# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_ket
_database_code_depnum_ccdc_archive 'CCDC 1006415'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H28 Cu N2 O2'
_chemical_formula_weight         428.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0615(3)
_cell_length_b                   12.4388(6)
_cell_length_c                   13.4851(8)
_cell_angle_alpha                70.511(5)
_cell_angle_beta                 83.469(4)
_cell_angle_gamma                76.344(4)
_cell_volume                     1084.26(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7008
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3822
_reflns_number_gt                3330
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] 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_extinction_coef       ?
_refine_ls_number_reflns         3822
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.69759(4) 0.75016(3) 0.19942(2) 0.03548(17) Uani 1 1 d . . .
O2 O 0.9381(3) 0.7049(2) 0.11414(19) 0.0513(6) Uani 1 1 d . . .
O1 O 0.8619(3) 0.87175(19) 0.1390(2) 0.0548(6) Uani 1 1 d . . .
N1 N 0.4966(4) 0.8320(2) 0.26980(19) 0.0391(6) Uani 1 1 d . . .
N2 N 0.5914(3) 0.6141(2) 0.23169(19) 0.0367(5) Uani 1 1 d . . .
C15 C 0.8213(5) 0.4311(3) 0.3020(3) 0.0486(8) Uani 1 1 d . . .
C10 C 0.1706(5) 0.8768(4) 0.3507(3) 0.0606(10) Uani 1 1 d . . .
H10A H 0.2128 0.8754 0.4164 0.091 Uiso 1 1 calc R . .
H10B H 0.0522 0.8483 0.3625 0.091 Uiso 1 1 calc R . .
H10C H 0.1478 0.9553 0.3033 0.091 Uiso 1 1 calc R . .
C14 C 0.7195(4) 0.5120(2) 0.2169(2) 0.0394(7) Uani 1 1 d . . .
C13 C 0.3313(5) 0.5026(3) 0.2800(3) 0.0597(9) Uani 1 1 d . . .
H13A H 0.3776 0.4750 0.2212 0.090 Uiso 1 1 calc R . .
H13B H 0.1913 0.5219 0.2822 0.090 Uiso 1 1 calc R . .
H13C H 0.3759 0.4428 0.3440 0.090 Uiso 1 1 calc R . .
C8 C 0.5378(4) 0.9304(3) 0.2908(2) 0.0418(7) Uani 1 1 d . . .
C12 C 0.4083(5) 0.6099(3) 0.2681(2) 0.0425(7) Uani 1 1 d . . .
C22 C 0.9748(4) 0.8036(3) 0.0967(2) 0.0399(7) Uani 1 1 d . . .
C9 C 0.3256(4) 0.8006(3) 0.3035(2) 0.0415(7) Uani 1 1 d . . .
C23 C 1.1471(5) 0.8373(3) 0.0284(3) 0.0549(9) Uani 1 1 d . . .
H23A H 1.2516 0.8294 0.0718 0.082 Uiso 1 1 calc R . .
H23B H 1.1119 0.9168 -0.0160 0.082 Uiso 1 1 calc R . .
H23C H 1.1886 0.7873 -0.0144 0.082 Uiso 1 1 calc R . .
C20 C 0.7453(4) 0.4989(3) 0.1163(3) 0.0446(7) Uani 1 1 d . . .
C6 C 0.6266(4) 0.9106(3) 0.3824(3) 0.0511(8) Uani 1 1 d . . .
C16 C 0.7970(7) 0.4478(4) 0.4089(3) 0.0753(12) Uani 1 1 d . . .
H16A H 0.8164 0.5238 0.4022 0.113 Uiso 1 1 calc R . .
H16B H 0.8912 0.3894 0.4550 0.113 Uiso 1 1 calc R . .
H16C H 0.6680 0.4409 0.4376 0.113 Uiso 1 1 calc R . .
C11 C 0.2832(4) 0.7000(3) 0.2975(3) 0.0459(8) Uani 1 1 d . . .
H11 H 0.1553 0.6914 0.3154 0.055 Uiso 1 1 calc R . .
C2 C 0.4966(5) 1.0411(3) 0.2149(3) 0.0535(8) Uani 1 1 d . . .
C19 C 0.8749(5) 0.4008(3) 0.1052(3) 0.0607(10) Uani 1 1 d . . .
H19 H 0.8958 0.3902 0.0394 0.073 Uiso 1 1 calc R . .
C3 C 0.5465(7) 1.1329(4) 0.2354(4) 0.0765(13) Uani 1 1 d . . .
