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

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

data_8cl_gud266
_database_code_depnum_ccdc_archive 'CCDC 1414814'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 1-chloro-N,N-diethyl-1-(2,2,6,6-tetramethylpiperidin-1-yl)phosphanamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H32 Cl N2 P'
_chemical_formula_sum            'C15 H32 Cl N2 P'
_chemical_formula_weight         306.84

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.3991(5)
_cell_length_b                   12.2633(6)
_cell_length_c                   13.9503(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.325(2)
_cell_angle_gamma                90
_cell_volume                     1764.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4519
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      30.53

_exptl_crystal_description       blocks
_exptl_crystal_colour            .
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.506
_exptl_crystal_size_min          0.361
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9272
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   'SADABS in ApexII software suite'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            20257
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         30.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5385
_reflns_number_gt                4525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'SHELXL-2014, publCIF'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.7190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5385
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.70848(3) 0.46467(2) 0.24770(2) 0.01185(7) Uani 1 1 d . . . . .
Cl1 Cl 0.76331(3) 0.35067(2) 0.36707(2) 0.02148(8) Uani 1 1 d . . . . .
N2 N 0.69772(8) 0.58934(7) 0.30223(6) 0.01212(16) Uani 1 1 d . . . . .
C3 C 0.57843(10) 0.64692(9) 0.24902(8) 0.0146(2) Uani 1 1 d . . . . .
C4 C 0.58563(12) 0.76969(9) 0.26986(9) 0.0211(2) Uani 1 1 d . . . . .
H4A H 0.6564 0.8014 0.2376 0.025 Uiso 1 1 calc R U . . .
H4B H 0.5035 0.8039 0.2411 0.025 Uiso 1 1 calc R U . . .
C5 C 0.60874(13) 0.79798(10) 0.37624(9) 0.0251(3) Uani 1 1 d . . . . .
H5A H 0.5370 0.7700 0.4096 0.030 Uiso 1 1 calc R U . . .
H5B H 0.6137 0.8781 0.3849 0.030 Uiso 1 1 calc R U . . .
C6 C 0.73585(12) 0.74528(10) 0.41748(9) 0.0213(2) Uani 1 1 d . . . . .
H6A H 0.7540 0.7640 0.4869 0.026 Uiso 1 1 calc R U . . .
H6B H 0.8064 0.7766 0.3847 0.026 Uiso 1 1 calc R U . . .
C7 C 0.73812(10) 0.62015(9) 0.40697(7) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.87900(11) 0.58732(11) 0.44110(8) 0.0208(2) Uani 1 1 d . . . . .
H8A H 0.9017 0.6084 0.5089 0.031 Uiso 1 1 calc R U . . .
H8B H 0.8883 0.5082 0.4348 0.031 Uiso 1 1 calc R U . . .
H8C H 0.9368 0.6244 0.4014 0.031 Uiso 1 1 calc R U . . .
C9 C 0.65020(12) 0.56978(11) 0.47647(8) 0.0223(2) Uani 1 1 d . . . . .
H9A H 0.6808 0.5924 0.5428 0.034 Uiso 1 1 calc R U . . .
H9B H 0.5609 0.5949 0.4587 0.034 Uiso 1 1 calc R U . . .
H9C H 0.6531 0.4901 0.4720 0.034 Uiso 1 1 calc R U . . .
C10 C 0.57870(12) 0.63788(10) 0.13881(8) 0.0199(2) Uani 1 1 d . . . . .
H10A H 0.5742 0.5609 0.1198 0.030 Uiso 1 1 calc R U . . .
H10B H 0.5035 0.6768 0.1056 0.030 Uiso 1 1 calc R U . . .
H10C H 0.6585 0.6702 0.1210 0.030 Uiso 1 1 calc R U . . .
C11 C 0.44968(11) 0.59917(10) 0.27324(9) 0.0212(2) Uani 1 1 d . . . . .
H11A H 0.4471 0.5208 0.2594 0.032 Uiso 1 1 calc R U . . .
H11B H 0.4427 0.6110 0.3419 0.032 Uiso 1 1 calc R U . . .
H11C H 0.3772 0.6353 0.2339 0.032 Uiso 1 1 calc R U . . .
N12 N 0.83845(8) 0.47210(7) 0.18956(6) 0.01254(17) Uani 1 1 d . . . . .
C13 C 0.84423(11) 0.39175(9) 0.10956(8) 0.0156(2) Uani 1 1 d . . . . .
H13 H 0.9312 0.4002 0.0870 0.019 Uiso 1 1 calc R U . . .
C14 C 0.74310(12) 0.41739(11) 0.02337(8) 0.0227(2) Uani 1 1 d . . . . .
H14A H 0.7491 0.3636 -0.0278 0.034 Uiso 1 1 calc R U . . .
H14B H 0.6563 0.4146 0.0436 0.034 Uiso 1 1 calc R U . . .
H14C H 0.7589 0.4905 -0.0011 0.034 Uiso 1 1 calc R U . . .
