# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_JCK_NiCl2tBu1C1H_HCl_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bs6v6
_database_code_depnum_ccdc_archive 'CCDC 2168228'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 Cl3 N2 Ni P'
_chemical_formula_sum            'C14 H26 Cl3 N2 Ni P'
_chemical_formula_weight         418.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.5512(8)
_cell_length_b                   14.6926(7)
_cell_length_c                   16.9036(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3862.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.762
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    1.498
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.7175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.192
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.707
_diffrn_reflns_theta_min         2.256
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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                   'fine focus sealed tube X-ray source'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3580
_reflns_number_total             4434
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.066
_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)+(0.0409P)²+2.8410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0998
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2
 0.9 with sigma of 0.02
 P1-H2
 2.07 with sigma of 0.04
 C6-H2
 1.93 with sigma of 0.04
 P1-C7 \\sim P1-C11
 with sigma of 0.02
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Ni1 Ni 0.34505(2) 0.88131(2) 0.61427(2) 0.04472(11) Uani 1 1 d . . . . .
Cl1 Cl 0.20824(4) 0.89458(5) 0.57512(4) 0.05620(18) Uani 1 1 d . . . . .
Cl2 Cl 0.40975(5) 1.00912(5) 0.57604(5) 0.06012(19) Uani 1 1 d . . . . .
Cl3 Cl 0.38052(5) 0.85290(5) 0.74139(4) 0.06016(19) Uani 1 1 d . . . . .
P1 P 0.24690(4) 0.59861(4) 0.75108(3) 0.03546(14) Uani 1 1 d D . . . .
N1 N 0.39625(11) 0.77103(13) 0.55943(11) 0.0375(4) Uani 1 1 d . . . . .
N2 N 0.30250(13) 0.65948(14) 0.68857(11) 0.0421(4) Uani 1 1 d D . . . .
C1 C 0.46952(15) 0.78719(18) 0.51935(14) 0.0454(5) Uani 1 1 d . . . . .
H1A H 0.493593 0.845064 0.521835 0.054 Uiso 1 1 calc R U . . .
C2 C 0.51015(17) 0.7219(2) 0.47502(16) 0.0554(7) Uani 1 1 d . . . . .
H2A H 0.560592 0.735444 0.447928 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4756(2) 0.6370(2) 0.47127(18) 0.0628(8) Uani 1 1 d . . . . .
H3 H 0.501631 0.591948 0.440889 0.075 Uiso 1 1 calc R U . . .
C4 C 0.40164(19) 0.61841(18) 0.51297(17) 0.0540(6) Uani 1 1 d . . . . .
H4 H 0.377783 0.560399 0.511469 0.065 Uiso 1 1 calc R U . . .
C5 C 0.36280(14) 0.68631(16) 0.55718(13) 0.0385(5) Uani 1 1 d . . . . .
C6 C 0.28212(15) 0.66769(17) 0.60381(13) 0.0424(5) Uani 1 1 d D . . . .
H6A H 0.241420 0.716884 0.595891 0.051 Uiso 1 1 calc R U . . .
H6B H 0.255816 0.611764 0.585267 0.051 Uiso 1 1 calc R U . . .
C7 C 0.32381(16) 0.54507(17) 0.81896(15) 0.0452(5) Uani 1 1 d D . . . .
C8 C 0.3806(2) 0.6176(2) 0.8579(2) 0.0657(8) Uani 1 1 d . . . . .
H8A H 0.408307 0.653262 0.817684 0.099 Uiso 1 1 calc R U . . .
H8B H 0.423422 0.588555 0.890103 0.099 Uiso 1 1 calc R U . . .
H8C H 0.345726 0.656538 0.890335 0.099 Uiso 1 1 calc R U . . .
C9 C 0.3789(2) 0.4811(2) 0.76750(19) 0.0655(8) Uani 1 1 d . . . . .
H9A H 0.343026 0.434786 0.744908 0.098 Uiso 1 1 calc R U . . .
H9B H 0.422521 0.453288 0.799622 0.098 Uiso 1 1 calc R U . . .
H9C H 0.405626 0.515510 0.725903 0.098 Uiso 1 1 calc R U . . .
C10 C 0.2774(2) 0.4893(2) 0.88206(17) 0.0623(8) Uani 1 1 d . . . . .
H10A H 0.237796 0.448211 0.857067 0.093 Uiso 1 1 calc R U . . .
H10B H 0.246425 0.529437 0.916679 0.093 Uiso 1 1 calc R U . . .
H10C H 0.318658 0.455196 0.912112 0.093 Uiso 1 1 calc R U . . .
C11 C 0.15546(15) 0.65973(17) 0.79515(15) 0.0445(5) Uani 1 1 d D . . . .
C12 C 0.1845(2) 0.7286(2) 0.85697(18) 0.0608(7) Uani 1 1 d . . . . .
H12A H 0.230294 0.764982 0.835705 0.091 Uiso 1 1 calc R U . . .
H12B H 0.204579 0.696990 0.903148 0.091 Uiso 1 1 calc R U . . .
H12C H 0.137105 0.767119 0.871023 0.091 Uiso 1 1 calc R U . . .
C13 C 0.0914(2) 0.5913(2) 0.8306(2) 0.0688(9) Uani 1 1 d . . . . .
H13A H 0.039982 0.622610 0.846330 0.103 Uiso 1 1 calc R U . . .
H13B H 0.116747 0.562409 0.875914 0.103 Uiso 1 1 calc R U . . .
H13C H 0.077386 0.545981 0.791736 0.103 Uiso 1 1 calc R U . . .
C14 C 0.11199(19) 0.7093(2) 0.72565(19) 0.0629(8) Uani 1 1 d . . . . .
H14A H 0.150472 0.754479 0.704823 0.094 Uiso 1 1 calc R U . . .
H14B H 0.060297 0.738296 0.743821 0.094 Uiso 1 1 calc R U . . .
H14C H 0.098104 0.666224 0.684941 0.094 Uiso 1 1 calc R U . . .
H2 H 0.3284(19) 0.7040(16) 0.7093(15) 0.075 Uiso 1 1 d D U . . .
H1 H 0.2129(16) 0.5337(17) 0.7090(15) 0.046(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.2366(7) . ?
Ni1 Cl2 2.2264(8) . ?
Ni1 Cl3 2.2573(8) . ?
Ni1 N1 2.0294(19) . ?
P1 N2 1.632(2) . ?
P1 C7 1.835(2) . ?
P1 C11 1.840(2) . ?
P1 H1 1.30(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.350(3) . ?
N2 C6 1.472(3) . ?
N2 H2 0.845(16) . ?
C1 H1A 0.9300 . ?
C1 C2 1.372(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.360(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 C6 1.507(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.533(4) . ?
C7 C9 1.541(4) . ?
C7 C10 1.527(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.523(4) . ?
C11 C13 1.538(4) . ?
C11 C14 1.539(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
Cl1 Ni1 Cl3 122.02(3) . . ?
Cl2 Ni1 Cl1 105.69(3) . . ?
Cl2 Ni1 Cl3 108.77(3) . . ?
N1 Ni1 Cl1 107.91(6) . . ?
N1 Ni1 Cl2 111.31(6) . . ?
N1 Ni1 Cl3 101.03(6) . . ?
N2 P1 C7 107.13(11) . . ?
N2 P1 C11 113.84(11) . . ?
N2 P1 H1 105.2(11) . . ?
C7 P1 C11 117.39(12) . . ?
C7 P1 H1 107.0(11) . . ?
C11 P1 H1 105.4(11) . . ?
C1 N1 Ni1 114.90(16) . . ?
C1 N1 C5 118.3(2) . . ?
C5 N1 Ni1 126.73(15) . . ?
P1 N2 H2 114.1(19) . . ?
C6 N2 P1 124.11(16) . . ?
C6 N2 H2 116.3(19) . . ?
N1 C1 H1A 118.6 . . ?
N1 C1 C2 122.8(2) . . ?
C2 C1 H1A 118.6 . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.8(2) . . ?
N1 C5 C6 118.3(2) . . ?
C4 C5 C6 121.0(2) . . ?
N2 C6 C5 110.16(19) . . ?
N2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 P1 110.25(18) . . ?
C8 C7 C9 110.2(2) . . ?
C9 C7 P1 105.73(18) . . ?
C10 C7 P1 111.01(19) . . ?
C10 C7 C8 110.2(2) . . ?
C10 C7 C9 109.3(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 P1 111.87(18) . . ?
C12 C11 C13 111.1(2) . . ?
C12 C11 C14 109.9(2) . . ?
C13 C11 P1 109.84(19) . . ?
C13 C11 C14 108.8(2) . . ?
C14 C11 P1 105.16(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N1 C1 C2 -176.06(19) . . . . ?
Ni1 N1 C5 C4 175.62(18) . . . . ?
Ni1 N1 C5 C6 -4.2(3) . . . . ?
P1 N2 C6 C5 -151.96(18) . . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
N1 C5 C6 N2 -76.1(3) . . . . ?
N2 P1 C7 C8 55.3(2) . . . . ?
N2 P1 C7 C9 -63.8(2) . . . . ?
N2 P1 C7 C10 177.77(19) . . . . ?
N2 P1 C11 C12 -74.4(2) . . . . ?
N2 P1 C11 C13 161.7(2) . . . . ?
N2 P1 C11 C14 44.8(2) . . . . ?
C1 N1 C5 C4 -1.8(3) . . . . ?
C1 N1 C5 C6 178.4(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 N2 104.0(3) . . . . ?
C5 N1 C1 C2 1.6(3) . . . . ?
C7 P1 N2 C6 141.5(2) . . . . ?
C7 P1 C11 C12 51.8(2) . . . . ?
C7 P1 C11 C13 -72.0(2) . . . . ?
C7 P1 C11 C14 171.03(18) . . . . ?
C11 P1 N2 C6 -87.0(2) . . . . ?
C11 P1 C7 C8 -74.2(2) . . . . ?
C11 P1 C7 C9 166.70(19) . . . . ?
C11 P1 C7 C10 48.3(2) . . . . ?

_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_JCK_CutBu2C_yellow_02082021
_audit_block_doi                 10.5517/ccdc.csd.cc2bs6y9
_database_code_depnum_ccdc_archive 'CCDC 2168231'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H30 Cl3 Cu N2 O P'
_chemical_formula_sum            'C16 H30 Cl3 Cu N2 O P'
_chemical_formula_weight         467.28
_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'
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      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                   8.4135(2)
_cell_length_b                   13.9973(3)
_cell_length_c                   17.9874(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.0770(10)
_cell_angle_gamma                90
_cell_volume                     2116.92(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9087
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    1.492
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.082
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26748
_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         27.504
_diffrn_reflns_theta_min         1.844
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             4858
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.016
_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)+(0.0377P)²+1.0642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0984
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.06 with sigma of 0.04
 C7-H2N
 1.93 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6AB), C7(H7A,H7AB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.36308(5) 0.51531(3) 0.76795(2) 0.03927(13) Uani 1 1 d . . . . .
Cl1 Cl 0.50624(12) 0.57449(8) 0.86434(5) 0.0651(3) Uani 1 1 d . . . . .
Cl2 Cl 0.11995(11) 0.52632(7) 0.81346(5) 0.0559(2) Uani 1 1 d . . . . .
Cl3 Cl 0.30668(12) 0.56481(7) 0.65147(5) 0.0606(3) Uani 1 1 d . . . . .
P1 P 0.29916(10) 0.27623(6) 0.51371(4) 0.03226(19) Uani 1 1 d D . . . .
O1 O 0.3899(3) 0.37597(14) 0.51091(11) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.5275(3) 0.41677(18) 0.74073(13) 0.0354(6) Uani 1 1 d . . . . .
N2 N 0.2877(3) 0.24449(17) 0.59999(13) 0.0345(6) Uani 1 1 d D . . . .
H2N H 0.279(4) 0.1843(12) 0.6065(14) 0.041 Uiso 1 1 d D U . . .
C1 C 0.6778(4) 0.4464(3) 0.73279(17) 0.0433(8) Uani 1 1 d . . . . .
H1 H 0.700973 0.510620 0.740894 0.052 Uiso 1 1 calc R U . . .
C2 C 0.7991(4) 0.3867(3) 0.71332(19) 0.0487(9) Uani 1 1 d . . . . .
H2 H 0.901005 0.410279 0.706875 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7660(4) 0.2913(3) 0.70361(18) 0.0478(9) Uani 1 1 d . . . . .
H3 H 0.845970 0.248757 0.691618 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6128(4) 0.2597(2) 0.71189(16) 0.0404(8) Uani 1 1 d . . . . .
H4 H 0.588803 0.195231 0.705620 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4940(4) 0.3237(2) 0.72958(15) 0.0324(7) Uani 1 1 d . . . . .
C6 C 0.3253(4) 0.2914(2) 0.73379(16) 0.0361(7) Uani 1 1 d . . . . .
H6A H 0.274660 0.327571 0.772384 0.043 Uiso 1 1 calc R U . . .
H6AB H 0.324346 0.224657 0.748171 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2279(4) 0.3031(2) 0.66094(16) 0.0374(7) Uani 1 1 d D . . . .
H7A H 0.118388 0.285587 0.669162 0.045 Uiso 1 1 calc R U . . .
H7AB H 0.229268 0.369751 0.646235 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1094(4) 0.3103(2) 0.46657(17) 0.0417(8) Uani 1 1 d . . . . .
C9 C 0.0130(4) 0.3681(3) 0.5219(2) 0.0656(12) Uani 1 1 d . . . . .
H9A H 0.076529 0.420066 0.541211 0.098 Uiso 1 1 calc R U . . .
H9B H -0.016637 0.327435 0.562068 0.098 Uiso 1 1 calc R U . . .
H9C H -0.081000 0.392904 0.496984 0.098 Uiso 1 1 calc R U . . .
C10 C 0.0104(5) 0.2230(3) 0.4425(2) 0.0691(12) Uani 1 1 d . . . . .
H10A H -0.089268 0.243769 0.420410 0.104 Uiso 1 1 calc R U . . .
H10B H -0.008724 0.183994 0.485137 0.104 Uiso 1 1 calc R U . . .
H10C H 0.067273 0.186599 0.406866 0.104 Uiso 1 1 calc R U . . .
C11 C 0.1376(5) 0.3747(3) 0.39866(19) 0.0603(11) Uani 1 1 d . . . . .
H11A H 0.204311 0.341951 0.364798 0.090 Uiso 1 1 calc R U . . .
H11B H 0.188448 0.432838 0.414914 0.090 Uiso 1 1 calc R U . . .
H11C H 0.037410 0.389414 0.374020 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4113(4) 0.1819(2) 0.46855(17) 0.0396(8) Uani 1 1 d . . . . .
C13 C 0.4328(6) 0.2088(3) 0.3872(2) 0.0764(14) Uani 1 1 d . . . . .
H13A H 0.499969 0.162589 0.364479 0.115 Uiso 1 1 calc R U . . .
H13B H 0.481089 0.270847 0.384679 0.115 Uiso 1 1 calc R U . . .
H13C H 0.331036 0.209983 0.361327 0.115 Uiso 1 1 calc R U . . .
C14 C 0.3270(5) 0.0849(2) 0.4730(2) 0.0579(10) Uani 1 1 d . . . . .
H14A H 0.225754 0.088386 0.446703 0.087 Uiso 1 1 calc R U . . .
H14B H 0.311321 0.069113 0.524122 0.087 Uiso 1 1 calc R U . . .
H14C H 0.391098 0.036654 0.450861 0.087 Uiso 1 1 calc R U . . .
C15 C 0.5755(4) 0.1723(3) 0.5076(2) 0.0627(11) Uani 1 1 d . . . . .
H15A H 0.632566 0.120733 0.485651 0.094 Uiso 1 1 calc R U . . .
H15B H 0.563019 0.159512 0.559494 0.094 Uiso 1 1 calc R U . . .
H15C H 0.633731 0.230720 0.502103 0.094 Uiso 1 1 calc R U . . .
C16 C 0.5338(4) 0.3998(2) 0.54593(18) 0.0475(9) Uani 1 1 d . . . . .
H16A H 0.612159 0.409767 0.509235 0.071 Uiso 1 1 calc R U . . .
H16B H 0.567500 0.348797 0.578543 0.071 Uiso 1 1 calc R U . . .
H16C H 0.521415 0.457228 0.574275 0.071 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
Cu1 Cl1 2.2342(10) . ?
Cu1 Cl2 2.2360(10) . ?
Cu1 Cl3 2.2412(9) . ?
Cu1 N1 2.026(3) . ?
P1 O1 1.593(2) . ?
P1 N2 1.621(2) . ?
P1 C8 1.843(3) . ?
P1 C12 1.830(3) . ?
O1 C16 1.385(4) . ?
N1 C1 1.343(4) . ?
N1 C5 1.347(4) . ?
N2 H2N 0.854(16) . ?
N2 C7 1.472(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 C6 1.493(4) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C6 C7 1.529(4) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 C9 1.536(5) . ?
C8 C10 1.533(5) . ?
C8 C11 1.543(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.528(5) . ?
C12 C14 1.535(5) . ?
C12 C15 1.533(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
Cl1 Cu1 Cl2 99.50(4) . . ?
Cl1 Cu1 Cl3 134.49(5) . . ?
Cl2 Cu1 Cl3 98.94(4) . . ?
N1 Cu1 Cl1 94.95(7) . . ?
N1 Cu1 Cl2 141.00(8) . . ?
N1 Cu1 Cl3 96.19(7) . . ?
O1 P1 N2 108.40(12) . . ?
O1 P1 C8 99.58(13) . . ?
O1 P1 C12 111.29(14) . . ?
N2 P1 C8 115.54(14) . . ?
N2 P1 C12 106.06(14) . . ?
C12 P1 C8 115.75(15) . . ?
C16 O1 P1 127.48(19) . . ?
C1 N1 Cu1 118.0(2) . . ?
C1 N1 C5 118.4(3) . . ?
C5 N1 Cu1 123.6(2) . . ?
P1 N2 H2N 114.2(17) . . ?
C7 N2 P1 126.5(2) . . ?
C7 N2 H2N 114.5(18) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.4(3) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 C6 118.6(3) . . ?
C4 C5 C6 120.7(3) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6AB 108.8 . . ?