H3 H 0.5186 1.2074 0.1869 0.092 Uiso 1 1 calc R . .
C17 C 0.9485(5) 0.3342(3) 0.2853(4) 0.0654(11) Uani 1 1 d . . .
H17 H 1.0184 0.2786 0.3412 0.079 Uiso 1 1 calc R . .
C18 C 0.9728(6) 0.3189(3) 0.1890(4) 0.0697(11) Uani 1 1 d . . .
H18 H 1.0564 0.2525 0.1801 0.084 Uiso 1 1 calc R . .
C5 C 0.6749(5) 1.0060(5) 0.3993(4) 0.0717(12) Uani 1 1 d . . .
H5 H 0.7341 0.9952 0.4611 0.086 Uiso 1 1 calc R . .
C21 C 0.6403(6) 0.5895(3) 0.0256(3) 0.0583(9) Uani 1 1 d . . .
H21A H 0.6838 0.5702 -0.0376 0.087 Uiso 1 1 calc R . .
H21B H 0.6664 0.6640 0.0188 0.087 Uiso 1 1 calc R . .
H21C H 0.5026 0.5927 0.0371 0.087 Uiso 1 1 calc R . .
C7 C 0.6687(6) 0.7900(4) 0.4634(3) 0.0713(11) Uani 1 1 d . . .
H7A H 0.5575 0.7552 0.4725 0.107 Uiso 1 1 calc R . .
H7B H 0.6953 0.7963 0.5293 0.107 Uiso 1 1 calc R . .
H7C H 0.7799 0.7422 0.4397 0.107 Uiso 1 1 calc R . .
C4 C 0.6359(7) 1.1154(5) 0.3259(5) 0.0833(15) Uani 1 1 d . . .
H4 H 0.6704 1.1776 0.3378 0.100 Uiso 1 1 calc R . .
C1 C 0.4000(7) 1.0601(3) 0.1152(3) 0.0737(11) Uani 1 1 d . . .
H1A H 0.4752 1.0084 0.0791 0.110 Uiso 1 1 calc R . .
H1B H 0.3918 1.1395 0.0708 0.110 Uiso 1 1 calc R . .
H1C H 0.2712 1.0447 0.1317 0.110 Uiso 1 1 calc R . .


_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 1.899(2) . ?
Cu1 N2 1.910(2) . ?
Cu1 O2 2.015(2) . ?
Cu1 O1 2.022(2) . ?
O2 C22 1.255(4) . ?
O1 C22 1.256(4) . ?
N1 C9 1.340(4) . ?
N1 C8 1.443(4) . ?
N2 C12 1.336(4) . ?
N2 C14 1.434(4) . ?
C15 C14 1.386(4) . ?
C15 C17 1.391(5) . ?
C15 C16 1.509(5) . ?
C10 C9 1.501(4) . ?
C14 C20 1.406(4) . ?
C13 C12 1.511(4) . ?
C8 C6 1.371(5) . ?
C8 C2 1.402(5) . ?
C12 C11 1.394(5) . ?
C22 C23 1.495(4) . ?
C9 C11 1.382(5) . ?
C20 C19 1.383(5) . ?
C20 C21 1.485(5) . ?
C6 C5 1.402(5) . ?
C6 C7 1.517(6) . ?
C2 C3 1.387(5) . ?
C2 C1 1.501(5) . ?
C19 C18 1.366(6) . ?
C3 C4 1.366(7) . ?
C17 C18 1.361(6) . ?
C5 C4 1.377(7) . ?

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 N2 96.27(10) . . ?
N1 Cu1 O2 163.99(10) . . ?
N2 Cu1 O2 99.72(10) . . ?
N1 Cu1 O1 99.75(10) . . ?
N2 Cu1 O1 163.78(10) . . ?
O2 Cu1 O1 64.23(9) . . ?
C22 O2 Cu1 89.31(18) . . ?
C22 O1 Cu1 88.95(18) . . ?
C9 N1 C8 119.5(2) . . ?
C9 N1 Cu1 123.8(2) . . ?
C8 N1 Cu1 116.65(18) . . ?
C12 N2 C14 119.7(2) . . ?
C12 N2 Cu1 123.5(2) . . ?
C14 N2 Cu1 116.86(18) . . ?
C14 C15 C17 117.7(3) . . ?
C14 C15 C16 121.4(3) . . ?
C17 C15 C16 121.0(3) . . ?
C15 C14 C20 121.8(3) . . ?
C15 C14 N2 118.6(3) . . ?
C20 C14 N2 119.5(3) . . ?
