# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_yv508
_database_code_depnum_ccdc_archive 'CCDC 2069784'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;


_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_chemical_name_common            CK273
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.060 #?# in millimeters
_exptl_crystal_size_mid          0.050 #?# in millimeters
_exptl_crystal_size_min          0.040 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      102.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   33.2658(19)
_cell_length_b                   4.8664(3)
_cell_length_c                   27.5320(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.702(2)
_cell_angle_gamma                90
_cell_volume                     4290.7(4)
_cell_measurement_temperature    102.(2) #?# in K
_cell_measurement_reflns_used    5802
_cell_measurement_theta_min      2.9921
_cell_measurement_theta_max      26.6605
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8951
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'

_diffrn_reflns_number            4419 #xl
_diffrn_reflns_av_R_equivalents  0.0683 #xl
_diffrn_reflns_av_unetI/netI     0.0482 #xl
_diffrn_reflns_limit_h_min       -42 #xl
_diffrn_reflns_limit_h_max       39 #xl
_diffrn_reflns_limit_k_min       0 #xl
_diffrn_reflns_limit_k_max       6 #xl
_diffrn_reflns_limit_l_min       0 #xl
_diffrn_reflns_limit_l_max       34 #xl
_diffrn_reflns_theta_min         2.992 #xl
_diffrn_reflns_theta_max         26.733 #xl
_diffrn_measured_fraction_theta_max 0.971 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.984 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.971 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.984 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.971 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.984 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15

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

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

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'

_reflns_number_total             4419 #xl
_reflns_number_gt                3699 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+11.0748P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         4419 #xl
_refine_ls_number_parameters     279 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0752 #xl
_refine_ls_R_factor_gt           0.0556 #xl
_refine_ls_wR_factor_ref         0.1235 #xl
_refine_ls_wR_factor_gt          0.1143 #xl
_refine_ls_goodness_of_fit_ref   1.118 #xl
_refine_ls_restrained_S_all      1.118 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.322 #xl
_refine_diff_density_min         -0.297 #xl
_refine_diff_density_rms         0.061 #xl

_refine_special_details          
;
The site occupation factor of the water O-atom refined to 0.56. Its hydrogen 
atoms could not be located and have been omitted from the refinement. The
structure has been refined as a 2-component twin. The volume ratio of the
minor twin domain refined to 0.23.
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'

_computing_publication_material  ?

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 0.34776(9) 0.4033(6) 0.38359(11) 0.0208(6) Uani 1 1 d . . . . .
H1A H 0.323622 0.414690 0.353320 0.025 Uiso 1 1 calc R U . . .
H1AB H 0.353374 0.206350 0.391591 0.025 Uiso 1 1 calc R U . . .
C2 C 0.33626(9) 0.5372(6) 0.42657(10) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.29682(9) 0.8457(6) 0.45472(12) 0.0253(7) Uani 1 1 d . . . . .
C4 C 0.34090(10) 0.5650(7) 0.50944(12) 0.0301(7) Uani 1 1 d . . . . .
C5 C 0.26344(10) 1.0582(7) 0.44423(13) 0.0348(8) Uani 1 1 d . . . . .
H5A H 0.271611 1.208967 0.468505 0.052 Uiso 1 1 calc R U . . .
H5B H 0.237331 0.976397 0.447352 0.052 Uiso 1 1 calc R U . . .
H5C H 0.259375 1.129255 0.409937 0.052 Uiso 1 1 calc R U . . .
C6 C 0.35787(13) 0.4607(11) 0.56192(13) 0.0553(12) Uani 1 1 d . . . . .
H6A H 0.379606 0.323754 0.562579 0.083 Uiso 1 1 calc R U . . .
H6B H 0.335319 0.376050 0.573387 0.083 Uiso 1 1 calc R U . . .
H6C H 0.369835 0.613845 0.584292 0.083 Uiso 1 1 calc R U . . .
C7 C 0.43843(9) 0.4098(6) 0.41351(11) 0.0216(6) Uani 1 1 d . . . . .
H7A H 0.436632 0.444828 0.448281 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.439151 0.208438 0.408694 0.026 Uiso 1 1 calc R U . . .
C8 C 0.47751(9) 0.5349(6) 0.40672(11) 0.0228(6) Uani 1 1 d . . . . .
C9 C 0.53043(9) 0.8421(7) 0.43078(12) 0.0269(7) Uani 1 1 d . . . . .
C10 C 0.52452(10) 0.5756(8) 0.36147(12) 0.0345(8) Uani 1 1 d . . . . .
C11 C 0.55439(10) 1.0462(7) 0.46772(13) 0.0342(8) Uani 1 1 d . . . . .
H11A H 0.562224 1.201589 0.449564 0.051 Uiso 1 1 calc R U . . .
H11B H 0.579648 0.959298 0.488935 0.051 Uiso 1 1 calc R U . . .
H11C H 0.537053 1.112011 0.488986 0.051 Uiso 1 1 calc R U . . .
C12 C 0.54032(12) 0.4907(11) 0.31795(14) 0.0571(13) Uani 1 1 d . . . . .
H12A H 0.527754 0.314414 0.304731 0.086 Uiso 1 1 calc R U . . .
H12B H 0.570760 0.471378 0.329116 0.086 Uiso 1 1 calc R U . . .
H12C H 0.532816 0.630389 0.291394 0.086 Uiso 1 1 calc R U . . .
C13 C 0.39271(10) 0.4064(6) 0.30807(10) 0.0226(6) Uani 1 1 d . . . . .
H13A H 0.420653 0.432236 0.302518 0.027 Uiso 1 1 calc R U . . .
H13B H 0.387469 0.206365 0.308718 0.027 Uiso 1 1 calc R U . . .
C14 C 0.36059(10) 0.5320(6) 0.26496(11) 0.0246(6) Uani 1 1 d . . . . .
C15 C 0.34364(13) 0.8252(7) 0.19926(12) 0.0373(9) Uani 1 1 d . . . . .
C16 C 0.29483(11) 0.5417(8) 0.21446(12) 0.0365(8) Uani 1 1 d . . . . .
C17 C 0.35655(15) 1.0394(8) 0.16752(14) 0.0546(11) Uani 1 1 d . . . . .
H17A H 0.331670 1.118796 0.144150 0.082 Uiso 1 1 calc R U . . .
H17B H 0.374209 0.955281 0.148306 0.082 Uiso 1 1 calc R U . . .
H17C H 0.372244 1.184306 0.189313 0.082 Uiso 1 1 calc R U . . .
C18 C 0.25106(12) 0.4332(10) 0.20077(15) 0.0560(11) Uani 1 1 d . . . . .
H18A H 0.245862 0.339236 0.229967 0.084 Uiso 1 1 calc R U . . .
H18B H 0.247313 0.303327 0.172687 0.084 Uiso 1 1 calc R U . . .
H18C H 0.231373 0.585968 0.190694 0.084 Uiso 1 1 calc R U . . .
N1 N 0.30775(8) 0.7371(5) 0.41552(9) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.31235(8) 0.7636(6) 0.50256(10) 0.0297(6) Uani 1 1 d . . . . .
N3 N 0.35477(8) 0.4470(6) 0.47291(9) 0.0269(6) Uani 1 1 d . . . . .
N4 N 0.49618(8) 0.7302(5) 0.43974(9) 0.0246(6) Uani 1 1 d . . . . .
N5 N 0.54522(8) 0.7749(6) 0.39174(10) 0.0339(7) Uani 1 1 d . . . . .
N6 N 0.49067(8) 0.4477(6) 0.36769(10) 0.0310(6) Uani 1 1 d . . . . .
N7 N 0.37323(9) 0.7308(5) 0.23905(9) 0.0308(6) Uani 1 1 d . . . . .
N8 N 0.30471(11) 0.7363(6) 0.18507(10) 0.0412(8) Uani 1 1 d . . . . .
N9 N 0.32177(8) 0.4334(6) 0.25479(9) 0.0298(6) Uani 1 1 d . . . . .
O1 O 0.39254(7) 0.8576(4) 0.36874(8) 0.0238(4) Uani 1 1 d . . . . .
O2 O 0.46372(16) -0.0381(11) 0.2845(2) 0.058(2) Uani 0.564(10) 1 d . . . . .
P1 P 0.39282(2) 0.55220(14) 0.36872(3) 0.01816(16) Uani 1 1 d . . . . .


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 1.489(4) . ?
C1 P1 1.809(3) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 N3 1.332(4) . ?
C2 N1 1.335(4) . ?
C3 N1 1.337(4) . ?
C3 N2 1.339(4) . ?
C3 C5 1.487(4) . ?
C4 N2 1.332(4) . ?
C4 N3 1.344(4) . ?
C4 C6 1.491(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.492(4) . ?
C7 P1 1.814(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 N6 1.335(4) . ?
C8 N4 1.345(4) . ?
C9 N5 1.338(4) . ?
C9 N4 1.344(4) . ?
C9 C11 1.489(5) . ?
C10 N6 1.338(4) . ?
C10 N5 1.341(4) . ?
C10 C12 1.491(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.496(4) . ?
C13 P1 1.813(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N9 1.334(4) . ?
C14 N7 1.336(4) . ?
C15 N8 1.320(5) . ?
C15 N7 1.340(4) . ?
C15 C17 1.496(5) . ?
C16 N9 1.332(4) . ?
C16 N8 1.343(5) . ?
C16 C18 1.498(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1 P1 1.4863(19) . ?

