# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_YT-19
_database_code_depnum_ccdc_archive 'CCDC 2036929'
loop_
_audit_author_name
_audit_author_address
'Pascal retailleau'
;icsn cnrs  gif sur yvette
France
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT601_YT-19               
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of 251 Ang**3
RESPONSE: Indeed The structure contains a channel propagating along
the b direction in zig-zag around the two-fold screwed axis located
at the unit cell origin. Examination of the refined structure using
the SQUEEZE procedure as implemented within PLATON (Spek, 2015) 
showed the presence of 88 electrons per unit cell. But there were 
no significant peaks in the difference maps, thus no plausible solvent
model -that could be one disordered or mobile hexane molecule 
(50 electrons) per complex- could be developed. Nevertheless the 
SQUEEZE procedure by omitting the solvent contribution to the 
diffraction did not improve at all the model refinement, so it 
was abandoned for the present crystal structure.

;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cl3 N3 Ni O3'
_chemical_formula_sum            'C28 H22 Cl3 N3 Ni O3'
_chemical_formula_weight         613.54

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.80049(17)
_cell_length_b                   11.6264(2)
_cell_length_c                   13.6934(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.1849(17)
_cell_angle_gamma                90
_cell_volume                     1482.36(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12471
_cell_measurement_theta_min      3.6630
_cell_measurement_theta_max      24.8150