C5 C6 C7 113.9(2) . . ?
H6A C6 H6AB 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6AB 108.8 . . ?
N2 C7 C6 113.1(3) . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7AB 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7AB 109.0 . . ?
H7A C7 H7AB 107.8 . . ?
C9 C8 P1 107.9(2) . . ?
C9 C8 C11 107.8(3) . . ?
C10 C8 P1 112.1(2) . . ?
C10 C8 C9 108.0(3) . . ?
C10 C8 C11 109.8(3) . . ?
C11 C8 P1 111.1(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 109.1(2) . . ?
C13 C12 C14 109.8(3) . . ?
C13 C12 C15 108.9(3) . . ?
C14 C12 P1 111.6(2) . . ?
C15 C12 P1 109.3(2) . . ?
C15 C12 C14 108.0(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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_JCK_NiCl2tBu1C1H_03252022
_audit_block_doi                 10.5517/ccdc.csd.cc2bs6x8
_database_code_depnum_ccdc_archive 'CCDC 2168230'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H25 Cl2 N2 Ni P'
_chemical_formula_sum            'C14 H25 Cl2 N2 Ni P'
_chemical_formula_weight         381.94
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   13.3712(10)
_cell_length_b                   12.0474(9)
_cell_length_c                   23.5918(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.837(4)
_cell_angle_gamma                90
_cell_volume                     3673.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5295
_cell_measurement_theta_min      2.3110
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.723
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.077
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            49071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         1.600
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6409
_reflns_number_total             8444
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         8444
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.8654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0869
_olex2_refinement_description    
;
1. Restrained distances
 N2B-H2BN
 0.9 with sigma of 0.02
 N2A-H2AN
 0.9 with sigma of 0.02
 P1B-H2BN
 2.13 with sigma of 0.04
 C6B-H2BN
 1.94 with sigma of 0.04
 P1A-H2AN
 2.12 with sigma of 0.04
 C6A-H2AN
 1.92 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C6B(H6BA,H6BB)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C2A(H2A), C2B(H2B), C3A(H3A), C3B(H3B), C4A(H4A), C4B(H4B)
2.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC), C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,
 H9BC), C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F), C12A(H12A,H12B,H12C),
 C12B(H12D,H12E,H12F), C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F), C14A(H14A,
 H14B,H14C), C14B(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Ni1A Ni 0.34132(2) 0.30001(2) 0.46868(2) 0.04241(8) Uani 1 1 d . . . . .
Ni1B Ni 0.38781(2) 0.71873(2) 0.76163(2) 0.04548(8) Uani 1 1 d . . . . .
Cl1A Cl 0.50678(4) 0.28182(6) 0.51758(3) 0.06434(17) Uani 1 1 d . . . . .
Cl1B Cl 0.22688(5) 0.76698(6) 0.71466(4) 0.0800(2) Uani 1 1 d . . . . .
Cl2A Cl 0.29654(4) 0.35700(5) 0.37560(2) 0.05665(15) Uani 1 1 d . . . . .
Cl2B Cl 0.43149(6) 0.66734(6) 0.85580(3) 0.07265(19) Uani 1 1 d . . . . .
P1A P 0.22560(4) 0.16122(4) 0.47541(2) 0.03761(12) Uani 1 1 d D . . . .
P1B P 0.51778(4) 0.83138(4) 0.74337(2) 0.03866(12) Uani 1 1 d D . . . .
N1A N 0.28486(13) 0.40606(15) 0.51815(7) 0.0450(4) Uani 1 1 d . . . . .
N1B N 0.41962(12) 0.59203(14) 0.71358(7) 0.0428(4) Uani 1 1 d . . . . .
N2A N 0.21217(14) 0.17562(16) 0.54335(7) 0.0474(4) Uani 1 1 d D . . . .
H2AN H 0.1611(14) 0.1517(18) 0.5532(9) 0.057 Uiso 1 1 d D U . . .
N2B N 0.52180(14) 0.79782(16) 0.67472(7) 0.0461(4) Uani 1 1 d D . . . .
H2BN H 0.5808(12) 0.7853(19) 0.6700(9) 0.055 Uiso 1 1 d D U . . .
C1A C 0.26945(19) 0.5123(2) 0.50186(11) 0.0611(6) Uani 1 1 d . . . . .
H1A H 0.287176 0.535615 0.468137 0.073 Uiso 1 1 calc R U . . .
C1B C 0.42233(17) 0.48910(19) 0.73515(10) 0.0516(5) Uani 1 1 d . . . . .
H1B H 0.402234 0.478162 0.769672 0.062 Uiso 1 1 calc R U . . .
C2A C 0.2281(2) 0.5889(2) 0.53333(14) 0.0773(8) Uani 1 1 d . . . . .
H2A H 0.218918 0.662548 0.521263 0.093 Uiso 1 1 calc R U . . .
C2B C 0.45355(19) 0.3988(2) 0.70846(11) 0.0590(6) Uani 1 1 d . . . . .
H2B H 0.454382 0.328239 0.724520 0.071 Uiso 1 1 calc R U . . .
C3A C 0.2009(2) 0.5539(3) 0.58262(14) 0.0777(8) Uani 1 1 d . . . . .
H3A H 0.172897 0.603624 0.604522 0.093 Uiso 1 1 calc R U . . .
C3B C 0.48362(17) 0.4151(2) 0.65739(11) 0.0571(6) Uani 1 1 d . . . . .
H3B H 0.507127 0.355876 0.639055 0.069 Uiso 1 1 calc R U . . .
C4A C 0.21545(18) 0.4450(2) 0.59926(11) 0.0628(7) Uani 1 1 d . . . . .
H4A H 0.196655 0.420303 0.632429 0.075 Uiso 1 1 calc R U . . .
C4B C 0.47844(16) 0.5195(2) 0.63405(9) 0.0510(5) Uani 1 1 d . . . . .
H4B H 0.496777 0.531196 0.599060 0.061 Uiso 1 1 calc R U . . .
C5A C 0.25789(15) 0.37198(19) 0.56695(9) 0.0453(5) Uani 1 1 d . . . . .
C5B C 0.44583(15) 0.60806(18) 0.66250(8) 0.0434(5) Uani 1 1 d . . . . .
C6A C 0.27754(17) 0.25236(19) 0.58436(8) 0.0474(5) Uani 1 1 d D . . . .
H6AA H 0.349489 0.235115 0.587102 0.057 Uiso 1 1 calc R U . . .
H6AB H 0.265798 0.241661 0.622896 0.057 Uiso 1 1 calc R U . . .
C6B C 0.44169(17) 0.72481(19) 0.63966(9) 0.0490(5) Uani 1 1 d D . . . .
H6BA H 0.448857 0.722898 0.599781 0.059 Uiso 1 1 calc R U . . .
H6BB H 0.374332 0.756049 0.638496 0.059 Uiso 1 1 calc R U . . .
C7A C 0.27982(16) 0.01978(18) 0.46961(9) 0.0466(5) Uani 1 1 d . . . . .
C7B C 0.48621(18) 0.98252(18) 0.74208(9) 0.0505(5) Uani 1 1 d . . . . .
C8A C 0.3684(2) 0.0053(2) 0.52449(10) 0.0655(7) Uani 1 1 d . . . . .
H8AA H 0.403078 -0.063723 0.522239 0.098 Uiso 1 1 calc R U . . .
H8AB H 0.341425 0.005014 0.558485 0.098 Uiso 1 1 calc R U . . .
H8AC H 0.416512 0.065457 0.527306 0.098 Uiso 1 1 calc R U . . .
C8B C 0.3920(2) 0.9997(2) 0.69154(13) 0.0839(9) Uani 1 1 d . . . . .
H8BA H 0.409926 0.986305 0.655241 0.126 Uiso 1 1 calc R U . . .
H8BB H 0.367839 1.074629 0.692140 0.126 Uiso 1 1 calc R U . . .
H8BC H 0.338494 0.949168 0.695117 0.126 Uiso 1 1 calc R U . . .
C9A C 0.32538(19) 0.0183(2) 0.41583(10) 0.0608(6) Uani 1 1 d . . . . .
H9AA H 0.270886 0.029181 0.380836 0.091 Uiso 1 1 calc R U . . .
H9AB H 0.358233 -0.051884 0.413806 0.091 Uiso 1 1 calc R U . . .
H9AC H 0.375393 0.076792 0.419375 0.091 Uiso 1 1 calc R U . . .
C9B C 0.5726(3) 1.0585(2) 0.73461(17) 0.0966(11) Uani 1 1 d . . . . .
H9BA H 0.593170 1.037688 0.699967 0.145 Uiso 1 1 calc R U . . .
H9BB H 0.630699 1.051947 0.768182 0.145 Uiso 1 1 calc R U . . .
H9BC H 0.548576 1.133904 0.730973 0.145 Uiso 1 1 calc R U . . .
C10A C 0.2035(2) -0.0762(2) 0.46558(13) 0.0747(8) Uani 1 1 d . . . . .
H10A H 0.148489 -0.068590 0.430555 0.112 Uiso 1 1 calc R U . . .
H10B H 0.175450 -0.075035 0.499172 0.112 Uiso 1 1 calc R U . . .
H10C H 0.238776 -0.145301 0.464495 0.112 Uiso 1 1 calc R U . . .
C10B C 0.4571(3) 1.0107(3) 0.79899(12) 0.0971(11) Uani 1 1 d . . . . .
H10D H 0.439489 1.087938 0.799021 0.146 Uiso 1 1 calc R U . . .
H10E H 0.514651 0.995238 0.831814 0.146 Uiso 1 1 calc R U . . .
H10F H 0.398798 0.966560 0.801874 0.146 Uiso 1 1 calc R U . . .
C11A C 0.09189(16) 0.1792(2) 0.42735(9) 0.0503(5) Uani 1 1 d . . . . .
C11B C 0.65153(17) 0.7996(2) 0.78828(9) 0.0503(5) Uani 1 1 d . . . . .
C12A C 0.01050(18) 0.1124(3) 0.44863(12) 0.0716(7) Uani 1 1 d . . . . .
H12A H -0.056840 0.126488 0.423270 0.107 Uiso 1 1 calc R U . . .
H12B H 0.011638 0.134341 0.487907 0.107 Uiso 1 1 calc R U . . .
H12C H 0.025863 0.034625 0.447997 0.107 Uiso 1 1 calc R U . . .
C12B C 0.6667(2) 0.8408(2) 0.85145(10) 0.0699(7) Uani 1 1 d . . . . .
H12D H 0.666201 0.920497 0.851820 0.105 Uiso 1 1 calc R U . . .
H12E H 0.731728 0.814402 0.875168 0.105 Uiso 1 1 calc R U . . .
H12F H 0.611599 0.813371 0.866875 0.105 Uiso 1 1 calc R U . . .
C13A C 0.08675(19) 0.1498(2) 0.36383(10) 0.0656(7) Uani 1 1 d . . . . .
H13A H 0.019578 0.168267 0.339517 0.098 Uiso 1 1 calc R U . . .
H13B H 0.098852 0.071689 0.360867 0.098 Uiso 1 1 calc R U . . .
H13C H 0.138579 0.190818 0.351107 0.098 Uiso 1 1 calc R U . . .
C13B C 0.73735(19) 0.8473(3) 0.76246(13) 0.0742(8) Uani 1 1 d . . . . .
H13D H 0.725706 0.824438 0.722318 0.111 Uiso 1 1 calc R U . . .
H13E H 0.803406 0.820420 0.784577 0.111 Uiso 1 1 calc R U . . .
H13F H 0.736366 0.926913 0.764400 0.111 Uiso 1 1 calc R U . . .
C14A C 0.06535(18) 0.3027(2) 0.43062(12) 0.0652(7) Uani 1 1 d . . . . .
H14A H 0.113974 0.346792 0.416715 0.098 Uiso 1 1 calc R U . . .
H14B H 0.068739 0.322264 0.470519 0.098 Uiso 1 1 calc R U . . .
H14C H -0.003239 0.316266 0.406677 0.098 Uiso 1 1 calc R U . . .
C14B C 0.66145(19) 0.6727(2) 0.78916(11) 0.0606(6) Uani 1 1 d . . . . .
H14D H 0.651733 0.645776 0.749821 0.091 Uiso 1 1 calc R U . . .
H14E H 0.609857 0.640962 0.806059 0.091 Uiso 1 1 calc R U . . .
H14F H 0.728981 0.651872 0.812167 0.091 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
Ni1A Cl1A 2.2285(7) . ?
Ni1A Cl2A 2.2312(6) . ?
Ni1A P1A 2.3111(6) . ?
Ni1A N1A 2.0039(17) . ?
Ni1B Cl1B 2.2306(7) . ?
Ni1B Cl2B 2.2350(7) . ?
Ni1B P1B 2.3305(6) . ?
Ni1B N1B 2.0107(16) . ?
P1A N2A 1.6669(17) . ?
P1A C7A 1.870(2) . ?
P1A C11A 1.868(2) . ?
P1B N2B 1.6835(17) . ?
P1B C7B 1.868(2) . ?
P1B C11B 1.870(2) . ?
N1A C1A 1.337(3) . ?
N1A C5A 1.355(2) . ?
N1B C1B 1.337(3) . ?
N1B C5B 1.352(2) . ?
N2A H2AN 0.827(14) . ?
N2A C6A 1.457(3) . ?
N2B H2BN 0.838(14) . ?
N2B C6B 1.467(3) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.386(4) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.374(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.370(4) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.378(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.369(4) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.368(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.378(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.389(3) . ?
C5A C6A 1.503(3) . ?
C5B C6B 1.502(3) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7A C8A 1.525(3) . ?
C7A C9A 1.542(3) . ?
C7A C10A 1.529(3) . ?
C7B C8B 1.510(3) . ?
C7B C9B 1.519(4) . ?
C7B C10B 1.529(3) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11A C12A 1.537(3) . ?
C11A C13A 1.524(3) . ?
C11A C14A 1.537(3) . ?
C11B C12B 1.534(3) . ?
C11B C13B 1.542(3) . ?
C11B C14B 1.534(3) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?

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
Cl1A Ni1A Cl2A 121.36(2) . . ?
Cl1A Ni1A P1A 119.12(3) . . ?
Cl2A Ni1A P1A 105.94(2) . . ?
N1A Ni1A Cl1A 103.50(5) . . ?
N1A Ni1A Cl2A 109.32(5) . . ?
N1A Ni1A P1A 93.59(5) . . ?
Cl1B Ni1B Cl2B 122.64(3) . . ?
Cl1B Ni1B P1B 115.25(3) . . ?
Cl2B Ni1B P1B 109.12(3) . . ?
N1B Ni1B Cl1B 103.54(5) . . ?
N1B Ni1B Cl2B 108.12(5) . . ?
N1B Ni1B P1B 93.58(5) . . ?
N2A P1A Ni1A 103.28(7) . . ?
N2A P1A C7A 107.72(10) . . ?
N2A P1A C11A 104.45(9) . . ?
C7A P1A Ni1A 112.04(7) . . ?
C11A P1A Ni1A 115.35(7) . . ?
C11A P1A C7A 112.93(10) . . ?
N2B P1B Ni1B 104.30(7) . . ?
N2B P1B C7B 106.33(10) . . ?
N2B P1B C11B 103.55(10) . . ?
C7B P1B Ni1B 113.25(7) . . ?
C7B P1B C11B 112.86(11) . . ?
C11B P1B Ni1B 115.22(7) . . ?
C1A N1A Ni1A 119.75(15) . . ?
C1A N1A C5A 118.64(19) . . ?
C5A N1A Ni1A 121.56(15) . . ?
C1B N1B Ni1B 118.58(13) . . ?
C1B N1B C5B 118.93(18) . . ?
C5B N1B Ni1B 122.31(14) . . ?
P1A N2A H2AN 122.2(14) . . ?
C6A N2A P1A 120.71(13) . . ?
C6A N2A H2AN 115.6(15) . . ?
P1B N2B H2BN 115.8(15) . . ?
C6B N2B P1B 119.21(13) . . ?
C6B N2B H2BN 113.1(15) . . ?
N1A C1A H1A 118.8 . . ?
N1A C1A C2A 122.5(2) . . ?
C2A C1A H1A 118.8 . . ?
N1B C1B H1B 118.6 . . ?
N1B C1B C2B 122.8(2) . . ?
C2B C1B H1B 118.6 . . ?
C1A C2A H2A 120.7 . . ?
C3A C2A C1A 118.6(3) . . ?
C3A C2A H2A 120.7 . . ?
C1B C2B H2B 120.7 . . ?
C1B C2B C3B 118.6(2) . . ?
C3B C2B H2B 120.7 . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A C2A 119.3(2) . . ?
C4A C3A H3A 120.4 . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B C2B 119.1(2) . . ?
C4B C3B H3B 120.4 . . ?
C3A C4A H4A 119.9 . . ?
C3A C4A C5A 120.1(2) . . ?
C5A C4A H4A 119.9 . . ?
C3B C4B H4B 120.0 . . ?
C3B C4B C5B 120.1(2) . . ?
C5B C4B H4B 120.0 . . ?
N1A C5A C4A 120.9(2) . . ?
N1A C5A C6A 117.18(17) . . ?
C4A C5A C6A 121.9(2) . . ?
N1B C5B C4B 120.4(2) . . ?
N1B C5B C6B 117.35(18) . . ?
C4B C5B C6B 122.22(18) . . ?
N2A C6A C5A 113.19(18) . . ?
N2A C6A H6AA 108.9 . . ?
N2A C6A H6AB 108.9 . . ?
C5A C6A H6AA 108.9 . . ?
C5A C6A H6AB 108.9 . . ?
H6AA C6A H6AB 107.8 . . ?
N2B C6B C5B 113.87(18) . . ?
N2B C6B H6BA 108.8 . . ?
N2B C6B H6BB 108.8 . . ?
C5B C6B H6BA 108.8 . . ?
C5B C6B H6BB 108.8 . . ?
H6BA C6B H6BB 107.7 . . ?
C8A C7A P1A 105.87(15) . . ?
C8A C7A C9A 108.22(18) . . ?
C8A C7A C10A 109.1(2) . . ?
C9A C7A P1A 108.23(15) . . ?
C10A C7A P1A 115.39(16) . . ?