C15 C 0.83386(14) 0.27337(10) 0.14123(9) 0.0254(3) Uani 1 1 d . . . . .
H15A H 0.8383 0.2251 0.0857 0.038 Uiso 1 1 calc R U . . .
H15B H 0.9055 0.2566 0.1918 0.038 Uiso 1 1 calc R U . . .
H15C H 0.7511 0.2624 0.1666 0.038 Uiso 1 1 calc R U . . .
C16 C 0.95417(10) 0.54110(9) 0.21491(8) 0.0153(2) Uani 1 1 d . . . . .
H16 H 0.9327 0.5942 0.2649 0.018 Uiso 1 1 calc R U . . .
C17 C 1.07128(12) 0.47525(12) 0.26012(10) 0.0260(3) Uani 1 1 d . . . . .
H17A H 1.1456 0.5241 0.2758 0.039 Uiso 1 1 calc R U . . .
H17B H 1.0507 0.4399 0.3193 0.039 Uiso 1 1 calc R U . . .
H17C H 1.0926 0.4196 0.2143 0.039 Uiso 1 1 calc R U . . .
C18 C 0.98632(13) 0.60763(11) 0.12865(9) 0.0258(3) Uani 1 1 d . . . . .
H18A H 1.0634 0.6523 0.1482 0.039 Uiso 1 1 calc R U . . .
H18B H 1.0033 0.5582 0.0765 0.039 Uiso 1 1 calc R U . . .
H18C H 0.9130 0.6551 0.1059 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N12 1.6650(9) . ?
P1 N2 1.7176(9) . ?
P1 Cl1 2.1933(4) . ?
N2 C7 1.5159(13) . ?
N2 C3 1.5341(13) . ?
C3 C4 1.5334(15) . ?
C3 C11 1.5379(16) . ?
C3 C10 1.5418(15) . ?
C4 C5 1.5131(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5173(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5420(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5353(15) . ?
C7 C9 1.5438(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N12 C16 1.4767(13) . ?
N12 C13 1.4958(13) . ?
C13 C15 1.5252(16) . ?
C13 C14 1.5258(16) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.5259(16) . ?
C16 C17 1.5287(16) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
N12 P1 N2 105.65(4) . . ?
N12 P1 Cl1 104.84(3) . . ?
N2 P1 Cl1 104.86(3) . . ?
C7 N2 C3 117.34(8) . . ?
C7 N2 P1 128.54(7) . . ?
C3 N2 P1 106.84(6) . . ?
C4 C3 N2 110.08(9) . . ?
C4 C3 C11 110.80(9) . . ?
N2 C3 C11 113.04(9) . . ?
C4 C3 C10 104.68(9) . . ?
N2 C3 C10 110.19(9) . . ?
C11 C3 C10 107.70(9) . . ?
C5 C4 C3 114.13(10) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 107.22(10) . . ?
C4 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 C7 114.27(10) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C8 111.71(9) . . ?
N2 C7 C6 109.51(9) . . ?
C8 C7 C6 104.89(9) . . ?
N2 C7 C9 113.08(9) . . ?
C8 C7 C9 108.57(9) . . ?
C6 C7 C9 108.72(9) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 N12 C13 116.56(8) . . ?
C16 N12 P1 127.02(7) . . ?
C13 N12 P1 116.09(7) . . ?
N12 C13 C15 113.56(9) . . ?
N12 C13 C14 111.28(9) . . ?
C15 C13 C14 110.94(10) . . ?
N12 C13 H13 106.9 . . ?
C15 C13 H13 106.9 . . ?
C14 C13 H13 106.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 C18 111.80(9) . . ?
N12 C16 C17 112.22(10) . . ?
C18 C16 C17 111.39(10) . . ?
N12 C16 H16 107.0 . . ?
C18 C16 H16 107.0 . . ?
C17 C16 H16 107.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N12 P1 N2 C7 -101.12(9) . . . . ?
Cl1 P1 N2 C7 9.33(9) . . . . ?
N12 P1 N2 C3 110.15(7) . . . . ?
Cl1 P1 N2 C3 -139.39(6) . . . . ?
C7 N2 C3 C4 45.38(12) . . . . ?
P1 N2 C3 C4 -161.82(8) . . . . ?
C7 N2 C3 C11 -79.10(11) . . . . ?
P1 N2 C3 C11 73.70(9) . . . . ?
C7 N2 C3 C10 160.34(9) . . . . ?
P1 N2 C3 C10 -46.86(10) . . . . ?
N2 C3 C4 C5 -52.07(13) . . . . ?
C11 C3 C4 C5 73.69(13) . . . . ?
C10 C3 C4 C5 -170.47(10) . . . . ?
C3 C4 C5 C6 59.06(14) . . . . ?
C4 C5 C6 C7 -59.61(14) . . . . ?
C3 N2 C7 C8 -161.27(9) . . . . ?
P1 N2 C7 C8 52.74(13) . . . . ?
C3 N2 C7 C6 -45.51(12) . . . . ?
P1 N2 C7 C6 168.49(8) . . . . ?
C3 N2 C7 C9 75.89(12) . . . . ?
P1 N2 C7 C9 -70.10(12) . . . . ?
C5 C6 C7 N2 52.96(13) . . . . ?
C5 C6 C7 C8 172.97(10) . . . . ?
C5 C6 C7 C9 -71.04(13) . . . . ?
N2 P1 N12 C16 27.60(10) . . . . ?
Cl1 P1 N12 C16 -82.87(9) . . . . ?
N2 P1 N12 C13 -159.35(7) . . . . ?
Cl1 P1 N12 C13 90.18(7) . . . . ?
C16 N12 C13 C15 117.83(11) . . . . ?
P1 N12 C13 C15 -55.96(11) . . . . ?
C16 N12 C13 C14 -116.13(11) . . . . ?
P1 N12 C13 C14 70.07(11) . . . . ?
C13 N12 C16 C18 58.35(13) . . . . ?
P1 N12 C16 C18 -128.64(10) . . . . ?
C13 N12 C16 C17 -67.65(12) . . . . ?
P1 N12 C16 C17 105.37(10) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3


