1 C -0.1068(3) 0.2062(5) 0.0988(4) 0.0253(15) Uani 1 1 d . . .
C2 C -0.0600(3) 0.2361(6) 0.1526(4) 0.0251(15) Uani 1 1 d . . .
H2 H -0.0623 0.2887 0.1843 0.030 Uiso 1 1 calc R . .
C3 C -0.0096(3) 0.1883(6) 0.1598(4) 0.0271(16) Uani 1 1 d . . .
H3 H 0.0227 0.2096 0.1961 0.033 Uiso 1 1 calc R . .
C4 C -0.0062(3) 0.1105(5) 0.1149(4) 0.0225(14) Uani 1 1 d . . .
C5 C -0.0540(3) 0.0801(5) 0.0607(3) 0.0210(14) Uani 1 1 d . . .
H5 H -0.0518 0.0265 0.0295 0.025 Uiso 1 1 calc R . .
C6 C -0.1046(3) 0.1278(6) 0.0526(3) 0.0227(14) Uani 1 1 d . . .
H6 H -0.1370 0.1073 0.0161 0.027 Uiso 1 1 calc R . .
C7 C 0.0483(3) 0.0609(6) 0.1176(4) 0.0261(15) Uani 1 1 d . . .
H7A H 0.0410 -0.0110 0.0964 0.031 Uiso 1 1 calc R . .
H7B H 0.0646 0.1055 0.0903 0.031 Uiso 1 1 calc R . .
C8 C 0.1289(3) 0.1250(5) 0.2120(4) 0.0225(14) Uani 1 1 d . . .
H8 H 0.1296 0.1858 0.1849 0.027 Uiso 1 1 calc R . .
C9 C 0.1685(3) 0.1143(5) 0.2747(3) 0.0202(14) Uani 1 1 d . . .
H9 H 0.1964 0.1673 0.2908 0.024 Uiso 1 1 calc R . .
C10 C 0.1683(3) 0.0260(5) 0.3155(4) 0.0210(14) Uani 1 1 d . . .
C11 C 0.1257(3) -0.0477(6) 0.2904(4) 0.0255(15) Uani 1 1 d . . .
H11 H 0.1235 -0.1079 0.3172 0.031 Uiso 1 1 calc R . .
C12 C 0.0863(3) -0.0330(6) 0.2263(4) 0.0282(16) Uani 1 1 d . . .
H12 H 0.0572 -0.0834 0.2097 0.034 Uiso 1 1 calc R . .
C13 C 0.2137(3) 0.0091(5) 0.3817(3) 0.0195(13) Uani 1 1 d . . .
C14 C 0.2667(3) 0.0505(5) 0.3926(4) 0.0207(14) Uani 1 1 d . . .
H14 H 0.2742 0.0908 0.3582 0.025 Uiso 1 1 calc R . .
C15 C 0.3080(3) 0.0308(5) 0.4553(3) 0.0200(13) Uani 1 1 d . . .
C16 C 0.2499(3) -0.0662(5) 0.4942(3) 0.0221(14) Uani 1 1 d . . .
C17 C 0.2058(3) -0.0493(5) 0.4353(4) 0.0219(14) Uani 1 1 d . . .
H17 H 0.1703 -0.0767 0.4307 0.026 Uiso 1 1 calc R . .
C18 C 0.3650(3) 0.0747(5) 0.4710(4) 0.0202(14) Uani 1 1 d . . .
C19 C 0.4034(3) 0.0421(5) 0.5290(3) 0.0162(12) Uani 1 1 d . . .
H19 H 0.3929 -0.0072 0.5568 0.019 Uiso 1 1 calc R . .
C20 C 0.4553(3) 0.0748(6) 0.5498(4) 0.0292(16) Uani 1 1 d . . .
H20 H 0.4808 0.0512 0.5923 0.035 Uiso 1 1 calc R . .
C21 C 0.4722(3) 0.1444(6) 0.5085(4) 0.0257(15) Uani 1 1 d . . .
H21 H 0.5098 0.1652 0.5211 0.031 Uiso 1 1 calc R . .
C22 C 0.4336(3) 0.1820(6) 0.4497(4) 0.0258(15) Uani 1 1 d . . .
H22 H 0.4442 0.2329 0.4228 0.031 Uiso 1 1 calc R . .
C23 C 0.2459(3) -0.1311(5) 0.5522(4) 0.0210(14) Uani 1 1 d . . .
C24 C 0.2889(3) -0.1282(5) 0.6110(3) 0.0174(13) Uani 1 1 d . . .
H24 H 0.3196 -0.0843 0.6134 0.021 Uiso 1 1 calc R . .
C25 C 0.2908(4) -0.1844(7) 0.6669(4) 0.0357(19) Uani 1 1 d . . .
H25 H 0.3217 -0.1788 0.7080 0.043 Uiso 1 1 calc R . .
C26 C 0.2468(4) -0.2505(6) 0.6631(4) 0.0322(18) Uani 1 1 d . . .
H26 H 0.2479 -0.2924 0.7014 0.039 Uiso 1 1 calc R . .
C27 C 0.2017(4) -0.2558(6) 0.6045(5) 0.0337(19) Uani 1 1 d . . .
H27 H 0.1714 -0.3009 0.6021 0.040 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
Br1 C1 1.899(7) . ?
Cl1 O2 1.412(7) . ?
Cl1 O1 1.421(7) . ?
Cl1 O4 1.443(6) . ?
Cl1 O3 1.445(7) . ?
Cl2 O5 1.430(5) . ?
Cl2 O6 1.433(6) . ?
Cl2 O7 1.446(6) . ?
Cl2 O8 1.452(6) . ?
Cl3 O11 1.400(7) . ?
Cl3 O12 1.415(6) . ?
Cl3 O9 1.446(6) . ?
Cl3 O10 1.448(7) . ?
N1 C12 1.340(9) . ?
N1 C8 1.358(9) . ?
N1 C7 1.469(9) . ?
N2 C15 1.314(9) . ?
N2 C16 1.349(9) . ?
N3 C22 1.385(10) . ?
N3 C18 1.403(10) . ?
N3 H1 0.8800 . ?
N4 C23 1.389(10) . ?
N4 C27 1.400(11) . ?
N4 H4 0.8800 . ?
C1 C2 1.384(11) . ?
C1 C6 1.391(10) . ?
C2 C3 1.390(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(10) . ?
C4 C7 1.519(9) . ?
C5 C6 1.390(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.359(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(10) . ?
