####################################################################### 
# 
# 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_e4528a_a
_database_code_depnum_ccdc_archive 'CCDC 2040825'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N6 O'
_chemical_formula_sum            'C18 H20 N6 O'
_chemical_formula_weight         336.40

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'

_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                   9.3898(5)
_cell_length_b                   11.5181(6)
_cell_length_c                   16.5570(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.597(2)
_cell_angle_gamma                90
_cell_volume                     1770.56(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1500
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57755
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         30.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4879
_reflns_number_gt                4049
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0764P)²+0.4680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4879
_refine_ls_number_parameters     227
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.37550(12) 0.57566(9) 0.38952(7) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.41566(11) 0.59896(7) 0.31800(6) 0.0275(2) Uani 1 1 d . . . . .
C2 C 0.45219(12) 0.71526(8) 0.32371(7) 0.0248(2) Uani 1 1 d . . . . .
C3 C 0.50039(13) 0.79069(9) 0.26532(7) 0.0264(2) Uani 1 1 d . . . . .
O1 O 0.52603(11) 0.76613(7) 0.19675(5) 0.0372(2) Uani 1 1 d . . . . .
N2 N 0.51724(11) 0.90442(7) 0.29477(5) 0.0263(2) Uani 1 1 d . . . . .
H2 H 0.5401 0.9579 0.2610 0.032 Uiso 1 1 calc R U . . .
C4 C 0.50101(12) 0.93952(8) 0.37214(6) 0.0239(2) Uani 1 1 d . . . . .
N3 N 0.46063(10) 0.86904(7) 0.42787(5) 0.0243(2) Uani 1 1 d . . . . .
C5 C 0.43519(11) 0.75990(8) 0.39912(6) 0.0224(2) Uani 1 1 d . . . . .
N4 N 0.38666(10) 0.67055(7) 0.44145(6) 0.02332(19) Uani 1 1 d . . . . .
N5 N 0.53037(12) 1.05057(7) 0.39138(6) 0.0303(2) Uani 1 1 d . . . . .
H5A H 0.5228 1.0762 0.4406 0.036 Uiso 1 1 calc R U . . .
H5B H 0.5572 1.0980 0.3548 0.036 Uiso 1 1 calc R U . . .
C6 C 0.32443(12) 0.46848(9) 0.41587(7) 0.0283(2) Uani 1 1 d . . . . .
C7 C 0.28181(13) 0.38289(10) 0.44507(8) 0.0310(2) Uani 1 1 d . . . . .
C8 C 0.23509(12) 0.27939(10) 0.48064(8) 0.0330(3) Uani 1 1 d . . . . .
C9 C 0.22466(15) 0.17529(10) 0.43698(10) 0.0413(3) Uani 1 1 d D . . . .
H9 H 0.2481 0.1738 0.3831 0.050 Uiso 1 1 calc DR U . . .
N6 N 0.18144(15) 0.07616(10) 0.47043(10) 0.0485(4) Uani 0.5 1 d . . P . .
C11A C 0.18144(15) 0.07616(10) 0.47043(10) 0.0485(4) Uani 0.5 1 d . . P . .
H11A H 0.1734 0.0055 0.4405 0.058 Uiso 0.5 1 calc R U P . .
C10 C 0.15051(16) 0.08040(13) 0.54631(11) 0.0508(4) Uani 1 1 d . . . . .
H10 H 0.1209 0.0107 0.5695 0.061 Uiso 1 1 calc R U . . .
C11 C 0.15873(16) 0.17871(13) 0.59277(10) 0.0527(4) Uani 0.5 1 d . . P . .
H11 H 0.1356 0.1775 0.6467 0.063 Uiso 0.5 1 calc R U P . .
N6A N 0.15873(16) 0.17871(13) 0.59277(10) 0.0527(4) Uani 0.5 1 d . . P . .
C12 C 0.20141(16) 0.27900(12) 0.55922(10) 0.0440(3) Uani 1 1 d D . . . .
H12 H 0.2080 0.3489 0.5901 0.053 Uiso 1 1 calc DR U . . .
C13 C 0.34772(12) 0.67520(9) 0.52321(7) 0.0245(2) Uani 1 1 d . . . . .
H13A H 0.4206 0.7213 0.5590 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3483 0.5956 0.5457 0.029 Uiso 1 1 calc R U . . .
C14 C 0.20008(14) 0.72887(12) 0.52369(9) 0.0367(3) Uani 1 1 d . . . . .
H14A H 0.1279 0.6849 0.4859 0.044 Uiso 1 1 calc R U . . .
H14B H 0.2009 0.8097 0.5034 0.044 Uiso 1 1 calc R U . . .
C15 C 0.15562(15) 0.72924(13) 0.60842(9) 0.0418(3) Uani 1 1 d . . . . .
H15A H 0.2315 0.7685 0.6468 0.050 Uiso 1 1 calc R U . . .
H15B H 0.0660 0.7750 0.6066 0.050 Uiso 1 1 calc R U . . .
C16 C 0.13077(17) 0.60863(15) 0.64111(10) 0.0487(4) Uani 1 1 d . . . . .
H16A H 0.0635 0.5662 0.5996 0.058 Uiso 1 1 calc R U . . .
H16B H 0.2234 0.5661 0.6488 0.058 Uiso 1 1 calc R U . . .
C17 C 0.0706(2) 0.6076(2) 0.72086(13) 0.0759(6) Uani 1 1 d . . . . .
H17A H -0.0205 0.6522 0.7143 0.091 Uiso 1 1 calc R U . . .
H17B H 0.1396 0.6462 0.7635 0.091 Uiso 1 1 calc R U . . .
C18 C 0.0424(4) 0.4844(3) 0.74832(19) 0.1219(12) Uani 1 1 d . . . . .
H18A H -0.0289 0.4470 0.7072 0.183 Uiso 1 1 calc R U . . .
H18B H 0.0057 0.4871 0.8007 0.183 Uiso 1 1 calc R U . . .
H18C H 0.1324 0.4399 0.7547 0.183 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3229(15) . ?
C1 N4 1.3848(13) . ?
C1 C6 1.4166(15) . ?
N1 C2 1.3825(13) . ?
C2 C5 1.3814(15) . ?
C2 C3 1.4230(15) . ?
C3 O1 1.2284(15) . ?
C3 N2 1.3984(13) . ?
N2 C4 1.3734(14) . ?
N2 H2 0.8800 . ?
C4 N3 1.3263(13) . ?
C4 N5 1.3369(12) . ?
N3 C5 1.3528(12) . ?
C5 N4 1.3614(13) . ?
N4 C13 1.4550(14) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C6 C7 1.1931(16) . ?
C7 C8 1.4275(15) . ?
C8 C12 1.384(2) . ?
C8 C9 1.3960(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3675(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.5190(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.512(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 112.98(9) . . ?
N1 C1 C6 127.40(10) . . ?
N4 C1 C6 119.62(10) . . ?
C1 N1 C2 103.67(9) . . ?
C5 C2 N1 111.19(10) . . ?
C5 C2 C3 118.57(9) . . ?
N1 C2 C3 130.23(10) . . ?
O1 C3 N2 120.69(10) . . ?
O1 C3 C2 127.84(10) . . ?
N2 C3 C2 111.47(9) . . ?
C4 N2 C3 125.34(9) . . ?
C4 N2 H2 117.3 . . ?
C3 N2 H2 117.3 . . ?
N3 C4 N5 119.34(10) . . ?
N3 C4 N2 123.50(9) . . ?
N5 C4 N2 117.15(10) . . ?
C4 N3 C5 112.19(9) . . ?
N3 C5 N4 125.20(10) . . ?
N3 C5 C2 128.74(10) . . ?
N4 C5 C2 106.06(9) . . ?
C5 N4 C1 106.09(9) . . ?
C5 N4 C13 126.95(8) . . ?
C1 N4 C13 126.90(9) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 C6 C1 173.87(13) . . ?
C6 C7 C8 178.32(13) . . ?
C12 C8 C9 118.41(12) . . ?
C12 C8 C7 121.20(12) . . ?
C9 C8 C7 120.38(13) . . ?
C8 C9 H9 119.6 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 117.86(15) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C8 120.43(15) . . ?
C11 C12 H12 119.8 . . ?
C8 C12 H12 119.8 . . ?
N4 C13 C14 112.11(9) . . ?
N4 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 112.47(11) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 113.77(12) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 114.52(16) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 111.8(2) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4564a_a
_database_code_depnum_ccdc_archive 'CCDC 2040826'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C18H20N6O,C17H20N4O,2(CH4O)
_chemical_formula_sum            'C37 H48 N10 O4'
_chemical_formula_weight         696.85

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'

_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                   8.4429(6)
_cell_length_b                   15.7140(9)
_cell_length_c                   16.1715(8)
_cell_angle_alpha                112.591(2)
_cell_angle_beta                 104.239(2)
_cell_angle_gamma                95.640(3)
_cell_volume                     1874.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6071
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.79


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31016
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         30.189
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             10205
_reflns_number_gt                6620
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0758P)²+1.0104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10205
_refine_ls_number_parameters     466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.019
_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
C1 C 1.0384(2) 0.69444(13) 0.24995(13) 0.0282(4) Uani 1 1 d . . . . .
N1 N 1.10607(18) 0.78878(11) 0.31070(11) 0.0260(3) Uani 1 1 d . . . . .
C2 C 1.2723(2) 0.79398(12) 0.34940(12) 0.0234(4) Uani 1 1 d . . . . .
N2 N 1.38694(18) 0.87381(10) 0.41257(11) 0.0255(3) Uani 1 1 d . . . . .
C3 C 1.5384(2) 0.85704(12) 0.43780(13) 0.0249(4) Uani 1 1 d . . . . .
N3 N 1.57414(18) 0.76955(10) 0.40338(11) 0.0264(3) Uani 1 1 d . . . . .
H3 H 1.6790 0.7656 0.4227 0.032 Uiso 1 1 calc R U . . .
C4 C 1.4584(2) 0.68593(13) 0.34020(13) 0.0265(4) Uani 1 1 d . . . . .
C5 C 1.2958(2) 0.70313(12) 0.31136(13) 0.0253(4) Uani 1 1 d . . . . .
N4 N 1.14943(19) 0.64119(11) 0.24904(11) 0.0296(4) Uani 1 1 d . . . . .
N5 N 1.6654(2) 0.92763(11) 0.50100(12) 0.0346(4) Uani 1 1 d . . . . .
H5A H 1.6488 0.9852 0.5259 0.042 Uiso 1 1 calc R U . . .
H5B H 1.7658 0.9166 0.5177 0.042 Uiso 1 1 calc R U . . .
O1 O 1.50193(17) 0.61000(9) 0.31574(10) 0.0373(4) Uani 1 1 d . . . . .
C6 C 0.8684(2) 0.66353(14) 0.19253(14) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.7283(2) 0.64293(14) 0.14136(15) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.5663(2) 0.62293(13) 0.07503(14) 0.0287(4) Uani 1 1 d . . . . .
C9 C 0.5537(2) 0.62229(14) -0.01225(15) 0.0342(5) Uani 1 1 d . . . . .
H9 H 0.6539 0.6331 -0.0269 0.041 Uiso 1 1 calc R U . . .
N6 N 0.4080(2) 0.60722(13) -0.07687(13) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.2695(3) 0.59178(16) -0.05476(16) 0.0412(5) Uani 1 1 d . . . . .
H10 H 0.1649 0.5819 -0.0997 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2686(3) 0.58922(17) 0.02886(17) 0.0428(5) Uani 1 1 d . . . . .
H11 H 0.1659 0.5771 0.0407 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4196(2) 0.60456(15) 0.09585(15) 0.0355(5) Uani 1 1 d . . . . .
H12 H 0.4231 0.6026 0.1543 0.043 Uiso 1 1 calc R U . . .
C13 C 1.0203(2) 0.86756(13) 0.32758(14) 0.0309(4) Uani 1 1 d . . . . .
H13A H 1.0657 0.9125 0.3948 0.037 Uiso 1 1 calc R U . . .
H13B H 0.8997 0.8433 0.3140 0.037 Uiso 1 1 calc R U . . .
C14 C 1.0407(3) 0.91945(15) 0.26698(16) 0.0425(5) Uani 1 1 d . . . . .
H14A H 0.9955 0.9772 0.2878 0.051 Uiso 1 1 calc R U . . .
H14B H 1.1614 0.9391 0.2768 0.051 Uiso 1 1 calc R U . . .
C15 C 0.9530(4) 0.86038(19) 0.16301(18) 0.0569(7) Uani 1 1 d . . . . .
H15A H 1.0069 0.8062 0.1411 0.068 Uiso 1 1 calc R U . . .
H15B H 0.8353 0.8347 0.1544 0.068 Uiso 1 1 calc R U . . .
C16 C 0.9545(5) 0.9115(2) 0.1031(2) 0.0694(9) Uani 1 1 d . . . . .
H16A H 1.0714 0.9356 0.1088 0.083 Uiso 1 1 calc R U . . .
H16B H 0.9012 0.9661 0.1240 0.083 Uiso 1 1 calc R U . . .
C17 C 0.8579(6) 0.8438(3) -0.0012(2) 0.0970(13) Uani 1 1 d . . . . .
H17A H 0.9192 0.7930 -0.0221 0.116 Uiso 1 1 calc R U . . .
H17B H 0.7469 0.8140 -0.0037 0.116 Uiso 1 1 calc R U . . .
C18 C 0.8335(7) 0.8835(4) -0.0650(3) 0.134(2) Uani 1 1 d . . . . .
H18A H 0.7704 0.9330 -0.0466 0.201 Uiso 1 1 calc R U . . .
H18B H 0.7706 0.8346 -0.1280 0.201 Uiso 1 1 calc R U . . .
H18C H 0.9422 0.9109 -0.0658 0.201 Uiso 1 1 calc R U . . .
C19 C 0.1190(2) 0.64842(13) 0.47126(13) 0.0255(4) Uani 1 1 d . . . . .
C20 C 0.2368(2) 0.72916(13) 0.52807(13) 0.0270(4) Uani 1 1 d . . . . .
H20 H 0.3496 0.7251 0.5504 0.032 Uiso 1 1 calc R U . . .
N7 N 0.19757(18) 0.81500(11) 0.55367(11) 0.0268(3) Uani 1 1 d . . . . .
C21 C 0.0320(2) 0.82374(13) 0.52358(13) 0.0256(4) Uani 1 1 d . . . . .
N8 N -0.08649(18) 0.74482(11) 0.46308(11) 0.0265(3) Uani 1 1 d . . . . .
C22 C -0.0483(2) 0.65980(13) 0.43565(13) 0.0245(4) Uani 1 1 d . . . . .
C23 C 0.3278(2) 0.90101(14) 0.61597(14) 0.0312(4) Uani 1 1 d . . . . .
H23A H 0.2987 0.9535 0.6000 0.037 Uiso 1 1 calc R U . . .
H23B H 0.4357 0.8906 0.6045 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3488(3) 0.92908(14) 0.71926(14) 0.0350(5) Uani 1 1 d . . . . .
H24A H 0.3912 0.8802 0.7374 0.042 Uiso 1 1 calc R U . . .
H24B H 0.2385 0.9326 0.7298 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4697(3) 1.02414(16) 0.78116(16) 0.0445(6) Uani 1 1 d . . . . .
H25A H 0.5748 1.0229 0.7643 0.053 Uiso 1 1 calc R U . . .
H25B H 0.4202 1.0740 0.7681 0.053 Uiso 1 1 calc R U . . .
C26 C 0.5105(3) 1.04902(17) 0.88520(16) 0.0505(6) Uani 1 1 d . . . . .
H26A H 0.5658 1.0009 0.8984 0.061 Uiso 1 1 calc R U . . .
H26B H 0.4045 1.0460 0.9009 0.061 Uiso 1 1 calc R U . . .
C27 C 0.6228(4) 1.14591(18) 0.94915(19) 0.0627(8) Uani 1 1 d . . . . .
H27A H 0.7242 1.1517 0.9296 0.075 Uiso 1 1 calc R U . . .
H27B H 0.5630 1.1948 0.9415 0.075 Uiso 1 1 calc R U . . .
C28 C 0.6752(5) 1.1639(2) 1.0523(2) 0.0864(12) Uani 1 1 d . . . . .
H28A H 0.5756 1.1608 1.0728 0.130 Uiso 1 1 calc R U . . .
H28B H 0.7487 1.2266 1.0902 0.130 Uiso 1 1 calc R U . . .
H28C H 0.7350 1.1158 1.0605 0.130 Uiso 1 1 calc R U . . .
O2 O -0.00016(16) 0.90293(9) 0.55210(10) 0.0336(3) Uani 1 1 d . . . . .
N9 N -0.1679(2) 0.58563(11) 0.37542(11) 0.0313(4) Uani 1 1 d . . . . .
H9A H -0.2698 0.5929 0.3544 0.038 Uiso 1 1 calc R U . . .
H9B H -0.1458 0.5289 0.3563 0.038 Uiso 1 1 calc R U . . .
C29 C 0.1542(2) 0.55655(14) 0.44655(13) 0.0287(4) Uani 1 1 d . . . . .
C30 C 0.1704(2) 0.47713(14) 0.42455(14) 0.0304(4) Uani 1 1 d . . . . .
C31 C 0.1871(2) 0.38081(13) 0.39452(14) 0.0283(4) Uani 1 1 d . . . . .
C32 C 0.3350(2) 0.35745(14) 0.43160(15) 0.0323(4) Uani 1 1 d . . . . .
H32 H 0.4235 0.4071 0.4794 0.039 Uiso 1 1 calc R U . . .
N10 N 0.3592(2) 0.26955(13) 0.40382(14) 0.0383(4) Uani 1 1 d . . . . .
C33 C 0.2324(3) 0.20100(15) 0.33832(17) 0.0391(5) Uani 1 1 d . . . . .
H33 H 0.2474 0.1379 0.3182 0.047 Uiso 1 1 calc R U . . .
C34 C 0.0800(3) 0.21632(15) 0.29784(16) 0.0394(5) Uani 1 1 d . . . . .
H34 H -0.0070 0.1649 0.2514 0.047 Uiso 1 1 calc R U . . .
C35 C 0.0564(2) 0.30746(15) 0.32605(15) 0.0350(5) Uani 1 1 d . . . . .
H35 H -0.0470 0.3201 0.2993 0.042 Uiso 1 1 calc R U . . .
C37 C 0.4030(4) 0.6397(3) 0.7116(2) 0.0683(9) Uani 1 1 d . . . . .
H37A H 0.4781 0.6995 0.7586 0.102 Uiso 1 1 calc R U . . .
H37B H 0.3479 0.6472 0.6547 0.102 Uiso 1 1 calc R U . . .
H37C H 0.4678 0.5905 0.6958 0.102 Uiso 1 1 calc R U . . .
O3 O 0.28209(19) 0.61363(11) 0.74802(10) 0.0388(4) Uani 1 1 d . . . . .
H3A H 0.3295 0.6132 0.8000 0.058 Uiso 1 1 calc R U . . .
C38 C 0.1738(5) 0.4094(2) 0.1859(2) 0.0780(10) Uani 1 1 d . . . . .
H38A H 0.2838 0.4421 0.2326 0.117 Uiso 1 1 calc R U . . .
H38B H 0.1743 0.3428 0.1514 0.117 Uiso 1 1 calc R U . . .
H38C H 0.0882 0.4142 0.2179 0.117 Uiso 1 1 calc R U . . .
O4 O 0.1398(2) 0.44938(13) 0.12526(13) 0.0543(5) Uani 1 1 d . . . . .
H4 H 0.1370 0.5061 0.1546 0.081 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.316(2) . ?
C1 N1 1.388(2) . ?
C1 C6 1.421(3) . ?
N1 C2 1.369(2) . ?
N1 C13 1.465(2) . ?
C2 N2 1.358(2) . ?
C2 C5 1.377(2) . ?
N2 C3 1.328(2) . ?
C3 N5 1.335(2) . ?
C3 N3 1.366(2) . ?
N3 C4 1.397(2) . ?
N3 H3 0.8800 . ?
C4 O1 1.229(2) . ?
C4 C5 1.425(2) . ?
C5 N4 1.374(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C6 C7 1.194(3) . ?
C7 C8 1.434(3) . ?
C8 C9 1.385(3) . ?
C8 C12 1.393(3) . ?
C9 N6 1.335(3) . ?
C9 H9 0.9500 . ?
N6 C10 1.331(3) . ?
C10 C11 1.370(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.513(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.479(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.554(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.382(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.360(3) . ?
C19 C29 1.425(3) . ?
C19 C22 1.444(2) . ?
C20 N7 1.351(2) . ?
C20 H20 0.9500 . ?
N7 C21 1.402(2) . ?
N7 C23 1.472(2) . ?
C21 O2 1.234(2) . ?
C21 N8 1.356(2) . ?
N8 C22 1.336(2) . ?
C22 N9 1.319(2) . ?
C23 C24 1.513(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.525(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.512(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.520(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.520(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C29 C30 1.191(3) . ?
C30 C31 1.434(3) . ?
C31 C35 1.393(3) . ?
C31 C32 1.394(3) . ?
C32 N10 1.333(3) . ?
C32 H32 0.9500 . ?
N10 C33 1.330(3) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C37 O3 1.399(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
O3 H3A 0.8400 . ?
C38 O4 1.345(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O4 H4 0.8400 . ?

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
N4 C1 N1 112.83(16) . . ?
N4 C1 C6 125.71(17) . . ?
N1 C1 C6 121.37(17) . . ?
C2 N1 C1 105.72(15) . . ?
C2 N1 C13 126.68(15) . . ?
C1 N1 C13 127.56(15) . . ?
N2 C2 N1 125.68(16) . . ?
N2 C2 C5 128.42(16) . . ?
N1 C2 C5 105.90(15) . . ?
C3 N2 C2 112.14(15) . . ?
N2 C3 N5 119.95(16) . . ?
N2 C3 N3 123.66(15) . . ?
N5 C3 N3 116.38(16) . . ?
C3 N3 C4 125.52(15) . . ?
C3 N3 H3 117.2 . . ?
C4 N3 H3 117.2 . . ?
O1 C4 N3 120.66(16) . . ?
O1 C4 C5 127.98(16) . . ?
N3 C4 C5 111.36(15) . . ?
N4 C5 C2 111.36(16) . . ?
N4 C5 C4 129.81(16) . . ?
C2 C5 C4 118.83(15) . . ?
C1 N4 C5 104.19(15) . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 C6 C1 174.5(2) . . ?
C6 C7 C8 174.3(2) . . ?
C9 C8 C12 118.51(18) . . ?
C9 C8 C7 119.59(19) . . ?
C12 C8 C7 121.9(2) . . ?
N6 C9 C8 123.4(2) . . ?
N6 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C10 N6 C9 117.1(2) . . ?
N6 C10 C11 123.94(19) . . ?
N6 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C8 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C8 C12 H12 121.0 . . ?
N1 C13 C14 112.37(17) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 113.2(2) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 114.7(2) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 109.6(3) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 116.7(4) . . ?
C18 C17 H17A 108.1 . . ?
C16 C17 H17A 108.1 . . ?
C18 C17 H17B 108.1 . . ?
C16 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C29 123.29(16) . . ?
C20 C19 C22 116.29(16) . . ?
C29 C19 C22 120.42(16) . . ?
N7 C20 C19 121.78(16) . . ?
N7 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 N7 C21 120.77(15) . . ?
C20 N7 C23 120.44(15) . . ?
C21 N7 C23 118.77(15) . . ?
O2 C21 N8 122.49(16) . . ?
O2 C21 N7 118.87(16) . . ?
N8 C21 N7 118.64(16) . . ?
C22 N8 C21 120.92(15) . . ?
N9 C22 N8 118.31(16) . . ?
N9 C22 C19 120.34(17) . . ?
N8 C22 C19 121.34(16) . . ?
N7 C23 C24 112.97(16) . . ?
N7 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N7 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 111.63(18) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 113.2(2) . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27 114.5(2) . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C26 112.7(3) . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
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 . . ?
C22 N9 H9A 120.0 . . ?
C22 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C30 C29 C19 174.7(2) . . ?
C29 C30 C31 177.9(2) . . ?
C35 C31 C32 117.77(18) . . ?
C35 C31 C30 120.90(17) . . ?
C32 C31 C30 121.33(18) . . ?
N10 C32 C31 123.77(19) . . ?
N10 C32 H32 118.1 . . ?
C31 C32 H32 118.1 . . ?
C33 N10 C32 117.12(18) . . ?
N10 C33 C34 123.7(2) . . ?
N10 C33 H33 118.1 . . ?
C34 C33 H33 118.1 . . ?
C35 C34 C33 118.85(19) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C31 118.73(19) . . ?
C34 C35 H35 120.6 . . ?
C31 C35 H35 120.6 . . ?
O3 C37 H37A 109.5 . . ?
O3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C37 O3 H3A 109.5 . . ?
O4 C38 H38A 109.5 . . ?
O4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C38 O4 H4 109.5 . . ?

