# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Compound_13
_database_code_depnum_ccdc_archive 'CCDC 2258974'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
velabo.mdluli@merck.com
mohammad.chaudhry1@merck.com
justin.newman@merck.com
_chemical_name_common            Compound_13
_chemical_name_systematic        Compound_13
_chemical_formula_moiety         'C21 H20 N3 P'
_chemical_formula_sum            'C21 H20 N3 P'
_chemical_formula_weight         345.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P1 C10 N3 H10'
_chemical_oxdiff_usercomment     SWMS-339-47
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.7059(3)
_cell_length_b                   10.7086(2)
_cell_length_c                   12.8648(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.7679(18)
_cell_angle_gamma                90
_cell_volume                     1748.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17240
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.5140
_cell_measurement_theta_min      4.7420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -1 0.1219
-1 -2 1 0.0614
0 -1 -2 0.0745
-1 -2 -1 0.0791
1 -1 -2 0.0646
-1 1 2 0.0152
-2 -1 0 0.0756
0 -1 1 0.0597
1 0 1 0.0405
-1 0 -1 0.1020
1 1 -1 0.1139
2 -1 -1 0.0716
-2 1 1 0.0114

_exptl_crystal_recrystallization_method 
'grown via slow evaporation from a solution of mds029 in methanol, water, and acetonitrile'
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0028 1.9995 -0.9996 -0.0224 -0.0456 -0.3288
-1.0028 -1.9995 0.9996 0.0224 0.0456 0.3288
-0.0032 -0.9990 -2.0003 0.2011 -0.1862 0.0548
-1.0044 -1.9988 -1.0003 0.1435 -0.1510 0.2645
0.9972 -0.9992 -2.0010 0.2780 -0.1126 -0.0036
-0.9972 0.9992 2.0010 -0.2780 0.1126 0.0036
-2.0024 -0.9993 0.0008 -0.0739 -0.1367 0.2359
-0.0008 -1.0000 0.9994 0.0194 0.1088 0.1513
1.0012 -0.0005 0.9993 0.0164 0.1719 -0.0262
-1.0012 0.0005 -0.9993 -0.0164 -0.1719 0.0262
1.0012 0.9998 -1.0001 0.0575 -0.0352 -0.2097
1.9984 -0.9998 -1.0017 0.2943 0.0593 -0.0297
-1.9984 0.9998 1.0017 -0.2943 -0.0593 0.0297

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.215
_diffrn_reflns_theta_min         4.778
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -41.00   0.50    0.57    --  -50.08 -45.00 112.00  162
  2  ω    -53.00  22.00   0.50    0.57    --  -50.08  45.00 -97.00  150
  3  ω     41.00 122.00   0.50    0.57    --   50.08  45.00 -97.00  162
  4  ω    -21.00  51.00   0.50    0.57    --   50.08 -45.00 112.00  144
  5  ω    -53.00 -18.00   0.50    2.28    --  -90.00  45.00 -97.00   70
  6  ω   -161.00 -81.00   0.50    2.28    --  -90.00 -45.00 112.00  160
  7  ω     98.00 178.00   0.50    2.28    --  107.23  45.00 -97.00  160
  8  ω   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00   0.00  158
  9  ω   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00 -30.00  158
 10  ω    -46.00  21.00   0.50    0.57    --  -50.08  38.00 120.00  134
 11  ω   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00 -90.00  158
 12  ω     43.00 122.00   0.50    0.57    --   50.08  38.00 -30.00  158
 13  ω     43.00 122.00   0.50    0.57    --   50.08  38.00  90.00  158
 14  ω     34.00  96.00   0.50    0.57    --   50.08-125.00 -60.00  124
 15  ω     43.00 122.00   0.50    0.57    --   50.08  38.00  60.00  158
 16  ω   -161.00 -81.00   0.50    2.28    --  -90.00 -41.00 -29.51  160
 17  ω   -161.00 -85.00   0.50    2.28    --  -90.00 -42.00 -66.76  152
 18  ω   -161.00-111.00   0.50    2.28    --  -90.00 -57.00-150.00  100
 19  ω   -161.00 -82.00   0.50    2.28    --  -90.00 -38.00   0.00  158
 20  ω   -156.00 -82.00   0.50    2.28    --  -90.00 -38.00 -30.00  148
 21  ω   -108.00 -82.00   0.50    2.28    --  -90.00 -35.00 -29.62   52
 22  ω   -121.00 -83.00   0.50    2.28    --  -90.00 -35.00 -59.42   76
 23  ω    -66.00 -18.00   0.50    2.28    --  -90.00  57.00-150.00   96
 24  ω   -136.00 -84.00   0.50    2.28    --  -90.00 -41.00  25.40  104
 25  ω   -139.00-113.00   0.50    2.28    --  -90.00 -36.00  62.00   52
 26  ω    -44.00 -19.00   0.50    2.28    --  -90.00  38.00 -60.00   50
 27  ω    -45.00 -19.00   0.50    2.28    --  -90.00  38.00  90.00   52
 28  ω    -46.00 -21.00   0.50    2.28    --  -90.00  57.00   0.00   50
 29  ω   -120.00 -82.00   0.50    2.28    --  -90.00 -41.00 -59.72   76
 30  ω   -112.00 -85.00   0.50    2.28    --  -90.00 -37.00   4.47   54
 31  ω   -159.00 -95.00   0.50    2.28    --  -90.00 -44.00  54.74  128
 32  ω   -155.00-121.00   0.50    2.28    --  -90.00 -57.00-120.00   68
 33  ω   -156.00-130.00   0.50    2.28    --  -90.00 -33.00 -53.18   52
 34  ω   -112.00 -86.00   0.50    2.28    --  -90.00 -33.00 -53.18   52
 35  ω   -143.00-102.00   0.50    2.28    --  -90.00-125.00  30.00   82
 36  ω    -45.00 -18.00   0.50    2.28    --  -90.00  38.00 120.00   54
 37  ω   -110.00 -82.00   0.50    2.28    --  -90.00 -32.00 -22.03   56
 38  ω    -45.00 -20.00   0.50    2.28    --  -90.00  38.00   0.00   50
 39  ω   -160.00-121.00   0.50    2.28    --  -90.00 -77.00-120.00   78
 40  ω     42.00  98.00   0.50    2.28    --  107.23 -77.00 -60.00  112
 41  ω     75.00 100.00   0.50    2.28    --  107.23-125.00 -30.00   50
 42  ω     37.00  64.00   0.50    2.28    --  107.23 -57.00-150.00   54
 43  ω     36.00  62.00   0.50    2.28    --  107.23-125.00 -30.00   52
 44  ω    118.00 178.00   0.50    2.28    --  107.23  77.00 120.00  120
 45  ω     36.00  62.00   0.50    2.28    --  107.23 -57.00 150.00   52
 46  ω     35.00  64.00   0.50    2.28    --  107.23 -57.00   0.00   58
 47  ω     35.00  95.00   0.50    2.28    --  107.23 -77.00 120.00  120
 48  ω     37.00  63.00   0.50    2.28    --  107.23 -57.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0768370000
_diffrn_orient_matrix_UB_12      -0.0800596000
_diffrn_orient_matrix_UB_13      -0.0606496000
_diffrn_orient_matrix_UB_21      0.0736178000
_diffrn_orient_matrix_UB_22      -0.0106189000
_diffrn_orient_matrix_UB_23      0.0982708000
_diffrn_orient_matrix_UB_31      -0.0583330000
_diffrn_orient_matrix_UB_32      -0.1191123000
_diffrn_orient_matrix_UB_33      0.0321997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3197
_reflns_number_total             3506
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+1.0371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C6(H6), C17(H17), C8(H8), C15(H15), C12(H12), C2(H2),
 C5(H5), C10(H10), C11(H11), C9(H9), C4(H4), C3(H3)
1.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.38963(3) 0.83806(4) 0.22475(3) 0.02454(13) Uani 1 1 d . . . . .
N3 N 0.54835(12) 0.32610(13) 0.13038(11) 0.0325(3) Uani 1 1 d . . . . .
N1 N 0.46425(11) 0.94828(14) 0.18919(13) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.65754(12) 0.94933(16) 0.18155(15) 0.0442(4) Uani 1 1 d . . . . .
C1 C 0.36526(12) 0.85043(15) 0.36160(12) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.26586(12) 0.85792(15) 0.15265(12) 0.0256(3) Uani 1 1 d . . . . .
C14 C 0.37581(12) 0.60131(16) 0.13506(12) 0.0278(3) Uani 1 1 d . . . . .
H14 H 0.308568 0.626480 0.107064 0.033 Uiso 1 1 calc R U . . .
C18 C 0.53437(13) 0.64469(16) 0.23744(12) 0.0270(3) Uani 1 1 d . . . . .
H18 H 0.575969 0.699251 0.280722 0.032 Uiso 1 1 calc R U . . .
C13 C 0.43437(12) 0.68399(15) 0.19930(12) 0.0249(3) Uani 1 1 d . . . . .
C21 C 0.56644(13) 0.94419(16) 0.18632(13) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.32511(13) 0.75009(16) 0.41670(12) 0.0301(4) Uani 1 1 d . . . . .
H6 H 0.314477 0.671595 0.383433 0.036 Uiso 1 1 calc R U . . .
C16 C 0.51287(13) 0.44352(15) 0.15100(12) 0.0268(3) Uani 1 1 d . . . . .
C17 C 0.57360(13) 0.52840(16) 0.21340(12) 0.0278(3) Uani 1 1 d . . . . .
H17 H 0.642173 0.505094 0.239056 0.033 Uiso 1 1 calc R U . . .
C8 C 0.26448(14) 0.91981(16) 0.05717(12) 0.0296(3) Uani 1 1 d . . . . .
H8 H 0.326603 0.958517 0.034467 0.036 Uiso 1 1 calc R U . . .
C15 C 0.41314(13) 0.48440(16) 0.11138(12) 0.0287(3) Uani 1 1 d . . . . .
H15 H 0.371195 0.430538 0.067776 0.034 Uiso 1 1 calc R U . . .
C12 C 0.17380(13) 0.80393(18) 0.18674(13) 0.0317(4) Uani 1 1 d . . . . .
H12 H 0.174300 0.762989 0.252270 0.038 Uiso 1 1 calc R U . . .
C19 C 0.48650(14) 0.24285(16) 0.06193(13) 0.0333(4) Uani 1 1 d . . . . .
H19A H 0.421000 0.220643 0.094660 0.050 Uiso 1 1 calc R U . . .
H19B H 0.527103 0.166940 0.049518 0.050 Uiso 1 1 calc R U . . .
H19C H 0.469784 0.284958 -0.004465 0.050 Uiso 1 1 calc R U . . .
C2 C 0.38236(13) 0.96479(17) 0.41142(14) 0.0334(4) Uani 1 1 d . . . . .
H2 H 0.409770 1.033201 0.374265 0.040 Uiso 1 1 calc R U . . .
C5 C 0.30066(14) 0.76501(19) 0.52038(13) 0.0360(4) Uani 1 1 d . . . . .
H5 H 0.272125 0.697270 0.557498 0.043 Uiso 1 1 calc R U . . .
C10 C 0.08125(14) 0.86921(17) 0.02898(14) 0.0350(4) Uani 1 1 d . . . . .
H10 H 0.018383 0.871745 -0.014046 0.042 Uiso 1 1 calc R U . . .
C11 C 0.08127(13) 0.81009(18) 0.12467(14) 0.0341(4) Uani 1 1 d . . . . .
H11 H 0.018299 0.773871 0.147852 0.041 Uiso 1 1 calc R U . . .
C9 C 0.17175(15) 0.92454(17) -0.00455(14) 0.0359(4) Uani 1 1 d . . . . .
H9 H 0.170605 0.965905 -0.069922 0.043 Uiso 1 1 calc R U . . .
C4 C 0.31815(15) 0.8792(2) 0.56925(14) 0.0401(4) Uani 1 1 d . . . . .
H4 H 0.301833 0.889378 0.640041 0.048 Uiso 1 1 calc R U . . .
C3 C 0.35942(15) 0.9789(2) 0.51516(15) 0.0403(4) Uani 1 1 d . . . . .
H3 H 0.371909 1.056627 0.549181 0.048 Uiso 1 1 calc R U . . .
C20 C 0.65605(15) 0.28964(19) 0.16228(15) 0.0402(4) Uani 1 1 d . . . . .
H20A H 0.705996 0.339729 0.124211 0.060 Uiso 1 1 calc R U . . .
H20B H 0.666295 0.200975 0.146824 0.060 Uiso 1 1 calc R U . . .
H20C H 0.668022 0.303770 0.237183 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 N1 1.5947(15) . ?
P1 C1 1.8072(16) . ?
P1 C7 1.7994(16) . ?
P1 C13 1.7805(17) . ?
N3 C16 1.366(2) . ?
N3 C19 1.456(2) . ?
N3 C20 1.463(2) . ?
N1 C21 1.301(2) . ?
N2 C21 1.163(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.394(2) . ?
C7 C8 1.395(2) . ?
C7 C12 1.394(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.400(2) . ?
C14 C15 1.378(2) . ?
C18 H18 0.9500 . ?
C18 C13 1.404(2) . ?
C18 C17 1.382(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.393(2) . ?
C16 C17 1.416(2) . ?
C16 C15 1.412(2) . ?
C17 H17 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C15 H15 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.391(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C10 C9 1.381(3) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
N1 P1 C1 110.94(8) . . ?
N1 P1 C7 106.35(8) . . ?
N1 P1 C13 115.70(8) . . ?
C7 P1 C1 107.87(7) . . ?
C13 P1 C1 108.56(7) . . ?
C13 P1 C7 107.07(7) . . ?
C16 N3 C19 120.49(14) . . ?
C16 N3 C20 120.28(15) . . ?
C19 N3 C20 118.46(14) . . ?
C21 N1 P1 126.22(13) . . ?
C6 C1 P1 121.45(12) . . ?
C2 C1 P1 118.81(13) . . ?
C2 C1 C6 119.66(15) . . ?
C8 C7 P1 118.92(12) . . ?
C12 C7 P1 120.96(12) . . ?
C12 C7 C8 119.92(15) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C15 C14 C13 121.74(15) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C13 121.47(15) . . ?
C14 C13 P1 121.95(12) . . ?
C14 C13 C18 117.56(15) . . ?
C18 C13 P1 120.33(12) . . ?
N2 C21 N1 175.15(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.08(16) . . ?
C5 C6 H6 120.0 . . ?
N3 C16 C17 121.66(15) . . ?
N3 C16 C15 120.93(15) . . ?
C15 C16 C17 117.41(15) . . ?
C18 C17 C16 120.83(15) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.65(16) . . ?
C9 C8 H8 120.2 . . ?
C14 C15 C16 120.95(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.91(16) . . ?
C11 C12 H12 120.0 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.16(18) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.76(18) . . ?
C4 C5 H5 120.1 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.64(16) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.74(17) . . ?
C10 C11 H11 120.1 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.11(16) . . ?
C10 C9 H9 119.9 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.38(17) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 119.95(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C6 C5 -175.78(13) . . . . ?
P1 C1 C2 C3 176.82(13) . . . . ?
P1 C7 C8 C9 173.28(13) . . . . ?
P1 C7 C12 C11 -173.66(13) . . . . ?
N3 C16 C17 C18 -176.94(15) . . . . ?
N3 C16 C15 C14 177.78(15) . . . . ?
N1 P1 C1 C6 -163.75(13) . . . . ?
N1 P1 C1 C2 19.36(15) . . . . ?
N1 P1 C7 C8 25.52(15) . . . . ?
N1 P1 C7 C12 -159.68(14) . . . . ?
N1 P1 C13 C14 -119.41(14) . . . . ?
N1 P1 C13 C18 55.79(15) . . . . ?
C1 P1 N1 C21 92.82(17) . . . . ?
C1 P1 C7 C8 144.60(13) . . . . ?
C1 P1 C7 C12 -40.60(16) . . . . ?
C1 P1 C13 C14 115.14(13) . . . . ?
C1 P1 C13 C18 -69.66(14) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C7 P1 N1 C21 -150.13(16) . . . . ?
C7 P1 C1 C6 80.13(14) . . . . ?
C7 P1 C1 C2 -96.76(14) . . . . ?
C7 P1 C13 C14 -1.08(15) . . . . ?
C7 P1 C13 C18 174.13(12) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C7 C12 C11 C10 0.4(3) . . . . ?
C13 P1 N1 C21 -31.40(19) . . . . ?
C13 P1 C1 C6 -35.57(15) . . . . ?
C13 P1 C1 C2 147.55(13) . . . . ?
C13 P1 C7 C8 -98.73(14) . . . . ?
C13 P1 C7 C12 76.07(15) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C13 C18 C17 C16 -1.4(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C17 C18 C13 P1 -175.92(12) . . . . ?
C17 C18 C13 C14 -0.5(2) . . . . ?
C17 C16 C15 C14 -1.6(2) . . . . ?
C8 C7 C12 C11 1.1(3) . . . . ?
C15 C14 C13 P1 176.69(12) . . . . ?
C15 C14 C13 C18 1.4(2) . . . . ?
C15 C16 C17 C18 2.4(2) . . . . ?
C12 C7 C8 C9 -1.6(2) . . . . ?
C19 N3 C16 C17 -177.05(15) . . . . ?
C19 N3 C16 C15 3.6(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C11 C10 C9 C8 0.9(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C20 N3 C16 C17 -7.3(2) . . . . ?
C20 N3 C16 C15 173.35(15) . . . . ?

_olex2_date_sample_data_collection 2023-02-08
_olex2_date_sample_submission    2023-02-08
_olex2_exptl_crystal_mounting_method 
'mounted onto a MiTiGen loop using paratone oil.'
_olex2_submission_original_sample_id mds029
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.552
####################################################################### 
# 
# 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_Compound_26
_database_code_depnum_ccdc_archive 'CCDC 2258976'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mohammad.chaudhry1@merck.com
velabo.mdluli@merck.com
_chemical_name_common            Compound_26
_chemical_name_systematic        Compound_26
_chemical_formula_moiety         'C14 H12 N2 P, H2 O'
_chemical_formula_sum            'C14 H14 N2 O P'
_chemical_formula_weight         257.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P2 N6 C30 H30'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.4855(4)
_cell_length_b                   24.4855(4)
_cell_length_c                   11.1476(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5788.0(2)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6680
_cell_measurement_theta_min      3.6030
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2430
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 1 0.0677
1 -2 -1 0.0370
2 0 1 0.1102
-1 1 1 0.0537
-2 1 0 0.0156
0 0 -1 0.0277
1 2 0 0.0820
-2 2 -1 0.0088
2 -1 -1 0.0403
1 -2 2 0.0849
0 -1 1 0.0703
-1 -2 2 0.0555
-1 -1 1 0.0419

_exptl_crystal_recrystallization_method 
'Grown from slow evaporation of a solution of mds008 in acetonitrile, water, and methanol.'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 2.0000 1.0000 -0.1520 0.0505 0.1205
1.0000 -2.0000 -1.0000 0.1761 -0.0201 -0.0590
2.0000 -0.0000 1.0000 -0.0443 -0.0121 0.1952
-1.0000 1.0000 1.0000 -0.1463 -0.0416 0.0349
-2.0000 1.0000 0.0000 -0.0780 0.0009 -0.0988
0.0000 0.0000 -1.0000 0.0924 0.0729 -0.0723
1.0000 2.0000 -0.0000 -0.0355 0.1538 0.1097
-2.0000 2.0000 -1.0000 -0.0154 0.1355 -0.1470
2.0000 -1.0000 -1.0000 0.1704 0.0720 0.0265
1.0000 -2.0000 2.0000 -0.1012 -0.2388 0.1579
-0.0000 -1.0000 1.0000 -0.0626 -0.1346 0.0482
-1.0000 -2.0000 2.0000 -0.1493 -0.2996 0.0350
-1.0000 -1.0000 1.0000 -0.0867 -0.1650 -0.0132

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.664
_diffrn_reflns_theta_min         3.610
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  31.00   0.50    0.07    --   50.08 -19.00  90.00  106
  2  ω     43.00 122.00   0.50    0.07    --   50.08  38.00  30.00  158
  3  ω    106.00 176.00   0.50    0.29    --  105.02  98.00 -10.00  140
  4  ω     98.00 176.00   0.50    0.29    --  105.02 125.00-180.00  156
  5  ω    -33.00  23.00   0.50    0.07    --  -50.08  19.00 -60.00  112
  6  ω    -46.00 -18.00   0.50    0.29    --  -90.00  38.00 -30.00   56
  7  ω    -61.00 -18.00   0.50    0.29    --  -90.00  53.00 -26.00   86
  8  ω    -51.00 -18.00   0.50    0.29    --  -90.00  43.00 -52.00   66
  9  ω    -46.00 -18.00   0.50    0.29    --  -90.00  38.00 -90.00   56
 10  ω    -46.00 -18.00   0.50    0.29    --  -90.00  38.00-180.00   56
 11  ω    -46.00 -18.00   0.50    0.29    --  -90.00  38.00 -60.00   56
 12  ω    -33.00  23.00   0.50    0.07    --  -50.08  19.00  90.00  112
 13  ω   -161.00 -81.00   0.50    0.29    --  -90.00 -43.00 155.00  160
 14  ω   -161.00-110.00   0.50    0.29    --  -90.00 -99.00 -60.00  102
 15  ω   -161.00-111.00   0.50    0.29    --  -90.00 -57.00 -60.00  100
 16  ω   -122.00 -74.00   0.50    0.07    --  -50.08 -74.00-140.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0240872000
_diffrn_orient_matrix_UB_12      -0.0298089000
_diffrn_orient_matrix_UB_13      -0.0924301000
_diffrn_orient_matrix_UB_21      0.0303944000
_diffrn_orient_matrix_UB_22      0.0617047000
_diffrn_orient_matrix_UB_23      -0.0729140000
_diffrn_orient_matrix_UB_31      0.0614571000
_diffrn_orient_matrix_UB_32      0.0240974000
_diffrn_orient_matrix_UB_33      0.0723054000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2308
_reflns_number_total             2504
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+9.5803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Free rotating group:
 O1(H1A,H1B)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C2(H2), C9(H9), C6(H6), C11(H11), C4(H4), C5(H5), C10(H10),
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.80158(2) 0.70960(2) 0.53065(4) 0.02157(17) Uani 1 1 d . . . . .
N1 N 0.75106(7) 0.64780(7) 0.46060(14) 0.0272(4) Uani 1 1 d . . . . .
N2 N 0.77867(9) 0.57201(9) 0.37490(17) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.84870(8) 0.77433(8) 0.43200(15) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.90932(9) 0.82273(9) 0.46093(16) 0.0255(4) Uani 1 1 d . . . . .
H8 H 0.928976 0.820726 0.532960 0.031 Uiso 1 1 calc R U . . .
C1 C 0.75811(9) 0.73336(8) 0.62450(15) 0.0245(4) Uani 1 1 d . . . . .
C12 C 0.82039(9) 0.77792(10) 0.32504(16) 0.0277(4) Uani 1 1 d . . . . .
H12 H 0.779210 0.745188 0.304630 0.033 Uiso 1 1 calc R U . . .
C13 C 0.76741(9) 0.60900(9) 0.41521(16) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.78913(10) 0.77850(9) 0.71386(17) 0.0310(4) Uani 1 1 d . . . . .
H2 H 0.832937 0.795140 0.727441 0.037 Uiso 1 1 calc R U . . .
C9 C 0.94074(9) 0.87381(10) 0.38386(18) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.981946 0.906708 0.403616 0.037 Uiso 1 1 calc R U . . .
C14 C 0.85312(8) 0.69461(8) 0.62430(15) 0.0246(4) Uani 1 1 d . . . . .
H14A H 0.880200 0.684806 0.573255 0.030 Uiso 1 1 calc R U . . .
H14B H 0.880778 0.732697 0.672057 0.030 Uiso 1 1 calc R U . . .
C6 C 0.69366(9) 0.70877(9) 0.60363(17) 0.0283(4) Uani 1 1 d . . . . .
H6 H 0.672705 0.678004 0.542899 0.034 Uiso 1 1 calc R U . . .
C11 C 0.85247(10) 0.82920(10) 0.24914(17) 0.0320(4) Uani 1 1 d . . . . .
H11 H 0.833196 0.831413 0.176745 0.038 Uiso 1 1 calc R U . . .
C4 C 0.69166(12) 0.77450(10) 0.7615(2) 0.0408(5) Uani 1 1 d . . . . .
H4 H 0.668815 0.788645 0.808589 0.049 Uiso 1 1 calc R U . . .
C5 C 0.66064(11) 0.72983(10) 0.67266(19) 0.0362(5) Uani 1 1 d . . . . .
H5 H 0.616906 0.713670 0.659071 0.043 Uiso 1 1 calc R U . . .
C10 C 0.91251(10) 0.87725(10) 0.27830(17) 0.0317(4) Uani 1 1 d . . . . .
H10 H 0.934259 0.912396 0.226257 0.038 Uiso 1 1 calc R U . . .
C3 C 0.75552(12) 0.79887(10) 0.78259(19) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.776150 0.829369 0.843875 0.046 Uiso 1 1 calc R U . . .
O1 O 0.73400(8) 0.44261(8) 0.39923(17) 0.0483(4) Uani 1 1 d G . . . .
H1A H 0.760629 0.432182 0.370836 0.072 Uiso 1 1 d G U . . .
H1B H 0.751066 0.482670 0.383698 0.072 Uiso 1 1 d G 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 N1 1.5993(15) . ?
P1 C7 1.7955(18) . ?
P1 C1 1.7846(18) . ?
P1 C14 1.8112(18) . ?
N1 C13 1.304(2) . ?
N2 C13 1.161(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.404(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.399(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C14 C14 1.542(3) 13_666 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C4 C3 1.387(4) . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
O1 H1A 0.8701 . ?
O1 H1B 0.8700 . ?

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
N1 P1 C7 112.81(8) . . ?
N1 P1 C1 106.83(9) . . ?
N1 P1 C14 112.18(8) . . ?
C7 P1 C14 109.06(8) . . ?
C1 P1 C7 107.22(8) . . ?
C1 P1 C14 108.53(8) . . ?
C13 N1 P1 120.33(13) . . ?
C8 C7 P1 123.27(13) . . ?
C8 C7 C12 119.42(17) . . ?
C12 C7 P1 117.13(14) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.73(17) . . ?
C9 C8 H8 120.1 . . ?
C2 C1 P1 119.94(15) . . ?
C2 C1 C6 120.60(18) . . ?
C6 C1 P1 119.38(14) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.06(18) . . ?
C11 C12 H12 120.0 . . ?
N2 C13 N1 176.4(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.66(19) . . ?
C10 C9 H9 119.7 . . ?
P1 C14 H14A 109.7 . . ?
P1 C14 H14B 109.7 . . ?
C14 C14 P1 109.90(16) 13_666 . ?
C14 C14 H14A 109.7 13_666 . ?
C14 C14 H14B 109.7 13_666 . ?
H14A C14 H14B 108.2 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.27(19) . . ?
C5 C6 H6 120.4 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.38(17) . . ?
C10 C11 H11 119.8 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.04(19) . . ?
C3 C4 H4 119.5 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.75(18) . . ?
C11 C10 H10 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
H1A O1 H1B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C7 C8 C9 -174.81(14) . . . . ?
P1 C7 C12 C11 175.20(14) . . . . ?
P1 C1 C2 C3 176.96(15) . . . . ?
P1 C1 C6 C5 -176.62(14) . . . . ?
N1 P1 C7 C8 -154.13(15) . . . . ?
N1 P1 C7 C12 30.77(17) . . . . ?
N1 P1 C1 C2 167.47(14) . . . . ?
N1 P1 C1 C6 -15.75(16) . . . . ?
N1 P1 C14 C14 -53.78(19) . . . 13_666 ?
C7 P1 N1 C13 83.79(16) . . . . ?
C7 P1 C1 C2 -71.35(16) . . . . ?
C7 P1 C1 C6 105.43(15) . . . . ?
C7 P1 C14 C14 -179.50(16) . . . 13_666 ?
C7 C8 C9 C10 0.0(3) . . . . ?
C7 C12 C11 C10 -0.1(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C1 P1 N1 C13 -158.65(15) . . . . ?
C1 P1 C7 C8 88.54(16) . . . . ?
C1 P1 C7 C12 -86.55(15) . . . . ?
C1 P1 C14 C14 64.01(18) . . . 13_666 ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C12 C11 C10 C9 0.3(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C14 P1 N1 C13 -39.85(18) . . . . ?
C14 P1 C7 C8 -28.78(17) . . . . ?
C14 P1 C7 C12 156.12(14) . . . . ?
C14 P1 C1 C2 46.32(17) . . . . ?
C14 P1 C1 C6 -136.89(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?