_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.957
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            27122
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5410
_reflns_number_gt                4849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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 2076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5384
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.5027(6) 0.7518(5) 0.3043(4) 0.0648(14) Uani 1 1 d . . . . .
H1 H 0.556684 0.798574 0.357414 0.078 Uiso 1 1 calc R U . . .
Ni1 Ni 0.79186(5) 0.48703(4) 0.32973(4) 0.04135(16) Uani 1 1 d . . . . .
C2 C 0.3600(6) 0.7775(6) 0.2575(5) 0.0733(16) Uani 1 1 d . . . . .
H2 H 0.318671 0.841218 0.278182 0.088 Uiso 1 1 calc R U . . .
C3 C 0.2796(5) 0.7078(6) 0.1796(4) 0.0659(15) Uani 1 1 d . . . . .
C4 C 0.3391(5) 0.6146(6) 0.1502(4) 0.0619(14) Uani 1 1 d . . . . .
H4 H 0.282250 0.567829 0.098207 0.074 Uiso 1 1 calc R U . . .
C5 C 0.4852(5) 0.5860(4) 0.1962(3) 0.0498(11) Uani 1 1 d . . . . .
C6 C 0.5691(5) 0.6571(4) 0.2743(3) 0.0496(11) Uani 1 1 d . . . . .
C7 C 0.5378(4) 0.4843(5) 0.1566(3) 0.0497(9) Uani 1 1 d . . . . .
C8 C 0.4469(5) 0.4334(5) 0.0593(4) 0.0610(13) Uani 1 1 d . . . . .
C9 C 0.4199(7) 0.4939(9) -0.0321(4) 0.0884(19) Uani 1 1 d . . . . .
H9 H 0.459195 0.566687 -0.032378 0.106 Uiso 1 1 calc R U . . .
C10 C 0.3343(11) 0.4454(11) -0.1228(6) 0.120(4) Uani 1 1 d . . . . .
H10 H 0.315443 0.485142 -0.184566 0.145 Uiso 1 1 calc R U . . .
C11 C 0.2767(9) 0.3361(13) -0.1203(7) 0.126(4) Uani 1 1 d . . . . .
H11 H 0.219029 0.303582 -0.181264 0.151 Uiso 1 1 calc R U . . .
C12 C 0.3023(8) 0.2760(9) -0.0319(7) 0.111(3) Uani 1 1 d . . . . .
H12 H 0.263852 0.202854 -0.032035 0.134 Uiso 1 1 calc R U . . .
C13 C 0.3872(7) 0.3257(7) 0.0597(5) 0.0819(18) Uani 1 1 d . . . . .
H13 H 0.403837 0.286150 0.121335 0.098 Uiso 1 1 calc R U . . .
N14 N 0.7151(4) 0.6328(3) 0.3242(3) 0.0440(8) Uani 1 1 d . . . . .
C15 C 0.8077(5) 0.7146(4) 0.3783(3) 0.0485(10) Uani 1 1 d . . . . .
C16 C 0.9555(5) 0.6668(4) 0.4339(3) 0.0461(10) Uani 1 1 d . . . . .
H16A H 0.992434 0.702297 0.502020 0.055 Uiso 1 1 calc R U . . .
N17 N 0.6614(4) 0.4379(3) 0.2071(3) 0.0476(9) Uani 1 1 d . . . . .
O18 O 0.7865(4) 0.8173(3) 0.3820(3) 0.0702(10) Uani 1 1 d . . . . .
C20 C 0.7244(5) 0.3405(5) 0.1725(4) 0.0572(13) Uani 1 1 d . . . . .
C21 C 0.8202(5) 0.2757(5) 0.2632(4) 0.0562(12) Uani 1 1 d . . . . .
O22 O 0.8577(4) 0.1775(3) 0.2571(3) 0.0773(12) Uani 1 1 d . . . . .
O23 O 0.8611(4) 0.3372(3) 0.3470(3) 0.0544(8) Uani 1 1 d . . . . .
C24 C 0.7234(8) 0.3159(7) 0.0794(5) 0.089(2) Uani 1 1 d . . . . .
H24A H 0.677515 0.364683 0.025271 0.106 Uiso 1 1 calc R U . . .
H24B H 0.768474 0.249583 0.067084 0.106 Uiso 1 1 calc R U . . .
Cl24 Cl 0.09944(17) 0.7408(2) 0.11902(13) 0.0970(6) Uani 1 1 d . . . . .
