# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DPA-Ox_2
_database_code_depnum_ccdc_archive 'CCDC 1994422'
loop_
_audit_author_name
_audit_author_address
'Hiroaki Imoto'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C32 H22 As2 N4 O2'
_chemical_formula_moiety         'C32 H22 As2 N4 O2'
_chemical_formula_weight         644.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.366(3)
_cell_length_b                   8.971(3)
_cell_length_c                   9.981(4)
_cell_angle_alpha                70.613(13)
_cell_angle_beta                 73.295(15)
_cell_angle_gamma                74.157(14)
_cell_volume                     663.5(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1852
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324.00
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.880

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            7075
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3030
_reflns_number_gt                2663
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0779
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0466P)²+0.1365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
As As 0.0499 2.0058
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.39358(3) 0.60266(3) 0.09338(2) 0.03693(10) Uani 1 2 d . . .
O1 O 0.4009(2) 0.50042(19) -0.07001(18) 0.0394(3) Uani 1 2 d . . .
N1 N 0.4625(3) 0.7596(3) 0.4286(3) 0.0613(6) Uani 1 2 d . . .
N2 N 0.2037(4) 0.9963(3) -0.2334(3) 0.0634(7) Uani 1 2 d . . .
C1 C 0.4033(3) 0.7211(3) 0.2241(3) 0.0422(5) Uani 1 2 d . . .
C2 C 0.3338(3) 0.8852(3) 0.1775(3) 0.0437(5) Uani 1 2 d . . .
C3 C 0.2808(3) 0.9349(3) 0.0368(3) 0.0424(5) Uani 1 2 d . . .
C4 C 0.3072(3) 0.8114(3) -0.0275(3) 0.0408(5) Uani 1 2 d . . .
C5 C 0.2182(3) 0.4844(3) 0.2122(3) 0.0388(5) Uani 1 2 d . . .
C6 C 0.4685(4) 0.6659(4) 0.3482(3) 0.0523(6) Uani 1 2 d . . .
C7 C 0.3891(4) 0.9154(4) 0.3855(4) 0.0659(8) Uani 1 2 d . . .
C8 C 0.3253(4) 0.9847(4) 0.2598(3) 0.0571(7) Uani 1 2 d . . .
C9 C 0.2685(4) 0.8474(3) -0.1623(3) 0.0503(6) Uani 1 2 d . . .
C10 C 0.1796(5) 1.1131(4) -0.1703(4) 0.0665(8) Uani 1 2 d . . .
C11 C 0.2153(4) 1.0894(3) -0.0368(3) 0.0572(7) Uani 1 2 d . . .
C12 C 0.2348(4) 0.3845(3) 0.3499(3) 0.0527(6) Uani 1 2 d . . .
C13 C 0.1055(5) 0.3015(4) 0.4347(3) 0.0688(9) Uani 1 2 d . . .
C14 C -0.0381(5) 0.3220(5) 0.3841(4) 0.0751(10) Uani 1 2 d . . .
C15 C -0.0545(4) 0.4218(4) 0.2487(4) 0.0660(8) Uani 1 2 d . . .
C16 C 0.0746(3) 0.5018(3) 0.1619(3) 0.0508(6) Uani 1 2 d . . .
H6 H 0.5191 0.55759 0.37658 0.0628 Uiso 1 2 calc R . .
H7 H 0.38037 0.98106 0.44338 0.0791 Uiso 1 2 calc R . .
H8 H 0.27861 1.09417 0.23235 0.0685 Uiso 1 2 calc R . .
H9 H 0.28851 0.7643 -0.20479 0.0604 Uiso 1 2 calc R . .
H10 H 0.13572 1.21757 -0.21954 0.0798 Uiso 1 2 calc R . .
H11 H 0.19554 1.17527 0.00216 0.0687 Uiso 1 2 calc R . .
H12 H 0.33057 0.3734 0.38462 0.0632 Uiso 1 2 calc R . .
H13 H 0.11606 0.23185 0.52589 0.0826 Uiso 1 2 calc R . .
H14 H -0.12478 0.26756 0.44238 0.0901 Uiso 1 2 calc R . .
H15 H -0.15217 0.43547 0.21555 0.0792 Uiso 1 2 calc R . .
H16 H 0.06502 0.56762 0.06923 0.0610 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
As1 As1 2.9356(9) yes . 2_665
As1 O1 2.100(2) yes . .
As1 O1 1.7057(16) yes . 2_665
As1 C1 1.966(3) yes . .
As1 C4 1.936(2) yes . .
As1 C5 1.923(2) yes . .
N1 C6 1.325(5) yes . .
N1 C7 1.341(4) yes . .
N2 C9 1.334(3) yes . .
N2 C10 1.335(5) yes . .
C1 C2 1.398(3) yes . .
C1 C6 1.382(4) yes . .
C2 C3 1.484(4) yes . .
C2 C8 1.376(5) yes . .
C3 C4 1.395(4) yes . .
C3 C11 1.379(3) yes . .
C4 C9 1.387(4) yes . .
C5 C12 1.391(3) yes . .
C5 C16 1.383(4) yes . .
C7 C8 1.390(5) yes . .
C10 C11 1.384(5) yes . .
C12 C13 1.392(5) yes . .
C13 C14 1.377(6) yes . .
C14 C15 1.373(5) yes . .
C15 C16 1.380(4) yes . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
As1 As1 O1 34.85(5) yes 2_665 . .
As1 As1 O1 44.70(7) yes 2_665 . 2_665
As1 As1 C1 142.84(7) yes 2_665 . .
As1 As1 C4 109.16(8) yes 2_665 . .
As1 As1 C5 103.55(8) yes 2_665 . .
O1 As1 O1 79.55(9) yes . . 2_665
O1 As1 C1 171.86(8) yes . . .
O1 As1 C4 88.75(10) yes . . .
O1 As1 C5 86.88(10) yes . . .
O1 As1 C1 98.80(10) yes 2_665 . .
O1 As1 C4 126.28(8) yes 2_665 . .
O1 As1 C5 118.05(9) yes 2_665 . .
C1 As1 C4 85.85(12) yes . . .
C1 As1 C5 100.84(11) yes . . .
C4 As1 C5 113.32(10) yes . . .
As1 O1 As1 100.45(10) yes . . 2_665
C6 N1 C7 117.4(3) yes . . .
C9 N2 C10 117.0(3) yes . . .
As1 C1 C2 111.8(2) yes . . .
As1 C1 C6 129.7(2) yes . . .
C2 C1 C6 118.5(3) yes . . .
C1 C2 C3 114.4(3) yes . . .
C1 C2 C8 119.2(3) yes . . .
C3 C2 C8 126.4(2) yes . . .
C2 C3 C4 115.3(2) yes . . .
C2 C3 C11 126.5(3) yes . . .
C4 C3 C11 118.1(3) yes . . .
As1 C4 C3 112.35(19) yes . . .
As1 C4 C9 128.2(2) yes . . .
C3 C4 C9 119.5(2) yes . . .
As1 C5 C12 119.7(2) yes . . .
As1 C5 C16 119.92(17) yes . . .
C12 C5 C16 120.3(2) yes . . .
N1 C6 C1 123.2(3) yes . . .
N1 C7 C8 124.1(4) yes . . .
C2 C8 C7 117.4(3) yes . . .
N2 C9 C4 122.7(3) yes . . .
N2 C10 C11 124.6(3) yes . . .
C3 C11 C10 118.2(3) yes . . .
C5 C12 C13 118.8(3) yes . . .
C12 C13 C14 120.3(3) yes . . .
C13 C14 C15 120.7(3) yes . . .
C14 C15 C16 119.6(4) yes . . .
C5 C16 C15 120.3(3) yes . . .
N1 C6 H6 118.385 no . . .
C1 C6 H6 118.388 no . . .
N1 C7 H7 117.945 no . . .
C8 C7 H7 117.943 no . . .
C2 C8 H8 121.290 no . . .
C7 C8 H8 121.284 no . . .
N2 C9 H9 118.665 no . . .
C4 C9 H9 118.664 no . . .
N2 C10 H10 117.713 no . . .
C11 C10 H10 117.723 no . . .
C3 C11 H11 120.919 no . . .
C10 C11 H11 120.917 no . . .
C5 C12 H12 120.610 no . . .
C13 C12 H12 120.617 no . . .
C12 C13 H13 119.864 no . . .
C14 C13 H13 119.861 no . . .
C13 C14 H14 119.644 no . . .
C15 C14 H14 119.636 no . . .
C14 C15 H15 120.188 no . . .
C16 C15 H15 120.189 no . . .
C5 C16 H16 119.878 no . . .
C15 C16 H16 119.866 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
As1 As1 O1 As1 0.0 no 2_665 . . 2_665
O1 As1 As1 O1 180.00(8) no . . 2_665 2_665
O1 As1 As1 O1 0.00(7) no . . 2_665 .
O1 As1 As1 C1 -13.30(7) no . . 2_665 2_665
O1 As1 As1 C4 -122.65(7) no . . 2_665 2_665
O1 As1 As1 C5 116.36(7) no . . 2_665 2_665
As1 As1 O1 As1 0.0 no 2_665 . 2_665 2_665
O1 As1 As1 O1 -0.00(7) no 2_665 . 2_665 2_665
O1 As1 As1 O1 -180.00(7) no 2_665 . 2_665 .
O1 As1 As1 C1 166.70(7) no 2_665 . 2_665 2_665
O1 As1 As1 C4 57.35(7) no 2_665 . 2_665 2_665
O1 As1 As1 C5 -63.64(7) no 2_665 . 2_665 2_665
As1 As1 C1 C2 121.76(11) no 2_665 . . .
As1 As1 C1 C6 -57.3(2) no 2_665 . . .
C1 As1 As1 O1 13.30(11) no . . 2_665 2_665
C1 As1 As1 O1 -166.70(11) no . . 2_665 .
C1 As1 As1 C1 -180.00(11) no . . 2_665 2_665
C1 As1 As1 C4 70.65(11) no . . 2_665 2_665
C1 As1 As1 C5 -50.34(11) no . . 2_665 2_665
As1 As1 C4 C3 -150.08(11) no 2_665 . . .
As1 As1 C4 C9 31.1(2) no 2_665 . . .
C4 As1 As1 O1 122.65(9) no . . 2_665 2_665
C4 As1 As1 O1 -57.35(9) no . . 2_665 .
C4 As1 As1 C1 -70.65(9) no . . 2_665 2_665
C4 As1 As1 C4 180.00(9) no . . 2_665 2_665
C4 As1 As1 C5 59.01(9) no . . 2_665 2_665
As1 As1 C5 C12 95.84(17) no 2_665 . . .
As1 As1 C5 C16 -85.61(16) no 2_665 . . .
C5 As1 As1 O1 -116.36(8) no . . 2_665 2_665
C5 As1 As1 O1 63.64(8) no . . 2_665 .
C5 As1 As1 C1 50.34(8) no . . 2_665 2_665
C5 As1 As1 C4 -59.01(8) no . . 2_665 2_665
C5 As1 As1 C5 -180.00(8) no . . 2_665 2_665
O1 As1 O1 As1 -0.00(6) no . . 2_665 2_665
O1 As1 O1 As1 0.00(7) no 2_665 . . 2_665
O1 As1 C4 C3 -178.84(14) no . . . .
O1 As1 C4 C9 2.36(18) no . . . .
C4 As1 O1 As1 127.29(9) no . . . 2_665
O1 As1 C5 C12 126.69(17) no . . . .
O1 As1 C5 C16 -54.77(17) no . . . .
C5 As1 O1 As1 -119.27(9) no . . . 2_665
O1 As1 C1 C2 131.18(13) no 2_665 . . .
O1 As1 C1 C6 -47.9(2) no 2_665 . . .
C1 As1 O1 As1 -171.92(8) no . . 2_665 2_665
O1 As1 C4 C3 -102.80(15) no 2_665 . . .
O1 As1 C4 C9 78.4(2) no 2_665 . . .
C4 As1 O1 As1 -80.62(15) no . . 2_665 2_665
O1 As1 C5 C12 50.3(2) no 2_665 . . .
O1 As1 C5 C16 -131.18(15) no 2_665 . . .
C5 As1 O1 As1 80.74(12) no . . 2_665 2_665
C1 As1 C4 C3 -4.93(15) no . . . .
C1 As1 C4 C9 176.3(2) no . . . .
C4 As1 C1 C2 5.09(14) no . . . .
C4 As1 C1 C6 -174.0(2) no . . . .
C1 As1 C5 C12 -55.89(18) no . . . .
C1 As1 C5 C16 122.65(18) no . . . .
C5 As1 C1 C2 -107.88(14) no . . . .
C5 As1 C1 C6 73.0(2) no . . . .
C4 As1 C5 C12 -146.03(16) no . . . .
C4 As1 C5 C16 32.5(2) no . . . .
C5 As1 C4 C3 95.10(18) no . . . .
C5 As1 C4 C9 -83.7(2) no . . . .
C6 N1 C7 C8 -2.5(5) no . . . .
C7 N1 C6 C1 -0.1(4) no . . . .
C9 N2 C10 C11 -0.7(5) no . . . .
C10 N2 C9 C4 1.2(4) no . . . .