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

data_82_gud235
_database_code_depnum_ccdc_archive 'CCDC 1414815'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
N¹,N¹,N²,N²-tetraethyl-1,2-bis(2,2,6,6-tetramethylpiperidin-1-yl)-diphosphane-1,2-diamine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H56 N4 P2'
_chemical_formula_sum            'C26 H56 N4 P2'
_chemical_formula_weight         486.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.3594(6)
_cell_length_b                   9.0786(6)
_cell_length_c                   18.6456(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.968(3)
_cell_angle_gamma                90
_cell_volume                     1413.15(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2248
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.46

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            19728
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2903
_reflns_number_gt                2249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII Software-Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software-Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software-Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'SHELXL-2014, publCIF'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.1372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.48913(6) 0.61072(5) 0.52883(2) 0.01272(14) Uani 1 1 d . . . . .
N2 N 0.48139(18) 0.56917(17) 0.61966(8) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.6102(2) 0.4908(2) 0.66513(9) 0.0157(4) Uani 1 1 d . . . . .
C31 C 0.7609(2) 0.5852(2) 0.68095(11) 0.0208(4) Uani 1 1 d . . . . .
H31A H 0.8394 0.5286 0.7105 0.031 Uiso 1 1 calc R U . . .
H31B H 0.8073 0.6127 0.6357 0.031 Uiso 1 1 calc R U . . .
H31C H 0.7318 0.6744 0.7068 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6606(2) 0.3499(2) 0.62788(10) 0.0179(4) Uani 1 1 d . . . . .
H32A H 0.7439 0.3000 0.6578 0.027 Uiso 1 1 calc R U . . .
H32B H 0.5677 0.2846 0.6207 0.027 Uiso 1 1 calc R U . . .
H32C H 0.7025 0.3744 0.5812 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5441(2) 0.4400(2) 0.73683(10) 0.0191(4) Uani 1 1 d . . . . .
H4A H 0.4660 0.3596 0.7269 0.023 Uiso 1 1 calc R U . . .
H4B H 0.6334 0.3992 0.7676 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4632(2) 0.5607(2) 0.77786(10) 0.0209(4) Uani 1 1 d . . . . .
H5A H 0.4214 0.5207 0.8226 0.025 Uiso 1 1 calc R U . . .
H5B H 0.5406 0.6401 0.7907 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3273(2) 0.6200(2) 0.72943(10) 0.0214(4) Uani 1 1 d . . . . .
H6A H 0.2719 0.6986 0.7553 0.026 Uiso 1 1 calc R U . . .
H6B H 0.2491 0.5398 0.7192 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3801(2) 0.6824(2) 0.65776(10) 0.0177(4) Uani 1 1 d . . . . .
C71 C 0.2236(2) 0.7176(2) 0.61434(11) 0.0223(5) Uani 1 1 d . . . . .
H71A H 0.1622 0.7903 0.6403 0.033 Uiso 1 1 calc R U . . .
H71B H 0.2485 0.7577 0.5674 0.033 Uiso 1 1 calc R U . . .
H71C H 0.1603 0.6274 0.6076 0.033 Uiso 1 1 calc R U . . .
C72 C 0.4676(3) 0.8302(2) 0.67117(11) 0.0233(5) Uani 1 1 d . . . . .
H72A H 0.3975 0.8982 0.6956 0.035 Uiso 1 1 calc R U . . .
H72B H 0.5655 0.8135 0.7013 0.035 Uiso 1 1 calc R U . . .
H72C H 0.4955 0.8727 0.6252 0.035 Uiso 1 1 calc R U . . .
N8 N 0.66449(19) 0.69002(17) 0.50594(8) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.8184(2) 0.6218(2) 0.49288(10) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.8070 0.5134 0.4956 0.021 Uiso 1 1 calc R U . . .
H9B H 0.8979 0.6524 0.5312 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8812(3) 0.6626(2) 0.42008(11) 0.0245(5) Uani 1 1 d . . . . .