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4635a_a
_database_code_depnum_ccdc_archive 'CCDC 2040833'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 Cd N8 O7, C2 H4 Cl2'
_chemical_formula_sum            'C20 H26 Cd Cl2 N8 O7'
_chemical_formula_weight         673.79

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.3987(3)
_cell_length_b                   10.8657(4)
_cell_length_c                   13.6960(4)
_cell_angle_alpha                73.878(2)
_cell_angle_beta                 80.4940(10)
_cell_angle_gamma                62.957(2)
_cell_volume                     1322.73(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.084
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23768
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         30.152
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             7185
_reflns_number_gt                6546
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0307P)²+0.8872P] 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         7185
_refine_ls_number_parameters     350
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_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
Cd1 Cd 0.55873(2) 0.64253(2) 0.05564(2) 0.01917(5) Uani 1 1 d . . . . .
C1 C 0.1509(2) 0.6154(2) 0.48713(15) 0.0186(4) Uani 1 1 d . . . . .
N1 N 0.07441(16) 0.66743(18) 0.39980(13) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.17347(19) 0.6595(2) 0.32112(15) 0.0182(4) Uani 1 1 d . . . . .
N2 N 0.14691(17) 0.6991(2) 0.22155(13) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.2660(2) 0.6821(2) 0.16483(16) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.2554 0.7059 0.0935 0.029 Uiso 1 1 calc R U . . .
N3 N 0.40244(17) 0.63502(19) 0.19414(13) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.42684(19) 0.5953(2) 0.29547(15) 0.0170(4) Uani 1 1 d . . . . .
C5 C 0.30651(19) 0.6044(2) 0.36348(15) 0.0170(4) Uani 1 1 d . . . . .
N4 N 0.29241(17) 0.57535(18) 0.46828(13) 0.0192(3) Uani 1 1 d . . . . .
N5 N 0.55817(17) 0.5515(2) 0.32681(13) 0.0237(4) Uani 1 1 d . . . . .
H5A H 0.6303 0.5479 0.2821 0.028 Uiso 1 1 calc R U . . .
H5B H 0.5730 0.5260 0.3923 0.028 Uiso 1 1 calc R U . . .
C6 C -0.08329(19) 0.7286(2) 0.39037(17) 0.0222(4) Uani 1 1 d . . . . .
H6A H -0.1268 0.6914 0.4546 0.027 Uiso 1 1 calc R U . . .
H6B H -0.1024 0.6969 0.3354 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1557(2) 0.8891(2) 0.36744(17) 0.0263(4) Uani 1 1 d . . . . .
H7A H -0.1061 0.9254 0.3064 0.032 Uiso 1 1 calc R U . . .
H7B H -0.2569 0.9222 0.3505 0.032 Uiso 1 1 calc R U . . .
C8 C -0.1566(2) 0.9535(3) 0.45240(19) 0.0311(5) Uani 1 1 d . . . . .
H8A H -0.0557 0.9227 0.4687 0.037 Uiso 1 1 calc R U . . .
H8B H -0.2054 0.9172 0.5139 0.037 Uiso 1 1 calc R U . . .
C9 C -0.2330(3) 1.1157(3) 0.4257(2) 0.0398(6) Uani 1 1 d . . . . .
H9A H -0.2162 1.1508 0.4796 0.048 Uiso 1 1 calc R U . . .
H9B H -0.1882 1.1511 0.3613 0.048 Uiso 1 1 calc R U . . .
C10 C -0.3957(3) 1.1790(3) 0.4137(2) 0.0471(7) Uani 1 1 d . . . . .
H10A H -0.4304 1.2809 0.3796 0.057 Uiso 1 1 calc R U . . .
H10B H -0.4137 1.1316 0.3689 0.057 Uiso 1 1 calc R U . . .
C11 C -0.4828(4) 1.1652(4) 0.5125(3) 0.0662(10) Uani 1 1 d . . . . .
H11A H -0.4523 1.0645 0.5456 0.099 Uiso 1 1 calc R U . . .
H11B H -0.5856 1.2094 0.4987 0.099 Uiso 1 1 calc R U . . .
H11C H -0.4668 1.2129 0.5573 0.099 Uiso 1 1 calc R U . . .
C12 C 0.0778(2) 0.6074(2) 0.58394(16) 0.0226(4) Uani 1 1 d . . . . .
C13 C -0.0001(2) 0.6071(2) 0.65866(16) 0.0237(4) Uani 1 1 d . . . . .
C14 C -0.0974(2) 0.6098(2) 0.74540(16) 0.0221(4) Uani 1 1 d . . . . .
C15 C -0.2462(2) 0.6901(3) 0.73482(17) 0.0303(5) Uani 1 1 d . . . . .
H15 H -0.2838 0.7415 0.6696 0.036 Uiso 1 1 calc R U . . .
C16 C -0.3378(2) 0.6936(3) 0.82023(17) 0.0295(5) Uani 1 1 d . . . . .
H16 H -0.4388 0.7483 0.8122 0.035 Uiso 1 1 calc R U . . .
N6 N -0.29073(17) 0.62327(19) 0.91405(13) 0.0209(3) Uani 1 1 d . . . . .
C17 C -0.1486(2) 0.5431(2) 0.92315(16) 0.0247(4) Uani 1 1 d . . . . .
H17 H -0.1144 0.4900 0.9890 0.030 Uiso 1 1 calc R U . . .
C18 C -0.0496(2) 0.5335(2) 0.84233(17) 0.0265(5) Uani 1 1 d . . . . .
H18 H 0.0505 0.4753 0.8526 0.032 Uiso 1 1 calc R U . . .
O1 O 0.59855(16) 0.40344(16) 0.06374(12) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.75334(17) 0.39182(18) 0.15736(13) 0.0312(4) Uani 1 1 d . . . . .
O3 O 0.73136(19) 0.20138(17) 0.16121(14) 0.0350(4) Uani 1 1 d . . . . .
N7 N 0.69689(18) 0.32965(19) 0.12858(13) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.70367(16) 0.67033(16) 0.15032(12) 0.0272(3) Uani 1 1 d . . . . .
O5 O 0.7097(2) 0.8385(2) 0.20230(17) 0.0546(6) Uani 1 1 d . . . . .
O6 O 0.5848(2) 0.88888(19) 0.07513(16) 0.0485(5) Uani 1 1 d . . . . .
N8 N 0.66622(19) 0.8021(2) 0.14386(14) 0.0269(4) Uani 1 1 d . . . . .
O7 O 0.39312(17) 0.85498(17) -0.02687(13) 0.0284(3) Uani 1 1 d D . . . .
H7C H 0.345(3) 0.848(3) -0.0695(19) 0.038 Uiso 1 1 d D U . . .
H7D H 0.415(3) 0.923(2) -0.039(2) 0.038 Uiso 1 1 d D U . . .
Cl1 Cl 0.03540(8) 0.16681(9) -0.00767(6) 0.0542(2) Uani 1 1 d . . . . .
C20 C 0.1913(7) 0.0624(6) 0.1551(3) 0.111(2) Uani 1 1 d . . . . .
H20A H 0.1874 0.1582 0.1430 0.134 Uiso 1 1 calc R U . . .
H20B H 0.2753 0.0069 0.1147 0.134 Uiso 1 1 calc R U . . .
C19 C 0.0705(4) 0.0745(5) 0.1231(3) 0.0956(18) Uani 1 1 d . . . . .
H19A H -0.0125 0.1252 0.1664 0.115 Uiso 1 1 calc R U . . .
H19B H 0.0771 -0.0218 0.1324 0.115 Uiso 1 1 calc R U . . .
Cl2 Cl 0.21678(15) -0.02165(10) 0.28656(7) 0.0818(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O7 2.2695(15) . ?
Cd1 N6 2.2758(17) 1_654 ?
Cd1 N3 2.2940(16) . ?
Cd1 O4 2.3069(16) . ?
Cd1 O1 2.4104(16) . ?
C1 N4 1.333(2) . ?
C1 N1 1.383(2) . ?
C1 C12 1.416(3) . ?
N1 C2 1.354(3) . ?
N1 C6 1.476(2) . ?
C2 N2 1.346(3) . ?
C2 C5 1.389(2) . ?
N2 C3 1.313(3) . ?
C3 N3 1.360(2) . ?
C3 H3 0.9500 . ?
N3 C4 1.364(2) . ?
C4 N5 1.329(2) . ?
C4 C5 1.413(3) . ?
C5 N4 1.379(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C6 C7 1.512(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.529(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.509(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.196(3) . ?
C13 C14 1.425(3) . ?
C14 C18 1.389(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 N6 1.341(3) . ?
C16 H16 0.9500 . ?
N6 C17 1.337(2) . ?
N6 Cd1 2.2759(17) 1_456 ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1 N7 1.279(2) . ?
O2 N7 1.241(2) . ?
O3 N7 1.234(2) . ?
O4 N8 1.282(2) . ?
O5 N8 1.208(2) . ?
O6 N8 1.239(2) . ?
O7 H7C 0.866(15) . ?
O7 H7D 0.840(16) . ?
Cl1 C19 1.797(4) . ?
C20 C19 1.337(6) . ?
C20 Cl2 1.780(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Cd1 N6 91.09(6) . 1_654 ?
O7 Cd1 N3 91.87(6) . . ?
N6 Cd1 N3 171.56(6) 1_654 . ?
O7 Cd1 O4 111.66(5) . . ?
N6 Cd1 O4 95.82(6) 1_654 . ?
N3 Cd1 O4 90.43(6) . . ?
O7 Cd1 O1 131.00(5) . . ?
N6 Cd1 O1 86.06(6) 1_654 . ?
N3 Cd1 O1 86.03(6) . . ?
O4 Cd1 O1 117.30(5) . . ?
N4 C1 N1 113.15(17) . . ?
N4 C1 C12 126.76(18) . . ?
N1 C1 C12 120.08(17) . . ?
C2 N1 C1 105.94(15) . . ?
C2 N1 C6 125.39(16) . . ?
C1 N1 C6 128.56(17) . . ?
N2 C2 N1 126.39(16) . . ?
N2 C2 C5 127.09(18) . . ?
N1 C2 C5 106.52(17) . . ?
C3 N2 C2 111.13(16) . . ?
N2 C3 N3 128.91(19) . . ?
N2 C3 H3 115.5 . . ?
N3 C3 H3 115.5 . . ?
C3 N3 C4 118.92(17) . . ?
C3 N3 Cd1 111.01(13) . . ?
C4 N3 Cd1 130.04(12) . . ?
N5 C4 N3 120.54(17) . . ?
N5 C4 C5 122.68(18) . . ?
N3 C4 C5 116.77(16) . . ?
N4 C5 C2 110.95(16) . . ?
N4 C5 C4 131.88(16) . . ?
C2 C5 C4 117.07(17) . . ?
C1 N4 C5 103.43(15) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N1 C6 C7 113.40(17) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 115.19(18) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 113.0(2) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.9(2) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 114.4(3) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 171.2(2) . . ?
C12 C13 C14 177.9(2) . . ?
C18 C14 C15 117.66(19) . . ?
C18 C14 C13 122.04(18) . . ?
C15 C14 C13 120.30(19) . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N6 C16 C15 122.93(19) . . ?
N6 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C17 N6 C16 117.53(18) . . ?
C17 N6 Cd1 119.83(14) . 1_456 ?
C16 N6 Cd1 122.59(13) . 1_456 ?
N6 C17 C18 123.44(19) . . ?
N6 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C17 C18 C14 119.21(18) . . ?
C17 C18 H18 120.4 . . ?
C14 C18 H18 120.4 . . ?
N7 O1 Cd1 102.36(12) . . ?
O3 N7 O2 122.31(18) . . ?
O3 N7 O1 119.90(17) . . ?
O2 N7 O1 117.79(17) . . ?
N8 O4 Cd1 111.03(11) . . ?
O5 N8 O6 122.2(2) . . ?
O5 N8 O4 120.84(19) . . ?
O6 N8 O4 116.96(18) . . ?
Cd1 O7 H7C 113.5(18) . . ?
Cd1 O7 H7D 115.7(19) . . ?
H7C O7 H7D 121(2) . . ?
C19 C20 Cl2 112.8(4) . . ?
C19 C20 H20A 109.0 . . ?
Cl2 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
Cl2 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C19 Cl1 114.4(3) . . ?
C20 C19 H19A 108.7 . . ?
Cl1 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
Cl1 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?

_refine_diff_density_max         1.151
_refine_diff_density_min         -1.255
_refine_diff_density_rms         0.083

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4576a_a
_database_code_depnum_ccdc_archive 'CCDC 2040828'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N4 O'
_chemical_formula_sum            'C17 H20 N4 O'
_chemical_formula_weight         296.37

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'

_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                   13.2843(10)
_cell_length_b                   9.9419(6)
_cell_length_c                   13.1958(11)
_cell_angle_alpha                90
_cell_angle_beta                 115.219(3)
_cell_angle_gamma                90
_cell_volume                     1576.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      29.93


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11119
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.659
_diffrn_reflns_theta_max         30.091
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4601
_reflns_number_gt                3358
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1140P)²+0.9659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.2175
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_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
C1 C 0.62972(13) 0.75471(17) 0.22216(15) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.56549(14) 0.72427(18) 0.27659(16) 0.0271(4) Uani 1 1 d . . . . .
H2 H 0.5923 0.6610 0.3362 0.033 Uiso 1 1 calc R U . . .
N1 N 0.46498(12) 0.78134(15) 0.24821(14) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.42138(14) 0.87292(17) 0.15786(16) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.48545(11) 0.90754(15) 0.10470(13) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.58533(13) 0.85215(17) 0.13303(14) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.73511(14) 0.69162(19) 0.25353(16) 0.0282(4) Uani 1 1 d . . . . .
C6 C 0.82178(15) 0.6345(2) 0.28314(16) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.92228(14) 0.5577(2) 0.32013(15) 0.0281(4) Uani 1 1 d . . . . .
C8 C 0.93014(15) 0.43341(19) 0.37047(17) 0.0299(4) Uani 1 1 d . . . . .
H8 H 0.8693 0.3980 0.3819 0.036 Uiso 1 1 calc R U . . .
C9 C 1.02858(16) 0.3618(2) 0.40382(17) 0.0329(4) Uani 1 1 d . . . . .
H9 H 1.0331 0.2769 0.4385 0.039 Uiso 1 1 calc R U . . .
N3 N 1.11729(14) 0.40402(19) 0.39050(16) 0.0372(4) Uani 1 1 d . . . . .
C10 C 1.10917(18) 0.5244(3) 0.3448(2) 0.0484(6) Uani 1 1 d . . . . .
H10 H 1.1721 0.5580 0.3364 0.058 Uiso 1 1 calc R U . . .
C11 C 1.01518(18) 0.6046(2) 0.3086(2) 0.0442(6) Uani 1 1 d . . . . .
H11 H 1.0143 0.6902 0.2764 0.053 Uiso 1 1 calc R U . . .
C12 C 0.39607(17) 0.7486(2) 0.3071(2) 0.0352(4) Uani 1 1 d . . . . .
H12A H 0.4237 0.6642 0.3497 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3187 0.7328 0.2511 0.042 Uiso 1 1 calc R U . . .
C13 C 0.39614(18) 0.8581(2) 0.3866(2) 0.0383(5) Uani 1 1 d . . . . .
H13A H 0.3898 0.9472 0.3509 0.046 Uiso 1 1 calc R U . . .
H13B H 0.4669 0.8556 0.4554 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2982(2) 0.8368(3) 0.4167(2) 0.0482(6) Uani 1 1 d . . . . .
H14A H 0.2287 0.8380 0.3466 0.058 Uiso 1 1 calc R U . . .
H14B H 0.3051 0.7461 0.4500 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2869(3) 0.9355(3) 0.4949(2) 0.0558(7) Uani 1 1 d . . . . .
H15A H 0.2874 1.0275 0.4664 0.067 Uiso 1 1 calc R U . . .
H15B H 0.3515 0.9272 0.5688 0.067 Uiso 1 1 calc R U . . .
C16 C 0.1787(2) 0.9147(4) 0.5096(3) 0.0628(8) Uani 1 1 d . . . . .
H16A H 0.1143 0.9254 0.4360 0.075 Uiso 1 1 calc R U . . .
H16B H 0.1773 0.8217 0.5357 0.075 Uiso 1 1 calc R U . . .
C17 C 0.1671(3) 1.0100(4) 0.5903(3) 0.0800(11) Uani 1 1 d . . . . .
H17A H 0.2285 0.9967 0.6644 0.120 Uiso 1 1 calc R U . . .
H17B H 0.0962 0.9940 0.5945 0.120 Uiso 1 1 calc R U . . .
H17C H 0.1689 1.1025 0.5653 0.120 Uiso 1 1 calc R U . . .
O1 O 0.32752(10) 0.91880(14) 0.13031(13) 0.0328(3) Uani 1 1 d . . . . .
N4 N 0.64254(12) 0.89012(16) 0.07599(14) 0.0285(3) Uani 1 1 d . . . . .
H4A H 0.6142 0.9497 0.0218 0.034 Uiso 1 1 calc R U . . .
H4B H 0.7087 0.8556 0.0925 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.363(3) . ?
C1 C5 1.425(2) . ?
C1 C4 1.442(2) . ?
C2 N1 1.349(2) . ?
C2 H2 0.9500 . ?
N1 C3 1.413(2) . ?
N1 C12 1.467(2) . ?
C3 O1 1.228(2) . ?
C3 N2 1.358(2) . ?
N2 C4 1.334(2) . ?
C4 N4 1.332(2) . ?
C5 C6 1.190(3) . ?
C6 C7 1.431(2) . ?
C7 C11 1.387(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 N3 1.331(3) . ?
C9 H9 0.9500 . ?
N3 C10 1.324(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.478(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.543(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.482(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?

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
C2 C1 C5 120.48(16) . . ?
C2 C1 C4 116.67(15) . . ?
C5 C1 C4 122.85(16) . . ?
N1 C2 C1 121.88(16) . . ?
N1 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 N1 C3 120.45(15) . . ?
C2 N1 C12 121.80(16) . . ?
C3 N1 C12 117.73(15) . . ?
O1 C3 N2 122.26(17) . . ?
O1 C3 N1 119.24(16) . . ?
N2 C3 N1 118.51(15) . . ?
C4 N2 C3 121.19(15) . . ?
N4 C4 N2 117.60(16) . . ?
N4 C4 C1 121.19(15) . . ?
N2 C4 C1 121.20(16) . . ?
C6 C5 C1 176.6(2) . . ?
C5 C6 C7 176.0(2) . . ?
C11 C7 C8 117.58(17) . . ?
C11 C7 C6 121.88(18) . . ?
C8 C7 C6 120.54(17) . . ?
C9 C8 C7 118.59(18) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N3 C9 C8 124.40(19) . . ?
N3 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
C10 N3 C9 116.11(17) . . ?
N3 C10 C11 124.4(2) . . ?
N3 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C7 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C7 C11 H11 120.6 . . ?
N1 C12 C13 113.08(16) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 109.4(2) . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 116.2(2) . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C13 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 112.1(3) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 113.1(3) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4604a_a
_database_code_depnum_ccdc_archive 'CCDC 2040832'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N6 O, C17 H20 N4 O'
_chemical_formula_sum            'C35 H40 N10 O2'
_chemical_formula_weight         632.77

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'

_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                   8.3993(3)
_cell_length_b                   18.1256(7)
_cell_length_c                   21.8533(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.942(2)
_cell_angle_gamma                90
_cell_volume                     3322.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3974
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.10