As1 C1 C2 C3 -4.2(2) no . . . .
As1 C1 C2 C8 177.78(14) no . . . .
As1 C1 C6 N1 -178.19(16) no . . . .
C2 C1 C6 N1 2.7(4) no . . . .
C6 C1 C2 C3 175.0(2) no . . . .
C6 C1 C2 C8 -3.0(3) no . . . .
C1 C2 C3 C4 0.3(3) no . . . .
C1 C2 C3 C11 -177.2(2) no . . . .
C1 C2 C8 C7 0.7(4) no . . . .
C3 C2 C8 C7 -177.0(2) no . . . .
C8 C2 C3 C4 178.1(2) no . . . .
C8 C2 C3 C11 0.6(4) no . . . .
C2 C3 C4 As1 3.9(3) no . . . .
C2 C3 C4 C9 -177.23(19) no . . . .
C2 C3 C11 C10 177.4(2) no . . . .
C4 C3 C11 C10 -0.1(4) no . . . .
C11 C3 C4 As1 -178.4(2) no . . . .
C11 C3 C4 C9 0.5(3) no . . . .
As1 C4 C9 N2 177.60(17) no . . . .
C3 C4 C9 N2 -1.1(4) no . . . .
As1 C5 C12 C13 179.28(17) no . . . .
As1 C5 C16 C15 -177.66(17) no . . . .
C12 C5 C16 C15 0.9(4) no . . . .
C16 C5 C12 C13 0.7(4) no . . . .
N1 C7 C8 C2 2.1(5) no . . . .
N2 C10 C11 C3 0.2(5) no . . . .
C5 C12 C13 C14 -1.8(5) no . . . .
C12 C13 C14 C15 1.3(6) no . . . .
C13 C14 C15 C16 0.4(6) no . . . .
C14 C15 C16 C5 -1.4(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C6 3.353(4) no . 2_665
O1 C9 2.927(3) no . .
O1 C16 3.030(3) no . .
N1 C2 2.778(4) no . .
N2 C3 2.795(4) no . .
C1 C7 2.699(6) no . .
C1 C12 3.387(4) no . .
C4 C10 2.689(4) no . .
C4 C16 3.525(4) no . .
C5 C14 2.756(4) no . .
C6 C8 2.731(4) no . .
C6 C12 3.583(5) no . .
C8 C11 3.121(5) no . .
C9 C11 2.727(5) no . .
C12 C15 2.781(5) no . .
C13 C16 2.759(4) no . .
N1 C10 3.520(4) no . 2_675
N1 C12 3.537(5) no . 2_666
N2 C7 3.498(5) no . 2_675
C6 C6 3.521(4) no . 2_666
C7 N2 3.498(5) no . 2_675
C10 N1 3.520(4) no . 2_675
C10 C16 3.542(4) no . 2_575
C12 N1 3.537(5) no . 2_666
C16 C10 3.542(4) no . 2_575
As1 H6 3.1578 no . .
As1 H9 3.1104 no . .
As1 H12 2.9494 no . .
As1 H16 2.9351 no . .
O1 H6 3.1259 no . 2_665
O1 H9 2.3865 no . .
O1 H12 3.3407 no . 2_665
O1 H16 2.7527 no . .
N1 H8 3.2432 no . .
N2 H11 3.2343 no . .
C1 H8 3.2436 no . .
C1 H12 3.1345 no . .
C2 H6 3.2242 no . .
C2 H7 3.1971 no . .
C2 H11 2.7691 no . .
C3 H8 2.7688 no . .
C3 H9 3.2354 no . .
C3 H10 3.2010 no . .
C4 H11 3.2297 no . .
C4 H16 3.1166 no . .
C5 H13 3.2362 no . .
C5 H15 3.2355 no . .
C6 H7 3.1119 no . .
C6 H12 3.0208 no . .
C7 H6 3.1175 no . .
C8 H11 2.8957 no . .
C9 H10 3.1109 no . .
C9 H16 3.2798 no . .
C10 H9 3.1168 no . .
C11 H8 2.8996 no . .
C12 H6 3.2853 no . .
C12 H14 3.2382 no . .
C12 H16 3.2437 no . .
C13 H15 3.2289 no . .
C14 H12 3.2420 no . .
C14 H16 3.2186 no . .
C15 H13 3.2263 no . .
C16 H12 3.2470 no . .
C16 H14 3.2184 no . .
H6 H12 2.5468 no . .
H7 H8 2.3089 no . .
H8 H11 2.4131 no . .
H9 H12 3.3071 no . 2_665
H9 H16 3.1219 no . .
H10 H11 2.2948 no . .
H12 H13 2.3285 no . .
H13 H14 2.3005 no . .
H14 H15 2.3006 no . .
H15 H16 2.3110 no . .
O1 H11 3.5509 no . 1_545
O1 H15 2.7021 no . 2_565
N1 H6 2.8567 no . 2_666
N1 H9 3.5382 no . 1_556
N1 H10 3.4284 no . 2_675
N1 H12 2.6738 no . 2_666
N1 H14 2.7883 no . 2_566
N2 H7 3.1705 no . 1_554
N2 H7 3.5284 no . 2_675
N2 H13 2.7515 no . 1_564
C1 H14 3.4866 no . 2_566
C5 H8 3.3429 no . 1_545
C5 H10 3.4065 no . 2_575
C6 H6 2.8234 no . 2_666
C6 H10 3.5014 no . 2_675
C6 H12 3.4196 no . 2_666
C6 H14 3.0709 no . 2_566
C6 H15 3.4517 no . 1_655
C7 H7 3.3802 no . 2_676
C7 H13 3.5358 no . 1_565
C7 H14 2.9083 no . 2_566
C8 H14 3.3928 no . 2_566
C9 H15 3.1954 no . 2_565
C10 H13 3.0138 no . 1_564
C10 H16 3.3079 no . 2_575
C11 H16 3.3024 no . 2_575
C12 H7 3.3846 no . 1_545
C12 H8 3.0909 no . 1_545
C13 H7 3.1458 no . 1_545
C13 H8 2.9958 no . 1_545
C13 H10 3.3486 no . 1_546
C14 H8 3.2063 no . 1_545
C14 H9 3.4861 no . 2_565
C15 H6 3.4465 no . 1_455
C15 H8 3.4665 no . 1_545
C15 H9 3.0939 no . 2_565
C15 H10 3.0497 no . 2_575
C15 H16 3.1684 no . 2_565
C16 H8 3.5146 no . 1_545
C16 H10 2.7796 no . 2_575
C16 H11 3.5636 no . 1_545
C16 H11 3.4037 no . 2_575
C16 H15 3.5095 no . 2_565
C16 H16 3.1581 no . 2_565
H6 N1 2.8567 no . 2_666
H6 C6 2.8234 no . 2_666
H6 C15 3.4465 no . 1_655
H6 H6 2.2972 no . 2_666
H6 H12 3.2823 no . 2_666
H6 H14 3.4401 no . 1_655
H6 H14 3.4981 no . 2_566
H6 H15 2.8860 no . 1_655
H7 N2 3.1705 no . 1_556
H7 N2 3.5284 no . 2_675
H7 C7 3.3802 no . 2_676
H7 C12 3.3846 no . 1_565
H7 C13 3.1458 no . 1_565
H7 H7 2.7067 no . 2_676
H7 H9 3.3814 no . 1_556
H7 H12 3.2976 no . 1_565
H7 H13 2.8453 no . 1_565
H7 H14 3.2187 no . 2_566
H8 C5 3.3429 no . 1_565
H8 C12 3.0909 no . 1_565
H8 C13 2.9958 no . 1_565
H8 C14 3.2063 no . 1_565
H8 C15 3.4665 no . 1_565
H8 C16 3.5146 no . 1_565
H8 H12 3.5035 no . 1_565
H8 H13 3.3396 no . 1_565
H9 N1 3.5382 no . 1_554
H9 C14 3.4861 no . 2_565
H9 C15 3.0939 no . 2_565
H9 H7 3.3814 no . 1_554
H9 H14 3.1799 no . 2_565
H9 H15 2.4162 no . 2_565
H10 N1 3.4284 no . 2_675
H10 C5 3.4065 no . 2_575
H10 C6 3.5014 no . 2_675
H10 C13 3.3486 no . 1_564
H10 C15 3.0497 no . 2_575
H10 C16 2.7796 no . 2_575
H10 H13 2.5518 no . 1_564
H10 H15 3.1666 no . 2_575
H10 H16 2.7364 no . 2_575
H11 O1 3.5509 no . 1_565
H11 C16 3.5636 no . 1_565
H11 C16 3.4037 no . 2_575
H11 H15 3.4309 no . 2_575
H11 H16 2.7632 no . 2_575
H12 N1 2.6738 no . 2_666
H12 C6 3.4196 no . 2_666
H12 H6 3.2823 no . 2_666
H12 H7 3.2976 no . 1_545
H12 H8 3.5035 no . 1_545
H13 N2 2.7515 no . 1_546
H13 C7 3.5358 no . 1_545
H13 C10 3.0138 no . 1_546
H13 H7 2.8453 no . 1_545
H13 H8 3.3396 no . 1_545
H13 H10 2.5518 no . 1_546
H14 N1 2.7883 no . 2_566
H14 C1 3.4866 no . 2_566
H14 C6 3.0709 no . 2_566
H14 C7 2.9083 no . 2_566
H14 C8 3.3928 no . 2_566
H14 H6 3.4401 no . 1_455
H14 H6 3.4981 no . 2_566
H14 H7 3.2187 no . 2_566
H14 H9 3.1799 no . 2_565
H15 O1 2.7021 no . 2_565
H15 C6 3.4517 no . 1_455
H15 C9 3.1954 no . 2_565
H15 C16 3.5095 no . 2_565
H15 H6 2.8860 no . 1_455
H15 H9 2.4162 no . 2_565
H15 H10 3.1666 no . 2_575
H15 H11 3.4309 no . 2_575
H15 H16 2.7315 no . 2_565
H16 C10 3.3079 no . 2_575
H16 C11 3.3024 no . 2_575
H16 C15 3.1684 no . 2_565
H16 C16 3.1581 no . 2_565
H16 H10 2.7364 no . 2_575
H16 H11 2.7632 no . 2_575
H16 H15 2.7315 no . 2_565
H16 H16 2.6950 no . 2_565

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_DPP_5
_database_code_depnum_ccdc_archive 'CCDC 1994424'
loop_
_audit_author_name
_audit_author_address
'Hiroaki Imoto'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 N2 P'
_chemical_formula_moiety         'C16 H11 N2 P'
_chemical_formula_weight         262.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.597(4)
_cell_length_b                   11.204(3)
_cell_length_c                   8.645(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.655(14)
_cell_angle_gamma                90.0000
_cell_volume                     1279.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1844
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544.00
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            13536
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_theta_max         27.676
_diffrn_reflns_theta_min         3.031
_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
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2995
_reflns_number_gt                1660
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1523
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2995
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0799P)²+0.5683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.67783(7) 0.99640(8) 0.49400(10) 0.0546(3) Uani 1 4 d . . .
N1 N 0.5546(2) 0.6871(3) 0.6228(4) 0.0717(9) Uani 1 4 d . . .
N2 N 0.9282(2) 0.9518(3) 0.3118(4) 0.0706(9) Uani 1 4 d . . .
C1 C 0.6502(2) 0.8447(3) 0.5432(4) 0.0495(8) Uani 1 4 d . . .
C2 C 0.7133(2) 0.7620(3) 0.4968(3) 0.0472(7) Uani 1 4 d . . .
C3 C 0.7922(2) 0.8172(3) 0.4321(4) 0.0475(7) Uani 1 4 d . . .
C4 C 0.7859(2) 0.9418(3) 0.4292(4) 0.0515(8) Uani 1 4 d . . .
C5 C 0.7321(2) 1.0630(3) 0.6879(4) 0.0492(7) Uani 1 4 d . . .
C6 C 0.5718(3) 0.8030(4) 0.6063(4) 0.0623(9) Uani 1 4 d . . .
C7 C 0.6158(3) 0.6110(4) 0.5748(5) 0.0681(10) Uani 1 4 d . . .
C8 C 0.6954(3) 0.6423(3) 0.5126(4) 0.0573(9) Uani 1 4 d . . .
C9 C 0.8563(3) 1.0027(4) 0.3673(4) 0.0630(9) Uani 1 4 d . . .
C10 C 0.9324(3) 0.8335(4) 0.3175(5) 0.0694(10) Uani 1 4 d . . .
C11 C 0.8674(3) 0.7629(3) 0.3760(4) 0.0586(9) Uani 1 4 d . . .
C12 C 0.6663(3) 1.1219(3) 0.7613(4) 0.0563(9) Uani 1 4 d . . .
C13 C 0.7007(3) 1.1735(3) 0.9091(5) 0.0640(10) Uani 1 4 d . . .
C14 C 0.8020(3) 1.1680(3) 0.9821(5) 0.0660(10) Uani 1 4 d . . .
C15 C 0.8677(3) 1.1119(3) 0.9096(4) 0.0601(9) Uani 1 4 d . . .
C16 C 0.8341(3) 1.0589(3) 0.7635(4) 0.0542(8) Uani 1 4 d . . .
