# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 
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data_dg467_a
_audit_block_doi                 10.5517/ccdc.csd.cc2003sy
_database_code_depnum_ccdc_archive 'CCDC 1847159'
_audit_update_record             
;
2018-06-04 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2018-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1



_chemical_name_common            ?
_chemical_name_systematic        
'Lithium Δ-fac-tris[1,2-phenyleneoxy(methylamino)]-phosphate'
_chemical_formula_moiety         'C33 H45 Li N3 O6 P'
_chemical_formula_sum            'C33 H45 Li N3 O6 P'
_chemical_formula_weight         617.63
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   13.6248(5)
_cell_length_b                   14.4725(6)
_cell_length_c                   16.0410(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3163.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0499 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9036.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       square
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.518
_diffrn_reflns_theta_min         1.895
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                8292
_reflns_number_total             9477
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.666
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 3273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         9477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.025
_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)+(0.0499P)²+0.6277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0993
_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:
 C00M(H00A,H00B), C00Q(H00J,H00M), C00Y(H00Z,H), C00Z(H00,HA), C010(H01A,H01B),
  C011(H01C,H01D), C012(H01E,H01F), C013(H01G,H01H), C014(H01I,H01J), C015(H01K,
 H01L), C016(H01M,H01N), C017(H01O,H01P)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00N(H00N), C00P(H00P), C00S(H00S), C00T(H00T), C00W(H00X), C00X(H00Y)
2.c Idealised Me refined as rotating group:
 C00O(H00D,H00F,H00G), C00U(H00O,H00Q,H00R), C00V(H00U,H00V,H00W)
;
_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
P001 P 0.49992(4) 0.50182(3) 0.50409(3) 0.01098(10) Uani 1 1 d . . . . .
O002 O 0.44179(11) 0.39265(10) 0.50410(9) 0.0124(3) Uani 1 1 d . . . . .
O003 O 0.46513(11) 0.50399(11) 0.39828(9) 0.0137(3) Uani 1 1 d . . . . .
O004 O 0.60143(11) 0.43819(10) 0.46756(9) 0.0136(3) Uani 1 1 d . . . . .
O005 O 0.54312(12) 0.21979(10) 0.42159(10) 0.0171(3) Uani 1 1 d . . . . .
O006 O 0.38194(12) 0.31526(11) 0.32567(10) 0.0188(3) Uani 1 1 d . . . . .
O007 O 0.59648(13) 0.35623(11) 0.28952(10) 0.0199(3) Uani 1 1 d . . . . .
N008 N 0.52900(13) 0.48222(12) 0.61021(11) 0.0130(3) Uani 1 1 d . . . . .
N009 N 0.57306(13) 0.60226(11) 0.49605(12) 0.0134(3) Uani 1 1 d . . . . .
N00A N 0.38952(13) 0.56128(12) 0.52638(11) 0.0131(3) Uani 1 1 d . . . . .
C00B C 0.68293(15) 0.49032(14) 0.45461(12) 0.0125(4) Uani 1 1 d . . . . .
C00C C 0.51227(16) 0.35847(14) 0.71837(13) 0.0147(4) Uani 1 1 d . . . . .
H00C H 0.544833 0.391031 0.759999 0.018 Uiso 1 1 calc R . . . .
C00D C 0.37217(16) 0.53588(14) 0.38548(13) 0.0142(4) Uani 1 1 d . . . . .
C00E C 0.74562(16) 0.64598(15) 0.46030(13) 0.0152(4) Uani 1 1 d . . . . .
H00E H 0.737113 0.708666 0.470794 0.018 Uiso 1 1 calc R . . . .
C00F C 0.44912(15) 0.34668(14) 0.57798(12) 0.0120(4) Uani 1 1 d . . . . .
C00G C 0.49849(16) 0.39720(13) 0.63953(12) 0.0117(3) Uani 1 1 d . . . . .
C00H C 0.77215(16) 0.45660(15) 0.42765(13) 0.0149(4) Uani 1 1 d . . . . .
H00H H 0.780370 0.393971 0.416697 0.018 Uiso 1 1 calc R . . . .
C00I C 0.85014(17) 0.51862(16) 0.41709(13) 0.0176(4) Uani 1 1 d . . . . .
H00I H 0.910821 0.497185 0.398897 0.021 Uiso 1 1 calc R . . . .
C00J C 0.32684(16) 0.56798(14) 0.45865(13) 0.0132(4) Uani 1 1 d . . . . .
C00K C 0.22784(18) 0.57048(16) 0.30633(14) 0.0200(5) Uani 1 1 d . . . . .
H00K H 0.194750 0.572586 0.255656 0.024 Uiso 1 1 calc R . . . .
C00L C 0.41393(16) 0.25932(15) 0.59242(13) 0.0158(4) Uani 1 1 d . . . . .
H00L H 0.381927 0.226594 0.550576 0.019 Uiso 1 1 calc R . . . .
C00M C 0.65041(18) 0.28044(17) 0.25256(14) 0.0209(5) Uani 1 1 d . . . . .
H00A H 0.610755 0.224777 0.252444 0.025 Uiso 1 1 calc R . . . .
H00B H 0.709942 0.268472 0.283922 0.025 Uiso 1 1 calc R . . . .
C00N C 0.32485(18) 0.53742(15) 0.30979(13) 0.0172(4) Uani 1 1 d . . . . .
H00N H 0.356374 0.516989 0.261787 0.021 Uiso 1 1 calc R . . . .
C00O C 0.35226(17) 0.58859(16) 0.60737(13) 0.0176(4) Uani 1 1 d . . . . .
H00D H 0.302283 0.545977 0.624741 0.026 Uiso 1 1 calc GR . . . .
H00F H 0.324958 0.649612 0.603826 0.026 Uiso 1 1 calc GR . . . .
H00G H 0.404866 0.588258 0.647187 0.026 Uiso 1 1 calc GR . . . .
C00P C 0.42741(17) 0.22024(15) 0.67218(14) 0.0182(4) Uani 1 1 d . . . . .
H00P H 0.403591 0.161354 0.683545 0.022 Uiso 1 1 calc R . . . .
C00Q C 0.50317(19) 0.13077(15) 0.39952(15) 0.0200(4) Uani 1 1 d . . . . .
H00J H 0.493064 0.126896 0.339764 0.024 Uiso 1 1 calc R . . . .
H00M H 0.440687 0.121111 0.427155 0.024 Uiso 1 1 calc R . . . .
C00R C 0.66824(15) 0.58471(14) 0.47064(13) 0.0123(4) Uani 1 1 d . . . . .
C00S C 0.47591(16) 0.26936(16) 0.73338(13) 0.0178(4) Uani 1 1 d . . . . .
H00S H 0.484662 0.242807 0.785646 0.021 Uiso 1 1 calc R . . . .
C00T C 0.23037(16) 0.59921(15) 0.45567(14) 0.0155(4) Uani 1 1 d . . . . .
H00T H 0.198827 0.619210 0.503818 0.019 Uiso 1 1 calc R . . . .
C00U C 0.59300(19) 0.53572(16) 0.66340(14) 0.0213(5) Uani 1 1 d . . . . .
H00O H 0.653755 0.503207 0.671064 0.032 Uiso 1 1 calc GR . . . .
H00Q H 0.562043 0.544927 0.716517 0.032 Uiso 1 1 calc GR . . . .
H00R H 0.605733 0.594553 0.637973 0.032 Uiso 1 1 calc GR . . . .
C00V C 0.54059(18) 0.69738(14) 0.49718(16) 0.0211(5) Uani 1 1 d . . . . .
H00U H 0.552810 0.725077 0.443803 0.032 Uiso 1 1 calc GR . . . .
H00V H 0.575842 0.730647 0.539422 0.032 Uiso 1 1 calc GR . . . .
H00W H 0.471578 0.699549 0.509072 0.032 Uiso 1 1 calc GR . . . .
C00W C 0.83716(17) 0.61190(16) 0.43370(14) 0.0175(4) Uani 1 1 d . . . . .
H00X H 0.889584 0.652408 0.427169 0.021 Uiso 1 1 calc R . . . .
C00X C 0.18157(17) 0.59997(15) 0.37877(14) 0.0184(4) Uani 1 1 d . . . . .
H00Y H 0.116998 0.620606 0.376184 0.022 Uiso 1 1 calc R . . . .
C00Y C 0.67544(19) 0.30908(16) 0.16330(15) 0.0222(5) Uani 1 1 d . . . . .
H00Z H 0.651148 0.264009 0.123587 0.027 Uiso 1 1 calc R . . . .
H H 0.745815 0.315484 0.156184 0.027 Uiso 1 1 calc R . . . .
C00Z C 0.6238(2) 0.40215(18) 0.15191(15) 0.0246(5) Uani 1 1 d . . . . .
H00 H 0.662370 0.443586 0.117497 0.029 Uiso 1 1 calc R . . . .
HA H 0.559393 0.394362 0.127087 0.029 Uiso 1 1 calc R . . . .
C010 C 0.63209(18) 0.20509(16) 0.46846(16) 0.0215(5) Uani 1 1 d . . . . .
H01A H 0.618245 0.201638 0.527696 0.026 Uiso 1 1 calc R . . . .
H01B H 0.678531 0.254726 0.458698 0.026 Uiso 1 1 calc R . . . .
C011 C 0.6162(2) 0.43750(15) 0.24058(14) 0.0215(5) Uani 1 1 d . . . . .
H01C H 0.677038 0.466464 0.257907 0.026 Uiso 1 1 calc R . . . .
H01D H 0.563242 0.481952 0.245827 0.026 Uiso 1 1 calc R . . . .
C012 C 0.57760(18) 0.05824(15) 0.42779(16) 0.0214(5) Uani 1 1 d . . . . .
H01E H 0.558489 0.030930 0.480574 0.026 Uiso 1 1 calc R . . . .
H01F H 0.584668 0.009701 0.386533 0.026 Uiso 1 1 calc R . . . .
C013 C 0.67226(19) 0.11378(16) 0.43660(16) 0.0224(5) Uani 1 1 d . . . . .
H01G H 0.716807 0.085688 0.476380 0.027 Uiso 1 1 calc R . . . .
H01H H 0.705370 0.121059 0.383469 0.027 Uiso 1 1 calc R . . . .
C014 C 0.28992(18) 0.30680(18) 0.36906(16) 0.0240(5) Uani 1 1 d . . . . .
H01I H 0.245072 0.355463 0.352381 0.029 Uiso 1 1 calc R . . . .
H01J H 0.299743 0.310244 0.428869 0.029 Uiso 1 1 calc R . . . .
C015 C 0.3671(2) 0.2748(2) 0.24488(15) 0.0264(5) Uani 1 1 d . . . . .
H01K H 0.426874 0.245456 0.225553 0.032 Uiso 1 1 calc R . . . .
H01L H 0.348165 0.321849 0.204891 0.032 Uiso 1 1 calc R . . . .
C016 C 0.2500(2) 0.2127(2) 0.34433(19) 0.0347(6) Uani 1 1 d . . . . .
H01M H 0.178947 0.211158 0.347453 0.042 Uiso 1 1 calc R . . . .
H01N H 0.276806 0.164132 0.379273 0.042 Uiso 1 1 calc R . . . .
C017 C 0.2856(2) 0.2037(2) 0.25452(19) 0.0383(7) Uani 1 1 d . . . . .
H01O H 0.310422 0.141896 0.244126 0.046 Uiso 1 1 calc R . . . .
H01P H 0.232567 0.216148 0.215797 0.046 Uiso 1 1 calc R . . . .
Li18 Li 0.5060(3) 0.3506(3) 0.3868(2) 0.0180(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 O002 1.7673(15) . ?
P001 O003 1.7624(15) . ?
P001 O004 1.7619(15) . ?
P001 N008 1.7707(18) . ?
P001 N009 1.7671(17) . ?
P001 N00A 1.7693(19) . ?
P001 Li18 2.887(4) . ?
O002 C00F 1.363(2) . ?
O002 Li18 2.162(4) . ?
O003 C00D 1.364(3) . ?
O003 Li18 2.296(4) . ?
O004 C00B 1.358(3) . ?
O004 Li18 2.231(4) . ?
O005 C00Q 1.443(3) . ?
O005 C010 1.442(3) . ?
O005 Li18 2.038(4) . ?
O006 C014 1.439(3) . ?
O006 C015 1.436(3) . ?
O006 Li18 2.020(4) . ?
O007 C00M 1.447(3) . ?
O007 C011 1.439(3) . ?
O007 Li18 1.990(4) . ?
N008 C00G 1.381(3) . ?
N008 C00U 1.445(3) . ?
N009 C00R 1.383(3) . ?
N009 C00V 1.446(3) . ?
N00A C00J 1.385(3) . ?
N00A C00O 1.450(3) . ?
C00B C00H 1.379(3) . ?
C00B C00R 1.404(3) . ?
C00C C00G 1.396(3) . ?
C00C C00S 1.402(3) . ?
C00D C00J 1.405(3) . ?
C00D C00N 1.375(3) . ?
C00E C00R 1.388(3) . ?
C00E C00W 1.407(3) . ?
C00F C00G 1.401(3) . ?
C00F C00L 1.372(3) . ?
C00H C00I 1.401(3) . ?
C00I C00W 1.387(3) . ?
C00J C00T 1.391(3) . ?
C00K C00N 1.407(3) . ?
C00K C00X 1.389(3) . ?
C00L C00P 1.411(3) . ?
C00M C00Y 1.529(3) . ?
C00P C00S 1.380(3) . ?
C00Q C012 1.528(3) . ?
C00T C00X 1.401(3) . ?
C00Y C00Z 1.531(3) . ?
C00Z C011 1.515(3) . ?
C010 C013 1.519(3) . ?
C012 C013 1.526(3) . ?
C014 C016 1.519(4) . ?
C015 C017 1.522(4) . ?
C016 C017 1.526(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
O002 P001 N008 87.54(8) . . ?
O002 P001 N00A 93.08(8) . . ?
O002 P001 Li18 48.34(9) . . ?
O003 P001 O002 84.00(7) . . ?
O003 P001 N008 171.43(8) . . ?
O003 P001 N009 93.83(8) . . ?
O003 P001 N00A 87.56(8) . . ?
