# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ppda-p-Cl-TBABr-1a
_database_code_depnum_ccdc_archive 'CCDC 1860326'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl2 N4 O2, 2(C16 H36 N), 2(Br)'
_chemical_formula_sum            'C52 H88 Br2 Cl2 N6 O2'
_chemical_formula_weight         1059.98

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.9461(6)
_cell_length_b                   16.1753(10)
_cell_length_c                   20.8774(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.396(8)
_cell_angle_gamma                90
_cell_volume                     2971.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1938
_cell_measurement_theta_min      3.5340
_cell_measurement_theta_max      21.4930

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             1124.0
_exptl_transmission_factor_min   0.636
_exptl_transmission_factor_max   0.699
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    1.494
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11706
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.959
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5232
_reflns_number_gt                2896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5232
_refine_ls_number_parameters     293
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54857(7) 0.36192(4) 0.26710(3) 0.0871(3) Uani 1 1 d . . . . .
Cl1 Cl 0.0785(3) 0.70230(16) 0.01218(10) 0.1494(9) Uani 1 1 d . . . . .
O1 O 0.2784(4) 0.6154(2) 0.33931(18) 0.0770(10) Uani 1 1 d . . . . .
N2 N 0.4195(4) 0.4978(2) 0.3640(2) 0.0685(11) Uani 1 1 d . . . . .
H2N H 0.4530 0.4553 0.3463 0.082 Uiso 1 1 calc R U . . .
N1 N 0.3333(4) 0.5325(3) 0.2586(2) 0.0724(12) Uani 1 1 d . . . . .
H1N H 0.3763 0.4865 0.2520 0.087 Uiso 1 1 calc R U . . .
N3 N 0.1808(4) 0.3620(2) 0.6687(2) 0.0721(12) Uani 1 1 d . . . . .
C8 C 0.4562(5) 0.5014(3) 0.4321(2) 0.0599(12) Uani 1 1 d . . . . .
C6 C 0.2687(5) 0.5762(3) 0.2024(3) 0.0675(14) Uani 1 1 d . . . . .
C7 C 0.3374(5) 0.5530(3) 0.3221(3) 0.0637(13) Uani 1 1 d . . . . .
C9 C 0.5328(6) 0.4354(3) 0.4635(3) 0.0726(14) Uani 1 1 d . . . . .
H9 H 0.5566 0.3908 0.4390 0.087 Uiso 1 1 calc R U . . .
C10 C 0.5760(6) 0.4329(3) 0.5304(3) 0.0737(15) Uani 1 1 d . . . . .
H10 H 0.6268 0.3869 0.5503 0.088 Uiso 1 1 calc R U . . .
C1 C 0.2770(7) 0.5387(4) 0.1431(3) 0.0931(18) Uani 1 1 d . . . . .
H1 H 0.3224 0.4870 0.1426 0.112 Uiso 1 1 calc R U . . .
C14 C -0.0929(9) 0.6329(4) 0.5989(4) 0.130(3) Uani 1 1 d . . . . .
H14A H -0.1752 0.6062 0.5705 0.195 Uiso 1 1 calc R U . . .
H14B H -0.0740 0.6859 0.5813 0.195 Uiso 1 1 calc R U . . .
H14C H -0.1193 0.6400 0.6411 0.195 Uiso 1 1 calc R U . . .
C4 C 0.1452(6) 0.6918(4) 0.1439(3) 0.0855(17) Uani 1 1 d . . . . .
H4 H 0.1006 0.7438 0.1437 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2009(6) 0.6547(3) 0.2016(3) 0.0713(15) Uani 1 1 d . . . . .
H5 H 0.1941 0.6811 0.2405 0.086 Uiso 1 1 calc R U . . .
C23 C 0.0503(5) 0.3097(3) 0.6351(3) 0.0743(15) Uani 1 1 d . . . . .
H23A H 0.0565 0.2561 0.6564 0.089 Uiso 1 1 calc R U . . .
H23B H -0.0438 0.3353 0.6416 0.089 Uiso 1 1 calc R U . . .
C11 C 0.1786(6) 0.4470(3) 0.6380(3) 0.0838(17) Uani 1 1 d . . . . .
H11A H 0.1960 0.4405 0.5938 0.101 Uiso 1 1 calc R U . . .
H11B H 0.2632 0.4785 0.6617 0.101 Uiso 1 1 calc R U . . .
C15 C 0.1623(6) 0.3684(3) 0.7388(3) 0.0760(15) Uani 1 1 d . . . . .
H15A H 0.1602 0.3128 0.7559 0.091 Uiso 1 1 calc R U . . .
H15B H 0.0639 0.3931 0.7398 0.091 Uiso 1 1 calc R U . . .
C17 C 0.2343(13) 0.4223(8) 0.8523(4) 0.196(5) Uani 1 1 d . . . . .
H17A H 0.1272 0.4361 0.8464 0.235 Uiso 1 1 calc R U . . .
H17B H 0.2475 0.3682 0.8726 0.235 Uiso 1 1 calc R U . . .
C21 C 0.5117(8) 0.2088(5) 0.6792(5) 0.140(3) Uani 1 1 d D . . . .
H21A H 0.5868 0.2443 0.7050 0.168 Uiso 1 1 calc R U . . .
H21B H 0.5229 0.2135 0.6340 0.168 Uiso 1 1 calc R U . . .
C22 C 0.5395(14) 0.1187(5) 0.7018(7) 0.252(7) Uani 1 1 d D . . . .
H22A H 0.4553 0.0996 0.7206 0.378 Uiso 1 1 calc R U . . .
H22B H 0.6311 0.1156 0.7338 0.378 Uiso 1 1 calc R U . . .
H22C H 0.5496 0.0846 0.6652 0.378 Uiso 1 1 calc R U . . .
C18 C 0.3164(17) 0.4803(10) 0.8944(6) 0.258(7) Uani 1 1 d . . . . .
H18A H 0.4210 0.4636 0.9048 0.387 Uiso 1 1 calc R U . . .
H18B H 0.2750 0.4834 0.9337 0.387 Uiso 1 1 calc R U . . .
H18C H 0.3094 0.5335 0.8737 0.387 Uiso 1 1 calc R U . . .
C12 C 0.0345(6) 0.4975(4) 0.6360(3) 0.0949(19) Uani 1 1 d . . . . .
H12A H -0.0512 0.4676 0.6115 0.114 Uiso 1 1 calc R U . . .
H12B H 0.0159 0.5054 0.6799 0.114 Uiso 1 1 calc R U . . .
C19 C 0.3313(6) 0.3233(4) 0.6622(3) 0.0893(18) Uani 1 1 d . . . . .
H19A H 0.3402 0.3246 0.6166 0.107 Uiso 1 1 calc R U . . .
H19B H 0.4120 0.3576 0.6856 0.107 Uiso 1 1 calc R U . . .
C3 C 0.1537(7) 0.6540(5) 0.0866(3) 0.0937(19) Uani 1 1 d . . . . .
C13 C 0.0484(7) 0.5801(4) 0.6048(3) 0.1001(19) Uani 1 1 d . . . . .
H13A H 0.0716 0.5714 0.5617 0.120 Uiso 1 1 calc R U . . .
H13B H 0.1329 0.6099 0.6302 0.120 Uiso 1 1 calc R U . . .
C2 C 0.2191(8) 0.5771(5) 0.0860(3) 0.111(2) Uani 1 1 d . . . . .
H2 H 0.2238 0.5513 0.0466 0.134 Uiso 1 1 calc R U . . .
C20 C 0.3575(7) 0.2362(4) 0.6861(4) 0.122(3) Uani 1 1 d . . . . .
H20A H 0.3470 0.2331 0.7315 0.146 Uiso 1 1 calc R U . . .
H20B H 0.2822 0.2000 0.6612 0.146 Uiso 1 1 calc R U . . .
C24 C 0.0418(8) 0.2961(5) 0.5636(3) 0.109(2) Uani 1 1 d . . . . .
H24A H 0.1319 0.2667 0.5563 0.130 Uiso 1 1 calc R U . . .
H24B H 0.0392 0.3491 0.5417 0.130 Uiso 1 1 calc R U . . .
C16 C 0.2809(9) 0.4171(5) 0.7847(3) 0.117(2) Uani 1 1 d . . . . .
H16A H 0.2894 0.4723 0.7676 0.141 Uiso 1 1 calc R U . . .
H16B H 0.3790 0.3902 0.7886 0.141 Uiso 1 1 calc R U . . .
C25 C -0.1032(11) 0.2450(5) 0.5341(4) 0.151(3) Uani 1 1 d D . . . .
H25A H -0.1921 0.2687 0.5478 0.181 Uiso 1 1 calc R U . . .
H25B H -0.1187 0.2465 0.4870 0.181 Uiso 1 1 calc R U . . .
C26 C -0.0806(18) 0.1552(6) 0.5583(6) 0.268(7) Uani 1 1 d D . . . .
H26A H -0.0257 0.1250 0.5304 0.402 Uiso 1 1 calc R U . . .
H26B H -0.1778 0.1298 0.5575 0.402 Uiso 1 1 calc R U . . .
H26C H -0.0241 0.1549 0.6020 0.402 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.760(7) . ?
O1 C7 1.222(6) . ?
N2 C7 1.368(6) . ?
N2 C8 1.401(6) . ?
N1 C7 1.362(6) . ?
N1 C6 1.402(6) . ?
N3 C15 1.506(7) . ?
N3 C23 1.509(6) . ?
N3 C19 1.513(6) . ?
N3 C11 1.515(6) . ?
C8 C9 1.371(7) . ?
C8 C10 1.380(7) 3_666 ?
C6 C1 1.392(7) . ?
C6 C5 1.406(7) . ?
C9 C10 1.382(7) . ?
C10 C8 1.380(7) 3_666 ?
C1 C2 1.362(8) . ?
C14 C13 1.511(9) . ?
C4 C5 1.357(8) . ?
C4 C3 1.359(8) . ?
C23 C24 1.499(7) . ?
C11 C12 1.520(7) . ?
C15 C16 1.516(8) . ?
C17 C18 1.400(14) . ?
C17 C16 1.543(10) . ?
C21 C20 1.480(9) . ?
C21 C22 1.5385(10) . ?
C12 C13 1.502(7) . ?
C19 C20 1.500(8) . ?
C3 C2 1.376(9) . ?
C24 C25 1.567(10) . ?
C25 C26 1.5388(10) . ?

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 N2 C8 128.4(4) . . ?
C7 N1 C6 128.9(5) . . ?
C15 N3 C23 106.2(4) . . ?
C15 N3 C19 111.8(4) . . ?
C23 N3 C19 110.6(4) . . ?
C15 N3 C11 110.7(4) . . ?
C23 N3 C11 111.3(4) . . ?
C19 N3 C11 106.3(4) . . ?
C9 C8 C10 117.8(5) . 3_666 ?
C9 C8 N2 117.2(4) . . ?
C10 C8 N2 125.0(5) 3_666 . ?
C1 C6 N1 116.3(5) . . ?
C1 C6 C5 118.4(5) . . ?
N1 C6 C5 125.2(5) . . ?
O1 C7 N1 123.3(5) . . ?
O1 C7 N2 124.2(5) . . ?
N1 C7 N2 112.4(5) . . ?
C8 C9 C10 122.0(5) . . ?
C8 C10 C9 120.1(5) 3_666 . ?
C2 C1 C6 120.4(6) . . ?
C5 C4 C3 120.8(6) . . ?
C4 C5 C6 119.9(6) . . ?
C24 C23 N3 116.2(4) . . ?
N3 C11 C12 116.4(4) . . ?
N3 C15 C16 117.6(4) . . ?
C18 C17 C16 114.4(8) . . ?
C20 C21 C22 110.8(7) . . ?
C13 C12 C11 110.8(5) . . ?
C20 C19 N3 116.5(4) . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 Cl1 120.3(6) . . ?
C2 C3 Cl1 119.3(6) . . ?
C12 C13 C14 113.9(6) . . ?
C1 C2 C3 120.0(6) . . ?
C21 C20 C19 109.9(5) . . ?
C23 C24 C25 110.9(6) . . ?
C15 C16 C17 109.4(6) . . ?
C26 C25 C24 108.5(8) . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_ppda-p-Cl-TBASO4-1d
_database_code_depnum_ccdc_archive 'CCDC 1860329'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H16 Cl2 N4 O2), 2(C16 H36 N), O4 S'
_chemical_formula_sum            'C72 H104 Cl4 N10 O8 S'
_chemical_formula_weight         1411.51

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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.1061(11)
_cell_length_b                   13.5141(7)
_cell_length_c                   17.5192(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.113(6)
_cell_angle_gamma                90
_cell_volume                     3999.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3593
_cell_measurement_theta_min      3.6140
_cell_measurement_theta_max      21.6610