H6 H 0.52958 0.85816 0.63849 0.0748 Uiso 1 4 calc R . .
H7 H 0.60355 0.53 0.58428 0.0817 Uiso 1 4 calc R . .
H8 H 0.73621 0.58471 0.48186 0.0687 Uiso 1 4 calc R . .
H9 H 0.85265 1.08562 0.36463 0.0756 Uiso 1 4 calc R . .
H10 H 0.98286 0.79602 0.27909 0.0833 Uiso 1 4 calc R . .
H11 H 0.87408 0.68022 0.37768 0.0703 Uiso 1 4 calc R . .
H12 H 0.59798 1.12682 0.71063 0.0675 Uiso 1 4 calc R . .
H13 H 0.65578 1.21156 0.95892 0.0768 Uiso 1 4 calc R . .
H14 H 0.8258 1.20288 1.08153 0.0792 Uiso 1 4 calc R . .
H15 H 0.93619 1.10947 0.95957 0.0722 Uiso 1 4 calc R . .
H16 H 0.8796 1.0204 0.71524 0.0650 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
P1 C1 1.813(4) yes . .
P1 C4 1.800(4) yes . .
P1 C5 1.823(3) yes . .
N1 C6 1.333(5) yes . .
N1 C7 1.325(6) yes . .
N2 C9 1.316(5) yes . .
N2 C10 1.327(6) yes . .
C1 C2 1.385(5) yes . .
C1 C6 1.388(5) yes . .
C2 C3 1.459(5) yes . .
C2 C8 1.376(5) yes . .
C3 C4 1.398(5) yes . .
C3 C11 1.375(5) yes . .
C4 C9 1.382(5) yes . .
C5 C12 1.382(5) yes . .
C5 C16 1.388(4) yes . .
C7 C8 1.363(6) yes . .
C10 C11 1.368(6) yes . .
C12 C13 1.379(5) yes . .
C13 C14 1.375(6) yes . .
C14 C15 1.360(6) yes . .
C15 C16 1.373(5) yes . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 P1 C4 89.10(16) yes . . .
C1 P1 C5 103.23(14) yes . . .
C4 P1 C5 104.03(15) yes . . .
C6 N1 C7 117.0(4) yes . . .
C9 N2 C10 116.7(4) yes . . .
P1 C1 C2 112.5(3) yes . . .
P1 C1 C6 129.0(3) yes . . .
C2 C1 C6 118.3(3) yes . . .
C1 C2 C3 112.9(3) yes . . .
C1 C2 C8 119.2(3) yes . . .
C3 C2 C8 127.9(3) yes . . .
C2 C3 C4 112.5(3) yes . . .
C2 C3 C11 128.6(3) yes . . .
C4 C3 C11 118.9(3) yes . . .
P1 C4 C3 112.6(3) yes . . .
P1 C4 C9 130.1(3) yes . . .
C3 C4 C9 117.1(3) yes . . .
P1 C5 C12 116.9(2) yes . . .
P1 C5 C16 124.2(3) yes . . .
C12 C5 C16 118.9(3) yes . . .
N1 C6 C1 122.7(4) yes . . .
N1 C7 C8 125.0(4) yes . . .
C2 C8 C7 117.7(3) yes . . .
N2 C9 C4 124.6(4) yes . . .
N2 C10 C11 124.4(4) yes . . .
C3 C11 C10 118.3(4) yes . . .
C5 C12 C13 120.7(3) yes . . .
C12 C13 C14 119.4(4) yes . . .
C13 C14 C15 120.3(3) yes . . .
C14 C15 C16 120.8(3) yes . . .
C5 C16 C15 119.9(3) yes . . .
N1 C6 H6 118.629 no . . .
C1 C6 H6 118.629 no . . .
N1 C7 H7 117.487 no . . .
C8 C7 H7 117.483 no . . .
C2 C8 H8 121.132 no . . .
C7 C8 H8 121.130 no . . .
N2 C9 H9 117.695 no . . .
C4 C9 H9 117.691 no . . .
N2 C10 H10 117.795 no . . .
C11 C10 H10 117.793 no . . .
C3 C11 H11 120.869 no . . .
C10 C11 H11 120.853 no . . .
C5 C12 H12 119.643 no . . .
C13 C12 H12 119.641 no . . .
C12 C13 H13 120.300 no . . .
C14 C13 H13 120.309 no . . .
C13 C14 H14 119.822 no . . .
C15 C14 H14 119.840 no . . .
C14 C15 H15 119.602 no . . .
C16 C15 H15 119.611 no . . .
C5 C16 H16 120.065 no . . .
C15 C16 H16 120.070 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 P1 C4 C3 5.39(19) no . . . .
C1 P1 C4 C9 179.7(2) no . . . .
C4 P1 C1 C2 -5.86(19) no . . . .
C4 P1 C1 C6 180.0(2) no . . . .
C1 P1 C5 C12 -92.9(2) no . . . .
C1 P1 C5 C16 87.9(3) no . . . .
C5 P1 C1 C2 -110.1(2) no . . . .
C5 P1 C1 C6 75.8(3) no . . . .
C4 P1 C5 C12 174.7(2) no . . . .
C4 P1 C5 C16 -4.5(3) no . . . .
C5 P1 C4 C3 108.81(19) no . . . .
C5 P1 C4 C9 -76.8(3) no . . . .
C6 N1 C7 C8 1.1(5) no . . . .
C7 N1 C6 C1 -0.4(5) no . . . .
C9 N2 C10 C11 0.2(5) no . . . .
C10 N2 C9 C4 -0.3(5) no . . . .
P1 C1 C2 C3 4.9(3) no . . . .
P1 C1 C2 C8 -173.95(17) no . . . .
P1 C1 C6 N1 173.4(2) no . . . .
C2 C1 C6 N1 -0.5(4) no . . . .
C6 C1 C2 C3 179.8(2) no . . . .
C6 C1 C2 C8 0.9(4) no . . . .
C1 C2 C3 C4 -0.8(3) no . . . .
C1 C2 C3 C11 179.6(2) no . . . .
C1 C2 C8 C7 -0.4(4) no . . . .
C3 C2 C8 C7 -179.1(2) no . . . .
C8 C2 C3 C4 178.0(3) no . . . .
C8 C2 C3 C11 -1.6(5) no . . . .
C2 C3 C4 P1 -3.7(3) no . . . .
C2 C3 C4 C9 -178.9(2) no . . . .
C2 C3 C11 C10 178.7(2) no . . . .
C4 C3 C11 C10 -0.9(4) no . . . .
C11 C3 C4 P1 175.9(2) no . . . .
C11 C3 C4 C9 0.8(4) no . . . .
P1 C4 C9 N2 -174.3(2) no . . . .
C3 C4 C9 N2 -0.1(4) no . . . .
P1 C5 C12 C13 179.2(2) no . . . .
P1 C5 C16 C15 179.9(2) no . . . .
C12 C5 C16 C15 0.7(5) no . . . .
C16 C5 C12 C13 -1.6(5) no . . . .
N1 C7 C8 C2 -0.6(5) no . . . .
N2 C10 C11 C3 0.4(5) no . . . .
C5 C12 C13 C14 1.3(5) no . . . .
C12 C13 C14 C15 -0.2(5) no . . . .
C13 C14 C15 C16 -0.6(5) no . . . .
C14 C15 C16 C5 0.4(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C2 2.767(5) no . .
N2 C3 2.772(5) no . .
C1 C7 2.685(5) no . .
C4 C10 2.698(6) no . .
C4 C16 3.100(5) no . .
C5 C14 2.760(5) no . .
C6 C8 2.713(5) no . .
C8 C11 3.162(6) no . .
C9 C11 2.692(5) no . .
C9 C16 3.565(5) no . .
C12 C15 2.739(5) no . .
C13 C16 2.757(6) no . .
N1 C1 3.577(5) no . 4_565
N1 C2 3.484(4) no . 4_565
N1 C12 3.460(5) no . 2_646
N1 C13 3.420(5) no . 2_646
N2 N2 3.545(4) no . 3_776
N2 C9 3.564(4) no . 3_776
N2 C16 3.447(5) no . 3_776
C1 N1 3.577(5) no . 4_564
C2 N1 3.484(4) no . 4_564
C2 C6 3.544(4) no . 4_564
C2 C11 3.460(4) no . 4_565
C3 C7 3.527(5) no . 4_564
C3 C8 3.583(5) no . 4_564
C4 C7 3.426(5) no . 4_564
C6 C2 3.544(4) no . 4_565
C6 C8 3.570(5) no . 4_565
C7 C3 3.527(5) no . 4_565
C7 C4 3.426(5) no . 4_565
C8 C3 3.583(5) no . 4_565
C8 C6 3.570(5) no . 4_564
C9 N2 3.564(4) no . 3_776
C11 C2 3.460(4) no . 4_564
C12 N1 3.460(5) no . 2_656
C13 N1 3.420(5) no . 2_656
C16 N2 3.447(5) no . 3_776
P1 H6 3.0351 no . .
P1 H9 3.0259 no . .
P1 H12 2.7895 no . .
P1 H16 2.9631 no . .
N1 H8 3.2123 no . .
N2 H11 3.2126 no . .
C1 H8 3.2296 no . .
C2 H6 3.2161 no . .
C2 H7 3.1764 no . .
C2 H11 2.7830 no . .
C3 H8 2.7757 no . .
C3 H9 3.2075 no . .
C3 H10 3.1860 no . .
C3 H16 3.3487 no . .
C4 H11 3.2365 no . .
C4 H16 2.6508 no . .
C5 H6 3.5317 no . .
C5 H9 3.5670 no . .
C5 H13 3.2384 no . .
C5 H15 3.2271 no . .
C6 H7 3.1010 no . .
C7 H6 3.1066 no . .
C8 H11 2.9634 no . .
C9 H10 3.0862 no . .
C9 H16 2.9562 no . .
C10 H9 3.0876 no . .
C11 H8 2.9627 no . .
C12 H6 3.5186 no . .
C12 H14 3.2182 no . .
C12 H16 3.2270 no . .
C13 H15 3.2090 no . .
C14 H12 3.2162 no . .
C14 H16 3.2120 no . .
C15 H13 3.2112 no . .
C16 H9 3.5286 no . .
C16 H12 3.2252 no . .
C16 H14 3.2126 no . .
H6 H12 3.1688 no . .
H7 H8 2.2732 no . .
H8 H11 2.5036 no . .
H9 H16 3.0546 no . .
H10 H11 2.2788 no . .
H12 H13 2.3086 no . .
H13 H14 2.3066 no . .
H14 H15 2.2819 no . .
H15 H16 2.2982 no . .