_olex2_date_sample_data_collection 2023-01-25
_olex2_date_sample_submission    2023-01-25
_olex2_exptl_crystal_mounting_method 
'Mounted onto a MiTeGen loop using paratone oil.'
_olex2_submission_original_sample_id mds008
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.889
####################################################################### 
# 
# 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_Compound_22
_database_code_depnum_ccdc_archive 'CCDC 2258975'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
velabo.mdluli@merck.com
mohammad.chaudhry1@merck.com
justin.newman@merck.com
_chemical_name_common            Compound_22
_chemical_name_systematic        Compound_22
_chemical_formula_moiety         'C30 H33 N4 P'
_chemical_formula_sum            'C30 H33 N4 P'
_chemical_formula_weight         480.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P1 C20 N3 H20'
_chemical_oxdiff_usercomment     'MWMS-339-48 other sample from velabo'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.3525(2)
_cell_length_b                   9.81549(15)
_cell_length_c                   17.3460(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.1105(13)
_cell_angle_gamma                90
_cell_volume                     2587.77(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15608
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3910
_cell_measurement_theta_min      3.5650
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 -2 0.0855
2 -1 2 0.1226
-1 -2 -2 0.0847
-1 0 -1 0.0966
0 1 0 0.0723
0 2 -1 0.0768
2 2 1 0.0935
-1 -1 0 0.0837
-2 -1 2 0.0680
2 1 -2 0.0719
1 0 0 0.0895
-1 0 1 0.0438
1 0 -1 0.0505
-1 1 1 0.0578
1 -1 -1 0.1080
1 0 2 0.0999

_exptl_crystal_recrystallization_method 
'Grown via slow evaporation of mds042 in acetonitrile/methanol/water'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.094
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 1.0000 -2.0000 0.0093 -0.0061 0.3288
2.0000 -1.0000 2.0000 -0.0093 0.0061 -0.3288
-1.0000 -2.0000 -2.0000 -0.0873 -0.3710 0.0294
-1.0000 -0.0000 -1.0000 -0.0012 -0.0711 0.1258
0.0000 1.0000 -0.0000 0.0117 0.1362 0.0772
-0.0000 2.0000 -1.0000 -0.0392 0.2448 0.2124
2.0000 2.0000 1.0000 -0.0368 0.3871 -0.0392
-1.0000 -1.0000 0.0000 0.0497 -0.1798 -0.0094
-2.0000 -1.0000 2.0000 0.2365 -0.1684 -0.0576
2.0000 1.0000 -2.0000 -0.2365 0.1684 0.0576
1.0000 -0.0000 -0.0000 -0.0614 0.0436 -0.0678
-1.0000 0.0000 1.0000 0.1241 -0.0161 0.0098
1.0000 -0.0000 -1.0000 -0.1241 0.0161 -0.0098
-1.0000 1.0000 1.0000 0.1358 0.1201 0.0870
1.0000 -1.0000 -1.0000 -0.1358 -0.1201 -0.0870
1.0000 0.0000 2.0000 0.0639 0.0986 -0.1838

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25482
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.449
_diffrn_reflns_theta_min         3.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 130.00   0.50    0.13    --  107.23 -82.00-155.00  190
  2  ω    -21.00  73.00   0.50    0.05    --   50.08 -82.00-155.00  188
  3  ω    -64.00 -24.00   0.50    0.13    --  -90.00  57.00 -90.00   80
  4  ω    -45.00 -20.00   0.50    0.13    --  -90.00  38.00 -90.00   50
  5  ω    -46.00 -21.00   0.50    0.13    --  -90.00  38.00-180.00   50
  6  ω    -33.00  23.00   0.50    0.05    --  -50.08  19.00 -60.00  112
  7  ω    -45.00 -19.00   0.50    0.13    --  -90.00  38.00  30.00   52
  8  ω    -46.00 -21.00   0.50    0.13    --  -90.00  38.00 120.00   50
  9  ω    -46.00  21.00   0.50    0.05    --  -50.08  38.00  60.00  134
 10  ω   -159.00-125.00   0.50    0.13    --  -90.00 -99.00 150.00   68
 11  ω   -155.00-119.00   0.50    0.13    --  -90.00 -77.00 -30.00   72
 12  ω   -161.00 -79.00   0.50    0.13    --  -90.00 -82.00-155.00  164
 13  ω   -153.00-127.00   0.50    0.13    --  -90.00 -57.00 -90.00   52
 14  ω   -159.00-110.00   0.50    0.13    --  -90.00 -99.00 -90.00   98
 15  ω   -159.00-117.00   0.50    0.13    --  -90.00 -77.00  90.00   84
 16  ω   -161.00-120.00   0.50    0.13    --  -90.00 -57.00 120.00   82
 17  ω   -113.00 -18.00   0.50    0.13    --  -90.00  82.00 -34.00  190
 18  ω    -73.00  22.00   0.50    0.05    --  -50.08  82.00 -34.00  190
 19  ω   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00-150.00  158
 20  ω    -19.00  26.00   0.50    0.05    --   50.08 -19.00-180.00   90
 21  ω     37.00  64.00   0.50    0.13    --  107.23 -57.00-120.00   54
 22  ω     36.00  63.00   0.50    0.13    --  107.23 -57.00 -90.00   54
 23  ω     35.00  60.00   0.50    0.13    --  107.23 -57.00 -30.00   50
 24  ω     35.00  60.00   0.50    0.13    --  107.23 -57.00   0.00   50
 25  ω     37.00  64.00   0.50    0.13    --  107.23 -57.00  30.00   54
 26  ω     38.00  64.00   0.50    0.13    --  107.23 -57.00 120.00   52
 27  ω    101.00 178.00   0.50    0.13    --  107.23  82.00 -34.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0614338000
_diffrn_orient_matrix_UB_12      0.0117194000
_diffrn_orient_matrix_UB_13      0.0626533000
_diffrn_orient_matrix_UB_21      0.0436126000
_diffrn_orient_matrix_UB_22      0.1361701000
_diffrn_orient_matrix_UB_23      0.0275050000
_diffrn_orient_matrix_UB_31      -0.0678028000
_diffrn_orient_matrix_UB_32      0.0772075000
_diffrn_orient_matrix_UB_33      -0.0580031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4613
_reflns_number_total             5086
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+1.1393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0877
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C24(H24), C23(H23), C22(H22),
 C21(H21), C20(H20), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
1.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C8(H8A,H8B,
 H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.35884(2) 0.27780(3) 0.16926(2) 0.01639(9) Uani 1 1 d . . . . .
N1 N 0.37557(7) 0.15733(11) 0.23126(6) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.50902(7) 0.01733(12) 0.26438(7) 0.0295(3) Uani 1 1 d . . . . .
N3 N 0.47271(6) 0.37125(11) 0.33655(6) 0.0186(2) Uani 1 1 d . . . . .
N4 N 0.40033(7) 0.34389(11) 0.37082(6) 0.0192(2) Uani 1 1 d . . . . .
C6 C 0.46511(8) 0.46460(13) 0.27272(7) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.41466(8) 0.43796(13) 0.20018(7) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.40959(8) 0.54297(14) 0.14442(7) 0.0222(3) Uani 1 1 d . . . . .
H2 H 0.374860 0.529242 0.095219 0.027 Uiso 1 1 calc R U . . .
C3 C 0.45350(9) 0.66560(14) 0.15887(8) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.449067 0.733905 0.119709 0.029 Uiso 1 1 calc R U . . .
C4 C 0.50391(8) 0.68864(14) 0.23045(8) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.534865 0.771996 0.240550 0.030 Uiso 1 1 calc R U . . .
C5 C 0.50849(8) 0.58848(14) 0.28698(8) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.541916 0.604579 0.336527 0.027 Uiso 1 1 calc R U . . .
C16 C 0.54839(8) 0.32067(13) 0.37858(7) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.52254(8) 0.25361(14) 0.44078(7) 0.0207(3) Uani 1 1 d . . . . .
H17 H 0.559032 0.205270 0.480397 0.025 Uiso 1 1 calc R U . . .
C18 C 0.43029(8) 0.27115(13) 0.43388(7) 0.0182(3) Uani 1 1 d . . . . .
C19 C 0.63702(8) 0.34425(13) 0.35582(7) 0.0190(3) Uani 1 1 d . . . . .
C24 C 0.68814(8) 0.45290(14) 0.38879(7) 0.0219(3) Uani 1 1 d . . . . .
H24 H 0.667171 0.508436 0.427094 0.026 Uiso 1 1 calc R U . . .
C23 C 0.76938(8) 0.47999(14) 0.36582(8) 0.0232(3) Uani 1 1 d . . . . .
H23 H 0.803138 0.555292 0.387616 0.028 Uiso 1 1 calc R U . . .
C22 C 0.80162(8) 0.39777(14) 0.31121(8) 0.0238(3) Uani 1 1 d . . . . .
H22 H 0.856940 0.417165 0.295112 0.029 Uiso 1 1 calc R U . . .
C21 C 0.75235(9) 0.28681(15) 0.28026(8) 0.0247(3) Uani 1 1 d . . . . .
H21 H 0.774971 0.228567 0.244090 0.030 Uiso 1 1 calc R U . . .
C20 C 0.67016(8) 0.26052(14) 0.30190(7) 0.0222(3) Uani 1 1 d . . . . .
H20 H 0.636502 0.185292 0.279873 0.027 Uiso 1 1 calc R U . . .
C25 C 0.36837(8) 0.22265(13) 0.48539(7) 0.0190(3) Uani 1 1 d . . . . .
C26 C 0.39620(9) 0.14150(15) 0.55025(7) 0.0243(3) Uani 1 1 d . . . . .
H26 H 0.456607 0.117901 0.562182 0.029 Uiso 1 1 calc R U . . .
C27 C 0.33671(9) 0.09470(16) 0.59767(8) 0.0285(3) Uani 1 1 d . . . . .
H27 H 0.356587 0.039477 0.641620 0.034 Uiso 1 1 calc R U . . .
C28 C 0.24833(9) 0.12859(15) 0.58083(8) 0.0278(3) Uani 1 1 d . . . . .
H28 H 0.207469 0.096160 0.612889 0.033 Uiso 1 1 calc R U . . .
C29 C 0.22003(9) 0.21016(14) 0.51687(7) 0.0240(3) Uani 1 1 d . . . . .
H29 H 0.159658 0.234323 0.505554 0.029 Uiso 1 1 calc R U . . .
C30 C 0.27916(8) 0.25677(14) 0.46926(7) 0.0209(3) Uani 1 1 d . . . . .
H30 H 0.258944 0.312166 0.425469 0.025 Uiso 1 1 calc R U . . .
C15 C 0.44783(8) 0.08682(13) 0.24787(7) 0.0203(3) Uani 1 1 d . . . . .
C11 C 0.23864(8) 0.30709(13) 0.15988(7) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.20767(9) 0.43725(14) 0.11519(8) 0.0240(3) Uani 1 1 d . . . . .
H12A H 0.235428 0.516673 0.142752 0.036 Uiso 1 1 calc R U . . .
H12B H 0.143576 0.444972 0.111579 0.036 Uiso 1 1 calc R U . . .
H12C H 0.224217 0.433234 0.062700 0.036 Uiso 1 1 calc R U . . .
C13 C 0.19047(8) 0.18238(14) 0.12067(8) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.200647 0.177458 0.066222 0.036 Uiso 1 1 calc R U . . .
H13B H 0.127241 0.190808 0.122765 0.036 Uiso 1 1 calc R U . . .
H13C H 0.212833 0.099417 0.148041 0.036 Uiso 1 1 calc R U . . .
C14 C 0.21651(8) 0.32036(14) 0.24332(7) 0.0220(3) Uani 1 1 d . . . . .
H14A H 0.230738 0.234878 0.271485 0.033 Uiso 1 1 calc R U . . .
H14B H 0.153656 0.339947 0.241486 0.033 Uiso 1 1 calc R U . . .
H14C H 0.251026 0.394718 0.270137 0.033 Uiso 1 1 calc R U . . .
C7 C 0.40072(9) 0.22607(14) 0.07665(8) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.38470(9) 0.07164(15) 0.06541(8) 0.0273(3) Uani 1 1 d . . . . .
H8A H 0.414585 0.022528 0.110780 0.041 Uiso 1 1 calc R U . . .
H8B H 0.407950 0.041281 0.018489 0.041 Uiso 1 1 calc R U . . .
H8C H 0.321406 0.053052 0.059807 0.041 Uiso 1 1 calc R U . . .
C10 C 0.50092(9) 0.25032(17) 0.08875(9) 0.0318(3) Uani 1 1 d . . . . .
H10A H 0.512767 0.348450 0.089235 0.048 Uiso 1 1 calc R U . . .
H10B H 0.526746 0.207547 0.046208 0.048 Uiso 1 1 calc R U . . .
H10C H 0.526962 0.210388 0.138481 0.048 Uiso 1 1 calc R U . . .
C9 C 0.35878(10) 0.29886(16) 0.00188(8) 0.0299(3) Uani 1 1 d . . . . .
H9A H 0.295166 0.282557 -0.006119 0.045 Uiso 1 1 calc R U . . .
H9B H 0.384408 0.263398 -0.042721 0.045 Uiso 1 1 calc R U . . .
H9C H 0.370074 0.396954 0.006896 0.045 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 N1 1.5946(11) . ?
P1 C1 1.8340(13) . ?
P1 C11 1.8521(12) . ?
P1 C7 1.8823(13) . ?
N1 C15 1.3049(16) . ?
N2 C15 1.1635(17) . ?
N3 N4 1.3591(14) . ?
N3 C6 1.4291(16) . ?
N3 C16 1.3744(16) . ?
N4 C18 1.3327(16) . ?
C6 C1 1.4060(17) . ?
C6 C5 1.3916(18) . ?
C1 C2 1.4080(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3851(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3833(19) . ?
C5 H5 0.9500 . ?
C16 C17 1.3695(18) . ?
C16 C19 1.4874(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.4149(17) . ?
C18 C25 1.4726(17) . ?
C19 C24 1.3977(18) . ?
C19 C20 1.3943(18) . ?
C24 H24 0.9500 . ?
C24 C23 1.3875(18) . ?
C23 H23 0.9500 . ?
C23 C22 1.3878(19) . ?
C22 H22 0.9500 . ?
C22 C21 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.3903(19) . ?
C20 H20 0.9500 . ?
C25 C26 1.3954(18) . ?
C25 C30 1.3993(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3905(19) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.3881(18) . ?
C30 H30 0.9500 . ?
C11 C12 1.5347(17) . ?
C11 C13 1.5382(18) . ?
C11 C14 1.5380(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C7 C8 1.5436(19) . ?
C7 C10 1.5416(19) . ?
C7 C9 1.5400(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
N1 P1 C1 114.48(6) . . ?
N1 P1 C11 103.77(5) . . ?
N1 P1 C7 109.49(6) . . ?
C1 P1 C11 108.14(6) . . ?
C1 P1 C7 106.20(6) . . ?
C11 P1 C7 115.02(6) . . ?
C15 N1 P1 126.39(9) . . ?
N4 N3 C6 118.89(10) . . ?
N4 N3 C16 112.26(10) . . ?
C16 N3 C6 127.81(10) . . ?
C18 N4 N3 104.83(10) . . ?
C1 C6 N3 123.27(11) . . ?
C5 C6 N3 115.96(11) . . ?
C5 C6 C1 120.73(12) . . ?
C6 C1 P1 126.64(10) . . ?
C6 C1 C2 116.66(11) . . ?
C2 C1 P1 116.64(9) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.25(12) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.99(12) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.03(12) . . ?
C5 C4 H4 120.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.32(12) . . ?
C4 C5 H5 119.3 . . ?
N3 C16 C19 122.65(11) . . ?
C17 C16 N3 105.92(11) . . ?
C17 C16 C19 131.41(11) . . ?
C16 C17 H17 127.1 . . ?
C16 C17 C18 105.82(11) . . ?
C18 C17 H17 127.1 . . ?
N4 C18 C17 111.11(11) . . ?
N4 C18 C25 119.58(11) . . ?
C17 C18 C25 129.31(11) . . ?
C24 C19 C16 119.48(11) . . ?
C20 C19 C16 121.37(11) . . ?
C20 C19 C24 119.16(12) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.29(12) . . ?
C23 C24 H24 119.9 . . ?
C24 C23 H23 119.8 . . ?
C24 C23 C22 120.41(12) . . ?
C22 C23 H23 119.8 . . ?
C23 C22 H22 120.3 . . ?
C23 C22 C21 119.49(12) . . ?
C21 C22 H22 120.3 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C20 120.42(12) . . ?
C20 C21 H21 119.8 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.18(12) . . ?
C21 C20 H20 119.9 . . ?
C26 C25 C18 121.56(11) . . ?
C26 C25 C30 118.53(12) . . ?
C30 C25 C18 119.91(11) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.90(12) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.05(13) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.56(12) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.57(12) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 119.8 . . ?
C29 C30 C25 120.39(12) . . ?
C29 C30 H30 119.8 . . ?
N2 C15 N1 175.60(14) . . ?
C12 C11 P1 114.04(9) . . ?
C12 C11 C13 110.11(10) . . ?
C12 C11 C14 108.12(10) . . ?
C13 C11 P1 109.04(9) . . ?
C13 C11 C14 109.10(10) . . ?
C14 C11 P1 106.27(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C7 P1 107.78(9) . . ?
C10 C7 P1 107.26(9) . . ?
C10 C7 C8 107.88(11) . . ?
C9 C7 P1 116.17(9) . . ?
C9 C7 C8 108.00(11) . . ?
C9 C7 C10 109.49(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -175.84(10) . . . . ?
N1 P1 C1 C6 -3.54(13) . . . . ?
N1 P1 C1 C2 173.53(9) . . . . ?
N1 P1 C11 C12 168.75(9) . . . . ?
N1 P1 C11 C13 -67.73(9) . . . . ?
N1 P1 C11 C14 49.75(10) . . . . ?
N1 P1 C7 C8 34.79(11) . . . . ?
N1 P1 C7 C10 -81.13(11) . . . . ?
N1 P1 C7 C9 156.06(10) . . . . ?
N3 N4 C18 C17 0.95(14) . . . . ?
N3 N4 C18 C25 -179.65(10) . . . . ?
N3 C6 C1 P1 -6.39(17) . . . . ?
N3 C6 C1 C2 176.54(11) . . . . ?
N3 C6 C5 C4 -178.13(11) . . . . ?
N3 C16 C17 C18 -1.65(14) . . . . ?
N3 C16 C19 C24 94.68(15) . . . . ?
N3 C16 C19 C20 -85.01(16) . . . . ?
N4 N3 C6 C1 -66.54(16) . . . . ?
N4 N3 C6 C5 111.13(12) . . . . ?
N4 N3 C16 C17 2.38(14) . . . . ?
N4 N3 C16 C19 -176.29(11) . . . . ?
N4 C18 C25 C26 177.33(12) . . . . ?
N4 C18 C25 C30 -2.03(18) . . . . ?
C6 N3 N4 C18 -171.32(10) . . . . ?
C6 N3 C16 C17 170.45(12) . . . . ?
C6 N3 C16 C19 -8.2(2) . . . . ?
C6 C1 C2 C3 1.54(18) . . . . ?
C1 P1 N1 C15 -73.89(12) . . . . ?
C1 P1 C11 C12 46.80(11) . . . . ?
C1 P1 C11 C13 170.32(8) . . . . ?
C1 P1 C11 C14 -72.20(10) . . . . ?
C1 P1 C7 C8 158.88(9) . . . . ?
C1 P1 C7 C10 42.96(11) . . . . ?
C1 P1 C7 C9 -79.85(11) . . . . ?
C1 C6 C5 C4 -0.40(19) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.86(19) . . . . ?
C3 C4 C5 C6 1.37(19) . . . . ?
C5 C6 C1 P1 176.05(9) . . . . ?
C5 C6 C1 C2 -1.02(17) . . . . ?
C16 N3 N4 C18 -2.07(14) . . . . ?
C16 N3 C6 C1 126.08(14) . . . . ?
C16 N3 C6 C5 -56.25(17) . . . . ?
C16 C17 C18 N4 0.46(15) . . . . ?
C16 C17 C18 C25 -178.87(12) . . . . ?
C16 C19 C24 C23 -177.26(12) . . . . ?
C16 C19 C20 C21 178.46(12) . . . . ?
C17 C16 C19 C24 -83.61(18) . . . . ?
C17 C16 C19 C20 96.70(17) . . . . ?
C17 C18 C25 C26 -3.4(2) . . . . ?
C17 C18 C25 C30 177.25(13) . . . . ?
C18 C25 C26 C27 -178.98(12) . . . . ?
C18 C25 C30 C29 179.18(12) . . . . ?
C19 C16 C17 C18 176.85(13) . . . . ?
C19 C24 C23 C22 -1.5(2) . . . . ?
C24 C19 C20 C21 -1.24(19) . . . . ?
C24 C23 C22 C21 -0.8(2) . . . . ?
C23 C22 C21 C20 2.0(2) . . . . ?
C22 C21 C20 C19 -1.0(2) . . . . ?
C20 C19 C24 C23 2.45(19) . . . . ?
C25 C26 C27 C28 0.0(2) . . . . ?
C26 C25 C30 C29 -0.20(19) . . . . ?
C26 C27 C28 C29 -0.5(2) . . . . ?
C27 C28 C29 C30 0.7(2) . . . . ?
C28 C29 C30 C25 -0.3(2) . . . . ?
C30 C25 C26 C27 0.39(19) . . . . ?
C11 P1 N1 C15 168.49(11) . . . . ?
C11 P1 C1 C6 111.56(11) . . . . ?
C11 P1 C1 C2 -71.37(11) . . . . ?
C11 P1 C7 C8 -81.55(10) . . . . ?
C11 P1 C7 C10 162.53(9) . . . . ?
C11 P1 C7 C9 39.72(12) . . . . ?
C7 P1 N1 C15 45.21(13) . . . . ?
C7 P1 C1 C6 -124.47(11) . . . . ?
C7 P1 C1 C2 52.60(11) . . . . ?
C7 P1 C11 C12 -71.68(11) . . . . ?
C7 P1 C11 C13 51.83(10) . . . . ?
C7 P1 C11 C14 169.31(8) . . . . ?

_olex2_date_sample_data_collection 2023-02-13
_olex2_date_sample_submission    2023-02-13
_olex2_exptl_crystal_mounting_method 
'Mounted onto a MiTiGen loop using paratone oil.'
_olex2_submission_original_sample_id mds042
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_Compound_36
_database_code_depnum_ccdc_archive 'CCDC 2258979'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mohammad.chaudhry1@merck.com
velabo.mdluli@merck.com
_chemical_name_common            Compound_36
_chemical_name_systematic        Compound_36
_chemical_formula_moiety         '2(C27 H24 N2 P2)'
_chemical_formula_sum            'C54 H48 N4 P4'
_chemical_formula_weight         876.84
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P2 N2 C30 H30'
_chemical_oxdiff_usercomment     SWMS-339-53
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.10450(10)
_cell_length_b                   26.3845(3)
_cell_length_c                   9.35170(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.6980(10)
_cell_angle_gamma                90
_cell_volume                     2241.77(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    29506
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5160
_cell_measurement_theta_min      3.3580
_shelx_estimated_absorpt_T_max   0.735
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.197
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0855
-1 0 -1 0.0882
0 -1 0 0.1357
0 1 0 0.1753
-1 1 -2 0.0860
1 0 2 0.0857
1 2 -1 0.1110
0 -1 -1 0.0875
-2 1 2 0.0857
1 -2 -2 0.0975
1 1 0 0.0979
-1 -1 0 0.1040
0 -2 -1 0.1016
-1 1 1 0.0893

_exptl_crystal_recrystallization_method 
'Grown via. slow evaporation from a solution of mds066 in MeCN, MeOH, and H2O.'
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.174
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0005 -0.0087 1.0032 -0.0344 -0.1449 -0.1940
-1.0005 0.0087 -1.0032 0.0344 0.1449 0.1940
-0.0010 -0.9993 -0.0007 0.0054 -0.0469 0.0343
0.0010 0.9993 0.0007 -0.0054 0.0469 -0.0343
-1.0015 1.0151 -2.0027 -0.0666 0.2638 0.2734
1.0025 -0.0158 2.0034 0.0613 -0.2169 -0.3076
0.9985 2.0041 -0.9959 -0.2364 0.0930 -0.0351
-0.0030 -0.9922 -1.0009 -0.0903 0.0251 0.1479
-1.9920 0.9884 1.9951 0.4461 0.0487 -0.1010
0.9925 -1.9861 -1.9987 -0.3106 -0.0228 0.2156
0.9995 0.9977 0.0037 -0.1354 -0.0259 -0.1146
-0.9995 -0.9977 -0.0037 0.1354 0.0259 0.1146
-0.0040 -1.9915 -1.0015 -0.0849 -0.0219 0.1822
-0.9955 0.9938 0.9979 0.2203 0.0478 -0.0677

