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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1835650'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Cd N9, C8 H19 Cl P'
_chemical_formula_sum            'C14 H19 Cd Cl N9 P'
_chemical_formula_weight         492.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.7129(4)
_cell_length_b                   12.1860(5)
_cell_length_c                   16.3333(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2132.27(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3874
_cell_measurement_theta_min      2.494
_cell_measurement_theta_max      31.633

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    1.241
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14198
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         31.633
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5690
_reflns_number_gt                3874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.844
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.27(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5690
_refine_ls_number_parameters     194
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.1210
_refine_ls_wR_factor_ref         0.3542
_refine_ls_wR_factor_gt          0.3370
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_restrained_S_all      1.379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.22054(5) 0.93917(4) 0.19177(3) 0.06112(11) Uani 1 1 d . U . . .
N1 N 0.3788(9) 1.0691(8) 0.1793(5) 0.1175(6) Uani 1 1 d . U . . .
N6 N 0.0776(11) 1.2554(6) 0.1842(6) 0.1354(5) Uani 1 1 d . U . . .
N4 N 0.0863(10) 1.0732(6) 0.1315(5) 0.1041(7) Uani 1 1 d . U . . .
N2 N 0.2875(8) 0.8726(6) 0.0686(4) 0.0894(5) Uani 1 1 d . U . . .
N5 N 0.3938(9) 0.8913(13) -0.0582(6) 0.2049(7) Uani 1 1 d . U . . .
C4 C 0.0746(9) 1.1550(7) 0.1593(5) 0.0781(8) Uani 1 1 d . U . . .
C2 C 0.3308(11) 0.8925(10) 0.0088(6) 0.11058(18) Uani 1 1 d . U . . .
C1 C 0.4493(11) 1.1324(10) 0.1758(6) 0.11058(18) Uani 1 1 d . U . . .
P1 P 0.8040(3) 0.9873(3) 0.96435(17) 0.11058(18) Uani 1 1 d . U . . .
C10 C 0.8084(10) 0.9082(10) 1.0605(6) 0.11058(18) Uani 1 1 d . U . . .
H10A H 0.8473 0.8380 1.0493 0.133 Uiso 1 1 calc R U . . .
H10B H 0.8616 0.9469 1.0989 0.133 Uiso 1 1 calc R U . . .
N9 N 0.5145(15) 1.2135(12) 0.1564(6) 0.2704(5) Uani 1 1 d . U . . .
C13 C 0.6932(12) 0.9739(17) 0.8158(9) 0.1632(13) Uani 1 1 d . U . . .
H13A H 0.6468 0.9278 0.7792 0.245 Uiso 1 1 calc R U . . .
H13B H 0.6452 1.0383 0.8283 0.245 Uiso 1 1 calc R U . . .
H13C H 0.7703 0.9951 0.7904 0.245 Uiso 1 1 calc R U . . .
C14 C 0.7208(11) 0.9112(10) 0.8946(6) 0.11058(18) Uani 1 1 d . U . . .
H14A H 0.7677 0.8455 0.8813 0.133 Uiso 1 1 calc R U . . .
H14B H 0.6426 0.8886 0.9193 0.133 Uiso 1 1 calc R U . . .
C12 C 0.80302(9) 1.12294(2) 0.96586(2) 0.11058(18) Uani 1 1 d D U . . .
H12A H 0.8529 1.1520 0.9212 0.133 Uiso 1 1 d R U . . .
H12B H 0.7168 1.1368 0.9514 0.133 Uiso 1 1 d R U . . .
C11 C 0.81207(9) 1.20705(2) 1.03265(2) 0.197(3) Uani 1 1 d D U . . .
H11A H 0.8080 1.2792 1.0092 0.296 Uiso 1 1 calc R U . . .
H11B H 0.7442 1.1974 1.0703 0.296 Uiso 1 1 calc R U . . .
H11C H 0.8898 1.1984 1.0611 0.296 Uiso 1 1 calc R U . . .
C15 C 0.9739(9) 1.0009(10) 0.9237(6) 0.11058(18) Uani 1 1 d . U . . .
H15A H 0.9732 1.0533 0.8787 0.133 Uiso 1 1 d R U . . .
H15B H 1.0189 1.0354 0.9686 0.133 Uiso 1 1 d R U . . .
C16 C 1.0223(17) 0.9023(17) 0.9080(17) 0.2813(17) Uani 1 1 d . U . . .
H16A H 1.1061 0.9107 0.8880 0.422 Uiso 1 1 calc R U . . .
H16B H 1.0232 0.8594 0.9572 0.422 Uiso 1 1 calc R U . . .
H16C H 0.9726 0.8660 0.8673 0.422 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6800(3) 0.8057(2) 1.18030(14) 0.11058(18) Uani 1 1 d . U . . .
C17 C 0.6939(11) 0.8888(14) 1.0985(6) 0.1307(6) Uani 1 1 d . U . . .
H17A H 0.6382 0.8603 1.0567 0.157 Uiso 1 1 calc R U . . .
H17B H 0.6610 0.9597 1.1146 0.157 Uiso 1 1 calc R U . . .
N7A N 0.6564(8) 1.3125(8) 0.2373(5) 0.1173(8) Uani 1 1 d . U . . .
C8A C 0.5863(12) 1.2760(10) 0.2057(5) 0.1233(6) Uani 1 1 d . U . . .
N3A N -0.0453(8) 1.3229(5) 0.2955(4) 0.0874(9) Uani 1 1 d . U . . .
C3A C 0.0083(7) 1.2890(5) 0.2468(5) 0.0678(6) Uani 1 1 d . U . . .
N8A N 0.3461(7) 0.9882(8) -0.1835(4) 0.0986(15) Uani 1 1 d . U . . .
C7A C 0.3639(8) 0.9585(11) -0.1195(5) 0.1046(13) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N2 2.285(7) . ?
Cd1 N1 2.329(9) . ?
Cd1 N7A 2.337(9) 3_645 ?
Cd1 N8A 2.333(8) 2_575 ?
Cd1 N3A 2.361(8) 3_545 ?
Cd1 N4 2.388(9) . ?
N1 C1 1.081(15) . ?
N6 C4 1.289(12) . ?
N6 C3A 1.328(13) . ?
N4 C4 1.103(11) . ?
N2 C2 1.108(12) . ?
N5 C2 1.286(14) . ?
N5 C7A 1.333(15) . ?
C1 N9 1.251(18) . ?
P1 C12 1.653(4) . ?
P1 C14 1.718(12) . ?
P1 C10 1.843(11) . ?
P1 C15 1.945(10) . ?
C10 C17 1.395(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N9 C8A 1.350(17) . ?
C13 C14 1.526(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 C11 1.50000(11) . ?
C12 H12A 0.9704 . ?
C12 H12B 0.9684 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C16 1.33(2) . ?
C15 H15A 0.9742 . ?
C15 H15B 0.9727 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
Cl1 C17 1.683(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N7A C8A 1.015(14) . ?
N7A Cd1 2.337(9) 3_655 ?
N3A C3A 1.064(11) . ?
N3A Cd1 2.361(8) 3 ?
N8A C7A 1.122(11) . ?
N8A Cd1 2.333(8) 2_574 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cd1 N1 86.3(3) . . ?
N2 Cd1 N7A 91.4(3) . 3_645 ?
N1 Cd1 N7A 94.7(3) . 3_645 ?
N2 Cd1 N8A 178.5(3) . 2_575 ?
N1 Cd1 N8A 92.4(3) . 2_575 ?
N7A Cd1 N8A 89.4(3) 3_645 2_575 ?
N2 Cd1 N3A 96.6(3) . 3_545 ?
N1 Cd1 N3A 174.0(3) . 3_545 ?
N7A Cd1 N3A 90.5(3) 3_645 3_545 ?
N8A Cd1 N3A 84.7(3) 2_575 3_545 ?
N2 Cd1 N4 93.9(3) . . ?
N1 Cd1 N4 86.4(3) . . ?
N7A Cd1 N4 174.6(3) 3_645 . ?
N8A Cd1 N4 85.2(3) 2_575 . ?
N3A Cd1 N4 88.2(3) 3_545 . ?
C1 N1 Cd1 176.8(10) . . ?
C4 N6 C3A 121.4(9) . . ?
C4 N4 Cd1 121.2(8) . . ?
C2 N2 Cd1 146.1(8) . . ?
C2 N5 C7A 120.4(11) . . ?
N4 C4 N6 170.0(11) . . ?
N2 C2 N5 165.3(14) . . ?
N1 C1 N9 165.3(13) . . ?
C12 P1 C14 123.1(4) . . ?
C12 P1 C10 120.7(4) . . ?
C14 P1 C10 107.2(5) . . ?
C12 P1 C15 85.7(4) . . ?
C14 P1 C15 107.8(5) . . ?
C10 P1 C15 108.1(5) . . ?
C17 C10 P1 116.5(9) . . ?
C17 C10 H10A 108.2 . . ?
P1 C10 H10A 108.2 . . ?
C17 C10 H10B 108.2 . . ?
P1 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C1 N9 C8A 127.8(10) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C13 C14 P1 112.9(10) . . ?
C13 C14 H14A 109.0 . . ?
P1 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
P1 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C11 C12 P1 133.92(10) . . ?
C11 C12 H12A 105.2 . . ?
P1 C12 H12A 110.5 . . ?
C11 C12 H12B 96.9 . . ?
P1 C12 H12B 100.1 . . ?
H12A C12 H12B 106.2 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C15 P1 110.7(11) . . ?
C16 C15 H15A 116.6 . . ?
P1 C15 H15A 107.8 . . ?
C16 C15 H15B 110.0 . . ?
P1 C15 H15B 104.1 . . ?
H15A C15 H15B 106.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 Cl1 122.2(10) . . ?
C10 C17 H17A 106.8 . . ?
Cl1 C17 H17A 106.8 . . ?
C10 C17 H17B 106.8 . . ?
Cl1 C17 H17B 106.8 . . ?
H17A C17 H17B 106.6 . . ?
C8A N7A Cd1 163.7(11) . 3_655 ?
N7A C8A N9 166.8(15) . . ?
C3A N3A Cd1 136.7(7) . 3 ?
N3A C3A N6 175.1(8) . . ?
C7A N8A Cd1 170.9(8) . 2_574 ?
N8A C7A N5 159.9(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 N4 C4 N6 88(6) . . . . ?
C3A N6 C4 N4 -169(6) . . . . ?
Cd1 N2 C2 N5 145(4) . . . . ?
C7A N5 C2 N2 161(4) . . . . ?
C12 P1 C10 C17 84.8(11) . . . . ?
C14 P1 C10 C17 -63.3(11) . . . . ?
C15 P1 C10 C17 -179.2(10) . . . . ?
N1 C1 N9 C8A 151(5) . . . . ?
C12 P1 C14 C13 24.5(11) . . . . ?
C10 P1 C14 C13 171.6(9) . . . . ?
C15 P1 C14 C13 -72.2(10) . . . . ?
C14 P1 C12 C11 146.9(5) . . . . ?
C10 P1 C12 C11 4.0(5) . . . . ?
C15 P1 C12 C11 -104.6(3) . . . . ?
P1 C10 C17 Cl1 172.7(8) . . . . ?
Cd1 N7A C8A N9 151(4) 3_655 . . . ?
C1 N9 C8A N7A 101(5) . . . . ?
C2 N5 C7A N8A -139(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C15 H15B N4 0.97 2.80 3.707(13) 156.5 1_656
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C15 H15B N4 0.97 2.80 3.707(13) 156.5 1_656
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C15 H15B N4 0.97 2.80 3.707(13) 156.5 1_656
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C15 H15B N4 0.97 2.80 3.707(13) 156.5 1_656
C14 H14B N5 0.97 2.69 3.595(15) 155.4 1_556
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C15 H15B N4 0.97 2.80 3.707(13) 156.5 1_656
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576
C13 H13B N6 0.96 2.62 3.52(2) 156.1 4_576
C12 H12A N9 0.97 2.70 3.618(14) 157.9 4_576

