# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_298-11Co
_database_code_depnum_ccdc_archive 'CCDC 1536677'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 Co N2 O10'
_chemical_formula_weight         575.34

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4612(4)
_cell_length_b                   9.1588(3)
_cell_length_c                   14.0450(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.333(4)
_cell_angle_gamma                90
_cell_volume                     1155.26(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3614
_cell_measurement_theta_min      3.781
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             586
_exptl_transmission_factor_min   0.816
_exptl_transmission_factor_max   0.837
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.811
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3614
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.781
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2041
_reflns_number_gt                1756
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0440P)²+0.6779P] 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         2041
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Co1 Co 0.5000 0.0000 0.0000 0.01873(16) Uani 1 2 d S . P . .
N1 N 0.8090(2) 0.3839(2) 0.41544(14) 0.0225(5) Uani 1 1 d . . . . .
O1 O 0.53200(19) 0.14945(19) 0.11690(12) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.6579(2) 0.3543(2) 0.10765(13) 0.0412(5) Uani 1 1 d . . . . .
H2 H 0.6332 0.3340 0.0478 0.062 Uiso 1 1 calc R U . . .
O3 O 0.5066(2) 0.1894(3) 0.46924(14) 0.0479(6) Uani 1 1 d . . . . .
O4 O 0.64256(19) 0.11068(19) 0.93321(12) 0.0282(4) Uani 1 1 d . . . . .
O5 O 0.6117(2) 0.3524(2) 0.92602(13) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.6079(3) 0.2588(3) 0.15343(18) 0.0230(5) Uani 1 1 d . . . . .
C2 C 0.6448(3) 0.2824(3) 0.26457(17) 0.0222(5) Uani 1 1 d . . . . .
C3 C 0.7678(3) 0.3656(3) 0.31585(17) 0.0226(5) Uani 1 1 d . . . . .
H3 H 0.8234 0.4100 0.2799 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7244(3) 0.3249(3) 0.46607(18) 0.0267(6) Uani 1 1 d . . . . .
H4 H 0.7519 0.3384 0.5351 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5981(3) 0.2447(3) 0.41944(18) 0.0288(6) Uani 1 1 d . . . . .
C6 C 0.5598(3) 0.2202(3) 0.31742(18) 0.0297(6) Uani 1 1 d . . . . .
H6 H 0.4779 0.1626 0.2849 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5487(3) 0.2074(3) 0.57396(19) 0.0335(7) Uani 1 1 d . . . . .
C8 C 0.6453(3) 0.1099(3) 0.6351(2) 0.0382(7) Uani 1 1 d . . . . .
H8 H 0.6920 0.0389 0.6083 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6720(3) 0.1191(3) 0.7378(2) 0.0340(6) Uani 1 1 d . . . . .
H9 H 0.7339 0.0511 0.7802 0.041 Uiso 1 1 calc R U . . .
C10 C 0.6075(3) 0.2284(3) 0.77756(18) 0.0243(5) Uani 1 1 d . . . . .
C11 C 0.6234(3) 0.2285(3) 0.88712(18) 0.0247(6) Uani 1 1 d . . . . .
C12 C 0.5166(3) 0.3308(3) 0.71424(19) 0.0329(6) Uani 1 1 d . . . . .
H12 H 0.4769 0.4077 0.7409 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4851(3) 0.3182(3) 0.6113(2) 0.0379(7) Uani 1 1 d . . . . .
H13 H 0.4215 0.3842 0.5682 0.045 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
Co1 O1 2.0853(16) . ?
Co1 O1 2.0853(16) 3_655 ?
Co1 N1 2.1111(19) 4_565 ?
Co1 N1 2.1111(19) 2_645 ?
Co1 O4 2.1267(17) 1_554 ?
Co1 O4 2.1267(17) 3_656 ?
N1 C3 1.339(3) . ?
N1 C4 1.340(3) . ?
N1 Co1 2.1111(19) 2_655 ?
O1 C1 1.245(3) . ?
O2 C1 1.262(3) . ?
O2 H2 0.8200 . ?
O3 C5 1.370(3) . ?
O3 C7 1.407(3) . ?
O4 C11 1.242(3) . ?
O4 Co1 2.1267(17) 1_556 ?
O5 C11 1.279(3) . ?
C1 C2 1.504(3) . ?
C2 C6 1.377(3) . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C13 1.365(4) . ?
C7 C8 1.370(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.388(4) . ?
C10 C11 1.498(3) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 180.0 . 3_655 ?
O1 Co1 N1 89.95(7) . 4_565 ?
O1 Co1 N1 90.05(7) 3_655 4_565 ?
O1 Co1 N1 90.05(7) . 2_645 ?
O1 Co1 N1 89.95(7) 3_655 2_645 ?
N1 Co1 N1 180.00(17) 4_565 2_645 ?
O1 Co1 O4 94.55(7) . 1_554 ?
O1 Co1 O4 85.45(7) 3_655 1_554 ?
N1 Co1 O4 93.52(7) 4_565 1_554 ?
N1 Co1 O4 86.48(7) 2_645 1_554 ?
O1 Co1 O4 85.45(7) . 3_656 ?
O1 Co1 O4 94.55(7) 3_655 3_656 ?
N1 Co1 O4 86.49(7) 4_565 3_656 ?
N1 Co1 O4 93.51(7) 2_645 3_656 ?
O4 Co1 O4 180.0 1_554 3_656 ?
C3 N1 C4 118.5(2) . . ?
C3 N1 Co1 124.53(16) . 2_655 ?
C4 N1 Co1 116.93(15) . 2_655 ?
C1 O1 Co1 140.77(16) . . ?
C1 O2 H2 109.5 . . ?
C5 O3 C7 118.3(2) . . ?
C11 O4 Co1 129.43(16) . 1_556 ?
O1 C1 O2 127.4(2) . . ?
O1 C1 C2 117.3(2) . . ?
O2 C1 C2 115.3(2) . . ?
C6 C2 C3 118.9(2) . . ?
C6 C2 C1 121.1(2) . . ?
C3 C2 C1 120.0(2) . . ?
N1 C3 C2 122.1(2) . . ?