C6 C8 C2 122.3(3) . . ?
C6 C8 N1 118.3(3) . . ?
C2 C8 N1 119.4(3) . . ?
N2 C12 C11 123.0(3) . . ?
N2 C12 C13 119.4(3) . . ?
C11 C12 C13 117.6(3) . . ?
O2 C22 O1 117.5(3) . . ?
O2 C22 C23 120.6(3) . . ?
O1 C22 C23 122.0(3) . . ?
N1 C9 C11 123.2(3) . . ?
N1 C9 C10 119.4(3) . . ?
C11 C9 C10 117.4(3) . . ?
C19 C20 C14 117.4(3) . . ?
C19 C20 C21 121.9(3) . . ?
C14 C20 C21 120.6(3) . . ?
C8 C6 C5 117.7(4) . . ?
C8 C6 C7 121.2(3) . . ?
C5 C6 C7 121.1(4) . . ?
C9 C11 C12 128.1(3) . . ?
C3 C2 C8 117.9(4) . . ?
C3 C2 C1 121.0(4) . . ?
C8 C2 C1 121.1(3) . . ?
C18 C19 C20 121.4(4) . . ?
C4 C3 C2 121.0(4) . . ?
C18 C17 C15 121.4(4) . . ?
C17 C18 C19 120.3(4) . . ?
C4 C5 C6 121.0(4) . . ?
C3 C4 C5 120.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.193
_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/. 
# 
# Audit and citation data items have may 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_exp_2009
_database_code_depnum_ccdc_archive 'CCDC 1007056'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C75 H96 Cu7 N6 O23, C2 H3 N'
_chemical_formula_sum            'C77 H99 Cu7 N7 O23'
_chemical_formula_weight         1935.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   'P21 3'
_space_group_name_Hall           'P 2ac 2ab 3'
_chemical_absolute_configuration unk

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

_cell_length_a                   22.7589(3)
_cell_length_b                   22.7589(3)
_cell_length_c                   22.7589(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     11788.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3964
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15585
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         25.24
_reflns_number_total             6992
_reflns_number_gt                5668
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

DFIX 1.48 0.001 C25 C24
DELU 0.005 C24 C25
SIMU 0.005 C24 C25
ISOR 0.01 C24 C25  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.6774P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(19)
_refine_ls_number_reflns         6992
_refine_ls_number_parameters     352
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu2 Cu 0.34812(3) 0.34812(3) 0.34812(3) 0.0340(3) Uani 1 3 d S . .
Cu1 Cu 0.36789(3) 0.48397(3) 0.39698(3) 0.03581(17) Uani 1 1 d . . .
O5 O 0.31074(14) 0.42122(15) 0.39040(15) 0.0365(8) Uani 1 1 d . . .
C11 C 0.2684(2) 0.4280(2) 0.3450(2) 0.0319(10) Uani 1 1 d . . .
N2 N 0.17242(18) 0.38380(18) 0.35129(19) 0.0361(9) Uani 1 1 d . . .
C12 C 0.2059(2) 0.4247(2) 0.3711(2) 0.0361(12) Uani 1 1 d . . .
C17 C 0.0382(3) 0.3325(3) 0.4276(3) 0.0661(19) Uani 1 1 d . . .
H17 H 0.0276 0.3054 0.4564 0.079 Uiso 1 1 calc R . .
C20 C 0.0693(3) 0.4108(3) 0.3388(3) 0.0602(18) Uani 1 1 d . . .
C14 C 0.1126(2) 0.3791(2) 0.3698(2) 0.0419(12) Uani 1 1 d . . .
C13 C 0.1880(2) 0.4697(2) 0.4162(2) 0.0438(13) Uani 1 1 d . . .
H13A H 0.1660 0.5005 0.3974 0.066 Uiso 1 1 calc R . .
H13B H 0.2225 0.4861 0.4342 0.066 Uiso 1 1 calc R . .
H13C H 0.1642 0.4514 0.4457 0.066 Uiso 1 1 calc R . .
C15 C 0.0964(3) 0.3398(3) 0.4140(3) 0.0531(15) Uani 1 1 d . . .
C21 C 0.0865(3) 0.4520(4) 0.2885(4) 0.095(3) Uani 1 1 d . . .
H21A H 0.0538 0.4566 0.2623 0.143 Uiso 1 1 calc R . .
H21B H 0.1192 0.4357 0.2675 0.143 Uiso 1 1 calc R . .
H21C H 0.0973 0.4897 0.3042 0.143 Uiso 1 1 calc R . .