P1 H6 3.2243 no . 3_676
P1 H7 3.4589 no . 4_564
P1 H13 3.2933 no . 4_574
N1 H7 3.4537 no . 3_666
N1 H12 2.8713 no . 2_646
N1 H13 2.7934 no . 2_646
N2 H8 3.4059 no . 4_564
N2 H9 3.5981 no . 3_776
N2 H14 3.5366 no . 1_554
N2 H15 3.5444 no . 1_554
N2 H15 3.3793 no . 3_776
N2 H16 2.6969 no . 3_776
C1 H12 3.5786 no . 3_676
C2 H11 3.5555 no . 4_565
C4 H7 3.4129 no . 4_564
C5 H8 3.0220 no . 4_565
C5 H11 3.5141 no . 4_565
C5 H13 3.2260 no . 4_574
C5 H14 3.1475 no . 4_574
C6 H12 3.2359 no . 3_676
C6 H13 3.1814 no . 2_646
C7 H7 3.3686 no . 3_666
C8 H6 3.4784 no . 4_564
C9 H8 3.4869 no . 4_564
C9 H14 3.2891 no . 1_554
C10 H8 3.5663 no . 4_564
C10 H14 3.5156 no . 2_746
C10 H15 3.4031 no . 2_746
C10 H15 3.3704 no . 3_776
C10 H16 3.1048 no . 3_776
C11 H10 3.5300 no . 4_565
C11 H15 3.2112 no . 2_746
C11 H16 3.4840 no . 4_564
C12 H7 3.5412 no . 4_565
C12 H8 3.0068 no . 4_565
C12 H13 3.1878 no . 4_574
C12 H14 3.5454 no . 4_574
C13 H7 3.1905 no . 4_565
C13 H8 2.9754 no . 4_565
C13 H9 3.4754 no . 4_575
C14 H8 2.9697 no . 4_565
C14 H9 3.3449 no . 1_556
C14 H9 3.0747 no . 4_575
C14 H10 3.4674 no . 2_756
C15 H8 2.9949 no . 4_565
C15 H9 3.4115 no . 4_575
C15 H10 3.0687 no . 3_776
C15 H11 3.2880 no . 4_565
C15 H14 3.4509 no . 4_574
C16 H8 3.0187 no . 4_565
C16 H10 3.0666 no . 3_776
C16 H11 2.8631 no . 4_565
C16 H14 3.0863 no . 4_574
H6 P1 3.2243 no . 3_676
H6 C8 3.4784 no . 4_565
H6 H12 3.5350 no . 2_646
H6 H12 3.1103 no . 3_676
H6 H13 2.9593 no . 2_646
H7 P1 3.4589 no . 4_565
H7 N1 3.4537 no . 3_666
H7 C4 3.4129 no . 4_565
H7 C7 3.3686 no . 3_666
H7 C12 3.5412 no . 4_564
H7 C13 3.1905 no . 4_564
H7 H7 2.9271 no . 3_666
H7 H13 3.0607 no . 4_564
H8 N2 3.4059 no . 4_565
H8 C5 3.0220 no . 4_564
H8 C9 3.4869 no . 4_565
H8 C10 3.5663 no . 4_565
H8 C12 3.0068 no . 4_564
H8 C13 2.9754 no . 4_564
H8 C14 2.9697 no . 4_564
H8 C15 2.9949 no . 4_564
H8 C16 3.0187 no . 4_564
H8 H12 3.5450 no . 4_564
H8 H13 3.4860 no . 4_564
H8 H14 3.4805 no . 4_564
H8 H15 3.5231 no . 4_564
H8 H16 3.5528 no . 4_564
H9 N2 3.5981 no . 3_776
H9 C13 3.4754 no . 4_574
H9 C14 3.3449 no . 1_554
H9 C14 3.0747 no . 4_574
H9 C15 3.4115 no . 4_574
H9 H14 2.7252 no . 1_554
H9 H14 3.0964 no . 4_574
H10 C11 3.5300 no . 4_564
H10 C14 3.4674 no . 2_746
H10 C15 3.0687 no . 3_776
H10 C16 3.0666 no . 3_776
H10 H11 3.4463 no . 4_564
H10 H14 2.7982 no . 2_746
H10 H15 3.0839 no . 2_746
H10 H15 2.7680 no . 3_776
H10 H16 2.7727 no . 3_776
H11 C2 3.5555 no . 4_564
H11 C5 3.5141 no . 4_564
H11 C15 3.2880 no . 4_564
H11 C16 2.8631 no . 4_564
H11 H10 3.4463 no . 4_565
H11 H15 2.7477 no . 2_746
H11 H15 3.3864 no . 4_564
H11 H16 2.6608 no . 4_564
H12 N1 2.8713 no . 2_656
H12 C1 3.5786 no . 3_676
H12 C6 3.2359 no . 3_676
H12 H6 3.5350 no . 2_656
H12 H6 3.1103 no . 3_676
H12 H8 3.5450 no . 4_565
H12 H13 3.0723 no . 4_574
H13 P1 3.2933 no . 4_575
H13 N1 2.7934 no . 2_656
H13 C5 3.2260 no . 4_575
H13 C6 3.1814 no . 2_656
H13 C12 3.1878 no . 4_575
H13 H6 2.9593 no . 2_656
H13 H7 3.0607 no . 4_565
H13 H8 3.4860 no . 4_565
H13 H12 3.0723 no . 4_575
H14 N2 3.5366 no . 1_556
H14 C5 3.1475 no . 4_575
H14 C9 3.2891 no . 1_556
H14 C10 3.5156 no . 2_756
H14 C12 3.5454 no . 4_575
H14 C15 3.4509 no . 4_575
H14 C16 3.0863 no . 4_575
H14 H8 3.4805 no . 4_565
H14 H9 2.7252 no . 1_556
H14 H9 3.0964 no . 4_575
H14 H10 2.7982 no . 2_756
H14 H16 3.3294 no . 4_575
H15 N2 3.5444 no . 1_556
H15 N2 3.3793 no . 3_776
H15 C10 3.4031 no . 2_756
H15 C10 3.3704 no . 3_776
H15 C11 3.2112 no . 2_756
H15 H8 3.5231 no . 4_565
H15 H10 3.0839 no . 2_756
H15 H10 2.7680 no . 3_776
H15 H11 2.7477 no . 2_756
H15 H11 3.3864 no . 4_565
H15 H15 2.9908 no . 3_777
H16 N2 2.6969 no . 3_776
H16 C10 3.1048 no . 3_776
H16 C11 3.4840 no . 4_565
H16 H8 3.5528 no . 4_565
H16 H10 2.7727 no . 3_776
H16 H11 2.6608 no . 4_565
H16 H14 3.3294 no . 4_574

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_DPA_1
_database_code_depnum_ccdc_archive 'CCDC 1994425'
loop_
_audit_author_name
_audit_author_address
'Hiroaki Imoto'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 As N2'
_chemical_formula_moiety         'C16 H11 As N2'
_chemical_formula_weight         306.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.672(9)
_cell_length_b                   11.334(8)
_cell_length_c                   8.756(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.051(9)
_cell_angle_gamma                90.0000
_cell_volume                     1316.2(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2808
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    2.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.598

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            13572
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3012
_reflns_number_gt                2282
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0769
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0325P)²+0.3521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
As As 0.0499 2.0058
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.66821(2) 0.50025(2) 0.48515(3) 0.04555(11) Uani 1 4 d . . .
N1 N 0.92755(19) 0.5524(3) 0.3088(3) 0.0637(7) Uani 1 4 d . . .
N2 N 0.55628(18) 0.8251(2) 0.6171(3) 0.0587(6) Uani 1 4 d . . .
C1 C 0.7851(2) 0.5614(2) 0.4219(3) 0.0443(6) Uani 1 4 d . . .
C2 C 0.79109(18) 0.6846(2) 0.4294(3) 0.0405(5) Uani 1 4 d . . .
C3 C 0.71257(17) 0.7410(2) 0.4928(3) 0.0385(5) Uani 1 4 d . . .
C4 C 0.64655(18) 0.6628(2) 0.5395(3) 0.0404(5) Uani 1 4 d . . .
C5 C 0.73031(19) 0.4338(2) 0.6917(3) 0.0398(5) Uani 1 4 d . . .
C6 C 0.8549(2) 0.5007(3) 0.3610(4) 0.0549(7) Uani 1 4 d . . .
C7 C 0.9319(2) 0.6697(3) 0.3175(4) 0.0606(8) Uani 1 4 d . . .
C8 C 0.86677(19) 0.7394(3) 0.3756(3) 0.0501(6) Uani 1 4 d . . .
C9 C 0.5709(2) 0.7096(3) 0.6013(3) 0.0534(7) Uani 1 4 d . . .
C10 C 0.6192(2) 0.8975(3) 0.5685(3) 0.0552(7) Uani 1 4 d . . .
C11 C 0.6981(2) 0.8610(2) 0.5079(3) 0.0463(6) Uani 1 4 d . . .
C12 C 0.8331(2) 0.4384(2) 0.7611(3) 0.0448(6) Uani 1 4 d . . .
C13 C 0.8707(2) 0.3869(3) 0.9073(4) 0.0555(7) Uani 1 4 d . . .
C14 C 0.8062(3) 0.3307(3) 0.9829(4) 0.0587(8) Uani 1 4 d . . .
C15 C 0.7050(2) 0.3264(2) 0.9151(4) 0.0569(7) Uani 1 4 d . . .
C16 C 0.6670(2) 0.3772(2) 0.7695(3) 0.0484(6) Uani 1 4 d . . .
H6 H 0.85057 0.41881 0.35649 0.0659 Uiso 1 4 calc R . .
H7 H 0.98259 0.70728 0.28181 0.0727 Uiso 1 4 calc R . .
H8 H 0.87344 0.82107 0.37856 0.0602 Uiso 1 4 calc R . .
H9 H 0.52754 0.65735 0.63386 0.0640 Uiso 1 4 calc R . .
H10 H 0.60916 0.97823 0.57586 0.0662 Uiso 1 4 calc R . .
H11 H 0.7407 0.91552 0.47791 0.0556 Uiso 1 4 calc R . .
H12 H 0.87657 0.47585 0.70973 0.0538 Uiso 1 4 calc R . .
H13 H 0.93932 0.39032 0.95446 0.0666 Uiso 1 4 calc R . .
H14 H 0.83174 0.29562 1.08048 0.0704 Uiso 1 4 calc R . .
H15 H 0.66182 0.28929 0.96718 0.0683 Uiso 1 4 calc R . .
H16 H 0.59818 0.37326 0.72334 0.0581 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
As1 C1 1.942(3) yes . .
As1 C4 1.944(3) yes . .
As1 C5 1.953(3) yes . .
N1 C6 1.327(5) yes . .
N1 C7 1.333(5) yes . .
N2 C9 1.337(4) yes . .
N2 C10 1.332(4) yes . .
C1 C2 1.399(4) yes . .
C1 C6 1.384(4) yes . .
C2 C3 1.469(4) yes . .
C2 C8 1.384(4) yes . .
C3 C4 1.395(4) yes . .
C3 C11 1.385(4) yes . .
C4 C9 1.384(4) yes . .
C5 C12 1.391(4) yes . .
C5 C16 1.383(4) yes . .
C7 C8 1.376(4) yes . .
C10 C11 1.376(4) yes . .
C12 C13 1.387(4) yes . .
C13 C14 1.379(5) yes . .
C14 C15 1.368(4) yes . .
C15 C16 1.380(4) yes . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 As1 C4 85.20(11) yes . . .
C1 As1 C5 101.48(11) yes . . .
C4 As1 C5 101.35(10) yes . . .
C6 N1 C7 116.6(3) yes . . .
C9 N2 C10 116.5(3) yes . . .
As1 C1 C2 112.7(2) yes . . .
As1 C1 C6 128.6(2) yes . . .
C2 C1 C6 118.5(3) yes . . .
C1 C2 C3 114.3(2) yes . . .
C1 C2 C8 118.2(3) yes . . .
C3 C2 C8 127.5(2) yes . . .
C2 C3 C4 114.7(2) yes . . .
C2 C3 C11 126.7(2) yes . . .
C4 C3 C11 118.5(2) yes . . .
As1 C4 C3 112.48(19) yes . . .
As1 C4 C9 129.2(2) yes . . .
C3 C4 C9 118.0(2) yes . . .
As1 C5 C12 123.8(2) yes . . .
As1 C5 C16 116.85(18) yes . . .
C12 C5 C16 119.3(2) yes . . .
N1 C6 C1 123.9(3) yes . . .
N1 C7 C8 124.8(3) yes . . .
C2 C8 C7 118.2(3) yes . . .
N2 C9 C4 124.1(3) yes . . .
N2 C10 C11 124.5(3) yes . . .
C3 C11 C10 118.4(3) yes . . .
C5 C12 C13 119.7(3) yes . . .
C12 C13 C14 120.1(3) yes . . .
C13 C14 C15 120.3(3) yes . . .
C14 C15 C16 120.1(3) yes . . .
C5 C16 C15 120.5(3) yes . . .
N1 C6 H6 118.055 no . . .
C1 C6 H6 118.073 no . . .
N1 C7 H7 117.623 no . . .
C8 C7 H7 117.620 no . . .
C2 C8 H8 120.904 no . . .
C7 C8 H8 120.902 no . . .
N2 C9 H9 117.962 no . . .
C4 C9 H9 117.960 no . . .
N2 C10 H10 117.766 no . . .
C11 C10 H10 117.776 no . . .
C3 C11 H11 120.798 no . . .
C10 C11 H11 120.796 no . . .
C5 C12 H12 120.139 no . . .
C13 C12 H12 120.132 no . . .
C12 C13 H13 119.965 no . . .
C14 C13 H13 119.964 no . . .
C13 C14 H14 119.851 no . . .
C15 C14 H14 119.844 no . . .
C14 C15 H15 119.959 no . . .
C16 C15 H15 119.964 no . . .
C5 C16 H16 119.751 no . . .
C15 C16 H16 119.756 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 As1 C4 C3 6.87(14) no . . . .
C1 As1 C4 C9 179.88(19) no . . . .
C4 As1 C1 C2 -5.90(14) no . . . .
C4 As1 C1 C6 179.71(19) no . . . .
C1 As1 C5 C12 1.2(2) no . . . .
C1 As1 C5 C16 -177.46(16) no . . . .
C5 As1 C1 C2 -106.53(15) no . . . .
C5 As1 C1 C6 79.1(2) no . . . .
C4 As1 C5 C12 -86.17(19) no . . . .
C4 As1 C5 C16 95.20(17) no . . . .
C5 As1 C4 C3 107.64(15) no . . . .
C5 As1 C4 C9 -79.35(19) no . . . .
C6 N1 C7 C8 -0.3(4) no . . . .
C7 N1 C6 C1 0.3(4) no . . . .
C9 N2 C10 C11 -1.7(4) no . . . .
C10 N2 C9 C4 0.4(4) no . . . .
As1 C1 C2 C3 3.8(2) no . . . .
As1 C1 C2 C8 -175.07(13) no . . . .
As1 C1 C6 N1 174.00(16) no . . . .
C2 C1 C6 N1 -0.1(4) no . . . .
C6 C1 C2 C3 178.84(19) no . . . .
C6 C1 C2 C8 -0.0(3) no . . . .
C1 C2 C3 C4 1.8(3) no . . . .
C1 C2 C3 C11 -177.39(18) no . . . .
C1 C2 C8 C7 0.0(3) no . . . .
C3 C2 C8 C7 -178.68(19) no . . . .
C8 C2 C3 C4 -179.4(2) no . . . .
C8 C2 C3 C11 1.4(4) no . . . .
C2 C3 C4 As1 -6.5(2) no . . . .
C2 C3 C4 C9 179.63(16) no . . . .
C2 C3 C11 C10 179.17(18) no . . . .