N1 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
N1 C4 C5 122.4(2) . . ?
N1 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
O3 C5 C4 123.1(2) . . ?
O3 C5 C6 117.9(2) . . ?
C4 C5 C6 119.0(2) . . ?
C2 C6 C5 119.0(2) . . ?
C2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C13 C7 C8 122.1(2) . . ?
C13 C7 O3 118.3(3) . . ?
C8 C7 O3 119.5(3) . . ?
C7 C8 C9 118.7(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C12 119.7(2) . . ?
C9 C10 C11 120.1(2) . . ?
C12 C10 C11 120.0(2) . . ?
O4 C11 O5 124.5(2) . . ?
O4 C11 C10 119.1(2) . . ?
O5 C11 C10 116.4(2) . . ?
C13 C12 C10 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C10 C12 H12 120.1 . . ?
C7 C13 C12 119.1(3) . . ?
C7 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 O2 30.7(4) . . . . ?
Co1 O1 C1 C2 -149.65(19) . . . . ?
O1 C1 C2 C6 -22.0(4) . . . . ?
O2 C1 C2 C6 157.6(2) . . . . ?
O1 C1 C2 C3 156.7(2) . . . . ?
O2 C1 C2 C3 -23.6(3) . . . . ?
C4 N1 C3 C2 -2.9(4) . . . . ?
Co1 N1 C3 C2 176.92(18) 2_655 . . . ?
C6 C2 C3 N1 1.9(4) . . . . ?
C1 C2 C3 N1 -176.8(2) . . . . ?
C3 N1 C4 C5 0.8(4) . . . . ?
Co1 N1 C4 C5 -179.0(2) 2_655 . . . ?
C7 O3 C5 C4 -4.2(4) . . . . ?
C7 O3 C5 C6 176.8(3) . . . . ?
N1 C4 C5 O3 -176.8(2) . . . . ?
N1 C4 C5 C6 2.2(4) . . . . ?
C3 C2 C6 C5 1.1(4) . . . . ?
C1 C2 C6 C5 179.9(2) . . . . ?
O3 C5 C6 C2 176.0(2) . . . . ?
C4 C5 C6 C2 -3.1(4) . . . . ?
C5 O3 C7 C13 99.1(3) . . . . ?
C5 O3 C7 C8 -84.3(3) . . . . ?
C13 C7 C8 C9 3.9(4) . . . . ?
O3 C7 C8 C9 -172.6(2) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C8 C9 C10 C12 -0.8(4) . . . . ?
C8 C9 C10 C11 173.4(3) . . . . ?
Co1 O4 C11 O5 64.2(3) 1_556 . . . ?
Co1 O4 C11 C10 -113.7(2) 1_556 . . . ?
C9 C10 C11 O4 -26.8(4) . . . . ?
C12 C10 C11 O4 147.3(3) . . . . ?
C9 C10 C11 O5 155.1(3) . . . . ?
C12 C10 C11 O5 -30.8(3) . . . . ?
C9 C10 C12 C13 3.3(4) . . . . ?
C11 C10 C12 C13 -170.9(3) . . . . ?
C8 C7 C13 C12 -1.4(4) . . . . ?
O3 C7 C13 C12 175.1(2) . . . . ?
C10 C12 C13 C7 -2.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O1 0.93 2.54 3.022(3) 112.8 4_666
O2 H2 O5 0.82 1.67 2.449(2) 158.9 1_554
O2 H2 O4 0.82 2.62 3.283(2) 138.9 1_554
C4 H4 O1 0.93 2.54 3.022(3) 112.8 4_666
O2 H2 O5 0.82 1.67 2.449(2) 158.9 1_554
O2 H2 O4 0.82 2.62 3.283(2) 138.9 1_554
C4 H4 O1 0.93 2.54 3.022(3) 112.8 4_666
O2 H2 O5 0.82 1.67 2.449(2) 158.9 1_554
O2 H2 O4 0.82 2.62 3.283(2) 138.9 1_554
O2 H2 O4 0.82 2.62 3.283(2) 138.9 1_554
O2 H2 O5 0.82 1.67 2.449(2) 158.9 1_554
C4 H4 O1 0.93 2.54 3.022(3) 112.8 4_666

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_291-1Cd
_database_code_depnum_ccdc_archive 'CCDC 1536682'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_audit_creation_date             2016-11-14
_chemical_formula_sum            'C23 H19 Cd N3 O7'
_chemical_formula_weight         561.810
_refine_ls_R_factor_all          0.040
_cell_length_a                   14.1855(5)
_cell_length_b                   10.1391(3)
_cell_length_c                   16.7657(6)
_cell_angle_alpha                90.000
_cell_angle_beta                 108.483(4)
_cell_angle_gamma                90.000
_cell_volume                     2287.0(1)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P_2ybc

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Cd ? 1.200
N ? 1.200
O ? 1.200
H ? 1.200
C ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
Cd1 Cd 0.1438(0) 0.1286(0) 0.1193(0) 1.000 4 e ? d Uani 0.03272(10)
N1 N 0.1539(2) 0.2414(3) 0.2406(2) 1.000 4 e ? d Uani 0.0332(6)
N2 N 0.2376(2) 0.3071(3) 0.0806(2) 1.000 4 e ? d Uani 0.0490(8)
N3 N 0.0421(2) 0.2588(3) 0.0091(2) 1.000 4 e ? d Uani 0.0397(7)
O1 O -0.0944(2) 0.4316(3) 0.2649(2) 1.000 4 e ? d Uani 0.0538(7)
O2 O -0.0019(2) 0.5328(3) 0.3802(2) 1.000 4 e ? d Uani 0.0515(7)
O3 O 0.3386(2) 0.3371(3) 0.4362(1) 1.000 4 e ? d Uani 0.0427(6)
O4 O 0.6883(2) 0.5480(3) 0.3097(2) 1.000 4 e ? d Uani 0.0519(7)