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8774
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.962
_diffrn_reflns_theta_min         3.350
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  89.00   0.50    0.17    --  107.23 -73.00  31.00  108
  2  ω    -21.00  69.00   0.50    0.05    --   50.08 -73.00  31.00  180
  3  ω    -22.00  31.00   0.50    0.05    --   50.08 -19.00   0.00  106
  4  ω     35.00  64.00   0.50    0.17    --  107.23 -57.00-180.00   58
  5  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00 -90.00  140
  6  ω     35.00 112.00   0.50    0.17    --  107.23-125.00-180.00  154
  7  ω     35.00 112.00   0.50    0.17    --  107.23-125.00-150.00  154
  8  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00 -60.00  140
  9  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00  90.00  140
 10  ω     35.00 112.00   0.50    0.17    --  107.23-125.00 120.00  154
 11  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00 150.00  140
 12  ω     34.00  96.00   0.50    0.05    --   50.08-125.00 150.00  124
 13  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00  30.00  140
 14  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00   0.00  140
 15  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00 -30.00  140
 16  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00-120.00  140
 17  ω     35.00 105.00   0.50    0.17    --  107.23 -99.00-150.00  140
 18  ω     43.00 122.00   0.50    0.05    --   50.08  38.00 -90.00  158
 19  ω    115.00 178.00   0.50    0.17    --  107.23  77.00-180.00  126
 20  ω     42.00  98.00   0.50    0.05    --   50.08  40.00 -26.91  112
 21  ω    100.00 178.00   0.50    0.17    --  107.23  38.00 120.00  156
 22  ω     88.00 178.00   0.50    0.17    --  107.23  73.00 160.00  180
 23  ω     31.00 122.00   0.50    0.05    --   50.08  73.00 160.00  182
 24  ω    -69.00  22.00   0.50    0.05    --  -50.08  73.00 160.00  182
 25  ω    -66.00 -18.00   0.50    0.17    --  -90.00  57.00 150.00   96
 26  ω    -91.00 -18.00   0.50    0.17    --  -90.00  73.00 160.00  146
 27  ω    -33.00  23.00   0.50    0.05    --  -50.08  19.00 150.00  112
 28  ω    -46.00 -18.00   0.50    0.17    --  -90.00  38.00   0.00   56
 29  ω    -66.00 -18.00   0.50    0.17    --  -90.00  57.00   0.00   96
 30  ω    -46.00 -18.00   0.50    0.17    --  -90.00  38.00 -90.00   56
 31  ω   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00  60.00  158
 32  ω   -122.00 -31.00   0.50    0.05    --  -50.08 -73.00  31.00  182
 33  ω   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 -60.00   92
 34  ω   -161.00-111.00   0.50    0.17    --  -90.00 -57.00   0.00  100
 35  ω   -161.00 -71.00   0.50    0.17    --  -90.00 -73.00  31.00  180
 36  ω   -161.00-105.00   0.50    0.17    --  -90.00 -50.00 -50.31  112
 37  ω   -161.00-115.00   0.50    0.17    --  -90.00 -77.00  90.00   92
 38  ω   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 120.00   92
 39  ω   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1305356000
_diffrn_orient_matrix_UB_12      -0.0053009000
_diffrn_orient_matrix_UB_13      0.0958682000
_diffrn_orient_matrix_UB_21      -0.0726978000
_diffrn_orient_matrix_UB_22      0.0470993000
_diffrn_orient_matrix_UB_23      -0.0715045000
_diffrn_orient_matrix_UB_31      -0.0801207000
_diffrn_orient_matrix_UB_32      -0.0341339000
_diffrn_orient_matrix_UB_33      -0.1137346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                8472
_reflns_number_total             8774
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 
;
 Flack x determined using 3665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8774
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1088P)²+1.7790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.00105
 -0.00105
2.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C13(H13A,H13B), C14(H14A,H14B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C29(H29), C17(H17), C45(H45), C43(H43), C26(H26), C44(H44),
 C16(H16), C47(H47), C53(H53), C4(H4), C35(H35), C37(H37), C19(H19), C49(H49),
 C10(H10), C31(H31), C12(H12), C2(H2), C8(H8), C11(H11), C3(H3), C38(H38),
 C6(H6), C46(H46), C18(H18), C30(H30), C33(H33), C36(H36), C22(H22), C39(H39),
 C52(H52), C5(H5), C51(H51), C50(H50), C25(H25), C32(H32), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P3 P 0.63070(12) 0.40440(4) 0.77594(12) 0.0177(2) Uani 1 1 d . . . . .
P1 P 0.79095(12) 0.65107(4) 0.34399(12) 0.0181(2) Uani 1 1 d . . . . .
P2 P 0.36205(13) 0.61588(5) 0.11633(12) 0.0204(3) Uani 1 1 d . . . . .
P4 P 0.85230(13) 0.37483(5) 0.37638(12) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.8721(5) 0.59853(16) 0.3149(4) 0.0235(8) Uani 1 1 d . . . . .
N3 N 0.6762(5) 0.35269(16) 0.8580(4) 0.0228(8) Uani 1 1 d . . . . .
C42 C 1.0444(5) 0.35245(19) 0.3836(5) 0.0211(9) Uani 1 1 d . . . . .
C15 C 0.3413(5) 0.60063(18) -0.0757(5) 0.0213(9) Uani 1 1 d . . . . .
C9 C 0.8788(6) 0.7815(2) 0.1372(5) 0.0255(10) Uani 1 1 d . . . . .
H9 H 0.829363 0.812283 0.112643 0.031 Uiso 1 1 calc R U . . .
N4 N 0.5465(5) 0.27144(19) 0.8069(6) 0.0332(10) Uani 1 1 d . . . . .
C20 C 0.2092(6) 0.6133(2) -0.1493(6) 0.0273(10) Uani 1 1 d . . . . .
H20 H 0.133956 0.629278 -0.099706 0.033 Uiso 1 1 calc R U . . .
C29 C 0.7761(5) 0.49661(19) 0.7863(5) 0.0225(10) Uani 1 1 d . . . . .
H29 H 0.748957 0.499296 0.686815 0.027 Uiso 1 1 calc R U . . .
C40 C 0.6649(5) 0.40346(19) 0.5881(5) 0.0203(9) Uani 1 1 d . . . . .
H40A H 0.599892 0.378112 0.538236 0.024 Uiso 1 1 calc R U . . .
H40B H 0.641506 0.437094 0.545604 0.024 Uiso 1 1 calc R U . . .
C34 C 0.4400(5) 0.41964(18) 0.7939(5) 0.0196(9) Uani 1 1 d . . . . .
C17 C 0.4250(7) 0.5656(2) -0.2956(6) 0.0312(11) Uani 1 1 d . . . . .
H17 H 0.499283 0.549248 -0.345563 0.037 Uiso 1 1 calc R U . . .
C45 C 1.3300(6) 0.3135(2) 0.3713(6) 0.0271(11) Uani 1 1 d . . . . .
H45 H 1.426844 0.300452 0.367263 0.033 Uiso 1 1 calc R U . . .
C28 C 0.7393(5) 0.45307(18) 0.8623(5) 0.0193(9) Uani 1 1 d . . . . .
C43 C 1.1313(6) 0.3423(2) 0.5090(5) 0.0239(10) Uani 1 1 d . . . . .
H43 H 1.093305 0.348427 0.599637 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5950(5) 0.64928(19) 0.2962(5) 0.0212(9) Uani 1 1 d . . . . .
H13A H 0.548901 0.623774 0.356735 0.025 Uiso 1 1 calc R U . . .
H13B H 0.551992 0.682716 0.317203 0.025 Uiso 1 1 calc R U . . .
C26 C 0.2380(6) 0.5343(2) 0.2466(5) 0.0264(10) Uani 1 1 d . . . . .
H26 H 0.153533 0.555472 0.242821 0.032 Uiso 1 1 calc R U . . .
C44 C 1.2732(6) 0.3231(2) 0.5019(6) 0.0267(11) Uani 1 1 d . . . . .
H44 H 1.331424 0.316528 0.587847 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4486(6) 0.5754(2) -0.1501(5) 0.0242(10) Uani 1 1 d . . . . .
H16 H 0.537830 0.564919 -0.100557 0.029 Uiso 1 1 calc R U . . .
C47 C 1.1044(6) 0.3428(2) 0.2528(5) 0.0256(10) Uani 1 1 d . . . . .
H47 H 1.047773 0.349903 0.166217 0.031 Uiso 1 1 calc R U . . .
C53 C 0.7458(5) 0.2785(2) 0.4676(5) 0.0233(10) Uani 1 1 d . . . . .
H53 H 0.782925 0.286997 0.561839 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8772(5) 0.69765(18) 0.2399(5) 0.0190(9) Uani 1 1 d . . . . .
C4 C 0.8579(6) 0.6945(2) 0.8176(5) 0.0255(10) Uani 1 1 d . . . . .
H4 H 0.874120 0.702348 0.916503 0.031 Uiso 1 1 calc R U . . .
C35 C 0.3823(6) 0.4100(2) 0.9255(5) 0.0269(10) Uani 1 1 d . . . . .
H35 H 0.441888 0.394564 1.000386 0.032 Uiso 1 1 calc R U . . .
C37 C 0.1504(6) 0.4457(2) 0.8376(6) 0.0267(10) Uani 1 1 d . . . . .
H37 H 0.051567 0.454691 0.852680 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1855(7) 0.6029(2) -0.2947(6) 0.0318(12) Uani 1 1 d . . . . .
H19 H 0.094562 0.612019 -0.343487 0.038 Uiso 1 1 calc R U . . .
C49 C 0.7001(6) 0.3003(2) 0.2196(6) 0.0250(10) Uani 1 1 d . . . . .
H49 H 0.704732 0.324017 0.143614 0.030 Uiso 1 1 calc R U . . .
C10 C 1.0241(6) 0.7754(2) 0.1065(5) 0.0271(11) Uani 1 1 d . . . . .
H10 H 1.074593 0.802252 0.062882 0.032 Uiso 1 1 calc R U . . .
C31 C 0.8910(6) 0.5324(2) 1.0020(6) 0.0269(11) Uani 1 1 d . . . . .
H31 H 0.941379 0.559633 1.049865 0.032 Uiso 1 1 calc R U . . .
C21 C 0.3697(6) 0.55240(19) 0.1963(5) 0.0233(10) Uani 1 1 d . . . . .
C1 C 0.8106(5) 0.67038(18) 0.5287(5) 0.0193(9) Uani 1 1 d . . . . .
C14 C 0.5577(5) 0.6363(2) 0.1373(5) 0.0231(10) Uani 1 1 d . . . . .
H14A H 0.622514 0.608683 0.106932 0.028 Uiso 1 1 calc R U . . .
H14B H 0.573165 0.666324 0.076775 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0231(5) 0.69117(19) 0.2056(5) 0.0225(9) Uani 1 1 d . . . . .
H12 H 1.072158 0.660073 0.227460 0.027 Uiso 1 1 calc R U . . .
C48 C 0.7578(5) 0.31314(19) 0.3558(5) 0.0204(9) Uani 1 1 d . . . . .
N2 N 0.8515(8) 0.5202(2) 0.4583(6) 0.0468(15) Uani 1 1 d . . . . .
C2 C 0.9275(5) 0.7028(2) 0.5756(5) 0.0243(10) Uani 1 1 d . . . . .
H2 H 0.989857 0.716927 0.508363 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8040(5) 0.74306(19) 0.2037(5) 0.0223(9) Uani 1 1 d . . . . .
H8 H 0.704010 0.747534 0.224405 0.027 Uiso 1 1 calc R U . . .
C41 C 0.8276(5) 0.39018(19) 0.5660(5) 0.0215(9) Uani 1 1 d . . . . .
H41A H 0.857842 0.360817 0.626879 0.026 Uiso 1 1 calc R U . . .
H41B H 0.891087 0.419284 0.595650 0.026 Uiso 1 1 calc R U . . .
C11 C 1.0969(6) 0.7298(2) 0.1397(5) 0.0252(10) Uani 1 1 d . . . . .
H11 H 1.196301 0.725299 0.117287 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9508(6) 0.7140(2) 0.7197(6) 0.0263(10) Uani 1 1 d . . . . .
H3 H 1.030833 0.735100 0.751734 0.032 Uiso 1 1 calc R U . . .
C38 C 0.2075(6) 0.4552(2) 0.7069(6) 0.0269(10) Uani 1 1 d . . . . .
H38 H 0.147164 0.470150 0.631713 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7178(6) 0.6516(2) 0.6282(5) 0.0263(10) Uani 1 1 d . . . . .
H6 H 0.637514 0.630414 0.597463 0.032 Uiso 1 1 calc R U . . .
C46 C 1.2451(6) 0.3231(2) 0.2466(6) 0.0283(11) Uani 1 1 d . . . . .
H46 H 1.283093 0.316164 0.156347 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2931(7) 0.5795(2) -0.3689(6) 0.0342(12) Uani 1 1 d . . . . .
H18 H 0.277371 0.572993 -0.468590 0.041 Uiso 1 1 calc R U . . .
C30 C 0.8522(6) 0.5358(2) 0.8571(6) 0.0274(11) Uani 1 1 d . . . . .
H30 H 0.877829 0.565142 0.805491 0.033 Uiso 1 1 calc R U . . .
C33 C 0.7814(5) 0.4493(2) 1.0077(5) 0.0236(10) Uani 1 1 d . . . . .
H33 H 0.758836 0.419506 1.058925 0.028 Uiso 1 1 calc R U . . .
C36 C 0.2378(6) 0.4231(2) 0.9472(6) 0.0307(12) Uani 1 1 d . . . . .
H36 H 0.198474 0.416499 1.036973 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4929(6) 0.5213(2) 0.2076(6) 0.0275(11) Uani 1 1 d . . . . .
H22 H 0.583642 0.533469 0.176246 0.033 Uiso 1 1 calc R U . . .
C39 C 0.3523(6) 0.4429(2) 0.6846(6) 0.0248(10) Uani 1 1 d . . . . .
H39 H 0.391832 0.450313 0.595405 0.030 Uiso 1 1 calc R U . . .
C52 C 0.6794(6) 0.2313(2) 0.4412(6) 0.0278(11) Uani 1 1 d . . . . .
H52 H 0.671106 0.207935 0.517673 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7414(6) 0.6636(2) 0.7718(6) 0.0289(11) Uani 1 1 d . . . . .
H5 H 0.677495 0.650499 0.839217 0.035 Uiso 1 1 calc R U . . .
C51 C 0.6262(6) 0.2185(2) 0.3050(6) 0.0288(11) Uani 1 1 d . . . . .
H51 H 0.582927 0.186188 0.287151 0.035 Uiso 1 1 calc R U . . .
C50 C 0.6356(6) 0.2531(2) 0.1926(6) 0.0272(10) Uani 1 1 d . . . . .
H50 H 0.598317 0.244471 0.098569 0.033 Uiso 1 1 calc R U . . .
C25 C 0.2295(7) 0.4851(2) 0.3025(6) 0.0331(12) Uani 1 1 d . . . . .
H25 H 0.139246 0.472754 0.334504 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8564(6) 0.4889(2) 1.0787(5) 0.0282(11) Uani 1 1 d . . . . .
H32 H 0.883695 0.486489 1.178190 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4856(7) 0.4725(2) 0.2644(6) 0.0347(13) Uani 1 1 d . . . . .
H23 H 0.570651 0.451562 0.271352 0.042 Uiso 1 1 calc R U . . .
C54 C 0.6033(5) 0.31086(19) 0.8275(5) 0.0237(10) Uani 1 1 d . . . . .
C27 C 0.8571(6) 0.5580(2) 0.3954(5) 0.0266(11) Uani 1 1 d . . . . .
C24 C 0.3531(8) 0.4548(2) 0.3107(6) 0.0357(14) Uani 1 1 d . . . . .
H24 H 0.347527 0.421456 0.348292 0.043 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
P3 N3 1.606(4) . ?
P3 C40 1.804(5) . ?
P3 C34 1.800(5) . ?
P3 C28 1.782(5) . ?
P1 N1 1.602(4) . ?
P1 C13 1.811(5) . ?
P1 C7 1.782(5) . ?
P1 C1 1.799(5) . ?
P2 C15 1.838(5) . ?
P2 C21 1.834(5) . ?
P2 C14 1.859(5) . ?
P4 C42 1.843(5) . ?
P4 C48 1.845(5) . ?
P4 C41 1.847(5) . ?
N1 C27 1.321(7) . ?
N3 C54 1.310(7) . ?
C42 C43 1.398(7) . ?
C42 C47 1.395(7) . ?
C15 C20 1.388(7) . ?
C15 C16 1.403(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(8) . ?
C9 C8 1.390(7) . ?
N4 C54 1.172(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.390(8) . ?
C29 H29 0.9500 . ?
C29 C28 1.402(7) . ?
C29 C30 1.388(7) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.548(6) . ?
C34 C35 1.392(7) . ?
C34 C39 1.398(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.388(7) . ?
C17 C18 1.392(9) . ?
C45 H45 0.9500 . ?
C45 C44 1.380(8) . ?
C45 C46 1.380(8) . ?
C28 C33 1.393(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.393(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.542(6) . ?
C26 H26 0.9500 . ?
C26 C21 1.400(7) . ?
C26 C25 1.403(8) . ?
C44 H44 0.9500 . ?
C16 H16 0.9500 . ?
C47 H47 0.9500 . ?
C47 C46 1.387(8) . ?
C53 H53 0.9500 . ?
C53 C48 1.399(7) . ?
C53 C52 1.399(8) . ?
C7 C12 1.397(7) . ?
C7 C8 1.402(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(8) . ?
C4 C5 1.384(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.382(8) . ?
C37 C36 1.391(8) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(9) . ?
C49 H49 0.9500 . ?
C49 C48 1.388(7) . ?
C49 C50 1.392(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(8) . ?
C31 H31 0.9500 . ?
C31 C30 1.381(8) . ?
C31 C32 1.398(8) . ?
C21 C22 1.388(8) . ?
C1 C2 1.414(7) . ?
C1 C6 1.388(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C11 1.386(7) . ?
N2 C27 1.160(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(7) . ?
C8 H8 0.9500 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.386(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.382(7) . ?
C46 H46 0.9500 . ?
C18 H18 0.9500 . ?
C30 H30 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.393(7) . ?
C36 H36 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.397(8) . ?
C39 H39 0.9500 . ?
C52 H52 0.9500 . ?
C52 C51 1.376(8) . ?
C5 H5 0.9500 . ?
C51 H51 0.9500 . ?
C51 C50 1.398(8) . ?
C50 H50 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.378(9) . ?
C32 H32 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.389(10) . ?
C24 H24 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
N3 P3 C40 113.4(2) . . ?
N3 P3 C34 111.5(2) . . ?
N3 P3 C28 106.1(2) . . ?
C34 P3 C40 108.8(2) . . ?
C28 P3 C40 109.0(2) . . ?
C28 P3 C34 107.9(2) . . ?
N1 P1 C13 113.2(2) . . ?
N1 P1 C7 106.2(2) . . ?
N1 P1 C1 112.9(2) . . ?
C7 P1 C13 110.2(2) . . ?
C7 P1 C1 108.0(2) . . ?
C1 P1 C13 106.2(2) . . ?
C15 P2 C14 101.8(2) . . ?
C21 P2 C15 101.4(2) . . ?
C21 P2 C14 102.1(2) . . ?
C42 P4 C48 99.0(2) . . ?
C42 P4 C41 102.1(2) . . ?
C48 P4 C41 102.0(2) . . ?
C27 N1 P1 122.5(4) . . ?
C54 N3 P3 120.0(3) . . ?
C43 C42 P4 125.2(4) . . ?
C47 C42 P4 116.8(4) . . ?
C47 C42 C43 117.9(5) . . ?
C20 C15 P2 117.6(4) . . ?
C20 C15 C16 118.5(5) . . ?
C16 C15 P2 123.8(4) . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.8(5) . . ?
C8 C9 H9 119.6 . . ?
C15 C20 H20 119.6 . . ?
C15 C20 C19 120.8(5) . . ?
C19 C20 H20 119.6 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C30 C29 C28 119.8(5) . . ?
P3 C40 H40A 109.4 . . ?
P3 C40 H40B 109.4 . . ?
H40A C40 H40B 108.0 . . ?
C41 C40 P3 111.1(3) . . ?
C41 C40 H40A 109.4 . . ?
C41 C40 H40B 109.4 . . ?
C35 C34 P3 117.6(4) . . ?
C35 C34 C39 119.7(5) . . ?
C39 C34 P3 122.6(4) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C44 C45 H45 120.2 . . ?
C44 C45 C46 119.5(5) . . ?
C46 C45 H45 120.2 . . ?
C29 C28 P3 120.3(4) . . ?
C33 C28 P3 120.1(4) . . ?
C33 C28 C29 119.6(4) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.4(5) . . ?
C44 C43 H43 119.8 . . ?
P1 C13 H13A 108.9 . . ?
P1 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 P1 113.3(3) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C21 C26 H26 119.7 . . ?
C21 C26 C25 120.7(5) . . ?
C25 C26 H26 119.7 . . ?
C45 C44 C43 120.7(5) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C42 C47 H47 119.3 . . ?
C46 C47 C42 121.3(5) . . ?
C46 C47 H47 119.3 . . ?
C48 C53 H53 119.9 . . ?
C48 C53 C52 120.2(5) . . ?
C52 C53 H53 119.9 . . ?
C12 C7 P1 120.0(4) . . ?
C12 C7 C8 119.6(5) . . ?
C8 C7 P1 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(5) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(5) . . ?
C36 C35 H35 120.0 . . ?
C38 C37 H37 120.0 . . ?
C38 C37 C36 120.0(5) . . ?
C36 C37 H37 120.0 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C48 C49 H49 119.5 . . ?
C48 C49 C50 121.0(5) . . ?
C50 C49 H49 119.5 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.3(5) . . ?
C32 C31 H31 119.8 . . ?
C26 C21 P2 116.0(4) . . ?
C22 C21 P2 125.4(4) . . ?
C22 C21 C26 118.5(5) . . ?
C2 C1 P1 119.7(4) . . ?
C6 C1 P1 121.0(4) . . ?
C6 C1 C2 119.1(4) . . ?
P2 C14 H14A 110.0 . . ?
P2 C14 H14B 110.0 . . ?
C13 C14 P2 108.5(3) . . ?
C13 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.5(5) . . ?
C11 C12 H12 119.8 . . ?
C53 C48 P4 123.9(4) . . ?
C49 C48 P4 117.2(4) . . ?
C49 C48 C53 118.9(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C9 C8 C7 119.5(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
P4 C41 H41A 109.5 . . ?
P4 C41 H41B 109.5 . . ?
C40 C41 P4 110.8(3) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 H11 120.2 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.4(5) . . ?
C39 C38 H38 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C45 C46 C47 120.1(5) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(5) . . ?
C19 C18 H18 120.4 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.5(5) . . ?
C31 C30 H30 119.8 . . ?
C28 C33 H33 119.8 . . ?
C28 C33 C32 120.5(5) . . ?
C32 C33 H33 119.8 . . ?
C35 C36 C37 120.1(5) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.1(5) . . ?
C23 C22 H22 119.5 . . ?
C34 C39 H39 120.1 . . ?
C38 C39 C34 119.8(5) . . ?
C38 C39 H39 120.1 . . ?
C53 C52 H52 119.9 . . ?
C51 C52 C53 120.2(5) . . ?
C51 C52 H52 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C52 C51 H51 119.9 . . ?
C52 C51 C50 120.1(5) . . ?
C50 C51 H51 119.9 . . ?
C49 C50 C51 119.5(5) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.5(5) . . ?
C24 C25 H25 120.2 . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.4(5) . . ?
C33 C32 H32 120.3 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(6) . . ?
C24 C23 H23 120.3 . . ?
N4 C54 N3 174.7(5) . . ?
N2 C27 N1 174.1(6) . . ?
C25 C24 C23 120.7(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P3 C40 C41 P4 166.9(2) . . . . ?
P3 C34 C35 C36 177.2(4) . . . . ?
P3 C34 C39 C38 -177.9(4) . . . . ?
P3 C28 C33 C32 -175.0(4) . . . . ?
P1 C13 C14 P2 162.3(3) . . . . ?
P1 C7 C12 C11 -172.2(4) . . . . ?
P1 C7 C8 C9 172.5(4) . . . . ?
P1 C1 C2 C3 -174.1(4) . . . . ?
P1 C1 C6 C5 174.8(4) . . . . ?
P2 C15 C20 C19 -180.0(4) . . . . ?
P2 C15 C16 C17 -179.5(4) . . . . ?
P2 C21 C22 C23 -176.9(4) . . . . ?
P4 C42 C43 C44 176.8(4) . . . . ?
P4 C42 C47 C46 -176.3(4) . . . . ?
N1 P1 C13 C14 -58.8(4) . . . . ?
N1 P1 C7 C12 -27.0(4) . . . . ?
N1 P1 C7 C8 159.0(4) . . . . ?
N1 P1 C1 C2 92.7(4) . . . . ?
N1 P1 C1 C6 -83.6(5) . . . . ?
N3 P3 C40 C41 -55.0(4) . . . . ?
N3 P3 C34 C35 38.5(5) . . . . ?
N3 P3 C34 C39 -145.1(4) . . . . ?
N3 P3 C28 C29 152.4(4) . . . . ?
N3 P3 C28 C33 -31.1(4) . . . . ?
C42 P4 C48 C53 75.6(4) . . . . ?
C42 P4 C48 C49 -102.2(4) . . . . ?
C42 P4 C41 C40 -172.6(3) . . . . ?
C42 C43 C44 C45 -0.4(8) . . . . ?
C42 C47 C46 C45 -1.3(8) . . . . ?
C15 P2 C21 C26 -98.5(4) . . . . ?
C15 P2 C21 C22 80.1(5) . . . . ?
C15 P2 C14 C13 -178.5(3) . . . . ?
C15 C20 C19 C18 0.3(8) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C20 C15 C16 C17 3.0(7) . . . . ?
C20 C19 C18 C17 1.1(8) . . . . ?
C29 C28 C33 C32 1.6(7) . . . . ?
C40 P3 N3 C54 -67.4(5) . . . . ?
C40 P3 C34 C35 164.3(4) . . . . ?
C40 P3 C34 C39 -19.2(5) . . . . ?
C40 P3 C28 C29 29.9(4) . . . . ?
C40 P3 C28 C33 -153.6(4) . . . . ?
C34 P3 N3 C54 55.8(5) . . . . ?
C34 P3 C40 C41 -179.6(3) . . . . ?
C34 P3 C28 C29 -88.1(4) . . . . ?
C34 P3 C28 C33 88.4(4) . . . . ?
C34 C35 C36 C37 0.0(9) . . . . ?
C28 P3 N3 C54 173.0(4) . . . . ?
C28 P3 C40 C41 63.0(4) . . . . ?
C28 P3 C34 C35 -77.6(4) . . . . ?
C28 P3 C34 C39 98.9(4) . . . . ?
C28 C29 C30 C31 -0.5(8) . . . . ?
C28 C33 C32 C31 -0.9(8) . . . . ?
C43 C42 C47 C46 0.8(8) . . . . ?
C13 P1 N1 C27 -72.9(5) . . . . ?
C13 P1 C7 C12 -149.9(4) . . . . ?
C13 P1 C7 C8 36.1(4) . . . . ?
C13 P1 C1 C2 -142.7(4) . . . . ?
C13 P1 C1 C6 41.0(5) . . . . ?
C26 C21 C22 C23 1.6(8) . . . . ?
C26 C25 C24 C23 0.1(8) . . . . ?
C44 C45 C46 C47 0.8(8) . . . . ?
C16 C15 C20 C19 -2.3(7) . . . . ?
C16 C17 C18 C19 -0.4(9) . . . . ?
C47 C42 C43 C44 0.0(8) . . . . ?
C53 C52 C51 C50 -1.2(8) . . . . ?
C7 P1 N1 C27 166.1(4) . . . . ?
C7 P1 C13 C14 59.9(4) . . . . ?
C7 P1 C1 C2 -24.5(5) . . . . ?
C7 P1 C1 C6 159.2(4) . . . . ?
C7 C12 C11 C10 -0.5(7) . . . . ?
C35 C34 C39 C38 -1.5(8) . . . . ?
C37 C38 C39 C34 1.7(8) . . . . ?
C10 C9 C8 C7 0.0(7) . . . . ?
C21 P2 C15 C20 113.0(4) . . . . ?
C21 P2 C15 C16 -64.5(5) . . . . ?
C21 P2 C14 C13 -74.0(4) . . . . ?
C21 C26 C25 C24 1.4(8) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C1 P1 N1 C27 47.9(5) . . . . ?
C1 P1 C13 C14 176.7(4) . . . . ?
C1 P1 C7 C12 94.4(4) . . . . ?
C1 P1 C7 C8 -79.6(4) . . . . ?
C1 C2 C3 C4 -1.6(8) . . . . ?
C1 C6 C5 C4 0.1(9) . . . . ?
C14 P2 C15 C20 -141.8(4) . . . . ?
C14 P2 C15 C16 40.7(5) . . . . ?
C14 P2 C21 C26 156.7(4) . . . . ?
C14 P2 C21 C22 -24.8(5) . . . . ?
C12 C7 C8 C9 -1.6(7) . . . . ?
C48 P4 C42 C43 -94.4(5) . . . . ?
C48 P4 C42 C47 82.4(4) . . . . ?
C48 P4 C41 C40 -70.6(4) . . . . ?
C48 C53 C52 C51 0.4(8) . . . . ?
C48 C49 C50 C51 1.3(8) . . . . ?
C2 C1 C6 C5 -1.5(8) . . . . ?
C8 C9 C10 C11 1.3(8) . . . . ?
C8 C7 C12 C11 1.8(7) . . . . ?
C41 P4 C42 C43 10.0(5) . . . . ?
C41 P4 C42 C47 -173.1(4) . . . . ?
C41 P4 C48 C53 -28.9(5) . . . . ?
C41 P4 C48 C49 153.3(4) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C38 C37 C36 C35 0.1(8) . . . . ?
C6 C1 C2 C3 2.2(8) . . . . ?
C46 C45 C44 C43 0.0(8) . . . . ?
C18 C17 C16 C15 -1.7(8) . . . . ?
C30 C29 C28 P3 175.7(4) . . . . ?
C30 C29 C28 C33 -0.9(7) . . . . ?
C30 C31 C32 C33 -0.5(8) . . . . ?
C36 C37 C38 C39 -1.0(8) . . . . ?
C22 C23 C24 C25 -0.7(8) . . . . ?
C39 C34 C35 C36 0.7(8) . . . . ?
C52 C53 C48 P4 -176.4(4) . . . . ?
C52 C53 C48 C49 1.3(7) . . . . ?
C52 C51 C50 C49 0.4(8) . . . . ?
C5 C4 C3 C2 0.2(8) . . . . ?
C50 C49 C48 P4 175.8(4) . . . . ?
C50 C49 C48 C53 -2.1(7) . . . . ?
C25 C26 C21 P2 176.5(4) . . . . ?
C25 C26 C21 C22 -2.2(7) . . . . ?
C32 C31 C30 C29 1.2(8) . . . . ?

_olex2_date_sample_data_collection 2023-02-24
_olex2_date_sample_submission    2023-02-24
_olex2_exptl_crystal_mounting_method 
'mounted ontoa nylon loop using paratone oil.'
_olex2_submission_original_sample_id mds066
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.651
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.00105
2 -0.00105

####################################################################### 
# 
# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 2259467'
loop_
_audit_author_name
_audit_author_address
'Justin Newman'
;Merck and Co, Inc
United States of America
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C20 H17 N4 P)'
_chemical_formula_sum            'C20 H17 N4 P'
_chemical_formula_weight         344.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H18N4P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.8140(3)
_cell_length_b                   14.2764(2)
_cell_length_c                   14.7633(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.840(2)
_cell_angle_gamma                90
_cell_volume                     3574.06(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20486
_cell_measurement_temperature    297.42(10)
_cell_measurement_theta_max      76.8330
_cell_measurement_theta_min      2.5940
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 2 0.0751
0 -1 0 0.0662
-1 -2 1 0.0736
-1 2 2 0.1403
1 1 -1 0.0619
1 -2 -2 0.0987
-1 0 0 0.0461
1 0 0 0.0575
-2 -1 -1 0.0769
-2 0 1 0.0580
1 0 -2 0.1057

_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.104
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 2.0000 -0.1213 0.0108 -0.1711
0.0000 -1.0000 -0.0000 -0.0880 0.0015 0.0624
-1.0000 -2.0000 1.0000 -0.2414 -0.0365 0.0335
-1.0000 2.0000 2.0000 0.0546 0.0079 -0.2960
1.0000 1.0000 -1.0000 0.1534 0.0379 0.0289
1.0000 -2.0000 -2.0000 -0.0546 -0.0079 0.2960
-1.0000 -0.0000 0.0000 -0.0096 -0.0896 -0.0116
1.0000 0.0000 -0.0000 0.0096 0.0896 0.0116
-2.0000 -1.0000 -1.0000 -0.0512 -0.2280 0.1191
-2.0000 -0.0000 1.0000 -0.0750 -0.1290 -0.1029
1.0000 0.0000 -2.0000 0.1213 -0.0108 0.1711