_refine_diff_density_max         3.019
_refine_diff_density_min         -4.653
_refine_diff_density_rms         0.251




# start Validation Reply Form
_vrf_EXPT005_1                   
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: ...
;
_vrf_DIFF003_1                   
;
PROBLEM: _diffrn_measurement_device_type is missing
RESPONSE: ...
;
_vrf_PLAT183_1                   
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do ! 
RESPONSE: ...
;
_vrf_PLAT184_1                   
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 
RESPONSE: ...
;
_vrf_PLAT185_1                   
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 
RESPONSE: ...
;
_vrf_PLAT241_1                   
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         N9 Check 
RESPONSE: This atom has relatively high atomic displacement
parameters compared with the connected atoms.
;
_vrf_PLAT972_1                   
;
PROBLEM: Check Calcd Resid. Dens.  0.13A   From Cl1            -4.47 eA-3  
RESPONSE: The residual density is larger than expected residual 
density minimum.
;
_vrf_PLAT242_1                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: This atom has relatively low atomic displacement
parameters compared with the Connected atoms.
;
_vrf_PLAT360_1                   
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C15      - C16      .       1.33 Ang.  
RESPONSE: This problem may arise because of disorder.
;
_vrf_PLAT410_1                   
;
PROBLEM: Short Intra H...H Contact  H12A     ..H15A     .       1.89 Ang.  
RESPONSE: The data quality is not good.
;
_vrf_PLAT934_1                   
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check 
RESPONSE: The data quality is not good.

;
_vrf_PLAT971_1                   
;
PROBLEM: Check Calcd Resid. Dens.  1.39A   From C11             2.89 eA-3  
RESPONSE: The residual density is larger than expected residual
density maximum.
;

####################################################################### 
# 
# 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_C2C
_database_code_depnum_ccdc_archive 'CCDC 1835651'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Cd N9, C8 H18 F P'
_chemical_formula_sum            'C14 H18 Cd F N9 P'
_chemical_formula_weight         474.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.909(4)
_cell_length_b                   10.618(2)
_cell_length_c                   10.507(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.75(3)
_cell_angle_gamma                90
_cell_volume                     1959.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2248
_cell_measurement_theta_min      3.344
_cell_measurement_theta_max      27.484

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    1.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6580
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.344
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2248
_reflns_number_gt                1981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+1.2878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0238(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.2500 0.2500 0.0000 0.03333(11) Uani 1 2 d S . P . .
N4 N 0.25746(15) 0.24409(19) 0.2255(2) 0.0553(6) Uani 1 1 d . . . . .
C2 C 0.43925(13) 0.2640(2) 0.1685(3) 0.0428(5) Uani 1 1 d . . . . .
N2 N 0.38313(12) 0.2291(2) 0.0908(2) 0.0553(6) Uani 1 1 d . . . . .
P1 P 0.0000 0.70306(8) 0.7500 0.03322(17) Uani 1 2 d S T P . .
C4 C 0.08449(11) 0.6077(2) 0.8117(2) 0.0402(5) Uani 1 1 d . . . . .
H4A H 0.1276 0.6615 0.8595 0.048 Uiso 1 1 calc R U . . .
H4B H 0.0796 0.5478 0.8777 0.048 Uiso 1 1 calc R U . . .
C5 C 0.10118(13) 0.5359(2) 0.7015(2) 0.0506(6) Uani 1 1 d . . . . .
H5A H 0.1132 0.5957 0.6426 0.061 Uiso 1 1 calc R U . . .
H5B H 0.1457 0.4835 0.7446 0.061 Uiso 1 1 calc R U . . .
C6 C -0.00297(12) 0.8003(2) 0.8879(2) 0.0465(5) Uani 1 1 d . . . . .
H6A H -0.0062 0.7465 0.9602 0.056 Uiso 1 1 calc R U . . .
H6B H 0.0442 0.8475 0.9251 0.056 Uiso 1 1 calc R U . . .
C3 C 0.28027(12) 0.2941(2) 0.3294(2) 0.0438(5) Uani 1 1 d . . . . .
C7 C -0.06923(14) 0.8919(2) 0.8453(3) 0.0572(6) Uani 1 1 d . . . . .
H7A H -0.0646 0.9492 0.7782 0.086 Uiso 1 1 calc R U . . .
H7B H -0.0689 0.9383 0.9239 0.086 Uiso 1 1 calc R U . . .
H7C H -0.1162 0.8461 0.8068 0.086 Uiso 1 1 calc R U . . .
N5 N 0.31007(13) 0.3417(2) 0.4518(2) 0.0687(7) Uani 1 1 d . . . . .
F1 F 0.04544(16) 0.4654(3) 0.6268(3) 0.0640(8) Uani 0.5 1 d . . P . .
N3 N 0.5000 0.3194(3) 0.2500 0.0842(12) Uani 1 2 d S T P . .
C1 C 0.28451(12) 0.4457(2) 0.4807(2) 0.0451(5) Uani 1 1 d . . . . .
N1 N 0.26546(14) 0.5357(2) 0.5169(2) 0.0653(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.292(2) 6_565 ?
Cd1 N1 2.292(2) 4_545 ?
Cd1 N4 2.322(2) 7 ?
Cd1 N4 2.322(2) . ?
Cd1 N2 2.349(2) 7 ?
Cd1 N2 2.349(2) . ?
N4 C3 1.145(3) . ?
C2 N2 1.135(3) . ?
C2 N3 1.292(3) . ?
P1 C6 1.797(2) 2_556 ?
P1 C6 1.797(2) . ?
P1 C4 1.797(2) 2_556 ?
P1 C4 1.798(2) . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 F1 1.294(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 N5 1.300(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N5 C1 1.286(3) . ?
N3 C2 1.292(3) 2_655 ?
C1 N1 1.135(3) . ?
N1 Cd1 2.292(2) 4 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 N1 180.0 6_565 4_545 ?
N1 Cd1 N4 90.57(7) 6_565 7 ?
N1 Cd1 N4 89.43(7) 4_545 7 ?
N1 Cd1 N4 89.43(7) 6_565 . ?
N1 Cd1 N4 90.57(7) 4_545 . ?
N4 Cd1 N4 180.0 7 . ?
N1 Cd1 N2 91.41(8) 6_565 7 ?
N1 Cd1 N2 88.59(8) 4_545 7 ?
N4 Cd1 N2 86.11(9) 7 7 ?
N4 Cd1 N2 93.89(9) . 7 ?
N1 Cd1 N2 88.59(8) 6_565 . ?
N1 Cd1 N2 91.41(8) 4_545 . ?
N4 Cd1 N2 93.89(9) 7 . ?
N4 Cd1 N2 86.11(9) . . ?
N2 Cd1 N2 180.00(4) 7 . ?
C3 N4 Cd1 145.0(2) . . ?
N2 C2 N3 171.9(3) . . ?
C2 N2 Cd1 146.9(2) . . ?
C6 P1 C6 109.87(18) 2_556 . ?
C6 P1 C4 108.79(10) 2_556 2_556 ?
C6 P1 C4 108.99(10) . 2_556 ?
C6 P1 C4 108.99(10) 2_556 . ?
C6 P1 C4 108.79(10) . . ?
C4 P1 C4 111.42(15) 2_556 . ?
C5 C4 P1 114.65(15) . . ?
C5 C4 H4A 108.6 . . ?
P1 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
P1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
F1 C5 C4 113.6(2) . . ?
F1 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
F1 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 P1 113.55(17) . . ?
C7 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N4 C3 N5 174.7(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N5 C3 120.3(2) . . ?
C2 N3 C2 125.9(3) . 2_655 ?
N1 C1 N5 174.5(3) . . ?
C1 N1 Cd1 148.9(2) . 4 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C4 C5 -51.0(2) 2_556 . . . ?
C6 P1 C4 C5 -170.77(17) . . . . ?
C4 P1 C4 C5 69.06(16) 2_556 . . . ?
P1 C4 C5 F1 -55.2(3) . . . . ?
C6 P1 C6 C7 56.73(16) 2_556 . . . ?
C4 P1 C6 C7 -62.4(2) 2_556 . . . ?
C4 P1 C6 C7 175.97(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556
C4 H4A N5 0.97 2.69 3.557(3) 148.7 4_556
C4 H4B F1 0.97 2.50 3.148(4) 123.7 2_556
C6 H6B N5 0.97 2.57 3.433(3) 147.5 4_556