N25 N 0.9491(4) 0.5395(3) 0.4452(3) 0.0420(8) Uani 1 1 d . . . . .
C26 C 1.0908(4) 0.4976(5) 0.4379(3) 0.0497(10) Uani 1 1 d . . . . .
H26A H 1.167299 0.510283 0.501842 0.060 Uiso 1 1 calc R U . . .
H26B H 1.086650 0.416457 0.420871 0.060 Uiso 1 1 calc R U . . .
C27 C 1.1119(6) 0.5688(5) 0.3537(4) 0.0602(13) Uani 1 1 d . . . . .
H27A H 1.054873 0.539731 0.287032 0.072 Uiso 1 1 calc R U . . .
H27B H 1.212186 0.569841 0.356827 0.072 Uiso 1 1 calc R U . . .
C28 C 1.0618(6) 0.6883(5) 0.3729(5) 0.0646(14) Uani 1 1 d . . . . .
H28A H 1.014444 0.727083 0.308519 0.078 Uiso 1 1 calc R U . . .
H28B H 1.142172 0.734802 0.412517 0.078 Uiso 1 1 calc R U . . .
C29 C 0.9325(5) 0.5042(5) 0.5460(3) 0.0498(11) Uani 1 1 d . . . . .
H29A H 0.934059 0.420909 0.550163 0.060 Uiso 1 1 calc R U . . .
H29B H 1.013859 0.532926 0.601095 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7975(5) 0.5470(4) 0.5620(3) 0.0469(10) Uani 1 1 d . . . . .
C31 C 0.7985(5) 0.6494(5) 0.6135(4) 0.0545(12) Uani 1 1 d . . . . .
H31A H 0.883810 0.690379 0.638955 0.065 Uiso 1 1 calc R U . . .
C32 C 0.6737(6) 0.6917(5) 0.6274(4) 0.0583(12) Uani 1 1 d . . . . .
C33 C 0.5472(5) 0.6296(5) 0.5935(4) 0.0615(13) Uani 1 1 d . . . . .
C34 C 0.5463(6) 0.5271(5) 0.5425(4) 0.0640(14) Uani 1 1 d . . . . .
H34A H 0.461782 0.484780 0.518744 0.077 Uiso 1 1 calc R U . . .
C35 C 0.6682(5) 0.4877(5) 0.5268(3) 0.0564(10) Uani 1 1 d . . . . .
H35A H 0.665164 0.418965 0.491416 0.068 Uiso 1 1 calc R U . . .
Cl36 Cl 0.39307(18) 0.67896(18) 0.61511(17) 0.0973(6) Uani 1 1 d . . . . .
Cl37 Cl 0.6763(2) 0.82403(15) 0.68591(17) 0.0938(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(8) . ?
C1 C6 1.404(7) . ?
C1 H1 0.9300 . ?
Ni1 N14 1.846(4) . ?
Ni1 N17 1.855(4) . ?
Ni1 O23 1.858(3) . ?
Ni1 N25 1.930(4) . ?
C2 C3 1.375(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(8) . ?
C3 Cl24 1.743(5) . ?
C4 C5 1.412(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(7) . ?
C5 C7 1.460(7) . ?
C6 N14 1.408(6) . ?
C7 N17 1.309(6) . ?
C7 C8 1.476(7) . ?
C8 C13 1.383(10) . ?
C8 C9 1.387(10) . ?
C9 C10 1.383(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N14 C15 1.364(6) . ?
C15 O18 1.215(6) . ?
C15 C16 1.516(6) . ?
C16 N25 1.491(6) . ?
C16 C28 1.546(7) . ?
C16 H16A 0.9800 . ?
N17 C20 1.440(6) . ?
C20 C24 1.303(8) . ?
C20 C21 1.505(7) . ?
C21 O22 1.210(6) . ?
C21 O23 1.304(6) . ?
C24 H24A 0.9300 . ?
C24 H24B 0.9300 . ?
N25 C29 1.497(6) . ?
N25 C26 1.504(6) . ?
C26 C27 1.485(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.524(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.492(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.382(7) . ?
C30 C35 1.390(7) . ?
C31 C32 1.385(8) . ?
C31 H31A 0.9300 . ?
C32 C33 1.384(8) . ?
C32 Cl37 1.732(6) . ?
C33 C34 1.380(8) . ?
C33 Cl36 1.726(5) . ?
C34 C35 1.358(8) . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9300 . ?