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23116
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6661
_reflns_number_gt                4572
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0894P)²+1.0068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6661
_refine_ls_number_parameters     466
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.013
_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_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
C1 C 0.6997(2) 0.73670(12) 0.62870(9) 0.0264(5) Uani 1 1 d . . . . .
N1 N 0.70729(19) 0.66785(10) 0.60100(8) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.5608(2) 0.65805(11) 0.57130(9) 0.0221(4) Uani 1 1 d . . . . .
N2 N 0.51529(19) 0.59753(9) 0.53783(7) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.3669(2) 0.60357(11) 0.51370(9) 0.0217(4) Uani 1 1 d . . . . .
N3 N 0.27164(19) 0.66385(10) 0.52298(8) 0.0251(4) Uani 1 1 d . . . . .
H3 H 0.1749 0.6632 0.5055 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3150(2) 0.72582(12) 0.55770(9) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.4741(2) 0.72050(11) 0.58261(9) 0.0244(5) Uani 1 1 d . . . . .
N4 N 0.5615(2) 0.76987(10) 0.61890(8) 0.0284(4) Uani 1 1 d . . . . .
C6 C 0.8395(2) 0.61494(12) 0.60404(10) 0.0269(5) Uani 1 1 d D . . . .
H6A H 0.9409 0.6423 0.6109 0.032 Uiso 1 1 calc R U . . .
H6B H 0.8429 0.5893 0.5642 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8270(3) 0.55788(13) 0.65432(10) 0.0311(5) Uani 1 1 d D . . . .
H7A H 0.9035 0.5176 0.6471 0.037 Uiso 1 1 calc R U . . .
H7B H 0.7186 0.5363 0.6512 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8589(3) 0.58673(15) 0.71893(11) 0.0408(6) Uani 1 1 d D . . . .
H8A H 0.7796 0.6254 0.7273 0.049 Uiso 1 1 calc R U . . .
H8B H 0.9659 0.6097 0.7222 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8503(3) 0.52558(17) 0.76713(11) 0.0502(7) Uani 1 1 d D . . . .
C10 C 0.8435(11) 0.5567(5) 0.8327(3) 0.067(3) Uani 0.535(11) 1 d D . P A 1
H10A H 0.7500 0.5899 0.8339 0.080 Uiso 0.535(11) 1 calc R U P A 1
H10B H 0.8258 0.5152 0.8610 0.080 Uiso 0.535(11) 1 calc R U P A 1
C11 C 0.9912(13) 0.5992(7) 0.8564(5) 0.084(3) Uani 0.535(11) 1 d D . P A 1
H11A H 1.0856 0.5678 0.8538 0.125 Uiso 0.535(11) 1 calc R U P A 1
H11B H 0.9789 0.6134 0.8992 0.125 Uiso 0.535(11) 1 calc R U P A 1
H11C H 1.0037 0.6436 0.8316 0.125 Uiso 0.535(11) 1 calc R U P A 1
C10A C 0.9505(12) 0.5358(4) 0.8277(3) 0.056(3) Uani 0.465(11) 1 d D . P A 2
H10C H 0.9312 0.4942 0.8557 0.067 Uiso 0.465(11) 1 calc R U P A 2
H10D H 1.0653 0.5366 0.8195 0.067 Uiso 0.465(11) 1 calc R U P A 2
C11A C 0.9040(15) 0.6074(7) 0.8568(6) 0.072(3) Uani 0.465(11) 1 d D . P A 2
H11D H 0.9303 0.6486 0.8301 0.108 Uiso 0.465(11) 1 calc R U P A 2
H11E H 0.9624 0.6129 0.8966 0.108 Uiso 0.465(11) 1 calc R U P A 2
H11F H 0.7892 0.6074 0.8628 0.108 Uiso 0.465(11) 1 calc R U P A 2
N5 N 0.3035(2) 0.55006(10) 0.47848(8) 0.0301(4) Uani 1 1 d . . . . .
H5A H 0.3596 0.5104 0.4710 0.036 Uiso 1 1 calc R U . . .
H5B H 0.2054 0.5544 0.4627 0.036 Uiso 1 1 calc R U . . .
O1 O 0.21811(17) 0.77646(8) 0.56385(7) 0.0330(4) Uani 1 1 d . . . . .
C12 C 0.8316(3) 0.76641(13) 0.66452(10) 0.0311(5) Uani 1 1 d . . . . .
C13 C 0.9434(3) 0.78941(13) 0.69491(11) 0.0340(5) Uani 1 1 d . . . . .
C14 C 1.0782(3) 0.81378(13) 0.73247(11) 0.0324(5) Uani 1 1 d . . . . .
C15 C 1.2234(3) 0.82854(14) 0.70722(11) 0.0378(6) Uani 1 1 d . . . . .
H15 H 1.2344 0.8248 0.6643 0.045 Uiso 1 1 calc R U . . .
C16 C 1.3510(3) 0.84868(15) 0.74589(12) 0.0419(6) Uani 1 1 d . . . . .
H16 H 1.4499 0.8581 0.7282 0.050 Uiso 1 1 calc R U . . .
N6 N 1.3448(2) 0.85580(13) 0.80642(10) 0.0460(6) Uani 1 1 d . . . . .
C17 C 1.2047(3) 0.84223(16) 0.82980(12) 0.0461(7) Uani 1 1 d . . . . .
H17 H 1.1969 0.8474 0.8728 0.055 Uiso 1 1 calc R U . . .
C18 C 1.0699(3) 0.82101(14) 0.79539(12) 0.0398(6) Uani 1 1 d . . . . .
H18 H 0.9730 0.8115 0.8145 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6951(2) 0.74413(12) 0.44193(9) 0.0258(5) Uani 1 1 d . . . . .
C20 C 0.8510(2) 0.74188(12) 0.47282(9) 0.0246(5) Uani 1 1 d . . . . .
N7 N 0.94486(19) 0.68211(10) 0.46857(8) 0.0255(4) Uani 1 1 d . . . . .
C21 C 0.8929(2) 0.62099(12) 0.43803(9) 0.0235(5) Uani 1 1 d . . . . .
N8 N 0.73934(19) 0.62132(10) 0.40987(8) 0.0259(4) Uani 1 1 d . . . . .
C22 C 0.6462(2) 0.68234(13) 0.41156(10) 0.0281(5) Uani 1 1 d . . . . .
H22 H 0.5439 0.6817 0.3909 0.034 Uiso 1 1 calc R U . . .
N9 N 0.9065(2) 0.79815(10) 0.50597(8) 0.0317(4) Uani 1 1 d . . . . .
H9A H 1.0020 0.7957 0.5244 0.038 Uiso 1 1 calc R U . . .
H9B H 0.8479 0.8380 0.5096 0.038 Uiso 1 1 calc R U . . .
O2 O 0.97559(17) 0.56498(8) 0.43452(7) 0.0320(4) Uani 1 1 d . . . . .
C23 C 0.6795(2) 0.55487(13) 0.37719(10) 0.0310(5) Uani 1 1 d D . . . .
H23A H 0.5618 0.5536 0.3777 0.037 Uiso 1 1 calc R U . . .
H23B H 0.7216 0.5104 0.3988 0.037 Uiso 1 1 calc R U . . .
C24 C 0.7282(3) 0.55310(14) 0.31134(11) 0.0358(6) Uani 1 1 d D . . . .
H24A H 0.8451 0.5465 0.3110 0.043 Uiso 1 1 calc R U . . .
H24B H 0.7015 0.6011 0.2918 0.043 Uiso 1 1 calc R U . . .
C25 C 0.6473(3) 0.49190(15) 0.27398(13) 0.0468(7) Uani 1 1 d D . . . .
H25A H 0.5310 0.5013 0.2708 0.056 Uiso 1 1 calc R U . . .
H25B H 0.6864 0.4929 0.2320 0.056 Uiso 1 1 calc R U . . .
C26 C 0.6768(5) 0.41635(18) 0.30106(15) 0.0727(10) Uani 1 1 d D . . . .
C27 C 0.5784(9) 0.3546(3) 0.2646(4) 0.072(3) Uani 0.587(12) 1 d D . P B 1
H27A H 0.5746 0.3089 0.2893 0.086 Uiso 0.587(12) 1 calc R U P B 1
H27B H 0.4679 0.3715 0.2549 0.086 Uiso 0.587(12) 1 calc R U P B 1
C28 C 0.6645(15) 0.3407(4) 0.2058(3) 0.099(4) Uani 0.587(12) 1 d D . P B 1
H28A H 0.6809 0.3876 0.1849 0.148 Uiso 0.587(12) 1 calc R U P B 1
H28B H 0.5998 0.3079 0.1789 0.148 Uiso 0.587(12) 1 calc R U P B 1
H28C H 0.7680 0.3175 0.2159 0.148 Uiso 0.587(12) 1 calc R U P B 1
C27A C 0.6771(18) 0.3550(7) 0.2539(9) 0.134(8) Uani 0.413(12) 1 d D . P B 2
H27C H 0.7495 0.3692 0.2215 0.160 Uiso 0.413(12) 1 calc R U P B 2
H27D H 0.7214 0.3100 0.2740 0.160 Uiso 0.413(12) 1 calc R U P B 2
C28A C 0.5208(13) 0.3367(6) 0.2245(6) 0.077(3) Uani 0.413(12) 1 d D . P B 2
H28D H 0.4478 0.3220 0.2559 0.116 Uiso 0.413(12) 1 calc R U P B 2
H28E H 0.5326 0.2960 0.1956 0.116 Uiso 0.413(12) 1 calc R U P B 2
H28F H 0.4777 0.3800 0.2025 0.116 Uiso 0.413(12) 1 calc R U P B 2
C29 C 0.5941(2) 0.80762(13) 0.44432(10) 0.0298(5) Uani 1 1 d . . . . .
C30 C 0.5113(3) 0.86119(13) 0.44611(11) 0.0327(5) Uani 1 1 d . . . . .
C31 C 0.4123(2) 0.92566(13) 0.44977(10) 0.0307(5) Uani 1 1 d . . . . .
C32 C 0.2982(3) 0.93036(14) 0.49354(12) 0.0393(6) Uani 1 1 d . . . . .
H32 H 0.2816 0.8903 0.5205 0.047 Uiso 1 1 calc R U . . .
C33 C 0.2095(3) 0.99417(16) 0.49712(12) 0.0435(6) Uani 1 1 d . . . . .
H33 H 0.1326 0.9966 0.5275 0.052 Uiso 1 1 calc R U . . .
N10 N 0.2245(2) 1.05254(12) 0.46078(10) 0.0437(5) Uani 1 1 d . . . . .
C34 C 0.3328(3) 1.04708(14) 0.41824(12) 0.0436(6) Uani 1 1 d . . . . .
H34 H 0.3448 1.0875 0.3912 0.052 Uiso 1 1 calc R U . . .
C35 C 0.4281(3) 0.98575(14) 0.41145(11) 0.0381(6) Uani 1 1 d . . . . .
H35 H 0.5039 0.9849 0.3807 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.315(3) . ?
C1 N1 1.390(3) . ?
C1 C12 1.429(3) . ?
N1 C2 1.373(2) . ?
N1 C6 1.466(3) . ?
C2 N2 1.362(2) . ?
C2 C5 1.375(3) . ?
N2 C3 1.333(2) . ?
C3 N5 1.332(3) . ?
C3 N3 1.375(3) . ?
N3 C4 1.394(3) . ?
N3 H3 0.8800 . ?
C4 O1 1.238(2) . ?
C4 C5 1.420(3) . ?
C5 N4 1.382(3) . ?
C6 C7 1.516(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.533(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10A 1.543(7) . ?
C9 C10 1.543(7) . ?
C10 C11 1.528(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10A C11A 1.506(13) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C12 C13 1.197(3) . ?
C13 C14 1.434(3) . ?
C14 C18 1.387(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 N6 1.333(3) . ?
C16 H16 0.9500 . ?
N6 C17 1.330(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C22 1.355(3) . ?
C19 C29 1.432(3) . ?
C19 C20 1.442(3) . ?
C20 N9 1.322(3) . ?
C20 N7 1.346(3) . ?
N7 C21 1.354(3) . ?
C21 O2 1.235(2) . ?
C21 N8 1.400(3) . ?
N8 C22 1.357(3) . ?
N8 C23 1.475(3) . ?
C22 H22 0.9500 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.517(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.507(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27A 1.517(13) . ?
C26 C27 1.581(8) . ?
C27 C28 1.528(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C27A C28A 1.468(15) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
C29 C30 1.196(3) . ?
C30 C31 1.438(3) . ?
C31 C35 1.384(3) . ?
C31 C32 1.391(3) . ?
C32 C33 1.380(3) . ?
C32 H32 0.9500 . ?
C33 N10 1.333(3) . ?
C33 H33 0.9500 . ?
N10 C34 1.337(3) . ?
C34 C35 1.382(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 113.55(17) . . ?
N4 C1 C12 124.8(2) . . ?
N1 C1 C12 121.69(18) . . ?
C2 N1 C1 105.19(16) . . ?
C2 N1 C6 126.53(17) . . ?
C1 N1 C6 128.25(16) . . ?
N2 C2 N1 125.30(18) . . ?
N2 C2 C5 128.52(18) . . ?
N1 C2 C5 106.18(18) . . ?
C3 N2 C2 112.15(16) . . ?
N5 C3 N2 120.46(18) . . ?
N5 C3 N3 116.43(17) . . ?
N2 C3 N3 123.12(18) . . ?
C3 N3 C4 125.66(16) . . ?
C3 N3 H3 117.2 . . ?
C4 N3 H3 117.2 . . ?
O1 C4 N3 120.12(18) . . ?
O1 C4 C5 128.27(19) . . ?
N3 C4 C5 111.61(17) . . ?
C2 C5 N4 111.42(17) . . ?
C2 C5 C4 118.92(19) . . ?
N4 C5 C4 129.65(19) . . ?
C1 N4 C5 103.66(17) . . ?
N1 C6 C7 113.48(17) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 115.1(2) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 112.2(2) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10A 117.4(4) . . ?
C8 C9 C10 112.2(4) . . ?
C11 C10 C9 115.5(8) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C11A C10A C9 108.9(8) . . ?
C11A C10A H10C 109.9 . . ?
C9 C10A H10C 109.9 . . ?
C11A C10A H10D 109.9 . . ?
C9 C10A H10D 109.9 . . ?
H10C C10A H10D 108.3 . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C13 C12 C1 178.3(3) . . ?
C12 C13 C14 177.5(3) . . ?
C18 C14 C15 117.7(2) . . ?
C18 C14 C13 121.2(2) . . ?
C15 C14 C13 121.0(2) . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N6 C16 C15 124.4(2) . . ?
N6 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C17 N6 C16 116.3(2) . . ?
N6 C17 C18 124.0(2) . . ?
N6 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
C17 C18 C14 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C14 C18 H18 120.5 . . ?
C22 C19 C29 121.11(19) . . ?
C22 C19 C20 116.81(19) . . ?
C29 C19 C20 122.1(2) . . ?
N9 C20 N7 117.86(18) . . ?
N9 C20 C19 121.38(19) . . ?
N7 C20 C19 120.76(19) . . ?
C20 N7 C21 121.14(17) . . ?
O2 C21 N7 122.33(18) . . ?
O2 C21 N8 118.99(19) . . ?
N7 C21 N8 118.67(17) . . ?
C22 N8 C21 120.73(18) . . ?
C22 N8 C23 119.76(17) . . ?
C21 N8 C23 119.50(17) . . ?
C19 C22 N8 121.77(18) . . ?
C19 C22 H22 119.1 . . ?
N8 C22 H22 119.1 . . ?
C20 N9 H9A 120.0 . . ?
C20 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
N8 C23 C24 112.02(18) . . ?
N8 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N8 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 C25 113.0(2) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 113.1(2) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27A 113.9(8) . . ?
C25 C26 C27 112.0(4) . . ?
C28 C27 C26 106.5(7) . . ?
C28 C27 H27A 110.4 . . ?
C26 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
C26 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
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 . . ?
C28A C27A C26 115.4(12) . . ?
C28A C27A H27C 108.4 . . ?
C26 C27A H27C 108.4 . . ?
C28A C27A H27D 108.4 . . ?
C26 C27A H27D 108.4 . . ?
H27C C27A H27D 107.5 . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C30 C29 C19 179.2(3) . . ?
C29 C30 C31 178.7(2) . . ?
C35 C31 C32 117.3(2) . . ?
C35 C31 C30 122.2(2) . . ?
C32 C31 C30 120.6(2) . . ?
C33 C32 C31 118.9(2) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
N10 C33 C32 124.3(2) . . ?
N10 C33 H33 117.9 . . ?
C32 C33 H33 117.9 . . ?
C33 N10 C34 116.4(2) . . ?
N10 C34 C35 123.5(2) . . ?
N10 C34 H34 118.2 . . ?
C35 C34 H34 118.2 . . ?
C34 C35 C31 119.6(2) . . ?
C34 C35 H35 120.2 . . ?
C31 C35 H35 120.2 . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4594a_a
_database_code_depnum_ccdc_archive 'CCDC 2040831'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C17 H20 N4 O), 3(H2 O)'
_chemical_formula_sum            'C51 H66 N12 O6'
_chemical_formula_weight         943.15

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'

_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                   11.9317(6)
_cell_length_b                   14.0535(8)
_cell_length_c                   15.9543(9)
_cell_angle_alpha                97.164(2)
_cell_angle_beta                 105.719(2)
_cell_angle_gamma                97.882(2)
_cell_volume                     2513.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4660
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.88


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17746
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.120
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             9576
_reflns_number_gt                6235
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0861P)²+1.2647P] 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         9576
_refine_ls_number_parameters     728
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.009

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
C1 C 0.1492(2) 0.23086(16) 0.55947(16) 0.0270(5) Uani 1 1 d . . . . .
N1 N 0.18053(18) 0.28618(13) 0.50260(13) 0.0295(5) Uani 1 1 d . . . . .
C2 C 0.1710(2) 0.38045(16) 0.50981(16) 0.0298(6) Uani 1 1 d . . . . .
C3 C 0.1327(2) 0.42760(16) 0.57992(16) 0.0283(5) Uani 1 1 d . . . . .
C4 C 0.0991(2) 0.37002(16) 0.63446(16) 0.0294(5) Uani 1 1 d . . . . .
H4 H 0.0706 0.3980 0.6802 0.035 Uiso 1 1 calc R U . . .
N2 N 0.10528(18) 0.27413(13) 0.62555(13) 0.0276(5) Uani 1 1 d . . . . .
O1 O 0.15613(16) 0.14346(11) 0.55470(12) 0.0353(4) Uani 1 1 d . . . . .
N3 N 0.1973(2) 0.42966(15) 0.45037(15) 0.0397(6) Uani 1 1 d . . . . .
H3A H 0.2203 0.4004 0.4075 0.048 Uiso 1 1 calc R U . . .
H3B H 0.1917 0.4917 0.4536 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1276(2) 0.52875(17) 0.58837(16) 0.0306(6) Uani 1 1 d . . . . .
C6 C 0.1262(2) 0.61401(17) 0.59145(17) 0.0321(6) Uani 1 1 d . . . . .
C7 C 0.1199(2) 0.71508(16) 0.59323(17) 0.0299(6) Uani 1 1 d . . . . .
C8 C 0.1516(2) 0.76331(17) 0.52980(17) 0.0321(6) Uani 1 1 d . . . . .
H8 H 0.1783 0.7276 0.4867 0.039 Uiso 1 1 calc R U . . .
N4 N 0.1464(2) 0.85744(14) 0.52620(15) 0.0374(5) Uani 1 1 d . . . . .
C9 C 0.1072(2) 0.90588(17) 0.58703(18) 0.0381(6) Uani 1 1 d . . . . .
H9 H 0.1027 0.9726 0.5854 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0730(3) 0.86401(18) 0.65181(19) 0.0398(7) Uani 1 1 d . . . . .
H10 H 0.0458 0.9013 0.6937 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0787(3) 0.76736(18) 0.65514(18) 0.0386(6) Uani 1 1 d . . . . .
H11 H 0.0550 0.7368 0.6990 0.046 Uiso 1 1 calc R U . . .
C12 C 0.0654(3) 0.21474(18) 0.68481(18) 0.0378(6) Uani 1 1 d . . . . .
H12A H 0.0286 0.1485 0.6515 0.045 Uiso 1 1 calc R U . . .
H12B H 0.0039 0.2436 0.7048 0.045 Uiso 1 1 calc R U . . .
C13 C 0.1625(4) 0.2068(4) 0.7638(3) 0.1057(19) Uani 1 1 d D . . . .
C14 C 0.1463(6) 0.1860(4) 0.8496(4) 0.0527(19) Uani 0.541(8) 1 d D . P A 1
H14A H 0.0779 0.2117 0.8613 0.063 Uiso 0.541(8) 1 calc R U P A 1
H14B H 0.2182 0.2134 0.8995 0.063 Uiso 0.541(8) 1 calc R U P A 1
C15 C 0.1239(9) 0.0745(5) 0.8330(5) 0.053(3) Uani 0.541(8) 1 d D . P A 1
H15A H 0.1823 0.0514 0.8053 0.063 Uiso 0.541(8) 1 calc R U P A 1
H15B H 0.0440 0.0498 0.7913 0.063 Uiso 0.541(8) 1 calc R U P A 1
C16 C 0.1335(11) 0.0318(7) 0.9215(7) 0.073(4) Uani 0.541(8) 1 d D . P A 1
H16A H 0.2173 0.0411 0.9574 0.088 Uiso 0.541(8) 1 calc R U P A 1
H16B H 0.0894 0.0654 0.9568 0.088 Uiso 0.541(8) 1 calc R U P A 1
C17 C 0.0808(8) -0.0760(6) 0.8952(5) 0.051(2) Uani 0.541(8) 1 d D . P A 1
H17A H 0.0052 -0.0850 0.8489 0.076 Uiso 0.541(8) 1 calc R U P A 1
H17B H 0.0678 -0.1017 0.9468 0.076 Uiso 0.541(8) 1 calc R U P A 1
H17C H 0.1354 -0.1109 0.8729 0.076 Uiso 0.541(8) 1 calc R U P A 1
C14A C 0.0889(6) 0.1232(5) 0.8050(4) 0.0361(19) Uani 0.459(8) 1 d D . P A 2
H14C H 0.0336 0.1534 0.8317 0.043 Uiso 0.459(8) 1 calc R U P A 2
H14D H 0.0419 0.0697 0.7567 0.043 Uiso 0.459(8) 1 calc R U P A 2
C15A C 0.1760(9) 0.0812(9) 0.8761(8) 0.069(3) Uani 0.459(8) 1 d D . P A 2
H15C H 0.2292 0.1341 0.9223 0.083 Uiso 0.459(8) 1 calc R U P A 2
H15D H 0.2245 0.0425 0.8491 0.083 Uiso 0.459(8) 1 calc R U P A 2
C16A C 0.0942(12) 0.0157(11) 0.9151(10) 0.069(5) Uani 0.459(8) 1 d D . P A 2
H16C H 0.0876 0.0521 0.9703 0.083 Uiso 0.459(8) 1 calc R U P A 2
H16D H 0.0140 -0.0029 0.8726 0.083 Uiso 0.459(8) 1 calc R U P A 2
C17A C 0.1449(19) -0.0742(11) 0.9339(15) 0.166(9) Uani 0.459(8) 1 d D . P A 2
H17D H 0.1852 -0.0928 0.8901 0.249 Uiso 0.459(8) 1 calc R U P A 2
H17E H 0.0809 -0.1276 0.9308 0.249 Uiso 0.459(8) 1 calc R U P A 2
H17F H 0.2016 -0.0610 0.9932 0.249 Uiso 0.459(8) 1 calc R U P A 2
C18 C 0.5627(2) -0.05443(16) 0.18985(16) 0.0289(5) Uani 1 1 d . . . . .
N5 N 0.53759(19) -0.00846(13) 0.11909(13) 0.0309(5) Uani 1 1 d . . . . .
C19 C 0.5390(2) 0.08725(16) 0.12944(16) 0.0295(5) Uani 1 1 d . . . . .
C20 C 0.5683(2) 0.14598(16) 0.21580(16) 0.0285(5) Uani 1 1 d . . . . .
C21 C 0.5911(2) 0.09766(16) 0.28540(16) 0.0287(5) Uani 1 1 d . . . . .
H21 H 0.6099 0.1335 0.3435 0.034 Uiso 1 1 calc R U . . .
N6 N 0.58779(18) 0.00018(13) 0.27473(13) 0.0278(5) Uani 1 1 d . . . . .
O2 O 0.56390(17) -0.14259(11) 0.18241(11) 0.0356(4) Uani 1 1 d . . . . .
N7 N 0.5120(2) 0.12792(15) 0.05769(15) 0.0442(6) Uani 1 1 d . . . . .
H7A H 0.4938 0.0918 0.0050 0.053 Uiso 1 1 calc R U . . .
H7B H 0.5123 0.1910 0.0627 0.053 Uiso 1 1 calc R U . . .
C22 C 0.5716(2) 0.24882(17) 0.22522(17) 0.0338(6) Uani 1 1 d . . . . .
C23 C 0.5723(3) 0.33429(17) 0.22647(18) 0.0384(6) Uani 1 1 d . . . . .
C24 C 0.5699(3) 0.43608(17) 0.22838(18) 0.0377(6) Uani 1 1 d . . . . .
C25 C 0.5624(4) 0.4764(2) 0.1524(2) 0.0714(12) Uani 1 1 d . . . . .
H25 H 0.5613 0.4350 0.1002 0.086 Uiso 1 1 calc R U . . .
N8 N 0.5566(3) 0.57006(17) 0.14844(18) 0.0790(11) Uani 1 1 d . . . . .
C26 C 0.5578(3) 0.62677(18) 0.2227(2) 0.0523(8) Uani 1 1 d . . . . .
H26 H 0.5527 0.6934 0.2211 0.063 Uiso 1 1 calc R U . . .
C27 C 0.5658(3) 0.59378(18) 0.2998(2) 0.0473(8) Uani 1 1 d . . . . .
H27 H 0.5669 0.6369 0.3510 0.057 Uiso 1 1 calc R U . . .
C28 C 0.5724(3) 0.49709(18) 0.30361(19) 0.0425(7) Uani 1 1 d . . . . .
H28 H 0.5786 0.4730 0.3574 0.051 Uiso 1 1 calc R U . . .
C29 C 0.6127(2) -0.04939(17) 0.35214(16) 0.0319(6) Uani 1 1 d . . . . .
H29A H 0.6564 -0.0004 0.4053 0.038 Uiso 1 1 calc R U . . .
H29B H 0.6647 -0.0967 0.3441 0.038 Uiso 1 1 calc R U . . .
C30 C 0.5028(2) -0.10275(19) 0.36817(18) 0.0386(6) Uani 1 1 d . . . . .
H30A H 0.4587 -0.1523 0.3156 0.046 Uiso 1 1 calc R U . . .
H30B H 0.4507 -0.0559 0.3773 0.046 Uiso 1 1 calc R U . . .
C31 C 0.5357(3) -0.1525(2) 0.44906(18) 0.0400(7) Uani 1 1 d . . . . .
H31A H 0.5898 -0.1978 0.4401 0.048 Uiso 1 1 calc R U . . .
H31B H 0.5790 -0.1024 0.5014 0.048 Uiso 1 1 calc R U . . .
C32 C 0.4300(3) -0.2086(2) 0.4672(2) 0.0478(7) Uani 1 1 d . . . . .
H32A H 0.3830 -0.2546 0.4130 0.057 Uiso 1 1 calc R U . . .
H32B H 0.3795 -0.1623 0.4812 0.057 Uiso 1 1 calc R U . . .
C33 C 0.4621(3) -0.2654(2) 0.5428(2) 0.0463(7) Uani 1 1 d . . . . .
H33A H 0.5201 -0.2216 0.5942 0.056 Uiso 1 1 calc R U . . .
H33B H 0.3902 -0.2862 0.5602 0.056 Uiso 1 1 calc R U . . .
C34 C 0.5139(3) -0.3544(2) 0.5206(2) 0.0563(9) Uani 1 1 d . . . . .
H34A H 0.4566 -0.3989 0.4704 0.084 Uiso 1 1 calc R U . . .
H34B H 0.5319 -0.3876 0.5719 0.084 Uiso 1 1 calc R U . . .
H34C H 0.5867 -0.3344 0.5051 0.084 Uiso 1 1 calc R U . . .
C35 C 0.2338(3) 0.37069(18) 0.22283(19) 0.0390(7) Uani 1 1 d . . . . .
N9 N 0.2230(2) 0.31886(14) 0.28678(14) 0.0359(5) Uani 1 1 d . . . . .
C36 C 0.2292(2) 0.22415(17) 0.27760(17) 0.0310(6) Uani 1 1 d . . . . .
C37 C 0.2493(2) 0.17399(17) 0.19996(17) 0.0311(6) Uani 1 1 d . . . . .
C38 C 0.2628(2) 0.22834(18) 0.13804(18) 0.0372(6) Uani 1 1 d . . . . .
H38 H 0.2775 0.1982 0.0863 0.045 Uiso 1 1 calc R U . . .
N10 N 0.2562(2) 0.32391(16) 0.14718(16) 0.0419(6) Uani 1 1 d . . . . .
O3 O 0.2264(2) 0.45775(13) 0.22810(15) 0.0603(7) Uani 1 1 d . . . . .
N11 N 0.2169(2) 0.17722(15) 0.34199(15) 0.0413(6) Uani 1 1 d . . . . .
H11A H 0.2050 0.2083 0.3893 0.050 Uiso 1 1 calc R U . . .
H11B H 0.2206 0.1148 0.3377 0.050 Uiso 1 1 calc R U . . .
C39 C 0.2518(2) 0.07181(18) 0.19058(17) 0.0338(6) Uani 1 1 d . . . . .
C40 C 0.2493(2) -0.01385(18) 0.18582(18) 0.0363(6) Uani 1 1 d . . . . .
C41 C 0.2451(2) -0.11673(17) 0.18074(18) 0.0341(6) Uani 1 1 d . . . . .
C42 C 0.2045(3) -0.16461(18) 0.24120(19) 0.0392(7) Uani 1 1 d . . . . .
H42 H 0.1789 -0.1273 0.2840 0.047 Uiso 1 1 calc R U . . .
N12 N 0.1997(2) -0.25984(15) 0.24253(16) 0.0442(6) Uani 1 1 d . . . . .
C43 C 0.2371(3) -0.31095(19) 0.1818(2) 0.0474(8) Uani 1 1 d . . . . .
H43 H 0.2343 -0.3789 0.1815 0.057 Uiso 1 1 calc R U . . .
C44 C 0.2792(3) -0.26989(19) 0.1200(2) 0.0478(8) Uani 1 1 d . . . . .
H44 H 0.3055 -0.3089 0.0787 0.057 Uiso 1 1 calc R U . . .
C45 C 0.2831(3) -0.17179(19) 0.11834(19) 0.0413(7) Uani 1 1 d . . . . .
H45 H 0.3110 -0.1423 0.0756 0.050 Uiso 1 1 calc R U . . .
C46 C 0.2661(4) 0.3793(3) 0.0763(2) 0.0776(13) Uani 1 1 d D . . . .
C47 C 0.1727(6) 0.4128(5) 0.0234(4) 0.052(2) Uani 0.470(7) 1 d D . P B 1
H47A H 0.1399 0.4554 0.0614 0.062 Uiso 0.470(7) 1 calc R U P B 1
H47B H 0.1095 0.3565 -0.0084 0.062 Uiso 0.470(7) 1 calc R U P B 1
C48 C 0.2070(6) 0.4685(4) -0.0426(4) 0.0352(17) Uani 0.470(7) 1 d D . P B 1
H48A H 0.2531 0.4311 -0.0734 0.042 Uiso 0.470(7) 1 calc R U P B 1
H48B H 0.2581 0.5315 -0.0115 0.042 Uiso 0.470(7) 1 calc R U P B 1
C49 C 0.0986(7) 0.4874(6) -0.1103(6) 0.049(2) Uani 0.470(7) 1 d D . P B 1
H49A H 0.0472 0.5168 -0.0789 0.059 Uiso 0.470(7) 1 calc R U P B 1
H49B H 0.0530 0.4246 -0.1464 0.059 Uiso 0.470(7) 1 calc R U P B 1
C50 C 0.1310(14) 0.5552(9) -0.1712(8) 0.049(3) Uani 0.470(7) 1 d D . P B 1
H50A H 0.1883 0.5283 -0.1978 0.059 Uiso 0.470(7) 1 calc R U P B 1
H50B H 0.0588 0.5549 -0.2199 0.059 Uiso 0.470(7) 1 calc R U P B 1
C51 C 0.1839(13) 0.6609(10) -0.1275(10) 0.052(2) Uani 0.470(7) 1 d D . P B 1
H51A H 0.1319 0.6865 -0.0955 0.078 Uiso 0.470(7) 1 calc R U P B 1
H51B H 0.1915 0.7002 -0.1729 0.078 Uiso 0.470(7) 1 calc R U P B 1
H51C H 0.2621 0.6636 -0.0860 0.078 Uiso 0.470(7) 1 calc R U P B 1
C47A C 0.1317(7) 0.3558(6) 0.0069(4) 0.070(2) Uani 0.530(7) 1 d D . P B 2
H47C H 0.1078 0.2841 -0.0088 0.084 Uiso 0.530(7) 1 calc R U P B 2
H47D H 0.0781 0.3795 0.0392 0.084 Uiso 0.530(7) 1 calc R U P B 2
C48A C 0.1081(6) 0.3966(4) -0.0789(4) 0.060(2) Uani 0.530(7) 1 d D . P B 2
H48C H 0.1546 0.3690 -0.1156 0.072 Uiso 0.530(7) 1 calc R U P B 2
H48D H 0.0232 0.3772 -0.1122 0.072 Uiso 0.530(7) 1 calc R U P B 2
C49A C 0.1413(8) 0.5068(5) -0.0611(5) 0.052(2) Uani 0.530(7) 1 d D . P B 2
H49C H 0.2276 0.5255 -0.0319 0.063 Uiso 0.530(7) 1 calc R U P B 2
H49D H 0.1004 0.5336 -0.0197 0.063 Uiso 0.530(7) 1 calc R U P B 2
C50A C 0.1097(16) 0.5531(10) -0.1450(8) 0.076(4) Uani 0.530(7) 1 d D . P B 2
H50C H 0.1548 0.5306 -0.1851 0.092 Uiso 0.530(7) 1 calc R U P B 2
H50D H 0.0242 0.5323 -0.1764 0.092 Uiso 0.530(7) 1 calc R U P B 2
C51A C 0.139(2) 0.6639(12) -0.1209(13) 0.148(10) Uani 0.530(7) 1 d D . P B 2
H51D H 0.1005 0.6855 -0.0766 0.222 Uiso 0.530(7) 1 calc R U P B 2
H51E H 0.1101 0.6926 -0.1738 0.222 Uiso 0.530(7) 1 calc R U P B 2
H51F H 0.2247 0.6848 -0.0967 0.222 Uiso 0.530(7) 1 calc R U P B 2
O4 O 0.1729(2) 0.00296(13) 0.41554(14) 0.0546(6) Uani 1 1 d D . . . .
H4B H 0.179(4) -0.0520(18) 0.435(3) 0.126 Uiso 1 1 d D U . . .
H4C H 0.172(4) 0.0538(19) 0.450(3) 0.126 Uiso 1 1 d D U . . .
O5 O 0.5361(2) 0.71260(14) 0.03368(13) 0.0565(6) Uani 1 1 d D . . . .
H5B H 0.541(4) 0.7667(18) 0.067(3) 0.134 Uiso 1 1 d D U . . .
H5C H 0.530(4) 0.6580(18) 0.053(3) 0.134 Uiso 1 1 d D U . . .
O6 O 0.1587(2) 0.58971(14) 0.34665(15) 0.0542(6) Uani 1 1 d D . . . .
H6B H 0.170(4) 0.6477(16) 0.330(3) 0.105 Uiso 1 1 d D U . . .
H6C H 0.179(4) 0.5428(19) 0.316(3) 0.105 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.236(3) . ?
C1 N1 1.359(3) . ?
C1 N2 1.408(3) . ?
N1 C2 1.338(3) . ?
C2 N3 1.319(3) . ?
C2 C3 1.440(3) . ?
C3 C4 1.359(3) . ?
C3 C5 1.422(3) . ?
C4 N2 1.351(3) . ?
C4 H4 0.9500 . ?
N2 C12 1.466(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C5 C6 1.196(3) . ?
C6 C7 1.430(3) . ?
C7 C8 1.391(3) . ?
C7 C11 1.392(4) . ?
C8 N4 1.340(3) . ?
C8 H8 0.9500 . ?
N4 C9 1.339(3) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.491(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.492(5) . ?
C13 C14A 1.675(6) . ?
C14 C15 1.530(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.584(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C14A C15A 1.552(8) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A C16A 1.554(9) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A C17A 1.503(9) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17D 0.9801 . ?
C17A H17E 0.9801 . ?
C17A H17F 0.9801 . ?
C18 O2 1.232(3) . ?
C18 N5 1.354(3) . ?
C18 N6 1.404(3) . ?
N5 C19 1.332(3) . ?
C19 N7 1.325(3) . ?
C19 C20 1.442(3) . ?
C20 C21 1.358(3) . ?
C20 C22 1.428(3) . ?
C21 N6 1.353(3) . ?
C21 H21 0.9500 . ?
N6 C29 1.474(3) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
C22 C23 1.198(3) . ?
C23 C24 1.431(3) . ?
C24 C28 1.376(4) . ?
C24 C25 1.388(4) . ?
C25 N8 1.336(3) . ?
C25 H25 0.9500 . ?
N8 C26 1.338(4) . ?
C26 C27 1.353(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.519(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.528(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.509(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.520(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.514(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 O3 1.233(3) . ?
C35 N9 1.349(3) . ?
C35 N10 1.409(3) . ?
N9 C36 1.335(3) . ?
C36 N11 1.317(3) . ?
C36 C37 1.442(3) . ?
C37 C38 1.351(3) . ?
C37 C39 1.430(3) . ?
C38 N10 1.348(3) . ?
C38 H38 0.9500 . ?
N10 C46 1.472(4) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
C39 C40 1.192(3) . ?
C40 C41 1.431(3) . ?
C41 C42 1.394(4) . ?
C41 C45 1.395(4) . ?
C42 N12 1.335(3) . ?
C42 H42 0.9500 . ?
N12 C43 1.343(3) . ?
C43 C44 1.374(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.377(4) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.382(6) . ?
C46 C47A 1.645(7) . ?
C47 C48 1.498(7) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.523(8) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.529(10) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.528(11) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C47A C48A 1.521(6) . ?
C47A H47C 0.9900 . ?
C47A H47D 0.9900 . ?
C48A C49A 1.515(8) . ?
C48A H48C 0.9900 . ?
C48A H48D 0.9900 . ?
C49A C50A 1.539(12) . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
C50A C51A 1.525(13) . ?
C50A H50C 0.9900 . ?
C50A H50D 0.9900 . ?
C51A H51D 0.9800 . ?
C51A H51E 0.9800 . ?
C51A H51F 0.9800 . ?
O4 H4B 0.869(18) . ?
O4 H4C 0.848(18) . ?
O5 H5B 0.856(18) . ?
O5 H5C 0.865(18) . ?
O6 H6B 0.889(18) . ?
O6 H6C 0.868(18) . ?