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.065

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1845895'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C6 Cd N9, 0.5(C8 H19 Cl P), C H2 Cl0.50, C H2.50, C H2.50, C H2'
_chemical_formula_sum            'C14 H19 Cd Cl N9 P'
_chemical_formula_weight         492.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   16.650(5)
_cell_length_b                   16.667(5)
_cell_length_c                   15.809(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4387(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    333(2)
_cell_measurement_reflns_used    3815
_cell_measurement_theta_min      2.447
_cell_measurement_theta_max      24.998

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    1.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      333(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Rigaku,SCXmini
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17662
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3815
_reflns_number_gt                2104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+55.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3815
_refine_ls_number_parameters     316
_refine_ls_number_restraints     358
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.1289
_refine_ls_wR_factor_ref         0.3685
_refine_ls_wR_factor_gt          0.3511
_refine_ls_goodness_of_fit_ref   0.719
_refine_ls_restrained_S_all      1.476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.18733(6) 0.29073(7) 0.50936(8) 0.1277(7) Uani 1 1 d . U . . .
C1 C 0.2853(15) 0.2903(15) 0.6927(15) 0.192(8) Uani 1 1 d . U . . .
N1 N 0.1740(14) 0.1526(11) 0.5194(17) 0.260(10) Uani 1 1 d D U . . .
P1 P 0.5000 -0.0069(4) 0.2500 0.194(3) Uani 1 2 d DS TU P . .
N2 N 0.2453(13) 0.2994(13) 0.6417(13) 0.210(7) Uani 1 1 d . U . . .
C2 C 0.1920(14) 0.0925(16) 0.503(2) 0.225(10) Uani 1 1 d . U . . .
N3 N 0.3123(11) 0.2828(19) 0.4487(19) 0.276(10) Uani 1 1 d . U . . .
C6 C 0.3681(14) 0.272(2) 0.4349(18) 0.257(10) Uani 1 1 d . U . . .
N7 N 0.1986(15) 0.0219(12) 0.4702(18) 0.276(10) Uani 1 1 d D U . . .
N8 N 0.3434(13) 0.2990(13) 0.7535(14) 0.221(8) Uani 1 1 d . U . . .
N9 N 0.4432(11) 0.2621(17) 0.3856(14) 0.267(9) Uani 1 1 d . U . . .
C7 C 0.3992(4) 0.0184(8) 0.2816(11) 0.275(12) Uani 0.5 1 d D U P . .
H7A H 0.4186 0.0428 0.3327 0.330 Uiso 0.5 1 d R U P . .
H7B H 0.3873 -0.0369 0.2928 0.330 Uiso 0.5 1 d R U P . .
C8 C 0.5380(6) 0.0680(5) 0.1783(7) 0.194(3) Uani 0.5 1 d D U P . .
H8A H 0.4996 0.0571 0.1344 0.233 Uiso 0.5 1 d R U P . .
H8B H 0.5854 0.0914 0.1541 0.233 Uiso 0.5 1 d R U P . .
C9 C 0.3805(6) 0.1028(7) 0.2554(13) 0.340(18) Uani 0.5 1 d D U P . .
H9A H 0.3377 0.0642 0.2553 0.408 Uiso 0.5 1 d R U P . .
H9B H 0.3908 0.1160 0.1973 0.408 Uiso 0.5 1 d R U P . .
C10 C 0.5000(10) -0.1013(4) 0.1944(7) 0.267(13) Uani 0.5 1 d D U P . .
H10A H 0.5496 -0.1091 0.1647 0.321 Uiso 0.5 1 d R U P . .
H10B H 0.4579 -0.0934 0.1537 0.321 Uiso 0.5 1 d R U P . .
Cl1 Cl 0.3166(19) 0.124(3) 0.3469(13) 0.57(2) Uani 0.5 1 d D U P . .
C12 C 0.434(2) -0.1012(17) 0.129(2) 0.263(18) Uani 0.5 1 d D U P . .
H12A H 0.4301 -0.1484 0.0947 0.395 Uiso 0.5 1 d R U P . .
H12B H 0.4770 -0.1083 0.1696 0.395 Uiso 0.5 1 d R U P . .
H12C H 0.3847 -0.0925 0.1586 0.395 Uiso 0.5 1 d R U P . .
C11 C 0.5082(7) 0.1491(4) 0.2044(12) 0.248(15) Uani 0.5 1 d D U P . .
H11A H 0.4671 0.1670 0.1662 0.373 Uiso 0.5 1 d R U P . .
H11B H 0.4863 0.1449 0.2605 0.373 Uiso 0.5 1 d R U P . .
H11C H 0.5517 0.1869 0.2044 0.373 Uiso 0.5 1 d R U P . .
C7A C 0.5640(8) -0.0134(11) 0.3416(7) 0.237(12) Uani 0.5 1 d D U P . .
H7AA H 0.6031 -0.0068 0.2975 0.284 Uiso 0.5 1 d R U P . .
H7AB H 0.5765 -0.0616 0.3720 0.284 Uiso 0.5 1 d R U P . .
C9A C 0.5204(18) -0.056(3) 0.4114(12) 0.256(17) Uani 0.5 1 d D U P . .
H9AA H 0.5731 -0.0519 0.4356 0.385 Uiso 0.5 1 d R U P . .
H9AB H 0.5084 -0.0078 0.3806 0.385 Uiso 0.5 1 d R U P . .
H9AC H 0.4816 -0.0631 0.4557 0.385 Uiso 0.5 1 d R U P . .
P2 P 0.5000 0.4907(13) 0.2500 0.197(4) Uani 0.6 2 d DS TU P . .
C22 C 0.3645(9) 0.4018(14) 0.245(3) 0.355(16) Uani 0.5 1 d D U P . .
H22A H 0.3455 0.4206 0.1913 0.426 Uiso 0.5 1 d R U P . .
H22B H 0.3927 0.3523 0.2361 0.426 Uiso 0.5 1 d R U P . .
Cl2 Cl 0.2651(10) 0.442(2) 0.2587(18) 0.464(15) Uani 0.5 1 d D U P . .
C21 C 0.4171(7) 0.464(2) 0.2039(12) 0.282(11) Uani 0.5 1 d D U P . .
H21A H 0.4194 0.5074 0.1643 0.339 Uiso 0.5 1 d R U P . .
H21D H 0.3912 0.4844 0.2537 0.339 Uiso 0.5 1 d R U P . .
C22A C 0.6275(15) 0.4105(19) 0.313(2) 0.32(2) Uani 0.5 1 d D U P . .
H22C H 0.6353 0.3658 0.3505 0.487 Uiso 0.5 1 d R U P . .
H22D H 0.6617 0.4048 0.2647 0.487 Uiso 0.5 1 d R U P . .
H22E H 0.6406 0.4594 0.3422 0.487 Uiso 0.5 1 d R U P . .
C21A C 0.5381(13) 0.4139(12) 0.3012(13) 0.273(12) Uani 0.5 1 d D U P . .