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 122.0(5) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
N14 Ni1 N17 95.06(16) . . ?
N14 Ni1 O23 173.77(17) . . ?
N17 Ni1 O23 87.00(16) . . ?
N14 Ni1 N25 87.41(15) . . ?
N17 Ni1 N25 170.91(17) . . ?
O23 Ni1 N25 91.46(15) . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 Cl24 120.1(5) . . ?
C2 C3 Cl24 119.3(4) . . ?
C3 C4 C5 121.9(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.3(5) . . ?
C6 C5 C7 124.8(4) . . ?
C4 C5 C7 116.8(4) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 N14 121.2(4) . . ?
C1 C6 N14 120.6(4) . . ?
N17 C7 C5 120.9(4) . . ?
N17 C7 C8 120.7(5) . . ?
C5 C7 C8 118.5(4) . . ?
C13 C8 C9 120.1(6) . . ?
C13 C8 C7 119.8(5) . . ?
C9 C8 C7 120.2(6) . . ?
C10 C9 C8 119.7(9) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.0(9) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 118.9(9) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C8 C13 C12 120.4(8) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 N14 C6 121.8(4) . . ?
C15 N14 Ni1 115.1(3) . . ?
C6 N14 Ni1 123.0(3) . . ?
O18 C15 N14 127.9(5) . . ?
O18 C15 C16 119.2(4) . . ?
N14 C15 C16 112.8(4) . . ?
N25 C16 C15 110.6(4) . . ?
N25 C16 C28 105.9(4) . . ?
C15 C16 C28 111.6(4) . . ?
N25 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C28 C16 H16A 109.6 . . ?
C7 N17 C20 124.8(4) . . ?
C7 N17 Ni1 127.9(3) . . ?
C20 N17 Ni1 107.2(3) . . ?
C24 C20 N17 128.4(6) . . ?
C24 C20 C21 120.7(5) . . ?
N17 C20 C21 110.1(4) . . ?
O22 C21 O23 124.1(5) . . ?
O22 C21 C20 122.7(5) . . ?
O23 C21 C20 113.2(4) . . ?
C21 O23 Ni1 113.7(3) . . ?
C20 C24 H24A 120.0 . . ?
C20 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C16 N25 C29 112.8(4) . . ?
C16 N25 C26 104.2(4) . . ?
C29 N25 C26 110.0(3) . . ?
C16 N25 Ni1 106.1(3) . . ?
C29 N25 Ni1 112.3(3) . . ?
C26 N25 Ni1 111.1(3) . . ?
C27 C26 N25 103.1(4) . . ?
C27 C26 H26A 111.1 . . ?
N25 C26 H26A 111.1 . . ?
C27 C26 H26B 111.1 . . ?
N25 C26 H26B 111.1 . . ?
H26A C26 H26B 109.1 . . ?
C26 C27 C28 104.0(4) . . ?
C26 C27 H27A 110.9 . . ?
C28 C27 H27A 110.9 . . ?
C26 C27 H27B 110.9 . . ?
C28 C27 H27B 110.9 . . ?
H27A C27 H27B 109.0 . . ?
C27 C28 C16 104.7(4) . . ?
C27 C28 H28A 110.8 . . ?
C16 C28 H28A 110.8 . . ?
C27 C28 H28B 110.8 . . ?
C16 C28 H28B 110.8 . . ?
H28A C28 H28B 108.9 . . ?
C30 C29 N25 113.6(4) . . ?
C30 C29 H29A 108.8 . . ?
N25 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
N25 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C31 C30 C35 117.7(5) . . ?
C31 C30 C29 119.7(4) . . ?
C35 C30 C29 122.5(4) . . ?
C30 C31 C32 120.6(5) . . ?
C30 C31 H31A 119.7 . . ?
C32 C31 H31A 119.7 . . ?
C33 C32 C31 120.4(5) . . ?
C33 C32 Cl37 120.1(4) . . ?
C31 C32 Cl37 119.5(4) . . ?
C34 C33 C32 118.9(5) . . ?
C34 C33 Cl36 120.4(4) . . ?
C32 C33 Cl36 120.6(5) . . ?
C35 C34 C33 120.3(5) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C34 C35 C30 122.0(5) . . ?
C34 C35 H35A 119.0 . . ?
C30 C35 H35A 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(9) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
C1 C2 C3 Cl24 -179.3(5) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
