# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20170591
_database_code_depnum_ccdc_archive 'CCDC 1553255'
_audit_update_record             
;
2017-05-31 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;
_audit_creation_method           'Olex2 1.2'

_audit_creation_date             2017-05-25
_chemical_formula_sum            'C44 H32 N2 O2 P2'
_chemical_formula_weight         682.650
_refine_ls_R_factor_all          0.059
_cell_length_a                   8.4342(6)
_cell_length_b                   9.2098(7)
_cell_length_c                   12.2670(9)
_cell_angle_alpha                68.985(7)
_cell_angle_beta                 88.068(6)
_cell_angle_gamma                74.661(7)
_cell_volume                     855.8(1)
_cell_formula_units_Z            1
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200
P ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C 0.7972(3) -0.3192(3) 0.8142(2) 1.000 2 i ? d Uani 0.0363(5)
C2 C 0.9050(3) -0.4721(3) 0.8440(2) 1.000 2 i ? d Uani 0.0481(6)
H2 H 0.8649 -0.5602 0.8525 1.000 2 i ? calc Uiso 0.05800
C3 C 1.0725(4) -0.4938(4) 0.8613(3) 1.000 2 i ? d Uani 0.0601(7)
H3 H 1.1448 -0.5965 0.8809 1.000 2 i ? calc Uiso 0.07200
C4 C 1.1316(4) -0.3647(4) 0.8494(3) 1.000 2 i ? d Uani 0.0635(8)
H4 H 1.2442 -0.3798 0.8605 1.000 2 i ? calc Uiso 0.07600
C5 C 1.0252(4) -0.2118(4) 0.8211(3) 1.000 2 i ? d Uani 0.0642(8)
H5 H 1.0659 -0.1246 0.8142 1.000 2 i ? calc Uiso 0.07700
C6 C 0.8582(3) -0.1891(3) 0.8032(2) 1.000 2 i ? d Uani 0.0505(6)
H6 H 0.7865 -0.0862 0.7837 1.000 2 i ? calc Uiso 0.06100
C7 C 0.4621(3) -0.1688(3) 0.8622(2) 1.000 2 i ? d Uani 0.0371(5)
C8 C 0.4323(3) -0.2205(3) 0.9788(2) 1.000 2 i ? d Uani 0.0464(6)
H8 H 0.4842 -0.3250 1.0286 1.000 2 i ? calc Uiso 0.05600
C9 C 0.3233(4) -0.1139(3) 1.0209(2) 1.000 2 i ? d Uani 0.0570(7)
H9 H 0.3023 -0.1470 1.0997 1.000 2 i ? calc Uiso 0.06800
C10 C 0.2461(4) 0.0402(3) 0.9468(2) 1.000 2 i ? d Uani 0.0576(8)
H10 H 0.1724 0.1095 0.9762 1.000 2 i ? calc Uiso 0.06900
C11 C 0.2761(3) 0.0950(3) 0.8281(2) 1.000 2 i ? d Uani 0.0468(6)
H11 H 0.2240 0.1997 0.7788 1.000 2 i ? calc Uiso 0.05600
C12 C 0.3855(3) -0.0107(3) 0.7856(2) 1.000 2 i ? d Uani 0.0363(5)
C13 C 0.4303(3) 0.0082(3) 0.6651(2) 1.000 2 i ? d Uani 0.0349(5)
C14 C 0.5203(3) -0.1303(3) 0.6471(2) 1.000 2 i ? d Uani 0.0341(5)
C15 C 0.5391(3) -0.0816(2) 0.5260(2) 1.000 2 i ? d Uani 0.0325(5)
C16 C 0.3292(3) 0.3070(3) 0.5426(2) 1.000 2 i ? d Uani 0.0337(5)
C17 C 0.3862(3) 0.3738(3) 0.6131(2) 1.000 2 i ? d Uani 0.0407(5)
H17 H 0.4664 0.3095 0.6736 1.000 2 i ? calc Uiso 0.04900
C18 C 0.3230(3) 0.5365(3) 0.5929(2) 1.000 2 i ? d Uani 0.0479(6)
H18 H 0.3583 0.5802 0.6422 1.000 2 i ? calc Uiso 0.05800
C19 C 0.2085(3) 0.6354(3) 0.5008(2) 1.000 2 i ? d Uani 0.0512(6)
C20 C 0.1570(3) 0.5669(3) 0.4296(2) 1.000 2 i ? d Uani 0.0514(7)
H20 H 0.0818 0.6323 0.3662 1.000 2 i ? calc Uiso 0.06200
C21 C 0.2148(3) 0.4038(3) 0.4505(2) 1.000 2 i ? d Uani 0.0420(5)
H21 H 0.1767 0.3596 0.4028 1.000 2 i ? calc Uiso 0.05000
C22 C 0.1400(5) 0.8134(4) 0.4807(3) 1.000 2 i ? d Uani 0.0817(11)
H22A H 0.1206 0.8265 0.5546 1.000 2 i ? calc Uiso 0.12200
H22B H 0.0382 0.8555 0.4333 1.000 2 i ? calc Uiso 0.12200
H22C H 0.2177 0.8709 0.4415 1.000 2 i ? calc Uiso 0.12200
N1 N 0.3952(2) 0.1389(2) 0.5608(1) 1.000 2 i ? d Uani 0.0345(4)
O1 O 0.5442(2) -0.4478(2) 0.8062(1) 1.000 2 i ? d Uani 0.0430(4)
P1 P 0.5811(1) -0.2923(1) 0.785() 1.000 2 i ? d Uani 0.03355(18)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.386(3) no
C1 C6 . . 1.387(3) no
C1 P1 . . 1.803(2) no
C2 H2 . . 0.9300 no
C2 C3 . . 1.386(4) no
C3 H3 . . 0.9300 no
C3 C4 . . 1.367(4) no
C4 H4 . . 0.9300 no
C4 C5 . . 1.382(4) no
