# 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. 
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data_p-1
_database_code_depnum_ccdc_archive 'CCDC 2302172'
loop_
_audit_author_name
_audit_author_address
'Susanne Margot Rupf'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H27 N4 O P'
_chemical_formula_sum            'C29 H27 N4 O P'
_chemical_formula_weight         478.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.539(2)
_cell_length_b                   10.9798(18)
_cell_length_c                   11.7826(15)
_cell_angle_alpha                92.457(9)
_cell_angle_beta                 108.816(4)
_cell_angle_gamma                103.145(4)
_cell_volume                     1246.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8194
_cell_measurement_temperature    102.0
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15240
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.401
_diffrn_reflns_theta_min         2.111
_diffrn_ambient_temperature      102.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3966
_reflns_number_total             4583
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.067
_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)+(0.0370P)²+1.1105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1073
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C31(H31), C11(H11), C42(H42), C34(H34), C32(H32), C12(H12), C24(H24),
 C41(H41), C44(H44), C22(H22), C14(H14), C21(H21)
2.b Idealised Me refined with everything fixed:
 C45(H45A,H45B,H45C)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C25(H25A,H25B,H25C), C15(H15A,H15B,H15C)
;
_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 0.91454(5) 0.35149(5) 0.24323(5) 0.01766(14) Uani 1 1 d . . . . .
H1 H 0.874(2) 0.2871(18) 0.1337(18) 0.013(5) Uiso 1 1 d . . . . .
O1 O 1.06613(15) 0.40865(13) 0.28974(13) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.60932(18) 0.55045(16) 0.40127(16) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.75353(18) 0.04337(16) 0.19882(16) 0.0237(4) Uani 1 1 d . . . . .
N3 N 0.85303(18) 0.51067(16) 0.05858(15) 0.0222(4) Uani 1 1 d . . . . .
N4 N 0.88431(18) 0.11582(16) 0.53689(15) 0.0232(4) Uani 1 1 d . . . . .
C1 C 0.8587(2) 0.23647(18) 0.33507(18) 0.0183(4) Uani 1 1 d . . . . .
H1A H 0.934(2) 0.1948(19) 0.3578(18) 0.012(5) Uiso 1 1 d . . . . .
C2 C 0.84611(19) 0.30106(18) 0.44524(17) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.8126(2) 0.41202(18) 0.44359(18) 0.0189(4) Uani 1 1 d . . . . .
H3 H 0.809148 0.447641 0.517122 0.023 Uiso 1 1 calc R U . . .
C4 C 0.78070(19) 0.48428(18) 0.34079(17) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.8092(2) 0.46097(18) 0.23816(18) 0.0180(4) Uani 1 1 d . . . . .
C30 C 0.7741(2) 0.52186(18) 0.12653(18) 0.0191(4) Uani 1 1 d . . . . .
C31 C 0.6651(2) 0.57934(19) 0.08810(18) 0.0213(4) Uani 1 1 d . . . . .
H31 H 0.608818 0.584836 0.135914 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7179(2) 0.58733(18) 0.36402(17) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.7743(2) 0.71246(18) 0.35705(17) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.850271 0.735215 0.328773 0.023 Uiso 1 1 calc R U . . .
C20 C 0.7302(2) 0.13483(18) 0.26246(17) 0.0189(4) Uani 1 1 d . . . . .
C42 C 0.9031(2) 0.2194(2) 0.76214(19) 0.0250(5) Uani 1 1 d . . . . .
H42 H 0.908879 0.255098 0.839088 0.030 Uiso 1 1 calc R U . . .
C34 C 0.8271(2) 0.5596(2) -0.04626(18) 0.0232(4) Uani 1 1 d . . . . .
H34 H 0.883894 0.552130 -0.093177 0.028 Uiso 1 1 calc R U . . .
C33 C 0.7219(2) 0.62069(19) -0.09097(18) 0.0215(4) Uani 1 1 d . . . . .
C32 C 0.6405(2) 0.62823(19) -0.02081(18) 0.0227(4) Uani 1 1 d . . . . .
H32 H 0.566396 0.667602 -0.047884 0.027 Uiso 1 1 calc R U . . .
C43 C 0.9213(2) 0.0991(2) 0.74797(19) 0.0256(5) Uani 1 1 d . . . . .
C40 C 0.8688(2) 0.23331(18) 0.55324(18) 0.0187(4) Uani 1 1 d . . . . .
C12 C 0.7184(2) 0.80367(19) 0.39185(18) 0.0210(4) Uani 1 1 d . . . . .
H12 H 0.757074 0.890228 0.389749 0.025 Uiso 1 1 calc R U . . .
C23 C 0.5106(2) -0.0650(2) 0.13860(19) 0.0264(5) Uani 1 1 d . . . . .
C24 C 0.6451(2) -0.0525(2) 0.13932(19) 0.0267(5) Uani 1 1 d . . . . .
H24 H 0.661009 -0.117457 0.093879 0.032 Uiso 1 1 calc R U . . .
C41 C 0.8766(2) 0.2874(2) 0.66516(18) 0.0221(4) Uani 1 1 d . . . . .
H41 H 0.863872 0.369710 0.674561 0.027 Uiso 1 1 calc R U . . .
C44 C 0.9098(2) 0.0524(2) 0.6329(2) 0.0270(5) Uani 1 1 d . . . . .
H44 H 0.920652 -0.030279 0.621346 0.032 Uiso 1 1 calc R U . . .
C22 C 0.4890(2) 0.0341(2) 0.19986(19) 0.0275(5) Uani 1 1 d . . . . .
H22 H 0.398288 0.032637 0.199256 0.033 Uiso 1 1 calc R U . . .
C35 C 0.6948(2) 0.6722(2) -0.21072(19) 0.0281(5) Uani 1 1 d . . . . .
H35A H 0.764664 0.660613 -0.245557 0.042 Uiso 1 1 calc R U . . .
H35B H 0.699698 0.762269 -0.198518 0.042 Uiso 1 1 calc R U . . .
H35C H 0.602342 0.627302 -0.265885 0.042 Uiso 1 1 calc R U . . .
C14 C 0.5548(2) 0.6401(2) 0.4315(2) 0.0268(5) Uani 1 1 d . . . . .
H14 H 0.476066 0.614478 0.455719 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6053(2) 0.7679(2) 0.42987(19) 0.0245(5) Uani 1 1 d . . . . .
C21 C 0.5990(2) 0.1353(2) 0.26210(18) 0.0238(5) Uani 1 1 d . . . . .
H21 H 0.584622 0.204043 0.303874 0.029 Uiso 1 1 calc R U . . .
C25 C 0.3968(3) -0.1809(2) 0.0755(2) 0.0384(6) Uani 1 1 d . . . . .
H25A H 0.404588 -0.206141 -0.002298 0.058 Uiso 1 1 calc R U . . .
H25B H 0.306646 -0.162632 0.061835 0.058 Uiso 1 1 calc R U . . .
H25C H 0.405152 -0.249439 0.125798 0.058 Uiso 1 1 calc R U . . .
C45 C 0.9545(3) 0.0239(2) 0.8523(2) 0.0368(6) Uani 1 1 d . . . . .
H45A H 1.042098 0.069690 0.914327 0.055 Uiso 1 1 calc . U . . .
H45B H 0.963111 -0.058036 0.824052 0.055 Uiso 1 1 calc . U . . .
H45C H 0.880011 0.011155 0.886724 0.055 Uiso 1 1 calc . U . . .
C15 C 0.5409(3) 0.8630(2) 0.4704(2) 0.0369(6) Uani 1 1 d . . . . .
H15A H 0.579918 0.882593 0.558654 0.055 Uiso 1 1 calc R U . . .
H15B H 0.440415 0.828130 0.445646 0.055 Uiso 1 1 calc R U . . .
H15C H 0.560597 0.940135 0.433465 0.055 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 H1 1.33(2) . ?
P1 O1 1.4819(15) . ?
P1 C1 1.8170(19) . ?
P1 C5 1.803(2) . ?
N1 C10 1.340(3) . ?
N1 C14 1.336(3) . ?
N2 C20 1.341(3) . ?
N2 C24 1.334(3) . ?
N3 C30 1.347(3) . ?
N3 C34 1.340(3) . ?
N4 C40 1.350(3) . ?
N4 C44 1.339(3) . ?
C1 H1A 0.98(2) . ?
C1 C2 1.510(3) . ?
C1 C20 1.515(3) . ?
C2 C3 1.343(3) . ?
C2 C40 1.482(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.467(3) . ?
C4 C5 1.364(3) . ?
C4 C10 1.491(3) . ?
C5 C30 1.479(3) . ?
C30 C31 1.393(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.382(3) . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C20 C21 1.383(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(3) . ?
C42 C41 1.380(3) . ?
C34 H34 0.9500 . ?
C34 C33 1.396(3) . ?
C33 C32 1.383(3) . ?
C33 C35 1.508(3) . ?
C32 H32 0.9500 . ?
C43 C44 1.386(3) . ?
C43 C45 1.502(3) . ?
C40 C41 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C23 C24 1.390(3) . ?
C23 C22 1.381(3) . ?
C23 C25 1.503(3) . ?
C24 H24 0.9500 . ?
C41 H41 0.9500 . ?
C44 H44 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.383(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C13 1.387(3) . ?
C13 C15 1.505(3) . ?
C21 H21 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 H1 111.7(8) . . ?
O1 P1 C1 112.94(9) . . ?
O1 P1 C5 115.02(9) . . ?
C1 P1 H1 104.3(8) . . ?
C5 P1 H1 108.5(8) . . ?
C5 P1 C1 103.60(9) . . ?
C14 N1 C10 117.23(18) . . ?
C24 N2 C20 117.13(18) . . ?
C34 N3 C30 118.43(17) . . ?
C44 N4 C40 117.79(18) . . ?
P1 C1 H1A 102.2(11) . . ?
C2 C1 P1 110.79(13) . . ?
C2 C1 H1A 111.0(12) . . ?
C2 C1 C20 113.68(16) . . ?
C20 C1 P1 112.60(13) . . ?
C20 C1 H1A 105.8(12) . . ?
C3 C2 C1 121.49(17) . . ?
C3 C2 C40 122.27(18) . . ?
C40 C2 C1 116.21(16) . . ?
C2 C3 H3 116.4 . . ?
C2 C3 C4 127.16(18) . . ?
C4 C3 H3 116.4 . . ?
C3 C4 C10 111.88(16) . . ?
C5 C4 C3 123.40(18) . . ?
C5 C4 C10 124.69(17) . . ?
C4 C5 P1 116.07(15) . . ?
C4 C5 C30 128.11(18) . . ?
C30 C5 P1 115.63(14) . . ?
N3 C30 C5 113.68(17) . . ?
N3 C30 C31 121.38(18) . . ?
C31 C30 C5 124.83(18) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 C30 118.82(18) . . ?
C32 C31 H31 120.6 . . ?
N1 C10 C4 114.57(17) . . ?
N1 C10 C11 122.70(18) . . ?
C11 C10 C4 122.53(17) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.95(18) . . ?
C12 C11 H11 120.5 . . ?
N2 C20 C1 114.75(17) . . ?
N2 C20 C21 122.36(19) . . ?
C21 C20 C1 122.89(18) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C41 C42 C43 120.4(2) . . ?
N3 C34 H34 117.9 . . ?
N3 C34 C33 124.19(19) . . ?
C33 C34 H34 117.9 . . ?
C34 C33 C35 122.38(18) . . ?
C32 C33 C34 116.17(18) . . ?
C32 C33 C35 121.43(19) . . ?
C31 C32 C33 120.99(19) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C42 C43 C45 121.8(2) . . ?
C44 C43 C42 116.66(19) . . ?
C44 C43 C45 121.5(2) . . ?
N4 C40 C2 115.57(17) . . ?
N4 C40 C41 121.83(18) . . ?
C41 C40 C2 122.58(18) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.49(19) . . ?
C13 C12 H12 120.3 . . ?
C24 C23 C25 121.2(2) . . ?
C22 C23 C24 116.2(2) . . ?
C22 C23 C25 122.6(2) . . ?
N2 C24 C23 125.1(2) . . ?
N2 C24 H24 117.4 . . ?
C23 C24 H24 117.4 . . ?
C42 C41 C40 118.81(19) . . ?
C42 C41 H41 120.6 . . ?
C40 C41 H41 120.6 . . ?
N4 C44 C43 124.5(2) . . ?
N4 C44 H44 117.8 . . ?
C43 C44 H44 117.8 . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N1 C14 H14 117.8 . . ?
N1 C14 C13 124.46(19) . . ?
C13 C14 H14 117.8 . . ?
C12 C13 C14 117.14(19) . . ?
C12 C13 C15 121.95(19) . . ?
C14 C13 C15 120.9(2) . . ?
C20 C21 C22 118.9(2) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 30.2(2) . . . . ?
P1 C1 C2 C40 -151.46(14) . . . . ?
P1 C1 C20 N2 79.70(18) . . . . ?
P1 C1 C20 C21 -100.72(19) . . . . ?
P1 C5 C30 N3 -15.5(2) . . . . ?
P1 C5 C30 C31 160.65(17) . . . . ?
O1 P1 C1 C2 80.50(15) . . . . ?
O1 P1 C1 C20 -150.94(13) . . . . ?
O1 P1 C5 C4 -87.88(17) . . . . ?
O1 P1 C5 C30 87.37(16) . . . . ?
N1 C10 C11 C12 1.2(3) . . . . ?
N1 C14 C13 C12 1.3(3) . . . . ?
N1 C14 C13 C15 -177.4(2) . . . . ?
N2 C20 C21 C22 4.0(3) . . . . ?
N3 C30 C31 C32 -1.5(3) . . . . ?
N3 C34 C33 C32 -0.8(3) . . . . ?
N3 C34 C33 C35 -178.8(2) . . . . ?
N4 C40 C41 C42 1.1(3) . . . . ?
C1 P1 C5 C4 35.86(17) . . . . ?
C1 P1 C5 C30 -148.88(15) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C1 C2 C40 N4 -6.5(2) . . . . ?
C1 C2 C40 C41 172.32(18) . . . . ?
C1 C20 C21 C22 -175.50(18) . . . . ?
C2 C1 C20 N2 -153.26(16) . . . . ?
C2 C1 C20 C21 26.3(3) . . . . ?
C2 C3 C4 C5 -14.4(3) . . . . ?
C2 C3 C4 C10 167.23(19) . . . . ?
C2 C40 C41 C42 -177.64(18) . . . . ?
C3 C2 C40 N4 171.84(18) . . . . ?
C3 C2 C40 C41 -9.4(3) . . . . ?
C3 C4 C5 P1 -9.6(3) . . . . ?
C3 C4 C5 C30 175.84(19) . . . . ?
C3 C4 C10 N1 -51.5(2) . . . . ?
C3 C4 C10 C11 123.6(2) . . . . ?
C4 C5 C30 N3 159.1(2) . . . . ?
C4 C5 C30 C31 -24.8(3) . . . . ?
C4 C10 C11 C12 -173.42(18) . . . . ?
C5 P1 C1 C2 -44.59(16) . . . . ?
C5 P1 C1 C20 83.97(15) . . . . ?
C5 C4 C10 N1 130.2(2) . . . . ?
C5 C4 C10 C11 -54.8(3) . . . . ?
C5 C30 C31 C32 -177.38(19) . . . . ?
C30 N3 C34 C33 -0.7(3) . . . . ?
C30 C31 C32 C33 0.0(3) . . . . ?
C10 N1 C14 C13 -1.8(3) . . . . ?
C10 C4 C5 P1 168.54(15) . . . . ?
C10 C4 C5 C30 -6.0(3) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C11 C12 C13 C15 179.2(2) . . . . ?
C20 N2 C24 C23 -0.2(3) . . . . ?
C20 C1 C2 C3 -97.8(2) . . . . ?
C20 C1 C2 C40 80.6(2) . . . . ?
C42 C43 C44 N4 0.9(3) . . . . ?
C34 N3 C30 C5 178.16(18) . . . . ?
C34 N3 C30 C31 1.9(3) . . . . ?
C34 C33 C32 C31 1.1(3) . . . . ?
C43 C42 C41 C40 -0.1(3) . . . . ?
C40 N4 C44 C43 0.0(3) . . . . ?
C40 C2 C3 C4 -176.59(18) . . . . ?
C23 C22 C21 C20 -0.5(3) . . . . ?
C24 N2 C20 C1 175.92(17) . . . . ?
C24 N2 C20 C21 -3.7(3) . . . . ?
C24 C23 C22 C21 -3.0(3) . . . . ?
C41 C42 C43 C44 -0.8(3) . . . . ?
C41 C42 C43 C45 178.1(2) . . . . ?
C44 N4 C40 C2 177.80(18) . . . . ?
C44 N4 C40 C41 -1.0(3) . . . . ?
C22 C23 C24 N2 3.5(3) . . . . ?
C35 C33 C32 C31 179.2(2) . . . . ?
C14 N1 C10 C4 175.51(18) . . . . ?
C14 N1 C10 C11 0.5(3) . . . . ?
C25 C23 C24 N2 -175.8(2) . . . . ?
C25 C23 C22 C21 176.3(2) . . . . ?
C45 C43 C44 N4 -178.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/acetonitrile'
####################################################################### 
# 
# 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_lg012
_database_code_depnum_ccdc_archive 'CCDC 2304990'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_refine_special_details          
;
The structure exhibits inversion disorder about the central phosphinine ring.
To obtain a satisfactory model for the phosphinine core, the C atoms bound
directly to the two crystallgoraphically unique pyridyl rings were split and 
all atoms comprising the central phosphinine unit were given an occupancy of 0.5.
To conform with other structures reported containing phosphinine moieties, the 
structure was then grown and the two carbons furthest from P1, (to account for
the longer P-C bonds) and the two carbons closest to C3 (to account for the 
shorter C-C bonds) were selected and using the command'part -1 -c' in olex2
to generate a full two-fold disorder of the central phosphinine ring was formed. 
The carbons bound to the pyridyl units  (C1, C2, C4, C5) had their thermal 
parameters constrained (EADP) due to substantial spatial overlap of the 
ellipsoids with its inversion component.