H10A H 0.9843 0.6139 0.4143 0.037 Uiso 1 1 calc R U . . .
H10B H 0.8043 0.6305 0.3818 0.037 Uiso 1 1 calc R U . . .
H10C H 0.8952 0.7696 0.4174 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6601(2) 0.8504(2) 0.49608(11) 0.0201(4) Uani 1 1 d . . . . .
H11A H 0.5515 0.8862 0.5058 0.024 Uiso 1 1 calc R U . . .
H11B H 0.6792 0.8728 0.4453 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7825(3) 0.9351(2) 0.54405(12) 0.0267(5) Uani 1 1 d . . . . .
H12A H 0.7720 1.0409 0.5343 0.040 Uiso 1 1 calc R U . . .
H12B H 0.7630 0.9161 0.5946 0.040 Uiso 1 1 calc R U . . .
H12C H 0.8909 0.9027 0.5340 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N8 1.7070(16) . ?
P1 N2 1.7395(15) . ?
P1 P1 2.2914(10) 3_666 ?
N2 C3 1.513(2) . ?
N2 C7 1.530(2) . ?
C3 C32 1.525(3) . ?
C3 C31 1.540(3) . ?
C3 C4 1.543(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C4 C5 1.516(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.537(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C71 1.536(3) . ?
C7 C72 1.542(3) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
N8 C9 1.460(2) . ?
N8 C11 1.468(2) . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.531(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N8 P1 N2 114.24(8) . . ?
N8 P1 P1 99.37(6) . 3_666 ?
N2 P1 P1 105.93(6) . 3_666 ?
C3 N2 C7 116.79(14) . . ?
C3 N2 P1 125.89(12) . . ?
C7 N2 P1 110.83(12) . . ?
N2 C3 C32 110.17(14) . . ?
N2 C3 C31 113.38(15) . . ?
C32 C3 C31 108.15(16) . . ?
N2 C3 C4 110.47(15) . . ?
C32 C3 C4 105.27(16) . . ?
C31 C3 C4 109.05(15) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C5 C4 C3 114.21(16) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 107.27(16) . . ?
C6 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 . . ?
C6 C5 H5B 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 C7 114.14(16) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N2 C7 C71 111.82(15) . . ?
N2 C7 C6 110.28(16) . . ?
C71 C7 C6 105.05(16) . . ?
N2 C7 C72 113.00(16) . . ?
C71 C7 C72 106.76(17) . . ?
C6 C7 C72 109.57(16) . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C7 C72 H72A 109.5 . . ?
C7 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C7 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C9 N8 C11 114.60(16) . . ?
C9 N8 P1 129.68(13) . . ?
C11 N8 P1 115.70(13) . . ?
N8 C9 C10 113.08(16) . . ?
N8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N8 C11 C12 114.44(17) . . ?
N8 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N8 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N8 P1 N2 C3 -47.67(17) . . . . ?
P1 P1 N2 C3 60.63(15) 3_666 . . . ?
N8 P1 N2 C7 102.85(13) . . . . ?
P1 P1 N2 C7 -148.85(11) 3_666 . . . ?
C7 N2 C3 C32 160.99(16) . . . . ?
P1 N2 C3 C32 -50.0(2) . . . . ?
C7 N2 C3 C31 -77.7(2) . . . . ?
P1 N2 C3 C31 71.3(2) . . . . ?
C7 N2 C3 C4 45.1(2) . . . . ?
P1 N2 C3 C4 -165.92(13) . . . . ?
N2 C3 C4 C5 -52.2(2) . . . . ?
C32 C3 C4 C5 -171.11(16) . . . . ?
C31 C3 C4 C5 73.0(2) . . . . ?
C3 C4 C5 C6 58.6(2) . . . . ?
C4 C5 C6 C7 -59.0(2) . . . . ?
C3 N2 C7 C71 -161.84(16) . . . . ?
P1 N2 C7 C71 44.69(19) . . . . ?
C3 N2 C7 C6 -45.4(2) . . . . ?
P1 N2 C7 C6 161.18(13) . . . . ?
C3 N2 C7 C72 77.7(2) . . . . ?
P1 N2 C7 C72 -75.81(17) . . . . ?
C5 C6 C7 N2 52.6(2) . . . . ?
C5 C6 C7 C71 173.21(17) . . . . ?
C5 C6 C7 C72 -72.4(2) . . . . ?
N2 P1 N8 C9 80.64(18) . . . . ?
P1 P1 N8 C9 -31.65(17) 3_666 . . . ?
N2 P1 N8 C11 -101.03(14) . . . . ?
P1 P1 N8 C11 146.69(13) 3_666 . . . ?
C11 N8 C9 C10 -52.6(2) . . . . ?
P1 N8 C9 C10 125.75(17) . . . . ?
C9 N8 C11 C12 -58.7(2) . . . . ?
P1 N8 C11 C12 122.69(16) . . . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