O5 O 0.7732(2) 0.4793(2) 0.4367(1) 1.000 4 e ? d Uani 0.0409(6)
O7 O 0.1870(4) 0.7333(6) 0.3459(4) 1.000 4 e ? d Uani 0.206(3)
H3W H 0.1983 0.7732 0.3223 1.000 4 e ? d Uiso 0.24700
H4W H 0.1561 0.7933 0.3114 1.000 4 e ? d Uiso 0.24700
C1 C -0.0143(2) 0.4540(3) 0.3195(2) 1.000 4 e ? d Uani 0.0363(8)
C2 C 0.0781(2) 0.3844(3) 0.3157(2) 1.000 4 e ? d Uani 0.0311(7)
C3 C 0.0745(2) 0.3058(3) 0.2482(2) 1.000 4 e ? d Uani 0.0318(7)
H3 H 0.0142 0.2968 0.2055 1.000 4 e ? calc Uiso 0.03800
C4 C 0.2400(2) 0.2524(3) 0.3023(2) 1.000 4 e ? d Uani 0.0370(8)
H4 H 0.2951 0.2063 0.2985 1.000 4 e ? calc Uiso 0.04400
C5 C 0.2495(2) 0.3307(3) 0.3718(2) 1.000 4 e ? d Uani 0.0326(7)
C6 C 0.1692(2) 0.3985(3) 0.3792(2) 1.000 4 e ? d Uani 0.0324(7)
H6 H 0.1751 0.4526 0.4253 1.000 4 e ? calc Uiso 0.03900
C7 C 0.4234(2) 0.3698(3) 0.4160(2) 1.000 4 e ? d Uani 0.0345(8)
C8 C 0.4203(2) 0.4480(4) 0.3484(2) 1.000 4 e ? d Uani 0.0459(9)
H8 H 0.3597 0.4770 0.3120 1.000 4 e ? calc Uiso 0.05500
C9 C 0.5082(2) 0.4830(4) 0.3352(2) 1.000 4 e ? d Uani 0.0470(9)
H9 H 0.5064 0.5345 0.2888 1.000 4 e ? calc Uiso 0.05600
C10 C 0.5988(2) 0.4429(4) 0.3895(2) 1.000 4 e ? d Uani 0.0365(8)
C11 C 0.6924(2) 0.4915(4) 0.3772(2) 1.000 4 e ? d Uani 0.0399(8)
C12 C 0.6002(2) 0.3657(3) 0.4585(2) 1.000 4 e ? d Uani 0.0396(8)
H12 H 0.6607 0.3391 0.4962 1.000 4 e ? calc Uiso 0.04700
C13 C 0.5124(2) 0.3279(4) 0.4713(2) 1.000 4 e ? d Uani 0.0378(8)
H13 H 0.5136 0.2748 0.5169 1.000 4 e ? calc Uiso 0.04500
C14 C 0.3345(3) 0.3289(5) 0.1178(3) 1.000 4 e ? d Uani 0.0669(12)
H14 H 0.3672 0.2802 0.1655 1.000 4 e ? calc Uiso 0.08000
C15 C 0.3887(4) 0.4195(6) 0.0893(4) 1.000 4 e ? d Uani 0.0822(16)
H15 H 0.4560 0.4326 0.1172 1.000 4 e ? calc Uiso 0.09900
O6 O 0.3545(5) 0.8682(7) 0.3317(4) 1.000 4 e ? d Uani 0.214(3)
H1W H 0.3418 0.9206 0.2900 1.000 4 e ? d Uiso 0.25700
H2W H 0.3437 0.8275 0.3553 1.000 4 e ? d Uiso 0.25700
C16 C 0.3398(4) 0.4899(5) 0.0183(4) 1.000 4 e ? d Uani 0.0944(18)
H16 H 0.3741 0.5509 -0.0034 1.000 4 e ? calc Uiso 0.11300
C17 C 0.2405(4) 0.4697(5) -0.0204(3) 1.000 4 e ? d Uani 0.0771(14)
H17 H 0.2070 0.5172 -0.0685 1.000 4 e ? calc Uiso 0.09300
C18 C 0.1899(3) 0.3785(4) 0.0122(3) 1.000 4 e ? d Uani 0.0478(10)
C19 C 0.0823(3) 0.3539(3) -0.0262(2) 1.000 4 e ? d Uani 0.0427(9)
C20 C 0.0234(4) 0.4239(4) -0.0948(3) 1.000 4 e ? d Uani 0.0602(11)
H20 H 0.0513 0.4890 -0.1193 1.000 4 e ? calc Uiso 0.07200
C21 C -0.0756(4) 0.3970(4) -0.1265(3) 1.000 4 e ? d Uani 0.0679(13)
H21 H -0.1153 0.4437 -0.1727 1.000 4 e ? calc Uiso 0.08100
C22 C -0.1165(3) 0.3024(4) -0.0907(3) 1.000 4 e ? d Uani 0.0583(11)
H22 H -0.1841 0.2837 -0.1115 1.000 4 e ? calc Uiso 0.07000
C23 C -0.0554(3) 0.2349(4) -0.0230(2) 1.000 4 e ? d Uani 0.0465(9)
H23 H -0.0831 0.1696 0.0016 1.000 4 e ? calc Uiso 0.05600



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cd1 O2 . 2_545 2.237(2) no
Cd1 O5 . 2_645 2.294(2) no
Cd1 N1 . . 2.298(3) no
Cd1 N3 . . 2.356(3) no
Cd1 O4 . 2_645 2.441(2) no
Cd1 N2 . . 2.453(3) no
Cd1 C11 . 2_645 2.692(3) no
N1 C4 . . 1.333(4) no
N1 C3 . . 1.342(4) no
N2 C14 . . 1.335(5) no
N2 C18 . . 1.344(5) no
N3 C23 . . 1.338(4) no
N3 C19 . . 1.348(4) no
O1 C1 . . 1.234(4) no
O2 C1 . . 1.262(4) no
O2 Cd1 . 2 2.237(2) no
O3 C5 . . 1.380(4) no
O3 C7 . . 1.390(4) no
O4 C11 . . 1.254(4) no
O4 Cd1 . 2_655 2.441(2) no
O5 C11 . . 1.264(4) no
O5 Cd1 . 2_655 2.294(2) no
O7 H3W . . 0.6205 no
O7 H4W . . 0.8577 no
C1 C2 . . 1.507(4) no
C2 C3 . . 1.372(4) no
C2 C6 . . 1.397(4) no
C3 H3 . . 0.9300 no
C4 C5 . . 1.380(4) no
C4 H4 . . 0.9300 no
C5 C6 . . 1.369(4) no
C6 H6 . . 0.9300 no
C7 C8 . . 1.371(5) no
C7 C13 . . 1.376(4) no
C8 C9 . . 1.382(5) no
C8 H8 . . 0.9300 no
C9 C10 . . 1.380(5) no
C9 H9 . . 0.9300 no
C10 C12 . . 1.391(5) no
C10 C11 . . 1.491(4) no
C11 Cd1 . 2_655 2.692(3) no
C12 C13 . . 1.384(4) no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 C15 . . 1.377(6) no