No further disorder is present in the model, and all non-H atoms were refined
anisotropically to convergence. All H atoms in the structure were placed in
calculated positions and refined using a riding model.
;
_audit_creation_date             2023-10-30
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 N4 P'
_chemical_formula_sum            'C25 H17 N4 P'
_chemical_formula_weight         404.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.0233(2)
_cell_length_b                   7.6255(2)
_cell_length_c                   21.2045(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.2936(9)
_cell_angle_gamma                90
_cell_volume                     972.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9367
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1385 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9407.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -3.00 0.1230
0.00 -1.00 3.00 0.1360
-1.00 3.00 4.00 0.1810
1.00 -5.00 2.00 0.1530
-6.00 -1.00 -9.00 0.1520
7.00 0.00 6.00 0.2270
4.00 1.00 8.00 0.2120
0.00 -2.00 -7.00 0.1150
0.00 2.00 7.00 0.1520
-1.00 1.00 3.00 0.2270

_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.272
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.510
_diffrn_reflns_theta_min         2.839
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2936
_reflns_number_total             2955
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.299
_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)+(0.0228P)²+1.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1350
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C4) = Uanis(C5)
3. Others
 Fixed Sof: P1(0.5) C5(0.5) C1(0.5) C4(0.5) C3(0.5) H3(0.5) C2(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C7(H7), C14(H14), C8(H8), C10(H10), C13(H13), C9(H9),
 C3(H3)
;
_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 0.37648(18) 0.68243(15) 0.45493(5) 0.01503(19) Uani 0.5 1 d . . P A -1
N2 N 0.3163(2) 0.85426(19) 0.60700(7) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.348(2) 0.6240(17) 0.534(3) 0.0139(13) Uani 0.5 1 d . . P A -1
C6 C 0.6015(3) 0.5596(2) 0.36615(8) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.4300(3) 0.6253(2) 0.32980(8) 0.0273(3) Uani 1 1 d . . . . .
C12 C -0.0107(3) 0.7755(2) 0.54290(8) 0.0209(3) Uani 1 1 d . . . . .
H12 H -0.077753 0.703291 0.510654 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2128(2) 0.75394(19) 0.56237(7) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.1961(3) 0.9805(2) 0.63283(8) 0.0227(3) Uani 1 1 d . . . . .
H15 H 0.268088 1.054311 0.663757 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8141(3) 0.5433(2) 0.34395(8) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.933052 0.499319 0.370752 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0278(3) 1.0094(2) 0.61696(8) 0.0234(3) Uani 1 1 d . . . . .
H14 H -0.106778 1.099546 0.636992 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8499(3) 0.5921(3) 0.28231(8) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.993057 0.580390 0.266141 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4694(4) 0.6728(3) 0.27069(9) 0.0319(4) Uani 1 1 d . . . . .
H10 H 0.349154 0.719599 0.245029 0.038 Uiso 1 1 calc R U . . .
C13 C -0.1334(3) 0.9041(2) 0.57136(9) 0.0241(3) Uani 1 1 d . . . . .
H13 H -0.286815 0.919529 0.559771 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6731(4) 0.6583(3) 0.24463(9) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.691916 0.692545 0.202194 0.038 Uiso 1 1 calc R U . . .
C1 C 0.553(4) 0.520(3) 0.4288(7) 0.0139(13) Uani 0.5 1 d . . P A -1
C4 C 0.449(4) 0.478(3) 0.5633(7) 0.0139(13) Uani 0.5 1 d . . P A -1
C3 C 0.5883(7) 0.3707(6) 0.5304(2) 0.0169(8) Uani 0.5 1 d . . P A -1
H3 H 0.654919 0.275537 0.553345 0.020 Uiso 0.5 1 calc R U P A -1
C2 C 0.641(2) 0.3861(17) 0.468(3) 0.0139(13) Uani 0.5 1 d . . P A -1


_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 C5 1.75(5) . ?
P1 C1 1.75(4) . ?
N2 C11 1.342(2) . ?
N2 C15 1.340(2) . ?
C5 C11 1.44(3) . ?
C5 C4 1.402(14) . ?
C6 N1 1.349(2) . ?
C6 C7 1.395(2) . ?
C6 C1 1.410(15) . ?
N1 C10 1.339(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.395(2) . ?
C12 C13 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.378(3) . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C1 C2 1.405(16) . ?
C4 C3 1.39(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.38(6) . ?

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
C1 P1 C5 102.6(7) . . ?
C15 N2 C11 117.20(14) . . ?
C11 C5 P1 108.4(14) . . ?
C4 C5 P1 124(4) . . ?
C4 C5 C11 127(5) . . ?
N1 C6 C7 121.85(16) . . ?
N1 C6 C1 115.2(11) . . ?
C7 C6 C1 122.9(10) . . ?
C10 N1 C6 117.66(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 118.95(15) . . ?
N2 C11 C5 116.0(13) . . ?
N2 C11 C12 122.88(14) . . ?
C12 C11 C5 121.1(13) . . ?
N2 C15 H15 118.1 . . ?
N2 C15 C14 123.72(16) . . ?
C14 C15 H15 118.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.32(16) . . ?
C8 C7 H7 120.3 . . ?
C15 C14 H14 120.7 . . ?
C13 C14 C15 118.56(16) . . ?
C13 C14 H14 120.7 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.89(19) . . ?
C9 C8 H8 120.6 . . ?
N1 C10 H10 117.9 . . ?
N1 C10 C9 124.26(17) . . ?
C9 C10 H10 117.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.66(15) . . ?
C14 C13 H13 120.7 . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.99(17) . . ?
C10 C9 H9 121.0 . . ?
C6 C1 P1 108.0(13) . . ?
C2 C1 P1 123(3) . . ?
C2 C1 C6 129(5) . . ?
C3 C4 C5 120(3) . . ?
C4 C3 H3 116.1 . . ?
C2 C3 C4 127.7(6) . . ?
C2 C3 H3 116.1 . . ?
C3 C2 C1 122(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C11 N2 -112.3(14) . . . . ?
P1 C5 C11 C12 66.0(9) . . . . ?
P1 C5 C4 C3 2(2) . . . . ?
P1 C1 C2 C3 2(2) . . . . ?
N2 C15 C14 C13 -0.9(3) . . . . ?
C5 P1 C1 C6 -176.0(9) . . . . ?
C5 P1 C1 C2 -1.6(9) . . . . ?
C5 C4 C3 C2 -1.6(10) . . . . ?
C6 N1 C10 C9 0.3(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C6 C1 C2 C3 175.5(6) . . . . ?
N1 C6 C7 C8 -1.5(3) . . . . ?
N1 C6 C1 P1 -38.5(8) . . . . ?
N1 C6 C1 C2 147.6(15) . . . . ?
N1 C10 C9 C8 -0.8(3) . . . . ?
C11 N2 C15 C14 1.5(3) . . . . ?
C11 C5 C4 C3 -175.3(8) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C15 N2 C11 C5 177.8(17) . . . . ?
C15 N2 C11 C12 -0.5(2) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C7 C6 N1 C10 0.9(3) . . . . ?
C7 C6 C1 P1 137.7(6) . . . . ?
C7 C6 C1 C2 -36(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C13 C12 C11 N2 -1.1(3) . . . . ?
C13 C12 C11 C5 -179.3(17) . . . . ?
C1 P1 C5 C11 177.3(10) . . . . ?
C1 P1 C5 C4 -0.5(16) . . . . ?
C1 C6 N1 C10 177.1(11) . . . . ?
C1 C6 C7 C8 -177.4(12) . . . . ?
C4 C5 C11 N2 65.5(16) . . . . ?
C4 C5 C11 C12 -116(2) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?

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

data_skl025_lkcntc
_database_code_depnum_ccdc_archive 'CCDC 2304991'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
"6,6',6'',6'''-(phosphinine-2,3,5,6-tetrayl)tetrakis(3-methylpyridine) toluene solvate"
_chemical_formula_moiety         'C29 H25 N4 P, C7 H8'
_chemical_formula_sum            'C36 H33 N4 P'
_chemical_formula_weight         552.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.0439(2)
_cell_length_b                   10.8817(5)
_cell_length_c                   11.4035(5)
_cell_angle_alpha                102.992(2)
_cell_angle_beta                 95.8210(10)
_cell_angle_gamma                93.2140(10)
_cell_volume                     724.61(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0972 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9471.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             292
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -8.00 0.0550
-5.00 1.00 0.00 0.1800
0.00 -1.00 9.00 0.0760
9.00 -3.00 7.00 0.1940
0.00 9.00 -8.00 0.0400
0.00 -3.00 2.00 0.0640

_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40058
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4067
_reflns_number_total             4445
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.267
_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)+0.8739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1556
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger.

The structure crystallises in the triclinic space group P-1 and features
half a molecule of 
6,6',6'',6'''-(phosphinine-2,3,5,6-tetrayl)tetrakis(3-methylpyridine) in
the asymmetric unit. The central phosphinine ring core is situated
across an inversion centre and disordered by symmetry with occupancy
0.5 as per symmetry requirement.
To obtain a suitable model for the phosphinine core, the carbons adjacent to 
the pyridyl ring were split and all atoms forming the central phosphinine unit
were given an occupancy of 0.5. To fit with other phosphinine moieties, the 
structure was then grown and the two carbons furthest from P1, (to account for 
the longer P-C bonds) and the two carbons closest to C3 (to account for the 
shorter C-C bonds) were selected and using the command'part -1 -c' in olex2
the central phosphinine ring was formed. The carbons bound to the pyridyl units 
(C1, C2, C4, C5) had their thermal parameters constrained (EADP) due to
substantial spatial overlap of the ellipsoids with the second component.
A toluene molecule of crystallisation is also present in the crystal which
features disorder by inversion, and was modelled as a twofold whole body
disordered site by placing in part -1. The occupancy of this molecule refined
to 0.498(3), which was later constrained to 0.5 in the final model giving
a total solvate occupancy of unity. The six carbon central core of the 
toluene molecule was constrained using AFIX 66 to ensure a chemically
sensible geometry. A FLAT restraint was also used across the entire seven
carbon skeleton of the toluene molecule, in addition to the displacement
parameter restraint combination SIMU/RIGU about the entire molecule.
No further disorder is present in the model, and all non-H atoms were refined
anisotropically with H atoms placed in calculated positions and refined using
a riding model.