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33748
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.435
_diffrn_reflns_theta_min         2.606
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  22.00   0.50    0.16    --  -50.08  74.00  63.00  182
  2  ω    -93.00 -18.00   0.50    0.64    --  -90.00  74.00  63.00  150
  3  ω    -65.00 -18.00   0.50    0.64    --  -90.00  57.00  60.00   94
  4  ω    -65.00 -39.00   0.50    0.64    --  -90.00  57.00   0.00   52
  5  ω    -46.00 -18.00   0.50    0.64    --  -90.00  38.00   0.00   56
  6  ω    -46.00 -18.00   0.50    0.64    --  -90.00  38.00 -90.00   56
  7  ω    -46.00 -21.00   0.50    0.64    --  -90.00  38.00-150.00   50
  8  ω    -43.00 -18.00   0.50    0.64    --  -90.00  38.00-180.00   50
  9  ω    -33.00  23.00   0.50    0.16    --  -50.08  19.00-150.00  112
 10  ω   -122.00 -31.00   0.50    0.16    --  -50.08 -74.00 -65.00  182
 11  ω   -161.00-111.00   0.50    0.64    --  -90.00 -57.00-120.00  100
 12  ω   -159.00-133.00   0.50    0.64    --  -90.00 -74.00 -65.00   52
 13  ω   -161.00-116.00   0.50    0.64    --  -90.00 -57.00 -30.00   90
 14  ω   -161.00-128.00   0.50    0.64    --  -90.00 -57.00  30.00   66
 15  ω   -145.00-112.00   0.50    0.64    --  -90.00 -99.00   0.00   66
 16  ω   -159.00-114.00   0.50    0.64    --  -90.00 -99.00-150.00   90
 17  ω    -21.00  70.00   0.50    0.16    --   50.08 -74.00 -65.00  182
 18  ω     35.00  91.00   0.50    0.64    --  107.23 -74.00 -65.00  112
 19  ω     37.00  63.00   0.50    0.64    --  107.23 -57.00 -30.00   52
 20  ω     37.00  63.00   0.50    0.64    --  107.23 -57.00   0.00   52
 21  ω     36.00  64.00   0.50    0.64    --  107.23 -57.00-180.00   56
 22  ω    -22.00  31.00   0.50    0.16    --   50.08 -19.00 -60.00  106
 23  ω     35.00  60.00   0.50    0.64    --  107.23 -57.00  90.00   50
 24  ω     35.00  60.00   0.50    0.64    --  107.23 -57.00 120.00   50
 25  ω    118.00 178.00   0.50    0.64    --  107.23  57.00 150.00  120
 26  ω     88.00 178.00   0.50    0.64    --  107.23  74.00  63.00  180
 27  ω     31.00 122.00   0.50    0.16    --   50.08  74.00  63.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0095668000
_diffrn_orient_matrix_UB_12      0.0879799000
_diffrn_orient_matrix_UB_13      -0.0558728000
_diffrn_orient_matrix_UB_21      0.0896160000
_diffrn_orient_matrix_UB_22      -0.0014590000
_diffrn_orient_matrix_UB_23      0.0502209000
_diffrn_orient_matrix_UB_31      0.0115616000
_diffrn_orient_matrix_UB_32      -0.0624399000
_diffrn_orient_matrix_UB_33      -0.0797909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6049
_reflns_number_total             7085
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         7085
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.5289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1099
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C7A-C8A \\sim C7A-C1
 with sigma of 0.02
 C7A-C12A \\sim C7A-C4
 with sigma of 0.02
 C8A-C9A \\sim C1-C2
 with sigma of 0.02
 C7A-C11A \\sim C7A-C3
 with sigma of 0.04
 C10A-C12A \\sim C10A-C4
 with sigma of 0.04
 C9A-C10A \\sim C2-C10A
 with sigma of 0.02
 C7A-C9A \\sim C7A-C2
 with sigma of 0.04
 C8A-C10A \\sim C1-C10A
 with sigma of 0.04
 C10A-C11A \\sim C10A-C3
 with sigma of 0.02
 C11A-C12A \\sim C3-C4
 with sigma of 0.02
 P1B-C18B \\sim P1B-C18C
 with sigma of 0.04
 C14B-C16B \\sim C14C-C16C
 with sigma of 0.04
 N1B-N3B \\sim N1B-N3C
 with sigma of 0.04
 C16B-C18B \\sim C16C-C18C
 with sigma of 0.04
 N3B-N4B \\sim N3C-N4C
 with sigma of 0.04
 P1B-C13B \\sim P1B-C13C
 with sigma of 0.02
 C13B-C17B \\sim C13C-C17C
 with sigma of 0.04
 N1B-C19B \\sim N1B-C19C
 with sigma of 0.02
 N2B-C19B \\sim N2C-C19C
 with sigma of 0.02
 N3B-C19B \\sim N3C-C19C
 with sigma of 0.02
 P1B-C14B \\sim P1B-C14C
 with sigma of 0.04
 N3B-C20B \\sim N3C-C20C
 with sigma of 0.02
 N1B-N2B \\sim N1B-N2C
 with sigma of 0.04
 N4B-C20B \\sim N4C-C20C
 with sigma of 0.02
 N2B-N3B \\sim N2C-N3C
 with sigma of 0.04
 C13B-C14B \\sim C13C-C14C
 with sigma of 0.02
 C13B-C18B \\sim C13C-C18C
 with sigma of 0.02
 C13B-C15B \\sim C13C-C15C
 with sigma of 0.04
 C14B-C15B \\sim C14C-C15C
 with sigma of 0.02
 C15B-C16B \\sim C15C-C16C
 with sigma of 0.02
 C14B-C18B \\sim C14C-C18C
 with sigma of 0.04
 C16B-C17B \\sim C16C-C17C
 with sigma of 0.02
 C15B-C17B \\sim C15C-C17C
 with sigma of 0.04
 C17B-C18B \\sim C17C-C18C
 with sigma of 0.02
 C19B-C20B \\sim C19C-C20C
 with sigma of 0.04
2. Others
 Sof(H10C)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=1-
 FVAR(1)
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=FVAR(1)
 Sof(N4C)=Sof(C20C)=Sof(N3C)=Sof(C19C)=Sof(N2C)=Sof(H2CA)=Sof(H2CB)=Sof(C13C)=
 Sof(C14C)=Sof(H14C)=Sof(C15C)=Sof(H15C)=Sof(C16C)=Sof(H16C)=Sof(C17C)=
 Sof(H17C)=Sof(C18C)=Sof(H18C)=1-FVAR(2)
 Sof(N2B)=Sof(H2BA)=Sof(H2BB)=Sof(N3B)=Sof(N4B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=
 Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=
 Sof(H18B)=Sof(C19B)=Sof(C20B)=FVAR(2)
3.a Rotating group:
 N2B(H2BA,H2BB), N2C(H2CA,H2CB)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A),
 C10A(H10A), C10A(H10C), C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B),
 C6B(H6B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C14B(H14B),
 C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C1(H1), C2(H2), C3(H3), C4(H4),
  C14C(H14C), C15C(H15C), C16C(H16C), C17C(H17C), C18C(H18C)
3.c X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.90837(2) 0.73210(3) 0.94799(2) 0.04622(11) Uani 1 1 d . . . . .
N1A N 0.83681(7) 0.72103(9) 0.85099(8) 0.0531(3) Uani 1 1 d . . . . .
N2A N 0.76224(9) 0.63344(11) 0.72671(10) 0.0698(4) Uani 1 1 d . . . . .
H2AA H 0.750925 0.581504 0.696030 0.084 Uiso 1 1 calc R U . . .
H2AB H 0.734520 0.682680 0.705854 0.084 Uiso 1 1 calc R U . . .
N3A N 0.86767(8) 0.56301(9) 0.84201(9) 0.0589(3) Uani 1 1 d . . . . .
N4A N 0.83178(11) 0.40585(12) 0.77182(13) 0.0813(4) Uani 1 1 d . . . . .
C1A C 1.00443(8) 0.72301(10) 0.93213(10) 0.0489(3) Uani 1 1 d . . . . .
C2A C 1.01046(10) 0.73841(11) 0.84156(11) 0.0585(4) Uani 1 1 d . . . . .
H2A H 0.965248 0.748484 0.790538 0.070 Uiso 1 1 calc R U . . .
C3A C 1.08396(12) 0.73874(13) 0.82736(14) 0.0699(5) Uani 1 1 d . . . . .
H3A H 1.087790 0.749120 0.766744 0.084 Uiso 1 1 calc R U . . .
C4A C 1.15087(12) 0.72389(14) 0.90196(16) 0.0759(5) Uani 1 1 d . . . . .
H4A H 1.199893 0.724472 0.891841 0.091 Uiso 1 1 calc R U . . .
C5A C 1.14586(11) 0.70814(14) 0.99164(15) 0.0729(5) Uani 1 1 d . . . . .
H5A H 1.191446 0.697416 1.041939 0.087 Uiso 1 1 calc R U . . .
C6A C 1.07294(10) 0.70815(12) 1.00755(12) 0.0609(4) Uani 1 1 d . . . . .
H6A H 1.069844 0.698231 1.068560 0.073 Uiso 1 1 calc R U . . .
C7A C 0.90048(9) 0.84916(10) 0.98924(10) 0.0517(3) Uani 1 1 d D . . . .
C8A C 0.9677(4) 0.8938(6) 1.0502(9) 0.082(2) Uani 0.477(16) 1 d D . P A 1
H8A H 1.016740 0.864864 1.065270 0.098 Uiso 0.477(16) 1 calc R U P A 1
C9A C 0.9602(5) 0.9805(6) 1.0873(9) 0.094(3) Uani 0.477(16) 1 d D . P A 1
H9A H 1.003968 1.010168 1.128364 0.112 Uiso 0.477(16) 1 calc R U P A 1
C10A C 0.88599(16) 1.02376(14) 1.06256(16) 0.0900(6) Uani 1 1 d D . . . .
H10A H 0.878547 1.078386 1.093055 0.108 Uiso 0.477(16) 1 calc R U P A 1
H10C H 0.885088 1.085024 1.083628 0.108 Uiso 0.523(16) 1 calc R U P A 2
C11A C 0.8268(6) 0.9860(8) 0.9955(10) 0.098(4) Uani 0.477(16) 1 d D . P A 1
H11A H 0.779326 1.018353 0.974038 0.117 Uiso 0.477(16) 1 calc R U P A 1
C12A C 0.8335(7) 0.9002(9) 0.9565(9) 0.081(4) Uani 0.477(16) 1 d D . P A 1
H12A H 0.791590 0.876947 0.907100 0.097 Uiso 0.477(16) 1 calc R U P A 1
C13A C 0.90340(8) 0.65715(10) 1.04421(10) 0.0481(3) Uani 1 1 d . . . . .
C14A C 0.85012(9) 0.67956(12) 1.09260(11) 0.0596(4) Uani 1 1 d . . . . .
H14A H 0.821181 0.734766 1.078321 0.072 Uiso 1 1 calc R U . . .
C15A C 0.83988(11) 0.62028(14) 1.16182(13) 0.0697(5) Uani 1 1 d . . . . .
H15A H 0.803518 0.635130 1.193293 0.084 Uiso 1 1 calc R U . . .
C16A C 0.88342(10) 0.53938(13) 1.18418(12) 0.0662(4) Uani 1 1 d . . . . .
H16A H 0.876782 0.499772 1.231152 0.079 Uiso 1 1 calc R U . . .
C17A C 0.93682(11) 0.51685(12) 1.13724(13) 0.0681(4) Uani 1 1 d . . . . .
H17A H 0.966115 0.461963 1.152403 0.082 Uiso 1 1 calc R U . . .
C18A C 0.94695(11) 0.57541(11) 1.06789(12) 0.0619(4) Uani 1 1 d . . . . .
H18A H 0.983337 0.559989 1.036625 0.074 Uiso 1 1 calc R U . . .
C19A C 0.82297(9) 0.63764(11) 0.80690(10) 0.0518(3) Uani 1 1 d . . . . .
C20A C 0.84673(10) 0.48063(12) 0.80136(11) 0.0602(4) Uani 1 1 d . . . . .
P1B P 0.44120(2) 0.68803(3) 0.28025(3) 0.05575(12) Uani 1 1 d D . . . .
N1B N 0.53279(12) 0.70277(14) 0.29491(15) 0.0800(5) Uani 1 1 d D . . . .
N2B N 0.6629(3) 0.7510(6) 0.3941(8) 0.0940(18) Uani 0.621(16) 1 d D . P B 1
H2BA H 0.670776 0.766528 0.340288 0.113 Uiso 0.621(16) 1 d R U P B 1
H2BB H 0.683351 0.794688 0.436188 0.113 Uiso 0.621(16) 1 d R U P B 1
N3B N 0.5610(5) 0.7588(8) 0.4585(7) 0.0679(19) Uani 0.621(16) 1 d D . P B 1
N4B N 0.6514(3) 0.7943(5) 0.6213(6) 0.0759(14) Uani 0.621(16) 1 d D . P B 1
C1B C 0.41439(9) 0.61854(11) 0.36728(10) 0.0517(3) Uani 1 1 d . . . . .
C2B C 0.42424(11) 0.52204(12) 0.36660(12) 0.0648(4) Uani 1 1 d . . . . .
H2B H 0.443462 0.494622 0.321003 0.078 Uiso 1 1 calc R U . . .
C3B C 0.40563(12) 0.46669(14) 0.43334(14) 0.0781(5) Uani 1 1 d . . . . .
H3B H 0.411961 0.402075 0.432346 0.094 Uiso 1 1 calc R U . . .
C4B C 0.37785(13) 0.50686(16) 0.50098(14) 0.0818(6) Uani 1 1 d . . . . .
H4B H 0.364965 0.469372 0.545560 0.098 Uiso 1 1 calc R U . . .
C5B C 0.36895(13) 0.60209(16) 0.50327(13) 0.0795(5) Uani 1 1 d . . . . .
H5B H 0.350342 0.628896 0.549674 0.095 Uiso 1 1 calc R U . . .
C6B C 0.38745(11) 0.65861(13) 0.43708(11) 0.0627(4) Uani 1 1 d . . . . .
H6B H 0.381843 0.723257 0.439371 0.075 Uiso 1 1 calc R U . . .
C7B C 0.38826(9) 0.79722(11) 0.26744(10) 0.0541(3) Uani 1 1 d . . . . .
C8B C 0.30751(11) 0.79798(13) 0.25053(13) 0.0672(4) Uani 1 1 d . . . . .
H8B H 0.280105 0.742020 0.247432 0.081 Uiso 1 1 calc R U . . .
C9B C 0.26796(13) 0.88216(15) 0.23831(16) 0.0826(6) Uani 1 1 d . . . . .
H9B H 0.213599 0.883002 0.226466 0.099 Uiso 1 1 calc R U . . .
C10B C 0.30845(14) 0.96500(14) 0.24352(14) 0.0801(6) Uani 1 1 d . . . . .
H10B H 0.281268 1.021521 0.235885 0.096 Uiso 1 1 calc R U . . .
C11B C 0.38788(13) 0.96514(13) 0.25973(12) 0.0722(5) Uani 1 1 d . . . . .
H11B H 0.414748 1.021448 0.262567 0.087 Uiso 1 1 calc R U . . .
C12B C 0.42849(11) 0.88112(12) 0.27198(11) 0.0634(4) Uani 1 1 d . . . . .
H12B H 0.482792 0.880907 0.283267 0.076 Uiso 1 1 calc R U . . .
C13B C 0.4117(8) 0.6290(13) 0.1696(8) 0.064(2) Uani 0.621(16) 1 d D . P B 1
C14B C 0.3417(7) 0.5815(8) 0.1444(6) 0.083(3) Uani 0.621(16) 1 d D . P B 1
H14B H 0.310702 0.582447 0.184956 0.099 Uiso 0.621(16) 1 calc R U P B 1
C15B C 0.3161(7) 0.5322(8) 0.0604(7) 0.093(3) Uani 0.621(16) 1 d D . P B 1
H15B H 0.269305 0.498204 0.043964 0.112 Uiso 0.621(16) 1 calc R U P B 1
C16B C 0.3629(8) 0.5359(8) 0.0021(6) 0.090(4) Uani 0.621(16) 1 d D . P B 1
H16B H 0.347744 0.502247 -0.054548 0.108 Uiso 0.621(16) 1 calc R U P B 1
C17B C 0.4305(8) 0.5866(8) 0.0239(7) 0.092(3) Uani 0.621(16) 1 d D . P B 1
H17B H 0.459566 0.588830 -0.018795 0.110 Uiso 0.621(16) 1 calc R U P B 1
C18B C 0.4565(6) 0.6349(7) 0.1089(6) 0.0733(17) Uani 0.621(16) 1 d D . P B 1
H18B H 0.502699 0.670005 0.124463 0.088 Uiso 0.621(16) 1 calc R U P B 1
C19B C 0.5819(4) 0.7371(10) 0.3804(7) 0.079(3) Uani 0.621(16) 1 d D . P B 1
C20B C 0.6104(4) 0.7802(7) 0.5435(6) 0.0623(16) Uani 0.621(16) 1 d D . P B 1
C1 C 0.9454(5) 0.8749(4) 1.0808(4) 0.0697(17) Uani 0.523(16) 1 d D . P A 2
H1 H 0.982027 0.833128 1.118092 0.084 Uiso 0.523(16) 1 calc R U P A 2
C2 C 0.9362(6) 0.9611(5) 1.1162(4) 0.0831(19) Uani 0.523(16) 1 d D . P A 2
H2 H 0.965122 0.976434 1.178348 0.100 Uiso 0.523(16) 1 calc R U P A 2
C3 C 0.8361(7) 0.9964(8) 0.9764(7) 0.094(4) Uani 0.523(16) 1 d D . P A 2
H3 H 0.797447 1.037372 0.941359 0.112 Uiso 0.523(16) 1 calc R U P A 2
C4 C 0.8426(7) 0.9081(7) 0.9409(7) 0.071(3) Uani 0.523(16) 1 d D . P A 2
H4 H 0.807095 0.889234 0.883363 0.085 Uiso 0.523(16) 1 calc R U P A 2
N4C N 0.6630(6) 0.7882(9) 0.5881(8) 0.076(2) Uani 0.379(16) 1 d D . P B 2
C20C C 0.6198(6) 0.7711(12) 0.5154(9) 0.062(3) Uani 0.379(16) 1 d D . P B 2
N3C N 0.5607(7) 0.7537(13) 0.4412(10) 0.076(4) Uani 0.379(16) 1 d D . P B 2
C19C C 0.5842(8) 0.7321(17) 0.3678(11) 0.092(6) Uani 0.379(16) 1 d D . P B 2
N2C N 0.6553(4) 0.7308(7) 0.3500(8) 0.0702(19) Uani 0.379(16) 1 d D . P B 2
H2CA H 0.687988 0.693560 0.388973 0.084 Uiso 0.379(16) 1 d R U P B 2
H2CB H 0.650132 0.712505 0.292458 0.084 Uiso 0.379(16) 1 d R U P B 2
C13C C 0.3961(12) 0.6215(19) 0.1699(12) 0.050(2) Uani 0.379(16) 1 d D . P B 2
C14C C 0.3258(7) 0.5718(11) 0.1523(8) 0.0492(19) Uani 0.379(16) 1 d D . P B 2
H14C H 0.299513 0.570806 0.197813 0.059 Uiso 0.379(16) 1 calc R U P B 2
C15C C 0.2939(7) 0.5224(11) 0.0652(9) 0.062(2) Uani 0.379(16) 1 d D . P B 2
H15C H 0.245396 0.492732 0.053057 0.074 Uiso 0.379(16) 1 calc R U P B 2
C16C C 0.3340(9) 0.5178(14) -0.0019(12) 0.064(2) Uani 0.379(16) 1 d D . P B 2
H16C H 0.314042 0.482752 -0.057170 0.077 Uiso 0.379(16) 1 calc R U P B 2
C17C C 0.4032(8) 0.5658(11) 0.0150(9) 0.075(4) Uani 0.379(16) 1 d D . P B 2
H17C H 0.429860 0.565392 -0.030203 0.090 Uiso 0.379(16) 1 calc R U P B 2
C18C C 0.4343(7) 0.6156(10) 0.1000(9) 0.065(2) Uani 0.379(16) 1 d D . P B 2
H18C H 0.482357 0.646045 0.110489 0.077 Uiso 0.379(16) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1A N1A 1.6068(12) . ?
P1A C1A 1.8016(15) . ?
P1A C7A 1.7989(15) . ?
P1A C13A 1.8021(14) . ?
N1A C19A 1.3430(19) . ?
N2A H2AA 0.8600 . ?
N2A H2AB 0.8600 . ?
N2A C19A 1.338(2) . ?
N3A C19A 1.336(2) . ?
N3A C20A 1.321(2) . ?
N4A C20A 1.153(2) . ?
C1A C2A 1.391(2) . ?
C1A C6A 1.393(2) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.388(2) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.369(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.373(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.389(2) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.411(6) . ?
C7A C12A 1.355(9) . ?
C7A C1 1.393(5) . ?
C7A C4 1.353(8) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.376(8) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.402(8) . ?
C10A H10A 0.9300 . ?
C10A H10C 0.9300 . ?
C10A C11A 1.320(10) . ?
C10A C2 1.339(7) . ?
C10A C3 1.367(8) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.374(10) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.389(2) . ?
C13A C18A 1.386(2) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.381(2) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.374(3) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.376(2) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.376(2) . ?
C18A H18A 0.9300 . ?
P1B N1B 1.5926(19) . ?
P1B C1B 1.7998(14) . ?
P1B C7B 1.8017(16) . ?
P1B C13B 1.769(7) . ?
P1B C13C 1.843(11) . ?
N1B C19B 1.386(7) . ?
N1B C19C 1.252(13) . ?
N2B H2BA 0.8763 . ?
N2B H2BB 0.8776 . ?
N2B C19B 1.408(7) . ?
N3B C19B 1.352(9) . ?
N3B C20B 1.329(8) . ?
N4B C20B 1.175(8) . ?
C1B C2B 1.389(2) . ?
C1B C6B 1.387(2) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.380(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.369(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.370(3) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.383(2) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.383(2) . ?
C7B C12B 1.387(2) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.377(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.375(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.361(3) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.384(3) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.367(8) . ?
C13B C18B 1.373(8) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.376(8) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.371(8) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.357(8) . ?
C17B H17B 0.9300 . ?
C17B C18B 1.382(9) . ?
C18B H18B 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.367(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(9) . ?
C4 H4 0.9300 . ?
N4C C20C 1.140(11) . ?
C20C N3C 1.289(11) . ?
N3C C19C 1.313(12) . ?
C19C N2C 1.369(12) . ?
N2C H2CA 0.8650 . ?
N2C H2CB 0.8665 . ?
C13C C14C 1.393(11) . ?
C13C C18C 1.402(11) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.422(11) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.388(13) . ?
C16C H16C 0.9300 . ?
C16C C17C 1.365(12) . ?
C17C H17C 0.9300 . ?
C17C C18C 1.400(12) . ?
C18C H18C 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A P1A C1A 113.76(7) . . ?
N1A P1A C7A 105.67(7) . . ?
N1A P1A C13A 115.28(7) . . ?
C1A P1A C13A 109.73(7) . . ?
C7A P1A C1A 106.66(7) . . ?
C7A P1A C13A 104.89(7) . . ?
C19A N1A P1A 119.79(11) . . ?
H2AA N2A H2AB 120.0 . . ?
C19A N2A H2AA 120.0 . . ?
C19A N2A H2AB 120.0 . . ?
C20A N3A C19A 118.81(14) . . ?
C2A C1A P1A 118.01(12) . . ?
C2A C1A C6A 119.04(14) . . ?
C6A C1A P1A 122.78(11) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 119.98(16) . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.47(17) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 119.9 . . ?
C3A C4A C5A 120.23(17) . . ?
C5A C4A H4A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C4A C5A C6A 120.24(18) . . ?
C6A C5A H5A 119.9 . . ?
C1A C6A H6A 120.0 . . ?
C5A C6A C1A 120.03(16) . . ?
C5A C6A H6A 120.0 . . ?
C8A C7A P1A 119.8(3) . . ?
C12A C7A P1A 122.0(5) . . ?
C12A C7A C8A 117.9(6) . . ?
C1 C7A P1A 119.5(2) . . ?
C4 C7A P1A 121.7(4) . . ?
C4 C7A C1 117.8(4) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A C7A 119.6(5) . . ?
C9A C8A H8A 120.2 . . ?
C8A C9A H9A 120.3 . . ?
C8A C9A C10A 119.4(5) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 120.4 . . ?
C11A C10A C9A 119.2(5) . . ?
C11A C10A H10A 120.4 . . ?
C2 C10A H10C 120.5 . . ?
C2 C10A C3 119.1(5) . . ?
C3 C10A H10C 120.5 . . ?
C10A C11A H11A 119.1 . . ?
C10A C11A C12A 121.8(9) . . ?
C12A C11A H11A 119.1 . . ?
C7A C12A C11A 120.6(9) . . ?
C7A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C14A C13A P1A 118.36(11) . . ?
C18A C13A P1A 122.68(11) . . ?
C18A C13A C14A 118.83(14) . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A C13A 120.36(15) . . ?
C15A C14A H14A 119.8 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.00(15) . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A H16A 119.9 . . ?
C15A C16A C17A 120.14(15) . . ?
C17A C16A H16A 119.9 . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.09(16) . . ?
C18A C17A H17A 120.0 . . ?
C13A C18A H18A 119.7 . . ?
C17A C18A C13A 120.57(15) . . ?
C17A C18A H18A 119.7 . . ?
N2A C19A N1A 116.56(14) . . ?
N3A C19A N1A 121.31(13) . . ?
N3A C19A N2A 122.12(14) . . ?
N4A C20A N3A 175.1(2) . . ?
N1B P1B C1B 117.44(8) . . ?
N1B P1B C7B 112.42(9) . . ?
N1B P1B C13B 101.0(4) . . ?
N1B P1B C13C 109.8(5) . . ?
C1B P1B C7B 107.88(7) . . ?
C1B P1B C13C 102.0(7) . . ?
C7B P1B C13C 106.3(10) . . ?
C13B P1B C1B 109.1(5) . . ?
C13B P1B C7B 108.5(7) . . ?
C19B N1B P1B 120.3(3) . . ?
C19C N1B P1B 127.6(7) . . ?
H2BA N2B H2BB 108.3 . . ?
C19B N2B H2BA 110.3 . . ?
C19B N2B H2BB 112.7 . . ?
C20B N3B C19B 125.7(7) . . ?
C2B C1B P1B 118.67(12) . . ?
C6B C1B P1B 122.08(12) . . ?
C6B C1B C2B 119.20(14) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B C1B 120.27(17) . . ?
C3B C2B H2B 119.9 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.03(19) . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B H4B 119.9 . . ?
C3B C4B C5B 120.27(17) . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B H5B 119.8 . . ?
C4B C5B C6B 120.47(18) . . ?
C6B C5B H5B 119.8 . . ?
C1B C6B H6B 120.1 . . ?
C5B C6B C1B 119.74(17) . . ?
C5B C6B H6B 120.1 . . ?
C8B C7B P1B 120.53(13) . . ?
C8B C7B C12B 119.71(15) . . ?
C12B C7B P1B 119.74(13) . . ?
C7B C8B H8B 120.2 . . ?
C9B C8B C7B 119.52(18) . . ?
C9B C8B H8B 120.2 . . ?
C8B C9B H9B 119.8 . . ?
C10B C9B C8B 120.33(19) . . ?
C10B C9B H9B 119.8 . . ?
C9B C10B H10B 119.7 . . ?
C11B C10B C9B 120.69(18) . . ?
C11B C10B H10B 119.7 . . ?
C10B C11B H11B 120.1 . . ?
C10B C11B C12B 119.70(18) . . ?
C12B C11B H11B 120.1 . . ?
C7B C12B H12B 120.0 . . ?
C11B C12B C7B 120.04(18) . . ?
C11B C12B H12B 120.0 . . ?
C14B C13B P1B 118.4(6) . . ?
C14B C13B C18B 121.2(6) . . ?
C18B C13B P1B 120.4(6) . . ?
C13B C14B H14B 119.3 . . ?
C13B C14B C15B 121.4(7) . . ?
C15B C14B H14B 119.3 . . ?
C14B C15B H15B 121.7 . . ?
C16B C15B C14B 116.7(7) . . ?
C16B C15B H15B 121.7 . . ?
C15B C16B H16B 118.7 . . ?
C17B C16B C15B 122.6(7) . . ?
C17B C16B H16B 118.7 . . ?
C16B C17B H17B 119.8 . . ?
C16B C17B C18B 120.5(7) . . ?
C18B C17B H17B 119.8 . . ?
C13B C18B C17B 117.5(6) . . ?
C13B C18B H18B 121.3 . . ?
C17B C18B H18B 121.3 . . ?
N1B C19B N2B 120.9(8) . . ?
N3B C19B N1B 126.6(6) . . ?
N3B C19B N2B 112.5(8) . . ?
N4B C20B N3B 175.3(10) . . ?
C7A C1 H1 119.7 . . ?
C2 C1 C7A 120.6(5) . . ?
C2 C1 H1 119.7 . . ?
C10A C2 C1 120.8(5) . . ?
C10A C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C10A C3 H3 119.8 . . ?
C10A C3 C4 120.4(8) . . ?
C4 C3 H3 119.8 . . ?
C7A C4 C3 120.4(7) . . ?
C7A C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N4C C20C N3C 168.9(11) . . ?
C20C N3C C19C 111.2(11) . . ?
N1B C19C N3C 117.0(11) . . ?
N1B C19C N2C 107.8(10) . . ?
N3C C19C N2C 135.2(13) . . ?
C19C N2C H2CA 110.8 . . ?
C19C N2C H2CB 111.5 . . ?
H2CA N2C H2CB 108.3 . . ?
C14C C13C P1B 123.5(9) . . ?
C14C C13C C18C 116.2(9) . . ?
C18C C13C P1B 120.2(9) . . ?
C13C C14C H14C 119.7 . . ?
C13C C14C C15C 120.6(9) . . ?
C15C C14C H14C 119.7 . . ?
C14C C15C H15C 119.4 . . ?
C16C C15C C14C 121.2(10) . . ?
C16C C15C H15C 119.4 . . ?
C15C C16C H16C 120.7 . . ?
C17C C16C C15C 118.6(12) . . ?
C17C C16C H16C 120.7 . . ?
C16C C17C H17C 119.8 . . ?
C16C C17C C18C 120.4(11) . . ?
C18C C17C H17C 119.8 . . ?
C13C C18C H18C 118.6 . . ?
C17C C18C C13C 122.9(8) . . ?
C17C C18C H18C 118.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H2AB N4B 0.86 2.27 3.116(7) 167.6 . yes
N2A H2AB N4C 0.86 2.36 3.159(11) 155.2 . yes

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
P1A N1A C19A N2A 179.73(11) . . . . ?
P1A N1A C19A N3A 0.0(2) . . . . ?
P1A C1A C2A C3A 175.42(13) . . . . ?
P1A C1A C6A C5A -175.62(13) . . . . ?
P1A C7A C8A C9A -175.2(5) . . . . ?
P1A C7A C12A C11A 174.1(11) . . . . ?
P1A C7A C1 C2 -175.1(4) . . . . ?
P1A C7A C4 C3 177.3(9) . . . . ?
P1A C13A C14A C15A 174.94(14) . . . . ?
P1A C13A C18A C17A -175.10(14) . . . . ?
N1A P1A C1A C2A 20.60(14) . . . . ?
N1A P1A C1A C6A -164.22(13) . . . . ?
N1A P1A C7A C8A -156.3(7) . . . . ?
N1A P1A C7A C12A 17.1(9) . . . . ?
N1A P1A C7A C1 168.4(5) . . . . ?
N1A P1A C7A C4 0.1(7) . . . . ?
N1A P1A C13A C14A -75.27(14) . . . . ?
N1A P1A C13A C18A 100.70(14) . . . . ?
C1A P1A N1A C19A 68.88(13) . . . . ?
C1A P1A C7A C8A -35.0(7) . . . . ?
C1A P1A C7A C12A 138.5(9) . . . . ?
C1A P1A C7A C1 -70.2(5) . . . . ?
C1A P1A C7A C4 121.5(7) . . . . ?
C1A P1A C13A C14A 154.74(12) . . . . ?
C1A P1A C13A C18A -29.29(16) . . . . ?
C1A C2A C3A C4A 0.1(3) . . . . ?
C2A C1A C6A C5A -0.5(2) . . . . ?
C2A C3A C4A C5A 0.3(3) . . . . ?
C3A C4A C5A C6A -0.7(3) . . . . ?
C4A C5A C6A C1A 0.8(3) . . . . ?
C6A C1A C2A C3A 0.1(2) . . . . ?
C7A P1A N1A C19A -174.45(12) . . . . ?
C7A P1A C1A C2A -95.49(13) . . . . ?
C7A P1A C1A C6A 79.69(14) . . . . ?
C7A P1A C13A C14A 40.50(14) . . . . ?
C7A P1A C13A C18A -143.53(14) . . . . ?
C7A C8A C9A C10A -1.0(10) . . . . ?
C7A C1 C2 C10A -2.5(8) . . . . ?
C8A C7A C12A C11A -12.3(17) . . . . ?
C8A C9A C10A C11A -8.2(12) . . . . ?
C9A C10A C11A C12A 7.3(18) . . . . ?
C10A C11A C12A C7A 3(2) . . . . ?
C10A C3 C4 C7A -2.6(19) . . . . ?
C12A C7A C8A C9A 11.1(11) . . . . ?
C13A P1A N1A C19A -59.14(13) . . . . ?
C13A P1A C1A C2A 151.41(12) . . . . ?
C13A P1A C1A C6A -33.41(15) . . . . ?
C13A P1A C7A C8A 81.4(7) . . . . ?
C13A P1A C7A C12A -105.1(9) . . . . ?
C13A P1A C7A C1 46.2(5) . . . . ?
C13A P1A C7A C4 -122.1(7) . . . . ?
C13A C14A C15A C16A 1.0(3) . . . . ?
C14A C13A C18A C17A 0.8(3) . . . . ?
C14A C15A C16A C17A -0.5(3) . . . . ?
C15A C16A C17A C18A 0.2(3) . . . . ?
C16A C17A C18A C13A -0.3(3) . . . . ?
C18A C13A C14A C15A -1.2(2) . . . . ?
C20A N3A C19A N1A 173.19(14) . . . . ?
C20A N3A C19A N2A -6.6(2) . . . . ?
P1B N1B C19B N2B -179.7(8) . . . . ?
P1B N1B C19B N3B 1.9(16) . . . . ?
P1B N1B C19C N3C 0(3) . . . . ?
P1B N1B C19C N2C 178.1(7) . . . . ?
P1B C1B C2B C3B 178.85(14) . . . . ?
P1B C1B C6B C5B -178.86(14) . . . . ?
P1B C7B C8B C9B -178.18(15) . . . . ?
P1B C7B C12B C11B 178.32(12) . . . . ?
P1B C13B C14B C15B -178.4(11) . . . . ?
P1B C13B C18B C17B 179.5(11) . . . . ?
P1B C13C C14C C15C 179.5(17) . . . . ?
P1B C13C C18C C17C 179.7(16) . . . . ?
N1B P1B C1B C2B -73.93(16) . . . . ?
N1B P1B C1B C6B 103.31(16) . . . . ?
N1B P1B C7B C8B 177.57(14) . . . . ?
N1B P1B C7B C12B -0.67(16) . . . . ?
N1B P1B C13B C14B 162.3(14) . . . . ?
N1B P1B C13B C18B -20.7(17) . . . . ?
N1B P1B C13C C14C 159(2) . . . . ?
N1B P1B C13C C18C -19(3) . . . . ?
C1B P1B N1B C19B -53.5(7) . . . . ?
C1B P1B N1B C19C -52.7(15) . . . . ?
C1B P1B C7B C8B -51.37(15) . . . . ?
C1B P1B C7B C12B 130.39(12) . . . . ?
C1B P1B C13B C14B 38.0(17) . . . . ?
C1B P1B C13B C18B -145.0(14) . . . . ?
C1B P1B C13C C14C 33(3) . . . . ?
C1B P1B C13C C18C -144(2) . . . . ?
C1B C2B C3B C4B -0.5(3) . . . . ?
C2B C1B C6B C5B -1.6(3) . . . . ?
C2B C3B C4B C5B -0.5(3) . . . . ?
C3B C4B C5B C6B 0.4(3) . . . . ?
C4B C5B C6B C1B 0.7(3) . . . . ?
C6B C1B C2B C3B 1.5(3) . . . . ?
C7B P1B N1B C19B 72.6(7) . . . . ?
C7B P1B N1B C19C 73.4(15) . . . . ?
C7B P1B C1B C2B 157.82(13) . . . . ?
C7B P1B C1B C6B -24.94(16) . . . . ?
C7B P1B C13B C14B -79.3(16) . . . . ?
C7B P1B C13B C18B 97.7(15) . . . . ?
C7B P1B C13C C14C -80(2) . . . . ?
C7B P1B C13C C18C 103(2) . . . . ?
C7B C8B C9B C10B -0.5(3) . . . . ?
C8B C7B C12B C11B 0.1(2) . . . . ?
C8B C9B C10B C11B 0.7(3) . . . . ?
C9B C10B C11B C12B -0.6(3) . . . . ?
C10B C11B C12B C7B 0.2(3) . . . . ?
C12B C7B C8B C9B 0.1(3) . . . . ?
C13B P1B N1B C19B -172.0(10) . . . . ?
C13B P1B C1B C2B 40.1(6) . . . . ?
C13B P1B C1B C6B -142.6(6) . . . . ?
C13B P1B C7B C8B 66.7(4) . . . . ?
C13B P1B C7B C12B -111.5(4) . . . . ?
C13B C14B C15B C16B -2(2) . . . . ?
C14B C13B C18B C17B -4(2) . . . . ?
C14B C15B C16B C17B -1.3(18) . . . . ?
C15B C16B C17B C18B 2.3(17) . . . . ?
C16B C17B C18B C13B 0.2(18) . . . . ?
C18B C13B C14B C15B 5(3) . . . . ?
C20B N3B C19B N1B 170.8(11) . . . . ?
C20B N3B C19B N2B -7.7(19) . . . . ?
C1 C7A C4 C3 8.7(16) . . . . ?
C2 C10A C3 C4 -6.4(15) . . . . ?
C3 C10A C2 C1 8.8(10) . . . . ?
C4 C7A C1 C2 -6.4(10) . . . . ?
N4C C20C N3C C19C -178(9) . . . . ?
C20C N3C C19C N1B 171.6(18) . . . . ?
C20C N3C C19C N2C -6(4) . . . . ?
C13C P1B N1B C19C -168.5(18) . . . . ?
C13C P1B C1B C2B 46.1(9) . . . . ?
C13C P1B C1B C6B -136.6(9) . . . . ?
C13C P1B C7B C8B 57.4(5) . . . . ?
C13C P1B C7B C12B -120.8(5) . . . . ?
C13C C14C C15C C16C 4(3) . . . . ?
C14C C13C C18C C17C 2(4) . . . . ?
C14C C15C C16C C17C -3(3) . . . . ?
C15C C16C C17C C18C 2(3) . . . . ?
C16C C17C C18C C13C -2(3) . . . . ?
C18C C13C C14C C15C -3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.832
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, acetone, hexane'
####################################################################### 
# 
# 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_Compound_R_23
_database_code_depnum_ccdc_archive 'CCDC 2259466'
loop_
_audit_author_name
_audit_author_address
'Justin Newman'
;Merck and Co, Inc
United States of America
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N3 O P'
_chemical_formula_sum            'C25 H24 N3 O P'
_chemical_formula_weight         413.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H24 N3 O P '
_chemical_oxdiff_usercomment     5057422-0090
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.39428(9)
_cell_length_b                   11.00098(13)
_cell_length_c                   20.6966(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2138.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2970
_cell_measurement_theta_min      4.0080
_shelx_estimated_absorpt_T_max   0.792
_shelx_estimated_absorpt_T_min   0.677
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.243
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 1 0.0947
0 1 -1 0.1600
-1 -1 0 0.0693
0 -1 1 0.1349
1 0 1 0.1037
-1 2 -2 0.1692
0 -2 1 0.1237
-2 -2 -1 0.0758
-1 0 -1 0.1166
1 1 1 0.1078
-1 -1 -1 0.0851
0 -1 0 0.1175
-1 -2 -1 0.0901
-2 -1 -2 0.0971
1 1 2 0.1045
0 2 1 0.1412
0 -2 -1 0.1094
1 -2 0 0.1256
-1 2 0 0.1639
1 0 -2 0.0730
-1 0 2 0.1151
0 0 1 0.1279
0 1 2 0.0831
-1 0 -2 0.1166
1 -2 -2 0.0981
0 -1 -2 0.1117
1 -1 -2 0.0777
2 0 -1 0.0719
0 1 -2 0.1436

_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.188
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0016 0.9997 0.9964 0.2280 0.1160 0.2595
0.0006 0.9997 -1.0020 0.1296 0.0450 -0.0797
-1.0011 -0.9997 0.0028 -0.1788 -0.0805 -0.0899
-0.0006 -0.9997 1.0020 -0.1296 -0.0450 0.0797
1.0005 0.0000 0.9992 0.0492 0.0355 0.1696
-0.9991 1.9996 -2.0036 0.1694 0.1072 -0.2955
-0.0014 -1.9996 1.0044 -0.2186 -0.1427 0.1259
-2.0025 -1.9997 -0.9940 -0.3170 -0.2137 -0.2133
-1.0005 -0.0000 -0.9992 -0.0492 -0.0355 -0.1696
1.0014 1.0000 0.9968 0.1382 0.1332 0.1233
-1.0014 -1.0000 -0.9968 -0.1382 -0.1332 -0.1233
-0.0009 -0.9999 0.0024 -0.0890 -0.0977 0.0463
-1.0022 -1.9999 -0.9945 -0.2272 -0.2309 -0.0771
-2.0019 -1.0000 -1.9960 -0.1875 -0.1687 -0.2929
1.0016 1.0002 1.9965 0.0977 0.1859 0.1567
0.0020 2.0002 0.9949 0.1375 0.2481 -0.0592
-0.0020 -2.0002 -0.9949 -0.1375 -0.2481 0.0592
0.9985 -2.0001 0.0043 -0.0882 -0.2126 0.2288
-0.9985 2.0001 -0.0043 0.0882 0.2126 -0.2288
0.9997 -0.0008 -1.9998 0.1709 -0.1225 0.0694
-0.9997 0.0008 1.9998 -0.1709 0.1225 -0.0694
0.0003 0.0003 0.9997 -0.0406 0.0527 0.0334
0.0014 1.0005 1.9969 0.0079 0.2031 0.0205
-1.0008 -0.0003 -1.9989 -0.0087 -0.0882 -0.2030
0.9980 -2.0007 -1.9950 -0.0071 -0.3180 0.1620
-0.0014 -1.0005 -1.9969 -0.0079 -0.2031 -0.0205
0.9989 -1.0008 -1.9974 0.0819 -0.2203 0.1157
2.0002 -0.0008 -1.0006 0.2201 -0.0870 0.2390
0.0003 0.9994 -2.0017 0.1701 -0.0077 -0.1130