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 C1 N1 122.6(2) . . ?
O1 C1 N2 118.6(2) . . ?
N1 C1 N2 118.86(19) . . ?
C2 N1 C1 120.6(2) . . ?
N3 C2 N1 118.1(2) . . ?
N3 C2 C3 120.4(2) . . ?
N1 C2 C3 121.5(2) . . ?
C4 C3 C5 122.9(2) . . ?
C4 C3 C2 116.6(2) . . ?
C5 C3 C2 120.5(2) . . ?
N2 C4 C3 121.9(2) . . ?
N2 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 N2 C1 120.4(2) . . ?
C4 N2 C12 119.7(2) . . ?
C1 N2 C12 119.84(19) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C6 C5 C3 176.1(3) . . ?
C5 C6 C7 177.8(3) . . ?
C8 C7 C11 117.9(2) . . ?
C8 C7 C6 119.9(2) . . ?
C11 C7 C6 122.1(2) . . ?
N4 C8 C7 123.5(2) . . ?
N4 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C9 N4 C8 117.1(2) . . ?
N4 C9 C10 123.4(2) . . ?
N4 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C7 118.9(3) . . ?
C10 C11 H11 120.5 . . ?
C7 C11 H11 120.5 . . ?
N2 C12 C13 113.4(3) . . ?
N2 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 125.1(4) . . ?
C12 C13 C14A 99.3(4) . . ?
C13 C14 C15 101.1(5) . . ?
C13 C14 H14A 111.6 . . ?
C15 C14 H14A 111.4 . . ?
C13 C14 H14B 111.6 . . ?
C15 C14 H14B 111.7 . . ?
H14A C14 H14B 109.4 . . ?
C14 C15 C16 111.9(6) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 107.1(8) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.1 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15A C14A C13 110.8(6) . . ?
C15A C14A H14C 109.8 . . ?
C13 C14A H14C 109.4 . . ?
C15A C14A H14D 109.3 . . ?
C13 C14A H14D 109.5 . . ?
H14C C14A H14D 108.1 . . ?
C14A C15A C16A 104.1(8) . . ?
C14A C15A H15C 110.7 . . ?
C16A C15A H15C 110.5 . . ?
C14A C15A H15D 111.2 . . ?
C16A C15A H15D 111.3 . . ?
H15C C15A H15D 108.9 . . ?
C17A C16A C15A 109.4(11) . . ?
C17A C16A H16C 111.0 . . ?
C15A C16A H16C 110.2 . . ?
C17A C16A H16D 108.3 . . ?
C15A C16A H16D 109.6 . . ?
H16C C16A H16D 108.2 . . ?
C16A C17A H17D 110.2 . . ?
C16A C17A H17E 110.3 . . ?
H17D C17A H17E 109.5 . . ?
C16A C17A H17F 107.9 . . ?
H17D C17A H17F 109.4 . . ?
H17E C17A H17F 109.5 . . ?
O2 C18 N5 122.4(2) . . ?
O2 C18 N6 118.8(2) . . ?
N5 C18 N6 118.86(19) . . ?
C19 N5 C18 120.9(2) . . ?
N7 C19 N5 118.2(2) . . ?
N7 C19 C20 120.2(2) . . ?
N5 C19 C20 121.6(2) . . ?
C21 C20 C22 123.3(2) . . ?
C21 C20 C19 116.1(2) . . ?
C22 C20 C19 120.6(2) . . ?
N6 C21 C20 122.1(2) . . ?
N6 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C21 N6 C18 120.27(19) . . ?
C21 N6 C29 120.4(2) . . ?
C18 N6 C29 119.36(18) . . ?
C19 N7 H7A 120.0 . . ?
C19 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C23 C22 C20 175.2(3) . . ?
C22 C23 C24 178.4(3) . . ?
C28 C24 C25 117.4(2) . . ?
C28 C24 C23 122.3(2) . . ?
C25 C24 C23 120.3(2) . . ?
N8 C25 C24 123.7(3) . . ?
N8 C25 H25 118.1 . . ?
C24 C25 H25 118.1 . . ?
C25 N8 C26 117.0(3) . . ?
N8 C26 C27 123.2(2) . . ?
N8 C26 H26 118.4 . . ?
C27 C26 H26 118.4 . . ?
C26 C27 C28 119.5(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C24 C28 C27 119.1(3) . . ?
C24 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
N6 C29 C30 114.0(2) . . ?
N6 C29 H29A 108.8 . . ?
C30 C29 H29A 108.7 . . ?
N6 C29 H29B 108.8 . . ?
C30 C29 H29B 108.8 . . ?
H29A C29 H29B 107.6 . . ?
C29 C30 C31 110.9(2) . . ?
C29 C30 H30A 109.4 . . ?
C31 C30 H30A 109.4 . . ?
C29 C30 H30B 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 108.0 . . ?
C32 C31 C30 113.3(2) . . ?
C32 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 C33 113.9(2) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 113.9(3) . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O3 C35 N9 122.8(2) . . ?
O3 C35 N10 118.4(2) . . ?
N9 C35 N10 118.7(2) . . ?
C36 N9 C35 120.9(2) . . ?
N11 C36 N9 118.1(2) . . ?
N11 C36 C37 120.5(2) . . ?
N9 C36 C37 121.4(2) . . ?
C38 C37 C39 123.4(2) . . ?
C38 C37 C36 116.3(2) . . ?
C39 C37 C36 120.3(2) . . ?
N10 C38 C37 122.2(2) . . ?
N10 C38 H38 118.9 . . ?
C37 C38 H38 118.9 . . ?
C38 N10 C35 120.3(2) . . ?
C38 N10 C46 120.4(2) . . ?
C35 N10 C46 119.2(2) . . ?
C36 N11 H11A 120.0 . . ?
C36 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C40 C39 C37 176.0(3) . . ?
C39 C40 C41 179.2(3) . . ?
C42 C41 C45 117.8(2) . . ?
C42 C41 C40 119.7(2) . . ?
C45 C41 C40 122.4(2) . . ?
N12 C42 C41 123.8(2) . . ?
N12 C42 H42 118.1 . . ?
C41 C42 H42 118.1 . . ?
C42 N12 C43 117.0(2) . . ?
N12 C43 C44 123.2(2) . . ?
N12 C43 H43 118.4 . . ?
C44 C43 H43 118.4 . . ?
C43 C44 C45 119.6(3) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C44 C45 C41 118.5(3) . . ?
C44 C45 H45 120.8 . . ?
C41 C45 H45 120.8 . . ?
C47 C46 N10 123.9(4) . . ?
N10 C46 C47A 104.1(3) . . ?
C46 C47 C48 113.1(5) . . ?
C46 C47 H47A 109.1 . . ?
C48 C47 H47A 109.1 . . ?
C46 C47 H47B 108.8 . . ?
C48 C47 H47B 108.8 . . ?
H47A C47 H47B 107.8 . . ?
C47 C48 C49 111.3(6) . . ?
C47 C48 H48A 109.5 . . ?
C49 C48 H48A 109.3 . . ?
C47 C48 H48B 109.2 . . ?
C49 C48 H48B 109.4 . . ?
H48A C48 H48B 108.0 . . ?
C48 C49 C50 112.5(9) . . ?
C48 C49 H49A 109.0 . . ?
C50 C49 H49A 109.1 . . ?
C48 C49 H49B 109.2 . . ?
C50 C49 H49B 109.1 . . ?
H49A C49 H49B 107.9 . . ?
C51 C50 C49 115.6(11) . . ?
C51 C50 H50A 108.4 . . ?
C49 C50 H50A 108.3 . . ?
C51 C50 H50B 108.5 . . ?
C49 C50 H50B 108.4 . . ?
H50A C50 H50B 107.4 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.3 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.6 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C48A C47A C46 119.6(6) . . ?
C48A C47A H47C 107.2 . . ?
C46 C47A H47C 107.3 . . ?
C48A C47A H47D 107.5 . . ?
C46 C47A H47D 107.6 . . ?
H47C C47A H47D 107.0 . . ?
C49A C48A C47A 111.1(6) . . ?
C49A C48A H48C 109.4 . . ?
C47A C48A H48C 109.4 . . ?
C49A C48A H48D 109.3 . . ?
C47A C48A H48D 109.7 . . ?
H48C C48A H48D 108.0 . . ?
C48A C49A C50A 113.5(8) . . ?
C48A C49A H49C 108.8 . . ?
C50A C49A H49C 108.7 . . ?
C48A C49A H49D 108.9 . . ?
C50A C49A H49D 109.0 . . ?
H49C C49A H49D 107.7 . . ?
C51A C50A C49A 110.2(11) . . ?
C51A C50A H50C 109.5 . . ?
C49A C50A H50C 109.7 . . ?
C51A C50A H50D 109.8 . . ?
C49A C50A H50D 109.5 . . ?
H50C C50A H50D 108.1 . . ?
C50A C51A H51D 109.3 . . ?
C50A C51A H51E 109.4 . . ?
H51D C51A H51E 109.5 . . ?
C50A C51A H51F 109.7 . . ?
H51D C51A H51F 109.5 . . ?
H51E C51A H51F 109.5 . . ?
H4B O4 H4C 121(3) . . ?
H5B O5 H5C 121(3) . . ?
H6B O6 H6C 116(3) . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4693a_a
_database_code_depnum_ccdc_archive 'CCDC 2040834'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H40 Cu F12 N6 O8, 2(C2 H4 Cl2)'
_chemical_formula_sum            'C48 H48 Cl4 Cu F12 N6 O8'
_chemical_formula_weight         1270.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3272(2)
_cell_length_b                   13.2769(5)
_cell_length_c                   17.4210(6)
_cell_angle_alpha                100.252(2)
_cell_angle_beta                 96.189(2)
_cell_angle_gamma                91.859(2)
_cell_volume                     1429.71(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.74

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             647
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.662
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45858
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         30.044
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             7580
_reflns_number_gt                6559
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1052P)²+1.1662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7580
_refine_ls_number_parameters     359
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.000000 0.500000 1.000000 0.01963(11) Uani 1 2 d S . P A 1
C1 C 0.5298(4) 0.38968(17) 0.54292(11) 0.0257(4) Uani 1 1 d . . . A 1
C2 C 0.7334(4) 0.43144(17) 0.52939(11) 0.0251(4) Uani 1 1 d . . . A 1
O1 O 0.8562(3) 0.48885(15) 0.57943(9) 0.0351(4) Uani 1 1 d . . . A 1
N2 N 0.7832(3) 0.40418(15) 0.45373(10) 0.0271(4) Uani 1 1 d . . . A 1
H2 H 0.907562 0.427775 0.444355 0.033 Uiso 1 1 calc R U . A 1
C3 C 0.6607(4) 0.34425(17) 0.39103(12) 0.0303(5) Uani 1 1 d . . . A 1
O2 O 0.7213(4) 0.32309(15) 0.32684(10) 0.0427(5) Uani 1 1 d . . . A 1
N1 N 0.4624(4) 0.31171(16) 0.40712(10) 0.0322(4) Uani 1 1 d . . . A 1
C4 C 0.4037(4) 0.33344(18) 0.48087(12) 0.0295(5) Uani 1 1 d . . . A 1
H4 H 0.267823 0.308056 0.489485 0.035 Uiso 1 1 calc R U . A 1
C5 C 0.3131(5) 0.2525(2) 0.34272(14) 0.0399(6) Uani 1 1 d . . . A 1
H5A H 0.346026 0.269635 0.292125 0.048 Uiso 1 1 calc R U . A 1
H5B H 0.166003 0.271977 0.350277 0.048 Uiso 1 1 calc R U . A 1
C6 C 0.3268(6) 0.1377(2) 0.33956(18) 0.0486(7) Uani 1 1 d . . . A 1
H6A H 0.280906 0.119631 0.388170 0.058 Uiso 1 1 calc R U . A 1
H6B H 0.476590 0.119238 0.336995 0.058 Uiso 1 1 calc R U . A 1
C7 C 0.1871(6) 0.0761(3) 0.2682(2) 0.0593(9) Uani 1 1 d . . . A 1
H7A H 0.232505 0.095910 0.220097 0.071 Uiso 1 1 calc R U . A 1
H7B H 0.212500 0.002456 0.265737 0.071 Uiso 1 1 calc R U . A 1
C8 C -0.0490(7) 0.0900(3) 0.2681(3) 0.0712(12) Uani 1 1 d . . . A 1
H8A H -0.075389 0.163161 0.268448 0.085 Uiso 1 1 calc R U . A 1
H8B H -0.093786 0.072535 0.317046 0.085 Uiso 1 1 calc R U . A 1
C9 C -0.1877(7) 0.0248(4) 0.1977(3) 0.0769(13) Uani 1 1 d . . . A 1
H9A H -0.151591 -0.047677 0.194616 0.092 Uiso 1 1 calc R U . A 1
H9B H -0.338714 0.029326 0.207352 0.092 Uiso 1 1 calc R U . A 1
C10 C -0.1646(8) 0.0548(4) 0.1203(3) 0.0818(14) Uani 1 1 d . . . A 1
H10A H -0.190414 0.127766 0.123548 0.123 Uiso 1 1 calc R U . A 1
H10B H -0.268083 0.014106 0.079818 0.123 Uiso 1 1 calc R U . A 1
H10C H -0.020211 0.042325 0.106780 0.123 Uiso 1 1 calc R U . A 1
C11 C 0.4580(4) 0.41318(18) 0.61866(12) 0.0272(4) Uani 1 1 d . . . A 1
C12 C 0.3921(4) 0.43326(19) 0.68102(12) 0.0282(5) Uani 1 1 d . . . A 1
C13 C 0.3053(4) 0.45437(17) 0.75475(11) 0.0243(4) Uani 1 1 d . . . A 1
C14 C 0.1020(4) 0.4886(2) 0.75972(11) 0.0317(5) Uani 1 1 d . . . A 1
H14 H 0.017285 0.500696 0.714170 0.038 Uiso 1 1 calc R U . A 1
C15 C 0.0237(4) 0.50494(19) 0.83189(11) 0.0283(5) Uani 1 1 d . . . A 1
H15 H -0.115266 0.529244 0.834925 0.034 Uiso 1 1 calc R U . A 1
N3 N 0.1367(3) 0.48776(14) 0.89799(9) 0.0212(3) Uani 1 1 d . . . A 1
C16 C 0.3325(3) 0.45569(19) 0.89305(11) 0.0269(4) Uani 1 1 d . . . A 1
H16 H 0.414111 0.444775 0.939619 0.032 Uiso 1 1 calc R U . A 1
C17 C 0.4234(4) 0.4374(2) 0.82316(11) 0.0281(5) Uani 1 1 d . . . A 1
H17 H 0.563349 0.413718 0.821966 0.034 Uiso 1 1 calc R U . A 1
O3 O -0.2129(3) 0.36228(13) 0.93763(9) 0.0299(3) Uani 1 1 d . . . A 1
C18 C -0.1644(4) 0.27371(19) 0.93921(14) 0.0327(5) Uani 1 1 d . . . A 1
C19 C 0.0121(5) 0.2386(2) 0.98109(17) 0.0381(6) Uani 1 1 d . . . A 1
H19 H 0.022402 0.166738 0.977925 0.046 Uiso 1 1 calc R U . A 1
C20 C 0.1718(4) 0.30341(19) 1.02678(12) 0.0286(4) Uani 1 1 d . . . A 1
O4 O 0.1961(3) 0.39984(13) 1.03754(8) 0.0268(3) Uani 1 1 d . . . A 1
C21 C -0.3185(6) 0.1923(2) 0.8860(2) 0.0542(8) Uani 1 1 d . . . A 1
F1 F -0.2785(6) 0.1861(2) 0.81172(15) 0.1001(10) Uani 1 1 d . . . A 1
F2 F -0.5186(4) 0.21596(18) 0.88815(17) 0.0773(8) Uani 1 1 d . . . A 1
F3 F -0.3020(4) 0.09915(16) 0.90244(19) 0.0903(10) Uani 1 1 d . . . A 1
C22 C 0.3449(5) 0.2562(2) 1.07486(17) 0.0424(6) Uani 1 1 d . . . A 1
F4 F 0.3404(4) 0.15471(16) 1.05883(17) 0.0745(7) Uani 1 1 d . . . A 1
F5 F 0.3229(4) 0.2818(2) 1.15030(12) 0.0792(8) Uani 1 1 d . . . A 1
F6 F 0.5376(3) 0.29101(17) 1.06568(14) 0.0593(5) Uani 1 1 d . . . A 1
Cl1 Cl -0.1082(3) 0.16768(11) 0.50285(10) 0.1004(4) Uani 1 1 d D . . B 1
C23 C -0.0721(19) 0.1591(17) 0.5998(6) 0.309(12) Uani 1 1 d D . . B 1
H23A H -0.153820 0.214217 0.626853 0.371 Uiso 1 1 calc R U . B 1
H23B H -0.145963 0.093647 0.603740 0.371 Uiso 1 1 calc R U . B 1
C24 C 0.1220(16) 0.1630(8) 0.6457(6) 0.175(4) Uani 1 1 d D . . B 1
H24A H 0.103632 0.122475 0.687256 0.209 Uiso 1 1 calc R U . B 1
H24B H 0.154641 0.235055 0.672151 0.209 Uiso 1 1 calc R U . B 1
Cl2 Cl 0.3444(5) 0.1205(2) 0.6010(2) 0.1917(14) Uani 1 1 d D . . B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.9945(17) 2_567 ?
Cu1 O4 1.9945(17) . ?
Cu1 N3 2.0422(15) . ?
Cu1 N3 2.0422(15) 2_567 ?
Cu1 O3 2.2706(16) 2_567 ?
Cu1 O3 2.2706(16) . ?
C1 C4 1.360(3) . ?
C1 C11 1.427(3) . ?
C1 C2 1.446(3) . ?
C2 O1 1.234(3) . ?
C2 N2 1.376(2) . ?
N2 C3 1.377(3) . ?
N2 H2 0.8800 . ?
C3 O2 1.210(2) . ?
C3 N1 1.387(3) . ?
N1 C4 1.360(3) . ?
N1 C5 1.476(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.521(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.510(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.538(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.492(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.195(3) . ?
C12 C13 1.437(3) . ?
C13 C14 1.384(3) . ?
C13 C17 1.394(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 N3 1.347(3) . ?
C15 H15 0.9500 . ?
N3 C16 1.329(3) . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O3 C18 1.229(3) . ?
C18 C19 1.406(4) . ?
C18 C21 1.536(4) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 O4 1.262(3) . ?
C20 C22 1.526(4) . ?
C21 F2 1.317(4) . ?
C21 F3 1.323(4) . ?
C21 F1 1.334(5) . ?
C22 F5 1.321(4) . ?
C22 F4 1.325(4) . ?
C22 F6 1.326(4) . ?
Cl1 C23 1.704(7) . ?
C23 C24 1.385(12) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 Cl2 1.742(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O4 180.0 2_567 . ?
O4 Cu1 N3 89.24(7) 2_567 . ?
O4 Cu1 N3 90.76(7) . . ?
O4 Cu1 N3 90.76(7) 2_567 2_567 ?
O4 Cu1 N3 89.24(7) . 2_567 ?
N3 Cu1 N3 180.0 . 2_567 ?
O4 Cu1 O3 86.70(7) 2_567 2_567 ?
O4 Cu1 O3 93.30(7) . 2_567 ?
N3 Cu1 O3 94.22(6) . 2_567 ?
N3 Cu1 O3 85.78(6) 2_567 2_567 ?
O4 Cu1 O3 93.30(7) 2_567 . ?
O4 Cu1 O3 86.70(7) . . ?
N3 Cu1 O3 85.78(6) . . ?
N3 Cu1 O3 94.22(6) 2_567 . ?
O3 Cu1 O3 180.0 2_567 . ?
C4 C1 C11 121.2(2) . . ?
C4 C1 C2 118.43(17) . . ?
C11 C1 C2 120.28(19) . . ?
O1 C2 N2 120.56(19) . . ?
O1 C2 C1 124.74(18) . . ?
N2 C2 C1 114.68(18) . . ?
C2 N2 C3 127.48(19) . . ?
C2 N2 H2 116.3 . . ?
C3 N2 H2 116.3 . . ?
O2 C3 N2 122.3(2) . . ?
O2 C3 N1 123.0(2) . . ?
N2 C3 N1 114.71(17) . . ?
C4 N1 C3 121.20(19) . . ?
C4 N1 C5 119.7(2) . . ?
C3 N1 C5 119.07(19) . . ?
N1 C4 C1 123.3(2) . . ?
N1 C4 H4 118.3 . . ?
C1 C4 H4 118.3 . . ?
N1 C5 C6 111.6(3) . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 111.6(3) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 115.0(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 114.4(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 114.9(4) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
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 . . ?
C12 C11 C1 178.1(3) . . ?
C11 C12 C13 177.6(2) . . ?
C14 C13 C17 118.32(18) . . ?
C14 C13 C12 121.52(19) . . ?
C17 C13 C12 120.1(2) . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
N3 C15 C14 122.6(2) . . ?
N3 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C16 N3 C15 117.94(17) . . ?
C16 N3 Cu1 121.54(13) . . ?
C15 N3 Cu1 120.34(15) . . ?
N3 C16 C17 123.21(19) . . ?
N3 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C13 118.7(2) . . ?
C16 C17 H17 120.7 . . ?
C13 C17 H17 120.7 . . ?
C18 O3 Cu1 122.41(16) . . ?
O3 C18 C19 128.9(2) . . ?
O3 C18 C21 113.9(2) . . ?
C19 C18 C21 117.1(2) . . ?
C20 C19 C18 123.3(2) . . ?
C20 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
O4 C20 C19 129.7(2) . . ?
O4 C20 C22 112.1(2) . . ?
C19 C20 C22 118.2(2) . . ?
C20 O4 Cu1 128.71(16) . . ?
F2 C21 F3 107.7(3) . . ?
F2 C21 F1 106.8(3) . . ?
F3 C21 F1 106.7(3) . . ?
F2 C21 C18 112.1(2) . . ?
F3 C21 C18 114.0(3) . . ?
F1 C21 C18 109.2(3) . . ?
F5 C22 F4 106.4(3) . . ?
F5 C22 F6 106.9(3) . . ?
F4 C22 F6 107.8(3) . . ?
F5 C22 C20 109.5(3) . . ?
F4 C22 C20 114.3(2) . . ?
F6 C22 C20 111.5(2) . . ?
C24 C23 Cl1 126.0(9) . . ?
C24 C23 H23A 105.8 . . ?
Cl1 C23 H23A 105.9 . . ?
C24 C23 H23B 105.8 . . ?
Cl1 C23 H23B 105.8 . . ?
H23A C23 H23B 106.2 . . ?
C23 C24 Cl2 118.9(9) . . ?
C23 C24 H24A 107.6 . . ?
Cl2 C24 H24A 107.6 . . ?
C23 C24 H24B 107.5 . . ?
Cl2 C24 H24B 107.6 . . ?
H24A C24 H24B 107.0 . . ?