The erroneous reflection (0,1,0) was removed during refinement due to partial
obscuration by the beamstop.
;
_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 planarity
 C24, C19, C20, C21, C22, C23, C18
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C18: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C1) = Uanis(C2) = Uanis(C5) = Uanis(C4)
4. Rigid body (RIGU) restrains
 C24, C23, C22, C21, C20, C19, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: P1(0.5) C2(0.5) C1(0.5) C19(0.5) C24(0.5) H24(0.5) C23(0.5)
 H23(0.5) C22(0.5) H22(0.5) C21(0.5) H21(0.5) C20(0.5) H20(0.5) C18(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5) C3(0.5) H3(0.5) C5(0.5) C4(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C10(H10), C16(H16), C7(H7), C8(H8), C24(H24), C23(H23),
 C22(H22), C21(H21), C20(H20), C3(H3)
6.b Fitted hexagon refined as free rotating group:
 C19(C24,C23,C22,C21,C20)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.85105(18) 0.36241(11) -0.11882(10) 0.0205(2) Uani 0.5 1 d . . P A -1
N1 N 0.7527(3) 0.25487(17) 0.14760(16) 0.0278(4) Uani 1 1 d . . . . .
N2 N 1.0562(3) 0.59172(16) 0.33902(17) 0.0276(4) Uani 1 1 d . . . . .
C12 C 0.8858(3) 0.54618(17) 0.25224(17) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.6792(4) 0.31680(18) 0.06340(18) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.6215(3) 0.58863(19) 0.39689(18) 0.0261(4) Uani 1 1 d . . . . .
H14 H 0.472141 0.586965 0.415926 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6652(3) 0.54136(18) 0.27888(17) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.546768 0.506177 0.216947 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6119(4) 0.1643(2) 0.16942(19) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.663336 0.120427 0.228802 0.036 Uiso 1 1 calc R U . . .
C2 C 0.933(3) 0.5087(12) 0.1161(5) 0.0183(12) Uani 0.5 1 d . . P A -1
C15 C 0.7952(3) 0.63833(19) 0.48726(18) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.8166(13) 0.4047(8) 0.0329(13) 0.0183(12) Uani 0.5 1 d . . P A -1
C9 C 0.3960(4) 0.1307(2) 0.1108(2) 0.0320(5) Uani 1 1 d . . . . .
C16 C 1.0094(3) 0.63428(19) 0.4522(2) 0.0291(4) Uani 1 1 d . . . . .
H16 H 1.131286 0.664056 0.513448 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4667(4) 0.2903(2) 0.0017(2) 0.0421(6) Uani 1 1 d . . . . .
H7 H 0.418238 0.335350 -0.057190 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2493(4) 0.0276(2) 0.1389(3) 0.0426(6) Uani 1 1 d . . . . .
H11A H 0.247650 -0.049779 0.075197 0.064 Uiso 1 1 calc R U . . .
H11B H 0.097285 0.053912 0.142925 0.064 Uiso 1 1 calc R U . . .
H11C H 0.307312 0.011562 0.217037 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3256(4) 0.1976(2) 0.0267(3) 0.0448(6) Uani 1 1 d . . . . .
H8 H 0.178698 0.179759 -0.014600 0.054 Uiso 1 1 calc R U . . .
C19 C 0.389(3) 1.0627(18) 0.6005(18) 0.037(3) Uani 0.5 1 d G U P B -1
C24 C 0.599(3) 1.1150(18) 0.5890(18) 0.043(3) Uani 0.5 1 d G U P B -1
H24 H 0.660205 1.191193 0.643836 0.051 Uiso 0.5 1 calc R U P B -1
C23 C 0.718(3) 1.0558(18) 0.4972(18) 0.040(3) Uani 0.5 1 d G U P B -1
H23 H 0.861140 1.091594 0.489364 0.048 Uiso 0.5 1 calc R U P B -1
C22 C 0.628(3) 0.9444(17) 0.4170(18) 0.0315(19) Uani 0.5 1 d G U P B -1
H22 H 0.709268 0.903916 0.354243 0.038 Uiso 0.5 1 calc R U P B -1
C21 C 0.418(3) 0.8920(17) 0.4284(17) 0.0322(16) Uani 0.5 1 d G U P B -1
H21 H 0.356458 0.815838 0.373592 0.039 Uiso 0.5 1 calc R U P B -1
C20 C 0.299(3) 0.9512(18) 0.5202(17) 0.033(2) Uani 0.5 1 d G U P B -1
H20 H 0.155519 0.915436 0.528064 0.040 Uiso 0.5 1 calc R U P B -1
C17 C 0.7569(4) 0.6975(2) 0.6151(2) 0.0384(5) Uani 1 1 d . . . . .
H17A H 0.708283 0.782649 0.619291 0.058 Uiso 1 1 calc R U . . .
H17B H 0.895976 0.702929 0.668955 0.058 Uiso 1 1 calc R U . . .
H17C H 0.641466 0.645569 0.640498 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2524(9) 1.1174(5) 0.6882(5) 0.0421(11) Uani 0.5 1 d . U P B -1
H18A H 0.343055 1.146978 0.766940 0.063 Uiso 0.5 1 calc R U P B -1
H18B H 0.134749 1.054196 0.694242 0.063 Uiso 0.5 1 calc R U P B -1
H18C H 0.184553 1.189189 0.664345 0.063 Uiso 0.5 1 calc R U P B -1
C3 C 1.0853(7) 0.5867(4) 0.0783(4) 0.0230(8) Uani 0.5 1 d . . P A -1
H3 H 1.161227 0.654046 0.139556 0.028 Uiso 0.5 1 calc R U P A -1
C5 C 1.046(3) 0.4793(12) -0.1359(5) 0.0183(12) Uani 0.5 1 d . . P A -1
C4 C 1.1417(13) 0.5782(8) -0.0394(13) 0.0183(12) Uani 0.5 1 d . . P A -1


_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 C1 1.725(13) . ?
P1 C5 1.742(18) . ?
N1 C6 1.346(3) . ?
N1 C10 1.348(3) . ?
N2 C12 1.342(2) . ?
N2 C16 1.334(3) . ?
C12 C13 1.398(2) . ?
C12 C2 1.573(6) . ?
C6 C1 1.358(6) . ?
C6 C7 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(3) . ?
C14 C15 1.387(3) . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.394(3) . ?
C2 C1 1.402(6) . ?
C2 C3 1.383(18) . ?
C15 C16 1.393(3) . ?
C15 C17 1.502(3) . ?
C9 C11 1.501(3) . ?
C9 C8 1.378(3) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 H8 0.9500 . ?
C19 C24 1.3900 . ?
C19 C20 1.3900 . ?
C19 C18 1.411(18) . ?
C24 H24 0.9500 . ?
C24 C23 1.3900 . ?
C23 H23 0.9500 . ?
C23 C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 C21 1.3900 . ?
C21 H21 0.9500 . ?
C21 C20 1.3900 . ?
C20 H20 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.403(12) . ?
C5 C4 1.404(5) . ?

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
C1 P1 C5 103.4(4) . . ?
C6 N1 C10 117.56(18) . . ?
C16 N2 C12 118.11(17) . . ?
N2 C12 C13 121.44(18) . . ?
N2 C12 C2 119.3(7) . . ?
C13 C12 C2 119.0(6) . . ?
N1 C6 C1 120.4(5) . . ?
N1 C6 C7 121.8(2) . . ?
C1 C6 C7 117.7(6) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.23(18) . . ?
C15 C14 H14 119.9 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.08(17) . . ?
C14 C13 H13 120.5 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C9 124.5(2) . . ?
C9 C10 H10 117.8 . . ?
C1 C2 C12 122.1(14) . . ?
C3 C2 C12 117.5(10) . . ?
C3 C2 C1 120.3(6) . . ?
C14 C15 C16 116.18(18) . . ?
C14 C15 C17 122.50(19) . . ?
C16 C15 C17 121.29(19) . . ?
C6 C1 P1 110.9(8) . . ?
C6 C1 C2 124.3(13) . . ?
C2 C1 P1 124.5(5) . . ?
C10 C9 C11 121.5(2) . . ?
C8 C9 C10 116.2(2) . . ?
C8 C9 C11 122.3(2) . . ?
N2 C16 C15 124.89(18) . . ?
N2 C16 H16 117.6 . . ?
C15 C16 H16 117.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C24 C19 C20 120.0 . . ?
C24 C19 C18 124.2(8) . . ?
C20 C19 C18 115.8(8) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 116.1 . . ?
C2 C3 C4 127.8(9) . . ?
C4 C3 H3 116.1 . . ?
C4 C5 P1 123.1(7) . . ?
C3 C4 C5 120.8(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 C5 C4 C3 0.9(7) . . . . ?
N1 C6 C1 P1 119.7(6) . . . . ?
N1 C6 C1 C2 -54.2(7) . . . . ?
N1 C6 C7 C8 -0.2(4) . . . . ?
N1 C10 C9 C11 179.3(2) . . . . ?
N1 C10 C9 C8 -1.0(3) . . . . ?
N2 C12 C13 C14 2.2(3) . . . . ?
N2 C12 C2 C1 143.7(5) . . . . ?
N2 C12 C2 C3 -39.8(8) . . . . ?
C12 N2 C16 C15 -1.8(3) . . . . ?
C12 C2 C1 P1 177.1(7) . . . . ?
C12 C2 C1 C6 -9.8(7) . . . . ?
C12 C2 C3 C4 -174.8(4) . . . . ?
C6 N1 C10 C9 0.0(3) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C14 C15 C16 N2 3.0(3) . . . . ?
C13 C12 C2 C1 -41.7(7) . . . . ?
C13 C12 C2 C3 134.8(7) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C13 C14 C15 C17 176.4(2) . . . . ?
C10 N1 C6 C1 -176.7(6) . . . . ?
C10 N1 C6 C7 0.6(3) . . . . ?
C10 C9 C8 C7 1.4(4) . . . . ?
C2 C12 C13 C14 -172.3(5) . . . . ?
C2 C3 C4 C5 -2.5(10) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C1 P1 C5 C4 1.0(7) . . . . ?
C1 C6 C7 C8 177.2(6) . . . . ?
C1 C2 C3 C4 1.7(12) . . . . ?
C16 N2 C12 C13 -0.9(3) . . . . ?
C16 N2 C12 C2 173.6(5) . . . . ?
C7 C6 C1 P1 -57.7(5) . . . . ?
C7 C6 C1 C2 128.3(5) . . . . ?
C11 C9 C8 C7 -178.9(2) . . . . ?
C19 C24 C23 C22 0.0 . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C17 C15 C16 N2 -175.0(2) . . . . ?
C18 C19 C24 C23 -178.1(11) . . . . ?
C18 C19 C20 C21 178.2(10) . . . . ?
C3 C2 C1 P1 0.7(8) . . . . ?
C3 C2 C1 C6 173.8(8) . . . . ?
C5 P1 C1 C6 -175.7(3) . . . . ?
C5 P1 C1 C2 -1.8(6) . . . . ?

_olex2_submission_original_sample_id SKL025
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rok211_final_lkc
_database_code_depnum_ccdc_archive 'CCDC 2305850'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2023-11-05 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C100 H72 Li4 N16 O4 P4, 3.44(C H2 Cl2)'
_chemical_formula_sum            'C103.44 H78.88 Cl6.88 Li4 N16 O4 P4'
_chemical_formula_weight         2005.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 '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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   22.4512(8)
_cell_length_b                   22.4512(8)
_cell_length_c                   10.3077(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5195.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7249
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      72.68
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_T_max  0.8082
_exptl_absorpt_correction_T_min  0.5739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1424 before and 0.1130 after correction.
The Ratio of minimum to maximum transmission is 0.7101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2065
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20616
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.538
_diffrn_reflns_theta_max         66.538
_diffrn_reflns_theta_min         2.783
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'BRUKER PHOTON II'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3751
_reflns_number_total             4550
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.038
_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)+(0.0686P)²+0.9692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger.

The structure presented was isolated as a tetrameric coordination complex,
crystallising in the tetragonal space group I-4 with one quarter of the
tetramer itself comprising the asymmetric unit and a molecule of
dichloromethane of crystallisation. The dichloromethane molecule features
a minor whole body disorder, and was split into parts '1' and '2' for
the sites 'C1...Cl2' and 'C1A...Cl2A' respectively. Though a residual
electron density squeeze calculation prior to modelling the dichlormethane
sites suggested 100% cumulative occupancy across the two sites, the thermal
parameters were unacceptable and suggested either addional disorder or a
net occupancy slightly less than one. The occupancies of the dichloromethane
sites were then refined against net occupancies between 0.8 and 1.0, with
0.86 yielding the best convergence and lowest refinement parameters. In
this model, the individual occupancies of the dichloromethane sites '1' and
'2' refined to 0.52(3) and 0.34(3) respectively. A number of restraints
were applied to ensure both dichloromethane sites conformed to sensible
molecular geometries. DFIX 1.77 A restraints were placed between C1-Cl1 and
C1-Cl2, and all 1,2- C-Cl distances were subject to a SADI same distance
restraint. All 1,3- Cl-Cl distances were restrained through combined use of
DANG 2.92 and a SADI same distance restraint across both sites. Combined
displacement parameter restraijnts SIMU and RIGU were also used across both
sites. Finally, EADP constraints were applied linking the complementary
atoms of the two different sites to 'C1,C1A' and 'Cl1,Cl1A' as the atoms
observe a significant portion of spatial overlap in the structure.
There is no further disorder present in the model, and all non-H atoms
were refined anisotropically with all H-atoms placed in calculated
positions and allowed to refine using a riding model.