H21B H 0.5240 0.3655 0.2716 0.327 Uiso 0.5 1 d R U P . .
H21C H 0.5030 0.4199 0.3489 0.327 Uiso 0.5 1 d R U P . .
C23 C 0.4837(15) 0.5637(15) 0.3163(11) 0.232(11) Uani 0.5 1 d D U P . .
H23A H 0.4758 0.6107 0.2822 0.279 Uiso 0.5 1 d R U P . .
H23B H 0.5406 0.5551 0.3203 0.279 Uiso 0.5 1 d R U P . .
C24A C 0.6324(13) 0.464(2) 0.156(2) 0.314(19) Uani 0.5 1 d D U P . .
H24A H 0.6609 0.4552 0.1036 0.471 Uiso 0.5 1 d R U P . .
H24B H 0.6581 0.5055 0.1873 0.471 Uiso 0.5 1 d R U P . .
H24C H 0.6325 0.4149 0.1880 0.471 Uiso 0.5 1 d R U P . .
C23A C 0.5652(10) 0.5198(17) 0.1785(11) 0.271(11) Uani 0.5 1 d D U P . .
H23C H 0.5665 0.5674 0.1443 0.326 Uiso 0.5 1 d R U P . .
H23D H 0.5412 0.4781 0.1450 0.326 Uiso 0.5 1 d R U P . .
C24 C 0.533(2) 0.568(2) 0.3959(16) 0.28(2) Uani 0.5 1 d D U P . .
H24D H 0.5604 0.6142 0.4182 0.414 Uiso 0.5 1 d R U P . .
H24E H 0.4762 0.5793 0.3934 0.414 Uiso 0.5 1 d R U P . .
H24F H 0.5420 0.5229 0.4320 0.414 Uiso 0.5 1 d R U P . .
P2' P 0.5000 0.497(2) 0.2500 0.199(5) Uani 0.4 2 d S TU P . .
N4 N 0.3061(13) -0.0712(12) 0.5025(13) 0.211(9) Uani 1 1 d . U . . .
C5 C 0.260(2) -0.0261(16) 0.4899(19) 0.237(10) Uani 1 1 d . U . . .
C4 C 0.3482(13) 0.2445(17) 0.8160(15) 0.172(7) Uani 1 1 d . U . . .
N5 N 0.3620(13) 0.2122(12) 0.8727(13) 0.192(7) Uani 1 1 d . U . . .
C3 C 0.5061(13) 0.2323(18) 0.4203(16) 0.208(8) Uani 1 1 d . U . . .
N6 N 0.5625(9) 0.2050(12) 0.4375(11) 0.181(6) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N6 2.242(15) 4_456 ?
Cd1 N4 2.31(2) 8_665 ?
Cd1 N3 2.296(19) . ?
Cd1 N5 2.31(2) 2_554 ?
Cd1 N2 2.308(19) . ?
Cd1 N1 2.32(2) . ?
C1 N2 1.06(2) . ?
C1 N8 1.37(3) . ?
N1 C2 1.08(3) . ?
P1 C7 1.8003(11) . ?
P1 C7 1.8003(11) 3_655 ?
P1 C7A 1.8002(10) 3_655 ?
P1 C7A 1.8002(10) . ?
P1 C8 1.8012(10) . ?
P1 C8 1.8013(10) 3_655 ?
P1 C10 1.8013(11) 3_655 ?
P1 C10 1.8013(11) . ?
C2 N7 1.29(3) . ?
N3 C6 0.97(2) . ?
C6 N9 1.48(3) . ?
N7 C5 1.33(3) . ?
N8 C4 1.34(3) . ?
N9 C3 1.28(3) . ?
C7 C8 1.475(18) 3_655 ?
C7 C9 1.499(2) . ?
C8 C7 1.475(18) 3_655 ?
C8 C11 1.500(2) . ?
C8 C9 1.809(18) 3_655 ?
C9 C8 1.809(18) 3_655 ?
C9 Cl1 1.8300(11) . ?
C10 C12 1.500(2) . ?
C10 C10 1.76(2) 3_655 ?
C10 C9A 1.87(3) 3_655 ?
C10 C7A 1.90(2) 3_655 ?
C12 C9A 1.24(6) 3_655 ?
C12 C7A 1.54(3) 3_655 ?
C11 C11 1.47(4) 3_655 ?
C7A C12 1.54(3) 3_655 ?
C7A C9A 1.500(2) . ?
C7A C10 1.90(2) 3_655 ?
C9A C12 1.24(6) 3_655 ?
C9A C10 1.87(3) 3_655 ?
P2 C21 1.624(4) . ?
P2 C21 1.624(5) 3_655 ?
P2 C23 1.629(5) . ?
P2 C23 1.629(5) 3_655 ?
P2 C23A 1.641(5) . ?
P2 C23A 1.641(5) 3_655 ?
P2 C21A 1.643(5) 3_655 ?
P2 C21A 1.643(5) . ?
C22 C22A 0.94(5) 3_655 ?
C22 C21 1.502(5) . ?
C22 C21A 1.79(3) 3_655 ?
C22 Cl2 1.800(2) . ?
C22 C24A 1.88(5) 3_655 ?
Cl2 C22A 2.18(4) 3_655 ?
Cl2 C24A 2.21(4) 3_655 ?
C21 C21A 1.12(4) 3_655 ?
C21 C22A 1.19(3) 3_655 ?
C21 P2' 1.66(2) . ?
C22A C22 0.94(5) 3_655 ?
C22A C21 1.19(3) 3_655 ?
C22A C21A 1.501(5) . ?
C22A Cl2 2.18(4) 3_655 ?
C21A C21 1.12(4) 3_655 ?
C21A P2' 1.73(4) . ?
C21A C22 1.79(3) 3_655 ?
C23 C23A 1.10(4) 3_655 ?
C23 C24 1.501(5) . ?
C23 P2' 1.55(4) . ?
C24A C23A 1.502(5) . ?
C24A C22 1.88(5) 3_655 ?
C24A Cl2 2.21(4) 3_655 ?
C23A C23 1.10(4) 3_655 ?
C23A P2' 1.613(14) . ?
P2' C23 1.55(4) 3_655 ?
P2' C23A 1.613(14) 3_655 ?
P2' C21 1.66(2) 3_655 ?
P2' C21A 1.73(4) 3_655 ?
N4 C5 1.10(3) . ?
N4 Cd1 2.31(2) 8_655 ?
C4 N5 1.07(2) . ?
N5 Cd1 2.31(2) 2 ?
C3 N6 1.08(2) . ?
N6 Cd1 2.242(15) 4_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 Cd1 N4 91.7(8) 4_456 8_665 ?
N6 Cd1 N3 176.9(9) 4_456 . ?
N4 Cd1 N3 89.7(10) 8_665 . ?
N6 Cd1 N5 91.2(7) 4_456 2_554 ?
N4 Cd1 N5 89.7(7) 8_665 2_554 ?
N3 Cd1 N5 86.0(9) . 2_554 ?
N6 Cd1 N2 92.6(7) 4_456 . ?
N4 Cd1 N2 87.7(7) 8_665 . ?
N3 Cd1 N2 90.1(9) . . ?
N5 Cd1 N2 175.4(8) 2_554 . ?
N6 Cd1 N1 85.2(8) 4_456 . ?
N4 Cd1 N1 176.9(9) 8_665 . ?
N3 Cd1 N1 93.4(10) . . ?
N5 Cd1 N1 90.5(8) 2_554 . ?
N2 Cd1 N1 92.3(8) . . ?
N2 C1 N8 165(3) . . ?
C2 N1 Cd1 151(3) . . ?
C7 P1 C7 152.9(7) . 3_655 ?
C7 P1 C7A 71.7(3) . 3_655 ?
C7 P1 C7A 110.00(11) 3_655 3_655 ?
C7 P1 C7A 110.00(11) . . ?
C7 P1 C7A 71.7(3) 3_655 . ?
C7A P1 C7A 173.1(10) 3_655 . ?
C7 P1 C8 109.89(11) . . ?
C7 P1 C8 48.4(6) 3_655 . ?
C7A P1 C8 75.1(7) 3_655 . ?
C7A P1 C8 109.86(11) . . ?
C7 P1 C8 48.4(6) . 3_655 ?
C7 P1 C8 109.89(11) 3_655 3_655 ?
C7A P1 C8 109.86(11) 3_655 3_655 ?
C7A P1 C8 75.1(7) . 3_655 ?
C8 P1 C8 92.3(7) . 3_655 ?
C7 P1 C10 94.0(6) . 3_655 ?
C7 P1 C10 109.84(11) 3_655 3_655 ?
C7A P1 C10 109.89(11) 3_655 3_655 ?
C7A P1 C10 63.6(9) . 3_655 ?
C8 P1 C10 155.7(6) . 3_655 ?
C8 P1 C10 107.31(6) 3_655 3_655 ?
C7 P1 C10 109.84(11) . . ?
C7 P1 C10 94.0(6) 3_655 . ?
C7A P1 C10 63.6(9) 3_655 . ?
C7A P1 C10 109.89(11) . . ?
C8 P1 C10 107.32(6) . . ?
C8 P1 C10 155.7(6) 3_655 . ?
C10 P1 C10 58.4(8) 3_655 . ?