O003 P001 Li18 52.67(9) . . ?
O004 P001 O002 83.37(7) . . ?
O004 P001 O003 84.27(7) . . ?
O004 P001 N008 93.45(8) . . ?
O004 P001 N009 87.88(8) . . ?
O004 P001 N00A 171.39(8) . . ?
O004 P001 Li18 50.56(10) . . ?
N008 P001 Li18 119.92(10) . . ?
N009 P001 O002 171.15(8) . . ?
N009 P001 N008 94.34(9) . . ?
N009 P001 N00A 95.40(8) . . ?
N009 P001 Li18 124.04(10) . . ?
N00A P001 N008 94.24(8) . . ?
N00A P001 Li18 121.64(11) . . ?
P001 O002 Li18 94.02(12) . . ?
C00F O002 P001 113.81(12) . . ?
C00F O002 Li18 126.15(16) . . ?
P001 O003 Li18 89.71(11) . . ?
C00D O003 P001 113.64(13) . . ?
C00D O003 Li18 122.70(17) . . ?
P001 O004 Li18 91.85(12) . . ?
C00B O004 P001 113.72(13) . . ?
C00B O004 Li18 134.69(16) . . ?
C00Q O005 Li18 131.98(17) . . ?
C010 O005 C00Q 108.26(16) . . ?
C010 O005 Li18 119.25(17) . . ?
C014 O006 Li18 121.05(17) . . ?
C015 O006 C014 106.18(18) . . ?
C015 O006 Li18 131.25(18) . . ?
C00M O007 Li18 127.21(17) . . ?
C011 O007 C00M 107.54(17) . . ?
C011 O007 Li18 125.19(17) . . ?
C00G N008 P001 113.75(13) . . ?
C00G N008 C00U 117.25(17) . . ?
C00U N008 P001 128.10(15) . . ?
C00R N009 P001 113.53(14) . . ?
C00R N009 C00V 117.74(17) . . ?
C00V N009 P001 127.56(15) . . ?
C00J N00A P001 113.55(14) . . ?
C00J N00A C00O 117.89(18) . . ?
C00O N00A P001 127.69(15) . . ?
O004 C00B C00H 124.87(19) . . ?
O004 C00B C00R 113.31(18) . . ?
C00H C00B C00R 121.8(2) . . ?
C00G C00C C00S 118.51(19) . . ?
O003 C00D C00J 113.21(18) . . ?
O003 C00D C00N 125.04(19) . . ?
C00N C00D C00J 121.7(2) . . ?
C00R C00E C00W 119.1(2) . . ?
O002 C00F C00G 113.17(17) . . ?
O002 C00F C00L 124.82(19) . . ?
C00L C00F C00G 122.00(19) . . ?
N008 C00G C00C 128.73(19) . . ?
N008 C00G C00F 111.68(17) . . ?
C00C C00G C00F 119.57(19) . . ?
C00B C00H C00I 118.7(2) . . ?
C00W C00I C00H 120.2(2) . . ?
N00A C00J C00D 111.16(19) . . ?
N00A C00J C00T 129.2(2) . . ?
C00T C00J C00D 119.6(2) . . ?
C00X C00K C00N 119.9(2) . . ?
C00F C00L C00P 118.5(2) . . ?
O007 C00M C00Y 106.93(19) . . ?
C00D C00N C00K 118.8(2) . . ?
C00S C00P C00L 120.1(2) . . ?
O005 C00Q C012 106.87(19) . . ?
N009 C00R C00B 111.49(18) . . ?
N009 C00R C00E 129.08(19) . . ?
C00E C00R C00B 119.43(19) . . ?
C00P C00S C00C 121.4(2) . . ?
C00J C00T C00X 118.8(2) . . ?
C00I C00W C00E 120.8(2) . . ?
C00K C00X C00T 121.2(2) . . ?
C00M C00Y C00Z 104.34(19) . . ?
C011 C00Z C00Y 102.51(19) . . ?
O005 C010 C013 104.82(19) . . ?
O007 C011 C00Z 104.41(18) . . ?
C013 C012 C00Q 103.09(18) . . ?
C010 C013 C012 100.65(19) . . ?
O006 C014 C016 105.2(2) . . ?
O006 C015 C017 106.7(2) . . ?
C014 C016 C017 102.1(2) . . ?
C015 C017 C016 105.6(2) . . ?
O002 Li18 P001 37.64(7) . . ?
O002 Li18 O003 63.91(11) . . ?
O002 Li18 O004 64.57(12) . . ?
O003 Li18 P001 37.62(7) . . ?
O004 Li18 P001 37.59(7) . . ?
O004 Li18 O003 62.97(11) . . ?
O005 Li18 P001 122.20(17) . . ?
O005 Li18 O002 97.09(16) . . ?
O005 Li18 O003 159.5(2) . . ?
O005 Li18 O004 102.94(18) . . ?
O006 Li18 P001 118.98(17) . . ?
O006 Li18 O002 98.93(18) . . ?
O006 Li18 O003 94.66(17) . . ?
O006 Li18 O004 156.0(2) . . ?
O006 Li18 O005 96.04(17) . . ?
O007 Li18 P001 119.85(17) . . ?
O007 Li18 O002 157.1(2) . . ?
O007 Li18 O003 100.01(16) . . ?
O007 Li18 O004 94.07(17) . . ?
O007 Li18 O005 95.66(17) . . ?
O007 Li18 O006 98.52(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dg426_a
_audit_block_doi                 10.5517/ccdc.csd.cc202b9r
_database_code_depnum_ccdc_archive 'CCDC 1849283'
_audit_update_record             
;
2018-06-14 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl1.07 N2 O2 P'
_chemical_formula_sum            'C14 H14 Cl1.07 N2 O2 P'
_chemical_formula_weight         311.17
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.061(2)
_cell_length_b                   8.4030(13)
_cell_length_c                   12.2579(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.932(7)
_cell_angle_gamma                90
_cell_volume                     1411.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7265
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0451 after correction.
The ratio of minimum to maximum transmission is 0.9048.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       square
_exptl_crystal_F_000             645
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17828
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.471
_diffrn_reflns_theta_min         2.843
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3806
_reflns_number_total             4276
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.9425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-C2 \\sim Cl2-C4
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.26250(3) 0.57288(5) 0.67589(3) 0.03064(10) Uani 1 1 d . . . . .
Cl2 Cl -0.0758(4) 0.1825(7) 0.2794(5) 0.033(2) Uani 0.071(3) 1 d D . . A 2
P1 P 0.25910(3) 0.66965(5) 0.51620(3) 0.02180(10) Uani 1 1 d . . . . .
O1 O 0.14008(8) 0.61897(15) 0.47666(10) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.37811(7) 0.71682(12) 0.55804(9) 0.0226(2) Uani 1 1 d . . . . .
N1 N 0.28484(9) 0.54238(15) 0.42104(10) 0.0230(2) Uani 1 1 d . . . . .
N2 N 0.22947(9) 0.86366(16) 0.50681(11) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.12266(11) 0.48993(19) 0.40665(12) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.03461(11) 0.4118(2) 0.37312(14) 0.0284(3) Uani 1 1 d D . . . .
H2 H -0.020908 0.441835 0.400462 0.034 Uiso 1 1 calc R . . . .
C3 C 0.03070(12) 0.2862(2) 0.29690(15) 0.0316(3) Uani 1 1 d . . . . .
H3 H -0.031(2) 0.228(3) 0.2703(19) 0.039(6) Uiso 1 1 d . . . B 1
C4 C 0.11243(13) 0.2424(2) 0.25838(15) 0.0337(4) Uani 1 1 d D . . . .
H4 H 0.107730 0.158173 0.205770 0.040 Uiso 1 1 calc R . . . .
C5 C 0.20221(12) 0.32074(19) 0.29592(13) 0.0281(3) Uani 1 1 d . . . . .
H5 H 0.258552 0.289267 0.270732 0.034 Uiso 1 1 calc R . . . .
C6 C 0.20582(11) 0.44512(17) 0.37072(12) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.37802(11) 0.51262(19) 0.38919(13) 0.0250(3) Uani 1 1 d . . . . .
H7A H 0.424972 0.595636 0.421173 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.367727 0.513905 0.307434 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.403482 0.408465 0.417718 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.39442(10) 0.87491(17) 0.58304(11) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.48295(11) 0.94214(17) 0.63181(11) 0.0212(3) Uani 1 1 d . . . . .
H9 H 0.540250 0.879251 0.653148 0.025 Uiso 1 1 calc R . . . .
C10 C 0.48516(11) 1.10712(18) 0.64873(12) 0.0242(3) Uani 1 1 d . . . . .
H10 H 0.544867 1.157536 0.682918 0.029 Uiso 1 1 calc R . . . .
C11 C 0.40092(12) 1.19779(18) 0.61602(12) 0.0266(3) Uani 1 1 d . . . . .
H11 H 0.404284 1.309689 0.627263 0.032 Uiso 1 1 calc R . . . .
C12 C 0.31100(12) 1.12760(18) 0.56675(12) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.253562 1.189954 0.544531 0.031 Uiso 1 1 calc R . . . .
C13 C 0.30897(11) 0.96368(18) 0.55161(11) 0.0218(3) Uani 1 1 d . . . . .
C14 C 0.13133(13) 0.9355(2) 0.48081(17) 0.0389(4) Uani 1 1 d . . . . .
H14A H 0.084338 0.859060 0.439039 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.131917 1.031454 0.435478 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.112514 0.963892 0.550618 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 P1 2.1103(6) . ?
Cl2 C3 1.704(6) . ?
P1 O1 1.6893(12) . ?
P1 O2 1.6842(11) . ?
P1 N1 1.6805(13) . ?
P1 N2 1.6803(14) . ?
O1 C1 1.3704(18) . ?
O2 C8 1.3710(17) . ?
N1 C6 1.4057(19) . ?
N1 C7 1.4699(18) . ?
N2 C13 1.4080(19) . ?
N2 C14 1.474(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.403(2) . ?
C3 H3 0.99(3) . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.406(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.376(2) . ?
C8 C13 1.3933(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 Cl1 89.10(5) . . ?
O2 P1 Cl1 89.63(4) . . ?
O2 P1 O1 178.63(6) . . ?
N1 P1 Cl1 115.78(5) . . ?
N1 P1 O1 89.65(6) . . ?
N1 P1 O2 90.43(6) . . ?
N2 P1 Cl1 113.03(5) . . ?
N2 P1 O1 90.60(6) . . ?
N2 P1 O2 90.38(6) . . ?
N2 P1 N1 131.19(7) . . ?
C1 O1 P1 113.94(9) . . ?
C8 O2 P1 113.65(9) . . ?
C6 N1 P1 113.75(10) . . ?
C6 N1 C7 116.65(12) . . ?
C7 N1 P1 129.48(10) . . ?
C13 N2 P1 112.92(10) . . ?
C13 N2 C14 117.56(13) . . ?
C14 N2 P1 128.17(12) . . ?
O1 C1 C2 125.83(14) . . ?
O1 C1 C6 111.57(13) . . ?
C2 C1 C6 122.60(14) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.08(15) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 Cl2 111.8(2) . . ?
C2 C3 H3 119.5(14) . . ?
C4 C3 Cl2 126.4(2) . . ?
C4 C3 C2 120.96(15) . . ?
C4 C3 H3 119.6(14) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.08(15) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.86(14) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 N1 109.98(13) . . ?
C5 C6 N1 129.65(14) . . ?
C5 C6 C1 120.38(14) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 125.78(13) . . ?
O2 C8 C13 111.48(12) . . ?
C9 C8 C13 122.73(13) . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.29(14) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.70(14) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.42(14) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.63(14) . . ?
C13 C12 H12 121.2 . . ?
C8 C13 N2 110.39(13) . . ?
C12 C13 N2 129.40(14) . . ?
C12 C13 C8 120.21(14) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 P1 O1 C1 -105.63(11) . . . . ?
Cl1 P1 O2 C8 -102.65(9) . . . . ?
Cl1 P1 N1 C6 80.18(11) . . . . ?
Cl1 P1 N1 C7 -95.60(13) . . . . ?
Cl1 P1 N2 C13 80.81(11) . . . . ?
Cl1 P1 N2 C14 -85.44(15) . . . . ?
Cl2 C3 C4 C5 -167.6(3) . . . . ?
P1 O1 C1 C2 171.48(13) . . . . ?
P1 O1 C1 C6 -9.10(17) . . . . ?
P1 O2 C8 C9 171.59(11) . . . . ?
P1 O2 C8 C13 -9.07(14) . . . . ?
P1 N1 C6 C1 5.19(16) . . . . ?
P1 N1 C6 C5 -174.85(14) . . . . ?
P1 N2 C13 C8 5.51(15) . . . . ?
P1 N2 C13 C12 -174.34(13) . . . . ?
O1 P1 N1 C6 -8.65(11) . . . . ?
O1 P1 N1 C7 175.57(14) . . . . ?
O1 P1 N2 C13 170.09(11) . . . . ?
O1 P1 N2 C14 3.84(16) . . . . ?
O1 C1 C2 C3 177.23(16) . . . . ?
O1 C1 C6 N1 2.43(18) . . . . ?
O1 C1 C6 C5 -177.53(14) . . . . ?
O2 P1 N1 C6 169.98(11) . . . . ?
O2 P1 N1 C7 -5.80(14) . . . . ?
O2 P1 N2 C13 -8.95(11) . . . . ?
O2 P1 N2 C14 -175.20(15) . . . . ?
O2 C8 C9 C10 178.76(13) . . . . ?
O2 C8 C13 N2 2.20(16) . . . . ?
O2 C8 C13 C12 -177.93(12) . . . . ?
N1 P1 O1 C1 10.16(12) . . . . ?
N1 P1 O2 C8 141.57(10) . . . . ?
N1 P1 N2 C13 -99.86(12) . . . . ?
N1 P1 N2 C14 93.89(16) . . . . ?
N2 P1 O1 C1 141.35(12) . . . . ?
N2 P1 O2 C8 10.37(10) . . . . ?
N2 P1 N1 C6 -99.14(12) . . . . ?
N2 P1 N1 C7 85.09(16) . . . . ?
