# 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 2017

####################################################################### 
# 
# 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_Cuibufgamapic
_database_code_depnum_ccdc_archive 'CCDC 1509592'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H50 Cu N2 O5, H2 O'

_chemical_formula_sum            'C38 H52 Cu N2 O6'
_chemical_formula_weight         696.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2706(2)
_cell_length_b                   11.8221(3)
_cell_length_c                   17.2366(3)
_cell_angle_alpha                104.3850(14)
_cell_angle_beta                 95.6170(14)
_cell_angle_gamma                109.5680(13)
_cell_volume                     1872.19(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    29876
_cell_measurement_theta_min      3.
_cell_measurement_theta_max      28.

_exptl_crystal_description       prismatic
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             742
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.629
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29871
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.106
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             8977
_reflns_number_gt                7084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
;
 SHELXL-97 (Sheldrick, 1997); WINGX (Farrugia, 1999)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0879P)²+0.2746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8977
_refine_ls_number_parameters     432
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51496(2) 0.22690(2) -0.01224(2) 0.04215(10) Uani 1 1 d . . . . .
O1 O 0.49818(17) 0.30018(15) -0.10246(9) 0.0551(4) Uani 1 1 d . . . . .
O1W O 0.60909(19) 0.08297(16) -0.07571(11) 0.0557(4) Uani 1 1 d D . . . .
O2 O 0.5122(2) 0.1446(2) -0.20077(12) 0.0760(5) Uani 1 1 d . . . . .
O3 O 0.52117(15) 0.17248(14) 0.08771(8) 0.0457(3) Uani 1 1 d . . . . .
O4 O 0.4772(2) 0.34136(18) 0.14317(13) 0.0704(5) Uani 1 1 d . . . . .
N1 N 0.30745(17) 0.11918(17) -0.04978(10) 0.0432(4) Uani 1 1 d . . . . .
N2 N 0.70799(18) 0.36134(18) 0.03614(11) 0.0462(4) Uani 1 1 d . . . . .
C1 C 0.2143(2) 0.1756(2) -0.04215(15) 0.0542(5) Uani 1 1 d . . . . .
H1 H 0.2476 0.2621 -0.0175 0.065 Uiso 1 1 calc R U . . .
C2 C 0.0715(2) 0.1115(3) -0.06912(16) 0.0598(6) Uani 1 1 d . . . . .
H2 H 0.0106 0.1546 -0.0615 0.072 Uiso 1 1 calc R U . . .
C3 C 0.0181(2) -0.0166(3) -0.10759(14) 0.0551(6) Uani 1 1 d . . . . .
C4 C 0.1140(2) -0.0751(2) -0.11538(15) 0.0560(5) Uani 1 1 d . . . . .
H4 H 0.0831 -0.1614 -0.1403 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2564(2) -0.0052(2) -0.08609(14) 0.0507(5) Uani 1 1 d . . . . .
H5 H 0.3193 -0.0465 -0.0919 0.061 Uiso 1 1 calc R U . . .
C6 C -0.1374(3) -0.0885(4) -0.1399(2) 0.0818(9) Uani 1 1 d . . . . .
H6A H -0.1648 -0.0723 -0.1896 0.123 Uiso 1 1 calc R U . . .
H6B H -0.1889 -0.0621 -0.1001 0.123 Uiso 1 1 calc R U . . .
H6C H -0.1577 -0.1769 -0.1504 0.123 Uiso 1 1 calc R U . . .
C7 C 0.7242(2) 0.4820(2) 0.06982(15) 0.0535(5) Uani 1 1 d . . . . .
H7 H 0.6452 0.5037 0.0665 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8533(3) 0.5748(2) 0.10908(15) 0.0576(6) Uani 1 1 d . . . . .
H8 H 0.8598 0.6569 0.1325 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9726(2) 0.5459(2) 0.11360(14) 0.0566(6) Uani 1 1 d . . . . .
C10 C 0.9559(2) 0.4221(3) 0.07843(15) 0.0584(6) Uani 1 1 d . . . . .
H10 H 1.0339 0.3988 0.0798 0.070 Uiso 1 1 calc R U . . .
C11 C 0.8231(2) 0.3328(2) 0.04118(14) 0.0530(5) Uani 1 1 d . . . . .
H11 H 0.8137 0.2497 0.0188 0.064 Uiso 1 1 calc R U . . .
C12 C 1.1155(3) 0.6458(3) 0.15660(18) 0.0773(9) Uani 1 1 d . . . . .
H12A H 1.1330 0.6476 0.2127 0.116 Uiso 1 1 calc R U . . .
H12B H 1.1171 0.7264 0.1540 0.116 Uiso 1 1 calc R U . . .
H12C H 1.1871 0.6268 0.1303 0.116 Uiso 1 1 calc R U . . .
C13 C 0.4889(2) 0.2416(2) -0.17714(14) 0.0550(6) Uani 1 1 d . . . . .
C14 C 0.4436(3) 0.2997(3) -0.24027(15) 0.0623(6) Uani 1 1 d . . . . .
H14 H 0.4726 0.3903 -0.2139 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5168(3) 0.2815(5) -0.3126(2) 0.0985(13) Uani 1 1 d . . . . .
H15A H 0.4971 0.1935 -0.3362 0.148 Uiso 1 1 calc R U . . .
H15B H 0.6167 0.3259 -0.2942 0.148 Uiso 1 1 calc R U . . .
H15C H 0.4828 0.3138 -0.3528 0.148 Uiso 1 1 calc R U . . .
C16 C 0.2848(3) 0.2452(2) -0.26891(13) 0.0540(5) Uani 1 1 d . . . . .
C17 C 0.1980(3) 0.1313(2) -0.26220(15) 0.0589(6) Uani 1 1 d . . . . .
H17 H 0.2379 0.0843 -0.2391 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0537(3) 0.0856(3) -0.28895(16) 0.0665(7) Uani 1 1 d . . . . .
H18 H -0.0017 0.0089 -0.2833 0.080 Uiso 1 1 calc R U . . .
C19 C -0.0106(3) 0.1531(3) -0.32433(16) 0.0684(7) Uani 1 1 d . . . . .
C20 C 0.0754(4) 0.2649(3) -0.3322(2) 0.0796(8) Uani 1 1 d . . . . .
H20 H 0.0355 0.3109 -0.3563 0.096 Uiso 1 1 calc R U . . .
C21 C 0.2210(3) 0.3115(3) -0.30514(18) 0.0722(7) Uani 1 1 d . . . . .
H21 H 0.2763 0.3879 -0.3113 0.087 Uiso 1 1 calc R U . . .
C22 C -0.1691(4) 0.1022(4) -0.3518(2) 0.0922(11) Uani 1 1 d . . . . .
H22A H -0.1968 0.1696 -0.3604 0.111 Uiso 1 1 calc R U . . .
H22B H -0.2121 0.0767 -0.3081 0.111 Uiso 1 1 calc R U . . .
C23 C -0.2283(4) -0.0092(5) -0.4298(3) 0.1119(15) Uani 1 1 d . . . . .
H23 H -0.1876 -0.0716 -0.4243 0.134 Uiso 1 1 calc R U . . .
C24 C -0.3872(5) -0.0698(7) -0.4398(4) 0.174(3) Uani 1 1 d . . . . .
H24A H -0.4313 -0.0235 -0.4640 0.260 Uiso 1 1 calc R U . . .
H24B H -0.4111 -0.0690 -0.3873 0.260 Uiso 1 1 calc R U . . .
H24C H -0.4196 -0.1550 -0.4745 0.260 Uiso 1 1 calc R U . . .
C25 C -0.1905(7) 0.0295(9) -0.5000(3) 0.209(4) Uani 1 1 d . . . . .
