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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042843'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C9 H12 N4 P), C2 H3 N, 3(Br)'
_chemical_formula_sum            'C29 H39 Br3 N13 P3'
_chemical_formula_weight         902.37

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.1735(3)
_cell_length_b                   12.6747(4)
_cell_length_c                   16.2901(5)
_cell_angle_alpha                83.7780(10)
_cell_angle_beta                 72.5960(10)
_cell_angle_gamma                73.1770(10)
_cell_volume                     1918.05(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.88

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    3.320
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_process_details   'SADABS; Bruker,2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36505
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         27.913
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9153
_reflns_number_gt                7160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+0.7902P] 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         9153
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P1 P 0.33690(6) 0.79510(5) 0.09206(4) 0.02825(14) Uani 1 1 d . . . . .
C11 C 0.4732(2) 0.86262(18) 0.07980(15) 0.0245(5) Uani 1 1 d . . . . .
N12 N 0.4567(2) 0.96011(15) 0.11289(13) 0.0259(4) Uani 1 1 d . . . . .
N15 N 0.61452(19) 0.82547(15) 0.03800(12) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.5876(3) 0.9844(2) 0.09224(16) 0.0291(5) Uani 1 1 d . . . . .
H13 H 0.6044 1.0483 0.1080 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6861(3) 0.9008(2) 0.04582(16) 0.0285(5) Uani 1 1 d . . . . .
H14 H 0.7856 0.8942 0.0227 0.034 Uiso 1 1 calc R U . . .
C16 C 0.6702(2) 0.72773(19) -0.01355(15) 0.0264(5) Uani 1 1 d . . . . .
H16A H 0.6455 0.7442 -0.0688 0.032 Uiso 1 1 calc R U . . .
H16B H 0.7757 0.7026 -0.0262 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6731(3) 0.53076(19) 0.03955(16) 0.0287(5) Uani 1 1 d . . . . .
H18 H 0.7715 0.4948 0.0159 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5708(3) 0.48328(19) 0.08429(17) 0.0306(6) Uani 1 1 d . . . . .
H19 H 0.5833 0.4069 0.0983 0.037 Uiso 1 1 calc R U . . .
C110 C 0.3073(3) 0.5515(2) 0.16253(18) 0.0336(6) Uani 1 1 d . . . . .
H11A H 0.2804 0.5931 0.2151 0.050 Uiso 1 1 calc R U . . .
H11B H 0.3174 0.4731 0.1775 0.050 Uiso 1 1 calc R U . . .
H11C H 0.2331 0.5787 0.1326 0.050 Uiso 1 1 calc R U . . .
N17 N 0.6074(2) 0.64280(15) 0.03443(12) 0.0236(4) Uani 1 1 d . . . . .
N110 N 0.4430(2) 0.56568(16) 0.10654(13) 0.0263(4) Uani 1 1 d . . . . .
C111 C 0.4661(2) 0.66313(18) 0.07552(15) 0.0235(5) Uani 1 1 d . . . . .
C121 C 0.3227(3) 1.0227(2) 0.16970(18) 0.0356(6) Uani 1 1 d . . . . .
H12A H 0.2485 1.0425 0.1396 0.053 Uiso 1 1 calc R U . . .
H12B H 0.3360 1.0900 0.1866 0.053 Uiso 1 1 calc R U . . .
H12C H 0.2936 0.9778 0.2212 0.053 Uiso 1 1 calc R U . . .
P2 P 0.96148(7) 0.14874(5) 0.32594(4) 0.03035(15) Uani 1 1 d . . . . .
C21 C 0.9606(2) 0.27971(19) 0.27166(15) 0.0238(5) Uani 1 1 d . . . . .
N22 N 1.0043(2) 0.36040(16) 0.29343(13) 0.0260(4) Uani 1 1 d . . . . .
N25 N 0.9180(2) 0.31669(16) 0.19990(12) 0.0245(4) Uani 1 1 d . . . . .
C23 C 0.9882(3) 0.4489(2) 0.23539(17) 0.0313(6) Uani 1 1 d . . . . .
H23 H 1.0111 0.5162 0.2366 0.038 Uiso 1 1 calc R U . . .
C24 C 0.9346(3) 0.4218(2) 0.17759(17) 0.0315(6) Uani 1 1 d . . . . .
H24 H 0.9120 0.4662 0.1302 0.038 Uiso 1 1 calc R U . . .
C26 C 0.8366(3) 0.26307(19) 0.16691(16) 0.0280(5) Uani 1 1 d . . . . .
H26A H 0.8376 0.2896 0.1073 0.034 Uiso 1 1 calc R U . . .
H26B H 0.7359 0.2806 0.2030 0.034 Uiso 1 1 calc R U . . .
C28 C 0.9030(3) 0.0702(2) 0.11163(19) 0.0381(6) Uani 1 1 d . . . . .
H28 H 0.8788 0.0873 0.0588 0.046 Uiso 1 1 calc R U . . .
C29 C 0.9455(3) -0.0314(2) 0.1457(2) 0.0412(7) Uani 1 1 d . . . . .
H29 H 0.9572 -0.0995 0.1213 0.049 Uiso 1 1 calc R U . . .
C210 C 1.0185(3) -0.1077(2) 0.28019(19) 0.0426(7) Uani 1 1 d . . . . .
H21A H 1.0211 -0.0770 0.3322 0.064 Uiso 1 1 calc R U . . .
H21B H 1.1147 -0.1517 0.2507 0.064 Uiso 1 1 calc R U . . .
H21C H 0.9529 -0.1547 0.2961 0.064 Uiso 1 1 calc R U . . .
N27 N 0.9012(2) 0.14483(16) 0.16832(13) 0.0280(4) Uani 1 1 d . . . . .
N210 N 0.9690(2) -0.01777(17) 0.22281(15) 0.0327(5) Uani 1 1 d . . . . .
C211 C 0.9411(2) 0.09063(19) 0.23745(16) 0.0275(5) Uani 1 1 d . . . . .
C221 C 1.0675(3) 0.3535(2) 0.36390(17) 0.0360(6) Uani 1 1 d . . . . .
H22A H 1.0236 0.3091 0.4115 0.054 Uiso 1 1 calc R U . . .
H22B H 1.0507 0.4278 0.3838 0.054 Uiso 1 1 calc R U . . .
H22C H 1.1707 0.3190 0.3438 0.054 Uiso 1 1 calc R U . . .
P3 P 0.67067(7) 0.18020(5) 0.57153(4) 0.03094(15) Uani 1 1 d . . . . .
C31 C 0.6464(2) 0.30166(19) 0.50384(15) 0.0255(5) Uani 1 1 d . . . . .
N32 N 0.6974(2) 0.38937(16) 0.50126(13) 0.0287(4) Uani 1 1 d . . . . .
N35 N 0.5851(2) 0.31866(15) 0.43881(13) 0.0245(4) Uani 1 1 d . . . . .
C33 C 0.6702(3) 0.4596(2) 0.43360(17) 0.0331(6) Uani 1 1 d . . . . .
H33 H 0.6959 0.5269 0.4180 0.040 Uiso 1 1 calc R U . . .
C34 C 0.6010(2) 0.41571(19) 0.39391(16) 0.0294(5) Uani 1 1 d . . . . .
H34 H 0.5693 0.4452 0.3448 0.035 Uiso 1 1 calc R U . . .
C36 C 0.5035(2) 0.24838(19) 0.42678(16) 0.0263(5) Uani 1 1 d . . . . .
H36A H 0.4838 0.2645 0.3701 0.032 Uiso 1 1 calc R U . . .
H36B H 0.4110 0.2610 0.4722 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6011(3) 0.04723(19) 0.38277(16) 0.0279(5) Uani 1 1 d . . . . .
H38 H 0.5658 0.0508 0.3345 0.034 Uiso 1 1 calc R U . . .
C39 C 0.6736(3) -0.0437(2) 0.41713(16) 0.0295(5) Uani 1 1 d . . . . .
H39 H 0.6983 -0.1169 0.3980 0.035 Uiso 1 1 calc R U . . .
C310 C 0.7889(3) -0.0816(2) 0.53946(19) 0.0410(7) Uani 1 1 d . . . . .
H31A H 0.8624 -0.0485 0.5438 0.062 Uiso 1 1 calc R U . . .
H31B H 0.8348 -0.1543 0.5137 0.062 Uiso 1 1 calc R U . . .
H31C H 0.7256 -0.0896 0.5970 0.062 Uiso 1 1 calc R U . . .
C311 C 0.6527(2) 0.09923(19) 0.49454(15) 0.0251(5) Uani 1 1 d . . . . .
C321 C 0.7712(3) 0.4059(2) 0.56144(19) 0.0400(6) Uani 1 1 d . . . . .
H32A H 0.7024 0.4235 0.6181 0.060 Uiso 1 1 calc R U . . .
H32B H 0.8147 0.4669 0.5403 0.060 Uiso 1 1 calc R U . . .
H32C H 0.8460 0.3384 0.5661 0.060 Uiso 1 1 calc R U . . .
N37 N 0.5880(2) 0.13466(15) 0.43135(12) 0.0235(4) Uani 1 1 d . . . . .
N310 N 0.7055(2) -0.01092(16) 0.48567(13) 0.0276(4) Uani 1 1 d . . . . .
Br1 Br 0.87042(3) 0.66218(2) 0.41503(2) 0.03036(7) Uani 1 1 d . . . . .
Br2 Br 0.00080(3) 0.31651(2) 0.94694(2) 0.03149(7) Uani 1 1 d . . . . .
Br3 Br 0.46428(3) 0.24230(2) 0.21456(2) 0.03133(7) Uani 1 1 d . . . . .
C41 C 0.5968(3) 0.6703(2) 0.25283(16) 0.0372(6) Uani 1 1 d . . . . .
C42 C 0.6772(3) 0.7497(3) 0.24491(19) 0.0481(8) Uani 1 1 d . . . . .
H42A H 0.6121 0.8242 0.2506 0.072 Uiso 1 1 calc R U . . .
H42B H 0.7485 0.7434 0.1885 0.072 Uiso 1 1 calc R U . . .
H42C H 0.7257 0.7354 0.2903 0.072 Uiso 1 1 calc R U . . .
N41 N 0.5326(3) 0.6082(2) 0.25962(17) 0.0542(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C11 1.783(2) . ?
P1 C111 1.792(2) . ?
C11 N12 1.348(3) . ?
C11 N15 1.358(3) . ?
N12 C13 1.389(3) . ?
N12 C121 1.457(3) . ?
N15 C14 1.394(3) . ?
N15 C16 1.448(3) . ?
C13 C14 1.344(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 N17 1.447(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 C19 1.338(4) . ?
C18 N17 1.389(3) . ?
C18 H18 0.9500 . ?
C19 N110 1.388(3) . ?
C19 H19 0.9500 . ?
C110 N110 1.457(3) . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
N17 C111 1.352(3) . ?
N110 C111 1.341(3) . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
P2 C211 1.778(3) . ?
P2 C21 1.793(2) . ?
C21 N22 1.344(3) . ?
C21 N25 1.357(3) . ?
N22 C23 1.391(3) . ?
N22 C221 1.458(3) . ?
N25 C24 1.387(3) . ?
N25 C26 1.452(3) . ?
C23 C24 1.337(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C26 N27 1.453(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 C29 1.349(4) . ?
C28 N27 1.385(3) . ?
C28 H28 0.9500 . ?
C29 N210 1.384(4) . ?
C29 H29 0.9500 . ?
C210 N210 1.465(3) . ?
C210 H21A 0.9800 . ?
C210 H21B 0.9800 . ?
C210 H21C 0.9800 . ?
N27 C211 1.360(3) . ?
N210 C211 1.353(3) . ?
C221 H22A 0.9800 . ?
C221 H22B 0.9800 . ?
C221 H22C 0.9800 . ?
P3 C311 1.784(3) . ?
P3 C31 1.795(2) . ?
C31 N32 1.348(3) . ?
C31 N35 1.351(3) . ?
N32 C33 1.382(3) . ?
N32 C321 1.465(3) . ?
N35 C34 1.387(3) . ?
N35 C36 1.444(3) . ?
C33 C34 1.342(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C36 N37 1.456(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C38 C39 1.341(3) . ?
C38 N37 1.383(3) . ?
C38 H38 0.9500 . ?
C39 N310 1.386(3) . ?
C39 H39 0.9500 . ?
C310 N310 1.458(3) . ?
C310 H31A 0.9800 . ?
C310 H31B 0.9800 . ?
C310 H31C 0.9800 . ?
C311 N310 1.350(3) . ?
C311 N37 1.353(3) . ?
C321 H32A 0.9800 . ?
C321 H32B 0.9800 . ?
C321 H32C 0.9800 . ?
C41 N41 1.137(4) . ?