The structure is an inversion twin, and refined against the twin law
(-1,0,0,0,-1,0,0,0,-1) with a final BASF of 0.07(3).
An extinction correction was refined to 0.0008(2).
Two bad reflections were removed from the final refinement, (0,2,0)
and (1,3,0), however no systematic origin of the cause of the
error could be ascertained. The data was truncated at 0.84 A, as the
crystal diffracts only very weakly at higher angle, which may be
a consequence of the onset of loss of solvent leading to a drop
in crystallinity. The final R1 refined to 0.0505.,Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.93(3)
 0.07(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 Cl2-C1 = Cl1-C1
 1.77 with sigma of 0.02
 Cl1-Cl2
 2.92 with sigma of 0.04
 Cl1A-Cl2A
 2.92 with sigma of 0.04
 Cl1-Cl2 \\sim Cl1A-Cl2A
 with sigma of 0.01
 Cl1A-C1A \\sim Cl2A-C1A \\sim Cl1-C1 \\sim Cl2-C1
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Cl1A \\sim Cl2A \\sim C1A \\sim Cl1 \\sim Cl2 \\sim C1: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C1) = Uanis(C1A)
Uanis(Cl1) = Uanis(Cl1A)
5. Rigid body (RIGU) restrains
 Cl1A, Cl2A, C1A, Cl1, Cl2, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=0.86*(1-FVAR(2))
 Sof(Cl1)=Sof(Cl2)=Sof(C1)=Sof(H1A)=Sof(H1B)=0.86*FVAR(2)
7.a Everything fixed:
 H1
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1A(H1AA,H1AB)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.62305(5) 0.46030(5) 0.81459(13) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.584000 0.505500 0.734300 0.050 Uiso 1 1 d . . . . .
O1 O 0.59251(14) 0.45775(14) 0.9455(3) 0.0310(8) Uani 1 1 d . . . . .
N1 N 0.6970(2) 0.30520(19) 0.5049(5) 0.0373(11) Uani 1 1 d . . . . .
N2 N 0.84746(18) 0.42906(18) 0.7442(5) 0.0373(11) Uani 1 1 d . . . . .
N3 N 0.51691(18) 0.37924(18) 0.7727(4) 0.0333(10) Uani 1 1 d . . . . .
N4 N 0.67141(17) 0.56980(16) 0.9291(4) 0.0300(10) Uani 1 1 d . . . . .
C26 C 0.6199(2) 0.3943(2) 0.7220(5) 0.0268(10) Uani 1 1 d . . . . .
C2 C 0.6720(2) 0.36418(19) 0.6915(5) 0.0283(10) Uani 1 1 d . . . . .
C3 C 0.7293(2) 0.3828(2) 0.7272(5) 0.0308(11) Uani 1 1 d . . . . .
H3 H 0.761706 0.357108 0.707749 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7421(2) 0.4367(2) 0.7894(5) 0.0286(11) Uani 1 1 d . . . . .
C5 C 0.6987(2) 0.47923(19) 0.8197(5) 0.0279(10) Uani 1 1 d . . . . .
C6 C 0.6707(2) 0.3056(2) 0.6221(5) 0.0316(11) Uani 1 1 d . . . . .
C7 C 0.6446(3) 0.2557(2) 0.6753(7) 0.0430(13) Uani 1 1 d . . . . .
H7 H 0.625873 0.257507 0.757898 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6462(3) 0.2027(3) 0.6060(7) 0.0533(17) Uani 1 1 d . . . . .
H8 H 0.629825 0.167296 0.641735 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6717(3) 0.2022(3) 0.4851(7) 0.0517(17) Uani 1 1 d . . . . .
H9 H 0.672053 0.166949 0.434233 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6970(3) 0.2541(2) 0.4388(7) 0.0455(14) Uani 1 1 d . . . . .
H10 H 0.715232 0.253444 0.355615 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8057(2) 0.44355(19) 0.8320(5) 0.0315(11) Uani 1 1 d . . . . .
C12 C 0.8200(2) 0.4585(2) 0.9584(6) 0.0386(13) Uani 1 1 d . . . . .
H12 H 0.789537 0.469365 1.017841 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8784(3) 0.4577(3) 0.9973(7) 0.0499(16) Uani 1 1 d . . . . .
H13 H 0.888744 0.467456 1.084071 0.060 Uiso 1 1 calc R U . . .
C14 C 0.9219(2) 0.4424(3) 0.9089(8) 0.0534(18) Uani 1 1 d . . . . .
H14 H 0.962629 0.441327 0.933616 0.064 Uiso 1 1 calc R U . . .
C15 C 0.9050(2) 0.4289(2) 0.7844(7) 0.0473(16) Uani 1 1 d . . . . .
H15 H 0.935140 0.419040 0.723273 0.057 Uiso 1 1 calc R U . . .
C16 C 0.55982(19) 0.37402(19) 0.6820(5) 0.0276(10) Uani 1 1 d . . . . .
C17 C 0.5473(2) 0.3519(2) 0.5594(5) 0.0325(11) Uani 1 1 d . . . . .
H17 H 0.577829 0.350027 0.495606 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4902(2) 0.3326(2) 0.5301(6) 0.0388(13) Uani 1 1 d . . . . .
H18 H 0.481495 0.315833 0.447620 0.047 Uiso 1 1 calc R U . . .
C19 C 0.4459(2) 0.3381(2) 0.6235(6) 0.0415(13) Uani 1 1 d . . . . .
H19 H 0.406266 0.325740 0.605918 0.050 Uiso 1 1 calc R U . . .
C20 C 0.4607(2) 0.3617(2) 0.7410(6) 0.0404(13) Uani 1 1 d . . . . .
H20 H 0.430196 0.366212 0.804120 0.048 Uiso 1 1 calc R U . . .
C21 C 0.7124(2) 0.5409(2) 0.8553(5) 0.0279(11) Uani 1 1 d . . . . .
C22 C 0.7637(2) 0.5706(2) 0.8120(6) 0.0352(12) Uani 1 1 d . . . . .
H22 H 0.791124 0.550883 0.756534 0.042 Uiso 1 1 calc R U . . .
C23 C 0.7738(2) 0.6280(2) 0.8501(6) 0.0426(15) Uani 1 1 d . . . . .
H23 H 0.809412 0.647690 0.824633 0.051 Uiso 1 1 calc R U . . .
C24 C 0.7322(3) 0.6574(2) 0.9258(7) 0.0452(15) Uani 1 1 d . . . . .
H24 H 0.738463 0.697378 0.952449 0.054 Uiso 1 1 calc R U . . .
C25 C 0.6819(2) 0.6270(2) 0.9611(6) 0.0394(13) Uani 1 1 d . . . . .
H25 H 0.652754 0.647488 1.010967 0.047 Uiso 1 1 calc R U . . .
Li1 Li 0.5307(3) 0.3995(3) 0.9633(9) 0.0297(18) Uani 1 1 d . . . . .
Cl1 Cl 0.8998(8) 0.3912(6) 1.4026(19) 0.074(2) Uani 0.52(3) 1 d D U P A 1
Cl2 Cl 0.8246(5) 0.4936(4) 1.373(2) 0.103(4) Uani 0.52(3) 1 d D U P A 1
C1 C 0.8288(9) 0.4204(9) 1.427(4) 0.055(3) Uani 0.52(3) 1 d D U P A 1
H1A H 0.799380 0.395813 1.379117 0.066 Uiso 0.52(3) 1 calc R U P A 1
H1B H 0.818839 0.418833 1.519989 0.066 Uiso 0.52(3) 1 calc R U P A 1
Cl1A Cl 0.8847(7) 0.3853(9) 1.405(3) 0.074(2) Uani 0.34(3) 1 d D U P A 2
Cl2A Cl 0.8132(7) 0.4850(9) 1.3287(19) 0.079(4) Uani 0.34(3) 1 d D U P A 2
C1A C 0.8164(13) 0.4207(18) 1.422(6) 0.055(3) Uani 0.34(3) 1 d D U P A 2
H1AA H 0.784256 0.393236 1.394535 0.066 Uiso 0.34(3) 1 calc R U P A 2
H1AB H 0.809881 0.430962 1.514039 0.066 Uiso 0.34(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 H1 1.5758 . ?
P1 O1 1.514(4) . ?
P1 C26 1.764(5) . ?
P1 C5 1.752(5) . ?
P1 Li1 2.918(8) . ?
P1 Li1 2.828(9) 4_657 ?
O1 Li1 1.897(9) 4_657 ?
O1 Li1 1.916(8) . ?
N1 C6 1.345(7) . ?
N1 C10 1.334(7) . ?
N2 C11 1.343(7) . ?
N2 C15 1.357(7) . ?
N3 C16 1.348(7) . ?
N3 C20 1.361(7) . ?
N3 Li1 2.040(10) . ?
N4 C21 1.358(6) . ?
N4 C25 1.348(6) . ?
N4 Li1 2.130(9) 4_657 ?
C26 C2 1.389(7) . ?
C26 C16 1.482(6) . ?
C2 C3 1.401(7) . ?
C2 C6 1.497(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(7) . ?
C4 C5 1.398(6) . ?
C4 C11 1.503(6) . ?
C5 C21 1.464(6) . ?
C6 C7 1.379(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.372(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.363(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.404(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.366(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(8) . ?
C25 H25 0.9500 . ?
Li1 Li1 3.421(11) 3_567 ?
Li1 Li1 3.421(11) 4_657 ?
Cl1 C1 1.740(8) . ?
Cl2 C1 1.737(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
Cl1A C1A 1.736(11) . ?
Cl2A C1A 1.735(12) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 H1 103.9 . . ?
O1 P1 C26 115.6(2) . . ?
O1 P1 C5 114.9(2) . . ?
O1 P1 Li1 36.2(2) . . ?
O1 P1 Li1 38.6(2) . 4_657 ?
C26 P1 H1 103.5 . . ?
C26 P1 Li1 82.1(2) . . ?
C26 P1 Li1 154.2(2) . 4_657 ?
C5 P1 H1 113.5 . . ?
C5 P1 C26 105.0(2) . . ?
C5 P1 Li1 90.8(2) . 4_657 ?
C5 P1 Li1 141.9(2) . . ?
Li1 P1 H1 100.5 . . ?
Li1 P1 H1 88.0 4_657 . ?
Li1 P1 Li1 73.1(2) 4_657 . ?
P1 O1 Li1 116.1(3) . . ?
P1 O1 Li1 111.5(3) . 4_657 ?
Li1 O1 Li1 127.6(4) 4_657 . ?
C10 N1 C6 117.7(5) . . ?
C11 N2 C15 117.4(5) . . ?
C16 N3 C20 118.1(5) . . ?
C16 N3 Li1 125.4(4) . . ?
C20 N3 Li1 115.8(4) . . ?
C21 N4 Li1 126.9(4) . 4_657 ?
C25 N4 C21 118.3(4) . . ?
C25 N4 Li1 113.4(4) . 4_657 ?
C2 C26 P1 119.8(3) . . ?
C2 C26 C16 123.7(4) . . ?
C16 C26 P1 116.5(3) . . ?
C26 C2 C3 124.7(4) . . ?
C26 C2 C6 121.3(4) . . ?
C3 C2 C6 113.9(4) . . ?
C2 C3 H3 117.8 . . ?
C4 C3 C2 124.5(4) . . ?
C4 C3 H3 117.8 . . ?
C3 C4 C11 114.7(4) . . ?
C5 C4 C3 123.4(4) . . ?
C5 C4 C11 121.8(4) . . ?
C4 C5 P1 120.2(3) . . ?
C4 C5 C21 123.8(4) . . ?
C21 C5 P1 116.0(3) . . ?
N1 C6 C2 115.3(4) . . ?
N1 C6 C7 122.5(5) . . ?
C7 C6 C2 122.2(5) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(6) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(6) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(6) . . ?
C10 C9 H9 120.7 . . ?
N1 C10 C9 123.3(6) . . ?
N1 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N2 C11 C4 116.2(5) . . ?
N2 C11 C12 122.1(5) . . ?
C12 C11 C4 121.4(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(6) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(6) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 H14 120.7 . . ?
N2 C15 C14 123.2(6) . . ?
N2 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N3 C16 C26 115.5(4) . . ?
N3 C16 C17 121.3(4) . . ?
C17 C16 C26 123.2(4) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(5) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.4(5) . . ?
C20 C19 H19 120.8 . . ?
N3 C20 C19 123.5(5) . . ?
N3 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
N4 C21 C5 116.8(4) . . ?
N4 C21 C22 120.4(4) . . ?
C22 C21 C5 122.7(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.9(5) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 121.0 . . ?
C25 C24 C23 118.1(5) . . ?
C25 C24 H24 121.0 . . ?
N4 C25 C24 123.6(5) . . ?
N4 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
P1 Li1 P1 155.0(3) 3_567 . ?
P1 Li1 Li1 54.7(3) 3_567 3_567 ?
P1 Li1 Li1 120.9(2) . 3_567 ?
P1 Li1 Li1 52.3(2) . 4_657 ?
P1 Li1 Li1 103.3(4) 3_567 4_657 ?
O1 Li1 P1 146.1(4) 3_567 . ?
O1 Li1 P1 127.2(4) . 3_567 ?
O1 Li1 P1 29.89(17) 3_567 3_567 ?
O1 Li1 P1 27.80(17) . . ?
O1 Li1 O1 127.5(5) 3_567 . ?
O1 Li1 N3 111.6(4) 3_567 . ?
O1 Li1 N3 99.8(4) . . ?
O1 Li1 N4 99.7(4) 3_567 3_567 ?
O1 Li1 N4 105.1(4) . 3_567 ?
O1 Li1 Li1 26.3(2) 3_567 3_567 ?
O1 Li1 Li1 101.8(3) 3_567 4_657 ?
O1 Li1 Li1 26.1(2) . 4_657 ?
O1 Li1 Li1 109.4(2) . 3_567 ?
N3 Li1 P1 130.9(3) . 3_567 ?
N3 Li1 P1 72.9(3) . . ?
N3 Li1 N4 113.4(4) . 3_567 ?
N3 Li1 Li1 100.7(4) . 3_567 ?
N3 Li1 Li1 118.3(4) . 4_657 ?
N4 Li1 P1 71.0(3) 3_567 3_567 ?
N4 Li1 P1 109.3(3) 3_567 . ?
N4 Li1 Li1 109.8(4) 3_567 4_657 ?
N4 Li1 Li1 125.6(5) 3_567 3_567 ?
Li1 Li1 Li1 87.19(13) 3_567 4_657 ?
Cl1 C1 H1A 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
Cl2 C1 Cl1 111.1(7) . . ?
Cl2 C1 H1A 109.4 . . ?
Cl2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
Cl1A C1A H1AA 109.4 . . ?
Cl1A C1A H1AB 109.4 . . ?
Cl2A C1A Cl1A 111.3(10) . . ?
Cl2A C1A H1AA 109.4 . . ?
Cl2A C1A H1AB 109.4 . . ?
H1AA C1A H1AB 108.0 . . ?