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20050
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.560
_diffrn_reflns_theta_min         4.272
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  22.00   0.50    0.05    --  -50.08  98.00 101.00  204
  2  ω    -46.00 -18.00   0.50    0.05    --  -90.00  38.00 120.00   56
  3  ω    -46.00 -18.00   0.50    0.05    --  -90.00  38.00  90.00   56
  4  ω    -46.00 -18.00   0.50    0.05    --  -90.00  38.00 -90.00   56
  5  ω    -33.00  23.00   0.50    0.05    --  -50.08  19.00 -30.00  112
  6  ω   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00 -30.00  158
  7  ω   -161.00-115.00   0.50    0.05    --  -90.00 -77.00-120.00   92
  8  ω   -161.00-111.00   0.50    0.05    --  -90.00 -57.00-150.00  100
  9  ω   -161.00-111.00   0.50    0.05    --  -90.00 -57.00-180.00  100
 10  ω   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00-120.00  158
 11  ω   -161.00 -81.00   0.50    0.05    --  -90.00 -45.00  93.00  160
 12  ω   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00 150.00  158
 13  ω   -121.00 -65.00   0.50    0.05    --  -50.08 -38.00  30.00  112
 14  ω   -161.00 -79.00   0.50    0.05    --  -90.00 -87.00-111.00  164
 15  ω   -161.00 -98.00   0.50    0.05    --  -90.00-125.00-180.00  126
 16  ω    -11.00  71.00   0.50    0.05    --   50.08 -77.00   0.00  164
 17  ω     35.00  98.00   0.50    0.05    --  107.23 -77.00 -60.00  126
 18  ω     35.00  64.00   0.50    0.05    --  107.23 -57.00 -90.00   58
 19  ω     35.00  64.00   0.50    0.05    --  107.23 -57.00 -30.00   58
 20  ω     35.00  64.00   0.50    0.05    --  107.23 -57.00  30.00   58
 21  ω     35.00  64.00   0.50    0.05    --  107.23 -57.00  90.00   58
 22  ω    106.00 178.00   0.50    0.05    --  107.23  98.00 101.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0897681000
_diffrn_orient_matrix_UB_12      0.0888421000
_diffrn_orient_matrix_UB_13      -0.0406258000
_diffrn_orient_matrix_UB_21      -0.0171296000
_diffrn_orient_matrix_UB_22      0.0978559000
_diffrn_orient_matrix_UB_23      0.0526753000
_diffrn_orient_matrix_UB_31      0.1361830000
_diffrn_orient_matrix_UB_32      -0.0463094000
_diffrn_orient_matrix_UB_33      0.0333737000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                4100
_reflns_number_total             4197
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.5366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0649
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
1.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.10317(5) 0.08991(4) 0.10972(2) 0.01645(12) Uani 1 1 d . . . . .
O1 O 0.52129(13) 0.31826(12) 0.10196(7) 0.0236(3) Uani 1 1 d . . . . .
N1 N -0.05883(16) 0.07095(15) 0.08696(8) 0.0216(4) Uani 1 1 d . . . . .
N2 N -0.22146(17) -0.09675(15) 0.11562(9) 0.0270(4) Uani 1 1 d . . . . .
N3 N 0.40357(17) 0.16194(14) 0.14903(8) 0.0201(3) Uani 1 1 d . . . . .
C1 C -0.13936(19) -0.02039(17) 0.10350(9) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.14008(19) 0.24230(17) 0.07949(9) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.0262(2) 0.29763(18) 0.04708(9) 0.0203(4) Uani 1 1 d . . . . .
H3 H -0.061159 0.254841 0.042841 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0380(2) 0.41358(19) 0.02101(9) 0.0225(4) Uani 1 1 d . . . . .
H4 H -0.040469 0.448736 -0.001094 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1635(2) 0.47786(19) 0.02714(10) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.171127 0.557956 0.010329 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2782(2) 0.42437(18) 0.05803(9) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.364812 0.468355 0.061772 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2696(2) 0.30712(17) 0.08389(9) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.39852(19) 0.25619(16) 0.11405(9) 0.0186(4) Uani 1 1 d . . . . .
C9 C 0.6308(2) 0.2545(2) 0.13788(10) 0.0274(5) Uani 1 1 d . . . . .
H9A H 0.671965 0.307659 0.171660 0.033 Uiso 1 1 calc R U . . .
H9B H 0.707970 0.227235 0.108743 0.033 Uiso 1 1 calc R U . . .
C10 C 0.55410(19) 0.14449(18) 0.16859(10) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.591170 0.067888 0.148744 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5698(2) 0.13693(19) 0.24214(10) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.529388 0.212709 0.261528 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7272(2) 0.1279(2) 0.26112(11) 0.0333(5) Uani 1 1 d . . . . .
H12A H 0.768419 0.054063 0.242388 0.050 Uiso 1 1 calc R U . . .
H12B H 0.735393 0.124723 0.308294 0.050 Uiso 1 1 calc R U . . .
H12C H 0.778399 0.199214 0.244810 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4888(2) 0.0283(2) 0.26920(11) 0.0331(5) Uani 1 1 d . . . . .
H13A H 0.388080 0.034757 0.257425 0.050 Uiso 1 1 calc R U . . .
H13B H 0.497968 0.027020 0.316367 0.050 Uiso 1 1 calc R U . . .
H13C H 0.528382 -0.046921 0.251224 0.050 Uiso 1 1 calc R U . . .
C14 C 0.21283(19) -0.02582(17) 0.07282(9) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.1786(2) -0.05935(18) 0.00917(9) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.105920 -0.017222 -0.013582 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2510(2) -0.15400(19) -0.02034(10) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.226471 -0.177958 -0.063004 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3596(2) -0.21399(19) 0.01240(10) 0.0266(5) Uani 1 1 d . . . . .
H17 H 0.410056 -0.277986 -0.008228 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3943(2) -0.18068(18) 0.07498(10) 0.0258(4) Uani 1 1 d . . . . .
H18 H 0.468741 -0.221792 0.097089 0.031 Uiso 1 1 calc R U . . .
C19 C 0.32095(19) -0.08752(17) 0.10551(10) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.344245 -0.065708 0.148643 0.025 Uiso 1 1 calc R U . . .
C20 C 0.11371(19) 0.07694(17) 0.19622(9) 0.0179(4) Uani 1 1 d . . . . .
C21 C 0.08352(19) -0.03690(17) 0.22297(9) 0.0198(4) Uani 1 1 d . . . . .
H21 H 0.069001 -0.105154 0.195630 0.024 Uiso 1 1 calc R U . . .
C22 C 0.07480(19) -0.04993(19) 0.28960(9) 0.0221(4) Uani 1 1 d . . . . .
H22 H 0.055267 -0.127301 0.307960 0.026 Uiso 1 1 calc R U . . .
C23 C 0.0946(2) 0.05005(19) 0.32922(9) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.087647 0.041123 0.374762 0.030 Uiso 1 1 calc R U . . .
C24 C 0.1247(2) 0.16337(19) 0.30286(9) 0.0243(4) Uani 1 1 d . . . . .
H24 H 0.138322 0.231594 0.330317 0.029 Uiso 1 1 calc R U . . .
C25 C 0.13485(19) 0.17661(17) 0.23643(9) 0.0202(4) Uani 1 1 d . . . . .
H25 H 0.156243 0.253841 0.218341 0.024 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 N1 1.6068(16) . ?
P1 C2 1.8227(19) . ?
P1 C14 1.8070(19) . ?
P1 C20 1.7986(18) . ?
O1 C8 1.364(2) . ?
O1 C9 1.450(2) . ?
N1 C1 1.304(2) . ?
N2 C1 1.168(2) . ?
N3 C8 1.266(2) . ?
N3 C10 1.483(2) . ?
C2 C3 1.402(2) . ?
C2 C7 1.414(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(3) . ?
C7 C8 1.473(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.545(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.532(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.533(3) . ?
C11 C13 1.524(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.405(3) . ?
C14 C19 1.396(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(3) . ?
C20 C25 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 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
N1 P1 C2 101.48(8) . . ?
N1 P1 C14 108.94(9) . . ?
N1 P1 C20 109.49(8) . . ?
C14 P1 C2 113.23(8) . . ?
C20 P1 C2 113.84(9) . . ?
C20 P1 C14 109.47(9) . . ?
C8 O1 C9 105.30(14) . . ?
C1 N1 P1 124.94(14) . . ?
C8 N3 C10 107.33(16) . . ?
N2 C1 N1 173.9(2) . . ?
C3 C2 P1 114.73(14) . . ?
C3 C2 C7 117.97(17) . . ?
C7 C2 P1 127.28(14) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.56(18) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.19(18) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.29(18) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.62(19) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C8 122.90(17) . . ?
C6 C7 C2 119.34(17) . . ?
C6 C7 C8 117.76(17) . . ?
O1 C8 C7 115.29(15) . . ?
N3 C8 O1 118.92(17) . . ?
N3 C8 C7 125.80(17) . . ?
O1 C9 H9A 110.7 . . ?
O1 C9 H9B 110.7 . . ?
O1 C9 C10 105.02(15) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N3 C10 C9 103.33(15) . . ?
N3 C10 H10 109.2 . . ?
N3 C10 C11 111.71(16) . . ?
C9 C10 H10 109.2 . . ?
C11 C10 C9 113.98(16) . . ?
C11 C10 H10 109.2 . . ?
C10 C11 H11 108.5 . . ?
C10 C11 C12 110.55(17) . . ?
C12 C11 H11 108.5 . . ?
C13 C11 C10 111.09(17) . . ?
C13 C11 H11 108.5 . . ?
C13 C11 C12 109.66(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 P1 116.79(14) . . ?
C19 C14 P1 123.53(15) . . ?
C19 C14 C15 119.54(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.87(19) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.13(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.18(19) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 119.99(18) . . ?
C18 C19 H19 120.0 . . ?
C21 C20 P1 117.00(14) . . ?
C25 C20 P1 122.74(15) . . ?
C25 C20 C21 119.88(17) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.83(18) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.87(18) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.50(17) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.84(18) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 120.07(18) . . ?
C24 C25 H25 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C2 C3 C4 -179.71(14) . . . . ?
P1 C2 C7 C6 -179.65(14) . . . . ?
P1 C2 C7 C8 1.1(3) . . . . ?
P1 C14 C15 C16 -175.01(15) . . . . ?
P1 C14 C19 C18 175.85(15) . . . . ?
P1 C20 C21 C22 -173.12(14) . . . . ?
P1 C20 C25 C24 172.11(14) . . . . ?
O1 C9 C10 N3 -3.0(2) . . . . ?
O1 C9 C10 C11 -124.42(17) . . . . ?
N1 P1 C2 C3 0.02(16) . . . . ?
N1 P1 C2 C7 -178.24(16) . . . . ?
N1 P1 C14 C15 37.26(17) . . . . ?
N1 P1 C14 C19 -138.29(16) . . . . ?
N1 P1 C20 C21 65.84(16) . . . . ?
N1 P1 C20 C25 -107.06(16) . . . . ?
N3 C10 C11 C12 -176.03(17) . . . . ?
N3 C10 C11 C13 62.0(2) . . . . ?
C2 P1 N1 C1 -172.05(16) . . . . ?
C2 P1 C14 C15 -74.84(17) . . . . ?
C2 P1 C14 C19 109.61(16) . . . . ?
C2 P1 C20 C21 178.62(14) . . . . ?
C2 P1 C20 C25 5.72(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C7 C8 O1 166.17(16) . . . . ?
C2 C7 C8 N3 -13.6(3) . . . . ?
C3 C2 C7 C6 2.1(3) . . . . ?
C3 C2 C7 C8 -177.08(17) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C5 C6 C7 C8 178.07(17) . . . . ?
C6 C7 C8 O1 -13.1(2) . . . . ?
C6 C7 C8 N3 167.17(18) . . . . ?
C7 C2 C3 C4 -1.3(3) . . . . ?
C8 O1 C9 C10 3.0(2) . . . . ?
C8 N3 C10 C9 1.9(2) . . . . ?
C8 N3 C10 C11 124.83(17) . . . . ?
C9 O1 C8 N3 -2.1(2) . . . . ?
C9 O1 C8 C7 178.11(16) . . . . ?
C9 C10 C11 C12 -59.4(2) . . . . ?
C9 C10 C11 C13 178.65(17) . . . . ?
C10 N3 C8 O1 0.1(2) . . . . ?
C10 N3 C8 C7 179.82(17) . . . . ?
C14 P1 N1 C1 68.27(18) . . . . ?
C14 P1 C2 C3 116.60(14) . . . . ?
C14 P1 C2 C7 -61.66(19) . . . . ?
C14 P1 C20 C21 -53.53(16) . . . . ?
C14 P1 C20 C25 133.58(16) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C14 -0.9(3) . . . . ?
C19 C14 C15 C16 0.7(3) . . . . ?
C20 P1 N1 C1 -51.43(19) . . . . ?
C20 P1 C2 C3 -117.50(14) . . . . ?
C20 P1 C2 C7 64.24(18) . . . . ?
C20 P1 C14 C15 156.97(14) . . . . ?
C20 P1 C14 C19 -18.58(18) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C20 C25 C24 -0.6(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C20 0.6(3) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.786
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, acetone'
####################################################################### 
# 
# 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_mds322
_database_code_depnum_ccdc_archive 'CCDC 2329725'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;Merck Research Labs
United States of America
;
_audit_update_record             
;
2024-01-30 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
velabo.mdluli@merck.com
mohammad.chaudhry1@merck.com
_chemical_name_common            ?
_chemical_name_systematic        mds322
_chemical_formula_moiety         'C48 H37 Br3 N7 Ni2 O P2, Br, 1[N1H3C2]'
_chemical_formula_sum            'C49 H40 Br4 N9 Ni2 O P2'
_chemical_formula_weight         1269.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P1 N4 C20 H20'
_chemical_oxdiff_usercomment     'BpyP=NCN ligand, methanol, Nickel II complex'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0937(3)
_cell_length_b                   27.1340(6)
_cell_length_c                   15.1168(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.658(2)
_cell_angle_gamma                90
_cell_volume                     4799.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18900
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1180
_cell_measurement_theta_min      2.5890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.231
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2524
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0715
-1 -1 2 0.0853
0 2 -1 0.0516
-1 1 2 0.0937
1 -1 -2 0.0407
-1 0 -1 0.0249
1 0 1 0.0157
0 -1 0 0.0620
-2 -1 2 0.0859
2 1 -2 0.0508
-1 -2 -1 0.0378
2 2 1 0.0323
-2 -1 0 0.0492

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Slow evaporation from MeCN/MeOH.'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.041
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 1.0000 -0.0000 -0.0212 0.0071 -0.0135
-1.0000 -1.0000 2.0000 0.0663 -0.0350 -0.0719
0.0000 2.0000 -1.0000 -0.0495 0.0512 0.0035
-1.0000 1.0000 2.0000 0.0238 -0.0208 -0.0990
1.0000 -1.0000 -2.0000 -0.0238 0.0208 0.0990
-1.0000 0.0000 -1.0000 0.0239 0.0831 0.0062
1.0000 -0.0000 1.0000 -0.0239 -0.0831 -0.0062
-0.0000 -1.0000 0.0000 0.0212 -0.0071 0.0135
-2.0000 -1.0000 2.0000 0.0972 0.0111 -0.0963
2.0000 1.0000 -2.0000 -0.0972 -0.0111 0.0963
-1.0000 -2.0000 -1.0000 0.0663 0.0689 0.0332
2.0000 2.0000 1.0000 -0.0972 -0.1150 -0.0088
-2.0000 -1.0000 0.0000 0.0831 0.0851 -0.0352

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.299
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  14.00   0.50   46.46    --   -6.11 -80.00  99.00   90
  2  ω    -29.00  -4.00   0.50   46.46    --   -6.11  80.00-136.00   50
  3  ω    -41.00  13.00   0.50   46.46    --    7.21 -80.00  99.00  108
  4  ω    -28.00  11.00   0.50   46.46    --   -6.11  77.00 120.00   78
  5  ω    -10.00  16.00   0.50   46.46    --   -6.11 -77.00 -60.00   52
  6  ω    -27.00  14.00   0.50   46.46    --   -6.11  73.00 -46.82   82
  7  ω    -11.00  15.00   0.50   46.46    --   -6.11 -77.00-180.00   52
  8  ω     -9.00  17.00   0.50   46.46    --   -6.11 -77.00-150.00   52
  9  ω      7.00  41.00   0.50   46.46    --    7.21 -99.00-120.00   68
 10  ω     -8.00  20.00   0.50   46.46    --    7.21  57.00-150.00   56
 11  ω     14.00  39.00   0.50   46.46    --    7.21 -99.00 -30.00   50
 12  ω      6.00  31.00   0.50   46.46    --    7.21 -99.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0309306000
_diffrn_orient_matrix_UB_12      -0.0212175000
_diffrn_orient_matrix_UB_13      0.0070583000
_diffrn_orient_matrix_UB_21      -0.0461015000
_diffrn_orient_matrix_UB_22      0.0071024000
_diffrn_orient_matrix_UB_23      -0.0370124000
_diffrn_orient_matrix_UB_31      0.0243708000
_diffrn_orient_matrix_UB_32      -0.0135099000
_diffrn_orient_matrix_UB_33      -0.0305367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8569
_reflns_number_total             10590
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.204
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         10590
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+16.7053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C47A = O1B-C47B
 1.427 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(O1B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N9, C48, C49, H49A, H49B, H49C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Br3B)=Sof(O1A)=Sof(C47A)=Sof(H47D)=Sof(H47E)=Sof(H47F)=1-FVAR(1)
 Sof(Br3A)=Sof(O1B)=Sof(C47B)=Sof(H47A)=Sof(H47B)=Sof(H47C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32),
 C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43),
  C44(H44), C45(H45)
6.b Idealised Me refined as rotating group:
 C47A(H47D,H47E,H47F), C47B(H47A,H47B,H47C), C49(H49A,H49B,H49C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.64538(4) 0.56788(2) 0.21639(3) 0.02616(11) Uani 1 1 d . . . . .
Br2 Br 0.62710(4) 0.70550(2) 0.57971(3) 0.03404(13) Uani 1 1 d . . . . .
Br3A Br 0.6629(3) 0.48010(10) 0.4144(2) 0.0425(9) Uani 0.249(2) 1 d . . P A 1
Br3B Br 0.84448(8) 0.55608(3) 0.49970(5) 0.0231(2) Uani 0.751(2) 1 d . . P A 1
Ni1 Ni 0.51552(5) 0.50609(2) 0.27001(4) 0.02303(13) Uani 1 1 d . . . . .
Ni2 Ni 0.73289(4) 0.63239(2) 0.53572(3) 0.01881(12) Uani 1 1 d . . . . .
P1 P 0.34674(10) 0.59796(4) 0.26261(7) 0.0215(2) Uani 1 1 d . . . . .
P2 P 0.85670(9) 0.61157(4) 0.74808(7) 0.0188(2) Uani 1 1 d . . . . .
O1A O 0.6456(5) 0.4889(2) 0.3727(4) 0.0350(14) Uani 0.751(2) 1 d D . P A 2
O1B O 0.8063(13) 0.5774(7) 0.4831(13) 0.045(4) Uani 0.249(2) 1 d D U P A 2
N1 N 0.5405(3) 0.45315(14) 0.1798(3) 0.0269(8) Uani 1 1 d . . . . .
N2 N 0.3925(3) 0.52509(13) 0.1584(2) 0.0224(8) Uani 1 1 d . . . . .
N3 N 0.4427(3) 0.56580(13) 0.3335(2) 0.0212(7) Uani 1 1 d . . . . .
N4 N 0.5849(3) 0.60168(14) 0.4647(2) 0.0253(8) Uani 1 1 d . . . . .
N5 N 0.7718(3) 0.67371(13) 0.4341(2) 0.0208(7) Uani 1 1 d . . . . .
N6 N 0.8824(3) 0.66323(13) 0.6043(2) 0.0191(7) Uani 1 1 d . . . . .
N7 N 0.7435(3) 0.59941(13) 0.6673(2) 0.0225(8) Uani 1 1 d . . . . .
N8 N 0.5973(3) 0.54110(14) 0.6905(2) 0.0261(8) Uani 1 1 d . . . . .
C1 C 0.6179(4) 0.41691(18) 0.1988(4) 0.0326(11) Uani 1 1 d . . . . .
H1 H 0.672174 0.416719 0.256527 0.039 Uiso 1 1 calc R U . . .
C2 C 0.6211(5) 0.37960(18) 0.1369(4) 0.0359(12) Uani 1 1 d . . . . .
H2 H 0.677512 0.354480 0.151267 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5405(5) 0.37971(19) 0.0537(4) 0.0405(13) Uani 1 1 d . . . . .
H3 H 0.539430 0.353951 0.010883 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4615(5) 0.41755(18) 0.0331(3) 0.0337(11) Uani 1 1 d . . . . .
H4 H 0.406333 0.418485 -0.024172 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4645(4) 0.45428(16) 0.0982(3) 0.0261(10) Uani 1 1 d . . . . .
C6 C 0.3850(4) 0.49666(16) 0.0839(3) 0.0261(10) Uani 1 1 d . . . . .
C7 C 0.3100(4) 0.50975(18) 0.0009(3) 0.0283(10) Uani 1 1 d . . . . .
H7 H 0.305246 0.490365 -0.052246 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2432(4) 0.55112(18) -0.0029(3) 0.0296(10) Uani 1 1 d . . . . .
H8 H 0.191373 0.560139 -0.058991 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2508(4) 0.57970(17) 0.0743(3) 0.0257(9) Uani 1 1 d . . . . .
H9 H 0.204661 0.608217 0.072288 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3279(4) 0.56537(16) 0.1544(3) 0.0225(9) Uani 1 1 d . . . . .
C11 C 0.3840(4) 0.66077(16) 0.2519(3) 0.0262(9) Uani 1 1 d . . . . .
C12 C 0.4115(5) 0.6788(2) 0.1756(4) 0.0362(12) Uani 1 1 d . . . . .
H12 H 0.413788 0.657482 0.126126 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4362(5) 0.7287(2) 0.1715(4) 0.0500(15) Uani 1 1 d . . . . .
H13 H 0.454043 0.741732 0.118424 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4350(5) 0.7594(2) 0.2435(4) 0.0434(14) Uani 1 1 d . . . . .
H14 H 0.451160 0.793435 0.239608 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4106(6) 0.7411(2) 0.3208(4) 0.0519(15) Uani 1 1 d . . . . .
H15 H 0.412341 0.762222 0.371203 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3836(6) 0.6921(2) 0.3253(4) 0.0506(16) Uani 1 1 d . . . . .
H16 H 0.364629 0.679493 0.378253 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2116(4) 0.59864(17) 0.2903(3) 0.0253(9) Uani 1 1 d . . . . .
C18 C 0.1326(4) 0.63548(19) 0.2534(3) 0.0320(11) Uani 1 1 d . . . . .
H18 H 0.150358 0.659473 0.213294 0.038 Uiso 1 1 calc R U . . .
C19 C 0.0296(5) 0.6368(2) 0.2752(4) 0.0383(12) Uani 1 1 d . . . . .
H19 H -0.025203 0.661140 0.248736 0.046 Uiso 1 1 calc R U . . .
C20 C 0.0049(4) 0.6030(2) 0.3354(4) 0.0377(12) Uani 1 1 d . . . . .
H20 H -0.065455 0.605141 0.352396 0.045 Uiso 1 1 calc R U . . .
C21 C 0.0818(5) 0.5660(2) 0.3714(4) 0.0406(12) Uani 1 1 d . . . . .
H21 H 0.063942 0.542587 0.412408 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1849(4) 0.56306(19) 0.3475(3) 0.0331(11) Uani 1 1 d . . . . .
H22 H 0.236691 0.536958 0.369979 0.040 Uiso 1 1 calc R U . . .
C23 C 0.5163(4) 0.58651(16) 0.4032(3) 0.0218(9) Uani 1 1 d . . . . .
C24 C 0.7098(4) 0.67636(16) 0.3471(3) 0.0231(9) Uani 1 1 d . . . . .
H24 H 0.640823 0.657991 0.329159 0.028 Uiso 1 1 calc R U . . .
C25 C 0.7431(4) 0.70508(16) 0.2824(3) 0.0255(9) Uani 1 1 d . . . . .
H25 H 0.697613 0.706516 0.221255 0.031 Uiso 1 1 calc R U . . .
C26 C 0.8423(4) 0.73119(16) 0.3083(3) 0.0246(9) Uani 1 1 d . . . . .
H26 H 0.866432 0.751044 0.264865 0.030 Uiso 1 1 calc R U . . .
C27 C 0.9082(4) 0.72885(16) 0.3978(3) 0.0244(9) Uani 1 1 d . . . . .
H27 H 0.978080 0.746530 0.416427 0.029 Uiso 1 1 calc R U . . .
C28 C 0.8692(4) 0.69984(16) 0.4597(3) 0.0218(9) Uani 1 1 d . . . . .
C29 C 0.9300(4) 0.69542(16) 0.5580(3) 0.0217(9) Uani 1 1 d . . . . .
C30 C 1.0268(4) 0.72267(18) 0.6010(3) 0.0304(10) Uani 1 1 d . . . . .
H30 H 1.058831 0.745896 0.567493 0.037 Uiso 1 1 calc R U . . .
C31 C 1.0751(4) 0.71515(19) 0.6933(3) 0.0318(11) Uani 1 1 d . . . . .
H31 H 1.140906 0.733299 0.723815 0.038 Uiso 1 1 calc R U . . .
C32 C 1.0272(4) 0.68100(17) 0.7415(3) 0.0263(9) Uani 1 1 d . . . . .
H32 H 1.059531 0.675176 0.804705 0.032 Uiso 1 1 calc R U . . .
C33 C 0.9307(4) 0.65578(16) 0.6941(3) 0.0212(9) Uani 1 1 d . . . . .
C34 C 0.8227(4) 0.63815(16) 0.8467(3) 0.0224(9) Uani 1 1 d . . . . .
C35 C 0.7184(4) 0.66219(16) 0.8364(3) 0.0251(9) Uani 1 1 d . . . . .
H35 H 0.664926 0.663617 0.778381 0.030 Uiso 1 1 calc R U . . .
C36 C 0.6940(4) 0.68398(18) 0.9122(3) 0.0311(10) Uani 1 1 d . . . . .
H36 H 0.623563 0.700831 0.905979 0.037 Uiso 1 1 calc R U . . .
C37 C 0.7719(5) 0.68135(19) 0.9973(3) 0.0359(12) Uani 1 1 d . . . . .
H37 H 0.753726 0.695945 1.048990 0.043 Uiso 1 1 calc R U . . .
C38 C 0.8758(5) 0.65758(19) 1.0073(3) 0.0346(11) Uani 1 1 d . . . . .
H38 H 0.928776 0.656060 1.065541 0.042 Uiso 1 1 calc R U . . .
C39 C 0.9021(4) 0.63600(17) 0.9318(3) 0.0267(10) Uani 1 1 d . . . . .
H39 H 0.973488 0.619931 0.937973 0.032 Uiso 1 1 calc R U . . .
C40 C 0.9487(4) 0.55998(16) 0.7849(3) 0.0218(9) Uani 1 1 d . . . . .
C41 C 1.0401(4) 0.55103(17) 0.7455(3) 0.0274(10) Uani 1 1 d . . . . .
H41 H 1.056829 0.573655 0.702757 0.033 Uiso 1 1 calc R U . . .
C42 C 1.1055(4) 0.50910(18) 0.7694(3) 0.0314(10) Uani 1 1 d . . . . .
H42 H 1.167903 0.502957 0.743454 0.038 Uiso 1 1 calc R U . . .
C43 C 1.0803(4) 0.47609(18) 0.8310(3) 0.0301(10) Uani 1 1 d . . . . .
H43 H 1.125225 0.447169 0.846643 0.036 Uiso 1 1 calc R U . . .
C44 C 0.9905(4) 0.48460(17) 0.8701(3) 0.0301(10) Uani 1 1 d . . . . .
H44 H 0.974280 0.461692 0.912623 0.036 Uiso 1 1 calc R U . . .
C45 C 0.9239(4) 0.52654(17) 0.8473(3) 0.0254(9) Uani 1 1 d . . . . .
H45 H 0.861852 0.532462 0.873860 0.031 Uiso 1 1 calc R U . . .
C46 C 0.6672(4) 0.56795(16) 0.6818(3) 0.0211(9) Uani 1 1 d . . . . .
C47A C 0.6319(8) 0.4632(4) 0.4516(5) 0.058(3) Uani 0.751(2) 1 d D . P A 2
H47D H 0.589934 0.432484 0.432620 0.087 Uiso 0.751(2) 1 calc R U P A 2
H47E H 0.589225 0.483826 0.484574 0.087 Uiso 0.751(2) 1 calc R U P A 2
H47F H 0.707284 0.455564 0.491614 0.087 Uiso 0.751(2) 1 calc R U P A 2
C47B C 0.9096(17) 0.5519(8) 0.5246(13) 0.032(5) Uani 0.249(2) 1 d D . P A 2
H47A H 0.973173 0.566827 0.504730 0.048 Uiso 0.249(2) 1 calc R U P A 2
H47B H 0.902149 0.517211 0.506290 0.048 Uiso 0.249(2) 1 calc R U P A 2
H47C H 0.924577 0.554315 0.591268 0.048 Uiso 0.249(2) 1 calc R U P A 2
Br4 Br 0.18970(4) 0.80237(2) 0.47188(3) 0.03511(13) Uani 1 1 d . . . . .
N9 N 0.8258(12) 0.3814(4) 0.3816(9) 0.188(7) Uani 1 1 d . . . B 2
C48 C 0.7705(11) 0.3563(4) 0.4206(7) 0.102(3) Uani 1 1 d . . . B 2
C49 C 0.7279(12) 0.3286(4) 0.4819(7) 0.135(5) Uani 1 1 d . . . B 2
H49A H 0.718792 0.294209 0.461280 0.202 Uiso 1 1 calc R U . B 2
H49B H 0.653597 0.341784 0.485082 0.202 Uiso 1 1 calc R U . B 2
H49C H 0.781269 0.330108 0.542608 0.202 Uiso 1 1 calc R U . B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.5649(7) . ?
Br2 Ni2 2.5387(7) . ?
Br3A Ni1 2.544(3) . ?
Br3B Ni2 2.6033(10) . ?
Ni1 O1A 1.967(7) . ?
Ni1 N1 2.056(4) . ?
Ni1 N2 2.014(4) . ?
Ni1 N3 2.179(4) . ?
Ni1 N8 2.067(4) 3_666 ?
Ni2 O1B 2.001(16) . ?
Ni2 N4 2.019(4) . ?
Ni2 N5 2.051(4) . ?
Ni2 N6 2.024(3) . ?
Ni2 N7 2.155(3) . ?
P1 N3 1.621(4) . ?
P1 C10 1.822(4) . ?
P1 C11 1.781(5) . ?
P1 C17 1.787(5) . ?
P2 N7 1.621(4) . ?
P2 C33 1.810(4) . ?
P2 C34 1.795(4) . ?
P2 C40 1.787(4) . ?
O1A C47A 1.4264(10) . ?
O1B C47B 1.4268(10) . ?
N1 C1 1.337(6) . ?
N1 C5 1.339(6) . ?
N2 C6 1.349(5) . ?
N2 C10 1.336(6) . ?
N3 C23 1.320(6) . ?
N4 C23 1.154(6) . ?
N5 C24 1.340(5) . ?
N5 C28 1.345(5) . ?
N6 C29 1.337(5) . ?
N6 C33 1.350(5) . ?
N7 C46 1.316(6) . ?
N8 C46 1.149(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(6) . ?
C5 C6 1.479(7) . ?
C6 C7 1.395(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(6) . ?
C11 C12 1.370(7) . ?
C11 C16 1.398(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.368(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(7) . ?
C17 C22 1.387(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(7) . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.387(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.363(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(6) . ?
C28 C29 1.488(6) . ?
C29 C30 1.398(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(6) . ?
C34 C35 1.393(6) . ?
C34 C39 1.399(6) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.391(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.386(8) . ?
C38 H38 0.9500 . ?
C38 C39 1.389(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.402(6) . ?
C40 C45 1.395(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.380(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.381(7) . ?
C44 H44 0.9500 . ?
C44 C45 1.386(7) . ?
C45 H45 0.9500 . ?
C47A H47D 0.9800 . ?
C47A H47E 0.9800 . ?
C47A H47F 0.9800 . ?
C47B H47A 0.9800 . ?
C47B H47B 0.9800 . ?
C47B H47C 0.9800 . ?
N9 C48 1.209(14) . ?
C48 C49 1.390(13) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 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
Br3A Ni1 Br1 95.75(9) . . ?
O1A Ni1 Br1 88.44(19) . . ?
O1A Ni1 N1 97.8(2) . . ?
O1A Ni1 N2 174.9(2) . . ?
O1A Ni1 N3 99.2(2) . . ?
O1A Ni1 N8 94.6(2) . 3_666 ?
N1 Ni1 Br1 92.44(10) . . ?
N1 Ni1 Br3A 100.78(14) . . ?
N1 Ni1 N3 162.87(15) . . ?
N1 Ni1 N8 88.71(15) . 3_666 ?
N2 Ni1 Br1 87.11(10) . . ?
N2 Ni1 Br3A 177.02(14) . . ?
N2 Ni1 N1 79.89(15) . . ?
N2 Ni1 N3 83.32(14) . . ?
N2 Ni1 N8 89.91(14) . 3_666 ?
N3 Ni1 Br1 90.07(9) . . ?
N3 Ni1 Br3A 95.82(12) . . ?
N8 Ni1 Br1 176.57(11) 3_666 . ?
N8 Ni1 Br3A 87.20(14) 3_666 . ?
N8 Ni1 N3 87.90(14) 3_666 . ?
Br2 Ni2 Br3B 176.97(3) . . ?
O1B Ni2 Br2 172.1(6) . . ?
O1B Ni2 N4 84.5(5) . . ?
O1B Ni2 N5 84.3(6) . . ?
O1B Ni2 N6 94.8(5) . . ?
O1B Ni2 N7 97.4(6) . . ?
N4 Ni2 Br2 91.37(11) . . ?
N4 Ni2 Br3B 89.85(11) . . ?
N4 Ni2 N5 99.67(14) . . ?
N4 Ni2 N6 178.74(14) . . ?
N4 Ni2 N7 99.02(14) . . ?
N5 Ni2 Br2 89.74(10) . . ?
N5 Ni2 Br3B 92.79(10) . . ?
N5 Ni2 N7 161.31(14) . . ?
N6 Ni2 Br2 89.26(10) . . ?
N6 Ni2 Br3B 89.58(10) . . ?
N6 Ni2 N5 79.24(14) . . ?
N6 Ni2 N7 82.06(13) . . ?
N7 Ni2 Br2 89.95(10) . . ?
N7 Ni2 Br3B 87.11(10) . . ?
N3 P1 C10 103.8(2) . . ?
N3 P1 C11 114.8(2) . . ?
N3 P1 C17 113.3(2) . . ?
C11 P1 C10 111.1(2) . . ?
C11 P1 C17 106.2(2) . . ?
C17 P1 C10 107.5(2) . . ?
N7 P2 C33 102.39(19) . . ?
N7 P2 C34 112.4(2) . . ?
N7 P2 C40 114.6(2) . . ?
C34 P2 C33 110.6(2) . . ?
C40 P2 C33 108.6(2) . . ?
C40 P2 C34 108.2(2) . . ?
C47A O1A Ni1 122.5(5) . . ?
C47B O1B Ni2 127.8(13) . . ?
C1 N1 Ni1 125.7(3) . . ?
C1 N1 C5 119.7(4) . . ?
C5 N1 Ni1 114.4(3) . . ?
C6 N2 Ni1 115.6(3) . . ?
C10 N2 Ni1 123.2(3) . . ?
C10 N2 C6 121.0(4) . . ?
P1 N3 Ni1 114.21(18) . . ?
C23 N3 Ni1 113.7(3) . . ?
C23 N3 P1 121.6(3) . . ?
C23 N4 Ni2 159.2(3) . . ?
C24 N5 Ni2 125.9(3) . . ?
C24 N5 C28 119.1(4) . . ?
C28 N5 Ni2 115.0(3) . . ?
C29 N6 Ni2 116.7(3) . . ?
C29 N6 C33 119.3(4) . . ?
C33 N6 Ni2 123.8(3) . . ?
P2 N7 Ni2 116.93(19) . . ?
C46 N7 Ni2 122.9(3) . . ?
C46 N7 P2 120.0(3) . . ?
C46 N8 Ni1 170.2(3) . 3_666 ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 121.9(5) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(5) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.5(5) . . ?
N1 C5 C6 114.9(4) . . ?
C4 C5 C6 123.6(5) . . ?
N2 C6 C5 114.8(4) . . ?
N2 C6 C7 119.8(4) . . ?
C7 C6 C5 125.4(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.1(4) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.8(4) . . ?
C10 C9 H9 121.1 . . ?
N2 C10 P1 114.7(3) . . ?
N2 C10 C9 121.7(4) . . ?
C9 C10 P1 123.6(3) . . ?
C12 C11 P1 122.6(4) . . ?
C12 C11 C16 120.2(5) . . ?
C16 C11 P1 117.2(4) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(6) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 H16 120.0 . . ?
C18 C17 P1 119.1(4) . . ?
C22 C17 P1 120.7(4) . . ?
C22 C17 C18 120.2(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.3(5) . . ?
C21 C22 H22 120.3 . . ?
N4 C23 N3 175.3(5) . . ?
N5 C24 H24 119.0 . . ?
N5 C24 C25 122.0(4) . . ?
C25 C24 H24 119.0 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(4) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(4) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.9 . . ?
C26 C27 C28 118.2(4) . . ?
C28 C27 H27 120.9 . . ?
N5 C28 C27 121.7(4) . . ?
N5 C28 C29 114.9(4) . . ?
C27 C28 C29 123.4(4) . . ?
N6 C29 C28 114.0(4) . . ?
N6 C29 C30 121.6(4) . . ?
C30 C29 C28 124.5(4) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 C29 118.7(4) . . ?
C31 C30 H30 120.7 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 121.1 . . ?
C33 C32 C31 117.8(4) . . ?
C33 C32 H32 121.1 . . ?
N6 C33 P2 114.5(3) . . ?
N6 C33 C32 122.7(4) . . ?
C32 C33 P2 122.8(3) . . ?
C35 C34 P2 119.1(3) . . ?
C35 C34 C39 120.9(4) . . ?
C39 C34 P2 119.9(3) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 C34 118.9(4) . . ?
C36 C35 H35 120.5 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.4(5) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 119.7 . . ?
C38 C37 C36 120.5(4) . . ?
C38 C37 H37 119.7 . . ?
C37 C38 H38 120.1 . . ?
C37 C38 C39 119.8(5) . . ?
C39 C38 H38 120.1 . . ?
C34 C39 H39 120.3 . . ?
C38 C39 C34 119.4(5) . . ?
C38 C39 H39 120.3 . . ?
C41 C40 P2 119.9(3) . . ?
C45 C40 P2 119.7(3) . . ?
C45 C40 C41 120.1(4) . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.5(4) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.1(5) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(4) . . ?
C44 C43 H43 119.6 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.1(4) . . ?
C45 C44 H44 120.0 . . ?
C40 C45 H45 120.3 . . ?
C44 C45 C40 119.4(4) . . ?
C44 C45 H45 120.3 . . ?
N8 C46 N7 176.8(5) . . ?
O1A C47A H47D 109.5 . . ?
O1A C47A H47E 109.5 . . ?
O1A C47A H47F 109.5 . . ?
H47D C47A H47E 109.5 . . ?
H47D C47A H47F 109.5 . . ?
H47E C47A H47F 109.5 . . ?
O1B C47B H47A 109.5 . . ?
O1B C47B H47B 109.5 . . ?
O1B C47B H47C 109.5 . . ?
H47A C47B H47B 109.5 . . ?
H47A C47B H47C 109.5 . . ?
H47B C47B H47C 109.5 . . ?
N9 C48 C49 167.2(15) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 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
Ni1 N1 C1 C2 173.0(3) . . . . ?
Ni1 N1 C5 C4 -172.6(3) . . . . ?
Ni1 N1 C5 C6 6.8(5) . . . . ?
Ni1 N2 C6 C5 3.3(5) . . . . ?
Ni1 N2 C6 C7 -173.7(3) . . . . ?
Ni1 N2 C10 P1 -7.5(4) . . . . ?
Ni1 N2 C10 C9 174.3(3) . . . . ?
Ni2 N5 C24 C25 -179.5(3) . . . . ?
Ni2 N5 C28 C27 178.6(3) . . . . ?
Ni2 N5 C28 C29 -1.7(5) . . . . ?
Ni2 N6 C29 C28 -5.3(5) . . . . ?
Ni2 N6 C29 C30 173.3(4) . . . . ?
Ni2 N6 C33 P2 4.7(5) . . . . ?
Ni2 N6 C33 C32 -173.5(3) . . . . ?
P1 C11 C12 C13 178.0(4) . . . . ?
P1 C11 C16 C15 -179.4(5) . . . . ?
P1 C17 C18 C19 -179.0(4) . . . . ?
P1 C17 C22 C21 176.8(4) . . . . ?
P2 C34 C35 C36 -178.0(3) . . . . ?
P2 C34 C39 C38 178.7(4) . . . . ?
P2 C40 C41 C42 -175.2(4) . . . . ?
P2 C40 C45 C44 175.0(3) . . . . ?
N1 C1 C2 C3 -1.1(7) . . . . ?
N1 C5 C6 N2 -6.7(5) . . . . ?
N1 C5 C6 C7 170.1(4) . . . . ?
N2 C6 C7 C8 -1.3(6) . . . . ?
N3 P1 C10 N2 0.4(4) . . . . ?
N3 P1 C10 C9 178.6(4) . . . . ?
N3 P1 C11 C12 108.0(4) . . . . ?
N3 P1 C11 C16 -72.4(5) . . . . ?
N3 P1 C17 C18 161.2(3) . . . . ?
N3 P1 C17 C22 -19.1(4) . . . . ?
N5 C24 C25 C26 0.3(7) . . . . ?
N5 C28 C29 N6 4.6(6) . . . . ?
N5 C28 C29 C30 -174.0(4) . . . . ?
N6 C29 C30 C31 1.2(7) . . . . ?
N7 P2 C33 N6 -5.8(4) . . . . ?
N7 P2 C33 C32 172.4(4) . . . . ?
N7 P2 C34 C35 -23.4(4) . . . . ?
N7 P2 C34 C39 158.8(3) . . . . ?
N7 P2 C40 C41 93.1(4) . . . . ?
N7 P2 C40 C45 -81.7(4) . . . . ?
C1 N1 C5 C4 2.0(6) . . . . ?
C1 N1 C5 C6 -178.6(4) . . . . ?
C1 C2 C3 C4 2.1(7) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 N1 -1.0(7) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 N2 172.6(4) . . . . ?
C4 C5 C6 C7 -10.5(7) . . . . ?
C5 N1 C1 C2 -1.0(7) . . . . ?
C5 C6 C7 C8 -178.1(4) . . . . ?
C6 N2 C10 P1 178.2(3) . . . . ?
C6 N2 C10 C9 0.0(6) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C8 C9 C10 P1 -178.7(3) . . . . ?
C8 C9 C10 N2 -0.7(6) . . . . ?
C10 P1 N3 Ni1 5.7(2) . . . . ?
C10 P1 N3 C23 148.3(3) . . . . ?
C10 P1 C11 C12 -9.4(5) . . . . ?
C10 P1 C11 C16 170.2(4) . . . . ?
C10 P1 C17 C18 -84.7(4) . . . . ?
C10 P1 C17 C22 95.0(4) . . . . ?
C10 N2 C6 C5 178.1(4) . . . . ?
C10 N2 C6 C7 1.0(6) . . . . ?
C11 P1 N3 Ni1 -115.8(2) . . . . ?
C11 P1 N3 C23 26.8(4) . . . . ?
C11 P1 C10 N2 124.3(3) . . . . ?
C11 P1 C10 C9 -57.5(4) . . . . ?
C11 P1 C17 C18 34.3(4) . . . . ?
C11 P1 C17 C22 -146.0(4) . . . . ?
C11 C12 C13 C14 1.2(9) . . . . ?
C12 C11 C16 C15 0.2(9) . . . . ?
C12 C13 C14 C15 0.7(9) . . . . ?
C13 C14 C15 C16 -2.1(10) . . . . ?
C14 C15 C16 C11 1.7(10) . . . . ?
C16 C11 C12 C13 -1.5(8) . . . . ?
C17 P1 N3 Ni1 122.0(2) . . . . ?
C17 P1 N3 C23 -95.4(4) . . . . ?
C17 P1 C10 N2 -119.9(3) . . . . ?
C17 P1 C10 C9 58.3(4) . . . . ?
C17 P1 C11 C12 -126.0(4) . . . . ?
C17 P1 C11 C16 53.6(5) . . . . ?
C17 C18 C19 C20 2.0(8) . . . . ?
C18 C17 C22 C21 -3.5(7) . . . . ?
C18 C19 C20 C21 -2.9(8) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C20 C21 C22 C17 2.5(8) . . . . ?
C22 C17 C18 C19 1.2(7) . . . . ?
C24 N5 C28 C27 -1.2(6) . . . . ?
C24 N5 C28 C29 178.5(4) . . . . ?
C24 C25 C26 C27 0.0(7) . . . . ?
C25 C26 C27 C28 -0.9(7) . . . . ?
C26 C27 C28 N5 1.5(7) . . . . ?
C26 C27 C28 C29 -178.2(4) . . . . ?
C27 C28 C29 N6 -175.8(4) . . . . ?
C27 C28 C29 C30 5.7(7) . . . . ?
C28 N5 C24 C25 0.3(6) . . . . ?
C28 C29 C30 C31 179.7(4) . . . . ?
C29 N6 C33 P2 179.6(3) . . . . ?
C29 N6 C33 C32 1.4(6) . . . . ?
C29 C30 C31 C32 0.0(8) . . . . ?
C30 C31 C32 C33 -0.5(7) . . . . ?
C31 C32 C33 P2 -178.2(4) . . . . ?
C31 C32 C33 N6 -0.2(7) . . . . ?
C33 P2 N7 Ni2 4.8(3) . . . . ?
C33 P2 N7 C46 -179.9(4) . . . . ?
C33 P2 C34 C35 90.4(4) . . . . ?
C33 P2 C34 C39 -87.5(4) . . . . ?
C33 P2 C40 C41 -20.6(4) . . . . ?
C33 P2 C40 C45 164.6(3) . . . . ?
C33 N6 C29 C28 179.5(4) . . . . ?
C33 N6 C29 C30 -1.9(6) . . . . ?
C34 P2 N7 Ni2 123.5(2) . . . . ?
C34 P2 N7 C46 -61.2(4) . . . . ?
C34 P2 C33 N6 -125.7(3) . . . . ?
C34 P2 C33 C32 52.5(4) . . . . ?
C34 P2 C40 C41 -140.7(4) . . . . ?
C34 P2 C40 C45 44.5(4) . . . . ?
C34 C35 C36 C37 -0.8(7) . . . . ?
C35 C34 C39 C38 0.9(7) . . . . ?
C35 C36 C37 C38 1.0(7) . . . . ?
C36 C37 C38 C39 -0.3(8) . . . . ?
C37 C38 C39 C34 -0.6(7) . . . . ?
C39 C34 C35 C36 -0.2(7) . . . . ?
C40 P2 N7 Ni2 -112.6(2) . . . . ?
C40 P2 N7 C46 62.8(4) . . . . ?
C40 P2 C33 N6 115.7(3) . . . . ?
C40 P2 C33 C32 -66.0(4) . . . . ?
C40 P2 C34 C35 -150.8(3) . . . . ?
C40 P2 C34 C39 31.4(4) . . . . ?
C40 C41 C42 C43 0.6(7) . . . . ?
C41 C40 C45 C44 0.2(7) . . . . ?
C41 C42 C43 C44 -0.6(7) . . . . ?
C42 C43 C44 C45 0.4(7) . . . . ?
C43 C44 C45 C40 -0.2(7) . . . . ?
C45 C40 C41 C42 -0.4(7) . . . . ?