C14 H14 . . 0.9300 no
C15 C16 . . 1.372(8) no
C15 H15 . . 0.9300 no
O6 H1W . . 0.8500 no
O6 H2W . . 0.6239 no
C16 C17 . . 1.367(7) no
C16 H16 . . 0.9300 no
C17 C18 . . 1.386(5) no
C17 H17 . . 0.9300 no
C18 C19 . . 1.477(5) no
C19 C20 . . 1.385(5) no
C20 C21 . . 1.362(6) no
C20 H20 . . 0.9300 no
C21 C22 . . 1.355(6) no
C21 H21 . . 0.9300 no
C22 C23 . . 1.372(5) no
C22 H22 . . 0.9300 no
C23 H23 . . 0.9300 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cd1 O5 2_545 . 2_645 107.10(9) no
O2 Cd1 N1 2_545 . . 90.96(9) no
O5 Cd1 N1 2_645 . . 142.63(8) no
O2 Cd1 N3 2_545 . . 85.33(9) no
O5 Cd1 N3 2_645 . . 108.37(9) no
N1 Cd1 N3 . . . 105.43(9) no
O2 Cd1 O4 2_545 . 2_645 126.35(9) no
O5 Cd1 O4 2_645 . 2_645 55.29(8) no
N1 Cd1 O4 . . 2_645 87.57(8) no
N3 Cd1 O4 . . 2_645 146.12(9) no
O2 Cd1 N2 2_545 . . 152.34(10) no
O5 Cd1 N2 2_645 . . 89.24(9) no
N1 Cd1 N2 . . . 88.85(10) no
N3 Cd1 N2 . . . 68.13(10) no
O4 Cd1 N2 2_645 . . 81.28(10) no
O2 Cd1 C11 2_545 . 2_645 123.17(11) no
O5 Cd1 C11 2_645 . 2_645 27.93(9) no
N1 Cd1 C11 . . 2_645 115.26(10) no
N3 Cd1 C11 . . 2_645 128.01(10) no
O4 Cd1 C11 2_645 . 2_645 27.73(9) no
N2 Cd1 C11 . . 2_645 81.34(10) no
C4 N1 C3 . . . 118.4(3) no
C4 N1 Cd1 . . . 120.9(2) no
C3 N1 Cd1 . . . 120.5(2) no
C14 N2 C18 . . . 118.3(4) no
C14 N2 Cd1 . . . 124.3(3) no
C18 N2 Cd1 . . . 117.0(2) no
C23 N3 C19 . . . 118.8(3) no
C23 N3 Cd1 . . . 120.8(2) no
C19 N3 Cd1 . . . 120.4(2) no
C1 O2 Cd1 . . 2 112.5(2) no
C5 O3 C7 . . . 118.0(2) no
C11 O4 Cd1 . . 2_655 87.33(19) no
C11 O5 Cd1 . . 2_655 93.8(2) no
H3W O7 H4W . . . 44.60 no
O1 C1 O2 . . . 125.1(3) no
O1 C1 C2 . . . 119.5(3) no
O2 C1 C2 . . . 115.5(3) no
C3 C2 C6 . . . 118.1(3) no
C3 C2 C1 . . . 120.1(3) no
C6 C2 C1 . . . 121.8(3) no
N1 C3 C2 . . . 123.3(3) no
N1 C3 H3 . . . 118.40 no
C2 C3 H3 . . . 118.40 no
N1 C4 C5 . . . 121.6(3) no
N1 C4 H4 . . . 119.20 no
C5 C4 H4 . . . 119.20 no
C6 C5 O3 . . . 119.2(3) no
C6 C5 C4 . . . 120.3(3) no
O3 C5 C4 . . . 120.5(3) no
C5 C6 C2 . . . 118.4(3) no
C5 C6 H6 . . . 120.80 no
C2 C6 H6 . . . 120.80 no
C8 C7 C13 . . . 121.2(3) no
C8 C7 O3 . . . 122.4(3) no
C13 C7 O3 . . . 116.2(3) no
C7 C8 C9 . . . 119.1(3) no
C7 C8 H8 . . . 120.40 no
C9 C8 H8 . . . 120.40 no
C10 C9 C8 . . . 121.2(3) no
C10 C9 H9 . . . 119.40 no
C8 C9 H9 . . . 119.40 no
C9 C10 C12 . . . 118.7(3) no
C9 C10 C11 . . . 119.7(3) no
C12 C10 C11 . . . 121.5(3) no
O4 C11 O5 . . . 121.9(3) no
O4 C11 C10 . . . 119.2(3) no
O5 C11 C10 . . . 118.9(3) no
O4 C11 Cd1 . . 2_655 64.94(18) no
O5 C11 Cd1 . . 2_655 58.23(16) no
C10 C11 Cd1 . . 2_655 165.5(2) no
C13 C12 C10 . . . 120.6(3) no
C13 C12 H12 . . . 119.70 no
C10 C12 H12 . . . 119.70 no
C7 C13 C12 . . . 119.2(3) no
C7 C13 H13 . . . 120.40 no
C12 C13 H13 . . . 120.40 no
N2 C14 C15 . . . 123.7(5) no
N2 C14 H14 . . . 118.20 no
C15 C14 H14 . . . 118.20 no
C16 C15 C14 . . . 117.6(5) no
C16 C15 H15 . . . 121.20 no
C14 C15 H15 . . . 121.20 no
H1W O6 H2W . . . 154.70 no
C17 C16 C15 . . . 119.7(5) no
C17 C16 H16 . . . 120.10 no
C15 C16 H16 . . . 120.10 no
C16 C17 C18 . . . 119.8(5) no
C16 C17 H17 . . . 120.10 no
C18 C17 H17 . . . 120.10 no
N2 C18 C17 . . . 120.8(4) no
N2 C18 C19 . . . 116.9(3) no
C17 C18 C19 . . . 122.2(4) no
N3 C19 C20 . . . 120.2(4) no
N3 C19 C18 . . . 116.9(3) no
C20 C19 C18 . . . 123.0(4) no
C21 C20 C19 . . . 119.9(4) no
C21 C20 H20 . . . 120.10 no
C19 C20 H20 . . . 120.10 no
C22 C21 C20 . . . 120.2(4) no
C22 C21 H21 . . . 119.90 no
C20 C21 H21 . . . 119.90 no
C21 C22 C23 . . . 118.2(4) no
C21 C22 H22 . . . 120.90 no
C23 C22 H22 . . . 120.90 no
N3 C23 C22 . . . 122.9(4) no
N3 C23 H23 . . . 118.60 no
C22 C23 H23 . . . 118.60 no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cd1 O2 C1 O1 2 . . . 0.8(5) no
Cd1 O2 C1 C2 2 . . . -179.3(2) no
O1 C1 C2 C3 . . . . 5.7(5) no
O2 C1 C2 C3 . . . . -174.2(3) no
O1 C1 C2 C6 . . . . -175.1(3) no