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 C26 C2 C3 -1.2(7) . . . . ?
P1 C26 C2 C6 175.2(4) . . . . ?
P1 C26 C16 N3 -40.8(5) . . . . ?
P1 C26 C16 C17 138.1(4) . . . . ?
P1 C5 C21 N4 25.9(6) . . . . ?
P1 C5 C21 C22 -151.5(4) . . . . ?
O1 P1 C26 C2 -116.6(4) . . . . ?
O1 P1 C26 C16 62.9(4) . . . . ?
O1 P1 C5 C4 110.6(5) . . . . ?
O1 P1 C5 C21 -70.0(4) . . . . ?
N1 C6 C7 C8 0.9(9) . . . . ?
N2 C11 C12 C13 -1.3(7) . . . . ?
N3 C16 C17 C18 -2.5(7) . . . . ?
N4 C21 C22 C23 3.4(8) . . . . ?
C26 P1 O1 Li1 178.8(3) . . . 4_657 ?
C26 P1 O1 Li1 -24.0(4) . . . . ?
C26 P1 C5 C4 -17.5(5) . . . . ?
C26 P1 C5 C21 161.8(4) . . . . ?
C26 C2 C3 C4 -5.3(9) . . . . ?
C26 C2 C6 N1 117.4(5) . . . . ?
C26 C2 C6 C7 -62.9(7) . . . . ?
C26 C16 C17 C18 178.6(5) . . . . ?
C2 C26 C16 N3 138.6(5) . . . . ?
C2 C26 C16 C17 -42.4(7) . . . . ?
C2 C3 C4 C5 -2.1(8) . . . . ?
C2 C3 C4 C11 173.0(5) . . . . ?
C2 C6 C7 C8 -178.8(5) . . . . ?
C3 C2 C6 N1 -65.8(6) . . . . ?
C3 C2 C6 C7 113.9(6) . . . . ?
C3 C4 C5 P1 14.7(7) . . . . ?
C3 C4 C5 C21 -164.6(5) . . . . ?
C3 C4 C11 N2 46.6(6) . . . . ?
C3 C4 C11 C12 -127.5(5) . . . . ?
C4 C5 C21 N4 -154.8(5) . . . . ?
C4 C5 C21 C22 27.9(8) . . . . ?
C4 C11 C12 C13 172.5(5) . . . . ?
C5 P1 O1 Li1 -146.6(3) . . . . ?
C5 P1 O1 Li1 56.1(4) . . . 4_657 ?
C5 P1 C26 C2 11.2(5) . . . . ?
C5 P1 C26 C16 -169.3(4) . . . . ?
C5 C4 C11 N2 -138.2(5) . . . . ?
C5 C4 C11 C12 47.6(7) . . . . ?
C5 C21 C22 C23 -179.4(5) . . . . ?
C6 N1 C10 C9 -0.4(8) . . . . ?
C6 C2 C3 C4 178.0(5) . . . . ?
C6 C7 C8 C9 -2.3(9) . . . . ?
C7 C8 C9 C10 2.4(10) . . . . ?
C8 C9 C10 N1 -1.1(10) . . . . ?
C10 N1 C6 C2 -179.8(5) . . . . ?
C10 N1 C6 C7 0.5(8) . . . . ?
C11 N2 C15 C14 0.4(8) . . . . ?
C11 C4 C5 P1 -160.1(4) . . . . ?
C11 C4 C5 C21 20.6(8) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C13 C14 C15 N2 -0.9(9) . . . . ?
C15 N2 C11 C4 -173.4(4) . . . . ?
C15 N2 C11 C12 0.7(7) . . . . ?
C16 N3 C20 C19 1.4(8) . . . . ?
C16 C26 C2 C3 179.3(5) . . . . ?
C16 C26 C2 C6 -4.2(8) . . . . ?
C16 C17 C18 C19 2.6(8) . . . . ?
C17 C18 C19 C20 -0.8(8) . . . . ?
C18 C19 C20 N3 -1.2(9) . . . . ?
C20 N3 C16 C26 179.5(4) . . . . ?
C20 N3 C16 C17 0.5(7) . . . . ?
C21 N4 C25 C24 -1.5(9) . . . . ?
C21 C22 C23 C24 -3.1(9) . . . . ?
C22 C23 C24 C25 0.6(9) . . . . ?
C23 C24 C25 N4 1.8(10) . . . . ?
C25 N4 C21 C5 -178.5(5) . . . . ?
C25 N4 C21 C22 -1.1(7) . . . . ?
Li1 P1 O1 Li1 157.2(5) 4_657 . . . ?
Li1 P1 O1 Li1 -157.2(5) . . . 4_657 ?
Li1 P1 C26 C2 -114.9(6) 4_657 . . . ?
Li1 P1 C26 C2 -130.6(4) . . . . ?
Li1 P1 C26 C16 64.6(7) 4_657 . . . ?
Li1 P1 C26 C16 48.9(4) . . . . ?
Li1 P1 C5 C4 141.8(5) 4_657 . . . ?
Li1 P1 C5 C4 78.8(6) . . . . ?
Li1 P1 C5 C21 -101.8(5) . . . . ?
Li1 P1 C5 C21 -38.8(4) 4_657 . . . ?
Li1 N3 C16 C26 -10.3(6) . . . . ?
Li1 N3 C16 C17 170.7(4) . . . . ?
Li1 N3 C20 C19 -169.8(5) . . . . ?
Li1 N4 C21 C5 16.0(7) 4_657 . . . ?
Li1 N4 C21 C22 -166.6(5) 4_657 . . . ?
Li1 N4 C25 C24 165.9(6) 4_657 . . . ?

_olex2_date_sample_data_collection 2023-11-01
_olex2_submission_original_sample_id ROK211
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.93(3)
2 0.07(3)

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

data_rok200_cellnow
_database_code_depnum_ccdc_archive 'CCDC 2304992'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        1,2-bis(5-methylpyridin-2-yl)ethyne
_chemical_formula_moiety         'C14 H12 N2'
_chemical_formula_sum            'C14 H12 N2'
_chemical_formula_weight         208.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.4144(5)
_cell_length_b                   9.2664(5)
_cell_length_c                   14.4244(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.942(2)
_cell_angle_gamma                90
_cell_volume                     1091.55(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5369
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9119
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1011 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9119.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16349
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_min         3.325
_diffrn_ambient_temperature      100
_diffrn_detector                 'BRUKER PHOTON II'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                998
_reflns_number_total             1658
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.058
_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)+(0.1151P)²+0.7839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2543
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based 
on F, with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F² are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger.

The structure crystallises in the monoclinic space group C2/c, with the
asymmetric unit comprised of half a molecule of 
1,2-bis(5-methylpyridin-2-yl)ethyne disordered by symmetry across an
inversion centre. The final model presented yields relatively poor
refinement parameters, which is believed to be due to the presence of
a secondary minor component also exhibiting whole body disorder by
symmetry situated across the same geometric space of the major component
in the crystal, evidence of which is present in the residual fourier
difference map. It was not viable to model this disordered minor
component sensibly, given that the structure is comprised only of light
atoms and this would result in an unsatisfactorily low data-to-parameter
ratio. The model is instead presented as is as a twofold disordered
structure. Extensive efforts were made to look for additional signs of
twinning to account for the poor quality of the refinement, but there 
was no evidence in the raw data or most disagreeable reflections for
the existence of either pseudo- or non-merohedral twinning at play.
There is no further disordered ijn the model, and all non-H atoms in the
structure were subject to full anisotropic refinement. All H atoms in the
structure were placed in calculated positions and refined using a riding
model.

The erroneous reflection (3,3,9) was rempoved from the model, however no
systematic origin of this error could be ascertained.
;
_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. Others
 Fixed Sof: N2(0.5) C2(0.5) C9(0.5) C12(0.5) C14(0.5) H14B(0.5) H14C(0.5)
 H14A(0.5) C10(0.5) H10(0.5) C13(0.5) H13(0.5) C11(0.5) H11(0.5) C1(0.5)
 C3(0.5) C4(0.5) H4(0.5) N1(0.5) C7(0.5) H7(0.5) C6(0.5) C5(0.5) H5(0.5)
 C8(0.5) H8C(0.5) H8B(0.5) H8A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C11(H11), C4(H4), C7(H7), C5(H5)
3.b Idealised Me refined as rotating group:
 C14(H14B,H14C,H14A), C8(H8C,H8B,H8A)
;
_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
N2 N 0.7872(7) 0.8565(7) 0.3644(4) 0.0445(12) Uani 0.5 1 d . . P A -1
C2 C 0.9647(7) 0.7354(8) 0.2847(4) 0.0334(10) Uani 0.5 1 d . . P A -1
C9 C 0.8309(7) 0.7319(8) 0.3312(3) 0.0334(10) Uani 0.5 1 d . . P A -1
C12 C 0.5724(6) 0.7303(6) 0.4165(3) 0.0368(10) Uani 0.5 1 d . . P A -1
C14 C 0.4295(7) 0.7360(8) 0.4631(4) 0.0470(13) Uani 0.5 1 d . . P A -1
H14B H 0.442640 0.661114 0.512316 0.071 Uiso 0.5 1 calc R U P A -1
H14C H 0.327256 0.719736 0.414714 0.071 Uiso 0.5 1 calc R U P A -1
H14A H 0.425925 0.831012 0.492444 0.071 Uiso 0.5 1 calc R U P A -1
C10 C 0.7585(6) 0.6009(6) 0.3456(3) 0.0446(11) Uani 0.5 1 d . . P A -1
H10 H 0.797858 0.512784 0.325935 0.054 Uiso 0.5 1 calc R U P A -1
C13 C 0.6602(7) 0.8540(7) 0.4053(4) 0.0430(12) Uani 0.5 1 d . . P A -1
H13 H 0.627774 0.942601 0.428327 0.052 Uiso 0.5 1 calc R U P A -1
C11 C 0.6283(6) 0.6012(5) 0.3890(3) 0.0461(10) Uani 0.5 1 d . . P A -1
H11 H 0.577917 0.513013 0.399672 0.055 Uiso 0.5 1 calc R U P A -1
C1 C 1.0742(7) 0.7391(8) 0.2451(4) 0.0334(10) Uani 0.5 1 d . . P A -1
C3 C 1.2079(6) 0.7368(8) 0.1992(3) 0.0322(10) Uani 0.5 1 d . . P A -1
C4 C 1.2922(6) 0.6136(6) 0.1943(4) 0.0465(11) Uani 0.5 1 d . . P A -1
H4 H 1.261865 0.526021 0.219703 0.056 Uiso 0.5 1 calc R U P A -1
N1 N 1.2545(7) 0.8626(7) 0.1701(4) 0.0423(11) Uani 0.5 1 d . . P A -1
C7 C 1.3838(7) 0.8610(8) 0.1303(4) 0.0444(13) Uani 0.5 1 d . . P A -1
H7 H 1.418186 0.951080 0.110361 0.053 Uiso 0.5 1 calc R U P A -1
C6 C 1.4687(6) 0.7431(7) 0.1161(3) 0.0379(10) Uani 0.5 1 d . . P A -1
C5 C 1.4237(6) 0.6171(5) 0.1515(3) 0.0465(10) Uani 0.5 1 d . . P A -1
H5 H 1.482632 0.531010 0.146912 0.056 Uiso 0.5 1 calc R U P A -1
C8 C 1.6107(7) 0.7513(8) 0.0707(4) 0.0451(12) Uani 0.5 1 d . . P A -1
H8C H 1.571282 0.741395 0.001283 0.068 Uiso 0.5 1 calc R U P A -1
H8B H 1.688002 0.673329 0.095343 0.068 Uiso 0.5 1 calc R U P A -1
H8A H 1.665756 0.844610 0.085636 0.068 Uiso 0.5 1 calc R U P A -1


_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
N2 C9 1.334(10) . ?
N2 C13 1.340(10) . ?
C2 C9 1.444(10) . ?
C2 C1 1.195(3) . ?
C9 C10 1.396(9) . ?
C12 C14 1.514(8) . ?
C12 C13 1.393(9) . ?
C12 C11 1.378(8) . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14A 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.386(7) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C1 C3 1.437(9) . ?
C3 C4 1.354(9) . ?
C3 N1 1.330(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(7) . ?
N1 C7 1.348(9) . ?
C7 H7 0.9500 . ?
C7 C6 1.348(9) . ?
C6 C5 1.364(8) . ?
C6 C8 1.497(8) . ?
C5 H5 0.9500 . ?
C8 H8C 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8A 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
C9 N2 C13 117.5(6) . . ?
C1 C2 C9 179.1(7) . . ?
N2 C9 C2 117.4(7) . . ?
N2 C9 C10 122.1(6) . . ?
C10 C9 C2 120.4(6) . . ?
C13 C12 C14 121.5(6) . . ?
C11 C12 C14 121.4(5) . . ?
C11 C12 C13 117.0(5) . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14B C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
N2 C13 C12 124.5(6) . . ?
N2 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C2 C1 C3 177.3(10) . . ?
C4 C3 C1 121.0(6) . . ?
N1 C3 C1 117.1(7) . . ?
N1 C3 C4 121.7(6) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C3 N1 C7 117.0(6) . . ?
N1 C7 H7 117.1 . . ?
N1 C7 C6 125.8(7) . . ?
C6 C7 H7 117.1 . . ?
C7 C6 C5 115.6(5) . . ?
C7 C6 C8 122.2(6) . . ?
C5 C6 C8 122.0(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C6 C8 H8C 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8A 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 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
N2 C9 C10 C11 5.2(8) . . . . ?
C2 C9 C10 C11 -178.9(4) . . . . ?
C9 N2 C13 C12 0.8(8) . . . . ?
C9 C10 C11 C12 0.4(8) . . . . ?
C14 C12 C13 N2 -179.6(4) . . . . ?
C14 C12 C11 C10 179.3(4) . . . . ?
C13 N2 C9 C2 178.3(4) . . . . ?
C13 N2 C9 C10 -5.7(8) . . . . ?
C13 C12 C11 C10 -4.8(7) . . . . ?
C11 C12 C13 N2 4.5(8) . . . . ?
C1 C3 C4 C5 -178.2(4) . . . . ?
C1 C3 N1 C7 177.6(4) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C3 N1 C7 C6 0.9(8) . . . . ?
C4 C3 N1 C7 3.8(8) . . . . ?
N1 C3 C4 C5 -4.7(8) . . . . ?
N1 C7 C6 C5 -4.4(8) . . . . ?
N1 C7 C6 C8 179.6(4) . . . . ?
C7 C6 C5 C4 3.4(7) . . . . ?
C8 C6 C5 C4 179.3(4) . . . . ?