Cl24 C3 C4 C5 178.9(4) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C3 C4 C5 C7 -178.9(5) . . . . ?
C4 C5 C6 C1 1.4(7) . . . . ?
C7 C5 C6 C1 -179.8(5) . . . . ?
C4 C5 C6 N14 179.2(4) . . . . ?
C7 C5 C6 N14 -1.9(7) . . . . ?
C2 C1 C6 C5 -1.7(8) . . . . ?
C2 C1 C6 N14 -179.6(5) . . . . ?
C6 C5 C7 N17 15.2(8) . . . . ?
C4 C5 C7 N17 -166.0(5) . . . . ?
C6 C5 C7 C8 -166.2(5) . . . . ?
C4 C5 C7 C8 12.7(7) . . . . ?
N17 C7 C8 C13 65.8(7) . . . . ?
C5 C7 C8 C13 -112.8(6) . . . . ?
N17 C7 C8 C9 -115.0(6) . . . . ?
C5 C7 C8 C9 66.4(7) . . . . ?
C13 C8 C9 C10 -0.7(10) . . . . ?
C7 C8 C9 C10 -179.8(6) . . . . ?
C8 C9 C10 C11 0.0(12) . . . . ?
C9 C10 C11 C12 -0.1(14) . . . . ?
C10 C11 C12 C13 0.9(14) . . . . ?
C9 C8 C13 C12 1.4(10) . . . . ?
C7 C8 C13 C12 -179.4(6) . . . . ?
C11 C12 C13 C8 -1.5(12) . . . . ?
C5 C6 N14 C15 161.3(4) . . . . ?
C1 C6 N14 C15 -20.9(7) . . . . ?
C5 C6 N14 Ni1 -23.5(6) . . . . ?
C1 C6 N14 Ni1 154.3(4) . . . . ?
N17 Ni1 N14 C15 -155.9(3) . . . . ?
N25 Ni1 N14 C15 15.3(3) . . . . ?
N17 Ni1 N14 C6 28.5(4) . . . . ?
N25 Ni1 N14 C6 -160.2(4) . . . . ?
C6 N14 C15 O18 -9.3(8) . . . . ?
Ni1 N14 C15 O18 175.2(4) . . . . ?
C6 N14 C15 C16 174.5(4) . . . . ?
Ni1 N14 C15 C16 -1.1(5) . . . . ?
O18 C15 C16 N25 164.0(4) . . . . ?
N14 C15 C16 N25 -19.4(5) . . . . ?
O18 C15 C16 C28 -78.4(6) . . . . ?
N14 C15 C16 C28 98.3(5) . . . . ?
C5 C7 N17 C20 -177.6(5) . . . . ?
C8 C7 N17 C20 3.7(8) . . . . ?
C5 C7 N17 Ni1 -1.4(7) . . . . ?
C8 C7 N17 Ni1 180.0(4) . . . . ?
N14 Ni1 N17 C7 -16.8(5) . . . . ?
O23 Ni1 N17 C7 157.3(5) . . . . ?
N14 Ni1 N17 C20 160.0(3) . . . . ?
O23 Ni1 N17 C20 -25.9(3) . . . . ?
C7 N17 C20 C24 38.2(9) . . . . ?
Ni1 N17 C20 C24 -138.7(6) . . . . ?
C7 N17 C20 C21 -152.4(5) . . . . ?
Ni1 N17 C20 C21 30.8(5) . . . . ?
C24 C20 C21 O22 -27.9(9) . . . . ?
N17 C20 C21 O22 161.7(5) . . . . ?
C24 C20 C21 O23 150.2(6) . . . . ?
N17 C20 C21 O23 -20.2(6) . . . . ?
O22 C21 O23 Ni1 177.2(5) . . . . ?
C20 C21 O23 Ni1 -0.9(5) . . . . ?
N17 Ni1 O23 C21 15.8(4) . . . . ?
N25 Ni1 O23 C21 -155.3(3) . . . . ?
C15 C16 N25 C29 -94.3(4) . . . . ?
C28 C16 N25 C29 144.6(4) . . . . ?
C15 C16 N25 C26 146.4(4) . . . . ?
C28 C16 N25 C26 25.4(4) . . . . ?
C15 C16 N25 Ni1 29.1(4) . . . . ?
C28 C16 N25 Ni1 -92.0(4) . . . . ?
C16 N25 C26 C27 -41.3(5) . . . . ?
C29 N25 C26 C27 -162.4(4) . . . . ?
Ni1 N25 C26 C27 72.5(4) . . . . ?
N25 C26 C27 C28 40.7(5) . . . . ?
C26 C27 C28 C16 -24.7(6) . . . . ?
N25 C16 C28 C27 -0.6(5) . . . . ?
C15 C16 C28 C27 -121.0(5) . . . . ?
C16 N25 C29 C30 61.5(5) . . . . ?
C26 N25 C29 C30 177.3(4) . . . . ?
Ni1 N25 C29 C30 -58.3(5) . . . . ?
N25 C29 C30 C31 -93.5(5) . . . . ?
N25 C29 C30 C35 86.3(6) . . . . ?
C35 C30 C31 C32 -1.1(7) . . . . ?
C29 C30 C31 C32 178.8(5) . . . . ?
C30 C31 C32 C33 2.5(8) . . . . ?
C30 C31 C32 Cl37 -176.5(4) . . . . ?
C31 C32 C33 C34 -2.3(8) . . . . ?
Cl37 C32 C33 C34 176.8(4) . . . . ?
C31 C32 C33 Cl36 177.4(4) . . . . ?
Cl37 C32 C33 Cl36 -3.5(7) . . . . ?
C32 C33 C34 C35 0.6(9) . . . . ?
Cl36 C33 C34 C35 -179.1(4) . . . . ?
C33 C34 C35 C30 0.9(8) . . . . ?
C31 C30 C35 C34 -0.7(7) . . . . ?
C29 C30 C35 C34 179.5(5) . . . . ?

