# 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 2024

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

data_jmy-14-1
_database_code_depnum_ccdc_archive 'CCDC 1942668'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C40 H32 Cu N O P2'
_chemical_formula_sum            'C40 H32 Cu N O P2'
_chemical_formula_weight         668.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

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

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

_cell_length_a                   17.3563(2)
_cell_length_b                   11.8638(2)
_cell_length_c                   8.15090(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1678.37(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    5655
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      66.57

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            10246
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.726
_diffrn_reflns_theta_max         66.566
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_point_group_measured_fraction_full 0.745
_reflns_number_total             2286
_reflns_number_gt                2228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.396
_reflns_Friedel_fraction_max     0.457
_reflns_Friedel_fraction_full    0.458

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 615 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2286
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036

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 0.000000 0.40762(4) 0.11312(7) 0.02409(14) Uani 1 2 d S T P . .
P1 P 0.09192(3) 0.28624(5) 0.04043(9) 0.02182(15) Uani 1 1 d . . . . .
O1 O 0.000000 0.5504(2) -0.0269(4) 0.0294(6) Uani 1 2 d S T P . .
N1 N 0.000000 0.5179(3) 0.3012(4) 0.0245(7) Uani 1 2 d S T P . .
C1 C 0.000000 0.6388(3) 0.0665(5) 0.0258(8) Uani 1 2 d S T P . .
C2 C 0.000000 0.7496(3) 0.0063(6) 0.0374(10) Uani 1 2 d S T P . .
H2 H 0.000000 0.761959 -0.108878 0.045 Uiso 1 2 calc R U P . .
C3 C 0.000000 0.8418(3) 0.1122(8) 0.0421(10) Uani 1 2 d S T P . .
H3 H 0.000000 0.915485 0.066575 0.051 Uiso 1 2 calc R U P . .
C4 C 0.000000 0.8306(3) 0.2782(6) 0.0373(10) Uani 1 2 d S T P . .
H4 H 0.000000 0.895360 0.346699 0.045 Uiso 1 2 calc R U P . .
C5 C 0.000000 0.7213(3) 0.3476(6) 0.0304(9) Uani 1 2 d S T P . .
C6 C 0.000000 0.6269(3) 0.2418(5) 0.0236(8) Uani 1 2 d S T P . .
C7 C 0.000000 0.6988(4) 0.5181(6) 0.0384(10) Uani 1 2 d S T P . .
H7 H 0.000000 0.759501 0.594110 0.046 Uiso 1 2 calc R U P . .
C8 C 0.000000 0.5902(4) 0.5737(5) 0.0378(10) Uani 1 2 d S T P . .
H8 H 0.000000 0.575454 0.688266 0.045 Uiso 1 2 calc R U P . .
C9 C 0.000000 0.5000(4) 0.4609(5) 0.0312(9) Uani 1 2 d S T P . .
C10 C 0.000000 0.3794(4) 0.5175(6) 0.0471(11) Uani 1 2 d S T P . .