_olex2_submission_original_sample_id ROK200
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rok173_mje_mp
_database_code_depnum_ccdc_archive 'CCDC 2305048'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2023-11-01 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C58 H50 Cu4 I4 N8 P2, [C H2 Cl2]'
_chemical_formula_sum            'C59 H52 Cl2 Cu4 I4 N8 P2'
_chemical_formula_weight         1767.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   19.1051(8)
_cell_length_b                   17.5837(7)
_cell_length_c                   19.9459(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.8850(10)
_cell_angle_gamma                90
_cell_volume                     6601.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9299
_cell_measurement_temperature    105
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.692
_shelx_estimated_absorpt_T_min   0.437
_exptl_absorpt_coefficient_mu    3.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0821 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.8374.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3.00 -3.00 2.00 0.0490
-2.00 1.00 -1.00 0.1440
-2.00 -1.00 2.00 0.0460
-1.00 0.00 -4.00 0.1030
-1.00 1.00 3.00 0.0680
0.00 1.00 0.00 0.0750
0.00 -1.00 0.00 0.0580
1.00 0.00 4.00 0.0860
1.00 -1.00 -2.00 0.0500
3.00 4.00 -4.00 0.0300
4.00 0.00 -3.00 0.0620
4.00 -2.00 3.00 0.1070