C5 H5 . . 0.9300 no
C5 C6 . . 1.381(4) no
C6 H6 . . 0.9300 no
C7 C8 . . 1.373(3) no
C7 C12 . . 1.408(3) no
C7 P1 . . 1.818(2) no
C8 H8 . . 0.9300 no
C8 C9 . . 1.390(4) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.375(4) no
C10 H10 . . 0.9300 no
C10 C11 . . 1.398(3) no
C11 H11 . . 0.9300 no
C11 C12 . . 1.388(3) no
C12 C13 . . 1.473(3) no
C13 C14 . . 1.389(3) no
C13 N1 . . 1.381(3) no
C14 C15 . . 1.406(3) no
C14 P1 . . 1.787(2) no
C15 C15 . 2_656 1.384(4) no
C15 N1 . 2_656 1.390(3) no
C16 C17 . . 1.387(3) no
C16 C21 . . 1.378(3) no
C16 N1 . . 1.435(3) no
C17 H17 . . 0.9300 no
C17 C18 . . 1.383(3) no
C18 H18 . . 0.9300 no
C18 C19 . . 1.381(4) no
C19 C20 . . 1.384(4) no
C19 C22 . . 1.517(4) no
C20 H20 . . 0.9300 no
C20 C21 . . 1.380(3) no
C21 H21 . . 0.9300 no
C22 H22A . . 0.9600 no
C22 H22B . . 0.9600 no
C22 H22C . . 0.9600 no
N1 C15 . 2_656 1.390(3) no
O1 P1 . . 1.4761(16) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . . 119.5(2) no
C2 C1 P1 . . . 119.16(19) no
C6 C1 P1 . . . 121.35(19) no
C1 C2 H2 . . . 120.00 no
C1 C2 C3 . . . 120.0(3) no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 119.90 no
C4 C3 C2 . . . 120.1(3) no
C4 C3 H3 . . . 119.90 no
C3 C4 H4 . . . 119.80 no
C3 C4 C5 . . . 120.5(3) no
C5 C4 H4 . . . 119.80 no
C4 C5 H5 . . . 120.10 no
C6 C5 C4 . . . 119.7(3) no
C6 C5 H5 . . . 120.10 no
C1 C6 H6 . . . 119.90 no
C5 C6 C1 . . . 120.2(3) no
C5 C6 H6 . . . 119.90 no
C8 C7 C12 . . . 121.4(2) no
C8 C7 P1 . . . 126.40(19) no
C12 C7 P1 . . . 111.93(16) no
C7 C8 H8 . . . 120.60 no
C7 C8 C9 . . . 118.8(2) no
C9 C8 H8 . . . 120.60 no
C8 C9 H9 . . . 119.80 no
C10 C9 C8 . . . 120.4(2) no
C10 C9 H9 . . . 119.80 no
C9 C10 H10 . . . 119.30 no
C9 C10 C11 . . . 121.4(2) no
C11 C10 H10 . . . 119.30 no
C10 C11 H11 . . . 120.80 no
C12 C11 C10 . . . 118.4(2) no
C12 C11 H11 . . . 120.80 no
C7 C12 C13 . . . 109.9(2) no
C11 C12 C7 . . . 119.5(2) no
C11 C12 C13 . . . 130.4(2) no
C14 C13 C12 . . . 116.71(19) no
N1 C13 C12 . . . 132.6(2) no
N1 C13 C14 . . . 110.67(18) no
C13 C14 C15 . . . 105.35(19) no
C13 C14 P1 . . . 109.57(15) no
C15 C14 P1 . . . 144.74(17) no
C15 C15 C14 2_656 . . 108.9(2) no
C15 C15 N1 2_656 . 2_656 108.4(2) no
N1 C15 C14 2_656 . . 142.7(2) no
C17 C16 N1 . . . 120.4(2) no
C21 C16 C17 . . . 120.0(2) no
C21 C16 N1 . . . 119.5(2) no
C16 C17 H17 . . . 120.20 no
C18 C17 C16 . . . 119.5(2) no
C18 C17 H17 . . . 120.20 no
C17 C18 H18 . . . 119.40 no
C19 C18 C17 . . . 121.2(2) no
C19 C18 H18 . . . 119.40 no
C18 C19 C20 . . . 118.2(2) no
C18 C19 C22 . . . 120.3(3) no
C20 C19 C22 . . . 121.5(3) no
C19 C20 H20 . . . 119.30 no
C21 C20 C19 . . . 121.5(2) no
C21 C20 H20 . . . 119.30 no
C16 C21 C20 . . . 119.6(2) no
C16 C21 H21 . . . 120.20 no
C20 C21 H21 . . . 120.20 no
C19 C22 H22A . . . 109.50 no
C19 C22 H22B . . . 109.50 no
C19 C22 H22C . . . 109.50 no
H22A C22 H22B . . . 109.50 no
H22A C22 H22C . . . 109.50 no
H22B C22 H22C . . . 109.50 no
C13 N1 C15 . . 2_656 106.65(17) no
C13 N1 C16 . . . 128.56(17) no
C15 N1 C16 2_656 . . 124.07(17) no
C1 P1 C7 . . . 108.67(10) no
C14 P1 C1 . . . 106.68(10) no
C14 P1 C7 . . . 91.44(10) no
O1 P1 C1 . . . 111.71(10) no
O1 P1 C7 . . . 116.13(10) no
O1 P1 C14 . . . 120.18(10) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 0.3(4) no
C2 C1 C6 C5 . . . . 0.4(4) no
C2 C1 P1 C7 . . . . 133.73(18) no
C2 C1 P1 C14 . . . . -128.86(19) no
C2 C1 P1 O1 . . . . 4.3(2) no
C2 C3 C4 C5 . . . . 0.5(4) no
C3 C4 C5 C6 . . . . -0.8(5) no
C4 C5 C6 C1 . . . . 0.4(4) no
C6 C1 C2 C3 . . . . -0.8(4) no
C6 C1 P1 C7 . . . . -48.7(2) no
C6 C1 P1 C14 . . . . 48.8(2) no
C6 C1 P1 O1 . . . . -178.07(18) no
C7 C8 C9 C10 . . . . 0.3(4) no
C7 C12 C13 C14 . . . . 6.5(3) no