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 P1 114.3(2) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1AB 108.7 . . ?
P1 C1 H1AB 108.7 . . ?
H1A C1 H1AB 107.6 . . ?
N3 C2 N1 125.0(3) . . ?
N3 C2 C1 117.7(3) . . ?
N1 C2 C1 117.2(2) . . ?
N1 C3 N2 124.0(3) . . ?
N1 C3 C5 118.0(3) . . ?
N2 C3 C5 117.9(3) . . ?
N2 C4 N3 125.4(3) . . ?
N2 C4 C6 116.9(3) . . ?
N3 C4 C6 117.6(3) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 P1 110.8(2) . . ?
C8 C7 H7A 109.5 . . ?
P1 C7 H7A 109.5 . . ?
C8 C7 H7AB 109.5 . . ?
P1 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
N6 C8 N4 125.2(3) . . ?
N6 C8 C7 117.2(3) . . ?
N4 C8 C7 117.5(3) . . ?
N5 C9 N4 124.2(3) . . ?
N5 C9 C11 117.8(3) . . ?
N4 C9 C11 117.9(3) . . ?
N6 C10 N5 124.4(3) . . ?
N6 C10 C12 117.8(3) . . ?
N5 C10 C12 117.8(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 P1 113.2(2) . . ?
C14 C13 H13A 108.9 . . ?
P1 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
P1 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
N9 C14 N7 125.1(3) . . ?
N9 C14 C13 117.6(3) . . ?
N7 C14 C13 117.3(3) . . ?
N8 C15 N7 125.0(3) . . ?
N8 C15 C17 118.0(3) . . ?
N7 C15 C17 116.9(4) . . ?
N9 C16 N8 124.2(3) . . ?
N9 C16 C18 117.3(3) . . ?
N8 C16 C18 118.5(3) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 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 . . ?
C2 N1 C3 115.8(3) . . ?
C4 N2 C3 115.3(3) . . ?
C2 N3 C4 114.4(3) . . ?
C9 N4 C8 114.9(3) . . ?
C9 N5 C10 115.9(3) . . ?
C8 N6 C10 115.2(3) . . ?
C14 N7 C15 114.6(3) . . ?
C15 N8 C16 115.7(3) . . ?
C16 N9 C14 115.3(3) . . ?
O1 P1 C1 113.26(13) . . ?
O1 P1 C13 113.14(13) . . ?
C1 P1 C13 104.86(13) . . ?
O1 P1 C7 112.70(13) . . ?
C1 P1 C7 106.57(13) . . ?
C13 P1 C7 105.62(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 N3 -87.2(3) . . . . ?
P1 C1 C2 N1 93.5(3) . . . . ?
P1 C7 C8 N6 -76.6(3) . . . . ?
P1 C7 C8 N4 102.1(3) . . . . ?
P1 C13 C14 N9 -83.8(3) . . . . ?
P1 C13 C14 N7 97.4(3) . . . . ?
N3 C2 N1 C3 -1.9(4) . . . . ?
C1 C2 N1 C3 177.4(3) . . . . ?
N2 C3 N1 C2 -0.7(4) . . . . ?
C5 C3 N1 C2 -176.6(3) . . . . ?
N3 C4 N2 C3 0.4(5) . . . . ?
C6 C4 N2 C3 -177.9(3) . . . . ?
N1 C3 N2 C4 1.4(5) . . . . ?
C5 C3 N2 C4 177.3(3) . . . . ?
N1 C2 N3 C4 3.3(4) . . . . ?
C1 C2 N3 C4 -175.9(3) . . . . ?
N2 C4 N3 C2 -2.5(5) . . . . ?
C6 C4 N3 C2 175.7(3) . . . . ?
N5 C9 N4 C8 1.6(4) . . . . ?
C11 C9 N4 C8 -176.0(3) . . . . ?
N6 C8 N4 C9 0.8(4) . . . . ?
C7 C8 N4 C9 -177.8(3) . . . . ?
N4 C9 N5 C10 -2.4(5) . . . . ?
C11 C9 N5 C10 175.2(3) . . . . ?
N6 C10 N5 C9 1.0(5) . . . . ?
C12 C10 N5 C9 -179.0(3) . . . . ?
N4 C8 N6 C10 -2.0(5) . . . . ?
C7 C8 N6 C10 176.6(3) . . . . ?
N5 C10 N6 C8 1.1(5) . . . . ?
C12 C10 N6 C8 -178.9(3) . . . . ?
N9 C14 N7 C15 -2.1(4) . . . . ?
C13 C14 N7 C15 176.6(3) . . . . ?
N8 C15 N7 C14 -0.1(5) . . . . ?
C17 C15 N7 C14 -177.4(3) . . . . ?
N7 C15 N8 C16 1.9(5) . . . . ?
C17 C15 N8 C16 179.2(3) . . . . ?
N9 C16 N8 C15 -1.9(5) . . . . ?
C18 C16 N8 C15 179.5(3) . . . . ?
N8 C16 N9 C14 0.1(5) . . . . ?
C18 C16 N9 C14 178.6(3) . . . . ?
N7 C14 N9 C16 2.1(5) . . . . ?
C13 C14 N9 C16 -176.6(3) . . . . ?
C2 C1 P1 O1 -43.9(3) . . . . ?
C2 C1 P1 C13 -167.7(2) . . . . ?
C2 C1 P1 C7 80.6(2) . . . . ?
C14 C13 P1 O1 -47.9(3) . . . . ?
C14 C13 P1 C1 76.0(2) . . . . ?
C14 C13 P1 C7 -171.7(2) . . . . ?
C8 C7 P1 O1 -51.3(2) . . . . ?
C8 C7 P1 C1 -176.1(2) . . . . ?
C8 C7 P1 C13 72.8(2) . . . . ?

_geom_special_details            
;

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

_audit_block_code                C18H24N9OP_H20_yv508_karaghiosoff
_audit_creation_method           'APEX3 v2018.7-2'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 N9 O P, 0.564(H2 O)'
_chemical_formula_sum            'C18 H25.13 N9 O1.56 P'
_chemical_formula_weight         423.59 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            8 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1789 #?# check!

####################################################################### 
# 
# 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_px333
_database_code_depnum_ccdc_archive 'CCDC 2072410'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'tris((3,5,6-trimethylpyrazin-2-yl)methyl)phosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H33 N6 O P'
_chemical_formula_sum            'C24 H33 N6 O P'
_chemical_formula_weight         452.53

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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   23.6498(4)
_cell_length_b                   23.6498(4)
_cell_length_c                   19.4811(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10896.0(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6789
_cell_measurement_theta_min      2.1790
_cell_measurement_theta_max      24.9410