C18 C -0.0043(3) 0.3639(4) 0.4000(3) 0.074(2) Uani 1 1 d . . .
H18 H -0.0436 0.3591 0.4104 0.089 Uiso 1 1 calc R . .
C16 C 0.1415(3) 0.3041(3) 0.4468(3) 0.068(2) Uani 1 1 d . . .
H16A H 0.1491 0.3221 0.4842 0.102 Uiso 1 1 calc R . .
H16B H 0.1772 0.3024 0.4244 0.102 Uiso 1 1 calc R . .
H16C H 0.1268 0.2650 0.4528 0.102 Uiso 1 1 calc R . .
C19 C 0.0115(3) 0.4031(3) 0.3562(4) 0.075(2) Uani 1 1 d . . .
H19 H -0.0177 0.4250 0.3378 0.090 Uiso 1 1 calc R . .
N1 N 0.31552(18) 0.52260(17) 0.33788(18) 0.0341(10) Uani 1 1 d . . .
C9 C 0.2764(2) 0.4899(2) 0.3167(2) 0.0316(11) Uani 1 1 d . . .
C10 C 0.2349(2) 0.5048(2) 0.2683(2) 0.0429(13) Uani 1 1 d . . .
H10A H 0.2032 0.5280 0.2837 0.064 Uiso 1 1 calc R . .
H10B H 0.2195 0.4693 0.2516 0.064 Uiso 1 1 calc R . .
H10C H 0.2552 0.5267 0.2386 0.064 Uiso 1 1 calc R . .
C6 C 0.3656(2) 0.5905(2) 0.2706(2) 0.0438(13) Uani 1 1 d . . .
C8 C 0.3260(2) 0.5818(2) 0.3160(2) 0.0389(12) Uani 1 1 d . . .
C2 C 0.2977(3) 0.6286(2) 0.3447(3) 0.0470(14) Uani 1 1 d . . .
C5 C 0.3744(3) 0.6474(3) 0.2501(3) 0.0552(16) Uani 1 1 d . . .
H5 H 0.3981 0.6536 0.2174 0.066 Uiso 1 1 calc R . .
O4 O 0.42920(13) 0.42920(13) 0.42920(13) 0.0326(13) Uani 1 3 d S . .
O2 O 0.42874(17) 0.54468(16) 0.38939(18) 0.0461(9) Uani 1 1 d . . .
O3 O 0.3317(2) 0.51872(19) 0.4860(2) 0.0627(12) Uani 1 1 d . . .
C3 C 0.3116(3) 0.6855(3) 0.3248(3) 0.0655(19) Uani 1 1 d . . .
H3A H 0.2958 0.7180 0.3439 0.079 Uiso 1 1 calc R . .
C4 C 0.3489(3) 0.6938(3) 0.2769(3) 0.0608(18) Uani 1 1 d . . .
H4 H 0.3562 0.7316 0.2632 0.073 Uiso 1 1 calc R . .
C1 C 0.2560(3) 0.6201(3) 0.3941(3) 0.070(2) Uani 1 1 d . . .
H1A H 0.2190 0.6064 0.3791 0.106 Uiso 1 1 calc R . .
H1B H 0.2503 0.6567 0.4142 0.106 Uiso 1 1 calc R . .
H1C H 0.2717 0.5916 0.4210 0.106 Uiso 1 1 calc R . .
C7 C 0.3979(3) 0.5400(3) 0.2423(3) 0.0595(17) Uani 1 1 d . . .
H7A H 0.4316 0.5301 0.2656 0.089 Uiso 1 1 calc R . .
H7B H 0.4103 0.5512 0.2036 0.089 Uiso 1 1 calc R . .
H7C H 0.3723 0.5066 0.2398 0.089 Uiso 1 1 calc R . .
C22 C 0.4311(3) 0.5959(3) 0.4137(4) 0.0655(19) Uani 1 1 d . . .
C23 C 0.4758(4) 0.6362(4) 0.3890(5) 0.110(3) Uani 1 1 d . . .
H23A H 0.4566 0.6665 0.3668 0.165 Uiso 1 1 calc R . .
H23B H 0.5018 0.6146 0.3638 0.165 Uiso 1 1 calc R . .
H23C H 0.4979 0.6537 0.4204 0.165 Uiso 1 1 calc R . .
O1 O 0.3987(3) 0.6123(2) 0.4549(3) 0.0898(17) Uani 1 1 d . . .
O6 O 0.27626(15) 0.38530(14) 0.30301(15) 0.0367(8) Uani 1 1 d . . .