C7 C12 C13 N1 . . . . -176.4(2) no
C8 C7 C12 C11 . . . . -0.8(4) no
C8 C7 C12 C13 . . . . -176.1(2) no
C8 C7 P1 C1 . . . . -80.0(2) no
C8 C7 P1 C14 . . . . 171.8(2) no
C8 C7 P1 O1 . . . . 46.9(2) no
C8 C9 C10 C11 . . . . -0.9(5) no
C9 C10 C11 C12 . . . . 0.5(4) no
C10 C11 C12 C7 . . . . 0.3(4) no
C10 C11 C12 C13 . . . . 174.4(2) no
C11 C12 C13 C14 . . . . -168.1(2) no
C11 C12 C13 N1 . . . . 9.0(4) no
C12 C7 C8 C9 . . . . 0.5(4) no
C12 C7 P1 C1 . . . . 106.14(18) no
C12 C7 P1 C14 . . . . -2.02(18) no
C12 C7 P1 O1 . . . . -126.94(17) no
C12 C13 C14 C15 . . . . 177.06(19) no
C12 C13 C14 P1 . . . . -7.9(3) no
C12 C13 N1 C15 . . . 2_656 -175.8(2) no
C12 C13 N1 C16 . . . . 13.8(4) no
C13 C14 C15 C15 . . . 2_656 -0.4(3) no
C13 C14 C15 N1 . . . 2_656 -178.4(3) no
C13 C14 P1 C1 . . . . -104.49(17) no
C13 C14 P1 C7 . . . . 5.50(18) no
C13 C14 P1 O1 . . . . 127.12(17) no
C14 C13 N1 C15 . . . 2_656 1.4(3) no
C14 C13 N1 C16 . . . . -169.0(2) no
C15 C14 P1 C1 . . . . 67.1(3) no
C15 C14 P1 C7 . . . . 177.1(3) no
C15 C14 P1 O1 . . . . -61.3(3) no
C16 C17 C18 C19 . . . . -2.5(4) no
C17 C16 C21 C20 . . . . -0.4(4) no
C17 C16 N1 C13 . . . . 42.9(3) no
C17 C16 N1 C15 . . . 2_656 -126.0(2) no
C17 C18 C19 C20 . . . . 0.6(4) no
C17 C18 C19 C22 . . . . 179.6(3) no
C18 C19 C20 C21 . . . . 1.4(4) no
C19 C20 C21 C16 . . . . -1.6(4) no
C21 C16 C17 C18 . . . . 2.4(3) no
C21 C16 N1 C13 . . . . -140.6(2) no
C21 C16 N1 C15 . . . 2_656 50.5(3) no
C22 C19 C20 C21 . . . . -177.5(3) no
N1 C13 C14 C15 . . . . -0.7(3) no
N1 C13 C14 P1 . . . . 174.32(15) no
N1 C16 C17 C18 . . . . 178.9(2) no
N1 C16 C21 C20 . . . . -176.9(2) no
P1 C1 C2 C3 . . . . 176.9(2) no
P1 C1 C6 C5 . . . . -177.2(2) no
P1 C7 C8 C9 . . . . -172.8(2) no
P1 C7 C12 C11 . . . . 173.42(19) no
P1 C7 C12 C13 . . . . -1.9(2) no
P1 C14 C15 C15 . . . 2_656 -172.2(2) no
P1 C14 C15 N1 . . . 2_656 9.8(6) no
####################################################################### 
# 
# 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_201709163
_database_code_depnum_ccdc_archive 'CCDC 1578987'
_audit_update_record             
;
2017-10-10 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;
_audit_creation_date             2017-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H32 N2 O2 P2, C H2 Cl2'
_chemical_formula_sum            'C45 H34 Cl2 N2 O2 P2'
_chemical_formula_weight         767.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H41N2P1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2229(5)
_cell_length_b                   10.3244(7)
_cell_length_c                   19.8604(11)
_cell_angle_alpha                91.554(5)
_cell_angle_beta                 104.445(4)
_cell_angle_gamma                108.309(5)
_cell_volume                     1914.41(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8630
_cell_measurement_theta_min      4.5250
_shelx_estimated_absorpt_T_max   0.778
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.541
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00    4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega   71.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega   14.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  9 omega   16.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   69.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -123.0000 -108.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   33.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -148.0000   87.0000 69

#__ type_ start__ end____ width___ exp.time_
 14 omega  104.00  173.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00  103.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 71