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_F_000             3872
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            72089
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5363
_reflns_number_gt                3936
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ortep
_computing_publication_material  platon
_refine_special_details          custom
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+9.5251P] 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         5363
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.74236(2) 0.52549(2) 0.52174(3) 0.01910(15) Uani 1 1 d . . . . .
O1 O 0.72790(6) 0.52281(6) 0.44742(7) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.62945(7) 0.60605(8) 0.57292(9) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.68118(8) 0.51789(9) 0.57705(10) 0.0210(4) Uani 1 1 d . . . . .
H1A H 0.669896 0.477612 0.579037 0.025 Uiso 1 1 calc R U . . .
H1B H 0.691023 0.530200 0.624130 0.025 Uiso 1 1 calc R U . . .
N2 N 0.55037(8) 0.56312(8) 0.48146(9) 0.0296(4) Uani 1 1 d . . . . .
C2 C 0.63254(8) 0.55268(9) 0.55084(10) 0.0206(4) Uani 1 1 d . . . . .
N3 N 0.86864(8) 0.58400(8) 0.49779(10) 0.0324(5) Uani 1 1 d . . . . .
C3 C 0.59308(9) 0.53088(9) 0.50414(11) 0.0240(5) Uani 1 1 d . . . . .
N4 N 0.84561(8) 0.65328(8) 0.38715(9) 0.0291(4) Uani 1 1 d . . . . .
C4 C 0.59575(10) 0.47107(10) 0.47846(13) 0.0333(6) Uani 1 1 d . . . . .
H4A H 0.564381 0.464269 0.446648 0.050 Uiso 1 1 calc R U . . .
H4B H 0.592899 0.444948 0.517355 0.050 Uiso 1 1 calc R U . . .
H4C H 0.631726 0.464962 0.454616 0.050 Uiso 1 1 calc R U . . .
N5 N 0.73382(7) 0.39204(8) 0.52592(9) 0.0250(4) Uani 1 1 d . . . . .
C5 C 0.54650(9) 0.61639(10) 0.50441(12) 0.0296(5) Uani 1 1 d . . . . .
N6 N 0.81020(8) 0.34405(8) 0.43513(9) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.49719(11) 0.65070(12) 0.47958(15) 0.0448(7) Uani 1 1 d . . . . .
H6A H 0.510697 0.687209 0.462363 0.067 Uiso 1 1 calc R U . . .
H6B H 0.470781 0.656957 0.517601 0.067 Uiso 1 1 calc R U . . .
H6C H 0.477878 0.630321 0.442578 0.067 Uiso 1 1 calc R U . . .
C7 C 0.58662(9) 0.63822(9) 0.54987(12) 0.0283(5) Uani 1 1 d . . . . .
C8 C 0.58392(11) 0.69778(10) 0.57562(15) 0.0411(6) Uani 1 1 d . . . . .
H8A H 0.581935 0.723821 0.536573 0.062 Uiso 1 1 calc R U . . .
H8B H 0.617814 0.706017 0.602784 0.062 Uiso 1 1 calc R U . . .
H8C H 0.550251 0.702487 0.604382 0.062 Uiso 1 1 calc R U . . .
C9 C 0.77501(9) 0.59268(9) 0.54465(11) 0.0234(5) Uani 1 1 d . . . . .
H9A H 0.745794 0.622567 0.547552 0.028 Uiso 1 1 calc R U . . .
H9B H 0.793654 0.589490 0.589984 0.028 Uiso 1 1 calc R U . . .
C10 C 0.81793(9) 0.60784(9) 0.49070(11) 0.0231(5) Uani 1 1 d . . . . .
C11 C 0.80550(9) 0.64186(9) 0.43404(11) 0.0248(5) Uani 1 1 d . . . . .
C19 C 0.82243(9) 0.39273(9) 0.46744(10) 0.0258(5) Uani 1 1 d . . . . .
C16 C 0.96390(12) 0.56472(15) 0.4577(2) 0.0720(11) Uani 1 1 d . . . . .
H16A H 0.969626 0.538490 0.419382 0.108 Uiso 1 1 calc R U . . .
H16B H 0.964397 0.543694 0.501040 0.108 Uiso 1 1 calc R U . . .
H16C H 0.994234 0.592953 0.457908 0.108 Uiso 1 1 calc R U . . .
C18 C 0.78359(9) 0.41715(9) 0.51299(10) 0.0222(5) Uani 1 1 d . . . . .
C17 C 0.79334(9) 0.47268(9) 0.54846(11) 0.0238(5) Uani 1 1 d . . . . .
H17A H 0.831969 0.486281 0.537930 0.029 Uiso 1 1 calc R U . . .
H17B H 0.790583 0.467198 0.598727 0.029 Uiso 1 1 calc R U . . .
C12 C 0.74795(10) 0.66637(10) 0.42067(12) 0.0339(6) Uani 1 1 d . . . . .
H12A H 0.746097 0.680291 0.373343 0.051 Uiso 1 1 calc R U . . .
H12B H 0.741048 0.697721 0.452482 0.051 Uiso 1 1 calc R U . . .
H12C H 0.719167 0.637094 0.427467 0.051 Uiso 1 1 calc R U . . .
C13 C 0.89649(10) 0.62988(10) 0.39480(12) 0.0313(5) Uani 1 1 d . . . . .
C14 C 0.94072(11) 0.64398(12) 0.34225(14) 0.0459(7) Uani 1 1 d . . . . .
H14A H 0.954977 0.609020 0.321524 0.069 Uiso 1 1 calc R U . . .
H14B H 0.971958 0.664185 0.364401 0.069 Uiso 1 1 calc R U . . .
H14C H 0.924090 0.667946 0.306517 0.069 Uiso 1 1 calc R U . . .
C15 C 0.90780(10) 0.59393(10) 0.44966(14) 0.0371(6) Uani 1 1 d . . . . .
C23 C 0.72155(10) 0.34381(9) 0.49323(11) 0.0272(5) Uani 1 1 d . . . . .
C24 C 0.66451(10) 0.31838(10) 0.50693(13) 0.0371(6) Uani 1 1 d . . . . .
H24A H 0.642151 0.318570 0.464573 0.056 Uiso 1 1 calc R U . . .
H24B H 0.644983 0.340589 0.542174 0.056 Uiso 1 1 calc R U . . .
H24C H 0.669137 0.279386 0.522988 0.056 Uiso 1 1 calc R U . . .
C20 C 0.87838(10) 0.41929(11) 0.45146(13) 0.0366(6) Uani 1 1 d . . . . .
H20A H 0.901829 0.392386 0.425904 0.055 Uiso 1 1 calc R U . . .
H20B H 0.897448 0.429545 0.494352 0.055 Uiso 1 1 calc R U . . .
H20C H 0.872464 0.453323 0.423676 0.055 Uiso 1 1 calc R U . . .
C21 C 0.76020(10) 0.31974(9) 0.44739(11) 0.0284(5) Uani 1 1 d . . . . .
C22 C 0.74699(12) 0.26618(10) 0.40909(12) 0.0416(6) Uani 1 1 d . . . . .
H22A H 0.712274 0.271326 0.382344 0.062 Uiso 1 1 calc R U . . .
H22B H 0.741745 0.235181 0.441866 0.062 Uiso 1 1 calc R U . . .
H22C H 0.778336 0.257097 0.378091 0.062 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 O1 1.4889(14) . ?
P1 C17 1.812(2) . ?
P1 C1 1.813(2) . ?
P1 C9 1.822(2) . ?
N1 C2 1.336(3) . ?
N1 C7 1.344(3) . ?
C1 C2 1.504(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C5 1.340(3) . ?
N2 C3 1.340(3) . ?
C2 C3 1.402(3) . ?
N3 C10 1.332(3) . ?
N3 C15 1.339(3) . ?
C3 C4 1.502(3) . ?
N4 C13 1.333(3) . ?
N4 C11 1.344(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C23 1.338(3) . ?
N5 C18 1.342(3) . ?
C5 C7 1.397(3) . ?
C5 C6 1.501(3) . ?
N6 C21 1.336(3) . ?
N6 C19 1.344(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.497(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.397(3) . ?
C11 C12 1.502(3) . ?
C19 C18 1.402(3) . ?
C19 C20 1.497(3) . ?
C16 C15 1.504(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C17 1.502(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.392(3) . ?
C13 C14 1.501(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C23 C21 1.399(3) . ?
C23 C24 1.501(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.503(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C17 113.75(9) . . ?
O1 P1 C1 112.98(9) . . ?
C17 P1 C1 106.97(10) . . ?
O1 P1 C9 111.88(9) . . ?
C17 P1 C9 104.40(10) . . ?
C1 P1 C9 106.21(10) . . ?
C2 N1 C7 117.94(18) . . ?
C2 C1 P1 110.76(14) . . ?
C2 C1 H1A 109.5 . . ?
P1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C5 N2 C3 118.45(19) . . ?
N1 C2 C3 121.35(19) . . ?
N1 C2 C1 116.72(18) . . ?
C3 C2 C1 121.91(18) . . ?
C10 N3 C15 118.4(2) . . ?
N2 C3 C2 120.4(2) . . ?
N2 C3 C4 117.24(19) . . ?
C2 C3 C4 122.32(19) . . ?
C13 N4 C11 118.55(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C23 N5 C18 118.54(19) . . ?
N2 C5 C7 120.8(2) . . ?
N2 C5 C6 117.0(2) . . ?
C7 C5 C6 122.2(2) . . ?
C21 N6 C19 118.38(19) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C5 121.0(2) . . ?
N1 C7 C8 116.9(2) . . ?
C5 C7 C8 122.1(2) . . ?
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 . . ?
C10 C9 P1 108.82(14) . . ?
C10 C9 H9A 109.9 . . ?
P1 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
P1 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N3 C10 C11 121.00(19) . . ?
N3 C10 C9 115.73(18) . . ?
C11 C10 C9 123.16(19) . . ?
N4 C11 C10 120.3(2) . . ?
N4 C11 C12 116.37(19) . . ?
C10 C11 C12 123.4(2) . . ?
N6 C19 C18 120.6(2) . . ?
N6 C19 C20 116.90(19) . . ?
C18 C19 C20 122.5(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C18 C19 120.74(19) . . ?
N5 C18 C17 115.79(18) . . ?
C19 C18 C17 123.4(2) . . ?
C18 C17 P1 111.62(14) . . ?
C18 C17 H17A 109.3 . . ?
P1 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
P1 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
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 . . ?
N4 C13 C15 120.9(2) . . ?
N4 C13 C14 117.4(2) . . ?
C15 C13 C14 121.7(2) . . ?
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 . . ?
N3 C15 C13 120.8(2) . . ?
N3 C15 C16 117.2(2) . . ?
C13 C15 C16 122.0(2) . . ?
N5 C23 C21 120.6(2) . . ?
N5 C23 C24 116.9(2) . . ?
C21 C23 C24 122.5(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 C23 121.1(2) . . ?
N6 C21 C22 117.2(2) . . ?
C23 C21 C22 121.6(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 P1 C1 C2 -43.84(17) . . . . ?
C17 P1 C1 C2 -169.76(14) . . . . ?
C9 P1 C1 C2 79.17(16) . . . . ?
C7 N1 C2 C3 1.1(3) . . . . ?
C7 N1 C2 C1 179.51(18) . . . . ?
P1 C1 C2 N1 -88.76(19) . . . . ?
P1 C1 C2 C3 89.6(2) . . . . ?
C5 N2 C3 C2 0.1(3) . . . . ?
C5 N2 C3 C4 179.0(2) . . . . ?
N1 C2 C3 N2 -1.3(3) . . . . ?
C1 C2 C3 N2 -179.62(19) . . . . ?
N1 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C3 N2 C5 C7 1.2(3) . . . . ?
C3 N2 C5 C6 -178.2(2) . . . . ?
C2 N1 C7 C5 0.2(3) . . . . ?
C2 N1 C7 C8 179.70(19) . . . . ?
N2 C5 C7 N1 -1.4(3) . . . . ?
C6 C5 C7 N1 178.0(2) . . . . ?
N2 C5 C7 C8 179.1(2) . . . . ?
C6 C5 C7 C8 -1.5(3) . . . . ?
O1 P1 C9 C10 -43.77(17) . . . . ?
C17 P1 C9 C10 79.67(16) . . . . ?
C1 P1 C9 C10 -167.47(14) . . . . ?
C15 N3 C10 C11 0.8(3) . . . . ?
C15 N3 C10 C9 177.1(2) . . . . ?
P1 C9 C10 N3 -83.1(2) . . . . ?
P1 C9 C10 C11 93.1(2) . . . . ?
C13 N4 C11 C10 2.3(3) . . . . ?
C13 N4 C11 C12 -176.34(19) . . . . ?
N3 C10 C11 N4 -3.1(3) . . . . ?
C9 C10 C11 N4 -179.17(19) . . . . ?
N3 C10 C11 C12 175.4(2) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C21 N6 C19 C18 0.2(3) . . . . ?
C21 N6 C19 C20 -178.9(2) . . . . ?
C23 N5 C18 C19 -1.4(3) . . . . ?
C23 N5 C18 C17 176.82(18) . . . . ?
N6 C19 C18 N5 0.9(3) . . . . ?
C20 C19 C18 N5 179.9(2) . . . . ?
N6 C19 C18 C17 -177.22(19) . . . . ?
C20 C19 C18 C17 1.8(3) . . . . ?
N5 C18 C17 P1 -62.6(2) . . . . ?
C19 C18 C17 P1 115.6(2) . . . . ?
O1 P1 C17 C18 -38.26(18) . . . . ?
C1 P1 C17 C18 87.21(16) . . . . ?
C9 P1 C17 C18 -160.48(15) . . . . ?
C11 N4 C13 C15 0.7(3) . . . . ?
C11 N4 C13 C14 -179.2(2) . . . . ?
C10 N3 C15 C13 2.2(4) . . . . ?
C10 N3 C15 C16 -177.8(3) . . . . ?
N4 C13 C15 N3 -3.1(4) . . . . ?
C14 C13 C15 N3 176.8(2) . . . . ?
N4 C13 C15 C16 177.0(3) . . . . ?
C14 C13 C15 C16 -3.2(4) . . . . ?
C18 N5 C23 C21 0.9(3) . . . . ?
C18 N5 C23 C24 -177.54(19) . . . . ?
C19 N6 C21 C23 -0.7(3) . . . . ?
C19 N6 C21 C22 178.4(2) . . . . ?
N5 C23 C21 N6 0.1(3) . . . . ?
C24 C23 C21 N6 178.5(2) . . . . ?
N5 C23 C21 C22 -178.9(2) . . . . ?
C24 C23 C21 C22 -0.5(3) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_ox070
_database_code_depnum_ccdc_archive 'CCDC 2072408'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'tris(pyrazin-2-ylmethyl)phosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N6 O P'
_chemical_formula_sum            'C15 H15 N6 O P'
_chemical_formula_weight         326.30