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
_geom_hbond_publ_flag
C26 H26B O23 0.97 2.32 2.889(6) 117.1 . yes
C31 H31A O22 0.93 2.49 3.297(6) 144.8 2_756 yes
C16 H16A O23 0.98 2.63 3.577(5) 161.2 2_756 yes
C28 H28A Cl24 0.97 2.97 3.660(6) 129.4 1_655 yes
C1 H1 O18 0.93 2.18 2.757(7) 119.2 . yes
C29 H29B O22 0.97 2.58 3.478(6) 154.0 2_756 yes

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.092




####################################################################### 
# 
# 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_YT-96
_database_code_depnum_ccdc_archive 'CCDC 2036930'
loop_
_audit_author_name
_audit_author_address
'Pascal retailleau'
;icsn cnrs  gif sur yvette
France
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;'(R)-2-((tert-butoxycarbonyl)amino)-3-(diethoxyphosphoryl)propanoic acid'
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N O7 P'
_chemical_formula_sum            'C12 H24 N O7 P'
_chemical_formula_weight         325.29

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'

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

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

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

_cell_length_a                   9.4385(3)
_cell_length_b                   10.4341(2)
_cell_length_c                   16.9555(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.82(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    10488
_cell_measurement_theta_min      3.7910
_cell_measurement_theta_max      28.6980