C1 C2 C3 Cl2 170.8(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C1 C6 N1 -178.12(14) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 N1 179.93(16) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C7 N1 C6 C1 -178.46(13) . . . . ?
C7 N1 C6 C5 1.5(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C8 C13 N2 -178.43(12) . . . . ?
C9 C8 C13 C12 1.4(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 N2 178.72(14) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C13 C8 C9 C10 -0.5(2) . . . . ?
C14 N2 C13 C8 173.34(14) . . . . ?
C14 N2 C13 C12 -6.5(2) . . . . ?

_olex2_diffrn_ambient_temperature_device Kryoflex
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dg314
_audit_block_doi                 10.5517/ccdc.csd.cc1ph4nz
_database_code_depnum_ccdc_archive 'CCDC 1563691'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
Spiro{bis[1,2-phenyleneoxy(phenylamino)]-2-(phenylamino)phenoxy-phosphorane}
_chemical_formula_moiety         'C36 H28 N3 O3 P'
_chemical_formula_sum            'C36 H28 N3 O3 P'
_chemical_formula_weight         581.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.3599(11)
_cell_length_b                   10.9120(11)
_cell_length_c                   13.4535(14)
_cell_angle_alpha                77.059(2)
_cell_angle_beta                 88.933(2)
_cell_angle_gamma                72.200(2)
_cell_volume                     1409.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.026
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0445 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9314.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.043
_diffrn_reflns_theta_min         1.555
_diffrn_ambient_temperature      90.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6547
_reflns_number_total             8246
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8246
_refine_ls_number_restraints     477
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.7867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1348
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(N3A)=Sof(H3AA)=Sof(C25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=
 Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C36A)=
 Sof(C35A)=Sof(H35A)=Sof(C34A)=Sof(H34A)=Sof(C33A)=Sof(H33A)=Sof(C32A)=
 Sof(H32A)=Sof(C31A)=1-FVAR(1)
 Sof(N3)=Sof(H3A)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=
 Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
  C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
 C33(H33), C34(H34), C35(H35), N3A(H3AA), C26A(H26A), C27A(H27A), C28A(H28A),
 C29A(H29A), C30A(H30A), C35A(H35A), C34A(H34A), C33A(H33A), C32A(H32A)
4.b Fitted hexagon refined as free rotating group:
 C25A(C26A,C27A,C28A,C29A,C30A), C36A(C35A,C34A,C33A,C32A,C31A)
;
_atom_sites_solution_hydrogens   mixed
_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
P1 P 0.39075(4) 0.52110(4) 0.74833(3) 0.01612(9) Uani 1 1 d . U . . .
O1 O 0.47570(11) 0.35644(10) 0.78462(8) 0.0192(2) Uani 1 1 d . U . . .
O2 O 0.30463(10) 0.68501(10) 0.71959(8) 0.0180(2) Uani 1 1 d . U . . .
O3 O 0.42620(11) 0.51592(11) 0.63153(8) 0.0192(2) Uani 1 1 d . U . . .
N1 N 0.51163(13) 0.55147(12) 0.81220(10) 0.0177(2) Uani 1 1 d . U . . .
N2 N 0.24639(12) 0.49122(12) 0.79098(10) 0.0176(2) Uani 1 1 d . U . . .
C1 C 0.52344(15) 0.68045(15) 0.80711(12) 0.0192(3) Uani 1 1 d . U . . .
C2 C 0.58499(17) 0.73712(17) 0.72366(13) 0.0259(3) Uani 1 1 d . U . . .
H2 H 0.6209 0.6898 0.6729 0.031 Uiso 1 1 calc R . . . .
C3 C 0.59294(19) 0.86365(19) 0.71612(15) 0.0325(4) Uani 1 1 d . U . . .
H3 H 0.6336 0.9039 0.6595 0.039 Uiso 1 1 calc R . . . .
C4 C 0.5418(2) 0.93090(18) 0.79105(15) 0.0336(4) Uani 1 1 d . U . . .
H4 H 0.5464 1.0178 0.7852 0.040 Uiso 1 1 calc R . . . .
C5 C 0.4834(2) 0.87223(18) 0.87509(14) 0.0316(4) Uani 1 1 d . U . . .
H5 H 0.4500 0.9186 0.9269 0.038 Uiso 1 1 calc R . . . .
C6 C 0.47371(18) 0.74603(16) 0.88342(13) 0.0247(3) Uani 1 1 d . U . . .
H6 H 0.4337 0.7056 0.9404 0.030 Uiso 1 1 calc R . . . .
C7 C 0.61935(15) 0.43827(15) 0.85751(11) 0.0185(3) Uani 1 1 d . U . . .
C8 C 0.73581(16) 0.42827(17) 0.91193(12) 0.0226(3) Uani 1 1 d . U . . .
H8 H 0.7531 0.5046 0.9236 0.027 Uiso 1 1 calc R . . . .
C9 C 0.82724(17) 0.30149(17) 0.94915(13) 0.0264(3) Uani 1 1 d . U . . .
H9 H 0.9081 0.2919 0.9865 0.032 Uiso 1 1 calc R . . . .
C10 C 0.80164(17) 0.18980(17) 0.93240(12) 0.0247(3) Uani 1 1 d . U . . .
H10 H 0.8651 0.1050 0.9583 0.030 Uiso 1 1 calc R . . . .
C11 C 0.68317(16) 0.20088(16) 0.87769(12) 0.0222(3) Uani 1 1 d . U . . .
H11 H 0.6646 0.1249 0.8664 0.027 Uiso 1 1 calc R . . . .
C12 C 0.59418(15) 0.32656(15) 0.84074(11) 0.0181(3) Uani 1 1 d . U . . .
C13 C 0.22229(15) 0.36494(14) 0.81753(11) 0.0168(3) Uani 1 1 d . U . . .
C14 C 0.25717(17) 0.28357(16) 0.91450(12) 0.0221(3) Uani 1 1 d . U . . .
H14 H 0.2988 0.3099 0.9650 0.027 Uiso 1 1 calc R . . . .
C15 C 0.23068(19) 0.16335(17) 0.93711(13) 0.0270(3) Uani 1 1 d . U . . .
H15 H 0.2543 0.1072 1.0034 0.032 Uiso 1 1 calc R . . . .
C16 C 0.16990(18) 0.12438(17) 0.86345(13) 0.0256(3) Uani 1 1 d . U . . .
H16 H 0.1539 0.0411 0.8790 0.031 Uiso 1 1 calc R . . . .
C17 C 0.13289(18) 0.20725(17) 0.76758(13) 0.0251(3) Uani 1 1 d . U . . .
H17 H 0.0908 0.1812 0.7173 0.030 Uiso 1 1 calc R . . . .
C18 C 0.15720(16) 0.32817(16) 0.74484(12) 0.0217(3) Uani 1 1 d . U . . .
H18 H 0.1294 0.3861 0.6796 0.026 Uiso 1 1 calc R . . . .
C19 C 0.13720(15) 0.60564(15) 0.79264(11) 0.0173(3) Uani 1 1 d . U . . .
C20 C 0.00910(15) 0.61639(16) 0.82927(12) 0.0216(3) Uani 1 1 d . U . . .
H20 H -0.0180 0.5403 0.8560 0.026 Uiso 1 1 calc R . . . .
C21 C -0.07880(16) 0.74409(17) 0.82533(13) 0.0253(3) Uani 1 1 d . U . . .
H21 H -0.1674 0.7547 0.8494 0.030 Uiso 1 1 calc R . . . .
C22 C -0.03881(17) 0.85544(17) 0.78685(12) 0.0252(3) Uani 1 1 d . U . . .
H22 H -0.1001 0.9407 0.7858 0.030 Uiso 1 1 calc R . . . .
C23 C 0.09069(16) 0.84358(16) 0.74957(12) 0.0209(3) Uani 1 1 d . U . . .
H23 H 0.1189 0.9191 0.7232 0.025 Uiso 1 1 calc R . . . .
C24 C 0.17560(14) 0.71722(15) 0.75280(11) 0.0173(3) Uani 1 1 d . U . . .
N3 N 0.32687(15) 0.37333(15) 0.53529(11) 0.0202(3) Uani 0.911(2) 1 d . U P A 1
H3A H 0.395(2) 0.344(2) 0.5823(18) 0.027(6) Uiso 0.911(2) 1 d . . P A 1
C25 C 0.26629(18) 0.28033(18) 0.52166(14) 0.0197(3) Uani 0.911(2) 1 d . U P A 1
C26 C 0.33930(19) 0.14682(19) 0.56042(16) 0.0244(4) Uani 0.911(2) 1 d . U P A 1
H26 H 0.4286 0.1238 0.5898 0.029 Uiso 0.911(2) 1 calc R . P A 1
C27 C 0.2827(2) 0.0483(2) 0.55635(18) 0.0309(4) Uani 0.911(2) 1 d . U P A 1
H27 H 0.3321 -0.0416 0.5848 0.037 Uiso 0.911(2) 1 calc R . P A 1
C28 C 0.1533(3) 0.0809(3) 0.51051(16) 0.0321(5) Uani 0.911(2) 1 d . U P A 1
H28 H 0.1155 0.0133 0.5056 0.038 Uiso 0.911(2) 1 calc R . P A 1
C29 C 0.0803(2) 0.2127(3) 0.47219(16) 0.0308(5) Uani 0.911(2) 1 d . U P A 1
H29 H -0.0084 0.2349 0.4418 0.037 Uiso 0.911(2) 1 calc R . P A 1
C30 C 0.1350(2) 0.3128(2) 0.47753(15) 0.0253(4) Uani 0.911(2) 1 d . U P A 1
H30 H 0.0837 0.4027 0.4514 0.030 Uiso 0.911(2) 1 calc R . P A 1
C31 C 0.29354(16) 0.50787(17) 0.49088(12) 0.0177(3) Uani 0.911(2) 1 d . U P A 1
C32 C 0.22240(17) 0.57083(19) 0.39603(13) 0.0228(4) Uani 0.911(2) 1 d . U P A 1
H32 H 0.1866 0.5221 0.3597 0.027 Uiso 0.911(2) 1 calc R . P A 1
C33 C 0.20422(18) 0.7041(2) 0.35520(13) 0.0269(4) Uani 0.911(2) 1 d . U P A 1
H33 H 0.1545 0.7458 0.2916 0.032 Uiso 0.911(2) 1 calc R . P A 1
C34 C 0.2570(2) 0.7770(2) 0.40512(15) 0.0268(4) Uani 0.911(2) 1 d . U P A 1
H34 H 0.2445 0.8678 0.3758 0.032 Uiso 0.911(2) 1 calc R . P A 1
C35 C 0.32913(18) 0.71615(18) 0.49933(13) 0.0227(4) Uani 0.911(2) 1 d . U P A 1
H35 H 0.3674 0.7648 0.5339 0.027 Uiso 0.911(2) 1 calc R . P A 1
C36 C 0.34400(16) 0.58484(17) 0.54142(12) 0.0173(3) Uani 0.911(2) 1 d . U P A 1
N3A N 0.6146(17) 0.6363(17) 0.5388(14) 0.030(3) Uani 0.089(2) 1 d . U P A 2
H3AA H 0.6454 0.5547 0.5755 0.036 Uiso 0.089(2) 1 calc R . P A 2
C25A C 0.7070(13) 0.7103(13) 0.5252(13) 0.029(3) Uani 0.089(2) 1 d . U P A 2
C26A C 0.6652(12) 0.8471(13) 0.4917(13) 0.030(4) Uani 0.089(2) 1 d G U P A 2
H26A H 0.5723 0.8939 0.4730 0.036 Uiso 0.089(2) 1 calc R . P A 2
C27A C 0.7595(17) 0.9156(12) 0.4854(13) 0.027(4) Uani 0.089(2) 1 d G U P A 2
H27A H 0.7309 1.0091 0.4624 0.033 Uiso 0.089(2) 1 calc R . P A 2
C28A C 0.8955(15) 0.8471(18) 0.5127(14) 0.040(7) Uani 0.089(2) 1 d G U P A 2
H28A H 0.9599 0.8939 0.5084 0.048 Uiso 0.089(2) 1 calc R . P A 2
C29A C 0.9373(11) 0.7102(18) 0.5463(13) 0.036(4) Uani 0.089(2) 1 d G U P A 2
H29A H 1.0303 0.6634 0.5649 0.043 Uiso 0.089(2) 1 calc R . P A 2
C30A C 0.8431(15) 0.6418(12) 0.5525(12) 0.032(4) Uani 0.089(2) 1 d G U P A 2
H30A H 0.8717 0.5483 0.5755 0.038 Uiso 0.089(2) 1 calc R . P A 2
C36A C 0.3912(12) 0.6235(12) 0.5594(7) 0.027(3) Uani 0.089(2) 1 d . U P A 2
C35A C 0.2569(11) 0.6560(12) 0.5244(9) 0.020(3) Uani 0.089(2) 1 d G U P A 2
H35A H 0.1960 0.6186 0.5647 0.024 Uiso 0.089(2) 1 calc R . P A 2
C34A C 0.2116(10) 0.7431(14) 0.4305(10) 0.034(5) Uani 0.089(2) 1 d G U P A 2
H34A H 0.1198 0.7653 0.4066 0.041 Uiso 0.089(2) 1 calc R . P A 2
C33A C 0.3007(14) 0.7977(13) 0.3716(8) 0.034(5) Uani 0.089(2) 1 d G U P A 2
H33A H 0.2697 0.8572 0.3073 0.041 Uiso 0.089(2) 1 calc R . P A 2
C32A C 0.4350(12) 0.7652(13) 0.4066(9) 0.032(4) Uani 0.089(2) 1 d G U P A 2
H32A H 0.4959 0.8025 0.3663 0.038 Uiso 0.089(2) 1 calc R . P A 2
C31A C 0.4803(10) 0.6781(13) 0.5005(9) 0.025(3) Uani 0.089(2) 1 d G U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.7022(11) . ?
P1 O2 1.6947(11) . ?
P1 O3 1.6164(11) . ?
P1 N1 1.6845(13) . ?
P1 N2 1.6895(13) . ?
O1 C12 1.3647(18) . ?
O2 C24 1.3679(18) . ?
O3 C36 1.4139(18) . ?
O3 C36A 1.301(9) . ?