C10 C13 1.486(10) . ?
C11 C12 1.382(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.405(9) . ?
C13 C17 1.410(9) . ?
C14 C15 1.394(10) . ?
C14 H14 0.9500 . ?
C15 C18 1.494(9) . ?
C16 C17 1.371(10) . ?
C16 C23 1.492(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.334(10) . ?
C19 C20 1.321(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(11) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.339(10) . ?
C24 C25 1.350(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.365(13) . ?
C26 H26 0.9500 . ?
C27 H27 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
O2 Cl1 O1 110.5(5) . . ?
O2 Cl1 O4 109.4(4) . . ?
O1 Cl1 O4 109.9(5) . . ?
O2 Cl1 O3 110.7(5) . . ?
O1 Cl1 O3 107.1(4) . . ?
O4 Cl1 O3 109.2(4) . . ?
O5 Cl2 O6 109.8(4) . . ?
O5 Cl2 O7 109.2(3) . . ?
O6 Cl2 O7 110.0(4) . . ?
O5 Cl2 O8 109.7(3) . . ?
O6 Cl2 O8 108.7(4) . . ?
O7 Cl2 O8 109.5(4) . . ?
O11 Cl3 O12 110.7(4) . . ?
O11 Cl3 O9 110.6(4) . . ?
O12 Cl3 O9 109.1(4) . . ?
O11 Cl3 O10 109.3(5) . . ?
O12 Cl3 O10 110.4(5) . . ?
O9 Cl3 O10 106.6(4) . . ?
C12 N1 C8 119.4(6) . . ?
C12 N1 C7 120.5(6) . . ?
C8 N1 C7 120.2(6) . . ?
C15 N2 C16 118.3(6) . . ?
C22 N3 C18 117.6(7) . . ?
C22 N3 H1 121.2 . . ?
C18 N3 H1 121.2 . . ?
C23 N4 C27 119.3(8) . . ?
C23 N4 H4 120.4 . . ?
C27 N4 H4 120.4 . . ?
C2 C1 C6 121.2(7) . . ?
C2 C1 Br1 120.0(5) . . ?
C6 C1 Br1 118.8(6) . . ?
C1 C2 C3 119.4(7) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.6(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.5(6) . . ?
C3 C4 C7 122.8(7) . . ?
C5 C4 C7 117.5(6) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.7(7) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C4 113.4(6) . . ?
N1 C7 H7A 108.9 . . ?
C4 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 121.3(6) . . ?
N1 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 120.4(7) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 117.6(7) . . ?
C11 C10 C13 121.5(6) . . ?
C9 C10 C13 120.8(6) . . ?
C12 C11 C10 119.7(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C11 121.5(7) . . ?
N1 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C17 117.7(6) . . ?
C14 C13 C10 120.5(6) . . ?
C17 C13 C10 121.8(6) . . ?
C15 C14 C13 118.0(6) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
N2 C15 C14 123.9(7) . . ?
N2 C15 C18 115.2(6) . . ?
C14 C15 C18 120.9(6) . . ?
N2 C16 C17 122.9(6) . . ?
N2 C16 C23 114.3(6) . . ?
C17 C16 C23 122.9(6) . . ?
C16 C17 C13 119.1(6) . . ?
C16 C17 H17 120.4 . . ?
C13 C17 H17 120.4 . . ?
C19 C18 N3 119.5(6) . . ?
C19 C18 C15 116.8(6) . . ?
N3 C18 C15 123.6(6) . . ?
C20 C19 C18 123.6(7) . . ?
C20 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
C19 C20 C21 119.3(7) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 118.8(7) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 N3 121.2(7) . . ?
C21 C22 H22 119.4 . . ?
N3 C22 H22 119.4 . . ?
C24 C23 N4 119.0(6) . . ?
C24 C23 C16 117.5(6) . . ?
N4 C23 C16 123.5(7) . . ?
C23 C24 C25 123.2(7) . . ?
C23 C24 H24 118.4 . . ?
C25 C24 H24 118.4 . . ?
C24 C25 C26 118.6(8) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C27 C26 C25 120.5(7) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 N4 119.3(8) . . ?
C26 C27 H27 120.3 . . ?
N4 C27 H27 120.3 . . ?

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
C6 C1 C2 C3 1.2(11) . . . . ?
Br1 C1 C2 C3 -178.0(6) . . . . ?
C1 C2 C3 C4 -1.3(11) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C2 C3 C4 C7 175.9(7) . . . . ?
C3 C4 C5 C6 -0.3(10) . . . . ?
C7 C4 C5 C6 -175.6(6) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C2 C1 C6 C5 -0.7(10) . . . . ?
Br1 C1 C6 C5 178.6(5) . . . . ?
C12 N1 C7 C4 83.1(8) . . . . ?
C8 N1 C7 C4 -98.4(7) . . . . ?
C3 C4 C7 N1 34.1(10) . . . . ?
C5 C4 C7 N1 -150.7(6) . . . . ?
C12 N1 C8 C9 2.3(10) . . . . ?
C7 N1 C8 C9 -176.2(6) . . . . ?
N1 C8 C9 C10 -0.2(10) . . . . ?
C8 C9 C10 C11 -1.8(9) . . . . ?
C8 C9 C10 C13 175.2(6) . . . . ?
C9 C10 C11 C12 1.6(10) . . . . ?
C13 C10 C11 C12 -175.3(6) . . . . ?
C8 N1 C12 C11 -2.4(10) . . . . ?
C7 N1 C12 C11 176.0(6) . . . . ?
C10 C11 C12 N1 0.5(11) . . . . ?
C11 C10 C13 C14 150.3(7) . . . . ?
C9 C10 C13 C14 -26.5(9) . . . . ?
C11 C10 C13 C17 -29.0(10) . . . . ?
C9 C10 C13 C17 154.2(6) . . . . ?
C17 C13 C14 C15 0.3(9) . . . . ?
C10 C13 C14 C15 -179.0(6) . . . . ?
C16 N2 C15 C14 -1.4(10) . . . . ?
C16 N2 C15 C18 178.5(5) . . . . ?
C13 C14 C15 N2 1.5(10) . . . . ?
C13 C14 C15 C18 -178.4(6) . . . . ?
C15 N2 C16 C17 -0.6(10) . . . . ?
C15 N2 C16 C23 179.0(6) . . . . ?
N2 C16 C17 C13 2.3(10) . . . . ?
C23 C16 C17 C13 -177.2(6) . . . . ?