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             1508.0
_exptl_transmission_factor_min   0.929
_exptl_transmission_factor_max   0.946
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17306
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7031
_reflns_number_gt                4069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7031
_refine_ls_number_parameters     453
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5000 0.5000 1.0000 0.0657(4) Uani 1 2 d S . P . .
Cl1 Cl 0.01378(7) 0.56850(12) -0.29057(7) 0.1333(6) Uani 1 1 d . . . . .
Cl2 Cl 0.92845(10) 0.79161(15) 0.87487(10) 0.1865(8) Uani 1 1 d . . . . .
O2 O 0.67742(15) 0.66772(19) 0.49089(15) 0.0867(8) Uani 1 1 d . . . . .
O1 O 0.27670(15) 0.6977(2) 0.09088(15) 0.0904(8) Uani 1 1 d . . . . .
N2 N 0.40106(17) 0.6348(2) 0.11954(15) 0.0669(8) Uani 1 1 d . . . . .
H2N H 0.4275 0.5966 0.0995 0.080 Uiso 1 1 calc R U . . .
N1 N 0.30984(17) 0.6162(2) -0.00670(16) 0.0722(8) Uani 1 1 d . . . . .
H1N H 0.3502 0.5944 -0.0164 0.087 Uiso 1 1 calc R U . . .
N4 N 0.65708(17) 0.7991(2) 0.56323(16) 0.0706(8) Uani 1 1 d . . . . .
H4N H 0.6236 0.8452 0.5613 0.085 Uiso 1 1 calc R U . . .
N3 N 0.57438(16) 0.7747(2) 0.43399(15) 0.0684(8) Uani 1 1 d . . . . .
H3N H 0.5556 0.8293 0.4445 0.082 Uiso 1 1 calc R U . . .
N5 N 0.24770(17) 0.5651(2) 0.33717(17) 0.0682(8) Uani 1 1 d . . . . .
C11 C 0.5324(2) 0.7347(2) 0.35644(18) 0.0570(8) Uani 1 1 d . . . . .
C13 C 0.4165(2) 0.7491(2) 0.23382(19) 0.0628(9) Uani 1 1 d . . . . .
H13 H 0.3691 0.7809 0.2047 0.075 Uiso 1 1 calc R U . . .
C8 C 0.4418(2) 0.6701(2) 0.19940(18) 0.0579(8) Uani 1 1 d . . . . .
C12 C 0.4618(2) 0.7802(3) 0.31142(19) 0.0650(9) Uani 1 1 d . . . . .
H12 H 0.4444 0.8334 0.3342 0.078 Uiso 1 1 calc R U . . .
C9 C 0.5119(2) 0.6236(3) 0.2447(2) 0.0654(9) Uani 1 1 d . . . . .
H9 H 0.5289 0.5699 0.2222 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2372(2) 0.6087(2) -0.07145(19) 0.0623(9) Uani 1 1 d . . . . .
C15 C 0.7229(2) 0.7922(2) 0.6358(2) 0.0652(9) Uani 1 1 d . . . . .
C7 C 0.3254(2) 0.6536(3) 0.0704(2) 0.0661(9) Uani 1 1 d . . . . .
C10 C 0.5571(2) 0.6550(3) 0.32226(19) 0.0644(9) Uani 1 1 d . . . . .
H10 H 0.6041 0.6227 0.3516 0.077 Uiso 1 1 calc R U . . .
C14 C 0.6397(2) 0.7411(3) 0.4949(2) 0.0631(9) Uani 1 1 d . . . . .
C21 C 0.2757(2) 0.4782(3) 0.2986(2) 0.0743(10) Uani 1 1 d . . . . .
H21A H 0.3068 0.4342 0.3421 0.089 Uiso 1 1 calc R U . . .
H21B H 0.2295 0.4416 0.2644 0.089 Uiso 1 1 calc R U . . .
C16 C 0.7136(2) 0.8230(3) 0.7071(2) 0.0811(11) Uani 1 1 d . . . . .
H16 H 0.6643 0.8443 0.7056 0.097 Uiso 1 1 calc R U . . .
C1 C 0.2397(2) 0.5736(3) -0.1448(2) 0.0797(11) Uani 1 1 d . . . . .
H1 H 0.2881 0.5582 -0.1490 0.096 Uiso 1 1 calc R U . . .
C29 C 0.2027(2) 0.5198(3) 0.3863(2) 0.0731(10) Uani 1 1 d . . . . .
H29A H 0.1596 0.4808 0.3495 0.088 Uiso 1 1 calc R U . . .
H29B H 0.2379 0.4746 0.4259 0.088 Uiso 1 1 calc R U . . .
C33 C 0.3170(2) 0.6266(3) 0.3910(2) 0.0807(11) Uani 1 1 d . . . . .
H33A H 0.3485 0.6456 0.3588 0.097 Uiso 1 1 calc R U . . .
H33B H 0.2963 0.6868 0.4057 0.097 Uiso 1 1 calc R U . . .
C5 C 0.1655(2) 0.6319(3) -0.0670(2) 0.0837(12) Uani 1 1 d . . . . .
H5 H 0.1629 0.6560 -0.0183 0.100 Uiso 1 1 calc R U . . .
C20 C 0.7962(2) 0.7612(3) 0.6386(3) 0.0856(12) Uani 1 1 d . . . . .
H20 H 0.8032 0.7404 0.5910 0.103 Uiso 1 1 calc R U . . .
C3 C 0.1002(2) 0.5845(3) -0.2055(2) 0.0850(12) Uani 1 1 d . . . . .
C34 C 0.3714(2) 0.5780(3) 0.4689(2) 0.0858(12) Uani 1 1 d . . . . .
H34A H 0.3426 0.5669 0.5054 0.103 Uiso 1 1 calc R U . . .
H34B H 0.3885 0.5142 0.4559 0.103 Uiso 1 1 calc R U . . .
C2 C 0.1708(3) 0.5613(3) -0.2117(2) 0.0886(12) Uani 1 1 d . . . . .
H2 H 0.1727 0.5372 -0.2607 0.106 Uiso 1 1 calc R U . . .
C25 C 0.1962(2) 0.6346(3) 0.2718(2) 0.0831(11) Uani 1 1 d . . . . .
H25A H 0.1782 0.6872 0.2985 0.100 Uiso 1 1 calc R U . . .
H25B H 0.2290 0.6647 0.2448 0.100 Uiso 1 1 calc R U . . .
C17 C 0.7770(3) 0.8222(3) 0.7806(2) 0.1006(14) Uani 1 1 d . . . . .
H17 H 0.7704 0.8427 0.8284 0.121 Uiso 1 1 calc R U . . .
C4 C 0.0970(2) 0.6199(3) -0.1341(3) 0.0966(14) Uani 1 1 d . . . . .
H4 H 0.0484 0.6361 -0.1306 0.116 Uiso 1 1 calc R U . . .
C30 C 0.1691(2) 0.5906(3) 0.4313(2) 0.0945(13) Uani 1 1 d . . . . .
H30A H 0.1253 0.6272 0.3929 0.113 Uiso 1 1 calc R U . . .
H30B H 0.2093 0.6374 0.4624 0.113 Uiso 1 1 calc R U . . .
C22 C 0.3244(2) 0.5053(3) 0.2476(2) 0.0877(12) Uani 1 1 d . . . . .
H22A H 0.3765 0.5271 0.2831 0.105 Uiso 1 1 calc R U . . .
H22B H 0.2992 0.5595 0.2113 0.105 Uiso 1 1 calc R U . . .
C18 C 0.8486(3) 0.7915(4) 0.7825(3) 0.1062(15) Uani 1 1 d . . . . .
C19 C 0.8597(3) 0.7610(3) 0.7124(3) 0.1063(15) Uani 1 1 d . . . . .
H19 H 0.9095 0.7403 0.7146 0.128 Uiso 1 1 calc R U . . .
C26 C 0.1249(3) 0.5899(3) 0.2070(2) 0.1028(14) Uani 1 1 d . . . . .
H26A H 0.1419 0.5398 0.1773 0.123 Uiso 1 1 calc R U . . .
H26B H 0.0919 0.5581 0.2328 0.123 Uiso 1 1 calc R U . . .
O5 O 0.5253(3) 0.5831(4) 1.0564(3) 0.0810(15) Uani 0.5 1 d . . P . .
O3 O 0.5332(3) 0.5254(3) 0.9310(2) 0.0721(14) Uani 0.5 1 d . . P . .
C35 C 0.4420(3) 0.6409(4) 0.5108(3) 0.1122(15) Uani 1 1 d . . . . .
H35A H 0.4736 0.6443 0.4765 0.135 Uiso 1 1 calc R U . . .
H35B H 0.4240 0.7075 0.5154 0.135 Uiso 1 1 calc R U . . .
C23 C 0.3328(3) 0.4168(3) 0.1970(3) 0.1098(16) Uani 1 1 d . . . . .
H23A H 0.3777 0.4280 0.1803 0.132 Uiso 1 1 calc R U . . .
H23B H 0.3441 0.3582 0.2313 0.132 Uiso 1 1 calc R U . . .
C36 C 0.4935(3) 0.6078(4) 0.5931(3) 0.1209(17) Uani 1 1 d . . . . .
H36A H 0.4660 0.6152 0.6305 0.181 Uiso 1 1 calc R U . . .
H36B H 0.5408 0.6472 0.6115 0.181 Uiso 1 1 calc R U . . .
H36C H 0.5073 0.5395 0.5909 0.181 Uiso 1 1 calc R U . . .
O4 O 0.4522(3) 0.5901(4) 0.9632(3) 0.0845(15) Uani 0.5 1 d . . P . .
C31 C 0.1401(3) 0.5287(4) 0.4894(3) 0.136(2) Uani 1 1 d D . . . .
H31A H 0.0975 0.4855 0.4572 0.163 Uiso 1 1 calc R U . . .
H31B H 0.1832 0.4876 0.5238 0.163 Uiso 1 1 calc R U . . .
C27 C 0.0779(4) 0.6669(4) 0.1488(3) 0.143(2) Uani 1 1 d . . . . .
H27A H 0.0614 0.7166 0.1793 0.172 Uiso 1 1 calc R U . . .
H27B H 0.1119 0.6992 0.1244 0.172 Uiso 1 1 calc R U . . .
C24 C 0.2605(4) 0.3974(4) 0.1218(3) 0.139(2) Uani 1 1 d . . . . .
H24A H 0.2157 0.3859 0.1377 0.208 Uiso 1 1 calc R U . . .
H24B H 0.2693 0.3403 0.0937 0.208 Uiso 1 1 calc R U . . .
H24C H 0.2503 0.4538 0.0862 0.208 Uiso 1 1 calc R U . . .
C28 C 0.0074(4) 0.6290(6) 0.0829(4) 0.195(3) Uani 1 1 d . . . . .
H28A H 0.0228 0.5781 0.0535 0.292 Uiso 1 1 calc R U . . .
H28B H -0.0176 0.6820 0.0462 0.292 Uiso 1 1 calc R U . . .
H28C H -0.0290 0.6023 0.1061 0.292 Uiso 1 1 calc R U . . .
C32 C 0.1107(5) 0.5953(5) 0.5436(4) 0.258(5) Uani 1 1 d D . . . .
H32A H 0.1551 0.6263 0.5845 0.387 Uiso 1 1 calc R U . . .
H32B H 0.0824 0.5559 0.5697 0.387 Uiso 1 1 calc R U . . .
H32C H 0.0760 0.6451 0.5105 0.387 Uiso 1 1 calc R U . . .
O6 O 0.4215(3) 0.4839(4) 0.9675(4) 0.103(2) Uani 0.5 1 d . . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O6 1.345(5) 3_667 ?
S1 O6 1.345(5) . ?
S1 O5 1.457(4) 3_667 ?
S1 O5 1.457(4) . ?
S1 O4 1.499(5) . ?
S1 O4 1.499(5) 3_667 ?
S1 O3 1.570(4) 3_667 ?
S1 O3 1.570(4) . ?
Cl1 C3 1.742(4) . ?
Cl2 C18 1.740(4) . ?
O2 C14 1.222(4) . ?
O1 C7 1.221(4) . ?
N2 C7 1.354(4) . ?
N2 C8 1.409(4) . ?
N2 H2N 0.8600 . ?
N1 C7 1.373(4) . ?
N1 C6 1.397(4) . ?
N1 H1N 0.8600 . ?
N4 C14 1.369(4) . ?
N4 C15 1.398(4) . ?
N4 H4N 0.8600 . ?
N3 C14 1.354(4) . ?
N3 C11 1.404(4) . ?
N3 H3N 0.8600 . ?
N5 C29 1.511(4) . ?
N5 C25 1.515(4) . ?
N5 C33 1.518(4) . ?
N5 C21 1.529(4) . ?
C11 C12 1.382(4) . ?
C11 C10 1.382(4) . ?
C13 C12 1.377(4) . ?
C13 C8 1.383(4) . ?
C13 H13 0.9300 . ?
C8 C9 1.381(4) . ?
C12 H12 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C6 C5 1.364(5) . ?
C6 C1 1.385(4) . ?
C15 C20 1.376(5) . ?
C15 C16 1.384(5) . ?
C10 H10 0.9300 . ?
C21 C22 1.510(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C16 C17 1.383(5) . ?
C16 H16 0.9300 . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
C29 C30 1.501(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C33 C34 1.515(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C5 C4 1.378(5) . ?
C5 H5 0.9300 . ?
C20 C19 1.387(5) . ?
C20 H20 0.9300 . ?
C3 C2 1.357(5) . ?
C3 C4 1.360(5) . ?
C34 C35 1.491(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C2 H2 0.9300 . ?
C25 C26 1.505(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C17 C18 1.349(6) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C30 C31 1.547(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C22 C23 1.529(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C18 C19 1.377(6) . ?
C19 H19 0.9300 . ?
C26 C27 1.491(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
O5 O6 1.488(7) 3_667 ?
O5 O4 1.695(7) . ?
O3 O6 1.674(7) 3_667 ?
C35 C36 1.476(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C23 C24 1.509(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O4 O6 1.552(7) . ?
C31 C32 1.5370(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C27 C28 1.471(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O6 O5 1.488(7) 3_667 ?
O6 O3 1.674(7) 3_667 ?

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
O6 S1 O6 180.0(5) 3_667 . ?
O6 S1 O5 116.0(3) 3_667 3_667 ?
O6 S1 O5 64.0(3) . 3_667 ?
O6 S1 O5 64.0(3) 3_667 . ?
O6 S1 O5 116.0(3) . . ?
O5 S1 O5 180.0 3_667 . ?
O6 S1 O4 114.1(3) 3_667 . ?
O6 S1 O4 65.9(3) . . ?
O5 S1 O4 110.0(3) 3_667 . ?
O5 S1 O4 70.0(3) . . ?
O6 S1 O4 65.9(3) 3_667 3_667 ?
O6 S1 O4 114.1(3) . 3_667 ?
O5 S1 O4 70.0(3) 3_667 3_667 ?
O5 S1 O4 110.0(3) . 3_667 ?
O4 S1 O4 180.0 . 3_667 ?
O6 S1 O3 110.4(3) 3_667 3_667 ?
O6 S1 O3 69.6(3) . 3_667 ?
O5 S1 O3 103.9(2) 3_667 3_667 ?
O5 S1 O3 76.1(2) . 3_667 ?
O4 S1 O3 100.8(2) . 3_667 ?
O4 S1 O3 79.2(2) 3_667 3_667 ?
O6 S1 O3 69.6(3) 3_667 . ?
O6 S1 O3 110.4(3) . . ?
O5 S1 O3 76.1(2) 3_667 . ?
O5 S1 O3 103.9(2) . . ?
O4 S1 O3 79.2(2) . . ?
O4 S1 O3 100.8(2) 3_667 . ?
O3 S1 O3 180.0 3_667 . ?
C7 N2 C8 128.1(3) . . ?
C7 N2 H2N 116.0 . . ?
C8 N2 H2N 116.0 . . ?
C7 N1 C6 128.7(3) . . ?
C7 N1 H1N 115.7 . . ?
C6 N1 H1N 115.7 . . ?
C14 N4 C15 127.5(3) . . ?
C14 N4 H4N 116.2 . . ?
C15 N4 H4N 116.2 . . ?
C14 N3 C11 130.5(3) . . ?
C14 N3 H3N 114.8 . . ?
C11 N3 H3N 114.8 . . ?
C29 N5 C25 111.8(3) . . ?
C29 N5 C33 111.3(3) . . ?
C25 N5 C33 106.0(3) . . ?
C29 N5 C21 105.8(3) . . ?
C25 N5 C21 110.7(3) . . ?
C33 N5 C21 111.3(3) . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 N3 116.6(3) . . ?
C10 C11 N3 124.9(3) . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C9 C8 C13 118.7(3) . . ?
C9 C8 N2 117.4(3) . . ?
C13 C8 N2 123.8(3) . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 N1 125.0(3) . . ?
C1 C6 N1 116.3(3) . . ?
C20 C15 C16 119.3(3) . . ?
C20 C15 N4 123.3(3) . . ?
C16 C15 N4 117.4(3) . . ?
O1 C7 N2 125.2(3) . . ?
O1 C7 N1 123.8(3) . . ?
N2 C7 N1 111.0(3) . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
O2 C14 N3 125.0(3) . . ?
O2 C14 N4 123.9(3) . . ?
N3 C14 N4 111.0(3) . . ?
C22 C21 N5 115.6(3) . . ?
C22 C21 H21A 108.4 . . ?
N5 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
N5 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C2 C1 C6 120.5(4) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C30 C29 N5 116.4(3) . . ?
C30 C29 H29A 108.2 . . ?
N5 C29 H29A 108.2 . . ?
C30 C29 H29B 108.2 . . ?
N5 C29 H29B 108.2 . . ?
H29A C29 H29B 107.3 . . ?
C34 C33 N5 116.5(3) . . ?
C34 C33 H33A 108.2 . . ?
N5 C33 H33A 108.2 . . ?
C34 C33 H33B 108.2 . . ?
N5 C33 H33B 108.2 . . ?
H33A C33 H33B 107.3 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C15 C20 C19 120.0(4) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 Cl1 119.0(3) . . ?
C4 C3 Cl1 120.5(3) . . ?
C35 C34 C33 111.1(4) . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C26 C25 N5 116.6(3) . . ?
C26 C25 H25A 108.1 . . ?
N5 C25 H25A 108.1 . . ?
C26 C25 H25B 108.1 . . ?
N5 C25 H25B 108.1 . . ?
H25A C25 H25B 107.3 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C29 C30 C31 107.4(4) . . ?
C29 C30 H30A 110.2 . . ?
C31 C30 H30A 110.2 . . ?
C29 C30 H30B 110.2 . . ?
C31 C30 H30B 110.2 . . ?
H30A C30 H30B 108.5 . . ?
C21 C22 C23 110.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C17 C18 C19 121.2(4) . . ?
C17 C18 Cl2 119.4(4) . . ?
C19 C18 Cl2 119.3(4) . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C27 C26 C25 111.0(4) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
S1 O5 O6 54.4(2) . 3_667 ?
S1 O5 O4 56.2(2) . . ?
O6 O5 O4 97.0(4) 3_667 . ?
S1 O3 O6 48.9(2) . 3_667 ?
C36 C35 C34 115.9(4) . . ?
C36 C35 H35A 108.3 . . ?
C34 C35 H35A 108.3 . . ?
C36 C35 H35B 108.3 . . ?
C34 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C24 C23 C22 113.9(4) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
S1 O4 O6 52.3(3) . . ?
S1 O4 O5 53.9(2) . . ?
O6 O4 O5 94.1(4) . . ?
C32 C31 C30 111.5(5) . . ?
C32 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
C28 C27 C26 114.5(5) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
S1 O6 O5 61.6(3) . 3_667 ?
S1 O6 O4 61.8(3) . . ?
O5 O6 O4 105.6(4) 3_667 . ?
S1 O6 O3 61.5(3) . 3_667 ?
O5 O6 O3 97.7(4) 3_667 3_667 ?
O4 O6 O3 94.2(4) . 3_667 ?

_refine_diff_density_max         0.692
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_ppda-p-Br-TBACl-2a
_database_code_depnum_ccdc_archive 'CCDC 1860331'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br2 N4 O2, 2(C16 H36 N), 2(Cl)'
_chemical_formula_sum            'C52 H88 Br2 Cl2 N6 O2'
_chemical_formula_weight         1059.98

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.0143(6)
_cell_length_b                   15.6469(17)
_cell_length_c                   21.0997(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.821(7)
_cell_angle_gamma                90
_cell_volume                     2940.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1569
_cell_measurement_theta_min      3.4920
_cell_measurement_theta_max      19.3300

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             1124.0
_exptl_transmission_factor_min   0.652
_exptl_transmission_factor_max   0.728
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    1.509
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12250
_diffrn_reflns_av_unetI/netI     0.1203
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5174
_reflns_number_gt                3780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+1.0010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5174
_refine_ls_number_parameters     294
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2100
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1850
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57229(12) 0.31114(9) 0.01055(5) 0.1531(7) Uani 1 1 d . . . . .
Cl1 Cl 0.0513(2) 0.64177(13) 0.27335(9) 0.0921(7) Uani 1 1 d . . . . .
O1 O 0.7794(5) 0.3883(4) 0.3404(2) 0.0912(16) Uani 1 1 d . . . . .
N2 N 0.9242(6) 0.5079(4) 0.3651(3) 0.0807(17) Uani 1 1 d . . . . .
H2N H 0.9586 0.5519 0.3477 0.097 Uiso 1 1 calc R U . . .
C7 C 0.8417(7) 0.4515(6) 0.3240(4) 0.078(2) Uani 1 1 d . . . . .
N3 N 0.3192(6) 0.3638(4) 0.3275(3) 0.0816(18) Uani 1 1 d . . . . .
N1 N 0.8427(5) 0.4768(4) 0.2609(3) 0.0825(18) Uani 1 1 d . . . . .
H1N H 0.8871 0.5242 0.2553 0.099 Uiso 1 1 calc R U . . .
C8 C 0.9595(7) 0.5020(5) 0.4330(4) 0.071(2) Uani 1 1 d . . . . .
C9 C 1.0390(7) 0.5689(5) 0.4669(4) 0.086(2) Uani 1 1 d . . . . .
H9 H 1.0653 0.6161 0.4443 0.103 Uiso 1 1 calc R U . . .
C1 C 0.7864(8) 0.4744(6) 0.1482(4) 0.101(3) Uani 1 1 d . . . . .
H1 H 0.8315 0.5279 0.1483 0.121 Uiso 1 1 calc R U . . .
C6 C 0.7789(7) 0.4331(5) 0.2056(4) 0.076(2) Uani 1 1 d . . . . .
C23 C 0.4463(7) 0.3088(5) 0.3582(4) 0.088(2) Uani 1 1 d . . . . .
H23A H 0.5399 0.3351 0.3512 0.106 Uiso 1 1 calc R U . . .
H23B H 0.4393 0.2539 0.3366 0.106 Uiso 1 1 calc R U . . .
C3 C 0.6589(9) 0.3603(7) 0.0908(4) 0.100(3) Uani 1 1 d . . . . .
C5 C 0.7077(7) 0.3541(6) 0.2036(4) 0.084(2) Uani 1 1 d . . . . .
H5 H 0.7017 0.3255 0.2418 0.101 Uiso 1 1 calc R U . . .
C2 C 0.7276(10) 0.4365(8) 0.0910(5) 0.122(3) Uani 1 1 d . . . . .
H2 H 0.7353 0.4637 0.0525 0.147 Uiso 1 1 calc R U . . .
C20 C 0.2264(9) 0.4263(6) 0.2135(4) 0.127(3) Uani 1 1 d D . . . .
H20A H 0.1278 0.4006 0.2113 0.152 Uiso 1 1 calc R U . . .
H20B H 0.2217 0.4840 0.2298 0.152 Uiso 1 1 calc R U . . .
C10 C 0.9209(7) 0.4327(6) 0.4685(4) 0.090(2) Uani 1 1 d . . . . .
H10 H 0.8674 0.3873 0.4478 0.108 Uiso 1 1 calc R U . . .
C4 C 0.6464(7) 0.3179(6) 0.1469(4) 0.091(2) Uani 1 1 d . . . . .
H4 H 0.5972 0.2656 0.1461 0.110 Uiso 1 1 calc R U . . .
C19 C 0.3414(7) 0.3743(5) 0.2584(3) 0.090(2) Uani 1 1 d . . . . .
H19A H 0.3454 0.3176 0.2401 0.108 Uiso 1 1 calc R U . . .
H19B H 0.4389 0.4004 0.2582 0.108 Uiso 1 1 calc R U . . .
C11 C 0.3206(8) 0.4502(6) 0.3602(4) 0.099(3) Uani 1 1 d . . . . .
H11A H 0.2396 0.4843 0.3376 0.119 Uiso 1 1 calc R U . . .
H11B H 0.2994 0.4414 0.4035 0.119 Uiso 1 1 calc R U . . .
C21 C 0.2699(15) 0.4282(10) 0.1501(4) 0.232(8) Uani 1 1 d D . . . .
H21A H 0.3772 0.4381 0.1548 0.279 Uiso 1 1 calc R U . . .
H21B H 0.2503 0.3724 0.1306 0.279 Uiso 1 1 calc R U . . .
C15 C 0.1686(8) 0.3242(6) 0.3336(4) 0.105(3) Uani 1 1 d . . . . .
H15A H 0.1592 0.3209 0.3787 0.126 Uiso 1 1 calc R U . . .
H15B H 0.0897 0.3616 0.3131 0.126 Uiso 1 1 calc R U . . .
C13 C 0.4519(9) 0.5858(6) 0.3967(4) 0.121(3) Uani 1 1 d . . . . .
H13A H 0.3736 0.6192 0.3713 0.145 Uiso 1 1 calc R U . . .
H13B H 0.4220 0.5761 0.4383 0.145 Uiso 1 1 calc R U . . .
C12 C 0.4644(9) 0.5009(6) 0.3642(4) 0.117(3) Uani 1 1 d . . . . .
H12A H 0.5462 0.4684 0.3880 0.141 Uiso 1 1 calc R U . . .
H12B H 0.4873 0.5103 0.3213 0.141 Uiso 1 1 calc R U . . .
C24 C 0.4522(10) 0.2938(6) 0.4287(4) 0.125(3) Uani 1 1 d D . . . .
H24A H 0.4464 0.3484 0.4500 0.150 Uiso 1 1 calc R U . . .
H24B H 0.3657 0.2602 0.4356 0.150 Uiso 1 1 calc R U . . .
C16 C 0.1447(9) 0.2376(8) 0.3052(5) 0.153(4) Uani 1 1 d D . . . .
H16A H 0.2194 0.1980 0.3261 0.184 Uiso 1 1 calc R U . . .
H16B H 0.1513 0.2390 0.2597 0.184 Uiso 1 1 calc R U . . .
C25 C 0.5879(12) 0.2499(8) 0.4570(7) 0.220(7) Uani 1 1 d D . . . .
H25A H 0.6717 0.2693 0.4370 0.264 Uiso 1 1 calc R U . . .
H25B H 0.6096 0.2631 0.5024 0.264 Uiso 1 1 calc R U . . .
C14 C 0.5955(11) 0.6365(7) 0.4055(5) 0.167(5) Uani 1 1 d . . . . .
H14A H 0.6670 0.6101 0.4380 0.251 Uiso 1 1 calc R U . . .
H14B H 0.5758 0.6937 0.4182 0.251 Uiso 1 1 calc R U . . .
H14C H 0.6353 0.6378 0.3658 0.251 Uiso 1 1 calc R U . . .
C17 C -0.0138(9) 0.2103(8) 0.3159(7) 0.230(8) Uani 1 1 d D . . . .
H17A H -0.0187 0.2088 0.3615 0.276 Uiso 1 1 calc R U . . .
H17B H -0.0870 0.2514 0.2961 0.276 Uiso 1 1 calc R U . . .
C22 C 0.1947(17) 0.4921(9) 0.1069(7) 0.329(11) Uani 1 1 d D . . . .
H22A H 0.0880 0.4850 0.1035 0.493 Uiso 1 1 calc R U . . .
H22B H 0.2242 0.4856 0.0653 0.493 Uiso 1 1 calc R U . . .
H22C H 0.2222 0.5481 0.1233 0.493 Uiso 1 1 calc R U . . .
C18 C -0.0504(18) 0.1213(9) 0.2866(9) 0.330(11) Uani 1 1 d D . . . .
H18A H -0.0703 0.1259 0.2407 0.495 Uiso 1 1 calc R U . . .
H18B H -0.1371 0.0986 0.3020 0.495 Uiso 1 1 calc R U . . .
H18C H 0.0335 0.0839 0.2987 0.495 Uiso 1 1 calc R U . . .
C26 C 0.570(2) 0.1583(9) 0.4486(10) 0.342(13) Uani 1 1 d D . . . .
H26A H 0.5838 0.1309 0.4898 0.512 Uiso 1 1 calc R U . . .
H26B H 0.6436 0.1373 0.4240 0.512 Uiso 1 1 calc R U . . .
H26C H 0.4714 0.1461 0.4264 0.512 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.915(8) . ?
O1 C7 1.214(8) . ?
N2 C7 1.373(8) . ?
N2 C8 1.423(8) . ?
C7 N1 1.390(9) . ?
N3 C23 1.498(8) . ?
N3 C19 1.511(8) . ?
N3 C15 1.516(8) . ?
N3 C11 1.517(9) . ?
N1 C6 1.397(8) . ?
C8 C10 1.392(9) . ?
C8 C9 1.401(9) . ?
C9 C10 1.355(9) 3_766 ?
C1 C2 1.376(10) . ?
C1 C6 1.383(9) . ?
C6 C5 1.391(10) . ?
C23 C24 1.499(10) . ?
C3 C2 1.344(11) . ?
C3 C4 1.376(10) . ?
C5 C4 1.362(9) . ?
C20 C21 1.4509(10) . ?
C20 C19 1.526(9) . ?
C10 C9 1.355(9) 3_766 ?
C11 C12 1.511(9) . ?
C21 C22 1.4497(10) . ?
C15 C16 1.485(11) . ?
C13 C14 1.505(10) . ?
C13 C12 1.507(10) . ?
C24 C25 1.4505(10) . ?
C16 C17 1.5404(10) . ?
C25 C26 1.4491(10) . ?
C17 C18 1.5388(10) . ?