C1 N2 Cd1 161(3) . . ?
N1 C2 N7 166(3) . . ?
C6 N3 Cd1 166(3) . . ?
N3 C6 N9 161(4) . . ?
C2 N7 C5 121(3) . . ?
C4 N8 C1 119(2) . . ?
C3 N9 C6 120(2) . . ?
C8 C7 C9 74.9(11) 3_655 . ?
C8 C7 P1 65.9(3) 3_655 . ?
C9 C7 P1 109.67(18) . . ?
C7 C8 C11 128.4(8) 3_655 . ?
C7 C8 C9 53.1(5) 3_655 3_655 ?
C11 C8 C9 78.4(9) . 3_655 ?
C7 C8 P1 65.8(3) 3_655 . ?
C11 C8 P1 109.5(3) . . ?
C9 C8 P1 96.9(6) 3_655 . ?
C7 C9 C8 51.9(8) . 3_655 ?
C7 C9 Cl1 94.8(14) . . ?
C8 C9 Cl1 92.3(14) 3_655 . ?
C12 C10 P1 109.6(3) . . ?
C12 C10 C10 133(2) . 3_655 ?
P1 C10 C10 60.8(4) . 3_655 ?
C12 C10 C9A 42(2) . 3_655 ?
P1 C10 C9A 94.8(12) . 3_655 ?
C10 C10 C9A 153.7(9) 3_655 3_655 ?
C12 C10 C7A 52.1(7) . 3_655 ?
P1 C10 C7A 58.2(5) . 3_655 ?
C10 C10 C7A 107.5(5) 3_655 3_655 ?
C9A C10 C7A 46.9(6) 3_655 3_655 ?
C9A C12 C7A 64.3(16) 3_655 3_655 ?
C9A C12 C10 85(2) 3_655 . ?
C7A C12 C10 77.4(5) 3_655 . ?
C11 C11 C8 109.4(7) 3_655 . ?
C12 C7A C9A 48(2) 3_655 . ?
C12 C7A P1 108.0(14) 3_655 . ?
C9A C7A P1 109.5(3) . . ?
C12 C7A C10 50.5(8) 3_655 3_655 ?
C9A C7A C10 65.4(14) . 3_655 ?
P1 C7A C10 58.2(5) . 3_655 ?
C12 C9A C7A 67.3(19) 3_655 . ?
C12 C9A C10 53.2(13) 3_655 3_655 ?
C7A C9A C10 67.6(12) . 3_655 ?
C21 P2 C21 148.0(18) . 3_655 ?
C21 P2 C23 110.7(4) . . ?
C21 P2 C23 93.4(13) 3_655 . ?
C21 P2 C23 93.4(13) . 3_655 ?
C21 P2 C23 110.7(4) 3_655 3_655 ?
C23 P2 C23 83.4(17) . 3_655 ?
C21 P2 C23A 109.6(4) . . ?
C21 P2 C23A 80.1(9) 3_655 . ?
C23 P2 C23A 109.4(4) . . ?
C23 P2 C23A 39.3(15) 3_655 . ?
C21 P2 C23A 80.1(9) . 3_655 ?
C21 P2 C23A 109.6(4) 3_655 3_655 ?
C23 P2 C23A 39.3(15) . 3_655 ?
C23 P2 C23A 109.4(4) 3_655 3_655 ?
C23A P2 C23A 145.6(17) . 3_655 ?
C21 P2 C21A 40.1(16) . 3_655 ?
C21 P2 C21A 109.5(4) 3_655 3_655 ?
C23 P2 C21A 146.7(14) . 3_655 ?
C23 P2 C21A 109.2(4) 3_655 3_655 ?
C23A P2 C21A 98.4(13) . 3_655 ?
C23A P2 C21A 108.3(4) 3_655 3_655 ?
C21 P2 C21A 109.5(4) . . ?
C21 P2 C21A 40.1(16) 3_655 . ?
C23 P2 C21A 109.2(4) . . ?
C23 P2 C21A 146.7(14) 3_655 . ?
C23A P2 C21A 108.3(4) . . ?
C23A P2 C21A 98.4(13) 3_655 . ?
C21A P2 C21A 77.5(17) 3_655 . ?
C22A C22 C21 52.3(16) 3_655 . ?
C22A C22 C21A 57.0(14) 3_655 3_655 ?
C21 C22 C21A 38.6(17) . 3_655 ?
C22A C22 Cl2 101(3) 3_655 . ?
C21 C22 Cl2 109.3(3) . . ?
C21A C22 Cl2 147(2) 3_655 . ?
C22A C22 C24A 137(3) 3_655 3_655 ?
C21 C22 C24A 88.2(12) . 3_655 ?
C21A C22 C24A 104.8(10) 3_655 3_655 ?
Cl2 C22 C24A 73.8(17) . 3_655 ?
C22 Cl2 C22A 25.1(17) . 3_655 ?
C22 Cl2 C24A 54.8(16) . 3_655 ?
C22A Cl2 C24A 74.1(9) 3_655 3_655 ?
C21A C21 C22A 81(3) 3_655 3_655 ?
C21A C21 C22 85(2) 3_655 . ?
C22A C21 C22 39(3) 3_655 . ?
C21A C21 P2 70.8(10) 3_655 . ?
C22A C21 P2 147(4) 3_655 . ?
C22 C21 P2 119.4(5) . . ?
C21A C21 P2' 74(2) 3_655 . ?
C22A C21 P2' 150(5) 3_655 . ?
C22 C21 P2' 121.7(12) . . ?
P2 C21 P2' 3.5(18) . . ?
C22 C22A C21 88.9(17) 3_655 3_655 ?
C22 C22A C21A 91.3(18) 3_655 . ?
C21 C22A C21A 47.5(19) 3_655 . ?
C22 C22A Cl2 54(2) 3_655 3_655 ?
C21 C22A Cl2 102(3) 3_655 3_655 ?
C21A C22A Cl2 137.5(15) . 3_655 ?
C21 C21A C22A 51.4(10) 3_655 . ?
C21 C21A P2 69.0(8) 3_655 . ?
C22A C21A P2 118.3(4) . . ?
C21 C21A P2' 67.3(9) 3_655 . ?
C22A C21A P2' 117.0(8) . . ?
P2 C21A P2' 2.2(11) . . ?
C21 C21A C22 56.7(12) 3_655 3_655 ?
C22A C21A C22 31.7(17) . 3_655 ?
P2 C21A C22 103.6(12) . 3_655 ?
P2' C21A C22 103.4(12) . 3_655 ?
C23A C23 C24 112(3) 3_655 . ?
C23A C23 P2' 72.7(15) 3_655 . ?
C24 C23 P2' 120.5(8) . . ?
C23A C23 P2 70.9(8) 3_655 . ?
C24 C23 P2 119.1(5) . . ?
P2' C23 P2 2.6(15) . . ?
C23A C24A C22 99.3(11) . 3_655 ?
C23A C24A Cl2 122(2) . 3_655 ?
C22 C24A Cl2 51.5(10) 3_655 3_655 ?
C23 C23A C24A 170(2) 3_655 . ?
C23 C23A P2' 66.8(17) 3_655 . ?
C24A C23A P2' 121.5(18) . . ?
C23 C23A P2 69.8(8) 3_655 . ?
C24A C23A P2 118.3(4) . . ?
P2' C23A P2 3.6(19) . . ?
C23 P2' C23 89(3) . 3_655 ?
C23 P2' C23A 115(3) . . ?
C23 P2' C23A 40.6(15) 3_655 . ?
C23 P2' C23A 40.6(16) . 3_655 ?
C23 P2' C23A 115(3) 3_655 3_655 ?
C23A P2' C23A 153(4) . 3_655 ?
C23 P2' C21 113.0(11) . . ?
C23 P2' C21 95.0(18) 3_655 . ?
C23A P2' C21 109.4(5) . . ?
C23A P2' C21 79.9(8) 3_655 . ?
C23 P2' C21 95.0(18) . 3_655 ?
C23 P2' C21 113.0(11) 3_655 3_655 ?
C23A P2' C21 79.9(8) . 3_655 ?
C23A P2' C21 109.4(5) 3_655 3_655 ?
C21 P2' C21 141(5) . 3_655 ?
C23 P2' C21A 145.9(17) . 3_655 ?
C23 P2' C21A 108.8(5) 3_655 3_655 ?
C23A P2' C21A 96.2(17) . 3_655 ?
C23A P2' C21A 105.7(15) 3_655 3_655 ?
C21 P2' C21A 39(2) . 3_655 ?
C21 P2' C21A 104(3) 3_655 3_655 ?
C23 P2' C21A 108.8(5) . . ?
C23 P2' C21A 145.9(17) 3_655 . ?
C23A P2' C21A 105.7(15) . . ?
C23A P2' C21A 96.2(17) 3_655 . ?
C21 P2' C21A 104(3) . . ?
C21 P2' C21A 39(2) 3_655 . ?
C21A P2' C21A 73(2) 3_655 . ?
C5 N4 Cd1 136(2) . 8_655 ?
N4 C5 N7 173(3) . . ?
N5 C4 N8 165(3) . . ?
C4 N5 Cd1 136(2) . 2 ?
N6 C3 N9 169(3) . . ?
C3 N6 Cd1 153(2) . 4_556 ?