#__ type_ start__ end____ width___ exp.time_
 17 omega  120.00  156.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 18 omega   84.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   97.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   77.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 21 omega   95.00  174.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega  131.00  159.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 24 omega   73.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   37.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 26 omega   82.00  122.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 27 omega   42.00  102.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
 29 omega   46.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   94.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
 31 omega  101.00  167.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
 32 omega  145.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 33 omega   49.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0267318000
_diffrn_orient_matrix_UB_12      -0.1388907000
_diffrn_orient_matrix_UB_13      0.0302164000
_diffrn_orient_matrix_UB_21      -0.0761881000
_diffrn_orient_matrix_UB_22      -0.0755621000
_diffrn_orient_matrix_UB_23      -0.0742639000
_diffrn_orient_matrix_UB_31      0.1438309000
_diffrn_orient_matrix_UB_32      -0.0056917000
_diffrn_orient_matrix_UB_33      -0.0085861000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5029
_reflns_number_total             6833
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1153P)²+0.4160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.2006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36), C39(H39),
 C40(H40), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C 0.7262(4) 0.5046(3) 0.28367(19) 0.0550(8) Uani 1 1 d . . . . .
H1 H 0.6548 0.5046 0.2441 0.066 Uiso 1 1 calc R . . . .
C2 C 0.8439(4) 0.6236(4) 0.3112(2) 0.0602(9) Uani 1 1 d . . . . .
H2 H 0.8495 0.7036 0.2899 0.072 Uiso 1 1 calc R . . . .
C3 C 0.9509(4) 0.6245(3) 0.3689(2) 0.0576(8) Uani 1 1 d . . . . .
H3 H 1.0278 0.7047 0.3864 0.069 Uiso 1 1 calc R . . . .
C4 C 0.9449(3) 0.5072(3) 0.40099(17) 0.0503(7) Uani 1 1 d . . . . .
H4 H 1.0177 0.5076 0.4400 0.060 Uiso 1 1 calc R . . . .
C5 C 0.8299(3) 0.3887(3) 0.37468(16) 0.0446(7) Uani 1 1 d . . . . .
C6 C 0.7181(3) 0.3874(3) 0.31640(16) 0.0444(7) Uani 1 1 d . . . . .
C7 C 0.6071(3) 0.2504(3) 0.30042(16) 0.0450(7) Uani 1 1 d . . . . .
C8 C 0.6292(3) 0.1528(3) 0.34479(15) 0.0422(6) Uani 1 1 d . . . . .
C9 C 0.5156(3) 0.0305(3) 0.31617(16) 0.0424(6) Uani 1 1 d . . . . .
C10 C 0.4275(3) 0.0559(3) 0.25611(15) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.3109(3) -0.0652(3) 0.22903(15) 0.0418(6) Uani 1 1 d . . . . .
C12 C 0.3343(3) -0.1611(3) 0.27422(15) 0.0416(6) Uani 1 1 d . . . . .
C13 C 0.2294(3) -0.2998(3) 0.25800(16) 0.0445(7) Uani 1 1 d . . . . .
C14 C 0.1219(3) -0.3079(3) 0.19550(16) 0.0460(7) Uani 1 1 d . . . . .
C15 C 0.0090(3) -0.4284(4) 0.17059(18) 0.0568(8) Uani 1 1 d . . . . .
H15 H -0.0618 -0.4339 0.1297 0.068 Uiso 1 1 calc R . . . .
C16 C 0.0030(4) -0.5418(4) 0.2077(2) 0.0628(9) Uani 1 1 d . . . . .
H16 H -0.0726 -0.6237 0.1915 0.075 Uiso 1 1 calc R . . . .
C17 C 0.1078(4) -0.5337(4) 0.2679(2) 0.0581(8) Uani 1 1 d . . . . .
H17 H 0.1023 -0.6106 0.2918 0.070 Uiso 1 1 calc R . . . .
C18 C 0.2214(3) -0.4135(3) 0.29377(17) 0.0514(7) Uani 1 1 d . . . . .
H18 H 0.2914 -0.4095 0.3347 0.062 Uiso 1 1 calc R . . . .
C19 C 0.9163(3) 0.1445(3) 0.38008(17) 0.0466(7) Uani 1 1 d . . . . .
C20 C 0.9197(4) 0.1327(4) 0.31107(19) 0.0594(9) Uani 1 1 d . . . . .