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 N2 C8 127.7(7) . . ?
O1 C7 N2 125.0(8) . . ?
O1 C7 N1 125.2(8) . . ?
N2 C7 N1 109.9(7) . . ?
C23 N3 C19 105.9(5) . . ?
C23 N3 C15 111.3(6) . . ?
C19 N3 C15 112.3(6) . . ?
C23 N3 C11 111.2(6) . . ?
C19 N3 C11 110.5(6) . . ?
C15 N3 C11 105.7(6) . . ?
C7 N1 C6 126.7(7) . . ?
C10 C8 C9 117.2(7) . . ?
C10 C8 N2 123.8(8) . . ?
C9 C8 N2 119.0(7) . . ?
C10 C9 C8 122.4(7) 3_766 . ?
C2 C1 C6 120.2(8) . . ?
C1 C6 C5 118.2(8) . . ?
C1 C6 N1 115.7(8) . . ?
C5 C6 N1 126.1(7) . . ?
N3 C23 C24 115.3(6) . . ?
C2 C3 C4 121.6(8) . . ?
C2 C3 Br1 119.0(8) . . ?
C4 C3 Br1 119.4(8) . . ?
C4 C5 C6 121.3(8) . . ?
C3 C2 C1 120.0(9) . . ?
C21 C20 C19 109.2(7) . . ?
C9 C10 C8 120.4(7) 3_766 . ?
C5 C4 C3 118.6(8) . . ?
N3 C19 C20 118.6(6) . . ?
C12 C11 N3 116.1(6) . . ?
C22 C21 C20 115.4(10) . . ?
C16 C15 N3 114.5(6) . . ?
C14 C13 C12 113.4(7) . . ?
C13 C12 C11 111.4(7) . . ?
C25 C24 C23 112.5(9) . . ?
C15 C16 C17 105.9(9) . . ?
C26 C25 C24 110.3(11) . . ?
C18 C17 C16 109.7(11) . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_ppda-p-Br-TBAOAc-2c
_database_code_depnum_ccdc_archive 'CCDC 1860333'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br2 N4 O2, 2(C16 H36 N), 2(C2 H3 O2)'
_chemical_formula_sum            'C56 H94 Br2 N6 O6'
_chemical_formula_weight         1107.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.2635(9)
_cell_length_b                   16.5661(12)
_cell_length_c                   28.231(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.852(7)
_cell_angle_gamma                90
_cell_volume                     6189.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2641
_cell_measurement_theta_min      3.4780
_cell_measurement_theta_max      19.8510