_refine_diff_density_max         0.879
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_e4696a_a
_database_code_depnum_ccdc_archive 'CCDC 2040835'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H52 Cu2 N8 O10, 2(H2 O)'
_chemical_formula_sum            'C42 H56 Cu2 N8 O12'
_chemical_formula_weight         992.02

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'

_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                   8.3684(4)
_cell_length_b                   11.1355(6)
_cell_length_c                   12.3497(7)
_cell_angle_alpha                90.561(2)
_cell_angle_beta                 92.993(2)
_cell_angle_gamma                92.055(2)
_cell_volume                     1148.44(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8200
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.995
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52487
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         30.225
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6261
_reflns_number_gt                5700
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-97 '
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0322P)²+0.6208P] 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         6261
_refine_ls_number_parameters     298
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.043
_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 0.44469(2) 0.88806(2) 0.51481(2) 0.01814(5) Uani 1 1 d . . . . .
N1 N -0.18705(14) 0.20375(10) 0.16001(9) 0.0212(2) Uani 1 1 d . . . . .
C1 C -0.17989(17) 0.26908(12) 0.06324(11) 0.0226(3) Uani 1 1 d . . . . .
O1 O -0.25297(14) 0.22758(10) -0.01901(8) 0.0316(2) Uani 1 1 d . . . . .
N2 N -0.09355(16) 0.37385(10) 0.06462(9) 0.0242(2) Uani 1 1 d . . . . .
C2 C -0.01419(17) 0.41421(12) 0.15489(11) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.06766(17) 0.51794(11) 0.15062(10) 0.0295(3) Uani 1 1 d . . . . .
H3A H 0.0685 0.5579 0.0895 0.035 Uiso 1 1 calc R U . . .
H3B H 0.1213 0.5469 0.2089 0.035 Uiso 1 1 calc R U . . .
C3 C -0.01621(17) 0.34760(12) 0.25508(11) 0.0210(3) Uani 1 1 d . . . . .
C4 C -0.10539(17) 0.24280(12) 0.25183(10) 0.0210(3) Uani 1 1 d . . . . .
H4 H -0.1104 0.1960 0.3156 0.025 Uiso 1 1 calc R U . . .
C5 C -0.28164(17) 0.08996(12) 0.15757(11) 0.0228(3) Uani 1 1 d . . . . .
H5A H -0.3814 0.0997 0.1123 0.027 Uiso 1 1 calc R U . . .
H5B H -0.3121 0.0709 0.2320 0.027 Uiso 1 1 calc R U . . .
C6 C -0.19204(18) -0.01388(13) 0.11314(13) 0.0279(3) Uani 1 1 d . . . . .
H6A H -0.0978 -0.0291 0.1623 0.033 Uiso 1 1 calc R U . . .
H6B H -0.1529 0.0077 0.0414 0.033 Uiso 1 1 calc R U . . .
C7 C -0.29821(19) -0.12781(13) 0.10178(14) 0.0302(3) Uani 1 1 d . . . . .
H7A H -0.3873 -0.1146 0.0477 0.036 Uiso 1 1 calc R U . . .
H7B H -0.3451 -0.1452 0.1722 0.036 Uiso 1 1 calc R U . . .
C8 C -0.2056(2) -0.23588(15) 0.06650(18) 0.0428(4) Uani 1 1 d . . . . .
H8A H -0.1469 -0.2141 0.0015 0.051 Uiso 1 1 calc R U . . .
H8B H -0.1254 -0.2549 0.1250 0.051 Uiso 1 1 calc R U . . .
C9 C -0.3114(3) -0.34795(15) 0.04041(16) 0.0439(4) Uani 1 1 d . . . . .
H9A H -0.2442 -0.4193 0.0435 0.053 Uiso 1 1 calc R U . . .
H9B H -0.3912 -0.3571 0.0965 0.053 Uiso 1 1 calc R U . . .
C10 C -0.3986(3) -0.34405(18) -0.07017(18) 0.0504(5) Uani 1 1 d . . . . .
H10A H -0.4652 -0.2735 -0.0740 0.076 Uiso 1 1 calc R U . . .
H10B H -0.4665 -0.4171 -0.0816 0.076 Uiso 1 1 calc R U . . .
H10C H -0.3203 -0.3391 -0.1264 0.076 Uiso 1 1 calc R U . . .
C11 C 0.07214(18) 0.39472(12) 0.34892(11) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.15203(18) 0.44624(12) 0.41953(11) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.25098(17) 0.51192(12) 0.49944(11) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.27631(17) 0.63565(12) 0.48756(11) 0.0204(3) Uani 1 1 d . . . . .
H14 H 0.2212 0.6739 0.4290 0.025 Uiso 1 1 calc R U . . .
N4 N 0.37412(14) 0.70281(10) 0.55430(9) 0.0198(2) Uani 1 1 d . . . . .
C15 C 0.44817(18) 0.64840(12) 0.63860(11) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.5173 0.6954 0.6870 0.029 Uiso 1 1 calc R U . . .
C16 C 0.42791(19) 0.52690(13) 0.65780(12) 0.0272(3) Uani 1 1 d . . . . .
H16 H 0.4814 0.4919 0.7187 0.033 Uiso 1 1 calc R U . . .
C17 C 0.32905(18) 0.45670(12) 0.58753(11) 0.0248(3) Uani 1 1 d . . . . .
H17 H 0.3145 0.3728 0.5989 0.030 Uiso 1 1 calc R U . . .
O2 O 0.64922(13) 0.84431(9) 0.45553(9) 0.0301(2) Uani 1 1 d . . . . .
O3 O 0.74570(12) 1.03186(9) 0.43417(9) 0.0254(2) Uani 1 1 d . . . . .
C18 C 0.75713(17) 0.91890(12) 0.43232(11) 0.0223(3) Uani 1 1 d . . . . .
C19 C 0.9135(2) 0.86955(16) 0.40029(15) 0.0362(4) Uani 1 1 d . . . . .
H19A H 0.9657 0.8306 0.4628 0.054 Uiso 1 1 calc R U . . .
H19B H 0.9833 0.9353 0.3759 0.054 Uiso 1 1 calc R U . . .
H19C H 0.8930 0.8106 0.3413 0.054 Uiso 1 1 calc R U . . .
O4 O 0.56051(13) 0.91618(9) 0.65629(8) 0.0267(2) Uani 1 1 d . . . . .
O5 O 0.65196(14) 1.10487(9) 0.63426(8) 0.0288(2) Uani 1 1 d . . . . .
C20 C 0.63895(16) 1.00919(13) 0.68792(11) 0.0219(3) Uani 1 1 d . . . . .
C21 C 0.7236(2) 1.00589(16) 0.79826(12) 0.0337(4) Uani 1 1 d . . . . .
H21A H 0.6495 1.0273 0.8536 0.050 Uiso 1 1 calc R U . . .
H21B H 0.8152 1.0634 0.8013 0.050 Uiso 1 1 calc R U . . .
H21C H 0.7614 0.9248 0.8118 0.050 Uiso 1 1 calc R U . . .
O6 O 0.67100(19) 0.32128(11) 0.77533(10) 0.0421(3) Uani 1 1 d D . . . .
H6C H 0.699(3) 0.305(2) 0.8415(14) 0.082 Uiso 1 1 d D U . . .
H6D H 0.664(3) 0.263(2) 0.7300(18) 0.082 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.9701(10) . ?
Cu1 O2 1.9714(11) . ?
Cu1 O5 1.9751(10) 2_676 ?
Cu1 O3 1.9815(10) 2_676 ?
Cu1 N4 2.1919(11) . ?
Cu1 Cu1 2.6633(3) 2_676 ?
N1 C4 1.3529(16) . ?
N1 C1 1.4080(18) . ?
N1 C5 1.4689(17) . ?
C1 O1 1.2349(16) . ?
C1 N2 1.3496(18) . ?
N2 C2 1.3332(17) . ?
C2 N3 1.3245(18) . ?
C2 C3 1.4493(19) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C3 C4 1.3616(19) . ?
C3 C11 1.4268(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.514(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.527(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.1993(19) . ?
C12 C13 1.4324(18) . ?
C13 C14 1.3969(18) . ?
C13 C17 1.3985(19) . ?
C14 N4 1.3349(16) . ?
C14 H14 0.9500 . ?
N4 C15 1.3443(17) . ?
C15 C16 1.3819(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3834(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O2 C18 1.2512(19) . ?
O3 C18 1.2650(17) . ?
O3 Cu1 1.9814(10) 2_676 ?
C18 C19 1.507(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O4 C20 1.2541(17) . ?
O5 C20 1.2647(18) . ?
O5 Cu1 1.9751(10) 2_676 ?
C20 C21 1.5042(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O6 H6C 0.860(16) . ?
O6 H6D 0.854(16) . ?

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
O4 Cu1 O2 88.28(5) . . ?
O4 Cu1 O5 167.46(4) . 2_676 ?
O2 Cu1 O5 89.54(5) . 2_676 ?
O4 Cu1 O3 91.18(4) . 2_676 ?
O2 Cu1 O3 167.46(4) . 2_676 ?
O5 Cu1 O3 88.27(5) 2_676 2_676 ?
O4 Cu1 N4 92.98(4) . . ?
O2 Cu1 N4 94.31(4) . . ?
O5 Cu1 N4 99.50(4) 2_676 . ?
O3 Cu1 N4 98.23(4) 2_676 . ?
O4 Cu1 Cu1 80.85(3) . 2_676 ?
O2 Cu1 Cu1 83.60(3) . 2_676 ?
O5 Cu1 Cu1 86.63(3) 2_676 2_676 ?
O3 Cu1 Cu1 83.94(3) 2_676 2_676 ?
N4 Cu1 Cu1 173.53(3) . 2_676 ?
C4 N1 C1 120.98(11) . . ?
C4 N1 C5 120.90(11) . . ?
C1 N1 C5 118.09(11) . . ?
O1 C1 N2 123.11(13) . . ?
O1 C1 N1 118.32(12) . . ?
N2 C1 N1 118.58(11) . . ?
C2 N2 C1 121.06(12) . . ?
N3 C2 N2 117.90(13) . . ?
N3 C2 C3 120.46(12) . . ?
N2 C2 C3 121.64(12) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 C3 C11 124.68(13) . . ?
C4 C3 C2 116.16(11) . . ?
C11 C3 C2 119.16(12) . . ?
N1 C4 C3 121.56(12) . . ?
N1 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N1 C5 C6 112.77(12) . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 111.53(13) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.08(14) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 113.68(16) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 113.13(17) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
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 . . ?
C12 C11 C3 171.63(15) . . ?
C11 C12 C13 176.88(16) . . ?
C14 C13 C17 118.05(12) . . ?
C14 C13 C12 119.16(12) . . ?
C17 C13 C12 122.74(12) . . ?
N4 C14 C13 123.30(12) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C14 N4 C15 117.89(11) . . ?
C14 N4 Cu1 121.53(9) . . ?
C15 N4 Cu1 119.81(9) . . ?
N4 C15 C16 122.74(12) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 119.46(13) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C13 118.53(13) . . ?
C16 C17 H17 120.7 . . ?
C13 C17 H17 120.7 . . ?
C18 O2 Cu1 124.02(9) . . ?
C18 O3 Cu1 122.87(10) . 2_676 ?
O2 C18 O3 125.31(13) . . ?
O2 C18 C19 117.03(13) . . ?
O3 C18 C19 117.66(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O4 Cu1 127.42(9) . . ?
C20 O5 Cu1 119.99(9) . 2_676 ?
O4 C20 O5 125.02(12) . . ?
O4 C20 C21 117.10(13) . . ?
O5 C20 C21 117.88(12) . . ?
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 . . ?
H6C O6 H6D 117(2) . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4590a_a
_database_code_depnum_ccdc_archive 'CCDC 2040830'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C36 H40 Cd N14 O6, 0.5(C2 H4 Cl2), C H4 O [+ solvent]'
_chemical_formula_sum            'C38 H46 Cd Cl N14 O7[+ solvent]'
_chemical_formula_weight         958.74

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   15.2454(9)
_cell_length_b                   11.9330(11)
_cell_length_c                   25.571(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.001(3)
_cell_angle_gamma                90
_cell_volume                     4651.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3128
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.38


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             1972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            98162
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.567
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             10065
_reflns_number_gt                8061
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
Because of the disorder of the chains we let the atoms isotropic
and we didn't put the hydrogens
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1810P)²+38.2240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10065
_refine_ls_number_parameters     521
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0929
_refine_ls_wR_factor_ref         0.2953
_refine_ls_wR_factor_gt          0.2748
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.041

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
Cd1 Cd 0.50302(3) 0.57921(3) 0.75922(2) 0.0271(2) Uani 1 1 d . . . . .
C1 C 0.8192(5) 0.0825(5) 0.8072(3) 0.0306(15) Uani 1 1 d . . . . .
N1 N 0.7698(4) -0.0083(5) 0.8231(2) 0.0309(12) Uani 1 1 d . . . . .
C2 C 0.8112(3) -0.0936(3) 0.80679(18) 0.0325(15) Uani 1 1 d G . . . .
N2 N 0.7910(2) -0.2068(3) 0.81110(18) 0.0326(13) Uani 1 1 d G . . . .
C3 C 0.8444(3) -0.2866(2) 0.78809(18) 0.0366(16) Uani 1 1 d G . . . .
H3 H 0.8306 -0.3639 0.7910 0.044 Uiso 1 1 calc R U . . .
N3 N 0.9180(2) -0.2532(2) 0.76077(17) 0.0272(12) Uani 1 1 d G . . . .
C4 C 0.9382(2) -0.1400(3) 0.75647(17) 0.0270(13) Uani 1 1 d G . . . .
C5 C 0.8848(3) -0.0602(2) 0.77947(19) 0.0287(14) Uani 1 1 d G . . . .
N4 N 0.8885(4) 0.0543(4) 0.7807(2) 0.0301(12) Uani 1 1 d . . . . .
N5 N 1.0062(4) -0.1118(4) 0.7265(3) 0.0299(13) Uani 1 1 d . . . . .
H5A H 1.0181 -0.0407 0.7208 0.036 Uiso 1 1 calc R U . . .
H5B H 1.0387 -0.1643 0.7124 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6888(5) -0.0084(6) 0.8530(3) 0.0393(17) Uani 1 1 d D . . . .
H6A H 0.6483 -0.0655 0.8382 0.047 Uiso 1 1 calc R U . . .
H6B H 0.6601 0.0657 0.8495 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7058(8) -0.0335(15) 0.9110(4) 0.091(4) Uani 1 1 d D . . . .
C8 C 0.6165(13) -0.020(3) 0.9370(7) 0.091(4) Uani 0.480(9) 1 d D . P A 1
C9 C 0.6317(14) -0.012(3) 0.9975(7) 0.091(4) Uani 0.480(9) 1 d D . P A 1
C10 C 0.5400(14) -0.024(3) 1.0252(8) 0.091(4) Uani 0.480(9) 1 d D . P A 1
C11 C 0.5583(16) -0.036(3) 1.0849(7) 0.091(4) Uani 0.480(9) 1 d D . P A 1
C8A C 0.7411(13) 0.0661(16) 0.9400(9) 0.091(4) Uani 0.520(9) 1 d D . P A 2
C9A C 0.6736(15) 0.158(2) 0.9463(9) 0.091(4) Uani 0.520(9) 1 d D . P A 2
C10A C 0.6037(14) 0.240(2) 0.9355(8) 0.091(4) Uani 0.520(9) 1 d D . P A 2
C11A C 0.5373(14) 0.283(3) 0.8962(8) 0.091(4) Uani 0.520(9) 1 d D . P A 2
C12 C 0.7922(5) 0.1949(6) 0.8190(3) 0.0334(15) Uani 1 1 d . . . . .
C13 C 0.7658(5) 0.2857(5) 0.8300(3) 0.0306(14) Uani 1 1 d . . . . .
C14 C 0.7293(4) 0.3937(5) 0.8392(3) 0.0272(13) Uani 1 1 d . . . . .
C15 C 0.6652(5) 0.4334(5) 0.8050(3) 0.0300(14) Uani 1 1 d . . . . .
H15 H 0.6482 0.3877 0.7762 0.036 Uiso 1 1 calc R U . . .
N6 N 0.6256(4) 0.5331(4) 0.8105(2) 0.0273(12) Uani 1 1 d . . . . .
C16 C 0.6534(5) 0.5986(5) 0.8496(3) 0.0317(15) Uani 1 1 d . . . . .
H16 H 0.6276 0.6707 0.8530 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7176(5) 0.5671(5) 0.8853(3) 0.0328(15) Uani 1 1 d . . . . .
H17 H 0.7355 0.6168 0.9125 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7559(5) 0.4616(6) 0.8810(3) 0.0329(15) Uani 1 1 d . . . . .
H18 H 0.7988 0.4367 0.9057 0.039 Uiso 1 1 calc R U . . .
C19 C 0.1873(5) 1.0753(5) 0.6908(3) 0.0358(17) Uani 1 1 d . . . . .
N7 N 0.2388(5) 1.1652(5) 0.6768(3) 0.0478(18) Uani 1 1 d . . . . .
C20 C 0.1919(5) 1.2571(6) 0.6903(4) 0.0440(19) Uani 1 1 d . . . . .
N8 N 0.2159(5) 1.3657(5) 0.6846(4) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.1547(6) 1.4349(6) 0.7021(4) 0.049(2) Uani 1 1 d . . . . .
H21 H 0.1656 1.5125 0.6971 0.059 Uiso 1 1 calc R U . . .
N9 N 0.0795(4) 1.4097(4) 0.7258(3) 0.0324(13) Uani 1 1 d . . . . .
C22 C 0.0571(4) 1.2998(5) 0.7333(3) 0.0271(14) Uani 1 1 d . . . . .
C23 C 0.1154(4) 1.2187(5) 0.7124(3) 0.0303(14) Uani 1 1 d . . . . .
N10 N 0.1131(4) 1.1041(4) 0.7131(2) 0.0308(13) Uani 1 1 d . . . . .
N11 N -0.0152(4) 1.2725(5) 0.7608(3) 0.0387(15) Uani 1 1 d . . . . .
H11G H -0.0482 1.3256 0.7740 0.046 Uiso 1 1 calc R U . . .
H11H H -0.0291 1.2016 0.7654 0.046 Uiso 1 1 calc R U . . .
C24 C 0.3297(6) 1.1632(7) 0.6560(4) 0.055(2) Uani 1 1 d D . . . .
H24A H 0.3626 1.0988 0.6709 0.066 Uiso 1 1 calc R U . . .
H24B H 0.3610 1.2329 0.6658 0.066 Uiso 1 1 calc R U . . .
C25 C 0.3230(7) 1.1529(9) 0.5979(4) 0.069(3) Uani 1 1 d D . . . .
H25A H 0.2919 1.2185 0.5829 0.083 Uiso 1 1 calc R U . . .
H25B H 0.2904 1.0842 0.5881 0.083 Uiso 1 1 calc R U . . .
C26 C 0.4211(9) 1.1472(12) 0.5768(7) 0.113(6) Uani 1 1 d D . . . .
C27 C 0.452(2) 1.028(3) 0.591(2) 0.113(6) Uani 0.55(2) 1 d D . P B 1
C28 C 0.5437(18) 0.988(3) 0.578(2) 0.113(6) Uani 0.55(2) 1 d D . P B 1
C29 C 0.550(3) 0.859(3) 0.584(2) 0.113(6) Uani 0.55(2) 1 d D . P B 1
C27A C 0.454(2) 1.049(3) 0.6112(10) 0.113(6) Uani 0.45(2) 1 d D . P B 2
C28A C 0.439(2) 0.939(2) 0.581(2) 0.113(6) Uani 0.45(2) 1 d D . P B 2
C29A C 0.512(3) 0.853(3) 0.593(2) 0.113(6) Uani 0.45(2) 1 d D . P B 2
C30 C 0.2170(5) 0.9621(6) 0.6825(3) 0.0365(16) Uani 1 1 d . . . . .
C31 C 0.2466(5) 0.8719(6) 0.6758(3) 0.0326(15) Uani 1 1 d . . . . .
C32 C 0.2839(4) 0.7630(5) 0.6694(3) 0.0287(14) Uani 1 1 d . . . . .
C33 C 0.3465(4) 0.7273(5) 0.7054(3) 0.0291(14) Uani 1 1 d . . . . .
H33 H 0.3637 0.7770 0.7327 0.035 Uiso 1 1 calc R U . . .
N12 N 0.3843(4) 0.6253(4) 0.7037(3) 0.0304(12) Uani 1 1 d . . . . .
C34 C 0.3582(5) 0.5560(5) 0.6650(3) 0.0343(16) Uani 1 1 d . . . . .
H34 H 0.3831 0.4831 0.6637 0.041 Uiso 1 1 calc R U . . .
C35 C 0.2977(5) 0.5850(6) 0.6274(3) 0.0355(16) Uani 1 1 d . . . . .
H35 H 0.2819 0.5339 0.6003 0.043 Uiso 1 1 calc R U . . .
C36 C 0.2598(5) 0.6904(6) 0.6294(3) 0.0330(15) Uani 1 1 d . . . . .
H36 H 0.2177 0.7127 0.6036 0.040 Uiso 1 1 calc R U . . .
O1 O 0.5728(3) 0.4750(4) 0.69581(19) 0.0311(10) Uani 1 1 d . . . . .
O2 O 0.5383(5) 0.3992(6) 0.6217(3) 0.0568(16) Uani 1 1 d . . . . .
O3 O 0.5491(5) 0.5803(5) 0.6281(2) 0.0505(15) Uani 1 1 d . . . . .
N13 N 0.5525(4) 0.4855(5) 0.6468(2) 0.0334(13) Uani 1 1 d . . . . .
O4 O 0.4367(4) 0.6842(4) 0.8227(2) 0.0377(12) Uani 1 1 d . . . . .
O5 O 0.4547(7) 0.7446(10) 0.9017(4) 0.111(4) Uani 1 1 d . . . . .
O6 O 0.4568(7) 0.5688(8) 0.8860(4) 0.092(3) Uani 1 1 d . . . . .
N14 N 0.4503(5) 0.6642(8) 0.8718(3) 0.0525(19) Uani 1 1 d . . . . .
C37 C 0.4882(11) 0.4361(16) 0.4972(6) 0.154(10) Uani 1 1 d D . . . .
H37A H 0.5192 0.3910 0.5242 0.185 Uiso 1 1 calc R U . . .
H37B H 0.5038 0.4075 0.4622 0.185 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3709(3) 0.4319(5) 0.50607(14) 0.1126(15) Uani 1 1 d D . . . .
O8 O 0.6456(9) 0.7233(17) 0.0077(6) 0.168(8) Uani 1 1 d D . . . .
H8 H 0.6138 0.7552 0.0297 0.252 Uiso 1 1 calc R U . . .
C38 C 0.6462(14) 0.6063(18) 0.0173(9) 0.131(8) Uani 1 1 d D . . . .
H38A H 0.6901 0.5890 0.0446 0.196 Uiso 1 1 calc R U . . .
H38B H 0.6609 0.5665 -0.0149 0.196 Uiso 1 1 calc R U . . .
H38C H 0.5881 0.5826 0.0288 0.196 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O4 2.299(5) . ?
Cd1 O1 2.317(5) . ?
Cd1 N6 2.330(6) . ?
Cd1 N12 2.346(6) . ?
Cd1 N3 2.394(10) 2_666 ?
Cd1 N9 2.416(5) 2_546 ?
C1 N4 1.309(10) . ?
C1 N1 1.384(9) . ?
C1 C12 1.435(9) . ?
N1 C2 1.273(6) . ?
N1 C6 1.462(10) . ?
C2 N2 1.3900 . ?
C2 C5 1.3900 . ?
N2 C3 1.3900 . ?
C3 N3 1.3900 . ?
C3 H3 0.9500 . ?
N3 C4 1.3900 . ?
N3 Cd1 2.394(3) 2_646 ?
C4 N5 1.344(6) . ?
C4 C5 1.3900 . ?
C5 N4 1.369(6) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C6 C7 1.532(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8A 1.496(10) . ?
C7 C8 1.534(16) . ?
C8 C9 1.564(17) . ?
C9 C10 1.584(17) . ?
C10 C11 1.554(18) . ?
C10 C10 1.85(5) 3_657 ?
C8A C9A 1.511(10) . ?
C9A C10A 1.476(10) . ?
C10A C11A 1.503(7) . ?
C12 C13 1.192(9) . ?
C13 C14 1.425(8) . ?
C14 C15 1.384(10) . ?
C14 C18 1.394(10) . ?
C15 N6 1.341(8) . ?
C15 H15 0.9500 . ?
N6 C16 1.332(9) . ?
C16 C17 1.380(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N10 1.321(10) . ?
C19 N7 1.380(10) . ?
C19 C30 1.441(9) . ?
N7 C20 1.357(9) . ?
N7 C24 1.493(12) . ?
C20 N8 1.355(9) . ?
C20 C23 1.384(11) . ?
N8 C21 1.329(10) . ?
C21 N9 1.340(10) . ?
C21 H21 0.9500 . ?
N9 C22 1.369(8) . ?
N9 Cd1 2.416(5) 2_566 ?
C22 N11 1.359(9) . ?
C22 C23 1.423(9) . ?
C23 N10 1.369(8) . ?
N11 H11G 0.8800 . ?
N11 H11H 0.8800 . ?
C24 C25 1.491(12) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.600(13) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.539(10) . ?
C26 C27A 1.541(10) . ?
C27 C28 1.516(10) . ?
C28 C29 1.548(10) . ?
C27A C28A 1.543(10) . ?
C28A C29A 1.536(10) . ?
C30 C31 1.181(10) . ?
C31 C32 1.429(9) . ?
C32 C36 1.386(10) . ?
C32 C33 1.382(10) . ?
C33 N12 1.348(8) . ?
C33 H33 0.9500 . ?
N12 C34 1.345(10) . ?
C34 C35 1.365(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(9) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O1 N13 1.291(8) . ?
O2 N13 1.230(8) . ?
O3 N13 1.229(8) . ?
O4 N14 1.289(9) . ?
O5 N14 1.229(12) . ?
O6 N14 1.198(11) . ?
C37 C37 1.57(4) 3_666 ?
C37 Cl1 1.808(17) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
O8 C38 1.417(9) . ?
O8 H8 0.9106 . ?
C38 H38A 0.9801 . ?
C38 H38B 0.9801 . ?
C38 H38C 0.9801 . ?