C14 C13 C17 C16 -2.1(9) . . . . ?
C10 C13 C17 C16 177.2(6) . . . . ?
C22 N3 C18 C19 -0.1(10) . . . . ?
C22 N3 C18 C15 179.6(6) . . . . ?
N2 C15 C18 C19 7.3(9) . . . . ?
C14 C15 C18 C19 -172.7(6) . . . . ?
N2 C15 C18 N3 -172.4(6) . . . . ?
C14 C15 C18 N3 7.6(10) . . . . ?
N3 C18 C19 C20 0.3(10) . . . . ?
C15 C18 C19 C20 -179.4(6) . . . . ?
C18 C19 C20 C21 -2.3(11) . . . . ?
C19 C20 C21 C22 4.0(11) . . . . ?
C20 C21 C22 N3 -4.0(11) . . . . ?
C18 N3 C22 C21 2.0(10) . . . . ?
C27 N4 C23 C24 -2.2(10) . . . . ?
C27 N4 C23 C16 177.3(7) . . . . ?
N2 C16 C23 C24 10.8(8) . . . . ?
C17 C16 C23 C24 -169.6(6) . . . . ?
N2 C16 C23 N4 -168.7(6) . . . . ?
C17 C16 C23 N4 10.9(10) . . . . ?
N4 C23 C24 C25 0.5(10) . . . . ?
C16 C23 C24 C25 -179.0(6) . . . . ?
C23 C24 C25 C26 1.6(11) . . . . ?
C24 C25 C26 C27 -2.0(11) . . . . ?
C25 C26 C27 N4 0.4(12) . . . . ?
C23 N4 C27 C26 1.7(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.894
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.229
####################################################################### 
# 
# 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_BPTP-1
_database_code_depnum_ccdc_archive 'CCDC 1016315'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Br Cl N4 O4'
_chemical_formula_sum            'C27 H20 Br Cl N4 O4'
_chemical_formula_weight         579.83

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'
Br Br -0.2901 2.4595 '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'
Cl Cl 0.1484 0.1585 '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                   9.458(4)
_cell_length_b                   11.123(4)
_cell_length_c                   13.733(6)
_cell_angle_alpha                110.053(16)
_cell_angle_beta                 96.92(3)
_cell_angle_gamma                102.05(2)
_cell_volume                     1297.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3315
_cell_measurement_theta_min      2.0551
_cell_measurement_theta_max      27.4700

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    1.727
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Saturn724
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1.0
_diffrn_reflns_number            11407
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             5855
_reflns_number_gt                1942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1998P)²+0.0000P] 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         5855
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.3493
_refine_ls_wR_factor_gt          0.2513
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      0.884
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.00618(17) 0.80029(9) 0.17586(9) 0.1424(7) Uani 1 1 d . . .
Cl1 Cl 0.3348(3) 0.1842(2) 0.09459(18) 0.0960(7) Uani 1 1 d . . .
O1 O 0.378(3) 0.2886(12) 0.104(2) 0.50(2) Uani 1 1 d . . .
O2 O 0.4080(17) 0.1090(18) 0.0360(12) 0.279(7) Uani 1 1 d . . .
O3 O 0.359(3) 0.179(3) 0.1791(13) 0.453(19) Uani 1 1 d . . .
O4 O 0.1974(14) 0.1320(17) 0.0417(16) 0.313(10) Uani 1 1 d . . .
N1 N -0.1539(7) 0.1668(5) 0.1635(4) 0.0749(15) Uani 1 1 d . . .
N2 N -0.3122(8) -0.0226(6) 0.5825(4) 0.0888(18) Uani 1 1 d . . .
N3 N -0.1589(10) -0.2839(7) 0.4405(6) 0.114(2) Uani 1 1 d . . .
N4 N -0.4229(9) 0.2844(9) 0.6611(6) 0.111(2) Uani 1 1 d . . .
C1 C -0.0416(9) 0.6153(7) 0.1442(6) 0.0783(19) Uani 1 1 d . . .
C2 C 0.0511(10) 0.5673(8) 0.1952(7) 0.104(3) Uani 1 1 d . . .
H2 H 0.1327 0.6252 0.2473 0.124 Uiso 1 1 calc R . .
C3 C 0.0231(10) 0.4316(8) 0.1689(7) 0.101(3) Uani 1 1 d . . .
H3 H 0.0879 0.3981 0.2020 0.121 Uiso 1 1 calc R . .
C4 C -0.0974(7) 0.3475(6) 0.0958(5) 0.0681(16) Uani 1 1 d . . .
C5 C -0.1925(10) 0.4001(9) 0.0479(7) 0.097(2) Uani 1 1 d . . .
H5 H -0.2780 0.3435 -0.0006 0.117 Uiso 1 1 calc R . .
C6 C -0.1625(10) 0.5335(9) 0.0707(7) 0.099(3) Uani 1 1 d . . .
H6 H -0.2247 0.5674 0.0360 0.119 Uiso 1 1 calc R . .
C7 C -0.1293(11) 0.2004(7) 0.0676(6) 0.095(2) Uani 1 1 d . . .
H7A H -0.0470 0.1696 0.0422 0.114 Uiso 1 1 calc R . .
H7B H -0.2167 0.1554 0.0112 0.114 Uiso 1 1 calc R . .
C8 C -0.0567(8) 0.1186(7) 0.2082(5) 0.0762(18) Uani 1 1 d . . .
H8 H 0.0265 0.1057 0.1807 0.091 Uiso 1 1 calc R . .
C9 C -0.0807(9) 0.0890(6) 0.2936(5) 0.0748(18) Uani 1 1 d . . .
H9 H -0.0127 0.0554 0.3236 0.090 Uiso 1 1 calc R . .
C10 C -0.1983(8) 0.1060(6) 0.3367(5) 0.0660(16) Uani 1 1 d . . .
C11 C -0.2970(8) 0.1597(8) 0.2903(7) 0.086(2) Uani 1 1 d . . .
H11 H -0.3795 0.1743 0.3183 0.103 Uiso 1 1 calc R . .
C12 C -0.2729(10) 0.1902(9) 0.2053(7) 0.101(3) Uani 1 1 d . . .
H12 H -0.3376 0.2270 0.1758 0.121 Uiso 1 1 calc R . .
C13 C -0.2345(8) 0.0648(6) 0.4253(5) 0.0703(16) Uani 1 1 d . . .
C14 C -0.2081(8) -0.0514(7) 0.4295(5) 0.0732(17) Uani 1 1 d . . .