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             2360.0
_exptl_transmission_factor_min   0.663
_exptl_transmission_factor_max   0.722
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    1.358
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25495
_diffrn_reflns_av_unetI/netI     0.1553
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10864
_reflns_number_gt                7625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00064(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10864
_refine_ls_number_parameters     642
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.2285
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.16209(6) 0.48833(5) 0.08995(3) 0.1124(4) Uani 1 1 d . . . . .
Br2 Br 1.71010(7) 0.48247(7) 0.35716(4) 0.1451(5) Uani 1 1 d . . . . .
O6 O 0.9616(4) 0.6020(3) 0.62109(19) 0.1053(18) Uani 1 1 d . . . . .
O2 O 1.2291(3) 0.4557(3) 0.24459(19) 0.0974(16) Uani 1 1 d . . . . .
O1 O 0.6403(3) 0.4571(3) 0.19540(19) 0.0890(15) Uani 1 1 d . . . . .
O4 O 0.8172(4) 0.1615(3) 0.56908(18) 0.1072(18) Uani 1 1 d . . . . .
O3 O 0.6787(4) 0.1201(3) 0.52848(18) 0.1103(18) Uani 1 1 d . . . . .
N4 N 1.2609(4) 0.4244(3) 0.32262(18) 0.0723(16) Uani 1 1 d . . . . .
H4N H 1.2325 0.4086 0.3475 0.087 Uiso 1 1 calc R U . . .
N1 N 0.6097(4) 0.4169(3) 0.11786(19) 0.0754(16) Uani 1 1 d . . . . .
H1N H 0.6374 0.3983 0.0934 0.091 Uiso 1 1 calc R U . . .
O5 O 0.8120(4) 0.6510(3) 0.59722(18) 0.0976(16) Uani 1 1 d . . . . .
N3 N 1.1020(4) 0.4102(3) 0.28740(18) 0.0732(16) Uani 1 1 d . . . . .
H3N H 1.0886 0.3935 0.3151 0.088 Uiso 1 1 calc R U . . .
N5 N 0.1012(4) 0.6568(3) 0.34935(19) 0.0762(16) Uani 1 1 d . . . . .
N6 N 0.4078(4) 0.1911(4) 0.3994(2) 0.0879(18) Uani 1 1 d . . . . .
C4 C 0.3612(6) 0.4652(4) 0.0618(3) 0.081(2) Uani 1 1 d . . . . .
H4 H 0.3332 0.4775 0.0316 0.098 Uiso 1 1 calc R U . . .
C3 C 0.3027(5) 0.4635(4) 0.0982(3) 0.081(2) Uani 1 1 d . . . . .
N2 N 0.7692(4) 0.4116(3) 0.15274(18) 0.0725(15) Uani 1 1 d . . . . .
H2N H 0.7835 0.3968 0.1248 0.087 Uiso 1 1 calc R U . . .
C15 C 1.3650(5) 0.4403(3) 0.3280(3) 0.0639(18) Uani 1 1 d . . . . .
C9 C 0.9461(5) 0.4160(3) 0.1724(2) 0.0680(18) Uani 1 1 d . . . . .
H9 H 0.9544 0.4173 0.1400 0.082 Uiso 1 1 calc R U . . .
C6 C 0.5058(5) 0.4325(4) 0.1137(3) 0.0687(19) Uani 1 1 d . . . . .
C14 C 1.1995(5) 0.4314(4) 0.2812(3) 0.0642(18) Uani 1 1 d . . . . .
C5 C 0.4634(5) 0.4488(4) 0.0685(2) 0.0735(19) Uani 1 1 d . . . . .
H5 H 0.5036 0.4487 0.0427 0.088 Uiso 1 1 calc R U . . .
C54 C 0.7622(6) 0.1536(4) 0.5322(3) 0.081(2) Uani 1 1 d . . . . .
C8 C 0.8495(5) 0.4155(4) 0.1880(3) 0.0689(19) Uani 1 1 d . . . . .
C11 C 1.0208(5) 0.4130(3) 0.2523(3) 0.0626(18) Uani 1 1 d . . . . .
C20 C 1.4058(5) 0.4517(3) 0.3741(2) 0.077(2) Uani 1 1 d . . . . .
H20 H 1.3644 0.4510 0.3994 0.093 Uiso 1 1 calc R U . . .
C49 C 0.4153(5) 0.2595(4) 0.4353(3) 0.086(2) Uani 1 1 d . . . . .
H49A H 0.3479 0.2805 0.4387 0.103 Uiso 1 1 calc R U . . .
H49B H 0.4548 0.3026 0.4225 0.103 Uiso 1 1 calc R U . . .
C7 C 0.6712(6) 0.4294(4) 0.1592(3) 0.070(2) Uani 1 1 d . . . . .
C18 C 1.5702(5) 0.4669(4) 0.3449(3) 0.083(2) Uani 1 1 d . . . . .
C10 C 1.0310(5) 0.4148(4) 0.2039(3) 0.077(2) Uani 1 1 d . . . . .
H10 H 1.0950 0.4151 0.1925 0.092 Uiso 1 1 calc R U . . .
C41 C 0.3553(5) 0.2263(4) 0.3549(3) 0.086(2) Uani 1 1 d . . . . .
H41A H 0.3957 0.2711 0.3447 0.103 Uiso 1 1 calc R U . . .
H41B H 0.2909 0.2482 0.3631 0.103 Uiso 1 1 calc R U . . .
C1 C 0.4447(6) 0.4289(4) 0.1498(3) 0.103(3) Uani 1 1 d . . . . .
H1 H 0.4722 0.4152 0.1799 0.123 Uiso 1 1 calc R U . . .
C25 C 0.0274(5) 0.7163(4) 0.3692(3) 0.086(2) Uani 1 1 d . . . . .
H25A H 0.0614 0.7432 0.3963 0.103 Uiso 1 1 calc R U . . .
H25B H 0.0112 0.7571 0.3453 0.103 Uiso 1 1 calc R U . . .
C13 C 0.8394(5) 0.4146(4) 0.2367(3) 0.075(2) Uani 1 1 d . . . . .
H13 H 0.7753 0.4153 0.2482 0.090 Uiso 1 1 calc R U . . .
C2 C 0.3410(5) 0.4450(4) 0.1436(3) 0.102(3) Uani 1 1 d . . . . .
H2 H 0.2997 0.4434 0.1689 0.122 Uiso 1 1 calc R U . . .
C21 C 0.0566(5) 0.6182(4) 0.3035(2) 0.092(2) Uani 1 1 d . . . . .
H21A H -0.0034 0.5882 0.3105 0.110 Uiso 1 1 calc R U . . .
H21B H 0.1051 0.5797 0.2925 0.110 Uiso 1 1 calc R U . . .
C16 C 1.4266(5) 0.4448(4) 0.2912(3) 0.083(2) Uani 1 1 d . . . . .
H16 H 1.3985 0.4401 0.2602 0.099 Uiso 1 1 calc R U . . .
C19 C 1.5098(6) 0.4641(4) 0.3819(3) 0.086(2) Uani 1 1 d . . . . .
H19 H 1.5379 0.4706 0.4128 0.104 Uiso 1 1 calc R U . . .
C37 C 0.3492(6) 0.1202(4) 0.4166(3) 0.095(2) Uani 1 1 d . . . . .
H37A H 0.3878 0.0956 0.4432 0.114 Uiso 1 1 calc R U . . .
H37B H 0.3423 0.0804 0.3913 0.114 Uiso 1 1 calc R U . . .
C38 C 0.2440(5) 0.1410(4) 0.4319(3) 0.093(2) Uani 1 1 d . . . . .
H38A H 0.2503 0.1715 0.4613 0.111 Uiso 1 1 calc R U . . .
H38B H 0.2092 0.1746 0.4079 0.111 Uiso 1 1 calc R U . . .
C17 C 1.5309(6) 0.4563(4) 0.2988(3) 0.096(2) Uani 1 1 d . . . . .
H17 H 1.5726 0.4568 0.2736 0.116 Uiso 1 1 calc R U . . .
C29 C 0.1260(6) 0.5889(4) 0.3833(3) 0.101(3) Uani 1 1 d . . . . .
H29A H 0.1717 0.5522 0.3687 0.121 Uiso 1 1 calc R U . . .
H29B H 0.0643 0.5594 0.3880 0.121 Uiso 1 1 calc R U . . .
C50 C 0.4619(5) 0.2389(5) 0.4847(3) 0.103(3) Uani 1 1 d . . . . .
H50A H 0.5279 0.2145 0.4824 0.124 Uiso 1 1 calc R U . . .
H50B H 0.4192 0.2011 0.5002 0.124 Uiso 1 1 calc R U . . .
C12 C 0.9237(5) 0.4126(4) 0.2682(2) 0.076(2) Uani 1 1 d . . . . .
H12 H 0.9155 0.4111 0.3006 0.091 Uiso 1 1 calc R U . . .
C33 C 0.1942(5) 0.7053(4) 0.3409(3) 0.089(2) Uani 1 1 d . . . . .
H33A H 0.2189 0.7291 0.3709 0.107 Uiso 1 1 calc R U . . .
H33B H 0.1746 0.7493 0.3195 0.107 Uiso 1 1 calc R U . . .
C53 C 0.8035(6) 0.1849(5) 0.4874(3) 0.123(3) Uani 1 1 d . . . . .
H53A H 0.8042 0.2428 0.4880 0.185 Uiso 1 1 calc R U . . .
H53B H 0.7616 0.1666 0.4605 0.185 Uiso 1 1 calc R U . . .
H53C H 0.8711 0.1651 0.4851 0.185 Uiso 1 1 calc R U . . .
C26 C -0.0698(6) 0.6814(4) 0.3845(3) 0.104(3) Uani 1 1 d . . . . .
H26A H -0.0564 0.6431 0.4101 0.125 Uiso 1 1 calc R U . . .
H26B H -0.1055 0.6537 0.3581 0.125 Uiso 1 1 calc R U . . .
C30 C 0.1736(6) 0.6135(4) 0.4317(3) 0.110(3) Uani 1 1 d . . . . .
H30A H 0.2381 0.6394 0.4277 0.132 Uiso 1 1 calc R U . . .
H30B H 0.1302 0.6526 0.4459 0.132 Uiso 1 1 calc R U . . .
C34 C 0.2818(6) 0.6597(4) 0.3202(3) 0.106(3) Uani 1 1 d . . . . .
H34A H 0.3062 0.6177 0.3420 0.127 Uiso 1 1 calc R U . . .
H34B H 0.2589 0.6346 0.2904 0.127 Uiso 1 1 calc R U . . .
C36 C 0.4502(9) 0.6839(7) 0.2950(5) 0.259(7) Uani 1 1 d . U . . .
H36A H 0.4930 0.6631 0.3210 0.389 Uiso 1 1 calc R U . . .
H36B H 0.4864 0.7237 0.2782 0.389 Uiso 1 1 calc R U . . .
H36C H 0.4299 0.6406 0.2739 0.389 Uiso 1 1 calc R U . . .
C52 C 0.5156(8) 0.3005(6) 0.5627(4) 0.207(5) Uani 1 1 d . . . . .
H52A H 0.4716 0.2648 0.5783 0.310 Uiso 1 1 calc R U . . .
H52B H 0.5226 0.3502 0.5802 0.310 Uiso 1 1 calc R U . . .
H52C H 0.5808 0.2757 0.5613 0.310 Uiso 1 1 calc R U . . .
C22 C 0.0283(5) 0.6774(4) 0.2629(2) 0.095(2) Uani 1 1 d . . . . .
H22A H -0.0281 0.7104 0.2713 0.114 Uiso 1 1 calc R U . . .
H22B H 0.0851 0.7128 0.2583 0.114 Uiso 1 1 calc R U . . .
C43 C 0.2971(7) 0.2158(6) 0.2685(3) 0.141(4) Uani 1 1 d . . . . .
H43A H 0.2359 0.2445 0.2751 0.169 Uiso 1 1 calc R U . . .
H43B H 0.3472 0.2552 0.2605 0.169 Uiso 1 1 calc R U . . .
C55 C 0.9492(6) 0.6738(5) 0.5481(3) 0.140(3) Uani 1 1 d . . . . .
H55A H 1.0196 0.6855 0.5549 0.210 Uiso 1 1 calc R U . . .
H55B H 0.9141 0.7224 0.5385 0.210 Uiso 1 1 calc R U . . .
H55C H 0.9419 0.6348 0.5229 0.210 Uiso 1 1 calc R U . . .
C23 C -0.0002(7) 0.6323(5) 0.2170(3) 0.118(3) Uani 1 1 d . . . . .
H23A H 0.0564 0.5991 0.2091 0.141 Uiso 1 1 calc R U . . .
H23B H -0.0565 0.5967 0.2221 0.141 Uiso 1 1 calc R U . . .
C39 C 0.1837(6) 0.0670(4) 0.4390(3) 0.105(3) Uani 1 1 d . . . . .
H39A H 0.1749 0.0387 0.4089 0.126 Uiso 1 1 calc R U . . .
H39B H 0.2220 0.0320 0.4610 0.126 Uiso 1 1 calc R U . . .
C56 C 0.9047(7) 0.6398(5) 0.5925(3) 0.088(2) Uani 1 1 d . . . . .
C45 C 0.5110(5) 0.1587(4) 0.3884(3) 0.106(3) Uani 1 1 d . . . . .
H45A H 0.5015 0.1168 0.3645 0.127 Uiso 1 1 calc R U . . .
H45B H 0.5421 0.1338 0.4169 0.127 Uiso 1 1 calc R U . . .
C24 C -0.0289(7) 0.6865(5) 0.1759(3) 0.140(3) Uani 1 1 d . . . . .
H24A H -0.0916 0.7129 0.1811 0.209 Uiso 1 1 calc R U . . .
H24B H -0.0364 0.6550 0.1473 0.209 Uiso 1 1 calc R U . . .
H24C H 0.0229 0.7263 0.1729 0.209 Uiso 1 1 calc R U . . .
C42 C 0.3361(7) 0.1692(5) 0.3132(3) 0.122(3) Uani 1 1 d . . . . .
H42A H 0.2867 0.1290 0.3209 0.146 Uiso 1 1 calc R U . . .
H42B H 0.3983 0.1415 0.3070 0.146 Uiso 1 1 calc R U . . .
C35 C 0.3655(7) 0.7189(6) 0.3124(4) 0.160(4) Uani 1 1 d . U . . .
H35A H 0.3400 0.7600 0.2902 0.192 Uiso 1 1 calc R U . . .
H35B H 0.3850 0.7454 0.3422 0.192 Uiso 1 1 calc R U . . .
C44 C 0.2761(8) 0.1620(7) 0.2285(4) 0.196(5) Uani 1 1 d . . . . .
H44A H 0.3327 0.1267 0.2255 0.294 Uiso 1 1 calc R U . . .
H44B H 0.2648 0.1932 0.2000 0.294 Uiso 1 1 calc R U . . .
H44C H 0.2170 0.1306 0.2336 0.294 Uiso 1 1 calc R U . . .
C27 C -0.1339(7) 0.7529(5) 0.4014(4) 0.142(4) Uani 1 1 d . . . . .
H27A H -0.0953 0.7822 0.4262 0.171 Uiso 1 1 calc R U . . .
H27B H -0.1488 0.7896 0.3751 0.171 Uiso 1 1 calc R U . . .
C40 C 0.0836(6) 0.0807(5) 0.4569(3) 0.131(3) Uani 1 1 d . . . . .
H40A H 0.0911 0.0937 0.4901 0.197 Uiso 1 1 calc R U . . .
H40B H 0.0434 0.0328 0.4524 0.197 Uiso 1 1 calc R U . . .
H40C H 0.0508 0.1247 0.4399 0.197 Uiso 1 1 calc R U . . .
C28 C -0.2290(8) 0.7246(7) 0.4195(4) 0.200(5) Uani 1 1 d . . . . .
H28A H -0.2693 0.6988 0.3944 0.300 Uiso 1 1 calc R U . . .
H28B H -0.2653 0.7698 0.4311 0.300 Uiso 1 1 calc R U . . .
H28C H -0.2145 0.6869 0.4449 0.300 Uiso 1 1 calc R U . . .
C32 C 0.2444(10) 0.5604(7) 0.5084(4) 0.253(8) Uani 1 1 d . . . . .
H32A H 0.3104 0.5366 0.5084 0.380 Uiso 1 1 calc R U . . .
H32B H 0.2089 0.5380 0.5339 0.380 Uiso 1 1 calc R U . . .
H32C H 0.2508 0.6177 0.5126 0.380 Uiso 1 1 calc R U . . .
C46 C 0.5841(6) 0.2217(5) 0.3707(4) 0.143(4) Uani 1 1 d . . . . .
H46A H 0.5506 0.2532 0.3453 0.172 Uiso 1 1 calc R U . . .
H46B H 0.6053 0.2581 0.3964 0.172 Uiso 1 1 calc R U . . .
C51 C 0.4715(8) 0.3178(6) 0.5129(3) 0.162(4) Uani 1 1 d . . . . .
H51A H 0.5149 0.3550 0.4973 0.194 Uiso 1 1 calc R U . . .
H51B H 0.4055 0.3425 0.5142 0.194 Uiso 1 1 calc R U . . .
C31 C 0.1895(8) 0.5440(5) 0.4642(3) 0.163(5) Uani 1 1 d . . . . .
H31A H 0.1239 0.5224 0.4707 0.196 Uiso 1 1 calc R U . . .
H31B H 0.2250 0.5023 0.4479 0.196 Uiso 1 1 calc R U . . .
C47 C 0.6748(7) 0.1795(6) 0.3529(4) 0.177(5) Uani 1 1 d . . . . .
H47A H 0.7070 0.1473 0.3783 0.213 Uiso 1 1 calc R U . . .
H47B H 0.6529 0.1433 0.3272 0.213 Uiso 1 1 calc R U . . .
C48 C 0.7480(9) 0.2367(9) 0.3360(6) 0.299(9) Uani 1 1 d . . . . .
H48A H 0.7236 0.2575 0.3056 0.448 Uiso 1 1 calc R U . . .
H48B H 0.8114 0.2098 0.3330 0.448 Uiso 1 1 calc R U . . .
H48C H 0.7571 0.2804 0.3582 0.448 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.909(7) . ?
Br2 C18 1.882(7) . ?
O6 C56 1.238(8) . ?
O2 C14 1.201(7) . ?
O1 C7 1.217(7) . ?
O4 C54 1.238(7) . ?
O3 C54 1.236(7) . ?
N4 C14 1.384(7) . ?
N4 C15 1.404(7) . ?
N1 C7 1.394(7) . ?
N1 C6 1.400(7) . ?
O5 C56 1.260(8) . ?
N3 C14 1.362(7) . ?
N3 C11 1.415(7) . ?
N5 C29 1.499(7) . ?
N5 C33 1.505(8) . ?
N5 C25 1.523(7) . ?
N5 C21 1.528(7) . ?
N6 C37 1.506(8) . ?
N6 C41 1.511(7) . ?
N6 C49 1.519(8) . ?
N6 C45 1.523(8) . ?
C4 C3 1.328(9) . ?
C4 C5 1.383(8) . ?
C3 C2 1.381(9) . ?
N2 C7 1.357(8) . ?
N2 C8 1.410(7) . ?
C15 C16 1.368(8) . ?
C15 C20 1.387(8) . ?
C9 C8 1.383(8) . ?
C9 C10 1.387(7) . ?
C6 C1 1.347(9) . ?
C6 C5 1.385(8) . ?
C54 C53 1.502(9) . ?
C8 C13 1.389(9) . ?
C11 C10 1.380(8) . ?
C11 C12 1.392(8) . ?
C20 C19 1.398(8) . ?
C49 C50 1.523(8) . ?
C18 C19 1.361(9) . ?
C18 C17 1.380(9) . ?
C41 C42 1.520(9) . ?
C1 C2 1.400(8) . ?
C25 C26 1.502(9) . ?
C13 C12 1.381(7) . ?
C21 C22 1.534(8) . ?
C16 C17 1.399(8) . ?
C37 C38 1.528(8) . ?
C38 C39 1.484(8) . ?
C29 C30 1.524(8) . ?
C50 C51 1.530(10) . ?
C33 C34 1.533(9) . ?
C26 C27 1.551(10) . ?
C30 C31 1.478(9) . ?
C34 C35 1.508(10) . ?
C36 C35 1.382(11) . ?
C52 C51 1.515(11) . ?
C22 C23 1.522(8) . ?
C43 C44 1.451(10) . ?
C43 C42 1.537(10) . ?
C55 C56 1.528(10) . ?
C23 C24 1.496(9) . ?
C39 C40 1.471(9) . ?
C45 C46 1.531(9) . ?
C27 C28 1.469(11) . ?
C32 C31 1.429(10) . ?
C46 C47 1.507(11) . ?
C47 C48 1.459(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
C14 N4 C15 126.5(6) . . ?
C7 N1 C6 124.1(6) . . ?
C14 N3 C11 125.9(6) . . ?
C29 N5 C33 110.8(5) . . ?
C29 N5 C25 111.6(6) . . ?
C33 N5 C25 105.5(5) . . ?
C29 N5 C21 106.4(5) . . ?
C33 N5 C21 111.4(6) . . ?
C25 N5 C21 111.2(5) . . ?
C37 N6 C41 110.4(5) . . ?
C37 N6 C49 112.3(6) . . ?
C41 N6 C49 105.8(5) . . ?
C37 N6 C45 106.3(5) . . ?
C41 N6 C45 109.6(6) . . ?
C49 N6 C45 112.3(5) . . ?
C3 C4 C5 120.6(7) . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 Br1 121.2(6) . . ?
C2 C3 Br1 117.1(7) . . ?
C7 N2 C8 125.5(6) . . ?
C16 C15 C20 119.3(6) . . ?
C16 C15 N4 124.2(6) . . ?
C20 C15 N4 116.5(7) . . ?
C8 C9 C10 121.7(7) . . ?
C1 C6 C5 118.6(7) . . ?
C1 C6 N1 124.5(6) . . ?
C5 C6 N1 116.8(7) . . ?
O2 C14 N3 124.4(6) . . ?
O2 C14 N4 123.2(6) . . ?
N3 C14 N4 112.4(7) . . ?
C4 C5 C6 119.8(7) . . ?
O3 C54 O4 126.3(8) . . ?
O3 C54 C53 117.3(7) . . ?
O4 C54 C53 116.4(7) . . ?
C9 C8 C13 117.9(6) . . ?
C9 C8 N2 116.6(7) . . ?
C13 C8 N2 125.5(6) . . ?
C10 C11 C12 118.2(6) . . ?
C10 C11 N3 125.0(6) . . ?
C12 C11 N3 116.8(6) . . ?
C15 C20 C19 119.2(7) . . ?
N6 C49 C50 116.6(6) . . ?
O1 C7 N2 125.1(6) . . ?
O1 C7 N1 123.3(7) . . ?
N2 C7 N1 111.5(7) . . ?
C19 C18 C17 121.1(7) . . ?
C19 C18 Br2 119.2(6) . . ?
C17 C18 Br2 119.7(7) . . ?
C11 C10 C9 120.4(7) . . ?
N6 C41 C42 116.6(6) . . ?
C6 C1 C2 122.1(7) . . ?
C26 C25 N5 116.2(6) . . ?
C12 C13 C8 120.6(6) . . ?
C3 C2 C1 117.1(7) . . ?
N5 C21 C22 115.2(5) . . ?
C15 C16 C17 121.7(7) . . ?
C18 C19 C20 120.6(7) . . ?
N6 C37 C38 114.6(5) . . ?
C39 C38 C37 111.2(6) . . ?
C18 C17 C16 118.0(7) . . ?
N5 C29 C30 115.6(5) . . ?
C49 C50 C51 107.4(6) . . ?
C13 C12 C11 121.2(7) . . ?
N5 C33 C34 116.6(6) . . ?
C25 C26 C27 107.1(6) . . ?
C31 C30 C29 112.4(6) . . ?
C35 C34 C33 108.7(7) . . ?
C23 C22 C21 110.9(6) . . ?
C44 C43 C42 111.5(8) . . ?
C24 C23 C22 113.8(6) . . ?
C40 C39 C38 115.2(7) . . ?
O6 C56 O5 124.2(9) . . ?
O6 C56 C55 118.0(8) . . ?
O5 C56 C55 117.8(8) . . ?
N6 C45 C46 115.0(6) . . ?
C41 C42 C43 110.7(6) . . ?
C36 C35 C34 113.8(9) . . ?
C28 C27 C26 111.4(8) . . ?
C47 C46 C45 109.2(7) . . ?
C52 C51 C50 109.7(8) . . ?
C32 C31 C30 115.8(9) . . ?
C48 C47 C46 111.8(10) . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_ppda-p-Cl-TBAOAC-1c
_database_code_depnum_ccdc_archive 'CCDC 1860328'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl2 N4 O2, 2(C16 H36 N), 2(C2 H3 O2)'
_chemical_formula_sum            'C56 H94 Cl2 N6 O6'
_chemical_formula_weight         1018.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.2862(6)
_cell_length_b                   16.5740(8)
_cell_length_c                   28.0803(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.874(5)
_cell_angle_gamma                90
_cell_volume                     6169.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4054
_cell_measurement_theta_min      3.5920
_cell_measurement_theta_max      22.1420