H10A H -0.030787 0.333673 0.441726 0.071 Uiso 0.5 1 calc R U P . .
H10B H -0.022217 0.374850 0.627801 0.071 Uiso 0.5 1 calc R U P . .
H10C H 0.053004 0.350933 0.519721 0.071 Uiso 0.5 1 calc R U P . .
C11 C 0.13887(15) 0.1957(2) 0.1912(4) 0.0276(6) Uani 1 1 d . . . . .
C12 C 0.1831(2) 0.2466(3) 0.3105(5) 0.0521(9) Uani 1 1 d . . . . .
H12 H 0.187113 0.326421 0.312922 0.063 Uiso 1 1 calc R U . . .
C13 C 0.2217(3) 0.1833(4) 0.4268(5) 0.0675(12) Uani 1 1 d . . . . .
H13 H 0.252787 0.219603 0.506795 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2150(2) 0.0666(3) 0.4266(5) 0.0510(9) Uani 1 1 d . . . . .
H14 H 0.241553 0.022600 0.505914 0.061 Uiso 1 1 calc R U . . .
C15 C 0.17028(18) 0.0165(3) 0.3120(5) 0.0434(8) Uani 1 1 d . . . . .
H15 H 0.164956 -0.063146 0.312239 0.052 Uiso 1 1 calc R U . . .
C16 C 0.13209(17) 0.0795(2) 0.1944(4) 0.0354(7) Uani 1 1 d . . . . .
H16 H 0.100934 0.042561 0.115053 0.042 Uiso 1 1 calc R U . . .
C17 C 0.17193(14) 0.3343(2) -0.0874(3) 0.0243(5) Uani 1 1 d . . . . .
C18 C 0.24364(15) 0.2814(2) -0.0930(4) 0.0315(6) Uani 1 1 d . . . . .
H18 H 0.253153 0.217009 -0.026820 0.038 Uiso 1 1 calc R U . . .
C19 C 0.30097(15) 0.3224(3) -0.1946(5) 0.0390(7) Uani 1 1 d . . . . .
H19 H 0.349665 0.285935 -0.197789 0.047 Uiso 1 1 calc R U . . .
C20 C 0.28803(18) 0.4160(3) -0.2915(5) 0.0421(8) Uani 1 1 d . . . . .
H20 H 0.327666 0.443943 -0.360795 0.051 Uiso 1 1 calc R U . . .
C21 C 0.21715(18) 0.4687(3) -0.2870(4) 0.0418(8) Uani 1 1 d . . . . .
H21 H 0.207633 0.532122 -0.355250 0.050 Uiso 1 1 calc R U . . .
C22 C 0.15964(16) 0.4293(2) -0.1830(4) 0.0330(6) Uani 1 1 d . . . . .
H22 H 0.111670 0.467706 -0.177442 0.040 Uiso 1 1 calc R U . . .
C23 C 0.04044(15) 0.1875(2) -0.0962(3) 0.0234(5) Uani 1 1 d . . . . .
C24 C 0.07953(16) 0.1167(3) -0.2031(4) 0.0346(7) Uani 1 1 d . . . . .
H24 H 0.134259 0.117131 -0.204529 0.042 Uiso 1 1 calc R U . . .
C25 C 0.04021(18) 0.0459(3) -0.3068(4) 0.0447(8) Uani 1 1 d . . . . .
H25 H 0.067657 -0.002866 -0.378380 0.054 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 N1 2.015(3) . ?
Cu1 O1 2.042(3) . ?
Cu1 P1 2.2293(7) 3 ?
Cu1 P1 2.2294(7) . ?
P1 C11 1.825(3) . ?
P1 C17 1.827(3) . ?
P1 C23 1.847(3) . ?
O1 C1 1.296(5) . ?
N1 C9 1.319(5) . ?
N1 C6 1.381(5) . ?
C1 C2 1.403(5) . ?
C1 C6 1.436(6) . ?
C2 C3 1.394(6) . ?
C3 C4 1.359(8) . ?
C4 C5 1.415(6) . ?
C5 C6 1.414(5) . ?
C5 C7 1.415(7) . ?
C7 C8 1.366(6) . ?
C8 C9 1.411(6) . ?
C9 C10 1.503(6) . ?
C11 C12 1.378(4) . ?
C11 C16 1.383(4) . ?
C12 C13 1.382(5) . ?
C13 C14 1.389(5) . ?
C14 C15 1.352(5) . ?
C15 C16 1.384(4) . ?
C17 C22 1.387(4) . ?
C17 C18 1.394(4) . ?
C18 C19 1.383(4) . ?
C19 C20 1.380(5) . ?
C20 C21 1.381(5) . ?
C21 C22 1.390(4) . ?
C23 C24 1.388(4) . ?
C23 C23 1.404(5) 3 ?
C24 C25 1.373(4) . ?
C25 C25 1.396(6) 3 ?