O2 C1 C2 C6 . . . . 5.1(5) no
C4 N1 C3 C2 . . . . 1.1(5) no
Cd1 N1 C3 C2 . . . . -174.0(2) no
C6 C2 C3 N1 . . . . 0.5(5) no
C1 C2 C3 N1 . . . . 179.8(3) no
C3 N1 C4 C5 . . . . -1.7(5) no
Cd1 N1 C4 C5 . . . . 173.4(2) no
C7 O3 C5 C6 . . . . -128.8(3) no
C7 O3 C5 C4 . . . . 54.0(4) no
N1 C4 C5 C6 . . . . 0.6(5) no
N1 C4 C5 O3 . . . . 177.8(3) no
O3 C5 C6 C2 . . . . -176.2(3) no
C4 C5 C6 C2 . . . . 1.1(5) no
C3 C2 C6 C5 . . . . -1.6(5) no
C1 C2 C6 C5 . . . . 179.1(3) no
C5 O3 C7 C8 . . . . 29.0(5) no
C5 O3 C7 C13 . . . . -155.9(3) no
C13 C7 C8 C9 . . . . 1.2(6) no
O3 C7 C8 C9 . . . . 176.0(3) no
C7 C8 C9 C10 . . . . -1.3(6) no
C8 C9 C10 C12 . . . . 0.2(6) no
C8 C9 C10 C11 . . . . -175.0(4) no
Cd1 O4 C11 O5 2_655 . . . -12.7(3) no
Cd1 O4 C11 C10 2_655 . . . 164.4(3) no
Cd1 O5 C11 O4 2_655 . . . 13.6(4) no
Cd1 O5 C11 C10 2_655 . . . -163.6(3) no
C9 C10 C11 O4 . . . . -13.0(5) no
C12 C10 C11 O4 . . . . 172.0(3) no
C9 C10 C11 O5 . . . . 164.2(3) no
C12 C10 C11 O5 . . . . -10.8(5) no
C9 C10 C11 Cd1 . . . 2_655 89.9(10) no
C12 C10 C11 Cd1 . . . 2_655 -85.2(11) no
C9 C10 C12 C13 . . . . 1.1(5) no
C11 C10 C12 C13 . . . . 176.2(3) no
C8 C7 C13 C12 . . . . 0.1(5) no
O3 C7 C13 C12 . . . . -175.1(3) no
C10 C12 C13 C7 . . . . -1.3(5) no
C18 N2 C14 C15 . . . . -0.8(6) no
Cd1 N2 C14 C15 . . . . 172.2(3) no
N2 C14 C15 C16 . . . . -0.6(8) no
C14 C15 C16 C17 . . . . 1.1(8) no
C15 C16 C17 C18 . . . . -0.1(8) no
C14 N2 C18 C17 . . . . 1.9(6) no
Cd1 N2 C18 C17 . . . . -171.7(3) no
C14 N2 C18 C19 . . . . -178.7(3) no
Cd1 N2 C18 C19 . . . . 7.8(4) no
C16 C17 C18 N2 . . . . -1.4(7) no
C16 C17 C18 C19 . . . . 179.1(4) no
C23 N3 C19 C20 . . . . -0.7(5) no
Cd1 N3 C19 C20 . . . . 175.4(3) no
C23 N3 C19 C18 . . . . 179.0(3) no
Cd1 N3 C19 C18 . . . . -5.0(4) no
N2 C18 C19 N3 . . . . -2.2(5) no
C17 C18 C19 N3 . . . . 177.3(3) no
N2 C18 C19 C20 . . . . 177.5(3) no
C17 C18 C19 C20 . . . . -3.1(6) no
N3 C19 C20 C21 . . . . 0.4(6) no
C18 C19 C20 C21 . . . . -179.2(4) no
C19 C20 C21 C22 . . . . 0.2(7) no
C20 C21 C22 C23 . . . . -0.6(7) no
C19 N3 C23 C22 . . . . 0.3(5) no
Cd1 N3 C23 C22 . . . . -175.7(3) no
C21 C22 C23 N3 . . . . 0.3(6) no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O7 H3W O1 . . 2 0.6200 2.3500 2.769(6) 127.20 no
O7 H3W O1 . . 2 0.6200 2.3500 2.769(6) 127.20 no
O6 H2W O7 . . . 0.6200 2.3800 2.816(9) 129.60 no
O6 H1W O4 . . 2_655 0.8500 2.0500 2.898(6) 179.60 no
####################################################################### 
# 
# 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_290-7Mn
_database_code_depnum_ccdc_archive 'CCDC 1536678'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 Mn N O6'
_chemical_formula_weight         330.15

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.6232(4)
_cell_length_b                   7.9638(3)
_cell_length_c                   23.9856(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.567(3)
_cell_angle_gamma                90
_cell_volume                     2573.22(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4708
_cell_measurement_theta_min      3.318
_cell_measurement_theta_max      25.037

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   0.768
_exptl_transmission_factor_max   0.793
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.054
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4708
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.318
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_full        25.037
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2277
_reflns_number_gt                2009
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0273P)²+2.6798P] 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         2277
_refine_ls_number_parameters     198
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
Mn1 Mn 0.05280(2) 1.13383(4) 0.45819(2) 0.02024(12) Uani 1 1 d . . . . .