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
O4 Cd1 O1 178.74(19) . . ?
O4 Cd1 N6 95.1(2) . . ?
O1 Cd1 N6 83.88(18) . . ?
O4 Cd1 N12 87.5(2) . . ?
O1 Cd1 N12 93.51(19) . . ?
N6 Cd1 N12 177.0(2) . . ?
O4 Cd1 N3 85.7(6) . 2_666 ?
O1 Cd1 N3 93.4(6) . 2_666 ?
N6 Cd1 N3 85.2(8) . 2_666 ?
N12 Cd1 N3 93.5(8) . 2_666 ?
O4 Cd1 N9 96.2(2) . 2_546 ?
O1 Cd1 N9 84.71(19) . 2_546 ?
N6 Cd1 N9 97.3(2) . 2_546 ?
N12 Cd1 N9 83.9(2) . 2_546 ?
N3 Cd1 N9 176.7(8) 2_666 2_546 ?
N4 C1 N1 113.5(6) . . ?
N4 C1 C12 125.7(6) . . ?
N1 C1 C12 120.7(6) . . ?
C2 N1 C1 104.7(5) . . ?
C2 N1 C6 126.8(5) . . ?
C1 N1 C6 128.5(6) . . ?
N1 C2 N2 129.7(4) . . ?
N1 C2 C5 110.2(4) . . ?
N2 C2 C5 120.0 . . ?
C2 N2 C3 120.0 . . ?
N3 C3 N2 120.0 . . ?
N3 C3 H3 120.0 . . ?
N2 C3 H3 120.0 . . ?
C3 N3 C4 120.0 . . ?
C3 N3 Cd1 106.35(17) . 2_646 ?
C4 N3 Cd1 132.97(17) . 2_646 ?
N5 C4 C5 122.2(3) . . ?
N5 C4 N3 117.6(3) . . ?
C5 C4 N3 120.0 . . ?
N4 C5 C4 132.1(3) . . ?
N4 C5 C2 107.9(3) . . ?
C4 C5 C2 120.0 . . ?
C1 N4 C5 103.6(5) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N1 C6 C7 112.1(7) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8A C7 C6 112.2(14) . . ?
C6 C7 C8 105.1(11) . . ?
C7 C8 C9 108.5(15) . . ?
C8 C9 C10 108.7(17) . . ?
C11 C10 C9 107.7(13) . . ?
C11 C10 C10 145(2) . 3_657 ?
C9 C10 C10 103.7(19) . 3_657 ?
C7 C8A C9A 113(2) . . ?
C10A C9A C8A 163(2) . . ?
C9A C10A C11A 146(2) . . ?
C13 C12 C1 176.3(8) . . ?
C12 C13 C14 174.9(8) . . ?
C15 C14 C18 118.5(6) . . ?
C15 C14 C13 118.6(6) . . ?
C18 C14 C13 122.9(6) . . ?
N6 C15 C14 123.5(6) . . ?
N6 C15 H15 118.3 . . ?
C14 C15 H15 118.2 . . ?
C16 N6 C15 117.4(6) . . ?
C16 N6 Cd1 121.6(4) . . ?
C15 N6 Cd1 120.6(4) . . ?
N6 C16 C17 123.3(6) . . ?
N6 C16 H16 118.4 . . ?
C17 C16 H16 118.3 . . ?
C16 C17 C18 119.2(6) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C14 118.0(7) . . ?
C17 C18 H18 121.0 . . ?
C14 C18 H18 121.0 . . ?
N10 C19 N7 113.9(6) . . ?
N10 C19 C30 125.5(7) . . ?
N7 C19 C30 120.6(7) . . ?
C20 N7 C19 105.0(6) . . ?
C20 N7 C24 126.9(7) . . ?
C19 N7 C24 128.0(6) . . ?
N8 C20 N7 127.0(7) . . ?
N8 C20 C23 126.2(7) . . ?
N7 C20 C23 106.7(6) . . ?
C21 N8 C20 111.5(7) . . ?
N8 C21 N9 128.6(7) . . ?
N8 C21 H21 115.7 . . ?
N9 C21 H21 115.7 . . ?
C21 N9 C22 119.6(6) . . ?
C21 N9 Cd1 109.6(4) . 2_566 ?
C22 N9 Cd1 130.4(5) . 2_566 ?
N11 C22 N9 120.5(6) . . ?
N11 C22 C23 123.2(6) . . ?
N9 C22 C23 116.2(6) . . ?
N10 C23 C20 111.0(6) . . ?
N10 C23 C22 131.2(6) . . ?
C20 C23 C22 117.6(6) . . ?
C19 N10 C23 103.5(6) . . ?
C22 N11 H11G 120.0 . . ?
C22 N11 H11H 120.0 . . ?
H11G N11 H11H 120.0 . . ?
N7 C24 C25 108.0(8) . . ?
N7 C24 H24A 110.1 . . ?
C25 C24 H24A 110.1 . . ?
N7 C24 H24B 110.1 . . ?
C25 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C24 C25 C26 107.0(10) . . ?
C24 C25 H25A 110.3 . . ?
C26 C25 H25A 110.4 . . ?
C24 C25 H25B 110.3 . . ?
C26 C25 H25B 110.3 . . ?
H25A C25 H25B 108.5 . . ?
C27 C26 C25 104.4(11) . . ?
C27A C26 C25 97.9(13) . . ?
C28 C27 C26 121.6(15) . . ?
C27 C28 C29 110.4(13) . . ?
C26 C27A C28A 108.1(14) . . ?
C29A C28A C27A 111.4(15) . . ?
C31 C30 C19 175.8(9) . . ?
C30 C31 C32 178.1(9) . . ?
C36 C32 C33 118.1(6) . . ?
C36 C32 C31 123.5(7) . . ?
C33 C32 C31 118.4(6) . . ?
N12 C33 C32 123.2(6) . . ?
N12 C33 H33 118.4 . . ?
C32 C33 H33 118.4 . . ?
C34 N12 C33 117.2(6) . . ?
C34 N12 Cd1 121.1(4) . . ?
C33 N12 Cd1 121.2(5) . . ?
N12 C34 C35 123.4(6) . . ?
N12 C34 H34 118.3 . . ?
C35 C34 H34 118.3 . . ?
C34 C35 C36 118.7(7) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
C32 C36 C35 119.3(7) . . ?
C32 C36 H36 120.3 . . ?
C35 C36 H36 120.4 . . ?
N13 O1 Cd1 121.5(4) . . ?
O3 N13 O2 124.2(7) . . ?
O3 N13 O1 118.3(6) . . ?
O2 N13 O1 117.5(6) . . ?
N14 O4 Cd1 121.4(5) . . ?
O6 N14 O5 123.2(10) . . ?
O6 N14 O4 118.8(9) . . ?
O5 N14 O4 117.9(9) . . ?
C37 C37 Cl1 103.9(14) 3_666 . ?
C37 C37 H37A 111.0 3_666 . ?
Cl1 C37 H37A 111.0 . . ?
C37 C37 H37B 111.0 3_666 . ?
Cl1 C37 H37B 111.0 . . ?
H37A C37 H37B 109.0 . . ?
C38 O8 H8 117.3 . . ?
O8 C38 H38A 110.3 . . ?
O8 C38 H38B 108.9 . . ?
H38A C38 H38B 109.4 . . ?
O8 C38 H38C 109.2 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         1.682
_refine_diff_density_min         -1.679
_refine_diff_density_rms         0.391

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4569a_a
_database_code_depnum_ccdc_archive 'CCDC 2040827'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N6, C2 H4 Cl2'
_chemical_formula_sum            'C20 H24 Cl2 N6'
_chemical_formula_weight         419.35

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'
Cl Cl 0.1484 0.1585 '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                   8.0332(3)
_cell_length_b                   10.5895(5)
_cell_length_c                   13.0038(7)
_cell_angle_alpha                90.712(2)
_cell_angle_beta                 91.103(2)
_cell_angle_gamma                105.311(2)
_cell_volume                     1066.57(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5538
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.14


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.322
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16152
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.567
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_full        25.142
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             4604
_reflns_number_gt                3414
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1396P)²+2.2998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4604
_refine_ls_number_parameters     255
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2925
_refine_ls_wR_factor_gt          0.2653
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
C1 C 0.6598(4) 0.6345(3) 0.5846(2) 0.0321(7) Uani 1 1 d . . . A 4
N1 N 0.6929(4) 0.5693(3) 0.6652(2) 0.0320(6) Uani 1 1 d . . . A 4
C2 C 0.5981(4) 0.6064(3) 0.7423(2) 0.0311(7) Uani 1 1 d . . . A 4
C3 C 0.5744(4) 0.5687(3) 0.8460(2) 0.0315(7) Uani 1 1 d . . . A 4
N2 N 0.4639(4) 0.6182(3) 0.9011(2) 0.0379(7) Uani 1 1 d . . . A 4
C4 C 0.3871(5) 0.7015(4) 0.8553(3) 0.0429(9) Uani 1 1 d . . . A 4
H4 H 0.3116 0.7338 0.8974 0.051 Uiso 1 1 calc R U . A 4
N3 N 0.4012(4) 0.7456(3) 0.7595(2) 0.0411(7) Uani 1 1 d . . . A 4
C6 C 0.5087(5) 0.6929(3) 0.7064(2) 0.0330(7) Uani 1 1 d . . . A 4
N4 N 0.5503(4) 0.7127(3) 0.6053(2) 0.0335(6) Uani 1 1 d . . . A 4
N5 N 0.6514(4) 0.4871(3) 0.8906(2) 0.0384(7) Uani 1 1 d . . . A 4
H5A H 0.6306 0.4656 0.9551 0.046 Uiso 1 1 calc R U . A 4
H5B H 0.7234 0.4542 0.8557 0.046 Uiso 1 1 calc R U . A 4
C7 C 0.7230(5) 0.6274(3) 0.4837(2) 0.0345(7) Uani 1 1 d . . . A 4
C8 C 0.7697(4) 0.6232(3) 0.3974(2) 0.0332(7) Uani 1 1 d . . . A 4
C9 C 0.8253(4) 0.6226(3) 0.2934(2) 0.0305(7) Uani 1 1 d . . . A 4
C10 C 0.9573(5) 0.5664(4) 0.2669(3) 0.0368(8) Uani 1 1 d . . . A 4
H10 H 1.0068 0.5249 0.3192 0.044 Uiso 1 1 calc R U . A 4
N6 N 1.0179(4) 0.5678(3) 0.1723(2) 0.0431(8) Uani 1 1 d . . . A 4
C11 C 0.9462(5) 0.6259(4) 0.0997(3) 0.0457(10) Uani 1 1 d . . . A 4
H11 H 0.9881 0.6273 0.0318 0.055 Uiso 1 1 calc R U . A 4
C12 C 0.8151(5) 0.6838(4) 0.1178(3) 0.0452(9) Uani 1 1 d . . . A 4
H12 H 0.7678 0.7241 0.0638 0.054 Uiso 1 1 calc R U . A 4
C13 C 0.7534(5) 0.6823(4) 0.2164(3) 0.0373(8) Uani 1 1 d . . . A 4
H13 H 0.6630 0.7217 0.2312 0.045 Uiso 1 1 calc R U . A 4
C14 C 0.4898(5) 0.7980(3) 0.5350(3) 0.0363(8) Uani 1 1 d . . . A 4
H14A H 0.5757 0.8262 0.4807 0.044 Uiso 1 1 calc R U . A 4
H14B H 0.4811 0.8774 0.5733 0.044 Uiso 1 1 calc R U . A 4
C15 C 0.3152(5) 0.7323(4) 0.4848(3) 0.0389(8) Uani 1 1 d . . . A 4
H15A H 0.2265 0.7111 0.5382 0.047 Uiso 1 1 calc R U . A 4
H15B H 0.3205 0.6493 0.4509 0.047 Uiso 1 1 calc R U . A 4
C16 C 0.2638(5) 0.8208(4) 0.4054(3) 0.0384(8) Uani 1 1 d . . . A 4
H16A H 0.1388 0.7874 0.3891 0.046 Uiso 1 1 calc R U . A 4
H16B H 0.2835 0.9098 0.4358 0.046 Uiso 1 1 calc R U . A 4
C17 C 0.3628(5) 0.8297(4) 0.3059(3) 0.0396(8) Uani 1 1 d . . . A 4
H17A H 0.3503 0.7400 0.2782 0.047 Uiso 1 1 calc R U . A 4
H17B H 0.4869 0.8692 0.3214 0.047 Uiso 1 1 calc R U . A 4
C18 C 0.3030(6) 0.9096(4) 0.2238(3) 0.0516(10) Uani 1 1 d . . . A 4
H18A H 0.1774 0.8736 0.2113 0.062 Uiso 1 1 calc R U . A 4
H18B H 0.3228 1.0008 0.2495 0.062 Uiso 1 1 calc R U . A 4
C19 C 0.3947(8) 0.9103(6) 0.1231(4) 0.0759(16) Uani 1 1 d . . . A 4
H19A H 0.5188 0.9489 0.1343 0.114 Uiso 1 1 calc R U . A 4
H19B H 0.3498 0.9621 0.0730 0.114 Uiso 1 1 calc R U . A 4
H19C H 0.3749 0.8203 0.0968 0.114 Uiso 1 1 calc R U . A 4
Cl1 Cl 0.1030(9) 0.9852(7) 0.6136(4) 0.1384(19) Uani 0.603(8) 1 d D . P B 1
Cl2 Cl -0.0030(8) 0.8481(8) 0.9086(3) 0.1384(19) Uani 0.603(8) 1 d D . P B 1
C20 C 0.120(2) 0.9575(16) 0.7410(9) 0.1384(19) Uani 0.603(8) 1 d D . P B 1
H20A H 0.2339 0.9413 0.7555 0.166 Uiso 0.603(8) 1 calc R U P B 1
H20B H 0.1156 1.0374 0.7800 0.166 Uiso 0.603(8) 1 calc R U P B 1
C21 C -0.018(2) 0.8437(17) 0.7793(10) 0.1384(19) Uani 0.603(8) 1 d D . P B 1
H21A H -0.0019 0.7602 0.7521 0.166 Uiso 0.603(8) 1 calc R U P B 1
H21B H -0.1338 0.8508 0.7563 0.166 Uiso 0.603(8) 1 calc R U P B 1
Cl2A Cl 0.0470(6) 0.9144(5) 0.8800(5) 0.0881(15) Uani 0.397(8) 1 d D . P B 2
C20A C -0.003(2) 0.8761(13) 0.6693(10) 0.0881(15) Uani 0.397(8) 1 d D . P B 2
H20C H -0.1257 0.8768 0.6653 0.106 Uiso 0.397(8) 1 calc R U P B 2
H20D H 0.0138 0.8135 0.6157 0.106 Uiso 0.397(8) 1 calc R U P B 2
C21A C 0.026(2) 0.8269(13) 0.7630(10) 0.0881(15) Uani 0.397(8) 1 d D . P B 2
H21C H 0.1326 0.7975 0.7565 0.106 Uiso 0.397(8) 1 calc R U P B 2
H21D H -0.0694 0.7468 0.7716 0.106 Uiso 0.397(8) 1 calc R U P B 2
Cl1A Cl 0.1157(9) 1.0256(5) 0.6378(6) 0.0881(15) Uani 0.397(8) 1 d D . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.323(4) . ?
C1 N4 1.386(5) . ?
C1 C7 1.425(4) . ?
N1 C2 1.384(4) . ?
C2 C6 1.384(5) . ?
C2 C3 1.413(4) . ?
C3 N5 1.322(5) . ?
C3 N2 1.355(4) . ?
N2 C4 1.341(5) . ?
C4 N3 1.332(5) . ?
C4 H4 0.9500 . ?
N3 C6 1.343(4) . ?
C6 N4 1.367(4) . ?
N4 C14 1.457(4) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C7 C8 1.194(5) . ?
C8 C9 1.432(4) . ?
C9 C13 1.387(5) . ?
C9 C10 1.393(5) . ?
C10 N6 1.331(4) . ?
C10 H10 0.9500 . ?
N6 C11 1.335(5) . ?
C11 C12 1.375(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.522(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.517(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.513(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Cl1 C20 1.696(12) . ?
Cl2 C21 1.682(13) . ?
C20 C21 1.504(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
Cl2A C21A 1.753(14) . ?
C20A C21A 1.370(14) . ?
C20A Cl1A 1.678(13) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 113.6(3) . . ?
N1 C1 C7 125.9(3) . . ?
N4 C1 C7 120.5(3) . . ?
C1 N1 C2 103.4(3) . . ?
N1 C2 C6 111.3(3) . . ?
N1 C2 C3 131.7(3) . . ?
C6 C2 C3 117.0(3) . . ?
N5 C3 N2 119.1(3) . . ?
N5 C3 C2 123.6(3) . . ?
N2 C3 C2 117.3(3) . . ?
C4 N2 C3 118.6(3) . . ?
N3 C4 N2 129.5(3) . . ?
N3 C4 H4 115.3 . . ?
N2 C4 H4 115.3 . . ?
C4 N3 C6 110.5(3) . . ?
N3 C6 N4 126.8(3) . . ?
N3 C6 C2 127.1(3) . . ?
N4 C6 C2 106.1(3) . . ?
C6 N4 C1 105.6(3) . . ?
C6 N4 C14 126.6(3) . . ?
C1 N4 C14 127.9(3) . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 C7 C1 177.0(4) . . ?
C7 C8 C9 178.1(4) . . ?
C13 C9 C10 117.8(3) . . ?
C13 C9 C8 120.9(3) . . ?
C10 C9 C8 121.3(3) . . ?
N6 C10 C9 123.5(3) . . ?
N6 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C10 N6 C11 117.4(3) . . ?
N6 C11 C12 123.6(3) . . ?
N6 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C9 C13 C12 119.2(3) . . ?
C9 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N4 C14 C15 112.9(3) . . ?
N4 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N4 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 111.2(3) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 113.6(3) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 113.8(3) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 113.2(4) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 Cl1 114.2(12) . . ?
C21 C20 H20A 108.7 . . ?
Cl1 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
Cl1 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 Cl2 107.4(11) . . ?
C20 C21 H21A 110.2 . . ?
Cl2 C21 H21A 110.2 . . ?
C20 C21 H21B 110.2 . . ?
Cl2 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21A C20A Cl1A 119.1(12) . . ?
C21A C20A H20C 107.5 . . ?
Cl1A C20A H20C 107.5 . . ?
C21A C20A H20D 107.5 . . ?
Cl1A C20A H20D 107.5 . . ?
H20C C20A H20D 107.0 . . ?
C20A C21A Cl2A 124.5(12) . . ?
C20A C21A H21C 106.2 . . ?
Cl2A C21A H21C 106.2 . . ?
C20A C21A H21D 106.2 . . ?
Cl2A C21A H21D 106.2 . . ?
H21C C21A H21D 106.4 . . ?

_refine_diff_density_max         1.175
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.083

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e4585a_a
_database_code_depnum_ccdc_archive 'CCDC 2040829'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C18 H20 N6 O) [+ solvent]'
_chemical_formula_sum            'C72 H80 N24 O4[+ solvent]'
_chemical_formula_weight         1345.60

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'

_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                   11.5373(5)
_cell_length_b                   18.3921(10)
_cell_length_c                   19.7362(10)
_cell_angle_alpha                105.323(2)
_cell_angle_beta                 101.496(2)
_cell_angle_gamma                106.603(2)
_cell_volume                     3695.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.13


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47301
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         27.716
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             16190
_reflns_number_gt                11844
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
Some Hydrogens weren't introduced because of the disorder
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0853P)²+2.2957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16190
_refine_ls_number_parameters     948
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.010