C10A C7A C9A 109.77(19) . . ?
C8B C7B P1B 106.61(17) . . ?
C8B C7B C9B 109.3(2) . . ?
C8B C7B C10B 108.3(2) . . ?
C9B C7B P1B 114.45(18) . . ?
C9B C7B C10B 109.9(2) . . ?
C10B C7B P1B 108.02(17) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C7A C9A H9AA 109.5 . . ?
C7A C9A H9AB 109.5 . . ?
C7A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7B C9B H9BA 109.5 . . ?
C7B C9B H9BB 109.5 . . ?
C7B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C7B C10B H10D 109.5 . . ?
C7B C10B H10E 109.5 . . ?
C7B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C12A C11A P1A 112.88(16) . . ?
C12A C11A C14A 107.4(2) . . ?
C13A C11A P1A 111.41(15) . . ?
C13A C11A C12A 110.0(2) . . ?
C13A C11A C14A 108.8(2) . . ?
C14A C11A P1A 106.20(16) . . ?
C12B C11B P1B 110.67(16) . . ?
C12B C11B C13B 109.6(2) . . ?
C12B C11B C14B 108.7(2) . . ?
C13B C11B P1B 113.59(17) . . ?
C14B C11B P1B 106.19(15) . . ?
C14B C11B C13B 107.9(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C11B C14B H14D 109.5 . . ?
C11B C14B H14E 109.5 . . ?
C11B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

_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_JCK_CutBu1C_orange_06072021
_audit_block_doi                 10.5517/ccdc.csd.cc2bs71f
_database_code_depnum_ccdc_archive 'CCDC 2168234'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 Cl3 Cu N2 O P, [+ 2(H2O)]'
_chemical_formula_sum            'C14 H26 Cl3 Cu N2 O P'
_chemical_formula_weight         439.23
_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'
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      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                   14.14310(10)
_cell_length_b                   8.98120(10)
_cell_length_c                   17.4366(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.1680(10)
_cell_angle_gamma                90
_cell_volume                     2172.89(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3107
_cell_measurement_theta_min      2.5438
_shelx_estimated_absorpt_T_max   0.704
_shelx_estimated_absorpt_T_min   0.531
_exptl_absorpt_coefficient_mu    1.449
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.871
_diffrn_reflns_theta_min         1.468
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5818
_reflns_number_total             7671
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         7671
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.046
_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)+(0.0673P)²+1.6017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1462
_olex2_refinement_description    
;
1. Restrained distances
 Cu1-Cl1 \\sim Cu1-Cl2 \\sim Cu1-Cl3 \\sim Cu1-Cl1' \\sim Cu1-Cl2' \\sim
Cu1-Cl3'
 with sigma of 0.02
2. Others
 Sof(Cl1')=Sof(Cl2')=Sof(Cl3')=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6AB)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.80491(2) 0.11858(3) 0.75026(2) 0.04415(10) Uani 1 1 d D . . . .
P1 P 0.72346(4) 0.45558(6) 0.67421(3) 0.04057(13) Uani 1 1 d . . . . .
O1 O 0.77342(14) 0.33119(19) 0.72327(12) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.87324(19) 0.5213(2) 0.87202(15) 0.0556(5) Uani 1 1 d . . . . .
N2 N 0.77962(18) 0.6114(2) 0.70355(14) 0.0534(5) Uani 1 1 d . . . . .
C1 C 0.8766(3) 0.5284(3) 0.9495(2) 0.0665(8) Uani 1 1 d . . . . .
H1 H 0.863968 0.444088 0.976829 0.080 Uiso 1 1 calc R U . . .
C2 C 0.8985(3) 0.6598(4) 0.98756(18) 0.0675(8) Uani 1 1 d . . . . .
H2 H 0.900195 0.666719 1.041030 0.081 Uiso 1 1 calc R U . . .
C3 C 0.9180(2) 0.7822(3) 0.94594(18) 0.0635(7) Uani 1 1 d . . . . .
H3 H 0.934860 0.872054 0.971427 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9126(2) 0.7714(3) 0.86633(15) 0.0502(5) Uani 1 1 d . . . . .
H4 H 0.924211 0.854710 0.837849 0.060 Uiso 1 1 calc R U . . .
C5 C 0.88998(17) 0.6381(2) 0.82923(15) 0.0442(5) Uani 1 1 d . . . . .
C6 C 0.8804(2) 0.6162(3) 0.74268(16) 0.0582(7) Uani 1 1 d . . . . .
H6A H 0.912605 0.697030 0.721244 0.070 Uiso 1 1 calc R U . . .
H6AB H 0.911685 0.523830 0.732999 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7352(2) 0.4261(4) 0.57214(16) 0.0587(6) Uani 1 1 d . . . . .
C8 C 0.6888(3) 0.2776(6) 0.5393(2) 0.0988(15) Uani 1 1 d . . . . .
H8A H 0.619881 0.285711 0.531597 0.148 Uiso 1 1 calc R U . . .
H8B H 0.710381 0.198802 0.575701 0.148 Uiso 1 1 calc R U . . .
H8C H 0.707194 0.256153 0.490323 0.148 Uiso 1 1 calc R U . . .
C9 C 0.8439(2) 0.4127(4) 0.57447(19) 0.0688(8) Uani 1 1 d . . . . .
H9A H 0.854655 0.384791 0.523714 0.103 Uiso 1 1 calc R U . . .
H9B H 0.870612 0.338208 0.611931 0.103 Uiso 1 1 calc R U . . .
H9C H 0.874339 0.506697 0.589217 0.103 Uiso 1 1 calc R U . . .
C10 C 0.6952(3) 0.5552(6) 0.5192(2) 0.0973(14) Uani 1 1 d . . . . .
H10A H 0.713892 0.544007 0.469458 0.146 Uiso 1 1 calc R U . . .
H10B H 0.720392 0.647251 0.542787 0.146 Uiso 1 1 calc R U . . .
H10C H 0.626205 0.555952 0.512042 0.146 Uiso 1 1 calc R U . . .
C11 C 0.5998(2) 0.4792(3) 0.69161(18) 0.0569(6) Uani 1 1 d . . . . .
C12 C 0.5389(3) 0.3426(5) 0.6625(3) 0.0874(12) Uani 1 1 d . . . . .
H12A H 0.531760 0.335238 0.606763 0.131 Uiso 1 1 calc R U . . .
H12B H 0.476465 0.352200 0.675992 0.131 Uiso 1 1 calc R U . . .
H12C H 0.570039 0.254718 0.686501 0.131 Uiso 1 1 calc R U . . .
C13 C 0.5494(3) 0.6188(4) 0.6534(3) 0.0810(10) Uani 1 1 d . . . . .
H13A H 0.545111 0.613714 0.597859 0.122 Uiso 1 1 calc R U . . .
H13B H 0.585672 0.705380 0.673601 0.122 Uiso 1 1 calc R U . . .
H13C H 0.485789 0.624913 0.664838 0.122 Uiso 1 1 calc R U . . .
C14 C 0.6095(3) 0.4928(6) 0.7805(2) 0.0911(12) Uani 1 1 d . . . . .
H14A H 0.647177 0.579281 0.798630 0.137 Uiso 1 1 calc R U . . .
H14B H 0.640822 0.405636 0.805256 0.137 Uiso 1 1 calc R U . . .
H14C H 0.546686 0.502027 0.793102 0.137 Uiso 1 1 calc R U . . .
H1B H 0.749(2) 0.696(4) 0.6966(19) 0.062(9) Uiso 1 1 d . . . . .
H5 H 0.869(3) 0.440(5) 0.850(2) 0.074(11) Uiso 1 1 d . . . . .
Cl1 Cl 0.8936(3) -0.0003(5) 0.6766(3) 0.0689(8) Uani 0.607(13) 1 d D . P A 1
Cl2 Cl 0.91092(18) 0.1724(3) 0.8628(2) 0.0576(6) Uani 0.607(13) 1 d D . P A 1
Cl3 Cl 0.6938(3) -0.0465(4) 0.7640(5) 0.0968(15) Uani 0.607(13) 1 d D . P A 1
Cl1' Cl 0.8628(7) 0.0207(6) 0.6556(4) 0.0806(13) Uani 0.393(13) 1 d D . P A 2
Cl2' Cl 0.8755(11) 0.1754(6) 0.8727(3) 0.096(3) Uani 0.393(13) 1 d D . P A 2
Cl3' Cl 0.6763(3) -0.0125(7) 0.7298(4) 0.0813(11) Uani 0.393(13) 1 d D . 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
Cu1 O1 1.9962(17) . ?
Cu1 Cl1 2.233(3) . ?
Cu1 Cl2 2.279(3) . ?
Cu1 Cl3 2.207(2) . ?
Cu1 Cl1' 2.166(4) . ?
Cu1 Cl2' 2.234(5) . ?
Cu1 Cl3' 2.138(4) . ?
P1 O1 1.4983(18) . ?
P1 N2 1.641(2) . ?
P1 C7 1.838(3) . ?
P1 C11 1.844(3) . ?
N1 C1 1.344(4) . ?
N1 C5 1.335(3) . ?
N1 H5 0.82(4) . ?
N2 C6 1.457(4) . ?
N2 H1B 0.87(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.360(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 C6 1.502(4) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 C8 1.547(5) . ?
C7 C9 1.534(4) . ?
C7 C10 1.521(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.528(5) . ?
C11 C13 1.530(4) . ?
C11 C14 1.533(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Cu1 Cl1 116.52(15) . . ?
O1 Cu1 Cl2 94.56(9) . . ?
O1 Cu1 Cl3 122.49(16) . . ?
O1 Cu1 Cl1' 107.98(17) . . ?
O1 Cu1 Cl2' 92.57(17) . . ?
O1 Cu1 Cl3' 110.1(2) . . ?
Cl1 Cu1 Cl2 104.33(18) . . ?
Cl3 Cu1 Cl1 103.41(11) . . ?
Cl3 Cu1 Cl2 114.4(2) . . ?
Cl1' Cu1 Cl2' 131.0(7) . . ?
Cl3' Cu1 Cl1' 94.8(3) . . ?
Cl3' Cu1 Cl2' 119.6(3) . . ?
O1 P1 N2 108.15(12) . . ?
O1 P1 C7 108.93(13) . . ?
O1 P1 C11 110.44(13) . . ?
N2 P1 C7 107.18(14) . . ?
N2 P1 C11 105.53(13) . . ?
C7 P1 C11 116.25(14) . . ?
P1 O1 Cu1 155.07(13) . . ?
C1 N1 H5 120(3) . . ?
C5 N1 C1 123.3(2) . . ?
C5 N1 H5 116(3) . . ?
P1 N2 H1B 120(2) . . ?
C6 N2 P1 122.79(19) . . ?
C6 N2 H1B 117(2) . . ?
N1 C1 H1 120.3 . . ?
N1 C1 C2 119.5(3) . . ?
C2 C1 H1 120.3 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 118.3(2) . . ?
N1 C5 C6 117.9(2) . . ?
C4 C5 C6 123.8(2) . . ?
N2 C6 C5 111.4(2) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6AB 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6AB 109.4 . . ?
H6A C6 H6AB 108.0 . . ?
C8 C7 P1 111.8(3) . . ?
C9 C7 P1 105.29(19) . . ?
C9 C7 C8 107.1(3) . . ?
C10 C7 P1 112.6(3) . . ?
C10 C7 C8 110.6(3) . . ?
C10 C7 C9 109.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 P1 110.2(2) . . ?
C12 C11 C13 109.1(3) . . ?
C12 C11 C14 109.5(3) . . ?
C13 C11 P1 113.6(2) . . ?
C13 C11 C14 108.5(3) . . ?
C14 C11 P1 105.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_JCK_BHT_tBu1C_04042022
_audit_block_doi                 10.5517/ccdc.csd.cc2bs70d
_database_code_depnum_ccdc_archive 'CCDC 2168233'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C23 H41 N O P'
_chemical_formula_sum            'C23 H41 Cl N O P'
_chemical_formula_weight         413.99
_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'
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      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                   11.8979(4)
_cell_length_b                   16.6511(5)
_cell_length_c                   12.3939(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.159(2)
_cell_angle_gamma                90
_cell_volume                     2448.93(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.89
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.9570.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.426
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.115
_diffrn_reflns_theta_min         2.052
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_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_current           45.0
_diffrn_source_power             2.25
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7515
_reflns_number_total             8770
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         8770
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.042
_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)+(0.0547P)²+0.6774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1066
_olex2_refinement_description    
;
1. Restrained distances
 N1-H1A
 0.89 with sigma of 0.02
 N1-H1B
 0.89 with sigma of 0.02
 H1A-H1B
 1.53 with sigma of 0.04
 P1-H1A \\sim P1-H1B
 with sigma of 0.02
 C10-C7 \\sim C10-C10A
 with sigma of 0.02
 C9-C7 \\sim C9-C9A
 with sigma of 0.02
 C8-C7 \\sim C8-C8A
 with sigma of 0.02
 C10A-C7 \\sim C10A-C10
 with sigma of 0.02
 C8A-C7 \\sim C8A-C8
 with sigma of 0.02
 C9A-C7 \\sim C9A-C9
 with sigma of 0.02
2. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
 Sof(O1A)=1-FVAR(2)
 Sof(O1)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C15(H15)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C8A(H8AA,H8AB,H8AC),
 C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,H10F), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.49712(3) 0.36617(2) 0.09830(2) 0.03156(7) Uani 1 1 d . . . . .
P1 P 0.58853(2) 0.60200(2) 0.24286(2) 0.01704(6) Uani 1 1 d D . . . .
O1 O 0.0358(3) 0.6181(3) 0.3472(10) 0.0422(13) Uani 0.54(3) 1 d . . P A 1
O1A O 0.0524(14) 0.6062(8) 0.3898(19) 0.062(4) Uani 0.46(3) 1 d . . P A 2
N1 N 0.53538(7) 0.55541(5) 0.13722(6) 0.02166(15) Uani 1 1 d D . . . .
H1A H 0.5279(12) 0.5033(7) 0.1365(11) 0.032 Uiso 1 1 d D U . . .
H1B H 0.5236(12) 0.5816(8) 0.0768(9) 0.032 Uiso 1 1 d D U . . .
C1 C 0.14266(9) 0.62063(6) 0.35530(10) 0.0319(2) Uani 1 1 d . . . . .
C2 C 0.20740(8) 0.68660(5) 0.41193(7) 0.02249(17) Uani 1 1 d . . . . .
C3 C 0.31758(8) 0.69381(6) 0.39634(8) 0.02410(17) Uani 1 1 d . . . . .
H3 H 0.358712 0.736314 0.431817 0.029 Uiso 1 1 calc R U . . .
C4 C 0.37703(8) 0.63973(5) 0.32780(7) 0.02041(16) Uani 1 1 d . . . . .
C5 C 0.31302(7) 0.57517(5) 0.27358(7) 0.01984(15) Uani 1 1 d . . . . .
H5 H 0.350582 0.539467 0.228434 0.024 Uiso 1 1 calc R U . . .
C6 C 0.20219(8) 0.56415(5) 0.28507(7) 0.02056(16) Uani 1 1 d . . . . .
C7 C 0.14702(9) 0.74667(6) 0.48119(8) 0.02721(19) Uani 1 1 d . . . . .
C8 C 0.0693(4) 0.7008(2) 0.5587(4) 0.0456(9) Uani 0.634(13) 1 d . . P B 1
H8A H 0.011387 0.670686 0.515332 0.068 Uiso 0.634(13) 1 calc R U P B 1
H8B H 0.033074 0.739624 0.604383 0.068 Uiso 0.634(13) 1 calc R U P B 1
H8C H 0.115123 0.663463 0.604490 0.068 Uiso 0.634(13) 1 calc R U P B 1
C9 C 0.0672(6) 0.7986(4) 0.4077(5) 0.0327(7) Uani 0.634(13) 1 d . . P B 1
H9A H 0.111186 0.830933 0.359952 0.049 Uiso 0.634(13) 1 calc R U P B 1
H9B H 0.023972 0.834110 0.452276 0.049 Uiso 0.634(13) 1 calc R U P B 1
H9C H 0.015326 0.763806 0.364022 0.049 Uiso 0.634(13) 1 calc R U P B 1
C10 C 0.2264(4) 0.7965(4) 0.5472(4) 0.0462(11) Uani 0.634(13) 1 d . . P B 1
H10A H 0.271817 0.828269 0.499976 0.069 Uiso 0.634(13) 1 calc R U P B 1
H10B H 0.275988 0.762020 0.593727 0.069 Uiso 0.634(13) 1 calc R U P B 1
H10C H 0.184649 0.832637 0.592259 0.069 Uiso 0.634(13) 1 calc R U P B 1
C8A C 0.1188(11) 0.7131(4) 0.5876(6) 0.052(2) Uani 0.366(13) 1 d . . P B 2
H8AA H 0.072240 0.664947 0.575594 0.078 Uiso 0.366(13) 1 calc R U P B 2
H8AB H 0.077224 0.753302 0.626529 0.078 Uiso 0.366(13) 1 calc R U P B 2
H8AC H 0.188469 0.699046 0.630482 0.078 Uiso 0.366(13) 1 calc R U P B 2
C9A C 0.0530(13) 0.7842(9) 0.4128(13) 0.062(3) Uani 0.366(13) 1 d . . P B 2
H9AA H 0.080506 0.801260 0.343816 0.093 Uiso 0.366(13) 1 calc R U P B 2
H9AB H 0.024508 0.830892 0.450430 0.093 Uiso 0.366(13) 1 calc R U P B 2
H9AC H -0.007866 0.744984 0.399283 0.093 Uiso 0.366(13) 1 calc R U P B 2
C10A C 0.2343(7) 0.8211(5) 0.5151(10) 0.052(2) Uani 0.366(13) 1 d . . P B 2
H10D H 0.258944 0.846464 0.449509 0.077 Uiso 0.366(13) 1 calc R U P B 2
H10E H 0.300003 0.800023 0.558360 0.077 Uiso 0.366(13) 1 calc R U P B 2
H10F H 0.195765 0.860815 0.557546 0.077 Uiso 0.366(13) 1 calc R U P B 2
C11 C 0.13518(8) 0.49611(6) 0.22828(8) 0.02286(17) Uani 1 1 d . . . . .