H14 H -0.1610 -0.1002 0.3807 0.088 Uiso 1 1 calc R . .
C15 C -0.2521(8) -0.0937(7) 0.5067(5) 0.0772(18) Uani 1 1 d . . .
C16 C -0.3333(9) 0.0907(8) 0.5812(5) 0.085(2) Uani 1 1 d . . .
C17 C -0.2977(8) 0.1388(7) 0.5037(6) 0.0811(19) Uani 1 1 d . . .
H17 H -0.3155 0.2181 0.5041 0.097 Uiso 1 1 calc R . .
C18 C -0.2357(9) -0.2229(8) 0.5095(6) 0.091(2) Uani 1 1 d . . .
C19 C -0.2981(11) -0.2774(10) 0.5773(7) 0.111(3) Uani 1 1 d . . .
H19 H -0.3494 -0.2320 0.6246 0.133 Uiso 1 1 calc R . .
C20 C -0.2825(14) -0.3984(13) 0.5731(10) 0.138(4) Uani 1 1 d . . .
H20 H -0.3244 -0.4377 0.6165 0.166 Uiso 1 1 calc R . .
C21 C -0.2043(15) -0.4600(12) 0.5043(12) 0.145(4) Uani 1 1 d . . .
H21 H -0.1862 -0.5395 0.5031 0.173 Uiso 1 1 calc R . .
C22 C -0.1532(15) -0.4043(11) 0.4377(10) 0.146(4) Uani 1 1 d . . .
H22 H -0.1105 -0.4535 0.3858 0.175 Uiso 1 1 calc R . .
C23 C -0.3991(8) 0.1719(10) 0.6673(5) 0.091(2) Uani 1 1 d . . .
C24 C -0.4342(11) 0.1276(11) 0.7455(6) 0.127(4) Uani 1 1 d . . .
H24 H -0.4184 0.0490 0.7486 0.152 Uiso 1 1 calc R . .
C25 C -0.4976(12) 0.213(2) 0.8225(7) 0.167(8) Uani 1 1 d . . .
H25 H -0.5157 0.1935 0.8812 0.200 Uiso 1 1 calc R . .
C26 C -0.5306(17) 0.318(2) 0.8122(14) 0.184(8) Uani 1 1 d . . .
H26 H -0.5827 0.3658 0.8574 0.221 Uiso 1 1 calc R . .
C27 C -0.4871(12) 0.3544(13) 0.7349(9) 0.138(4) Uani 1 1 d . . .
H27 H -0.5021 0.4332 0.7320 0.166 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
Br1 C1 1.891(7) . ?
Cl1 O1 1.106(15) . ?
Cl1 O3 1.179(12) . ?
Cl1 O4 1.313(12) . ?
Cl1 O2 1.319(13) . ?
N1 C8 1.344(8) . ?
N1 C12 1.356(10) . ?
N1 C7 1.517(8) . ?
N2 C16 1.322(10) . ?
N2 C15 1.341(10) . ?
N3 C22 1.339(11) . ?
N3 C18 1.348(11) . ?
N4 C27 1.344(13) . ?
N4 C23 1.344(12) . ?
C1 C6 1.346(11) . ?
C1 C2 1.359(11) . ?
C2 C3 1.384(11) . ?
C3 C4 1.348(10) . ?
C4 C5 1.388(9) . ?
C4 C7 1.500(10) . ?
C5 C6 1.366(11) . ?
C8 C9 1.355(9) . ?
C9 C10 1.339(9) . ?
C10 C11 1.409(9) . ?
C10 C13 1.491(8) . ?
C11 C12 1.354(11) . ?
C13 C14 1.386(9) . ?
C13 C17 1.395(10) . ?
C14 C15 1.373(9) . ?
C15 C18 1.489(11) . ?
C16 C17 1.392(10) . ?
C16 C23 1.510(11) . ?
C18 C19 1.397(11) . ?
C19 C20 1.368(14) . ?
C20 C21 1.358(17) . ?
C21 C22 1.351(16) . ?
C23 C24 1.374(12) . ?
C24 C25 1.444(18) . ?
C25 C26 1.32(2) . ?
C26 C27 1.34(2) . ?

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
O1 Cl1 O3 107.9(19) . . ?
O1 Cl1 O4 112.8(16) . . ?
O3 Cl1 O4 116.1(16) . . ?
O1 Cl1 O2 109.9(19) . . ?
O3 Cl1 O2 106.2(12) . . ?
O4 Cl1 O2 103.6(11) . . ?
C8 N1 C12 120.6(6) . . ?
C8 N1 C7 120.4(6) . . ?
C12 N1 C7 118.9(6) . . ?
C16 N2 C15 118.8(6) . . ?
C22 N3 C18 115.0(8) . . ?
C27 N4 C23 117.3(10) . . ?
C6 C1 C2 121.2(7) . . ?
C6 C1 Br1 120.4(6) . . ?
C2 C1 Br1 118.4(6) . . ?
C1 C2 C3 119.5(8) . . ?
C4 C3 C2 120.5(7) . . ?
C3 C4 C5 118.5(6) . . ?
C3 C4 C7 120.9(6) . . ?
C5 C4 C7 120.6(7) . . ?
C6 C5 C4 121.1(7) . . ?
C1 C6 C5 119.1(6) . . ?
C4 C7 N1 110.4(6) . . ?
N1 C8 C9 119.6(7) . . ?
C10 C9 C8 122.7(6) . . ?
C9 C10 C11 116.8(6) . . ?
C9 C10 C13 124.2(6) . . ?
C11 C10 C13 118.9(6) . . ?
C12 C11 C10 120.6(7) . . ?
C11 C12 N1 119.6(6) . . ?
C14 C13 C17 118.5(6) . . ?
C14 C13 C10 119.7(6) . . ?
C17 C13 C10 121.8(6) . . ?
C15 C14 C13 119.2(7) . . ?
N2 C15 C14 122.4(7) . . ?
N2 C15 C18 116.6(6) . . ?
C14 C15 C18 121.0(7) . . ?
N2 C16 C17 122.8(7) . . ?
N2 C16 C23 118.9(7) . . ?
C17 C16 C23 118.2(8) . . ?
C16 C17 C13 118.1(7) . . ?
N3 C18 C19 122.8(8) . . ?
N3 C18 C15 115.0(6) . . ?
C19 C18 C15 122.2(9) . . ?
C20 C19 C18 119.0(11) . . ?
C21 C20 C19 118.5(10) . . ?