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_F_000             2216.0
_exptl_transmission_factor_min   0.956
_exptl_transmission_factor_max   0.968
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25218
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10858
_reflns_number_gt                5267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00058(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10858
_refine_ls_number_parameters     642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2165
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.33303(9) 0.48673(9) 0.59190(5) 0.1147(5) Uani 1 1 d . . . . .
Cl2 Cl 1.19505(10) 0.48899(12) 0.85716(6) 0.1466(7) Uani 1 1 d . . . . .
O1 O 0.1353(2) 0.46113(19) 0.69722(11) 0.0862(9) Uani 1 1 d . . . . .
O2 O 0.7254(2) 0.4600(2) 0.74641(11) 0.0915(10) Uani 1 1 d . . . . .
O4 O 0.3129(3) 0.34206(19) 0.57021(10) 0.1006(10) Uani 1 1 d . . . . .
N3 N 0.5986(2) 0.41263(18) 0.78955(11) 0.0643(8) Uani 1 1 d . . . . .
H3N H 0.5857 0.3955 0.8174 0.077 Uiso 1 1 calc R U . . .
O6 O 0.6880(2) 0.15075(19) 0.40573(11) 0.0914(9) Uani 1 1 d . . . . .
N2 N 0.2646(2) 0.41595(19) 0.65439(11) 0.0671(9) Uani 1 1 d . . . . .
H2N H 0.2787 0.4009 0.6263 0.081 Uiso 1 1 calc R U . . .
N4 N 0.7567(2) 0.42545(19) 0.82468(11) 0.0668(9) Uani 1 1 d . . . . .
H4N H 0.7288 0.4084 0.8495 0.080 Uiso 1 1 calc R U . . .
N1 N 0.1043(2) 0.41962(19) 0.61963(11) 0.0710(9) Uani 1 1 d . . . . .
H1N H 0.1322 0.4003 0.5953 0.085 Uiso 1 1 calc R U . . .
O5 O 0.5382(2) 0.1015(2) 0.38226(11) 0.0996(10) Uani 1 1 d . . . . .
O3 O 0.1756(2) 0.3837(2) 0.52915(11) 0.1017(10) Uani 1 1 d . . . . .
N6 N 0.6021(3) 0.83887(19) 0.34851(11) 0.0713(9) Uani 1 1 d . . . . .
C11 C 0.5161(3) 0.4164(2) 0.75456(14) 0.0598(10) Uani 1 1 d . . . . .
C8 C 0.3458(3) 0.4198(2) 0.68935(13) 0.0600(10) Uani 1 1 d . . . . .
N5 N 0.0945(3) 0.6926(2) 0.59929(13) 0.0773(10) Uani 1 1 d . . . . .
C9 C 0.4423(3) 0.4200(2) 0.67395(13) 0.0625(10) Uani 1 1 d . . . . .
H9 H 0.4507 0.4217 0.6414 0.075 Uiso 1 1 calc R U . . .
C14 C 0.6954(3) 0.4334(2) 0.78332(15) 0.0650(10) Uani 1 1 d . . . . .
C7 C 0.1658(3) 0.4336(2) 0.66043(15) 0.0655(10) Uani 1 1 d . . . . .
C10 C 0.5269(3) 0.4178(2) 0.70561(13) 0.0637(10) Uani 1 1 d . . . . .
H10 H 0.5909 0.4174 0.6941 0.076 Uiso 1 1 calc R U . . .
C13 C 0.3352(3) 0.4189(2) 0.73828(14) 0.0693(11) Uani 1 1 d . . . . .
H13 H 0.2710 0.4193 0.7496 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0003(3) 0.4341(2) 0.61452(14) 0.0661(10) Uani 1 1 d . . . . .
C12 C 0.4195(3) 0.4173(2) 0.77035(14) 0.0657(10) Uani 1 1 d . . . . .
H12 H 0.4109 0.4168 0.8029 0.079 Uiso 1 1 calc R U . . .
C15 C 0.8610(3) 0.4427(2) 0.83015(14) 0.0634(10) Uani 1 1 d . . . . .
C3 C -0.2045(3) 0.4652(3) 0.60009(16) 0.0792(12) Uani 1 1 d . . . . .
C54 C 0.2602(4) 0.3508(3) 0.53223(16) 0.0750(12) Uani 1 1 d . . . . .
C5 C -0.0431(3) 0.4508(2) 0.56974(14) 0.0701(11) Uani 1 1 d . . . . .
H5 H -0.0030 0.4512 0.5438 0.084 Uiso 1 1 calc R U . . .
C20 C 0.9042(3) 0.4528(2) 0.87616(14) 0.0699(11) Uani 1 1 d . . . . .
H20 H 0.8637 0.4498 0.9019 0.084 Uiso 1 1 calc R U . . .
C41 C 0.6958(3) 0.7910(2) 0.33933(15) 0.0768(12) Uani 1 1 d . . . . .
H41A H 0.7211 0.7671 0.3693 0.092 Uiso 1 1 calc R U . . .
H41B H 0.6761 0.7472 0.3178 0.092 Uiso 1 1 calc R U . . .
C4 C -0.1460(3) 0.4670(2) 0.56232(16) 0.0787(12) Uani 1 1 d . . . . .
H4 H -0.1741 0.4788 0.5319 0.094 Uiso 1 1 calc R U . . .
C18 C 1.0669(3) 0.4710(3) 0.84713(18) 0.0881(14) Uani 1 1 d . . . . .
C49 C 0.5282(3) 0.7797(2) 0.36857(15) 0.0788(12) Uani 1 1 d . . . . .
H49A H 0.5113 0.7393 0.3444 0.095 Uiso 1 1 calc R U . . .
H49B H 0.5624 0.7523 0.3955 0.095 Uiso 1 1 calc R U . . .
C17 C 1.0257(3) 0.4613(3) 0.80109(17) 0.0920(14) Uani 1 1 d . . . . .
H17 H 1.0668 0.4646 0.7756 0.110 Uiso 1 1 calc R U . . .
C21 C 0.1472(3) 0.7279(2) 0.64417(15) 0.0817(12) Uani 1 1 d . . . . .
H21A H 0.2115 0.7496 0.6359 0.098 Uiso 1 1 calc R U . . .
H21B H 0.1071 0.7728 0.6544 0.098 Uiso 1 1 calc R U . . .
C45 C 0.5571(3) 0.8774(2) 0.30246(14) 0.0798(12) Uani 1 1 d . . . . .
H45A H 0.4977 0.9077 0.3098 0.096 Uiso 1 1 calc R U . . .
H45B H 0.6057 0.9154 0.2913 0.096 Uiso 1 1 calc R U . . .
C56 C 0.5967(4) 0.1390(3) 0.41085(16) 0.0799(12) Uani 1 1 d . . . . .
C16 C 0.9237(3) 0.4468(3) 0.79265(16) 0.0841(13) Uani 1 1 d . . . . .
H16 H 0.8967 0.4398 0.7615 0.101 Uiso 1 1 calc R U . . .
C29 C 0.0866(3) 0.7600(2) 0.56281(15) 0.0774(12) Uani 1 1 d . . . . .
H29A H 0.1540 0.7804 0.5589 0.093 Uiso 1 1 calc R U . . .
H29B H 0.0480 0.8036 0.5757 0.093 Uiso 1 1 calc R U . . .
C19 C 1.0058(3) 0.4672(3) 0.88436(16) 0.0829(13) Uani 1 1 d . . . . .
H19 H 1.0332 0.4744 0.9154 0.099 Uiso 1 1 calc R U . . .
C1 C -0.0613(3) 0.4319(3) 0.65200(16) 0.0958(15) Uani 1 1 d . . . . .
H1 H -0.0338 0.4200 0.6825 0.115 Uiso 1 1 calc R U . . .
C25 C 0.1535(3) 0.6220(2) 0.58170(17) 0.0885(14) Uani 1 1 d . . . . .
H25A H 0.1142 0.5972 0.5552 0.106 Uiso 1 1 calc R U . . .
H25B H 0.1611 0.5824 0.6071 0.106 Uiso 1 1 calc R U . . .
C46 C 0.5276(4) 0.8189(3) 0.26190(15) 0.0878(14) Uani 1 1 d . . . . .
H46A H 0.5833 0.7825 0.2573 0.105 Uiso 1 1 calc R U . . .
H46B H 0.4703 0.7868 0.2703 0.105 Uiso 1 1 calc R U . . .
C2 C -0.1645(3) 0.4471(3) 0.64476(17) 0.1015(16) Uani 1 1 d . . . . .
H2 H -0.2056 0.4450 0.6702 0.122 Uiso 1 1 calc R U . . .
C26 C 0.2576(3) 0.6420(3) 0.56545(17) 0.0871(13) Uani 1 1 d . . . . .
H26A H 0.2507 0.6689 0.5347 0.105 Uiso 1 1 calc R U . . .
H26B H 0.2918 0.6785 0.5882 0.105 Uiso 1 1 calc R U . . .
C37 C 0.6265(3) 0.9072(2) 0.38329(15) 0.0822(13) Uani 1 1 d . . . . .
H37A H 0.5648 0.9365 0.3880 0.099 Uiso 1 1 calc R U . . .
H37B H 0.6722 0.9441 0.3689 0.099 Uiso 1 1 calc R U . . .
C30 C 0.0388(3) 0.7386(3) 0.51376(17) 0.0928(14) Uani 1 1 d . . . . .
H30A H -0.0271 0.7147 0.5169 0.111 Uiso 1 1 calc R U . . .
H30B H 0.0805 0.6995 0.4986 0.111 Uiso 1 1 calc R U . . .
C53 C 0.3026(4) 0.3216(3) 0.48759(16) 0.1201(19) Uani 1 1 d . . . . .
H53A H 0.3637 0.2922 0.4954 0.180 Uiso 1 1 calc R U . . .
H53B H 0.3169 0.3670 0.4678 0.180 Uiso 1 1 calc R U . . .
H53C H 0.2546 0.2870 0.4707 0.180 Uiso 1 1 calc R U . . .
C55 C 0.5526(4) 0.1717(4) 0.45566(19) 0.132(2) Uani 1 1 d . . . . .
H55A H 0.4820 0.1823 0.4491 0.198 Uiso 1 1 calc R U . . .
H55B H 0.5866 0.2207 0.4653 0.198 Uiso 1 1 calc R U . . .
H55C H 0.5614 0.1325 0.4808 0.198 Uiso 1 1 calc R U . . .
C42 C 0.7810(4) 0.8358(3) 0.31876(19) 0.1015(15) Uani 1 1 d . . . . .
H42A H 0.8070 0.8765 0.3412 0.122 Uiso 1 1 calc R U . . .
H42B H 0.7569 0.8627 0.2895 0.122 Uiso 1 1 calc R U . . .
C24 C 0.2266(5) 0.6629(5) 0.7722(2) 0.176(3) Uani 1 1 d . . . . .
H24A H 0.1665 0.6341 0.7788 0.264 Uiso 1 1 calc R U . . .
H24B H 0.2491 0.6944 0.7996 0.264 Uiso 1 1 calc R U . . .
H24C H 0.2783 0.6252 0.7650 0.264 Uiso 1 1 calc R U . . .
C27 C 0.3194(4) 0.5669(3) 0.56136(19) 0.1010(16) Uani 1 1 d . . . . .
H27A H 0.3303 0.5428 0.5928 0.121 Uiso 1 1 calc R U . . .
H27B H 0.2814 0.5286 0.5411 0.121 Uiso 1 1 calc R U . . .
C47 C 0.5003(4) 0.8641(3) 0.21574(17) 0.1069(16) Uani 1 1 d . . . . .
H47A H 0.4450 0.9006 0.2208 0.128 Uiso 1 1 calc R U . . .
H47B H 0.5577 0.8964 0.2078 0.128 Uiso 1 1 calc R U . . .
C33 C -0.0097(3) 0.6610(3) 0.60971(19) 0.0999(16) Uani 1 1 d . . . . .
H33A H -0.0012 0.6186 0.6335 0.120 Uiso 1 1 calc R U . . .
H33B H -0.0403 0.6368 0.5808 0.120 Uiso 1 1 calc R U . . .
C28 C 0.4197(4) 0.5808(3) 0.5413(2) 0.122(2) Uani 1 1 d . . . . .
H28A H 0.4098 0.5941 0.5081 0.184 Uiso 1 1 calc R U . . .
H28B H 0.4598 0.5327 0.5449 0.184 Uiso 1 1 calc R U . . .
H28C H 0.4538 0.6244 0.5581 0.184 Uiso 1 1 calc R U . . .
C31 C 0.0281(5) 0.8147(4) 0.48309(19) 0.127(2) Uani 1 1 d . . . . .
H31A H -0.0131 0.8536 0.4988 0.152 Uiso 1 1 calc R U . . .
H31B H 0.0942 0.8384 0.4805 0.152 Uiso 1 1 calc R U . . .
C50 C 0.4311(4) 0.8143(3) 0.38463(18) 0.0972(15) Uani 1 1 d . . . . .
H50A H 0.3960 0.8435 0.3586 0.117 Uiso 1 1 calc R U . . .
H50B H 0.4455 0.8517 0.4108 0.117 Uiso 1 1 calc R U . . .
C38 C 0.6737(4) 0.8819(3) 0.43191(17) 0.1022(16) Uani 1 1 d . . . . .
H38A H 0.6305 0.8426 0.4460 0.123 Uiso 1 1 calc R U . . .
H38B H 0.7384 0.8565 0.4280 0.123 Uiso 1 1 calc R U . . .
C51 C 0.3649(4) 0.7450(3) 0.4008(2) 0.129(2) Uani 1 1 d . . . . .
H51A H 0.3505 0.7087 0.3741 0.155 Uiso 1 1 calc R U . . .
H51B H 0.4023 0.7149 0.4257 0.155 Uiso 1 1 calc R U . . .
C22 C 0.1665(4) 0.6717(3) 0.68623(19) 0.1106(17) Uani 1 1 d . . . . .
H22A H 0.2158 0.6314 0.6786 0.133 Uiso 1 1 calc R U . . .
H22B H 0.1044 0.6440 0.6925 0.133 Uiso 1 1 calc R U . . .
C48 C 0.4707(5) 0.8105(4) 0.17462(18) 0.132(2) Uani 1 1 d . . . . .
H48A H 0.5252 0.7743 0.1692 0.198 Uiso 1 1 calc R U . . .
H48B H 0.4558 0.8426 0.1466 0.198 Uiso 1 1 calc R U . . .
H48C H 0.4121 0.7799 0.1815 0.198 Uiso 1 1 calc R U . . .
C35 C -0.1754(4) 0.6840(5) 0.6446(3) 0.163(3) Uani 1 1 d . . . . .
H35A H -0.2075 0.6520 0.6190 0.195 Uiso 1 1 calc R U . . .
H35B H -0.1560 0.6480 0.6709 0.195 Uiso 1 1 calc R U . . .
C34 C -0.0826(4) 0.7239(4) 0.6275(2) 0.128(2) Uani 1 1 d . . . . .
H34A H -0.0492 0.7545 0.6534 0.154 Uiso 1 1 calc R U . . .
H34B H -0.1020 0.7612 0.6019 0.154 Uiso 1 1 calc R U . . .
C43 C 0.8646(4) 0.7766(4) 0.3085(2) 0.132(2) Uani 1 1 d . . . . .
H43A H 0.8846 0.7477 0.3376 0.158 Uiso 1 1 calc R U . . .
H43B H 0.8378 0.7373 0.2853 0.158 Uiso 1 1 calc R U . . .
C23 C 0.2048(4) 0.7178(4) 0.73034(19) 0.1237(19) Uani 1 1 d . . . . .
H23A H 0.2658 0.7465 0.7237 0.148 Uiso 1 1 calc R U . . .
H23B H 0.1547 0.7573 0.7382 0.148 Uiso 1 1 calc R U . . .
C39 C 0.6883(5) 0.9524(4) 0.46462(19) 0.137(2) Uani 1 1 d . . . . .
H39A H 0.7251 0.9939 0.4487 0.165 Uiso 1 1 calc R U . . .
H39B H 0.6228 0.9743 0.4708 0.165 Uiso 1 1 calc R U . . .
C40 C 0.7438(6) 0.9332(5) 0.5111(2) 0.197(4) Uani 1 1 d . . . . .
H40A H 0.7128 0.8878 0.5254 0.296 Uiso 1 1 calc R U . . .
H40B H 0.7418 0.9790 0.5320 0.296 Uiso 1 1 calc R U . . .
H40C H 0.8127 0.9205 0.5059 0.296 Uiso 1 1 calc R U . . .
C32 C -0.0190(5) 0.7981(4) 0.4337(2) 0.172(3) Uani 1 1 d . . . . .
H32A H 0.0281 0.7692 0.4156 0.258 Uiso 1 1 calc R U . . .
H32B H -0.0361 0.8483 0.4181 0.258 Uiso 1 1 calc R U . . .
H32C H -0.0789 0.7663 0.4360 0.258 Uiso 1 1 calc R U . . .
C52 C 0.2673(5) 0.7724(5) 0.4190(2) 0.172(3) Uani 1 1 d . . . . .
H52A H 0.2807 0.8093 0.4450 0.258 Uiso 1 1 calc R U . . .
H52B H 0.2311 0.7266 0.4299 0.258 Uiso 1 1 calc R U . . .
H52C H 0.2275 0.7989 0.3939 0.258 Uiso 1 1 calc R U . . .
C44 C 0.9523(6) 0.8129(5) 0.2907(3) 0.224(4) Uani 1 1 d . . . . .
H44A H 0.9322 0.8510 0.2661 0.335 Uiso 1 1 calc R U . . .
H44B H 0.9936 0.7718 0.2778 0.335 Uiso 1 1 calc R U . . .
H44C H 0.9900 0.8402 0.3162 0.335 Uiso 1 1 calc R U . . .
C36 C -0.2486(6) 0.7451(7) 0.6606(3) 0.271(6) Uani 1 1 d . . . . .
H36A H -0.2179 0.7752 0.6870 0.407 Uiso 1 1 calc R U . . .
H36B H -0.3077 0.7182 0.6705 0.407 Uiso 1 1 calc R U . . .
H36C H -0.2672 0.7811 0.6348 0.407 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.744(4) . ?
Cl2 C18 1.732(4) . ?
O1 C7 1.223(4) . ?
O2 C14 1.218(4) . ?
O4 C54 1.244(5) . ?
N3 C14 1.354(5) . ?
N3 C11 1.423(4) . ?
O6 C56 1.246(5) . ?
N2 C7 1.366(5) . ?
N2 C8 1.411(4) . ?
N4 C14 1.379(5) . ?
N4 C15 1.412(4) . ?
N1 C7 1.382(5) . ?
N1 C6 1.400(4) . ?
O5 C56 1.246(5) . ?
O3 C54 1.247(5) . ?
N6 C41 1.512(5) . ?
N6 C37 1.516(5) . ?
N6 C49 1.522(5) . ?
N6 C45 1.527(5) . ?
C11 C12 1.387(5) . ?
C11 C10 1.392(5) . ?
C8 C9 1.380(5) . ?
C8 C13 1.391(5) . ?
N5 C25 1.509(5) . ?
N5 C29 1.515(5) . ?
N5 C21 1.517(5) . ?
N5 C33 1.526(5) . ?
C9 C10 1.386(5) . ?
C13 C12 1.389(5) . ?
C6 C5 1.376(5) . ?
C6 C1 1.377(5) . ?
C15 C16 1.388(5) . ?
C15 C20 1.388(5) . ?
C3 C4 1.357(6) . ?
C3 C2 1.362(6) . ?
C54 C53 1.489(6) . ?
C5 C4 1.394(5) . ?
C20 C19 1.375(5) . ?
C41 C42 1.502(5) . ?
C18 C19 1.368(6) . ?
C18 C17 1.379(6) . ?
C49 C50 1.508(6) . ?
C17 C16 1.381(5) . ?
C21 C22 1.512(6) . ?
C45 C46 1.526(5) . ?
C56 C55 1.522(6) . ?
C29 C30 1.520(5) . ?
C1 C2 1.395(6) . ?
C25 C26 1.522(5) . ?
C46 C47 1.520(5) . ?
C26 C27 1.500(6) . ?
C37 C38 1.522(6) . ?
C30 C31 1.528(6) . ?
C42 C43 1.524(7) . ?
C24 C23 1.498(7) . ?
C27 C28 1.499(6) . ?
C47 C48 1.489(6) . ?
C33 C34 1.531(6) . ?
C31 C32 1.508(7) . ?
C50 C51 1.535(6) . ?
C38 C39 1.491(6) . ?
C51 C52 1.497(7) . ?
C22 C23 1.514(6) . ?
C35 C36 1.494(10) . ?
C35 C34 1.507(7) . ?
C43 C44 1.431(7) . ?
C39 C40 1.489(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
C14 N3 C11 126.4(3) . . ?
C7 N2 C8 126.9(3) . . ?
C14 N4 C15 126.3(3) . . ?
C7 N1 C6 125.5(4) . . ?
C41 N6 C37 111.0(3) . . ?
C41 N6 C49 106.5(3) . . ?
C37 N6 C49 111.0(3) . . ?
C41 N6 C45 110.7(3) . . ?
C37 N6 C45 106.8(3) . . ?
C49 N6 C45 110.9(3) . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 N3 117.8(3) . . ?
C10 C11 N3 123.8(4) . . ?
C9 C8 C13 117.9(4) . . ?
C9 C8 N2 117.7(3) . . ?
C13 C8 N2 124.2(4) . . ?
C25 N5 C29 111.3(3) . . ?
C25 N5 C21 110.5(3) . . ?
C29 N5 C21 106.5(3) . . ?
C25 N5 C33 107.1(3) . . ?
C29 N5 C33 111.2(3) . . ?
C21 N5 C33 110.3(3) . . ?
C8 C9 C10 122.0(4) . . ?
O2 C14 N3 124.8(4) . . ?
O2 C14 N4 122.8(4) . . ?
N3 C14 N4 112.3(4) . . ?
O1 C7 N2 124.1(4) . . ?
O1 C7 N1 123.5(4) . . ?
N2 C7 N1 112.4(4) . . ?
C9 C10 C11 120.1(4) . . ?
C12 C13 C8 120.6(4) . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 N1 118.6(4) . . ?
C1 C6 N1 123.4(4) . . ?
C11 C12 C13 121.1(4) . . ?
C16 C15 C20 117.9(4) . . ?
C16 C15 N4 124.2(4) . . ?
C20 C15 N4 117.8(4) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 Cl1 120.0(3) . . ?
C2 C3 Cl1 119.0(4) . . ?
O4 C54 O3 124.2(4) . . ?
O4 C54 C53 117.5(4) . . ?
O3 C54 C53 118.3(4) . . ?
C6 C5 C4 121.4(4) . . ?
C19 C20 C15 121.1(4) . . ?
C42 C41 N6 117.2(3) . . ?
C3 C4 C5 119.1(4) . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 Cl2 120.7(4) . . ?
C17 C18 Cl2 119.8(4) . . ?
C50 C49 N6 116.9(3) . . ?
C18 C17 C16 120.3(4) . . ?
C22 C21 N5 117.1(4) . . ?
C46 C45 N6 115.6(3) . . ?
O5 C56 O6 125.0(4) . . ?
O5 C56 C55 116.9(5) . . ?
O6 C56 C55 118.2(5) . . ?
C17 C16 C15 120.7(4) . . ?
N5 C29 C30 116.5(3) . . ?
C18 C19 C20 120.5(4) . . ?
C6 C1 C2 120.8(4) . . ?
N5 C25 C26 115.6(3) . . ?
C47 C46 C45 111.0(4) . . ?
C3 C2 C1 119.5(4) . . ?
C27 C26 C25 110.8(4) . . ?
N6 C37 C38 115.5(3) . . ?
C29 C30 C31 109.6(4) . . ?
C41 C42 C43 109.4(4) . . ?
C28 C27 C26 114.0(4) . . ?
C48 C47 C46 113.7(4) . . ?
N5 C33 C34 115.5(4) . . ?
C32 C31 C30 112.7(5) . . ?
C49 C50 C51 108.8(4) . . ?
C39 C38 C37 111.4(4) . . ?
C52 C51 C50 113.6(5) . . ?
C21 C22 C23 111.0(4) . . ?
C36 C35 C34 111.2(6) . . ?
C35 C34 C33 110.8(5) . . ?
C44 C43 C42 114.6(6) . . ?
C24 C23 C22 111.9(5) . . ?
C40 C39 C38 114.1(5) . . ?