H25A H -0.2443 0.0774 -0.5129 0.313 Uiso 1 1 calc R U . . .
H25B H -0.2102 -0.0435 -0.5458 0.313 Uiso 1 1 calc R U . . .
H25C H -0.0918 0.0805 -0.4883 0.313 Uiso 1 1 calc R U . . .
C26 C 0.5069(2) 0.2515(2) 0.14929(13) 0.0455(4) Uani 1 1 d . . . . .
C27 C 0.5314(2) 0.2288(2) 0.23154(13) 0.0521(5) Uani 1 1 d . . . . .
H27 H 0.4791 0.1395 0.2245 0.063 Uiso 1 1 calc R U . . .
C28 C 0.4771(3) 0.3062(4) 0.29618(18) 0.0810(9) Uani 1 1 d . . . . .
H28A H 0.4873 0.2843 0.3458 0.122 Uiso 1 1 calc R U . . .
H28B H 0.3794 0.2886 0.2768 0.122 Uiso 1 1 calc R U . . .
H28C H 0.5305 0.3941 0.3064 0.122 Uiso 1 1 calc R U . . .
C29 C 0.6875(2) 0.2571(2) 0.26104(12) 0.0479(5) Uani 1 1 d . . . . .
C30 C 0.7282(3) 0.1834(3) 0.30176(16) 0.0628(6) Uani 1 1 d . . . . .
H30 H 0.6604 0.1130 0.3083 0.075 Uiso 1 1 calc R U . . .
C31 C 0.8698(3) 0.2141(3) 0.33291(17) 0.0708(7) Uani 1 1 d . . . . .
H31 H 0.8949 0.1641 0.3607 0.085 Uiso 1 1 calc R U . . .
C32 C 0.9741(3) 0.3167(3) 0.32377(15) 0.0610(6) Uani 1 1 d . . . . .
C33 C 0.9322(3) 0.3880(3) 0.28149(15) 0.0611(6) Uani 1 1 d . . . . .
H33 H 1.0006 0.4566 0.2733 0.073 Uiso 1 1 calc R U . . .
C34 C 0.7919(2) 0.3604(2) 0.25106(14) 0.0555(5) Uani 1 1 d . . . . .
H34 H 0.7671 0.4111 0.2238 0.067 Uiso 1 1 calc R U . . .
C35 C 1.1271(3) 0.3480(4) 0.35839(18) 0.0813(9) Uani 1 1 d . . . . .
H35A H 1.1849 0.3919 0.3258 0.098 Uiso 1 1 calc R U . . .
H35B H 1.1424 0.2702 0.3535 0.098 Uiso 1 1 calc R U . . .
C36 C 1.1755(4) 0.4288(5) 0.4475(2) 0.1138(16) Uani 1 1 d . . . . .
H36 H 1.1080 0.3898 0.4785 0.137 Uiso 1 1 calc R U . . .
C37 C 1.1788(6) 0.5590(6) 0.4575(4) 0.163(3) Uani 1 1 d . . . . .
H37A H 1.2516 0.6022 0.4325 0.245 Uiso 1 1 calc R U . . .
H37B H 1.1977 0.6037 0.5146 0.245 Uiso 1 1 calc R U . . .
H37C H 1.0894 0.5547 0.4318 0.245 Uiso 1 1 calc R U . . .
C38 C 1.3173(7) 0.4300(9) 0.4807(4) 0.230(5) Uani 1 1 d . . . . .
H38A H 1.3853 0.4676 0.4510 0.345 Uiso 1 1 calc R U . . .
H38B H 1.3109 0.3453 0.4748 0.345 Uiso 1 1 calc R U . . .
H38C H 1.3462 0.4779 0.5375 0.345 Uiso 1 1 calc R U . . .
O2W O 0.2964(3) 0.4467(3) 0.0997(2) 0.1381(13) Uani 1 1 d . . . . .
H1W H 0.579(4) 0.0056(19) -0.082(3) 0.114(14) Uiso 1 1 d D . . . .
H2W H 0.582(4) 0.084(4) -0.1248(15) 0.106(13) Uiso 1 1 d 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
Cu1 O1 1.9788(15) . ?
Cu1 O3 1.9856(14) . ?
Cu1 N2 2.0147(17) . ?
Cu1 N1 2.0212(16) . ?
Cu1 O1W 2.3261(18) . ?
O1 C13 1.278(3) . ?
O1W H1W 0.836(19) . ?
O1W H2W 0.868(18) . ?
O2 C13 1.229(3) . ?
O3 C26 1.284(3) . ?
O4 C26 1.225(3) . ?
N1 C1 1.336(3) . ?
N1 C5 1.338(3) . ?
N2 C11 1.335(3) . ?
N2 C7 1.345(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 C6 1.505(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 C12 1.513(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.535(3) . ?
C14 C16 1.516(3) . ?
C14 C15 1.525(4) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.384(3) . ?
C16 C21 1.393(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(5) . ?
C19 C22 1.513(4) . ?
C20 C21 1.394(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.527(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C25 1.441(7) . ?
C23 C24 1.518(6) . ?
C23 H23 0.9800 . ?
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 C27 1.520(3) . ?
C27 C29 1.529(3) . ?
C27 C28 1.532(4) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.384(3) . ?
C29 C34 1.390(3) . ?
C30 C31 1.390(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.383(4) . ?
C32 C35 1.510(4) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.524(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.493(8) . ?
C36 C38 1.506(6) . ?
C36 H36 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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 O3 171.28(7) . . ?
O1 Cu1 N2 89.92(7) . . ?
O3 Cu1 N2 89.32(6) . . ?
O1 Cu1 N1 88.17(7) . . ?
O3 Cu1 N1 90.84(6) . . ?
N2 Cu1 N1 168.47(8) . . ?
O1 Cu1 O1W 97.63(7) . . ?
O3 Cu1 O1W 91.07(6) . . ?
N2 Cu1 O1W 92.04(7) . . ?
N1 Cu1 O1W 99.48(7) . . ?
C13 O1 Cu1 123.05(16) . . ?
Cu1 O1W H1W 127(3) . . ?
Cu1 O1W H2W 95(3) . . ?
H1W O1W H2W 101(4) . . ?
C26 O3 Cu1 111.99(14) . . ?
C1 N1 C5 117.11(18) . . ?
C1 N1 Cu1 118.49(15) . . ?
C5 N1 Cu1 124.29(15) . . ?
C11 N2 C7 117.56(19) . . ?
C11 N2 Cu1 121.31(16) . . ?
C7 N2 Cu1 120.96(15) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 C6 121.7(3) . . ?
C2 C3 C6 121.4(3) . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 122.9(2) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 122.6(2) . . ?
N2 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 117.4(2) . . ?
C8 C9 C12 121.0(3) . . ?
C10 C9 C12 121.6(3) . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C11 C10 122.5(2) . . ?
N2 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O1 125.1(2) . . ?
O2 C13 C14 119.3(2) . . ?
O1 C13 C14 115.6(2) . . ?
C16 C14 C15 110.7(2) . . ?
C16 C14 C13 111.23(19) . . ?
C15 C14 C13 110.8(3) . . ?
C16 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
C13 C14 H14 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.3(2) . . ?
C17 C16 C14 123.7(2) . . ?
C21 C16 C14 119.0(2) . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.4(3) . . ?
C20 C19 C22 122.6(3) . . ?
C18 C19 C22 120.1(3) . . ?
C19 C20 C21 121.8(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C16 C21 C20 120.8(3) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C19 C22 C23 115.1(3) . . ?
C19 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
C19 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C25 C23 C24 111.2(5) . . ?
C25 C23 C22 111.0(5) . . ?
C24 C23 C22 109.7(5) . . ?
C25 C23 H23 108.3 . . ?