_exptl_crystal_description       'small block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.24703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            20342
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.906
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3414
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.5848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3405
_refine_ls_number_parameters     219
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.098
_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
O1 O 0.2203(3) 0.6279(2) 0.65796(11) 0.0448(6) Uani 1 1 d . . . . .
H1O H 0.235809 0.594581 0.702241 0.067 Uiso 1 1 calc R U . . .
C2 C 0.2510(3) 0.5451(2) 0.60227(13) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.2294(3) 0.6029(2) 0.52012(13) 0.0183(5) Uani 1 1 d . . . . .
H3 H 0.125822 0.618912 0.512810 0.022 Uiso 1 1 calc R U . . .
O4 O 0.2885(3) 0.43812(19) 0.61411(12) 0.0446(6) Uani 1 1 d . . . . .
P7 P 0.23492(8) 0.55033(7) 0.35753(4) 0.02567(19) Uani 1 1 d . . . . .
N6 N 0.3024(2) 0.72452(19) 0.51313(12) 0.0185(4) Uani 1 1 d . . . . .
H6N H 0.393(4) 0.729(3) 0.5086(17) 0.022 Uiso 1 1 d . U . . .
C5 C 0.2768(3) 0.5078(2) 0.45700(14) 0.0209(5) Uani 1 1 d . . . . .
H5A H 0.232858 0.423720 0.468582 0.025 Uiso 1 1 calc R U . . .
H5AB H 0.380704 0.496952 0.461164 0.025 Uiso 1 1 calc R U . . .
O8 O 0.3188(3) 0.6737(2) 0.33528(12) 0.0448(6) Uani 1 1 d D U . . .
O9 O 0.2583(3) 0.4425(2) 0.30357(11) 0.0421(5) Uani 1 1 d . . . . .
O10 O 0.0789(2) 0.5989(3) 0.36425(13) 0.0439(6) Uani 1 1 d D . . . .
C11 C 0.2330(3) 0.8356(2) 0.50328(14) 0.0208(5) Uani 1 1 d . . . . .
O12 O 0.3276(2) 0.93060(17) 0.49258(14) 0.0323(5) Uani 1 1 d . . . . .
O13 O 0.10487(19) 0.84872(17) 0.50453(12) 0.0291(4) Uani 1 1 d . . . . .
C14 C 0.2820(3) 1.0653(3) 0.4878(3) 0.0441(8) Uani 1 1 d . U . . .
C15 C 0.4242(4) 1.1341(3) 0.4790(4) 0.0694(14) Uani 1 1 d . U . . .
H15A H 0.408593 1.226934 0.478028 0.104 Uiso 1 1 calc R U . . .
H15B H 0.469599 1.107363 0.429645 0.104 Uiso 1 1 calc R U . . .
H15C H 0.485615 1.112066 0.523563 0.104 Uiso 1 1 calc R U . . .
C16 C 0.1899(4) 1.0852(3) 0.4162(3) 0.0578(11) Uani 1 1 d . U . . .
H16A H 0.178620 1.177210 0.406401 0.087 Uiso 1 1 calc R U . . .
H16B H 0.096707 1.046469 0.425273 0.087 Uiso 1 1 calc R U . . .
H16C H 0.234430 1.044846 0.370229 0.087 Uiso 1 1 calc R U . . .
C17 C 0.2098(4) 1.1049(3) 0.5636(3) 0.0552(10) Uani 1 1 d . U . . .
H17A H 0.190944 1.197191 0.562397 0.083 Uiso 1 1 calc R U . . .
H17B H 0.271536 1.084837 0.608390 0.083 Uiso 1 1 calc R U . . .
H17C H 0.120263 1.058196 0.569036 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4590(6) 0.6642(6) 0.2987(4) 0.0702(17) Uani 0.856(9) 1 d D U P A 1
H18A H 0.532817 0.689230 0.337217 0.084 Uiso 0.856(9) 1 calc R U P A 1
H18B H 0.477104 0.574667 0.282229 0.084 Uiso 0.856(9) 1 calc R U P A 1
C19 C 0.4644(7) 0.7456(8) 0.2328(3) 0.101(3) Uani 0.856(9) 1 d D U P A 1
H19A H 0.395383 0.716945 0.193364 0.151 Uiso 0.856(9) 1 calc R U P A 1
H19B H 0.559756 0.743290 0.209895 0.151 Uiso 0.856(9) 1 calc R U P A 1
H19C H 0.441952 0.833435 0.249019 0.151 Uiso 0.856(9) 1 calc R U P A 1
C18B C 0.458(3) 0.716(3) 0.319(2) 0.064(3) Uani 0.144(9) 1 d D U P A 2
H18C H 0.504289 0.737284 0.369484 0.077 Uiso 0.144(9) 1 calc R U P A 2
H18D H 0.451023 0.796717 0.288229 0.077 Uiso 0.144(9) 1 calc R U P A 2
C19B C 0.554(3) 0.630(3) 0.276(2) 0.073(5) Uani 0.144(9) 1 d D U P A 2
H19D H 0.514305 0.543311 0.275380 0.109 Uiso 0.144(9) 1 calc R U P A 2
H19E H 0.646726 0.629414 0.301208 0.109 Uiso 0.144(9) 1 calc R U P A 2
H19F H 0.563921 0.660476 0.221094 0.109 Uiso 0.144(9) 1 calc R U P A 2
C20 C -0.0046(5) 0.6373(5) 0.2966(2) 0.0592(11) Uani 1 1 d D . . . .
H20A H -0.105971 0.635415 0.311506 0.071 Uiso 1 1 calc R U . . .
H20B H 0.009391 0.573520 0.254076 0.071 Uiso 1 1 calc R U . . .
C21 C 0.0284(7) 0.7635(6) 0.2657(4) 0.100(2) Uani 1 1 d D . . . .