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 Cu1 O1 83.49(13) . . ?
N1 Cu1 P1 128.42(4) . 3 ?
O1 Cu1 P1 112.78(6) . 3 ?
N1 Cu1 P1 128.42(4) . . ?
O1 Cu1 P1 112.78(6) . . ?
P1 Cu1 P1 91.39(3) 3 . ?
C11 P1 C17 103.20(12) . . ?
C11 P1 C23 104.42(12) . . ?
C17 P1 C23 102.81(12) . . ?
C11 P1 Cu1 121.40(10) . . ?
C17 P1 Cu1 119.60(9) . . ?
C23 P1 Cu1 102.92(8) . . ?
C1 O1 Cu1 110.1(3) . . ?
C9 N1 C6 119.8(3) . . ?
C9 N1 Cu1 130.3(3) . . ?
C6 N1 Cu1 110.0(3) . . ?
O1 C1 C2 123.5(4) . . ?
O1 C1 C6 120.3(4) . . ?
C2 C1 C6 116.1(4) . . ?
C3 C2 C1 121.2(4) . . ?
C4 C3 C2 122.7(4) . . ?
C3 C4 C5 119.2(4) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 C7 116.7(4) . . ?
C4 C5 C7 124.4(4) . . ?
N1 C6 C5 121.9(4) . . ?
N1 C6 C1 116.2(4) . . ?
C5 C6 C1 121.9(4) . . ?
C8 C7 C5 120.3(4) . . ?
C7 C8 C9 119.9(4) . . ?
N1 C9 C8 121.4(4) . . ?
N1 C9 C10 117.1(4) . . ?
C8 C9 C10 121.5(4) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 P1 117.8(2) . . ?
C16 C11 P1 124.1(2) . . ?
C11 C12 C13 121.0(3) . . ?
C12 C13 C14 120.0(4) . . ?
C15 C14 C13 119.1(3) . . ?
C14 C15 C16 121.1(3) . . ?
C11 C16 C15 120.6(3) . . ?
C22 C17 C18 119.0(3) . . ?
C22 C17 P1 117.2(2) . . ?
C18 C17 P1 123.8(2) . . ?
C19 C18 C17 120.2(3) . . ?
C20 C19 C18 120.5(3) . . ?
C19 C20 C21 119.6(3) . . ?
C20 C21 C22 120.2(3) . . ?
C17 C22 C21 120.4(3) . . ?
C24 C23 C23 119.27(16) . 3 ?
C24 C23 P1 121.7(2) . . ?
C23 C23 P1 118.94(8) 3 . ?
C25 C24 C23 120.9(3) . . ?
C24 C25 C25 119.81(17) . 3 ?