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      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                   18.8494(8)
_cell_length_b                   10.2782(4)
_cell_length_c                   7.9072(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.332(4)
_cell_angle_gamma                90
_cell_volume                     1531.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      3.8020
_cell_measurement_theta_max      30.0860

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            15037
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.407
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4277
_reflns_number_gt                3088
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ortep
_computing_publication_material  platon
_refine_special_details          custom
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.7155P] 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         4277
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.24279(2) 0.63949(4) 0.90397(6) 0.01780(12) Uani 1 1 d . . . . .
O1 O 0.22974(7) 0.77593(11) 0.85040(16) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.32152(9) 0.62138(16) 1.0387(2) 0.0193(3) Uani 1 1 d . . . . .
H1A H 0.312280 0.659755 1.150908 0.023 Uiso 1 1 calc R U . . .
H1B H 0.331429 0.527590 1.055278 0.023 Uiso 1 1 calc R U . . .
N2 N 0.38866(8) 0.81573(15) 0.9681(2) 0.0258(3) Uani 1 1 d . . . . .
C2 C 0.38550(9) 0.68534(17) 0.9665(2) 0.0198(4) Uani 1 1 d . . . . .
N3 N 0.32688(8) 0.34774(15) 0.8169(2) 0.0277(4) Uani 1 1 d . . . . .
C3 C 0.44047(10) 0.61237(18) 0.8998(3) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.436360 0.520248 0.900513 0.030 Uiso 1 1 calc R U . . .
C4 C 0.50050(10) 0.79465(19) 0.8351(3) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.540426 0.837459 0.789504 0.035 Uiso 1 1 calc R U . . .
N5 N 0.07533(8) 0.51195(14) 0.8282(2) 0.0251(3) Uani 1 1 d . . . . .
C5 C 0.44633(10) 0.86831(18) 0.8994(3) 0.0285(4) Uani 1 1 d . . . . .
H5 H 0.450033 0.960423 0.894941 0.034 Uiso 1 1 calc R U . . .
N6 N 0.49846(8) 0.66470(16) 0.8351(2) 0.0305(4) Uani 1 1 d . . . . .
C6 C 0.25528(10) 0.53307(16) 0.7229(2) 0.0213(4) Uani 1 1 d . . . . .
H6A H 0.214152 0.543692 0.643980 0.026 Uiso 1 1 calc R U . . .
H6B H 0.298046 0.562116 0.663145 0.026 Uiso 1 1 calc R U . . .
C7 C 0.26336(9) 0.39067(17) 0.7636(2) 0.0200(4) Uani 1 1 d . . . . .
N10 N -0.00202(9) 0.73568(16) 0.9077(2) 0.0317(4) Uani 1 1 d . . . . .
C10 C 0.33191(11) 0.22015(19) 0.8515(3) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.376405 0.186224 0.889223 0.036 Uiso 1 1 calc R U . . .
C11 C 0.06147(10) 0.71034(18) 0.9767(3) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.081315 0.771155 1.054939 0.032 Uiso 1 1 calc R U . . .
C12 C 0.10018(9) 0.59935(16) 0.9401(2) 0.0201(4) Uani 1 1 d . . . . .
C13 C 0.17104(9) 0.57356(17) 1.0248(2) 0.0204(4) Uani 1 1 d . . . . .
H13A H 0.177743 0.478548 1.038074 0.024 Uiso 1 1 calc R U . . .
H13B H 0.171983 0.613083 1.139012 0.024 Uiso 1 1 calc R U . . .
N15 N 0.21175(9) 0.17854(16) 0.7808(2) 0.0326(4) Uani 1 1 d . . . . .
C15 C 0.01135(10) 0.53718(18) 0.7591(3) 0.0278(4) Uani 1 1 d . . . . .
H15 H -0.008380 0.477195 0.679597 0.033 Uiso 1 1 calc R U . . .
C14 C -0.02708(10) 0.64660(19) 0.7985(3) 0.0280(4) Uani 1 1 d . . . . .
H14 H -0.072562 0.659109 0.746714 0.034 Uiso 1 1 calc R U . . .
C8 C 0.20641(10) 0.30497(18) 0.7465(3) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.161785 0.338224 0.708565 0.035 Uiso 1 1 calc R U . . .
C9 C 0.27524(10) 0.13670(18) 0.8345(2) 0.0256(4) Uani 1 1 d . . . . .
H9 H 0.281483 0.047322 0.861655 0.031 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 O1 1.4838(12) . ?
P1 C13 1.8059(18) . ?
P1 C1 1.8162(18) . ?
P1 C6 1.8212(18) . ?
C1 C2 1.498(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C5 1.340(2) . ?
N2 C2 1.342(2) . ?
C2 C3 1.393(2) . ?
N3 C7 1.335(2) . ?
N3 C10 1.343(2) . ?
C3 N6 1.331(2) . ?
C3 H3 0.9500 . ?
C4 N6 1.336(2) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
N5 C15 1.338(2) . ?
N5 C12 1.338(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.393(2) . ?
N10 C11 1.329(2) . ?
N10 C14 1.337(3) . ?
C10 C9 1.374(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.504(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N15 C8 1.331(2) . ?
N15 C9 1.332(3) . ?
C15 C14 1.377(3) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C13 112.61(8) . . ?
O1 P1 C1 113.09(8) . . ?
C13 P1 C1 105.24(8) . . ?
O1 P1 C6 111.52(8) . . ?
C13 P1 C6 107.61(8) . . ?
C1 P1 C6 106.31(8) . . ?
C2 C1 P1 112.67(12) . . ?
C2 C1 H1A 109.1 . . ?
P1 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
P1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C5 N2 C2 115.81(16) . . ?
N2 C2 C3 120.54(16) . . ?
N2 C2 C1 118.08(15) . . ?
C3 C2 C1 121.37(16) . . ?
C7 N3 C10 116.46(16) . . ?
N6 C3 C2 123.56(17) . . ?
N6 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N6 C4 C5 121.85(18) . . ?
N6 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C15 N5 C12 116.00(16) . . ?
N2 C5 C4 122.89(17) . . ?
N2 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 N6 C4 115.32(17) . . ?
C7 C6 P1 115.49(12) . . ?
C7 C6 H6A 108.4 . . ?
P1 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
P1 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N3 C7 C8 120.35(16) . . ?
N3 C7 C6 118.31(16) . . ?
C8 C7 C6 121.35(16) . . ?
C11 N10 C14 115.60(17) . . ?
N3 C10 C9 122.61(18) . . ?
N3 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N10 C11 C12 123.22(18) . . ?
N10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
N5 C12 C11 120.79(17) . . ?
N5 C12 C13 118.03(15) . . ?
C11 C12 C13 121.17(16) . . ?
C12 C13 P1 111.51(12) . . ?
C12 C13 H13A 109.3 . . ?
P1 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
P1 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C8 N15 C9 116.32(17) . . ?
N5 C15 C14 122.68(18) . . ?
N5 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
N10 C14 C15 121.68(18) . . ?
N10 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
N15 C8 C7 122.90(18) . . ?
N15 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N15 C9 C10 121.35(17) . . ?
N15 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?