C41 C42 1.444(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 P1 C111 91.43(10) . . ?
N12 C11 N15 106.04(19) . . ?
N12 C11 P1 126.48(17) . . ?
N15 C11 P1 127.45(17) . . ?
C11 N12 C13 110.07(19) . . ?
C11 N12 C121 123.6(2) . . ?
C13 N12 C121 126.0(2) . . ?
C11 N15 C14 109.71(19) . . ?
C11 N15 C16 121.76(19) . . ?
C14 N15 C16 128.2(2) . . ?
C14 C13 N12 107.3(2) . . ?
C14 C13 H13 126.4 . . ?
N12 C13 H13 126.4 . . ?
C13 C14 N15 106.9(2) . . ?
C13 C14 H14 126.5 . . ?
N15 C14 H14 126.5 . . ?
N17 C16 N15 108.18(19) . . ?
N17 C16 H16A 110.1 . . ?
N15 C16 H16A 110.1 . . ?
N17 C16 H16B 110.1 . . ?
N15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C19 C18 N17 106.7(2) . . ?
C19 C18 H18 126.7 . . ?
N17 C18 H18 126.7 . . ?
C18 C19 N110 107.6(2) . . ?
C18 C19 H19 126.2 . . ?
N110 C19 H19 126.2 . . ?
N110 C110 H11A 109.5 . . ?
N110 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
N110 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C111 N17 C18 109.69(19) . . ?
C111 N17 C16 122.25(19) . . ?
C18 N17 C16 127.8(2) . . ?
C111 N110 C19 109.5(2) . . ?
C111 N110 C110 124.6(2) . . ?
C19 N110 C110 125.7(2) . . ?
N110 C111 N17 106.49(19) . . ?
N110 C111 P1 126.42(18) . . ?
N17 C111 P1 126.96(17) . . ?
N12 C121 H12A 109.5 . . ?
N12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
N12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C211 P2 C21 93.13(11) . . ?
N22 C21 N25 106.21(19) . . ?
N22 C21 P2 126.66(18) . . ?
N25 C21 P2 127.12(18) . . ?
C21 N22 C23 109.7(2) . . ?
C21 N22 C221 125.1(2) . . ?
C23 N22 C221 125.1(2) . . ?
C21 N25 C24 109.6(2) . . ?
C21 N25 C26 122.56(19) . . ?
C24 N25 C26 126.2(2) . . ?
C24 C23 N22 107.4(2) . . ?
C24 C23 H23 126.3 . . ?
N22 C23 H23 126.3 . . ?
C23 C24 N25 107.1(2) . . ?
C23 C24 H24 126.5 . . ?
N25 C24 H24 126.5 . . ?
N25 C26 N27 108.38(18) . . ?
N25 C26 H26A 110.0 . . ?
N27 C26 H26A 110.0 . . ?
N25 C26 H26B 110.0 . . ?
N27 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C29 C28 N27 106.9(3) . . ?
C29 C28 H28 126.5 . . ?
N27 C28 H28 126.5 . . ?
C28 C29 N210 107.1(2) . . ?
C28 C29 H29 126.5 . . ?
N210 C29 H29 126.5 . . ?
N210 C210 H21A 109.5 . . ?
N210 C210 H21B 109.5 . . ?
H21A C210 H21B 109.5 . . ?
N210 C210 H21C 109.5 . . ?
H21A C210 H21C 109.5 . . ?
H21B C210 H21C 109.5 . . ?
C211 N27 C28 110.2(2) . . ?
C211 N27 C26 122.3(2) . . ?
C28 N27 C26 126.1(2) . . ?
C211 N210 C29 110.4(2) . . ?
C211 N210 C210 124.6(2) . . ?
C29 N210 C210 125.0(2) . . ?
N210 C211 N27 105.4(2) . . ?
N210 C211 P2 126.94(19) . . ?
N27 C211 P2 127.58(18) . . ?
N22 C221 H22A 109.5 . . ?
N22 C221 H22B 109.5 . . ?
H22A C221 H22B 109.5 . . ?
N22 C221 H22C 109.5 . . ?
H22A C221 H22C 109.5 . . ?
H22B C221 H22C 109.5 . . ?
C311 P3 C31 91.68(11) . . ?
N32 C31 N35 105.7(2) . . ?
N32 C31 P3 127.51(19) . . ?
N35 C31 P3 126.49(18) . . ?
C31 N32 C33 109.8(2) . . ?
C31 N32 C321 124.4(2) . . ?
C33 N32 C321 125.8(2) . . ?
C31 N35 C34 110.4(2) . . ?
C31 N35 C36 122.21(19) . . ?
C34 N35 C36 127.1(2) . . ?
C34 C33 N32 107.7(2) . . ?
C34 C33 H33 126.1 . . ?
N32 C33 H33 126.1 . . ?
C33 C34 N35 106.3(2) . . ?
C33 C34 H34 126.9 . . ?
N35 C34 H34 126.9 . . ?
N35 C36 N37 107.59(18) . . ?
N35 C36 H36A 110.2 . . ?
N37 C36 H36A 110.2 . . ?
N35 C36 H36B 110.2 . . ?
N37 C36 H36B 110.2 . . ?
H36A C36 H36B 108.5 . . ?
C39 C38 N37 106.6(2) . . ?
C39 C38 H38 126.7 . . ?
N37 C38 H38 126.7 . . ?
C38 C39 N310 107.3(2) . . ?
C38 C39 H39 126.3 . . ?
N310 C39 H39 126.3 . . ?
N310 C310 H31A 109.5 . . ?
N310 C310 H31B 109.5 . . ?
H31A C310 H31B 109.5 . . ?
N310 C310 H31C 109.5 . . ?
H31A C310 H31C 109.5 . . ?
H31B C310 H31C 109.5 . . ?
N310 C311 N37 105.4(2) . . ?
N310 C311 P3 126.79(18) . . ?
N37 C311 P3 127.80(18) . . ?
N32 C321 H32A 109.5 . . ?
N32 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
N32 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C311 N37 C38 110.57(19) . . ?
C311 N37 C36 121.1(2) . . ?
C38 N37 C36 127.9(2) . . ?
C311 N310 C39 110.1(2) . . ?
C311 N310 C310 123.4(2) . . ?
C39 N310 C310 126.4(2) . . ?
N41 C41 C42 179.4(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C111 P1 C11 N12 -154.6(2) . . . . ?
C111 P1 C11 N15 23.1(2) . . . . ?
N15 C11 N12 C13 -0.2(3) . . . . ?
P1 C11 N12 C13 177.96(18) . . . . ?
N15 C11 N12 C121 -174.0(2) . . . . ?
P1 C11 N12 C121 4.2(3) . . . . ?
N12 C11 N15 C14 0.3(3) . . . . ?
P1 C11 N15 C14 -177.81(18) . . . . ?
N12 C11 N15 C16 -173.36(19) . . . . ?
P1 C11 N15 C16 8.5(3) . . . . ?
C11 N12 C13 C14 0.0(3) . . . . ?
C121 N12 C13 C14 173.6(2) . . . . ?
N12 C13 C14 N15 0.2(3) . . . . ?
C11 N15 C14 C13 -0.3(3) . . . . ?
C16 N15 C14 C13 172.8(2) . . . . ?
C11 N15 C16 N17 -45.1(3) . . . . ?
C14 N15 C16 N17 142.5(2) . . . . ?
N17 C18 C19 N110 0.0(3) . . . . ?
C19 C18 N17 C111 -0.2(3) . . . . ?
C19 C18 N17 C16 -174.3(2) . . . . ?
N15 C16 N17 C111 45.5(3) . . . . ?
N15 C16 N17 C18 -141.1(2) . . . . ?
C18 C19 N110 C111 0.2(3) . . . . ?
C18 C19 N110 C110 -173.7(2) . . . . ?
C19 N110 C111 N17 -0.4(3) . . . . ?
C110 N110 C111 N17 173.7(2) . . . . ?
C19 N110 C111 P1 -176.42(18) . . . . ?
C110 N110 C111 P1 -2.4(3) . . . . ?
C18 N17 C111 N110 0.4(3) . . . . ?
C16 N17 C111 N110 174.80(19) . . . . ?
C18 N17 C111 P1 176.40(17) . . . . ?
C16 N17 C111 P1 -9.2(3) . . . . ?
C11 P1 C111 N110 152.5(2) . . . . ?
C11 P1 C111 N17 -22.8(2) . . . . ?
C211 P2 C21 N22 -163.7(2) . . . . ?
C211 P2 C21 N25 15.2(2) . . . . ?
N25 C21 N22 C23 0.4(3) . . . . ?
P2 C21 N22 C23 179.52(18) . . . . ?
N25 C21 N22 C221 -176.0(2) . . . . ?
P2 C21 N22 C221 3.1(3) . . . . ?
N22 C21 N25 C24 -0.5(3) . . . . ?
P2 C21 N25 C24 -179.60(18) . . . . ?
N22 C21 N25 C26 -167.0(2) . . . . ?
P2 C21 N25 C26 13.9(3) . . . . ?
C21 N22 C23 C24 -0.2(3) . . . . ?
C221 N22 C23 C24 176.3(2) . . . . ?
N22 C23 C24 N25 -0.1(3) . . . . ?
C21 N25 C24 C23 0.4(3) . . . . ?
C26 N25 C24 C23 166.3(2) . . . . ?
C21 N25 C26 N27 -45.1(3) . . . . ?
C24 N25 C26 N27 150.8(2) . . . . ?
N27 C28 C29 N210 0.2(3) . . . . ?
C29 C28 N27 C211 -0.5(3) . . . . ?
C29 C28 N27 C26 -167.3(2) . . . . ?
N25 C26 N27 C211 45.5(3) . . . . ?
N25 C26 N27 C28 -149.1(2) . . . . ?
C28 C29 N210 C211 0.2(3) . . . . ?
C28 C29 N210 C210 -179.1(2) . . . . ?
C29 N210 C211 N27 -0.5(3) . . . . ?
C210 N210 C211 N27 178.8(2) . . . . ?
C29 N210 C211 P2 -177.68(18) . . . . ?
C210 N210 C211 P2 1.7(3) . . . . ?
C28 N27 C211 N210 0.6(3) . . . . ?
C26 N27 C211 N210 168.0(2) . . . . ?
C28 N27 C211 P2 177.75(18) . . . . ?
C26 N27 C211 P2 -14.8(3) . . . . ?
C21 P2 C211 N210 161.7(2) . . . . ?
C21 P2 C211 N27 -14.8(2) . . . . ?
C311 P3 C31 N32 -152.5(2) . . . . ?
C311 P3 C31 N35 20.3(2) . . . . ?
N35 C31 N32 C33 -1.2(3) . . . . ?
P3 C31 N32 C33 172.79(18) . . . . ?
N35 C31 N32 C321 179.2(2) . . . . ?
P3 C31 N32 C321 -6.8(4) . . . . ?
N32 C31 N35 C34 1.6(3) . . . . ?
P3 C31 N35 C34 -172.43(17) . . . . ?
N32 C31 N35 C36 -172.7(2) . . . . ?
P3 C31 N35 C36 13.3(3) . . . . ?
C31 N32 C33 C34 0.3(3) . . . . ?
C321 N32 C33 C34 179.9(2) . . . . ?
N32 C33 C34 N35 0.7(3) . . . . ?
C31 N35 C34 C33 -1.4(3) . . . . ?
C36 N35 C34 C33 172.5(2) . . . . ?
C31 N35 C36 N37 -48.7(3) . . . . ?
C34 N35 C36 N37 138.0(2) . . . . ?
N37 C38 C39 N310 -0.7(3) . . . . ?
C31 P3 C311 N310 155.5(2) . . . . ?
C31 P3 C311 N37 -22.2(2) . . . . ?
N310 C311 N37 C38 -0.4(3) . . . . ?
P3 C311 N37 C38 177.68(17) . . . . ?
N310 C311 N37 C36 172.67(19) . . . . ?
P3 C311 N37 C36 -9.2(3) . . . . ?
C39 C38 N37 C311 0.7(3) . . . . ?
C39 C38 N37 C36 -171.8(2) . . . . ?
N35 C36 N37 C311 46.4(3) . . . . ?
N35 C36 N37 C38 -141.8(2) . . . . ?
N37 C311 N310 C39 0.0(3) . . . . ?
P3 C311 N310 C39 -178.16(17) . . . . ?
N37 C311 N310 C310 177.6(2) . . . . ?
P3 C311 N310 C310 -0.6(3) . . . . ?
C38 C39 N310 C311 0.5(3) . . . . ?
C38 C39 N310 C310 -177.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 Br3 0.95 2.92 3.711(3) 141.9 1_565
C14 H14 Br2 0.95 3.02 3.581(2) 119.5 2_666
C16 H16A Br3 0.99 2.88 3.853(2) 167.1 2_665
C16 H16B Br2 0.99 2.88 3.694(2) 140.7 2_666
C18 H18 Br2 0.95 2.78 3.661(2) 154.3 1_654
C19 H19 Br3 0.95 2.94 3.760(3) 145.4 .
C110 H11B Br3 0.98 2.96 3.885(3) 157.1 .
C110 H11C Br2 0.98 2.96 3.933(3) 173.7 2_566
C121 H12B Br3 0.98 2.76 3.707(3) 161.6 1_565
C26 H26A Br2 0.99 2.69 3.555(3) 146.0 1_654
C26 H26B Br3 0.99 2.89 3.713(2) 141.2 .
C29 H29 Br2 0.95 2.95 3.896(3) 177.1 2_656
C210 H21C Br1 0.98 3.00 3.844(3) 144.5 1_545
C221 H22B Br1 0.98 3.01 3.897(3) 151.1 .
C221 H22C Br3 0.98 3.05 3.972(3) 157.3 1_655
C33 H33 Br1 0.95 2.79 3.650(3) 150.9 .
C34 H34 N41 0.95 2.36 3.161(4) 141.5 .
C36 H36A Br3 0.99 2.65 3.608(2) 162.6 .
C36 H36B Br1 0.99 2.85 3.830(2) 168.6 2_666
C38 H38 Br3 0.95 3.08 3.792(2) 132.8 .
C39 H39 Br1 0.95 2.87 3.685(2) 143.8 1_545
C310 H31B Br1 0.98 2.85 3.769(3) 157.2 1_545
C321 H32B Br1 0.98 3.10 4.004(3) 153.3 .
C321 H32C Br1 0.98 2.99 3.623(3) 123.5 2_766
C42 H42B Br2 0.98 2.80 3.749(3) 164.0 2_666
C42 H42C Br1 0.98 2.78 3.755(3) 171.6 .