####################################################################### 
# 
# 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_jmy-14-2
_database_code_depnum_ccdc_archive 'CCDC 1943248'
loop_
_audit_author_name
_audit_author_address
'Lise-Marie Chamoreau'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_formula_moiety         'C37 H30 Cu N O2 P2'
_chemical_formula_sum            'C37 H30 Cu N O2 P2'
_chemical_formula_weight         646.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.3072(2)
_cell_length_b                   18.5057(4)
_cell_length_c                   19.9706(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.867(1)
_cell_angle_gamma                90
_cell_volume                     3059.02(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    8399
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      67.74

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            26598
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.261
_diffrn_reflns_theta_max         68.525
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5504
_reflns_number_gt                4645
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.4383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5504
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.047

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 0.59934(3) 0.28780(2) 0.26811(2) 0.02409(9) Uani 1 1 d . . . . .
P1 P 0.50039(6) 0.31944(3) 0.16482(2) 0.02241(11) Uani 1 1 d . . . . .
P2 P 0.52111(5) 0.39416(2) 0.30900(2) 0.02080(11) Uani 1 1 d . . . . .
O1 O 0.49634(16) 0.20231(7) 0.31429(8) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.5658(2) 0.11996(9) 0.39352(8) 0.0495(4) Uani 1 1 d . . . . .
N1 N 0.80600(18) 0.23616(8) 0.30288(8) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.5965(2) 0.16607(10) 0.35195(10) 0.0295(5) Uani 1 1 d . . . . .
C2 C 0.7745(2) 0.17998(10) 0.34313(9) 0.0254(4) Uani 1 1 d . . . . .
C3 C 0.8943(3) 0.13627(12) 0.37250(11) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.8691 0.0984 0.4020 0.047 Uiso 1 1 calc R U . . .
C4 C 1.0521(3) 0.14838(14) 0.35834(12) 0.0460(6) Uani 1 1 d . . . . .
H4 H 1.1369 0.1184 0.3773 0.055 Uiso 1 1 calc R U . . .
C5 C 1.0841(2) 0.20447(13) 0.31647(11) 0.0387(5) Uani 1 1 d . . . . .
H5 H 1.1916 0.2127 0.3054 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9601(2) 0.24921(11) 0.29030(10) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.9898(3) 0.31295(13) 0.24721(13) 0.0426(6) Uani 1 1 d . . . . .
H7A H 0.9854 0.2978 0.2001 0.064 Uiso 1 1 calc R U . . .
H7B H 1.0966 0.3332 0.2607 0.064 Uiso 1 1 calc R U . . .
H7C H 0.9069 0.3497 0.2525 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3631(2) 0.39475(10) 0.17965(9) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.3733(2) 0.42838(10) 0.24303(9) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.2672(2) 0.48419(11) 0.25464(10) 0.0288(4) Uani 1 1 d . . . . .
H10 H 0.2732 0.5067 0.2975 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1536(2) 0.50755(11) 0.20502(10) 0.0330(5) Uani 1 1 d . . . . .
H11 H 0.0832 0.5464 0.2135 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1427(2) 0.47401(12) 0.14273(11) 0.0337(5) Uani 1 1 d . . . . .
H12 H 0.0640 0.4896 0.1085 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2459(2) 0.41802(11) 0.13026(10) 0.0290(4) Uani 1 1 d . . . . .
H13 H 0.2369 0.3951 0.0875 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3679(2) 0.25875(10) 0.11304(10) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.2758(2) 0.21036(11) 0.14700(11) 0.0306(4) Uani 1 1 d . . . . .
H15 H 0.2888 0.2081 0.1947 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1653(3) 0.16540(11) 0.11161(12) 0.0383(5) Uani 1 1 d . . . . .
H16 H 0.1005 0.1335 0.1352 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1492(3) 0.16691(12) 0.04249(12) 0.0421(6) Uani 1 1 d . . . . .
H17 H 0.0737 0.1359 0.0184 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2426(3) 0.21339(13) 0.00824(12) 0.0428(6) Uani 1 1 d . . . . .
H18 H 0.2327 0.2137 -0.0395 0.051 Uiso 1 1 calc R U . . .
C19 C 0.3511(3) 0.25974(12) 0.04306(11) 0.0356(5) Uani 1 1 d . . . . .
H19 H 0.4140 0.2922 0.0192 0.043 Uiso 1 1 calc R U . . .
C20 C 0.6344(2) 0.35617(11) 0.10542(10) 0.0263(4) Uani 1 1 d . . . . .
C21 C 0.7480(3) 0.31004(12) 0.08151(12) 0.0401(5) Uani 1 1 d . . . . .
H21 H 0.7543 0.2614 0.0967 0.048 Uiso 1 1 calc R U . . .
C22 C 0.8523(3) 0.33401(14) 0.03572(12) 0.0456(6) Uani 1 1 d . . . . .
H22 H 0.9286 0.3016 0.0194 0.055 Uiso 1 1 calc R U . . .
C23 C 0.8458(3) 0.40401(14) 0.01390(12) 0.0436(6) Uani 1 1 d . . . . .
H23 H 0.9169 0.4203 -0.0178 0.052 Uiso 1 1 calc R U . . .
C24 C 0.7363(3) 0.45063(14) 0.03793(14) 0.0545(7) Uani 1 1 d . . . . .
H24 H 0.7330 0.4995 0.0234 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6300(3) 0.42702(12) 0.08332(12) 0.0425(6) Uani 1 1 d . . . . .