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

data_92_gud265
_database_code_depnum_ccdc_archive 'CCDC 1414816'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
N¹,N¹,N²,N²-tetraisopropyl-1,2-bis(2,2,6,6-tetramethylpiperidin-1-yl)-diphosphane-1,2-diamine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H64 N4 P2'
_chemical_formula_sum            'C30 H64 N4 P2'
_chemical_formula_weight         542.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

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

_cell_length_a                   16.522(2)
_cell_length_b                   17.526(2)
_cell_length_c                   11.2185(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3248.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3419
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      25.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_process_details   'SADABS in ApexII software suite'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            20756
_diffrn_reflns_av_unetI/netI     0.1761
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.694
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5756
_reflns_number_gt                3419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.977

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

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'SHELXL-2014, publCIF'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         5756
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.74210(10) 0.68458(9) 0.86664(14) 0.0124(4) Uani 1 1 d . . . . .
N2 N 0.7805(3) 0.6033(2) 0.7982(4) 0.0092(12) Uani 1 1 d . . . . .
C3 C 0.5085(4) 0.6908(4) 0.6333(6) 0.0219(17) Uani 1 1 d . . . . .
C3' C 0.7393(4) 0.5266(3) 0.7911(6) 0.0171(16) Uani 1 1 d . . . . .
C4 C 0.7732(4) 0.4786(3) 0.6866(6) 0.0219(18) Uani 1 1 d . . . . .
H4A H 0.7500 0.4266 0.6909 0.026 Uiso 1 1 calc R U . . .
H4B H 0.7554 0.5017 0.6104 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8644(4) 0.4728(3) 0.6866(6) 0.0237(17) Uani 1 1 d . . . . .
H5A H 0.8829 0.4420 0.6177 0.028 Uiso 1 1 calc R U . . .
H5B H 0.8834 0.4479 0.7607 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8978(4) 0.5533(3) 0.6783(6) 0.0203(18) Uani 1 1 d . . . . .
H6A H 0.8792 0.5765 0.6026 0.024 Uiso 1 1 calc R U . . .
H6B H 0.9576 0.5507 0.6757 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8725(4) 0.6052(3) 0.7818(6) 0.0149(15) Uani 1 1 d . . . . .
C8 C 0.9034(4) 0.6847(3) 0.7459(6) 0.0208(16) Uani 1 1 d . . . . .
H8A H 0.8755 0.7015 0.6734 0.031 Uiso 1 1 calc R U . . .
H8B H 0.8926 0.7209 0.8105 0.031 Uiso 1 1 calc R U . . .
H8C H 0.9618 0.6823 0.7309 0.031 Uiso 1 1 calc R U . . .
C9 C 0.9186(4) 0.5832(4) 0.8949(6) 0.0224(18) Uani 1 1 d . . . . .
H9A H 0.9770 0.5853 0.8795 0.034 Uiso 1 1 calc R U . . .
H9B H 0.9049 0.6188 0.9591 0.034 Uiso 1 1 calc R U . . .
H9C H 0.9036 0.5312 0.9186 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6503(4) 0.5368(3) 0.7676(6) 0.0187(17) Uani 1 1 d . . . . .
H10A H 0.6242 0.4866 0.7631 0.028 Uiso 1 1 calc R U . . .
H10B H 0.6260 0.5665 0.8323 0.028 Uiso 1 1 calc R U . . .
H10C H 0.6428 0.5638 0.6919 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7493(4) 0.4804(3) 0.9069(5) 0.0207(17) Uani 1 1 d . . . . .
H11A H 0.8070 0.4733 0.9236 0.031 Uiso 1 1 calc R U . . .
H11B H 0.7240 0.5081 0.9731 0.031 Uiso 1 1 calc R U . . .
H11C H 0.7233 0.4305 0.8978 0.031 Uiso 1 1 calc R U . . .
N12 N 0.6901(3) 0.6655(3) 0.9969(4) 0.0143(13) Uani 1 1 d . . . . .
C13 C 0.6028(4) 0.6501(3) 1.0099(6) 0.0158(16) Uani 1 1 d . . . . .
H13 H 0.5809 0.6422 0.9277 0.019 Uiso 1 1 calc R U . . .
C14 C 0.5837(4) 0.5775(3) 1.0804(6) 0.0243(19) Uani 1 1 d . . . . .
H14A H 0.5249 0.5709 1.0855 0.036 Uiso 1 1 calc R U . . .
H14B H 0.6076 0.5334 1.0399 0.036 Uiso 1 1 calc R U . . .
H14C H 0.6063 0.5818 1.1609 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5560(4) 0.7169(3) 1.0639(6) 0.0223(18) Uani 1 1 d . . . . .
H15A H 0.4986 0.7033 1.0704 0.033 Uiso 1 1 calc R U . . .