C4 C3 C11 C10 0.0(3) no . . . .
C11 C3 C4 As1 172.74(16) no . . . .
C11 C3 C4 C9 -1.1(3) no . . . .
As1 C4 C9 N2 -171.75(15) no . . . .
C3 C4 C9 N2 0.9(3) no . . . .
As1 C5 C12 C13 -178.93(15) no . . . .
As1 C5 C16 C15 179.16(16) no . . . .
C12 C5 C16 C15 0.5(4) no . . . .
C16 C5 C12 C13 -0.3(4) no . . . .
N1 C7 C8 C2 0.1(4) no . . . .
N2 C10 C11 C3 1.5(4) no . . . .
C5 C12 C13 C14 0.4(4) no . . . .
C12 C13 C14 C15 -0.7(4) no . . . .
C13 C14 C15 C16 0.8(4) no . . . .
C14 C15 C16 C5 -0.7(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C2 2.793(4) no . .
N2 C3 2.791(4) no . .
C1 C7 2.695(5) no . .
C1 C12 3.202(4) no . .
C4 C10 2.706(4) no . .
C5 C14 2.768(4) no . .
C6 C8 2.711(4) no . .
C8 C11 3.139(4) no . .
C9 C11 2.707(4) no . .
C12 C15 2.764(5) no . .
C13 C16 2.756(4) no . .
N1 C12 3.473(5) no . 3_766
N2 C3 3.540(4) no . 4_565
N2 C15 3.515(5) no . 2_656
N2 C16 3.481(5) no . 2_656
C1 C10 3.395(4) no . 4_564
C2 C10 3.574(4) no . 4_564
C3 N2 3.540(4) no . 4_564
C3 C8 3.507(4) no . 4_565
C3 C9 3.549(4) no . 4_564
C8 C3 3.507(4) no . 4_564
C9 C3 3.549(4) no . 4_565
C10 C1 3.395(4) no . 4_565
C10 C2 3.574(4) no . 4_565
C11 C16 3.594(4) no . 4_564
C12 N1 3.473(5) no . 3_766
C15 N2 3.515(5) no . 2_646
C16 N2 3.481(5) no . 2_646
C16 C11 3.594(4) no . 4_565
As1 H6 3.1146 no . .
As1 H9 3.1274 no . .
As1 H12 3.0558 no . .
As1 H16 2.8823 no . .
N1 H8 3.2273 no . .
N2 H11 3.2228 no . .
C1 H8 3.2381 no . .
C1 H12 2.7068 no . .
C2 H6 3.2240 no . .
C2 H7 3.1992 no . .
C2 H11 2.7654 no . .
C2 H12 3.4049 no . .
C3 H8 2.7803 no . .
C3 H9 3.2156 no . .
C3 H10 3.2025 no . .
C4 H11 3.2384 no . .
C5 H13 3.2419 no . .
C5 H15 3.2365 no . .
C6 H7 3.0986 no . .
C6 H12 3.0083 no . .
C7 H6 3.1022 no . .
C8 H11 2.9168 no . .
C9 H10 3.1067 no . .
C10 H9 3.1072 no . .
C11 H8 2.9244 no . .
C12 H14 3.2349 no . .
C12 H16 3.2337 no . .
C13 H15 3.2214 no . .
C14 H12 3.2355 no . .
C14 H16 3.2172 no . .
C15 H13 3.2198 no . .
C16 H12 3.2351 no . .
C16 H14 3.2197 no . .
H6 H12 3.0947 no . .
H7 H8 2.2851 no . .
H8 H11 2.4419 no . .
H9 H16 3.3979 no . .
H10 H11 2.2856 no . .
H12 H13 2.3184 no . .
H13 H14 2.3067 no . .
H14 H15 2.2950 no . .
H15 H16 2.3064 no . .
As1 H9 3.1756 no . 3_666
As1 H10 3.4857 no . 4_564
As1 H15 3.2854 no . 4_554
N1 H11 3.3849 no . 4_564
N1 H12 2.7406 no . 3_766
N1 H13 3.3293 no . 3_766
N1 H14 3.5925 no . 1_554
N2 H10 3.3293 no . 3_676
N2 H15 2.9210 no . 2_656
N2 H16 2.8532 no . 2_656
C1 H10 3.4100 no . 4_564
C4 H16 3.5945 no . 3_666
C5 H8 3.5598 no . 4_565
C5 H11 3.0078 no . 4_565
C5 H14 3.2071 no . 4_554
C5 H15 3.1997 no . 4_554
C6 H11 3.4712 no . 4_564
C6 H14 3.3404 no . 1_554
C7 H11 3.5825 no . 4_564
C7 H12 3.1529 no . 3_766
C7 H13 3.4103 no . 2_756
C7 H13 3.3574 no . 3_766
C7 H14 3.4462 no . 2_756
C8 H7 3.5762 no . 4_565
C8 H12 3.5549 no . 4_564
C8 H13 3.2021 no . 2_756
C9 H15 3.2208 no . 2_656
C9 H16 3.5870 no . 2_656
C9 H16 3.3340 no . 3_666
C10 H10 3.3785 no . 3_676
C11 H9 3.5357 no . 4_564
C12 H7 3.1104 no . 3_766
C12 H8 2.9184 no . 4_565
C12 H11 3.0176 no . 4_565
C12 H14 3.0858 no . 4_554
C13 H6 3.4959 no . 4_555
C13 H7 3.5956 no . 2_746
C13 H7 3.0858 no . 3_766
C13 H8 3.3199 no . 4_565
C13 H11 3.0140 no . 4_565
C13 H14 3.4662 no . 4_554
C14 H6 3.3317 no . 1_556
C14 H6 3.1493 no . 4_555
C14 H7 3.4130 no . 2_746
C14 H11 3.0093 no . 4_565
C15 H6 3.5277 no . 4_555
C15 H10 3.0815 no . 4_565
C15 H11 2.9938 no . 4_565
C16 H10 3.3965 no . 4_565
C16 H11 2.9957 no . 4_565
C16 H15 3.2373 no . 4_554
H6 C13 3.4959 no . 4_554
H6 C14 3.3317 no . 1_554
H6 C14 3.1493 no . 4_554
H6 C15 3.5277 no . 4_554
H6 H14 2.7485 no . 1_554
H6 H14 3.1724 no . 4_554
H7 C8 3.5762 no . 4_564
H7 C12 3.1104 no . 3_766
H7 C13 3.5956 no . 2_756
H7 C13 3.0858 no . 3_766
H7 C14 3.4130 no . 2_756
H7 H8 3.4984 no . 4_564
H7 H12 2.8199 no . 3_766
H7 H13 3.0950 no . 2_756
H7 H13 2.7777 no . 3_766
H7 H14 2.7228 no . 2_756
H8 C5 3.5598 no . 4_564
H8 C12 2.9184 no . 4_564
H8 C13 3.3199 no . 4_564
H8 H7 3.4984 no . 4_565
H8 H12 2.7414 no . 4_564
H8 H13 2.7367 no . 2_756
H8 H13 3.4149 no . 4_564
H9 As1 3.1756 no . 3_666
H9 C11 3.5357 no . 4_565
H9 H15 2.9341 no . 2_656
H9 H16 3.3984 no . 2_656
H9 H16 3.2010 no . 3_666
H10 As1 3.4857 no . 4_565
H10 N2 3.3293 no . 3_676
H10 C1 3.4100 no . 4_565
H10 C10 3.3785 no . 3_676
H10 C15 3.0815 no . 4_564
H10 C16 3.3965 no . 4_564
H10 H10 2.9987 no . 3_676
H10 H15 2.9494 no . 4_564
H10 H16 3.4869 no . 4_564
H11 N1 3.3849 no . 4_565
H11 C5 3.0078 no . 4_564
H11 C6 3.4712 no . 4_565
H11 C7 3.5825 no . 4_565
H11 C12 3.0176 no . 4_564
H11 C13 3.0140 no . 4_564
H11 C14 3.0093 no . 4_564
H11 C15 2.9938 no . 4_564
H11 C16 2.9957 no . 4_564
H11 H12 3.5494 no . 4_564
H11 H13 3.5396 no . 4_564
H11 H14 3.5399 no . 4_564
H11 H15 3.5093 no . 4_564
H11 H16 3.5195 no . 4_564
H12 N1 2.7406 no . 3_766
H12 C7 3.1529 no . 3_766
H12 C8 3.5549 no . 4_565
H12 H7 2.8199 no . 3_766
H12 H8 2.7414 no . 4_565
H12 H11 3.5494 no . 4_565
H12 H14 3.2842 no . 4_554
H13 N1 3.3293 no . 3_766
H13 C7 3.4103 no . 2_746
H13 C7 3.3574 no . 3_766
H13 C8 3.2021 no . 2_746
H13 H7 3.0950 no . 2_746
H13 H7 2.7777 no . 3_766
H13 H8 2.7367 no . 2_746
H13 H8 3.4149 no . 4_565
H13 H11 3.5396 no . 4_565
H13 H13 2.9878 no . 3_767
H14 N1 3.5925 no . 1_556
H14 C5 3.2071 no . 4_555
H14 C6 3.3404 no . 1_556
H14 C7 3.4462 no . 2_746
H14 C12 3.0858 no . 4_555
H14 C13 3.4662 no . 4_555
H14 H6 2.7485 no . 1_556
H14 H6 3.1724 no . 4_555
H14 H7 2.7228 no . 2_746
H14 H11 3.5399 no . 4_565
H14 H12 3.2842 no . 4_555
H15 As1 3.2854 no . 4_555
H15 N2 2.9210 no . 2_646
H15 C5 3.1997 no . 4_555
H15 C9 3.2208 no . 2_646
H15 C16 3.2373 no . 4_555
H15 H9 2.9341 no . 2_646
H15 H10 2.9494 no . 4_565
H15 H11 3.5093 no . 4_565
H15 H16 3.1827 no . 4_555
H16 N2 2.8532 no . 2_646
H16 C4 3.5945 no . 3_666
H16 C9 3.5870 no . 2_646
H16 C9 3.3340 no . 3_666
H16 H9 3.3984 no . 2_646
H16 H9 3.2010 no . 3_666
H16 H10 3.4869 no . 4_565
H16 H11 3.5195 no . 4_565
H16 H15 3.1827 no . 4_554

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_DPP-Ox_6
_database_code_depnum_ccdc_archive 'CCDC 1994423'
loop_
_audit_author_name
_audit_author_address
'Hiroaki Imoto'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H11 N2 O P'
_chemical_formula_moiety         'C16 H11 N2 O P'
_chemical_formula_weight         278.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.692(4)
_cell_length_b                   9.588(6)
_cell_length_c                   10.081(7)
_cell_angle_alpha                88.33(2)
_cell_angle_beta                 72.47(2)
_cell_angle_gamma                67.903(14)
_cell_volume                     653.9(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1666
_cell_measurement_theta_min      7.74
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288.00
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.970

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            6758
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         7.705
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2925
_reflns_number_gt                2415
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1027
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2925
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0577P)²+0.1418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.46952(6) 0.86344(4) 0.71304(4) 0.03533(15) Uani 1 2 d . . .
O1 O 0.65358(17) 0.86523(15) 0.61198(13) 0.0500(3) Uani 1 2 d . . .
N1 N 0.5925(2) 0.63042(17) 1.04677(17) 0.0504(4) Uani 1 2 d . . .
N2 N 0.0441(2) 1.29822(16) 0.81225(18) 0.0506(4) Uani 1 2 d . . .
C1 C 0.4807(2) 0.79706(17) 0.88150(16) 0.0371(3) Uani 1 2 d . . .
C2 C 0.3432(2) 0.90728(17) 0.99047(17) 0.0356(3) Uani 1 2 d . . .
C3 C 0.2269(2) 1.04821(17) 0.94119(17) 0.0356(3) Uani 1 2 d . . .
C4 C 0.2789(2) 1.04410(17) 0.79489(17) 0.0352(3) Uani 1 2 d . . .
C5 C 0.3484(2) 0.76750(17) 0.64608(16) 0.0360(3) Uani 1 2 d . . .
C6 C 0.6024(3) 0.66118(19) 0.91507(19) 0.0459(4) Uani 1 2 d . . .
C7 C 0.4606(3) 0.7374(2) 1.1480(2) 0.0506(4) Uani 1 2 d . . .
C8 C 0.3333(3) 0.8769(2) 1.12735(18) 0.0444(4) Uani 1 2 d . . .
C9 C 0.1852(3) 1.17213(18) 0.73527(19) 0.0429(4) Uani 1 2 d . . .
C10 C -0.0044(3) 1.29833(19) 0.9516(2) 0.0518(5) Uani 1 2 d . . .
C11 C 0.0824(3) 1.17753(19) 1.02117(19) 0.0450(4) Uani 1 2 d . . .
C12 C 0.3395(3) 0.6311(2) 0.6902(2) 0.0507(4) Uani 1 2 d . . .
C13 C 0.2361(4) 0.5662(3) 0.6391(3) 0.0676(6) Uani 1 2 d . . .
C14 C 0.1425(4) 0.6357(3) 0.5449(3) 0.0688(6) Uani 1 2 d . . .