Cu3 Cu 0.21361(3) 0.32733(3) 0.29855(3) 0.04392(19) Uani 1 1 d . . .
O9 O 0.1502(2) 0.2703(2) 0.3052(2) 0.0734(14) Uani 1 1 d . . .
O7 O 0.26621(15) 0.26621(15) 0.26621(15) 0.0349(13) Uani 1 3 d S . .
C24 C 0.1567(5) 0.2170(6) 0.3349(6) 0.129(3) Uani 1 1 d DU . .
O8 O 0.2034(3) 0.1868(3) 0.3565(3) 0.107(2) Uani 1 1 d . . .
C25 C 0.1018(5) 0.1841(5) 0.3467(6) 0.153(4) Uani 1 1 d DU . .
H25A H 0.0712 0.1983 0.3213 0.229 Uiso 1 1 calc R . .
H25B H 0.0905 0.1896 0.3869 0.229 Uiso 1 1 calc R . .
H25C H 0.1082 0.1430 0.3394 0.229 Uiso 1 1 calc R . .
N3 N 0.4120(4) 0.5880(4) 0.0880(4) 0.171(11) Uani 1 3 d S . .
C27 C 0.4759(9) 0.5241(9) 0.0241(9) 0.171(11) Uani 1 3 d S . .
H27A H 0.5039 0.5482 0.0037 0.256 Uiso 1 1 calc R . .
H27B H 0.4518 0.5037 -0.0039 0.256 Uiso 1 1 calc R . .
H27C H 0.4963 0.4961 0.0482 0.256 Uiso 1 1 calc R . .
C26 C 0.4387(9) 0.5613(9) 0.0613(9) 0.127(8) Uani 1 3 d S . .


_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
Cu2 O5 2.102(3) . ?
Cu2 O5 2.102(3) 4 ?
Cu2 O5 2.102(3) 9 ?
Cu2 O6 2.108(4) 4 ?
Cu2 O6 2.108(4) . ?
Cu2 O6 2.108(4) 9 ?
Cu1 O5 1.937(3) . ?
Cu1 O2 1.964(4) . ?
Cu1 N1 2.001(4) . ?
Cu1 O4 2.0097(15) . ?
Cu1 O3 2.325(4) . ?
O5 C11 1.422(6) . ?
C11 O6 1.374(6) . ?
C11 C12 1.544(7) . ?
C11 C9 1.559(7) . ?
N2 C12 1.285(7) . ?
N2 C14 1.429(7) . ?
N2 Cu3 1.993(4) . ?
C12 C13 1.506(7) . ?
C17 C18 1.357(10) . ?
C17 C15 1.372(9) . ?
C17 H17 0.9300 . ?
C20 C19 1.385(9) . ?
C20 C14 1.410(8) . ?
C20 C21 1.530(9) . ?
C14 C15 1.395(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.507(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 C19 1.387(10) . ?
C18 H18 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19 0.9300 . ?
N1 C9 1.257(6) . ?
N1 C8 1.455(6) . ?
C9 C10 1.489(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 C8 1.386(7) . ?
C6 C5 1.391(8) . ?
C6 C7 1.509(8) . ?
C8 C2 1.407(8) . ?
C2 C3 1.407(8) . ?
C2 C1 1.484(9) . ?
C5 C4 1.349(9) . ?
C5 H5 0.9300 . ?
O4 Cu1 2.0096(15) 4 ?
O4 Cu1 2.0098(15) 9 ?
O2 C22 1.293(8) . ?
C3 C4 1.396(10) . ?
C3 H3A 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C22 O1 1.250(9) . ?
C22 C23 1.480(10) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O6 Cu3 1.945(3) . ?
Cu3 O9 1.947(4) . ?
Cu3 O7 1.9773(17) . ?
Cu3 O8 2.346(6) 9 ?
O9 C24 1.397(14) . ?
O7 Cu3 1.9772(17) 4 ?
O7 Cu3 1.9774(17) 9 ?
C24 O8 1.357(14) . ?
C24 C25 1.4801(10) . ?
O8 Cu3 2.346(6) 4 ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N3 C26 1.05(3) . ?
C27 C26 1.47(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O5 Cu2 O5 98.23(12) . 4 ?
O5 Cu2 O5 98.23(12) . 9 ?
O5 Cu2 O5 98.23(12) 4 9 ?
O5 Cu2 O6 103.48(12) . 4 ?
O5 Cu2 O6 65.88(13) 4 4 ?
O5 Cu2 O6 154.57(12) 9 4 ?