C12 C 0.09051(11) 0.43903(7) 0.31211(9) 0.0360(2) Uani 1 1 d . . . . .
H12A H 0.047235 0.395814 0.274966 0.054 Uiso 1 1 calc R U . . .
H12B H 0.041748 0.468779 0.358463 0.054 Uiso 1 1 calc R U . . .
H12C H 0.153961 0.415963 0.356546 0.054 Uiso 1 1 calc R U . . .
C13 C 0.20773(11) 0.44808(9) 0.15539(11) 0.0435(3) Uani 1 1 d . . . . .
H13A H 0.162382 0.405285 0.119639 0.065 Uiso 1 1 calc R U . . .
H13B H 0.271287 0.424335 0.198951 0.065 Uiso 1 1 calc R U . . .
H13C H 0.236244 0.483662 0.100625 0.065 Uiso 1 1 calc R U . . .
C14 C 0.03497(11) 0.52933(9) 0.15611(14) 0.0494(4) Uani 1 1 d . . . . .
H14A H 0.063218 0.560356 0.096570 0.074 Uiso 1 1 calc R U . . .
H14B H -0.010817 0.564138 0.199222 0.074 Uiso 1 1 calc R U . . .
H14C H -0.011231 0.484636 0.126639 0.074 Uiso 1 1 calc R U . . .
C15 C 0.48874(8) 0.65377(6) 0.31924(7) 0.02183(16) Uani 1 1 d . . . . .
H15 H 0.518554 0.698053 0.360305 0.026 Uiso 1 1 calc R U . . .
C16 C 0.65433(9) 0.52584(6) 0.33534(8) 0.02858(19) Uani 1 1 d . . . . .
C17 C 0.56249(11) 0.46407(6) 0.35718(8) 0.0326(2) Uani 1 1 d . . . . .
H17A H 0.536594 0.437539 0.289294 0.049 Uiso 1 1 calc R U . . .
H17B H 0.498914 0.491471 0.387274 0.049 Uiso 1 1 calc R U . . .
H17C H 0.593479 0.423867 0.408879 0.049 Uiso 1 1 calc R U . . .
C18 C 0.69514(14) 0.56292(9) 0.44470(10) 0.0507(4) Uani 1 1 d . . . . .
H18A H 0.759919 0.597900 0.435151 0.076 Uiso 1 1 calc R U . . .
H18B H 0.717428 0.520039 0.496031 0.076 Uiso 1 1 calc R U . . .
H18C H 0.634125 0.594488 0.472713 0.076 Uiso 1 1 calc R U . . .
C19 C 0.75035(14) 0.48376(11) 0.28243(15) 0.0627(5) Uani 1 1 d . . . . .
H19A H 0.723163 0.464393 0.210551 0.094 Uiso 1 1 calc R U . . .
H19B H 0.777078 0.438206 0.327310 0.094 Uiso 1 1 calc R U . . .
H19C H 0.812377 0.521703 0.275483 0.094 Uiso 1 1 calc R U . . .
C20 C 0.67942(8) 0.68379(6) 0.19732(8) 0.02336(17) Uani 1 1 d . . . . .
C21 C 0.75533(11) 0.71956(8) 0.29049(10) 0.0381(3) Uani 1 1 d . . . . .
H21A H 0.810424 0.679227 0.317439 0.057 Uiso 1 1 calc R U . . .
H21B H 0.709118 0.735753 0.349080 0.057 Uiso 1 1 calc R U . . .
H21C H 0.794959 0.766540 0.264465 0.057 Uiso 1 1 calc R U . . .
C22 C 0.60006(10) 0.74980(6) 0.14888(9) 0.0298(2) Uani 1 1 d . . . . .
H22A H 0.644518 0.791377 0.115634 0.045 Uiso 1 1 calc R U . . .
H22B H 0.558618 0.773756 0.206338 0.045 Uiso 1 1 calc R U . . .
H22C H 0.546621 0.726217 0.093871 0.045 Uiso 1 1 calc R U . . .
C23 C 0.75156(10) 0.65229(8) 0.10840(10) 0.0340(2) Uani 1 1 d . . . . .
H23A H 0.702212 0.633433 0.046843 0.051 Uiso 1 1 calc R U . . .
H23B H 0.798640 0.607751 0.136973 0.051 Uiso 1 1 calc R U . . .
H23C H 0.799804 0.695604 0.084704 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.6111(8) . ?
P1 C15 1.7922(9) . ?
P1 C16 1.8452(10) . ?
P1 C20 1.8523(9) . ?
O1 C1 1.269(4) . ?
O1A C1 1.209(5) . ?
N1 H1A 0.872(11) . ?
N1 H1B 0.869(11) . ?
C1 C2 1.4880(14) . ?
C1 C6 1.4944(14) . ?
C2 C3 1.3442(13) . ?
C2 C7 1.5307(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.4560(12) . ?
C4 C5 1.4536(12) . ?
C4 C15 1.3611(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.3492(12) . ?
C6 C11 1.5275(13) . ?
C7 C8 1.578(4) . ?
C7 C9 1.534(6) . ?
C7 C10 1.462(4) . ?
C7 C8A 1.493(5) . ?
C7 C9A 1.491(14) . ?
C7 C10A 1.651(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11 C12 1.5315(14) . ?
C11 C13 1.5211(15) . ?
C11 C14 1.5404(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C16 C17 1.5389(16) . ?
C16 C18 1.5359(16) . ?
C16 C19 1.5279(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5337(14) . ?
C20 C22 1.5421(14) . ?
C20 C23 1.5374(15) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C15 115.14(4) . . ?
N1 P1 C16 107.32(5) . . ?
N1 P1 C20 108.05(4) . . ?
C15 P1 C16 105.66(5) . . ?
C15 P1 C20 103.36(4) . . ?
C16 P1 C20 117.63(5) . . ?
P1 N1 H1A 121.4(9) . . ?
P1 N1 H1B 119.2(9) . . ?
H1A N1 H1B 118.7(13) . . ?
O1 C1 C2 122.9(3) . . ?
O1 C1 C6 116.6(4) . . ?
O1A C1 C2 115.0(5) . . ?
O1A C1 C6 123.5(3) . . ?
C2 C1 C6 119.23(9) . . ?
C1 C2 C7 119.93(9) . . ?
C3 C2 C1 118.35(8) . . ?
C3 C2 C7 121.64(9) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.28(8) . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 117.82(8) . . ?
C15 C4 C3 117.24(8) . . ?
C15 C4 C5 124.94(8) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.35(8) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C11 118.79(8) . . ?
C5 C6 C1 118.95(8) . . ?
C5 C6 C11 122.26(8) . . ?
C2 C7 C8 110.14(16) . . ?
C2 C7 C9 109.3(3) . . ?
C2 C7 C10A 108.7(3) . . ?
C9 C7 C8 105.6(3) . . ?
C10 C7 C2 111.98(17) . . ?
C10 C7 C8 108.5(2) . . ?
C10 C7 C9 111.1(3) . . ?
C8A C7 C2 113.3(2) . . ?
C8A C7 C10A 103.5(4) . . ?
C9A C7 C2 108.6(6) . . ?
C9A C7 C8A 116.8(7) . . ?
C9A C7 C10A 105.2(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C8A H8AA 109.5 . . ?
C7 C8A H8AB 109.5 . . ?
C7 C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7 C9A H9AA 109.5 . . ?
C7 C9A H9AB 109.5 . . ?
C7 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7 C10A H10D 109.5 . . ?
C7 C10A H10E 109.5 . . ?
C7 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C6 C11 C12 110.06(8) . . ?
C6 C11 C14 110.93(9) . . ?
C12 C11 C14 108.95(9) . . ?
C13 C11 C6 111.35(8) . . ?
C13 C11 C12 108.45(10) . . ?
C13 C11 C14 107.01(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C15 H15 114.9 . . ?
C4 C15 P1 130.29(7) . . ?
C4 C15 H15 114.9 . . ?
C17 C16 P1 107.09(7) . . ?
C18 C16 P1 111.39(8) . . ?
C18 C16 C17 107.25(9) . . ?
C19 C16 P1 110.20(8) . . ?
C19 C16 C17 109.36(11) . . ?
C19 C16 C18 111.39(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 P1 112.40(7) . . ?
C21 C20 C22 109.08(9) . . ?
C21 C20 C23 110.08(9) . . ?
C22 C20 P1 106.75(7) . . ?
C23 C20 P1 109.64(7) . . ?
C23 C20 C22 108.78(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_original_sample_id JCK_BHT_tBu1C_04042022
_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_JCK_tBu2C1HNiCl2
_audit_block_doi                 10.5517/ccdc.csd.cc2bs6w7
_database_code_depnum_ccdc_archive 'CCDC 2168229'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 Cl2 N2 Ni P'
_chemical_formula_sum            'C15 H27 Cl2 N2 Ni P'
_chemical_formula_weight         395.96
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.8054(3)
_cell_length_b                   15.0567(6)
_cell_length_c                   14.6029(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.846(2)
_cell_angle_gamma                90
_cell_volume                     1907.54(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6828
_cell_measurement_theta_min      2.5256
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.513
_exptl_absorpt_coefficient_mu    1.377
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.732
_diffrn_reflns_theta_min         1.958
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5423
_reflns_number_total             6451
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         6451
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.027
_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)+(0.0402P)²+0.4173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0778
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.09 with sigma of 0.04
 C7-H2N
 1.91 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Ni1 Ni 0.39342(2) 0.26226(2) 0.55460(2) 0.03315(5) Uani 1 1 d . . . . .
Cl1 Cl 0.21835(4) 0.15315(3) 0.53302(3) 0.05157(9) Uani 1 1 d . . . . .
Cl2 Cl 0.42969(5) 0.33288(3) 0.42486(2) 0.05823(11) Uani 1 1 d . . . . .
P1 P 0.63536(3) 0.23169(2) 0.64367(2) 0.02815(6) Uani 1 1 d D . . . .
N1 N 0.33413(12) 0.35761(7) 0.63840(7) 0.0354(2) Uani 1 1 d . . . . .
N2 N 0.63758(13) 0.24353(8) 0.75753(7) 0.0390(2) Uani 1 1 d D . . . .
H2N H 0.7262(16) 0.2391(11) 0.7887(11) 0.047 Uiso 1 1 d D U . . .
C1 C 0.31051(19) 0.44131(10) 0.60661(12) 0.0500(3) Uani 1 1 d . . . . .
H1 H 0.307780 0.452065 0.543634 0.060 Uiso 1 1 calc R U . . .
C2 C 0.2902(2) 0.51153(11) 0.66357(15) 0.0620(4) Uani 1 1 d . . . . .
H2 H 0.272894 0.568466 0.639344 0.074 Uiso 1 1 calc R U . . .
C3 C 0.2960(2) 0.49624(11) 0.75642(14) 0.0604(4) Uani 1 1 d . . . . .
H3 H 0.284715 0.542762 0.796597 0.073 Uiso 1 1 calc R U . . .
C4 C 0.31878(18) 0.41128(11) 0.78916(11) 0.0517(4) Uani 1 1 d . . . . .
H4 H 0.322895 0.399919 0.852136 0.062 Uiso 1 1 calc R U . . .
C5 C 0.33578(14) 0.34189(9) 0.72908(9) 0.0356(2) Uani 1 1 d . . . . .
C6 C 0.35517(16) 0.24806(9) 0.76275(9) 0.0397(3) Uani 1 1 d . . . . .
H6A H 0.327979 0.208543 0.710032 0.048 Uiso 1 1 calc R U . . .
H6B H 0.283485 0.237118 0.805065 0.048 Uiso 1 1 calc R U . . .
C7 C 0.51634(17) 0.22524(11) 0.81173(9) 0.0453(3) Uani 1 1 d D . . . .
H7A H 0.537829 0.258624 0.869303 0.054 Uiso 1 1 calc R U . . .
H7B H 0.519500 0.162644 0.827671 0.054 Uiso 1 1 calc R U . . .
C8 C 0.69248(16) 0.11561(9) 0.61907(10) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.5872(2) 0.05505(10) 0.66475(13) 0.0550(4) Uani 1 1 d . . . . .
H9A H 0.481784 0.072447 0.645066 0.082 Uiso 1 1 calc R U . . .
H9B H 0.613365 0.060134 0.731108 0.082 Uiso 1 1 calc R U . . .
H9C H 0.600482 -0.005378 0.646693 0.082 Uiso 1 1 calc R U . . .
C10 C 0.8598(2) 0.09201(13) 0.65917(15) 0.0641(5) Uani 1 1 d . . . . .
H10A H 0.876607 0.029898 0.649876 0.096 Uiso 1 1 calc R U . . .
H10B H 0.879830 0.105060 0.724472 0.096 Uiso 1 1 calc R U . . .
H10C H 0.927947 0.126261 0.628292 0.096 Uiso 1 1 calc R U . . .
C11 C 0.6573(3) 0.10009(12) 0.51387(12) 0.0630(5) Uani 1 1 d . . . . .
H11A H 0.550208 0.111728 0.491396 0.094 Uiso 1 1 calc R U . . .
H11B H 0.680332 0.039601 0.500616 0.094 Uiso 1 1 calc R U . . .
H11C H 0.719274 0.139222 0.483684 0.094 Uiso 1 1 calc R U . . .
C12 C 0.78708(15) 0.31456(9) 0.62573(9) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.8372(2) 0.30168(13) 0.53105(12) 0.0573(4) Uani 1 1 d . . . . .
H13A H 0.747846 0.300883 0.483066 0.086 Uiso 1 1 calc R U . . .
H13B H 0.891543 0.246431 0.530812 0.086 Uiso 1 1 calc R U . . .
H13C H 0.903564 0.349661 0.520019 0.086 Uiso 1 1 calc R U . . .
C14 C 0.92968(18) 0.31173(14) 0.70253(13) 0.0629(5) Uani 1 1 d . . . . .
H14A H 0.977852 0.254511 0.702750 0.094 Uiso 1 1 calc R U . . .
H14B H 0.899191 0.322027 0.761682 0.094 Uiso 1 1 calc R U . . .
H14C H 1.001208 0.356865 0.691200 0.094 Uiso 1 1 calc R U . . .
C15 C 0.71251(18) 0.40659(10) 0.62789(12) 0.0498(3) Uani 1 1 d . . . . .
H15A H 0.787294 0.451653 0.621853 0.075 Uiso 1 1 calc R U . . .
H15B H 0.676245 0.414190 0.685768 0.075 Uiso 1 1 calc R U . . .
H15C H 0.627388 0.411451 0.577413 0.075 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
Ni1 Cl1 2.2380(4) . ?
Ni1 Cl2 2.2424(4) . ?
Ni1 P1 2.3440(3) . ?
Ni1 N1 2.0124(10) . ?
P1 N2 1.6690(11) . ?
P1 C8 1.8703(13) . ?
P1 C12 1.8789(13) . ?
N1 C1 1.3468(18) . ?
N1 C5 1.3428(16) . ?
N2 H2N 0.836(13) . ?
N2 C7 1.4599(17) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.3888(19) . ?
C5 C6 1.4961(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.515(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.532(2) . ?
C8 C10 1.531(2) . ?
C8 C11 1.532(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.534(2) . ?
C12 C14 1.534(2) . ?
C12 C15 1.536(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
Cl1 Ni1 Cl2 115.045(16) . . ?
Cl1 Ni1 P1 118.212(15) . . ?
Cl2 Ni1 P1 108.346(15) . . ?
N1 Ni1 Cl1 111.42(3) . . ?
N1 Ni1 Cl2 105.35(3) . . ?
N1 Ni1 P1 96.22(3) . . ?
N2 P1 Ni1 112.74(4) . . ?
N2 P1 C8 109.48(6) . . ?
N2 P1 C12 100.40(6) . . ?
C8 P1 Ni1 109.01(5) . . ?
C8 P1 C12 111.89(6) . . ?
C12 P1 Ni1 113.12(4) . . ?
C1 N1 Ni1 119.92(9) . . ?
C5 N1 Ni1 120.91(9) . . ?
C5 N1 C1 118.67(12) . . ?
P1 N2 H2N 112.6(12) . . ?
C7 N2 P1 129.41(10) . . ?
C7 N2 H2N 113.0(12) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.62(15) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.91(16) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.83(15) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.51(15) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 120.42(13) . . ?
N1 C5 C6 118.16(11) . . ?
C4 C5 C6 121.42(13) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.48(12) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
N2 C7 C6 114.45(10) . . ?
N2 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 P1 105.66(10) . . ?
C9 C8 C11 108.18(14) . . ?
C10 C8 P1 114.60(11) . . ?
C10 C8 C9 108.04(13) . . ?
C10 C8 C11 111.37(14) . . ?
C11 C8 P1 108.67(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 111.27(11) . . ?
C13 C12 C14 109.25(13) . . ?
C13 C12 C15 108.82(13) . . ?
C14 C12 P1 113.08(10) . . ?
C14 C12 C15 108.02(13) . . ?
C15 C12 P1 106.24(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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_JCK_CutBu2C_teal_01292021
_audit_block_doi                 10.5517/ccdc.csd.cc2bs6zb
_database_code_depnum_ccdc_archive 'CCDC 2168232'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H54 Cl4 Cu2 N4 O2 P2'
_chemical_formula_sum            'C30 H54 Cl4 Cu2 N4 O2 P2'
_chemical_formula_weight         833.59
_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'
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'
O O 0.0106 0.0060 '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                   8.3490(4)
_cell_length_b                   11.6402(6)
_cell_length_c                   11.6734(6)
_cell_angle_alpha                110.5230(10)
_cell_angle_beta                 101.0310(10)
_cell_angle_gamma                109.1720(10)
_cell_volume                     941.38(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5069
_cell_measurement_theta_min      2.6384
_shelx_estimated_absorpt_T_max   0.770
_shelx_estimated_absorpt_T_min   0.450
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12243
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.789
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5880
_reflns_number_total             6271
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         6271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.032
_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)+(0.0287P)²+0.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0567
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.12 with sigma of 0.04
 C7-H2N
 1.95 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.18959(2) 0.20615(2) 0.43160(2) 0.01336(4) Uani 1 1 d . . . . .
Cl1 Cl 0.08428(4) 0.32261(3) 0.57114(2) 0.02290(5) Uani 1 1 d . . . . .