C24 C23 H23 108.3 . . ?
C22 C23 H23 108.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 O3 122.6(2) . . ?
O4 C26 C27 121.2(2) . . ?
O3 C26 C27 116.18(19) . . ?
C26 C27 C29 110.98(17) . . ?
C26 C27 C28 111.9(2) . . ?
C29 C27 C28 110.12(19) . . ?
C26 C27 H27 107.9 . . ?
C29 C27 H27 107.9 . . ?
C28 C27 H27 107.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C34 118.3(2) . . ?
C30 C29 C27 120.6(2) . . ?
C34 C29 C27 121.1(2) . . ?
C29 C30 C31 120.3(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 121.8(2) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 117.2(2) . . ?
C31 C32 C35 120.7(3) . . ?
C33 C32 C35 122.1(3) . . ?
C32 C33 C34 122.0(2) . . ?
C32 C33 H33 119.0 . . ?
C34 C33 H33 119.0 . . ?
C33 C34 C29 120.3(2) . . ?
C33 C34 H34 119.8 . . ?
C29 C34 H34 119.8 . . ?
C32 C35 C36 114.1(3) . . ?
C32 C35 H35A 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C32 C35 H35B 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C37 C36 C38 111.6(5) . . ?
C37 C36 C35 111.7(4) . . ?
C38 C36 C35 109.3(4) . . ?
C37 C36 H36 108.0 . . ?
C38 C36 H36 108.0 . . ?
C35 C36 H36 108.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_pyrrolidine
_database_code_depnum_ccdc_archive 'CCDC 1509593'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H52 Cu N2 O4, 2(H2 O)'
_chemical_formula_sum            'C34 H56 Cu N2 O6'
_chemical_formula_weight         652.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   16.5388(4)
_cell_length_b                   6.1918(1)
_cell_length_c                   17.4653(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.8030(14)
_cell_angle_gamma                90
_cell_volume                     1782.25(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    24641
_cell_measurement_theta_min      2.
_cell_measurement_theta_max      28.

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.655
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24641
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.492
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4282
_reflns_number_gt                3371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014; WINGX (Farrugia, 1999)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+1.3811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4282
_refine_ls_number_parameters     235
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.5413(12) -0.277(2) 0.1432(14) 0.100(5) Uani 0.6 1 d D . P A 1
H15 H 0.5288 -0.3165 0.1952 0.120 Uiso 0.6 1 calc R U P A 1
C15A C 0.5299(19) -0.367(5) 0.1466(14) 0.112(9) Uani 0.4 1 d D . P A 2
H15A H 0.5036 -0.4725 0.1780 0.134 Uiso 0.4 1 calc R U P A 2
C16 C 0.6078(18) -0.423(6) 0.123(2) 0.174(12) Uani 0.6 1 d D . P A 1
H16A H 0.6337 -0.3636 0.0808 0.261 Uiso 0.6 1 calc R U P A 1
H16B H 0.5858 -0.5624 0.1094 0.261 Uiso 0.6 1 calc R U P A 1
H16C H 0.6469 -0.4372 0.1668 0.261 Uiso 0.6 1 calc R U P A 1
C17 C 0.5707(5) -0.065(2) 0.1478(7) 0.129(4) Uani 0.6 1 d D . P A 1
H17A H 0.5916 -0.0260 0.1000 0.194 Uiso 0.6 1 calc R U P A 1
H17B H 0.6133 -0.0548 0.1886 0.194 Uiso 0.6 1 calc R U P A 1
H17C H 0.5275 0.0317 0.1580 0.194 Uiso 0.6 1 calc R U P A 1
C16A C 0.599(3) -0.506(8) 0.121(2) 0.160(19) Uani 0.4 1 d D . P A 2
H16D H 0.6128 -0.4601 0.0715 0.239 Uiso 0.4 1 calc R U P A 2
H16E H 0.5821 -0.6547 0.1186 0.239 Uiso 0.4 1 calc R U P A 2
H16F H 0.6455 -0.4922 0.1576 0.239 Uiso 0.4 1 calc R U P A 2
C17A C 0.5549(7) -0.206(3) 0.2068(9) 0.126(6) Uani 0.4 1 d D . P A 2
H17D H 0.6026 -0.1317 0.1932 0.189 Uiso 0.4 1 calc R U P A 2
H17E H 0.5665 -0.2785 0.2551 0.189 Uiso 0.4 1 calc R U P A 2
H17F H 0.5119 -0.1039 0.2111 0.189 Uiso 0.4 1 calc R U P A 2
C14 C 0.4649(2) -0.3255(8) 0.0904(2) 0.0839(11) Uani 1 1 d . . . . .
H14A H 0.4757 -0.2954 0.0378 0.126 Uiso 0.6 1 calc R U P A 1
H14B H 0.4523 -0.4780 0.0940 0.126 Uiso 0.6 1 calc R U P A 1
H14C H 0.4450 -0.4645 0.0714 0.126 Uiso 0.4 1 calc R U P A 2
H14D H 0.4876 -0.2532 0.0479 0.126 Uiso 0.4 1 calc R U P A 2
Cu1 Cu 0.0000 0.0000 0.0000 0.04242(16) Uani 1 2 d S . P . .
N1 N -0.07285(13) 0.1978(4) 0.05294(13) 0.0507(5) Uani 1 1 d D . . . .
O1 O 0.09406(11) 0.1207(3) 0.05834(13) 0.0599(5) Uani 1 1 d . . . . .
O2 O 0.06444(19) -0.0361(4) 0.16430(15) 0.0817(7) Uani 1 1 d . . . . .
O1W O -0.0079(3) -0.4719(6) 0.1767(2) 0.1028(10) Uani 1 1 d D . . . .
C1 C -0.1195(2) 0.3590(5) 0.0047(2) 0.0646(8) Uani 1 1 d . . . . .
H1A H -0.1330 0.3023 -0.0466 0.078 Uiso 1 1 calc R U . . .
H1B H -0.0881 0.4903 0.0007 0.078 Uiso 1 1 calc R U . . .
C2 C -0.1953(2) 0.4037(8) 0.0437(3) 0.0889(12) Uani 1 1 d . . . . .
H2A H -0.1898 0.5368 0.0729 0.107 Uiso 1 1 calc R U . . .
H2B H -0.2416 0.4169 0.0060 0.107 Uiso 1 1 calc R U . . .
C3 C -0.2059(2) 0.2224(9) 0.0942(3) 0.1051(15) Uani 1 1 d . . . . .
H3A H -0.2541 0.1417 0.0762 0.126 Uiso 1 1 calc R U . . .
H3B H -0.2127 0.2739 0.1457 0.126 Uiso 1 1 calc R U . . .
C4 C -0.1342(2) 0.0828(7) 0.0950(2) 0.0818(11) Uani 1 1 d . . . . .
H4A H -0.1483 -0.0539 0.0703 0.098 Uiso 1 1 calc R U . . .
H4B H -0.1130 0.0543 0.1475 0.098 Uiso 1 1 calc R U . . .
C5 C 0.10755(18) 0.0800(6) 0.1279(2) 0.0621(8) Uani 1 1 d . . . . .
C6 C 0.1854(2) 0.1888(8) 0.1639(3) 0.0990(16) Uani 1 1 d . . . . .
H6 H 0.1901 0.3200 0.1332 0.119 Uiso 1 1 calc R U . . .
C7 C 0.1841(2) 0.2643(11) 0.2380(3) 0.133(2) Uani 1 1 d . . . . .
H7A H 0.1744 0.1462 0.2716 0.200 Uiso 1 1 calc R U . . .
H7B H 0.1418 0.3696 0.2400 0.200 Uiso 1 1 calc R U . . .
H7C H 0.2355 0.3296 0.2539 0.200 Uiso 1 1 calc R U . . .