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
C1 C 0.77348(18) 0.50815(12) 0.92939(10) 0.0260(4) Uani 1 1 d . . . A 4
N1 N 0.69395(15) 0.42798(10) 0.89962(8) 0.0270(3) Uani 1 1 d D . . A 4
C2 C 0.62213(18) 0.41859(11) 0.83192(10) 0.0249(4) Uani 1 1 d . . . A 4
N2 N 0.53364(15) 0.34921(10) 0.78286(9) 0.0272(4) Uani 1 1 d . . . A 4
C3 C 0.48013(18) 0.35753(12) 0.72072(10) 0.0263(4) Uani 1 1 d . . . A 4
N3 N 0.51313(15) 0.42942(10) 0.70761(9) 0.0269(3) Uani 1 1 d . . . A 4
H3 H 0.4729 0.4297 0.6649 0.032 Uiso 1 1 calc R U . A 4
C4 C 0.60554(18) 0.50194(11) 0.75683(10) 0.0260(4) Uani 1 1 d . . . A 4
C5 C 0.66192(18) 0.49335(11) 0.82394(10) 0.0247(4) Uani 1 1 d . . . A 4
N4 N 0.75725(15) 0.54947(10) 0.88529(9) 0.0268(3) Uani 1 1 d . . . A 4
C6 C 0.6934(2) 0.36435(14) 0.93243(13) 0.0441(6) Uani 1 1 d D . . A 4
C7 C 0.6303(5) 0.3662(3) 0.9931(3) 0.0652(13) Uani 0.699(5) 1 d D . P A 1
C8 C 0.4991(7) 0.3556(5) 0.9645(4) 0.112(2) Uani 0.699(5) 1 d D . P A 1
H8A H 0.4591 0.3056 0.9209 0.134 Uiso 0.699(5) 1 calc R U P A 1
H8B H 0.4959 0.4013 0.9474 0.134 Uiso 0.699(5) 1 calc R U P A 1
C9 C 0.4164(6) 0.3504(4) 1.0197(4) 0.099(2) Uani 0.699(5) 1 d D . P A 1
H9A H 0.4676 0.3887 1.0697 0.119 Uiso 0.699(5) 1 calc R U P A 1
H9B H 0.3422 0.3652 1.0036 0.119 Uiso 0.699(5) 1 calc R U P A 1
C10 C 0.3736(8) 0.2675(4) 1.0212(5) 0.114(3) Uani 0.699(5) 1 d D . P A 1
H10A H 0.4468 0.2589 1.0492 0.137 Uiso 0.699(5) 1 calc R U P A 1
H10B H 0.3463 0.2295 0.9702 0.137 Uiso 0.699(5) 1 calc R U P A 1
C11 C 0.2665(5) 0.2463(3) 1.0545(4) 0.0900(19) Uani 0.699(5) 1 d D . P A 1
H11A H 0.2868 0.2880 1.1024 0.135 Uiso 0.699(5) 1 calc R U P A 1
H11B H 0.2552 0.1940 1.0610 0.135 Uiso 0.699(5) 1 calc R U P A 1
H11C H 0.1881 0.2434 1.0216 0.135 Uiso 0.699(5) 1 calc R U P A 1
N5 N 0.39032(17) 0.29415(10) 0.66763(9) 0.0357(4) Uani 1 1 d . . . . .
H5A H 0.3666 0.2470 0.6738 0.043 Uiso 1 1 calc R U . A 4
H5B H 0.3544 0.2993 0.6263 0.043 Uiso 1 1 calc R U . A 4
O1 O 0.63081(14) 0.56277(9) 0.73939(8) 0.0359(3) Uani 1 1 d . . . . .
C12 C 0.8631(2) 0.53893(12) 1.00031(11) 0.0307(4) Uani 1 1 d . . . . .
C13 C 0.9375(2) 0.56170(13) 1.05977(11) 0.0322(4) Uani 1 1 d . . . . .
C14 C 1.0249(2) 0.58854(13) 1.13143(10) 0.0315(4) Uani 1 1 d . . . . .
C15 C 1.1051(2) 0.66900(14) 1.16586(11) 0.0352(5) Uani 1 1 d . . . . .
H15 H 1.1046 0.7074 1.1418 0.042 Uiso 1 1 calc R U . . .
C16 C 1.1855(2) 0.69141(15) 1.23615(12) 0.0411(5) Uani 1 1 d . . . . .
H16 H 1.2392 0.7465 1.2595 0.049 Uiso 1 1 calc R U . . .
N6 N 1.1927(2) 0.64104(13) 1.27323(10) 0.0454(5) Uani 1 1 d . . . . .
C17 C 1.1168(3) 0.56431(16) 1.23863(13) 0.0454(6) Uani 1 1 d . . . . .
H17 H 1.1213 0.5270 1.2635 0.054 Uiso 1 1 calc R U . . .
C18 C 1.0320(2) 0.53525(14) 1.16898(12) 0.0392(5) Uani 1 1 d . . . . .
H18 H 0.9796 0.4798 1.1472 0.047 Uiso 1 1 calc R U . . .
C19 C 0.37147(18) 0.48233(11) 0.53157(10) 0.0258(4) Uani 1 1 d . . . . .
N7 N 0.29091(15) 0.46521(9) 0.46262(8) 0.0249(3) Uani 1 1 d . . . . .
C20 C 0.21938(17) 0.38511(11) 0.43875(10) 0.0233(4) Uani 1 1 d . . . . .
N8 N 0.12700(15) 0.34332(9) 0.37406(8) 0.0258(3) Uani 1 1 d . . . . .
C21 C 0.07005(18) 0.26695(12) 0.36703(10) 0.0260(4) Uani 1 1 d . . . . .
N9 N 0.10518(15) 0.23353(10) 0.41845(9) 0.0279(4) Uani 1 1 d . . . . .
H9 H 0.0628 0.1821 0.4090 0.033 Uiso 1 1 calc R U . . .
C22 C 0.20260(19) 0.27435(12) 0.48449(10) 0.0277(4) Uani 1 1 d . . . . .
C23 C 0.25997(18) 0.35737(11) 0.49438(10) 0.0257(4) Uani 1 1 d . . . . .
N10 N 0.35574(16) 0.41849(10) 0.55254(9) 0.0274(3) Uani 1 1 d . . . . .
C24 C 0.2883(2) 0.52063(12) 0.42142(11) 0.0311(4) Uani 1 1 d D . . . .
H24A H 0.2806 0.4924 0.3696 0.037 Uiso 1 1 calc R U . . .
H24B H 0.3696 0.5670 0.4422 0.037 Uiso 1 1 calc R U . . .
C25 C 0.1809(2) 0.55182(15) 0.42320(13) 0.0428(5) Uani 1 1 d D . . . .
H25A H 0.0997 0.5057 0.3988 0.051 Uiso 1 1 calc R U . . .
H25B H 0.1852 0.5886 0.3944 0.051 Uiso 1 1 calc R U . . .
C26 C 0.1812(3) 0.59625(19) 0.49977(15) 0.0576(7) Uani 1 1 d D . . . .
H26A H 0.2637 0.6411 0.5251 0.069 Uiso 1 1 calc R U . . .
H26B H 0.1727 0.5588 0.5280 0.069 Uiso 1 1 calc R U . . .
C27 C 0.0759(3) 0.6303(2) 0.50014(19) 0.0661(8) Uani 1 1 d D . . . .
H27A H 0.0718 0.6488 0.5512 0.079 Uiso 1 1 calc R U . . .
H27B H -0.0058 0.5864 0.4701 0.079 Uiso 1 1 calc R U . . .
C28 C 0.0913(3) 0.70014(18) 0.47090(18) 0.0633(8) Uani 1 1 d D . . . .
H28A H 0.1044 0.6833 0.4219 0.076 Uiso 1 1 calc R U . . .
H28B H 0.0115 0.7112 0.4641 0.076 Uiso 1 1 calc R U . . .
C29 C 0.1993(4) 0.7774(2) 0.5195(2) 0.0892(11) Uani 1 1 d D . . . .
H29A H 0.1896 0.7935 0.5689 0.134 Uiso 1 1 calc R U . . .
H29B H 0.1984 0.8201 0.4986 0.134 Uiso 1 1 calc R U . . .
H29C H 0.2798 0.7688 0.5224 0.134 Uiso 1 1 calc R U . . .
N11 N -0.02559(17) 0.21812(11) 0.30723(9) 0.0348(4) Uani 1 1 d . . . . .
H11E H -0.0510 0.2365 0.2723 0.042 Uiso 1 1 calc R U . . .
H11F H -0.0634 0.1674 0.3026 0.042 Uiso 1 1 calc R U . . .
O2 O 0.22936(15) 0.23805(9) 0.52576(8) 0.0400(4) Uani 1 1 d . . . . .
C30 C 0.45651(19) 0.56206(12) 0.57320(10) 0.0281(4) Uani 1 1 d . . . . .
C31 C 0.5229(2) 0.63070(12) 0.60599(11) 0.0306(4) Uani 1 1 d . . . . .
C32 C 0.59935(19) 0.71362(12) 0.64622(11) 0.0300(4) Uani 1 1 d . . . . .
C33 C 0.6715(2) 0.73775(13) 0.71906(12) 0.0350(5) Uani 1 1 d . . . . .
H33 H 0.6730 0.6993 0.7430 0.042 Uiso 1 1 calc R U . . .
C34 C 0.7409(2) 0.81880(14) 0.75589(14) 0.0457(6) Uani 1 1 d . . . . .
H34 H 0.7893 0.8350 0.8058 0.055 Uiso 1 1 calc R U . . .
N12 N 0.7440(2) 0.87574(12) 0.72548(14) 0.0568(6) Uani 1 1 d . . . . .
C35 C 0.6758(3) 0.85135(16) 0.65518(18) 0.0618(8) Uani 1 1 d . . . . .
H35 H 0.6783 0.8909 0.6323 0.074 Uiso 1 1 calc R U . . .
C36 C 0.6022(3) 0.77232(14) 0.61389(14) 0.0479(6) Uani 1 1 d . . . . .
H36 H 0.5543 0.7582 0.5642 0.057 Uiso 1 1 calc R U . . .
C37 C 0.6121(2) 0.14482(13) 0.03402(12) 0.0352(5) Uani 1 1 d . . . . .
N13 N 0.67968(16) 0.17619(11) 0.10783(10) 0.0335(4) Uani 1 1 d . . . . .
C38 C 0.79751(19) 0.22403(12) 0.11219(11) 0.0297(4) Uani 1 1 d . . . . .
N14 N 0.89526(16) 0.26621(11) 0.17492(9) 0.0313(4) Uani 1 1 d . . . . .
C39 C 0.99807(19) 0.30816(12) 0.16301(11) 0.0284(4) Uani 1 1 d . . . . .
N15 N 1.00590(16) 0.30837(10) 0.09461(9) 0.0308(4) Uani 1 1 d . . . . .
H15A H 1.0775 0.3397 0.0923 0.037 Uiso 1 1 calc R U . . .
C40 C 0.9090(2) 0.26267(13) 0.02783(11) 0.0324(4) Uani 1 1 d . . . . .
C41 C 0.7966(2) 0.21925(12) 0.04121(11) 0.0309(4) Uani 1 1 d . . . . .
N16 N 0.67960(17) 0.16924(11) -0.00777(10) 0.0352(4) Uani 1 1 d . . . . .
C42 C 0.6336(2) 0.15947(16) 0.16823(13) 0.0433(6) Uani 1 1 d D . . . .
H42A H 0.7071 0.1739 0.2114 0.052 Uiso 1 1 calc R U . . .
H42B H 0.5856 0.1009 0.1531 0.052 Uiso 1 1 calc R U . . .
C43 C 0.5498(2) 0.20545(18) 0.19014(15) 0.0550(7) Uani 1 1 d D . . . .
H43A H 0.5222 0.1917 0.2310 0.066 Uiso 1 1 calc R U . . .
H43B H 0.4732 0.1877 0.1479 0.066 Uiso 1 1 calc R U . . .
C44 C 0.6139(3) 0.2970(2) 0.21425(17) 0.0665(8) Uani 1 1 d D . . . .
H44A H 0.5491 0.3222 0.2174 0.080 Uiso 1 1 calc R U . . .
H44B H 0.6529 0.3106 0.1767 0.080 Uiso 1 1 calc R U . . .
C45 C 0.7166(4) 0.3320(2) 0.28924(18) 0.0798(10) Uani 1 1 d D . . . .
C46 C 0.7462(14) 0.4273(9) 0.3091(9) 0.131(8) Uani 0.388(10) 1 d D . P B 1
H46A H 0.6678 0.4380 0.2929 0.157 Uiso 0.388(10) 1 calc R U P B 1
H46B H 0.7847 0.4559 0.3627 0.157 Uiso 0.388(10) 1 calc R U P B 1
C47 C 0.8401(9) 0.4544(6) 0.2669(5) 0.074(3) Uani 0.388(10) 1 d D . P B 1
H47A H 0.9020 0.4275 0.2704 0.110 Uiso 0.388(10) 1 calc R U P B 1
H47B H 0.8843 0.5130 0.2884 0.110 Uiso 0.388(10) 1 calc R U P B 1
H47C H 0.7937 0.4399 0.2151 0.110 Uiso 0.388(10) 1 calc R U P B 1
N17 N 1.10165(16) 0.35478(11) 0.22005(9) 0.0364(4) Uani 1 1 d . . . . .
H17A H 1.1008 0.3573 0.2651 0.044 Uiso 1 1 calc R U . . .
H17B H 1.1705 0.3829 0.2124 0.044 Uiso 1 1 calc R U . . .
O3 O 0.92717(17) 0.26409(11) -0.03071(8) 0.0479(4) Uani 1 1 d . . . . .
C48 C 0.4835(2) 0.09270(14) 0.00841(13) 0.0405(5) Uani 1 1 d . . . . .
C49 C 0.3751(2) 0.04988(14) -0.01217(13) 0.0426(5) Uani 1 1 d . . . . .
C50 C 0.2447(2) -0.00241(14) -0.03885(13) 0.0407(5) Uani 1 1 d . . . . .
C51 C 0.1789(2) -0.02621(16) 0.00726(14) 0.0473(6) Uani 1 1 d . . . . .
H51 H 0.2188 -0.0077 0.0588 0.057 Uiso 1 1 calc R U . . .
C52 C 0.0539(3) -0.07741(17) -0.02237(17) 0.0539(7) Uani 1 1 d . . . . .
H52 H 0.0104 -0.0937 0.0103 0.065 Uiso 1 1 calc R U . . .
N18 N -0.0091(2) -0.10529(15) -0.09290(14) 0.0614(7) Uani 1 1 d . . . . .
C53 C 0.0554(3) -0.0823(2) -0.13626(17) 0.0782(11) Uani 1 1 d . . . . .
H53 H 0.0125 -0.1020 -0.1875 0.094 Uiso 1 1 calc R U . . .
C54 C 0.1806(3) -0.0318(2) -0.11296(15) 0.0683(9) Uani 1 1 d . . . . .
H54 H 0.2218 -0.0177 -0.1473 0.082 Uiso 1 1 calc R U . . .
C55 C 1.01878(19) 1.00746(12) 0.40746(11) 0.0292(4) Uani 1 1 d . . . . .
N19 N 0.93469(15) 0.92850(10) 0.38330(9) 0.0279(4) Uani 1 1 d . . . . .
C56 C 0.82593(18) 0.92709(11) 0.33980(10) 0.0260(4) Uani 1 1 d . . . . .
N20 N 0.71819(15) 0.86173(10) 0.30443(9) 0.0284(4) Uani 1 1 d . . . . .
C57 C 0.62943(19) 0.87817(12) 0.26434(11) 0.0291(4) Uani 1 1 d . . . . .
N21 N 0.64529(16) 0.95325(10) 0.25921(9) 0.0306(4) Uani 1 1 d . . . . .
H21 H 0.5817 0.9582 0.2300 0.037 Uiso 1 1 calc R U . . .
C58 C 0.75289(19) 1.02200(12) 0.29607(11) 0.0300(4) Uani 1 1 d . . . . .
C59 C 0.84884(18) 1.00535(12) 0.33992(11) 0.0282(4) Uani 1 1 d . . . . .
N22 N 0.97021(16) 1.05566(10) 0.38248(9) 0.0314(4) Uani 1 1 d . . . . .
C60 C 0.9635(2) 0.86073(13) 0.39855(12) 0.0350(5) Uani 1 1 d D . . . .
H60A H 0.8835 0.8170 0.3911 0.042 Uiso 1 1 calc R U . . .
H60B H 1.0146 0.8788 0.4506 0.042 Uiso 1 1 calc R U . . .
C61 C 1.0355(2) 0.82831(15) 0.34930(14) 0.0442(6) Uani 1 1 d D . . . .
H61A H 1.0682 0.7909 0.3680 0.053 Uiso 1 1 calc R U . . .
H61B H 1.1091 0.8738 0.3517 0.053 Uiso 1 1 calc R U . . .
C62 C 0.9548(3) 0.78414(15) 0.26945(14) 0.0470(6) Uani 1 1 d D . . . .
H62A H 0.9014 0.8146 0.2556 0.056 Uiso 1 1 calc R U . . .
H62B H 1.0114 0.7833 0.2378 0.056 Uiso 1 1 calc R U . . .
C63 C 0.8698(3) 0.69811(16) 0.25434(14) 0.0500(6) Uani 1 1 d D . . . .
H63A H 0.8241 0.6976 0.2918 0.060 Uiso 1 1 calc R U . . .
H63B H 0.9229 0.6648 0.2590 0.060 Uiso 1 1 calc R U . . .
C64 C 0.7742(3) 0.66089(19) 0.17833(17) 0.0648(8) Uani 1 1 d D . . . .
H64A H 0.8195 0.6671 0.1414 0.078 Uiso 1 1 calc R U . . .
H64B H 0.7155 0.6909 0.1756 0.078 Uiso 1 1 calc R U . . .
C65 C 0.6974(3) 0.5719(2) 0.1588(2) 0.0786(10) Uani 1 1 d D . . . .
H65A H 0.7540 0.5410 0.1571 0.118 Uiso 1 1 calc R U . . .
H65B H 0.6341 0.5523 0.1105 0.118 Uiso 1 1 calc R U . . .
H65C H 0.6546 0.5649 0.1960 0.118 Uiso 1 1 calc R U . . .
N23 N 0.51688(17) 0.82093(11) 0.22570(11) 0.0405(5) Uani 1 1 d . . . . .
H23A H 0.5010 0.7716 0.2267 0.049 Uiso 1 1 calc R U . . .
H23B H 0.4584 0.8325 0.1992 0.049 Uiso 1 1 calc R U . . .
O4 O 0.75732(15) 1.08641(9) 0.28707(9) 0.0417(4) Uani 1 1 d . . . . .
C66 C 1.1435(2) 1.03011(13) 0.45419(11) 0.0333(5) Uani 1 1 d . . . . .
C67 C 1.2473(2) 1.04632(13) 0.49314(12) 0.0349(5) Uani 1 1 d . . . . .
C68 C 1.3735(2) 1.06907(14) 0.53919(11) 0.0336(5) Uani 1 1 d . . . . .
C69 C 1.4136(2) 1.01591(16) 0.56741(13) 0.0446(6) Uani 1 1 d . . . . .
H69 H 1.3576 0.9625 0.5569 0.054 Uiso 1 1 calc R U . . .
C70 C 1.5378(3) 1.0430(2) 0.61140(15) 0.0570(7) Uani 1 1 d . . . . .
H70 H 1.5647 1.0063 0.6306 0.068 Uiso 1 1 calc R U . . .
N24 N 1.6214(2) 1.11630(17) 0.62854(13) 0.0598(6) Uani 1 1 d . . . . .
C71 C 1.5814(2) 1.16613(19) 0.60086(14) 0.0557(7) Uani 1 1 d . . . . .
H71 H 1.6400 1.2190 0.6121 0.067 Uiso 1 1 calc R U . . .
C72 C 1.4605(2) 1.14633(15) 0.55695(12) 0.0443(6) Uani 1 1 d . . . . .
H72 H 1.4369 1.1848 0.5391 0.053 Uiso 1 1 calc R U . . .
C7A C 0.5646(9) 0.3250(7) 0.9469(6) 0.080(2) Uani 0.301(5) 1 d D . P A 2
C8A C 0.5532(11) 0.3800(7) 1.0178(6) 0.080(2) Uani 0.301(5) 1 d D . P A 2
H8A1 H 0.5242 0.4234 1.0092 0.096 Uiso 0.301(5) 1 calc R U P A 2
H8A2 H 0.6334 0.4038 1.0585 0.096 Uiso 0.301(5) 1 calc R U P A 2
C9A C 0.4479(9) 0.3135(10) 1.0315(8) 0.080(2) Uani 0.301(5) 1 d D . P A 2
H9A1 H 0.4682 0.2639 1.0171 0.096 Uiso 0.301(5) 1 calc R U P A 2
H9A2 H 0.4652 0.3306 1.0856 0.096 Uiso 0.301(5) 1 calc R U P A 2
C10A C 0.3006(9) 0.2851(7) 0.9996(7) 0.080(2) Uani 0.301(5) 1 d D . P A 2
H10C H 0.2646 0.2900 1.0414 0.096 Uiso 0.301(5) 1 calc R U P A 2
H10D H 0.2814 0.3230 0.9756 0.096 Uiso 0.301(5) 1 calc R U P A 2
C11A C 0.2332(11) 0.2015(7) 0.9458(6) 0.080(2) Uani 0.301(5) 1 d D . P A 2
H11D H 0.2743 0.1930 0.9069 0.120 Uiso 0.301(5) 1 calc R U P A 2
H11G H 0.1447 0.1941 0.9239 0.120 Uiso 0.301(5) 1 calc R U P A 2
H11H H 0.2362 0.1625 0.9710 0.120 Uiso 0.301(5) 1 calc R U P A 2
C46A C 0.8140(9) 0.4166(4) 0.3074(4) 0.096(3) Uani 0.612(10) 1 d D . P B 2
H46C H 0.8724 0.4313 0.3571 0.116 Uiso 0.612(10) 1 calc R U P B 2
H46D H 0.8645 0.4119 0.2725 0.116 Uiso 0.612(10) 1 calc R U P B 2
C47A C 0.7747(13) 0.4824(7) 0.3067(7) 0.165(6) Uani 0.612(10) 1 d D . P B 2
H47D H 0.7215 0.4716 0.2572 0.248 Uiso 0.612(10) 1 calc R U P B 2
H47E H 0.8492 0.5315 0.3207 0.248 Uiso 0.612(10) 1 calc R U P B 2
H47F H 0.7260 0.4898 0.3418 0.248 Uiso 0.612(10) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.318(2) . ?
C1 N1 1.384(2) . ?
C1 C12 1.421(3) . ?
N1 C2 1.363(2) . ?
N1 C6 1.479(3) . ?
C2 N2 1.348(2) . ?
C2 C5 1.382(3) . ?
N2 C3 1.327(2) . ?
C3 N5 1.327(2) . ?
C3 N3 1.376(2) . ?
N3 C4 1.396(2) . ?
N3 H3 0.8800 . ?
C4 O1 1.230(2) . ?
C4 C5 1.424(3) . ?
C5 N4 1.379(2) . ?
C6 C7 1.517(5) . ?
C6 C7A 1.574(8) . ?
C7 C8 1.443(8) . ?
C8 C9 1.589(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.472(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.514(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C12 C13 1.193(3) . ?
C13 C14 1.428(3) . ?
C14 C18 1.386(3) . ?
C14 C15 1.394(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 N6 1.334(3) . ?
C16 H16 0.9500 . ?
N6 C17 1.331(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N10 1.322(2) . ?
C19 N7 1.385(2) . ?
C19 C30 1.417(3) . ?
N7 C20 1.363(2) . ?
N7 C24 1.465(2) . ?
C20 N8 1.352(2) . ?
C20 C23 1.383(2) . ?
N8 C21 1.326(2) . ?
C21 N11 1.331(2) . ?
C21 N9 1.371(2) . ?
N9 C22 1.394(2) . ?
N9 H9 0.8800 . ?
C22 O2 1.229(2) . ?
C22 C23 1.422(3) . ?
C23 N10 1.380(2) . ?
C24 C25 1.510(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.515(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.518(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.522(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.511(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N11 H11E 0.8800 . ?
N11 H11F 0.8800 . ?
C30 C31 1.191(3) . ?
C31 C32 1.430(3) . ?
C32 C36 1.388(3) . ?
C32 C33 1.390(3) . ?
C33 C34 1.380(3) . ?
C33 H33 0.9500 . ?
C34 N12 1.333(3) . ?
C34 H34 0.9500 . ?
N12 C35 1.334(4) . ?
C35 C36 1.375(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N16 1.319(3) . ?
C37 N13 1.382(3) . ?
C37 C48 1.417(3) . ?
N13 C38 1.364(3) . ?
N13 C42 1.466(3) . ?
C38 N14 1.357(2) . ?
C38 C41 1.378(3) . ?
N14 C39 1.320(3) . ?
C39 N17 1.341(3) . ?
C39 N15 1.372(2) . ?
N15 C40 1.408(3) . ?
N15 H15A 0.8800 . ?
C40 O3 1.220(3) . ?
C40 C41 1.430(3) . ?
C41 N16 1.380(3) . ?
C42 C43 1.509(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.527(4) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.539(5) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46A 1.535(7) . ?
C45 C46 1.606(15) . ?
C46 C47 1.545(12) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
C48 C49 1.189(3) . ?
C49 C50 1.434(3) . ?
C50 C51 1.376(4) . ?
C50 C54 1.379(4) . ?
C51 C52 1.380(4) . ?
C51 H51 0.9500 . ?
C52 N18 1.317(4) . ?
C52 H52 0.9500 . ?
N18 C53 1.315(4) . ?
C53 C54 1.380(4) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 N22 1.322(3) . ?
C55 N19 1.386(2) . ?
C55 C66 1.421(3) . ?
N19 C56 1.361(2) . ?
N19 C60 1.466(3) . ?
C56 N20 1.354(2) . ?
C56 C59 1.387(3) . ?
N20 C57 1.322(3) . ?
C57 N23 1.333(3) . ?
C57 N21 1.374(2) . ?
N21 C58 1.388(3) . ?
N21 H21 0.8800 . ?
C58 O4 1.232(2) . ?
C58 C59 1.421(3) . ?
C59 N22 1.379(2) . ?
C60 C61 1.512(3) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.522(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 C63 1.517(4) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.517(4) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.522(4) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
N23 H23A 0.8800 . ?
N23 H23B 0.8800 . ?
C66 C67 1.192(3) . ?
C67 C68 1.430(3) . ?
C68 C69 1.387(3) . ?
C68 C72 1.390(3) . ?
C69 C70 1.387(4) . ?
C69 H69 0.9500 . ?
C70 N24 1.322(4) . ?
C70 H70 0.9500 . ?
N24 C71 1.326(4) . ?
C71 C72 1.374(3) . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
C7A C8A 1.549(9) . ?
C8A C9A 1.582(9) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.565(9) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.490(9) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11D 0.9800 . ?
C11A H11G 0.9800 . ?
C11A H11H 0.9800 . ?
C46A C47A 1.411(11) . ?
C46A H46C 0.9900 . ?
C46A H46D 0.9900 . ?
C47A H47D 0.9800 . ?
C47A H47E 0.9800 . ?
C47A H47F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 113.24(16) . . ?
N4 C1 C12 125.80(18) . . ?
N1 C1 C12 120.95(17) . . ?
C2 N1 C1 105.90(15) . . ?
C2 N1 C6 127.04(17) . . ?
C1 N1 C6 126.94(17) . . ?
N2 C2 N1 126.07(17) . . ?
N2 C2 C5 128.02(17) . . ?
N1 C2 C5 105.89(16) . . ?
C3 N2 C2 113.02(16) . . ?
N2 C3 N5 119.55(17) . . ?
N2 C3 N3 123.27(17) . . ?
N5 C3 N3 117.18(17) . . ?
C3 N3 C4 125.07(16) . . ?
C3 N3 H3 117.5 . . ?
C4 N3 H3 117.5 . . ?
O1 C4 N3 120.36(17) . . ?
O1 C4 C5 127.90(18) . . ?
N3 C4 C5 111.73(16) . . ?
N4 C5 C2 111.32(16) . . ?
N4 C5 C4 129.77(17) . . ?
C2 C5 C4 118.89(17) . . ?
C1 N4 C5 103.65(16) . . ?
C7 C8 C9 116.3(5) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 109.4(5) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 C11 115.8(5) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C13 C12 C1 177.4(2) . . ?
C12 C13 C14 179.1(2) . . ?
C18 C14 C15 118.03(19) . . ?
C18 C14 C13 120.9(2) . . ?
C15 C14 C13 121.11(19) . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N6 C16 C15 124.5(2) . . ?
N6 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
C17 N6 C16 116.13(19) . . ?
N6 C17 C18 124.4(2) . . ?
N6 C17 H17 117.8 . . ?
C18 C17 H17 117.8 . . ?
C17 C18 C14 118.7(2) . . ?
C17 C18 H18 120.6 . . ?
C14 C18 H18 120.6 . . ?
N10 C19 N7 112.94(16) . . ?
N10 C19 C30 126.38(17) . . ?
N7 C19 C30 120.65(17) . . ?
C20 N7 C19 106.20(15) . . ?
C20 N7 C24 126.67(16) . . ?
C19 N7 C24 127.02(16) . . ?
N8 C20 N7 125.91(16) . . ?
N8 C20 C23 128.28(17) . . ?
N7 C20 C23 105.80(16) . . ?
C21 N8 C20 112.51(15) . . ?
N8 C21 N11 120.02(17) . . ?
N8 C21 N9 123.45(17) . . ?
N11 C21 N9 116.52(17) . . ?
C21 N9 C22 125.32(16) . . ?
C21 N9 H9 117.3 . . ?
C22 N9 H9 117.3 . . ?
O2 C22 N9 120.19(18) . . ?
O2 C22 C23 128.12(18) . . ?
N9 C22 C23 111.69(16) . . ?
N10 C23 C20 111.34(16) . . ?
N10 C23 C22 130.01(17) . . ?
C20 C23 C22 118.64(17) . . ?
C19 N10 C23 103.71(15) . . ?
N7 C24 C25 113.22(17) . . ?
N7 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
N7 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 C26 114.3(2) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 C27 113.5(2) . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 C28 114.3(3) . . ?
C26 C27 H27A 108.7 . . ?
C28 C27 H27A 108.7 . . ?
C26 C27 H27B 108.7 . . ?
C28 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C29 C28 C27 114.8(3) . . ?
C29 C28 H28A 108.6 . . ?
C27 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 N11 H11E 120.0 . . ?
C21 N11 H11F 120.0 . . ?
H11E N11 H11F 120.0 . . ?
C31 C30 C19 176.0(2) . . ?
C30 C31 C32 178.1(2) . . ?
C36 C32 C33 118.2(2) . . ?
C36 C32 C31 120.9(2) . . ?
C33 C32 C31 120.90(19) . . ?
C34 C33 C32 118.5(2) . . ?
C34 C33 H33 120.7 . . ?
C32 C33 H33 120.7 . . ?
N12 C34 C33 123.8(2) . . ?
N12 C34 H34 118.1 . . ?
C33 C34 H34 118.1 . . ?
C34 N12 C35 116.9(2) . . ?
N12 C35 C36 123.9(3) . . ?
N12 C35 H35 118.0 . . ?
C36 C35 H35 118.1 . . ?
C35 C36 C32 118.7(2) . . ?
C35 C36 H36 120.6 . . ?
C32 C36 H36 120.6 . . ?
N16 C37 N13 112.90(18) . . ?
N16 C37 C48 125.3(2) . . ?
N13 C37 C48 121.8(2) . . ?
C38 N13 C37 105.78(17) . . ?
C38 N13 C42 127.65(18) . . ?
C37 N13 C42 126.56(18) . . ?
N14 C38 N13 125.58(18) . . ?
N14 C38 C41 127.95(19) . . ?
N13 C38 C41 106.46(17) . . ?
C39 N14 C38 112.64(17) . . ?
N14 C39 N17 119.59(18) . . ?
N14 C39 N15 123.73(18) . . ?
N17 C39 N15 116.67(18) . . ?
C39 N15 C40 125.53(17) . . ?
C39 N15 H15A 117.2 . . ?
C40 N15 H15A 117.2 . . ?
O3 C40 N15 120.6(2) . . ?
O3 C40 C41 128.9(2) . . ?
N15 C40 C41 110.48(17) . . ?
C38 C41 N16 110.65(18) . . ?
C38 C41 C40 119.56(18) . . ?
N16 C41 C40 129.79(19) . . ?
C37 N16 C41 104.21(17) . . ?
N13 C42 C43 112.8(2) . . ?
N13 C42 H42A 109.0 . . ?
C43 C42 H42A 109.0 . . ?
N13 C42 H42B 109.0 . . ?
C43 C42 H42B 109.0 . . ?
H42A C42 H42B 107.8 . . ?
C42 C43 C44 113.8(2) . . ?
C42 C43 H43A 108.8 . . ?
C44 C43 H43A 108.8 . . ?
C42 C43 H43B 108.8 . . ?
C44 C43 H43B 108.8 . . ?
H43A C43 H43B 107.7 . . ?
C43 C44 C45 112.2(3) . . ?
C43 C44 H44A 109.2 . . ?
C45 C44 H44A 109.2 . . ?
C43 C44 H44B 109.2 . . ?
C45 C44 H44B 109.2 . . ?
H44A C44 H44B 107.9 . . ?
C46A C45 C44 116.3(4) . . ?
C44 C45 C46 102.0(7) . . ?
C47 C46 C45 104.8(8) . . ?
C47 C46 H46A 110.9 . . ?
C45 C46 H46A 110.9 . . ?
C47 C46 H46B 110.7 . . ?
C45 C46 H46B 110.7 . . ?
H46A C46 H46B 108.9 . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.4 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C39 N17 H17A 120.0 . . ?
C39 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C49 C48 C37 178.9(3) . . ?
C48 C49 C50 178.5(3) . . ?
C51 C50 C54 117.2(2) . . ?
C51 C50 C49 122.2(2) . . ?
C54 C50 C49 120.5(2) . . ?
C50 C51 C52 119.1(2) . . ?
C50 C51 H51 120.5 . . ?
C52 C51 H51 120.5 . . ?
N18 C52 C51 124.4(3) . . ?
N18 C52 H52 117.8 . . ?
C51 C52 H52 117.8 . . ?
C53 N18 C52 115.8(2) . . ?
N18 C53 C54 124.9(3) . . ?
N18 C53 H53 117.6 . . ?
C54 C53 H53 117.6 . . ?
C50 C54 C53 118.6(3) . . ?
C50 C54 H54 120.7 . . ?
C53 C54 H54 120.7 . . ?
N22 C55 N19 113.19(17) . . ?
N22 C55 C66 126.09(18) . . ?
N19 C55 C66 120.72(18) . . ?
C56 N19 C55 105.95(16) . . ?
C56 N19 C60 128.28(17) . . ?
C55 N19 C60 125.65(17) . . ?
N20 C56 N19 126.07(17) . . ?
N20 C56 C59 127.95(18) . . ?
N19 C56 C59 105.98(17) . . ?
C57 N20 C56 112.45(16) . . ?
N20 C57 N23 120.72(18) . . ?
N20 C57 N21 123.55(18) . . ?
N23 C57 N21 115.73(18) . . ?
C57 N21 C58 125.63(17) . . ?
C57 N21 H21 117.2 . . ?
C58 N21 H21 117.2 . . ?
O4 C58 N21 120.27(18) . . ?
O4 C58 C59 128.29(19) . . ?
N21 C58 C59 111.42(17) . . ?
N22 C59 C56 111.26(17) . . ?
N22 C59 C58 129.73(18) . . ?
C56 C59 C58 118.93(18) . . ?
C55 N22 C59 103.63(16) . . ?
N19 C60 C61 111.72(18) . . ?
N19 C60 H60A 109.3 . . ?
C61 C60 H60A 109.3 . . ?
N19 C60 H60B 109.3 . . ?
C61 C60 H60B 109.3 . . ?
H60A C60 H60B 107.9 . . ?
C60 C61 C62 113.06(19) . . ?
C60 C61 H61A 109.0 . . ?
C62 C61 H61A 109.0 . . ?
C60 C61 H61B 109.0 . . ?
C62 C61 H61B 109.0 . . ?
H61A C61 H61B 107.8 . . ?
C63 C62 C61 113.8(2) . . ?
C63 C62 H62A 108.8 . . ?
C61 C62 H62A 108.8 . . ?
C63 C62 H62B 108.8 . . ?
C61 C62 H62B 108.8 . . ?
H62A C62 H62B 107.7 . . ?
C62 C63 C64 112.5(2) . . ?
C62 C63 H63A 109.1 . . ?
C64 C63 H63A 109.1 . . ?
C62 C63 H63B 109.1 . . ?
C64 C63 H63B 109.1 . . ?
H63A C63 H63B 107.8 . . ?
C63 C64 C65 113.5(3) . . ?
C63 C64 H64A 108.9 . . ?
C65 C64 H64A 108.9 . . ?
C63 C64 H64B 108.9 . . ?
C65 C64 H64B 108.9 . . ?
H64A C64 H64B 107.7 . . ?
C64 C65 H65A 109.5 . . ?
C64 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
C64 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C57 N23 H23A 120.0 . . ?
C57 N23 H23B 120.0 . . ?
H23A N23 H23B 120.0 . . ?
C67 C66 C55 177.7(2) . . ?
C66 C67 C68 177.4(2) . . ?
C69 C68 C72 117.8(2) . . ?
C69 C68 C67 122.0(2) . . ?
C72 C68 C67 120.2(2) . . ?
C70 C69 C68 118.1(2) . . ?
C70 C69 H69 121.0 . . ?
C68 C69 H69 121.0 . . ?
N24 C70 C69 124.6(3) . . ?
N24 C70 H70 117.7 . . ?
C69 C70 H70 117.7 . . ?
C70 N24 C71 116.4(2) . . ?
N24 C71 C72 124.3(3) . . ?
N24 C71 H71 117.9 . . ?
C72 C71 H71 117.9 . . ?
C71 C72 C68 118.8(2) . . ?
C71 C72 H72 120.6 . . ?
C68 C72 H72 120.6 . . ?
C7A C8A C9A 97.8(9) . . ?
C7A C8A H8A1 112.2 . . ?
C9A C8A H8A1 112.2 . . ?
C7A C8A H8A2 112.2 . . ?
C9A C8A H8A2 112.2 . . ?
H8A1 C8A H8A2 109.8 . . ?
C10A C9A C8A 128.2(12) . . ?
C10A C9A H9A1 105.2 . . ?
C8A C9A H9A1 105.3 . . ?
C10A C9A H9A2 105.3 . . ?
C8A C9A H9A2 105.3 . . ?
H9A1 C9A H9A2 106.0 . . ?
C11A C10A C9A 117.4(11) . . ?
C11A C10A H10C 108.3 . . ?
C9A C10A H10C 107.9 . . ?
C11A C10A H10D 107.7 . . ?
C9A C10A H10D 107.9 . . ?
H10C C10A H10D 107.2 . . ?
C10A C11A H11D 109.8 . . ?
C10A C11A H11G 109.4 . . ?
H11D C11A H11G 109.5 . . ?
C10A C11A H11H 109.1 . . ?
H11D C11A H11H 109.5 . . ?
H11G C11A H11H 109.5 . . ?
C47A C46A C45 120.7(9) . . ?
C47A C46A H46C 107.2 . . ?
C45 C46A H46C 107.2 . . ?
C47A C46A H46D 107.1 . . ?
C45 C46A H46D 107.1 . . ?
H46C C46A H46D 106.8 . . ?
C46A C47A H47D 109.5 . . ?
C46A C47A H47E 109.5 . . ?
H47D C47A H47E 109.5 . . ?
C46A C47A H47F 109.4 . . ?
H47D C47A H47F 109.5 . . ?
H47E C47A H47F 109.5 . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4732a_a
_database_code_depnum_ccdc_archive 'CCDC 2040836'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cu F12 N6 O4, H2 O'
_chemical_formula_sum            'C28 H24 Cu F12 N6 O5'
_chemical_formula_weight         816.07