N1 N 0.42339(12) 0.7405(2) 0.40263(7) 0.0231(4) Uani 1 1 d . . . . .
O1 O 0.20682(10) 1.0180(2) 0.46937(6) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.11723(10) 1.0351(2) 0.38525(6) 0.0270(4) Uani 1 1 d . . . . .
O3 O 0.34142(11) 0.7874(3) 0.25455(7) 0.0463(5) Uani 1 1 d . . . . .
O4 O -0.04905(14) 0.6617(2) 0.08079(8) 0.0438(5) Uani 1 1 d . . . . .
O5 O 0.01449(11) 0.87836(19) 0.03936(6) 0.0264(4) Uani 1 1 d . . . . .
O6 O 0.11891(13) 1.3774(2) 0.46899(8) 0.0395(5) Uani 1 1 d D . . . .
C1 C 0.19335(14) 0.9870(3) 0.41716(9) 0.0220(5) Uani 1 1 d . . . . .
C2 C 0.27067(14) 0.8921(3) 0.39184(9) 0.0222(5) Uani 1 1 d . . . . .
C3 C 0.35150(15) 0.8190(3) 0.42508(9) 0.0233(5) Uani 1 1 d . . . . .
H3 H 0.3559 0.8247 0.4641 0.028 Uiso 1 1 calc R U . . .
C4 C 0.41570(15) 0.7307(3) 0.34654(9) 0.0276(5) Uani 1 1 d . . . . .
H4 H 0.4656 0.6770 0.3308 0.033 Uiso 1 1 calc R U . . .
C5 C 0.33607(15) 0.7977(3) 0.31113(9) 0.0294(5) Uani 1 1 d . . . . .
C6 C 0.26261(15) 0.8804(3) 0.33399(9) 0.0272(5) Uani 1 1 d . . . . .
H6 H 0.2087 0.9273 0.3109 0.033 Uiso 1 1 calc R U . . .
C7 C 0.25566(17) 0.7916(3) 0.21465(9) 0.0332(6) Uani 1 1 d . . . . .
C8 C 0.26677(17) 0.8607(3) 0.16376(10) 0.0343(6) Uani 1 1 d . . . . .
H8 H 0.3269 0.9090 0.1585 0.041 Uiso 1 1 calc R U . . .
C9 C 0.18751(16) 0.8581(3) 0.12001(10) 0.0303(6) Uani 1 1 d . . . . .
H9 H 0.1942 0.9062 0.0855 0.036 Uiso 1 1 calc R U . . .
C10 C 0.09848(16) 0.7841(3) 0.12771(9) 0.0256(5) Uani 1 1 d . . . . .
C11 C 0.01474(16) 0.7704(3) 0.07985(9) 0.0269(5) Uani 1 1 d . . . . .
C12 C 0.08853(18) 0.7156(3) 0.17947(10) 0.0341(6) Uani 1 1 d . . . . .
H12 H 0.0288 0.6661 0.1848 0.041 Uiso 1 1 calc R U . . .
C13 C 0.16689(18) 0.7199(3) 0.22368(10) 0.0374(6) Uani 1 1 d . . . . .
H13 H 0.1598 0.6754 0.2587 0.045 Uiso 1 1 calc R U . . .
H1W H 0.1759(13) 1.396(3) 0.4894(11) 0.073(11) Uiso 1 1 d D . . . .
H2W H 0.0895(18) 1.465(2) 0.4531(12) 0.063(10) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O5 2.0916(15) 6_576 ?
Mn1 O6 2.1382(17) . ?
Mn1 N1 2.2148(17) 3_455 ?
Mn1 O2 2.2151(15) . ?
Mn1 O5 2.2359(15) 2 ?
Mn1 O1 2.2711(14) . ?
N1 C4 1.336(3) . ?
N1 C3 1.341(3) . ?
N1 Mn1 2.2148(17) 3_545 ?
O1 C1 1.263(3) . ?
O2 C1 1.254(2) . ?
O3 C5 1.372(3) . ?
O3 C7 1.396(3) . ?
O4 C11 1.229(3) . ?
O5 C11 1.297(3) . ?
O5 Mn1 2.0917(15) 6_575 ?
O5 Mn1 2.2360(15) 2 ?
O6 H1W 0.866(10) . ?
O6 H2W 0.866(10) . ?
C1 C2 1.496(3) . ?
C2 C6 1.379(3) . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(3) . ?
C7 C13 1.383(4) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C12 1.381(3) . ?
C10 C11 1.497(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Mn1 O6 95.07(7) 6_576 . ?
O5 Mn1 N1 106.93(6) 6_576 3_455 ?
O6 Mn1 N1 90.46(7) . 3_455 ?
O5 Mn1 O2 154.40(6) 6_576 . ?
O6 Mn1 O2 102.03(7) . . ?
N1 Mn1 O2 91.98(6) 3_455 . ?
O5 Mn1 O5 76.88(6) 6_576 2 ?
O6 Mn1 O5 171.61(7) . 2 ?
N1 Mn1 O5 94.14(6) 3_455 2 ?
O2 Mn1 O5 84.85(6) . 2 ?
O5 Mn1 O1 103.03(6) 6_576 . ?
O6 Mn1 O1 89.38(6) . . ?
N1 Mn1 O1 149.94(6) 3_455 . ?
O2 Mn1 O1 58.76(5) . . ?
O5 Mn1 O1 90.14(6) 2 . ?