N1 C1 1.436(2) . ?
N1 C7 1.4100(19) . ?
N2 C13 1.4406(19) . ?
N2 C19 1.4096(19) . ?
C1 C2 1.397(2) . ?
C1 C6 1.384(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 C12 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.403(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.402(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C13 C14 1.387(2) . ?
C13 C18 1.392(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 C24 1.387(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.402(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.402(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
N3 H3A 0.89(2) . ?
N3 C25 1.391(2) . ?
N3 C31 1.392(2) . ?
C25 C26 1.403(3) . ?
C25 C30 1.403(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.395(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.392(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.406(2) . ?
C31 C36 1.407(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.389(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.379(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.400(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.379(2) . ?
N3A H3AA 0.8800 . ?
N3A C25A 1.41(2) . ?
N3A C31A 1.394(19) . ?
C25A C26A 1.3900 . ?
C25A C30A 1.3900 . ?
C26A H26A 0.9500 . ?
C26A C27A 1.3900 . ?
C27A H27A 0.9500 . ?
C27A C28A 1.3900 . ?
C28A H28A 0.9500 . ?
C28A C29A 1.3900 . ?
C29A H29A 0.9500 . ?
C29A C30A 1.3900 . ?
C30A H30A 0.9500 . ?
C36A C35A 1.3900 . ?
C36A C31A 1.3900 . ?
C35A H35A 0.9500 . ?
C35A C34A 1.3900 . ?
C34A H34A 0.9500 . ?
C34A C33A 1.3900 . ?
C33A H33A 0.9500 . ?
C33A C32A 1.3900 . ?
C32A H32A 0.9500 . ?
C32A C31A 1.3900 . ?

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
O2 P1 O1 176.61(6) . . ?
O3 P1 O1 89.08(6) . . ?
O3 P1 O2 94.31(6) . . ?
O3 P1 N1 112.71(6) . . ?
O3 P1 N2 118.14(6) . . ?
N1 P1 O1 89.13(6) . . ?
N1 P1 O2 89.40(6) . . ?
N1 P1 N2 129.10(7) . . ?
N2 P1 O1 89.75(6) . . ?
N2 P1 O2 88.81(6) . . ?
C12 O1 P1 114.33(10) . . ?
C24 O2 P1 114.80(9) . . ?
C36 O3 P1 128.29(10) . . ?
C36A O3 P1 120.5(6) . . ?
C1 N1 P1 124.73(10) . . ?
C7 N1 P1 114.68(11) . . ?
C7 N1 C1 119.55(12) . . ?
C13 N2 P1 127.06(10) . . ?
C19 N2 P1 114.44(10) . . ?
C19 N2 C13 118.33(12) . . ?
C2 C1 N1 118.45(14) . . ?
C6 C1 N1 120.03(14) . . ?
C6 C1 C2 121.52(15) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.99(17) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.98(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.52(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.22(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.74(16) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C7 N1 129.64(15) . . ?
C8 C7 C12 121.02(14) . . ?
C12 C7 N1 109.35(13) . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.70(15) . . ?
C9 C8 H8 121.1 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.15(15) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.72(15) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.60(15) . . ?
C12 C11 H11 121.2 . . ?
O1 C12 C7 112.45(13) . . ?
O1 C12 C11 125.75(14) . . ?
C11 C12 C7 121.80(14) . . ?
C14 C13 N2 121.28(13) . . ?
C14 C13 C18 120.17(14) . . ?
C18 C13 N2 118.48(13) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.35(15) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.53(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.77(15) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.06(15) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.04(14) . . ?
C17 C18 H18 120.0 . . ?
C20 C19 N2 129.32(14) . . ?
C24 C19 N2 109.63(13) . . ?
C24 C19 C20 121.03(14) . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.33(15) . . ?
C21 C20 H20 121.3 . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.33(15) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 120.91(15) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 121.4 . . ?
C24 C23 C22 117.10(15) . . ?
C24 C23 H23 121.4 . . ?
O2 C24 C19 111.71(13) . . ?
O2 C24 C23 126.01(14) . . ?
C23 C24 C19 122.28(14) . . ?
C25 N3 H3A 115.6(15) . . ?
C25 N3 C31 130.41(15) . . ?
C31 N3 H3A 113.9(15) . . ?
N3 C25 C26 117.00(15) . . ?
N3 C25 C30 123.92(17) . . ?
C26 C25 C30 118.97(17) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.76(18) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(2) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 120.9(2) . . ?
C30 C29 H29 119.5 . . ?
C25 C30 H30 120.2 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.2 . . ?
N3 C31 C32 125.17(16) . . ?
N3 C31 C36 117.16(14) . . ?
C32 C31 C36 117.49(16) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.24(17) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.29(17) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.47(18) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 120.3 . . ?
C36 C35 C34 119.34(18) . . ?
C36 C35 H35 120.3 . . ?
C31 C36 O3 116.02(14) . . ?
C35 C36 O3 121.36(16) . . ?
C35 C36 C31 122.12(15) . . ?
C25A N3A H3AA 116.3 . . ?
C31A N3A H3AA 116.3 . . ?
C31A N3A C25A 127.4(15) . . ?
C26A C25A N3A 122.4(12) . . ?
C26A C25A C30A 120.0 . . ?
C30A C25A N3A 117.5(12) . . ?
C25A C26A H26A 120.0 . . ?
C27A C26A C25A 120.0 . . ?
C27A C26A H26A 120.0 . . ?
C26A C27A H27A 120.0 . . ?
C26A C27A C28A 120.0 . . ?
C28A C27A H27A 120.0 . . ?
C27A C28A H28A 120.0 . . ?
C27A C28A C29A 120.0 . . ?
C29A C28A H28A 120.0 . . ?
C28A C29A H29A 120.0 . . ?
C30A C29A C28A 120.0 . . ?
C30A C29A H29A 120.0 . . ?
C25A C30A H30A 120.0 . . ?
C29A C30A C25A 120.0 . . ?
C29A C30A H30A 120.0 . . ?
O3 C36A C35A 111.6(8) . . ?
O3 C36A C31A 125.5(8) . . ?
C35A C36A C31A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
C35A C34A H34A 120.0 . . ?
C35A C34A C33A 120.0 . . ?
C33A C34A H34A 120.0 . . ?
C34A C33A H33A 120.0 . . ?
C34A C33A C32A 120.0 . . ?
C32A C33A H33A 120.0 . . ?
C33A C32A H32A 120.0 . . ?
C33A C32A C31A 120.0 . . ?
C31A C32A H32A 120.0 . . ?
C36A C31A N3A 116.6(10) . . ?
C32A C31A N3A 123.4(11) . . ?
C32A C31A C36A 120.0 . . ?

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
C2 H2 N3A 0.95 2.02 2.912(18) 154.8 .

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
P1 O1 C12 C7 0.81(16) . . . . ?
P1 O1 C12 C11 -178.65(12) . . . . ?
P1 O2 C24 C19 -7.33(15) . . . . ?
P1 O2 C24 C23 172.08(12) . . . . ?
P1 O3 C36 C31 -109.50(15) . . . . ?
P1 O3 C36 C35 78.43(19) . . . . ?
P1 O3 C36A C35A -82.7(8) . . . . ?
P1 O3 C36A C31A 116.7(7) . . . . ?
P1 N1 C1 C2 -80.56(17) . . . . ?
P1 N1 C1 C6 99.04(16) . . . . ?
P1 N1 C7 C8 177.71(14) . . . . ?
P1 N1 C7 C12 -2.54(16) . . . . ?
P1 N2 C13 C14 86.14(17) . . . . ?
P1 N2 C13 C18 -96.72(16) . . . . ?
P1 N2 C19 C20 -175.12(13) . . . . ?
P1 N2 C19 C24 3.02(16) . . . . ?
O1 P1 O3 C36 142.79(13) . . . . ?
O1 P1 O3 C36A -176.4(6) . . . . ?
O1 P1 N1 C1 170.76(13) . . . . ?
O1 P1 N1 C7 2.53(11) . . . . ?
O1 P1 N2 C13 -13.90(13) . . . . ?
O1 P1 N2 C19 171.01(11) . . . . ?
O2 P1 O3 C36 -37.38(14) . . . . ?
O2 P1 O3 C36A 3.4(6) . . . . ?
O2 P1 N1 C1 -12.30(13) . . . . ?
O2 P1 N1 C7 179.47(11) . . . . ?
O2 P1 N2 C13 169.16(13) . . . . ?
O2 P1 N2 C19 -5.93(11) . . . . ?
O3 P1 O1 C12 110.84(10) . . . . ?
O3 P1 O2 C24 125.70(10) . . . . ?
O3 P1 N1 C1 82.12(13) . . . . ?
O3 P1 N1 C7 -86.11(11) . . . . ?
O3 P1 N2 C13 74.92(14) . . . . ?
O3 P1 N2 C19 -100.17(11) . . . . ?
O3 C36A C35A C34A -161.8(11) . . . . ?
O3 C36A C31A N3A -18.3(14) . . . . ?
O3 C36A C31A C32A 159.1(13) . . . . ?
N1 P1 O1 C12 -1.90(11) . . . . ?
N1 P1 O2 C24 -121.56(10) . . . . ?
N1 P1 O3 C36 -128.54(13) . . . . ?
N1 P1 O3 C36A -87.7(6) . . . . ?
N1 P1 N2 C13 -102.58(14) . . . . ?
N1 P1 N2 C19 82.33(12) . . . . ?
N1 C1 C2 C3 177.87(15) . . . . ?
N1 C1 C6 C5 -178.33(14) . . . . ?
N1 C7 C8 C9 179.88(15) . . . . ?
N1 C7 C12 O1 1.05(17) . . . . ?
N1 C7 C12 C11 -179.47(13) . . . . ?
N2 P1 O1 C12 -131.01(11) . . . . ?
N2 P1 O2 C24 7.57(10) . . . . ?
N2 P1 O3 C36 53.57(15) . . . . ?
N2 P1 O3 C36A 94.4(6) . . . . ?
N2 P1 N1 C1 -100.27(13) . . . . ?
N2 P1 N1 C7 91.50(12) . . . . ?
N2 C13 C14 C15 179.27(15) . . . . ?
N2 C13 C18 C17 179.73(14) . . . . ?
N2 C19 C20 C21 177.27(15) . . . . ?
N2 C19 C24 O2 2.64(17) . . . . ?
N2 C19 C24 C23 -176.79(13) . . . . ?
C1 N1 C7 C8 8.8(2) . . . . ?
C1 N1 C7 C12 -171.43(13) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
C7 N1 C1 C2 87.13(18) . . . . ?
C7 N1 C1 C6 -93.26(17) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C7 C12 O1 -179.17(13) . . . . ?
C8 C7 C12 C11 0.3(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 O1 178.78(14) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
C13 N2 C19 C20 9.3(2) . . . . ?
C13 N2 C19 C24 -172.53(12) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C13 C18 C17 -3.1(2) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C13 1.8(3) . . . . ?
C18 C13 C14 C15 2.2(2) . . . . ?
C19 N2 C13 C14 -98.93(17) . . . . ?
C19 N2 C13 C18 78.20(18) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C19 C24 O2 -179.04(13) . . . . ?
C20 C19 C24 C23 1.5(2) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 O2 179.46(14) . . . . ?
C22 C23 C24 C19 -1.2(2) . . . . ?
C24 C19 C20 C21 -0.7(2) . . . . ?
N3 C25 C26 C27 175.58(19) . . . . ?
N3 C25 C30 C29 -176.51(18) . . . . ?
N3 C31 C32 C33 -174.77(16) . . . . ?
N3 C31 C36 O3 1.3(2) . . . . ?
N3 C31 C36 C35 173.29(15) . . . . ?
C25 N3 C31 C32 -24.7(3) . . . . ?
C25 N3 C31 C36 160.36(17) . . . . ?
C25 C26 C27 C28 2.0(3) . . . . ?
C26 C25 C30 C29 -0.6(3) . . . . ?
C26 C27 C28 C29 -2.1(3) . . . . ?
C27 C28 C29 C30 0.9(3) . . . . ?
C28 C29 C30 C25 0.4(3) . . . . ?
C30 C25 C26 C27 -0.7(3) . . . . ?
C31 N3 C25 C26 166.83(17) . . . . ?
C31 N3 C25 C30 -17.1(3) . . . . ?
C31 C32 C33 C34 1.2(3) . . . . ?
C32 C31 C36 O3 -174.05(13) . . . . ?
C32 C31 C36 C35 -2.0(2) . . . . ?
C32 C33 C34 C35 -0.7(3) . . . . ?
C33 C34 C35 C36 -1.2(3) . . . . ?
C34 C35 C36 O3 174.15(15) . . . . ?
C34 C35 C36 C31 2.6(3) . . . . ?
C36 C31 C32 C33 0.2(2) . . . . ?
N3A C25A C26A C27A 176.3(17) . . . . ?
N3A C25A C30A C29A -176.4(16) . . . . ?
C25A N3A C31A C36A -148.5(15) . . . . ?
C25A N3A C31A C32A 34(2) . . . . ?
C25A C26A C27A C28A 0.0 . . . . ?
C26A C25A C30A C29A 0.0 . . . . ?
C26A C27A C28A C29A 0.0 . . . . ?
C27A C28A C29A C30A 0.0 . . . . ?
C28A C29A C30A C25A 0.0 . . . . ?
C30A C25A C26A C27A 0.0 . . . . ?
C36A C35A C34A C33A 0.0 . . . . ?
C35A C36A C31A N3A -177.3(14) . . . . ?
C35A C36A C31A C32A 0.0 . . . . ?
C35A C34A C33A C32A 0.0 . . . . ?
C34A C33A C32A C31A 0.0 . . . . ?
C33A C32A C31A N3A 177.2(15) . . . . ?
C33A C32A C31A C36A 0.0 . . . . ?
C31A N3A C25A C26A 16(2) . . . . ?
C31A N3A C25A C30A -167.4(14) . . . . ?