_refine_diff_density_max         0.974
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_ppda-p-Cl-TBAOH-HCO3-1b
_database_code_depnum_ccdc_archive 'CCDC 1860327'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl2 N4 O2, 2(C16 H36 N), 2(C H O3)'
_chemical_formula_sum            'C54 H90 Cl2 N6 O8'
_chemical_formula_weight         1022.22

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4539(7)
_cell_length_b                   10.2145(8)
_cell_length_c                   18.1488(15)
_cell_angle_alpha                92.095(7)
_cell_angle_beta                 99.967(7)
_cell_angle_gamma                107.977(7)
_cell_volume                     1461.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1632
_cell_measurement_theta_min      3.4480
_cell_measurement_theta_max      21.1850

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_F_000             554.0
_exptl_transmission_factor_min   0.922
_exptl_transmission_factor_max   0.945
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9820
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.872
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5119
_reflns_number_gt                2468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+3.0010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0032(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5119
_refine_ls_number_parameters     338
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2478
_refine_ls_wR_factor_gt          0.2052
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C26A C 0.6349(17) 0.928(2) 0.3735(14) 0.193(10) Uani 0.5 1 d D . P A 1
H26A H 0.6883 0.8639 0.3944 0.289 Uiso 0.5 1 calc R U P A 1
H26B H 0.6256 0.9882 0.4134 0.289 Uiso 0.5 1 calc R U P A 1
H26C H 0.7019 0.9825 0.3410 0.289 Uiso 0.5 1 calc R U P A 1
C26B C 0.504(3) 0.829(2) 0.4120(7) 0.199(11) Uani 0.5 1 d D . P A 2
H26E H 0.4041 0.7773 0.4293 0.298 Uiso 0.5 1 calc R U P A 2
H26F H 0.5525 0.9180 0.4405 0.298 Uiso 0.5 1 calc R U P A 2
H26D H 0.5850 0.7800 0.4183 0.298 Uiso 0.5 1 calc R U P A 2
Cl1 Cl 1.0543(3) 0.7445(2) 0.56730(9) 0.1293(8) Uani 1 1 d . . . . .
O2 O 0.6681(5) 0.5355(4) 0.1762(2) 0.0819(12) Uani 1 1 d . . . . .
O4 O 0.4898(5) 0.4004(4) 0.0800(2) 0.0849(12) Uani 1 1 d . . . . .
H4O H 0.4455 0.4070 0.0370 0.127 Uiso 1 1 calc R U . . .
O3 O 0.6490(5) 0.6085(4) 0.0626(2) 0.0881(13) Uani 1 1 d . . . . .
N2 N 0.9031(5) 0.8605(4) 0.1239(2) 0.0631(11) Uani 1 1 d . . . . .
H2N H 0.8168 0.7869 0.1120 0.076 Uiso 1 1 calc R U . . .
O1 O 1.0882(5) 0.9952(4) 0.22478(19) 0.0911(13) Uani 1 1 d . . . . .
N1 N 0.8964(5) 0.7884(4) 0.2401(2) 0.0643(11) Uani 1 1 d . . . . .
H1N H 0.8149 0.7190 0.2160 0.077 Uiso 1 1 calc R U . . .
C8 C 0.9555(6) 0.9347(5) 0.0639(3) 0.0556(12) Uani 1 1 d . . . . .
C7 C 0.9716(7) 0.8904(5) 0.1978(3) 0.0643(14) Uani 1 1 d . . . . .
C6 C 0.9381(6) 0.7850(5) 0.3185(3) 0.0600(13) Uani 1 1 d . . . . .
C10 C 1.1071(6) 1.0399(5) 0.0692(3) 0.0647(14) Uani 1 1 d . . . . .
H10 H 1.1806 1.0689 0.1154 0.078 Uiso 1 1 calc R U . . .
N3 N 0.1956(6) 0.4854(5) 0.2267(3) 0.0780(13) Uani 1 1 d . . . . .
C27 C 0.6106(6) 0.5211(5) 0.1080(3) 0.0640(13) Uani 1 1 d . . . . .
C9 C 0.8499(6) 0.8977(5) -0.0056(3) 0.0650(14) Uani 1 1 d . . . . .
H9 H 0.7461 0.8285 -0.0101 0.078 Uiso 1 1 calc R U . . .
C1 C 0.8705(7) 0.6603(6) 0.3476(3) 0.0700(15) Uani 1 1 d . . . . .
H1 H 0.8009 0.5841 0.3150 0.084 Uiso 1 1 calc R U . . .
C3 C 1.0060(8) 0.7586(7) 0.4708(3) 0.0827(18) Uani 1 1 d . . . . .
C5 C 1.0375(7) 0.8986(6) 0.3682(3) 0.0819(17) Uani 1 1 d . . . . .
H5 H 1.0802 0.9841 0.3504 0.098 Uiso 1 1 calc R U . . .
C19 C 0.2099(7) 0.5219(6) 0.1472(3) 0.0817(17) Uani 1 1 d . . . . .
H19A H 0.3288 0.5667 0.1464 0.098 Uiso 1 1 calc R U . . .
H19B H 0.1727 0.4365 0.1145 0.098 Uiso 1 1 calc R U . . .
C2 C 0.9038(7) 0.6470(7) 0.4229(3) 0.0788(16) Uani 1 1 d . . . . .
H2 H 0.8573 0.5627 0.4413 0.095 Uiso 1 1 calc R U . . .
C4 C 1.0728(8) 0.8846(7) 0.4438(3) 0.0908(19) Uani 1 1 d . . . . .
H4 H 1.1419 0.9602 0.4768 0.109 Uiso 1 1 calc R U . . .
C11 C 0.3056(7) 0.3941(7) 0.2473(3) 0.0865(18) Uani 1 1 d . . . . .
H11A H 0.2621 0.3111 0.2126 0.104 Uiso 1 1 calc R U . . .
H11B H 0.4195 0.4427 0.2403 0.104 Uiso 1 1 calc R U . . .
C20 C 0.1124(8) 0.6137(7) 0.1145(4) 0.095(2) Uani 1 1 d . . . . .
H20A H 0.1318 0.6919 0.1508 0.114 Uiso 1 1 calc R U . . .
H20B H -0.0079 0.5626 0.1042 0.114 Uiso 1 1 calc R U . . .
C15 C 0.0122(7) 0.4134(7) 0.2322(4) 0.0913(19) Uani 1 1 d . . . . .
H15A H 0.0093 0.3957 0.2842 0.110 Uiso 1 1 calc R U . . .
H15B H -0.0505 0.4774 0.2199 0.110 Uiso 1 1 calc R U . . .
C21 C 0.1656(10) 0.6657(8) 0.0426(4) 0.110(2) Uani 1 1 d . . . . .
H21A H 0.1743 0.5895 0.0119 0.132 Uiso 1 1 calc R U . . .
H21B H 0.0787 0.6983 0.0148 0.132 Uiso 1 1 calc R U . . .
C16 C -0.0794(8) 0.2814(8) 0.1845(4) 0.110(2) Uani 1 1 d . . . . .
H16A H -0.0130 0.2189 0.1911 0.132 Uiso 1 1 calc R U . . .
H16B H -0.0967 0.2987 0.1320 0.132 Uiso 1 1 calc R U . . .
C23 C 0.2547(8) 0.6174(7) 0.2799(4) 0.101(2) Uani 1 1 d . . . . .
H23A H 0.1792 0.6706 0.2650 0.121 Uiso 1 1 calc R U . . .
H23B H 0.2422 0.5917 0.3300 0.121 Uiso 1 1 calc R U . . .
C17 C -0.2496(9) 0.2165(9) 0.2071(5) 0.129(3) Uani 1 1 d . . . . .
H17A H -0.2287 0.1989 0.2594 0.155 Uiso 1 1 calc R U . . .
H17B H -0.3099 0.2836 0.2035 0.155 Uiso 1 1 calc R U . . .
C12 C 0.3158(10) 0.3523(9) 0.3256(4) 0.121(3) Uani 1 1 d . . . . .
H12A H 0.3492 0.4344 0.3607 0.146 Uiso 1 1 calc R U . . .
H12B H 0.2044 0.2947 0.3314 0.146 Uiso 1 1 calc R U . . .
C22 C 0.3322(11) 0.7806(8) 0.0564(5) 0.136(3) Uani 1 1 d . . . . .
H22A H 0.3241 0.8571 0.0861 0.205 Uiso 1 1 calc R U . . .
H22B H 0.3595 0.8098 0.0092 0.205 Uiso 1 1 calc R U . . .
H22C H 0.4195 0.7483 0.0827 0.205 Uiso 1 1 calc R U . . .
C13 C 0.4370(10) 0.2764(9) 0.3442(5) 0.128(3) Uani 1 1 d . . . . .
H13A H 0.5447 0.3294 0.3324 0.154 Uiso 1 1 calc R U . . .
H13B H 0.3960 0.1892 0.3130 0.154 Uiso 1 1 calc R U . . .
C24 C 0.4335(10) 0.7100(8) 0.2841(5) 0.134(3) Uani 1 1 d . . . . .
H24A H 0.4552 0.7255 0.2339 0.161 Uiso 1 1 calc R U . . .
H24B H 0.5127 0.6668 0.3092 0.161 Uiso 1 1 calc R U . . .
C18 C -0.3564(12) 0.0928(10) 0.1651(6) 0.173(4) Uani 1 1 d . . . . .
H18A H -0.3355 0.0920 0.1148 0.260 Uiso 1 1 calc R U . . .
H18B H -0.4726 0.0863 0.1638 0.260 Uiso 1 1 calc R U . . .
H18C H -0.3340 0.0155 0.1881 0.260 Uiso 1 1 calc R U . . .
C14 C 0.4653(12) 0.2476(11) 0.4262(5) 0.174(4) Uani 1 1 d . . . . .
H14A H 0.5388 0.3302 0.4564 0.261 Uiso 1 1 calc R U . . .
H14B H 0.5164 0.1758 0.4317 0.261 Uiso 1 1 calc R U . . .
H14C H 0.3585 0.2188 0.4424 0.261 Uiso 1 1 calc R U . . .
C25 C 0.4569(15) 0.8486(12) 0.3282(6) 0.205(6) Uani 1 1 d D . . . .
H25A H 0.4236 0.9086 0.2928 0.246 Uiso 0.5 1 calc DR U P A 1
H25B H 0.3787 0.8311 0.3627 0.246 Uiso 0.5 1 calc DR U P A 1
H25C H 0.520(10) 0.848(11) 0.377(2) 0.246 Uiso 0.5 1 d D U P B 2
H25D H 0.533(10) 0.881(14) 0.376(2) 0.246 Uiso 0.5 1 d D U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C26A C25 1.5393(11) . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C26B C25 1.5395(10) . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C26B H26D 0.9600 . ?
C26B H25C 0.69(6) . ?
C26B H25D 0.88(10) . ?
Cl1 C3 1.750(5) . ?
O2 C27 1.235(6) . ?
O4 C27 1.349(6) . ?
O4 H4O 0.8200 . ?
O3 C27 1.245(6) . ?
N2 C7 1.349(6) . ?
N2 C8 1.405(5) . ?
N2 H2N 0.8600 . ?
O1 C7 1.225(6) . ?
N1 C7 1.379(6) . ?
N1 C6 1.409(6) . ?
N1 H1N 0.8600 . ?
C8 C9 1.378(6) . ?
C8 C10 1.381(6) . ?
C6 C5 1.387(7) . ?
C6 C1 1.390(7) . ?
C10 C9 1.388(6) 2_775 ?
C10 H10 0.9300 . ?
N3 C19 1.519(7) . ?
N3 C11 1.522(7) . ?
N3 C15 1.520(7) . ?
N3 C23 1.524(7) . ?
C9 C10 1.388(6) 2_775 ?
C9 H9 0.9300 . ?
C1 C2 1.369(7) . ?
C1 H1 0.9300 . ?
C3 C2 1.364(8) . ?
C3 C4 1.382(8) . ?
C5 C4 1.375(7) . ?
C5 H5 0.9300 . ?
C19 C20 1.503(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.494(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C20 C21 1.514(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C15 C16 1.485(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C21 C22 1.503(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C16 C17 1.520(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C23 C24 1.502(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C17 C18 1.407(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 C13 1.468(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 C14 1.519(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C24 C25 1.541(12) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.961(8) . ?
C25 H25D 0.964(16) . ?

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
C25 C26A H26A 109.3 . . ?
C25 C26A H26B 109.6 . . ?
H26A C26A H26B 109.5 . . ?
C25 C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C25 C26B H26E 109.5 . . ?
C25 C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C25 C26B H26D 109.5 . . ?
H26E C26B H26D 109.5 . . ?
H26F C26B H26D 109.5 . . ?
C25 C26B H25C 25(6) . . ?
H26E C26B H25C 133.8 . . ?
H26F C26B H25C 99.3 . . ?
H26D C26B H25C 93.1 . . ?
C25 C26B H25D 35(2) . . ?
H26E C26B H25D 139.8 . . ?
H26F C26B H25D 80.1 . . ?
H26D C26B H25D 103.1 . . ?
H25C C26B H25D 20(10) . . ?
C27 O4 H4O 109.5 . . ?
C7 N2 C8 128.0(4) . . ?
C7 N2 H2N 116.0 . . ?
C8 N2 H2N 116.0 . . ?
C7 N1 C6 127.3(4) . . ?
C7 N1 H1N 116.4 . . ?
C6 N1 H1N 116.3 . . ?
C9 C8 C10 117.5(4) . . ?
C9 C8 N2 117.7(4) . . ?
C10 C8 N2 124.7(4) . . ?
O1 C7 N2 124.5(4) . . ?
O1 C7 N1 123.3(5) . . ?
N2 C7 N1 112.3(4) . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 N1 124.3(5) . . ?
C1 C6 N1 117.4(5) . . ?
C8 C10 C9 120.1(4) . 2_775 ?
C8 C10 H10 120.0 . . ?
C9 C10 H10 120.0 2_775 . ?
C19 N3 C11 107.0(4) . . ?
C19 N3 C15 111.1(4) . . ?
C11 N3 C15 111.7(5) . . ?
C19 N3 C23 109.5(5) . . ?
C11 N3 C23 111.4(5) . . ?
C15 N3 C23 106.0(5) . . ?
O2 C27 O3 126.6(5) . . ?
O2 C27 O4 116.9(5) . . ?
O3 C27 O4 116.4(5) . . ?
C8 C9 C10 122.4(4) . 2_775 ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 2_775 . ?
C2 C1 C6 121.6(5) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 Cl1 120.5(5) . . ?
C4 C3 Cl1 119.0(5) . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C20 C19 N3 116.8(5) . . ?
C20 C19 H19A 108.1 . . ?
N3 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
N3 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C5 C4 C3 120.3(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C11 N3 115.5(5) . . ?
C12 C11 H11A 108.4 . . ?
N3 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
N3 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C19 C20 C21 111.2(5) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C16 C15 N3 117.7(5) . . ?
C16 C15 H15A 107.9 . . ?
N3 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
N3 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C22 C21 C20 112.9(7) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C15 C16 C17 109.0(7) . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C24 C23 N3 116.8(5) . . ?
C24 C23 H23A 108.1 . . ?
N3 C23 H23A 108.1 . . ?
C24 C23 H23B 108.1 . . ?
N3 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C18 C17 C16 116.5(8) . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C16 C17 H17B 108.2 . . ?
H17A C17 H17B 107.3 . . ?
C13 C12 C11 112.7(6) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C13 C14 113.7(7) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C23 C24 C25 108.6(8) . . ?
C23 C24 H24A 110.0 . . ?
C25 C24 H24A 109.9 . . ?
C23 C24 H24B 110.0 . . ?
C25 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26B C25 C24 106.5(13) . . ?
C26A C25 C24 117.6(12) . . ?
C26A C25 H25A 107.8 . . ?
C24 C25 H25A 108.0 . . ?
C26A C25 H25B 107.9 . . ?
C24 C25 H25B 107.9 . . ?
H25A C25 H25B 107.2 . . ?
C26B C25 H25C 17(6) . . ?
C24 C25 H25C 107(6) . . ?
C26B C25 H25D 32(6) . . ?
C24 C25 H25D 123(10) . . ?
H25C C25 H25D 20(10) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_ppda-p-Br-TBABr-2b
_database_code_depnum_ccdc_archive 'CCDC 1860332'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br2 N4 O2, 2(C16 H36 N), 2(Br)'
_chemical_formula_sum            'C52 H88 Br4 N6 O2'
_chemical_formula_weight         1148.88

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.9473(16)
_cell_length_b                   16.101(4)
_cell_length_c                   21.153(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.90(2)
_cell_angle_gamma                90
_cell_volume                     2992.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1562
_cell_measurement_theta_min      3.5310
_cell_measurement_theta_max      19.5130