C8 C 0.2580(2) 0.0520(6) 0.1450(2) 0.0699(10) Uani 1 1 d . . . . .
C9 C 0.2718(2) -0.1520(8) 0.1767(2) 0.0804(11) Uani 1 1 d . . . . .
H9 H 0.2362 -0.2076 0.2101 0.096 Uiso 1 1 calc R U . . .
C10 C 0.3388(2) -0.2747(7) 0.1588(2) 0.0753(9) Uani 1 1 d . . . . .
H10 H 0.3473 -0.4108 0.1805 0.090 Uiso 1 1 calc R U . . .
C11 C 0.39192(17) -0.1961(6) 0.10958(19) 0.0643(8) Uani 1 1 d . . . . .
C12 C 0.3764(3) 0.0040(7) 0.0787(3) 0.0835(11) Uani 1 1 d . . . . .
H12 H 0.4115 0.0599 0.0448 0.100 Uiso 1 1 calc R U . . .
C13 C 0.3108(2) 0.1252(7) 0.0960(3) 0.0868(11) Uani 1 1 d . . . . .
H13 H 0.3026 0.2604 0.0735 0.104 Uiso 1 1 calc R U . . .
H1N H -0.0445(17) 0.276(5) 0.0864(15) 0.061(9) Uiso 1 1 d D . . . .
H1W H -0.021(3) -0.470(9) 0.2228(16) 0.13(2) Uiso 1 1 d D . . . .
H2W H 0.010(3) -0.341(5) 0.172(4) 0.14(2) Uiso 1 1 d 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
C15 C17 1.400(17) . ?
C15 C16 1.489(18) . ?
C15 C14 1.53(2) . ?
C15 H15 0.9800 . ?
C15A C14 1.42(3) . ?
C15A C17A 1.48(2) . ?
C15A C16A 1.53(2) . ?
C15A H15A 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C14 C11 1.509(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
Cu1 O1 1.9368(19) . ?
Cu1 O1 1.9368(19) 3 ?
Cu1 N1 1.998(2) . ?
Cu1 N1 1.998(2) 3 ?
N1 C1 1.481(4) . ?
N1 C4 1.484(4) . ?
N1 H1N 0.864(18) . ?
O1 C5 1.242(4) . ?
O2 C5 1.227(5) . ?
O1W H1W 0.85(2) . ?
O1W H2W 0.87(2) . ?
C1 C2 1.502(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.447(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.466(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.540(5) . ?
C6 C7 1.378(6) . ?
C6 C8 1.528(5) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.352(6) . ?
C8 C9 1.390(6) . ?
C9 C10 1.400(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 H13 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
C17 C15 C16 109(2) . . ?
C17 C15 C14 119.0(14) . . ?
C16 C15 C14 109.2(16) . . ?
C17 C15 H15 106.3 . . ?
C16 C15 H15 106.3 . . ?
C14 C15 H15 106.3 . . ?
C14 C15A C17A 121.4(17) . . ?
C14 C15A C16A 116.4(18) . . ?
C17A C15A C16A 115(2) . . ?
C14 C15A H15A 99.3 . . ?
C17A C15A H15A 99.3 . . ?
C16A C15A H15A 99.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C15A C14 C11 121.1(9) . . ?
C11 C14 C15 113.4(7) . . ?
C11 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C11 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15A C14 H14C 107.0 . . ?
C11 C14 H14C 107.0 . . ?
C15A C14 H14D 107.0 . . ?
C11 C14 H14D 107.0 . . ?
H14C C14 H14D 106.8 . . ?
O1 Cu1 O1 180.0 . 3 ?
O1 Cu1 N1 90.51(9) . . ?
O1 Cu1 N1 89.48(9) 3 . ?
O1 Cu1 N1 89.49(9) . 3 ?
O1 Cu1 N1 90.52(9) 3 3 ?
N1 Cu1 N1 180.0 . 3 ?
C1 N1 C4 105.1(2) . . ?
C1 N1 Cu1 117.09(18) . . ?
C4 N1 Cu1 113.5(2) . . ?
C1 N1 H1N 104(2) . . ?
C4 N1 H1N 107(2) . . ?
Cu1 N1 H1N 110(2) . . ?
C5 O1 Cu1 120.5(2) . . ?
H1W O1W H2W 101(5) . . ?
N1 C1 C2 106.3(3) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C3 C2 C1 106.4(3) . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 108.9(3) . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 N1 107.3(3) . . ?
C3 C4 H4A 110.2 . . ?
N1 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
N1 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O2 C5 O1 124.1(3) . . ?
O2 C5 C6 123.1(4) . . ?
O1 C5 C6 112.7(4) . . ?
C7 C6 C8 117.7(4) . . ?
C7 C6 C5 117.1(4) . . ?
C8 C6 C5 108.3(3) . . ?
C7 C6 H6 104.0 . . ?
C8 C6 H6 104.0 . . ?
C5 C6 H6 104.0 . . ?
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 117.5(3) . . ?
C13 C8 C6 120.8(4) . . ?
C9 C8 C6 121.6(4) . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 117.5(3) . . ?
C12 C11 C14 121.4(4) . . ?
C10 C11 C14 121.2(4) . . ?
C11 C12 C13 122.2(4) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C8 C13 C12 121.4(4) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_betapic
_database_code_depnum_ccdc_archive 'CCDC 1509591'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H50 Cu N2 O5'
_chemical_formula_sum            'C38 H50 Cu N2 O5'
_chemical_formula_weight         678.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4147(2)
_cell_length_b                   11.8811(3)
_cell_length_c                   17.5005(4)
_cell_angle_alpha                95.564(1)
_cell_angle_beta                 103.187(1)
_cell_angle_gamma                103.464(1)
_cell_volume                     1830.12(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    34072
_cell_measurement_theta_min      2.
_cell_measurement_theta_max      28.

_exptl_crystal_description       prismatic
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             722
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34072
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.735
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             8751
_reflns_number_gt                7084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014; WINGX (Farrugia, 1999)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1080P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8751
_refine_ls_number_parameters     423
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1690
_refine_ls_wR_factor_gt          0.1586
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.50515(3) 0.22340(2) -0.01707(2) 0.04407(12) Uani 1 1 d . . . . .
O1W O 0.3386(2) 0.04251(16) -0.06120(12) 0.0580(4) Uani 1 1 d D . . . .
O1 O 0.59237(19) 0.17063(15) 0.08167(10) 0.0496(4) Uani 1 1 d . . . . .
O2 O 0.7232(3) 0.35629(18) 0.12026(14) 0.0729(5) Uani 1 1 d . . . . .
O3 O 0.4361(2) 0.29859(18) -0.10863(11) 0.0606(4) Uani 1 1 d . . . . .
O4 O 0.2569(4) 0.1466(3) -0.18204(17) 0.1043(10) Uani 1 1 d . . . . .
N1 N 0.3637(2) 0.28367(18) 0.03766(12) 0.0481(4) Uani 1 1 d . . . . .
N2 N 0.6746(2) 0.19589(18) -0.06426(12) 0.0474(4) Uani 1 1 d . . . . .
C1 C 0.2392(3) 0.2105(2) 0.04697(15) 0.0512(5) Uani 1 1 d . . . . .
H1 H 0.2165 0.1320 0.0249 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1421(3) 0.2452(3) 0.08764(17) 0.0586(6) Uani 1 1 d . . . . .
C3 C 0.1793(4) 0.3623(3) 0.11989(18) 0.0681(7) Uani 1 1 d . . . . .
H3 H 0.1179 0.3896 0.1478 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3073(4) 0.4391(3) 0.11096(19) 0.0680(7) Uani 1 1 d . . . . .
H4 H 0.3329 0.5179 0.1329 0.082 Uiso 1 1 calc R U . . .