C31A C36A C35A C34A 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/pentane'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dg414_a
_audit_block_doi                 10.5517/ccdc.csd.cc1ph4my
_database_code_depnum_ccdc_archive 'CCDC 1563690'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Lithium tris[1,2-phenyleneoxy(methylamino)]-phosphate'
_chemical_formula_moiety         'C33 H45 Li N3 O6 P'
_chemical_formula_sum            'C33 H45 Li N3 O6 P'
_chemical_formula_weight         617.63
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   13.6235(8)
_cell_length_b                   14.4879(10)
_cell_length_c                   16.0517(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3168.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0547 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8455.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       square
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         1.894
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                8389
_reflns_number_total             9639
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 3358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         9639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.025
_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)+(0.0606P)²+0.5158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1091
_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:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B),
 C31(H31A,H31B), C32(H32A,H32B), C33(H33B,H33A)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.50133(16) 0.60277(13) 0.36056(13) 0.0120(3) Uani 1 1 d . . . . .
C2 C 0.48772(16) 0.64140(14) 0.28161(14) 0.0152(4) Uani 1 1 d . . . . .
H2 H 0.4553 0.6088 0.2400 0.018 Uiso 1 1 calc R . . . .
C3 C 0.52406(17) 0.73065(16) 0.26664(14) 0.0186(4) Uani 1 1 d . . . . .
H3 H 0.5152 0.7573 0.2145 0.022 Uiso 1 1 calc R . . . .
C4 C 0.57268(17) 0.77957(15) 0.32790(15) 0.0188(4) Uani 1 1 d . . . . .
H4 H 0.5966 0.8384 0.3165 0.023 Uiso 1 1 calc R . . . .
C5 C 0.58615(17) 0.74067(15) 0.40759(14) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.6181 0.7734 0.4494 0.020 Uiso 1 1 calc R . . . .
C6 C 0.55088(15) 0.65306(14) 0.42204(13) 0.0126(4) Uani 1 1 d . . . . .
C7 C 0.40687(19) 0.46435(16) 0.33661(15) 0.0223(5) Uani 1 1 d . . . . .
H7A H 0.3943 0.4055 0.3619 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.4377 0.4554 0.2834 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.3460 0.4968 0.3292 0.033 Uiso 1 1 calc GR . . . .
C8 C 0.33174(15) 0.41537(14) 0.52928(13) 0.0124(4) Uani 1 1 d . . . . .
C9 C 0.31702(15) 0.50964(14) 0.54549(13) 0.0127(4) Uani 1 1 d . . . . .
C10 C 0.22798(16) 0.54336(15) 0.57234(14) 0.0155(4) Uani 1 1 d . . . . .
H10 H 0.2198 0.6059 0.5832 0.019 Uiso 1 1 calc R . . . .
C11 C 0.14976(17) 0.48129(16) 0.58298(14) 0.0181(4) Uani 1 1 d . . . . .
H11 H 0.0890 0.5027 0.6011 0.022 Uiso 1 1 calc R . . . .
C12 C 0.16309(17) 0.38784(16) 0.56645(14) 0.0183(4) Uani 1 1 d . . . . .
H12 H 0.1108 0.3472 0.5732 0.022 Uiso 1 1 calc R . . . .
C13 C 0.25436(16) 0.35410(15) 0.53974(14) 0.0156(4) Uani 1 1 d . . . . .
H13 H 0.2629 0.2915 0.5292 0.019 Uiso 1 1 calc R . . . .
C14 C 0.45970(18) 0.30254(14) 0.50277(18) 0.0217(5) Uani 1 1 d . . . . .
H14A H 0.5290 0.3006 0.4919 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.4254 0.2695 0.4599 0.033 Uiso 1 1 calc GR . . . .
H14C H 0.4465 0.2745 0.5558 0.033 Uiso 1 1 calc GR . . . .
C15 C 0.67309(16) 0.43211(14) 0.54134(14) 0.0137(4) Uani 1 1 d . . . . .
C16 C 0.76965(16) 0.40078(14) 0.54445(14) 0.0158(4) Uani 1 1 d . . . . .
H16 H 0.8013 0.3808 0.4964 0.019 Uiso 1 1 calc R . . . .
C17 C 0.81829(17) 0.39995(16) 0.62130(16) 0.0199(5) Uani 1 1 d . . . . .
H17 H 0.8828 0.3791 0.6240 0.024 Uiso 1 1 calc R . . . .
C18 C 0.77220(18) 0.42966(16) 0.69342(15) 0.0204(5) Uani 1 1 d . . . . .
H18 H 0.8054 0.4278 0.7440 0.024 Uiso 1 1 calc R . . . .
C19 C 0.67530(18) 0.46255(16) 0.69019(14) 0.0178(4) Uani 1 1 d . . . . .
H19 H 0.6438 0.4830 0.7382 0.021 Uiso 1 1 calc R . . . .
C20 C 0.62776(16) 0.46394(14) 0.61432(14) 0.0147(4) Uani 1 1 d . . . . .
C21 C 0.64768(17) 0.41148(16) 0.39257(14) 0.0177(4) Uani 1 1 d . . . . .
H21A H 0.5948 0.4109 0.3531 0.027 Uiso 1 1 calc GR . . . .
H21B H 0.6760 0.3509 0.3962 0.027 Uiso 1 1 calc GR . . . .
H21C H 0.6968 0.4547 0.3748 0.027 Uiso 1 1 calc GR . . . .
C22 C 0.3838(2) 0.56268(16) 0.75950(16) 0.0230(5) Uani 1 1 d . . . . .
H22A H 0.4367 0.5183 0.7542 0.028 Uiso 1 1 calc R . . . .
H22B H 0.3229 0.5337 0.7422 0.028 Uiso 1 1 calc R . . . .
C23 C 0.3763(2) 0.59746(18) 0.84788(16) 0.0250(5) Uani 1 1 d . . . . .
H23A H 0.4407 0.6050 0.8727 0.030 Uiso 1 1 calc R . . . .
H23B H 0.3376 0.5560 0.8821 0.030 Uiso 1 1 calc R . . . .
C24 C 0.32449(19) 0.69108(16) 0.83674(16) 0.0226(5) Uani 1 1 d . . . . .
H24A H 0.2541 0.6848 0.8439 0.027 Uiso 1 1 calc R . . . .
H24B H 0.3490 0.7360 0.8764 0.027 Uiso 1 1 calc R . . . .
C25 C 0.34957(18) 0.71961(17) 0.74757(15) 0.0218(5) Uani 1 1 d . . . . .
H25A H 0.2901 0.7317 0.7163 0.026 Uiso 1 1 calc R . . . .
H25B H 0.3894 0.7751 0.7477 0.026 Uiso 1 1 calc R . . . .
C26 C 0.6328(2) 0.7251(2) 0.75525(16) 0.0269(5) Uani 1 1 d . . . . .
H26A H 0.6519 0.6781 0.7952 0.032 Uiso 1 1 calc R . . . .
H26B H 0.5730 0.7543 0.7746 0.032 Uiso 1 1 calc R . . . .
C27 C 0.7144(2) 0.7965(2) 0.7455(2) 0.0387(7) Uani 1 1 d . . . . .
H27A H 0.6895 0.8582 0.7559 0.046 Uiso 1 1 calc R . . . .
H27B H 0.7676 0.7841 0.7840 0.046 Uiso 1 1 calc R . . . .
C28 C 0.7495(2) 0.7875(2) 0.6556(2) 0.0342(6) Uani 1 1 d . . . . .
H28A H 0.7222 0.8358 0.6207 0.041 Uiso 1 1 calc R . . . .
H28B H 0.8206 0.7895 0.6522 0.041 Uiso 1 1 calc R . . . .
C29 C 0.71025(18) 0.69317(18) 0.63102(16) 0.0240(5) Uani 1 1 d . . . . .
H29A H 0.7005 0.6894 0.5713 0.029 Uiso 1 1 calc R . . . .
H29B H 0.7553 0.6448 0.6479 0.029 Uiso 1 1 calc R . . . .
C30 C 0.49679(19) 0.86935(15) 0.60060(16) 0.0205(4) Uani 1 1 d . . . . .
H30A H 0.5594 0.8790 0.5731 0.025 Uiso 1 1 calc R . . . .
H30B H 0.5068 0.8732 0.6603 0.025 Uiso 1 1 calc R . . . .
C31 C 0.42247(18) 0.94196(15) 0.57223(16) 0.0209(5) Uani 1 1 d . . . . .
H31A H 0.4417 0.9692 0.5195 0.025 Uiso 1 1 calc R . . . .
H31B H 0.4154 0.9905 0.6134 0.025 Uiso 1 1 calc R . . . .
C32 C 0.32758(19) 0.88638(16) 0.56337(17) 0.0226(5) Uani 1 1 d . . . . .
H32A H 0.2944 0.8792 0.6164 0.027 Uiso 1 1 calc R . . . .
H32B H 0.2831 0.9144 0.5236 0.027 Uiso 1 1 calc R . . . .
C33 C 0.36789(17) 0.79491(16) 0.53155(17) 0.0220(5) Uani 1 1 d . . . . .
H33B H 0.3214 0.7453 0.5413 0.026 Uiso 1 1 calc R . . . .
H33A H 0.3818 0.7983 0.4724 0.026 Uiso 1 1 calc R . . . .
Li1 Li 0.4942(3) 0.6494(3) 0.6135(2) 0.0189(7) Uani 1 1 d . . . . .
N1 N 0.47105(13) 0.51780(12) 0.38990(11) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.42688(13) 0.39765(11) 0.50387(12) 0.0141(3) Uani 1 1 d . . . . .
N3 N 0.61054(13) 0.43862(12) 0.47374(11) 0.0133(3) Uani 1 1 d . . . . .
O1 O 0.55837(11) 0.60745(10) 0.49592(10) 0.0130(3) Uani 1 1 d . . . . .
O2 O 0.39867(11) 0.56168(10) 0.53234(10) 0.0141(3) Uani 1 1 d . . . . .
O3 O 0.53486(11) 0.49602(11) 0.60175(9) 0.0142(3) Uani 1 1 d . . . . .
O4 O 0.40340(13) 0.64368(11) 0.71043(11) 0.0208(3) Uani 1 1 d . . . . .
O5 O 0.61803(12) 0.68475(12) 0.67447(10) 0.0194(3) Uani 1 1 d . . . . .
O6 O 0.45686(12) 0.78028(11) 0.57847(10) 0.0177(3) Uani 1 1 d . . . . .
P1 P 0.50007(4) 0.49817(3) 0.49597(3) 0.01147(10) 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 C2 1.398(3) . ?
C1 C6 1.400(3) . ?
C1 N1 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.410(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 O1 1.362(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 N1 1.448(3) . ?
C8 C9 1.405(3) . ?
C8 C13 1.388(3) . ?
C8 N2 1.383(3) . ?
C9 C10 1.377(3) . ?
C9 O2 1.360(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.405(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.403(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 N2 1.449(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.402(3) . ?
C15 N3 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.400(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.404(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C20 O3 1.363(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 N3 1.452(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.509(3) . ?
C22 O4 1.438(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.539(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.528(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 O4 1.450(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.527(4) . ?
C26 O5 1.436(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.526(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.520(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 O5 1.442(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.529(3) . ?
C30 O6 1.445(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.530(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.523(3) . ?
C33 H33B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 O6 1.443(3) . ?
Li1 O1 2.167(4) . ?
Li1 O2 2.237(4) . ?
Li1 O3 2.298(4) . ?
Li1 O4 1.989(4) . ?
Li1 O5 2.017(5) . ?
Li1 O6 2.042(4) . ?
Li1 P1 2.892(4) . ?
N1 P1 1.7709(19) . ?
N2 P1 1.7695(18) . ?
N3 P1 1.7710(19) . ?
O1 P1 1.7713(15) . ?
O2 P1 1.7595(15) . ?
O3 P1 1.7631(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.64(19) . . ?
N1 C1 C2 128.79(19) . . ?
N1 C1 C6 111.56(18) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 122.0(2) . . ?
O1 C6 C1 113.42(17) . . ?
O1 C6 C5 124.61(19) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
C13 C8 C9 119.40(19) . . ?
N2 C8 C9 111.66(18) . . ?
N2 C8 C13 128.95(19) . . ?
C10 C9 C8 121.92(19) . . ?
O2 C9 C8 113.16(17) . . ?
O2 C9 C10 124.92(19) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.1(2) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
C16 C15 C20 119.6(2) . . ?
N3 C15 C16 129.2(2) . . ?
N3 C15 C20 111.20(19) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.8(2) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C15 121.7(2) . . ?
O3 C20 C15 113.41(19) . . ?
O3 C20 C19 124.8(2) . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
O4 C22 H22A 110.8 . . ?
O4 C22 H22B 110.8 . . ?
O4 C22 C23 104.77(19) . . ?
C22 C23 H23A 111.3 . . ?
C22 C23 H23B 111.3 . . ?
C22 C23 C24 102.5(2) . . ?
H23A C23 H23B 109.2 . . ?
C24 C23 H23A 111.3 . . ?
C24 C23 H23B 111.3 . . ?
C23 C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
C25 C24 C23 104.17(19) . . ?
C25 C24 H24A 110.9 . . ?
C25 C24 H24B 110.9 . . ?
C24 C25 H25A 110.3 . . ?
C24 C25 H25B 110.3 . . ?
H25A C25 H25B 108.6 . . ?
O4 C25 C24 107.03(19) . . ?
O4 C25 H25A 110.3 . . ?
O4 C25 H25B 110.3 . . ?
H26A C26 H26B 108.6 . . ?
C27 C26 H26A 110.4 . . ?
C27 C26 H26B 110.4 . . ?
O5 C26 H26A 110.4 . . ?
O5 C26 H26B 110.4 . . ?
O5 C26 C27 106.6(2) . . ?
C26 C27 H27A 110.6 . . ?
C26 C27 H27B 110.6 . . ?
H27A C27 H27B 108.8 . . ?
C28 C27 C26 105.5(2) . . ?
C28 C27 H27A 110.6 . . ?
C28 C27 H27B 110.6 . . ?
C27 C28 H28A 111.3 . . ?
C27 C28 H28B 111.3 . . ?
H28A C28 H28B 109.2 . . ?
C29 C28 C27 102.2(2) . . ?
C29 C28 H28A 111.3 . . ?
C29 C28 H28B 111.3 . . ?
C28 C29 H29A 110.8 . . ?