H20 H 0.8615 0.1663 0.2774 0.071 Uiso 1 1 calc R . . . .
C21 C 1.0088(5) 0.0718(5) 0.2921(3) 0.0781(12) Uani 1 1 d . . . . .
H21 H 1.0123 0.0660 0.2458 0.094 Uiso 1 1 calc R . . . .
C22 C 1.0930(5) 0.0188(4) 0.3416(3) 0.0766(12) Uani 1 1 d . . . . .
H22 H 1.1512 -0.0247 0.3283 0.092 Uiso 1 1 calc R . . . .
C23 C 1.0909(5) 0.0304(5) 0.4100(3) 0.0761(12) Uani 1 1 d . . . . .
H23 H 1.1482 -0.0046 0.4433 0.091 Uiso 1 1 calc R . . . .
C24 C 1.0037(4) 0.0939(4) 0.4296(2) 0.0608(9) Uani 1 1 d . . . . .
H24 H 1.0036 0.1027 0.4763 0.073 Uiso 1 1 calc R . . . .
C25 C 0.1937(3) -0.1536(3) 0.07794(16) 0.0470(7) Uani 1 1 d . . . . .
C26 C 0.3040(4) -0.1953(5) 0.0703(2) 0.0704(11) Uani 1 1 d . . . . .
H26 H 0.3587 -0.2230 0.1082 0.084 Uiso 1 1 calc R . . . .
C27 C 0.3345(5) -0.1963(6) 0.0063(3) 0.0869(14) Uani 1 1 d . . . . .
H27 H 0.4104 -0.2237 0.0015 0.104 Uiso 1 1 calc R . . . .
C28 C 0.2530(6) -0.1569(5) -0.0501(2) 0.0841(13) Uani 1 1 d . . . . .
H28 H 0.2739 -0.1576 -0.0930 0.101 Uiso 1 1 calc R . . . .
C29 C 0.1437(6) -0.1176(5) -0.0433(2) 0.0869(14) Uani 1 1 d . . . . .
H29 H 0.0885 -0.0915 -0.0817 0.104 Uiso 1 1 calc R . . . .
C30 C 0.1120(5) -0.1154(5) 0.0205(2) 0.0691(10) Uani 1 1 d . . . . .
H30 H 0.0356 -0.0882 0.0246 0.083 Uiso 1 1 calc R . . . .
C31 C 0.4157(3) 0.2557(3) 0.19106(16) 0.0435(7) Uani 1 1 d . . . . .
C32 C 0.3698(4) 0.3623(4) 0.2062(2) 0.0654(10) Uani 1 1 d . . . . .
H32 H 0.3871 0.3969 0.2525 0.078 Uiso 1 1 calc R . . . .
C33 C 0.2983(5) 0.4173(5) 0.1528(2) 0.0729(11) Uani 1 1 d . . . . .
H33 H 0.2686 0.4900 0.1632 0.087 Uiso 1 1 calc R . . . .
C34 C 0.2701(4) 0.3660(4) 0.0837(2) 0.0692(11) Uani 1 1 d . . . . .
C35 C 0.3145(6) 0.2598(5) 0.0701(2) 0.0881(15) Uani 1 1 d . . . . .
H35 H 0.2939 0.2223 0.0240 0.106 Uiso 1 1 calc R . . . .
C36 C 0.3899(5) 0.2060(4) 0.1235(2) 0.0698(11) Uani 1 1 d . . . . .
H36 H 0.4228 0.1357 0.1129 0.084 Uiso 1 1 calc R . . . .
C37 C 0.1894(6) 0.4249(6) 0.0248(3) 0.107(2) Uani 1 1 d . . . . .
H37A H 0.1160 0.4486 0.0391 0.160 Uiso 1 1 calc GR . . . .
H37B H 0.1465 0.3578 -0.0157 0.160 Uiso 1 1 calc GR . . . .
H37C H 0.2545 0.5055 0.0136 0.160 Uiso 1 1 calc GR . . . .
C38 C 0.5114(3) -0.1689(3) 0.38648(15) 0.0419(6) Uani 1 1 d . . . . .
C39 C 0.4571(4) -0.1758(4) 0.44320(19) 0.0623(9) Uani 1 1 d . . . . .
H39 H 0.3858 -0.1382 0.4440 0.075 Uiso 1 1 calc R . . . .
C40 C 0.5088(5) -0.2390(5) 0.4990(2) 0.0716(11) Uani 1 1 d . . . . .
H40 H 0.4726 -0.2417 0.5378 0.086 Uiso 1 1 calc R . . . .
C41 C 0.6122(4) -0.2981(4) 0.4993(2) 0.0652(10) Uani 1 1 d . . . . .
C42 C 0.6644(5) -0.2904(5) 0.4417(2) 0.0789(12) Uani 1 1 d . . . . .
H42 H 0.7341 -0.3297 0.4402 0.095 Uiso 1 1 calc R . . . .
C43 C 0.6154(4) -0.2255(4) 0.3858(2) 0.0653(10) Uani 1 1 d . . . . .
H43 H 0.6533 -0.2202 0.3476 0.078 Uiso 1 1 calc R . . . .
C44 C 0.6656(6) -0.3683(5) 0.5611(3) 0.0955(16) Uani 1 1 d . . . . .