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
O1 P1 C1 C2 -50.05(14) . . . . ?
C13 P1 C1 C2 -173.37(12) . . . . ?
C6 P1 C1 C2 72.65(14) . . . . ?
C5 N2 C2 C3 1.3(3) . . . . ?
C5 N2 C2 C1 -178.89(16) . . . . ?
P1 C1 C2 N2 72.63(18) . . . . ?
P1 C1 C2 C3 -107.52(17) . . . . ?
N2 C2 C3 N6 0.2(3) . . . . ?
C1 C2 C3 N6 -179.67(17) . . . . ?
C2 N2 C5 C4 -1.8(3) . . . . ?
N6 C4 C5 N2 0.9(3) . . . . ?
C2 C3 N6 C4 -1.1(3) . . . . ?
C5 C4 N6 C3 0.6(3) . . . . ?
O1 P1 C6 C7 -175.54(12) . . . . ?
C13 P1 C6 C7 -51.57(15) . . . . ?
C1 P1 C6 C7 60.78(15) . . . . ?
C10 N3 C7 C8 0.1(3) . . . . ?
C10 N3 C7 C6 -179.89(17) . . . . ?
P1 C6 C7 N3 -81.15(19) . . . . ?
P1 C6 C7 C8 98.88(19) . . . . ?
C7 N3 C10 C9 -0.3(3) . . . . ?
C14 N10 C11 C12 -0.1(3) . . . . ?
C15 N5 C12 C11 -1.5(3) . . . . ?
C15 N5 C12 C13 178.39(16) . . . . ?
N10 C11 C12 N5 1.4(3) . . . . ?
N10 C11 C12 C13 -178.50(17) . . . . ?
N5 C12 C13 P1 88.92(17) . . . . ?
C11 C12 C13 P1 -91.15(18) . . . . ?
O1 P1 C13 C12 48.04(15) . . . . ?
C1 P1 C13 C12 171.66(12) . . . . ?
C6 P1 C13 C12 -75.27(14) . . . . ?
C12 N5 C15 C14 0.5(3) . . . . ?
C11 N10 C14 C15 -1.0(3) . . . . ?
N5 C15 C14 N10 0.8(3) . . . . ?
C9 N15 C8 C7 0.4(3) . . . . ?
N3 C7 C8 N15 -0.2(3) . . . . ?
C6 C7 C8 N15 179.82(18) . . . . ?
C8 N15 C9 C10 -0.6(3) . . . . ?
N3 C10 C9 N15 0.6(3) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_ox321
_database_code_depnum_ccdc_archive 'CCDC 2072407'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'bis((4,6-dimethyl-1,3,5-triazin-2-yl)methyl)(phenyl)phosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N6 O P'
_chemical_formula_sum            'C18 H21 N6 O P'
_chemical_formula_weight         368.38

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      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                   13.1900(7)
_cell_length_b                   5.2949(3)
_cell_length_c                   25.7235(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.212(5)
_cell_angle_gamma                90
_cell_volume                     1782.31(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      2.7200
_cell_measurement_theta_max      30.0160

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            8537
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4408
_reflns_number_gt                3059
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ortep
_computing_publication_material  platon
_refine_special_details          custom
_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+0.1827P] 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         4408
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.86299(4) 0.89082(10) 0.70309(2) 0.01372(13) Uani 1 1 d . . . . .
N1 N 1.00566(13) 0.9961(3) 0.82083(6) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.95024(14) 0.8927(4) 0.65444(7) 0.0153(4) Uani 1 1 d . . . . .
O1 O 0.83373(10) 1.1513(3) 0.71601(5) 0.0187(3) Uani 1 1 d . . . . .
C2 C 1.02092(15) 0.7025(4) 0.64961(8) 0.0185(4) Uani 1 1 d . . . . .
H2 H 1.029142 0.569142 0.674492 0.022 Uiso 1 1 calc R U . . .
N2 N 1.18523(13) 0.9653(3) 0.84301(7) 0.0221(4) Uani 1 1 d . . . . .
N3 N 1.10000(13) 0.6875(3) 0.78009(7) 0.0192(4) Uani 1 1 d . . . . .
C3 C 1.07977(16) 0.7071(4) 0.60830(8) 0.0229(5) Uani 1 1 d . . . . .
H3 H 1.128727 0.578057 0.605247 0.027 Uiso 1 1 calc R U . . .
C4 C 1.06696(16) 0.8987(4) 0.57190(8) 0.0247(5) Uani 1 1 d . . . . .
H4 H 1.106585 0.900143 0.543501 0.030 Uiso 1 1 calc R U . . .
N4 N 0.65933(12) 0.9770(3) 0.61185(7) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.99681(17) 1.0891(4) 0.57637(8) 0.0237(5) Uani 1 1 d . . . . .
H5 H 0.988367 1.220648 0.551086 0.028 Uiso 1 1 calc R U . . .
N5 N 0.67395(13) 0.9425(3) 0.52098(7) 0.0230(4) Uani 1 1 d . . . . .
N6 N 0.76095(12) 0.6524(3) 0.58128(6) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.93871(15) 1.0882(4) 0.61781(8) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.891243 1.220251 0.621197 0.023 Uiso 1 1 calc R U . . .
C7 C 0.91571(14) 0.7034(4) 0.75894(7) 0.0153(4) Uani 1 1 d . . . . .
H7A H 0.864076 0.691702 0.783641 0.018 Uiso 1 1 calc R U . . .
H7B H 0.928081 0.530223 0.746676 0.018 Uiso 1 1 calc R U . . .
C8 C 1.01303(15) 0.8018(4) 0.78805(7) 0.0161(4) Uani 1 1 d . . . . .
C14 C 0.72253(14) 0.7798(4) 0.61926(8) 0.0154(4) Uani 1 1 d . . . . .
C10 C 1.28365(16) 0.6529(5) 0.80261(9) 0.0310(6) Uani 1 1 d . . . . .
H10A H 1.332926 0.689151 0.833485 0.046 Uiso 1 1 calc R U . . .
H10B H 1.309475 0.719349 0.771234 0.046 Uiso 1 1 calc R U . . .
H10C H 1.274035 0.469892 0.799099 0.046 Uiso 1 1 calc R U . . .
C9 C 1.18395(16) 0.7752(4) 0.80873(8) 0.0207(5) Uani 1 1 d . . . . .
C11 C 1.09460(16) 1.0714(4) 0.84698(8) 0.0198(5) Uani 1 1 d . . . . .
C13 C 0.75599(14) 0.6988(4) 0.67414(7) 0.0143(4) Uani 1 1 d . . . . .
H13A H 0.776635 0.518988 0.674523 0.017 Uiso 1 1 calc R U . . .
H13B H 0.698386 0.715770 0.695136 0.017 Uiso 1 1 calc R U . . .
C16 C 0.56174(16) 1.2593(4) 0.55104(9) 0.0252(5) Uani 1 1 d . . . . .
H16A H 0.563457 1.367049 0.582104 0.038 Uiso 1 1 calc R U . . .
H16B H 0.492990 1.188833 0.542358 0.038 Uiso 1 1 calc R U . . .
H16C H 0.579422 1.359734 0.521470 0.038 Uiso 1 1 calc R U . . .
C15 C 0.63688(15) 1.0494(4) 0.56196(8) 0.0204(5) Uani 1 1 d . . . . .
C12 C 1.09225(16) 1.2832(4) 0.88493(8) 0.0247(5) Uani 1 1 d . . . . .
H12A H 1.081583 1.215696 0.919295 0.037 Uiso 1 1 calc R U . . .
H12B H 1.036303 1.398652 0.872544 0.037 Uiso 1 1 calc R U . . .
H12C H 1.157304 1.374726 0.887905 0.037 Uiso 1 1 calc R U . . .
C18 C 0.77723(19) 0.6083(5) 0.48950(8) 0.0308(6) Uani 1 1 d . . . . .
H18A H 0.757368 0.429950 0.489635 0.046 Uiso 1 1 calc R U . . .
H18B H 0.851930 0.621499 0.494359 0.046 Uiso 1 1 calc R U . . .
H18C H 0.750065 0.684840 0.455939 0.046 Uiso 1 1 calc R U . . .
C17 C 0.73499(16) 0.7434(4) 0.53311(8) 0.0215(5) 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
P1 O1 1.4813(14) . ?
P1 C1 1.8032(19) . ?
P1 C7 1.812(2) . ?
P1 C13 1.821(2) . ?
N1 C11 1.338(3) . ?
N1 C8 1.341(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
N2 C11 1.336(3) . ?
N2 C9 1.337(3) . ?
N3 C9 1.334(3) . ?
N3 C8 1.335(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
N4 C14 1.335(3) . ?
N4 C15 1.337(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
N5 C17 1.339(3) . ?
N5 C15 1.342(3) . ?
N6 C17 1.334(3) . ?
N6 C14 1.338(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.496(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 C13 1.488(3) . ?
C10 C9 1.492(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.490(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C16 C15 1.492(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C18 C17 1.496(3) . ?
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
O1 P1 C1 110.95(9) . . ?
O1 P1 C7 114.64(9) . . ?
C1 P1 C7 109.78(9) . . ?
O1 P1 C13 113.66(9) . . ?
C1 P1 C13 104.40(9) . . ?
C7 P1 C13 102.66(9) . . ?
C11 N1 C8 114.62(18) . . ?
C2 C1 C6 119.67(18) . . ?
C2 C1 P1 123.53(16) . . ?
C6 C1 P1 116.60(15) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C11 N2 C9 115.44(18) . . ?
C9 N3 C8 115.29(18) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.45(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C14 N4 C15 114.88(18) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C17 N5 C15 114.61(18) . . ?
C17 N6 C14 114.80(18) . . ?
C5 C6 C1 119.82(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 P1 115.21(14) . . ?
C8 C7 H7A 108.5 . . ?
P1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
P1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N3 C8 N1 125.13(19) . . ?
N3 C8 C7 117.71(18) . . ?
N1 C8 C7 117.15(17) . . ?
N4 C14 N6 125.24(19) . . ?
N4 C14 C13 117.79(18) . . ?
N6 C14 C13 116.94(18) . . ?
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 . . ?
N3 C9 N2 124.54(19) . . ?
N3 C9 C10 118.2(2) . . ?
N2 C9 C10 117.3(2) . . ?
N2 C11 N1 124.9(2) . . ?
N2 C11 C12 117.32(19) . . ?
N1 C11 C12 117.70(19) . . ?
C14 C13 P1 110.45(13) . . ?
C14 C13 H13A 109.6 . . ?
P1 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
P1 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C15 N5 125.1(2) . . ?
N4 C15 C16 117.16(19) . . ?
N5 C15 C16 117.72(19) . . ?
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 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C17 N5 125.30(19) . . ?
N6 C17 C18 116.6(2) . . ?
N5 C17 C18 118.12(19) . . ?