O5 Cu2 O6 65.87(13) . . ?
O5 Cu2 O6 154.57(12) 4 . ?
O5 Cu2 O6 103.48(12) 9 . ?
O6 Cu2 O6 97.42(12) 4 . ?
O5 Cu2 O6 154.57(12) . 9 ?
O5 Cu2 O6 103.48(12) 4 9 ?
O5 Cu2 O6 65.87(13) 9 9 ?
O6 Cu2 O6 97.42(12) 4 9 ?
O6 Cu2 O6 97.42(12) . 9 ?
O5 Cu1 O2 170.14(16) . . ?
O5 Cu1 N1 82.65(15) . . ?
O2 Cu1 N1 92.97(16) . . ?
O5 Cu1 O4 92.13(16) . . ?
O2 Cu1 O4 88.78(16) . . ?
N1 Cu1 O4 158.68(16) . . ?
O5 Cu1 O3 94.61(16) . . ?
O2 Cu1 O3 94.99(17) . . ?
N1 Cu1 O3 103.03(17) . . ?
O4 Cu1 O3 97.98(15) . . ?
C11 O5 Cu1 115.5(3) . . ?
C11 O5 Cu2 91.6(3) . . ?
Cu1 O5 Cu2 110.32(16) . . ?
O6 C11 O5 109.9(4) . . ?
O6 C11 C12 110.7(4) . . ?
O5 C11 C12 109.8(4) . . ?
O6 C11 C9 109.7(4) . . ?
O5 C11 C9 108.7(4) . . ?
C12 C11 C9 108.1(4) . . ?
C12 N2 C14 121.0(5) . . ?
C12 N2 Cu3 113.6(3) . . ?
C14 N2 Cu3 125.3(3) . . ?
N2 C12 C13 124.9(5) . . ?
N2 C12 C11 116.5(5) . . ?
C13 C12 C11 118.6(5) . . ?
C18 C17 C15 121.3(6) . . ?
C18 C17 H17 119.3 . . ?
C15 C17 H17 119.3 . . ?
C19 C20 C14 117.0(6) . . ?
C19 C20 C21 122.3(6) . . ?
C14 C20 C21 120.6(5) . . ?
C15 C14 C20 120.3(5) . . ?
C15 C14 N2 120.7(5) . . ?
C20 C14 N2 118.7(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C15 C14 119.7(6) . . ?
C17 C15 C16 118.6(6) . . ?
C14 C15 C16 121.6(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 C19 119.1(6) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
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 . . ?
C20 C19 C18 122.4(7) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C9 N1 C8 122.2(4) . . ?
C9 N1 Cu1 114.9(3) . . ?
C8 N1 Cu1 122.6(3) . . ?
N1 C9 C10 126.8(5) . . ?
N1 C9 C11 117.3(4) . . ?
C10 C9 C11 115.9(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C6 C5 118.5(6) . . ?
C8 C6 C7 121.7(5) . . ?
C5 C6 C7 119.7(5) . . ?
C6 C8 C2 122.4(5) . . ?
C6 C8 N1 119.6(5) . . ?
C2 C8 N1 117.9(5) . . ?
C8 C2 C3 116.4(6) . . ?
C8 C2 C1 123.0(5) . . ?
C3 C2 C1 120.5(6) . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
Cu1 O4 Cu1 113.80(12) 4 . ?
Cu1 O4 Cu1 113.80(12) 4 9 ?
Cu1 O4 Cu1 113.80(12) . 9 ?
C22 O2 Cu1 128.8(4) . . ?
C4 C3 C2 120.8(6) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C3 120.5(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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 . . ?
O1 C22 O2 124.4(6) . . ?
O1 C22 C23 120.4(7) . . ?
O2 C22 C23 115.1(8) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 O6 Cu3 114.9(3) . . ?
C11 O6 Cu2 92.7(3) . . ?
Cu3 O6 Cu2 108.76(15) . . ?
O6 Cu3 O9 172.47(19) . . ?
O6 Cu3 O7 93.03(17) . . ?
O9 Cu3 O7 90.54(19) . . ?
O6 Cu3 N2 82.87(15) . . ?
O9 Cu3 N2 91.93(18) . . ?
O7 Cu3 N2 164.31(18) . . ?
O6 Cu3 O8 92.7(2) . 9 ?
O9 Cu3 O8 93.9(2) . 9 ?
O7 Cu3 O8 90.7(2) . 9 ?
N2 Cu3 O8 104.6(2) . 9 ?
C24 O9 Cu3 122.6(5) . . ?