H44A H 0.7279 -0.3003 0.5992 0.143 Uiso 1 1 calc GR . . . .
H44B H 0.7171 -0.4236 0.5478 0.143 Uiso 1 1 calc GR . . . .
H44C H 0.5856 -0.4257 0.5754 0.143 Uiso 1 1 calc GR . . . .
N1 N 0.4843(3) 0.1934(3) 0.24649(13) 0.0443(6) Uani 1 1 d . . . . .
N2 N 0.4565(3) -0.1047(3) 0.32731(13) 0.0422(5) Uani 1 1 d . . . . .
O1 O 0.8105(2) 0.2176(3) 0.48347(11) 0.0543(6) Uani 1 1 d . . . . .
O2 O 0.0296(2) -0.0878(3) 0.15213(13) 0.0574(6) Uani 1 1 d . . . . .
P1 P 0.79955(8) 0.22192(8) 0.40772(4) 0.0418(2) Uani 1 1 d . . . . .
P2 P 0.14994(8) -0.14303(8) 0.16058(4) 0.0435(2) Uani 1 1 d . . . . .
C45 C 0.7014(6) 0.8108(8) 0.1372(4) 0.132(3) Uani 1 1 d . . . . .
H45A H 0.8021 0.8234 0.1568 0.159 Uiso 1 1 calc R . . . .
H45B H 0.6934 0.8625 0.0971 0.159 Uiso 1 1 calc R . . . .
Cl1 Cl 0.64112(19) 0.8753(4) 0.19756(11) 0.1980(14) Uani 1 1 d . . . . .
Cl2 Cl 0.6101(2) 0.6385(2) 0.10881(12) 0.1448(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.401(5) . ?
C1 C6 1.378(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 C6 1.405(4) . ?
C5 P1 1.822(3) . ?
C6 C7 1.475(4) . ?
C7 C8 1.391(4) . ?
C7 N1 1.378(4) . ?
C8 C9 1.406(4) . ?
C8 P1 1.786(3) . ?
C9 C10 1.390(4) . ?
C9 N2 1.384(4) . ?
C10 C11 1.408(4) . ?
C10 N1 1.393(4) . ?
C11 C12 1.391(4) . ?
C11 P2 1.787(3) . ?
C12 C13 1.463(4) . ?
C12 N2 1.366(4) . ?
C13 C14 1.419(4) . ?
C13 C18 1.380(5) . ?
C14 C15 1.380(4) . ?
C14 P2 1.821(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(5) . ?
C19 C24 1.387(5) . ?
C19 P1 1.808(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(5) . ?
C25 C30 1.383(5) . ?
C25 P2 1.815(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.382(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.373(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.338(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(5) . ?
C31 C36 1.354(5) . ?
C31 N1 1.434(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.375(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.383(6) . ?
C34 C35 1.356(6) . ?
C34 C37 1.514(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.385(6) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.369(5) . ?
C38 C43 1.367(5) . ?
C38 N2 1.443(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.377(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.376(6) . ?
C41 C42 1.372(6) . ?
C41 C44 1.513(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.380(5) . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
O1 P1 1.483(2) . ?
O2 P2 1.486(2) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 Cl1 1.687(7) . ?
C45 Cl2 1.730(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.8(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 P1 127.2(3) . . ?
C6 C5 P1 112.0(2) . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C7 130.6(3) . . ?
C5 C6 C7 110.0(3) . . ?
C8 C7 C6 116.7(3) . . ?
N1 C7 C6 132.8(3) . . ?
N1 C7 C8 110.4(3) . . ?
C7 C8 C9 105.8(3) . . ?
C7 C8 P1 109.8(2) . . ?
C9 C8 P1 143.5(2) . . ?
C10 C9 C8 108.5(3) . . ?
N2 C9 C8 143.0(3) . . ?
N2 C9 C10 108.4(3) . . ?
C9 C10 C11 108.5(3) . . ?
C9 C10 N1 108.3(3) . . ?
N1 C10 C11 143.2(3) . . ?
C10 C11 P2 145.3(2) . . ?
C12 C11 C10 105.1(2) . . ?
C12 C11 P2 109.7(2) . . ?
C11 C12 C13 117.3(3) . . ?
N2 C12 C11 111.1(3) . . ?
N2 C12 C13 131.6(3) . . ?
C14 C13 C12 109.9(3) . . ?
C18 C13 C12 130.4(3) . . ?
C18 C13 C14 119.7(3) . . ?
C13 C14 P2 111.7(2) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 P2 127.8(3) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 119.1(3) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C24 119.1(3) . . ?
C20 C19 P1 122.1(3) . . ?
C24 C19 P1 118.8(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C30 118.9(3) . . ?
C26 C25 P2 123.2(3) . . ?
C30 C25 P2 117.9(3) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(4) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.5(4) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 120.1(4) . . ?
C25 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C32 C31 N1 120.2(3) . . ?
C36 C31 C32 119.6(3) . . ?
C36 C31 N1 120.1(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.9(4) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 C37 121.0(4) . . ?
C35 C34 C33 118.3(4) . . ?
C35 C34 C37 120.7(4) . . ?
C34 C35 H35 119.4 . . ?