_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            169316
_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         27.499
_diffrn_reflns_theta_min         1.993
_diffrn_ambient_temperature      105
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12040
_reflns_number_total             15131
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       0.00029(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   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         15131
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.149
_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)+(0.0152P)²+50.1851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          
;The asymmetric unit conatins one molecule of the target complex and a
highly disordered equivalent of co-crystalised DCM. Attempts to model 
the solvent were unsuccessful and so squeeze was implemented. A solvent 
mask was calculated and 180 electrons were found in a volume of 1158Å³ 
in 3 voids per unit cell. This is consistent with the presence of 1 CH2Cl2 
per Asymmetric Unit which account for 168 electrons per unit cell.,SQUEEZE
;
_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. Uiso/Uaniso restraints and constraints
Uanis(C45) \\sim Ueq, Uanis(C47) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C58(H58), C25(H25), C33(H33), C10(H10), C22(H22), C20(H20),
 C3(H3), C19(H19), C13(H13), C49(H49), C28(H28), C55(H55), C52(H52), C46(H46),
 C40(H40), C56(H56), C14(H14), C37(H37), C50(H50), C16(H16), C26(H26), C43(H43),
  C44(H44), C38(H38)
3.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C23(H23A,H23B,H23C), C59(H59A,H59B,H59C), C11(H11A,H11B,
 H11C), C17(H17A,H17B,H17C), C47(H47A,H47B,H47C), C53(H53A,H53B,H53C), C41(H41A,
 H41B,H41C)
;
_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
I3 I 0.51282(2) 0.59136(2) 0.17919(2) 0.02306(8) Uani 1 1 d . . . . .
I2 I 0.28168(2) 0.08292(2) 0.13806(2) 0.02533(8) Uani 1 1 d . . . . .
I4 I 0.65308(2) 0.44521(2) 0.09996(2) 0.02567(8) Uani 1 1 d . . . . .
I1 I 0.47263(2) -0.05674(2) 0.22254(2) 0.03100(9) Uani 1 1 d . . . . .
Cu4 Cu 0.59909(3) 0.33797(3) 0.16744(3) 0.01698(12) Uani 1 1 d . . . . .
Cu2 Cu 0.36362(3) 0.19413(3) 0.19593(3) 0.01666(12) Uani 1 1 d . . . . .
Cu3 Cu 0.59062(3) 0.47675(3) 0.20414(3) 0.01825(12) Uani 1 1 d . . . . .
Cu1 Cu 0.39408(3) 0.05572(3) 0.23191(3) 0.02033(12) Uani 1 1 d . . . . .
P1 P 0.52747(6) 0.37604(6) 0.23853(6) 0.0154(2) Uani 1 1 d . . . . .
P2 P 0.47127(6) 0.15854(7) 0.24510(6) 0.0164(2) Uani 1 1 d . . . . .
N4 N 0.3697(2) 0.2832(2) 0.13310(19) 0.0168(7) Uani 1 1 d . . . . .
N8 N 0.5508(2) 0.2509(2) 0.11020(19) 0.0183(8) Uani 1 1 d . . . . .
N3 N 0.3078(2) 0.2514(2) 0.26067(19) 0.0181(8) Uani 1 1 d . . . . .
N1 N 0.6579(2) 0.4511(2) 0.29584(19) 0.0180(8) Uani 1 1 d . . . . .
N7 N 0.6889(2) 0.2756(2) 0.2077(2) 0.0209(8) Uani 1 1 d . . . . .
N5 N 0.3812(2) 0.0894(2) 0.32978(19) 0.0196(8) Uani 1 1 d . . . . .
N6 N 0.6266(2) 0.2091(2) 0.4741(2) 0.0219(8) Uani 1 1 d . . . . .
N2 N 0.5104(2) 0.3414(2) 0.4904(2) 0.0233(8) Uani 1 1 d . . . . .
C24 C 0.4017(2) 0.3480(2) 0.1574(2) 0.0165(9) Uani 1 1 d . . . . .
C54 C 0.5388(2) 0.1849(3) 0.1403(2) 0.0165(9) Uani 1 1 d . . . . .
C4 C 0.4055(2) 0.3422(2) 0.2876(2) 0.0168(9) Uani 1 1 d . . . . .
C35 C 0.5490(2) 0.1803(3) 0.2158(2) 0.0173(9) Uani 1 1 d . . . . .
C5 C 0.4381(2) 0.3530(2) 0.2300(2) 0.0156(8) Uani 1 1 d . . . . .
C6 C 0.6350(2) 0.4039(2) 0.3413(2) 0.0162(8) Uani 1 1 d . . . . .
C7 C 0.6819(2) 0.3728(3) 0.3954(2) 0.0192(9) Uani 1 1 d . . . . .
H7 H 0.665632 0.337391 0.425313 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5137(2) 0.3743(2) 0.3738(2) 0.0161(8) Uani 1 1 d . . . . .
C8 C 0.7529(3) 0.3942(3) 0.4052(3) 0.0237(10) Uani 1 1 d . . . . .
H8 H 0.785201 0.374496 0.442686 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7769(3) 0.4445(3) 0.3602(3) 0.0237(10) Uani 1 1 d . . . . .
C1 C 0.5582(2) 0.3840(2) 0.3260(2) 0.0158(8) Uani 1 1 d . . . . .
C48 C 0.6825(2) 0.2095(3) 0.2398(2) 0.0187(9) Uani 1 1 d . . . . .
C31 C 0.4929(2) 0.1532(3) 0.3334(2) 0.0181(9) Uani 1 1 d . . . . .
C58 C 0.5328(3) 0.2568(3) 0.0422(2) 0.0212(9) Uani 1 1 d . . . . .
H58 H 0.541252 0.303993 0.021754 0.025 Uiso 1 1 calc R U . . .
C25 C 0.4068(3) 0.4097(3) 0.1141(2) 0.0220(10) Uani 1 1 d . . . . .
H25 H 0.429422 0.455354 0.131712 0.026 Uiso 1 1 calc R U . . .
C34 C 0.6130(2) 0.1915(3) 0.2611(2) 0.0194(9) Uani 1 1 d . . . . .
C33 C 0.6173(2) 0.1835(3) 0.3321(2) 0.0192(9) Uani 1 1 d . . . . .
H33 H 0.662715 0.191890 0.358980 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7269(3) 0.4696(3) 0.3057(2) 0.0228(10) Uani 1 1 d . . . . .
H10 H 0.742775 0.501950 0.273195 0.027 Uiso 1 1 calc R U . . .
C22 C 0.2432(3) 0.2275(3) 0.2708(3) 0.0228(10) Uani 1 1 d . . . . .
H22 H 0.227622 0.178743 0.253862 0.027 Uiso 1 1 calc R U . . .
C18 C 0.3298(2) 0.3204(3) 0.2855(2) 0.0171(9) Uani 1 1 d . . . . .
C20 C 0.2198(3) 0.3414(3) 0.3260(2) 0.0250(10) Uani 1 1 d . . . . .
H20 H 0.189514 0.373127 0.346836 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5360(2) 0.3900(3) 0.4482(2) 0.0179(9) Uani 1 1 d . . . . .
C42 C 0.5850(3) 0.1540(3) 0.4422(2) 0.0206(9) Uani 1 1 d . . . . .
C32 C 0.5627(3) 0.1647(2) 0.3673(2) 0.0186(9) Uani 1 1 d . . . . .
C21 C 0.1981(3) 0.2691(3) 0.3041(3) 0.0261(10) Uani 1 1 d . . . . .
C3 C 0.4427(2) 0.3530(3) 0.3539(2) 0.0167(9) Uani 1 1 d . . . . .
H3 H 0.416461 0.344842 0.389634 0.020 Uiso 1 1 calc R U . . .
C19 C 0.2860(3) 0.3671(3) 0.3171(2) 0.0230(10) Uani 1 1 d . . . . .
H19 H 0.301653 0.416343 0.332480 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5758(2) 0.4532(3) 0.4720(2) 0.0201(9) Uani 1 1 d . . . . .
H13 H 0.592839 0.486696 0.440993 0.024 Uiso 1 1 calc R U . . .
C36 C 0.4305(3) 0.1369(3) 0.3660(2) 0.0220(10) Uani 1 1 d . . . . .
C49 C 0.7396(3) 0.1608(3) 0.2592(3) 0.0243(10) Uani 1 1 d . . . . .
H49 H 0.733845 0.114659 0.282420 0.029 Uiso 1 1 calc R U . . .
C28 C 0.3419(3) 0.2789(3) 0.0663(2) 0.0212(9) Uani 1 1 d . . . . .
H28 H 0.318420 0.233246 0.049921 0.025 Uiso 1 1 calc R U . . .
C55 C 0.5097(3) 0.1223(3) 0.1013(2) 0.0210(9) Uani 1 1 d . . . . .
H55 H 0.502276 0.075419 0.122679 0.025 Uiso 1 1 calc R U . . .
C52 C 0.7538(3) 0.2939(3) 0.1947(3) 0.0286(11) Uani 1 1 d . . . . .
H52 H 0.758898 0.341174 0.173016 0.034 Uiso 1 1 calc R U . . .
C46 C 0.6504(3) 0.1995(3) 0.5400(2) 0.0246(10) Uani 1 1 d . . . . .
H46 H 0.679067 0.238785 0.563109 0.030 Uiso 1 1 calc R U . . .
C57 C 0.5027(3) 0.1986(3) -0.0001(2) 0.0241(10) Uani 1 1 d . . . . .
C40 C 0.3205(3) 0.0757(3) 0.3539(3) 0.0280(11) Uani 1 1 d . . . . .
H40 H 0.286429 0.042640 0.328682 0.034 Uiso 1 1 calc R U . . .
C56 C 0.4920(3) 0.1298(3) 0.0310(2) 0.0234(10) Uani 1 1 d . . . . .
H56 H 0.472513 0.087732 0.004137 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5907(3) 0.4671(3) 0.5412(2) 0.0233(10) Uani 1 1 d . . . . .
H14 H 0.617942 0.510362 0.558016 0.028 Uiso 1 1 calc R U . . .
C27 C 0.3456(3) 0.3370(3) 0.0202(2) 0.0230(10) Uani 1 1 d . . . . .
C29 C 0.3143(3) 0.3288(3) -0.0542(3) 0.0323(12) Uani 1 1 d . . . . .
H29A H 0.295006 0.277394 -0.062705 0.049 Uiso 1 1 calc R U . . .
H29B H 0.351407 0.337487 -0.081686 0.049 Uiso 1 1 calc R U . . .
H29C H 0.276196 0.366148 -0.066446 0.049 Uiso 1 1 calc R U . . .
C37 C 0.4181(3) 0.1717(3) 0.4257(2) 0.0251(10) Uani 1 1 d . . . . .
H37 H 0.452074 0.205625 0.449926 0.030 Uiso 1 1 calc R U . . .
C50 C 0.8055(3) 0.1810(3) 0.2439(3) 0.0334(13) Uani 1 1 d . . . . .
H50 H 0.845042 0.148153 0.256485 0.040 Uiso 1 1 calc R U . . .
C16 C 0.5260(3) 0.3555(3) 0.5572(2) 0.0257(10) Uani 1 1 d . . . . .
H16 H 0.508906 0.320808 0.587037 0.031 Uiso 1 1 calc R U . . .
C26 C 0.3788(3) 0.4038(3) 0.0456(3) 0.0274(11) Uani 1 1 d . . . . .
H26 H 0.382368 0.445376 0.015920 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5657(3) 0.4175(3) 0.5862(2) 0.0242(10) Uani 1 1 d . . . . .
C43 C 0.5677(3) 0.0890(3) 0.4748(3) 0.0312(12) Uani 1 1 d . . . . .
H43 H 0.538078 0.051017 0.450775 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1277(3) 0.2368(3) 0.3142(3) 0.0374(14) Uani 1 1 d . . . . .
H23A H 0.089122 0.267263 0.288559 0.056 Uiso 1 1 calc R U . . .
H23B H 0.124381 0.238067 0.362679 0.056 Uiso 1 1 calc R U . . .
H23C H 0.123633 0.184189 0.297895 0.056 Uiso 1 1 calc R U . . .
C59 C 0.4817(3) 0.2103(3) -0.0754(3) 0.0336(12) Uani 1 1 d . . . . .
H59A H 0.494107 0.262061 -0.087236 0.050 Uiso 1 1 calc R U . . .
H59B H 0.430319 0.202775 -0.088623 0.050 Uiso 1 1 calc R U . . .
H59C H 0.506878 0.173595 -0.099626 0.050 Uiso 1 1 calc R U . . .
C44 C 0.5948(3) 0.0804(3) 0.5438(3) 0.0369(14) Uani 1 1 d . . . . .
H44 H 0.584280 0.035938 0.567197 0.044 Uiso 1 1 calc R U . . .
C39 C 0.3052(3) 0.1070(3) 0.4132(3) 0.0348(13) Uani 1 1 d . . . . .
C51 C 0.8138(3) 0.2482(3) 0.2108(3) 0.0371(14) Uani 1 1 d . . . . .
C11 C 0.8530(3) 0.4709(4) 0.3687(3) 0.0393(14) Uani 1 1 d . . . . .
H11A H 0.868229 0.489476 0.415279 0.059 Uiso 1 1 calc R U . . .
H11B H 0.856892 0.512038 0.336425 0.059 Uiso 1 1 calc R U . . .
H11C H 0.883373 0.428363 0.360057 0.059 Uiso 1 1 calc R U . . .
C45 C 0.6368(3) 0.1363(3) 0.5780(3) 0.0345(12) Uani 1 1 d . U . . .
C38 C 0.3551(3) 0.1560(3) 0.4492(3) 0.0347(13) Uani 1 1 d . . . . .
H38 H 0.346170 0.178967 0.489978 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5788(3) 0.4302(4) 0.6616(2) 0.0347(13) Uani 1 1 d . . . . .
H17A H 0.630111 0.432836 0.678268 0.052 Uiso 1 1 calc R U . . .
H17B H 0.558421 0.388115 0.683999 0.052 Uiso 1 1 calc R U . . .
H17C H 0.556596 0.478109 0.671856 0.052 Uiso 1 1 calc R U . . .
C47 C 0.6683(4) 0.1309(4) 0.6523(4) 0.0540(17) Uani 1 1 d . U . . .
H47A H 0.714907 0.106298 0.657420 0.081 Uiso 1 1 calc R U . . .
H47B H 0.636822 0.100875 0.675972 0.081 Uiso 1 1 calc R U . . .
H47C H 0.673656 0.182109 0.671984 0.081 Uiso 1 1 calc R U . . .
C53 C 0.8836(3) 0.2724(4) 0.1931(5) 0.058(2) Uani 1 1 d . . . . .
H53A H 0.898066 0.236144 0.160806 0.088 Uiso 1 1 calc R U . . .
H53B H 0.919563 0.273758 0.234529 0.088 Uiso 1 1 calc R U . . .
H53C H 0.878687 0.323131 0.172534 0.088 Uiso 1 1 calc R U . . .
C41 C 0.2366(4) 0.0872(5) 0.4372(4) 0.056(2) Uani 1 1 d . . . . .
H41A H 0.203728 0.063776 0.399746 0.084 Uiso 1 1 calc R U . . .
H41B H 0.215231 0.133498 0.452052 0.084 Uiso 1 1 calc R U . . .
H41C H 0.246399 0.051352 0.475291 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
I3 Cu3 2.5029(6) . ?
I2 Cu2 2.6432(6) . ?
I2 Cu1 2.6389(7) . ?
I4 Cu4 2.6283(6) . ?
I4 Cu3 2.6268(6) . ?
I1 Cu1 2.5088(7) . ?
Cu4 Cu3 2.5608(8) . ?
Cu4 P1 2.2354(12) . ?
Cu4 N8 2.033(4) . ?
Cu4 N7 2.077(4) . ?
Cu2 Cu1 2.5754(8) . ?
Cu2 P2 2.2114(12) . ?
Cu2 N4 2.022(4) . ?
Cu2 N3 2.072(4) . ?
Cu3 P1 2.3123(12) . ?
Cu3 N1 2.097(4) . ?
Cu1 P2 2.3193(13) . ?
Cu1 N5 2.095(4) . ?
P1 C5 1.735(5) . ?
P1 C1 1.748(4) . ?
P2 C35 1.730(5) . ?
P2 C31 1.740(5) . ?
N4 C24 1.344(6) . ?
N4 C28 1.349(6) . ?
N8 C54 1.345(6) . ?
N8 C58 1.345(6) . ?
N3 C22 1.352(6) . ?
N3 C18 1.350(6) . ?
N1 C6 1.356(6) . ?
N1 C10 1.339(6) . ?
N7 C48 1.343(6) . ?
N7 C52 1.348(6) . ?
N5 C36 1.369(6) . ?
N5 C40 1.351(6) . ?
N6 C42 1.342(6) . ?
N6 C46 1.325(6) . ?
N2 C12 1.349(6) . ?
N2 C16 1.336(6) . ?
C24 C5 1.496(6) . ?
C24 C25 1.400(6) . ?
C54 C35 1.487(6) . ?
C54 C55 1.407(6) . ?
C4 C5 1.411(6) . ?
C4 C18 1.488(6) . ?
C4 C3 1.403(6) . ?
C35 C34 1.403(6) . ?
C6 C7 1.392(6) . ?
C6 C1 1.487(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(7) . ?
C2 C1 1.393(6) . ?
C2 C12 1.498(6) . ?
C2 C3 1.397(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(7) . ?
C9 C10 1.390(7) . ?
C9 C11 1.507(7) . ?
C48 C34 1.496(6) . ?
C48 C49 1.389(6) . ?
C31 C32 1.403(6) . ?
C31 C36 1.482(6) . ?
C58 H58 0.9500 . ?
C58 C57 1.387(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.384(7) . ?
C34 C33 1.411(6) . ?
C33 H33 0.9500 . ?
C33 C32 1.394(7) . ?
C10 H10 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.385(7) . ?
C18 C19 1.398(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(7) . ?
C20 C19 1.382(7) . ?
C12 C13 1.384(6) . ?
C42 C32 1.494(6) . ?
C42 C43 1.384(7) . ?
C21 C23 1.505(7) . ?
C3 H3 0.9500 . ?
C19 H19 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.383(6) . ?
C36 C37 1.395(7) . ?
C49 H49 0.9500 . ?
C49 C50 1.390(7) . ?
C28 H28 0.9500 . ?
C28 C27 1.385(7) . ?
C55 H55 0.9500 . ?
C55 C56 1.391(6) . ?
C52 H52 0.9500 . ?
C52 C51 1.392(7) . ?
C46 H46 0.9500 . ?
C46 C45 1.396(7) . ?
C57 C56 1.391(7) . ?
C57 C59 1.501(7) . ?
C40 H40 0.9500 . ?
C40 C39 1.380(8) . ?
C56 H56 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.394(7) . ?
C27 C29 1.507(6) . ?
C27 C26 1.388(7) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C37 H37 0.9500 . ?
C37 C38 1.391(7) . ?
C50 H50 0.9500 . ?
C50 C51 1.376(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.395(7) . ?
C26 H26 0.9500 . ?