_refine_diff_density_max         2.130
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.176


# start Validation Reply Form
_vrf_PLAT260_1                   
;
PROBLEM: Large Average Ueq of Residue Including       CD1      0.219 Check 
RESPONSE:  The measured temperature is high and the data quality is not good. 
;
_vrf_PLAT084_1                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE:As the measured temperature is high, the thermal vibrations of 
all atoms are intense, the data quality is not good.
;
_vrf_PLAT241_1                   
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         N1 Check 
RESPONSE: This atom has relatively high atomic
displacement parameters compared with the connected atoms. 
;
_vrf_PLAT242_1                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Cd1 Check 
RESPONSE: This atom has relatively Low  atomic
displacement parameters compared with the connected atoms. 
;

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1845896'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Cd N9, C8 H18 F P'
_chemical_formula_sum            'C14 H18 Cd F N9 P'
_chemical_formula_weight         474.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

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

_cell_length_a                   16.172(2)
_cell_length_b                   15.6943(17)
_cell_length_c                   16.8867(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4286.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    3329
_cell_measurement_theta_min      2.519
_cell_measurement_theta_max      31.717

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    1.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Rigaku,SCXmini
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20435
_diffrn_reflns_av_unetI/netI     0.0983
_diffrn_reflns_av_R_equivalents  0.1384
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         31.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3329
_reflns_number_gt                1379
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+25.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     185
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.2682
_refine_ls_R_factor_gt           0.1470
_refine_ls_wR_factor_ref         0.4619
_refine_ls_wR_factor_gt          0.3692
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.0000 0.23575(12) 0.32458(8) 0.1551(11) Uani 1 2 d S TU P . .
P1 P 0.2452(4) 0.0000 0.0000 0.189(3) Uani 1 2 d DS TU P . .
N9 N 0.2500 0.293(3) 0.2500 0.349(17) Uani 1 2 d S TU P . .
N7 N 0.0000 0.018(2) 0.158(2) 0.305(12) Uani 1 2 d S TU P . .
N1 N 0.0000 0.3013(18) 0.1972(12) 0.230(9) Uani 1 2 d S TU P . .
C3 C 0.0000 0.058(2) 0.230(3) 0.264(12) Uani 1 2 d S TU P . .
N5 N 0.0000 0.1005(18) 0.2727(19) 0.252(10) Uani 1 2 d S TU P . .
C5 C 0.191(3) 0.252(3) 0.305(4) 0.308(14) Uani 1 1 d . U . . .
C2 C 0.0000 0.313(2) 0.1383(15) 0.253(11) Uani 1 2 d S TU P . .
N3 N 0.1428(19) 0.238(2) 0.325(2) 0.275(13) Uani 1 1 d . U . . .
N6 N 0.0000 0.3615(19) 0.0766(12) 0.277(10) Uani 1 2 d S TU P . .
C7 C 0.308(4) 0.0049(16) 0.1479(15) 0.306(16) Uani 0.5 1 d D U P . .
H7A H 0.2750 -0.0036 0.1943 0.367 Uiso 0.5 1 d R U P . .
H7B H 0.3651 -0.0052 0.1616 0.367 Uiso 0.5 1 d R U P . .
C9 C 0.152(2) -0.1376(18) -0.0364(15) 0.275(17) Uani 0.5 1 d D U P . .
H9A H 0.1377 -0.1755 -0.0787 0.413 Uiso 0.5 1 d R U P . .
H9B H 0.1979 -0.1611 -0.0072 0.413 Uiso 0.5 1 d R U P . .
H9C H 0.1059 -0.1303 -0.0017 0.413 Uiso 0.5 1 d R U P . .
C8 C 0.2105(10) -0.0739(7) -0.0723(7) 0.249(12) Uani 0.5 1 d D U P . .
H8A H 0.2565 -0.0813 -0.1076 0.299 Uiso 0.5 1 d R U P . .
H8B H 0.1652 -0.0507 -0.1022 0.299 Uiso 0.5 1 d R U P . .
F1 F 0.3099(18) 0.0832(12) 0.1140(15) 0.35(2) Uani 0.25 1 d D U P . .
C6 C 0.2741(12) -0.0557(8) 0.0875(5) 0.273(13) Uani 0.5 1 d D U P . .
H6A H 0.3203 -0.0896 0.0710 0.328 Uiso 0.5 1 d R U P . .
H6B H 0.2321 -0.0933 0.1073 0.328 Uiso 0.5 1 d R U P . .
C7A C 0.3918(13) -0.0039(15) -0.076(2) 0.35(2) Uani 0.5 1 d D U P . .
H7AA H 0.3879 -0.0004 -0.1331 0.419 Uiso 0.5 1 d R U P . .
H7AB H 0.4440 0.0195 -0.0604 0.419 Uiso 0.5 1 d R U P . .
C9A C 0.1985(14) 0.1621(7) 0.029(3) 0.275(17) Uani 0.5 1 d D U P . .
H9AA H 0.1502 0.1930 0.0458 0.412 Uiso 0.5 1 d R U P . .
H9AB H 0.2453 0.1806 0.0598 0.412 Uiso 0.5 1 d R U P . .
H9AC H 0.2086 0.1725 -0.0258 0.412 Uiso 0.5 1 d R U P . .
C8A C 0.1650(7) 0.0733(7) 0.0223(10) 0.241(12) Uani 0.5 1 d D U P . .
H8AA H 0.1540 0.0630 0.0774 0.289 Uiso 0.5 1 d R U P . .
H8AB H 0.1176 0.0549 -0.0075 0.289 Uiso 0.5 1 d R U P . .
F1A F 0.3790(13) -0.0819(12) -0.043(2) 0.39(2) Uani 0.25 1 d D U P . .
C6A C 0.3325(7) 0.0564(8) -0.0372(10) 0.301(15) Uani 0.5 1 d D U P . .
H6AA H 0.3535 0.0896 0.0061 0.361 Uiso 0.5 1 d R U P . .
H6AB H 0.3089 0.0947 -0.0753 0.361 Uiso 0.5 1 d R U P . .
N2 N 0.0000 -0.1379(19) 0.1316(19) 0.242(10) Uani 1 2 d S TU P . .
C1 C 0.0000 -0.068(2) 0.1435(18) 0.235(10) Uani 1 2 d S TU P . .
N4 N 0.0000 0.3220(18) -0.0515(13) 0.223(9) Uani 1 2 d S TU P . .
C4 C 0.0000 0.3304(19) 0.0105(15) 0.215(10) Uani 1 2 d S TU P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N2 2.12(3) 10_566 ?
Cd1 N4 2.28(2) 2 ?
Cd1 N3 2.31(3) 11 ?
Cd1 N3 2.31(3) . ?
Cd1 N5 2.30(3) . ?
Cd1 N1 2.38(2) . ?
P1 C8 1.7747(18) . ?
P1 C8 1.7748(18) 3 ?
P1 C8A 1.7746(18) . ?
P1 C8A 1.7746(18) 3 ?
P1 C6 1.7793(18) . ?
P1 C6 1.7793(18) 3 ?
P1 C6A 1.7805(18) . ?
P1 C6A 1.7805(18) 3 ?