H15B H 0.5775 0.7283 1.1433 0.033 Uiso 1 1 calc R U . . .
H15C H 0.5619 0.7618 1.0126 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7310(4) 0.6818(3) 1.1134(5) 0.0170(15) Uani 1 1 d . . . . .
H16 H 0.6865 0.6878 1.1731 0.020 Uiso 1 1 calc R U . . .
C17 C 0.7770(5) 0.7565(4) 1.1147(6) 0.034(2) Uani 1 1 d . . . . .
H17A H 0.8022 0.7637 1.1930 0.051 Uiso 1 1 calc R U . . .
H17B H 0.8191 0.7555 1.0531 0.051 Uiso 1 1 calc R U . . .
H17C H 0.7396 0.7987 1.0989 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7834(5) 0.6165(4) 1.1588(6) 0.033(2) Uani 1 1 d . . . . .
H18A H 0.8082 0.6311 1.2349 0.049 Uiso 1 1 calc R U . . .
H18B H 0.7499 0.5710 1.1703 0.049 Uiso 1 1 calc R U . . .
H18C H 0.8260 0.6055 1.1005 0.049 Uiso 1 1 calc R U . . .
P1' P 0.63425(11) 0.74566(9) 0.76755(14) 0.0136(4) Uani 1 1 d . . . . .
N2' N 0.6001(3) 0.7041(3) 0.6360(5) 0.0144(13) Uani 1 1 d . . . . .
C4' C 0.4886(5) 0.6221(4) 0.5530(6) 0.032(2) Uani 1 1 d . . . . .
H4'1 H 0.5082 0.5751 0.5925 0.038 Uiso 1 1 calc R U . . .
H4'2 H 0.4290 0.6179 0.5457 0.038 Uiso 1 1 calc R U . . .
C5' C 0.5246(4) 0.6260(4) 0.4294(6) 0.030(2) Uani 1 1 d . . . . .
H5'1 H 0.5032 0.6709 0.3863 0.036 Uiso 1 1 calc R U . . .
H5'2 H 0.5103 0.5795 0.3838 0.036 Uiso 1 1 calc R U . . .
C6' C 0.6159(4) 0.6321(4) 0.4421(6) 0.0219(18) Uani 1 1 d . . . . .
H6'1 H 0.6402 0.6362 0.3617 0.026 Uiso 1 1 calc R U . . .
H6'2 H 0.6366 0.5848 0.4794 0.026 Uiso 1 1 calc R U . . .
C7' C 0.6431(4) 0.7007(3) 0.5170(5) 0.0188(16) Uani 1 1 d . . . . .
C8' C 0.7337(4) 0.6911(3) 0.5379(5) 0.0206(16) Uani 1 1 d . . . . .
H8'1 H 0.7618 0.6889 0.4610 0.031 Uiso 1 1 calc R U . . .
H8'2 H 0.7541 0.7345 0.5840 0.031 Uiso 1 1 calc R U . . .
H8'3 H 0.7435 0.6438 0.5821 0.031 Uiso 1 1 calc R U . . .
C9' C 0.6316(4) 0.7747(3) 0.4433(6) 0.0233(18) Uani 1 1 d . . . . .
H9'1 H 0.6604 0.7699 0.3673 0.035 Uiso 1 1 calc R U . . .
H9'2 H 0.5738 0.7828 0.4281 0.035 Uiso 1 1 calc R U . . .
H9'3 H 0.6533 0.8181 0.4879 0.035 Uiso 1 1 calc R U . . .
C10' C 0.4746(4) 0.6685(4) 0.7554(5) 0.0241(18) Uani 1 1 d . . . . .
H10D H 0.5032 0.6233 0.7850 0.036 Uiso 1 1 calc R U . . .
H10E H 0.4821 0.7108 0.8114 0.036 Uiso 1 1 calc R U . . .
H10F H 0.4167 0.6570 0.7479 0.036 Uiso 1 1 calc R U . . .
C11' C 0.4612(4) 0.7610(4) 0.5936(6) 0.0300(19) Uani 1 1 d . . . . .
H11D H 0.4808 0.7777 0.5154 0.045 Uiso 1 1 calc R U . . .
H11E H 0.4036 0.7484 0.5883 0.045 Uiso 1 1 calc R U . . .
H11F H 0.4689 0.8022 0.6517 0.045 Uiso 1 1 calc R U . . .
N12' N 0.6825(3) 0.8311(3) 0.7472(4) 0.0146(13) Uani 1 1 d . . . . .
C13' C 0.7702(4) 0.8445(3) 0.7255(5) 0.0144(15) Uani 1 1 d . . . . .
H13' H 0.7944 0.7935 0.7074 0.017 Uiso 1 1 calc R U . . .
C14' C 0.7887(4) 0.8957(3) 0.6172(6) 0.0239(18) Uani 1 1 d . . . . .
H14D H 0.8474 0.9017 0.6089 0.036 Uiso 1 1 calc R U . . .
H14E H 0.7667 0.8721 0.5449 0.036 Uiso 1 1 calc R U . . .
H14F H 0.7636 0.9458 0.6288 0.036 Uiso 1 1 calc R U . . .
C15' C 0.8155(4) 0.8752(3) 0.8339(6) 0.0204(18) Uani 1 1 d . . . . .
H15D H 0.8726 0.8826 0.8135 0.031 Uiso 1 1 calc R U . . .
H15E H 0.7917 0.9240 0.8582 0.031 Uiso 1 1 calc R U . . .
H15F H 0.8111 0.8386 0.8997 0.031 Uiso 1 1 calc R U . . .
C16' C 0.6378(4) 0.9036(3) 0.7716(6) 0.0217(17) Uani 1 1 d . . . . .
H16' H 0.6795 0.9422 0.7951 0.026 Uiso 1 1 calc R U . . .
C17' C 0.5787(4) 0.8984(3) 0.8748(6) 0.0234(17) Uani 1 1 d . . . . .
H17D H 0.5518 0.9477 0.8856 0.035 Uiso 1 1 calc R U . . .
H17E H 0.5381 0.8591 0.8577 0.035 Uiso 1 1 calc R U . . .
H17F H 0.6080 0.8850 0.9478 0.035 Uiso 1 1 calc R U . . .
C18' C 0.5945(5) 0.9359(4) 0.6629(7) 0.035(2) Uani 1 1 d . . . . .
H18D H 0.5666 0.9832 0.6849 0.052 Uiso 1 1 calc R U . . .
H18E H 0.6341 0.9466 0.6001 0.052 Uiso 1 1 calc R U . . .
H18F H 0.5549 0.8987 0.6338 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N12 1.727(5) . ?
P1 N2 1.738(5) . ?
P1 P1' 2.357(2) . ?
N2 C3' 1.509(7) . ?
N2 C7 1.532(8) . ?
C3 C11' 1.524(8) . ?
C3 C10' 1.530(8) . ?
C3 N2' 1.531(8) . ?
C3 C4' 1.540(9) . ?
C3' C10 1.504(9) . ?
C3' C11 1.540(8) . ?