C5 C 0.3963(3) 0.3968(2) 0.06900(16) 0.0571(6) Uani 1 1 d . . . . .
H5 H 0.4817 0.4485 0.0623 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0050(3) 0.1581(4) 0.0955(2) 0.0792(9) Uani 1 1 d . . . . .
H6A H 0.0251 0.1354 0.1473 0.119 Uiso 1 1 calc R U . . .
H6B H -0.0193 0.0902 0.0556 0.119 Uiso 1 1 calc R U . . .
H6C H -0.0786 0.1927 0.0887 0.119 Uiso 1 1 calc R U . . .
C7 C 0.7898(3) 0.2873(2) -0.06349(16) 0.0526(5) Uani 1 1 d . . . . .
H7 H 0.7916 0.3605 -0.0383 0.063 Uiso 1 1 calc R U . . .
C8 C 0.9062(3) 0.2792(3) -0.09799(16) 0.0558(6) Uani 1 1 d . . . . .
C9 C 0.9038(3) 0.1685(3) -0.13280(17) 0.0618(6) Uani 1 1 d . . . . .
H9 H 0.9808 0.1583 -0.1557 0.074 Uiso 1 1 calc R U . . .
C10 C 0.7869(4) 0.0742(3) -0.13320(18) 0.0646(7) Uani 1 1 d . . . . .
H10 H 0.7837 -0.0002 -0.1568 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6746(3) 0.0906(2) -0.09838(16) 0.0557(6) Uani 1 1 d . . . . .
H11 H 0.5962 0.0262 -0.0987 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0302(4) 0.3858(3) -0.0975(2) 0.0780(9) Uani 1 1 d . . . . .
H12A H 1.0161 0.4530 -0.0680 0.117 Uiso 1 1 calc R U . . .
H12B H 1.0269 0.3986 -0.1511 0.117 Uiso 1 1 calc R U . . .
H12C H 1.1264 0.3736 -0.0730 0.117 Uiso 1 1 calc R U . . .
C13 C 0.6826(3) 0.2563(2) 0.13448(15) 0.0528(5) Uani 1 1 d . . . . .
C14 C 0.7339(3) 0.2227(3) 0.21672(16) 0.0642(7) Uani 1 1 d . . . . .
H14 H 0.7780 0.1565 0.2102 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8570(4) 0.3245(5) 0.2727(2) 0.1010(14) Uani 1 1 d . . . . .
H15A H 0.9447 0.3409 0.2522 0.151 Uiso 1 1 calc R U . . .
H15B H 0.8835 0.3031 0.3245 0.151 Uiso 1 1 calc R U . . .
H15C H 0.8196 0.3929 0.2761 0.151 Uiso 1 1 calc R U . . .
C16 C 0.6011(3) 0.1834(3) 0.25169(15) 0.0602(6) Uani 1 1 d . . . . .
C17 C 0.5870(5) 0.0861(3) 0.2909(2) 0.0758(8) Uani 1 1 d . . . . .
H17 H 0.6595 0.0440 0.2951 0.091 Uiso 1 1 calc R U . . .
C18 C 0.4671(5) 0.0521(3) 0.3232(2) 0.0867(10) Uani 1 1 d . . . . .
H18 H 0.4609 -0.0130 0.3491 0.104 Uiso 1 1 calc R U . . .
C19 C 0.3546(5) 0.1107(3) 0.3191(2) 0.0806(9) Uani 1 1 d . . . . .
C20 C 0.3696(4) 0.2077(3) 0.28040(19) 0.0742(8) Uani 1 1 d . . . . .
H20 H 0.2973 0.2498 0.2767 0.089 Uiso 1 1 calc R U . . .
C21 C 0.4896(4) 0.2433(3) 0.24719(17) 0.0649(7) Uani 1 1 d . . . . .
H21 H 0.4957 0.3084 0.2214 0.078 Uiso 1 1 calc R U . . .
C22 C 0.2177(6) 0.0692(5) 0.3499(3) 0.1137(16) Uani 1 1 d . . . . .
H22A H 0.1303 0.0764 0.3107 0.136 Uiso 1 1 calc R U . . .
H22B H 0.2046 -0.0136 0.3525 0.136 Uiso 1 1 calc R U . . .
C23 C 0.2147(11) 0.1272(9) 0.4277(5) 0.194(4) Uani 1 1 d D . . . .
H23 H 0.1153 0.0973 0.4374 0.233 Uiso 1 1 calc R U . . .
C24 C 0.2685(18) 0.2573(9) 0.4539(9) 0.271(7) Uani 1 1 d D U . . .
H24A H 0.2563 0.2760 0.5063 0.407 Uiso 1 1 calc R U . . .
H24B H 0.3733 0.2838 0.4547 0.407 Uiso 1 1 calc R U . . .
H24C H 0.2102 0.2954 0.4176 0.407 Uiso 1 1 calc R U . . .
C25 C 0.3360(12) 0.1158(13) 0.4962(6) 0.235(6) Uani 1 1 d D U . . .
H25A H 0.3265 0.1557 0.5444 0.353 Uiso 1 1 calc R U . . .
H25B H 0.3260 0.0344 0.5000 0.353 Uiso 1 1 calc R U . . .
H25C H 0.4333 0.1501 0.4881 0.353 Uiso 1 1 calc R U . . .
C26 C 0.3357(3) 0.2477(3) -0.17093(17) 0.0638(7) Uani 1 1 d . . . . .
C27 C 0.3138(4) 0.3207(4) -0.2375(2) 0.0809(10) Uani 1 1 d . . . . .
H27 H 0.3061 0.3967 -0.2141 0.097 Uiso 1 1 calc R U . . .
C28 C 0.1710(5) 0.2670(7) -0.3016(3) 0.135(2) Uani 1 1 d . . . . .
H28A H 0.1594 0.3183 -0.3404 0.202 Uiso 1 1 calc R U . . .
H28B H 0.0862 0.2552 -0.2787 0.202 Uiso 1 1 calc R U . . .
H28C H 0.1758 0.1930 -0.3268 0.202 Uiso 1 1 calc R U . . .
C29 C 0.4491(4) 0.3444(3) -0.27318(16) 0.0649(7) Uani 1 1 d . . . . .
C30 C 0.5493(4) 0.2742(3) -0.26797(18) 0.0691(7) Uani 1 1 d . . . . .
H30 H 0.5340 0.2094 -0.2420 0.083 Uiso 1 1 calc R U . . .
C31 C 0.6710(4) 0.2994(3) -0.30083(19) 0.0751(8) Uani 1 1 d . . . . .
H31 H 0.7375 0.2520 -0.2954 0.090 Uiso 1 1 calc R U . . .
C32 C 0.6972(4) 0.3940(3) -0.34191(18) 0.0741(8) Uani 1 1 d . . . . .
C33 C 0.5959(5) 0.4633(3) -0.3462(2) 0.0869(11) Uani 1 1 d . . . . .
H33 H 0.6104 0.5280 -0.3722 0.104 Uiso 1 1 calc R U . . .
C34 C 0.4759(5) 0.4392(3) -0.3133(2) 0.0814(10) Uani 1 1 d . . . . .
H34 H 0.4106 0.4875 -0.3179 0.098 Uiso 1 1 calc R U . . .
C35 C 0.8260(5) 0.4186(5) -0.3800(2) 0.0963(13) Uani 1 1 d . . . . .
H35A H 0.9112 0.3981 -0.3471 0.116 Uiso 1 1 calc R U . . .
H35B H 0.8562 0.5021 -0.3812 0.116 Uiso 1 1 calc R U . . .
C36 C 0.7916(7) 0.3522(6) -0.4658(3) 0.1138(16) Uani 1 1 d . . . . .