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.077

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042844'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 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         'C21 H20 N4 P, Br'
_chemical_formula_sum            'C21 H20 Br N4 P'
_chemical_formula_weight         439.29

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.2417(10)
_cell_length_b                   4.8288(4)
_cell_length_c                   33.910(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.281(3)
_cell_angle_gamma                90
_cell_volume                     1983.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      24.65

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    2.166
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   SADABS;Bruker,2012
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34945
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         3.147
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4384
_reflns_number_gt                3465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+1.0762P] 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         4384
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P P 0.18953(5) 0.10915(12) 0.40629(2) 0.02966(14) Uani 1 1 d . . . . .
C1 C 0.29946(16) 0.3291(4) 0.42860(6) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.39933(14) 0.3673(4) 0.41696(5) 0.0271(4) Uani 1 1 d . . . . .
N5 N 0.29734(14) 0.5005(4) 0.46001(5) 0.0273(4) Uani 1 1 d . . . . .
C3 C 0.45808(18) 0.5661(5) 0.44061(6) 0.0325(5) Uani 1 1 d . . . . .
H3 H 0.5302 0.6305 0.4384 0.039 Uiso 1 1 calc R U . . .
C4 C 0.39423(17) 0.6512(5) 0.46737(6) 0.0306(5) Uani 1 1 d . . . . .
H4 H 0.4121 0.7879 0.4874 0.037 Uiso 1 1 calc R U . . .
C6 C 0.20635(18) 0.4985(5) 0.48314(6) 0.0307(5) Uani 1 1 d . . . . .
H6A H 0.2104 0.3315 0.5002 0.037 Uiso 1 1 calc R U . . .
H6B H 0.2099 0.6642 0.5005 0.037 Uiso 1 1 calc R U . . .
C8 C 0.00913(18) 0.6494(5) 0.45799(6) 0.0297(5) Uani 1 1 d . . . . .
H8 H 0.0004 0.7906 0.4768 0.036 Uiso 1 1 calc R U . . .
C9 C -0.06825(18) 0.5585(4) 0.42889(6) 0.0301(5) Uani 1 1 d . . . . .
H9 H -0.1425 0.6207 0.4235 0.036 Uiso 1 1 calc R U . . .
C11 C 0.08749(16) 0.3230(4) 0.42421(6) 0.0248(4) Uani 1 1 d . . . . .
N7 N 0.10441(14) 0.4985(3) 0.45550(5) 0.0266(4) Uani 1 1 d . . . . .
N10 N -0.01946(14) 0.3565(4) 0.40814(5) 0.0263(4) Uani 1 1 d . . . . .
C21 C 0.43665(17) 0.2360(5) 0.38198(6) 0.0304(5) Uani 1 1 d . . . . .
H21A H 0.3854 0.0842 0.3722 0.036 Uiso 1 1 calc R U . . .
H21B H 0.5109 0.1548 0.3898 0.036 Uiso 1 1 calc R U . . .
C22 C 0.44113(17) 0.4430(4) 0.34897(6) 0.0287(5) Uani 1 1 d . . . . .
C23 C 0.53701(19) 0.5925(5) 0.34666(7) 0.0394(6) Uani 1 1 d . . . . .
H23 H 0.6009 0.5616 0.3656 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5395(2) 0.7857(6) 0.31680(8) 0.0486(7) Uani 1 1 d . . . . .
H24 H 0.6050 0.8885 0.3155 0.058 Uiso 1 1 calc R U . . .
C25 C 0.4483(2) 0.8309(6) 0.28897(7) 0.0489(7) Uani 1 1 d . . . . .
H25 H 0.4510 0.9626 0.2683 0.059 Uiso 1 1 calc R U . . .
C26 C 0.3529(2) 0.6849(6) 0.29109(7) 0.0489(7) Uani 1 1 d . . . . .
H26 H 0.2895 0.7164 0.2719 0.059 Uiso 1 1 calc R U . . .
C27 C 0.3491(2) 0.4924(5) 0.32100(7) 0.0391(6) Uani 1 1 d . . . . .
H27 H 0.2827 0.3930 0.3224 0.047 Uiso 1 1 calc R U . . .
C101 C -0.07264(17) 0.2278(5) 0.37149(6) 0.0298(5) Uani 1 1 d . . . . .
H10A H -0.1469 0.1615 0.3753 0.036 Uiso 1 1 calc R U . . .
H10B H -0.0288 0.0655 0.3652 0.036 Uiso 1 1 calc R U . . .
C102 C -0.08330(18) 0.4283(4) 0.33702(6) 0.0284(5) Uani 1 1 d . . . . .
C103 C -0.1843(2) 0.4733(5) 0.31384(7) 0.0397(6) Uani 1 1 d . . . . .
H103 H -0.2478 0.3771 0.3196 0.048 Uiso 1 1 calc R U . . .
C104 C -0.1934(2) 0.6580(6) 0.28221(7) 0.0474(6) Uani 1 1 d . . . . .
H104 H -0.2629 0.6863 0.2663 0.057 Uiso 1 1 calc R U . . .
C105 C -0.1026(2) 0.7997(5) 0.27379(7) 0.0470(7) Uani 1 1 d . . . . .
H105 H -0.1094 0.9263 0.2521 0.056 Uiso 1 1 calc R U . . .
C106 C -0.0016(2) 0.7589(5) 0.29669(7) 0.0437(6) Uani 1 1 d . . . . .
H106 H 0.0613 0.8576 0.2909 0.052 Uiso 1 1 calc R U . . .
C107 C 0.00805(19) 0.5733(5) 0.32823(7) 0.0358(5) Uani 1 1 d . . . . .
H107 H 0.0779 0.5452 0.3440 0.043 Uiso 1 1 calc R U . . .
Br Br 0.29177(2) 0.52598(4) 0.06260(2) 0.03084(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P C11 1.793(2) . ?
P C1 1.794(2) . ?
C1 N2 1.351(3) . ?
C1 N5 1.352(3) . ?
N2 C3 1.384(3) . ?
N2 C21 1.474(3) . ?
N5 C4 1.383(3) . ?
N5 C6 1.452(3) . ?
C3 C4 1.344(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 N7 1.449(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.339(3) . ?
C8 N7 1.388(3) . ?
C8 H8 0.9500 . ?
C9 N10 1.387(3) . ?
C9 H9 0.9500 . ?
C11 N7 1.350(3) . ?
C11 N10 1.353(3) . ?
N10 C101 1.457(3) . ?
C21 C22 1.508(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.385(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C101 C102 1.509(3) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 C103 1.383(3) . ?
C102 C107 1.388(3) . ?
C103 C104 1.387(4) . ?
C103 H103 0.9500 . ?
C104 C105 1.370(4) . ?
C104 H104 0.9500 . ?
C105 C106 1.376(4) . ?
C105 H105 0.9500 . ?
C106 C107 1.388(3) . ?
C106 H106 0.9500 . ?
C107 H107 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 P C1 91.89(10) . . ?
N2 C1 N5 105.52(18) . . ?
N2 C1 P 127.82(16) . . ?
N5 C1 P 126.61(15) . . ?
C1 N2 C3 109.99(17) . . ?
C1 N2 C21 125.10(18) . . ?
C3 N2 C21 124.69(17) . . ?
C1 N5 C4 110.54(17) . . ?
C1 N5 C6 121.66(18) . . ?
C4 N5 C6 127.64(18) . . ?
C4 C3 N2 107.40(19) . . ?
C4 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C3 C4 N5 106.52(19) . . ?
C3 C4 H4 126.7 . . ?
N5 C4 H4 126.7 . . ?
N7 C6 N5 107.87(16) . . ?
N7 C6 H6A 110.1 . . ?
N5 C6 H6A 110.1 . . ?
N7 C6 H6B 110.1 . . ?
N5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C9 C8 N7 107.14(19) . . ?
C9 C8 H8 126.4 . . ?
N7 C8 H8 126.4 . . ?
C8 C9 N10 107.06(19) . . ?
C8 C9 H9 126.5 . . ?
N10 C9 H9 126.5 . . ?
N7 C11 N10 105.74(17) . . ?
N7 C11 P 126.33(16) . . ?
N10 C11 P 127.81(16) . . ?
C11 N7 C8 110.00(18) . . ?
C11 N7 C6 121.91(17) . . ?
C8 N7 C6 127.86(18) . . ?
C11 N10 C9 110.00(18) . . ?
C11 N10 C101 125.46(17) . . ?
C9 N10 C101 124.10(18) . . ?
N2 C21 C22 111.15(17) . . ?
N2 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N2 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C27 C22 C23 118.8(2) . . ?
C27 C22 C21 120.6(2) . . ?
C23 C22 C21 120.5(2) . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.7(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 120.5(2) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
N10 C101 C102 111.43(17) . . ?
N10 C101 H10A 109.3 . . ?
C102 C101 H10A 109.3 . . ?
N10 C101 H10B 109.3 . . ?
C102 C101 H10B 109.3 . . ?
H10A C101 H10B 108.0 . . ?
C103 C102 C107 118.7(2) . . ?
C103 C102 C101 120.8(2) . . ?
C107 C102 C101 120.5(2) . . ?
C102 C103 C104 120.4(2) . . ?
C102 C103 H103 119.8 . . ?
C104 C103 H103 119.8 . . ?
C105 C104 C103 120.3(2) . . ?
C105 C104 H104 119.8 . . ?
C103 C104 H104 119.8 . . ?
C104 C105 C106 120.1(2) . . ?
C104 C105 H105 120.0 . . ?
C106 C105 H105 120.0 . . ?
C105 C106 C107 119.8(2) . . ?
C105 C106 H106 120.1 . . ?
C107 C106 H106 120.1 . . ?
C106 C107 C102 120.7(2) . . ?
C106 C107 H107 119.7 . . ?
C102 C107 H107 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P C1 N2 -153.17(19) . . . . ?
C11 P C1 N5 24.06(19) . . . . ?
N5 C1 N2 C3 -1.2(2) . . . . ?
P C1 N2 C3 176.50(16) . . . . ?
N5 C1 N2 C21 -176.05(17) . . . . ?
P C1 N2 C21 1.6(3) . . . . ?
N2 C1 N5 C4 1.6(2) . . . . ?
P C1 N5 C4 -176.09(15) . . . . ?
N2 C1 N5 C6 -174.08(17) . . . . ?
P C1 N5 C6 8.2(3) . . . . ?
C1 N2 C3 C4 0.3(2) . . . . ?
C21 N2 C3 C4 175.20(19) . . . . ?
N2 C3 C4 N5 0.7(2) . . . . ?
C1 N5 C4 C3 -1.5(2) . . . . ?
C6 N5 C4 C3 173.93(19) . . . . ?
C1 N5 C6 N7 -46.4(2) . . . . ?
C4 N5 C6 N7 138.6(2) . . . . ?
N7 C8 C9 N10 -1.3(2) . . . . ?
C1 P C11 N7 -22.61(19) . . . . ?
C1 P C11 N10 152.80(18) . . . . ?
N10 C11 N7 C8 -2.3(2) . . . . ?
P C11 N7 C8 173.91(15) . . . . ?
N10 C11 N7 C6 172.62(17) . . . . ?
P C11 N7 C6 -11.2(3) . . . . ?
C9 C8 N7 C11 2.3(2) . . . . ?
C9 C8 N7 C6 -172.29(19) . . . . ?
N5 C6 N7 C11 48.1(2) . . . . ?
N5 C6 N7 C8 -137.9(2) . . . . ?
N7 C11 N10 C9 1.5(2) . . . . ?
P C11 N10 C9 -174.62(15) . . . . ?
N7 C11 N10 C101 174.14(17) . . . . ?
P C11 N10 C101 -2.0(3) . . . . ?
C8 C9 N10 C11 -0.2(2) . . . . ?
C8 C9 N10 C101 -172.89(18) . . . . ?
C1 N2 C21 C22 107.7(2) . . . . ?
C3 N2 C21 C22 -66.5(3) . . . . ?
N2 C21 C22 C27 -88.4(2) . . . . ?
N2 C21 C22 C23 90.1(2) . . . . ?
C27 C22 C23 C24 -0.2(3) . . . . ?
C21 C22 C23 C24 -178.6(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C27 -0.3(4) . . . . ?
C25 C26 C27 C22 -0.4(4) . . . . ?
C23 C22 C27 C26 0.7(3) . . . . ?
C21 C22 C27 C26 179.1(2) . . . . ?
C11 N10 C101 C102 -101.2(2) . . . . ?
C9 N10 C101 C102 70.4(2) . . . . ?
N10 C101 C102 C103 -127.2(2) . . . . ?
N10 C101 C102 C107 52.1(3) . . . . ?
C107 C102 C103 C104 0.6(3) . . . . ?
C101 C102 C103 C104 180.0(2) . . . . ?
C102 C103 C104 C105 -0.6(4) . . . . ?
C103 C104 C105 C106 0.2(4) . . . . ?
C104 C105 C106 C107 0.2(4) . . . . ?
C105 C106 C107 C102 -0.1(4) . . . . ?
C103 C102 C107 C106 -0.3(3) . . . . ?
C101 C102 C107 C106 -179.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Br 0.95 2.90 3.797(2) 157.7 2_655
C6 H6A Br 0.99 2.80 3.736(2) 157.9 4_566
C6 H6B Br 0.99 2.66 3.580(2) 154.7 4_576
C9 H9 Br 0.95 2.76 3.591(2) 146.0 2
C21 H21B Br 0.99 2.78 3.717(2) 159.0 2_645
C101 H10A Br 0.99 3.01 3.856(2) 143.8 2_545

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042845'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 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         'C9 H12 N4 P, C F3 O3 S'
_chemical_formula_sum            'C10 H12 F3 N4 O3 P S'
_chemical_formula_weight         356.27

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   8.2477(3)
_cell_length_b                   8.4833(3)
_cell_length_c                   10.7821(4)
_cell_angle_alpha                97.8660(10)
_cell_angle_beta                 104.3960(10)
_cell_angle_gamma                93.2520(10)
_cell_volume                     720.59(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      35.55

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.387
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   'SADABS;Bruker, 2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19018
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.886
_diffrn_reflns_theta_max         35.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6604
_reflns_number_gt                4651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.1774P] 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         6604
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P P 1.34622(5) 0.44329(5) 0.16685(4) 0.02681(10) Uani 1 1 d . . . . .
N2 N 1.17707(15) 0.62935(14) -0.01097(11) 0.0229(2) Uani 1 1 d . . . . .
N5 N 1.18776(15) 0.72856(13) 0.18643(11) 0.0203(2) Uani 1 1 d . . . . .
C1 C 1.23550(17) 0.60604(16) 0.11336(12) 0.0202(2) Uani 1 1 d . . . . .
C3 C 1.09479(19) 0.76676(18) -0.01453(14) 0.0269(3) Uani 1 1 d . . . . .
H3 H 1.0429 0.8093 -0.0901 0.032 Uiso 1 1 calc R U . . .
C4 C 1.10138(19) 0.82938(17) 0.10827(14) 0.0252(3) Uani 1 1 d . . . . .
H4 H 1.0557 0.9242 0.1360 0.030 Uiso 1 1 calc R U . . .
C6 C 1.24817(19) 0.76041(16) 0.32626(13) 0.0234(3) Uani 1 1 d . . . . .
H6A H 1.1769 0.8339 0.3629 0.028 Uiso 1 1 calc R U . . .
H6B H 1.3651 0.8113 0.3518 0.028 Uiso 1 1 calc R U . . .
C8 C 1.2083(2) 0.58391(19) 0.49109(15) 0.0311(3) Uani 1 1 d . . . . .
H8 H 1.1681 0.6577 0.5484 0.037 Uiso 1 1 calc R U . . .
C9 C 1.2437(2) 0.4342(2) 0.50643(16) 0.0334(3) Uani 1 1 d . . . . .
H9 H 1.2327 0.3822 0.5770 0.040 Uiso 1 1 calc R U . . .
C11 C 1.29749(17) 0.47700(16) 0.31970(13) 0.0222(2) Uani 1 1 d . . . . .
N7 N 1.24175(16) 0.60981(14) 0.37508(11) 0.0228(2) Uani 1 1 d . . . . .
N10 N 1.29884(16) 0.36927(15) 0.40135(13) 0.0265(2) Uani 1 1 d . . . . .
C21 C 1.1937(2) 0.5217(2) -0.12397(15) 0.0333(3) Uani 1 1 d . . . . .
H21A H 1.3080 0.5389 -0.1341 0.050 Uiso 1 1 calc R U . . .
H21B H 1.1125 0.5433 -0.2016 0.050 Uiso 1 1 calc R U . . .
H21C H 1.1719 0.4108 -0.1121 0.050 Uiso 1 1 calc R U . . .
C101 C 1.3452(2) 0.20705(18) 0.37584(18) 0.0349(4) Uani 1 1 d . . . . .
H10A H 1.2907 0.1605 0.2857 0.052 Uiso 1 1 calc R U . . .
H10B H 1.3085 0.1420 0.4341 0.052 Uiso 1 1 calc R U . . .
H10C H 1.4675 0.2095 0.3906 0.052 Uiso 1 1 calc R U . . .
O1 O 0.86306(16) 0.82232(14) 0.31769(11) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.93697(15) 1.09907(14) 0.30423(11) 0.0347(3) Uani 1 1 d . . . . .
O3 O 0.72328(17) 1.03267(15) 0.41385(11) 0.0370(3) Uani 1 1 d . . . . .
S S 0.81186(4) 0.98181(4) 0.31835(3) 0.02189(9) Uani 1 1 d . . . . .
C01 C 0.65079(19) 0.96720(19) 0.16619(14) 0.0274(3) Uani 1 1 d . . . . .
F1 F 0.59665(15) 1.10953(15) 0.14908(11) 0.0487(3) Uani 1 1 d . . . . .
F2 F 0.51916(15) 0.86882(18) 0.16337(13) 0.0616(4) Uani 1 1 d . . . . .
F3 F 0.70967(14) 0.91549(13) 0.06599(9) 0.0398(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P C1 1.7810(14) . ?
P C11 1.7813(15) . ?
N2 C1 1.3530(17) . ?
N2 C3 1.3820(19) . ?
N2 C21 1.4594(18) . ?
N5 C1 1.3538(17) . ?
N5 C4 1.3846(17) . ?
N5 C6 1.4470(17) . ?
C3 C4 1.344(2) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 N7 1.4500(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.342(2) . ?
C8 N7 1.3890(18) . ?
C8 H8 0.9500 . ?
C9 N10 1.381(2) . ?
C9 H9 0.9500 . ?
C11 N10 1.3516(18) . ?
C11 N7 1.3595(17) . ?
N10 C101 1.4574(19) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
O1 S 1.4397(11) . ?
O2 S 1.4424(12) . ?
O3 S 1.4382(11) . ?
S C01 1.8203(15) . ?
C01 F2 1.3228(18) . ?
C01 F3 1.3232(18) . ?
C01 F1 1.3314(19) . ?