N9 C5 1.48(6) 8_545 ?
N9 C5 1.48(6) . ?
N7 C3 1.36(4) . ?
N7 C1 1.38(4) . ?
N1 C2 1.01(3) . ?
C3 N5 0.99(4) . ?
C5 N3 0.88(5) . ?
C2 N6 1.29(3) . ?
N6 C4 1.22(3) . ?
C7 F1 1.356(12) . ?
C7 C6 1.500(2) . ?
C7 C7A 1.81(6) 3 ?
C7 H7A 0.9601 . ?
C7 H7B 0.9600 . ?
C9 C9A 0.85(5) 3 ?
C9 C8A 1.056(19) 3 ?
C9 C8 1.500(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9601 . ?
C9 H9C 0.9601 . ?
C8 C8A 1.12(3) 3 ?
C8 C9A 1.58(4) 3 ?
C8 F1 1.76(3) 3 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9601 . ?
F1 C8 1.76(3) 3 ?
F1 F1A 1.64(5) 3 ?
C6 C6A 1.27(3) 3 ?
C6 C7A 2.13(3) 3 ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C7A F1A 1.363(18) . ?
C7A C6A 1.501(2) . ?
C7A C7 1.81(6) 3 ?
C7A C6 2.13(3) 3 ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9599 . ?
C9A C9 0.85(5) 3 ?
C9A C8 1.58(4) 3 ?
C9A C8A 1.500(2) . ?
C9A H9AA 0.9599 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8A C8 1.12(3) 3 ?
C8A C9 1.056(19) 3 ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9601 . ?
F1A C6A 1.60(3) 3 ?
F1A F1 1.64(5) 3 ?
C6A C6 1.27(3) 3 ?
C6A F1A 1.60(3) 3 ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
N2 C1 1.12(4) . ?
N2 Cd1 2.12(3) 10_556 ?
N4 C4 1.06(2) . ?
N4 Cd1 2.28(2) 2_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cd1 N4 93.0(11) 10_566 2 ?
N2 Cd1 N3 89.1(8) 10_566 11 ?
N4 Cd1 N3 90.1(9) 2 11 ?
N2 Cd1 N3 89.1(8) 10_566 . ?
N4 Cd1 N3 90.1(9) 2 . ?
N3 Cd1 N3 178.2(17) 11 . ?
N2 Cd1 N5 178.1(12) 10_566 . ?
N4 Cd1 N5 89.0(10) 2 . ?
N3 Cd1 N5 90.9(8) 11 . ?
N3 Cd1 N5 90.9(8) . . ?
N2 Cd1 N1 84.9(11) 10_566 . ?
N4 Cd1 N1 177.9(10) 2 . ?
N3 Cd1 N1 89.8(9) 11 . ?
N3 Cd1 N1 89.8(9) . . ?
N5 Cd1 N1 93.1(10) . . ?
C8 P1 C8 143.1(10) . 3 ?
C8 P1 C8A 109.76(11) . . ?
C8 P1 C8A 36.8(9) 3 . ?
C8 P1 C8A 36.8(9) . 3 ?
C8 P1 C8A 109.76(11) 3 3 ?
C8A P1 C8A 86.0(9) . 3 ?
C8 P1 C6 109.50(11) . . ?
C8 P1 C6 80.3(5) 3 . ?
C8A P1 C6 109.49(11) . . ?
C8A P1 C6 92.9(9) 3 . ?
C8 P1 C6 80.3(5) . 3 ?
C8 P1 C6 109.49(11) 3 3 ?
C8A P1 C6 92.9(9) . 3 ?
C8A P1 C6 109.49(11) 3 3 ?
C6 P1 C6 149.6(12) . 3 ?
C8 P1 C6A 109.42(11) . . ?
C8 P1 C6A 99.7(8) 3 . ?
C8A P1 C6A 109.43(11) . . ?
C8A P1 C6A 145.8(9) 3 . ?
C6 P1 C6A 109.22(11) . . ?
C6 P1 C6A 41.8(11) 3 . ?
C8 P1 C6A 99.7(8) . 3 ?
C8 P1 C6A 109.42(11) 3 3 ?
C8A P1 C6A 145.8(9) . 3 ?
C8A P1 C6A 109.43(11) 3 3 ?
C6 P1 C6A 41.8(11) . 3 ?
C6 P1 C6A 109.22(11) 3 3 ?
C6A P1 C6A 75.1(11) . 3 ?
C5 N9 C5 128(6) 8_545 . ?
C3 N7 C1 127(4) . . ?
C2 N1 Cd1 165(3) . . ?
N5 C3 N7 164(5) . . ?
C3 N5 Cd1 155(4) . . ?
N3 C5 N9 157(7) . . ?
N1 C2 N6 154(4) . . ?
C5 N3 Cd1 153(6) . . ?
C4 N6 C2 120(3) . . ?
F1 C7 C6 107.1(6) . . ?
F1 C7 C7A 73(3) . 3 ?
C6 C7 C7A 79(2) . 3 ?
F1 C7 H7A 118.7 . . ?
C6 C7 H7A 105.0 . . ?
C7A C7 H7A 164.0 3 . ?
F1 C7 H7B 103.6 . . ?
C6 C7 H7B 114.3 . . ?
C7A C7 H7B 56.4 3 . ?
H7A C7 H7B 108.5 . . ?
C9A C9 C8A 104(2) 3 3 ?
C9A C9 C8 79(3) 3 . ?
C8A C9 C8 48.2(14) 3 . ?
C9A C9 H9A 92.3 3 . ?
C8A C9 H9A 143.9 3 . ?
C8 C9 H9A 105.6 . . ?
C9A C9 H9B 22.9 3 . ?
C8A C9 H9B 96.0 3 . ?
C8 C9 H9B 89.1 . . ?
H9A C9 H9B 109.5 . . ?
C9A C9 H9C 131.1 3 . ?
C8A C9 H9C 84.2 3 . ?
C8 C9 H9C 131.1 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8A C8 C9A 65.1(16) 3 3 ?
C8A C8 C9 44.7(10) 3 . ?
C9A C8 C9 31.9(19) 3 . ?
C8A C8 F1 154.4(13) 3 3 ?
C9A C8 F1 102.9(14) 3 3 ?
C9 C8 F1 132.7(17) . 3 ?
C8A C8 P1 71.6(5) 3 . ?
C9A C8 P1 107.2(18) 3 . ?
C9 C8 P1 110.81(19) . . ?
F1 C8 P1 92.3(11) 3 . ?
C8A C8 H8A 167.9 3 . ?
C9A C8 H8A 105.9 3 . ?
C9 C8 H8A 130.9 . . ?
F1 C8 H8A 15.2 3 . ?
P1 C8 H8A 105.1 . . ?
C8A C8 H8B 83.8 3 . ?
C9A C8 H8B 118.8 3 . ?
C9 C8 H8B 89.3 . . ?
F1 C8 H8B 121.2 3 . ?
P1 C8 H8B 110.8 . . ?
H8A C8 H8B 108.1 . . ?
C7 F1 C8 94(2) . 3 ?
C7 F1 F1A 108(3) . 3 ?
C8 F1 F1A 109.3(16) 3 3 ?
C6A C6 C7 101(3) 3 . ?
C6A C6 P1 69.1(6) 3 . ?
C7 C6 P1 110.49(18) . . ?
C6A C6 C7A 44.0(11) 3 3 ?
C7 C6 C7A 57(2) . 3 ?
P1 C6 C7A 86.9(10) . 3 ?
C6A C6 H6A 38.9 3 . ?
C7 C6 H6A 105.1 . . ?
P1 C6 H6A 103.6 . . ?
C7A C6 H6A 61.4 3 . ?
C6A C6 H6B 138.8 3 . ?
C7 C6 H6B 114.6 . . ?
P1 C6 H6B 113.9 . . ?
C7A C6 H6B 158.9 3 . ?
H6A C6 H6B 108.1 . . ?
F1A C7A C6A 106.7(9) . . ?
F1A C7A C7 98.8(17) . 3 ?
C6A C7A C7 79.9(14) . 3 ?
F1A C7A C6 107.2(10) . 3 ?
C6A C7A C6 36.0(10) . 3 ?
C7 C7A C6 43.9(8) 3 3 ?
F1A C7A H7AA 116.8 . . ?
C6A C7A H7AA 111.3 . . ?
C7 C7A H7AA 44.6 3 . ?
C6 C7A H7AA 80.2 3 . ?
F1A C7A H7AB 111.2 . . ?
C6A C7A H7AB 101.4 . . ?
C7 C7A H7AB 147.9 3 . ?
C6 C7A H7AB 130.1 3 . ?
H7AA C7A H7AB 108.4 . . ?
C9 C9A C8 69(2) 3 3 ?
C9 C9A C8A 43.2(6) 3 . ?
C8 C9A C8A 42.6(12) 3 . ?
C9 C9A H9AA 58.3 3 . ?
C8 C9A H9AA 114.3 3 . ?
C8A C9A H9AA 101.5 . . ?
C9 C9A H9AB 139.2 3 . ?
C8 C9A H9AB 85.6 3 . ?
C8A C9A H9AB 127.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C9 C9A H9AC 111.3 3 . ?
C8 C9A H9AC 125.1 3 . ?
C8A C9A H9AC 98.2 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8 C8A C9 87.1(19) 3 3 ?
C8 C8A C9A 72(2) 3 . ?
C9 C8A C9A 33(2) 3 . ?
C8 C8A P1 71.6(5) 3 . ?
C9 C8A P1 144(2) 3 . ?
C9A C8A P1 110.77(19) . . ?
C8 C8A H8AA 52.6 3 . ?
C9 C8A H8AA 84.7 3 . ?
C9A C8A H8AA 98.4 . . ?
P1 C8A H8AA 103.4 . . ?
C8 C8A H8AB 157.1 3 . ?
C9 C8A H8AB 104.6 3 . ?
C9A C8A H8AB 127.5 . . ?
P1 C8A H8AB 106.1 . . ?
H8AA C8A H8AB 108.1 . . ?
C7A F1A C6A 101.2(12) . 3 ?
C7A F1A F1 79(2) . 3 ?
C6A F1A F1 107.6(13) 3 3 ?
C6 C6A C7A 100.0(17) 3 . ?
C6 C6A F1A 156.5(19) 3 3 ?
C7A C6A F1A 103(2) . 3 ?
C6 C6A P1 69.0(6) 3 . ?
C7A C6A P1 110.44(19) . . ?
F1A C6A P1 101.4(12) 3 . ?