C28 C29 H29B 110.8 . . ?
H29A C29 H29B 108.8 . . ?
O5 C29 C28 104.9(2) . . ?
O5 C29 H29A 110.8 . . ?
O5 C29 H29B 110.8 . . ?
H30A C30 H30B 108.6 . . ?
C31 C30 H30A 110.3 . . ?
C31 C30 H30B 110.3 . . ?
O6 C30 H30A 110.3 . . ?
O6 C30 H30B 110.3 . . ?
O6 C30 C31 106.97(19) . . ?
C30 C31 H31A 111.2 . . ?
C30 C31 H31B 111.2 . . ?
C30 C31 C32 103.01(18) . . ?
H31A C31 H31B 109.1 . . ?
C32 C31 H31A 111.2 . . ?
C32 C31 H31B 111.2 . . ?
C31 C32 H32A 111.6 . . ?
C31 C32 H32B 111.6 . . ?
H32A C32 H32B 109.4 . . ?
C33 C32 C31 100.63(19) . . ?
C33 C32 H32A 111.6 . . ?
C33 C32 H32B 111.6 . . ?
C32 C33 H33B 110.8 . . ?
C32 C33 H33A 110.8 . . ?
H33B C33 H33A 108.9 . . ?
O6 C33 C32 104.82(19) . . ?
O6 C33 H33B 110.8 . . ?
O6 C33 H33A 110.8 . . ?
O1 Li1 O2 64.42(12) . . ?
O1 Li1 O3 63.90(12) . . ?
O1 Li1 P1 37.66(7) . . ?
O2 Li1 O3 62.82(11) . . ?
O2 Li1 P1 37.44(7) . . ?
O3 Li1 P1 37.56(7) . . ?
O4 Li1 O1 157.0(2) . . ?
O4 Li1 O2 94.03(18) . . ?
O4 Li1 O3 100.03(17) . . ?
O4 Li1 O5 98.71(19) . . ?
O4 Li1 O6 95.69(18) . . ?
O4 Li1 P1 119.74(17) . . ?
O5 Li1 O1 98.98(18) . . ?
O5 Li1 O2 156.0(2) . . ?
O5 Li1 O3 94.81(17) . . ?
O5 Li1 O6 96.08(17) . . ?
O5 Li1 P1 119.06(18) . . ?
O6 Li1 O1 96.93(17) . . ?
O6 Li1 O2 102.83(18) . . ?
O6 Li1 O3 159.3(2) . . ?
O6 Li1 P1 122.04(18) . . ?
C1 N1 C7 117.10(18) . . ?
C1 N1 P1 113.85(14) . . ?
C7 N1 P1 128.10(15) . . ?
C8 N2 C14 118.00(17) . . ?
C8 N2 P1 113.36(14) . . ?
C14 N2 P1 127.44(15) . . ?
C15 N3 C21 118.10(18) . . ?
C15 N3 P1 113.50(15) . . ?
C21 N3 P1 127.50(15) . . ?
C6 O1 Li1 126.33(16) . . ?
C6 O1 P1 113.62(13) . . ?
P1 O1 Li1 93.97(12) . . ?
C9 O2 Li1 134.42(17) . . ?
C9 O2 P1 113.81(12) . . ?
P1 O2 Li1 91.92(12) . . ?
C20 O3 Li1 122.79(17) . . ?
C20 O3 P1 113.45(13) . . ?
P1 O3 Li1 89.84(12) . . ?
C22 O4 C25 107.45(17) . . ?
C22 O4 Li1 125.27(17) . . ?
C25 O4 Li1 127.19(18) . . ?
C26 O5 C29 106.25(18) . . ?
C26 O5 Li1 131.20(19) . . ?
C29 O5 Li1 121.05(18) . . ?
C30 O6 Li1 131.91(17) . . ?
C33 O6 C30 108.26(17) . . ?
C33 O6 Li1 119.30(18) . . ?
N1 P1 Li1 119.96(10) . . ?
N1 P1 N3 94.26(9) . . ?
N1 P1 O1 87.49(8) . . ?
N2 P1 Li1 124.12(11) . . ?
N2 P1 N1 94.31(9) . . ?
N2 P1 N3 95.30(8) . . ?
N2 P1 O1 171.24(8) . . ?
N3 P1 Li1 121.60(11) . . ?
N3 P1 O1 93.11(8) . . ?
O1 P1 Li1 48.38(9) . . ?
O2 P1 Li1 50.63(10) . . ?
O2 P1 N1 93.42(8) . . ?
O2 P1 N2 87.95(8) . . ?
O2 P1 N3 171.41(9) . . ?
O2 P1 O1 83.38(7) . . ?
O2 P1 O3 84.31(8) . . ?
O3 P1 Li1 52.60(9) . . ?
O3 P1 N1 171.40(9) . . ?
O3 P1 N2 93.90(9) . . ?
O3 P1 N3 87.54(8) . . ?
O3 P1 O1 84.01(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C6 O1 Li1 -116.5(2) . . . . ?
C1 C6 O1 P1 -2.0(2) . . . . ?
C1 N1 P1 Li1 35.4(2) . . . . ?
C1 N1 P1 N2 169.21(15) . . . . ?
C1 N1 P1 N3 -95.13(16) . . . . ?
C1 N1 P1 O1 -2.20(15) . . . . ?
C1 N1 P1 O2 81.01(15) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 O1 179.64(18) . . . . ?
C2 C1 N1 C7 -8.0(3) . . . . ?
C2 C1 N1 P1 -177.75(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 O1 -179.7(2) . . . . ?
C5 C6 O1 Li1 62.4(3) . . . . ?
C5 C6 O1 P1 176.93(17) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 N1 C7 171.39(19) . . . . ?
C6 C1 N1 P1 1.6(2) . . . . ?
C6 O1 P1 Li1 -132.72(19) . . . . ?
C6 O1 P1 N1 2.33(14) . . . . ?
C6 O1 P1 N3 96.46(14) . . . . ?
C6 O1 P1 O2 -91.41(14) . . . . ?
C6 O1 P1 O3 -176.35(14) . . . . ?
C7 N1 P1 Li1 -133.1(2) . . . . ?
C7 N1 P1 N2 0.8(2) . . . . ?
C7 N1 P1 N3 96.4(2) . . . . ?
C7 N1 P1 O1 -170.6(2) . . . . ?
C7 N1 P1 O2 -87.4(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 O2 Li1 -117.3(2) . . . . ?
C8 C9 O2 P1 1.6(2) . . . . ?
C8 N2 P1 Li1 40.1(2) . . . . ?
C8 N2 P1 N1 -90.92(16) . . . . ?
C8 N2 P1 N3 174.39(16) . . . . ?
C8 N2 P1 O2 2.35(16) . . . . ?
C8 N2 P1 O3 86.50(16) . . . . ?
C9 C8 C13 C12 -0.1(3) . . . . ?
C9 C8 N2 C14 166.5(2) . . . . ?
C9 C8 N2 P1 -2.0(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 O2 P1 Li1 -141.29(19) . . . . ?
C9 O2 P1 N1 91.98(15) . . . . ?
C9 O2 P1 N2 -2.22(15) . . . . ?
C9 O2 P1 O1 179.05(15) . . . . ?
C9 O2 P1 O3 -96.34(14) . . . . ?
C10 C9 O2 Li1 62.3(3) . . . . ?
C10 C9 O2 P1 -178.75(18) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
C13 C8 C9 O2 -179.70(19) . . . . ?
C13 C8 N2 C14 -13.6(3) . . . . ?
C13 C8 N2 P1 177.98(19) . . . . ?
C14 N2 P1 Li1 -127.0(2) . . . . ?
C14 N2 P1 N1 102.0(2) . . . . ?
C14 N2 P1 N3 7.3(2) . . . . ?
C14 N2 P1 O2 -164.8(2) . . . . ?
C14 N2 P1 O3 -80.6(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C15 C20 O3 Li1 -111.1(2) . . . . ?
C15 C20 O3 P1 -5.1(2) . . . . ?
C15 N3 P1 Li1 33.40(19) . . . . ?
C15 N3 P1 N1 162.73(15) . . . . ?
C15 N3 P1 N2 -102.53(16) . . . . ?
C15 N3 P1 O1 75.02(15) . . . . ?
C15 N3 P1 O3 -8.84(15) . . . . ?
C16 C15 C20 C19 -2.0(3) . . . . ?
C16 C15 C20 O3 177.46(18) . . . . ?
C16 C15 N3 C21 -1.3(3) . . . . ?
C16 C15 N3 P1 -171.30(18) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C15 1.1(3) . . . . ?
C18 C19 C20 O3 -178.3(2) . . . . ?
C19 C20 O3 Li1 68.3(3) . . . . ?
C19 C20 O3 P1 174.35(18) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
C20 C15 N3 C21 177.80(18) . . . . ?
C20 C15 N3 P1 7.8(2) . . . . ?
C20 O3 P1 Li1 -126.09(19) . . . . ?
C20 O3 P1 N2 102.94(14) . . . . ?
C20 O3 P1 N3 7.78(15) . . . . ?
C20 O3 P1 O1 -85.60(14) . . . . ?
C20 O3 P1 O2 -169.52(14) . . . . ?
C21 N3 P1 Li1 -135.41(19) . . . . ?
C21 N3 P1 N1 -6.09(19) . . . . ?
C21 N3 P1 N2 88.7(2) . . . . ?
C21 N3 P1 O1 -93.80(19) . . . . ?
C21 N3 P1 O3 -177.66(19) . . . . ?
C22 C23 C24 C25 -25.0(3) . . . . ?
C23 C22 O4 C25 -35.5(3) . . . . ?
C23 C22 O4 Li1 141.4(2) . . . . ?
C23 C24 C25 O4 4.7(3) . . . . ?
C24 C25 O4 C22 18.9(3) . . . . ?
C24 C25 O4 Li1 -157.9(2) . . . . ?
C26 C27 C28 C29 -17.9(3) . . . . ?
C27 C26 O5 C29 26.9(3) . . . . ?
C27 C26 O5 Li1 -138.9(3) . . . . ?
C27 C28 C29 O5 34.5(3) . . . . ?
C28 C29 O5 C26 -39.0(3) . . . . ?
C28 C29 O5 Li1 128.6(2) . . . . ?
C30 C31 C32 C33 -35.6(2) . . . . ?
C31 C30 O6 C33 5.4(3) . . . . ?
C31 C30 O6 Li1 -165.9(2) . . . . ?
C31 C32 C33 O6 39.9(2) . . . . ?
C32 C33 O6 C30 -28.8(2) . . . . ?
C32 C33 O6 Li1 143.8(2) . . . . ?
Li1 O1 P1 N1 135.05(13) . . . . ?
Li1 O1 P1 N3 -130.82(13) . . . . ?
Li1 O1 P1 O2 41.31(13) . . . . ?
Li1 O1 P1 O3 -43.63(13) . . . . ?
Li1 O2 P1 N1 -126.73(12) . . . . ?
Li1 O2 P1 N2 139.07(13) . . . . ?
Li1 O2 P1 O1 -39.67(12) . . . . ?
Li1 O2 P1 O3 44.94(12) . . . . ?
Li1 O3 P1 N2 -130.97(12) . . . . ?
Li1 O3 P1 N3 133.88(13) . . . . ?
Li1 O3 P1 O1 40.49(12) . . . . ?
Li1 O3 P1 O2 -43.43(12) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
N1 C1 C6 C5 -178.7(2) . . . . ?
N1 C1 C6 O1 0.2(3) . . . . ?
N2 C8 C9 C10 -179.4(2) . . . . ?
N2 C8 C9 O2 0.3(3) . . . . ?
N2 C8 C13 C12 179.9(2) . . . . ?
N3 C15 C16 C17 -179.4(2) . . . . ?
N3 C15 C20 C19 178.8(2) . . . . ?
N3 C15 C20 O3 -1.8(3) . . . . ?
O2 C9 C10 C11 179.8(2) . . . . ?
O4 C22 C23 C24 37.1(3) . . . . ?
O5 C26 C27 C28 -4.5(3) . . . . ?
O6 C30 C31 C32 19.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dg436_a_a
_audit_block_doi                 10.5517/ccdc.csd.cc1ph4lx
_database_code_depnum_ccdc_archive 'CCDC 1563689'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
Spiro{bis[1,2-phenyleneoxy(methylamino)]-2-(methylamino)phenoxy-phosphorane}
_chemical_formula_moiety         'C21 H22 N3 O3 P'
_chemical_formula_sum            'C21 H22 N3 O3 P'
_chemical_formula_weight         395.40
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   8.548(2)
_cell_length_b                   8.812(3)
_cell_length_c                   13.822(4)
_cell_angle_alpha                101.844(8)
_cell_angle_beta                 106.513(7)
_cell_angle_gamma                102.755(7)
_cell_volume                     932.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5016
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1698 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8621.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             373
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19607
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.740
_diffrn_reflns_theta_min         1.604
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4566
_reflns_number_total             5745
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.043
_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)+(0.0645P)²+0.3298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1328
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
  C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.49261(5) 0.61352(5) 0.23166(3) 0.01422(10) Uani 1 1 d . . . . .
O1 O 0.28720(13) 0.61571(12) 0.19297(8) 0.0167(2) Uani 1 1 d . . . . .
O2 O 0.48137(14) 0.56897(13) 0.33771(8) 0.0174(2) Uani 1 1 d . . . . .
O3 O 0.69794(13) 0.61113(13) 0.27115(8) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.29446(17) 0.32720(16) 0.38709(11) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.3435 0.3079 0.3415 0.024 Uiso 1 1 calc R . . . .
N3 N 0.44675(16) 0.45382(16) 0.12650(10) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.55657(16) 0.81082(15) 0.23605(10) 0.0168(2) Uani 1 1 d . . . . .
C1 C 0.26644(19) 0.76220(18) 0.18463(11) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.1121(2) 0.79413(19) 0.15581(12) 0.0194(3) Uani 1 1 d . . . . .
H2A H 0.0098 0.7147 0.1407 0.023 Uiso 1 1 calc R . . . .
C3 C 0.1162(2) 0.9516(2) 0.15023(13) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.0145 0.9780 0.1303 0.028 Uiso 1 1 calc R . . . .