Cu3 O7 Cu3 112.92(14) 4 . ?
Cu3 O7 Cu3 112.91(14) 4 9 ?
Cu3 O7 Cu3 112.92(14) . 9 ?
O8 C24 O9 134.2(7) . . ?
O8 C24 C25 109.8(11) . . ?
O9 C24 C25 115.9(11) . . ?
C24 O8 Cu3 119.3(6) . 4 ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C26 C27 180(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.069

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.037 0.002 0.285 4573 601 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_exp_1570
_database_code_depnum_ccdc_archive 'CCDC 1006417'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N3 O'
_chemical_formula_weight         335.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/c

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

_cell_length_a                   21.2119(14)
_cell_length_b                   7.8518(4)
_cell_length_c                   23.5414(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.420(6)
_cell_angle_gamma                90.00
_cell_volume                     3903.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8291
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3442
_reflns_number_gt                2194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.7407P] 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_extinction_coef       ?
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1977
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74078(9) 0.4249(2) 0.51383(8) 0.0551(6) Uani 1 1 d . . .
H1 H 0.7700 0.3568 0.5135 0.083 Uiso 1 1 calc R . .
N1 N 0.64984(9) 0.7291(2) 0.48265(8) 0.0381(5) Uani 1 1 d . . .
N2 N 0.65485(10) 0.8192(2) 0.62483(8) 0.0420(5) Uani 1 1 d . . .
N3 N 0.74816(10) 0.5196(2) 0.56347(9) 0.0438(5) Uani 1 1 d . . .
C9 C 0.64464(11) 0.6342(3) 0.52550(10) 0.0370(6) Uani 1 1 d . . .
C11 C 0.70141(11) 0.6196(3) 0.56842(10) 0.0368(6) Uani 1 1 d . . .
C12 C 0.70261(12) 0.7213(3) 0.62131(10) 0.0405(6) Uani 1 1 d . . .
C8 C 0.59704(12) 0.7536(3) 0.44020(10) 0.0431(6) Uani 1 1 d . . .
C6 C 0.57998(13) 0.6303(3) 0.39958(11) 0.0518(7) Uani 1 1 d . . .
C14 C 0.65051(13) 0.9217(3) 0.67431(11) 0.0466(7) Uani 1 1 d . . .
C20 C 0.67737(14) 1.0834(3) 0.67702(13) 0.0594(8) Uani 1 1 d . . .
C2 C 0.56610(14) 0.9104(3) 0.44033(12) 0.0556(8) Uani 1 1 d . . .
C13 C 0.75676(14) 0.6987(3) 0.66614(11) 0.0564(8) Uani 1 1 d . . .
H13A H 0.7603 0.7974 0.6903 0.085 Uiso 1 1 calc R . .
H13B H 0.7953 0.6841 0.6483 0.085 Uiso 1 1 calc R . .
H13C H 0.7495 0.5999 0.6887 0.085 Uiso 1 1 calc R . .
C10 C 0.58718(14) 0.5375(4) 0.53855(13) 0.0581(8) Uani 1 1 d . . .
H10A H 0.5529 0.5621 0.5101 0.087 Uiso 1 1 calc R . .
H10B H 0.5755 0.5705 0.5754 0.087 Uiso 1 1 calc R . .
H10C H 0.5961 0.4176 0.5385 0.087 Uiso 1 1 calc R . .
C15 C 0.61472(14) 0.8618(4) 0.71686(12) 0.0567(8) Uani 1 1 d . . .
C4 C 0.49753(17) 0.8171(5) 0.35910(15) 0.0811(11) Uani 1 1 d . . .
H4 H 0.4634 0.8372 0.3321 0.097 Uiso 1 1 calc R . .
C17 C 0.60692(17) 0.9674(5) 0.76263(14) 0.0772(10) Uani 1 1 d . . .
H17 H 0.5832 0.9295 0.7914 0.093 Uiso 1 1 calc R . .
C1 C 0.58709(17) 1.0437(4) 0.48409(15) 0.0771(10) Uani 1 1 d . . .
H1A H 0.5570 1.1352 0.4820 0.116 Uiso 1 1 calc R . .
H1B H 0.6278 1.0868 0.4766 0.116 Uiso 1 1 calc R . .
H1C H 0.5899 0.9939 0.5215 0.116 Uiso 1 1 calc R . .
C7 C 0.61438(18) 0.4625(4) 0.39750(14) 0.0768(10) Uani 1 1 d . . .
H7A H 0.6562 0.4736 0.4166 0.115 Uiso 1 1 calc R . .