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             1196.0
_exptl_transmission_factor_min   0.483
_exptl_transmission_factor_max   0.579
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.729
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11098
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             5147
_reflns_number_gt                2196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.0010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5147
_refine_ls_number_parameters     293
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.05064(10) 0.35172(6) 0.27386(4) 0.0955(4) Uani 1 1 d . . . . .
Br1 Br 0.57034(14) 0.68642(10) 0.00490(6) 0.1498(6) Uani 1 1 d . . . . .
O1 O 0.7784(6) 0.6102(4) 0.3375(3) 0.0834(16) Uani 1 1 d . . . . .
N2 N 0.9206(6) 0.4922(4) 0.3648(3) 0.0732(17) Uani 1 1 d . . . . .
H2N H 0.9528 0.4485 0.3482 0.088 Uiso 1 1 calc R U . . .
N0AA N 0.3219(6) 0.6299(4) 0.3287(3) 0.0776(19) Uani 1 1 d . . . . .
C9 C 1.0326(9) 0.4336(6) 0.4657(4) 0.080(2) Uani 1 1 d . . . . .
H9 H 1.0543 0.3873 0.4428 0.096 Uiso 1 1 calc R U . . .
C7 C 0.8378(8) 0.5473(6) 0.3222(4) 0.072(2) Uani 1 1 d . . . . .
C8 C 0.9590(8) 0.4987(5) 0.4326(4) 0.069(2) Uani 1 1 d . . . . .
N1 N 0.8350(6) 0.5234(4) 0.2601(3) 0.0793(19) Uani 1 1 d . . . . .
H1N H 0.8785 0.4769 0.2551 0.095 Uiso 1 1 calc R U . . .
C12 C 0.4697(9) 0.4969(5) 0.3659(4) 0.095(3) Uani 1 1 d . . . . .
H12A H 0.5544 0.5285 0.3896 0.115 Uiso 1 1 calc R U . . .
H12B H 0.4894 0.4870 0.3229 0.115 Uiso 1 1 calc R U . . .
C6 C 0.7702(8) 0.5651(6) 0.2032(4) 0.069(2) Uani 1 1 d . . . . .
C20 C 0.4592(11) 0.7002(7) 0.4309(5) 0.120(4) Uani 1 1 d D . . . .
H20A H 0.4582 0.6471 0.4524 0.144 Uiso 1 1 calc R U . . .
H20B H 0.3683 0.7302 0.4362 0.144 Uiso 1 1 calc R U . . .
C11 C 0.3257(8) 0.5463(5) 0.3613(4) 0.082(2) Uani 1 1 d . . . . .
H11A H 0.3071 0.5548 0.4045 0.099 Uiso 1 1 calc R U . . .
H11B H 0.2422 0.5132 0.3383 0.099 Uiso 1 1 calc R U . . .
C5 C 0.7781(9) 0.5235(7) 0.1465(4) 0.100(3) Uani 1 1 d . . . . .
H5 H 0.8241 0.4715 0.1480 0.120 Uiso 1 1 calc R U . . .
C23 C 0.3412(9) 0.6199(6) 0.2603(4) 0.086(3) Uani 1 1 d . . . . .
H23A H 0.4404 0.5953 0.2608 0.103 Uiso 1 1 calc R U . . .
H23B H 0.3426 0.6749 0.2417 0.103 Uiso 1 1 calc R U . . .
C1 C 0.7018(8) 0.6427(6) 0.2002(4) 0.084(3) Uani 1 1 d . . . . .
H1 H 0.6945 0.6708 0.2379 0.101 Uiso 1 1 calc R U . . .
C3 C 0.6542(10) 0.6347(7) 0.0862(4) 0.092(3) Uani 1 1 d . . . . .
C19 C 0.4527(8) 0.6851(6) 0.3606(4) 0.085(2) Uani 1 1 d . . . . .
H19A H 0.5477 0.6598 0.3550 0.102 Uiso 1 1 calc R U . . .
H19B H 0.4442 0.7382 0.3386 0.102 Uiso 1 1 calc R U . . .
C15 C 0.1702(8) 0.6709(5) 0.3333(5) 0.088(3) Uani 1 1 d . . . . .
H15A H 0.0890 0.6354 0.3115 0.105 Uiso 1 1 calc R U . . .
H15B H 0.1620 0.6728 0.3784 0.105 Uiso 1 1 calc R U . . .
C4 C 0.7179(11) 0.5590(7) 0.0880(5) 0.107(3) Uani 1 1 d . . . . .
H4 H 0.7215 0.5307 0.0500 0.129 Uiso 1 1 calc R U . . .
C2 C 0.6450(8) 0.6778(6) 0.1418(5) 0.090(3) Uani 1 1 d . . . . .
H2 H 0.6007 0.7302 0.1395 0.108 Uiso 1 1 calc R U . . .
C10 C 1.0767(8) 0.4333(5) 0.5324(4) 0.082(2) Uani 1 1 d . . . . .
H10 H 1.1293 0.3883 0.5533 0.098 Uiso 1 1 calc R U . . .
C24 C 0.2223(10) 0.5678(7) 0.2151(5) 0.118(3) Uani 1 1 d . . . . .
H24A H 0.2208 0.5115 0.2314 0.142 Uiso 1 1 calc R U . . .
H24B H 0.1218 0.5917 0.2124 0.142 Uiso 1 1 calc R U . . .
C14 C 0.6020(12) 0.3639(7) 0.4071(6) 0.142(4) Uani 1 1 d . . . . .
H14A H 0.6282 0.3546 0.3657 0.212 Uiso 1 1 calc R U . . .
H14B H 0.5860 0.3114 0.4264 0.212 Uiso 1 1 calc R U . . .
H14C H 0.6832 0.3931 0.4342 0.212 Uiso 1 1 calc R U . . .
C16 C 0.1426(9) 0.7564(7) 0.3065(6) 0.126(4) Uani 1 1 d . . . . .
H16A H 0.2180 0.7943 0.3296 0.151 Uiso 1 1 calc R U . . .
H16B H 0.1514 0.7567 0.2615 0.151 Uiso 1 1 calc R U . . .
C25 C 0.2664(15) 0.5673(10) 0.1484(5) 0.204(8) Uani 1 1 d D . . . .
H25A H 0.3750 0.5579 0.1529 0.244 Uiso 1 1 calc R U . . .
H25B H 0.2428 0.6208 0.1278 0.244 Uiso 1 1 calc R U . . .
C17 C -0.0105(11) 0.7834(6) 0.3129(7) 0.148(5) Uani 1 1 d D . . . .
H17A H -0.0227 0.7756 0.3572 0.178 Uiso 1 1 calc R U . . .
H17B H -0.0854 0.7489 0.2858 0.178 Uiso 1 1 calc R U . . .
C13 C 0.4577(10) 0.4150(7) 0.3991(5) 0.114(3) Uani 1 1 d . . . . .
H13A H 0.3746 0.3833 0.3744 0.136 Uiso 1 1 calc R U . . .
H13B H 0.4336 0.4254 0.4412 0.136 Uiso 1 1 calc R U . . .
C21 C 0.5961(13) 0.7483(8) 0.4631(7) 0.176(6) Uani 1 1 d D . . . .
H21A H 0.6056 0.7452 0.5095 0.211 Uiso 1 1 calc R U . . .
H21B H 0.6874 0.7249 0.4518 0.211 Uiso 1 1 calc R U . . .
C18 C -0.0406(17) 0.8751(7) 0.2940(9) 0.242(8) Uani 1 1 d D . . . .
H18A H 0.0538 0.9017 0.2910 0.363 Uiso 1 1 calc R U . . .
H18B H -0.0855 0.9025 0.3262 0.363 Uiso 1 1 calc R U . . .
H18C H -0.1087 0.8782 0.2532 0.363 Uiso 1 1 calc R U . . .
C22 C 0.578(2) 0.8370(9) 0.4415(8) 0.290(12) Uani 1 1 d D . . . .
H22A H 0.6222 0.8443 0.4038 0.435 Uiso 1 1 calc R U . . .
H22B H 0.6291 0.8726 0.4752 0.435 Uiso 1 1 calc R U . . .
H22C H 0.4721 0.8509 0.4316 0.435 Uiso 1 1 calc R U . . .
C26 C 0.1785(19) 0.4984(11) 0.1066(8) 0.321(15) Uani 1 1 d D . . . .
H26A H 0.2124 0.4451 0.1240 0.481 Uiso 1 1 calc R U . . .
H26B H 0.1966 0.5029 0.0634 0.481 Uiso 1 1 calc R U . . .
H26C H 0.0715 0.5043 0.1063 0.481 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.930(9) . ?
O1 C7 1.216(9) . ?
N2 C7 1.376(9) . ?
N2 C8 1.415(9) . ?
N0AA C23 1.499(9) . ?
N0AA C11 1.509(9) . ?
N0AA C19 1.522(9) . ?
N0AA C15 1.529(9) . ?
C9 C8 1.360(10) . ?
C9 C10 1.390(10) . ?
C7 N1 1.366(9) . ?
C8 C10 1.392(10) 3_766 ?
N1 C6 1.403(9) . ?
C12 C11 1.501(10) . ?
C12 C13 1.508(11) . ?
C6 C5 1.387(11) . ?
C6 C1 1.389(11) . ?
C20 C19 1.497(11) . ?
C20 C21 1.5001(11) . ?
C5 C4 1.377(11) . ?
C23 C24 1.539(11) . ?
C1 C2 1.366(11) . ?
C3 C4 1.343(12) . ?
C3 C2 1.382(12) . ?
C15 C16 1.491(12) . ?
C10 C8 1.392(10) 3_766 ?
C24 C25 1.536(13) . ?
C14 C13 1.513(12) . ?
C16 C17 1.468(12) . ?
C25 C26 1.5397(11) . ?
C17 C18 1.5397(8) . ?
C21 C22 1.4994(11) . ?

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 N2 C8 127.8(7) . . ?
C23 N0AA C11 110.4(7) . . ?
C23 N0AA C19 105.7(5) . . ?
C11 N0AA C19 111.7(6) . . ?
C23 N0AA C15 111.9(6) . . ?
C11 N0AA C15 107.5(6) . . ?
C19 N0AA C15 109.7(7) . . ?
C8 C9 C10 122.8(8) . . ?
O1 C7 N1 124.2(9) . . ?
O1 C7 N2 124.8(8) . . ?
N1 C7 N2 111.0(7) . . ?
C9 C8 C10 118.0(7) . 3_766 ?
C9 C8 N2 117.8(8) . . ?
C10 C8 N2 124.2(8) 3_766 . ?
C7 N1 C6 128.3(7) . . ?
C11 C12 C13 110.9(7) . . ?
C5 C6 C1 119.3(8) . . ?
C5 C6 N1 115.4(8) . . ?
C1 C6 N1 125.3(8) . . ?
C19 C20 C21 114.2(9) . . ?
C12 C11 N0AA 116.5(6) . . ?
C4 C5 C6 120.1(9) . . ?
N0AA C23 C24 117.7(6) . . ?
C2 C1 C6 119.9(9) . . ?
C4 C3 C2 121.6(9) . . ?
C4 C3 Br1 120.6(8) . . ?
C2 C3 Br1 117.8(8) . . ?
C20 C19 N0AA 114.6(7) . . ?
C16 C15 N0AA 117.4(6) . . ?
C3 C4 C5 119.7(9) . . ?
C1 C2 C3 119.4(9) . . ?
C9 C10 C8 119.2(8) . 3_766 ?
C25 C24 C23 107.8(8) . . ?
C17 C16 C15 109.1(8) . . ?
C24 C25 C26 109.8(11) . . ?
C16 C17 C18 112.3(10) . . ?
C12 C13 C14 113.2(7) . . ?
C22 C21 C20 108.8(12) . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.478
_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_ppda-p-Br-TBAHSO4-2d
_database_code_depnum_ccdc_archive 'CCDC 1860334'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C20 H16 Br2 N4 O2, 2(C16 H36 N), 2(H O4 S), 2(C3 H7 N O)'
_chemical_formula_sum            'C58 H104 Br2 N8 O12 S2'
_chemical_formula_weight         1329.41

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2364(9)
_cell_length_b                   10.9069(14)
_cell_length_c                   20.0064(17)
_cell_angle_alpha                85.053(8)
_cell_angle_beta                 79.089(8)
_cell_angle_gamma                81.371(10)
_cell_volume                     1741.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1222
_cell_measurement_theta_min      3.4260
_cell_measurement_theta_max      18.7770

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             706.0
_exptl_transmission_factor_min   0.670
_exptl_transmission_factor_max   0.744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    1.283
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12265
_diffrn_reflns_av_unetI/netI     0.1549
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6100
_reflns_number_gt                4133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.0010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0016(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6100
_refine_ls_number_parameters     378
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2318
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.28255(17) 0.85450(13) 0.00063(5) 0.1739(8) Uani 1 1 d . . . . .
S1 S 0.5554(3) 0.48663(19) 0.59433(10) 0.0693(6) Uani 1 1 d . . . . .
O8 O 0.6927(6) 0.5238(5) 0.5339(2) 0.0845(15) Uani 1 1 d . . . . .
H8 H 0.6510 0.5438 0.4998 0.127 Uiso 1 1 calc R U . . .
O10 O 0.6480(6) 0.4252(4) 0.6448(2) 0.0853(16) Uani 1 1 d . . . . .
O9 O 0.4510(6) 0.5978(4) 0.6153(2) 0.0870(16) Uani 1 1 d . . . . .
O11 O 0.4661(6) 0.4008(4) 0.5687(2) 0.0789(15) Uani 1 1 d . . . . .
O7 O 0.3961(7) 1.0230(5) 0.3120(2) 0.0907(17) Uani 1 1 d . . . . .
N3 N 0.0306(8) 0.3080(6) 0.3248(3) 0.0754(18) Uani 1 1 d . . . . .
C8 C 0.4716(8) 0.9391(6) 0.4452(3) 0.0573(18) Uani 1 1 d . . . . .
N2 N 0.4476(6) 0.8691(5) 0.3929(3) 0.0664(16) Uani 1 1 d . . . . .
H2N H 0.4585 0.7897 0.4004 0.080 Uiso 1 1 calc R U . . .
C7 C 0.4091(9) 0.9140(8) 0.3320(4) 0.065(2) Uani 1 1 d . . . . .
C9 C 0.5010(7) 1.0614(6) 0.4364(3) 0.0621(19) Uani 1 1 d . . . . .
H9 H 0.5039 1.1034 0.3938 0.075 Uiso 1 1 calc R U . . .
N1 N 0.3820(7) 0.8230(5) 0.2936(3) 0.0738(18) Uani 1 1 d . . . . .
H1N H 0.3783 0.7499 0.3131 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5265(8) 1.1217(6) 0.4914(4) 0.0638(19) Uani 1 1 d . . . . .
H10 H 0.5426 1.2048 0.4853 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3601(9) 0.8381(7) 0.2262(4) 0.069(2) Uani 1 1 d . . . . .
C15 C -0.0274(10) 0.3155(9) 0.4011(4) 0.098(3) Uani 1 1 d . . . . .
H15A H -0.0084 0.3958 0.4130 0.117 Uiso 1 1 calc R U . . .
H15B H -0.1471 0.3144 0.4104 0.117 Uiso 1 1 calc R U . . .
C16 C 0.0456(11) 0.2212(8) 0.4476(5) 0.112(3) Uani 1 1 d . . . . .
H16A H 0.1658 0.2198 0.4384 0.135 Uiso 1 1 calc R U . . .
H16B H 0.0227 0.1405 0.4380 0.135 Uiso 1 1 calc R U . . .
C6 C 0.3123(11) 0.8482(11) 0.0930(4) 0.106(3) Uani 1 1 d . . . . .
C18 C 0.0441(14) 0.1563(12) 0.5694(5) 0.176(5) Uani 1 1 d . . . . .
H18A H 0.0241 0.0745 0.5620 0.265 Uiso 1 1 calc R U . . .
H18B H -0.0116 0.1787 0.6142 0.265 Uiso 1 1 calc R U . . .
H18C H 0.1618 0.1574 0.5655 0.265 Uiso 1 1 calc R U . . .
C11 C 0.2141(9) 0.3198(7) 0.3082(4) 0.085(2) Uani 1 1 d . . . . .
H11A H 0.2318 0.3898 0.3315 0.102 Uiso 1 1 calc R U . . .
H11B H 0.2741 0.2459 0.3275 0.102 Uiso 1 1 calc R U . . .
C2 C 0.3126(9) 0.7389(8) 0.1999(4) 0.087(3) Uani 1 1 d . . . . .
H2 H 0.2944 0.6682 0.2282 0.105 Uiso 1 1 calc R U . . .
C23 C -0.0705(10) 0.4104(8) 0.2891(4) 0.099(3) Uani 1 1 d . . . . .
H23A H -0.0374 0.4009 0.2404 0.119 Uiso 1 1 calc R U . . .
H23B H -0.1866 0.3973 0.3013 0.119 Uiso 1 1 calc R U . . .
C19 C 0.0030(14) 0.1842(9) 0.3033(5) 0.140(4) Uani 1 1 d . . . . .
H19A H 0.0631 0.1792 0.2567 0.168 Uiso 1 1 calc R U . . .
H19B H 0.0649 0.1226 0.3302 0.168 Uiso 1 1 calc R U . . .
C4 C 0.3838(10) 0.9417(8) 0.1836(4) 0.092(3) Uani 1 1 d . . . . .
H4 H 0.4156 1.0101 0.1999 0.111 Uiso 1 1 calc R U . . .
C1 C 0.2911(10) 0.7412(9) 0.1333(5) 0.103(3) Uani 1 1 d . . . . .
H1 H 0.2630 0.6723 0.1161 0.123 Uiso 1 1 calc R U . . .
C17 C -0.0167(13) 0.2407(11) 0.5212(5) 0.154(5) Uani 1 1 d . . . . .
H17A H 0.0060 0.3221 0.5298 0.184 Uiso 1 1 calc R U . . .
H17B H -0.1371 0.2435 0.5293 0.184 Uiso 1 1 calc R U . . .
C12 C 0.2911(10) 0.3365(8) 0.2362(4) 0.090(3) Uani 1 1 d . . . . .
H12A H 0.2390 0.4139 0.2170 0.108 Uiso 1 1 calc R U . . .
H12B H 0.2697 0.2695 0.2116 0.108 Uiso 1 1 calc R U . . .
C13 C 0.4744(11) 0.3385(8) 0.2259(4) 0.110(3) Uani 1 1 d . . . . .
H13A H 0.4948 0.4027 0.2527 0.132 Uiso 1 1 calc R U . . .
H13B H 0.5258 0.2596 0.2436 0.132 Uiso 1 1 calc R U . . .
C5 C 0.3610(11) 0.9461(9) 0.1167(4) 0.101(3) Uani 1 1 d . . . . .
H5 H 0.3793 1.0164 0.0881 0.121 Uiso 1 1 calc R U . . .
C24 C -0.0614(12) 0.5394(10) 0.3015(5) 0.132(4) Uani 1 1 d D . . . .
H24A H 0.0541 0.5544 0.2928 0.159 Uiso 1 1 calc R U . . .
H24B H -0.1088 0.5556 0.3486 0.159 Uiso 1 1 calc R U . . .
C14 C 0.5579(11) 0.3607(9) 0.1550(4) 0.143(4) Uani 1 1 d . . . . .
H14A H 0.5457 0.2947 0.1283 0.214 Uiso 1 1 calc R U . . .
H14B H 0.6744 0.3634 0.1539 0.214 Uiso 1 1 calc R U . . .
H14C H 0.5082 0.4384 0.1365 0.214 Uiso 1 1 calc R U . . .
C20 C -0.1313(16) 0.1418(12) 0.3031(8) 0.243(8) Uani 1 1 d . . . . .
H20A H -0.2054 0.2085 0.2848 0.292 Uiso 1 1 calc R U . . .
H20B H -0.1811 0.1258 0.3505 0.292 Uiso 1 1 calc R U . . .
C21 C -0.1361(13) 0.0252(10) 0.2658(6) 0.155(5) Uani 1 1 d . . . . .
H21A H -0.0418 -0.0349 0.2743 0.186 Uiso 1 1 calc R U . . .
H21B H -0.2362 -0.0096 0.2873 0.186 Uiso 1 1 calc R U . . .
C22 C -0.1332(14) 0.0352(11) 0.1908(6) 0.164(5) Uani 1 1 d . . . . .
H22A H -0.2132 0.1038 0.1798 0.246 Uiso 1 1 calc R U . . .
H22B H -0.1609 -0.0402 0.1771 0.246 Uiso 1 1 calc R U . . .
H22C H -0.0238 0.0484 0.1673 0.246 Uiso 1 1 calc R U . . .
C26 C -0.222(3) 0.7589(11) 0.2581(11) 0.452(18) Uani 1 1 d D . . . .
H26A H -0.1599 0.7971 0.2844 0.678 Uiso 1 1 calc R U . . .
H26B H -0.3381 0.7689 0.2793 0.678 Uiso 1 1 calc R U . . .
H26C H -0.2112 0.7976 0.2128 0.678 Uiso 1 1 calc R U . . .
C25 C -0.1573(19) 0.6233(11) 0.2547(7) 0.242(8) Uani 1 1 d D . . . .
H25A H -0.0885 0.6156 0.2098 0.291 Uiso 1 1 calc R U . . .
H25B H -0.2543 0.5833 0.2536 0.291 Uiso 1 1 calc R U . . .
N4 N 0.8230(13) 0.6636(13) 0.9868(5) 0.147(4) Uani 1 1 d D . . . .
O12 O 0.919(3) 0.5849(16) 0.9034(9) 0.437(13) Uani 1 1 d D . . . .
C29 C 0.936(3) 0.6910(18) 0.9180(8) 0.341(19) Uani 1 1 d D . . . .
H29 H 0.9905 0.7565 0.8970 0.409 Uiso 1 1 calc R U . . .
C27 C 0.804(2) 0.738(2) 1.0417(10) 0.310(10) Uani 1 1 d . . . . .
H27A H 0.6984 0.7907 1.0458 0.466 Uiso 1 1 calc R U . . .
H27B H 0.8924 0.7891 1.0342 0.466 Uiso 1 1 calc R U . . .
H27C H 0.8085 0.6869 1.0829 0.466 Uiso 1 1 calc R U . . .
C28 C 0.739(3) 0.5622(18) 0.9950(11) 0.331(14) Uani 1 1 d . . . . .
H28A H 0.7595 0.5137 1.0357 0.496 Uiso 1 1 calc R U . . .
H28B H 0.7767 0.5124 0.9564 0.496 Uiso 1 1 calc R U . . .
H28C H 0.6213 0.5896 0.9988 0.496 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.904(8) . ?
S1 O9 1.423(5) . ?
S1 O10 1.438(5) . ?
S1 O11 1.454(4) . ?
S1 O8 1.562(5) . ?
O7 C7 1.217(7) . ?
N3 C23 1.504(9) . ?
N3 C11 1.508(8) . ?
N3 C19 1.513(9) . ?
N3 C15 1.515(8) . ?
C8 C10 1.381(8) 2_676 ?
C8 C9 1.382(8) . ?
C8 N2 1.407(7) . ?
N2 C7 1.349(8) . ?
C7 N1 1.374(8) . ?
C9 C10 1.394(8) . ?
N1 C3 1.386(8) . ?
C10 C8 1.381(8) 2_676 ?
C3 C4 1.371(9) . ?
C3 C2 1.379(9) . ?
C15 C16 1.465(10) . ?
C16 C17 1.486(11) . ?
C6 C5 1.346(10) . ?
C6 C1 1.375(11) . ?
C18 C17 1.386(11) . ?
C11 C12 1.468(8) . ?
C2 C1 1.374(9) . ?
C23 C24 1.465(11) . ?
C19 C20 1.262(12) . ?
C4 C5 1.383(9) . ?
C12 C13 1.488(9) . ?
C13 C14 1.471(9) . ?
C24 C25 1.5006(10) . ?
C20 C21 1.539(13) . ?
C21 C22 1.490(11) . ?
C26 C25 1.4991(11) . ?
N4 C28 1.373(15) . ?
N4 C27 1.396(17) . ?
N4 C29 1.5400(11) . ?
O12 C29 1.2501(11) . ?