Cl2 Cl 0.10996(3) 0.00359(2) 0.26693(2) 0.01942(5) Uani 1 1 d . . . . .
P1 P 0.14889(3) 0.36572(2) 0.24209(2) 0.01250(5) Uani 1 1 d D . . . .
O1 O 0.20477(10) 0.30152(8) 0.32458(7) 0.01841(13) Uani 1 1 d . . . . .
N1 N 0.66320(11) 0.82721(8) 0.43922(8) 0.01455(14) Uani 1 1 d . . . . .
N2 N 0.20386(11) 0.52866(8) 0.33156(8) 0.01599(15) Uani 1 1 d D . . . .
C1 C 0.74031(15) 0.87564(11) 0.36444(10) 0.01953(18) Uani 1 1 d . . . . .
H1 H 0.856536 0.884399 0.369343 0.023 Uiso 1 1 calc R U . . .
C2 C 0.65217(17) 0.91280(12) 0.28052(11) 0.0244(2) Uani 1 1 d . . . . .
H2 H 0.708313 0.946345 0.230109 0.029 Uiso 1 1 calc R U . . .
C3 C 0.47843(17) 0.89899(12) 0.27311(11) 0.0254(2) Uani 1 1 d . . . . .
H3 H 0.416695 0.923983 0.218143 0.031 Uiso 1 1 calc R U . . .
C4 C 0.39801(15) 0.84740(11) 0.34880(11) 0.02125(19) Uani 1 1 d . . . . .
H4 H 0.280995 0.836238 0.343950 0.026 Uiso 1 1 calc R U . . .
C5 C 0.49347(13) 0.81246(9) 0.43202(9) 0.01497(16) Uani 1 1 d . . . . .
C6 C 0.41091(13) 0.75519(10) 0.51477(9) 0.01642(17) Uani 1 1 d . . . . .
H6A H 0.308378 0.775666 0.521088 0.020 Uiso 1 1 calc R U . . .
H6B H 0.499048 0.799403 0.602038 0.020 Uiso 1 1 calc R U . . .
C7 C 0.34802(13) 0.60140(10) 0.46103(9) 0.01622(16) Uani 1 1 d D . . . .
H7A H 0.449717 0.580060 0.453858 0.019 Uiso 1 1 calc R U . . .
H7B H 0.303057 0.571148 0.520966 0.019 Uiso 1 1 calc R U . . .
C8 C 0.27851(14) 0.35563(10) 0.12983(10) 0.01721(17) Uani 1 1 d . . . . .
C9 C 0.47559(15) 0.46035(12) 0.21227(12) 0.0254(2) Uani 1 1 d . . . . .
H9A H 0.549340 0.454729 0.158578 0.038 Uiso 1 1 calc R U . . .
H9B H 0.519243 0.441540 0.282743 0.038 Uiso 1 1 calc R U . . .
H9C H 0.480988 0.550043 0.246846 0.038 Uiso 1 1 calc R U . . .
C10 C 0.21149(19) 0.38940(15) 0.01972(13) 0.0318(3) Uani 1 1 d . . . . .
H10A H 0.292595 0.393441 -0.028530 0.048 Uiso 1 1 calc R U . . .
H10B H 0.207068 0.475681 0.056072 0.048 Uiso 1 1 calc R U . . .
H10C H 0.092787 0.320268 -0.037425 0.048 Uiso 1 1 calc R U . . .
C11 C 0.27408(16) 0.21329(12) 0.07223(12) 0.0254(2) Uani 1 1 d . . . . .
H11A H 0.153760 0.147795 0.014603 0.038 Uiso 1 1 calc R U . . .
H11B H 0.309801 0.190660 0.141532 0.038 Uiso 1 1 calc R U . . .
H11C H 0.355898 0.212614 0.024602 0.038 Uiso 1 1 calc R U . . .
C12 C -0.09821(13) 0.28685(10) 0.16043(9) 0.01598(16) Uani 1 1 d . . . . .
C13 C -0.18162(15) 0.28901(12) 0.26736(11) 0.0236(2) Uani 1 1 d . . . . .
H13A H -0.311047 0.246423 0.228761 0.035 Uiso 1 1 calc R U . . .
H13B H -0.142083 0.381361 0.329843 0.035 Uiso 1 1 calc R U . . .
H13C H -0.143807 0.240590 0.310203 0.035 Uiso 1 1 calc R U . . .
C14 C -0.16114(15) 0.13798(11) 0.06331(11) 0.0238(2) Uani 1 1 d . . . . .
H14A H -0.290690 0.092102 0.032602 0.036 Uiso 1 1 calc R U . . .
H14B H -0.110813 0.094142 0.105818 0.036 Uiso 1 1 calc R U . . .
H14C H -0.121233 0.134666 -0.009156 0.036 Uiso 1 1 calc R U . . .
C15 C -0.16275(16) 0.36275(12) 0.09165(12) 0.0250(2) Uani 1 1 d . . . . .
H15A H -0.113239 0.360748 0.023592 0.037 Uiso 1 1 calc R U . . .
H15B H -0.122985 0.455341 0.153635 0.037 Uiso 1 1 calc R U . . .
H15C H -0.292347 0.319597 0.054745 0.037 Uiso 1 1 calc R U . . .
H2N H 0.1134(19) 0.5474(16) 0.3338(15) 0.030 Uiso 1 1 d D 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
Cu1 Cl1 2.2465(3) . ?
Cu1 Cl2 2.2361(3) . ?
Cu1 O1 1.9364(7) . ?
Cu1 N1 1.9876(8) 2_666 ?
P1 O1 1.5050(7) . ?
P1 N2 1.6597(9) . ?
P1 C8 1.8494(10) . ?
P1 C12 1.8432(10) . ?
N1 C1 1.3475(13) . ?
N1 C5 1.3524(12) . ?
N2 C7 1.4788(12) . ?
N2 H2N 0.854(12) . ?
C1 H1 0.9300 . ?
C1 C2 1.3852(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.3880(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3878(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3922(14) . ?
C5 C6 1.5024(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5306(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5406(15) . ?
C8 C10 1.5308(15) . ?
C8 C11 1.5387(15) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.5381(14) . ?
C12 C14 1.5366(14) . ?
C12 C15 1.5363(14) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
Cl2 Cu1 Cl1 142.477(11) . . ?
O1 Cu1 Cl1 98.83(2) . . ?
O1 Cu1 Cl2 94.72(2) . . ?
O1 Cu1 N1 143.43(3) . 2_666 ?
N1 Cu1 Cl1 95.58(2) 2_666 . ?
N1 Cu1 Cl2 93.93(2) 2_666 . ?
O1 P1 N2 111.61(4) . . ?
O1 P1 C8 106.09(4) . . ?
O1 P1 C12 111.90(4) . . ?
N2 P1 C8 107.79(5) . . ?
N2 P1 C12 105.05(4) . . ?
C12 P1 C8 114.43(5) . . ?
P1 O1 Cu1 159.31(5) . . ?
C1 N1 Cu1 118.71(7) . 2_666 ?
C1 N1 C5 119.57(9) . . ?
C5 N1 Cu1 121.51(7) . 2_666 ?
P1 N2 H2N 114.3(11) . . ?
C7 N2 P1 118.51(6) . . ?
C7 N2 H2N 111.9(10) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.16(10) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.71(10) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.15(10) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.64(10) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.75(9) . . ?
N1 C5 C6 117.89(8) . . ?
C4 C5 C6 121.35(9) . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 113.12(8) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
N2 C7 C6 111.00(8) . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 P1 106.72(7) . . ?
C10 C8 P1 113.41(8) . . ?
C10 C8 C9 108.35(10) . . ?
C10 C8 C11 109.88(9) . . ?
C11 C8 P1 109.81(7) . . ?
C11 C8 C9 108.52(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 106.53(7) . . ?
C14 C12 P1 109.29(7) . . ?
C14 C12 C13 108.30(9) . . ?
C15 C12 P1 113.38(7) . . ?
C15 C12 C13 108.66(9) . . ?
C15 C12 C14 110.49(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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_JCK_tBu1C1H_CoCl2_02082020
_audit_block_doi                 10.5517/ccdc.csd.cc2bs74j
_database_code_depnum_ccdc_archive 'CCDC 2168237'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H25 Cl2 Co N2 P'
_chemical_formula_sum            'C14 H25 Cl2 Co N2 P'
_chemical_formula_weight         382.16
_chemical_absolute_configuration ?
_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'
Co Co 0.3494 0.9721 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5503(2)
_cell_length_b                   11.6343(2)
_cell_length_c                   14.8131(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1818.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.3283
_cell_measurement_theta_min      2.2259
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.4864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.930
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.806
_diffrn_reflns_theta_min         2.226
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                5802
_reflns_number_total             6389
_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 V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 2401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         6389
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.052
_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)+(0.0420P)²+0.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0707
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.12 with sigma of 0.04
 C6-H2N
 1.94 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Co1 Co 0.42663(2) 0.50117(2) 0.57407(2) 0.03353(6) Uani 1 1 d . . . . .
Cl1 Cl 0.61344(5) 0.53210(5) 0.63870(4) 0.05383(13) Uani 1 1 d . . . . .
Cl2 Cl 0.43811(5) 0.53181(5) 0.42392(3) 0.05026(12) Uani 1 1 d . . . . .
P1 P 0.24990(4) 0.58683(4) 0.65104(3) 0.03372(9) Uani 1 1 d D . . . .
N1 N 0.36198(16) 0.33585(14) 0.59156(12) 0.0410(3) Uani 1 1 d . . . . .
N2 N 0.20976(19) 0.48325(18) 0.72378(13) 0.0512(4) Uani 1 1 d D . . . .
C1 C 0.3625(3) 0.26334(19) 0.52079(19) 0.0544(5) Uani 1 1 d . . . . .
H1 H 0.405257 0.284614 0.468490 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3014(3) 0.1581(2) 0.5234(3) 0.0698(8) Uani 1 1 d . . . . .
H2 H 0.300900 0.110583 0.472900 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2428(3) 0.1255(2) 0.6000(3) 0.0812(10) Uani 1 1 d . . . . .
H3 H 0.201958 0.054714 0.603036 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2436(3) 0.1975(2) 0.6741(2) 0.0681(8) Uani 1 1 d . . . . .
H4 H 0.204783 0.174956 0.727597 0.082 Uiso 1 1 calc R U . . .
C5 C 0.3028(2) 0.30415(19) 0.66801(18) 0.0489(5) Uani 1 1 d . . . . .
C6 C 0.2997(3) 0.3903(2) 0.74373(16) 0.0562(6) Uani 1 1 d D . . . .
H6A H 0.275064 0.352190 0.799263 0.067 Uiso 1 1 calc R U . . .
H6B H 0.383749 0.422343 0.752277 0.067 Uiso 1 1 calc R U . . .
C7 C 0.2798(2) 0.7197(2) 0.71857(15) 0.0460(4) Uani 1 1 d . . . . .
C8 C 0.3648(3) 0.6828(3) 0.7977(2) 0.0697(8) Uani 1 1 d . . . . .
H8A H 0.440486 0.647647 0.774689 0.105 Uiso 1 1 calc R U . . .
H8B H 0.320018 0.628639 0.834818 0.105 Uiso 1 1 calc R U . . .
H8C H 0.386847 0.748967 0.833067 0.105 Uiso 1 1 calc R U . . .
C9 C 0.1618(3) 0.7774(3) 0.7569(2) 0.0666(7) Uani 1 1 d . . . . .
H9A H 0.110719 0.806329 0.708325 0.100 Uiso 1 1 calc R U . . .
H9B H 0.186458 0.839813 0.795495 0.100 Uiso 1 1 calc R U . . .
H9C H 0.113835 0.722391 0.791084 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3557(4) 0.8043(3) 0.6607(2) 0.0777(9) Uani 1 1 d . . . . .
H10A H 0.432704 0.768303 0.640897 0.117 Uiso 1 1 calc R U . . .
H10B H 0.375760 0.871230 0.695852 0.117 Uiso 1 1 calc R U . . .
H10C H 0.306270 0.826437 0.609175 0.117 Uiso 1 1 calc R U . . .
C11 C 0.11005(18) 0.6020(2) 0.57548(17) 0.0496(5) Uani 1 1 d . . . . .
C12 C -0.0161(2) 0.6153(3) 0.6249(2) 0.0755(9) Uani 1 1 d . . . . .
H12A H -0.019814 0.689752 0.652796 0.113 Uiso 1 1 calc R U . . .
H12B H -0.023208 0.556930 0.670455 0.113 Uiso 1 1 calc R U . . .
H12C H -0.084553 0.607651 0.582681 0.113 Uiso 1 1 calc R U . . .
C13 C 0.1335(3) 0.7041(3) 0.5116(2) 0.0727(8) Uani 1 1 d . . . . .
H13A H 0.213414 0.694161 0.481541 0.109 Uiso 1 1 calc R U . . .
H13B H 0.134905 0.774178 0.545757 0.109 Uiso 1 1 calc R U . . .
H13C H 0.066885 0.707629 0.467519 0.109 Uiso 1 1 calc R U . . .
C14 C 0.1058(2) 0.4913(3) 0.5194(2) 0.0685(7) Uani 1 1 d . . . . .
H14A H 0.038311 0.496216 0.476107 0.103 Uiso 1 1 calc R U . . .
H14B H 0.091477 0.426840 0.558553 0.103 Uiso 1 1 calc R U . . .
H14C H 0.184999 0.481497 0.488406 0.103 Uiso 1 1 calc R U . . .
H2N H 0.158(3) 0.499(3) 0.7665(18) 0.082 Uiso 1 1 d D 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
Co1 Cl1 2.2205(5) . ?
Co1 Cl2 2.2558(6) . ?
Co1 P1 2.4020(5) . ?
Co1 N1 2.0572(16) . ?
P1 N2 1.6711(19) . ?
P1 C7 1.868(2) . ?
P1 C11 1.860(2) . ?
N1 C1 1.346(3) . ?
N1 C5 1.345(3) . ?
N2 C6 1.469(3) . ?
N2 H2N 0.85(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.348(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(4) . ?
C5 C6 1.504(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.537(4) . ?
C7 C9 1.524(3) . ?
C7 C10 1.531(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.527(3) . ?
C11 C13 1.539(4) . ?
C11 C14 1.533(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
Cl1 Co1 Cl2 110.60(2) . . ?
Cl1 Co1 P1 114.65(2) . . ?
Cl2 Co1 P1 116.37(2) . . ?
N1 Co1 Cl1 113.05(5) . . ?
N1 Co1 Cl2 106.84(5) . . ?
N1 Co1 P1 94.06(5) . . ?
N2 P1 Co1 101.74(7) . . ?
N2 P1 C7 107.11(11) . . ?
N2 P1 C11 104.80(11) . . ?
C7 P1 Co1 117.80(7) . . ?
C11 P1 Co1 111.68(7) . . ?
C11 P1 C7 112.18(11) . . ?
C1 N1 Co1 119.12(15) . . ?
C5 N1 Co1 121.09(15) . . ?
C5 N1 C1 119.1(2) . . ?
P1 N2 H2N 119(2) . . ?
C6 N2 P1 119.80(15) . . ?
C6 N2 H2N 115(2) . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.1(3) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.5(3) . . ?
N1 C5 C6 117.1(2) . . ?
C4 C5 C6 122.4(2) . . ?
N2 C6 C5 110.8(2) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 P1 106.00(18) . . ?
C9 C7 P1 115.21(18) . . ?
C9 C7 C8 108.4(2) . . ?
C9 C7 C10 110.7(3) . . ?
C10 C7 P1 108.70(17) . . ?
C10 C7 C8 107.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 P1 114.3(2) . . ?
C12 C11 C13 110.9(2) . . ?
C12 C11 C14 108.6(2) . . ?
C13 C11 P1 108.41(17) . . ?
C14 C11 P1 105.63(15) . . ?
C14 C11 C13 108.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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_JCK_tBu2C1H_CoCl2_11122020
_audit_block_doi                 10.5517/ccdc.csd.cc2bs76l
_database_code_depnum_ccdc_archive 'CCDC 2168239'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 Cl2 Co N2 P'
_chemical_formula_sum            'C15 H27 Cl2 Co N2 P'
_chemical_formula_weight         396.18
_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'
Co Co 0.3494 0.9721 '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                   8.8055(2)
_cell_length_b                   15.0416(3)
_cell_length_c                   14.6897(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.7060(10)
_cell_angle_gamma                90
_cell_volume                     1923.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5109
_cell_measurement_theta_min      2.5396
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.552
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.814
_diffrn_reflns_theta_min         1.949
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5815
_reflns_number_total             6773
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0790
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.1 with sigma of 0.04
 C7-H2N
 1.91 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Co1 Co 0.60815(2) 0.73263(2) 0.44591(2) 0.03180(5) Uani 1 1 d . . . . .
Cl1 Cl 0.77952(4) 0.84363(2) 0.47399(3) 0.05028(8) Uani 1 1 d . . . . .
Cl2 Cl 0.57966(5) 0.66546(3) 0.57883(2) 0.05757(10) Uani 1 1 d . . . . .
P1 P 0.36459(3) 0.76902(2) 0.35632(2) 0.02859(6) Uani 1 1 d D . . . .
N1 N 0.67455(11) 0.63688(7) 0.36108(7) 0.03557(19) Uani 1 1 d . . . . .
N2 N 0.36615(12) 0.75673(8) 0.24333(7) 0.0386(2) Uani 1 1 d D . . . .
C1 C 0.69684(17) 0.55239(9) 0.39076(11) 0.0498(3) Uani 1 1 d . . . . .
H1 H 0.701763 0.540675 0.453299 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7126(2) 0.48288(10) 0.33212(14) 0.0613(4) Uani 1 1 d . . . . .
H2 H 0.729350 0.425396 0.354719 0.074 Uiso 1 1 calc R U . . .
C3 C 0.70307(18) 0.49985(10) 0.23978(13) 0.0593(4) Uani 1 1 d . . . . .
H3 H 0.711496 0.453849 0.198543 0.071 Uiso 1 1 calc R U . . .
C4 C 0.68094(17) 0.58573(11) 0.20903(10) 0.0506(3) Uani 1 1 d . . . . .