C15 C 0.1515(3) 0.7704(3) 0.4992(3) 0.0622(5) Uani 1 2 d . . .
C16 C 0.2550(3) 0.8355(2) 0.5483(2) 0.0493(4) Uani 1 2 d . . .
H6 H 0.69466 0.58861 0.8428 0.0551 Uiso 1 2 calc R . .
H7 H 0.45373 0.71658 1.23968 0.0607 Uiso 1 2 calc R . .
H8 H 0.2446 0.94753 1.2022 0.0533 Uiso 1 2 calc R . .
H9 H 0.22177 1.17017 0.63839 0.0515 Uiso 1 2 calc R . .
H10 H -0.10284 1.38514 1.00543 0.0622 Uiso 1 2 calc R . .
H11 H 0.04433 1.18362 1.11826 0.0541 Uiso 1 2 calc R . .
H12 H 0.40284 0.58327 0.75401 0.0608 Uiso 1 2 calc R . .
H13 H 0.23023 0.47492 0.66901 0.0811 Uiso 1 2 calc R . .
H14 H 0.07261 0.59172 0.51168 0.0825 Uiso 1 2 calc R . .
H15 H 0.08785 0.81727 0.43524 0.0746 Uiso 1 2 calc R . .
H16 H 0.26267 0.92554 0.51602 0.0591 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
P1 O1 1.4801(15) yes . .
P1 C1 1.811(2) yes . .
P1 C4 1.8096(16) yes . .
P1 C5 1.797(2) yes . .
N1 C6 1.337(3) yes . .
N1 C7 1.333(2) yes . .
N2 C9 1.342(2) yes . .
N2 C10 1.341(3) yes . .
C1 C2 1.403(2) yes . .
C1 C6 1.391(2) yes . .
C2 C3 1.481(2) yes . .
C2 C8 1.387(3) yes . .
C3 C4 1.405(3) yes . .
C3 C11 1.380(2) yes . .
C4 C9 1.393(2) yes . .
C5 C12 1.389(3) yes . .
C5 C16 1.397(3) yes . .
C7 C8 1.383(3) yes . .
C10 C11 1.390(3) yes . .
C12 C13 1.387(4) yes . .
C13 C14 1.371(4) yes . .
C14 C15 1.378(4) yes . .
C15 C16 1.377(4) yes . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 P1 C1 117.54(9) yes . . .
O1 P1 C4 117.15(9) yes . . .
O1 P1 C5 114.85(9) yes . . .
C1 P1 C4 91.38(8) yes . . .
C1 P1 C5 107.43(9) yes . . .
C4 P1 C5 105.60(9) yes . . .
C6 N1 C7 117.19(16) yes . . .
C9 N2 C10 117.45(16) yes . . .
P1 C1 C2 110.94(12) yes . . .
P1 C1 C6 130.46(12) yes . . .
C2 C1 C6 118.59(16) yes . . .
C1 C2 C3 113.41(15) yes . . .
C1 C2 C8 118.97(14) yes . . .
C3 C2 C8 127.59(13) yes . . .
C2 C3 C4 113.17(12) yes . . .
C2 C3 C11 127.72(16) yes . . .
C4 C3 C11 119.10(15) yes . . .
P1 C4 C3 111.08(11) yes . . .
P1 C4 C9 130.18(13) yes . . .
C3 C4 C9 118.74(13) yes . . .
P1 C5 C12 122.80(16) yes . . .
P1 C5 C16 118.35(15) yes . . .
C12 C5 C16 118.8(2) yes . . .
N1 C6 C1 122.83(14) yes . . .
N1 C7 C8 125.14(19) yes . . .
C2 C8 C7 117.28(14) yes . . .
N2 C9 C4 122.54(17) yes . . .
N2 C10 C11 124.44(14) yes . . .
C3 C11 C10 117.71(17) yes . . .
C5 C12 C13 120.0(2) yes . . .
C12 C13 C14 120.5(2) yes . . .
C13 C14 C15 120.2(3) yes . . .
C14 C15 C16 119.9(2) yes . . .
C5 C16 C15 120.6(2) yes . . .
N1 C6 H6 118.584 no . . .
C1 C6 H6 118.584 no . . .
N1 C7 H7 117.428 no . . .
C8 C7 H7 117.430 no . . .
C2 C8 H8 121.366 no . . .
C7 C8 H8 121.359 no . . .
N2 C9 H9 118.731 no . . .
C4 C9 H9 118.729 no . . .
N2 C10 H10 117.774 no . . .
C11 C10 H10 117.785 no . . .
C3 C11 H11 121.141 no . . .
C10 C11 H11 121.146 no . . .
C5 C12 H12 120.013 no . . .
C13 C12 H12 119.997 no . . .
C12 C13 H13 119.774 no . . .
C14 C13 H13 119.773 no . . .
C13 C14 H14 119.895 no . . .
C15 C14 H14 119.898 no . . .
C14 C15 H15 120.028 no . . .
C16 C15 H15 120.038 no . . .
C5 C16 H16 119.713 no . . .
C15 C16 H16 119.717 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 P1 C1 C2 123.01(12) no . . . .
O1 P1 C1 C6 -55.6(2) no . . . .
O1 P1 C4 C3 -123.69(12) no . . . .
O1 P1 C4 C9 55.3(2) no . . . .
O1 P1 C5 C12 110.62(11) no . . . .
O1 P1 C5 C16 -71.15(11) no . . . .
C1 P1 C4 C3 -1.54(13) no . . . .
C1 P1 C4 C9 177.50(18) no . . . .
C4 P1 C1 C2 1.18(14) no . . . .
C4 P1 C1 C6 -177.47(18) no . . . .
C1 P1 C5 C12 -22.19(11) no . . . .
C1 P1 C5 C16 156.04(8) no . . . .
C5 P1 C1 C2 -105.65(13) no . . . .
C5 P1 C1 C6 75.70(19) no . . . .
C4 P1 C5 C12 -118.73(11) no . . . .
C4 P1 C5 C16 59.51(11) no . . . .
C5 P1 C4 C3 106.99(13) no . . . .
C5 P1 C4 C9 -73.97(18) no . . . .
C6 N1 C7 C8 0.3(4) no . . . .
C7 N1 C6 C1 -0.9(3) no . . . .
C9 N2 C10 C11 0.5(3) no . . . .
C10 N2 C9 C4 0.6(3) no . . . .
P1 C1 C2 C3 -0.5(2) no . . . .
P1 C1 C2 C8 -178.91(12) no . . . .
P1 C1 C6 N1 179.33(15) no . . . .
C2 C1 C6 N1 0.8(3) no . . . .
C6 C1 C2 C3 178.28(17) no . . . .
C6 C1 C2 C8 -0.1(3) no . . . .
C1 C2 C3 C4 -0.6(2) no . . . .
C1 C2 C3 C11 -179.37(17) no . . . .
C1 C2 C8 C7 -0.4(3) no . . . .
C3 C2 C8 C7 -178.54(18) no . . . .
C8 C2 C3 C4 177.56(19) no . . . .
C8 C2 C3 C11 -1.2(3) no . . . .
C2 C3 C4 P1 1.5(2) no . . . .
C2 C3 C4 C9 -177.65(16) no . . . .
C2 C3 C11 C10 178.45(18) no . . . .
C4 C3 C11 C10 -0.2(3) no . . . .
C11 C3 C4 P1 -179.64(16) no . . . .
C11 C3 C4 C9 1.2(3) no . . . .
P1 C4 C9 N2 179.60(14) no . . . .
C3 C4 C9 N2 -1.4(3) no . . . .
P1 C5 C12 C13 177.08(9) no . . . .
P1 C5 C16 C15 -176.66(9) no . . . .
C12 C5 C16 C15 1.6(2) no . . . .
C16 C5 C12 C13 -1.2(2) no . . . .
N1 C7 C8 C2 0.4(4) no . . . .
N2 C10 C11 C3 -0.7(3) no . . . .
C5 C12 C13 C14 0.1(3) no . . . .
C12 C13 C14 C15 0.5(3) no . . . .
C13 C14 C15 C16 0.0(3) no . . . .
C14 C15 C16 C5 -1.1(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C6 3.581(3) no . .
O1 C9 3.567(2) no . .
O1 C16 3.428(3) no . .
N1 C2 2.790(3) no . .
N2 C3 2.792(3) no . .
C1 C7 2.701(3) no . .
C1 C12 3.190(3) no . .
C4 C10 2.710(2) no . .
C4 C16 3.325(3) no . .
C5 C14 2.776(4) no . .
C6 C8 2.741(3) no . .
C6 C12 3.543(4) no . .
C8 C11 3.171(3) no . .
C9 C11 2.746(3) no . .
C9 C16 3.564(4) no . .
C12 C15 2.767(4) no . .
C13 C16 2.755(4) no . .
O1 C9 3.323(3) no . 2_676
O1 C14 3.431(3) no . 1_655
O1 C15 3.407(3) no . 1_655
O1 C16 3.450(3) no . 2_676
N1 N1 3.576(3) no . 2_667
N1 C6 3.599(3) no . 2_667
N1 C10 3.410(3) no . 1_645
N1 C10 3.488(4) no . 2_677
N1 C11 3.532(3) no . 2_677
N2 C13 3.587(4) no . 1_565
C2 C2 3.541(3) no . 2_677
C3 C8 3.581(4) no . 2_677
C4 C7 3.558(4) no . 2_677
C6 N1 3.599(3) no . 2_667
C6 C11 3.536(4) no . 2_677
C7 C4 3.558(4) no . 2_677
C7 C15 3.566(4) no . 1_556
C8 C3 3.581(4) no . 2_677
C9 O1 3.323(3) no . 2_676
C10 N1 3.410(3) no . 1_465
C10 N1 3.488(4) no . 2_677
C11 N1 3.532(3) no . 2_677
C11 C6 3.536(4) no . 2_677
C11 C12 3.536(3) no . 2_577
C12 C11 3.536(3) no . 2_577
C13 N2 3.587(4) no . 1_545
C14 O1 3.431(3) no . 1_455
C15 O1 3.407(3) no . 1_455
C15 C7 3.566(4) no . 1_554
C16 O1 3.450(3) no . 2_676
P1 H6 3.0634 no . .
P1 H9 3.0604 no . .
P1 H12 2.9146 no . .
P1 H16 2.8200 no . .
O1 H6 3.4643 no . .
O1 H9 3.4435 no . .
O1 H16 3.2745 no . .
N1 H8 3.2389 no . .
N2 H11 3.2446 no . .
C1 H8 3.2549 no . .
C1 H12 2.7847 no . .
C2 H6 3.2382 no . .
C2 H7 3.1979 no . .
C2 H11 2.7924 no . .
C3 H8 2.8004 no . .
C3 H9 3.2429 no . .
C3 H10 3.2027 no . .
C4 H11 3.2506 no . .
C4 H16 3.1170 no . .
C5 H13 3.2411 no . .
C5 H15 3.2480 no . .
C6 H7 3.1125 no . .
C6 H12 2.8259 no . .
C7 H6 3.1188 no . .
C8 H11 2.9639 no . .
C9 H10 3.1275 no . .
C9 H16 3.0466 no . .
C10 H9 3.1330 no . .
C11 H8 2.9695 no . .
C12 H6 3.4136 no . .
C12 H14 3.2316 no . .
C12 H16 3.2380 no . .
C13 H15 3.2216 no . .
C14 H12 3.2300 no . .
C14 H16 3.2234 no . .
C15 H13 3.2211 no . .
C16 H9 3.2559 no . .
C16 H12 3.2410 no . .
C16 H14 3.2244 no . .
H6 H12 2.6723 no . .
H7 H8 2.2960 no . .
H8 H11 2.5027 no . .
H9 H16 2.5500 no . .
H10 H11 2.3045 no . .
H12 H13 2.3133 no . .
H13 H14 2.2962 no . .
H14 H15 2.3074 no . .
H15 H16 2.3039 no . .