C15 C17 1.499(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.392(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C44 H44 0.9500 . ?
C44 C45 1.373(8) . ?
C39 C38 1.390(8) . ?
C39 C41 1.510(8) . ?
C51 C53 1.498(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C45 C47 1.504(9) . ?
C38 H38 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 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
Cu1 I2 Cu2 58.362(18) . . ?
Cu3 I4 Cu4 58.325(18) . . ?
Cu3 Cu4 I4 60.809(19) . . ?
P1 Cu4 I4 116.54(4) . . ?
P1 Cu4 Cu3 57.16(3) . . ?
N8 Cu4 I4 115.62(11) . . ?
N8 Cu4 Cu3 146.41(11) . . ?
N8 Cu4 P1 108.28(11) . . ?
N8 Cu4 N7 94.84(15) . . ?
N7 Cu4 I4 101.87(11) . . ?
N7 Cu4 Cu3 118.75(11) . . ?
N7 Cu4 P1 117.89(12) . . ?
Cu1 Cu2 I2 60.735(19) . . ?
P2 Cu2 I2 114.86(4) . . ?
P2 Cu2 Cu1 57.36(3) . . ?
N4 Cu2 I2 113.27(10) . . ?
N4 Cu2 Cu1 150.53(11) . . ?
N4 Cu2 P2 110.27(11) . . ?
N4 Cu2 N3 95.73(15) . . ?
N3 Cu2 I2 107.59(11) . . ?
N3 Cu2 Cu1 113.69(11) . . ?
N3 Cu2 P2 113.60(11) . . ?
I3 Cu3 I4 110.34(2) . . ?
I3 Cu3 Cu4 140.80(3) . . ?
Cu4 Cu3 I4 60.866(19) . . ?
P1 Cu3 I3 110.69(4) . . ?
P1 Cu3 I4 113.83(4) . . ?
P1 Cu3 Cu4 54.32(3) . . ?
N1 Cu3 I3 126.96(11) . . ?
N1 Cu3 I4 110.53(11) . . ?
N1 Cu3 Cu4 89.12(11) . . ?
N1 Cu3 P1 81.34(11) . . ?
I1 Cu1 I2 120.95(3) . . ?
I1 Cu1 Cu2 146.47(3) . . ?
Cu2 Cu1 I2 60.903(19) . . ?
P2 Cu1 I2 111.31(4) . . ?
P2 Cu1 I1 104.25(4) . . ?
P2 Cu1 Cu2 53.41(3) . . ?
N5 Cu1 I2 113.46(11) . . ?
N5 Cu1 I1 117.37(11) . . ?
N5 Cu1 Cu2 86.31(11) . . ?
N5 Cu1 P2 81.28(11) . . ?
Cu4 P1 Cu3 68.52(4) . . ?
C5 P1 Cu4 124.55(15) . . ?
C5 P1 Cu3 134.78(15) . . ?
C5 P1 C1 105.9(2) . . ?
C1 P1 Cu4 121.29(15) . . ?
C1 P1 Cu3 97.53(15) . . ?
Cu2 P2 Cu1 69.24(4) . . ?
C35 P2 Cu2 125.07(16) . . ?
C35 P2 Cu1 134.43(16) . . ?
C35 P2 C31 106.6(2) . . ?
C31 P2 Cu2 120.32(16) . . ?
C31 P2 Cu1 96.25(16) . . ?
C24 N4 Cu2 120.3(3) . . ?
C24 N4 C28 118.8(4) . . ?
C28 N4 Cu2 120.9(3) . . ?
C54 N8 Cu4 119.7(3) . . ?
C54 N8 C58 118.9(4) . . ?
C58 N8 Cu4 121.4(3) . . ?
C22 N3 Cu2 121.5(3) . . ?
C18 N3 Cu2 120.2(3) . . ?
C18 N3 C22 117.4(4) . . ?
C6 N1 Cu3 119.6(3) . . ?
C10 N1 Cu3 121.1(3) . . ?
C10 N1 C6 118.3(4) . . ?
C48 N7 Cu4 120.3(3) . . ?
C48 N7 C52 117.4(4) . . ?
C52 N7 Cu4 121.7(3) . . ?
C36 N5 Cu1 119.0(3) . . ?
C40 N5 Cu1 121.8(3) . . ?
C40 N5 C36 118.3(4) . . ?
C46 N6 C42 117.0(4) . . ?
C16 N2 C12 117.5(4) . . ?
N4 C24 C5 120.4(4) . . ?
N4 C24 C25 120.7(4) . . ?
C25 C24 C5 118.7(4) . . ?
N8 C54 C35 119.8(4) . . ?
N8 C54 C55 120.7(4) . . ?
C55 C54 C35 119.2(4) . . ?
C5 C4 C18 125.0(4) . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 C18 113.2(4) . . ?
C54 C35 P2 112.5(3) . . ?
C34 C35 P2 121.1(3) . . ?
C34 C35 C54 126.4(4) . . ?
C24 C5 P1 113.3(3) . . ?
C4 C5 P1 121.1(3) . . ?
C4 C5 C24 125.7(4) . . ?
N1 C6 C7 121.3(4) . . ?
N1 C6 C1 115.3(4) . . ?
C7 C6 C1 123.2(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(4) . . ?
C8 C7 H7 120.5 . . ?
C1 C2 C12 123.6(4) . . ?
C1 C2 C3 121.1(4) . . ?
C3 C2 C12 115.3(4) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C11 122.8(5) . . ?
C10 C9 C8 116.5(4) . . ?
C10 C9 C11 120.7(5) . . ?
C6 C1 P1 112.0(3) . . ?
C2 C1 P1 122.2(3) . . ?
C2 C1 C6 125.8(4) . . ?
N7 C48 C34 118.4(4) . . ?
N7 C48 C49 122.4(4) . . ?
C49 C48 C34 119.0(4) . . ?
C32 C31 P2 121.4(3) . . ?
C32 C31 C36 125.9(4) . . ?
C36 C31 P2 112.7(3) . . ?
N8 C58 H58 117.8 . . ?
N8 C58 C57 124.3(4) . . ?
C57 C58 H58 117.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C35 C34 C48 124.4(4) . . ?
C35 C34 C33 121.8(4) . . ?
C33 C34 C48 113.8(4) . . ?
C34 C33 H33 116.2 . . ?
C32 C33 C34 127.5(4) . . ?
C32 C33 H33 116.2 . . ?
N1 C10 C9 124.4(5) . . ?
N1 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N3 C22 H22 117.7 . . ?
N3 C22 C21 124.5(4) . . ?
C21 C22 H22 117.7 . . ?
N3 C18 C4 118.8(4) . . ?
N3 C18 C19 121.3(4) . . ?
C19 C18 C4 119.4(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.5(5) . . ?
N2 C12 C2 115.5(4) . . ?
N2 C12 C13 122.1(4) . . ?
C13 C12 C2 122.2(4) . . ?
N6 C42 C32 115.3(4) . . ?
N6 C42 C43 122.9(4) . . ?
C43 C42 C32 121.6(4) . . ?
C31 C32 C42 123.3(4) . . ?
C33 C32 C31 121.5(4) . . ?
C33 C32 C42 115.1(4) . . ?
C22 C21 C23 120.6(5) . . ?
C20 C21 C22 117.3(4) . . ?
C20 C21 C23 122.1(5) . . ?
C4 C3 H3 116.0 . . ?
C2 C3 C4 127.9(4) . . ?
C2 C3 H3 116.0 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
N5 C36 C31 114.8(4) . . ?
N5 C36 C37 121.1(5) . . ?
C37 C36 C31 123.8(5) . . ?
C48 C49 H49 120.7 . . ?
C48 C49 C50 118.6(5) . . ?
C50 C49 H49 120.7 . . ?
N4 C28 H28 118.0 . . ?
N4 C28 C27 124.0(4) . . ?
C27 C28 H28 118.0 . . ?
C54 C55 H55 120.4 . . ?
C56 C55 C54 119.3(4) . . ?
C56 C55 H55 120.4 . . ?
N7 C52 H52 117.8 . . ?
N7 C52 C51 124.5(5) . . ?
C51 C52 H52 117.8 . . ?
N6 C46 H46 117.4 . . ?
N6 C46 C45 125.2(5) . . ?
C45 C46 H46 117.4 . . ?
C58 C57 C56 116.7(4) . . ?
C58 C57 C59 121.3(5) . . ?
C56 C57 C59 122.1(5) . . ?
N5 C40 H40 118.1 . . ?
N5 C40 C39 123.7(5) . . ?
C39 C40 H40 118.1 . . ?
C55 C56 C57 120.2(4) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 H56 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(5) . . ?
C15 C14 H14 120.0 . . ?
C28 C27 C29 121.7(4) . . ?
C28 C27 C26 117.0(4) . . ?
C26 C27 C29 121.3(4) . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C36 C37 H37 120.6 . . ?
C38 C37 C36 118.9(5) . . ?
C38 C37 H37 120.6 . . ?
C49 C50 H50 119.7 . . ?
C51 C50 C49 120.5(5) . . ?
C51 C50 H50 119.7 . . ?
N2 C16 H16 117.6 . . ?
N2 C16 C15 124.8(5) . . ?
C15 C16 H16 117.6 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C14 C15 C16 116.3(4) . . ?
C14 C15 C17 122.4(5) . . ?
C16 C15 C17 121.3(5) . . ?
C42 C43 H43 120.8 . . ?
C42 C43 C44 118.4(5) . . ?
C44 C43 H43 120.8 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 C43 120.0(5) . . ?
C45 C44 H44 120.0 . . ?
C40 C39 C38 117.5(5) . . ?
C40 C39 C41 120.1(6) . . ?
C38 C39 C41 122.4(5) . . ?
C52 C51 C53 120.8(5) . . ?
C50 C51 C52 116.7(5) . . ?
C50 C51 C53 122.5(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C46 C45 C47 120.4(5) . . ?
C44 C45 C46 116.6(5) . . ?
C44 C45 C47 123.1(5) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.4(5) . . ?
C39 C38 H38 119.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 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
Cu4 P1 C5 C24 -34.7(4) . . . . ?
Cu4 P1 C5 C4 146.3(3) . . . . ?
Cu4 P1 C1 C6 30.4(4) . . . . ?
Cu4 P1 C1 C2 -151.1(3) . . . . ?
Cu4 N8 C54 C35 10.7(5) . . . . ?
Cu4 N8 C54 C55 -175.9(3) . . . . ?
Cu4 N8 C58 C57 177.1(4) . . . . ?
Cu4 N7 C48 C34 -14.9(6) . . . . ?
Cu4 N7 C48 C49 170.9(4) . . . . ?
Cu4 N7 C52 C51 -169.4(5) . . . . ?
Cu2 P2 C35 C54 -32.8(4) . . . . ?
Cu2 P2 C35 C34 147.3(3) . . . . ?
Cu2 P2 C31 C32 -151.1(3) . . . . ?
Cu2 P2 C31 C36 28.1(4) . . . . ?
Cu2 N4 C24 C5 4.7(6) . . . . ?
Cu2 N4 C24 C25 179.3(3) . . . . ?
Cu2 N4 C28 C27 -178.5(4) . . . . ?
Cu2 N3 C22 C21 -169.0(4) . . . . ?
Cu2 N3 C18 C4 -22.2(5) . . . . ?
Cu2 N3 C18 C19 166.4(3) . . . . ?
Cu3 P1 C5 C24 58.5(4) . . . . ?
Cu3 P1 C5 C4 -120.4(3) . . . . ?
Cu3 P1 C1 C6 -39.0(3) . . . . ?
Cu3 P1 C1 C2 139.5(4) . . . . ?
Cu3 N1 C6 C7 166.4(3) . . . . ?
Cu3 N1 C6 C1 -9.5(5) . . . . ?
Cu3 N1 C10 C9 -169.7(4) . . . . ?
Cu1 P2 C35 C54 61.9(4) . . . . ?
Cu1 P2 C35 C34 -118.0(3) . . . . ?
Cu1 P2 C31 C32 139.3(4) . . . . ?
Cu1 P2 C31 C36 -41.4(3) . . . . ?
Cu1 N5 C36 C31 -6.0(5) . . . . ?
Cu1 N5 C36 C37 168.4(4) . . . . ?
Cu1 N5 C40 C39 -169.3(4) . . . . ?
P2 C35 C34 C48 179.2(3) . . . . ?
P2 C35 C34 C33 1.8(6) . . . . ?
P2 C31 C32 C33 2.3(6) . . . . ?
P2 C31 C32 C42 -174.4(3) . . . . ?
P2 C31 C36 N5 35.1(5) . . . . ?
P2 C31 C36 C37 -139.1(4) . . . . ?
N4 C24 C5 P1 121.4(4) . . . . ?
N4 C24 C5 C4 -59.7(6) . . . . ?
N4 C24 C25 C26 -0.2(7) . . . . ?
N4 C28 C27 C29 179.3(5) . . . . ?
N4 C28 C27 C26 -1.3(8) . . . . ?
N8 C54 C35 P2 117.8(4) . . . . ?
N8 C54 C35 C34 -62.3(6) . . . . ?
N8 C54 C55 C56 -1.4(7) . . . . ?
N8 C58 C57 C56 -1.1(8) . . . . ?
N8 C58 C57 C59 177.9(5) . . . . ?
N3 C22 C21 C20 2.8(8) . . . . ?
N3 C22 C21 C23 -178.7(5) . . . . ?
N3 C18 C19 C20 2.7(7) . . . . ?
N1 C6 C7 C8 3.8(7) . . . . ?
N1 C6 C1 P1 35.2(5) . . . . ?
N1 C6 C1 C2 -143.3(4) . . . . ?
N7 C48 C34 C35 64.3(6) . . . . ?
N7 C48 C34 C33 -118.1(5) . . . . ?
N7 C48 C49 C50 -0.8(8) . . . . ?
N7 C52 C51 C50 -1.9(10) . . . . ?
N7 C52 C51 C53 178.8(6) . . . . ?
N5 C36 C37 C38 1.6(7) . . . . ?
N5 C40 C39 C38 0.9(9) . . . . ?
N5 C40 C39 C41 -178.7(6) . . . . ?
N6 C42 C32 C31 -135.1(5) . . . . ?
N6 C42 C32 C33 47.9(6) . . . . ?
N6 C42 C43 C44 0.1(9) . . . . ?
N6 C46 C45 C44 -0.5(9) . . . . ?
N6 C46 C45 C47 178.4(6) . . . . ?
N2 C12 C13 C14 0.5(7) . . . . ?
N2 C16 C15 C14 -0.6(8) . . . . ?
N2 C16 C15 C17 178.2(5) . . . . ?
C24 N4 C28 C27 1.5(7) . . . . ?
C24 C25 C26 C27 0.3(8) . . . . ?
C54 N8 C58 C57 -0.6(7) . . . . ?
C54 C35 C34 C48 -0.7(7) . . . . ?
C54 C35 C34 C33 -178.0(4) . . . . ?
C54 C55 C56 C57 -0.3(7) . . . . ?
C4 C18 C19 C20 -168.7(4) . . . . ?
C35 P2 C31 C32 -0.8(4) . . . . ?
C35 P2 C31 C36 178.4(3) . . . . ?
C35 C54 C55 C56 172.1(4) . . . . ?
C35 C34 C33 C32 -0.3(8) . . . . ?
C5 P1 C1 C6 -180.0(3) . . . . ?
C5 P1 C1 C2 -1.4(4) . . . . ?
C5 C24 C25 C26 174.5(4) . . . . ?
C5 C4 C18 N3 65.4(6) . . . . ?
C5 C4 C18 C19 -123.0(5) . . . . ?
C5 C4 C3 C2 -0.5(7) . . . . ?
C6 N1 C10 C9 -1.1(7) . . . . ?
C6 C7 C8 C9 -1.8(7) . . . . ?
C7 C6 C1 P1 -140.6(4) . . . . ?
C7 C6 C1 C2 40.9(7) . . . . ?
C7 C8 C9 C10 -1.4(7) . . . . ?
C7 C8 C9 C11 178.9(5) . . . . ?
C2 C12 C13 C14 175.8(4) . . . . ?
C8 C9 C10 N1 3.0(8) . . . . ?
C1 P1 C5 C24 176.9(3) . . . . ?
C1 P1 C5 C4 -2.1(4) . . . . ?
C1 C6 C7 C8 179.3(4) . . . . ?
C1 C2 C12 N2 -142.4(4) . . . . ?
C1 C2 C12 C13 42.0(7) . . . . ?
C1 C2 C3 C4 -3.3(7) . . . . ?
C48 N7 C52 C51 1.6(8) . . . . ?
C48 C34 C33 C32 -177.9(4) . . . . ?
C48 C49 C50 C51 0.5(9) . . . . ?
C31 P2 C35 C54 178.7(3) . . . . ?
C31 P2 C35 C34 -1.2(4) . . . . ?
C31 C36 C37 C38 175.4(5) . . . . ?
C58 N8 C54 C35 -171.7(4) . . . . ?
C58 N8 C54 C55 1.8(7) . . . . ?
C58 C57 C56 C55 1.5(7) . . . . ?
C25 C24 C5 P1 -53.3(5) . . . . ?
C25 C24 C5 C4 125.6(5) . . . . ?
C34 C48 C49 C50 -175.0(5) . . . . ?
C34 C33 C32 C31 -2.0(7) . . . . ?
C34 C33 C32 C42 175.1(4) . . . . ?
C10 N1 C6 C7 -2.4(7) . . . . ?
C10 N1 C6 C1 -178.3(4) . . . . ?
C22 N3 C18 C4 168.0(4) . . . . ?
C22 N3 C18 C19 -3.4(6) . . . . ?
C18 N3 C22 C21 0.6(7) . . . . ?
C18 C4 C5 P1 -178.3(3) . . . . ?
C18 C4 C5 C24 2.9(7) . . . . ?
C18 C4 C3 C2 -179.2(4) . . . . ?
C12 N2 C16 C15 1.2(8) . . . . ?
C12 C2 C1 P1 -172.3(3) . . . . ?
C12 C2 C1 C6 6.0(7) . . . . ?
C12 C2 C3 C4 173.3(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C42 N6 C46 C45 1.4(8) . . . . ?
C42 C43 C44 C45 0.9(9) . . . . ?
C32 C31 C36 N5 -145.7(5) . . . . ?
C32 C31 C36 C37 40.1(7) . . . . ?
C32 C42 C43 C44 175.2(5) . . . . ?
C21 C20 C19 C18 0.9(7) . . . . ?
C3 C4 C5 P1 3.2(6) . . . . ?
C3 C4 C5 C24 -175.6(4) . . . . ?
C3 C4 C18 N3 -116.0(5) . . . . ?
C3 C4 C18 C19 55.6(6) . . . . ?
C3 C2 C1 P1 4.0(6) . . . . ?
C3 C2 C1 C6 -177.7(4) . . . . ?
C3 C2 C12 N2 41.1(6) . . . . ?
C3 C2 C12 C13 -134.4(5) . . . . ?
C19 C20 C21 C22 -3.4(7) . . . . ?
C19 C20 C21 C23 178.1(5) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C13 C14 C15 C17 -178.9(5) . . . . ?
C36 N5 C40 C39 0.1(8) . . . . ?
C36 C31 C32 C33 -176.8(4) . . . . ?
C36 C31 C32 C42 6.4(7) . . . . ?
C36 C37 C38 C39 -0.6(8) . . . . ?
C49 C48 C34 C35 -121.3(5) . . . . ?
C49 C48 C34 C33 56.3(6) . . . . ?
C49 C50 C51 C52 0.7(9) . . . . ?
C49 C50 C51 C53 -179.9(7) . . . . ?
C28 N4 C24 C5 -175.2(4) . . . . ?
C28 N4 C24 C25 -0.7(7) . . . . ?
C28 C27 C26 C25 0.4(8) . . . . ?
C55 C54 C35 P2 -55.7(5) . . . . ?
C55 C54 C35 C34 124.2(5) . . . . ?
C52 N7 C48 C34 174.0(4) . . . . ?
C52 N7 C48 C49 -0.3(7) . . . . ?
C46 N6 C42 C32 -176.6(4) . . . . ?
C46 N6 C42 C43 -1.2(8) . . . . ?
C40 N5 C36 C31 -175.7(4) . . . . ?
C40 N5 C36 C37 -1.3(7) . . . . ?
C40 C39 C38 C37 -0.6(9) . . . . ?
C29 C27 C26 C25 179.8(5) . . . . ?
C16 N2 C12 C2 -176.7(4) . . . . ?
C16 N2 C12 C13 -1.1(7) . . . . ?
C43 C42 C32 C31 49.4(7) . . . . ?
C43 C42 C32 C33 -127.6(5) . . . . ?
C43 C44 C45 C46 -0.7(9) . . . . ?
C43 C44 C45 C47 -179.6(6) . . . . ?
C59 C57 C56 C55 -177.5(5) . . . . ?
C11 C9 C10 N1 -177.4(5) . . . . ?
C41 C39 C38 C37 179.0(6) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 180 electrons were 
found in a volume of 1158Å³ in 3 voids per unit cell. 
This is consistent with the presence of 
[+ solvents] per Asymmetric Unit 
which account for 168 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 25.3 0.0 '2 ?'
2 -0.200 0.239 0.063 263.7 44.9 '1 CH2Cl2'
3 0.300 0.261 0.563 263.7 44.1 '1 CH2Cl2'
4 -0.300 0.739 0.437 263.7 44.2 '1 CH2Cl2'
5 0.200 0.761 0.937 263.7 43.4 '1 CH2Cl2'
6 0.170 -0.006 0.287 12.9 0.0 '1 ?'
7 0.330 0.494 0.213 12.9 0.0 '1 ?'
8 0.500 0.500 0.000 25.3 0.0 '2 ?'
9 0.670 0.506 0.787 12.9 0.3 '1 ?'
10 0.830 0.006 0.713 12.9 0.0 '1 ?'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