C34 C35 C36 121.3(4) . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 120.1(4) . . ?
C31 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N2 119.9(3) . . ?
C43 C38 C39 119.6(3) . . ?
C43 C38 N2 120.5(3) . . ?
C38 C39 H39 120.3 . . ?
C38 C39 C40 119.5(4) . . ?
C40 C39 H39 120.3 . . ?
C39 C40 H40 119.0 . . ?
C41 C40 C39 122.1(4) . . ?
C41 C40 H40 119.0 . . ?
C40 C41 C44 120.9(4) . . ?
C42 C41 C40 117.3(4) . . ?
C42 C41 C44 121.8(4) . . ?
C41 C42 H42 119.3 . . ?
C41 C42 C43 121.4(4) . . ?
C43 C42 H42 119.3 . . ?
C38 C43 C42 120.2(4) . . ?
C38 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C7 N1 C10 107.0(2) . . ?
C7 N1 C31 130.1(3) . . ?
C10 N1 C31 122.8(2) . . ?
C9 N2 C38 125.5(2) . . ?
C12 N2 C9 106.9(2) . . ?
C12 N2 C38 127.5(2) . . ?
C8 P1 C5 91.39(14) . . ?
C8 P1 C19 106.13(14) . . ?
C19 P1 C5 107.03(15) . . ?
O1 P1 C5 117.64(14) . . ?
O1 P1 C8 120.07(14) . . ?
O1 P1 C19 112.19(15) . . ?
C11 P2 C14 91.49(14) . . ?
C11 P2 C25 109.41(14) . . ?
C25 P2 C14 109.82(15) . . ?
O2 P2 C11 119.53(14) . . ?
O2 P2 C14 115.32(15) . . ?
O2 P2 C25 109.93(15) . . ?
H45A C45 H45B 107.7 . . ?
Cl1 C45 H45A 108.8 . . ?
Cl1 C45 H45B 108.8 . . ?
Cl1 C45 Cl2 113.7(3) . . ?
Cl2 C45 H45A 108.8 . . ?
Cl2 C45 H45B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C6 C7 C8 -178.8(3) . . . . ?
C1 C6 C7 N1 5.3(6) . . . . ?
C2 C1 C6 C5 -2.3(5) . . . . ?
C2 C1 C6 C7 178.4(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C3 C4 C5 P1 179.5(3) . . . . ?
C4 C5 C6 C1 2.3(5) . . . . ?
C4 C5 C6 C7 -178.2(3) . . . . ?
C4 C5 P1 C8 176.5(3) . . . . ?
C4 C5 P1 C19 -76.2(3) . . . . ?
C4 C5 P1 O1 51.1(3) . . . . ?
C5 C6 C7 C8 1.8(4) . . . . ?
C5 C6 C7 N1 -174.0(3) . . . . ?
C6 C1 C2 C3 1.0(6) . . . . ?
C6 C5 P1 C8 -3.0(2) . . . . ?
C6 C5 P1 C19 104.3(2) . . . . ?
C6 C5 P1 O1 -128.3(2) . . . . ?
C6 C7 C8 C9 -176.1(3) . . . . ?
C6 C7 C8 P1 -4.1(3) . . . . ?
C6 C7 N1 C10 175.4(3) . . . . ?
C6 C7 N1 C31 -7.7(6) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 N2 -177.0(4) . . . . ?
C7 C8 P1 C5 3.9(2) . . . . ?
C7 C8 P1 C19 -104.3(2) . . . . ?
C7 C8 P1 O1 127.3(2) . . . . ?
C8 C7 N1 C10 -0.7(3) . . . . ?
C8 C7 N1 C31 176.3(3) . . . . ?
C8 C9 C10 C11 -177.7(2) . . . . ?
C8 C9 C10 N1 0.0(4) . . . . ?
C8 C9 N2 C12 177.0(4) . . . . ?
C8 C9 N2 C38 0.3(6) . . . . ?
C9 C8 P1 C5 170.9(4) . . . . ?
C9 C8 P1 C19 62.7(4) . . . . ?
C9 C8 P1 O1 -65.7(4) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 P2 -179.3(3) . . . . ?
C9 C10 N1 C7 0.4(3) . . . . ?
C9 C10 N1 C31 -176.8(3) . . . . ?
C10 C9 N2 C12 0.5(3) . . . . ?
C10 C9 N2 C38 -176.2(3) . . . . ?
C10 C11 C12 C13 -178.9(3) . . . . ?
C10 C11 C12 N2 0.9(3) . . . . ?
C10 C11 P2 C14 177.5(4) . . . . ?
C10 C11 P2 C25 65.8(4) . . . . ?
C10 C11 P2 O2 -62.1(5) . . . . ?
C11 C10 N1 C7 176.8(4) . . . . ?
C11 C10 N1 C31 -0.4(6) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?
C11 C12 C13 C18 -177.5(3) . . . . ?
C11 C12 N2 C9 -0.9(3) . . . . ?
C11 C12 N2 C38 175.8(3) . . . . ?
C12 C11 P2 C14 -1.2(2) . . . . ?
C12 C11 P2 C25 -112.9(2) . . . . ?
C12 C11 P2 O2 119.2(2) . . . . ?
C12 C13 C14 C15 -178.4(3) . . . . ?