H36 H 0.8865 0.3756 -0.4813 0.137 Uiso 1 1 calc R U . . .
C37 C 0.7614(13) 0.2294(10) -0.4704(5) 0.207(4) Uani 1 1 d . U . . .
H37A H 0.6763 0.2012 -0.4494 0.310 Uiso 1 1 calc R U . . .
H37B H 0.8483 0.2097 -0.4400 0.310 Uiso 1 1 calc R U . . .
H37C H 0.7390 0.1937 -0.5249 0.310 Uiso 1 1 calc R U . . .
C38 C 0.6815(8) 0.3928(8) -0.5233(3) 0.145(2) Uani 1 1 d . U . . .
H38A H 0.6704 0.3542 -0.5759 0.217 Uiso 1 1 calc R U . . .
H38B H 0.7169 0.4760 -0.5208 0.217 Uiso 1 1 calc R U . . .
H38C H 0.5856 0.3748 -0.5105 0.217 Uiso 1 1 calc R U . . .
H1W H 0.323(5) 0.076(4) -0.1021(18) 0.095(13) Uiso 1 1 d D . . . .
H2W H 0.366(4) -0.021(2) -0.074(2) 0.083(11) Uiso 1 1 d 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
Cu1 O1 1.9636(16) . ?
Cu1 O3 1.9649(18) . ?
Cu1 N1 2.024(2) . ?
Cu1 N2 2.031(2) . ?
Cu1 O1W 2.2869(19) . ?
O1W H1W 0.853(19) . ?
O1W H2W 0.872(18) . ?
O1 C13 1.292(3) . ?
O2 C13 1.228(3) . ?
O3 C26 1.258(4) . ?
O4 C26 1.228(4) . ?
N1 C5 1.338(3) . ?
N1 C1 1.340(3) . ?
N2 C11 1.333(3) . ?
N2 C7 1.341(3) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(5) . ?
C2 C6 1.497(4) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(4) . ?
C8 C12 1.506(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.532(4) . ?
C14 C16 1.513(4) . ?
C14 C15 1.537(5) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.392(4) . ?
C16 C17 1.395(4) . ?
C17 C18 1.372(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(5) . ?
C19 C22 1.505(6) . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.474(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C25 1.496(8) . ?
C23 C24 1.4991(10) . ?
C23 H23 0.9800 . ?
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 C27 1.524(4) . ?
C27 C28 1.499(6) . ?
C27 C29 1.524(5) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C34 1.387(5) . ?
C29 C30 1.391(4) . ?
C30 C31 1.382(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.396(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.391(6) . ?
C32 C35 1.498(6) . ?
C33 C34 1.367(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.552(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.411(11) . ?
C36 C38 1.473(8) . ?
C36 H36 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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 O3 171.83(8) . . ?
O1 Cu1 N1 89.07(8) . . ?
O3 Cu1 N1 89.42(8) . . ?
O1 Cu1 N2 91.24(7) . . ?
O3 Cu1 N2 88.66(8) . . ?
N1 Cu1 N2 168.52(8) . . ?
O1 Cu1 O1W 90.21(7) . . ?
O3 Cu1 O1W 97.89(8) . . ?
N1 Cu1 O1W 92.90(8) . . ?
N2 Cu1 O1W 98.57(8) . . ?
Cu1 O1W H1W 78(3) . . ?
Cu1 O1W H2W 123(2) . . ?
H1W O1W H2W 109(4) . . ?
C13 O1 Cu1 112.31(16) . . ?
C26 O3 Cu1 125.1(2) . . ?
C5 N1 C1 118.3(2) . . ?
C5 N1 Cu1 120.67(18) . . ?
C1 N1 Cu1 120.98(17) . . ?
C11 N2 C7 118.0(2) . . ?
C11 N2 Cu1 122.77(17) . . ?
C7 N2 Cu1 119.23(17) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 116.6(3) . . ?
C3 C2 C6 122.8(3) . . ?
C1 C2 C6 120.6(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 123.8(2) . . ?
N2 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 C12 121.4(3) . . ?
C9 C8 C12 121.6(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N2 C11 C10 122.1(3) . . ?
N2 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O1 123.0(2) . . ?
O2 C13 C14 122.8(2) . . ?
O1 C13 C14 114.2(2) . . ?
C16 C14 C13 111.0(2) . . ?
C16 C14 C15 111.3(3) . . ?
C13 C14 C15 110.9(3) . . ?
C16 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.3(3) . . ?
C21 C16 C14 121.6(3) . . ?
C17 C16 C14 121.1(3) . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 122.8(3) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 116.3(3) . . ?
C20 C19 C22 120.6(4) . . ?
C18 C19 C22 123.0(4) . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C23 C22 C19 118.7(5) . . ?
C23 C22 H22A 107.6 . . ?
C19 C22 H22A 107.6 . . ?
C23 C22 H22B 107.6 . . ?
C19 C22 H22B 107.6 . . ?
H22A C22 H22B 107.1 . . ?
C22 C23 C25 114.5(9) . . ?
C22 C23 C24 123.4(8) . . ?
C25 C23 C24 87.6(10) . . ?
C22 C23 H23 109.8 . . ?
C25 C23 H23 109.8 . . ?
C24 C23 H23 109.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 O3 125.9(3) . . ?
O4 C26 C27 118.6(3) . . ?
O3 C26 C27 115.5(3) . . ?
C28 C27 C29 110.2(3) . . ?
C28 C27 C26 112.7(4) . . ?
C29 C27 C26 111.7(2) . . ?
C28 C27 H27 107.3 . . ?
C29 C27 H27 107.3 . . ?
C26 C27 H27 107.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 117.3(3) . . ?
C34 C29 C27 119.9(3) . . ?
C30 C29 C27 122.9(3) . . ?
C31 C30 C29 120.9(3) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 121.9(3) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C33 C32 C31 116.3(3) . . ?
C33 C32 C35 122.0(4) . . ?
C31 C32 C35 121.8(4) . . ?
C34 C33 C32 122.0(3) . . ?
C34 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C33 C34 C29 121.6(3) . . ?
C33 C34 H34 119.2 . . ?
C29 C34 H34 119.2 . . ?
C32 C35 C36 114.9(4) . . ?
C32 C35 H35A 108.5 . . ?
C36 C35 H35A 108.5 . . ?
C32 C35 H35B 108.5 . . ?
C36 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C37 C36 C38 114.8(7) . . ?
C37 C36 C35 113.7(5) . . ?
C38 C36 C35 112.5(5) . . ?
C37 C36 H36 104.9 . . ?
C38 C36 H36 104.9 . . ?
C35 C36 H36 104.9 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_betapic
_database_code_depnum_ccdc_archive 'CCDC 1509594'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H50 Cu N2 O5'
_chemical_formula_sum            'C38 H50 Cu N2 O5'
_chemical_formula_weight         678.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4147(2)
_cell_length_b                   11.8811(3)
_cell_length_c                   17.5005(4)
_cell_angle_alpha                95.564(1)
_cell_angle_beta                 103.187(1)
_cell_angle_gamma                103.464(1)
_cell_volume                     1830.12(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    34072
_cell_measurement_theta_min      2.
_cell_measurement_theta_max      28.

_exptl_crystal_description       prismatic
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             722
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34072
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.735
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             8751
_reflns_number_gt                7084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014; WINGX (Farrugia, 1999)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1108P)²+0.2845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8751
_refine_ls_number_parameters     423
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.50515(3) 0.22340(2) -0.01707(2) 0.04408(12) Uani 1 1 d . . . . .
O1W O 0.3386(2) 0.04250(16) -0.06118(12) 0.0579(4) Uani 1 1 d D . . . .
O1 O 0.59238(19) 0.17068(15) 0.08171(10) 0.0496(4) Uani 1 1 d . . . . .