H25 H 0.5538 0.4597 0.0993 0.051 Uiso 1 1 calc R U . . .
C26 C 0.6711(2) 0.46583(10) 0.32257(9) 0.0230(4) Uani 1 1 d . . . . .
C27 C 0.6550(3) 0.53517(12) 0.29628(11) 0.0363(5) Uani 1 1 d . . . . .
H27 H 0.5590 0.5485 0.2699 0.044 Uiso 1 1 calc R U . . .
C28 C 0.7786(3) 0.58509(13) 0.30852(12) 0.0452(6) Uani 1 1 d . . . . .
H28 H 0.7663 0.6327 0.2910 0.054 Uiso 1 1 calc R U . . .
C29 C 0.9184(3) 0.56610(14) 0.34567(12) 0.0437(6) Uani 1 1 d . . . . .
H29 H 1.0030 0.6004 0.3536 0.052 Uiso 1 1 calc R U . . .
C30 C 0.9361(3) 0.49758(14) 0.37146(13) 0.0455(6) Uani 1 1 d . . . . .
H30 H 1.0330 0.4845 0.3973 0.055 Uiso 1 1 calc R U . . .
C31 C 0.8136(2) 0.44757(12) 0.35993(11) 0.0351(5) Uani 1 1 d . . . . .
H31 H 0.8271 0.4002 0.3778 0.042 Uiso 1 1 calc R U . . .
C32 C 0.4074(2) 0.39732(10) 0.38345(9) 0.0242(4) Uani 1 1 d . . . . .
C33 C 0.3928(2) 0.45826(11) 0.42325(9) 0.0271(4) Uani 1 1 d . . . . .
H33 H 0.4487 0.5014 0.4138 0.032 Uiso 1 1 calc R U . . .
C34 C 0.2965(3) 0.45615(12) 0.47687(10) 0.0355(5) Uani 1 1 d . . . . .
H34 H 0.2876 0.4976 0.5043 0.043 Uiso 1 1 calc R U . . .
C35 C 0.2136(3) 0.39365(14) 0.49031(11) 0.0414(5) Uani 1 1 d . . . . .
H35 H 0.1464 0.3925 0.5265 0.050 Uiso 1 1 calc R U . . .
C36 C 0.2286(3) 0.33318(13) 0.45116(11) 0.0414(5) Uani 1 1 d . . . . .
H36 H 0.1710 0.2904 0.4602 0.050 Uiso 1 1 calc R U . . .
C37 C 0.3272(2) 0.33442(11) 0.39869(10) 0.0326(5) Uani 1 1 d . . . . .
H37 H 0.3401 0.2920 0.3729 0.039 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 N1 2.0348(15) . ?
Cu1 O1 2.0541(13) . ?
Cu1 P1 2.2329(6) . ?
Cu1 P2 2.2480(5) . ?
P1 C20 1.8256(19) . ?
P1 C14 1.8301(19) . ?
P1 C8 1.8409(18) . ?
P2 C26 1.8241(19) . ?
P2 C32 1.8288(19) . ?
P2 C9 1.8358(19) . ?
O1 C1 1.266(3) . ?
O2 C1 1.232(2) . ?
N1 C6 1.347(2) . ?
N1 C2 1.353(2) . ?
C1 C2 1.526(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.394(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.383(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.366(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.387(3) . ?
C26 C27 1.389(3) . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.369(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.372(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.388(3) . ?
C32 C33 1.391(3) . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.377(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.384(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O1 81.76(6) . . ?
N1 Cu1 P1 132.24(5) . . ?
O1 Cu1 P1 118.81(4) . . ?
N1 Cu1 P2 123.28(5) . . ?
O1 Cu1 P2 111.53(4) . . ?
P1 Cu1 P2 90.626(19) . . ?
C20 P1 C14 103.43(9) . . ?
C20 P1 C8 104.06(9) . . ?
C14 P1 C8 101.78(8) . . ?
C20 P1 Cu1 120.06(7) . . ?
C14 P1 Cu1 121.18(7) . . ?
C8 P1 Cu1 103.56(6) . . ?
C26 P2 C32 104.44(8) . . ?
C26 P2 C9 105.23(9) . . ?
C32 P2 C9 102.26(8) . . ?
C26 P2 Cu1 118.41(6) . . ?
C32 P2 Cu1 120.56(6) . . ?
C9 P2 Cu1 103.75(6) . . ?
C1 O1 Cu1 113.38(12) . . ?
C6 N1 C2 118.88(17) . . ?
C6 N1 Cu1 129.77(14) . . ?
C2 N1 Cu1 111.33(12) . . ?
O2 C1 O1 127.1(2) . . ?
O2 C1 C2 116.9(2) . . ?
O1 C1 C2 115.91(16) . . ?
N1 C2 C3 122.44(19) . . ?
N1 C2 C1 115.85(17) . . ?
C3 C2 C1 121.67(19) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 120.6(2) . . ?
N1 C6 C7 117.08(18) . . ?
C5 C6 C7 122.30(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.03(17) . . ?
C13 C8 P1 121.68(14) . . ?
C9 C8 P1 119.26(14) . . ?
C10 C9 C8 119.22(17) . . ?
C10 C9 P2 122.11(15) . . ?
C8 C9 P2 118.61(14) . . ?
C11 C10 C9 121.22(18) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.53(19) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.24(19) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.74(19) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C15 C14 C19 119.05(19) . . ?
C15 C14 P1 116.67(15) . . ?
C19 C14 P1 124.26(15) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C25 C20 C21 118.31(19) . . ?
C25 C20 P1 124.00(15) . . ?
C21 C20 P1 117.69(16) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.6(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.4(2) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C31 C26 C27 118.63(19) . . ?
C31 C26 P2 116.36(15) . . ?
C27 C26 P2 124.95(15) . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C26 120.7(2) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
C37 C32 C33 119.21(18) . . ?
C37 C32 P2 116.24(15) . . ?
C33 C32 P2 124.51(15) . . ?
C34 C33 C32 120.07(19) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 120.1(2) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 119.9(2) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.3(2) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C32 120.4(2) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?

_shelxl_version_number           2013-4