_olex2_date_sample_data_collection 2023-10-19
_olex2_date_sample_submission    2023-10-19
_olex2_exptl_crystal_mounting_method 'Mounted onto a MiTiGen loop with oil.'
_olex2_submission_original_sample_id mds322
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.609
####################################################################### 
# 
# 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_Compound_35
_database_code_depnum_ccdc_archive 'CCDC 2258978'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
velabo.mdluli@merck.com
mohammad.chaudhry1@merck.com
_chemical_name_common            Compound35
_chemical_name_systematic        Compound35
_chemical_formula_moiety         'C27 H24 N2 O P2'
_chemical_formula_sum            'C27 H24 N2 O P2'
_chemical_formula_weight         454.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N O P H'
_chemical_oxdiff_usercomment     Velabo
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0468(2)
_cell_length_b                   10.5532(2)
_cell_length_c                   11.2334(2)
_cell_angle_alpha                81.121(2)
_cell_angle_beta                 72.014(2)
_cell_angle_gamma                84.044(2)
_cell_volume                     1117.26(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    22036
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3970
_cell_measurement_theta_min      4.1500
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0349
1 0 0 0.0469
2 -2 1 0.0554
1 2 1 0.0726
-1 -2 0 0.0839
1 2 0 0.0553
1 -1 2 0.0844
2 1 2 0.0899
-1 0 -2 0.0968
1 0 2 0.0869
1 -2 0 0.0574
1 -1 0 0.0422
2 2 -1 0.0718
-1 1 0 0.0430
2 -2 -1 0.0574
2 0 -1 0.0671
-2 2 1 0.0583
0 0 -1 0.0858
0 0 1 0.0803
0 2 -1 0.0646
0 1 0 0.0425

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'cooling from a solution of msd001 in acetonitrile'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.082
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 0.0000 -0.0132 0.1535 0.0486
1.0000 0.0000 -0.0000 0.0132 -0.1535 -0.0486
2.0000 -2.0000 1.0000 0.0921 -0.3794 0.2350
1.0000 2.0000 1.0000 0.1988 -0.0084 -0.2539
-1.0000 -2.0000 -0.0000 -0.0731 0.0446 0.3173
1.0000 2.0000 0.0000 0.0731 -0.0446 -0.3173
1.0000 -1.0000 2.0000 0.2346 -0.1353 0.2126
2.0000 1.0000 2.0000 0.3077 -0.1799 -0.1046
-1.0000 -0.0000 -2.0000 -0.2646 0.0809 -0.0783
1.0000 0.0000 2.0000 0.2646 -0.0809 0.0783
1.0000 -2.0000 -0.0000 -0.0468 -0.2623 0.2201
1.0000 -1.0000 -0.0000 -0.0168 -0.2079 0.0858
2.0000 2.0000 -1.0000 -0.0395 -0.2344 -0.4293
-1.0000 1.0000 0.0000 0.0168 0.2079 -0.0858
2.0000 -2.0000 -1.0000 -0.1593 -0.4520 0.1081
2.0000 0.0000 -1.0000 -0.0994 -0.3432 -0.1606
-2.0000 2.0000 1.0000 0.1593 0.4520 -0.1081
0.0000 -0.0000 -1.0000 -0.1257 -0.0363 -0.0634
-0.0000 0.0000 1.0000 0.1257 0.0363 0.0634
-0.0000 2.0000 -1.0000 -0.0658 0.0725 -0.3321
-0.0000 1.0000 0.0000 0.0300 0.0544 -0.1344

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.500
_diffrn_reflns_theta_min         4.173
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -18.00   0.50    0.05    --  -90.00  88.00-105.00  196
  2  ω    -75.00  22.00   0.50    0.05    --  -49.83  88.00-105.00  194
  3  ω    -45.00 -20.00   0.50    0.05    --  -90.00  38.00 -30.00   50
  4  ω    -44.00 -18.00   0.50    0.05    --  -90.00  38.00  60.00   52
  5  ω    -86.00 -20.00   0.50    0.05    --  -49.83 125.00 120.00  132
  6  ω     -6.00  21.00   0.50    0.05    --   10.00  65.00 110.07   54
  7  ω     16.00  45.00   0.50    0.05    --   26.00  48.00 169.60   58
  8  ω      1.00  29.00   0.50    0.05    --   14.00  58.00  47.49   56
  9  ω     11.00  38.00   0.50    0.05    --   22.00  52.00 -36.39   54
 10  ω     11.00  39.00   0.50    0.05    --   22.00  51.00 -91.91   56
 11  ω     44.00  70.00   0.50    0.05    --  107.23 -88.00 137.00   52
 12  ω     50.00 105.00   0.50    0.05    --  107.23 -99.00 120.00  110
 13  ω     44.00  70.00   0.50    0.05    --  107.23-125.00   0.00   52
 14  ω     78.00 111.00   0.50    0.05    --  107.23-125.00   0.00   66
 15  ω     35.00 107.00   0.50    0.05    --  107.23-125.00 -30.00  144
 16  ω     36.00  84.00   0.50    0.05    --  107.23 -99.00   0.00   96
 17  ω     75.00 102.00   0.50    0.05    --  107.23 -99.00  30.00   54
 18  ω     39.00  99.00   0.50    0.05    --  107.23 -99.00  90.00  120
 19  ω    -21.00  76.00   0.50    0.05    --   49.83 -88.00 137.00  194
 20  ω     38.00  70.00   0.50    0.05    --  107.23 -99.00  30.00   64
 21  ω     35.00 105.00   0.50    0.05    --  107.23 -99.00-150.00  140
 22  ω    -22.00  31.00   0.50    0.05    --   49.83 -19.00-180.00  106
 23  ω     38.00  64.00   0.50    0.05    --  107.23 -57.00-150.00   52
 24  ω     35.00  60.00   0.50    0.05    --  107.23 -57.00 -30.00   50
 25  ω     37.00  62.00   0.50    0.05    --  107.23 -57.00-180.00   50
 26  ω     37.00  62.00   0.50    0.05    --  107.23 -57.00   0.00   50
 27  ω     36.00  64.00   0.50    0.05    --  107.23 -57.00  60.00   56
 28  ω     35.00  60.00   0.50    0.05    --  107.23 -57.00 150.00   50
 29  ω    146.00 176.00   0.50    0.05    --  107.23  38.00 -30.00   60
 30  ω    104.00 145.00   0.50    0.05    --  107.23 125.00-180.00   82
 31  ω    148.00 175.00   0.50    0.05    --  107.23 125.00-180.00   54
 32  ω    101.00 178.00   0.50    0.05    --  107.23  88.00-105.00  154
 33  ω    100.00 134.00   0.50    0.05    --  107.23  38.00 -30.00   68
 34  ω    -48.00 -20.00   0.50    0.05    --  -30.00 -47.00  -0.87   56
 35  ω   -117.00 -37.00   0.50    0.05    --  -46.00 -42.00 -87.16  160
 36  ω   -117.00 -37.00   0.50    0.05    --  -46.00 -42.00 -57.24  160
 37  ω   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00-137.64  160
 38  ω   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00 -10.09  160
 39  ω   -121.00 -42.00   0.50    0.05    --  -50.00 -40.00-110.48  158
 40  ω   -117.00 -37.00   0.50    0.05    --  -46.00 -41.00 -34.82  160
 41  ω   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00  67.40  160
 42  ω   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00 111.11  160
 43  ω    -57.00 -29.00   0.50    0.05    --  -38.00 -44.00 179.83   56
 44  ω   -121.00 -42.00   0.50    0.05    --  -50.00 -40.00 132.65  158
 45  ω   -161.00 -94.00   0.50    0.05    --  -90.00 -44.00 179.20  134
 46  ω   -145.00 -64.00   0.50    0.05    --  -74.00 -42.00 132.32  162
 47  ω   -142.00 -60.00   0.50    0.05    --  -70.00 -42.00  53.28  164
 48  ω   -150.00 -69.00   0.50    0.05    --  -78.00 -41.00 170.86  162
 49  ω   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00  70.30  162
 50  ω   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00  28.92  162
 51  ω   -145.00 -64.00   0.50    0.05    --  -74.00 -42.00  29.21  162
 52  ω   -149.00 -70.00   0.50    0.05    --  -78.00 -40.00 -81.45  158
 53  ω   -142.00 -60.00   0.50    0.05    --  -70.00 -42.00-141.97  164
 54  ω   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00-173.91  162
 55  ω   -145.00 -66.00   0.50    0.05    --  -74.00 -40.00 -54.68  158
 56  ω    -96.00 -70.00   0.50    0.05    --  -78.00 -39.00 -67.25   52
 57  ω   -101.00 -74.00   0.50    0.05    --  -82.00 -40.00 -10.30   54
 58  ω    -96.00 -70.00   0.50    0.05    --  -78.00 -39.00   5.73   52
 59  ω   -149.00 -70.00   0.50    0.05    --  -78.00 -39.00  -3.18  158
 60  ω   -104.00 -78.00   0.50    0.05    --  -86.00 -38.00 -25.23   52
 61  ω   -149.00 -70.00   0.50    0.05    --  -78.00 -38.00  41.40  158
 62  ω   -149.00 -70.00   0.50    0.05    --  -78.00 -38.00 147.99  158
 63  ω   -141.00 -62.00   0.50    0.05    --  -70.00 -40.00 174.17  158
 64  ω   -105.00 -78.00   0.50    0.05    --  -86.00 -40.00  98.19   54
 65  ω   -107.00 -82.00   0.50    0.05    --  -90.00 -38.00  60.00   50
 66  ω   -160.00-114.00   0.50    0.05    --  -90.00 -38.00  60.00   92
 67  ω   -160.00-135.00   0.50    0.05    --  -90.00 -38.00 -30.00   50
 68  ω   -161.00-122.00   0.50    0.05    --  -90.00 -38.00 -60.00   78
 69  ω   -115.00 -88.00   0.50    0.05    --  -90.00 -38.00 -30.00   54
 70  ω   -109.00 -83.00   0.50    0.05    --  -90.00 -38.00 -60.00   52
 71  ω   -145.00 -66.00   0.50    0.05    --  -74.00 -38.00-126.31  158
 72  ω   -116.00 -82.00   0.50    0.05    --  -90.00 -38.00-150.00   68
 73  ω   -110.00 -83.00   0.50    0.05    --  -90.00 -38.00-180.00   54
 74  ω   -116.00 -86.00   0.50    0.05    --  -90.00 -38.00  90.00   60
 75  ω   -133.00 -82.00   0.50    0.05    --  -90.00 -38.00 120.00  102
 76  ω    -96.00 -70.00   0.50    0.05    --  -78.00 -38.00  99.36   52
 77  ω   -126.00 -82.00   0.50    0.05    --  -90.00 -38.00 150.00   88
 78  ω   -161.00-127.00   0.50    0.05    --  -90.00 -38.00 150.00   68
 79  ω   -154.00-120.00   0.50    0.05    --  -90.00 -38.00  90.00   68
 80  ω   -130.00 -82.00   0.50    0.05    --  -90.00 -37.00   6.66   96
 81  ω   -115.00 -74.00   0.50    0.05    --  -82.00 -37.00 -99.66   82
 82  ω   -110.00 -81.00   0.50    0.05    --  -90.00 -36.00-162.05   58
 83  ω   -153.00-126.00   0.50    0.05    --  -90.00 -36.00-162.05   54
 84  ω   -161.00 -82.00   0.50    0.05    --  -90.00 -33.00-112.20  158
 85  ω   -107.00 -82.00   0.50    0.05    --  -90.00 -31.00-141.75   50
 86  ω   -117.00 -82.00   0.50    0.05    --  -90.00 -32.00  31.36   70
 87  ω   -155.00-129.00   0.50    0.05    --  -90.00 -32.00  31.36   52
 88  ω   -157.00-116.00   0.50    0.05    --  -90.00 -99.00  90.00   82
 89  ω   -160.00-113.00   0.50    0.05    --  -90.00 -99.00  30.00   94
 90  ω   -161.00 -79.00   0.50    0.05    --  -90.00 -88.00 137.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131634000
_diffrn_orient_matrix_UB_12      0.0299616000
_diffrn_orient_matrix_UB_13      0.1257051000
_diffrn_orient_matrix_UB_21      -0.1534595000
_diffrn_orient_matrix_UB_22      0.0544071000
_diffrn_orient_matrix_UB_23      0.0362878000
_diffrn_orient_matrix_UB_31      -0.0485875000
_diffrn_orient_matrix_UB_32      -0.1343527000
_diffrn_orient_matrix_UB_33      0.0634403000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4165
_reflns_number_total             4462
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.7902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C12(H12), C8(H8), C6(H6), C2(H2), C24(H24), C27(H27), C25(H25),
 C21(H21), C4(H4), C17(H17), C11(H11), C9(H9), C5(H5), C20(H20), C26(H26),
 C10(H10), C3(H3), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P2 P 0.49639(4) 0.79667(4) 0.68963(3) 0.01655(10) Uani 1 1 d . . . . .
P1 P 0.32496(4) 0.73154(4) 0.38444(3) 0.01620(10) Uani 1 1 d . . . . .
O1 O 0.54475(11) 0.92964(10) 0.65919(10) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.31026(14) 0.58001(12) 0.42370(12) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.18016(14) 0.48099(13) 0.63706(13) 0.0251(3) Uani 1 1 d . . . . .
C7 C 0.16972(16) 0.81707(15) 0.35780(14) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.47564(15) 0.73312(15) 0.55582(14) 0.0181(3) Uani 1 1 d . . . . .
H15A H 0.565724 0.736227 0.487370 0.022 Uiso 1 1 calc R U . . .
H15B H 0.452913 0.641934 0.581183 0.022 Uiso 1 1 calc R U . . .
C23 C 0.58648(16) 0.57592(15) 0.83008(14) 0.0201(3) Uani 1 1 d . . . . .
H23 H 0.490857 0.558369 0.869628 0.024 Uiso 1 1 calc R U . . .
C1 C 0.46782(15) 0.74854(14) 0.24071(14) 0.0177(3) Uani 1 1 d . . . . .
C22 C 0.62171(16) 0.68407(15) 0.74068(14) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.16149(16) 0.95136(15) 0.33395(15) 0.0213(3) Uani 1 1 d . . . . .
H12 H 0.238155 0.998743 0.330859 0.026 Uiso 1 1 calc R U . . .
C8 C 0.05663(16) 0.74781(16) 0.36313(14) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.062230 0.656706 0.379919 0.025 Uiso 1 1 calc R U . . .
C14 C 0.36054(16) 0.80688(14) 0.50499(14) 0.0179(3) Uani 1 1 d . . . . .
H14A H 0.389171 0.895169 0.469456 0.021 Uiso 1 1 calc R U . . .
H14B H 0.273297 0.813439 0.575846 0.021 Uiso 1 1 calc R U . . .
C6 C 0.45686(16) 0.82738(15) 0.13208(14) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.372095 0.876721 0.132551 0.024 Uiso 1 1 calc R U . . .
C2 C 0.59341(16) 0.67715(15) 0.23890(15) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.601208 0.622794 0.312470 0.025 Uiso 1 1 calc R U . . .
C24 C 0.69196(17) 0.49375(15) 0.86118(14) 0.0224(3) Uani 1 1 d . . . . .
H24 H 0.668188 0.420311 0.922355 0.027 Uiso 1 1 calc R U . . .
C16 C 0.32869(15) 0.78811(15) 0.81075(14) 0.0183(3) Uani 1 1 d . . . . .
C27 C 0.76280(16) 0.70777(15) 0.68181(15) 0.0210(3) Uani 1 1 d . . . . .
H27 H 0.787273 0.780762 0.620190 0.025 Uiso 1 1 calc R U . . .
C25 C 0.83177(17) 0.51899(16) 0.80293(15) 0.0229(3) Uani 1 1 d . . . . .
H25 H 0.903402 0.463172 0.824891 0.027 Uiso 1 1 calc R U . . .
C21 C 0.28942(16) 0.88780(16) 0.88547(15) 0.0223(3) Uani 1 1 d . . . . .
H21 H 0.349930 0.955560 0.871591 0.027 Uiso 1 1 calc R U . . .
C13 C 0.23909(15) 0.53123(14) 0.53764(15) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.69555(17) 0.76366(16) 0.02168(15) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.773131 0.769249 -0.052794 0.027 Uiso 1 1 calc R U . . .
C17 C 0.23733(16) 0.69058(16) 0.82933(15) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.263042 0.622755 0.778451 0.026 Uiso 1 1 calc R U . . .
C11 C 0.03999(17) 1.01459(16) 0.31485(15) 0.0246(3) Uani 1 1 d . . . . .
H11 H 0.033555 1.105707 0.298488 0.029 Uiso 1 1 calc R U . . .
C9 C -0.06430(17) 0.81238(16) 0.34382(15) 0.0234(3) Uani 1 1 d . . . . .
H9 H -0.141386 0.765399 0.347259 0.028 Uiso 1 1 calc R U . . .
C5 C 0.57070(17) 0.83356(15) 0.02275(14) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.562586 0.886154 -0.051632 0.026 Uiso 1 1 calc R U . . .
C20 C 0.16168(17) 0.88798(18) 0.98032(16) 0.0277(4) Uani 1 1 d . . . . .
H20 H 0.136172 0.954730 1.032482 0.033 Uiso 1 1 calc R U . . .
C26 C 0.86714(17) 0.62546(16) 0.71278(15) 0.0236(3) Uani 1 1 d . . . . .
H26 H 0.962889 0.641905 0.672293 0.028 Uiso 1 1 calc R U . . .
C10 C -0.07234(17) 0.94511(17) 0.31958(15) 0.0248(3) Uani 1 1 d . . . . .
H10 H -0.154950 0.989012 0.306101 0.030 Uiso 1 1 calc R U . . .
C3 C 0.70691(17) 0.68523(16) 0.13009(15) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.792381 0.637167 0.129674 0.028 Uiso 1 1 calc R U . . .
C18 C 0.10833(17) 0.69334(17) 0.92286(16) 0.0264(4) Uani 1 1 d . . . . .
H18 H 0.045287 0.628143 0.934683 0.032 Uiso 1 1 calc R U . . .
C19 C 0.07189(17) 0.79119(18) 0.99871(16) 0.0280(4) Uani 1 1 d . . . . .
H19 H -0.015171 0.791637 1.063572 0.034 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
P2 O1 1.4876(12) . ?
P2 C15 1.8129(15) . ?
P2 C22 1.8031(15) . ?
P2 C16 1.8099(15) . ?
P1 N1 1.6014(13) . ?
P1 C7 1.8026(15) . ?
P1 C1 1.7978(15) . ?
P1 C14 1.8122(15) . ?
N1 C13 1.312(2) . ?
N2 C13 1.163(2) . ?
C7 C12 1.400(2) . ?
C7 C8 1.395(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.534(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.395(2) . ?
C23 C24 1.393(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.397(2) . ?
C22 C27 1.397(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C16 C21 1.396(2) . ?
C16 C17 1.399(2) . ?
C27 H27 0.9500 . ?
C27 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C4 C3 1.391(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C5 H5 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.382(3) . ?
C26 H26 0.9500 . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 H19 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 P2 C15 113.75(7) . . ?
O1 P2 C22 111.62(7) . . ?
O1 P2 C16 111.33(7) . . ?
C22 P2 C15 104.07(7) . . ?
C22 P2 C16 109.04(7) . . ?
C16 P2 C15 106.64(7) . . ?
N1 P1 C7 113.77(7) . . ?
N1 P1 C1 105.55(7) . . ?
N1 P1 C14 112.10(7) . . ?
C7 P1 C14 105.51(7) . . ?
C1 P1 C7 109.40(7) . . ?
C1 P1 C14 110.56(7) . . ?
C13 N1 P1 121.98(11) . . ?
C12 C7 P1 120.62(12) . . ?
C8 C7 P1 119.15(12) . . ?
C8 C7 C12 120.23(14) . . ?
P2 C15 H15A 109.0 . . ?
P2 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C14 C15 P2 113.14(10) . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C24 C23 C22 119.80(15) . . ?
C6 C1 P1 122.76(11) . . ?
C6 C1 C2 119.49(14) . . ?
C2 C1 P1 117.74(11) . . ?
C23 C22 P2 124.46(12) . . ?
C23 C22 C27 119.54(14) . . ?
C27 C22 P2 115.97(12) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.27(15) . . ?
C11 C12 H12 120.4 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.86(15) . . ?
C9 C8 H8 120.1 . . ?
P1 C14 H14A 109.0 . . ?
P1 C14 H14B 109.0 . . ?
C15 C14 P1 113.05(10) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.79(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.33(14) . . ?
C3 C2 H2 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.13(15) . . ?
C25 C24 H24 119.9 . . ?
C21 C16 P2 116.77(12) . . ?
C21 C16 C17 119.66(14) . . ?
C17 C16 P2 123.54(12) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 C22 120.37(15) . . ?
C26 C27 H27 119.8 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.19(14) . . ?
C26 C25 H25 119.9 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.05(15) . . ?
C20 C21 H21 120.0 . . ?
N2 C13 N1 175.93(17) . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.76(15) . . ?
C3 C4 H4 120.1 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.72(15) . . ?
C18 C17 H17 120.1 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.33(15) . . ?
C10 C11 H11 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.99(15) . . ?
C10 C9 H9 120.0 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.56(14) . . ?
C4 C5 H5 119.7 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.11(15) . . ?
C19 C20 H20 119.9 . . ?
C27 C26 C25 119.97(15) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.32(15) . . ?
C9 C10 H10 119.8 . . ?
C2 C3 C4 120.06(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.12(16) . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.31(16) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P2 C15 C14 P1 -172.77(8) . . . . ?
P2 C22 C27 C26 -178.80(12) . . . . ?
P2 C16 C21 C20 179.81(12) . . . . ?
P2 C16 C17 C18 -178.28(12) . . . . ?
P1 C7 C12 C11 -179.45(12) . . . . ?
P1 C7 C8 C9 179.48(12) . . . . ?
P1 C1 C6 C5 -178.34(12) . . . . ?
P1 C1 C2 C3 179.28(12) . . . . ?
O1 P2 C15 C14 -64.41(13) . . . . ?
O1 P2 C22 C23 146.55(13) . . . . ?
O1 P2 C22 C27 -35.47(14) . . . . ?
O1 P2 C16 C21 -19.59(14) . . . . ?
O1 P2 C16 C17 158.31(12) . . . . ?
N1 P1 C7 C12 174.24(12) . . . . ?
N1 P1 C7 C8 -4.79(15) . . . . ?
N1 P1 C1 C6 128.43(13) . . . . ?
N1 P1 C1 C2 -50.34(14) . . . . ?
N1 P1 C14 C15 46.37(13) . . . . ?
C7 P1 N1 C13 -76.12(14) . . . . ?
C7 P1 C1 C6 5.64(15) . . . . ?
C7 P1 C1 C2 -173.13(12) . . . . ?
C7 P1 C14 C15 170.71(11) . . . . ?
C7 C12 C11 C10 0.1(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C15 P2 C22 C23 -90.36(14) . . . . ?
C15 P2 C22 C27 87.62(13) . . . . ?
C15 P2 C16 C21 -144.20(12) . . . . ?
C15 P2 C16 C17 33.70(14) . . . . ?
C23 C22 C27 C26 -0.7(2) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C1 P1 N1 C13 163.93(12) . . . . ?
C1 P1 C7 C12 -68.00(14) . . . . ?
C1 P1 C7 C8 112.97(13) . . . . ?
C1 P1 C14 C15 -71.11(12) . . . . ?
C1 C6 C5 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C22 P2 C15 C14 173.90(11) . . . . ?
C22 P2 C16 C21 103.99(12) . . . . ?
C22 P2 C16 C17 -78.11(14) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C22 C27 C26 C25 -0.2(2) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C12 C11 C10 C9 0.2(2) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C14 P1 N1 C13 43.49(15) . . . . ?
C14 P1 C7 C12 50.96(14) . . . . ?
C14 P1 C7 C8 -128.07(12) . . . . ?
C14 P1 C1 C6 -110.14(13) . . . . ?
C14 P1 C1 C2 71.09(14) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C24 C23 C22 P2 178.87(11) . . . . ?
C24 C23 C22 C27 1.0(2) . . . . ?
C24 C25 C26 C27 0.8(2) . . . . ?
C16 P2 C15 C14 58.69(12) . . . . ?
C16 P2 C22 C23 23.14(15) . . . . ?
C16 P2 C22 C27 -158.88(11) . . . . ?
C16 C21 C20 C19 -1.6(2) . . . . ?
C16 C17 C18 C19 -1.2(2) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
C21 C20 C19 C18 0.0(3) . . . . ?
C17 C16 C21 C20 1.8(2) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?