C6 C6A H6AA 141.0 3 . ?
C7A C6A H6AA 116.9 . . ?
F1A C6A H6AA 18.8 3 . ?
P1 C6A H6AA 106.4 . . ?
C6 C6A H6AB 42.4 3 . ?
C7A C6A H6AB 110.7 . . ?
F1A C6A H6AB 126.7 3 . ?
P1 C6A H6AB 103.5 . . ?
H6AA C6A H6AB 108.1 . . ?
C1 N2 Cd1 149(3) . 10_556 ?
N2 C1 N7 180(4) . . ?
C4 N4 Cd1 164(3) . 2_554 ?
N4 C4 N6 164(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N7 C3 N5 180.000(11) . . . . ?
N7 C3 N5 Cd1 0.000(15) . . . . ?
C5 N9 C5 N3 -117(18) 8_545 . . . ?
Cd1 N1 C2 N6 180.000(11) . . . . ?
N9 C5 N3 Cd1 7(28) . . . . ?
N1 C2 N6 C4 180.000(11) . . . . ?
C9A C9 C8 C8A -120(4) 3 . . 3 ?
C8A C9 C8 C9A 120(4) 3 . . 3 ?
C9A C9 C8 F1 25(4) 3 . . 3 ?
C8A C9 C8 F1 144(2) 3 . . 3 ?
C9A C9 C8 P1 -89(4) 3 . . . ?
C8A C9 C8 P1 30(3) 3 . . . ?
C8 P1 C8 C8A -32.7(10) 3 . . 3 ?
C8A P1 C8 C8A -52.9(15) . . . 3 ?
C6 P1 C8 C8A 67.4(15) . . . 3 ?
C6 P1 C8 C8A -142.4(9) 3 . . 3 ?
C6A P1 C8 C8A -173.0(15) . . . 3 ?
C6A P1 C8 C8A 109.5(8) 3 . . 3 ?
C8 P1 C8 C9A -88.1(15) 3 . . 3 ?
C8A P1 C8 C9A -108.3(17) . . . 3 ?
C8A P1 C8 C9A -55.4(12) 3 . . 3 ?
C6 P1 C8 C9A 11.9(17) . . . 3 ?
C6 P1 C8 C9A 162.1(17) 3 . . 3 ?
C6A P1 C8 C9A 131.6(17) . . . 3 ?
C6A P1 C8 C9A 54.1(17) 3 . . 3 ?
C8 P1 C8 C9 -55(2) 3 . . . ?
C8A P1 C8 C9 -75(2) . . . . ?
C8A P1 C8 C9 -22(2) 3 . . . ?
C6 P1 C8 C9 46(2) . . . . ?
C6 P1 C8 C9 -164(2) 3 . . . ?
C6A P1 C8 C9 165(2) . . . . ?
C6A P1 C8 C9 88(2) 3 . . . ?
C8 P1 C8 F1 167.6(6) 3 . . 3 ?
C8A P1 C8 F1 147.5(8) . . . 3 ?
C8A P1 C8 F1 -159.7(12) 3 . . 3 ?
C6 P1 C8 F1 -92.3(8) . . . 3 ?
C6 P1 C8 F1 57.9(8) 3 . . 3 ?
C6A P1 C8 F1 27.4(9) . . . 3 ?
C6A P1 C8 F1 -50.1(8) 3 . . 3 ?
C6 C7 F1 C8 44(4) . . . 3 ?
C7A C7 F1 C8 117.1(14) 3 . . 3 ?
C6 C7 F1 F1A -68(4) . . . 3 ?
C7A C7 F1 F1A 5.2(13) 3 . . 3 ?
F1 C7 C6 C6A 69(5) . . . 3 ?
C7A C7 C6 C6A -0.1(11) 3 . . 3 ?
F1 C7 C6 P1 -3(6) . . . . ?
C7A C7 C6 P1 -72(2) 3 . . . ?
F1 C7 C6 C7A 69(4) . . . 3 ?
C8 P1 C6 C6A 82.7(12) . . . 3 ?
C8 P1 C6 C6A -134.1(7) 3 . . 3 ?
C8A P1 C6 C6A -156.9(12) . . . 3 ?
C8A P1 C6 C6A 116.3(6) 3 . . 3 ?
C6 P1 C6 C6A -21.8(8) 3 . . 3 ?
C6A P1 C6 C6A -37.1(12) . . . 3 ?
C8 P1 C6 C7 177(3) . . . . ?
C8 P1 C6 C7 -40(3) 3 . . . ?
C8A P1 C6 C7 -63(3) . . . . ?
C8A P1 C6 C7 -150(3) 3 . . . ?
C6 P1 C6 C7 72(3) 3 . . . ?
C6A P1 C6 C7 57(3) . . . . ?
C6A P1 C6 C7 94(3) 3 . . . ?
C8 P1 C6 C7A 124.1(11) . . . 3 ?
C8 P1 C6 C7A -92.8(7) 3 . . 3 ?
C8A P1 C6 C7A -115.5(11) . . . 3 ?
C8A P1 C6 C7A 157.7(7) 3 . . 3 ?
C6 P1 C6 C7A 19.5(8) 3 . . 3 ?
C6A P1 C6 C7A 4.3(11) . . . 3 ?
C6A P1 C6 C7A 41.3(8) 3 . . 3 ?
C9 C9A C8A C8 -113(5) 3 . . 3 ?
C8 C9A C8A C9 113(5) 3 . . 3 ?
C9 C9A C8A P1 -175(4) 3 . . . ?
C8 C9A C8A P1 -61.6(16) 3 . . . ?
C8 P1 C8A C8 159.8(9) . . . 3 ?
C8A P1 C8A C8 131.2(12) 3 . . 3 ?
C6 P1 C8A C8 39.6(9) . . . 3 ?
C6 P1 C8A C8 -119.4(12) 3 . . 3 ?
C6A P1 C8A C8 -80.1(9) . . . 3 ?
C6A P1 C8A C8 12(2) 3 . . 3 ?
C8 P1 C8A C9 -143(3) . . . 3 ?
C8 P1 C8A C9 57(4) 3 . . 3 ?
C8A P1 C8A C9 -172(4) 3 . . 3 ?
C6 P1 C8A C9 97(3) . . . 3 ?
C6 P1 C8A C9 -62(4) 3 . . 3 ?
C6A P1 C8A C9 -23(3) . . . 3 ?
C6A P1 C8A C9 69(4) 3 . . 3 ?
C8 P1 C8A C9A -138(3) . . . . ?
C8 P1 C8A C9A 62(3) 3 . . . ?
C8A P1 C8A C9A -167(3) 3 . . . ?
C6 P1 C8A C9A 102(3) . . . . ?
C6 P1 C8A C9A -57(3) 3 . . . ?
C6A P1 C8A C9A -18(3) . . . . ?
C6A P1 C8A C9A 74(3) 3 . . . ?
C6A C7A F1A C6A -19(3) . . . 3 ?
C7 C7A F1A C6A -101.2(15) 3 . . 3 ?
C6 C7A F1A C6A -57(2) 3 . . 3 ?
C6A C7A F1A F1 87(2) . . . 3 ?
C7 C7A F1A F1 4.8(11) 3 . . 3 ?
C6 C7A F1A F1 49.1(15) 3 . . 3 ?
F1A C7A C6A C6 -96(2) . . . 3 ?
C7 C7A C6A C6 -0.1(11) 3 . . 3 ?
F1A C7A C6A F1A 83(2) . . . 3 ?
C7 C7A C6A F1A 178.9(17) 3 . . 3 ?
C6 C7A C6A F1A 179.0(11) 3 . . 3 ?
F1A C7A C6A P1 -25(3) . . . . ?
C7 C7A C6A P1 71.1(15) 3 . . . ?
C6 C7A C6A P1 71.2(9) 3 . . . ?
C8 P1 C6A C6 48.6(7) . . . 3 ?
C8 P1 C6A C6 -108.4(8) 3 . . 3 ?
C8A P1 C6A C6 -71.7(7) . . . 3 ?
C8A P1 C6A C6 41(2) 3 . . 3 ?
C6 P1 C6A C6 168.5(7) . . . 3 ?
C6A P1 C6A C6 143.9(10) 3 . . 3 ?
C8 P1 C6A C7A -45(2) . . . . ?
C8 P1 C6A C7A 158.3(18) 3 . . . ?
C8A P1 C6A C7A -165(2) . . . . ?
C8A P1 C6A C7A -52(3) 3 . . . ?
C6 P1 C6A C7A 75(2) . . . . ?
C6 P1 C6A C7A -93(2) 3 . . . ?
C6A P1 C6A C7A 50.7(19) 3 . . . ?
C8 P1 C6A F1A -153.7(15) . . . 3 ?
C8 P1 C6A F1A 49.2(14) 3 . . 3 ?
C8A P1 C6A F1A 86.0(15) . . . 3 ?
C8A P1 C6A F1A -161.2(8) 3 . . 3 ?
C6 P1 C6A F1A -33.9(15) . . . 3 ?
C6 P1 C6A F1A 158(2) 3 . . 3 ?
C6A P1 C6A F1A -58.4(13) 3 . . 3 ?
Cd1 N4 C4 N6 180.000(9) 2_554 . . . ?
C2 N6 C4 N4 180.000(10) . . . . ?

_refine_diff_density_max         0.777
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.189



# start Validation Reply Form
_vrf_PLAT084_19                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.46 Report
RESPONSE: wR2 will in general have a value twice of that of R1 with 
refinement on F2. High R1 value results in the high wR2 value.
;
_vrf_PLAT260_19                  
;
PROBLEM: Large Average Ueq of Residue Including       CD1      0.256 Check 
RESPONSE: The measured temperature is high and the data quality is not good. 
;
_vrf_PLAT241_19                  
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         N7 Check 
RESPONSE:This atom has relatively high atomic
displacement parameters compared with the Connected atoms
;
_vrf_PLAT242_19                  
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Cd1 Check 
RESPONSE: This atom has relatively low atomic
displacement parameters compared with the Connected atoms
;