C3' C4 1.548(8) . ?
C4 C5 1.511(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.530(8) . ?
C7 C8 1.536(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N12 C13 1.475(8) . ?
N12 C16 1.499(7) . ?
C13 C15 1.529(8) . ?
C13 C14 1.530(8) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.514(8) . ?
C16 C18 1.523(8) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
P1' N12' 1.711(5) . ?
P1' N2' 1.740(5) . ?
N2' C7' 1.513(8) . ?
C4' C5' 1.510(10) . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C5' C6' 1.519(9) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C6' C7' 1.534(8) . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C7' C8' 1.525(9) . ?
C7' C9' 1.549(8) . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
N12' C13' 1.488(7) . ?
N12' C16' 1.496(7) . ?
C13' C15' 1.525(8) . ?
C13' C14' 1.542(8) . ?
C13' H13' 1.0000 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' C17' 1.517(9) . ?
C16' C18' 1.523(9) . ?
C16' H16' 1.0000 . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 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
N12 P1 N2 113.4(2) . . ?
N12 P1 P1' 96.35(19) . . ?
N2 P1 P1' 116.08(17) . . ?
C3' N2 C7 117.5(4) . . ?
C3' N2 P1 126.1(4) . . ?
C7 N2 P1 113.4(4) . . ?
C11' C3 C10' 106.3(6) . . ?
C11' C3 N2' 112.9(5) . . ?
C10' C3 N2' 112.6(5) . . ?
C11' C3 C4' 110.5(5) . . ?
C10' C3 C4' 104.2(5) . . ?
N2' C3 C4' 110.0(5) . . ?
C10 C3' N2 110.2(5) . . ?
C10 C3' C11 108.4(6) . . ?
N2 C3' C11 112.0(5) . . ?
C10 C3' C4 106.6(5) . . ?
N2 C3' C4 111.2(5) . . ?
C11 C3' C4 108.3(5) . . ?
C5 C4 C3' 113.4(6) . . ?
C5 C4 H4A 108.9 . . ?
C3' C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3' C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 107.4(5) . . ?
C4 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 C7 114.0(5) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C9 C7 N2 112.9(5) . . ?
C9 C7 C6 110.0(5) . . ?
N2 C7 C6 110.4(5) . . ?
C9 C7 C8 106.3(5) . . ?
N2 C7 C8 112.4(5) . . ?
C6 C7 C8 104.4(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3' C10 H10A 109.5 . . ?
C3' C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3' C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3' C11 H11A 109.5 . . ?
C3' C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3' C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 N12 C16 112.9(5) . . ?
C13 N12 P1 127.3(4) . . ?
C16 N12 P1 118.5(4) . . ?
N12 C13 C15 113.2(5) . . ?
N12 C13 C14 114.0(5) . . ?
C15 C13 C14 109.1(5) . . ?
N12 C13 H13 106.7 . . ?
C15 C13 H13 106.7 . . ?
C14 C13 H13 106.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 C17 113.5(5) . . ?
N12 C16 C18 113.9(5) . . ?
C17 C16 C18 111.2(6) . . ?
N12 C16 H16 105.8 . . ?
C17 C16 H16 105.8 . . ?
C18 C16 H16 105.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N12' P1' N2' 113.8(2) . . ?
N12' P1' P1 96.20(18) . . ?
N2' P1' P1 117.08(18) . . ?
C7' N2' C3 116.1(5) . . ?
C7' N2' P1' 127.8(4) . . ?
C3 N2' P1' 113.6(4) . . ?
C5' C4' C3 114.7(6) . . ?
C5' C4' H4'1 108.6 . . ?
C3 C4' H4'1 108.6 . . ?
C5' C4' H4'2 108.6 . . ?
C3 C4' H4'2 108.6 . . ?
H4'1 C4' H4'2 107.6 . . ?
C4' C5' C6' 108.0(6) . . ?
C4' C5' H5'1 110.1 . . ?
C6' C5' H5'1 110.1 . . ?
C4' C5' H5'2 110.1 . . ?
C6' C5' H5'2 110.1 . . ?
H5'1 C5' H5'2 108.4 . . ?
C5' C6' C7' 113.4(6) . . ?
C5' C6' H6'1 108.9 . . ?
C7' C6' H6'1 108.9 . . ?
C5' C6' H6'2 108.9 . . ?
C7' C6' H6'2 108.9 . . ?
H6'1 C6' H6'2 107.7 . . ?
N2' C7' C8' 109.2(5) . . ?
N2' C7' C6' 112.1(5) . . ?
C8' C7' C6' 106.6(5) . . ?
N2' C7' C9' 112.4(5) . . ?
C8' C7' C9' 107.1(5) . . ?
C6' C7' C9' 109.1(5) . . ?
C7' C8' H8'1 109.5 . . ?
C7' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C7' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
C7' C9' H9'1 109.5 . . ?
C7' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C7' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
C3 C10' H10D 109.5 . . ?
C3 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C3 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C3 C11' H11D 109.5 . . ?