P1 H9 3.5658 no . 2_676
O1 H8 3.0795 no . 2_677
O1 H9 2.3983 no . 2_676
O1 H14 3.1812 no . 1_655
O1 H15 3.1384 no . 1_655
O1 H16 2.5348 no . 2_676
N1 H6 3.5213 no . 2_667
N1 H10 2.5533 no . 1_645
N1 H12 2.8250 no . 2_667
N1 H13 3.4983 no . 2_667
N2 H6 2.9988 no . 1_465
N2 H13 2.7280 no . 1_565
N2 H15 3.3186 no . 2_576
C4 H7 3.5618 no . 2_677
C5 H11 3.1088 no . 2_577
C6 H10 3.0926 no . 1_645
C6 H11 3.4889 no . 2_677
C7 H12 3.0905 no . 2_667
C7 H13 3.4617 no . 2_667
C7 H15 3.2662 no . 1_556
C8 H15 3.2715 no . 1_556
C9 H7 3.4034 no . 2_677
C9 H13 3.0821 no . 1_565
C9 H15 3.0626 no . 2_576
C10 H6 3.2883 no . 1_465
C10 H10 3.5007 no . 2_587
C10 H12 3.4037 no . 2_577
C12 H7 3.2700 no . 2_667
C12 H10 3.0938 no . 2_577
C12 H11 2.9016 no . 2_577
C13 H7 3.3514 no . 2_667
C13 H10 3.4105 no . 2_577
C13 H11 3.1080 no . 2_577
C14 H7 3.5525 no . 1_554
C14 H11 3.4827 no . 2_577
C14 H14 3.3419 no . 2_566
C15 H7 2.8328 no . 1_554
C15 H8 3.4186 no . 1_554
C15 H9 3.4078 no . 2_576
C15 H16 3.4573 no . 2_576
C16 H7 3.0569 no . 1_554
C16 H11 3.5004 no . 2_577
C16 H15 3.3509 no . 2_576
H6 N1 3.5213 no . 2_667
H6 N2 2.9988 no . 1_645
H6 C10 3.2883 no . 1_645
H6 H10 2.8259 no . 1_645
H6 H11 3.5746 no . 2_677
H7 C4 3.5618 no . 2_677
H7 C9 3.4034 no . 2_677
H7 C12 3.2700 no . 2_667
H7 C13 3.3514 no . 2_667
H7 C14 3.5525 no . 1_556
H7 C15 2.8328 no . 1_556
H7 C16 3.0569 no . 1_556
H7 H9 3.5895 no . 2_677
H7 H12 2.6707 no . 2_667
H7 H13 2.8318 no . 2_667
H7 H15 2.7318 no . 1_556
H7 H16 3.0948 no . 1_556
H8 O1 3.0795 no . 2_677
H8 C15 3.4186 no . 1_556
H8 H15 2.7907 no . 1_556
H8 H16 3.2055 no . 1_556
H9 P1 3.5658 no . 2_676
H9 O1 2.3983 no . 2_676
H9 C15 3.4078 no . 2_576
H9 H7 3.5895 no . 2_677
H9 H13 2.9742 no . 1_565
H9 H14 3.2559 no . 2_576
H9 H15 2.6610 no . 2_576
H9 H16 3.5520 no . 2_676
H10 N1 2.5533 no . 1_465
H10 C6 3.0926 no . 1_465
H10 C10 3.5007 no . 2_587
H10 C12 3.0938 no . 2_577
H10 C13 3.4105 no . 2_577
H10 H6 2.8259 no . 1_465
H10 H10 3.1416 no . 2_587
H10 H12 2.7281 no . 2_577
H10 H13 3.2956 no . 2_577
H11 C5 3.1088 no . 2_577
H11 C6 3.4889 no . 2_677
H11 C12 2.9016 no . 2_577
H11 C13 3.1080 no . 2_577
H11 C14 3.4827 no . 2_577
H11 C16 3.5004 no . 2_577
H11 H6 3.5746 no . 2_677
H11 H12 3.1937 no . 2_577
H11 H13 3.5010 no . 2_577
H12 N1 2.8250 no . 2_667
H12 C7 3.0905 no . 2_667
H12 C10 3.4037 no . 2_577
H12 H7 2.6707 no . 2_667
H12 H10 2.7281 no . 2_577
H12 H11 3.1937 no . 2_577
H13 N1 3.4983 no . 2_667
H13 N2 2.7280 no . 1_545
H13 C7 3.4617 no . 2_667
H13 C9 3.0821 no . 1_545
H13 H7 2.8318 no . 2_667
H13 H9 2.9742 no . 1_545
H13 H10 3.2956 no . 2_577
H13 H11 3.5010 no . 2_577
H13 H14 3.5910 no . 2_566
H14 O1 3.1812 no . 1_455
H14 C14 3.3419 no . 2_566
H14 H9 3.2559 no . 2_576
H14 H13 3.5910 no . 2_566
H14 H14 2.4612 no . 2_566
H15 O1 3.1384 no . 1_455
H15 N2 3.3186 no . 2_576
H15 C7 3.2662 no . 1_554
H15 C8 3.2715 no . 1_554
H15 C9 3.0626 no . 2_576
H15 C16 3.3509 no . 2_576
H15 H7 2.7318 no . 1_554
H15 H8 2.7907 no . 1_554
H15 H9 2.6610 no . 2_576
H15 H15 3.3840 no . 2_576
H15 H16 2.8039 no . 2_576
H16 O1 2.5348 no . 2_676
H16 C15 3.4573 no . 2_576
H16 H7 3.0948 no . 1_554
H16 H8 3.2055 no . 1_554
H16 H9 3.5520 no . 2_676
H16 H15 2.8039 no . 2_576

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_DPA-AuCl_3
_database_code_depnum_ccdc_archive 'CCDC 1994426'
loop_
_audit_author_name
_audit_author_address
'Hiroaki Imoto'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H13 As Au Cl3 N2'
_chemical_formula_moiety         'C17 H13 As Au Cl3 N2'
_chemical_formula_weight         623.55
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
_space_group_IT_number           43
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/4-X,1/4+Y,1/4+Z
3 1/4+X,1/4-Y,1/4+Z
4 1/2-X,-Y,1/2+Z
5 +X,1/2+Y,1/2+Z
6 1/4-X,3/4+Y,3/4+Z
7 1/4+X,3/4-Y,3/4+Z
8 1/2-X,1/2-Y,+Z
9 1/2+X,+Y,1/2+Z
10 3/4-X,1/4+Y,3/4+Z
11 3/4+X,1/4-Y,3/4+Z
12 -X,-Y,+Z
13 1/2+X,1/2+Y,+Z
14 3/4-X,3/4+Y,1/4+Z
15 3/4+X,3/4-Y,1/4+Z
16 -X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   16.402(5)
_cell_length_b                   47.390(13)
_cell_length_c                   9.844(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     7652(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      6.98
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4672.00
_exptl_absorpt_coefficient_mu    9.854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.199
_exptl_absorpt_correction_T_max  0.278

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            18916
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         6.975
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_k_max       61
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4311
_reflns_number_gt                3979
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0958
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4311
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0556P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.40
_refine_diff_density_min         -1.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.007(15)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
As As 0.0499 2.0058
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Au Au -2.0133 8.8022
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.47634(2) 0.03142(2) 0.49593(5) 0.04174(15) Uani 1 16 d . . .
As1 As 0.57343(6) 0.04274(2) 0.66089(11) 0.0361(2) Uani 1 16 d . . .
Cl1 Cl 0.3776(2) 0.02258(10) 0.3374(4) 0.0669(9) Uani 1 16 d . . .
Cl2 Cl 0.3749(5) 0.10550(17) 0.5153(10) 0.137(3) Uani 1 16 d . . .
Cl3 Cl 0.1988(5) 0.09626(15) 0.5463(8) 0.113(2) Uani 1 16 d . . .
N1 N 0.4709(8) 0.0829(3) 1.0037(18) 0.068(3) Uani 1 16 d . . .
N2 N 0.7108(8) -0.0295(2) 0.7645(16) 0.060(3) Uani 1 16 d . . .
C1 C 0.5365(7) 0.0542(2) 0.8396(13) 0.040(2) Uani 1 16 d . . .
C2 C 0.5645(8) 0.0354(2) 0.9375(13) 0.042(3) Uani 1 16 d . . .
C3 C 0.6150(6) 0.0118(2) 0.8890(11) 0.039(2) Uani 1 16 d . . .
C4 C 0.6304(6) 0.01200(19) 0.7485(12) 0.0352(19) Uani 1 16 d . . .
C5 C 0.6540(7) 0.0695(2) 0.6056(12) 0.039(2) Uani 1 16 d . . .
C6 C 0.4924(8) 0.0775(3) 0.8746(16) 0.055(3) Uani 1 16 d . . .
C7 C 0.4987(12) 0.0652(4) 1.0983(17) 0.071(4) Uani 1 16 d . . .
C8 C 0.5427(10) 0.0408(3) 1.0720(14) 0.058(3) Uani 1 16 d . . .
C9 C 0.6779(8) -0.0087(3) 0.6924(13) 0.048(3) Uani 1 16 d . . .
C10 C 0.6946(10) -0.0301(3) 0.8956(17) 0.062(4) Uani 1 16 d . . .
C11 C 0.6460(9) -0.0097(3) 0.9660(14) 0.056(3) Uani 1 16 d . . .
C12 C 0.6433(7) 0.0844(3) 0.4855(15) 0.051(3) Uani 1 16 d . . .
C13 C 0.7006(9) 0.1041(3) 0.4450(18) 0.062(4) Uani 1 16 d . . .
C14 C 0.7688(8) 0.1086(3) 0.5237(17) 0.060(4) Uani 1 16 d . . .
C15 C 0.7797(9) 0.0937(3) 0.6429(18) 0.061(3) Uani 1 16 d . . .
C16 C 0.7227(7) 0.0742(3) 0.6843(14) 0.051(3) Uani 1 16 d . . .
C17 C 0.2984(19) 0.0873(9) 0.587(4) 0.170(17) Uani 1 16 d . . .
H6 H 0.47681 0.09003 0.80692 0.0657 Uiso 1 16 calc R . .
H7 H 0.48793 0.06962 1.18863 0.0849 Uiso 1 16 calc R . .
H8 H 0.55697 0.02844 1.14154 0.0692 Uiso 1 16 calc R . .
H9 H 0.68768 -0.00816 0.59935 0.0571 Uiso 1 16 calc R . .
H10 H 0.71631 -0.04482 0.94625 0.0742 Uiso 1 16 calc R . .
H11 H 0.63612 -0.01098 1.05885 0.0673 Uiso 1 16 calc R . .
H12 H 0.59761 0.08107 0.43194 0.0617 Uiso 1 16 calc R . .
H13 H 0.69304 0.1143 0.36518 0.0748 Uiso 1 16 calc R . .
H14 H 0.80769 0.12174 0.49646 0.0715 Uiso 1 16 calc R . .
H15 H 0.82597 0.09679 0.69551 0.0738 Uiso 1 16 calc R . .
H16 H 0.73016 0.06431 0.76481 0.0610 Uiso 1 16 calc R . .
H17A H 0.30424 0.08905 0.68496 0.2035 Uiso 1 16 calc R . .
H17B H 0.30603 0.06759 0.56483 0.2035 Uiso 1 16 calc R . .



#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Au1 As1 2.3368(12) yes . .
Au1 Cl1 2.287(4) yes . .
As1 C1 1.938(12) yes . .
As1 C4 1.934(10) yes . .
As1 C5 1.912(11) yes . .
Cl2 C17 1.68(4) yes . .
Cl3 C17 1.74(3) yes . .
N1 C6 1.34(2) yes . .
N1 C7 1.33(2) yes . .
N2 C9 1.330(17) yes . .
N2 C10 1.32(2) yes . .
C1 C2 1.390(17) yes . .
C1 C6 1.363(18) yes . .
C2 C3 1.472(16) yes . .
C2 C8 1.395(19) yes . .
C3 C4 1.406(16) yes . .
C3 C11 1.367(18) yes . .
C4 C9 1.369(16) yes . .
C5 C12 1.387(18) yes . .
C5 C16 1.386(17) yes . .
C7 C8 1.39(2) yes . .
C10 C11 1.43(2) yes . .
C12 C13 1.384(19) yes . .
C13 C14 1.38(2) yes . .
C14 C15 1.38(2) yes . .
C15 C16 1.37(2) yes . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .
C17 H17A 0.970 no . .
C17 H17B 0.970 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
As1 Au1 Cl1 176.85(12) yes . . .
Au1 As1 C1 118.8(3) yes . . .
Au1 As1 C4 117.8(3) yes . . .
Au1 As1 C5 115.2(4) yes . . .
C1 As1 C4 87.5(5) yes . . .
C1 As1 C5 106.8(5) yes . . .
C4 As1 C5 107.1(4) yes . . .
C6 N1 C7 116.9(14) yes . . .
C9 N2 C10 117.1(12) yes . . .
As1 C1 C2 110.3(8) yes . . .
As1 C1 C6 128.4(10) yes . . .
C2 C1 C6 121.2(12) yes . . .
C1 C2 C3 116.6(11) yes . . .
C1 C2 C8 117.1(12) yes . . .
C3 C2 C8 126.3(12) yes . . .
C2 C3 C4 114.5(10) yes . . .
C2 C3 C11 126.5(11) yes . . .
C4 C3 C11 119.0(10) yes . . .
As1 C4 C3 111.0(7) yes . . .
As1 C4 C9 129.4(9) yes . . .
C3 C4 C9 119.6(10) yes . . .
As1 C5 C12 119.6(9) yes . . .
As1 C5 C16 120.6(9) yes . . .
C12 C5 C16 119.8(11) yes . . .
N1 C6 C1 122.2(13) yes . . .
N1 C7 C8 124.8(15) yes . . .
C2 C8 C7 117.6(13) yes . . .
N2 C9 C4 123.1(13) yes . . .
N2 C10 C11 125.0(14) yes . . .
C3 C11 C10 116.1(12) yes . . .
C5 C12 C13 120.2(13) yes . . .
C12 C13 C14 119.6(15) yes . . .
C13 C14 C15 120.2(13) yes . . .
C14 C15 C16 120.4(13) yes . . .
C5 C16 C15 119.7(13) yes . . .
Cl2 C17 Cl3 119(2) yes . . .
N1 C6 H6 118.899 no . . .
C1 C6 H6 118.898 no . . .
N1 C7 H7 117.592 no . . .
C8 C7 H7 117.604 no . . .