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
O1 P1 C1 C2 153.18(17) . . . . ?
C7 P1 C1 C2 25.4(2) . . . . ?
C13 P1 C1 C2 -84.01(19) . . . . ?
O1 P1 C1 C6 -31.92(18) . . . . ?
C7 P1 C1 C6 -159.67(15) . . . . ?
C13 P1 C1 C6 90.89(17) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
P1 C1 C2 C3 174.63(16) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
P1 C1 C6 C5 -174.13(16) . . . . ?
O1 P1 C7 C8 -62.25(17) . . . . ?
C1 P1 C7 C8 63.42(17) . . . . ?
C13 P1 C7 C8 174.01(14) . . . . ?
C9 N3 C8 N1 1.7(3) . . . . ?
C9 N3 C8 C7 -177.10(17) . . . . ?
C11 N1 C8 N3 -0.8(3) . . . . ?
C11 N1 C8 C7 178.07(17) . . . . ?
P1 C7 C8 N3 -103.00(19) . . . . ?
P1 C7 C8 N1 78.1(2) . . . . ?
C15 N4 C14 N6 -1.7(3) . . . . ?
C15 N4 C14 C13 176.27(17) . . . . ?
C17 N6 C14 N4 2.8(3) . . . . ?
C17 N6 C14 C13 -175.15(17) . . . . ?
C8 N3 C9 N2 -0.8(3) . . . . ?
C8 N3 C9 C10 178.84(19) . . . . ?
C11 N2 C9 N3 -1.0(3) . . . . ?
C11 N2 C9 C10 179.4(2) . . . . ?
C9 N2 C11 N1 2.1(3) . . . . ?
C9 N2 C11 C12 179.69(18) . . . . ?
C8 N1 C11 N2 -1.3(3) . . . . ?
C8 N1 C11 C12 -178.86(18) . . . . ?
N4 C14 C13 P1 -82.85(19) . . . . ?
N6 C14 C13 P1 95.26(19) . . . . ?
O1 P1 C13 C14 73.06(15) . . . . ?
C1 P1 C13 C14 -47.97(16) . . . . ?
C7 P1 C13 C14 -162.54(14) . . . . ?
C14 N4 C15 N5 -1.1(3) . . . . ?
C14 N4 C15 C16 176.49(18) . . . . ?
C17 N5 C15 N4 2.4(3) . . . . ?
C17 N5 C15 C16 -175.23(18) . . . . ?
C14 N6 C17 N5 -1.3(3) . . . . ?
C14 N6 C17 C18 179.36(19) . . . . ?
C15 N5 C17 N6 -1.0(3) . . . . ?
C15 N5 C17 C18 178.26(19) . . . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_xv082
_database_code_depnum_ccdc_archive 'CCDC 2072432'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'phenylbis(pyrazin-2-ylmethyl)phosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N4 O P'
_chemical_formula_sum            'C16 H15 N4 O P'
_chemical_formula_weight         310.29

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      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                   12.2538(6)
_cell_length_b                   5.6173(3)
_cell_length_c                   20.9600(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.397(2)
_cell_angle_gamma                90
_cell_volume                     1433.76(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7091
_cell_measurement_theta_min      3.2114
_cell_measurement_theta_max      26.3476