C4 C 0.2698(2) 1.0682(2) 0.17404(13) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.2692 1.1719 0.1694 0.028 Uiso 1 1 calc R . . . .
C5 C 0.4261(2) 1.03476(19) 0.20498(12) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.5291 1.1145 0.2220 0.025 Uiso 1 1 calc R . . . .
C6 C 0.42167(19) 0.87826(18) 0.20932(11) 0.0162(3) Uani 1 1 d . . . . .
C7 C 0.7301(2) 0.9111(2) 0.25599(14) 0.0237(3) Uani 1 1 d . . . . .
H7A H 0.7729 0.9877 0.3247 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.7282 0.9684 0.2038 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.8030 0.8429 0.2525 0.036 Uiso 1 1 calc GR . . . .
C8 C 0.38027(18) 0.60964(18) 0.39619(11) 0.0157(3) Uani 1 1 d . . . . .
C9 C 0.3782(2) 0.76732(19) 0.43041(12) 0.0187(3) Uani 1 1 d . . . . .
H9 H 0.4342 0.8482 0.4076 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2920(2) 0.80491(19) 0.49924(13) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.2880 0.9105 0.5216 0.026 Uiso 1 1 calc R . . . .
C11 C 0.2122(2) 0.6839(2) 0.53414(12) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.1570 0.7093 0.5816 0.025 Uiso 1 1 calc R . . . .
C12 C 0.21349(19) 0.52516(19) 0.49930(12) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.1594 0.4454 0.5237 0.021 Uiso 1 1 calc R . . . .
C13 C 0.29531(18) 0.48385(18) 0.42775(11) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.2127(2) 0.19446(19) 0.41962(14) 0.0236(3) Uani 1 1 d . . . . .
H14A H 0.2323 0.0965 0.3872 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.0921 0.1804 0.3984 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.2595 0.2183 0.4948 0.035 Uiso 1 1 calc GR . . . .
C15 C 0.7276(2) 0.48361(18) 0.21302(12) 0.0168(3) Uani 1 1 d . . . . .
C16 C 0.8821(2) 0.4504(2) 0.23407(13) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.9768 0.5143 0.2925 0.025 Uiso 1 1 calc R . . . .
C17 C 0.8895(2) 0.3157(2) 0.16322(14) 0.0254(4) Uani 1 1 d . . . . .
H17 H 0.9913 0.2890 0.1745 0.030 Uiso 1 1 calc R . . . .
C18 C 0.7477(2) 0.2221(2) 0.07682(14) 0.0256(4) Uani 1 1 d . . . . .
H18 H 0.7560 0.1338 0.0307 0.031 Uiso 1 1 calc R . . . .
C19 C 0.5915(2) 0.25735(19) 0.05716(12) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.4963 0.1938 -0.0011 0.026 Uiso 1 1 calc R . . . .
C20 C 0.5837(2) 0.38984(18) 0.12730(12) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.2885(2) 0.3850(2) 0.03542(12) 0.0221(3) Uani 1 1 d . . . . .
H21A H 0.2190 0.2902 0.0436 0.033 Uiso 1 1 calc GR . . . .
H21B H 0.3152 0.3555 -0.0275 0.033 Uiso 1 1 calc GR . . . .
H21C H 0.2274 0.4639 0.0303 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.6897(12) . ?
P1 O2 1.6161(12) . ?
P1 O3 1.6899(12) . ?
P1 N3 1.6851(13) . ?
P1 N1 1.6863(14) . ?
O1 C1 1.3645(17) . ?
O2 C8 1.3941(17) . ?
O3 C15 1.3580(17) . ?
N2 H2 0.8600 . ?
N2 C13 1.3770(19) . ?
N2 C14 1.447(2) . ?
N3 C20 1.4057(19) . ?
N3 C21 1.463(2) . ?
N1 C6 1.4036(19) . ?
N1 C7 1.465(2) . ?
C1 C2 1.374(2) . ?
C1 C6 1.387(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.399(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.379(2) . ?
C8 C13 1.404(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.379(2) . ?
C15 C20 1.386(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.401(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.402(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O3 179.60(6) . . ?
O2 P1 O1 92.23(6) . . ?
O2 P1 O3 87.37(6) . . ?
O2 P1 N3 115.54(7) . . ?
O2 P1 N1 118.64(6) . . ?
N3 P1 O1 90.79(6) . . ?
N3 P1 O3 89.41(6) . . ?
N3 P1 N1 125.75(7) . . ?
N1 P1 O1 89.67(6) . . ?
N1 P1 O3 90.49(6) . . ?
C1 O1 P1 114.52(10) . . ?
C8 O2 P1 128.39(9) . . ?
C15 O3 P1 114.49(10) . . ?
C13 N2 H2 119.4 . . ?
C13 N2 C14 121.27(13) . . ?
C14 N2 H2 119.4 . . ?
C20 N3 P1 113.74(10) . . ?
C20 N3 C21 118.74(13) . . ?
C21 N3 P1 127.41(11) . . ?
C6 N1 P1 113.74(10) . . ?
C6 N1 C7 118.39(13) . . ?
C7 N1 P1 127.69(11) . . ?
O1 C1 C2 125.12(14) . . ?
O1 C1 C6 111.77(13) . . ?
C2 C1 C6 123.11(14) . . ?
C1 C2 H2A 121.5 . . ?
C1 C2 C3 116.92(15) . . ?
C3 C2 H2A 121.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.61(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.86(15) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.42(15) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 N1 110.30(13) . . ?
C5 C6 N1 129.63(15) . . ?
C5 C6 C1 120.08(14) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C13 115.90(13) . . ?
C9 C8 O2 121.96(14) . . ?
C9 C8 C13 121.79(14) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.75(14) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.44(14) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.83(14) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.65(14) . . ?
C13 C12 H12 119.7 . . ?
N2 C13 C8 119.37(13) . . ?
N2 C13 C12 123.14(14) . . ?
C12 C13 C8 117.49(13) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C16 124.99(14) . . ?
O3 C15 C20 111.98(13) . . ?
C16 C15 C20 123.02(14) . . ?
C15 C16 H16 121.6 . . ?
C15 C16 C17 116.79(15) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.88(15) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.46(15) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 121.1 . . ?
C20 C19 C18 117.74(15) . . ?
C20 C19 H19 121.1 . . ?
C15 C20 N3 109.94(13) . . ?
C19 C20 N3 129.94(15) . . ?
C19 C20 C15 120.11(14) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 -179.21(12) . . . . ?
P1 O1 C1 C6 0.58(15) . . . . ?
P1 O2 C8 C9 -51.9(2) . . . . ?
P1 O2 C8 C13 134.75(12) . . . . ?
P1 O3 C15 C16 -175.78(12) . . . . ?
P1 O3 C15 C20 5.27(16) . . . . ?
P1 N3 C20 C15 -3.93(16) . . . . ?
P1 N3 C20 C19 177.44(14) . . . . ?
P1 N1 C6 C1 -0.55(16) . . . . ?
P1 N1 C6 C5 179.63(13) . . . . ?
O1 P1 O2 C8 -29.85(13) . . . . ?
O1 P1 N3 C20 -173.90(11) . . . . ?
O1 P1 N3 C21 10.03(14) . . . . ?
O1 P1 N1 C6 0.73(11) . . . . ?
O1 P1 N1 C7 -174.21(13) . . . . ?
O1 C1 C2 C3 -179.16(14) . . . . ?
O1 C1 C6 N1 -0.02(17) . . . . ?
O1 C1 C6 C5 179.82(13) . . . . ?
O2 P1 O1 C1 117.90(10) . . . . ?
O2 P1 O3 C15 109.29(11) . . . . ?
O2 P1 N3 C20 -81.05(12) . . . . ?
O2 P1 N3 C21 102.88(14) . . . . ?
O2 P1 N1 C6 -91.63(11) . . . . ?
O2 P1 N1 C7 93.43(14) . . . . ?
O2 C8 C9 C10 -172.07(14) . . . . ?
O2 C8 C13 N2 -9.8(2) . . . . ?
O2 C8 C13 C12 170.74(13) . . . . ?
O3 P1 O2 C8 150.11(13) . . . . ?
O3 P1 N3 C20 5.75(11) . . . . ?
O3 P1 N3 C21 -170.32(14) . . . . ?
O3 P1 N1 C6 -178.90(10) . . . . ?
O3 P1 N1 C7 6.16(14) . . . . ?
O3 C15 C16 C17 -178.15(14) . . . . ?
O3 C15 C20 N3 -0.82(18) . . . . ?
O3 C15 C20 C19 177.96(13) . . . . ?
N3 P1 O1 C1 -126.50(10) . . . . ?
N3 P1 O2 C8 -121.80(12) . . . . ?
N3 P1 O3 C15 -6.32(11) . . . . ?
N3 P1 N1 C6 91.47(12) . . . . ?
N3 P1 N1 C7 -83.47(15) . . . . ?
N1 P1 O1 C1 -0.75(10) . . . . ?
N1 P1 O2 C8 60.99(14) . . . . ?
N1 P1 O3 C15 -132.06(11) . . . . ?
N1 P1 N3 C20 95.94(12) . . . . ?
N1 P1 N3 C21 -80.13(15) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C2 C1 C6 N1 179.78(13) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 C5 C6 N1 179.12(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C7 N1 C6 C1 174.90(13) . . . . ?
C7 N1 C6 C5 -4.9(2) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C9 C8 C13 N2 176.80(14) . . . . ?
C9 C8 C13 C12 -2.6(2) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 N2 -177.16(14) . . . . ?
C11 C12 C13 C8 2.2(2) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
C14 N2 C13 C8 178.23(14) . . . . ?
C14 N2 C13 C12 -2.4(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C15 C20 N3 -179.79(14) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 N3 179.08(15) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C20 C15 C16 C17 0.7(2) . . . . ?
C21 N3 C20 C15 172.51(13) . . . . ?
C21 N3 C20 C19 -6.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

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

data_dg360_a_a
_audit_block_doi                 10.5517/ccdc.csd.cc1ph4p0
_database_code_depnum_ccdc_archive 'CCDC 1563692'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_audit_creation_date             2017-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C36 H13 F15 N3 O3 P, C H2 Cl2'
_chemical_formula_sum            'C37 H15 Cl2 F15 N3 O3 P'
_chemical_formula_weight         936.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.6228(13)
_cell_length_b                   14.2940(15)
_cell_length_c                   17.1808(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.875(4)
_cell_angle_gamma                90
_cell_volume                     3578.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.26
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.9035.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7381
_exptl_crystal_description       flake
_exptl_crystal_F_000             1864.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34486
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.76
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -17
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -12
_reflns_number_gt                4930
_reflns_number_total             6560
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.6834
_refine_diff_density_min         -0.6854
_refine_diff_density_rms         0.1084
_refine_ls_d_res_high            0.8294
_refine_ls_d_res_low             11.5922
_refine_ls_goodness_of_fit_ref   1.0403
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.0403
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+4.0168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0896
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C37(H37a,H37b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C32(H32), C33(H33), C34(H34), C35(H35), N2(H2a)
;
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_refinement_flags_posn
C1 C 0.38882(16) 0.27100(18) 0.65571(14) 0.0123(5) Uani 1.000000 .
C2 C 0.36581(17) 0.26593(19) 0.73135(14) 0.0162(6) Uani 1.000000 .
H2 H 0.31467(17) 0.29676(19) 0.74743(14) 0.0194(7) Uiso 1.000000 R
C3 C 0.42303(17) 0.2121(2) 0.78309(15) 0.0201(6) Uani 1.000000 .
H3 H 0.41011(17) 0.2074(2) 0.83502(15) 0.0241(7) Uiso 1.000000 R
C4 C 0.49838(18) 0.1659(2) 0.75850(15) 0.0203(6) Uani 1.000000 .
H4 H 0.53463(18) 0.1298(2) 0.79399(15) 0.0244(7) Uiso 1.000000 R
C5 C 0.52117(17) 0.17246(19) 0.68142(15) 0.0165(6) Uani 1.000000 .
H5 H 0.57215(17) 0.14180(19) 0.66485(15) 0.0198(7) Uiso 1.000000 R
C6 C 0.46521(16) 0.22600(18) 0.63116(14) 0.0126(5) Uani 1.000000 .
C7 C 0.54259(16) 0.20225(18) 0.51221(14) 0.0123(5) Uani 1.000000 .
C8 C 0.63198(17) 0.23534(19) 0.52383(14) 0.0151(6) Uani 1.000000 .
C9 C 0.70290(16) 0.1927(2) 0.48929(15) 0.0185(6) Uani 1.000000 .
C10 C 0.68541(18) 0.1171(2) 0.44071(16) 0.0208(6) Uani 1.000000 .
C11 C 0.59694(18) 0.08294(19) 0.42846(15) 0.0197(6) Uani 1.000000 .
C12 C 0.52713(17) 0.12478(19) 0.46454(15) 0.0166(6) Uani 1.000000 .
C13 C 0.37827(17) 0.49014(18) 0.56537(14) 0.0140(5) Uani 1.000000 .
C14 C 0.29468(17) 0.53279(19) 0.54813(15) 0.0165(6) Uani 1.000000 .
H14 H 0.25968(17) 0.51877(19) 0.50186(15) 0.0198(7) Uiso 1.000000 R
C15 C 0.26282(18) 0.5969(2) 0.60026(16) 0.0215(6) Uani 1.000000 .
H15 H 0.20638(18) 0.6262(2) 0.58919(16) 0.0258(8) Uiso 1.000000 R
C16 C 0.31588(18) 0.6169(2) 0.66878(16) 0.0213(6) Uani 1.000000 .
H16 H 0.29444(18) 0.6591(2) 0.70423(16) 0.0256(7) Uiso 1.000000 R
C17 C 0.40066(17) 0.57477(19) 0.68507(15) 0.0182(6) Uani 1.000000 .
H17 H 0.43585(17) 0.58945(19) 0.73109(15) 0.0219(7) Uiso 1.000000 R
C18 C 0.43368(16) 0.51081(18) 0.63343(14) 0.0142(5) Uani 1.000000 .
C19 C 0.57890(17) 0.47586(18) 0.71282(14) 0.0156(6) Uani 1.000000 .