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
O9 S1 O10 114.3(3) . . ?
O9 S1 O11 112.5(3) . . ?
O10 S1 O11 111.1(3) . . ?
O9 S1 O8 107.3(3) . . ?
O10 S1 O8 104.1(3) . . ?
O11 S1 O8 106.8(3) . . ?
C23 N3 C11 111.5(6) . . ?
C23 N3 C19 109.0(6) . . ?
C11 N3 C19 109.4(7) . . ?
C23 N3 C15 108.6(6) . . ?
C11 N3 C15 108.6(5) . . ?
C19 N3 C15 109.7(6) . . ?
C10 C8 C9 118.6(6) 2_676 . ?
C10 C8 N2 117.0(6) 2_676 . ?
C9 C8 N2 124.4(6) . . ?
C7 N2 C8 126.5(6) . . ?
O7 C7 N2 125.2(7) . . ?
O7 C7 N1 121.9(7) . . ?
N2 C7 N1 112.9(7) . . ?
C8 C9 C10 119.8(6) . . ?
C7 N1 C3 126.1(6) . . ?
C8 C10 C9 121.6(6) 2_676 . ?
C4 C3 C2 117.6(7) . . ?
C4 C3 N1 125.7(7) . . ?
C2 C3 N1 116.6(7) . . ?
C16 C15 N3 119.4(8) . . ?
C15 C16 C17 114.6(9) . . ?
C5 C6 C1 121.3(8) . . ?
C5 C6 Br1 119.6(8) . . ?
C1 C6 Br1 119.1(8) . . ?
C12 C11 N3 118.1(6) . . ?
C1 C2 C3 122.2(8) . . ?
C24 C23 N3 118.7(7) . . ?
C20 C19 N3 129.8(11) . . ?
C3 C4 C5 120.9(8) . . ?
C2 C1 C6 118.1(8) . . ?
C18 C17 C16 119.1(10) . . ?
C11 C12 C13 113.2(7) . . ?
C14 C13 C12 115.8(7) . . ?
C6 C5 C4 119.8(8) . . ?
C23 C24 C25 108.5(9) . . ?
C19 C20 C21 122.1(12) . . ?
C22 C21 C20 119.9(12) . . ?
C26 C25 C24 129.6(15) . . ?
C28 N4 C27 118.5(15) . . ?
C28 N4 C29 119.4(13) . . ?
C27 N4 C29 122.0(15) . . ?
O12 C29 N4 86.4(12) . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_ppda-p-Cl-TBAH2PO4-1e
_database_code_depnum_ccdc_archive 'CCDC 1860330'
_audit_update_record             
;
2018-08-05 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl2 N4 O2, 2(C16 H36 N), 2(H2 O4 P)'
_chemical_formula_sum            'C52 H92 Cl2 N6 O10 P2'
_chemical_formula_weight         1094.16

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'
O O 0.0106 0.0060 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4459(5)
_cell_length_b                   11.6202(10)
_cell_length_c                   15.6367(11)
_cell_angle_alpha                82.597(7)
_cell_angle_beta                 83.548(5)
_cell_angle_gamma                86.964(6)
_cell_volume                     1511.05(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2868
_cell_measurement_theta_min      3.5420
_cell_measurement_theta_max      23.1170

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             590.0
_exptl_transmission_factor_min   0.937
_exptl_transmission_factor_max   0.951
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10428
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.949
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5307
_reflns_number_gt                3542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5307
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P001 P 0.74882(9) 0.97614(8) 0.51053(6) 0.0474(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2082(2) 0.73389(17) 1.01687(9) 0.1210(6) Uani 1 1 d . . . . .
O5 O 0.6175(3) 0.9493(2) 0.58288(16) 0.0557(6) Uani 1 1 d . . . . .
O4 O 0.8799(3) 0.8840(2) 0.50633(19) 0.0618(7) Uani 1 1 d . . . . .
O3 O 0.8182(3) 1.0945(2) 0.52189(19) 0.0592(7) Uani 1 1 d . . . . .
H3O H 0.9146 1.0927 0.5074 0.089 Uiso 1 1 calc R U . . .
O2 O 0.6776(3) 0.9946(3) 0.42139(16) 0.0654(7) Uani 1 1 d . . . . .
H2O H 0.5808 1.0063 0.4296 0.098 Uiso 1 1 calc R U . . .
O1 O 0.7231(3) 0.5434(2) 0.71640(18) 0.0683(7) Uani 1 1 d . . . . .
N2 N 0.8438(3) 0.6614(2) 0.60261(19) 0.0491(7) Uani 1 1 d . . . . .
H2N H 0.8617 0.7330 0.5842 0.059 Uiso 1 1 calc R U . . .
N3 N 0.4764(3) 0.2514(3) 0.74711(18) 0.0549(8) Uani 1 1 d . . . . .
N1 N 0.6675(4) 0.7389(3) 0.7025(2) 0.0634(8) Uani 1 1 d . . . . .
H1N H 0.6847 0.8044 0.6712 0.076 Uiso 1 1 calc R U . . .
C8 C 0.9206(3) 0.5777(3) 0.5527(2) 0.0433(8) Uani 1 1 d . . . . .
C9 C 0.9680(4) 0.6125(3) 0.4665(2) 0.0482(8) Uani 1 1 d . . . . .
H9 H 0.9468 0.6889 0.4434 0.058 Uiso 1 1 calc R U . . .
C10 C 0.9541(4) 0.4628(3) 0.5862(2) 0.0475(8) Uani 1 1 d . . . . .
H10 H 0.9235 0.4374 0.6443 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7453(4) 0.6402(3) 0.6761(2) 0.0516(8) Uani 1 1 d . . . . .
C19 C 0.5693(4) 0.3160(3) 0.5866(2) 0.0515(8) Uani 1 1 d . . . . .
H19A H 0.6766 0.2822 0.5884 0.062 Uiso 1 1 calc R U . . .
H19B H 0.5694 0.3948 0.6007 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5189(4) 0.3173(4) 0.4962(2) 0.0593(10) Uani 1 1 d . . . . .
H20A H 0.4996 0.2386 0.4868 0.071 Uiso 1 1 calc R U . . .
H20B H 0.4196 0.3626 0.4922 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4554(4) 0.2456(3) 0.6524(2) 0.0555(9) Uani 1 1 d . . . . .
H18A H 0.4676 0.1650 0.6418 0.067 Uiso 1 1 calc R U . . .
H18B H 0.3473 0.2720 0.6426 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5611(5) 0.7368(3) 0.7784(3) 0.0615(10) Uani 1 1 d . . . . .
C21 C 0.6415(5) 0.3674(4) 0.4260(3) 0.0708(11) Uani 1 1 d . . . . .
H21A H 0.6732 0.4405 0.4396 0.106 Uiso 1 1 calc R U . . .
H21B H 0.5969 0.3789 0.3716 0.106 Uiso 1 1 calc R U . . .
H21C H 0.7328 0.3148 0.4221 0.106 Uiso 1 1 calc R U . . .
C22 C 0.4244(5) 0.3700(4) 0.7729(3) 0.0656(10) Uani 1 1 d . . . . .
H22A H 0.4469 0.3714 0.8323 0.079 Uiso 1 1 calc R U . . .
H22B H 0.4900 0.4272 0.7366 0.079 Uiso 1 1 calc R U . . .
C14 C 0.6508(4) 0.2312(4) 0.7625(2) 0.0638(11) Uani 1 1 d . . . . .
H14A H 0.7116 0.2916 0.7268 0.077 Uiso 1 1 calc R U . . .
H14B H 0.6607 0.2393 0.8226 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3751(5) 0.1573(4) 0.7997(3) 0.0690(11) Uani 1 1 d . . . . .
H11A H 0.2678 0.1672 0.7828 0.083 Uiso 1 1 calc R U . . .
H11B H 0.4179 0.0823 0.7851 0.083 Uiso 1 1 calc R U . . .
C1 C 0.4223(5) 0.8062(4) 0.7763(3) 0.0707(11) Uani 1 1 d . . . . .
H1 H 0.4017 0.8530 0.7256 0.085 Uiso 1 1 calc R U . . .
C5 C 0.5912(5) 0.6686(4) 0.8553(3) 0.0723(11) Uani 1 1 d . . . . .
H5 H 0.6844 0.6224 0.8574 0.087 Uiso 1 1 calc R U . . .
C15 C 0.7247(5) 0.1146(4) 0.7434(3) 0.0727(12) Uani 1 1 d . . . . .
H15A H 0.6983 0.0989 0.6874 0.087 Uiso 1 1 calc R U . . .
H15B H 0.6806 0.0543 0.7870 0.087 Uiso 1 1 calc R U . . .
C2 C 0.3149(6) 0.8058(4) 0.8496(3) 0.0779(12) Uani 1 1 d . . . . .
H2 H 0.2215 0.8518 0.8482 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4836(6) 0.6693(4) 0.9280(3) 0.0801(13) Uani 1 1 d . . . . .
H4 H 0.5040 0.6238 0.9793 0.096 Uiso 1 1 calc R U . . .
C23 C 0.2532(5) 0.4076(4) 0.7671(3) 0.0827(13) Uani 1 1 d . . . . .
H23A H 0.1852 0.3444 0.7918 0.099 Uiso 1 1 calc R U . . .
H23B H 0.2348 0.4279 0.7068 0.099 Uiso 1 1 calc R U . . .
C3 C 0.3462(6) 0.7371(4) 0.9248(3) 0.0784(13) Uani 1 1 d . . . . .
C16 C 0.9054(5) 0.1115(5) 0.7431(3) 0.0937(16) Uani 1 1 d . . . . .
H16A H 0.9496 0.1685 0.6969 0.112 Uiso 1 1 calc R U . . .
H16B H 0.9313 0.1333 0.7976 0.112 Uiso 1 1 calc R U . . .
C00V C 0.3665(7) 0.1563(5) 0.8973(3) 0.1002(17) Uani 1 1 d . . . . .
H00A H 0.4697 0.1312 0.9161 0.120 Uiso 1 1 calc R U . . .
H00B H 0.3430 0.2348 0.9113 0.120 Uiso 1 1 calc R U . . .
C17 C 0.9818(6) -0.0053(6) 0.7307(3) 0.112(2) Uani 1 1 d . . . . .
H17A H 0.9424 -0.0615 0.7777 0.169 Uiso 1 1 calc R U . . .
H17B H 1.0953 -0.0019 0.7296 0.169 Uiso 1 1 calc R U . . .
H17C H 0.9566 -0.0275 0.6769 0.169 Uiso 1 1 calc R U . . .
C24 C 0.2121(8) 0.5128(6) 0.8165(5) 0.123(2) Uani 1 1 d . . . . .
H24A H 0.2441 0.4932 0.8744 0.148 Uiso 1 1 calc R U . . .
H24B H 0.2766 0.5762 0.7880 0.148 Uiso 1 1 calc R U . . .
C12 C 0.2462(10) 0.0805(7) 0.9447(4) 0.145(3) Uani 1 1 d . . . . .
H12A H 0.1456 0.1016 0.9213 0.174 Uiso 1 1 calc R U . . .
H12B H 0.2752 0.0016 0.9334 0.174 Uiso 1 1 calc R U . . .
C13 C 0.2209(10) 0.0813(7) 1.0377(4) 0.149(3) Uani 1 1 d . . . . .
H13A H 0.3220 0.0748 1.0609 0.224 Uiso 1 1 calc R U . . .
H13B H 0.1576 0.0171 1.0634 0.224 Uiso 1 1 calc R U . . .
H13C H 0.1664 0.1527 1.0504 0.224 Uiso 1 1 calc R U . . .
C25 C 0.0557(10) 0.5526(10) 0.8241(9) 0.232(6) Uani 1 1 d . . . . .
H25A H 0.0191 0.5676 0.7677 0.349 Uiso 1 1 calc R U . . .
H25B H 0.0472 0.6231 0.8506 0.349 Uiso 1 1 calc R U . . .
H25C H -0.0085 0.4951 0.8595 0.349 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 O4 1.501(2) . ?
P001 O5 1.507(2) . ?
P001 O3 1.561(2) . ?
P001 O2 1.565(3) . ?
Cl1 C3 1.745(5) . ?
O3 H3O 0.8200 . ?
O2 H2O 0.8200 . ?
O1 C7 1.229(4) . ?
N2 C7 1.344(4) . ?
N2 C8 1.410(4) . ?
N2 H2N 0.8600 . ?
N3 C22 1.515(5) . ?
N3 C14 1.520(5) . ?
N3 C11 1.521(4) . ?
N3 C18 1.522(4) . ?
N1 C7 1.378(5) . ?
N1 C6 1.404(5) . ?
N1 H1N 0.8600 . ?
C8 C9 1.378(5) . ?
C8 C10 1.396(4) . ?
C9 C10 1.372(5) 2_766 ?
C9 H9 0.9300 . ?
C10 C9 1.372(5) 2_766 ?
C10 H10 0.9300 . ?
C19 C18 1.515(5) . ?
C19 C20 1.520(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.502(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C6 C1 1.389(6) . ?
C6 C5 1.393(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.497(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C14 C15 1.512(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 C00V 1.518(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 C2 1.378(6) . ?
C1 H1 0.9300 . ?
C5 C4 1.374(6) . ?
C5 H5 0.9300 . ?
C15 C16 1.524(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C4 C3 1.369(7) . ?
C4 H4 0.9300 . ?
C23 C24 1.532(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C16 C17 1.498(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C00V C12 1.455(7) . ?
C00V H00A 0.9700 . ?
C00V H00B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C24 C25 1.374(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C12 C13 1.446(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 P001 O5 114.23(14) . . ?
O4 P001 O3 110.13(13) . . ?
O5 P001 O3 107.88(15) . . ?
O4 P001 O2 108.27(16) . . ?
O5 P001 O2 109.69(13) . . ?
O3 P001 O2 106.35(16) . . ?
P001 O3 H3O 109.5 . . ?
P001 O2 H2O 109.5 . . ?
C7 N2 C8 126.4(3) . . ?
C7 N2 H2N 116.8 . . ?
C8 N2 H2N 116.8 . . ?
C22 N3 C14 107.0(3) . . ?
C22 N3 C11 111.0(3) . . ?
C14 N3 C11 110.9(3) . . ?
C22 N3 C18 111.0(3) . . ?
C14 N3 C18 110.5(3) . . ?
C11 N3 C18 106.4(3) . . ?
C7 N1 C6 122.6(3) . . ?
C7 N1 H1N 118.7 . . ?
C6 N1 H1N 118.7 . . ?
C9 C8 C10 118.4(3) . . ?
C9 C8 N2 117.8(3) . . ?
C10 C8 N2 123.8(3) . . ?
C10 C9 C8 121.5(3) 2_766 . ?
C10 C9 H9 119.2 2_766 . ?
C8 C9 H9 119.2 . . ?
C9 C10 C8 120.1(3) 2_766 . ?
C9 C10 H10 120.0 2_766 . ?
C8 C10 H10 120.0 . . ?
O1 C7 N2 124.6(3) . . ?
O1 C7 N1 122.2(3) . . ?
N2 C7 N1 113.2(3) . . ?
C18 C19 C20 110.0(3) . . ?
C18 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C21 C20 C19 112.8(3) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C19 C18 N3 115.7(3) . . ?
C19 C18 H18A 108.3 . . ?
N3 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
N3 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 N1 118.4(4) . . ?
C5 C6 N1 122.2(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N3 117.0(3) . . ?
C23 C22 H22A 108.1 . . ?
N3 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
N3 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C15 C14 N3 115.5(3) . . ?
C15 C14 H14A 108.4 . . ?
N3 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
N3 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C00V C11 N3 114.7(4) . . ?
C00V C11 H11A 108.6 . . ?
N3 C11 H11A 108.6 . . ?
C00V C11 H11B 108.6 . . ?
N3 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C2 C1 C6 119.9(4) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C14 C15 C16 111.5(4) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C22 C23 C24 109.6(4) . . ?
C22 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
C22 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 Cl1 119.3(4) . . ?
C2 C3 Cl1 119.9(4) . . ?
C17 C16 C15 113.0(5) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C12 C00V C11 113.1(5) . . ?
C12 C00V H00A 109.0 . . ?
C11 C00V H00A 109.0 . . ?
C12 C00V H00B 109.0 . . ?
C11 C00V H00B 109.0 . . ?
H00A C00V H00B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 C24 C23 117.4(6) . . ?
C25 C24 H24A 108.0 . . ?
C23 C24 H24A 108.0 . . ?
C25 C24 H24B 108.0 . . ?
C23 C24 H24B 108.0 . . ?
H24A C24 H24B 107.2 . . ?
C13 C12 C00V 116.8(6) . . ?
C13 C12 H12A 108.1 . . ?
C00V C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C00V C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.049