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9327
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            21211
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.211
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2916
_reflns_number_gt                2438
_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 Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ortep
_computing_publication_material  platon
_refine_special_details          custom
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+1.1739P] 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         2916
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.19309(3) 0.38058(7) 0.45356(2) 0.01420(12) Uani 1 1 d . . . . .
N1 N 0.09421(11) 0.4222(3) 0.59769(7) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.15359(13) 0.3313(3) 0.36908(7) 0.0160(3) Uani 1 1 d . . . . .
N3 N 0.54036(11) 0.5267(3) 0.39754(7) 0.0208(3) Uani 1 1 d . . . . .
O1 O 0.20435(10) 0.6380(2) 0.46975(5) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.17723(14) 0.5107(3) 0.32674(8) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.212891 0.652036 0.342825 0.024 Uiso 1 1 calc R U . . .
N2 N 0.20188(12) 0.0370(3) 0.66278(7) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.14877(14) 0.4833(3) 0.26101(8) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.165550 0.605302 0.232273 0.027 Uiso 1 1 calc R U . . .
C15 C 0.58844(13) 0.3359(3) 0.37546(8) 0.0207(4) Uani 1 1 d . . . . .
H15 H 0.653072 0.356202 0.354875 0.025 Uiso 1 1 calc R U . . .
C4 C 0.09611(14) 0.2786(3) 0.23754(8) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.076102 0.260949 0.192685 0.027 Uiso 1 1 calc R U . . .
N4 N 0.45813(12) 0.0671(3) 0.41160(7) 0.0221(3) Uani 1 1 d . . . . .
C13 C 0.41131(13) 0.2562(3) 0.43581(7) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.07241(14) 0.0995(3) 0.27910(8) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.036025 -0.040637 0.262696 0.027 Uiso 1 1 calc R U . . .
C16 C 0.54731(14) 0.1097(3) 0.38154(9) 0.0232(4) Uani 1 1 d . . . . .
H16 H 0.583281 -0.020420 0.363871 0.028 Uiso 1 1 calc R U . . .
C6 C 0.10166(13) 0.1237(3) 0.34484(8) 0.0191(4) Uani 1 1 d . . . . .
H6 H 0.086343 -0.000840 0.373201 0.023 Uiso 1 1 calc R U . . .
C7 C 0.09333(13) 0.2195(3) 0.49499(7) 0.0159(3) Uani 1 1 d . . . . .
H7A H 0.019712 0.289947 0.483491 0.019 Uiso 1 1 calc R U . . .
H7B H 0.090585 0.051749 0.480396 0.019 Uiso 1 1 calc R U . . .
C12 C 0.31678(13) 0.2067(3) 0.47403(8) 0.0164(3) Uani 1 1 d . . . . .
H12A H 0.342214 0.233662 0.519966 0.020 Uiso 1 1 calc R U . . .
H12B H 0.297388 0.036083 0.468996 0.020 Uiso 1 1 calc R U . . .
C9 C 0.17225(13) 0.0336(3) 0.59945(8) 0.0192(4) Uani 1 1 d . . . . .
H9 H 0.187092 -0.104961 0.575908 0.023 Uiso 1 1 calc R U . . .
C8 C 0.12038(12) 0.2258(3) 0.56659(7) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.12273(14) 0.4241(3) 0.66128(8) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.104708 0.559130 0.685309 0.027 Uiso 1 1 calc R U . . .
C10 C 0.17756(14) 0.2359(3) 0.69310(8) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.198601 0.248557 0.737983 0.027 Uiso 1 1 calc R U . . .
C14 C 0.45125(14) 0.4856(3) 0.42763(8) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.414066 0.616913 0.443911 0.023 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 O1 1.4880(12) . ?
P1 C1 1.8043(16) . ?
P1 C12 1.8141(16) . ?
P1 C7 1.8177(16) . ?
N1 C8 1.338(2) . ?
N1 C11 1.340(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.397(2) . ?
N3 C15 1.331(2) . ?
N3 C14 1.340(2) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
N2 C10 1.335(2) . ?
N2 C9 1.337(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
N4 C13 1.334(2) . ?
N4 C16 1.342(2) . ?
C13 C14 1.396(2) . ?
C13 C12 1.506(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C16 H16 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.501(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 C8 1.395(2) . ?
C9 H9 0.9500 . ?
C11 C10 1.384(3) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 112.38(7) . . ?
O1 P1 C12 114.56(7) . . ?
C1 P1 C12 105.98(7) . . ?
O1 P1 C7 115.15(7) . . ?
C1 P1 C7 105.74(7) . . ?
C12 P1 C7 101.98(7) . . ?
C8 N1 C11 116.17(15) . . ?
C2 C1 C6 119.37(15) . . ?
C2 C1 P1 117.51(13) . . ?
C6 C1 P1 123.12(13) . . ?
C15 N3 C14 116.14(15) . . ?
C3 C2 C1 120.23(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C10 N2 C9 115.73(15) . . ?
C4 C3 C2 120.00(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N3 C15 C16 121.98(15) . . ?
N3 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C3 C4 C5 120.24(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C13 N4 C16 116.34(15) . . ?
N4 C13 C14 121.12(15) . . ?
N4 C13 C12 116.38(14) . . ?
C14 C13 C12 122.46(15) . . ?
C4 C5 C6 120.26(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N4 C16 C15 122.23(16) . . ?
N4 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C5 C6 C1 119.88(16) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 P1 112.37(11) . . ?
C8 C7 H7A 109.1 . . ?
P1 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
P1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C13 C12 P1 116.52(11) . . ?
C13 C12 H12A 108.2 . . ?
P1 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
P1 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
N2 C9 C8 122.53(16) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N1 C8 C9 121.21(15) . . ?
N1 C8 C7 117.93(14) . . ?
C9 C8 C7 120.86(14) . . ?
N1 C11 C10 122.16(16) . . ?
N1 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
N2 C10 C11 122.14(16) . . ?
N2 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
N3 C14 C13 122.12(15) . . ?
N3 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?

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
O1 P1 C1 C2 23.29(15) . . . . ?
C12 P1 C1 C2 -102.54(13) . . . . ?
C7 P1 C1 C2 149.70(13) . . . . ?
O1 P1 C1 C6 -157.05(13) . . . . ?
C12 P1 C1 C6 77.12(15) . . . . ?
C7 P1 C1 C6 -30.64(15) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
P1 C1 C2 C3 -179.97(13) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C14 N3 C15 C16 1.8(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C16 N4 C13 C14 2.5(2) . . . . ?
C16 N4 C13 C12 -175.31(15) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C13 N4 C16 C15 -0.4(3) . . . . ?
N3 C15 C16 N4 -1.9(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
P1 C1 C6 C5 179.23(13) . . . . ?
O1 P1 C7 C8 -60.09(13) . . . . ?
C1 P1 C7 C8 175.20(11) . . . . ?
C12 P1 C7 C8 64.58(13) . . . . ?
N4 C13 C12 P1 -130.80(14) . . . . ?
C14 C13 C12 P1 51.4(2) . . . . ?
O1 P1 C12 C13 -68.30(14) . . . . ?
C1 P1 C12 C13 56.19(14) . . . . ?
C7 P1 C12 C13 166.63(12) . . . . ?
C10 N2 C9 C8 0.7(2) . . . . ?
C11 N1 C8 C9 1.3(2) . . . . ?
C11 N1 C8 C7 -177.99(14) . . . . ?
N2 C9 C8 N1 -2.3(2) . . . . ?
N2 C9 C8 C7 177.03(15) . . . . ?
P1 C7 C8 N1 79.74(16) . . . . ?
P1 C7 C8 C9 -99.59(16) . . . . ?
C8 N1 C11 C10 0.9(2) . . . . ?
C9 N2 C10 C11 1.6(2) . . . . ?
N1 C11 C10 N2 -2.5(3) . . . . ?
C15 N3 C14 C13 0.4(2) . . . . ?
N4 C13 C14 N3 -2.7(2) . . . . ?
C12 C13 C14 N3 175.03(15) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_ox161
_database_code_depnum_ccdc_archive 'CCDC 2072409'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'bis((3,5,6-trimethylpyrazin-2-yl)methyl)(phenyl)phosphine oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N4 O P'
_chemical_formula_sum            'C22 H27 N4 O P'
_chemical_formula_weight         394.44

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      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                   14.1437(4)
_cell_length_b                   17.3752(7)
_cell_length_c                   8.7363(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.662(3)
_cell_angle_gamma                90
_cell_volume                     2127.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3728
_cell_measurement_theta_min      3.6720
_cell_measurement_theta_max      32.0740