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.7579(3)
_cell_length_b                   11.3344(4)
_cell_length_c                   18.0717(6)
_cell_angle_alpha                78.807(2)
_cell_angle_beta                 85.372(2)
_cell_angle_gamma                82.349(2)
_cell_volume                     1741.33(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7300
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             822
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.737
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21635
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         28.857
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             8360
_reflns_number_gt                6395
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1579P)²+2.1351P] 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         8360
_refine_ls_number_parameters     479
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.2498
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.009

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 0.500000 1.000000 0.500000 0.02938(18) Uani 1 2 d S . P . .
Cu2 Cu 0.500000 0.000000 1.000000 0.0377(2) Uani 1 2 d S . P . .
N1 N 0.4050(4) 0.8416(3) 0.55532(18) 0.0379(7) Uani 1 1 d . . . . .
C1 C 0.3250(6) 0.8566(4) 0.6208(2) 0.0477(10) Uani 1 1 d . . . . .
H1 H 0.309116 0.937362 0.629709 0.057 Uiso 1 1 calc R U . . .
N2 N 0.2660(5) 0.7759(3) 0.6740(2) 0.0511(9) Uani 1 1 d . . . . .
C2 C 0.2959(4) 0.6631(3) 0.6561(2) 0.0371(8) Uani 1 1 d . . . . .
C3 C 0.3730(4) 0.6343(3) 0.59157(19) 0.0317(7) Uani 1 1 d . . . . .
C4 C 0.4278(4) 0.7290(3) 0.5375(2) 0.0330(7) Uani 1 1 d . . . . .
N3 N 0.2612(4) 0.5581(3) 0.69986(18) 0.0388(7) Uani 1 1 d . . . . .
C5 C 0.3195(4) 0.4692(3) 0.6602(2) 0.0353(7) Uani 1 1 d . . . . .
N4 N 0.3866(3) 0.5111(3) 0.59361(17) 0.0333(6) Uani 1 1 d . . . . .
N5 N 0.4997(4) 0.7113(3) 0.47232(18) 0.0396(7) Uani 1 1 d . . . . .
H5A H 0.532927 0.772563 0.440208 0.048 Uiso 1 1 calc R U . . .
H5B H 0.513969 0.638215 0.461221 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1728(6) 0.5426(4) 0.7735(2) 0.0551(12) Uani 1 1 d . . . . .
H6A H 0.164911 0.618218 0.793999 0.066 Uiso 1 1 calc R U . . .
H6B H 0.227859 0.476776 0.809582 0.066 Uiso 1 1 calc R U . . .
C7 C 0.0072(7) 0.5112(5) 0.7651(3) 0.0681(14) Uani 1 1 d . . . . .
H7A H 0.016438 0.432603 0.747950 0.082 Uiso 1 1 calc R U . . .
H7B H -0.048746 0.501353 0.815352 0.082 Uiso 1 1 calc R U . . .
C8 C -0.0859(8) 0.6044(7) 0.7110(5) 0.089(2) Uani 1 1 d . . . . .
H8A H -0.038756 0.604426 0.659349 0.106 Uiso 1 1 calc R U . . .
H8B H -0.080079 0.685149 0.723149 0.106 Uiso 1 1 calc R U . . .
C9 C -0.2542(9) 0.5861(11) 0.7114(6) 0.120(3) Uani 1 1 d . . . . .
H9A H -0.304090 0.595506 0.761430 0.143 Uiso 1 1 calc R U . . .
H9B H -0.304893 0.650918 0.673178 0.143 Uiso 1 1 calc R U . . .
C10 C -0.2809(12) 0.4733(13) 0.6966(7) 0.142(5) Uani 1 1 d . . . . .
H10A H -0.393266 0.467992 0.702168 0.170 Uiso 1 1 calc R U . . .
H10B H -0.231105 0.408268 0.735087 0.170 Uiso 1 1 calc R U . . .
C11 C -0.2216(13) 0.4506(13) 0.6190(11) 0.192(8) Uani 1 1 d . . . . .
H11A H -0.279566 0.508126 0.580495 0.288 Uiso 1 1 calc R U . . .
H11B H -0.235017 0.367718 0.614893 0.288 Uiso 1 1 calc R U . . .
H11C H -0.111892 0.461338 0.611473 0.288 Uiso 1 1 calc R U . . .
C12 C 0.3174(5) 0.3447(4) 0.6940(2) 0.0396(8) Uani 1 1 d . . . . .
C13 C 0.3190(5) 0.2468(4) 0.7328(2) 0.0401(8) Uani 1 1 d . . . . .
C14 C 0.3268(4) 0.1308(3) 0.7820(2) 0.0371(8) Uani 1 1 d . . . . .
C15 C 0.3948(4) 0.1166(3) 0.8501(2) 0.0374(8) Uani 1 1 d . . . . .
H15 H 0.434420 0.183960 0.862424 0.045 Uiso 1 1 calc R U . . .
N6 N 0.4071(4) 0.0115(3) 0.89934(18) 0.0392(7) Uani 1 1 d . . . . .
C16 C 0.3532(5) -0.0832(4) 0.8812(2) 0.0459(10) Uani 1 1 d . . . . .
H16 H 0.364282 -0.158550 0.915338 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2817(6) -0.0758(4) 0.8148(3) 0.0514(11) Uani 1 1 d . . . . .
H17 H 0.244376 -0.144996 0.803721 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2652(6) 0.0328(4) 0.7650(2) 0.0457(9) Uani 1 1 d . . . . .
H18 H 0.212926 0.040819 0.719904 0.055 Uiso 1 1 calc R U . . .
O1 O 0.4111(3) 0.9848(3) 0.39258(18) 0.0461(7) Uani 1 1 d . . . . .
C19 C 0.2803(5) 1.0304(4) 0.3744(3) 0.0444(9) Uani 1 1 d . . . . .
C20 C 0.1669(5) 1.0972(4) 0.4148(3) 0.0491(10) Uani 1 1 d . . . . .
H20 H 0.069917 1.124130 0.393336 0.059 Uiso 1 1 calc R U . . .
C21 C 0.1890(4) 1.1253(3) 0.4830(2) 0.0418(9) Uani 1 1 d . . . . .
O2 O 0.3052(3) 1.0978(2) 0.52280(17) 0.0410(6) Uani 1 1 d . . . . .
C22 C 0.2419(6) 1.0131(6) 0.2960(3) 0.0651(14) Uani 1 1 d . . . . .
F1 F 0.2800(6) 0.8998(5) 0.2882(3) 0.1114(16) Uani 1 1 d . . . . .
F2 F 0.3227(5) 1.0780(6) 0.2428(2) 0.1128(17) Uani 1 1 d . . . . .
F3 F 0.0945(4) 1.0425(4) 0.2817(2) 0.0903(12) Uani 1 1 d . . . . .
C23 C 0.0585(5) 1.2013(5) 0.5201(3) 0.0563(11) Uani 1 1 d . . . . .
F4 F 0.1026(6) 1.3045(4) 0.5266(4) 0.124(2) Uani 1 1 d . . . . .
F5 F -0.0679(4) 1.2217(5) 0.4874(3) 0.1206(19) Uani 1 1 d . . . . .
F6 F 0.0261(5) 1.1482(4) 0.5898(2) 0.0981(13) Uani 1 1 d . . . . .
O3 O 0.6618(4) -0.1564(3) 0.97805(19) 0.0568(8) Uani 1 1 d . . . . .
C24 C 0.7894(6) -0.1455(5) 0.9455(3) 0.0543(11) Uani 1 1 d . . . . .
C25 C 0.8586(6) -0.0389(5) 0.9179(3) 0.0648(14) Uani 1 1 d . . . . .
H25 H 0.960044 -0.047257 0.894967 0.078 Uiso 1 1 calc R U . . .
C26 C 0.7906(5) 0.0753(5) 0.9216(2) 0.0508(10) Uani 1 1 d . . . . .
O4 O 0.6608(4) 0.1082(3) 0.94869(18) 0.0533(8) Uani 1 1 d . . . . .
C27 C 0.8791(10) -0.2670(7) 0.9338(5) 0.090(2) Uani 1 1 d . . . . .
F7 F 0.8075(9) -0.3138(6) 0.8871(4) 0.167(3) Uani 1 1 d . . . . .
F8 F 1.0201(7) -0.2613(5) 0.9083(5) 0.185(4) Uani 1 1 d . . . . .
F9 F 0.8803(6) -0.3481(4) 0.9957(4) 0.1181(17) Uani 1 1 d . . . . .
C28 C 0.8824(9) 0.1791(6) 0.8865(4) 0.0797(18) Uani 1 1 d . . . . .
F10 F 0.9025(12) 0.1939(7) 0.8168(3) 0.218(5) Uani 1 1 d . . . . .
F11 F 0.8486(9) 0.2713(6) 0.9127(6) 0.221(5) Uani 1 1 d . . . . .
F12 F 1.0368(6) 0.1529(6) 0.9015(4) 0.138(2) Uani 1 1 d . . . . .
O5 O 0.4541(12) 0.5727(10) 0.8867(4) 0.173(4) Uani 1 1 d D . . . .
H5C H 0.404(18) 0.531(10) 0.863(4) 0.210 Uiso 1 1 d D U . . .
H5D H 0.474(17) 0.555(10) 0.936(2) 0.210 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.967(3) 2_676 ?
Cu1 O2 1.967(3) . ?
Cu1 N1 2.117(3) . ?
Cu1 N1 2.117(3) 2_676 ?
Cu1 O1 2.194(3) 2_676 ?
Cu1 O1 2.194(3) . ?
Cu2 N6 2.026(4) 2_657 ?
Cu2 N6 2.026(4) . ?
Cu2 O4 2.038(3) 2_657 ?
Cu2 O4 2.038(3) . ?
Cu2 O3 2.196(4) 2_657 ?
Cu2 O3 2.196(4) . ?
N1 C1 1.355(5) . ?
N1 C4 1.360(5) . ?
C1 N2 1.316(5) . ?
C1 H1 0.9500 . ?
N2 C2 1.366(5) . ?
C2 N3 1.352(5) . ?
C2 C3 1.372(5) . ?
C3 N4 1.379(5) . ?
C3 C4 1.411(5) . ?
C4 N5 1.328(5) . ?
N3 C5 1.369(5) . ?
N3 C6 1.477(5) . ?
C5 N4 1.325(5) . ?
C5 C12 1.426(5) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C6 C7 1.564(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.495(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.409(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.513(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9805 . ?
C11 H11B 0.9804 . ?
C11 H11C 0.9804 . ?
C12 C13 1.192(6) . ?
C13 C14 1.434(5) . ?
C14 C15 1.382(6) . ?
C14 C18 1.392(6) . ?
C15 N6 1.338(5) . ?
C15 H15 0.9500 . ?
N6 C16 1.333(6) . ?
C16 C17 1.381(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1 C19 1.235(5) . ?
C19 C20 1.410(6) . ?
C19 C22 1.536(7) . ?
C20 C21 1.367(7) . ?
C20 H20 0.9500 . ?
C21 O2 1.264(5) . ?
C21 C23 1.528(6) . ?
C22 F2 1.311(7) . ?
C22 F1 1.314(8) . ?
C22 F3 1.322(6) . ?
C23 F5 1.270(6) . ?
C23 F4 1.308(7) . ?
C23 F6 1.313(6) . ?
O3 C24 1.230(6) . ?
C24 C25 1.411(8) . ?
C24 C27 1.535(9) . ?
C25 C26 1.362(8) . ?
C25 H25 0.9500 . ?
C26 O4 1.241(6) . ?
C26 C28 1.521(8) . ?
C27 F8 1.288(9) . ?
C27 F9 1.302(9) . ?
C27 F7 1.318(10) . ?
C28 F11 1.220(8) . ?
C28 F10 1.240(8) . ?
C28 F12 1.382(9) . ?
O5 H5C 0.88(5) . ?
O5 H5D 0.91(4) . ?

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
O2 Cu1 O2 180.0 2_676 . ?
O2 Cu1 N1 90.44(12) 2_676 . ?
O2 Cu1 N1 89.56(12) . . ?
O2 Cu1 N1 89.56(12) 2_676 2_676 ?
O2 Cu1 N1 90.44(12) . 2_676 ?
N1 Cu1 N1 180.0 . 2_676 ?
O2 Cu1 O1 89.06(12) 2_676 2_676 ?
O2 Cu1 O1 90.94(12) . 2_676 ?
N1 Cu1 O1 89.17(12) . 2_676 ?
N1 Cu1 O1 90.83(12) 2_676 2_676 ?
O2 Cu1 O1 90.95(12) 2_676 . ?
O2 Cu1 O1 89.05(12) . . ?
N1 Cu1 O1 90.83(12) . . ?
N1 Cu1 O1 89.17(12) 2_676 . ?
O1 Cu1 O1 180.0 2_676 . ?
N6 Cu2 N6 180.00(18) 2_657 . ?
N6 Cu2 O4 90.13(13) 2_657 2_657 ?
N6 Cu2 O4 89.87(13) . 2_657 ?
N6 Cu2 O4 89.87(13) 2_657 . ?
N6 Cu2 O4 90.13(13) . . ?
O4 Cu2 O4 180.0 2_657 . ?
N6 Cu2 O3 90.15(13) 2_657 2_657 ?
N6 Cu2 O3 89.85(13) . 2_657 ?
O4 Cu2 O3 87.94(13) 2_657 2_657 ?
O4 Cu2 O3 92.06(13) . 2_657 ?
N6 Cu2 O3 89.85(13) 2_657 . ?
N6 Cu2 O3 90.15(13) . . ?
O4 Cu2 O3 92.06(13) 2_657 . ?
O4 Cu2 O3 87.94(13) . . ?
O3 Cu2 O3 180.0 2_657 . ?
C1 N1 C4 118.6(3) . . ?
C1 N1 Cu1 112.4(3) . . ?
C4 N1 Cu1 128.6(2) . . ?
N2 C1 N1 129.6(4) . . ?
N2 C1 H1 115.2 . . ?
N1 C1 H1 115.2 . . ?
C1 N2 C2 110.6(3) . . ?
N3 C2 N2 126.5(3) . . ?
N3 C2 C3 107.0(3) . . ?
N2 C2 C3 126.4(4) . . ?
C2 C3 N4 110.6(3) . . ?
C2 C3 C4 118.0(3) . . ?
N4 C3 C4 131.4(3) . . ?
N5 C4 N1 120.5(3) . . ?
N5 C4 C3 122.7(3) . . ?
N1 C4 C3 116.8(3) . . ?
C2 N3 C5 105.6(3) . . ?
C2 N3 C6 127.3(3) . . ?
C5 N3 C6 127.0(3) . . ?
N4 C5 N3 113.5(3) . . ?
N4 C5 C12 126.0(3) . . ?
N3 C5 C12 120.2(3) . . ?
C5 N4 C3 103.3(3) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N3 C6 C7 110.8(4) . . ?
N3 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 114.0(5) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 114.7(7) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 115.1(9) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 114.3(10) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.4 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.4 . . ?
H11B C11 H11C 109.4 . . ?
C13 C12 C5 169.5(4) . . ?
C12 C13 C14 176.8(5) . . ?
C15 C14 C18 118.6(4) . . ?
C15 C14 C13 118.6(4) . . ?
C18 C14 C13 122.7(4) . . ?
N6 C15 C14 122.5(4) . . ?
N6 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C16 N6 C15 118.4(4) . . ?
C16 N6 Cu2 121.4(3) . . ?
C15 N6 Cu2 120.1(3) . . ?
N6 C16 C17 122.5(4) . . ?
N6 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C14 118.6(4) . . ?
C17 C18 H18 120.7 . . ?
C14 C18 H18 120.7 . . ?
C19 O1 Cu1 121.8(3) . . ?
O1 C19 C20 128.7(4) . . ?
O1 C19 C22 113.8(4) . . ?
C20 C19 C22 117.4(4) . . ?
C21 C20 C19 123.5(4) . . ?
C21 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
O2 C21 C20 129.6(4) . . ?
O2 C21 C23 111.8(4) . . ?
C20 C21 C23 118.6(4) . . ?
C21 O2 Cu1 127.1(3) . . ?
F2 C22 F1 106.0(6) . . ?
F2 C22 F3 107.7(5) . . ?
F1 C22 F3 107.5(5) . . ?
F2 C22 C19 110.6(5) . . ?
F1 C22 C19 110.7(5) . . ?
F3 C22 C19 114.0(5) . . ?
F5 C23 F4 109.1(5) . . ?
F5 C23 F6 106.1(5) . . ?
F4 C23 F6 104.6(5) . . ?
F5 C23 C21 115.4(5) . . ?
F4 C23 C21 110.4(4) . . ?
F6 C23 C21 110.7(4) . . ?
C24 O3 Cu2 122.4(3) . . ?
O3 C24 C25 128.8(5) . . ?
O3 C24 C27 112.9(5) . . ?
C25 C24 C27 118.3(5) . . ?
C26 C25 C24 124.7(5) . . ?
C26 C25 H25 117.6 . . ?
C24 C25 H25 117.6 . . ?
O4 C26 C25 129.1(5) . . ?
O4 C26 C28 114.0(5) . . ?
C25 C26 C28 116.9(5) . . ?
C26 O4 Cu2 127.0(3) . . ?
F8 C27 F9 107.5(8) . . ?
F8 C27 F7 108.4(7) . . ?
F9 C27 F7 103.8(7) . . ?
F8 C27 C24 114.8(7) . . ?
F9 C27 C24 112.1(6) . . ?
F7 C27 C24 109.7(7) . . ?
F11 C28 F10 115.8(9) . . ?
F11 C28 F12 100.6(7) . . ?
F10 C28 F12 96.1(7) . . ?
F11 C28 C26 114.9(6) . . ?
F10 C28 C26 114.6(6) . . ?
F12 C28 C26 112.1(6) . . ?
H5C O5 H5D 127(5) . . ?

_refine_diff_density_max         1.771
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.131