O2 O 0.7233(3) 0.35624(18) 0.12023(14) 0.0730(5) Uani 1 1 d . . . . .
O3 O 0.4360(2) 0.29853(18) -0.10865(11) 0.0605(4) Uani 1 1 d . . . . .
O4 O 0.2571(4) 0.1464(3) -0.18214(17) 0.1045(10) Uani 1 1 d . . . . .
N1 N 0.3637(2) 0.28364(18) 0.03767(12) 0.0480(4) Uani 1 1 d . . . . .
N2 N 0.6746(2) 0.19593(18) -0.06421(12) 0.0475(4) Uani 1 1 d . . . . .
C1 C 0.2392(3) 0.2106(2) 0.04699(15) 0.0511(5) Uani 1 1 d . . . . .
H1 H 0.2165 0.1321 0.0249 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1420(3) 0.2452(3) 0.08766(17) 0.0587(6) Uani 1 1 d . . . . .
C3 C 0.1792(4) 0.3622(3) 0.11987(18) 0.0681(7) Uani 1 1 d . . . . .
H3 H 0.1178 0.3896 0.1478 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3072(4) 0.4391(3) 0.11086(19) 0.0681(7) Uani 1 1 d . . . . .
H4 H 0.3327 0.5179 0.1327 0.082 Uiso 1 1 calc R U . . .
C5 C 0.3963(3) 0.3969(2) 0.06905(16) 0.0572(6) Uani 1 1 d . . . . .
H5 H 0.4817 0.4486 0.0624 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0049(3) 0.1580(4) 0.0953(2) 0.0793(9) Uani 1 1 d . . . . .
H6A H 0.0248 0.1352 0.1471 0.119 Uiso 1 1 calc R U . . .
H6B H -0.0193 0.0902 0.0554 0.119 Uiso 1 1 calc R U . . .
H6C H -0.0788 0.1926 0.0885 0.119 Uiso 1 1 calc R U . . .
C7 C 0.7898(3) 0.2873(2) -0.06352(16) 0.0526(5) Uani 1 1 d . . . . .
H7 H 0.7915 0.3604 -0.0384 0.063 Uiso 1 1 calc R U . . .
C8 C 0.9062(3) 0.2792(2) -0.09801(16) 0.0559(6) Uani 1 1 d . . . . .
C9 C 0.9039(3) 0.1686(3) -0.13276(17) 0.0617(6) Uani 1 1 d . . . . .
H9 H 0.9808 0.1583 -0.1557 0.074 Uiso 1 1 calc R U . . .
C10 C 0.7871(4) 0.0743(3) -0.13307(18) 0.0647(7) Uani 1 1 d . . . . .
H10 H 0.7840 -0.0002 -0.1566 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6747(3) 0.0906(2) -0.09837(16) 0.0557(6) Uani 1 1 d . . . . .
H11 H 0.5962 0.0261 -0.0987 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0302(4) 0.3858(3) -0.0974(2) 0.0778(9) Uani 1 1 d . . . . .
H12A H 1.0161 0.4530 -0.0680 0.117 Uiso 1 1 calc R U . . .
H12B H 1.0271 0.3988 -0.1510 0.117 Uiso 1 1 calc R U . . .
H12C H 1.1265 0.3736 -0.0730 0.117 Uiso 1 1 calc R U . . .
C13 C 0.6825(3) 0.2562(2) 0.13442(15) 0.0528(5) Uani 1 1 d . . . . .
C14 C 0.7339(3) 0.2227(3) 0.21675(16) 0.0643(7) Uani 1 1 d . . . . .
H14 H 0.7779 0.1565 0.2103 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8568(4) 0.3243(5) 0.2726(2) 0.1005(14) Uani 1 1 d . . . . .
H15A H 0.9446 0.3407 0.2522 0.151 Uiso 1 1 calc R U . . .
H15B H 0.8834 0.3029 0.3245 0.151 Uiso 1 1 calc R U . . .
H15C H 0.8195 0.3927 0.2761 0.151 Uiso 1 1 calc R U . . .
C16 C 0.6012(3) 0.1835(3) 0.25174(15) 0.0603(6) Uani 1 1 d . . . . .
C17 C 0.5871(5) 0.0860(3) 0.2909(2) 0.0760(8) Uani 1 1 d . . . . .
H17 H 0.6595 0.0438 0.2950 0.091 Uiso 1 1 calc R U . . .
C18 C 0.4671(5) 0.0521(3) 0.3233(2) 0.0868(10) Uani 1 1 d . . . . .
H18 H 0.4608 -0.0130 0.3492 0.104 Uiso 1 1 calc R U . . .
C19 C 0.3547(5) 0.1108(3) 0.3191(2) 0.0803(9) Uani 1 1 d . . . . .
C20 C 0.3695(4) 0.2076(3) 0.28034(18) 0.0740(8) Uani 1 1 d . . . . .
H20 H 0.2969 0.2496 0.2765 0.089 Uiso 1 1 calc R U . . .
C21 C 0.4895(4) 0.2433(3) 0.24721(16) 0.0650(7) Uani 1 1 d . . . . .
H21 H 0.4957 0.3084 0.2214 0.078 Uiso 1 1 calc R U . . .
C22 C 0.2174(6) 0.0687(5) 0.3498(3) 0.1127(16) Uani 1 1 d . . . . .
H22A H 0.1292 0.0741 0.3105 0.135 Uiso 1 1 calc R U . . .
H22B H 0.2057 -0.0136 0.3542 0.135 Uiso 1 1 calc R U . . .
C23 C 0.2180(12) 0.1323(10) 0.4287(6) 0.193(4) Uani 1 1 d D . . . .
H23 H 0.1187 0.1018 0.4384 0.231 Uiso 1 1 calc R U . . .
C24 C 0.2594(17) 0.2537(12) 0.4510(9) 0.277(8) Uani 1 1 d D . . . .
H24A H 0.3076 0.2900 0.4135 0.416 Uiso 1 1 calc R U . . .
H24B H 0.3282 0.2743 0.5030 0.416 Uiso 1 1 calc R U . . .
H24C H 0.1708 0.2802 0.4517 0.416 Uiso 1 1 calc R U . . .
C25 C 0.3380(13) 0.1087(13) 0.4969(6) 0.240(7) Uani 1 1 d D . . . .
H25A H 0.4367 0.1388 0.4892 0.360 Uiso 1 1 calc R U . . .
H25B H 0.3194 0.0258 0.4972 0.360 Uiso 1 1 calc R U . . .
H25C H 0.3326 0.1468 0.5467 0.360 Uiso 1 1 calc R U . . .
C26 C 0.3357(3) 0.2478(3) -0.17085(17) 0.0640(7) Uani 1 1 d . . . . .
C27 C 0.3138(4) 0.3209(4) -0.2375(2) 0.0811(10) Uani 1 1 d . . . . .
H27 H 0.3061 0.3968 -0.2141 0.097 Uiso 1 1 calc R U . . .
C28 C 0.1710(5) 0.2667(7) -0.3016(3) 0.133(2) Uani 1 1 d . . . . .
H28A H 0.1593 0.3180 -0.3404 0.200 Uiso 1 1 calc R U . . .
H28B H 0.0862 0.2548 -0.2788 0.200 Uiso 1 1 calc R U . . .
H28C H 0.1760 0.1928 -0.3267 0.200 Uiso 1 1 calc R U . . .
C29 C 0.4491(4) 0.3443(3) -0.27318(16) 0.0650(7) Uani 1 1 d . . . . .
C30 C 0.5494(4) 0.2743(3) -0.26797(17) 0.0692(7) Uani 1 1 d . . . . .
H30 H 0.5342 0.2095 -0.2420 0.083 Uiso 1 1 calc R U . . .