C22 C21 C20 119.1(10) . . ?
N3 C22 C21 125.2(11) . . ?
N4 C23 C24 123.5(9) . . ?
N4 C23 C16 117.0(7) . . ?
C24 C23 C16 119.5(10) . . ?
C23 C24 C25 114.3(12) . . ?
C26 C25 C24 122.1(14) . . ?
C25 C26 C27 118.1(14) . . ?
C26 C27 N4 124.3(15) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.146
####################################################################### 
# 
# 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_BPTP-2
_database_code_depnum_ccdc_archive 'CCDC 1016316'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Br Cl N4 O4'
_chemical_formula_sum            'C27 H20 Br Cl N4 O4'
_chemical_formula_weight         579.83

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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.583(2)
_cell_length_b                   9.614(2)
_cell_length_c                   26.703(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.570(7)
_cell_angle_gamma                90.00
_cell_volume                     2418.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3320
_cell_measurement_theta_min      2.3277
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       block
_exptl_crystal_colour            Yellowish
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    1.854
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8864
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Saturn724
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1.0
_diffrn_reflns_number            19009
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5387
_reflns_number_gt                4417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1000P)²+0.0000P] 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         5387
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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
Br1 Br 0.92655(3) 0.62918(3) 0.438872(9) 0.05215(12) Uani 1 1 d . . .
Cl1 Cl 0.21882(7) 0.35062(7) 0.26772(3) 0.05578(17) Uani 1 1 d . . .
O1 O 0.2874(4) 0.3688(5) 0.22711(17) 0.1663(19) Uani 1 1 d . . .
O2 O 0.3000(4) 0.2722(4) 0.30550(14) 0.1471(14) Uani 1 1 d . . .
O3 O 0.1894(4) 0.4810(3) 0.28820(14) 0.1337(12) Uani 1 1 d . . .
O4 O 0.0891(3) 0.2829(3) 0.25172(13) 0.1239(12) Uani 1 1 d . . .
N1 N 0.6645(2) 0.33830(18) 0.20332(6) 0.0397(4) Uani 1 1 d . . .
N2 N 0.68237(18) 0.60831(16) -0.03980(6) 0.0353(4) Uani 1 1 d . . .
N3 N 0.41247(19) 0.83165(19) -0.00693(7) 0.0413(4) Uani 1 1 d . . .
N4 N 0.93539(19) 0.32931(19) -0.03633(7) 0.0391(4) Uani 1 1 d . . .
C1 C 0.8397(2) 0.5226(2) 0.38155(8) 0.0416(5) Uani 1 1 d . . .
C2 C 0.7374(2) 0.4246(2) 0.38645(8) 0.0445(5) Uani 1 1 d . . .
H2 H 0.7100 0.4090 0.4184 0.053 Uiso 1 1 calc R . .
C3 C 0.6759(2) 0.3495(2) 0.34376(8) 0.0434(5) Uani 1 1 d . . .
H3 H 0.6038 0.2835 0.3464 0.052 Uiso 1 1 calc R . .
C4 C 0.7178(3) 0.3692(2) 0.29760(8) 0.0399(5) Uani 1 1 d . . .
C5 C 0.8207(3) 0.4676(3) 0.29379(9) 0.0591(7) Uani 1 1 d . . .
H5 H 0.8495 0.4826 0.2620 0.071 Uiso 1 1 calc R . .
C6 C 0.8823(3) 0.5446(3) 0.33613(10) 0.0588(7) Uani 1 1 d . . .
H6 H 0.9533 0.6118 0.3335 0.071 Uiso 1 1 calc R . .
C7 C 0.6537(3) 0.2763(2) 0.25365(8) 0.0474(5) Uani 1 1 d . . .
H7A H 0.7031 0.1854 0.2572 0.057 Uiso 1 1 calc R . .
H7B H 0.5526 0.2595 0.2550 0.057 Uiso 1 1 calc R . .
C8 C 0.5638(2) 0.4273(2) 0.18116(8) 0.0444(5) Uani 1 1 d . . .
H8 H 0.4864 0.4484 0.1976 0.053 Uiso 1 1 calc R . .
C9 C 0.5708(2) 0.4879(2) 0.13546(8) 0.0408(5) Uani 1 1 d . . .
H9 H 0.4983 0.5502 0.1203 0.049 Uiso 1 1 calc R . .
C10 C 0.6846(2) 0.45840(19) 0.11082(7) 0.0338(4) Uani 1 1 d . . .
C11 C 0.7883(2) 0.3685(2) 0.13569(9) 0.0414(5) Uani 1 1 d . . .
H11 H 0.8688 0.3480 0.1209 0.050 Uiso 1 1 calc R . .
C12 C 0.7759(2) 0.3094(2) 0.18110(8) 0.0440(5) Uani 1 1 d . . .
H12 H 0.8471 0.2470 0.1972 0.053 Uiso 1 1 calc R . .
C13 C 0.6886(2) 0.51559(19) 0.05953(7) 0.0328(4) Uani 1 1 d . . .
C14 C 0.6055(2) 0.62919(19) 0.04025(8) 0.0360(4) Uani 1 1 d . . .
H14 H 0.5507 0.6775 0.0609 0.043 Uiso 1 1 calc R . .
C15 C 0.6041(2) 0.6707(2) -0.00982(8) 0.0341(4) Uani 1 1 d . . .
C16 C 0.7662(2) 0.50143(19) -0.02096(7) 0.0336(4) Uani 1 1 d . . .
C17 C 0.7711(2) 0.45145(19) 0.02822(7) 0.0343(4) Uani 1 1 d . . .
H17 H 0.8300 0.3746 0.0403 0.041 Uiso 1 1 calc R . .
C18 C 0.5087(2) 0.78483(19) -0.03372(7) 0.0348(4) Uani 1 1 d . . .
C19 C 0.5182(2) 0.8349(2) -0.08147(8) 0.0405(5) Uani 1 1 d . . .
H19 H 0.5896 0.8019 -0.0989 0.049 Uiso 1 1 calc R . .
C20 C 0.4212(3) 0.9346(2) -0.10352(9) 0.0479(5) Uani 1 1 d . . .
H20 H 0.4246 0.9699 -0.1365 0.057 Uiso 1 1 calc R . .
C21 C 0.3208(3) 0.9811(2) -0.07726(9) 0.0495(5) Uani 1 1 d . . .
H21 H 0.2524 1.0483 -0.0917 0.059 Uiso 1 1 calc R . .