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
C1 P C11 92.07(6) . . ?
C1 N2 C3 109.77(12) . . ?
C1 N2 C21 124.75(13) . . ?
C3 N2 C21 125.45(13) . . ?
C1 N5 C4 110.33(11) . . ?
C1 N5 C6 122.60(12) . . ?
C4 N5 C6 126.14(11) . . ?
N2 C1 N5 105.69(12) . . ?
N2 C1 P 126.39(10) . . ?
N5 C1 P 127.89(10) . . ?
C4 C3 N2 107.68(13) . . ?
C4 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
C3 C4 N5 106.52(13) . . ?
C3 C4 H4 126.7 . . ?
N5 C4 H4 126.7 . . ?
N5 C6 N7 108.27(11) . . ?
N5 C6 H6A 110.0 . . ?
N7 C6 H6A 110.0 . . ?
N5 C6 H6B 110.0 . . ?
N7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C9 C8 N7 106.58(14) . . ?
C9 C8 H8 126.7 . . ?
N7 C8 H8 126.7 . . ?
C8 C9 N10 107.78(13) . . ?
C8 C9 H9 126.1 . . ?
N10 C9 H9 126.1 . . ?
N10 C11 N7 105.66(12) . . ?
N10 C11 P 126.11(11) . . ?
N7 C11 P 128.11(10) . . ?
C11 N7 C8 110.04(12) . . ?
C11 N7 C6 121.82(11) . . ?
C8 N7 C6 127.29(12) . . ?
C11 N10 C9 109.94(12) . . ?
C11 N10 C101 123.56(13) . . ?
C9 N10 C101 126.44(13) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N10 C101 H10A 109.5 . . ?
N10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
N10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O3 S O1 115.28(7) . . ?
O3 S O2 115.36(8) . . ?
O1 S O2 114.56(8) . . ?
O3 S C01 102.99(7) . . ?
O1 S C01 103.57(7) . . ?
O2 S C01 102.56(7) . . ?
F2 C01 F3 108.16(13) . . ?
F2 C01 F1 107.63(14) . . ?
F3 C01 F1 107.23(12) . . ?
F2 C01 S 111.54(11) . . ?
F3 C01 S 111.34(10) . . ?
F1 C01 S 110.76(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N5 0.55(15) . . . . ?
C21 N2 C1 N5 -177.41(13) . . . . ?
C3 N2 C1 P 178.77(10) . . . . ?
C21 N2 C1 P 0.8(2) . . . . ?
C4 N5 C1 N2 -0.70(15) . . . . ?
C6 N5 C1 N2 -170.30(12) . . . . ?
C4 N5 C1 P -178.88(10) . . . . ?
C6 N5 C1 P 11.52(19) . . . . ?
C11 P C1 N2 -160.17(12) . . . . ?
C11 P C1 N5 17.66(13) . . . . ?
C1 N2 C3 C4 -0.20(16) . . . . ?
C21 N2 C3 C4 177.75(14) . . . . ?
N2 C3 C4 N5 -0.23(16) . . . . ?
C1 N5 C4 C3 0.59(16) . . . . ?
C6 N5 C4 C3 169.73(13) . . . . ?
C1 N5 C6 N7 -44.26(17) . . . . ?
C4 N5 C6 N7 147.83(13) . . . . ?
N7 C8 C9 N10 0.23(19) . . . . ?
C1 P C11 N10 158.95(13) . . . . ?
C1 P C11 N7 -16.53(13) . . . . ?
N10 C11 N7 C8 -0.12(16) . . . . ?
P C11 N7 C8 176.09(12) . . . . ?
N10 C11 N7 C6 170.10(12) . . . . ?
P C11 N7 C6 -13.7(2) . . . . ?
C9 C8 N7 C11 -0.07(18) . . . . ?
C9 C8 N7 C6 -169.61(15) . . . . ?
N5 C6 N7 C11 45.14(18) . . . . ?
N5 C6 N7 C8 -146.43(14) . . . . ?
N7 C11 N10 C9 0.26(16) . . . . ?
P C11 N10 C9 -176.04(12) . . . . ?
N7 C11 N10 C101 177.70(13) . . . . ?
P C11 N10 C101 1.4(2) . . . . ?
C8 C9 N10 C11 -0.32(19) . . . . ?
C8 C9 N10 C101 -177.66(15) . . . . ?
O3 S C01 F2 -56.86(14) . . . . ?
O1 S C01 F2 63.57(14) . . . . ?
O2 S C01 F2 -176.98(12) . . . . ?
O3 S C01 F3 -177.78(11) . . . . ?
O1 S C01 F3 -57.35(12) . . . . ?
O2 S C01 F3 62.10(12) . . . . ?
O3 S C01 F1 62.99(12) . . . . ?
O1 S C01 F1 -176.57(10) . . . . ?
O2 S C01 F1 -57.12(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O2 0.95 2.57 3.4236(19) 149.0 2_775
C4 H4 O2 0.95 2.60 3.4628(19) 151.1 .
C6 H6A O1 0.99 2.51 3.2295(19) 129.7 .
C6 H6A O3 0.99 2.43 3.0442(18) 119.5 2_776
C9 H9 O1 0.95 2.40 3.2938(19) 156.9 2_766
C101 H10B O3 0.98 2.41 3.371(2) 168.2 2_766
C101 H10C O3 0.98 2.64 3.483(2) 144.5 1_645

_refine_diff_density_max         0.642
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.086


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042846'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 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         'C21 H20 N4 P, C24 H20 B, C4 H8 O'
_chemical_formula_sum            'C49 H48 B N4 O P'
_chemical_formula_weight         750.69

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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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      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                   11.0003(4)
_cell_length_b                   13.6439(5)
_cell_length_c                   14.0585(5)
_cell_angle_alpha                77.876(2)
_cell_angle_beta                 79.118(2)
_cell_angle_gamma                87.493(2)
_cell_volume                     2025.82(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9383
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      29.62

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS; Bruker,2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            93422
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.878
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10259
_reflns_number_gt                8069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+0.9976P] 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         10259
_refine_ls_number_parameters     550
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P P 0.84486(4) 0.66770(3) 0.27806(3) 0.03034(11) Uani 1 1 d . . . . .
C1 C 0.72781(14) 0.74587(12) 0.22924(11) 0.0291(3) Uani 1 1 d . . . . .
N2 N 0.72373(13) 0.84705(11) 0.20995(10) 0.0338(3) Uani 1 1 d . . . . .
N5 N 0.62444(12) 0.71632(11) 0.20348(11) 0.0344(3) Uani 1 1 d . . . . .
C3 C 0.61527(18) 0.87982(15) 0.17559(14) 0.0427(4) Uani 1 1 d . . . . .
H3 H 0.5897 0.9476 0.1581 0.051 Uiso 1 1 calc R U . . .
C4 C 0.55383(17) 0.79928(15) 0.17164(14) 0.0428(4) Uani 1 1 d . . . . .
H4 H 0.4765 0.7987 0.1510 0.051 Uiso 1 1 calc R U . . .
C6 C 0.58343(15) 0.61375(14) 0.22858(15) 0.0391(4) Uani 1 1 d . . . . .
H6A H 0.5221 0.6045 0.1880 0.047 Uiso 1 1 calc R U . . .
H6B H 0.5434 0.5965 0.2992 0.047 Uiso 1 1 calc R U . . .
C11 C 0.79954(14) 0.56293(12) 0.23609(11) 0.0267(3) Uani 1 1 d . . . . .
N7 N 0.68960(12) 0.54906(11) 0.21021(10) 0.0313(3) Uani 1 1 d . . . . .
N10 N 0.86783(12) 0.48054(10) 0.22204(10) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.68930(17) 0.45762(14) 0.18203(13) 0.0383(4) Uani 1 1 d . . . . .
H8 H 0.6231 0.4302 0.1614 0.046 Uiso 1 1 calc R U . . .
C9 C 0.79995(16) 0.41538(14) 0.18945(13) 0.0363(4) Uani 1 1 d . . . . .
H9 H 0.8271 0.3522 0.1750 0.044 Uiso 1 1 calc R U . . .
C21 C 0.81801(17) 0.91188(13) 0.22238(15) 0.0405(4) Uani 1 1 d . . . . .
H21A H 0.8267 0.9715 0.1676 0.049 Uiso 1 1 calc R U . . .
H21B H 0.8982 0.8757 0.2177 0.049 Uiso 1 1 calc R U . . .
C22 C 0.79025(18) 0.94618(13) 0.31956(15) 0.0407(4) Uani 1 1 d . . . . .
C23 C 0.8680(2) 1.01590(17) 0.3361(2) 0.0620(6) Uani 1 1 d . . . . .
H23 H 0.9371 1.0412 0.2867 0.074 Uiso 1 1 calc R U . . .
C24 C 0.8441(3) 1.0485(2) 0.4249(3) 0.0864(11) Uani 1 1 d . . . . .
H24 H 0.8982 1.0952 0.4366 0.104 Uiso 1 1 calc R U . . .
C25 C 0.7429(4) 1.0137(2) 0.4960(2) 0.0873(11) Uani 1 1 d . . . . .
H25 H 0.7274 1.0365 0.5566 0.105 Uiso 1 1 calc R U . . .
C26 C 0.6648(3) 0.9467(2) 0.47967(17) 0.0714(8) Uani 1 1 d . . . . .
H26 H 0.5940 0.9237 0.5284 0.086 Uiso 1 1 calc R U . . .
C27 C 0.6884(2) 0.91177(16) 0.39191(15) 0.0509(5) Uani 1 1 d . . . . .
H27 H 0.6345 0.8641 0.3814 0.061 Uiso 1 1 calc R U . . .
B B 1.23594(15) 0.75697(12) 0.04832(12) 0.0229(3) Uani 1 1 d . . . . .
C31 C 1.09403(13) 0.75180(11) 0.02775(11) 0.0254(3) Uani 1 1 d . . . . .
C32 C 1.03849(15) 0.66341(13) 0.02191(11) 0.0308(3) Uani 1 1 d . . . . .
H32 H 1.0827 0.6020 0.0340 0.037 Uiso 1 1 calc R U . . .
C33 C 0.92074(16) 0.66208(16) -0.00100(13) 0.0401(4) Uani 1 1 d . . . . .
H33 H 0.8858 0.6003 -0.0033 0.048 Uiso 1 1 calc R U . . .
C34 C 0.85480(16) 0.75007(17) -0.02036(14) 0.0450(5) Uani 1 1 d . . . . .
H34 H 0.7746 0.7493 -0.0361 0.054 Uiso 1 1 calc R U . . .
C35 C 0.90659(17) 0.83916(16) -0.01659(14) 0.0428(4) Uani 1 1 d . . . . .
H35 H 0.8624 0.9003 -0.0305 0.051 Uiso 1 1 calc R U . . .
C36 C 1.02357(15) 0.83939(13) 0.00766(13) 0.0335(3) Uani 1 1 d . . . . .
H36 H 1.0571 0.9014 0.0107 0.040 Uiso 1 1 calc R U . . .
C41 C 1.24435(13) 0.84993(11) 0.10452(11) 0.0235(3) Uani 1 1 d . . . . .
C42 C 1.16494(14) 0.85400(12) 0.19470(12) 0.0287(3) Uani 1 1 d . . . . .
H42 H 1.1023 0.8047 0.2201 0.034 Uiso 1 1 calc R U . . .
C43 C 1.17473(16) 0.92748(13) 0.24799(13) 0.0352(4) Uani 1 1 d . . . . .
H43 H 1.1214 0.9262 0.3098 0.042 Uiso 1 1 calc R U . . .
C44 C 1.26215(16) 1.00259(13) 0.21108(13) 0.0358(4) Uani 1 1 d . . . . .
H44 H 1.2695 1.0528 0.2474 0.043 Uiso 1 1 calc R U . . .
C45 C 1.33838(15) 1.00355(12) 0.12102(13) 0.0320(3) Uani 1 1 d . . . . .
H45 H 1.3972 1.0557 0.0941 0.038 Uiso 1 1 calc R U . . .
C46 C 1.32956(14) 0.92840(11) 0.06936(12) 0.0268(3) Uani 1 1 d . . . . .
H46 H 1.3836 0.9304 0.0077 0.032 Uiso 1 1 calc R U . . .
C51 C 1.33225(14) 0.77648(10) -0.05905(11) 0.0240(3) Uani 1 1 d . . . . .
C52 C 1.29540(15) 0.81663(11) -0.14936(12) 0.0291(3) Uani 1 1 d . . . . .
H52 H 1.2103 0.8321 -0.1493 0.035 Uiso 1 1 calc R U . . .
C53 C 1.37797(17) 0.83500(13) -0.23949(12) 0.0363(4) Uani 1 1 d . . . . .
H53 H 1.3486 0.8623 -0.2990 0.044 Uiso 1 1 calc R U . . .
C54 C 1.50269(17) 0.81353(12) -0.24237(12) 0.0348(4) Uani 1 1 d . . . . .
H54 H 1.5594 0.8256 -0.3035 0.042 Uiso 1 1 calc R U . . .
C55 C 1.54311(15) 0.77432(12) -0.15506(12) 0.0309(3) Uani 1 1 d . . . . .
H55 H 1.6284 0.7595 -0.1558 0.037 Uiso 1 1 calc R U . . .
C56 C 1.45969(14) 0.75641(12) -0.06605(12) 0.0284(3) Uani 1 1 d . . . . .
H56 H 1.4902 0.7293 -0.0070 0.034 Uiso 1 1 calc R U . . .
C61 C 1.27234(13) 0.64931(11) 0.11734(11) 0.0252(3) Uani 1 1 d . . . . .
C62 C 1.25978(14) 0.62859(12) 0.22045(12) 0.0289(3) Uani 1 1 d . . . . .
H62 H 1.2329 0.6808 0.2549 0.035 Uiso 1 1 calc R U . . .
C63 C 1.28510(15) 0.53434(13) 0.27490(13) 0.0354(4) Uani 1 1 d . . . . .
H63 H 1.2735 0.5235 0.3450 0.042 Uiso 1 1 calc R U . . .
C64 C 1.32684(16) 0.45689(12) 0.22758(14) 0.0379(4) Uani 1 1 d . . . . .
H64 H 1.3442 0.3928 0.2644 0.045 Uiso 1 1 calc R U . . .
C65 C 1.34267(18) 0.47472(13) 0.12590(15) 0.0414(4) Uani 1 1 d . . . . .
H65 H 1.3724 0.4227 0.0918 0.050 Uiso 1 1 calc R U . . .
C66 C 1.31530(17) 0.56850(12) 0.07289(13) 0.0361(4) Uani 1 1 d . . . . .
H66 H 1.3263 0.5783 0.0029 0.043 Uiso 1 1 calc R U . . .
C101 C 0.99729(15) 0.46478(13) 0.23367(13) 0.0331(3) Uani 1 1 d . . . . .
H10A H 1.0325 0.5293 0.2368 0.040 Uiso 1 1 calc R U . . .
H10B H 1.0449 0.4425 0.1748 0.040 Uiso 1 1 calc R U . . .
C102 C 1.01226(15) 0.38830(13) 0.32513(14) 0.0363(4) Uani 1 1 d . . . . .
C103 C 1.0728(2) 0.29867(16) 0.3160(2) 0.0586(6) Uani 1 1 d . . . . .
H103 H 1.1001 0.2836 0.2524 0.070 Uiso 1 1 calc R U . . .
C104 C 1.0933(3) 0.2309(2) 0.4001(3) 0.0854(10) Uani 1 1 d . . . . .
H104 H 1.1367 0.1702 0.3937 0.102 Uiso 1 1 calc R U . . .
C105 C 1.0516(3) 0.2509(2) 0.4923(3) 0.0862(10) Uani 1 1 d . . . . .
H105 H 1.0657 0.2040 0.5495 0.103 Uiso 1 1 calc R U . . .
C106 C 0.9898(3) 0.3383(2) 0.50201(19) 0.0745(8) Uani 1 1 d . . . . .
H106 H 0.9597 0.3517 0.5660 0.089 Uiso 1 1 calc R U . . .
C107 C 0.9709(2) 0.40781(17) 0.41837(16) 0.0519(5) Uani 1 1 d . . . . .
H107 H 0.9292 0.4691 0.4254 0.062 Uiso 1 1 calc R U . . .
O70 O 0.5128(9) 0.7118(8) 0.4195(6) 0.106(3) Uani 0.5 1 d D U P A 1
C71 C 0.5495(14) 0.6684(13) 0.5107(9) 0.090(3) Uani 0.5 1 d D U P A 1
H71A H 0.6008 0.6081 0.5034 0.108 Uiso 0.5 1 calc R U P A 1
H71B H 0.5997 0.7169 0.5299 0.108 Uiso 0.5 1 calc R U P A 1
C72 C 0.4439(8) 0.6420(6) 0.5842(4) 0.0705(18) Uani 0.5 1 d . U P A 1
H72A H 0.4570 0.6500 0.6499 0.085 Uiso 0.5 1 calc R U P A 1
H72B H 0.4170 0.5726 0.5886 0.085 Uiso 0.5 1 calc R U P A 1
C73 C 0.3489(6) 0.7229(5) 0.5411(4) 0.0721(15) Uani 0.5 1 d . U P A 1
H73A H 0.2655 0.6935 0.5515 0.086 Uiso 0.5 1 calc R U P A 1
H73B H 0.3429 0.7816 0.5729 0.086 Uiso 0.5 1 calc R U P A 1
C74 C 0.3946(10) 0.7478(11) 0.4490(11) 0.134(4) Uani 0.5 1 d D U P A 1
H74A H 0.3963 0.8219 0.4301 0.160 Uiso 0.5 1 calc R U P A 1
H74B H 0.3382 0.7240 0.4115 0.160 Uiso 0.5 1 calc R U P A 1
O80 O 0.5029(7) 0.6982(7) 0.4143(4) 0.085(2) Uani 0.5 1 d D U P B 2
C81 C 0.5469(12) 0.6507(14) 0.4999(7) 0.091(4) Uani 0.5 1 d D U P B 2
H81A H 0.6169 0.6057 0.4825 0.109 Uiso 0.5 1 calc R U P B 2
H81B H 0.5768 0.7014 0.5310 0.109 Uiso 0.5 1 calc R U P B 2
C82 C 0.4693(13) 0.6060(10) 0.5532(12) 0.166(4) Uani 0.5 1 d . U P B 2
H82A H 0.4797 0.6055 0.6217 0.199 Uiso 0.5 1 calc R U P B 2
H82B H 0.4754 0.5358 0.5441 0.199 Uiso 0.5 1 calc R U P B 2
C83 C 0.3524(8) 0.6429(9) 0.5414(7) 0.128(3) Uani 0.5 1 d . U P B 2
H83A H 0.3152 0.6774 0.5954 0.153 Uiso 0.5 1 calc R U P B 2
H83B H 0.2966 0.5884 0.5400 0.153 Uiso 0.5 1 calc R U P B 2
C84 C 0.3766(7) 0.7153(7) 0.4434(7) 0.074(2) Uani 0.5 1 d D U P B 2
H84A H 0.3278 0.6989 0.3965 0.089 Uiso 0.5 1 calc R U P B 2
H84B H 0.3596 0.7854 0.4509 0.089 Uiso 0.5 1 calc R U P B 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
P C11 1.7797(16) . ?
P C1 1.7811(16) . ?
C1 N2 1.350(2) . ?
C1 N5 1.358(2) . ?
N2 C3 1.392(2) . ?
N2 C21 1.450(2) . ?
N5 C4 1.388(2) . ?
N5 C6 1.440(2) . ?
C3 C4 1.331(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 N7 1.450(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 N10 1.353(2) . ?
C11 N7 1.3586(19) . ?
N7 C8 1.386(2) . ?
N10 C9 1.384(2) . ?
N10 C101 1.465(2) . ?
C8 C9 1.336(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C21 C22 1.509(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.388(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.364(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
B C41 1.643(2) . ?
B C31 1.647(2) . ?
B C51 1.650(2) . ?
B C61 1.660(2) . ?
C31 C32 1.400(2) . ?
C31 C36 1.403(2) . ?
C32 C33 1.394(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.400(2) . ?
C41 C42 1.407(2) . ?
C42 C43 1.391(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.385(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.378(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.392(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.400(2) . ?
C51 C56 1.406(2) . ?
C52 C53 1.395(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.385(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.378(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.388(2) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.399(2) . ?
C61 C66 1.401(2) . ?
C62 C63 1.397(2) . ?
C62 H62 0.9500 . ?
C63 C64 1.381(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.377(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.391(2) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C101 C102 1.507(2) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 C107 1.381(3) . ?
C102 C103 1.385(3) . ?
C103 C104 1.389(4) . ?
C103 H103 0.9500 . ?
C104 C105 1.371(5) . ?
C104 H104 0.9500 . ?
C105 C106 1.366(5) . ?
C105 H105 0.9500 . ?
C106 C107 1.390(3) . ?
C106 H106 0.9500 . ?
C107 H107 0.9500 . ?
O70 C74 1.390(7) . ?
O70 C71 1.419(6) . ?
C71 C72 1.406(18) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C72 C73 1.592(10) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.276(15) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
O80 C84 1.396(6) . ?
O80 C81 1.402(6) . ?
C81 C82 1.13(2) . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
C82 C83 1.387(15) . ?
C82 H82A 0.9900 . ?
C82 H82B 0.9900 . ?
C83 C84 1.503(13) . ?
C83 H83A 0.9900 . ?
C83 H83B 0.9900 . ?
C84 H84A 0.9900 . ?
C84 H84B 0.9900 . ?