C31 C 0.6710(4) 0.2994(3) -0.30074(19) 0.0750(8) Uani 1 1 d . . . . .
H31 H 0.7375 0.2521 -0.2953 0.090 Uiso 1 1 calc R U . . .
C32 C 0.6972(4) 0.3942(3) -0.34187(18) 0.0742(8) Uani 1 1 d . . . . .
C33 C 0.5960(5) 0.4632(3) -0.3462(2) 0.0869(11) Uani 1 1 d . . . . .
H33 H 0.6104 0.5278 -0.3723 0.104 Uiso 1 1 calc R U . . .
C34 C 0.4759(5) 0.4392(3) -0.3133(2) 0.0814(9) Uani 1 1 d . . . . .
H34 H 0.4107 0.4876 -0.3179 0.098 Uiso 1 1 calc R U . . .
C35 C 0.8259(5) 0.4184(5) -0.3800(2) 0.0961(12) Uani 1 1 d . . . . .
H35A H 0.9110 0.3978 -0.3470 0.115 Uiso 1 1 calc R U . . .
H35B H 0.8564 0.5018 -0.3812 0.115 Uiso 1 1 calc R U . . .
C36 C 0.7912(7) 0.3518(6) -0.4657(3) 0.1145(16) Uani 1 1 d . . . . .
H36 H 0.8862 0.3762 -0.4811 0.137 Uiso 1 1 calc R U . . .
C37 C 0.7642(13) 0.2297(10) -0.4704(5) 0.201(4) Uani 1 1 d . . . . .
H37A H 0.6793 0.2000 -0.4496 0.302 Uiso 1 1 calc R U . . .
H37B H 0.8520 0.2113 -0.4399 0.302 Uiso 1 1 calc R U . . .
H37C H 0.7429 0.1944 -0.5249 0.302 Uiso 1 1 calc R U . . .
C38 C 0.6814(8) 0.3933(7) -0.5231(3) 0.144(2) Uani 1 1 d . . . . .
H38A H 0.6700 0.3548 -0.5758 0.216 Uiso 1 1 calc R U . . .
H38B H 0.7174 0.4765 -0.5205 0.216 Uiso 1 1 calc R U . . .
H38C H 0.5855 0.3756 -0.5104 0.216 Uiso 1 1 calc R U . . .
H1W H 0.320(5) 0.070(4) -0.1044(16) 0.089(12) Uiso 1 1 d D . . . .
H2W H 0.366(4) -0.021(2) -0.074(2) 0.079(11) Uiso 1 1 d 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
Cu1 O1 1.9639(16) . ?
Cu1 O3 1.9649(18) . ?
Cu1 N1 2.024(2) . ?
Cu1 N2 2.030(2) . ?
Cu1 O1W 2.2869(18) . ?
O1W H1W 0.849(19) . ?
O1W H2W 0.879(18) . ?
O1 C13 1.290(3) . ?
O2 C13 1.229(3) . ?
O3 C26 1.256(4) . ?
O4 C26 1.229(4) . ?
N1 C1 1.339(3) . ?
N1 C5 1.339(3) . ?
N2 C11 1.334(3) . ?
N2 C7 1.341(3) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(5) . ?
C2 C6 1.498(4) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(4) . ?
C8 C12 1.507(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.533(4) . ?
C14 C16 1.512(4) . ?
C14 C15 1.535(5) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.392(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.373(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(5) . ?
C19 C22 1.509(6) . ?
C20 C21 1.385(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.507(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.394(12) . ?
C23 C25 1.541(15) . ?
C23 H23 0.9800 . ?
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 C27 1.525(4) . ?
C27 C28 1.500(6) . ?
C27 C29 1.523(5) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C34 1.389(5) . ?
C29 C30 1.390(4) . ?
C30 C31 1.380(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.398(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.388(6) . ?
C32 C35 1.497(6) . ?
C33 C34 1.367(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.551(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.404(11) . ?
C36 C38 1.477(8) . ?
C36 H36 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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 O3 171.83(8) . . ?
O1 Cu1 N1 89.03(8) . . ?
O3 Cu1 N1 89.44(8) . . ?
O1 Cu1 N2 91.24(7) . . ?
O3 Cu1 N2 88.66(8) . . ?
N1 Cu1 N2 168.51(8) . . ?
O1 Cu1 O1W 90.22(7) . . ?
O3 Cu1 O1W 97.88(8) . . ?
N1 Cu1 O1W 92.89(8) . . ?
N2 Cu1 O1W 98.60(8) . . ?
Cu1 O1W H1W 83(3) . . ?
Cu1 O1W H2W 123(2) . . ?
H1W O1W H2W 104(4) . . ?
C13 O1 Cu1 112.33(16) . . ?
C26 O3 Cu1 125.1(2) . . ?
C1 N1 C5 118.2(2) . . ?
C1 N1 Cu1 121.03(17) . . ?
C5 N1 Cu1 120.68(18) . . ?
C11 N2 C7 117.9(2) . . ?
C11 N2 Cu1 122.77(17) . . ?
C7 N2 Cu1 119.28(17) . . ?
N1 C1 C2 123.9(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 116.6(3) . . ?
C3 C2 C6 122.9(3) . . ?
C1 C2 C6 120.6(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 123.9(2) . . ?
N2 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 C12 121.4(3) . . ?
C9 C8 C12 121.6(3) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N2 C11 C10 122.1(3) . . ?
N2 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O1 123.1(2) . . ?
O2 C13 C14 122.7(2) . . ?
O1 C13 C14 114.2(2) . . ?
C16 C14 C15 111.3(3) . . ?
C16 C14 C13 111.0(2) . . ?
C15 C14 C13 110.9(3) . . ?
C16 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.3(3) . . ?
C21 C16 C14 121.6(3) . . ?
C17 C16 C14 121.0(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 122.8(3) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 116.5(3) . . ?
C20 C19 C22 120.7(4) . . ?
C18 C19 C22 122.7(4) . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C23 C22 C19 116.6(5) . . ?
C23 C22 H22A 108.1 . . ?
C19 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C19 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C24 C23 C22 125.3(10) . . ?
C24 C23 C25 95.8(10) . . ?
C22 C23 C25 111.1(9) . . ?
C24 C23 H23 107.8 . . ?
C22 C23 H23 107.8 . . ?
C25 C23 H23 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 O3 125.9(3) . . ?
O4 C26 C27 118.6(3) . . ?
O3 C26 C27 115.5(3) . . ?
C28 C27 C29 110.2(3) . . ?
C28 C27 C26 112.6(4) . . ?
C29 C27 C26 111.6(2) . . ?
C28 C27 H27 107.4 . . ?
C29 C27 H27 107.4 . . ?
C26 C27 H27 107.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 117.2(3) . . ?
C34 C29 C27 119.8(3) . . ?
C30 C29 C27 123.0(3) . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 121.9(3) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C33 C32 C31 116.3(3) . . ?
C33 C32 C35 122.1(4) . . ?
C31 C32 C35 121.6(4) . . ?
C34 C33 C32 122.2(3) . . ?
C34 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
C33 C34 C29 121.5(3) . . ?
C33 C34 H34 119.2 . . ?
C29 C34 H34 119.2 . . ?
C32 C35 C36 114.9(4) . . ?
C32 C35 H35A 108.5 . . ?
C36 C35 H35A 108.5 . . ?
C32 C35 H35B 108.5 . . ?
C36 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C37 C36 C38 115.9(7) . . ?
C37 C36 C35 114.0(5) . . ?
C38 C36 C35 112.3(5) . . ?
C37 C36 H36 104.4 . . ?
C38 C36 H36 104.4 . . ?
C35 C36 H36 104.4 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         0.924
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.067