C22 C 0.3214(3) 0.9277(3) -0.02894(9) 0.0493(5) Uani 1 1 d . . .
H22 H 0.2527 0.9617 -0.0105 0.059 Uiso 1 1 calc R . .
C23 C 0.8523(2) 0.4354(2) -0.05551(7) 0.0355(4) Uani 1 1 d . . .
C24 C 0.8460(2) 0.4838(2) -0.10518(8) 0.0419(5) Uani 1 1 d . . .
H24 H 0.7871 0.5603 -0.1177 0.050 Uiso 1 1 calc R . .
C25 C 0.9286(3) 0.4168(3) -0.13594(9) 0.0469(5) Uani 1 1 d . . .
H25 H 0.9255 0.4461 -0.1701 0.056 Uiso 1 1 calc R . .
C26 C 1.0134(2) 0.3092(2) -0.11645(9) 0.0468(5) Uani 1 1 d . . .
H26 H 1.0708 0.2626 -0.1366 0.056 Uiso 1 1 calc R . .
C27 C 1.0146(2) 0.2688(2) -0.06662(9) 0.0449(5) Uani 1 1 d . . .
H27 H 1.0748 0.1940 -0.0532 0.054 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
Br1 C1 1.902(2) . ?
Cl1 O1 1.379(3) . ?
Cl1 O2 1.379(3) . ?
Cl1 O4 1.399(2) . ?
Cl1 O3 1.416(3) . ?
N1 C8 1.343(3) . ?
N1 C12 1.343(3) . ?
N1 C7 1.491(3) . ?
N2 C15 1.336(3) . ?
N2 C16 1.344(2) . ?
N3 C22 1.331(3) . ?
N3 C18 1.344(3) . ?
N4 C23 1.337(3) . ?
N4 C27 1.339(3) . ?
C1 C6 1.365(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 C13 1.483(3) . ?
C11 C12 1.364(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 C17 1.396(3) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C18 1.494(3) . ?
C16 C17 1.391(3) . ?
C16 C23 1.488(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.397(3) . ?
C24 C25 1.399(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.358(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
O1 Cl1 O2 111.0(2) . . ?
O1 Cl1 O4 110.1(2) . . ?
O2 Cl1 O4 108.6(2) . . ?
O1 Cl1 O3 110.4(2) . . ?
O2 Cl1 O3 109.1(2) . . ?
O4 Cl1 O3 107.53(18) . . ?
C8 N1 C12 120.16(18) . . ?
C8 N1 C7 119.29(18) . . ?
C12 N1 C7 120.51(19) . . ?
C15 N2 C16 118.80(17) . . ?
C22 N3 C18 117.10(19) . . ?
C23 N4 C27 117.64(18) . . ?
C6 C1 C2 121.5(2) . . ?
C6 C1 Br1 118.26(19) . . ?
C2 C1 Br1 120.27(16) . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 C7 118.0(2) . . ?
C5 C4 C7 122.7(2) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C4 112.22(17) . . ?
N1 C7 H7A 109.2 . . ?
C4 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C4 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 121.1(2) . . ?
N1 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 116.81(19) . . ?
C11 C10 C13 122.29(18) . . ?
C9 C10 C13 120.83(18) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N1 C12 C11 120.9(2) . . ?
N1 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C17 118.24(18) . . ?
C14 C13 C10 121.48(17) . . ?
C17 C13 C10 120.20(17) . . ?
C15 C14 C13 118.91(19) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N2 C15 C14 122.63(19) . . ?
N2 C15 C18 116.14(17) . . ?
C14 C15 C18 121.18(18) . . ?
N2 C16 C17 122.15(17) . . ?
N2 C16 C23 117.09(17) . . ?
C17 C16 C23 120.74(18) . . ?
C16 C17 C13 119.22(18) . . ?
C16 C17 H17 120.4 . . ?
C13 C17 H17 120.4 . . ?
N3 C18 C19 122.81(19) . . ?
N3 C18 C15 116.38(18) . . ?
C19 C18 C15 120.78(18) . . ?
C18 C19 C20 118.7(2) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 118.2(2) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
N3 C22 C21 123.9(2) . . ?
N3 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
N4 C23 C24 122.48(19) . . ?
N4 C23 C16 116.57(17) . . ?
C24 C23 C16 120.95(19) . . ?
C23 C24 C25 118.3(2) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C26 C25 C24 119.3(2) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 118.8(2) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
N4 C27 C26 123.6(2) . . ?
N4 C27 H27 118.2 . . ?
C26 C27 H27 118.2 . . ?

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
C6 C1 C2 C3 -1.2(3) . . . . ?
Br1 C1 C2 C3 179.60(16) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C2 C3 C4 C7 175.6(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C7 C4 C5 C6 -176.1(2) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
Br1 C1 C6 C5 179.8(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C8 N1 C7 C4 -85.5(3) . . . . ?
C12 N1 C7 C4 92.2(2) . . . . ?
C3 C4 C7 N1 159.1(2) . . . . ?
C5 C4 C7 N1 -24.1(3) . . . . ?
C12 N1 C8 C9 1.3(3) . . . . ?
C7 N1 C8 C9 179.0(2) . . . . ?
N1 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C8 C9 C10 C13 175.69(19) . . . . ?
C9 C10 C11 C12 2.0(3) . . . . ?
C13 C10 C11 C12 -174.97(19) . . . . ?
C8 N1 C12 C11 -0.6(3) . . . . ?
C7 N1 C12 C11 -178.3(2) . . . . ?
C10 C11 C12 N1 -1.1(4) . . . . ?
C11 C10 C13 C14 -164.45(19) . . . . ?
C9 C10 C13 C14 18.7(3) . . . . ?
C11 C10 C13 C17 18.9(3) . . . . ?
C9 C10 C13 C17 -157.94(19) . . . . ?
C17 C13 C14 C15 2.3(3) . . . . ?
C10 C13 C14 C15 -174.39(17) . . . . ?
C16 N2 C15 C14 -0.2(3) . . . . ?
C16 N2 C15 C18 -177.53(16) . . . . ?
C13 C14 C15 N2 -1.9(3) . . . . ?
C13 C14 C15 C18 175.32(17) . . . . ?
C15 N2 C16 C17 1.8(3) . . . . ?
C15 N2 C16 C23 -179.62(16) . . . . ?
N2 C16 C17 C13 -1.2(3) . . . . ?
C23 C16 C17 C13 -179.77(17) . . . . ?
C14 C13 C17 C16 -0.9(3) . . . . ?