C3 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C3 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C13' N12' C16' 112.1(5) . . ?
C13' N12' P1' 127.8(4) . . ?
C16' N12' P1' 119.3(4) . . ?
N12' C13' C15' 113.8(5) . . ?
N12' C13' C14' 114.4(5) . . ?
C15' C13' C14' 109.0(5) . . ?
N12' C13' H13' 106.3 . . ?
C15' C13' H13' 106.3 . . ?
C14' C13' H13' 106.3 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C13' C15' H15D 109.5 . . ?
C13' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C13' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
N12' C16' C17' 114.0(5) . . ?
N12' C16' C18' 113.6(5) . . ?
C17' C16' C18' 109.3(6) . . ?
N12' C16' H16' 106.5 . . ?
C17' C16' H16' 106.5 . . ?
C18' C16' H16' 106.5 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C16' C18' H18D 109.5 . . ?
C16' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C16' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 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
N12 P1 N2 C3' 37.9(5) . . . . ?
P1' P1 N2 C3' -72.3(5) . . . . ?
N12 P1 N2 C7 -121.6(4) . . . . ?
P1' P1 N2 C7 128.1(3) . . . . ?
C7 N2 C3' C10 -161.0(5) . . . . ?
P1 N2 C3' C10 40.3(7) . . . . ?
C7 N2 C3' C11 78.3(6) . . . . ?
P1 N2 C3' C11 -80.5(6) . . . . ?
C7 N2 C3' C4 -43.1(7) . . . . ?
P1 N2 C3' C4 158.1(4) . . . . ?
C10 C3' C4 C5 171.5(5) . . . . ?
N2 C3' C4 C5 51.4(7) . . . . ?
C11 C3' C4 C5 -72.1(7) . . . . ?
C3' C4 C5 C6 -59.3(7) . . . . ?
C4 C5 C6 C7 60.1(7) . . . . ?
C3' N2 C7 C9 -80.4(6) . . . . ?
P1 N2 C7 C9 81.0(5) . . . . ?
C3' N2 C7 C6 43.2(6) . . . . ?
P1 N2 C7 C6 -155.4(4) . . . . ?
C3' N2 C7 C8 159.3(5) . . . . ?
P1 N2 C7 C8 -39.3(6) . . . . ?
C5 C6 C7 C9 73.5(7) . . . . ?
C5 C6 C7 N2 -51.8(7) . . . . ?
C5 C6 C7 C8 -172.8(5) . . . . ?
N2 P1 N12 C13 -90.8(5) . . . . ?
P1' P1 N12 C13 31.3(5) . . . . ?
N2 P1 N12 C16 103.5(4) . . . . ?
P1' P1 N12 C16 -134.5(4) . . . . ?
C16 N12 C13 C15 60.5(7) . . . . ?
P1 N12 C13 C15 -105.9(6) . . . . ?
C16 N12 C13 C14 -64.9(7) . . . . ?
P1 N12 C13 C14 128.7(5) . . . . ?
C13 N12 C16 C17 -125.8(6) . . . . ?
P1 N12 C16 C17 42.0(7) . . . . ?
C13 N12 C16 C18 105.6(6) . . . . ?
P1 N12 C16 C18 -86.6(6) . . . . ?
N12 P1 P1' N12' 120.5(2) . . . . ?
N2 P1 P1' N12' -119.6(2) . . . . ?
N12 P1 P1' N2' -118.7(2) . . . . ?
N2 P1 P1' N2' 1.2(3) . . . . ?
C11' C3 N2' C7' -79.1(7) . . . . ?
C10' C3 N2' C7' 160.6(5) . . . . ?
C4' C3 N2' C7' 44.9(7) . . . . ?
C11' C3 N2' P1' 84.6(6) . . . . ?
C10' C3 N2' P1' -35.7(7) . . . . ?
C4' C3 N2' P1' -151.4(4) . . . . ?
N12' P1' N2' C7' 40.6(6) . . . . ?
P1 P1' N2' C7' -70.4(5) . . . . ?
N12' P1' N2' C3 -120.8(4) . . . . ?
P1 P1' N2' C3 128.2(4) . . . . ?
C11' C3 C4' C5' 73.0(8) . . . . ?
C10' C3 C4' C5' -173.2(6) . . . . ?
N2' C3 C4' C5' -52.4(8) . . . . ?
C3 C4' C5' C6' 58.5(8) . . . . ?
C4' C5' C6' C7' -57.0(8) . . . . ?
C3 N2' C7' C8' -163.2(5) . . . . ?
P1' N2' C7' C8' 35.8(7) . . . . ?
C3 N2' C7' C6' -45.2(7) . . . . ?
P1' N2' C7' C6' 153.8(4) . . . . ?
C3 N2' C7' C9' 78.1(7) . . . . ?
P1' N2' C7' C9' -82.9(6) . . . . ?
C5' C6' C7' N2' 51.4(8) . . . . ?
C5' C6' C7' C8' 170.9(6) . . . . ?
C5' C6' C7' C9' -73.8(7) . . . . ?
N2' P1' N12' C13' -89.6(6) . . . . ?
P1 P1' N12' C13' 33.6(5) . . . . ?
N2' P1' N12' C16' 101.1(5) . . . . ?
P1 P1' N12' C16' -135.6(4) . . . . ?
C16' N12' C13' C15' 65.2(6) . . . . ?
P1' N12' C13' C15' -104.7(6) . . . . ?
C16' N12' C13' C14' -61.0(7) . . . . ?
P1' N12' C13' C14' 129.1(5) . . . . ?
C13' N12' C16' C17' -135.9(6) . . . . ?
P1' N12' C16' C17' 34.9(7) . . . . ?
C13' N12' C16' C18' 97.9(7) . . . . ?
P1' N12' C16' C18' -91.2(6) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.073

_shelxl_version_number           2014-3




# start Validation Reply Form
_vrf_PLAT018_92_gud265           
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. _full           ! Check
RESPONSE: data collected until theta = 25 deg., theta_full is a
SHELXL-2014 property and 25.24 (therefrore above the collected theta range)
;
# end Validation Reply Form
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