_olex2_date_sample_data_collection 2023-01-09
_olex2_date_sample_submission    2023-01-09
_olex2_exptl_crystal_mounting_method 
'mounted using Paratone oil onto a MiTeGen loop'
_olex2_submission_original_sample_id msd001
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_Compound_31
_database_code_depnum_ccdc_archive 'CCDC 2258977'
loop_
_audit_author_name
_audit_author_address
'Mohammad Chaudhry'
;MRL
United States of America
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
velabo.mdluli@merck.com
mohammad.chaudhry1@merck.com
justin.newman@merck.com
_chemical_name_common            Compound_31
_chemical_name_systematic        Compound_31
_chemical_formula_moiety         
'0.8(C40 H32 N4 O2 P2), 0.4(H2 O), 1.6(C2 H3 N)'
_chemical_formula_sum            'C35.20 H31.20 N4.80 O2 P1.60'
_chemical_formula_weight         603.00
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N2 P1 O2 C40 H40'
_chemical_oxdiff_usercomment     SWMS-339-54-again-prism
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.02580(10)
_cell_length_b                   17.46940(10)
_cell_length_c                   19.01960(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.9480(10)
_cell_angle_gamma                90
_cell_volume                     3894.11(5)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    101143
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.6400
_cell_measurement_theta_min      3.4360
_shelx_estimated_absorpt_T_max   0.798
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1580
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1342
0 1 0 0.1100
0 -1 -1 0.1245
0 1 2 0.0949
0 -1 2 0.1137
1 -2 -2 0.1300
-1 2 2 0.1326
-2 0 1 0.0941
2 0 -1 0.0798
1 1 1 0.0836
-1 -1 -1 0.1302
-1 1 -2 0.1390
1 0 2 0.0786
1 0 -2 0.0965
-1 0 2 0.0870
2 -1 1 0.0870
-2 1 -1 0.1125

_exptl_crystal_recrystallization_method 
'Slow evaporation from a solution of mds081 in MeCN/H2O'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0013 -1.0003 -0.0001 0.0024 -0.0147 0.0869
-0.0013 1.0003 0.0001 -0.0024 0.0147 -0.0869
0.0007 -0.9999 -1.0002 0.0189 -0.0950 0.0728
-0.0002 0.9995 2.0002 -0.0354 0.1752 -0.0587
0.0023 -1.0010 2.0000 -0.0306 0.1457 0.1151
1.0013 -1.9997 -2.0007 0.1574 -0.1359 0.1516
-1.0013 1.9997 2.0007 -0.1574 0.1359 -0.1516
-1.9990 -0.0005 1.0008 -0.2558 -0.0280 0.0020
1.9990 0.0005 -1.0008 0.2558 0.0280 -0.0020
0.9990 0.9999 0.9998 0.1008 0.1491 -0.0667
-0.9990 -0.9999 -0.9998 -0.1008 -0.1491 0.0667
-1.0021 1.0010 -1.9996 -0.0891 -0.1999 -0.1212
1.0008 -0.0007 1.9997 0.0867 0.2146 0.0343
0.9987 0.0008 -2.0004 0.1527 -0.1064 -0.0222
-0.9987 -0.0008 2.0004 -0.1527 0.1064 0.0222
2.0014 -1.0005 0.9992 0.2252 0.1737 0.1131
-2.0014 1.0005 -0.9992 -0.2252 -0.1737 -0.1131