H4 H 0.674449 0.598177 0.146550 0.061 Uiso 1 1 calc R U . . .
C5 C 0.66822(12) 0.65406(8) 0.27094(8) 0.0350(2) Uani 1 1 d . . . . .
C6 C 0.64981(14) 0.74918(9) 0.24045(9) 0.0387(2) Uani 1 1 d . . . . .
H6A H 0.724544 0.761864 0.200002 0.046 Uiso 1 1 calc R U . . .
H6B H 0.673339 0.787098 0.294142 0.046 Uiso 1 1 calc R U . . .
C7 C 0.49129(15) 0.77336(10) 0.19074(8) 0.0438(3) Uani 1 1 d D . . . .
H7A H 0.490830 0.835929 0.174713 0.053 Uiso 1 1 calc R U . . .
H7B H 0.471921 0.739799 0.133780 0.053 Uiso 1 1 calc R U . . .
C8 C 0.30674(15) 0.88517(9) 0.38044(9) 0.0422(3) Uani 1 1 d . . . . .
C9 C 0.4148(2) 0.94533(10) 0.33576(13) 0.0574(4) Uani 1 1 d . . . . .
H9A H 0.393071 0.939350 0.270017 0.086 Uiso 1 1 calc R U . . .
H9B H 0.519383 0.928337 0.356713 0.086 Uiso 1 1 calc R U . . .
H9C H 0.399856 1.006027 0.352556 0.086 Uiso 1 1 calc R U . . .
C10 C 0.3378(2) 0.90047(12) 0.48482(11) 0.0651(4) Uani 1 1 d . . . . .
H10A H 0.444221 0.889281 0.507220 0.098 Uiso 1 1 calc R U . . .
H10B H 0.275195 0.860867 0.514512 0.098 Uiso 1 1 calc R U . . .
H10C H 0.313374 0.960850 0.498080 0.098 Uiso 1 1 calc R U . . .
C11 C 0.14095(19) 0.90940(12) 0.34074(14) 0.0645(4) Uani 1 1 d . . . . .
H11A H 0.123223 0.896845 0.275927 0.097 Uiso 1 1 calc R U . . .
H11B H 0.124296 0.971530 0.350458 0.097 Uiso 1 1 calc R U . . .
H11C H 0.071442 0.875010 0.370968 0.097 Uiso 1 1 calc R U . . .
C12 C 0.21333(13) 0.68555(9) 0.37475(9) 0.0402(2) Uani 1 1 d . . . . .
C13 C 0.07196(16) 0.68816(13) 0.29955(13) 0.0636(4) Uani 1 1 d . . . . .
H13A H 0.103536 0.679503 0.240424 0.095 Uiso 1 1 calc R U . . .
H13B H 0.022018 0.744788 0.300756 0.095 Uiso 1 1 calc R U . . .
H13C H 0.001907 0.641827 0.310414 0.095 Uiso 1 1 calc R U . . .
C14 C 0.28950(17) 0.59393(10) 0.37162(11) 0.0511(3) Uani 1 1 d . . . . .
H14A H 0.215422 0.548272 0.377501 0.077 Uiso 1 1 calc R U . . .
H14B H 0.373414 0.589166 0.421366 0.077 Uiso 1 1 calc R U . . .
H14C H 0.327259 0.587096 0.314045 0.077 Uiso 1 1 calc R U . . .
C15 C 0.16376(19) 0.69746(13) 0.46960(11) 0.0590(4) Uani 1 1 d . . . . .
H15A H 0.107005 0.751861 0.470538 0.088 Uiso 1 1 calc R U . . .
H15B H 0.253112 0.699635 0.515956 0.088 Uiso 1 1 calc R U . . .
H15C H 0.100122 0.648355 0.481721 0.088 Uiso 1 1 calc R U . . .
H2N H 0.2785(18) 0.7625(13) 0.2114(12) 0.071 Uiso 1 1 d D 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
Co1 Cl1 2.2463(3) . ?
Co1 Cl2 2.2460(4) . ?
Co1 P1 2.4035(3) . ?
Co1 N1 2.0469(10) . ?
P1 N2 1.6722(10) . ?
P1 C8 1.8687(13) . ?
P1 C12 1.8795(12) . ?
N1 C1 1.3482(16) . ?
N1 C5 1.3419(15) . ?
N2 C7 1.4599(16) . ?
N2 H2N 0.845(14) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3881(17) . ?
C5 C6 1.5005(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5183(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.531(2) . ?
C8 C10 1.534(2) . ?
C8 C11 1.532(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.5347(19) . ?
C12 C14 1.536(2) . ?
C12 C15 1.5323(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
Cl1 Co1 P1 116.760(13) . . ?
Cl2 Co1 Cl1 109.575(15) . . ?
Cl2 Co1 P1 111.752(14) . . ?
N1 Co1 Cl1 112.89(3) . . ?
N1 Co1 Cl2 107.01(3) . . ?
N1 Co1 P1 98.07(3) . . ?
N2 P1 Co1 112.19(4) . . ?
N2 P1 C8 109.57(6) . . ?
N2 P1 C12 100.46(6) . . ?
C8 P1 Co1 110.81(4) . . ?
C8 P1 C12 112.19(6) . . ?
C12 P1 Co1 111.23(4) . . ?
C1 N1 Co1 120.49(9) . . ?
C5 N1 Co1 119.48(8) . . ?
C5 N1 C1 118.88(11) . . ?
P1 N2 H2N 113.3(13) . . ?
C7 N2 P1 128.79(9) . . ?
C7 N2 H2N 112.8(13) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.53(14) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.80(15) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.04(13) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.18(14) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.56(12) . . ?
N1 C5 C6 117.69(10) . . ?
C4 C5 C6 121.74(12) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C5 C6 C7 114.95(11) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N2 C7 C6 114.65(10) . . ?
N2 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 P1 105.44(9) . . ?
C9 C8 C10 108.15(13) . . ?
C9 C8 C11 108.34(13) . . ?
C10 C8 P1 108.51(10) . . ?
C11 C8 P1 114.94(11) . . ?
C11 C8 C10 111.12(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 113.23(10) . . ?
C13 C12 C14 108.16(13) . . ?
C14 C12 P1 105.83(8) . . ?
C15 C12 P1 111.01(10) . . ?
C15 C12 C13 109.87(12) . . ?
C15 C12 C14 108.53(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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_JCK_NitBu2C_AgBF4_04122022
_audit_block_doi                 10.5517/ccdc.csd.cc2bv24f
_database_code_depnum_ccdc_archive 'CCDC 2170004'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-06 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C60 H108 Ag4 Cl2 N8 P4, 2(B F4)'
_chemical_formula_sum            'C60 H108 Ag4 B2 Cl2 F8 N8 P4'
_chemical_formula_weight         1741.42
_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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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                   12.3096(2)
_cell_length_b                   12.3824(2)
_cell_length_c                   13.0675(2)
_cell_angle_alpha                77.1240(10)
_cell_angle_beta                 84.4990(10)
_cell_angle_gamma                88.5690(10)
_cell_volume                     1932.74(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7173
_cell_measurement_theta_min      2.2014
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.065
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34628
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.937
_diffrn_reflns_theta_min         1.662
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9625
_reflns_number_total             13342
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         13342
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.1481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0765
_olex2_refinement_description    
;
1. Restrained distances
 N4-H4
 0.9 with sigma of 0.02
 N2-H2
 0.9 with sigma of 0.02
 P2-H4
 2.1 with sigma of 0.04
 C22-H4
 1.91 with sigma of 0.04
 P1-H2
 2.09 with sigma of 0.04
 C7-H2
 1.91 with sigma of 0.04
 B1-F4 \\sim B1A-F4A
 with sigma of 0.02
 F2-F3 \\sim F2A-F3A
 with sigma of 0.04
 B1-F2 \\sim B1A-F2A
 with sigma of 0.02
 B1-F1 \\sim B1A-F1A
 with sigma of 0.02
 B1-F3 \\sim B1A-F3A
 with sigma of 0.02
 F2-F4 \\sim F2A-F4A
 with sigma of 0.04
 F3-F4 \\sim F3A-F4A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A
 with sigma of 0.04
 F1-F3 \\sim F1A-F3A
 with sigma of 0.04
 F1-F4 \\sim F1A-F4A
 with sigma of 0.04
2. Rigid body (RIGU) restrains
 B1A, F3A, F4A, F2A, F1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 B1, F1, F2, F3, F4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(B1A)=Sof(F3A)=Sof(F4A)=Sof(F2A)=Sof(F1A)=1-FVAR(1)
 Sof(B1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C21(H21A,H21B), C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4A), C16(H16), C17(H17), C18(H18), C19(H19)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
B1 B 0.4331(5) 1.0459(5) 0.2767(5) 0.0502(17) Uani 0.723(8) 1 d D . P A 1
Cl1 Cl 0.04778(4) 0.54706(4) 0.33515(3) 0.04290(10) Uani 1 1 d . . . . .
Ag1 Ag 0.18067(2) 0.58497(2) 0.16761(2) 0.04607(5) Uani 1 1 d . . . . .
Ag2 Ag -0.01562(2) 0.65067(2) 0.49486(2) 0.04655(5) Uani 1 1 d . . . . .
P1 P 0.29230(4) 0.74634(4) 0.11706(3) 0.03585(9) Uani 1 1 d D . . . .
P2 P 0.18912(3) 0.25551(4) 0.52543(3) 0.03412(9) Uani 1 1 d D . . . .
F1 F 0.3467(5) 1.0610(6) 0.2176(5) 0.0975(18) Uani 0.723(8) 1 d D . P A 1
F2 F 0.4797(3) 0.9480(3) 0.2710(4) 0.1013(18) Uani 0.723(8) 1 d D . P A 1
F3 F 0.5008(4) 1.1312(4) 0.2417(3) 0.123(2) Uani 0.723(8) 1 d D . P A 1
F4 F 0.4006(3) 1.0429(4) 0.3778(2) 0.1242(17) Uani 0.723(8) 1 d D . P A 1
N1 N 0.14208(11) 0.68924(13) 0.56247(10) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.30176(15) 0.80659(14) 0.21689(12) 0.0505(4) Uani 1 1 d D . . . .
N3 N 0.16777(12) 0.44250(13) 0.08217(11) 0.0421(3) Uani 1 1 d . . . . .
N4 N 0.24126(13) 0.22928(17) 0.41158(11) 0.0533(5) Uani 1 1 d D . . . .
C1 C 0.15394(16) 0.64287(18) 0.66385(14) 0.0491(5) Uani 1 1 d . . . . .
H1 H 0.099994 0.594914 0.701813 0.059 Uiso 1 1 calc R U . . .
C2 C 0.24165(18) 0.6626(2) 0.71434(15) 0.0567(5) Uani 1 1 d . . . . .
H2A H 0.247163 0.627934 0.784505 0.068 Uiso 1 1 calc R U . . .
C3 C 0.32081(17) 0.7342(2) 0.65991(16) 0.0568(5) Uani 1 1 d . . . . .
H3 H 0.381010 0.749121 0.692335 0.068 Uiso 1 1 calc R U . . .
C4 C 0.30958(15) 0.78351(18) 0.55630(15) 0.0475(4) Uani 1 1 d . . . . .
H4A H 0.361879 0.833274 0.518054 0.057 Uiso 1 1 calc R U . . .
C5 C 0.21984(13) 0.75882(15) 0.50886(12) 0.0364(4) Uani 1 1 d . . . . .
C6 C 0.21219(14) 0.80619(17) 0.39391(13) 0.0432(4) Uani 1 1 d . . . . .
H6A H 0.228356 0.884757 0.378035 0.052 Uiso 1 1 calc R U . . .
H6B H 0.138406 0.797467 0.376818 0.052 Uiso 1 1 calc R U . . .
C7 C 0.29169(15) 0.74845(17) 0.32717(13) 0.0430(4) Uani 1 1 d D . . . .
H7A H 0.362786 0.744042 0.354111 0.052 Uiso 1 1 calc R U . . .
H7B H 0.266846 0.673472 0.332662 0.052 Uiso 1 1 calc R U . . .
C8 C 0.22891(17) 0.85705(17) 0.01897(14) 0.0490(4) Uani 1 1 d . . . . .
C9 C 0.1213(2) 0.8842(3) 0.0760(2) 0.0919(10) Uani 1 1 d . . . . .
H9A H 0.079465 0.933877 0.027303 0.138 Uiso 1 1 calc R U . . .
H9B H 0.135746 0.918559 0.132285 0.138 Uiso 1 1 calc R U . . .
H9C H 0.080869 0.817174 0.104449 0.138 Uiso 1 1 calc R U . . .
C10 C 0.2057(3) 0.8122(2) -0.07598(19) 0.0884(9) Uani 1 1 d . . . . .
H10A H 0.273250 0.800699 -0.115324 0.133 Uiso 1 1 calc R U . . .
H10B H 0.161570 0.864472 -0.120079 0.133 Uiso 1 1 calc R U . . .
H10C H 0.167487 0.743159 -0.052477 0.133 Uiso 1 1 calc R U . . .
C11 C 0.2956(3) 0.9633(2) -0.0178(2) 0.0830(8) Uani 1 1 d . . . . .
H11A H 0.360396 0.949162 -0.059895 0.124 Uiso 1 1 calc R U . . .
H11B H 0.315551 0.987971 0.042496 0.124 Uiso 1 1 calc R U . . .
H11C H 0.252812 1.019550 -0.058971 0.124 Uiso 1 1 calc R U . . .
C12 C 0.43424(16) 0.71054(19) 0.07098(17) 0.0549(5) Uani 1 1 d . . . . .
C13 C 0.4689(2) 0.6174(3) 0.1617(2) 0.0893(9) Uani 1 1 d . . . . .
H13A H 0.421173 0.555129 0.170902 0.134 Uiso 1 1 calc R U . . .
H13B H 0.464507 0.643920 0.225629 0.134 Uiso 1 1 calc R U . . .
H13C H 0.542536 0.595178 0.144992 0.134 Uiso 1 1 calc R U . . .
C14 C 0.5148(2) 0.8058(3) 0.0533(3) 0.0942(10) Uani 1 1 d . . . . .
H14A H 0.587124 0.779478 0.037519 0.141 Uiso 1 1 calc R U . . .
H14B H 0.512487 0.834718 0.115765 0.141 Uiso 1 1 calc R U . . .
H14C H 0.495525 0.863258 -0.004693 0.141 Uiso 1 1 calc R U . . .
C15 C 0.4362(2) 0.6640(3) -0.0281(2) 0.0840(8) Uani 1 1 d . . . . .
H15A H 0.419909 0.722154 -0.086708 0.126 Uiso 1 1 calc R U . . .
H15B H 0.382664 0.606530 -0.017252 0.126 Uiso 1 1 calc R U . . .
H15C H 0.507276 0.634112 -0.042593 0.126 Uiso 1 1 calc R U . . .
C16 C 0.12690(17) 0.46091(19) -0.01237(14) 0.0516(5) Uani 1 1 d . . . . .
H16 H 0.104602 0.532442 -0.041949 0.062 Uiso 1 1 calc R U . . .
C17 C 0.11646(19) 0.3805(2) -0.06699(15) 0.0606(6) Uani 1 1 d . . . . .
H17 H 0.087367 0.396694 -0.131809 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1498(2) 0.2755(2) -0.02418(17) 0.0673(6) Uani 1 1 d . . . . .
H18 H 0.142283 0.218640 -0.058955 0.081 Uiso 1 1 calc R U . . .
C19 C 0.1945(2) 0.25454(19) 0.07097(16) 0.0583(5) Uani 1 1 d . . . . .
H19 H 0.218821 0.183691 0.100322 0.070 Uiso 1 1 calc R U . . .
C20 C 0.20315(15) 0.34024(16) 0.12277(13) 0.0428(4) Uani 1 1 d . . . . .
C21 C 0.25374(18) 0.32080(18) 0.22484(14) 0.0507(5) Uani 1 1 d . . . . .
H21A H 0.265953 0.391740 0.241595 0.061 Uiso 1 1 calc R U . . .
H21B H 0.324257 0.285473 0.216488 0.061 Uiso 1 1 calc R U . . .
C22 C 0.18507(16) 0.2495(2) 0.31592(13) 0.0525(5) Uani 1 1 d D . . . .
H22A H 0.115975 0.286303 0.327629 0.063 Uiso 1 1 calc R U . . .
H22B H 0.169959 0.179433 0.298764 0.063 Uiso 1 1 calc R U . . .
C23 C 0.17109(15) 0.11690(17) 0.61810(14) 0.0456(4) Uani 1 1 d . . . . .
C24 C 0.1011(2) 0.0512(2) 0.5625(2) 0.0750(7) Uani 1 1 d . . . . .
H24A H 0.035179 0.091605 0.545752 0.113 Uiso 1 1 calc R U . . .
H24B H 0.083249 -0.019436 0.608143 0.113 Uiso 1 1 calc R U . . .
H24C H 0.141084 0.040379 0.498769 0.113 Uiso 1 1 calc R U . . .
C25 C 0.1063(2) 0.1295(2) 0.72101(17) 0.0699(7) Uani 1 1 d . . . . .
H25A H 0.043651 0.175837 0.705035 0.105 Uiso 1 1 calc R U . . .
H25B H 0.151726 0.162715 0.761173 0.105 Uiso 1 1 calc R U . . .
H25C H 0.082789 0.057939 0.761242 0.105 Uiso 1 1 calc R U . . .
C26 C 0.27727(19) 0.0535(2) 0.64211(19) 0.0659(6) Uani 1 1 d . . . . .
H26A H 0.320352 0.051748 0.577244 0.099 Uiso 1 1 calc R U . . .
H26B H 0.260638 -0.020865 0.680006 0.099 Uiso 1 1 calc R U . . .
H26C H 0.317436 0.089800 0.684145 0.099 Uiso 1 1 calc R U . . .
C27 C 0.29856(14) 0.33791(18) 0.56199(15) 0.0483(5) Uani 1 1 d . . . . .
C28 C 0.2920(2) 0.4527(2) 0.4900(2) 0.0714(7) Uani 1 1 d . . . . .
H28A H 0.308950 0.447486 0.417970 0.107 Uiso 1 1 calc R U . . .
H28B H 0.343332 0.500956 0.507984 0.107 Uiso 1 1 calc R U . . .