C10 C13 C17 C16 175.89(17) . . . . ?
C22 N3 C18 C19 1.8(3) . . . . ?
C22 N3 C18 C15 -176.27(19) . . . . ?
N2 C15 C18 N3 168.89(17) . . . . ?
C14 C15 C18 N3 -8.5(3) . . . . ?
N2 C15 C18 C19 -9.3(3) . . . . ?
C14 C15 C18 C19 173.40(19) . . . . ?
N3 C18 C19 C20 -2.2(3) . . . . ?
C15 C18 C19 C20 175.82(19) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C18 N3 C22 C21 -0.1(4) . . . . ?
C20 C21 C22 N3 -1.3(4) . . . . ?
C27 N4 C23 C24 0.0(3) . . . . ?
C27 N4 C23 C16 -179.60(17) . . . . ?
N2 C16 C23 N4 179.92(17) . . . . ?
C17 C16 C23 N4 -1.5(3) . . . . ?
N2 C16 C23 C24 0.4(3) . . . . ?
C17 C16 C23 C24 178.98(18) . . . . ?
N4 C23 C24 C25 0.9(3) . . . . ?
C16 C23 C24 C25 -179.52(18) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C23 N4 C27 C26 -0.7(3) . . . . ?
C25 C26 C27 N4 0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_BPTP-3
_database_code_depnum_ccdc_archive 'CCDC 1016317'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H26 Br Cl N4 O7'
_chemical_formula_sum            'C27 H26 Br Cl N4 O7'
_chemical_formula_weight         633.88

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   16.215(7)
_cell_length_b                   25.856(11)
_cell_length_c                   7.236(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.340(9)
_cell_angle_gamma                90.00
_cell_volume                     3015(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4711
_cell_measurement_theta_min      2.5277
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       needle
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6233
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Saturn724
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1.0
_diffrn_reflns_number            13117
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5983
_reflns_number_gt                3900
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1745P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.761(18)
_refine_ls_number_reflns         5983
_refine_ls_number_parameters     361
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2637
_refine_ls_wR_factor_gt          0.2357
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31963(7) 0.16708(4) 0.46940(12) 0.0841(4) Uani 1 1 d . . .
Cl1 Cl 0.6383(2) 0.1478(2) 0.1779(8) 0.153(2) Uani 1 1 d . . .
O1 O 0.5853(7) 0.1219(7) 0.058(3) 0.204(8) Uani 1 1 d . . .
O1W O 0.330(2) 0.5034(10) -0.372(3) 0.312(16) Uani 1 1 d . . .
O2W O 0.5729(9) 0.2065(4) -0.302(2) 0.156(5) Uani 1 1 d . . .
O2 O 0.6047(12) 0.1718(11) 0.317(3) 0.273(16) Uani 1 1 d . . .
O3 O 0.660(2) 0.1978(11) 0.103(5) 0.292(14) Uani 1 1 d . . .
O3W O 0.760(3) 0.0632(17) 0.717(5) 0.42(3) Uani 1 1 d . . .
O4 O 0.7054(7) 0.1200(7) 0.248(3) 0.239(10) Uani 1 1 d . . .
N1 N 0.4396(5) 0.3287(2) -0.1984(10) 0.0613(16) Uani 1 1 d . . .
N2 N 0.6929(3) 0.5431(2) 0.0606(7) 0.0428(11) Uani 1 1 d . . .
N3 N 0.5098(4) 0.6124(3) -0.1171(10) 0.0633(16) Uani 1 1 d . . .
N4 N 0.8337(4) 0.4407(2) 0.2245(9) 0.0563(14) Uani 1 1 d . . .
C1 C 0.3377(5) 0.2033(3) 0.2453(12) 0.0606(19) Uani 1 1 d . . .
C2 C 0.2921(6) 0.2472(4) 0.1967(15) 0.075(2) Uani 1 1 d . . .
H2 H 0.2524 0.2599 0.2726 0.090 Uiso 1 1 calc R . .
C3 C 0.3061(6) 0.2723(4) 0.0318(14) 0.074(2) Uani 1 1 d . . .
H3 H 0.2738 0.3016 -0.0089 0.089 Uiso 1 1 calc R . .
C4 C 0.3673(5) 0.2544(3) -0.0724(11) 0.0578(18) Uani 1 1 d . . .
C5 C 0.4112(6) 0.2100(3) -0.0182(14) 0.070(2) Uani 1 1 d . . .
H5 H 0.4508 0.1964 -0.0927 0.084 Uiso 1 1 calc R . .
C6 C 0.3968(6) 0.1852(4) 0.1464(17) 0.079(3) Uani 1 1 d . . .
H6 H 0.4286 0.1558 0.1882 0.095 Uiso 1 1 calc R . .
C7 C 0.3854(6) 0.2823(3) -0.2454(14) 0.072(2) Uani 1 1 d . . .
H7A H 0.3326 0.2935 -0.3159 0.086 Uiso 1 1 calc R . .
H7B H 0.4135 0.2584 -0.3252 0.086 Uiso 1 1 calc R . .
C8 C 0.4058(5) 0.3755(3) -0.1720(14) 0.067(2) Uani 1 1 d . . .
H8 H 0.3471 0.3793 -0.1884 0.081 Uiso 1 1 calc R . .
C9 C 0.4543(5) 0.4170(3) -0.1224(15) 0.070(2) Uani 1 1 d . . .
H9 H 0.4292 0.4496 -0.1055 0.084 Uiso 1 1 calc R . .
C10 C 0.5404(4) 0.4125(2) -0.0957(9) 0.0461(13) Uani 1 1 d . . .
C11 C 0.5729(4) 0.3642(3) -0.1254(11) 0.0549(16) Uani 1 1 d . . .
H11 H 0.6314 0.3598 -0.1096 0.066 Uiso 1 1 calc R . .
C12 C 0.5239(5) 0.3229(3) -0.1765(12) 0.0601(18) Uani 1 1 d . . .
H12 H 0.5480 0.2902 -0.1969 0.072 Uiso 1 1 calc R . .
C13 C 0.5921(4) 0.4584(2) -0.0402(9) 0.0445(13) Uani 1 1 d . . .
C14 C 0.5640(4) 0.5078(2) -0.0778(8) 0.0418(12) Uani 1 1 d . . .
H14 H 0.5096 0.5134 -0.1378 0.050 Uiso 1 1 calc R . .
C15 C 0.6159(4) 0.5497(2) -0.0272(9) 0.0440(13) Uani 1 1 d . . .