H21A H 0.022195 0.826827 0.308179 0.151 Uiso 1 1 calc R U . . .
H21B H -0.039234 0.785460 0.223970 0.151 Uiso 1 1 calc R U . . .
H21C H 0.124657 0.763288 0.243943 0.151 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
O1 C2 1.311(3) . ?
O1 H1O 0.8400 . ?
C2 O4 1.189(3) . ?
C2 C3 1.531(3) . ?
C3 N6 1.449(3) . ?
C3 C5 1.526(3) . ?
C3 H3 1.0000 . ?
P7 O9 1.467(2) . ?
P7 O8 1.557(2) . ?
P7 O10 1.561(2) . ?
P7 C5 1.788(2) . ?
N6 C11 1.342(3) . ?
N6 H6N 0.86(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
O8 C18B 1.42(2) . ?
O8 C18 1.465(6) . ?
O10 C20 1.448(4) . ?
C11 O13 1.217(3) . ?
C11 O12 1.346(3) . ?
O12 C14 1.472(3) . ?
C14 C16 1.508(6) . ?
C14 C17 1.512(6) . ?
C14 C15 1.530(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.406(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18B C19B 1.46(2) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20 C21 1.451(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 O1 H1O 109.5 . . ?
O4 C2 O1 124.2(2) . . ?
O4 C2 C3 124.3(2) . . ?
O1 C2 C3 111.5(2) . . ?
N6 C3 C5 111.9(2) . . ?
N6 C3 C2 110.8(2) . . ?
C5 C3 C2 110.09(19) . . ?
N6 C3 H3 108.0 . . ?
C5 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
O9 P7 O8 113.99(13) . . ?
O9 P7 O10 115.86(14) . . ?
O8 P7 O10 103.23(15) . . ?
O9 P7 C5 111.39(12) . . ?
O8 P7 C5 108.74(13) . . ?
O10 P7 C5 102.70(12) . . ?
C11 N6 C3 122.3(2) . . ?
C11 N6 H6N 115(2) . . ?
C3 N6 H6N 121.8(19) . . ?
C3 C5 P7 115.82(17) . . ?
C3 C5 H5A 108.3 . . ?
P7 C5 H5A 108.3 . . ?
C3 C5 H5AB 108.3 . . ?
P7 C5 H5AB 108.3 . . ?
H5A C5 H5AB 107.4 . . ?
C18B O8 P7 141.1(16) . . ?
C18 O8 P7 120.4(3) . . ?
C20 O10 P7 123.0(2) . . ?
O13 C11 N6 125.4(2) . . ?
O13 C11 O12 125.4(2) . . ?
N6 C11 O12 109.2(2) . . ?
C11 O12 C14 121.1(2) . . ?
O12 C14 C16 110.2(3) . . ?
O12 C14 C17 110.2(3) . . ?
C16 C14 C17 112.8(3) . . ?
O12 C14 C15 101.3(2) . . ?
C16 C14 C15 111.3(3) . . ?
C17 C14 C15 110.5(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 O8 109.2(6) . . ?
C19 C18 H18A 109.8 . . ?
O8 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
O8 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C18B C19B 119(2) . . ?
O8 C18B H18C 107.6 . . ?
C19B C18B H18C 107.6 . . ?
O8 C18B H18D 107.6 . . ?
C19B C18B H18D 107.6 . . ?
H18C C18B H18D 107.1 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
O10 C20 C21 114.9(4) . . ?
O10 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
O10 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 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
O4 C2 C3 N6 -129.8(3) . . . . ?
O1 C2 C3 N6 51.3(3) . . . . ?
O4 C2 C3 C5 -5.5(4) . . . . ?
O1 C2 C3 C5 175.7(2) . . . . ?
C5 C3 N6 C11 122.2(2) . . . . ?
C2 C3 N6 C11 -114.5(3) . . . . ?
N6 C3 C5 P7 -65.1(3) . . . . ?
C2 C3 C5 P7 171.18(18) . . . . ?
O9 P7 C5 C3 -168.43(19) . . . . ?
O8 P7 C5 C3 65.1(2) . . . . ?
O10 P7 C5 C3 -43.8(2) . . . . ?
O9 P7 O8 C18B -54(2) . . . . ?
O10 P7 O8 C18B 180(2) . . . . ?
C5 P7 O8 C18B 71(2) . . . . ?
O9 P7 O8 C18 -33.5(4) . . . . ?
O10 P7 O8 C18 -160.0(4) . . . . ?
C5 P7 O8 C18 91.4(4) . . . . ?
O9 P7 O10 C20 -54.5(3) . . . . ?
O8 P7 O10 C20 70.8(3) . . . . ?
C5 P7 O10 C20 -176.2(3) . . . . ?
C3 N6 C11 O13 5.3(4) . . . . ?
C3 N6 C11 O12 -175.3(2) . . . . ?
O13 C11 O12 C14 5.3(4) . . . . ?
N6 C11 O12 C14 -174.1(3) . . . . ?
C11 O12 C14 C16 -64.2(4) . . . . ?
C11 O12 C14 C17 60.9(4) . . . . ?
C11 O12 C14 C15 178.0(3) . . . . ?
P7 O8 C18 C19 132.0(4) . . . . ?
P7 O8 C18B C19B 36(5) . . . . ?
P7 O10 C20 C21 -77.6(5) . . . . ?

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
_geom_hbond_publ_flag
O1 H1O O9 0.84 1.76 2.584(3) 165.4 2_565 yes
N6 H6N O13 0.86(3) 2.17(3) 2.970(3) 155(3) 4_566 yes
C16 H16B O13 0.98 2.46 2.996(4) 113.8 . yes
C17 H17C O13 0.98 2.45 3.021(4) 116.9 . yes
C18 H18A O1 0.99 2.60 3.367(6) 133.8 4_566 yes
C18B H18C O13 0.99 2.50 3.37(4) 145.9 4_566 yes
C21 H21C O8 0.98 2.57 3.127(6) 115.7 . yes

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052