H28C H 0.219574 0.481987 0.498588 0.107 Uiso 1 1 calc R U . . .
C29 C 0.41393(16) 0.2920(2) 0.5459(2) 0.0737(7) Uani 1 1 d . . . . .
H29A H 0.426888 0.280357 0.475555 0.110 Uiso 1 1 calc R U . . .
H29B H 0.421226 0.222992 0.595668 0.110 Uiso 1 1 calc R U . . .
H29C H 0.466076 0.344001 0.556401 0.110 Uiso 1 1 calc R U . . .
C30 C 0.2736(2) 0.3497(2) 0.67673(19) 0.0764(7) Uani 1 1 d . . . . .
H30A H 0.317064 0.408179 0.688748 0.115 Uiso 1 1 calc R U . . .
H30B H 0.290624 0.281375 0.723851 0.115 Uiso 1 1 calc R U . . .
H30C H 0.197685 0.366755 0.689143 0.115 Uiso 1 1 calc R U . . .
H2 H 0.337(2) 0.8643(16) 0.2071(18) 0.092 Uiso 1 1 d D U . . .
H4 H 0.2946(17) 0.187(2) 0.4134(18) 0.092 Uiso 1 1 d D U . . .
B1A B 0.4360(11) 1.0491(12) 0.2814(13) 0.049(4) Uani 0.277(8) 1 d D . P A 2
F3A F 0.5184(9) 1.0361(16) 0.2154(6) 0.162(8) Uani 0.277(8) 1 d D . P A 2
F4A F 0.4502(7) 1.1369(9) 0.3185(14) 0.134(7) Uani 0.277(8) 1 d D . P A 2
F2A F 0.4386(8) 0.9607(11) 0.3595(11) 0.153(8) Uani 0.277(8) 1 d D . P A 2
F1A F 0.3324(11) 1.0541(13) 0.2535(17) 0.114(6) Uani 0.277(8) 1 d D . 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
B1 F1 1.359(6) . ?
B1 F2 1.342(7) . ?
B1 F3 1.332(6) . ?
B1 F4 1.336(7) . ?
Cl1 Ag1 2.5657(4) . ?
Cl1 Ag2 2.7279(4) . ?
Cl1 Ag2 2.9226(5) 2_566 ?
Ag1 P1 2.3858(5) . ?
Ag1 N3 2.3043(15) . ?
Ag2 P2 2.4142(4) 2_566 ?
Ag2 N1 2.3110(14) . ?
P1 N2 1.6550(16) . ?
P1 C8 1.867(2) . ?
P1 C12 1.868(2) . ?
P2 N4 1.6590(15) . ?
P2 C23 1.871(2) . ?
P2 C27 1.869(2) . ?
N1 C1 1.342(2) . ?
N1 C5 1.339(2) . ?
N2 C7 1.455(2) . ?
N2 H2 0.827(15) . ?
N3 C16 1.349(2) . ?
N3 C20 1.339(2) . ?
N4 C22 1.457(2) . ?
N4 H4 0.829(15) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.367(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.389(2) . ?
C5 C6 1.497(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.520(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.524(3) . ?
C8 C10 1.521(3) . ?
C8 C11 1.527(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.543(4) . ?
C12 C14 1.523(3) . ?
C12 C15 1.528(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.363(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(3) . ?
C20 C21 1.494(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.512(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.533(3) . ?
C23 C25 1.533(3) . ?
C23 C26 1.530(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.525(3) . ?
C27 C29 1.529(3) . ?
C27 C30 1.540(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
B1A F3A 1.297(14) . ?
B1A F4A 1.307(15) . ?
B1A F2A 1.322(15) . ?
B1A F1A 1.356(13) . ?

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
F2 B1 F1 108.3(6) . . ?
F3 B1 F1 108.5(6) . . ?
F3 B1 F2 113.1(5) . . ?
F3 B1 F4 108.1(5) . . ?
F4 B1 F1 110.9(5) . . ?
F4 B1 F2 108.0(5) . . ?
Ag1 Cl1 Ag2 130.868(18) . 2_566 ?
Ag1 Cl1 Ag2 136.978(19) . . ?
Ag2 Cl1 Ag2 82.141(12) . 2_566 ?
P1 Ag1 Cl1 122.552(15) . . ?
N3 Ag1 Cl1 108.59(4) . . ?
N3 Ag1 P1 128.85(4) . . ?
Cl1 Ag2 Cl1 97.859(12) . 2_566 ?
P2 Ag2 Cl1 112.971(14) 2_566 . ?
P2 Ag2 Cl1 108.115(15) 2_566 2_566 ?
N1 Ag2 Cl1 89.70(4) . 2_566 ?
N1 Ag2 Cl1 106.51(4) . . ?
N1 Ag2 P2 133.27(4) . 2_566 ?
N2 P1 Ag1 111.64(6) . . ?
N2 P1 C8 102.66(9) . . ?
N2 P1 C12 106.90(10) . . ?
C8 P1 Ag1 111.46(7) . . ?
C8 P1 C12 112.91(10) . . ?
C12 P1 Ag1 110.92(7) . . ?
N4 P2 Ag2 110.39(5) . 2_566 ?
N4 P2 C23 105.40(9) . . ?
N4 P2 C27 103.19(9) . . ?
C23 P2 Ag2 110.51(6) . 2_566 ?
C27 P2 Ag2 114.93(6) . 2_566 ?
C27 P2 C23 111.75(9) . . ?
C1 N1 Ag2 117.68(12) . . ?
C5 N1 Ag2 124.44(11) . . ?
C5 N1 C1 117.80(15) . . ?
P1 N2 H2 119.2(17) . . ?
C7 N2 P1 124.23(13) . . ?
C7 N2 H2 112.0(17) . . ?
C16 N3 Ag1 120.56(13) . . ?
C20 N3 Ag1 121.46(11) . . ?
C20 N3 C16 117.95(16) . . ?
P2 N4 H4 117.0(16) . . ?
C22 N4 P2 124.62(12) . . ?
C22 N4 H4 116.2(16) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.30(18) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 118.98(18) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.62(18) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4A 120.1 . . ?
C3 C4 C5 119.80(18) . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 121.48(16) . . ?
N1 C5 C6 118.87(15) . . ?
C4 C5 C6 119.58(16) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 C7 110.77(15) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
N2 C7 C6 111.84(16) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 P1 104.76(15) . . ?
C9 C8 C11 108.5(2) . . ?
C10 C8 P1 109.78(16) . . ?
C10 C8 C9 109.3(2) . . ?
C10 C8 C11 109.6(2) . . ?
C11 C8 P1 114.73(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 104.04(15) . . ?
C14 C12 P1 114.01(17) . . ?
C14 C12 C13 108.7(2) . . ?
C14 C12 C15 110.2(2) . . ?
C15 C12 P1 111.34(16) . . ?
C15 C12 C13 108.2(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16 118.2 . . ?
N3 C16 C17 123.6(2) . . ?
C17 C16 H16 118.2 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.36(18) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
N3 C20 C19 121.11(17) . . ?
N3 C20 C21 118.15(17) . . ?
C19 C20 C21 120.73(18) . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C20 C21 C22 113.52(17) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
N4 C22 C21 110.74(17) . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 P2 104.59(14) . . ?
C24 C23 C25 108.1(2) . . ?
C25 C23 P2 109.91(15) . . ?
C26 C23 P2 114.75(15) . . ?
C26 C23 C24 109.21(19) . . ?
C26 C23 C25 110.02(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 P2 105.25(13) . . ?
C28 C27 C29 108.67(19) . . ?
C28 C27 C30 108.1(2) . . ?
C29 C27 P2 114.38(16) . . ?
C29 C27 C30 110.13(18) . . ?
C30 C27 P2 110.01(15) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
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 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
F3A B1A F4A 110.1(13) . . ?
F3A B1A F2A 104.5(12) . . ?
F3A B1A F1A 121.2(16) . . ?
F4A B1A F2A 108.4(14) . . ?
F4A B1A F1A 106.9(12) . . ?
F2A B1A F1A 105.2(13) . . ?

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
Ag1 P1 N2 C7 27.53(19) . . . . ?
Ag1 P1 C8 C9 61.32(18) . . . . ?
Ag1 P1 C8 C10 -55.89(19) . . . . ?
Ag1 P1 C8 C11 -179.84(15) . . . . ?
Ag1 P1 C12 C13 -52.90(19) . . . . ?
Ag1 P1 C12 C14 -171.14(18) . . . . ?
Ag1 P1 C12 C15 63.42(19) . . . . ?
Ag1 N3 C16 C17 -179.68(17) . . . . ?
Ag1 N3 C20 C19 179.66(15) . . . . ?
Ag1 N3 C20 C21 -1.2(2) . . . . ?
Ag2 P2 N4 C22 -6.0(2) 2_566 . . . ?
Ag2 P2 C23 C24 64.14(16) 2_566 . . . ?
Ag2 P2 C23 C25 -51.63(16) 2_566 . . . ?
Ag2 P2 C23 C26 -176.23(14) 2_566 . . . ?
Ag2 P2 C27 C28 -45.17(17) 2_566 . . . ?
Ag2 P2 C27 C29 -164.37(14) 2_566 . . . ?
Ag2 P2 C27 C30 71.08(16) 2_566 . . . ?
Ag2 N1 C1 C2 -177.37(17) . . . . ?
Ag2 N1 C5 C4 176.00(13) . . . . ?
Ag2 N1 C5 C6 -7.1(2) . . . . ?
P1 N2 C7 C6 -130.55(17) . . . . ?
P2 N4 C22 C21 125.79(18) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
N1 C5 C6 C7 -103.39(18) . . . . ?
N2 P1 C8 C9 -58.31(19) . . . . ?
N2 P1 C8 C10 -175.52(18) . . . . ?
N2 P1 C8 C11 60.53(18) . . . . ?
N2 P1 C12 C13 69.02(19) . . . . ?
N2 P1 C12 C14 -49.2(2) . . . . ?
N2 P1 C12 C15 -174.66(18) . . . . ?
N3 C16 C17 C18 -0.4(4) . . . . ?
N3 C20 C21 C22 110.9(2) . . . . ?
N4 P2 C23 C24 -55.13(17) . . . . ?
N4 P2 C23 C25 -170.90(15) . . . . ?
N4 P2 C23 C26 64.50(17) . . . . ?
N4 P2 C27 C28 75.07(16) . . . . ?
N4 P2 C27 C29 -44.13(18) . . . . ?
N4 P2 C27 C30 -168.68(16) . . . . ?
C1 N1 C5 C4 -0.6(3) . . . . ?
C1 N1 C5 C6 176.23(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 N1 1.4(3) . . . . ?
C3 C4 C5 C6 -175.47(19) . . . . ?
C4 C5 C6 C7 73.5(2) . . . . ?
C5 N1 C1 C2 -0.5(3) . . . . ?
C5 C6 C7 N2 -168.62(16) . . . . ?
C8 P1 N2 C7 147.04(17) . . . . ?
C8 P1 C12 C13 -178.83(17) . . . . ?
C8 P1 C12 C14 62.9(2) . . . . ?
C8 P1 C12 C15 -62.5(2) . . . . ?
C12 P1 N2 C7 -93.94(18) . . . . ?
C12 P1 C8 C9 -173.04(18) . . . . ?
C12 P1 C8 C10 69.8(2) . . . . ?
C12 P1 C8 C11 -54.2(2) . . . . ?
C16 N3 C20 C19 -2.2(3) . . . . ?
C16 N3 C20 C21 176.92(17) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 N3 0.6(3) . . . . ?
C18 C19 C20 C21 -178.5(2) . . . . ?
C19 C20 C21 C22 -69.9(3) . . . . ?
C20 N3 C16 C17 2.2(3) . . . . ?
C20 C21 C22 N4 177.18(17) . . . . ?
C23 P2 N4 C22 113.40(19) . . . . ?
C23 P2 C27 C28 -172.15(15) . . . . ?
C23 P2 C27 C29 68.65(18) . . . . ?
C23 P2 C27 C30 -55.90(18) . . . . ?
C27 P2 N4 C22 -129.26(19) . . . . ?
C27 P2 C23 C24 -166.52(15) . . . . ?
C27 P2 C23 C25 77.71(16) . . . . ?
C27 P2 C23 C26 -46.89(18) . . . . ?

_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_JCK_CutBu2C_green_03092021
_audit_block_doi                 10.5517/ccdc.csd.cc2bs75k
_database_code_depnum_ccdc_archive 'CCDC 2168238'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 Cl2 Cu N2 O P'
_chemical_formula_sum            'C15 H27 Cl2 Cu N2 O P'
_chemical_formula_weight         416.79
_chemical_absolute_configuration ?
_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'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   9.670(4)
_cell_length_b                   24.423(9)
_cell_length_c                   8.680(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.684(9)
_cell_angle_gamma                90
_cell_volume                     2000.0(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9564
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.4622
_cell_measurement_theta_min      2.3143
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.469
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.085
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42015
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.563
_diffrn_reflns_theta_min         1.668
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                6473
_reflns_number_total             8823
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         8823
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.00114
 -0.00114
2. Restrained distances
 N2-H2N
 0.9 with sigma of 0.02
 P1-H2N
 2.08 with sigma of 0.04
 C7-H2N
 1.91 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6AB), C7(H7A,H7AB)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cu1 Cu 0.50008(3) 0.60877(2) 0.27781(3) 0.03742(9) Uani 1 1 d . . . . .
Cl1 Cl 0.70535(10) 0.60307(6) 0.20598(11) 0.0722(3) Uani 1 1 d . . . . .
Cl2 Cl 0.38253(12) 0.65838(5) 0.08104(11) 0.0718(3) Uani 1 1 d . . . . .
P1 P 0.63741(7) 0.63248(3) 0.66152(7) 0.03204(13) Uani 1 1 d D . . . .
O1 O 0.5705(2) 0.60744(8) 0.5052(2) 0.0412(4) Uani 1 1 d . . . . .
N1 N 0.3282(2) 0.43290(10) 0.8112(3) 0.0369(5) Uani 1 1 d . . . . .
N2 N 0.5886(3) 0.59709(10) 0.8011(3) 0.0359(4) Uani 1 1 d D . . . .
H2N H 0.613(4) 0.6056(13) 0.900(3) 0.043 Uiso 1 1 d D U . . .
C1 C 0.2054(4) 0.40632(17) 0.8017(5) 0.0551(8) Uani 1 1 d . . . . .
H1 H 0.196169 0.370820 0.761980 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0922(4) 0.4301(2) 0.8490(6) 0.0691(12) Uani 1 1 d . . . . .
H2 H 0.007847 0.410855 0.840343 0.083 Uiso 1 1 calc R U . . .
C3 C 0.1047(4) 0.48202(19) 0.9087(5) 0.0647(10) Uani 1 1 d . . . . .
H3 H 0.029719 0.498275 0.942753 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2292(4) 0.50984(15) 0.9178(4) 0.0509(7) Uani 1 1 d . . . . .
H4 H 0.239678 0.545261 0.957977 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3396(3) 0.48462(11) 0.8662(3) 0.0357(5) Uani 1 1 d . . . . .
C6 C 0.4760(3) 0.51446(11) 0.8728(4) 0.0410(6) Uani 1 1 d . . . . .
H6A H 0.540194 0.490870 0.831793 0.049 Uiso 1 1 calc R U . . .
H6AB H 0.519453 0.522668 0.981989 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4556(3) 0.56729(12) 0.7789(3) 0.0383(5) Uani 1 1 d D . . . .
H7A H 0.421207 0.559111 0.667708 0.046 Uiso 1 1 calc R U . . .
H7AB H 0.385244 0.589793 0.813060 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8315(3) 0.62421(14) 0.7046(4) 0.0449(6) Uani 1 1 d . . . . .
C9 C 0.8537(4) 0.56606(17) 0.6443(5) 0.0584(8) Uani 1 1 d . . . . .
H9A H 0.824870 0.565311 0.531183 0.088 Uiso 1 1 calc R U . . .
H9B H 0.797834 0.540389 0.688388 0.088 Uiso 1 1 calc R U . . .
H9C H 0.952004 0.556325 0.675795 0.088 Uiso 1 1 calc R U . . .
C10 C 0.8968(4) 0.6275(2) 0.8816(4) 0.0603(9) Uani 1 1 d . . . . .
H10A H 0.998267 0.628366 0.898002 0.090 Uiso 1 1 calc R U . . .
H10B H 0.868787 0.595994 0.933545 0.090 Uiso 1 1 calc R U . . .
H10C H 0.864422 0.660096 0.924307 0.090 Uiso 1 1 calc R U . . .
C11 C 0.9020(4) 0.6658(2) 0.6139(5) 0.0669(11) Uani 1 1 d . . . . .
H11A H 0.859697 0.663343 0.503163 0.100 Uiso 1 1 calc R U . . .
H11B H 1.001476 0.657999 0.630831 0.100 Uiso 1 1 calc R U . . .
H11C H 0.888840 0.702065 0.650806 0.100 Uiso 1 1 calc R U . . .
C12 C 0.5739(4) 0.70357(12) 0.6646(4) 0.0487(7) Uani 1 1 d . . . . .
C13 C 0.5959(5) 0.73477(16) 0.5166(5) 0.0697(11) Uani 1 1 d . . . . .
H13A H 0.552357 0.714716 0.423434 0.104 Uiso 1 1 calc R U . . .
H13B H 0.695473 0.738561 0.521063 0.104 Uiso 1 1 calc R U . . .
H13C H 0.553371 0.770398 0.513524 0.104 Uiso 1 1 calc R U . . .
C14 C 0.6454(5) 0.73331(16) 0.8154(6) 0.0740(12) Uani 1 1 d . . . . .
H14A H 0.744458 0.737696 0.817593 0.111 Uiso 1 1 calc R U . . .
H14B H 0.634191 0.712328 0.905338 0.111 Uiso 1 1 calc R U . . .
H14C H 0.602551 0.768657 0.818120 0.111 Uiso 1 1 calc R U . . .
C15 C 0.4157(4) 0.69998(17) 0.6582(5) 0.0628(9) Uani 1 1 d . . . . .
H15A H 0.376622 0.736210 0.654267 0.094 Uiso 1 1 calc R U . . .