C12 C13 C14 P2 -2.1(3) . . . . ?
C12 C13 C18 C17 178.4(3) . . . . ?
C13 C12 N2 C9 178.9(3) . . . . ?
C13 C12 N2 C38 -4.4(5) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C13 C14 P2 C11 2.0(2) . . . . ?
C13 C14 P2 C25 113.2(2) . . . . ?
C13 C14 P2 O2 -121.9(2) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C14 P2 C11 178.0(3) . . . . ?
C15 C14 P2 C25 -70.7(3) . . . . ?
C15 C14 P2 O2 54.1(4) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C13 -0.2(6) . . . . ?
C18 C13 C14 C15 0.4(5) . . . . ?
C18 C13 C14 P2 176.8(2) . . . . ?
C19 C20 C21 C22 1.5(6) . . . . ?
C20 C19 C24 C23 -1.2(6) . . . . ?
C20 C19 P1 C5 -51.9(3) . . . . ?
C20 C19 P1 C8 44.7(3) . . . . ?
C20 C19 P1 O1 177.6(3) . . . . ?
C20 C21 C22 C23 -1.8(7) . . . . ?
C21 C22 C23 C24 0.5(7) . . . . ?
C22 C23 C24 C19 0.9(6) . . . . ?
C24 C19 C20 C21 -0.1(5) . . . . ?
C24 C19 P1 C5 128.9(3) . . . . ?
C24 C19 P1 C8 -134.5(3) . . . . ?
C24 C19 P1 O1 -1.5(3) . . . . ?
C25 C26 C27 C28 -0.8(8) . . . . ?
C26 C25 C30 C29 -1.0(6) . . . . ?
C26 C25 P2 C11 44.1(4) . . . . ?
C26 C25 P2 C14 -54.9(4) . . . . ?
C26 C25 P2 O2 177.2(3) . . . . ?
C26 C27 C28 C29 -0.1(8) . . . . ?
C27 C28 C29 C30 0.4(8) . . . . ?
C28 C29 C30 C25 0.2(8) . . . . ?
C30 C25 C26 C27 1.3(6) . . . . ?
C30 C25 P2 C11 -135.0(3) . . . . ?
C30 C25 P2 C14 126.0(3) . . . . ?
C30 C25 P2 O2 -1.8(3) . . . . ?
C31 C32 C33 C34 0.8(7) . . . . ?
C32 C31 C36 C35 -1.7(7) . . . . ?
C32 C31 N1 C7 -59.0(5) . . . . ?
C32 C31 N1 C10 117.5(4) . . . . ?
C32 C33 C34 C35 0.1(7) . . . . ?
C32 C33 C34 C37 179.0(4) . . . . ?
C33 C34 C35 C36 -1.8(8) . . . . ?
C34 C35 C36 C31 2.7(8) . . . . ?
C36 C31 C32 C33 0.0(6) . . . . ?
C36 C31 N1 C7 123.9(4) . . . . ?
C36 C31 N1 C10 -59.5(5) . . . . ?
C37 C34 C35 C36 179.2(5) . . . . ?
C38 C39 C40 C41 -1.2(7) . . . . ?
C39 C38 C43 C42 0.6(6) . . . . ?
C39 C38 N2 C9 95.2(4) . . . . ?
C39 C38 N2 C12 -80.8(4) . . . . ?
C39 C40 C41 C42 0.9(7) . . . . ?
C39 C40 C41 C44 -179.2(4) . . . . ?
C40 C41 C42 C43 0.3(7) . . . . ?
C41 C42 C43 C38 -1.0(7) . . . . ?
C43 C38 C39 C40 0.5(6) . . . . ?
C43 C38 N2 C9 -86.1(4) . . . . ?
C43 C38 N2 C12 97.8(4) . . . . ?
C44 C41 C42 C43 -179.7(5) . . . . ?
N1 C7 C8 C9 0.7(4) . . . . ?
N1 C7 C8 P1 172.7(2) . . . . ?
N1 C10 C11 C12 -177.0(4) . . . . ?
N1 C10 C11 P2 4.3(8) . . . . ?
N1 C31 C32 C33 -177.1(4) . . . . ?
N1 C31 C36 C35 175.4(4) . . . . ?
N2 C9 C10 C11 0.1(4) . . . . ?
N2 C9 C10 N1 177.8(2) . . . . ?
N2 C12 C13 C14 -178.6(3) . . . . ?
N2 C12 C13 C18 2.7(6) . . . . ?
N2 C38 C39 C40 179.1(3) . . . . ?
N2 C38 C43 C42 -178.0(4) . . . . ?
P1 C5 C6 C1 -178.2(3) . . . . ?
P1 C5 C6 C7 1.3(3) . . . . ?
P1 C8 C9 C10 -167.7(3) . . . . ?
P1 C8 C9 N2 15.7(7) . . . . ?
P1 C19 C20 C21 -179.2(3) . . . . ?
P1 C19 C24 C23 178.0(3) . . . . ?
P2 C11 C12 C13 0.3(3) . . . . ?
P2 C11 C12 N2 -179.9(2) . . . . ?
P2 C14 C15 C16 -176.0(3) . . . . ?
P2 C25 C26 C27 -177.7(4) . . . . ?
P2 C25 C30 C29 178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