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            21620
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.322
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5257
_reflns_number_gt                3892
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ortep
_computing_publication_material  platon
_refine_special_details          custom
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.5574P] 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         5257
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.18071(3) 0.31967(3) 0.53448(5) 0.02004(12) Uani 1 1 d . . . . .
C1 C 0.17464(11) 0.39496(10) 0.67377(17) 0.0204(3) Uani 1 1 d . . . . .
N1 N -0.12135(10) 0.20191(9) 0.57524(16) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.20878(8) 0.24503(7) 0.61106(13) 0.0254(3) Uani 1 1 d . . . . .
N2 N -0.06359(10) 0.35206(9) 0.53906(15) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.22552(12) 0.38246(10) 0.81939(18) 0.0241(4) Uani 1 1 d . . . . .
H2 H 0.255227 0.334105 0.843209 0.029 Uiso 1 1 calc R U . . .
N3 N 0.50232(10) 0.35591(10) 0.67297(17) 0.0332(4) Uani 1 1 d . . . . .
C3 C 0.23305(13) 0.44035(11) 0.92996(19) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.267560 0.431541 1.029343 0.035 Uiso 1 1 calc R U . . .
C13 C -0.04278(12) 0.21698(10) 0.50972(18) 0.0240(4) Uani 1 1 d . . . . .
C14 C 0.01306(13) 0.14899(11) 0.4659(2) 0.0311(4) Uani 1 1 d . . . . .
H14A H 0.014494 0.149205 0.354035 0.047 Uiso 1 1 calc R U . . .
H14B H -0.017183 0.101474 0.495389 0.047 Uiso 1 1 calc R U . . .
H14C H 0.078388 0.151826 0.519545 0.047 Uiso 1 1 calc R U . . .
C4 C 0.19016(13) 0.51088(11) 0.8950(2) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.195831 0.550734 0.970056 0.037 Uiso 1 1 calc R U . . .
N4 N 0.35970(10) 0.45593(9) 0.54826(15) 0.0252(3) Uani 1 1 d . . . . .
C11 C -0.17093(12) 0.26088(11) 0.62279(19) 0.0280(4) Uani 1 1 d . . . . .
C5 C 0.13901(13) 0.52350(11) 0.7508(2) 0.0299(4) Uani 1 1 d . . . . .
H5 H 0.109571 0.571998 0.727369 0.036 Uiso 1 1 calc R U . . .
C9 C -0.14040(12) 0.33647(11) 0.60899(18) 0.0276(4) Uani 1 1 d . . . . .
C7 C 0.06842(11) 0.31486(10) 0.40667(18) 0.0238(4) Uani 1 1 d . . . . .
H7A H 0.055730 0.365575 0.356470 0.029 Uiso 1 1 calc R U . . .
H7B H 0.074494 0.276636 0.324509 0.029 Uiso 1 1 calc R U . . .
C12 C -0.25983(14) 0.24100(13) 0.6920(2) 0.0411(5) Uani 1 1 d . . . . .
H12A H -0.270918 0.185373 0.684413 0.062 Uiso 1 1 calc R U . . .
H12B H -0.314486 0.268207 0.635920 0.062 Uiso 1 1 calc R U . . .
H12C H -0.251928 0.256484 0.800873 0.062 Uiso 1 1 calc R U . . .
C6 C 0.13050(12) 0.46578(10) 0.64028(19) 0.0255(4) Uani 1 1 d . . . . .
H6 H 0.094631 0.474491 0.541915 0.031 Uiso 1 1 calc R U . . .
C16 C 0.35634(11) 0.38091(10) 0.51249(18) 0.0235(4) Uani 1 1 d . . . . .
C10 C -0.18994(15) 0.40413(13) 0.6701(2) 0.0407(5) Uani 1 1 d . . . . .
H10A H -0.243611 0.419920 0.593825 0.061 Uiso 1 1 calc R U . . .
H10B H -0.144879 0.446960 0.689754 0.061 Uiso 1 1 calc R U . . .
H10C H -0.213644 0.389636 0.766474 0.061 Uiso 1 1 calc R U . . .
C8 C -0.01569(11) 0.29312(10) 0.48809(17) 0.0216(3) Uani 1 1 d . . . . .
C15 C 0.26667(11) 0.35512(10) 0.41317(18) 0.0241(4) Uani 1 1 d . . . . .
H15A H 0.282062 0.313790 0.342499 0.029 Uiso 1 1 calc R U . . .
H15B H 0.238735 0.398796 0.349805 0.029 Uiso 1 1 calc R U . . .
C21 C 0.43292(12) 0.48097(11) 0.6488(2) 0.0291(4) Uani 1 1 d . . . . .
C19 C 0.50348(12) 0.43000(12) 0.7132(2) 0.0320(4) Uani 1 1 d . . . . .
C17 C 0.42904(12) 0.33029(11) 0.5719(2) 0.0287(4) Uani 1 1 d . . . . .
C20 C 0.58588(14) 0.45645(15) 0.8284(2) 0.0456(6) Uani 1 1 d . . . . .
H20A H 0.630181 0.486615 0.775250 0.068 Uiso 1 1 calc R U . . .
H20B H 0.619145 0.411557 0.877547 0.068 Uiso 1 1 calc R U . . .
H20C H 0.561914 0.488390 0.907296 0.068 Uiso 1 1 calc R U . . .
C18 C 0.43092(15) 0.24685(12) 0.5276(3) 0.0427(5) Uani 1 1 d . . . . .
H18A H 0.431204 0.242523 0.415829 0.064 Uiso 1 1 calc R U . . .
H18B H 0.374323 0.220984 0.556491 0.064 Uiso 1 1 calc R U . . .
H18C H 0.488472 0.222597 0.581624 0.064 Uiso 1 1 calc R U . . .
C22 C 0.43295(15) 0.56482(12) 0.6892(2) 0.0403(5) Uani 1 1 d . . . . .
H22A H 0.385192 0.591739 0.616870 0.060 Uiso 1 1 calc R U . . .
H22B H 0.496177 0.586627 0.682558 0.060 Uiso 1 1 calc R U . . .
H22C H 0.417501 0.570919 0.794588 0.060 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 O1 1.4888(12) . ?
P1 C1 1.7964(17) . ?
P1 C7 1.8175(16) . ?
P1 C15 1.8232(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.393(2) . ?
N1 C11 1.339(2) . ?
N1 C13 1.342(2) . ?
N2 C8 1.337(2) . ?
N2 C9 1.343(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
N3 C19 1.334(3) . ?
N3 C17 1.345(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C13 C8 1.397(2) . ?
C13 C14 1.499(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
N4 C21 1.338(2) . ?
N4 C16 1.340(2) . ?
C11 C9 1.393(3) . ?
C11 C12 1.506(3) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C9 C10 1.502(3) . ?
C7 C8 1.513(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C6 H6 0.9500 . ?
C16 C17 1.399(2) . ?
C16 C15 1.506(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 C19 1.396(3) . ?
C21 C22 1.499(3) . ?
C19 C20 1.506(2) . ?
C17 C18 1.502(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 111.34(7) . . ?
O1 P1 C7 113.25(8) . . ?
C1 P1 C7 109.45(8) . . ?
O1 P1 C15 113.38(8) . . ?
C1 P1 C15 104.10(8) . . ?
C7 P1 C15 104.73(7) . . ?
C2 C1 C6 119.48(15) . . ?
C2 C1 P1 116.09(13) . . ?
C6 C1 P1 124.16(12) . . ?
C11 N1 C13 118.75(16) . . ?
C8 N2 C9 118.27(16) . . ?
C3 C2 C1 120.32(16) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C19 N3 C17 118.29(16) . . ?
C4 C3 C2 119.81(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N1 C13 C8 120.00(16) . . ?
N1 C13 C14 116.73(16) . . ?
C8 C13 C14 123.26(15) . . ?
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 . . ?
C3 C4 C5 120.15(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C21 N4 C16 118.01(16) . . ?
N1 C11 C9 120.90(16) . . ?
N1 C11 C12 116.68(18) . . ?
C9 C11 C12 122.41(17) . . ?
C4 C5 C6 120.37(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N2 C9 C11 120.57(16) . . ?
N2 C9 C10 116.58(17) . . ?
C11 C9 C10 122.85(17) . . ?
C8 C7 P1 113.58(11) . . ?
C8 C7 H7A 108.8 . . ?
P1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
P1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
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 . . ?
C5 C6 C1 119.87(15) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N4 C16 C17 121.58(15) . . ?
N4 C16 C15 115.13(15) . . ?
C17 C16 C15 123.18(16) . . ?
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 . . ?
N2 C8 C13 121.34(15) . . ?
N2 C8 C7 115.50(15) . . ?
C13 C8 C7 123.16(15) . . ?
C16 C15 P1 109.95(11) . . ?
C16 C15 H15A 109.7 . . ?
P1 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
P1 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N4 C21 C19 120.51(17) . . ?
N4 C21 C22 116.52(17) . . ?
C19 C21 C22 122.96(16) . . ?
N3 C19 C21 121.54(16) . . ?
N3 C19 C20 116.86(18) . . ?
C21 C19 C20 121.59(19) . . ?
N3 C17 C16 119.96(17) . . ?
N3 C17 C18 116.76(17) . . ?
C16 C17 C18 123.29(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 P1 C1 C2 21.05(15) . . . . ?
C7 P1 C1 C2 147.02(13) . . . . ?
C15 P1 C1 C2 -101.46(14) . . . . ?
O1 P1 C1 C6 -165.06(13) . . . . ?
C7 P1 C1 C6 -39.08(16) . . . . ?
C15 P1 C1 C6 72.43(15) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
P1 C1 C2 C3 173.56(13) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C11 N1 C13 C8 -1.9(2) . . . . ?
C11 N1 C13 C14 176.93(15) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C13 N1 C11 C9 -1.9(2) . . . . ?
C13 N1 C11 C12 178.57(15) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C8 N2 C9 C11 -2.2(2) . . . . ?
C8 N2 C9 C10 177.69(15) . . . . ?
N1 C11 C9 N2 4.1(2) . . . . ?
C12 C11 C9 N2 -176.41(16) . . . . ?
N1 C11 C9 C10 -175.86(16) . . . . ?
C12 C11 C9 C10 3.7(3) . . . . ?
O1 P1 C7 C8 61.06(15) . . . . ?
C1 P1 C7 C8 -63.81(14) . . . . ?
C15 P1 C7 C8 -174.91(13) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
P1 C1 C6 C5 -172.51(13) . . . . ?
C21 N4 C16 C17 -3.0(2) . . . . ?
C21 N4 C16 C15 173.35(14) . . . . ?
C9 N2 C8 C13 -1.5(2) . . . . ?
C9 N2 C8 C7 178.41(13) . . . . ?
N1 C13 C8 N2 3.7(2) . . . . ?
C14 C13 C8 N2 -175.03(15) . . . . ?
N1 C13 C8 C7 -176.24(14) . . . . ?
C14 C13 C8 C7 5.0(2) . . . . ?
P1 C7 C8 N2 91.94(15) . . . . ?
P1 C7 C8 C13 -88.11(17) . . . . ?
N4 C16 C15 P1 -93.63(15) . . . . ?
C17 C16 C15 P1 82.65(17) . . . . ?
O1 P1 C15 C16 -70.44(14) . . . . ?
C1 P1 C15 C16 50.71(14) . . . . ?
C7 P1 C15 C16 165.61(12) . . . . ?
C16 N4 C21 C19 0.2(2) . . . . ?
C16 N4 C21 C22 -178.44(15) . . . . ?
C17 N3 C19 C21 -2.4(3) . . . . ?
C17 N3 C19 C20 179.15(16) . . . . ?
N4 C21 C19 N3 2.5(3) . . . . ?
C22 C21 C19 N3 -178.89(16) . . . . ?
N4 C21 C19 C20 -179.08(16) . . . . ?
C22 C21 C19 C20 -0.5(3) . . . . ?
C19 N3 C17 C16 -0.4(2) . . . . ?
C19 N3 C17 C18 179.14(17) . . . . ?
N4 C16 C17 N3 3.1(3) . . . . ?
C15 C16 C17 N3 -172.91(15) . . . . ?
N4 C16 C17 C18 -176.32(17) . . . . ?
C15 C16 C17 C18 7.6(3) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.052