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
C11 P C1 92.51(7) . . ?
N2 C1 N5 105.70(14) . . ?
N2 C1 P 127.03(12) . . ?
N5 C1 P 127.27(13) . . ?
C1 N2 C3 109.54(15) . . ?
C1 N2 C21 125.39(14) . . ?
C3 N2 C21 125.07(15) . . ?
C1 N5 C4 110.10(15) . . ?
C1 N5 C6 122.78(14) . . ?
C4 N5 C6 125.63(15) . . ?
C4 C3 N2 107.81(16) . . ?
C4 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
C3 C4 N5 106.81(16) . . ?
C3 C4 H4 126.6 . . ?
N5 C4 H4 126.6 . . ?
N5 C6 N7 108.82(13) . . ?
N5 C6 H6A 109.9 . . ?
N7 C6 H6A 109.9 . . ?
N5 C6 H6B 109.9 . . ?
N7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N10 C11 N7 105.24(13) . . ?
N10 C11 P 127.33(11) . . ?
N7 C11 P 127.43(12) . . ?
C11 N7 C8 110.26(14) . . ?
C11 N7 C6 122.49(14) . . ?
C8 N7 C6 126.31(14) . . ?
C11 N10 C9 110.13(13) . . ?
C11 N10 C101 125.19(13) . . ?
C9 N10 C101 124.59(14) . . ?
C9 C8 N7 106.84(15) . . ?
C9 C8 H8 126.6 . . ?
N7 C8 H8 126.6 . . ?
C8 C9 N10 107.52(15) . . ?
C8 C9 H9 126.2 . . ?
N10 C9 H9 126.2 . . ?
N2 C21 C22 113.54(15) . . ?
N2 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N2 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C27 C22 C23 119.1(2) . . ?
C27 C22 C21 122.11(18) . . ?
C23 C22 C21 118.8(2) . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 120.3(2) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C41 B C31 108.88(11) . . ?
C41 B C51 109.91(12) . . ?
C31 B C51 108.54(11) . . ?
C41 B C61 110.42(12) . . ?
C31 B C61 110.01(12) . . ?
C51 B C61 109.06(11) . . ?
C32 C31 C36 115.32(14) . . ?
C32 C31 B 123.68(13) . . ?
C36 C31 B 120.85(13) . . ?
C33 C32 C31 122.46(16) . . ?
C33 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
C34 C33 C32 120.24(17) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.26(16) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C34 C35 C36 119.98(17) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 122.72(17) . . ?
C35 C36 H36 118.6 . . ?
C31 C36 H36 118.6 . . ?
C46 C41 C42 115.22(13) . . ?
C46 C41 B 124.03(13) . . ?
C42 C41 B 120.73(13) . . ?
C43 C42 C41 122.49(15) . . ?
C43 C42 H42 118.8 . . ?
C41 C42 H42 118.8 . . ?
C44 C43 C42 120.12(15) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 119.13(15) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C44 C45 C46 120.24(15) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C45 C46 C41 122.71(15) . . ?
C45 C46 H46 118.6 . . ?
C41 C46 H46 118.6 . . ?
C52 C51 C56 114.69(14) . . ?
C52 C51 B 123.36(13) . . ?
C56 C51 B 121.92(13) . . ?
C53 C52 C51 122.95(15) . . ?
C53 C52 H52 118.5 . . ?
C51 C52 H52 118.5 . . ?
C54 C53 C52 120.08(15) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 118.90(15) . . ?
C55 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C54 C55 C56 120.28(15) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C55 C56 C51 123.11(15) . . ?
C55 C56 H56 118.4 . . ?
C51 C56 H56 118.4 . . ?
C62 C61 C66 114.48(14) . . ?
C62 C61 B 125.55(13) . . ?
C66 C61 B 119.93(13) . . ?
C63 C62 C61 122.79(15) . . ?
C63 C62 H62 118.6 . . ?
C61 C62 H62 118.6 . . ?
C64 C63 C62 120.51(16) . . ?
C64 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C65 C64 C63 118.52(15) . . ?
C65 C64 H64 120.7 . . ?
C63 C64 H64 120.7 . . ?
C64 C65 C66 120.26(17) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 123.42(16) . . ?
C65 C66 H66 118.3 . . ?
C61 C66 H66 118.3 . . ?
N10 C101 C102 112.90(13) . . ?
N10 C101 H10A 109.0 . . ?
C102 C101 H10A 109.0 . . ?
N10 C101 H10B 109.0 . . ?
C102 C101 H10B 109.0 . . ?
H10A C101 H10B 107.8 . . ?
C107 C102 C103 119.21(19) . . ?
C107 C102 C101 120.95(17) . . ?
C103 C102 C101 119.78(19) . . ?
C102 C103 C104 119.8(3) . . ?
C102 C103 H103 120.1 . . ?
C104 C103 H103 120.1 . . ?
C105 C104 C103 120.5(3) . . ?
C105 C104 H104 119.7 . . ?
C103 C104 H104 119.7 . . ?
C106 C105 C104 120.0(2) . . ?
C106 C105 H105 120.0 . . ?
C104 C105 H105 120.0 . . ?
C105 C106 C107 120.1(3) . . ?
C105 C106 H106 120.0 . . ?
C107 C106 H106 120.0 . . ?
C102 C107 C106 120.4(2) . . ?
C102 C107 H107 119.8 . . ?
C106 C107 H107 119.8 . . ?
C74 O70 C71 103.0(8) . . ?
C72 C71 O70 109.5(9) . . ?
C72 C71 H71A 109.8 . . ?
O70 C71 H71A 109.8 . . ?
C72 C71 H71B 109.8 . . ?
O70 C71 H71B 109.8 . . ?
H71A C71 H71B 108.2 . . ?
C71 C72 C73 99.4(6) . . ?
C71 C72 H72A 111.9 . . ?
C73 C72 H72A 111.9 . . ?
C71 C72 H72B 111.9 . . ?
C73 C72 H72B 111.9 . . ?
H72A C72 H72B 109.6 . . ?
C74 C73 C72 104.2(6) . . ?
C74 C73 H73A 110.9 . . ?
C72 C73 H73A 110.9 . . ?
C74 C73 H73B 110.9 . . ?
C72 C73 H73B 110.9 . . ?
H73A C73 H73B 108.9 . . ?
C73 C74 O70 116.0(10) . . ?
C73 C74 H74A 108.3 . . ?
O70 C74 H74A 108.3 . . ?
C73 C74 H74B 108.3 . . ?
O70 C74 H74B 108.3 . . ?
H74A C74 H74B 107.4 . . ?
C84 O80 C81 106.7(6) . . ?
C82 C81 O80 108.9(14) . . ?
C82 C81 H81A 109.9 . . ?
O80 C81 H81A 109.9 . . ?
C82 C81 H81B 109.9 . . ?
O80 C81 H81B 109.9 . . ?
H81A C81 H81B 108.3 . . ?
C81 C82 C83 113.7(12) . . ?
C81 C82 H82A 108.8 . . ?
C83 C82 H82A 108.8 . . ?
C81 C82 H82B 108.8 . . ?
C83 C82 H82B 108.8 . . ?
H82A C82 H82B 107.7 . . ?
C82 C83 C84 103.3(7) . . ?
C82 C83 H83A 111.1 . . ?
C84 C83 H83A 111.1 . . ?
C82 C83 H83B 111.1 . . ?
C84 C83 H83B 111.1 . . ?
H83A C83 H83B 109.1 . . ?
O80 C84 C83 99.9(6) . . ?
O80 C84 H84A 111.8 . . ?
C83 C84 H84A 111.8 . . ?
O80 C84 H84B 111.8 . . ?
C83 C84 H84B 111.8 . . ?
H84A C84 H84B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P C1 N2 -161.17(15) . . . . ?
C11 P C1 N5 18.66(15) . . . . ?
N5 C1 N2 C3 2.15(18) . . . . ?
P C1 N2 C3 -177.98(13) . . . . ?
N5 C1 N2 C21 -177.47(15) . . . . ?
P C1 N2 C21 2.4(2) . . . . ?
N2 C1 N5 C4 -2.22(19) . . . . ?
P C1 N5 C4 177.91(13) . . . . ?
N2 C1 N5 C6 -168.96(15) . . . . ?
P C1 N5 C6 11.2(2) . . . . ?
C1 N2 C3 C4 -1.3(2) . . . . ?
C21 N2 C3 C4 178.31(16) . . . . ?
N2 C3 C4 N5 -0.1(2) . . . . ?
C1 N5 C4 C3 1.5(2) . . . . ?
C6 N5 C4 C3 167.73(17) . . . . ?
C1 N5 C6 N7 -43.6(2) . . . . ?
C4 N5 C6 N7 151.78(16) . . . . ?
C1 P C11 N10 160.08(14) . . . . ?
C1 P C11 N7 -19.07(15) . . . . ?
N10 C11 N7 C8 1.09(17) . . . . ?
P C11 N7 C8 -179.61(12) . . . . ?
N10 C11 N7 C6 170.58(14) . . . . ?
P C11 N7 C6 -10.1(2) . . . . ?
N5 C6 N7 C11 43.0(2) . . . . ?
N5 C6 N7 C8 -149.24(16) . . . . ?
N7 C11 N10 C9 -1.07(17) . . . . ?
P C11 N10 C9 179.62(12) . . . . ?
N7 C11 N10 C101 175.50(14) . . . . ?
P C11 N10 C101 -3.8(2) . . . . ?
C11 N7 C8 C9 -0.70(19) . . . . ?
C6 N7 C8 C9 -169.70(16) . . . . ?
N7 C8 C9 N10 0.02(19) . . . . ?
C11 N10 C9 C8 0.67(19) . . . . ?
C101 N10 C9 C8 -175.92(15) . . . . ?
C1 N2 C21 C22 -96.49(19) . . . . ?
C3 N2 C21 C22 83.9(2) . . . . ?
N2 C21 C22 C27 4.6(2) . . . . ?
N2 C21 C22 C23 -174.12(16) . . . . ?
C27 C22 C23 C24 1.3(3) . . . . ?
C21 C22 C23 C24 180.0(2) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C27 1.2(4) . . . . ?
C23 C22 C27 C26 -0.1(3) . . . . ?
C21 C22 C27 C26 -178.78(19) . . . . ?
C25 C26 C27 C22 -1.1(3) . . . . ?
C41 B C31 C32 -151.49(14) . . . . ?
C51 B C31 C32 88.89(16) . . . . ?
C61 B C31 C32 -30.37(19) . . . . ?
C41 B C31 C36 33.17(19) . . . . ?
C51 B C31 C36 -86.45(16) . . . . ?
C61 B C31 C36 154.30(14) . . . . ?
C36 C31 C32 C33 -0.8(2) . . . . ?
B C31 C32 C33 -176.37(14) . . . . ?
C31 C32 C33 C34 0.9(3) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 -0.7(3) . . . . ?
C34 C35 C36 C31 0.9(3) . . . . ?
C32 C31 C36 C35 -0.1(2) . . . . ?
B C31 C36 C35 175.62(15) . . . . ?
C31 B C41 C46 -124.23(14) . . . . ?
C51 B C41 C46 -5.47(18) . . . . ?
C61 B C41 C46 114.90(15) . . . . ?
C31 B C41 C42 56.99(17) . . . . ?
C51 B C41 C42 175.75(12) . . . . ?
C61 B C41 C42 -63.89(16) . . . . ?
C46 C41 C42 C43 -3.4(2) . . . . ?
B C41 C42 C43 175.45(14) . . . . ?
C41 C42 C43 C44 2.4(2) . . . . ?
C42 C43 C44 C45 0.3(3) . . . . ?
C43 C44 C45 C46 -1.7(2) . . . . ?
C44 C45 C46 C41 0.5(2) . . . . ?
C42 C41 C46 C45 2.0(2) . . . . ?
B C41 C46 C45 -176.84(13) . . . . ?
C41 B C51 C52 -98.45(16) . . . . ?
C31 B C51 C52 20.52(18) . . . . ?
C61 B C51 C52 140.37(14) . . . . ?
C41 B C51 C56 79.59(16) . . . . ?
C31 B C51 C56 -161.44(13) . . . . ?
C61 B C51 C56 -41.59(18) . . . . ?
C56 C51 C52 C53 0.3(2) . . . . ?
B C51 C52 C53 178.47(14) . . . . ?
C51 C52 C53 C54 -0.1(3) . . . . ?
C52 C53 C54 C55 -0.2(2) . . . . ?
C53 C54 C55 C56 0.3(2) . . . . ?
C54 C55 C56 C51 0.0(2) . . . . ?
C52 C51 C56 C55 -0.2(2) . . . . ?
B C51 C56 C55 -178.44(14) . . . . ?
C41 B C61 C62 25.98(19) . . . . ?
C31 B C61 C62 -94.22(16) . . . . ?
C51 B C61 C62 146.85(14) . . . . ?
C41 B C61 C66 -156.62(14) . . . . ?
C31 B C61 C66 83.18(17) . . . . ?
C51 B C61 C66 -35.75(18) . . . . ?
C66 C61 C62 C63 -1.5(2) . . . . ?
B C61 C62 C63 176.03(14) . . . . ?
C61 C62 C63 C64 1.3(2) . . . . ?
C62 C63 C64 C65 -0.1(3) . . . . ?
C63 C64 C65 C66 -0.9(3) . . . . ?
C64 C65 C66 C61 0.7(3) . . . . ?
C62 C61 C66 C65 0.5(3) . . . . ?
B C61 C66 C65 -177.18(16) . . . . ?
C11 N10 C101 C102 107.40(18) . . . . ?
C9 N10 C101 C102 -76.5(2) . . . . ?
N10 C101 C102 C107 -68.5(2) . . . . ?
N10 C101 C102 C103 114.19(19) . . . . ?
C107 C102 C103 C104 -1.4(3) . . . . ?
C101 C102 C103 C104 176.0(2) . . . . ?
C102 C103 C104 C105 1.6(4) . . . . ?
C103 C104 C105 C106 -0.3(5) . . . . ?
C104 C105 C106 C107 -1.1(4) . . . . ?
C103 C102 C107 C106 0.0(3) . . . . ?
C101 C102 C107 C106 -177.3(2) . . . . ?
C105 C106 C107 C102 1.2(4) . . . . ?
C74 O70 C71 C72 24.2(16) . . . . ?
O70 C71 C72 C73 -28.0(13) . . . . ?
C71 C72 C73 C74 22.3(12) . . . . ?
C72 C73 C74 O70 -9.0(14) . . . . ?
C71 O70 C74 C73 -8.1(17) . . . . ?
C84 O80 C81 C82 29.2(19) . . . . ?
O80 C81 C82 C83 -26(2) . . . . ?
C81 C82 C83 C84 13(2) . . . . ?
C81 O80 C84 C83 -18.3(13) . . . . ?
C82 C83 C84 O80 5.2(13) . . . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042847'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 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         'C21 H20 N4 P, C24 H20 B, C H2 Cl2'
_chemical_formula_sum            'C46 H42 B Cl2 N4 P'
_chemical_formula_weight         763.51