C4 N1 C3 118.64(18) . . ?
C4 N1 Mn1 121.29(13) . 3_545 ?
C3 N1 Mn1 120.06(14) . 3_545 ?
C1 O1 Mn1 88.12(12) . . ?
C1 O2 Mn1 90.88(13) . . ?
C5 O3 C7 120.96(17) . . ?
C11 O5 Mn1 133.90(14) . 6_575 ?
C11 O5 Mn1 122.59(13) . 2 ?
Mn1 O5 Mn1 103.11(6) 6_575 2 ?
Mn1 O6 H1W 123.3(18) . . ?
Mn1 O6 H2W 121.3(17) . . ?
H1W O6 H2W 115.4(17) . . ?
O2 C1 O1 122.03(19) . . ?
O2 C1 C2 118.35(19) . . ?
O1 C1 C2 119.61(18) . . ?
C6 C2 C3 119.16(19) . . ?
C6 C2 C1 119.16(19) . . ?
C3 C2 C1 121.7(2) . . ?
N1 C3 C2 122.0(2) . . ?
N1 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
N1 C4 C5 122.2(2) . . ?
N1 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
O3 C5 C6 124.8(2) . . ?
O3 C5 C4 115.63(19) . . ?
C6 C5 C4 119.4(2) . . ?
C5 C6 C2 118.6(2) . . ?
C5 C6 H6 120.7 . . ?
C2 C6 H6 120.7 . . ?
C8 C7 C13 121.4(2) . . ?
C8 C7 O3 115.4(2) . . ?
C13 C7 O3 123.0(2) . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C10 C9 119.5(2) . . ?
C12 C10 C11 119.7(2) . . ?
C9 C10 C11 120.7(2) . . ?
O4 C11 O5 123.9(2) . . ?
O4 C11 C10 119.8(2) . . ?
O5 C11 C10 116.3(2) . . ?
C10 C12 C13 120.6(2) . . ?
C10 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C7 C13 C12 118.8(2) . . ?
C7 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O2 C1 O1 -4.7(2) . . . . ?
Mn1 O2 C1 C2 176.17(17) . . . . ?
Mn1 O1 C1 O2 4.6(2) . . . . ?
Mn1 O1 C1 C2 -176.30(18) . . . . ?
O2 C1 C2 C6 8.7(3) . . . . ?
O1 C1 C2 C6 -170.5(2) . . . . ?
O2 C1 C2 C3 -172.8(2) . . . . ?
O1 C1 C2 C3 8.0(3) . . . . ?
C4 N1 C3 C2 -1.0(3) . . . . ?
Mn1 N1 C3 C2 178.00(16) 3_545 . . . ?
C6 C2 C3 N1 1.6(3) . . . . ?
C1 C2 C3 N1 -176.9(2) . . . . ?
C3 N1 C4 C5 -0.4(4) . . . . ?
Mn1 N1 C4 C5 -179.41(18) 3_545 . . . ?
C7 O3 C5 C6 -29.1(4) . . . . ?
C7 O3 C5 C4 156.4(2) . . . . ?
N1 C4 C5 O3 176.0(2) . . . . ?
N1 C4 C5 C6 1.2(4) . . . . ?
O3 C5 C6 C2 -174.9(2) . . . . ?
C4 C5 C6 C2 -0.6(4) . . . . ?
C3 C2 C6 C5 -0.7(3) . . . . ?
C1 C2 C6 C5 177.8(2) . . . . ?
C5 O3 C7 C8 149.4(2) . . . . ?
C5 O3 C7 C13 -35.3(4) . . . . ?
C13 C7 C8 C9 -0.4(4) . . . . ?
O3 C7 C8 C9 174.9(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C12 1.1(3) . . . . ?
C8 C9 C10 C11 -176.0(2) . . . . ?
Mn1 O5 C11 O4 -77.7(3) 6_575 . . . ?
Mn1 O5 C11 O4 93.8(2) 2 . . . ?
Mn1 O5 C11 C10 102.8(2) 6_575 . . . ?
Mn1 O5 C11 C10 -85.7(2) 2 . . . ?
C12 C10 C11 O4 -20.7(3) . . . . ?
C9 C10 C11 O4 156.4(2) . . . . ?
C12 C10 C11 O5 158.8(2) . . . . ?
C9 C10 C11 O5 -24.1(3) . . . . ?
C9 C10 C12 C13 -0.2(4) . . . . ?
C11 C10 C12 C13 177.0(2) . . . . ?
C8 C7 C13 C12 1.4(4) . . . . ?
O3 C7 C13 C12 -173.6(2) . . . . ?
C10 C12 C13 C7 -1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H1W O1 0.866(10) 1.879(12) 2.733(2) 168(3) 7_576
O6 H2W O4 0.866(10) 1.811(12) 2.668(2) 170(3) 2_565

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_291-2Mn
_database_code_depnum_ccdc_archive 'CCDC 1536680'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Mn N3 O7'
_chemical_formula_weight         504.35

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'
Mn Mn 0.3368 0.7283 '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                   7.4796(5)
_cell_length_b                   10.1643(7)
_cell_length_c                   15.5357(9)
_cell_angle_alpha                95.151(5)
_cell_angle_beta                 92.019(5)
_cell_angle_gamma                111.113(6)
_cell_volume                     1094.46(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6778
_cell_measurement_theta_min      3.592
_cell_measurement_theta_max      25.047

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   0.843
_exptl_transmission_factor_max   0.866
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.655
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6778
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.592
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3852
_reflns_number_gt                2961
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0247P)²+0.1836P] 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         3852
_refine_ls_number_parameters     323
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Mn1 Mn 0.29087(6) 0.65383(5) 0.30330(3) 0.03083(15) Uani 1 1 d . . . . .
N1 N -0.2838(3) 0.4074(3) -0.01665(16) 0.0390(6) Uani 1 1 d . . . . .
N2 N 0.2837(3) 0.4672(3) 0.37713(15) 0.0338(6) Uani 1 1 d . . . . .
N3 N 0.2708(3) 0.7141(3) 0.44419(15) 0.0331(6) Uani 1 1 d . . . . .