C16 C 0.7213(4) 0.4949(3) 0.0971(9) 0.0456(14) Uani 1 1 d . . .
C17 C 0.6728(4) 0.4518(2) 0.0471(9) 0.0439(13) Uani 1 1 d . . .
H17 H 0.6943 0.4181 0.0721 0.053 Uiso 1 1 calc R . .
C18 C 0.5901(4) 0.6033(2) -0.0767(9) 0.0458(13) Uani 1 1 d . . .
C19 C 0.6513(5) 0.6418(3) -0.0846(12) 0.0636(19) Uani 1 1 d . . .
H19 H 0.7088 0.6346 -0.0572 0.076 Uiso 1 1 calc R . .
C20 C 0.6221(6) 0.6911(3) -0.1354(15) 0.076(3) Uani 1 1 d . . .
H20 H 0.6600 0.7189 -0.1435 0.091 Uiso 1 1 calc R . .
C21 C 0.5390(7) 0.6993(3) -0.1732(14) 0.077(3) Uani 1 1 d . . .
H21 H 0.5188 0.7329 -0.2065 0.093 Uiso 1 1 calc R . .
C22 C 0.4847(8) 0.6591(4) -0.1632(18) 0.083(3) Uani 1 1 d . . .
H22 H 0.4269 0.6655 -0.1908 0.099 Uiso 1 1 calc R . .
C23 C 0.8055(4) 0.4894(2) 0.1933(9) 0.0427(13) Uani 1 1 d . . .
C24 C 0.8530(5) 0.5329(3) 0.2443(11) 0.0554(16) Uani 1 1 d . . .
H24 H 0.8317 0.5667 0.2202 0.066 Uiso 1 1 calc R . .
C25 C 0.9337(5) 0.5251(4) 0.3330(12) 0.066(2) Uani 1 1 d . . .
H25 H 0.9680 0.5537 0.3716 0.079 Uiso 1 1 calc R . .
C26 C 0.9617(5) 0.4758(4) 0.3627(15) 0.071(2) Uani 1 1 d . . .
H26 H 1.0162 0.4697 0.4215 0.086 Uiso 1 1 calc R . .
C27 C 0.9122(5) 0.4359(3) 0.3086(14) 0.069(2) Uani 1 1 d . . .
H27 H 0.9335 0.4020 0.3306 0.083 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
Br1 C1 1.923(8) . ?
Cl1 O1 1.333(10) . ?
Cl1 O2 1.345(16) . ?
Cl1 O4 1.356(13) . ?
Cl1 O3 1.46(3) . ?
N1 C8 1.350(11) . ?
N1 C12 1.367(12) . ?
N1 C7 1.505(9) . ?
N2 C16 1.343(9) . ?
N2 C15 1.347(9) . ?
N3 C22 1.307(12) . ?
N3 C18 1.324(9) . ?
N4 C23 1.350(9) . ?
N4 C27 1.354(11) . ?
C1 C6 1.343(14) . ?
C1 C2 1.378(12) . ?
C2 C3 1.399(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(12) . ?
C4 C7 1.501(12) . ?
C5 C6 1.394(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.356(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(10) . ?
C10 C13 1.482(9) . ?
C11 C12 1.358(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.374(9) . ?
C13 C17 1.399(9) . ?
C14 C15 1.395(9) . ?
C14 H14 0.9500 . ?
C15 C18 1.482(9) . ?
C16 C17 1.388(9) . ?
C16 C23 1.470(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.411(10) . ?
C19 C20 1.396(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.361(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(17) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.390(10) . ?
C24 C25 1.407(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.363(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.338(14) . ?
C26 H26 0.9500 . ?
C27 H27 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
O1 Cl1 O2 115.7(12) . . ?
O1 Cl1 O4 114.2(11) . . ?
O2 Cl1 O4 109.8(14) . . ?
O1 Cl1 O3 111.6(17) . . ?
O2 Cl1 O3 90.1(19) . . ?
O4 Cl1 O3 113.2(18) . . ?
C8 N1 C12 120.0(6) . . ?
C8 N1 C7 120.6(7) . . ?
C12 N1 C7 119.3(7) . . ?
C16 N2 C15 119.3(5) . . ?
C22 N3 C18 119.4(9) . . ?
C23 N4 C27 116.3(6) . . ?
C6 C1 C2 123.0(9) . . ?
C6 C1 Br1 117.7(7) . . ?
C2 C1 Br1 119.3(7) . . ?
C1 C2 C3 117.9(9) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.1(9) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.8(8) . . ?
C5 C4 C7 119.5(8) . . ?
C3 C4 C7 120.7(8) . . ?
C4 C5 C6 119.6(9) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.5(9) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C7 N1 110.9(7) . . ?
C4 C7 H7A 109.4 . . ?
N1 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
N1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 120.9(7) . . ?
N1 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 120.9(8) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 116.6(6) . . ?
C11 C10 C13 123.5(6) . . ?
C9 C10 C13 120.0(6) . . ?
C12 C11 C10 122.2(7) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 N1 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
N1 C12 H12 120.3 . . ?
C14 C13 C17 118.4(6) . . ?
C14 C13 C10 121.7(6) . . ?
C17 C13 C10 119.9(6) . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N2 C15 C14 121.7(6) . . ?
N2 C15 C18 117.0(6) . . ?
C14 C15 C18 121.1(6) . . ?
N2 C16 C17 121.3(6) . . ?
N2 C16 C23 117.7(6) . . ?
C17 C16 C23 121.0(6) . . ?
C16 C17 C13 119.7(6) . . ?
C16 C17 H17 120.2 . . ?
C13 C17 H17 120.2 . . ?
N3 C18 C19 123.1(7) . . ?
N3 C18 C15 117.6(6) . . ?
C19 C18 C15 119.2(6) . . ?
C20 C19 C18 115.7(7) . . ?
C20 C19 H19 122.1 . . ?
C18 C19 H19 122.1 . . ?
C21 C20 C19 119.7(8) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.0(8) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N3 C22 C21 122.1(11) . . ?
N3 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
N4 C23 C24 122.9(6) . . ?
N4 C23 C16 116.7(6) . . ?
C24 C23 C16 120.3(6) . . ?
C23 C24 C25 117.7(7) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C26 C25 C24 118.9(8) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C27 C26 C25 119.7(8) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 N4 124.5(8) . . ?
C26 C27 H27 117.7 . . ?
N4 C27 H27 117.7 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.085