H7B H 0.6172 0.4306 0.3585 0.115 Uiso 1 1 calc R . .
H7C H 0.5916 0.3765 0.4161 0.115 Uiso 1 1 calc R . .
C3 C 0.51593(16) 0.9390(5) 0.39870(16) 0.0749(10) Uani 1 1 d . . .
H3 H 0.4947 1.0427 0.3979 0.090 Uiso 1 1 calc R . .
C19 C 0.66787(18) 1.1830(4) 0.72435(16) 0.0775(11) Uani 1 1 d . . .
H19 H 0.6856 1.2913 0.7274 0.093 Uiso 1 1 calc R . .
C5 C 0.52905(16) 0.6665(5) 0.35909(12) 0.0695(9) Uani 1 1 d . . .
H5 H 0.5165 0.5854 0.3315 0.083 Uiso 1 1 calc R . .
C18 C 0.63315(19) 1.1259(6) 0.76649(16) 0.0862(12) Uani 1 1 d . . .
H18 H 0.6274 1.1949 0.7977 0.103 Uiso 1 1 calc R . .
C16 C 0.58536(19) 0.6879(4) 0.71262(16) 0.0909(12) Uani 1 1 d . . .
H16A H 0.6181 0.6032 0.7137 0.136 Uiso 1 1 calc R . .
H16B H 0.5588 0.6785 0.6774 0.136 Uiso 1 1 calc R . .
H16C H 0.5604 0.6706 0.7441 0.136 Uiso 1 1 calc R . .
C21 C 0.7136(2) 1.1485(4) 0.62999(17) 0.0898(12) Uani 1 1 d . . .
H21A H 0.7457 1.0676 0.6224 0.135 Uiso 1 1 calc R . .
H21B H 0.7331 1.2552 0.6412 0.135 Uiso 1 1 calc R . .
H21C H 0.6852 1.1647 0.5962 0.135 Uiso 1 1 calc R . .


_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
O1 N3 1.381(2) . ?
N1 C9 1.267(3) . ?
N1 C8 1.442(3) . ?
N2 C12 1.280(3) . ?
N2 C14 1.426(3) . ?
N3 C11 1.279(3) . ?
C9 C11 1.502(3) . ?
C9 C10 1.492(3) . ?
C11 C12 1.478(3) . ?
C12 C13 1.495(4) . ?
C8 C6 1.385(4) . ?
C8 C2 1.395(4) . ?
C6 C5 1.401(4) . ?
C6 C7 1.509(4) . ?
C14 C15 1.394(4) . ?
C14 C20 1.391(4) . ?
C20 C19 1.391(4) . ?
C20 C21 1.496(4) . ?
C2 C3 1.395(4) . ?
C2 C1 1.506(4) . ?
C15 C17 1.382(4) . ?
C15 C16 1.500(4) . ?
C4 C5 1.358(5) . ?
C4 C3 1.367(5) . ?
C17 C18 1.362(5) . ?
C19 C18 1.366(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C8 120.7(2) . . ?
C12 N2 C14 120.3(2) . . ?
C11 N3 O1 112.4(2) . . ?
N1 C9 C11 117.1(2) . . ?
N1 C9 C10 126.7(2) . . ?
C11 C9 C10 116.2(2) . . ?
N3 C11 C12 117.2(2) . . ?
N3 C11 C9 124.4(2) . . ?
C12 C11 C9 118.33(19) . . ?
N2 C12 C11 115.4(2) . . ?
N2 C12 C13 125.8(2) . . ?
C11 C12 C13 118.8(2) . . ?
C6 C8 C2 121.7(2) . . ?
C6 C8 N1 121.4(2) . . ?
C2 C8 N1 116.8(2) . . ?
C8 C6 C5 117.5(3) . . ?
C8 C6 C7 122.5(2) . . ?
C5 C6 C7 120.0(3) . . ?
C15 C14 C20 121.6(3) . . ?
C15 C14 N2 118.6(2) . . ?
C20 C14 N2 119.7(2) . . ?
C14 C20 C19 117.4(3) . . ?
C14 C20 C21 121.0(3) . . ?
C19 C20 C21 121.6(3) . . ?
C3 C2 C8 117.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
C8 C2 C1 120.4(3) . . ?
C17 C15 C14 118.1(3) . . ?
C17 C15 C16 121.2(3) . . ?
C14 C15 C16 120.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C15 C17 C18 121.5(3) . . ?
C2 C3 C4 121.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C4 C5 C6 121.6(3) . . ?
C17 C18 C19 119.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