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'
B B 0.0013 0.0007 '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'
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                   11.0120(4)
_cell_length_b                   13.4813(5)
_cell_length_c                   13.8114(4)
_cell_angle_alpha                78.513(2)
_cell_angle_beta                 77.1380(10)
_cell_angle_gamma                87.889(2)
_cell_volume                     1958.84(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      36.23

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.205
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'SADABS; Bruker,2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67652
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8984
_reflns_number_gt                7290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+1.8456P] 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         8984
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1545
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P P 0.82977(5) 0.66107(4) 0.28735(4) 0.02386(14) Uani 1 1 d . . . . .
C1 C 0.71484(19) 0.73700(16) 0.23563(15) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.71328(17) 0.83878(14) 0.20941(14) 0.0265(4) Uani 1 1 d . . . . .
N5 N 0.61049(16) 0.70446(14) 0.21395(13) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.6067(2) 0.86936(19) 0.17326(17) 0.0327(5) Uani 1 1 d . . . . .
H3 H 0.5835 0.9372 0.1508 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5432(2) 0.78610(19) 0.17589(17) 0.0316(5) Uani 1 1 d . . . . .
H4 H 0.4666 0.7833 0.1556 0.038 Uiso 1 1 calc R U . . .
C6 C 0.56891(19) 0.60014(17) 0.24645(17) 0.0273(4) Uani 1 1 d . . . . .
H6A H 0.5053 0.5870 0.2098 0.033 Uiso 1 1 calc R U . . .
H6B H 0.5311 0.5862 0.3199 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6756(2) 0.44212(17) 0.19745(16) 0.0267(4) Uani 1 1 d . . . . .
H8 H 0.6087 0.4122 0.1799 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7883(2) 0.40222(16) 0.20020(15) 0.0259(4) Uani 1 1 d . . . . .
H9 H 0.8167 0.3387 0.1843 0.031 Uiso 1 1 calc R U . . .
C11 C 0.78623(18) 0.55214(15) 0.24668(14) 0.0203(4) Uani 1 1 d . . . . .
N7 N 0.67545(15) 0.53529(13) 0.22510(13) 0.0227(4) Uani 1 1 d . . . . .
N10 N 0.85620(15) 0.47061(13) 0.23056(12) 0.0210(3) Uani 1 1 d . . . . .
C21 C 0.8070(2) 0.90680(17) 0.21946(17) 0.0290(5) Uani 1 1 d . . . . .
H21A H 0.8159 0.9664 0.1633 0.035 Uiso 1 1 calc R U . . .
H21B H 0.8881 0.8717 0.2134 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7759(2) 0.94262(16) 0.31906(17) 0.0268(4) Uani 1 1 d . . . . .
C23 C 0.8509(2) 1.01609(19) 0.3344(2) 0.0374(6) Uani 1 1 d . . . . .
H23 H 0.9211 1.0424 0.2831 0.045 Uiso 1 1 calc R U . . .
C24 C 0.8231(3) 1.0510(2) 0.4249(3) 0.0515(8) Uani 1 1 d . . . . .
H24 H 0.8749 1.1008 0.4354 0.062 Uiso 1 1 calc R U . . .
C25 C 0.7201(3) 1.0135(2) 0.5000(2) 0.0544(8) Uani 1 1 d . . . . .
H25 H 0.7013 1.0375 0.5618 0.065 Uiso 1 1 calc R U . . .
C26 C 0.6459(3) 0.9417(2) 0.48431(19) 0.0457(7) Uani 1 1 d . . . . .
H26 H 0.5748 0.9165 0.5353 0.055 Uiso 1 1 calc R U . . .
C27 C 0.6731(2) 0.90546(18) 0.39490(17) 0.0337(5) Uani 1 1 d . . . . .
H27 H 0.6214 0.8550 0.3854 0.040 Uiso 1 1 calc R U . . .
C101 C 0.98716(18) 0.45750(15) 0.23718(16) 0.0233(4) Uani 1 1 d . . . . .
H10A H 1.0216 0.5233 0.2404 0.028 Uiso 1 1 calc R U . . .
H10B H 1.0351 0.4362 0.1751 0.028 Uiso 1 1 calc R U . . .
C102 C 1.00362(18) 0.38006(16) 0.32849(16) 0.0235(4) Uani 1 1 d . . . . .
C103 C 1.0632(2) 0.28976(18) 0.3157(2) 0.0356(5) Uani 1 1 d . . . . .
H103 H 1.0880 0.2743 0.2500 0.043 Uiso 1 1 calc R U . . .
C104 C 1.0868(3) 0.2215(2) 0.3997(2) 0.0469(7) Uani 1 1 d . . . . .
H104 H 1.1289 0.1601 0.3909 0.056 Uiso 1 1 calc R U . . .
C105 C 1.0495(3) 0.2430(2) 0.4949(2) 0.0493(7) Uani 1 1 d . . . . .
H105 H 1.0665 0.1966 0.5517 0.059 Uiso 1 1 calc R U . . .
C106 C 0.9879(3) 0.3311(2) 0.5084(2) 0.0437(6) Uani 1 1 d . . . . .
H106 H 0.9603 0.3448 0.5746 0.052 Uiso 1 1 calc R U . . .
C107 C 0.9655(2) 0.40050(19) 0.42519(18) 0.0333(5) Uani 1 1 d . . . . .
H107 H 0.9241 0.4620 0.4347 0.040 Uiso 1 1 calc R U . . .
B B 0.23137(19) 0.75809(15) 0.04737(16) 0.0168(4) Uani 1 1 d . . . . .
C31 C 0.09103(18) 0.75335(15) 0.02549(14) 0.0191(4) Uani 1 1 d . . . . .
C32 C 0.03259(19) 0.66358(16) 0.02283(15) 0.0241(4) Uani 1 1 d . . . . .
H32 H 0.0747 0.6013 0.0366 0.029 Uiso 1 1 calc R U . . .
C33 C -0.0849(2) 0.66208(19) 0.00076(16) 0.0315(5) Uani 1 1 d . . . . .
H33 H -0.1220 0.5994 0.0012 0.038 Uiso 1 1 calc R U . . .
C34 C -0.1473(2) 0.7514(2) -0.02161(17) 0.0354(5) Uani 1 1 d . . . . .
H34 H -0.2272 0.7507 -0.0368 0.043 Uiso 1 1 calc R U . . .
C35 C -0.0923(2) 0.8419(2) -0.02167(17) 0.0329(5) Uani 1 1 d . . . . .
H35 H -0.1337 0.9040 -0.0382 0.039 Uiso 1 1 calc R U . . .
C36 C 0.02409(19) 0.84200(16) 0.00248(16) 0.0248(4) Uani 1 1 d . . . . .
H36 H 0.0595 0.9049 0.0034 0.030 Uiso 1 1 calc R U . . .
C41 C 0.23892(17) 0.85211(14) 0.10512(14) 0.0171(4) Uani 1 1 d . . . . .
C42 C 0.15443(18) 0.85862(15) 0.19652(15) 0.0209(4) Uani 1 1 d . . . . .
H42 H 0.0885 0.8104 0.2215 0.025 Uiso 1 1 calc R U . . .
C43 C 0.16356(19) 0.93265(16) 0.25165(16) 0.0249(4) Uani 1 1 d . . . . .
H43 H 0.1066 0.9326 0.3144 0.030 Uiso 1 1 calc R U . . .
C44 C 0.2556(2) 1.00664(16) 0.21532(16) 0.0263(4) Uani 1 1 d . . . . .
H44 H 0.2623 1.0575 0.2526 0.032 Uiso 1 1 calc R U . . .
C45 C 0.33771(19) 1.00512(15) 0.12376(16) 0.0243(4) Uani 1 1 d . . . . .
H45 H 0.4000 1.0562 0.0971 0.029 Uiso 1 1 calc R U . . .
C46 C 0.32925(18) 0.92909(14) 0.07071(15) 0.0200(4) Uani 1 1 d . . . . .
H46 H 0.3873 0.9294 0.0084 0.024 Uiso 1 1 calc R U . . .
C51 C 0.33439(18) 0.77646(13) -0.06175(14) 0.0176(4) Uani 1 1 d . . . . .
C52 C 0.30479(19) 0.82103(14) -0.15430(15) 0.0205(4) Uani 1 1 d . . . . .
H52 H 0.2210 0.8403 -0.1547 0.025 Uiso 1 1 calc R U . . .
C53 C 0.3929(2) 0.83844(16) -0.24594(15) 0.0255(4) Uani 1 1 d . . . . .
H53 H 0.3684 0.8686 -0.3068 0.031 Uiso 1 1 calc R U . . .
C54 C 0.5159(2) 0.81181(15) -0.24810(15) 0.0250(4) Uani 1 1 d . . . . .
H54 H 0.5762 0.8225 -0.3103 0.030 Uiso 1 1 calc R U . . .
C55 C 0.54983(19) 0.76922(14) -0.15799(15) 0.0214(4) Uani 1 1 d . . . . .
H55 H 0.6342 0.7519 -0.1580 0.026 Uiso 1 1 calc R U . . .
C56 C 0.46066(18) 0.75185(14) -0.06782(15) 0.0202(4) Uani 1 1 d . . . . .
H56 H 0.4862 0.7219 -0.0073 0.024 Uiso 1 1 calc R U . . .
C61 C 0.26255(17) 0.64992(14) 0.11830(14) 0.0182(4) Uani 1 1 d . . . . .
C62 C 0.3049(2) 0.56657(15) 0.07379(16) 0.0259(4) Uani 1 1 d . . . . .
H62 H 0.3177 0.5746 0.0023 0.031 Uiso 1 1 calc R U . . .
C63 C 0.3292(2) 0.47284(16) 0.12886(17) 0.0297(5) Uani 1 1 d . . . . .
H63 H 0.3590 0.4191 0.0948 0.036 Uiso 1 1 calc R U . . .
C64 C 0.31000(19) 0.45750(16) 0.23352(17) 0.0268(4) Uani 1 1 d . . . . .
H64 H 0.3257 0.3935 0.2718 0.032 Uiso 1 1 calc R U . . .
C65 C 0.26766(19) 0.53720(16) 0.28089(16) 0.0244(4) Uani 1 1 d . . . . .
H65 H 0.2534 0.5280 0.3525 0.029 Uiso 1 1 calc R U . . .
C66 C 0.24581(18) 0.63110(15) 0.22409(15) 0.0205(4) Uani 1 1 d . . . . .
H66 H 0.2183 0.6849 0.2586 0.025 Uiso 1 1 calc R U . . .
C71 C 0.3662(4) 0.6811(5) 0.5407(3) 0.0967(17) Uani 1 1 d . . . . .
H71A H 0.3072 0.6231 0.5643 0.116 Uiso 1 1 calc R U . . .
H71B H 0.3420 0.7289 0.5874 0.116 Uiso 1 1 calc R U . . .
Cl71 Cl 0.35371(9) 0.74119(8) 0.41972(6) 0.0644(2) Uani 1 1 d . . . . .
Cl72 Cl 0.51752(11) 0.63699(9) 0.54578(8) 0.0813(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P C1 1.782(2) . ?
P C11 1.790(2) . ?
C1 N2 1.348(3) . ?
C1 N5 1.358(3) . ?
N2 C3 1.393(3) . ?
N2 C21 1.453(3) . ?
N5 C4 1.386(3) . ?
N5 C6 1.447(3) . ?
C3 C4 1.334(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 N7 1.449(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.341(3) . ?
C8 N7 1.384(3) . ?
C8 H8 0.9500 . ?
C9 N10 1.389(3) . ?
C9 H9 0.9500 . ?
C11 N10 1.345(3) . ?
C11 N7 1.356(2) . ?
N10 C101 1.467(3) . ?
C21 C22 1.512(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.389(3) . ?
C22 C27 1.390(3) . ?
C23 C24 1.389(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.368(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C101 C102 1.509(3) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 C103 1.385(3) . ?
C102 C107 1.387(3) . ?
C103 C104 1.397(4) . ?
C103 H103 0.9500 . ?
C104 C105 1.373(4) . ?
C104 H104 0.9500 . ?
C105 C106 1.371(4) . ?
C105 H105 0.9500 . ?
C106 C107 1.392(3) . ?
C106 H106 0.9500 . ?
C107 H107 0.9500 . ?
B C41 1.640(3) . ?
B C31 1.645(3) . ?
B C51 1.652(3) . ?
B C61 1.658(3) . ?
C31 C36 1.400(3) . ?
C31 C32 1.402(3) . ?
C32 C33 1.396(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.401(3) . ?
C41 C42 1.408(3) . ?
C42 C43 1.389(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.387(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.390(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.402(3) . ?
C51 C56 1.406(3) . ?
C52 C53 1.396(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.384(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.387(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.388(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.403(3) . ?
C61 C66 1.403(3) . ?
C62 C63 1.389(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.388(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.381(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.394(3) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C71 Cl71 1.739(4) . ?
C71 Cl72 1.760(5) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?