C2 C8 H8 121.236 no . . .
C7 C8 H8 121.208 no . . .
N2 C9 H9 118.393 no . . .
C4 C9 H9 118.465 no . . .
N2 C10 H10 117.493 no . . .
C11 C10 H10 117.497 no . . .
C3 C11 H11 121.928 no . . .
C10 C11 H11 121.929 no . . .
C5 C12 H12 119.893 no . . .
C13 C12 H12 119.897 no . . .
C12 C13 H13 120.207 no . . .
C14 C13 H13 120.203 no . . .
C13 C14 H14 119.890 no . . .
C15 C14 H14 119.898 no . . .
C14 C15 H15 119.764 no . . .
C16 C15 H15 119.793 no . . .
C5 C16 H16 120.153 no . . .
C15 C16 H16 120.126 no . . .
Cl2 C17 H17A 107.626 no . . .
Cl2 C17 H17B 107.624 no . . .
Cl3 C17 H17A 107.634 no . . .
Cl3 C17 H17B 107.639 no . . .
H17A C17 H17B 107.041 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Au1 As1 C1 C2 118.6(5) no . . . .
Au1 As1 C1 C6 -64.2(9) no . . . .
Au1 As1 C4 C3 -118.4(5) no . . . .
Au1 As1 C4 C9 58.9(8) no . . . .
Au1 As1 C5 C12 11.6(8) no . . . .
Au1 As1 C5 C16 -168.5(6) no . . . .
C1 As1 C4 C3 3.1(6) no . . . .
C1 As1 C4 C9 -179.6(8) no . . . .
C4 As1 C1 C2 -2.0(6) no . . . .
C4 As1 C1 C6 175.2(9) no . . . .
C1 As1 C5 C12 -122.7(7) no . . . .
C1 As1 C5 C16 57.2(8) no . . . .
C5 As1 C1 C2 -109.1(7) no . . . .
C5 As1 C1 C6 68.1(9) no . . . .
C4 As1 C5 C12 144.7(7) no . . . .
C4 As1 C5 C16 -35.4(9) no . . . .
C5 As1 C4 C3 109.9(6) no . . . .
C5 As1 C4 C9 -72.7(9) no . . . .
C6 N1 C7 C8 -5(2) no . . . .
C7 N1 C6 C1 4(2) no . . . .
C9 N2 C10 C11 -2(2) no . . . .
C10 N2 C9 C4 1.4(19) no . . . .
As1 C1 C2 C3 0.5(12) no . . . .
As1 C1 C2 C8 -179.8(7) no . . . .
As1 C1 C6 N1 -179.9(8) no . . . .
C2 C1 C6 N1 -2.9(19) no . . . .
C6 C1 C2 C3 -176.9(10) no . . . .
C6 C1 C2 C8 2.7(17) no . . . .
C1 C2 C3 C4 2.0(14) no . . . .
C1 C2 C3 C11 -177.1(9) no . . . .
C1 C2 C8 C7 -3.6(19) no . . . .
C3 C2 C8 C7 176.0(11) no . . . .
C8 C2 C3 C4 -177.6(12) no . . . .
C8 C2 C3 C11 3.4(19) no . . . .
C2 C3 C4 As1 -3.5(12) no . . . .
C2 C3 C4 C9 178.9(8) no . . . .
C2 C3 C11 C10 -179.1(10) no . . . .
C4 C3 C11 C10 1.8(16) no . . . .
C11 C3 C4 As1 175.6(9) no . . . .
C11 C3 C4 C9 -2.0(15) no . . . .
As1 C4 C9 N2 -176.8(7) no . . . .
C3 C4 C9 N2 0.3(16) no . . . .
As1 C5 C12 C13 179.1(7) no . . . .
As1 C5 C16 C15 -179.8(7) no . . . .
C12 C5 C16 C15 0.2(17) no . . . .
C16 C5 C12 C13 -0.8(18) no . . . .
N1 C7 C8 C2 5(3) no . . . .
N2 C10 C11 C3 -0(2) no . . . .
C5 C12 C13 C14 1(2) no . . . .
C12 C13 C14 C15 -1(2) no . . . .
C13 C14 C15 C16 -0(2) no . . . .
C14 C15 C16 C5 0(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C2 2.801(18) no . .
N2 C3 2.793(16) no . .
C1 C7 2.67(2) no . .
C1 C16 3.545(17) no . .
C4 C10 2.679(18) no . .
C4 C16 3.375(16) no . .
C5 C14 2.762(18) no . .
C6 C8 2.73(2) no . .
C8 C11 3.11(2) no . .
C9 C11 2.745(19) no . .
C12 C15 2.76(2) no . .
C13 C16 2.77(2) no . .
Au1 Au1 3.0775(15) no . 12_655
Au1 C9 3.362(13) no . 12_655
N1 C13 3.55(2) no . 11_455
N1 C14 3.537(19) no . 9_455
N1 C15 3.46(2) no . 9_455
N2 C17 3.25(4) no . 12_655
C8 C11 3.58(2) no . 12_655
C9 Au1 3.362(13) no . 12_655
C11 C8 3.58(2) no . 12_655
C13 N1 3.55(2) no . 3_554
C14 N1 3.537(19) no . 9_554
C15 N1 3.46(2) no . 9_554
C17 N2 3.25(4) no . 12_655
Au1 H12 3.1447 no . .
As1 H6 3.0984 no . .
As1 H9 3.1140 no . .
As1 H12 2.9217 no . .
As1 H16 2.9495 no . .
N1 H8 3.2383 no . .
N2 H11 3.2662 no . .
C1 H8 3.2302 no . .
C1 H16 3.2961 no . .
C2 H6 3.2293 no . .
C2 H7 3.2125 no . .
C2 H11 2.7630 no . .
C2 H16 3.4856 no . .
C3 H8 2.7767 no . .
C3 H9 3.2317 no . .
C3 H10 3.2048 no . .
C3 H16 3.3552 no . .
C4 H11 3.2445 no . .
C4 H16 2.9745 no . .
C5 H13 3.2418 no . .
C5 H15 3.2267 no . .
C6 H7 3.1141 no . .
C7 H6 3.1207 no . .
C8 H11 2.8950 no . .
C9 H10 3.0944 no . .
C10 H9 3.0980 no . .
C11 H8 2.8955 no . .
C12 H14 3.2266 no . .
C12 H16 3.2397 no . .
C13 H15 3.2298 no . .
C14 H12 3.2259 no . .
C14 H16 3.2322 no . .
C15 H13 3.2332 no . .
C16 H12 3.2380 no . .
C16 H14 3.2293 no . .
H7 H8 2.3034 no . .
H8 H11 2.4162 no . .
H10 H11 2.3517 no . .
H12 H13 2.3155 no . .
H13 H14 2.3088 no . .
H14 H15 2.3081 no . .
H15 H16 2.3031 no . .
Au1 H7 3.5305 no . 1_554
Au1 H9 3.0804 no . 12_655
Au1 H17B 3.3468 no . .
Cl1 H7 3.2230 no . 1_554
Cl1 H8 3.5282 no . 1_554
Cl1 H8 3.2734 no . 12_654
Cl1 H9 2.8744 no . 12_655
Cl1 H11 2.8060 no . 12_654
Cl1 H16 3.2050 no . 9_454
Cl1 H17B 3.3076 no . .
Cl2 H6 3.4022 no . .
Cl2 H6 3.5681 no . 11_454
Cl2 H15 3.2745 no . 9_454
Cl3 H6 3.0557 no . 11_454
Cl3 H13 3.2553 no . 9_455
Cl3 H14 3.3974 no . 3_455
Cl3 H16 3.1988 no . 9_454
N1 H13 2.7720 no . 11_455
N1 H14 3.2502 no . 9_455
N1 H14 3.5169 no . 11_455
N1 H15 3.1066 no . 9_455
N2 H17A 2.9387 no . 12_655
N2 H17B 2.6828 no . 12_655
C5 H10 2.8912 no . 4_654
C7 H11 3.4134 no . 12_655
C7 H13 3.4661 no . 11_455
C7 H14 3.4619 no . 11_455
C7 H15 3.3436 no . 9_455
C8 H11 3.2570 no . 12_655
C9 H11 3.4493 no . 4_654
C9 H17B 3.0724 no . 12_655
C10 H9 3.3215 no . 4_655
C10 H17A 3.4810 no . 12_655
C11 H9 3.1427 no . 4_655
C12 H10 2.9941 no . 4_654
C12 H14 3.4396 no . 11_454
C12 H15 3.4659 no . 11_454
C13 H10 3.1238 no . 4_654
C13 H14 3.2589 no . 11_454
C13 H15 3.0964 no . 11_454
C13 H17A 3.1549 no . 9_554
C14 H7 3.5387 no . 3_554
C14 H10 3.1276 no . 4_654
C14 H12 3.5023 no . 3_555
C14 H13 3.2593 no . 3_555
C14 H17A 3.5092 no . 9_554
C15 H10 3.0187 no . 4_654
C15 H13 3.3491 no . 3_555
C16 H10 2.9049 no . 4_654
C17 H13 3.4793 no . 9_455
C17 H16 3.5384 no . 9_454
H6 Cl2 3.4022 no . .
H6 Cl2 3.5681 no . 3_555
H6 Cl3 3.0557 no . 3_555
H6 H17A 3.0749 no . .
H7 Au1 3.5305 no . 1_556
H7 Cl1 3.2230 no . 1_556
H7 C14 3.5387 no . 11_455
H7 H12 3.0442 no . 1_556
H7 H13 3.2972 no . 11_455
H7 H14 3.0587 no . 11_455
H7 H15 2.9528 no . 9_455
H8 Cl1 3.5282 no . 1_556
H8 Cl1 3.2734 no . 12_656
H8 H8 3.2800 no . 12_655
H8 H11 3.3730 no . 12_655
H9 Au1 3.0804 no . 12_655
H9 Cl1 2.8744 no . 12_655
H9 C10 3.3215 no . 4_654
H9 C11 3.1427 no . 4_654
H9 H10 3.3249 no . 4_654
H9 H11 3.0551 no . 4_654
H9 H17B 2.8387 no . 12_655
H10 C5 2.8912 no . 4_655
H10 C12 2.9941 no . 4_655
H10 C13 3.1238 no . 4_655
H10 C14 3.1276 no . 4_655
H10 C15 3.0187 no . 4_655
H10 C16 2.9049 no . 4_655
H10 H9 3.3249 no . 4_655
H10 H12 3.5051 no . 4_655
H10 H15 3.5451 no . 4_655
H10 H16 3.3850 no . 4_655
H10 H17A 3.3351 no . 12_655
H11 Cl1 2.8060 no . 12_656
H11 C7 3.4134 no . 12_655
H11 C8 3.2570 no . 12_655
H11 C9 3.4493 no . 4_655
H11 H8 3.3730 no . 12_655
H11 H9 3.0551 no . 4_655
H12 C14 3.5023 no . 11_454
H12 H7 3.0442 no . 1_554
H12 H10 3.5051 no . 4_654
H12 H14 2.9604 no . 11_454
H12 H15 3.4397 no . 11_454
H13 Cl3 3.2553 no . 9_554
H13 N1 2.7720 no . 3_554
H13 C7 3.4661 no . 3_554
H13 C14 3.2593 no . 11_454
H13 C15 3.3491 no . 11_454
H13 C17 3.4793 no . 9_554
H13 H7 3.2972 no . 3_554
H13 H14 2.5946 no . 11_454
H13 H15 2.7771 no . 11_454
H13 H17A 2.8117 no . 9_554
H14 Cl3 3.3974 no . 11_554
H14 N1 3.5169 no . 3_554
H14 N1 3.2502 no . 9_554
H14 C7 3.4619 no . 3_554
H14 C12 3.4396 no . 3_555
H14 C13 3.2589 no . 3_555
H14 H7 3.0587 no . 3_554
H14 H12 2.9604 no . 3_555
H14 H13 2.5946 no . 3_555
H14 H17A 3.4360 no . 9_554
H15 Cl2 3.2745 no . 9_555
H15 N1 3.1066 no . 9_554
H15 C7 3.3436 no . 9_554
H15 C12 3.4659 no . 3_555
H15 C13 3.0964 no . 3_555
H15 H7 2.9528 no . 9_554
H15 H10 3.5451 no . 4_654
H15 H12 3.4397 no . 3_555
H15 H13 2.7771 no . 3_555
H16 Cl1 3.2050 no . 9_555
H16 Cl3 3.1988 no . 9_555
H16 C17 3.5384 no . 9_555
H16 H10 3.3850 no . 4_654
H16 H17B 3.2086 no . 9_555
H17A N2 2.9387 no . 12_655
H17A C10 3.4810 no . 12_655
H17A C13 3.1549 no . 9_455
H17A C14 3.5092 no . 9_455
H17A H6 3.0749 no . .
H17A H10 3.3351 no . 12_655
H17A H13 2.8117 no . 9_455
H17A H14 3.4360 no . 9_455
H17B Au1 3.3468 no . .
H17B Cl1 3.3076 no . .
H17B N2 2.6828 no . 12_655
H17B C9 3.0724 no . 12_655
H17B H9 2.8387 no . 12_655
H17B H16 3.2086 no . 9_454

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