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            137025
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.600
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  28.00   0.50    0.05    --   14.00  59.00-129.86   54
  2  ω     11.00  38.00   0.50    0.05    --   22.00  52.00 -98.63   54
  3  ω     15.00  41.00   0.50    0.05    --   26.00  50.00 -18.81   52
  4  ω     15.00  41.00   0.50    0.05    --   26.00  50.00  40.76   52
  5  ω      1.00  28.00   0.50    0.05    --   14.00  59.00  83.61   54
  6  ω     29.00  57.00   0.50    0.05    --   38.00  44.00-146.88   56
  7  ω     68.00 105.00   0.50    0.15    --  107.23 -99.00  30.00   74
  8  ω     59.00 121.00   0.50    0.05    --   50.08-174.00  97.00  124
  9  ω     59.00 146.00   0.50    0.15    --  107.23-174.00  97.00  174
 10  ω     75.00 105.00   0.50    0.15    --  107.23 -99.00  60.00   60
 11  ω     35.00  61.00   0.50    0.15    --  107.23 -99.00  30.00   52
 12  ω     35.00  66.00   0.50    0.15    --  107.23 -99.00 -30.00   62
 13  ω     71.00 105.00   0.50    0.15    --  107.23 -99.00 -30.00   68
 14  ω     27.00  91.00   0.50    0.05    --   50.08-115.00-123.00  128
 15  ω     36.00 101.00   0.50    0.15    --  107.23-125.00-150.00  130
 16  ω     35.00 102.00   0.50    0.15    --  107.23 -99.00-120.00  134
 17  ω     35.00 109.00   0.50    0.15    --  107.23-115.00-123.00  148
 18  ω     36.00 105.00   0.50    0.15    --  107.23 -99.00 -90.00  138
 19  ω     35.00  60.00   0.50    0.15    --  107.23 -99.00  60.00   50
 20  ω     35.00 105.00   0.50    0.15    --  107.23 -99.00 120.00  140
 21  ω     36.00 105.00   0.50    0.15    --  107.23 -99.00 150.00  138
 22  ω     35.00  62.00   0.50    0.15    --  107.23 -57.00  90.00   54
 23  ω     36.00  62.00   0.50    0.15    --  107.23 -57.00 120.00   52
 24  ω     35.00  97.00   0.50    0.15    --  107.23 -77.00  30.00  124
 25  ω     36.00  64.00   0.50    0.15    --  107.23 -57.00  30.00   56
 26  ω     37.00  64.00   0.50    0.15    --  107.23 -57.00 -60.00   54
 27  ω     35.00  60.00   0.50    0.15    --  107.23 -57.00 -90.00   50
 28  ω     38.00  64.00   0.50    0.15    --  107.23 -57.00-120.00   52
 29  ω    100.00 133.00   0.50    0.15    --  107.23  38.00-120.00   66
 30  ω     65.00 122.00   0.50    0.05    --   50.08 174.00 106.00  114
 31  ω     65.00 148.00   0.50    0.15    --  107.23 174.00 106.00  166
 32  ω    101.00 178.00   0.50    0.15    --  107.23 115.00 -33.00  154
 33  ω    144.00 173.00   0.50    0.15    --  107.23  38.00-120.00   58
 34  ω     42.00  67.00   0.50    0.05    --   50.08  41.00 179.18   50
 35  ω    -46.00 -18.00   0.50    0.15    --  -90.00  38.00 -90.00   56
 36  ω    -83.00 -18.00   0.50    0.15    --  -90.00 115.00 -33.00  130
 37  ω   -121.00 -37.00   0.50    0.15    --  -90.00 174.00 106.00  168
 38  ω   -120.00 -45.00   0.50    0.05    --  -50.08 174.00 106.00  150
 39  ω    -83.00  -6.00   0.50    0.05    --  -50.08 115.00 -33.00  154
 40  ω    -45.00 -19.00   0.50    0.15    --  -90.00  38.00 120.00   52
 41  ω   -120.00 -86.00   0.50    0.05    --  -50.00 -42.00   0.26   68
 42  ω    -61.00 -33.00   0.50    0.05    --  -42.00 -43.00-117.74   56
 43  ω    -41.00 -15.00   0.50    0.05    --  -26.00 -50.00 -21.83   52
 44  ω    -21.00   6.00   0.50    0.05    --  -10.00 -65.00 159.53   54
 45  ω    -50.00 -24.00   0.50    0.05    --  -34.00 -46.00 147.62   52
 46  ω    -30.00  -1.00   0.50    0.05    --  -14.00 -57.00  68.36   58
 47  ω    -69.00 -41.00   0.50    0.05    --  -50.00 -42.00  56.50   56
 48  ω    -69.00 -43.00   0.50    0.05    --  -50.00 -42.00  18.26   52
 49  ω    -69.00 -41.00   0.50    0.05    --  -50.00 -42.00   0.26   56
 50  ω    -75.00 -43.00   0.50    0.05    --  -50.00 -42.00  72.78   64
 51  ω   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00 -44.46  160
 52  ω    -75.00 -42.00   0.50    0.05    --  -50.00 -42.00 -64.85   66
 53  ω    -80.00 -43.00   0.50    0.05    --  -50.00 -42.00-145.09   74
 54  ω   -117.00 -83.00   0.50    0.05    --  -50.00 -42.00 -64.85   68
 55  ω   -118.00 -91.00   0.50    0.05    --  -50.00 -42.00 148.88   54
 56  ω    -81.00 -43.00   0.50    0.05    --  -50.00 -42.00 148.88   76
 57  ω    -86.00 -60.00   0.50    0.05    --  -70.00 -42.00 158.23   52
 58  ω    -91.00 -65.00   0.50    0.15    --  -74.00 -42.00 124.36   52
 59  ω    -90.00 -64.00   0.50    0.15    --  -74.00 -42.00  43.29   52
 60  ω    -86.00 -60.00   0.50    0.05    --  -70.00 -42.00  -2.91   52
 61  ω    -90.00 -64.00   0.50    0.15    --  -74.00 -42.00 -59.92   52
 62  ω    -88.00 -62.00   0.50    0.05    --  -70.00 -42.00 -83.75   52
 63  ω    -91.00 -65.00   0.50    0.15    --  -74.00 -42.00-139.86   52
 64  ω    -90.00 -64.00   0.50    0.15    --  -74.00 -42.00-155.32   52
 65  ω    -90.00 -64.00   0.50    0.15    --  -74.00 -42.00-176.19   52
 66  ω    -90.00 -64.00   0.50    0.15    --  -74.00 -42.00-124.59   52
 67  ω    -89.00 -64.00   0.50    0.15    --  -74.00 -42.00-101.68   50
 68  ω    -92.00 -57.00   0.50    0.05    --  -66.00 -41.00 -50.51   70
 69  ω   -138.00-112.00   0.50    0.05    --  -66.00 -41.00 -50.51   52
 70  ω   -118.00 -92.00   0.50    0.05    --  -54.00 -41.00 -31.07   52
 71  ω    -86.00 -61.00   0.50    0.05    --  -70.00 -41.00  51.38   50
 72  ω    -71.00 -45.00   0.50    0.05    --  -54.00 -41.00 -31.07   52
 73  ω    -88.00 -61.00   0.50    0.05    --  -70.00 -41.00  69.75   54
 74  ω    -91.00 -65.00   0.50    0.15    --  -74.00 -41.00 108.55   52
 75  ω    -84.00 -57.00   0.50    0.05    --  -66.00 -41.00 143.74   54
 76  ω    -89.00 -64.00   0.50    0.15    --  -74.00 -42.00 140.61   50
 77  ω    -93.00 -67.00   0.50    0.15    --  -74.00 -41.00 171.65   52
 78  ω   -148.00 -86.00   0.50    0.15    --  -90.00 -42.00 168.58  124
 79  ω   -137.00-109.00   0.50    0.05    --  -66.00 -41.00 143.74   56
 80  ω   -139.00 -82.00   0.50    0.15    --  -90.00 -40.00  39.16  114
 81  ω   -112.00 -81.00   0.50    0.15    --  -90.00 -41.00  70.25   62
 82  ω   -160.00-126.00   0.50    0.15    --  -90.00 -40.00  83.40   68
 83  ω    -99.00 -73.00   0.50    0.15    --  -82.00 -41.00  40.47   52
 84  ω   -119.00 -82.00   0.50    0.15    --  -90.00 -40.00  83.40   74
 85  ω    -94.00 -68.00   0.50    0.15    --  -74.00 -40.00 -11.36   52
 86  ω    -96.00 -70.00   0.50    0.15    --  -78.00 -39.00  21.35   52
 87  ω   -107.00 -81.00   0.50    0.15    --  -90.00 -41.00 -23.65   52
 88  ω   -104.00 -78.00   0.50    0.15    --  -86.00 -39.00 -38.26   52
 89  ω   -160.00-135.00   0.50    0.15    --  -90.00 -39.00 -91.07   50
 90  ω   -155.00-129.00   0.50    0.15    --  -86.00 -39.00 -65.38   52
 91  ω   -104.00 -78.00   0.50    0.15    --  -86.00 -39.00 -65.38   52
 92  ω    -67.00 -42.00   0.50    0.05    --  -50.08 -39.00-178.69   50
 93  ω    -97.00 -71.00   0.50    0.05    --  -50.08 -39.00-178.69   52
 94  ω   -113.00 -82.00   0.50    0.15    --  -90.00 -40.00-156.86   62
 95  ω   -117.00 -82.00   0.50    0.15    --  -90.00 -39.00 -91.07   70
 96  ω   -114.00 -78.00   0.50    0.15    --  -86.00 -39.00  11.52   72
 97  ω   -158.00-132.00   0.50    0.15    --  -90.00 -39.00 106.48   52
 98  ω   -161.00-132.00   0.50    0.15    --  -90.00 -39.00 140.06   58
 99  ω   -118.00 -82.00   0.50    0.15    --  -90.00 -39.00 140.06   72
100  ω   -109.00 -83.00   0.50    0.15    --  -90.00 -39.00 106.48   52
101  ω   -156.00 -78.00   0.50    0.15    --  -86.00 -38.00 -12.01  156
102  ω   -150.00-123.00   0.50    0.15    --  -86.00 -39.00 -38.26   54
103  ω   -109.00 -82.00   0.50    0.15    --  -90.00 -38.00-115.63   54
104  ω   -110.00 -82.00   0.50    0.15    --  -90.00 -38.00-127.87   56
105  ω   -109.00 -83.00   0.50    0.15    --  -90.00 -38.00-141.67   52
106  ω   -160.00-122.00   0.50    0.15    --  -90.00 -38.00-115.63   76
107  ω   -161.00-135.00   0.50    0.15    --  -90.00 -38.00-127.87   52
108  ω   -161.00-136.00   0.50    0.15    --  -90.00 -38.00-141.67   50
109  ω   -122.00 -83.00   0.50    0.15    --  -90.00 -37.00 -73.74   78
110  ω   -103.00 -78.00   0.50    0.15    --  -86.00 -37.00 -22.26   50
111  ω   -147.00-121.00   0.50    0.15    --  -86.00 -37.00 -22.26   52
112  ω   -159.00 -81.00   0.50    0.15    --  -90.00 -36.00 -48.91  156
113  ω   -121.00 -82.00   0.50    0.15    --  -90.00 -36.00  46.74   78
114  ω   -162.00-125.00   0.50    0.15    --  -90.00 -36.00  46.74   74
115  ω   -161.00-111.00   0.50    0.15    --  -90.00 -38.00 120.00  100
116  ω   -107.00 -82.00   0.50    0.15    --  -90.00 -38.00 120.00   50
117  ω   -107.00 -81.00   0.50    0.15    --  -90.00 -36.00  93.63   52
118  ω   -129.00 -81.00   0.50    0.15    --  -90.00 -36.00 168.64   96
119  ω   -122.00 -43.00   0.50    0.05    --  -50.08-174.00  97.00  158
120  ω   -131.00 -43.00   0.50    0.15    --  -90.00-174.00  97.00  176
121  ω   -161.00 -80.00   0.50    0.15    --  -90.00-115.00-123.00  162
122  ω   -161.00-100.00   0.50    0.15    --  -90.00-125.00-150.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1196784000
_diffrn_orient_matrix_UB_12      -0.0022372000
_diffrn_orient_matrix_UB_13      -0.0165620000
_diffrn_orient_matrix_UB_21      0.0541520000
_diffrn_orient_matrix_UB_22      0.0147942000
_diffrn_orient_matrix_UB_23      0.0802170000
_diffrn_orient_matrix_UB_31      0.0060635000
_diffrn_orient_matrix_UB_32      -0.0868699000
_diffrn_orient_matrix_UB_33      0.0140820000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                14343
_reflns_number_total             14585
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 6046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         14585
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+1.2378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C76(H76), C63(H63), C77(H77), C55(H55), C2(H2), C65(H65), C24(H24), C30(H30),
 C36(H36), C44(H44), C43(H43), C40(H40), C11(H11), C38(H38), C25(H25), C8(H8),
 C16(H16), C23(H23), C12(H12), C57(H57), C17(H17), C64(H64), C46(H46), C74(H74),
  C15(H15), C42(H42), C39(H39), C34(H34), C10(H10), C56(H56), C37(H37),
 C80(H80), C45(H45), C9(H9), C70(H70), C78(H78), C6(H6), C79(H79), C50(H50),
 C52(H52), C33(H33), C5(H5), C4(H4), C72(H72), C73(H73), C49(H49), C32(H32),
 C31(H31), C3(H3), C71(H71), C48(H48), C51(H51)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C85(H85A,H85B,H85C), C60(H60A,H60B,H60C), C67(H67A,H67B,
 H67C), C89(H89A,H89B,H89C), C20(H20A,H20B,H20C), C83(H83A,H83B,H83C), C87(H87A,
 H87B,H87C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P4 P 0.31952(4) 0.38977(3) 0.41175(3) 0.01763(12) Uani 1 1 d . . . . .
P2 P 0.67908(5) 0.58958(3) 1.08281(3) 0.01961(12) Uani 1 1 d . . . . .
P1 P 0.32250(4) 0.68139(3) 0.93456(3) 0.01702(11) Uani 1 1 d . . . . .
P3 P 0.70205(5) 0.47104(4) 0.58052(3) 0.02183(13) Uani 1 1 d . . . . .
O1 O 0.25151(14) 0.60796(10) 1.09020(9) 0.0256(4) Uani 1 1 d . . . . .
O3 O 0.47361(14) 0.46771(10) 0.31418(8) 0.0233(3) Uani 1 1 d . . . . .
O2 O 0.55514(14) 0.67717(10) 1.19730(8) 0.0225(3) Uani 1 1 d . . . . .
O4 O 0.76066(12) 0.38452(10) 0.44107(9) 0.0239(3) Uani 1 1 d . . . . .
O5 O 0.33541(17) 0.40594(13) 0.71143(11) 0.0397(5) Uani 1 1 d G . . . .
H5A H 0.350235 0.441061 0.744643 0.059 Uiso 1 1 d G U . . .
H5B H 0.401182 0.395791 0.701677 0.059 Uiso 1 1 d G U . . .
N2 N 0.3727(2) 0.51177(14) 0.82933(12) 0.0339(5) Uani 1 1 d . . . . .
N4 N 0.68089(18) 0.72991(13) 0.94019(12) 0.0289(5) Uani 1 1 d . . . . .
N1 N 0.39536(17) 0.60706(12) 0.92639(10) 0.0220(4) Uani 1 1 d . . . . .
C59 C 0.57260(17) 0.47082(14) 0.43465(11) 0.0174(4) Uani 1 1 d . . . . .
C13 C 0.68284(19) 0.70305(14) 0.99629(13) 0.0211(5) Uani 1 1 d . . . . .
N3 N 0.68890(17) 0.67751(13) 1.06211(10) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.33820(19) 0.56046(14) 1.08110(12) 0.0202(4) Uani 1 1 d . . . . .
C19 C 0.44182(18) 0.59741(13) 1.08103(11) 0.0178(4) Uani 1 1 d . . . . .
C58 C 0.52581(18) 0.51202(14) 0.37144(12) 0.0197(5) Uani 1 1 d . . . . .
C28 C 0.37915(19) 0.55843(14) 0.87355(12) 0.0216(5) Uani 1 1 d . . . . .
C61 C 0.56343(17) 0.38544(14) 0.43187(11) 0.0172(4) Uani 1 1 d . . . . .
C21 C 0.44527(17) 0.68284(14) 1.07946(11) 0.0176(4) Uani 1 1 d . . . . .
C62 C 0.66355(19) 0.34213(14) 0.43560(12) 0.0201(5) Uani 1 1 d . . . . .
N7 N 0.31663(17) 0.47828(12) 0.43112(11) 0.0260(4) Uani 1 1 d . . . . .
C76 C 0.16046(19) 0.27740(14) 0.42999(13) 0.0225(5) Uani 1 1 d . . . . .
H76 H 0.140579 0.272620 0.378946 0.027 Uiso 1 1 calc R U . . .
C63 C 0.66102(19) 0.26295(14) 0.43276(12) 0.0222(5) Uani 1 1 d . . . . .
H63 H 0.729769 0.234952 0.436269 0.027 Uiso 1 1 calc R U . . .
N10 N 0.0311(2) 0.67118(18) 0.69648(16) 0.0494(7) Uani 1 1 d . . . . .
C54 C 0.62857(18) 0.51292(13) 0.49549(12) 0.0183(4) Uani 1 1 d . . . . .
C77 C 0.1063(2) 0.23260(15) 0.47250(14) 0.0268(5) Uani 1 1 d . . . . .
H77 H 0.049913 0.196633 0.450522 0.032 Uiso 1 1 calc R U . . .
C75 C 0.24440(18) 0.32962(14) 0.46262(12) 0.0191(4) Uani 1 1 d . . . . .
C29 C 0.17439(18) 0.66466(14) 0.93420(12) 0.0204(5) Uani 1 1 d . . . . .
C55 C 0.63418(19) 0.59298(14) 0.49253(12) 0.0223(5) Uani 1 1 d . . . . .
H55 H 0.671032 0.620902 0.534107 0.027 Uiso 1 1 calc R U . . .
C22 C 0.50388(19) 0.72256(14) 1.14076(12) 0.0192(4) Uani 1 1 d . . . . .
C66 C 0.45922(19) 0.34572(13) 0.42243(11) 0.0188(4) Uani 1 1 d . . . . .
C35 C 0.32035(19) 0.74822(13) 0.86196(12) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.8604(2) 0.62496(16) 1.19461(14) 0.0284(5) Uani 1 1 d . . . . .
H2 H 0.882167 0.658655 1.160847 0.034 Uiso 1 1 calc R U . . .
C26 C 0.39305(18) 0.72585(13) 1.01853(12) 0.0183(4) Uani 1 1 d . . . . .
C65 C 0.4576(2) 0.26518(14) 0.41953(12) 0.0224(5) Uani 1 1 d . . . . .
H65 H 0.387280 0.238603 0.413938 0.027 Uiso 1 1 calc R U . . .
C24 C 0.4590(2) 0.84310(14) 1.08103(13) 0.0225(5) Uani 1 1 d . . . . .
H24 H 0.464215 0.897369 1.081342 0.027 Uiso 1 1 calc R U . . .
C30 C 0.1188(2) 0.60292(16) 0.89573(13) 0.0270(5) Uani 1 1 d . . . . .
H30 H 0.160315 0.567183 0.873981 0.032 Uiso 1 1 calc R U . . .
C36 C 0.4239(2) 0.76195(15) 0.84177(13) 0.0245(5) Uani 1 1 d . . . . .
H36 H 0.492094 0.738460 0.867611 0.029 Uiso 1 1 calc R U . . .
C69 C 0.24337(18) 0.38271(15) 0.31876(12) 0.0215(5) Uani 1 1 d . . . . .
C44 C 0.6574(2) 0.63401(16) 0.76190(13) 0.0279(5) Uani 1 1 d . . . . .
H44 H 0.648546 0.666901 0.800036 0.033 Uiso 1 1 calc R U . . .
N8 N 0.3369(2) 0.54301(15) 0.54823(14) 0.0392(6) Uani 1 1 d . . . . .
C43 C 0.5670(2) 0.58823(16) 0.72719(14) 0.0283(5) Uani 1 1 d . . . . .
H43 H 0.496515 0.589602 0.741865 0.034 Uiso 1 1 calc R U . . .
N5 N 0.6653(2) 0.38572(15) 0.59380(12) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.73775(19) 0.52755(14) 1.02477(13) 0.0218(5) Uani 1 1 d . . . . .
C40 C 0.22028(19) 0.78235(15) 0.82343(12) 0.0230(5) Uani 1 1 d . . . . .
H40 H 0.149914 0.773175 0.836774 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7344(2) 0.48498(15) 0.90339(13) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.700114 0.485321 0.853270 0.031 Uiso 1 1 calc R U . . .
C38 C 0.3264(2) 0.84324(15) 0.74550(13) 0.0278(5) Uani 1 1 d . . . . .
H38 H 0.328217 0.875322 0.705442 0.033 Uiso 1 1 calc R U . . .
C84 C 0.1195(2) 0.65129(17) 0.69264(14) 0.0335(6) Uani 1 1 d . . . . .
C25 C 0.39927(19) 0.80574(14) 1.01965(12) 0.0210(5) Uani 1 1 d . . . . .
H25 H 0.362707 0.834431 0.978516 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8355(2) 0.48336(16) 1.05023(14) 0.0286(5) Uani 1 1 d . . . . .
H8 H 0.869966 0.482536 1.100314 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5374(2) 0.55148(14) 1.07961(12) 0.0203(4) Uani 1 1 d . . . . .
C16 C 0.4206(2) 0.43778(15) 1.06953(13) 0.0251(5) Uani 1 1 d . . . . .
H16 H 0.413286 0.383878 1.063679 0.030 Uiso 1 1 calc R U . . .
C41 C 0.6843(2) 0.53691(14) 0.65074(12) 0.0214(5) Uani 1 1 d . . . . .
C23 C 0.51104(19) 0.80211(14) 1.14166(12) 0.0218(5) Uani 1 1 d . . . . .
H23 H 0.551340 0.828006 1.183597 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6872(2) 0.52772(14) 0.95086(13) 0.0230(5) Uani 1 1 d . . . . .
H12 H 0.620407 0.557196 0.933192 0.028 Uiso 1 1 calc R U . . .
C27 C 0.6329(2) 0.71417(15) 1.25630(12) 0.0239(5) Uani 1 1 d . . . . .
H27A H 0.687202 0.745468 1.237357 0.036 Uiso 1 1 calc R U . . .
H27B H 0.674501 0.675273 1.289052 0.036 Uiso 1 1 calc R U . . .
H27C H 0.589852 0.746905 1.282551 0.036 Uiso 1 1 calc R U . . .
C57 C 0.53188(19) 0.59106(15) 0.36849(12) 0.0231(5) Uani 1 1 d . . . . .
H57 H 0.499047 0.617423 0.325120 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3264(2) 0.48134(14) 1.07293(12) 0.0235(5) Uani 1 1 d . . . . .
H17 H 0.254233 0.457748 1.069756 0.028 Uiso 1 1 calc R U . . .
C47 C 0.8529(2) 0.46869(16) 0.58287(13) 0.0265(5) Uani 1 1 d . . . . .
C68 C 0.3280(2) 0.50955(16) 0.49385(15) 0.0287(5) Uani 1 1 d . . . . .
C64 C 0.5579(2) 0.22447(15) 0.42476(13) 0.0241(5) Uani 1 1 d . . . . .
H64 H 0.556123 0.170133 0.422883 0.029 Uiso 1 1 calc R U . . .
C53 C 0.5926(2) 0.36437(15) 0.63077(14) 0.0295(6) Uani 1 1 d . . . . .
C46 C 0.7745(2) 0.58286(16) 0.68574(13) 0.0257(5) Uani 1 1 d . . . . .
H46 H 0.845672 0.580864 0.671942 0.031 Uiso 1 1 calc R U . . .
C74 C 0.1451(2) 0.42711(16) 0.29755(14) 0.0283(5) Uani 1 1 d . . . . .
H74 H 0.122918 0.461117 0.330901 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5262(2) 0.47218(15) 1.07459(13) 0.0246(5) Uani 1 1 d . . . . .
H15 H 0.591382 0.441395 1.074630 0.030 Uiso 1 1 calc R U . . .
C42 C 0.5797(2) 0.54045(15) 0.67100(13) 0.0263(5) Uani 1 1 d . . . . .
H42 H 0.517361 0.510249 0.646432 0.032 Uiso 1 1 calc R U . . .
C39 C 0.2241(2) 0.82994(15) 0.76529(13) 0.0273(5) Uani 1 1 d . . . . .
H39 H 0.156153 0.853406 0.739047 0.033 Uiso 1 1 calc R U . . .
C34 C 0.1127(2) 0.71706(15) 0.96613(13) 0.0254(5) Uani 1 1 d . . . . .
H34 H 0.150650 0.759271 0.992618 0.030 Uiso 1 1 calc R U . . .
C1 C 0.7626(2) 0.58012(15) 1.17385(13) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.8318(2) 0.44170(16) 0.92925(15) 0.0285(5) Uani 1 1 d . . . . .
H10 H 0.864350 0.412571 0.896752 0.034 Uiso 1 1 calc R U . . .
C56 C 0.5864(2) 0.63163(15) 0.42948(13) 0.0250(5) Uani 1 1 d . . . . .
H56 H 0.590836 0.685875 0.427826 0.030 Uiso 1 1 calc R U . . .
C37 C 0.4264(2) 0.80984(16) 0.78403(14) 0.0287(5) Uani 1 1 d . . . . .
H37 H 0.496612 0.819823 0.770806 0.034 Uiso 1 1 calc R U . . .
C80 C 0.2728(2) 0.33692(15) 0.53799(13) 0.0248(5) Uani 1 1 d . . . . .
H80 H 0.330345 0.371941 0.560435 0.030 Uiso 1 1 calc R U . . .
C45 C 0.7605(2) 0.63158(16) 0.74079(13) 0.0275(5) Uani 1 1 d . . . . .
H45 H 0.821764 0.663406 0.764096 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8818(2) 0.44092(17) 1.00259(15) 0.0328(6) Uani 1 1 d . . . . .
H9 H 0.948240 0.411025 1.020053 0.039 Uiso 1 1 calc R U . . .
C70 C 0.2761(2) 0.33331(15) 0.26920(13) 0.0242(5) Uani 1 1 d . . . . .
H70 H 0.342495 0.302630 0.283704 0.029 Uiso 1 1 calc R U . . .
C78 C 0.1343(2) 0.24017(16) 0.54701(14) 0.0282(5) Uani 1 1 d . . . . .
H78 H 0.097062 0.209308 0.575860 0.034 Uiso 1 1 calc R U . . .
N6 N 0.5301(3) 0.33922(17) 0.6628(2) 0.0575(8) Uani 1 1 d . . . . .
C6 C 0.7312(2) 0.53063(15) 1.22373(13) 0.0265(5) Uani 1 1 d . . . . .
H6 H 0.664660 0.499934 1.209875 0.032 Uiso 1 1 calc R U . . .
C79 C 0.2163(2) 0.29255(16) 0.57948(13) 0.0279(5) Uani 1 1 d . . . . .
H79 H 0.233969 0.298141 0.630460 0.034 Uiso 1 1 calc R U . . .
C50 C 1.0891(2) 0.46829(19) 0.59933(17) 0.0403(7) Uani 1 1 d . . . . .
H50 H 1.169610 0.468279 0.604962 0.048 Uiso 1 1 calc R U . . .
C52 C 0.9034(2) 0.51588(16) 0.54017(14) 0.0286(5) Uani 1 1 d . . . . .
H52 H 0.857393 0.548374 0.505368 0.034 Uiso 1 1 calc R U . . .
C33 C -0.0036(2) 0.70737(17) 0.95909(14) 0.0300(6) Uani 1 1 d . . . . .
H33 H -0.045426 0.743031 0.980679 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7974(2) 0.52626(16) 1.29379(14) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.775906 0.492731 1.327775 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8950(2) 0.57102(16) 1.31397(14) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.940368 0.567738 1.361674 0.038 Uiso 1 1 calc R U . . .
C72 C 0.1133(2) 0.37262(17) 0.17847(14) 0.0340(6) Uani 1 1 d . . . . .
H72 H 0.068464 0.369031 0.130634 0.041 Uiso 1 1 calc R U . . .
C73 C 0.0798(2) 0.42146(18) 0.22743(15) 0.0348(6) Uani 1 1 d . . . . .
H73 H 0.012185 0.451045 0.213072 0.042 Uiso 1 1 calc R U . . .
C85 C 0.2337(2) 0.62723(18) 0.68841(15) 0.0355(6) Uani 1 1 d . . . . .
H85A H 0.232988 0.610361 0.639171 0.053 Uiso 1 1 calc R U . . .
H85B H 0.258358 0.584842 0.722049 0.053 Uiso 1 1 calc R U . . .
H85C H 0.286649 0.670267 0.701168 0.053 Uiso 1 1 calc R U . . .
C49 C 1.0396(2) 0.4218(2) 0.64127(16) 0.0417(7) Uani 1 1 d . . . . .
H49 H 1.086271 0.389686 0.676085 0.050 Uiso 1 1 calc R U . . .
C32 C -0.0589(2) 0.64586(18) 0.92068(15) 0.0333(6) Uani 1 1 d . . . . .
H32 H -0.138647 0.639362 0.915865 0.040 Uiso 1 1 calc R U . . .
N12 N 1.1127(2) 0.37567(19) 0.96909(17) 0.0525(7) Uani 1 1 d . . . . .
C60 C 0.4114(2) 0.50624(17) 0.25137(13) 0.0305(6) Uani 1 1 d . . . . .
H60A H 0.374301 0.468411 0.215687 0.046 Uiso 1 1 calc R U . . .
H60B H 0.463790 0.537552 0.230807 0.046 Uiso 1 1 calc R U . . .
H60C H 0.353259 0.539188 0.264529 0.046 Uiso 1 1 calc R U . . .
C67 C 0.8666(2) 0.34342(16) 0.44966(15) 0.0300(6) Uani 1 1 d . . . . .
H67A H 0.864492 0.311345 0.407110 0.045 Uiso 1 1 calc R U . . .
H67B H 0.877546 0.310991 0.492715 0.045 Uiso 1 1 calc R U . . .
H67C H 0.929785 0.379923 0.455006 0.045 Uiso 1 1 calc R U . . .
C31 C 0.0021(2) 0.59362(18) 0.88915(15) 0.0335(6) Uani 1 1 d . . . . .
H31 H -0.036140 0.551320 0.862970 0.040 Uiso 1 1 calc R U . . .
C88 C 1.1517(2) 0.36654(17) 0.92043(17) 0.0351(6) Uani 1 1 d . . . . .
C3 C 0.9262(2) 0.62040(18) 1.26470(15) 0.0338(6) Uani 1 1 d . . . . .
H3 H 0.992650 0.651166 1.278794 0.041 Uiso 1 1 calc R U . . .
C89 C 1.2035(3) 0.3530(2) 0.85991(18) 0.0438(7) Uani 1 1 d . . . . .
H89A H 1.143664 0.344524 0.816284 0.066 Uiso 1 1 calc R U . . .
H89B H 1.252614 0.307674 0.869495 0.066 Uiso 1 1 calc R U . . .
H89C H 1.249303 0.397559 0.852916 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1435(2) 0.57337(17) 1.09087(16) 0.0335(6) Uani 1 1 d . . . . .
H20A H 0.114014 0.547378 1.044799 0.050 Uiso 1 1 calc R U . . .
H20B H 0.089406 0.613032 1.097999 0.050 Uiso 1 1 calc R U . . .
H20C H 0.153183 0.536088 1.130284 0.050 Uiso 1 1 calc R U . . .
C71 C 0.2119(2) 0.32888(17) 0.19882(14) 0.0305(6) Uani 1 1 d . . . . .
H71 H 0.235174 0.296221 0.164856 0.037 Uiso 1 1 calc R U . . .
N11 N -0.1034(2) 0.1559(2) 0.56142(19) 0.0579(8) Uani 1 1 d . . . . .
C48 C 0.9212(3) 0.42084(18) 0.63382(15) 0.0365(6) Uani 1 1 d . . . . .
H48 H 0.887596 0.388007 0.663049 0.044 Uiso 1 1 calc R U . . .
C51 C 1.0215(2) 0.51559(18) 0.54836(16) 0.0365(6) Uani 1 1 d . . . . .
H51 H 1.055837 0.547815 0.519013 0.044 Uiso 1 1 calc R U . . .
C86 C -0.1825(3) 0.16793(19) 0.58385(17) 0.0414(7) Uani 1 1 d . . . . .
C82 C 0.1510(3) 0.7734(2) 1.20492(18) 0.0435(7) Uani 1 1 d . . . . .
N9 N 0.0631(3) 0.7788(2) 1.2169(2) 0.0704(10) Uani 1 1 d . . . . .
C83 C 0.2628(3) 0.7684(3) 1.1899(2) 0.0573(9) Uani 1 1 d . . . . .
H83A H 0.263482 0.795881 1.145137 0.086 Uiso 1 1 calc R U . . .
H83B H 0.282192 0.714508 1.184676 0.086 Uiso 1 1 calc R U . . .
H83C H 0.318798 0.791316 1.229787 0.086 Uiso 1 1 calc R U . . .
C87 C -0.2844(3) 0.1805(3) 0.61051(19) 0.0563(9) Uani 1 1 d . . . . .
H87A H -0.312896 0.232420 0.598040 0.084 Uiso 1 1 calc R U . . .
H87B H -0.266721 0.174284 0.663052 0.084 Uiso 1 1 calc R U . . .
H87C H -0.342888 0.143235 0.588515 0.084 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
P4 N7 1.592(2) . ?
P4 C75 1.802(2) . ?
P4 C66 1.817(2) . ?
P4 C69 1.805(2) . ?
P2 N3 1.597(2) . ?
P2 C7 1.800(2) . ?
P2 C14 1.817(2) . ?
P2 C1 1.804(2) . ?
P1 N1 1.593(2) . ?
P1 C29 1.803(2) . ?
P1 C35 1.804(2) . ?
P1 C26 1.807(2) . ?
P3 C54 1.814(2) . ?
P3 N5 1.591(3) . ?
P3 C41 1.811(2) . ?
P3 C47 1.805(3) . ?
O1 C18 1.373(3) . ?
O1 C20 1.436(3) . ?
O3 C58 1.369(3) . ?
O3 C60 1.428(3) . ?
O2 C22 1.367(3) . ?
O2 C27 1.443(3) . ?
O4 C62 1.367(3) . ?
O4 C67 1.439(3) . ?
O5 H5A 0.8700 . ?
O5 H5B 0.8701 . ?
N2 C28 1.161(3) . ?
N4 C13 1.161(3) . ?
N1 C28 1.297(3) . ?
C59 C58 1.406(3) . ?
C59 C61 1.496(3) . ?
C59 C54 1.408(3) . ?
C13 N3 1.316(3) . ?
C18 C19 1.404(3) . ?
C18 C17 1.394(4) . ?
C19 C21 1.493(3) . ?
C19 C14 1.407(3) . ?
C58 C57 1.384(4) . ?
C61 C62 1.410(3) . ?
C61 C66 1.408(3) . ?
C21 C22 1.403(3) . ?
C21 C26 1.406(3) . ?
C62 C63 1.384(4) . ?
N7 C68 1.291(3) . ?
C76 H76 0.9500 . ?
C76 C77 1.388(3) . ?
C76 C75 1.398(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.389(3) . ?
N10 C84 1.136(4) . ?
C54 C55 1.402(3) . ?
C77 H77 0.9500 . ?
C77 C78 1.387(4) . ?
C75 C80 1.403(3) . ?
C29 C30 1.388(3) . ?
C29 C34 1.399(3) . ?
C55 H55 0.9500 . ?
C55 C56 1.384(3) . ?
C22 C23 1.392(3) . ?
C66 C65 1.408(3) . ?
C35 C36 1.403(3) . ?
C35 C40 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.395(4) . ?
C2 C3 1.392(4) . ?
C26 C25 1.398(3) . ?
C65 H65 0.9500 . ?
C65 C64 1.384(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(3) . ?
C24 C23 1.382(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(4) . ?
C69 C74 1.395(3) . ?
C69 C70 1.398(3) . ?
C44 H44 0.9500 . ?
C44 C43 1.392(4) . ?
C44 C45 1.386(4) . ?
N8 C68 1.172(4) . ?
C43 H43 0.9500 . ?
C43 C42 1.391(4) . ?
N5 C53 1.293(4) . ?
C7 C8 1.399(3) . ?
C7 C12 1.401(3) . ?
C40 H40 0.9500 . ?
C40 C39 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C11 C10 1.388(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.384(4) . ?
C38 C37 1.389(4) . ?
C84 C85 1.455(4) . ?
C25 H25 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C14 C15 1.393(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(4) . ?
C16 C15 1.389(4) . ?
C41 C46 1.393(3) . ?
C41 C42 1.397(3) . ?
C23 H23 0.9500 . ?
C12 H12 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C57 H57 0.9500 . ?
C57 C56 1.392(3) . ?
C17 H17 0.9500 . ?
C47 C52 1.389(4) . ?
C47 C48 1.398(4) . ?
C64 H64 0.9500 . ?
C53 N6 1.155(4) . ?
C46 H46 0.9500 . ?
C46 C45 1.389(4) . ?
C74 H74 0.9500 . ?
C74 C73 1.392(4) . ?
C15 H15 0.9500 . ?
C42 H42 0.9500 . ?
C39 H39 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.386(3) . ?
C1 C6 1.397(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.390(4) . ?
C56 H56 0.9500 . ?
C37 H37 0.9500 . ?
C80 H80 0.9500 . ?
C80 C79 1.388(4) . ?
C45 H45 0.9500 . ?
C9 H9 0.9500 . ?
C70 H70 0.9500 . ?
C70 C71 1.389(3) . ?
C78 H78 0.9500 . ?
C78 C79 1.385(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.393(4) . ?
C79 H79 0.9500 . ?
C50 H50 0.9500 . ?
C50 C49 1.364(5) . ?
C50 C51 1.389(4) . ?
C52 H52 0.9500 . ?
C52 C51 1.393(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.391(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(4) . ?
C72 H72 0.9500 . ?
C72 C73 1.388(4) . ?
C72 C71 1.391(4) . ?
C73 H73 0.9500 . ?
C85 H85A 0.9800 . ?
C85 H85B 0.9800 . ?
C85 H85C 0.9800 . ?
C49 H49 0.9500 . ?
C49 C48 1.399(4) . ?
C32 H32 0.9500 . ?
C32 C31 1.388(4) . ?
N12 C88 1.139(4) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C31 H31 0.9500 . ?
C88 C89 1.446(4) . ?
C3 H3 0.9500 . ?
C89 H89A 0.9800 . ?
C89 H89B 0.9800 . ?
C89 H89C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C71 H71 0.9500 . ?
N11 C86 1.146(4) . ?
C48 H48 0.9500 . ?
C51 H51 0.9500 . ?
C86 C87 1.445(5) . ?
C82 N9 1.134(4) . ?
C82 C83 1.438(4) . ?
C83 H83A 0.9800 . ?
C83 H83B 0.9800 . ?
C83 H83C 0.9800 . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 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
N7 P4 C75 113.74(11) . . ?
N7 P4 C66 116.94(11) . . ?
N7 P4 C69 105.11(12) . . ?
C75 P4 C66 104.78(10) . . ?
C75 P4 C69 106.31(11) . . ?
C69 P4 C66 109.52(10) . . ?
N3 P2 C7 111.54(11) . . ?
N3 P2 C14 117.69(11) . . ?
N3 P2 C1 105.59(11) . . ?
C7 P2 C14 104.62(11) . . ?
C7 P2 C1 108.85(11) . . ?
C1 P2 C14 108.33(11) . . ?
N1 P1 C29 115.58(11) . . ?
N1 P1 C35 111.51(10) . . ?
N1 P1 C26 106.07(10) . . ?
C29 P1 C35 104.91(10) . . ?
C29 P1 C26 109.92(10) . . ?
C35 P1 C26 108.76(11) . . ?
N5 P3 C54 114.97(12) . . ?
N5 P3 C41 113.27(11) . . ?
N5 P3 C47 106.77(13) . . ?
C41 P3 C54 106.66(11) . . ?
C47 P3 C54 108.50(11) . . ?
C47 P3 C41 106.26(11) . . ?
C18 O1 C20 117.5(2) . . ?
C58 O3 C60 117.4(2) . . ?
C22 O2 C27 116.83(19) . . ?
C62 O4 C67 117.2(2) . . ?
H5A O5 H5B 104.5 . . ?
C28 N1 P1 128.23(17) . . ?
C58 C59 C61 117.91(19) . . ?
C58 C59 C54 117.5(2) . . ?
C54 C59 C61 124.6(2) . . ?
N4 C13 N3 175.6(3) . . ?
C13 N3 P2 124.72(18) . . ?
O1 C18 C19 114.9(2) . . ?
O1 C18 C17 123.5(2) . . ?
C17 C18 C19 121.6(2) . . ?
C18 C19 C21 119.2(2) . . ?
C18 C19 C14 117.8(2) . . ?
C14 C19 C21 122.9(2) . . ?
O3 C58 C59 114.5(2) . . ?
O3 C58 C57 123.4(2) . . ?
C57 C58 C59 122.0(2) . . ?
N2 C28 N1 174.3(3) . . ?
C62 C61 C59 118.54(19) . . ?
C66 C61 C59 123.53(19) . . ?
C66 C61 C62 117.9(2) . . ?
C22 C21 C19 119.25(19) . . ?
C22 C21 C26 118.0(2) . . ?
C26 C21 C19 122.8(2) . . ?
O4 C62 C61 114.7(2) . . ?
O4 C62 C63 123.7(2) . . ?
C63 C62 C61 121.5(2) . . ?
C68 N7 P4 128.4(2) . . ?
C77 C76 H76 120.1 . . ?
C77 C76 C75 119.7(2) . . ?
C75 C76 H76 120.1 . . ?
C62 C63 H63 120.0 . . ?
C62 C63 C64 119.9(2) . . ?
C64 C63 H63 120.0 . . ?
C59 C54 P3 124.71(18) . . ?
C55 C54 P3 114.83(17) . . ?
C55 C54 C59 120.4(2) . . ?
C76 C77 H77 119.9 . . ?
C78 C77 C76 120.2(2) . . ?
C78 C77 H77 119.9 . . ?
C76 C75 P4 122.75(18) . . ?
C76 C75 C80 120.0(2) . . ?
C80 C75 P4 117.30(18) . . ?
C30 C29 P1 119.11(18) . . ?
C30 C29 C34 119.9(2) . . ?
C34 C29 P1 120.74(19) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 C54 120.5(2) . . ?
C56 C55 H55 119.8 . . ?
O2 C22 C21 114.9(2) . . ?
O2 C22 C23 123.6(2) . . ?
C23 C22 C21 121.5(2) . . ?
C61 C66 P4 125.41(18) . . ?
C65 C66 P4 114.51(17) . . ?
C65 C66 C61 120.1(2) . . ?
C36 C35 P1 117.31(18) . . ?
C40 C35 P1 122.78(17) . . ?
C40 C35 C36 119.8(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C21 C26 P1 122.24(18) . . ?
C25 C26 P1 117.10(17) . . ?
C25 C26 C21 120.6(2) . . ?
C66 C65 H65 119.8 . . ?
C64 C65 C66 120.5(2) . . ?
C64 C65 H65 119.8 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.7(2) . . ?
C31 C30 H30 120.2 . . ?
C35 C36 H36 120.1 . . ?
C37 C36 C35 119.9(2) . . ?
C37 C36 H36 120.1 . . ?
C74 C69 P4 117.14(19) . . ?
C74 C69 C70 119.8(2) . . ?
C70 C69 P4 123.05(18) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C45 C44 C43 120.0(2) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 C44 120.0(2) . . ?
C42 C43 H43 120.0 . . ?
C53 N5 P3 127.0(2) . . ?
C8 C7 P2 122.30(19) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 P2 118.20(18) . . ?
C35 C40 H40 120.2 . . ?
C39 C40 C35 119.6(2) . . ?
C39 C40 H40 120.2 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C39 C38 H38 119.9 . . ?
C39 C38 C37 120.2(2) . . ?
C37 C38 H38 119.9 . . ?
N10 C84 C85 178.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.1 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C19 C14 P2 123.66(18) . . ?
C15 C14 P2 116.22(18) . . ?
C15 C14 C19 120.1(2) . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C46 C41 P3 120.69(18) . . ?
C46 C41 C42 119.7(2) . . ?
C42 C41 P3 119.59(18) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.3 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C58 C57 H57 120.2 . . ?
C58 C57 C56 119.6(2) . . ?
C56 C57 H57 120.2 . . ?
C18 C17 H17 120.4 . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C52 C47 P3 122.7(2) . . ?
C52 C47 C48 119.6(2) . . ?
C48 C47 P3 117.5(2) . . ?
N8 C68 N7 175.1(3) . . ?
C63 C64 H64 120.0 . . ?
C65 C64 C63 120.1(2) . . ?
C65 C64 H64 120.0 . . ?
N6 C53 N5 174.4(3) . . ?
C41 C46 H46 120.0 . . ?
C45 C46 C41 120.0(2) . . ?
C45 C46 H46 120.0 . . ?
C69 C74 H74 120.1 . . ?
C73 C74 C69 119.8(3) . . ?
C73 C74 H74 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C43 C42 C41 120.0(2) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C40 C39 H39 119.8 . . ?
C38 C39 C40 120.4(2) . . ?
C38 C39 H39 119.8 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 120.0(2) . . ?
C33 C34 H34 120.0 . . ?
C2 C1 P2 118.23(19) . . ?
C2 C1 C6 119.6(2) . . ?
C6 C1 P2 122.12(19) . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C9 C10 H10 119.9 . . ?
C55 C56 C57 120.0(2) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 H56 120.0 . . ?
C36 C37 C38 120.1(2) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C75 C80 H80 120.3 . . ?
C79 C80 C75 119.5(2) . . ?
C79 C80 H80 120.3 . . ?
C44 C45 C46 120.3(2) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C69 C70 H70 119.9 . . ?
C71 C70 C69 120.3(2) . . ?
C71 C70 H70 119.9 . . ?
C77 C78 H78 119.9 . . ?
C79 C78 C77 120.3(2) . . ?
C79 C78 H78 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C80 C79 H79 119.8 . . ?
C78 C79 C80 120.4(2) . . ?
C78 C79 H79 119.8 . . ?
C49 C50 H50 120.1 . . ?
C49 C50 C51 119.9(3) . . ?
C51 C50 H50 120.1 . . ?
C47 C52 H52 120.0 . . ?
C47 C52 C51 120.0(3) . . ?
C51 C52 H52 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.1(3) . . ?
C32 C33 H33 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C73 C72 H72 119.7 . . ?
C73 C72 C71 120.6(2) . . ?
C71 C72 H72 119.7 . . ?
C74 C73 H73 120.0 . . ?
C72 C73 C74 120.0(3) . . ?
C72 C73 H73 120.0 . . ?
C84 C85 H85A 109.5 . . ?
C84 C85 H85B 109.5 . . ?
C84 C85 H85C 109.5 . . ?
H85A C85 H85B 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?
C50 C49 H49 119.5 . . ?
C50 C49 C48 121.0(3) . . ?
C48 C49 H49 119.5 . . ?
C33 C32 H32 120.0 . . ?
C33 C32 C31 120.1(2) . . ?
C31 C32 H32 120.0 . . ?
O3 C60 H60A 109.5 . . ?
O3 C60 H60B 109.5 . . ?
O3 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
O4 C67 H67A 109.5 . . ?
O4 C67 H67B 109.5 . . ?
O4 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
N12 C88 C89 178.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C88 C89 H89A 109.5 . . ?
C88 C89 H89B 109.5 . . ?
C88 C89 H89C 109.5 . . ?
H89A C89 H89B 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C70 C71 C72 119.5(3) . . ?
C70 C71 H71 120.2 . . ?
C72 C71 H71 120.2 . . ?
C47 C48 C49 119.3(3) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C50 C51 C52 120.2(3) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
N11 C86 C87 177.7(4) . . ?
N9 C82 C83 178.7(4) . . ?
C82 C83 H83A 109.5 . . ?
C82 C83 H83B 109.5 . . ?
C82 C83 H83C 109.5 . . ?
H83A C83 H83B 109.5 . . ?
H83A C83 H83C 109.5 . . ?
H83B C83 H83C 109.5 . . ?
C86 C87 H87A 109.5 . . ?
C86 C87 H87B 109.5 . . ?
C86 C87 H87C 109.5 . . ?
H87A C87 H87B 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 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
P4 C75 C80 C79 179.16(19) . . . . ?
P4 C66 C65 C64 178.07(18) . . . . ?
P4 C69 C74 C73 -177.0(2) . . . . ?
P4 C69 C70 C71 178.1(2) . . . . ?
P2 C7 C8 C9 -175.3(2) . . . . ?
P2 C7 C12 C11 175.44(19) . . . . ?
P2 C14 C15 C16 -177.96(18) . . . . ?
P2 C1 C6 C5 -178.9(2) . . . . ?
P1 C29 C30 C31 -173.8(2) . . . . ?
P1 C29 C34 C33 173.49(19) . . . . ?
P1 C35 C36 C37 176.8(2) . . . . ?
P1 C35 C40 C39 -176.24(19) . . . . ?
P1 C26 C25 C24 -175.68(17) . . . . ?
P3 C54 C55 C56 176.79(18) . . . . ?
P3 C41 C46 C45 -178.3(2) . . . . ?
P3 C41 C42 C43 176.97(19) . . . . ?
P3 C47 C52 C51 175.1(2) . . . . ?
P3 C47 C48 C49 -175.0(2) . . . . ?
O1 C18 C19 C21 -9.0(3) . . . . ?
O1 C18 C19 C14 173.42(19) . . . . ?
O1 C18 C17 C16 -175.2(2) . . . . ?
O3 C58 C57 C56 179.8(2) . . . . ?
O2 C22 C23 C24 178.1(2) . . . . ?
O4 C62 C63 C64 -177.8(2) . . . . ?
N1 P1 C29 C30 -29.7(2) . . . . ?
N1 P1 C29 C34 156.53(18) . . . . ?
N1 P1 C35 C36 -43.8(2) . . . . ?
N1 P1 C35 C40 132.4(2) . . . . ?
N1 P1 C26 C21 -36.1(2) . . . . ?
N1 P1 C26 C25 140.54(18) . . . . ?
C59 C58 C57 C56 0.4(3) . . . . ?
C59 C61 C62 O4 -0.4(3) . . . . ?
C59 C61 C62 C63 -179.5(2) . . . . ?
C59 C61 C66 P4 0.3(3) . . . . ?
C59 C61 C66 C65 179.2(2) . . . . ?
C59 C54 C55 C56 -1.0(3) . . . . ?
N3 P2 C7 C8 113.8(2) . . . . ?
N3 P2 C7 C12 -62.1(2) . . . . ?
N3 P2 C14 C19 -19.3(2) . . . . ?
N3 P2 C14 C15 159.87(17) . . . . ?
N3 P2 C1 C2 -34.2(2) . . . . ?
N3 P2 C1 C6 144.8(2) . . . . ?
C18 C19 C21 C22 110.7(2) . . . . ?
C18 C19 C21 C26 -70.0(3) . . . . ?
C18 C19 C14 P2 -177.55(16) . . . . ?
C18 C19 C14 C15 3.3(3) . . . . ?
C19 C18 C17 C16 4.4(3) . . . . ?
C19 C21 C22 O2 1.0(3) . . . . ?
C19 C21 C22 C23 179.0(2) . . . . ?
C19 C21 C26 P1 -3.1(3) . . . . ?
C19 C21 C26 C25 -179.6(2) . . . . ?
C19 C14 C15 C16 1.3(3) . . . . ?
C58 C59 C61 C62 110.2(2) . . . . ?
C58 C59 C61 C66 -66.9(3) . . . . ?
C58 C59 C54 P3 -176.16(16) . . . . ?
C58 C59 C54 C55 1.4(3) . . . . ?
C58 C57 C56 C55 0.0(3) . . . . ?
C61 C59 C58 O3 1.7(3) . . . . ?
C61 C59 C58 C57 -178.9(2) . . . . ?
C61 C59 C54 P3 1.4(3) . . . . ?
C61 C59 C54 C55 179.0(2) . . . . ?
C61 C62 C63 C64 1.2(3) . . . . ?
C61 C66 C65 C64 -1.0(3) . . . . ?
C21 C19 C14 P2 5.0(3) . . . . ?
C21 C19 C14 C15 -174.2(2) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C21 C26 C25 C24 1.0(3) . . . . ?
C62 C61 C66 P4 -176.79(16) . . . . ?
C62 C61 C66 C65 2.2(3) . . . . ?
C62 C63 C64 C65 0.1(3) . . . . ?
N7 P4 C75 C76 127.4(2) . . . . ?
N7 P4 C75 C80 -52.4(2) . . . . ?
N7 P4 C66 C61 -13.8(2) . . . . ?
N7 P4 C66 C65 167.22(16) . . . . ?
N7 P4 C69 C74 -40.5(2) . . . . ?
N7 P4 C69 C70 142.0(2) . . . . ?
C76 C77 C78 C79 0.1(4) . . . . ?
C76 C75 C80 C79 -0.6(4) . . . . ?
C54 P3 N5 C53 -97.4(3) . . . . ?
C54 P3 C41 C46 -105.4(2) . . . . ?
C54 P3 C41 C42 75.9(2) . . . . ?
C54 P3 C47 C52 21.4(2) . . . . ?
C54 P3 C47 C48 -163.2(2) . . . . ?
C54 C59 C58 O3 179.42(18) . . . . ?
C54 C59 C58 C57 -1.2(3) . . . . ?
C54 C59 C61 C62 -67.4(3) . . . . ?
C54 C59 C61 C66 115.6(2) . . . . ?
C54 C55 C56 C57 0.3(4) . . . . ?
C77 C76 C75 P4 179.73(18) . . . . ?
C77 C76 C75 C80 -0.5(4) . . . . ?
C77 C78 C79 C80 -1.2(4) . . . . ?
C75 P4 N7 C68 41.5(3) . . . . ?
C75 P4 C66 C61 -140.70(19) . . . . ?
C75 P4 C66 C65 40.27(19) . . . . ?
C75 P4 C69 C74 80.4(2) . . . . ?
C75 P4 C69 C70 -97.1(2) . . . . ?
C75 C76 C77 C78 0.8(4) . . . . ?
C75 C80 C79 C78 1.5(4) . . . . ?
C29 P1 N1 C28 60.1(2) . . . . ?
C29 P1 C35 C36 -169.63(18) . . . . ?
C29 P1 C35 C40 6.6(2) . . . . ?
C29 P1 C26 C21 89.51(19) . . . . ?
C29 P1 C26 C25 -93.85(19) . . . . ?
C29 C30 C31 C32 0.2(4) . . . . ?
C29 C34 C33 C32 0.1(4) . . . . ?
C22 C21 C26 P1 176.18(16) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
C66 P4 N7 C68 -81.0(2) . . . . ?
C66 P4 C75 C76 -103.7(2) . . . . ?
C66 P4 C75 C80 76.5(2) . . . . ?
C66 P4 C69 C74 -166.93(19) . . . . ?
C66 P4 C69 C70 15.6(2) . . . . ?
C66 C61 C62 O4 176.80(18) . . . . ?
C66 C61 C62 C63 -2.3(3) . . . . ?
C66 C65 C64 C63 -0.2(3) . . . . ?
C35 P1 N1 C28 -59.6(2) . . . . ?
C35 P1 C29 C30 93.5(2) . . . . ?
C35 P1 C29 C34 -80.2(2) . . . . ?
C35 P1 C26 C21 -156.15(17) . . . . ?
C35 P1 C26 C25 20.5(2) . . . . ?
C35 C36 C37 C38 -1.0(4) . . . . ?
C35 C40 C39 C38 0.2(4) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C26 P1 N1 C28 -177.8(2) . . . . ?
C26 P1 C29 C30 -149.72(19) . . . . ?
C26 P1 C29 C34 36.5(2) . . . . ?
C26 P1 C35 C36 72.8(2) . . . . ?
C26 P1 C35 C40 -111.0(2) . . . . ?
C26 C21 C22 O2 -178.33(18) . . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?
C30 C29 C34 C33 -0.2(4) . . . . ?
C36 C35 C40 C39 -0.1(4) . . . . ?
C69 P4 N7 C68 157.4(2) . . . . ?
C69 P4 C75 C76 12.2(2) . . . . ?
C69 P4 C75 C80 -167.57(18) . . . . ?
C69 P4 C66 C61 105.6(2) . . . . ?
C69 P4 C66 C65 -73.42(19) . . . . ?
C69 C74 C73 C72 -1.0(4) . . . . ?
C69 C70 C71 C72 -1.5(4) . . . . ?
C44 C43 C42 C41 1.7(4) . . . . ?
C43 C44 C45 C46 -0.9(4) . . . . ?
N5 P3 C54 C59 -20.5(2) . . . . ?
N5 P3 C54 C55 161.73(17) . . . . ?
N5 P3 C41 C46 127.1(2) . . . . ?
N5 P3 C41 C42 -51.5(2) . . . . ?
N5 P3 C47 C52 145.9(2) . . . . ?
N5 P3 C47 C48 -38.8(2) . . . . ?
C7 P2 N3 C13 32.8(2) . . . . ?
C7 P2 C14 C19 -143.73(19) . . . . ?
C7 P2 C14 C15 35.4(2) . . . . ?
C7 P2 C1 C2 85.7(2) . . . . ?
C7 P2 C1 C6 -95.4(2) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C40 C35 C36 C37 0.5(4) . . . . ?
C11 C10 C9 C8 -0.3(4) . . . . ?
C25 C24 C23 C22 0.4(3) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
C14 P2 N3 C13 -88.1(2) . . . . ?
C14 P2 C7 C8 -117.9(2) . . . . ?
C14 P2 C7 C12 66.2(2) . . . . ?
C14 P2 C1 C2 -161.1(2) . . . . ?
C14 P2 C1 C6 17.8(2) . . . . ?
C14 C19 C21 C22 -71.9(3) . . . . ?
C14 C19 C21 C26 107.4(2) . . . . ?
C41 P3 C54 C59 -147.01(19) . . . . ?
C41 P3 C54 C55 35.3(2) . . . . ?
C41 P3 N5 C53 25.6(3) . . . . ?
C41 P3 C47 C52 -93.0(2) . . . . ?
C41 P3 C47 C48 82.4(2) . . . . ?
C41 C46 C45 C44 0.9(4) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
C12 C11 C10 C9 0.2(4) . . . . ?
C27 O2 C22 C21 169.21(19) . . . . ?
C27 O2 C22 C23 -8.8(3) . . . . ?
C17 C18 C19 C21 171.4(2) . . . . ?
C17 C18 C19 C14 -6.2(3) . . . . ?
C17 C16 C15 C14 -3.2(4) . . . . ?
C47 P3 C54 C59 98.9(2) . . . . ?
C47 P3 C54 C55 -78.84(19) . . . . ?
C47 P3 N5 C53 142.2(2) . . . . ?
C47 P3 C41 C46 10.2(2) . . . . ?
C47 P3 C41 C42 -168.4(2) . . . . ?
C47 C52 C51 C50 -0.2(4) . . . . ?
C46 C41 C42 C43 -1.7(4) . . . . ?
C74 C69 C70 C71 0.7(4) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C42 C41 C46 C45 0.4(4) . . . . ?
C39 C38 C37 C36 1.1(4) . . . . ?
C34 C29 C30 C31 0.0(4) . . . . ?
C34 C33 C32 C31 0.1(4) . . . . ?
C1 P2 N3 C13 150.9(2) . . . . ?
C1 P2 C7 C8 -2.3(3) . . . . ?
C1 P2 C7 C12 -178.22(19) . . . . ?
C1 P2 C14 C19 100.3(2) . . . . ?
C1 P2 C14 C15 -80.5(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C5 C4 -0.2(4) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C37 C38 C39 C40 -0.7(4) . . . . ?
C45 C44 C43 C42 -0.4(4) . . . . ?
C70 C69 C74 C73 0.6(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C50 C49 C48 C47 -0.5(4) . . . . ?
C52 C47 C48 C49 0.5(4) . . . . ?
C33 C32 C31 C30 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.5(4) . . . . ?
C73 C72 C71 C70 1.1(4) . . . . ?
C49 C50 C51 C52 0.2(4) . . . . ?
C60 O3 C58 C59 171.95(19) . . . . ?
C60 O3 C58 C57 -7.5(3) . . . . ?
C67 O4 C62 C61 176.17(19) . . . . ?
C67 O4 C62 C63 -4.8(3) . . . . ?
C3 C2 C1 P2 178.9(2) . . . . ?
C3 C2 C1 C6 -0.1(4) . . . . ?
C20 O1 C18 C19 -179.9(2) . . . . ?
C20 O1 C18 C17 -0.3(3) . . . . ?
C71 C72 C73 C74 0.1(4) . . . . ?
C48 C47 C52 C51 -0.2(4) . . . . ?
C51 C50 C49 C48 0.1(5) . . . . ?

_olex2_exptl_crystal_mounting_method 
'mounted onto a MiTiGen loop with paratone oil'
_olex2_submission_original_sample_id mds081
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.893