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
C1 P C11 92.08(9) . . ?
N2 C1 N5 105.45(18) . . ?
N2 C1 P 127.31(16) . . ?
N5 C1 P 127.24(16) . . ?
C1 N2 C3 109.85(19) . . ?
C1 N2 C21 125.24(18) . . ?
C3 N2 C21 124.90(19) . . ?
C1 N5 C4 110.39(19) . . ?
C1 N5 C6 121.81(17) . . ?
C4 N5 C6 126.75(18) . . ?
C4 C3 N2 107.6(2) . . ?
C4 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
C3 C4 N5 106.74(19) . . ?
C3 C4 H4 126.6 . . ?
N5 C4 H4 126.6 . . ?
N5 C6 N7 108.50(16) . . ?
N5 C6 H6A 110.0 . . ?
N7 C6 H6A 110.0 . . ?
N5 C6 H6B 110.0 . . ?
N7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C9 C8 N7 106.63(18) . . ?
C9 C8 H8 126.7 . . ?
N7 C8 H8 126.7 . . ?
C8 C9 N10 107.50(19) . . ?
C8 C9 H9 126.3 . . ?
N10 C9 H9 126.3 . . ?
N10 C11 N7 105.79(17) . . ?
N10 C11 P 127.42(15) . . ?
N7 C11 P 126.79(15) . . ?
C11 N7 C8 110.26(17) . . ?
C11 N7 C6 122.23(17) . . ?
C8 N7 C6 126.69(17) . . ?
C11 N10 C9 109.80(17) . . ?
C11 N10 C101 125.77(17) . . ?
C9 N10 C101 124.32(18) . . ?
N2 C21 C22 112.95(18) . . ?
N2 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N2 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C27 119.1(2) . . ?
C23 C22 C21 119.0(2) . . ?
C27 C22 C21 121.9(2) . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 120.7(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
N10 C101 C102 112.57(16) . . ?
N10 C101 H10A 109.1 . . ?
C102 C101 H10A 109.1 . . ?
N10 C101 H10B 109.1 . . ?
C102 C101 H10B 109.1 . . ?
H10A C101 H10B 107.8 . . ?
C103 C102 C107 119.4(2) . . ?
C103 C102 C101 119.9(2) . . ?
C107 C102 C101 120.6(2) . . ?
C102 C103 C104 119.8(2) . . ?
C102 C103 H103 120.1 . . ?
C104 C103 H103 120.1 . . ?
C105 C104 C103 120.2(3) . . ?
C105 C104 H104 119.9 . . ?
C103 C104 H104 119.9 . . ?
C106 C105 C104 120.2(2) . . ?
C106 C105 H105 119.9 . . ?
C104 C105 H105 119.9 . . ?
C105 C106 C107 120.1(3) . . ?
C105 C106 H106 119.9 . . ?
C107 C106 H106 119.9 . . ?
C102 C107 C106 120.2(2) . . ?
C102 C107 H107 119.9 . . ?
C106 C107 H107 119.9 . . ?
C41 B C31 109.24(15) . . ?
C41 B C51 109.57(15) . . ?
C31 B C51 108.97(15) . . ?
C41 B C61 110.05(15) . . ?
C31 B C61 110.08(15) . . ?
C51 B C61 108.91(15) . . ?
C36 C31 C32 115.22(18) . . ?
C36 C31 B 120.92(17) . . ?
C32 C31 B 123.78(17) . . ?
C33 C32 C31 122.6(2) . . ?
C33 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
C34 C33 C32 120.1(2) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.3(2) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 122.8(2) . . ?
C35 C36 H36 118.6 . . ?
C31 C36 H36 118.6 . . ?
C46 C41 C42 115.10(17) . . ?
C46 C41 B 123.90(17) . . ?
C42 C41 B 120.98(17) . . ?
C43 C42 C41 122.68(19) . . ?
C43 C42 H42 118.7 . . ?
C41 C42 H42 118.7 . . ?
C44 C43 C42 120.17(19) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 118.88(19) . . ?
C45 C44 H44 120.6 . . ?
C43 C44 H44 120.6 . . ?
C44 C45 C46 120.24(19) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C45 C46 C41 122.84(18) . . ?
C45 C46 H46 118.6 . . ?
C41 C46 H46 118.6 . . ?
C52 C51 C56 114.77(17) . . ?
C52 C51 B 123.26(17) . . ?
C56 C51 B 121.92(16) . . ?
C53 C52 C51 122.98(19) . . ?
C53 C52 H52 118.5 . . ?
C51 C52 H52 118.5 . . ?
C54 C53 C52 120.04(19) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 118.93(19) . . ?
C53 C54 H54 120.5 . . ?
C55 C54 H54 120.5 . . ?
C54 C55 C56 120.12(19) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C55 C56 C51 123.14(18) . . ?
C55 C56 H56 118.4 . . ?
C51 C56 H56 118.4 . . ?
C62 C61 C66 114.46(17) . . ?
C62 C61 B 120.25(17) . . ?
C66 C61 B 125.25(17) . . ?
C63 C62 C61 123.4(2) . . ?
C63 C62 H62 118.3 . . ?
C61 C62 H62 118.3 . . ?
C64 C63 C62 120.1(2) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C65 C64 C63 118.65(19) . . ?
C65 C64 H64 120.7 . . ?
C63 C64 H64 120.7 . . ?
C64 C65 C66 120.31(19) . . ?
C64 C65 H65 119.8 . . ?
C66 C65 H65 119.8 . . ?
C65 C66 C61 123.08(19) . . ?
C65 C66 H66 118.5 . . ?
C61 C66 H66 118.5 . . ?
Cl71 C71 Cl72 112.8(2) . . ?
Cl71 C71 H71A 109.0 . . ?
Cl72 C71 H71A 109.0 . . ?
Cl71 C71 H71B 109.0 . . ?
Cl72 C71 H71B 109.0 . . ?
H71A C71 H71B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P C1 N2 -158.21(19) . . . . ?
C11 P C1 N5 21.54(19) . . . . ?
N5 C1 N2 C3 1.1(2) . . . . ?
P C1 N2 C3 -179.10(16) . . . . ?
N5 C1 N2 C21 179.77(18) . . . . ?
P C1 N2 C21 -0.4(3) . . . . ?
N2 C1 N5 C4 -1.0(2) . . . . ?
P C1 N5 C4 179.21(16) . . . . ?
N2 C1 N5 C6 -170.01(18) . . . . ?
P C1 N5 C6 10.2(3) . . . . ?
C1 N2 C3 C4 -0.8(3) . . . . ?
C21 N2 C3 C4 -179.5(2) . . . . ?
N2 C3 C4 N5 0.2(3) . . . . ?
C1 N5 C4 C3 0.5(3) . . . . ?
C6 N5 C4 C3 168.8(2) . . . . ?
C1 N5 C6 N7 -45.5(3) . . . . ?
C4 N5 C6 N7 147.4(2) . . . . ?
N7 C8 C9 N10 0.6(2) . . . . ?
C1 P C11 N10 157.40(18) . . . . ?
C1 P C11 N7 -22.14(19) . . . . ?
N10 C11 N7 C8 1.2(2) . . . . ?
P C11 N7 C8 -179.17(15) . . . . ?
N10 C11 N7 C6 171.48(18) . . . . ?
P C11 N7 C6 -8.9(3) . . . . ?
C9 C8 N7 C11 -1.2(2) . . . . ?
C9 C8 N7 C6 -170.90(19) . . . . ?
N5 C6 N7 C11 44.9(3) . . . . ?
N5 C6 N7 C8 -146.52(19) . . . . ?
N7 C11 N10 C9 -0.8(2) . . . . ?
P C11 N10 C9 179.58(15) . . . . ?
N7 C11 N10 C101 175.49(17) . . . . ?
P C11 N10 C101 -4.1(3) . . . . ?
C8 C9 N10 C11 0.1(2) . . . . ?
C8 C9 N10 C101 -176.25(18) . . . . ?
C1 N2 C21 C22 -92.2(2) . . . . ?
C3 N2 C21 C22 86.3(3) . . . . ?
N2 C21 C22 C23 -173.42(19) . . . . ?
N2 C21 C22 C27 5.4(3) . . . . ?
C27 C22 C23 C24 0.4(3) . . . . ?
C21 C22 C23 C24 179.2(2) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C25 C26 C27 C22 -0.8(4) . . . . ?
C23 C22 C27 C26 0.3(3) . . . . ?
C21 C22 C27 C26 -178.5(2) . . . . ?
C11 N10 C101 C102 108.9(2) . . . . ?
C9 N10 C101 C102 -75.4(2) . . . . ?
N10 C101 C102 C103 112.7(2) . . . . ?
N10 C101 C102 C107 -70.7(2) . . . . ?
C107 C102 C103 C104 -1.5(4) . . . . ?
C101 C102 C103 C104 175.1(2) . . . . ?
C102 C103 C104 C105 1.0(4) . . . . ?
C103 C104 C105 C106 0.6(4) . . . . ?
C104 C105 C106 C107 -1.6(4) . . . . ?
C103 C102 C107 C106 0.4(3) . . . . ?
C101 C102 C107 C106 -176.1(2) . . . . ?
C105 C106 C107 C102 1.1(4) . . . . ?
C41 B C31 C36 34.6(2) . . . . ?
C51 B C31 C36 -85.1(2) . . . . ?
C61 B C31 C36 155.55(18) . . . . ?
C41 B C31 C32 -148.94(18) . . . . ?
C51 B C31 C32 91.4(2) . . . . ?
C61 B C31 C32 -28.0(2) . . . . ?
C36 C31 C32 C33 -1.2(3) . . . . ?
B C31 C32 C33 -177.81(18) . . . . ?
C31 C32 C33 C34 1.3(3) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 -1.1(3) . . . . ?
C34 C35 C36 C31 1.3(3) . . . . ?
C32 C31 C36 C35 -0.1(3) . . . . ?
B C31 C36 C35 176.61(19) . . . . ?
C31 B C41 C46 -125.86(19) . . . . ?
C51 B C41 C46 -6.6(2) . . . . ?
C61 B C41 C46 113.18(19) . . . . ?
C31 B C41 C42 56.0(2) . . . . ?
C51 B C41 C42 175.34(16) . . . . ?
C61 B C41 C42 -64.9(2) . . . . ?
C46 C41 C42 C43 -3.3(3) . . . . ?
B C41 C42 C43 174.98(18) . . . . ?
C41 C42 C43 C44 2.6(3) . . . . ?
C42 C43 C44 C45 -0.1(3) . . . . ?
C43 C44 C45 C46 -1.5(3) . . . . ?
C44 C45 C46 C41 0.7(3) . . . . ?
C42 C41 C46 C45 1.7(3) . . . . ?
B C41 C46 C45 -176.55(18) . . . . ?
C41 B C51 C52 -95.8(2) . . . . ?
C31 B C51 C52 23.6(2) . . . . ?
C61 B C51 C52 143.73(17) . . . . ?
C41 B C51 C56 81.5(2) . . . . ?
C31 B C51 C56 -159.00(17) . . . . ?
C61 B C51 C56 -38.9(2) . . . . ?
C56 C51 C52 C53 1.0(3) . . . . ?
B C51 C52 C53 178.50(18) . . . . ?
C51 C52 C53 C54 -0.3(3) . . . . ?
C52 C53 C54 C55 -0.9(3) . . . . ?
C53 C54 C55 C56 1.4(3) . . . . ?
C54 C55 C56 C51 -0.7(3) . . . . ?
C52 C51 C56 C55 -0.5(3) . . . . ?
B C51 C56 C55 -178.03(17) . . . . ?
C41 B C61 C62 -157.33(18) . . . . ?
C31 B C61 C62 82.2(2) . . . . ?
C51 B C61 C62 -37.2(2) . . . . ?
C41 B C61 C66 25.2(2) . . . . ?
C31 B C61 C66 -95.2(2) . . . . ?
C51 B C61 C66 145.35(18) . . . . ?
C66 C61 C62 C63 -0.2(3) . . . . ?
B C61 C62 C63 -178.0(2) . . . . ?
C61 C62 C63 C64 0.9(4) . . . . ?
C62 C63 C64 C65 -0.5(3) . . . . ?
C63 C64 C65 C66 -0.5(3) . . . . ?
C64 C65 C66 C61 1.2(3) . . . . ?
C62 C61 C66 C65 -0.8(3) . . . . ?
B C61 C66 C65 176.75(18) . . . . ?