H15B H 0.400566 0.681421 0.750548 0.094 Uiso 1 1 calc R U . . .
H15C H 0.370151 0.680031 0.565601 0.094 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
Cu1 Cl1 2.2117(12) . ?
Cu1 Cl2 2.1965(10) . ?
Cu1 O1 1.941(2) . ?
Cu1 N1 2.023(3) 2_564 ?
P1 O1 1.500(2) . ?
P1 N2 1.640(2) . ?
P1 C8 1.843(3) . ?
P1 C12 1.844(3) . ?
N1 C1 1.341(4) . ?
N1 C5 1.346(4) . ?
N2 H2N 0.86(2) . ?
N2 C7 1.454(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 C6 1.497(4) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C6 C7 1.516(4) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 C9 1.545(5) . ?
C8 C10 1.530(5) . ?
C8 C11 1.533(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.548(5) . ?
C12 C14 1.523(5) . ?
C12 C15 1.521(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
Cl2 Cu1 Cl1 99.14(5) . . ?
O1 Cu1 Cl1 98.59(8) . . ?
O1 Cu1 Cl2 143.68(7) . . ?
O1 Cu1 N1 87.79(9) . 2_564 ?
N1 Cu1 Cl1 145.59(8) 2_564 . ?
N1 Cu1 Cl2 95.04(8) 2_564 . ?
O1 P1 N2 108.47(12) . . ?
O1 P1 C8 110.91(14) . . ?
O1 P1 C12 108.56(13) . . ?
N2 P1 C8 103.77(14) . . ?
N2 P1 C12 109.55(15) . . ?
C8 P1 C12 115.34(16) . . ?
P1 O1 Cu1 153.95(13) . . ?
C1 N1 Cu1 119.5(2) . 2_565 ?
C1 N1 C5 118.6(3) . . ?
C5 N1 Cu1 121.16(18) . 2_565 ?
P1 N2 H2N 123(2) . . ?
C7 N2 P1 123.75(18) . . ?
C7 N2 H2N 107(2) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.9(4) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 118.2(2) . . ?
C4 C5 C6 120.3(3) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6AB 109.1 . . ?
C5 C6 C7 112.6(2) . . ?
H6A C6 H6AB 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6AB 109.1 . . ?
N2 C7 C6 110.4(2) . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7AB 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7AB 109.6 . . ?
H7A C7 H7AB 108.1 . . ?
C9 C8 P1 104.0(2) . . ?
C10 C8 P1 112.1(2) . . ?
C10 C8 C9 109.3(3) . . ?
C10 C8 C11 110.5(3) . . ?
C11 C8 P1 111.8(3) . . ?
C11 C8 C9 108.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 110.2(3) . . ?
C14 C12 P1 111.8(2) . . ?
C14 C12 C13 111.0(3) . . ?
C15 C12 P1 106.3(2) . . ?
C15 C12 C13 108.5(3) . . ?
C15 C12 C14 108.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.00114
2 -0.00114
####################################################################### 
# 
# 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_JCK_tBu1C1H_Oxidized
_audit_block_doi                 10.5517/ccdc.csd.cc2bs72g
_database_code_depnum_ccdc_archive 'CCDC 2168235'
loop_
_audit_author_name
_audit_author_address
'Jordan Kelly'
;Duquesne University
United States of America
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H25 N2 O P'
_chemical_formula_sum            'C14 H25 N2 O P'
_chemical_formula_weight         268.33
_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      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                   11.509(8)
_cell_length_b                   22.039(16)
_cell_length_c                   13.238(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.946(19)
_cell_angle_gamma                90
_cell_volume                     3212(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7607
_cell_measurement_theta_min      2.4559
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   mu*r=0.2000
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          1.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48890
_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         28.839
_diffrn_reflns_theta_min         1.848
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5581
_reflns_number_total             8391
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker Instrument Service V2017.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         8391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.035
_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)+(0.0747P)²+0.5205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1494
_olex2_refinement_description    
;
1. Others
 Sof(C15')=Sof(H15')=1-FVAR(1)
 Sof(C15)=Sof(H15)=FVAR(1)
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4A), C17(H17), C18(H18), C15(H15), C15'(H15')
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.53836(4) 0.31956(2) 0.21118(3) 0.04407(12) Uani 1 1 d . . . . .
P2 P 0.27972(4) 0.18252(2) 0.41578(3) 0.04753(13) Uani 1 1 d . . . . .
O1 O 0.44831(11) 0.28801(6) 0.25296(10) 0.0607(3) Uani 1 1 d . . . . .
O2 O 0.22123(12) 0.18182(6) 0.50187(10) 0.0584(3) Uani 1 1 d . . . . .
N1 N 0.51399(19) 0.11197(8) 0.08861(18) 0.0865(6) Uani 1 1 d . . . . .
N2 N 0.59400(14) 0.27275(6) 0.13972(12) 0.0472(3) Uani 1 1 d . . . . .
N3 N 0.3767(2) 0.40594(10) 0.48550(19) 0.0916(6) Uani 1 1 d . . . . .
N4 N 0.31928(14) 0.25212(7) 0.39377(12) 0.0521(4) Uani 1 1 d . . . . .
C1 C 0.5630(4) 0.05708(12) 0.1189(3) 0.1187(12) Uani 1 1 d . . . . .
H1 H 0.515438 0.023096 0.093916 0.142 Uiso 1 1 calc R U . . .
C2 C 0.6771(4) 0.04794(12) 0.1832(3) 0.1236(12) Uani 1 1 d . . . . .
H2 H 0.705734 0.008808 0.201706 0.148 Uiso 1 1 calc R U . . .
C3 C 0.7492(3) 0.09677(12) 0.2203(3) 0.1000(9) Uani 1 1 d . . . . .
H3 H 0.827927 0.091872 0.264405 0.120 Uiso 1 1 calc R U . . .
C4 C 0.7018(2) 0.15401(9) 0.19056(18) 0.0683(5) Uani 1 1 d . . . . .
H4A H 0.748913 0.188315 0.214263 0.082 Uiso 1 1 calc R U . . .
C5 C 0.58535(17) 0.15988(8) 0.12610(15) 0.0534(4) Uani 1 1 d . . . . .
C6 C 0.52560(17) 0.21971(8) 0.08923(14) 0.0563(4) Uani 1 1 d . . . . .
H6A H 0.512174 0.222847 0.013597 0.068 Uiso 1 1 calc R U . . .
H6B H 0.446711 0.220269 0.101850 0.068 Uiso 1 1 calc R U . . .
C7 C 0.67329(18) 0.34332(9) 0.31885(15) 0.0600(5) Uani 1 1 d . . . . .
C8 C 0.7014(2) 0.28845(12) 0.39538(17) 0.0850(7) Uani 1 1 d . . . . .
H8A H 0.631580 0.279613 0.418613 0.128 Uiso 1 1 calc R U . . .
H8B H 0.769102 0.298021 0.455332 0.128 Uiso 1 1 calc R U . . .
H8C H 0.720782 0.253735 0.359584 0.128 Uiso 1 1 calc R U . . .
C9 C 0.6464(2) 0.39766(11) 0.38071(19) 0.0866(7) Uani 1 1 d . . . . .
H9A H 0.632204 0.433020 0.336444 0.130 Uiso 1 1 calc R U . . .
H9B H 0.714569 0.404732 0.441658 0.130 Uiso 1 1 calc R U . . .
H9C H 0.575655 0.389267 0.402774 0.130 Uiso 1 1 calc R U . . .
C10 C 0.7855(2) 0.35637(12) 0.2814(2) 0.0858(7) Uani 1 1 d . . . . .
H10A H 0.804357 0.321182 0.246401 0.129 Uiso 1 1 calc R U . . .
H10B H 0.853358 0.366058 0.341166 0.129 Uiso 1 1 calc R U . . .
H10C H 0.768746 0.390008 0.233226 0.129 Uiso 1 1 calc R U . . .
C11 C 0.4599(2) 0.38261(9) 0.12517(16) 0.0653(5) Uani 1 1 d . . . . .
C12 C 0.3819(3) 0.41929(12) 0.1804(2) 0.0997(9) Uani 1 1 d . . . . .
H12A H 0.329495 0.446243 0.130492 0.150 Uiso 1 1 calc R U . . .
H12B H 0.433953 0.442457 0.237193 0.150 Uiso 1 1 calc R U . . .
H12C H 0.333701 0.391993 0.208070 0.150 Uiso 1 1 calc R U . . .
C13 C 0.3723(3) 0.35178(13) 0.02761(19) 0.0957(8) Uani 1 1 d . . . . .
H13A H 0.321634 0.381967 -0.016141 0.144 Uiso 1 1 calc R U . . .
H13B H 0.322552 0.322967 0.050235 0.144 Uiso 1 1 calc R U . . .
H13C H 0.418452 0.331254 -0.011905 0.144 Uiso 1 1 calc R U . . .
C14 C 0.5464(3) 0.42406(11) 0.0892(2) 0.0992(9) Uani 1 1 d . . . . .
H14A H 0.598299 0.399974 0.060057 0.149 Uiso 1 1 calc R U . . .
H14B H 0.594965 0.446698 0.148458 0.149 Uiso 1 1 calc R U . . .
H14C H 0.500309 0.451578 0.036378 0.149 Uiso 1 1 calc R U . . .
C16 C 0.2245(4) 0.47486(13) 0.3897(3) 0.1076(11) Uani 1 1 d . . . . .
C17 C 0.1512(3) 0.42783(13) 0.3460(3) 0.1078(9) Uani 1 1 d . . . . .
H17 H 0.074579 0.434870 0.299389 0.129 Uiso 1 1 calc R U . . .
C18 C 0.1920(3) 0.36906(11) 0.3720(2) 0.0883(7) Uani 1 1 d . . . . .
H18 H 0.143413 0.336171 0.342299 0.106 Uiso 1 1 calc R U . . .
C19 C 0.3048(2) 0.35986(9) 0.44194(16) 0.0633(5) Uani 1 1 d . . . . .
C20 C 0.3546(2) 0.29782(9) 0.47655(16) 0.0661(5) Uani 1 1 d . . . . .
H20A H 0.442539 0.300111 0.501014 0.079 Uiso 1 1 calc R U . . .
H20B H 0.326736 0.285116 0.535710 0.079 Uiso 1 1 calc R U . . .
C21 C 0.4178(2) 0.13389(10) 0.45849(18) 0.0686(5) Uani 1 1 d . . . . .
C22 C 0.3880(3) 0.07231(11) 0.5012(3) 0.1037(9) Uani 1 1 d . . . . .
H22A H 0.342439 0.047669 0.443371 0.156 Uiso 1 1 calc R U . . .
H22B H 0.340957 0.079100 0.549221 0.156 Uiso 1 1 calc R U . . .
H22C H 0.462202 0.051946 0.537377 0.156 Uiso 1 1 calc R U . . .
C23 C 0.5059(2) 0.16722(12) 0.5525(2) 0.0920(8) Uani 1 1 d . . . . .
H23A H 0.533288 0.204016 0.527984 0.138 Uiso 1 1 calc R U . . .
H23B H 0.574428 0.141627 0.583848 0.138 Uiso 1 1 calc R U . . .
H23C H 0.464838 0.176743 0.604025 0.138 Uiso 1 1 calc R U . . .
C24 C 0.4815(2) 0.12511(15) 0.3732(2) 0.1040(9) Uani 1 1 d . . . . .
H24A H 0.430278 0.101909 0.316005 0.156 Uiso 1 1 calc R U . . .
H24B H 0.556683 0.103906 0.402452 0.156 Uiso 1 1 calc R U . . .
H24C H 0.497618 0.163987 0.347416 0.156 Uiso 1 1 calc R U . . .
C25 C 0.17192(18) 0.15971(9) 0.28830(15) 0.0592(5) Uani 1 1 d . . . . .
C26 C 0.1392(3) 0.09215(11) 0.2884(2) 0.0882(7) Uani 1 1 d . . . . .
H26A H 0.076123 0.082661 0.224939 0.132 Uiso 1 1 calc R U . . .
H26B H 0.111326 0.083573 0.348595 0.132 Uiso 1 1 calc R U . . .
H26C H 0.209654 0.068006 0.291876 0.132 Uiso 1 1 calc R U . . .
C27 C 0.2160(2) 0.17389(12) 0.19199(16) 0.0834(7) Uani 1 1 d . . . . .
H27A H 0.154087 0.162923 0.128627 0.125 Uiso 1 1 calc R U . . .
H27B H 0.288492 0.151146 0.196517 0.125 Uiso 1 1 calc R U . . .
H27C H 0.233035 0.216477 0.190626 0.125 Uiso 1 1 calc R U . . .
C28 C 0.0557(2) 0.19682(12) 0.27929(19) 0.0797(6) Uani 1 1 d . . . . .
H28A H 0.072431 0.239170 0.273835 0.120 Uiso 1 1 calc R U . . .
H28B H 0.029438 0.190099 0.340858 0.120 Uiso 1 1 calc R U . . .
H28C H -0.007011 0.184276 0.217557 0.120 Uiso 1 1 calc R U . . .
H1B H 0.6375(17) 0.2870(9) 0.1086(15) 0.051(5) Uiso 1 1 d . . . . .
H4 H 0.3513(17) 0.2577(9) 0.3477(15) 0.054(5) Uiso 1 1 d . . . . .
H16 H 0.197(3) 0.5197(16) 0.380(2) 0.142(11) Uiso 1 1 d . . . . .
C15 C 0.3381(13) 0.4605(6) 0.4652(18) 0.107(3) Uani 0.82(4) 1 d . . P A 1
H15 H 0.386174 0.492175 0.501109 0.129 Uiso 0.82(4) 1 calc R U P A 1
C15' C 0.321(3) 0.4674(16) 0.431(3) 0.062(7) Uani 0.18(4) 1 d . . P A 2
H15' H 0.374448 0.499737 0.434721 0.074 Uiso 0.18(4) 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 O1 1.4824(14) . ?
P1 N2 1.6499(16) . ?
P1 C7 1.851(2) . ?
P1 C11 1.856(2) . ?
P2 O2 1.4831(15) . ?
P2 N4 1.6500(19) . ?
P2 C21 1.863(2) . ?
P2 C25 1.849(2) . ?
N1 C1 1.346(4) . ?
N1 C5 1.341(2) . ?
N2 C6 1.458(2) . ?
N2 H1B 0.80(2) . ?
N3 C19 1.331(3) . ?
N3 C15 1.284(16) . ?
N3 C15' 1.58(3) . ?
N4 C20 1.456(3) . ?
N4 H4 0.809(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.356(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.360(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.369(3) . ?
C5 C6 1.501(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.550(3) . ?
C7 C9 1.532(3) . ?
C7 C10 1.539(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.542(3) . ?
C11 C13 1.545(3) . ?
C11 C14 1.526(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.355(5) . ?
C16 H16 1.03(3) . ?
C16 C15 1.43(2) . ?
C16 C15' 1.10(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(3) . ?
C19 C20 1.502(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.546(3) . ?
C21 C23 1.543(3) . ?
C21 C24 1.528(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.536(3) . ?
C25 C27 1.536(3) . ?
C25 C28 1.542(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C15 H15 0.9300 . ?
C15' H15' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N2 110.56(9) . . ?
O1 P1 C7 111.49(10) . . ?
O1 P1 C11 108.18(10) . . ?
N2 P1 C7 103.86(10) . . ?
N2 P1 C11 108.49(10) . . ?
C7 P1 C11 114.17(10) . . ?
O2 P2 N4 110.84(8) . . ?
O2 P2 C21 107.39(9) . . ?
O2 P2 C25 111.37(10) . . ?
N4 P2 C21 109.48(10) . . ?
N4 P2 C25 103.76(9) . . ?
C25 P2 C21 114.00(10) . . ?
C5 N1 C1 116.0(2) . . ?
P1 N2 H1B 117.1(14) . . ?
C6 N2 P1 121.07(13) . . ?
C6 N2 H1B 114.5(14) . . ?
C19 N3 C15' 110.0(16) . . ?
C15 N3 C19 119.4(8) . . ?
P2 N4 H4 119.0(14) . . ?
C20 N4 P2 122.75(14) . . ?
C20 N4 H4 111.9(14) . . ?
N1 C1 H1 117.8 . . ?
N1 C1 C2 124.5(3) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 122.61(19) . . ?
N1 C5 C6 113.46(19) . . ?
C4 C5 C6 123.92(16) . . ?
N2 C6 C5 114.84(16) . . ?
N2 C6 H6A 108.6 . . ?
N2 C6 H6B 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 P1 104.52(14) . . ?
C9 C7 P1 112.20(16) . . ?
C9 C7 C8 107.25(19) . . ?
C9 C7 C10 110.18(18) . . ?
C10 C7 P1 113.52(15) . . ?
C10 C7 C8 108.8(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 P1 110.36(16) . . ?
C12 C11 C13 107.4(2) . . ?
C13 C11 P1 105.41(15) . . ?
C14 C11 P1 113.26(17) . . ?
C14 C11 C12 110.9(2) . . ?
C14 C11 C13 109.2(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C16 H16 123.3(19) . . ?
C17 C16 C15 117.3(5) . . ?
C15 C16 H16 118.7(19) . . ?
C15' C16 C17 121(2) . . ?
C15' C16 H16 116(3) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
N3 C19 C18 121.7(2) . . ?
N3 C19 C20 115.4(2) . . ?
C18 C19 C20 122.83(19) . . ?
N4 C20 C19 113.72(17) . . ?
N4 C20 H20A 108.8 . . ?
N4 C20 H20B 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 P2 110.82(17) . . ?
C23 C21 P2 105.84(15) . . ?
C23 C21 C22 106.7(2) . . ?
C24 C21 P2 113.54(17) . . ?
C24 C21 C22 111.4(2) . . ?
C24 C21 C23 108.2(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 P2 111.23(15) . . ?
C26 C25 C28 107.86(19) . . ?
C27 C25 P2 113.96(15) . . ?
C27 C25 C26 109.81(18) . . ?
C27 C25 C28 108.47(19) . . ?
C28 C25 P2 105.21(14) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C15 C16 122.9(9) . . ?
N3 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
N3 C15' H15' 117.6 . . ?
C16 C15' N3 125(3) . . ?
C16 C15' H15' 117.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