C20 C 0.5530(2) 0.4629(2) 0.78808(16) 0.0225(6) Uani 1.000000 .
C21 C 0.6147(2) 0.4748(2) 0.85313(16) 0.0304(8) Uani 1.000000 .
C22 C 0.7048(2) 0.4959(2) 0.84448(17) 0.0323(8) Uani 1.000000 .
C23 C 0.73350(19) 0.5048(2) 0.77097(18) 0.0266(7) Uani 1.000000 .
C24 C 0.67128(18) 0.49586(19) 0.70681(15) 0.0181(6) Uani 1.000000 .
C25 C 0.20500(16) 0.25892(18) 0.49903(13) 0.0122(5) Uani 1.000000 .
C26 C 0.20287(16) 0.17961(19) 0.54505(14) 0.0138(5) Uani 1.000000 .
C27 C 0.12375(17) 0.15221(19) 0.57735(14) 0.0165(6) Uani 1.000000 .
C28 C 0.04395(16) 0.2024(2) 0.56088(15) 0.0179(6) Uani 1.000000 .
C29 C 0.04294(16) 0.2796(2) 0.51326(15) 0.0174(6) Uani 1.000000 .
C30 C 0.12388(17) 0.30852(19) 0.48409(14) 0.0145(6) Uani 1.000000 .
C31 C 0.28775(16) 0.27122(17) 0.38221(14) 0.0113(5) Uani 1.000000 .
C32 C 0.21829(17) 0.24640(18) 0.32700(14) 0.0147(6) Uani 1.000000 .
H32 H 0.15861(17) 0.23790(18) 0.34052(14) 0.0177(7) Uiso 1.000000 R
C33 C 0.24002(18) 0.23440(19) 0.25034(15) 0.0168(6) Uani 1.000000 .
H33 H 0.19411(18) 0.21796(19) 0.21199(15) 0.0202(7) Uiso 1.000000 R
C34 C 0.32914(18) 0.24661(19) 0.23028(15) 0.0177(6) Uani 1.000000 .
H34 H 0.34232(18) 0.23764(19) 0.17879(15) 0.0213(7) Uiso 1.000000 R
C35 C 0.39932(17) 0.27222(18) 0.28645(14) 0.0144(6) Uani 1.000000 .
H35 H 0.45926(17) 0.28041(18) 0.27348(14) 0.0173(7) Uiso 1.000000 R
C36 C 0.37635(16) 0.28483(17) 0.36166(14) 0.0115(5) Uani 1.000000 .
F1 F 0.65016(9) 0.31011(11) 0.56987(8) 0.0191(3) Uani 1.000000 .
F2 F 0.78933(10) 0.22428(12) 0.50319(9) 0.0273(4) Uani 1.000000 .
F3 F 0.75348(11) 0.07711(12) 0.40558(10) 0.0316(4) Uani 1.000000 .
F4 F 0.57983(11) 0.00893(11) 0.38159(10) 0.0291(4) Uani 1.000000 .
F5 F 0.44161(10) 0.09054(11) 0.45196(9) 0.0221(4) Uani 1.000000 .
F6 F 0.46686(12) 0.43743(12) 0.79896(9) 0.0294(4) Uani 1.000000 .
F7 F 0.58524(16) 0.46242(13) 0.92455(9) 0.0472(5) Uani 1.000000 .
F8 F 0.76467(15) 0.50478(14) 0.90788(11) 0.0534(6) Uani 1.000000 .
F9 F 0.82214(11) 0.52232(13) 0.76169(11) 0.0411(5) Uani 1.000000 .
F10 F 0.70145(10) 0.50563(11) 0.63539(9) 0.0229(4) Uani 1.000000 .
F11 F 0.27901(9) 0.12788(10) 0.55935(8) 0.0172(3) Uani 1.000000 .
F12 F 0.12345(10) 0.07686(11) 0.62348(9) 0.0252(4) Uani 1.000000 .
F13 F -0.03306(10) 0.17538(12) 0.59208(9) 0.0283(4) Uani 1.000000 .
F14 F -0.03464(9) 0.32765(12) 0.49612(9) 0.0237(4) Uani 1.000000 .
F15 F 0.12298(9) 0.38585(10) 0.43979(8) 0.0185(3) Uani 1.000000 .
N1 N 0.47123(13) 0.24453(15) 0.55067(11) 0.0127(5) Uani 1.000000 .
N2 N 0.51925(14) 0.46512(16) 0.64563(12) 0.0159(5) Uani 1.000000 .
H2a H 0.53556(14) 0.42855(16) 0.60955(12) 0.0191(6) Uiso 1.000000 R
N3 N 0.28549(13) 0.28507(15) 0.46353(11) 0.0108(4) Uani 1.000000 .
O1 O 0.34023(11) 0.31819(12) 0.59559(9) 0.0123(4) Uani 1.000000 .
O2 O 0.41131(11) 0.42697(12) 0.51138(9) 0.0119(4) Uani 1.000000 .
O3 O 0.43614(10) 0.30903(12) 0.42440(9) 0.0123(4) Uani 1.000000 .
P0AA P 0.38839(4) 0.31624(5) 0.50988(4) 0.01054(14) Uani 1.000000 .
C37 C 0.1385(2) 0.4450(2) 0.69444(19) 0.0353(8) Uani 1.000000 .
H37a H 0.1412(2) 0.4937(2) 0.73389(19) 0.0423(10) Uiso 1.000000 R
H37b H 0.1977(2) 0.4424(2) 0.67306(19) 0.0423(10) Uiso 1.000000 R
Cl1 Cl 0.11640(5) 0.33643(5) 0.73834(4) 0.02881(18) Uani 1.000000 .
Cl2 Cl 0.05337(5) 0.47334(6) 0.61939(4) 0.03261(19) Uani 1.000000 .


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 C2 1.372(4) . ?
C1 C6 1.385(4) . ?
C1 O1 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C6 N1 1.418(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.384(4) . ?
C7 N1 1.417(3) . ?
C8 C9 1.380(4) . ?
C8 F1 1.343(3) . ?
C9 C10 1.375(4) . ?
C9 F2 1.344(3) . ?
C10 C11 1.382(4) . ?
C10 F3 1.336(3) . ?
C11 C12 1.376(4) . ?
C11 F4 1.340(3) . ?
C12 F5 1.343(3) . ?
C13 C14 1.375(3) . ?
C13 C18 1.396(3) . ?
C13 O2 1.409(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 N2 1.411(3) . ?
C19 C20 1.390(4) . ?
C19 C24 1.393(4) . ?
C19 N2 1.395(3) . ?
C20 C21 1.386(4) . ?
C20 F6 1.340(3) . ?
C21 C22 1.372(5) . ?
C21 F7 1.346(3) . ?
C22 C23 1.370(4) . ?
C22 F8 1.344(3) . ?
C23 C24 1.374(4) . ?
C23 F9 1.343(3) . ?
C24 F10 1.346(3) . ?
C25 C26 1.384(4) . ?
C25 C30 1.387(3) . ?
C25 N3 1.421(3) . ?
C26 C27 1.382(4) . ?
C26 F11 1.342(3) . ?
C27 C28 1.379(4) . ?
C27 F12 1.337(3) . ?
C28 C29 1.372(4) . ?
C28 F13 1.344(3) . ?
C29 C30 1.387(4) . ?
C29 F14 1.338(3) . ?
C30 F15 1.341(3) . ?
C31 C32 1.376(3) . ?
C31 C36 1.385(3) . ?
C31 N3 1.414(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.392(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.387(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.397(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.374(3) . ?
C36 O3 1.373(3) . ?
N1 P0AA 1.693(2) . ?
N2 H2a 0.8600 . ?
N3 P0AA 1.7009(19) . ?
O1 P0AA 1.6856(17) . ?
O2 P0AA 1.6176(18) . ?
O3 P0AA 1.6821(17) . ?
C37 H37a 0.9700 . ?
C37 H37b 0.9700 . ?
C37 Cl1 1.767(3) . ?
C37 Cl2 1.762(3) . ?

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
C6 C1 C2 122.2(2) . . ?
O1 C1 C2 125.7(2) . . ?
O1 C1 C6 112.1(2) . . ?
H2 C2 C1 121.64(15) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 H2 121.64(16) . . ?
H3 C3 C2 119.39(16) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.39(15) . . ?
H4 C4 C3 119.36(15) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.36(16) . . ?
H5 C5 C4 121.41(16) . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 H5 121.41(15) . . ?
C5 C6 C1 121.4(2) . . ?
N1 C6 C1 109.2(2) . . ?
N1 C6 C5 129.4(2) . . ?
C12 C7 C8 117.5(2) . . ?
N1 C7 C8 120.6(2) . . ?
N1 C7 C12 121.8(2) . . ?
C9 C8 C7 121.4(2) . . ?
F1 C8 C7 119.5(2) . . ?
F1 C8 C9 119.1(2) . . ?
C10 C9 C8 120.0(2) . . ?
F2 C9 C8 120.3(2) . . ?
F2 C9 C10 119.7(2) . . ?
C11 C10 C9 119.6(2) . . ?
F3 C10 C9 120.2(2) . . ?
F3 C10 C11 120.2(3) . . ?
C12 C11 C10 119.9(2) . . ?
F4 C11 C10 119.7(2) . . ?
F4 C11 C12 120.4(2) . . ?
C11 C12 C7 121.6(2) . . ?
F5 C12 C7 119.3(2) . . ?
F5 C12 C11 119.0(2) . . ?
C18 C13 C14 121.9(2) . . ?
O2 C13 C14 119.4(2) . . ?
O2 C13 C18 118.7(2) . . ?
H14 C14 C13 120.19(15) . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.19(15) . . ?
H15 C15 C14 120.32(15) . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.32(16) . . ?
H16 C16 C15 119.69(16) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.69(16) . . ?
H17 C17 C16 119.63(16) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.63(15) . . ?
C17 C18 C13 117.8(2) . . ?
N2 C18 C13 118.1(2) . . ?
N2 C18 C17 124.2(2) . . ?
C24 C19 C20 116.0(2) . . ?
N2 C19 C20 123.7(2) . . ?
N2 C19 C24 120.2(2) . . ?
C21 C20 C19 121.6(3) . . ?
F6 C20 C19 120.0(2) . . ?
F6 C20 C21 118.4(3) . . ?
C22 C21 C20 120.3(3) . . ?
F7 C21 C20 118.8(3) . . ?
F7 C21 C22 120.8(3) . . ?
C23 C22 C21 119.5(2) . . ?
F8 C22 C21 119.9(3) . . ?
F8 C22 C23 120.6(3) . . ?
C24 C23 C22 119.8(3) . . ?
F9 C23 C22 120.1(2) . . ?
F9 C23 C24 120.1(3) . . ?
C23 C24 C19 122.7(3) . . ?
F10 C24 C19 118.9(2) . . ?
F10 C24 C23 118.4(2) . . ?
C30 C25 C26 117.6(2) . . ?
N3 C25 C26 121.4(2) . . ?
N3 C25 C30 120.8(2) . . ?
C27 C26 C25 121.5(2) . . ?
F11 C26 C25 119.8(2) . . ?
F11 C26 C27 118.7(2) . . ?
C28 C27 C26 119.5(2) . . ?
F12 C27 C26 120.8(2) . . ?
F12 C27 C28 119.7(2) . . ?
C29 C28 C27 120.4(2) . . ?
F13 C28 C27 119.4(2) . . ?
F13 C28 C29 120.1(2) . . ?
C30 C29 C28 119.3(2) . . ?
F14 C29 C28 120.7(2) . . ?
F14 C29 C30 120.1(2) . . ?
C29 C30 C25 121.5(2) . . ?
F15 C30 C25 119.5(2) . . ?
F15 C30 C29 118.9(2) . . ?
C36 C31 C32 120.8(2) . . ?
N3 C31 C32 129.7(2) . . ?
N3 C31 C36 109.5(2) . . ?
H32 C32 C31 120.99(15) . . ?
C33 C32 C31 118.0(2) . . ?
C33 C32 H32 120.99(15) . . ?
H33 C33 C32 119.51(15) . . ?
C34 C33 C32 121.0(2) . . ?
C34 C33 H33 119.51(15) . . ?
H34 C34 C33 119.60(15) . . ?
C35 C34 C33 120.8(2) . . ?
C35 C34 H34 119.60(15) . . ?
H35 C35 C34 121.30(15) . . ?
C36 C35 C34 117.4(2) . . ?
C36 C35 H35 121.30(14) . . ?
C35 C36 C31 122.0(2) . . ?
O3 C36 C31 112.5(2) . . ?
O3 C36 C35 125.5(2) . . ?
C7 N1 C6 118.98(19) . . ?
P0AA N1 C6 114.53(16) . . ?
P0AA N1 C7 126.49(16) . . ?
C19 N2 C18 123.8(2) . . ?
H2a N2 C18 118.11(13) . . ?
H2a N2 C19 118.11(14) . . ?
C31 N3 C25 118.49(19) . . ?
P0AA N3 C25 126.87(16) . . ?
P0AA N3 C31 113.91(15) . . ?
P0AA O1 C1 114.79(15) . . ?
P0AA O2 C13 123.74(15) . . ?
P0AA O3 C36 114.64(14) . . ?
N3 P0AA N1 127.50(11) . . ?
O1 P0AA N1 89.19(9) . . ?
O1 P0AA N3 89.69(9) . . ?
O2 P0AA N1 116.49(10) . . ?
O2 P0AA N3 115.95(10) . . ?
O2 P0AA O1 94.08(9) . . ?
O3 P0AA N1 89.36(9) . . ?
O3 P0AA N3 89.51(9) . . ?
O3 P0AA O1 177.44(10) . . ?
O3 P0AA O2 88.45(9) . . ?
H37b C37 H37a 107.9 . . ?
Cl1 C37 H37a 109.26(12) . . ?
Cl1 C37 H37b 109.26(12) . . ?
Cl2 C37 H37a 109.26(12) . . ?
Cl2 C37 H37b 109.26(12) . . ?
Cl2 C37 Cl1 111.79(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
'Spiro{bis[1,2-phenyleneoxy(perfluorophenylamino)]-2-( perfluorophenylamino)phenoxy-phosphorane}'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/pentane'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