_refine_diff_density_max         2.152
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042848'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2015-03-27 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         'C18 H24 Au N8 P2, 2(C F3 O3 S), Cl'
_chemical_formula_sum            'C20 H24 Au Cl F6 N8 O6 P2 S2'
_chemical_formula_weight         944.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.7657(7)
_cell_length_b                   14.6302(7)
_cell_length_c                   13.2427(5)
_cell_angle_alpha                90
_cell_angle_beta                 123.628(2)
_cell_angle_gamma                90
_cell_volume                     3349.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9276
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      30.56

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    4.772
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_T_max  0.686
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61590
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_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             3862
_reflns_number_gt                3693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+11.7716P] 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         3862
_refine_ls_number_parameters     212
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.073
_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
Au Au 0.5000 0.35619(2) 0.2500 0.02293(8) Uani 1 2 d S T P . .
P P 0.37114(5) 0.34328(6) 0.18835(8) 0.02201(18) Uani 1 1 d . . . . .
C1 C 0.37039(18) 0.4281(2) 0.2879(3) 0.0200(6) Uani 1 1 d . . . . .
N2 N 0.33805(16) 0.5113(2) 0.2577(3) 0.0234(6) Uani 1 1 d . . . . .
N5 N 0.40254(16) 0.41826(19) 0.4072(3) 0.0222(5) Uani 1 1 d . . . . .
C3 C 0.3513(2) 0.5549(2) 0.3598(4) 0.0284(7) Uani 1 1 d . . . . .
H3 H 0.3350 0.6149 0.3630 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3914(2) 0.4971(2) 0.4542(4) 0.0287(7) Uani 1 1 d . . . . .
H4 H 0.4086 0.5080 0.5362 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4502(2) 0.3399(2) 0.4762(3) 0.0259(7) Uani 1 1 d . . . . .
H6A H 0.5020 0.3452 0.4899 0.031 Uiso 1 1 calc R U . . .
H6B H 0.4568 0.3373 0.5561 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4096(2) 0.1736(3) 0.4531(4) 0.0306(8) Uani 1 1 d . . . . .
H8 H 0.4260 0.1603 0.5342 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3795(2) 0.1142(3) 0.3594(4) 0.0328(8) Uani 1 1 d . . . . .
H9 H 0.3710 0.0508 0.3625 0.039 Uiso 1 1 calc R U . . .
C11 C 0.38348(18) 0.2502(2) 0.2886(3) 0.0205(6) Uani 1 1 d . . . . .
N7 N 0.41175(16) 0.25803(19) 0.4072(3) 0.0221(6) Uani 1 1 d . . . . .
N10 N 0.36348(19) 0.1626(2) 0.2588(3) 0.0277(6) Uani 1 1 d . . . . .
C21 C 0.2961(2) 0.5508(3) 0.1359(4) 0.0310(8) Uani 1 1 d . . . . .
H21A H 0.3320 0.5615 0.1111 0.046 Uiso 1 1 calc R U . . .
H21B H 0.2727 0.6090 0.1361 0.046 Uiso 1 1 calc R U . . .
H21C H 0.2554 0.5086 0.0789 0.046 Uiso 1 1 calc R U . . .
C101 C 0.3275(3) 0.1265(3) 0.1354(5) 0.0480(12) Uani 1 1 d . . . . .
H10A H 0.2794 0.1598 0.0801 0.072 Uiso 1 1 calc R U . . .
H10B H 0.3159 0.0614 0.1346 0.072 Uiso 1 1 calc R U . . .
H10C H 0.3630 0.1341 0.1093 0.072 Uiso 1 1 calc R U . . .
Cl Cl 0.0000 0.06584(7) 0.2500 0.0205(2) Uani 1 2 d S T P . .
O1 O 0.0904(2) 0.2871(3) 0.0638(4) 0.0727(13) Uani 1 1 d . . . . .
O2 O 0.2224(2) 0.2576(2) 0.2174(4) 0.0649(12) Uani 1 1 d . . . . .
O3 O 0.1806(2) 0.4117(2) 0.1460(4) 0.0580(10) Uani 1 1 d . . . . .
S S 0.16087(6) 0.32263(7) 0.16368(11) 0.0348(2) Uani 1 1 d . . . . .
C01 C 0.1385(6) 0.3425(4) 0.2747(9) 0.078(3) Uani 0.819(6) 1 d D . P A 1
F11 F 0.1947(4) 0.3732(4) 0.3748(6) 0.1012(15) Uani 0.819(6) 1 d D . P A 1
F12 F 0.0795(4) 0.4017(4) 0.2332(6) 0.1012(15) Uani 0.819(6) 1 d D . P A 1
F13 F 0.1164(5) 0.2630(4) 0.3014(7) 0.1012(15) Uani 0.819(6) 1 d D . P A 1
C02 C 0.1344(18) 0.3208(17) 0.276(3) 0.078(3) Uani 0.181(6) 1 d D . P A 2
F21 F 0.0672(16) 0.2738(17) 0.233(3) 0.1012(15) Uani 0.181(6) 1 d D . P A 2
F22 F 0.1789(16) 0.2735(16) 0.380(2) 0.1012(15) Uani 0.181(6) 1 d D . P A 2
F23 F 0.1214(19) 0.4016(13) 0.309(3) 0.1012(15) Uani 0.181(6) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au P 2.3329(9) . ?
Au P 2.3330(9) 2_655 ?
P C1 1.817(3) . ?
P C11 1.818(4) . ?
C1 N5 1.339(4) . ?
C1 N2 1.340(4) . ?
N2 C3 1.378(5) . ?
N2 C21 1.462(5) . ?
N5 C4 1.389(4) . ?
N5 C6 1.459(4) . ?
C3 C4 1.349(6) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 N7 1.449(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.351(6) . ?
C8 N7 1.388(4) . ?
C8 H8 0.9500 . ?
C9 N10 1.377(5) . ?
C9 H9 0.9500 . ?
C11 N10 1.337(4) . ?
C11 N7 1.343(4) . ?
N10 C101 1.468(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
O1 S 1.421(4) . ?
O2 S 1.426(3) . ?
O3 S 1.424(3) . ?
S C01 1.794(9) . ?
S C02 1.84(3) . ?
C01 F11 1.268(11) . ?
C01 F12 1.345(11) . ?
C01 F13 1.366(8) . ?
C02 F23 1.338(19) . ?
C02 F22 1.351(19) . ?
C02 F21 1.365(19) . ?

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
P Au P 170.71(4) . 2_655 ?
C1 P C11 92.08(15) . . ?
C1 P Au 99.20(11) . . ?
C11 P Au 97.73(10) . . ?
N5 C1 N2 106.9(3) . . ?
N5 C1 P 125.7(2) . . ?
N2 C1 P 127.4(3) . . ?
C1 N2 C3 109.4(3) . . ?
C1 N2 C21 125.6(3) . . ?
C3 N2 C21 124.9(3) . . ?
C1 N5 C4 109.9(3) . . ?
C1 N5 C6 123.1(3) . . ?
C4 N5 C6 126.5(3) . . ?
C4 C3 N2 107.7(3) . . ?
C4 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
C3 C4 N5 106.0(3) . . ?
C3 C4 H4 127.0 . . ?
N5 C4 H4 127.0 . . ?
N7 C6 N5 108.0(3) . . ?
N7 C6 H6A 110.1 . . ?
N5 C6 H6A 110.1 . . ?
N7 C6 H6B 110.1 . . ?
N5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C9 C8 N7 106.3(3) . . ?
C9 C8 H8 126.9 . . ?
N7 C8 H8 126.9 . . ?
C8 C9 N10 107.4(3) . . ?
C8 C9 H9 126.3 . . ?
N10 C9 H9 126.3 . . ?
N10 C11 N7 106.9(3) . . ?
N10 C11 P 127.4(3) . . ?
N7 C11 P 125.7(2) . . ?
C11 N7 C8 109.7(3) . . ?
C11 N7 C6 122.7(3) . . ?
C8 N7 C6 126.8(3) . . ?
C11 N10 C9 109.8(3) . . ?
C11 N10 C101 123.9(4) . . ?
C9 N10 C101 126.4(3) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N10 C101 H10A 109.5 . . ?
N10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
N10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O1 S O3 115.1(3) . . ?
O1 S O2 113.4(3) . . ?
O3 S O2 115.6(2) . . ?
O1 S C01 102.8(4) . . ?
O3 S C01 102.4(3) . . ?
O2 S C01 105.4(4) . . ?
O1 S C02 97.5(10) . . ?
O3 S C02 112.7(8) . . ?
O2 S C02 99.9(9) . . ?
F11 C01 F12 107.6(6) . . ?
F11 C01 F13 106.1(8) . . ?
F12 C01 F13 107.1(8) . . ?
F11 C01 S 114.1(7) . . ?
F12 C01 S 111.1(6) . . ?
F13 C01 S 110.6(5) . . ?
F23 C02 F22 105(2) . . ?
F23 C02 F21 104(2) . . ?
F22 C02 F21 97.6(18) . . ?
F23 C02 S 117(2) . . ?
F22 C02 S 119(2) . . ?
F21 C02 S 111(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P C1 N5 24.4(3) . . . . ?
Au P C1 N5 -73.8(3) . . . . ?
C11 P C1 N2 -155.4(3) . . . . ?
Au P C1 N2 106.4(3) . . . . ?
N5 C1 N2 C3 1.1(4) . . . . ?
P C1 N2 C3 -179.1(3) . . . . ?
N5 C1 N2 C21 -179.7(3) . . . . ?
P C1 N2 C21 0.1(5) . . . . ?
N2 C1 N5 C4 -0.8(4) . . . . ?
P C1 N5 C4 179.4(3) . . . . ?
N2 C1 N5 C6 -173.6(3) . . . . ?
P C1 N5 C6 6.7(5) . . . . ?
C1 N2 C3 C4 -0.9(4) . . . . ?
C21 N2 C3 C4 179.9(3) . . . . ?
N2 C3 C4 N5 0.4(4) . . . . ?
C1 N5 C4 C3 0.3(4) . . . . ?
C6 N5 C4 C3 172.7(3) . . . . ?
C1 N5 C6 N7 -44.9(5) . . . . ?
C4 N5 C6 N7 143.6(3) . . . . ?
N7 C8 C9 N10 -0.4(4) . . . . ?
C1 P C11 N10 155.1(3) . . . . ?
Au P C11 N10 -105.3(3) . . . . ?
C1 P C11 N7 -21.7(3) . . . . ?
Au P C11 N7 77.9(3) . . . . ?
N10 C11 N7 C8 0.1(4) . . . . ?
P C11 N7 C8 177.4(3) . . . . ?
N10 C11 N7 C6 170.3(3) . . . . ?
P C11 N7 C6 -12.4(5) . . . . ?
C9 C8 N7 C11 0.2(4) . . . . ?
C9 C8 N7 C6 -169.5(3) . . . . ?
N5 C6 N7 C11 47.8(4) . . . . ?
N5 C6 N7 C8 -143.7(3) . . . . ?
N7 C11 N10 C9 -0.3(4) . . . . ?
P C11 N10 C9 -177.6(3) . . . . ?
N7 C11 N10 C101 177.8(4) . . . . ?
P C11 N10 C101 0.5(6) . . . . ?
C8 C9 N10 C11 0.5(4) . . . . ?
C8 C9 N10 C101 -177.6(4) . . . . ?
O1 S C01 F11 178.6(6) . . . . ?
O3 S C01 F11 -61.7(6) . . . . ?
O2 S C01 F11 59.6(6) . . . . ?
O1 S C01 F12 -59.6(6) . . . . ?
O3 S C01 F12 60.1(6) . . . . ?
O2 S C01 F12 -178.6(5) . . . . ?
O1 S C01 F13 59.2(8) . . . . ?
O3 S C01 F13 178.9(7) . . . . ?
O2 S C01 F13 -59.8(8) . . . . ?
O1 S C02 F23 -108(2) . . . . ?
O3 S C02 F23 13(2) . . . . ?
O2 S C02 F23 136(2) . . . . ?
O1 S C02 F22 122.9(18) . . . . ?
O3 S C02 F22 -115.9(18) . . . . ?
O2 S C02 F22 7(2) . . . . ?
O1 S C02 F21 10.6(18) . . . . ?
O3 S C02 F21 131.8(16) . . . . ?
O2 S C02 F21 -104.8(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O2 0.95 2.35 3.232(5) 154.8 4
C4 H4 Cl 0.95 2.61 3.390(4) 139.1 7_556
C6 H6A O1 0.99 2.47 3.087(6) 120.3 8_556
C6 H6B Cl 0.99 2.62 3.459(4) 142.8 7_556
C9 H9 O3 0.95 2.27 3.201(5) 165.0 4_545
C21 H21A Cl 0.98 2.91 3.630(4) 131.4 3
C21 H21B F22 0.98 2.66 3.32(2) 125.1 4
C21 H21C O3 0.98 2.60 3.204(5) 120.3 .
C101 H10B F23 0.98 2.58 3.41(2) 142.9 4_545

_refine_diff_density_max         1.634
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.133


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