O1 O -0.0084(3) 0.5461(2) 0.27157(12) 0.0360(5) Uani 1 1 d . . . . .
O2 O -0.2672(3) 0.5908(3) 0.23673(14) 0.0583(7) Uani 1 1 d . . . . .
O3 O 0.0007(4) 0.1977(2) 0.01343(14) 0.0570(7) Uani 1 1 d . . . . .
O4 O 0.2652(3) -0.1608(2) 0.26456(15) 0.0505(6) Uani 1 1 d . . . . .
O5 O 0.5490(3) -0.0341(2) 0.22043(15) 0.0522(6) Uani 1 1 d . . . . .
O6 O 0.6133(3) 0.7846(2) 0.32269(13) 0.0396(5) Uani 1 1 d D . . . .
O7 O 0.3701(3) 0.5513(2) 0.18799(13) 0.0414(5) Uani 1 1 d D . . . .
C1 C -0.1444(4) 0.5378(3) 0.22003(18) 0.0318(7) Uani 1 1 d . . . . .
C2 C -0.1659(4) 0.4541(3) 0.13304(18) 0.0290(7) Uani 1 1 d . . . . .
C3 C -0.2686(4) 0.4756(3) 0.06304(19) 0.0376(8) Uani 1 1 d . . . . .
H3 H -0.3297 0.5403 0.0717 0.045 Uiso 1 1 calc R U . . .
C4 C -0.1969(4) 0.3150(3) -0.02744(19) 0.0396(8) Uani 1 1 d . . . . .
H4 H -0.2077 0.2661 -0.0821 0.047 Uiso 1 1 calc R U . . .
C5 C -0.0902(4) 0.2873(3) 0.03898(19) 0.0343(7) Uani 1 1 d . . . . .
C6 C -0.0742(4) 0.3585(3) 0.11992(18) 0.0327(7) Uani 1 1 d . . . . .
H6 H -0.0027 0.3427 0.1653 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0919(5) 0.1445(3) 0.0739(2) 0.0413(8) Uani 1 1 d . . . . .
C8 C 0.2809(5) 0.1694(3) 0.0659(2) 0.0559(10) Uani 1 1 d . . . . .
H8 H 0.3476 0.2297 0.0266 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3743(5) 0.1051(3) 0.1163(2) 0.0499(9) Uani 1 1 d . . . . .
H9 H 0.5042 0.1228 0.1112 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2754(4) 0.0147(3) 0.17425(19) 0.0343(7) Uani 1 1 d . . . . .
C11 C 0.3745(4) -0.0641(3) 0.22381(19) 0.0357(7) Uani 1 1 d . . . . .
C12 C 0.0832(4) -0.0086(3) 0.1821(2) 0.0398(8) Uani 1 1 d . . . . .
H12 H 0.0153 -0.0694 0.2208 0.048 Uiso 1 1 calc R U . . .
C13 C -0.0093(5) 0.0583(3) 0.1323(2) 0.0442(8) Uani 1 1 d . . . . .
H13 H -0.1378 0.0448 0.1386 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2766(5) 0.8419(3) 0.4760(2) 0.0475(9) Uani 1 1 d . . . . .
H14 H 0.2860 0.9086 0.4375 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2695(5) 0.8806(4) 0.5625(2) 0.0550(10) Uani 1 1 d . . . . .
H15 H 0.2778 0.9719 0.5822 0.066 Uiso 1 1 calc R U . . .
C16 C 0.2498(5) 0.7811(4) 0.6185(2) 0.0577(10) Uani 1 1 d . . . . .
H16 H 0.2411 0.8030 0.6773 0.069 Uiso 1 1 calc R U . . .
C17 C 0.2429(4) 0.6486(4) 0.5874(2) 0.0478(9) Uani 1 1 d . . . . .
H17 H 0.2303 0.5800 0.6250 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2549(4) 0.6177(3) 0.49976(19) 0.0339(7) Uani 1 1 d . . . . .
C19 C 0.2555(4) 0.4782(3) 0.46212(19) 0.0327(7) Uani 1 1 d . . . . .
C20 C 0.2309(4) 0.3670(4) 0.5115(2) 0.0457(9) Uani 1 1 d . . . . .
H20 H 0.2125 0.3771 0.5703 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2342(5) 0.2418(4) 0.4722(2) 0.0567(10) Uani 1 1 d . . . . .
H21 H 0.2198 0.1664 0.5046 0.068 Uiso 1 1 calc R U . . .
C22 C 0.2585(5) 0.2277(4) 0.3856(2) 0.0547(10) Uani 1 1 d . . . . .
H22 H 0.2585 0.1426 0.3579 0.066 Uiso 1 1 calc R U . . .
C23 C 0.2833(4) 0.3428(3) 0.3402(2) 0.0447(8) Uani 1 1 d . . . . .
H23 H 0.3004 0.3336 0.2812 0.054 Uiso 1 1 calc R U . . .
H1W H 0.608(5) 0.846(3) 0.2885(18) 0.087(14) Uiso 1 1 d D . . . .
H2W H 0.677(5) 0.732(3) 0.305(2) 0.096(15) Uiso 1 1 d D . . . .
H3W H 0.338(4) 0.561(4) 0.1353(11) 0.085(14) Uiso 1 1 d D . . . .
H4W H 0.4903(19) 0.562(3) 0.1975(18) 0.067(12) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O4 2.099(2) 1_565 ?
Mn1 O1 2.1242(18) . ?
Mn1 O7 2.198(2) . ?
Mn1 N3 2.244(2) . ?
Mn1 O6 2.289(2) . ?
Mn1 N2 2.289(2) . ?
N1 C4 1.324(4) . ?
N1 C3 1.344(4) . ?
N2 C23 1.340(4) . ?
N2 C19 1.346(4) . ?
N3 C14 1.332(4) . ?
N3 C18 1.340(3) . ?
O1 C1 1.245(3) . ?
O2 C1 1.245(3) . ?
O3 C5 1.360(3) . ?
O3 C7 1.397(3) . ?
O4 C11 1.267(3) . ?
O4 Mn1 2.099(2) 1_545 ?
O5 C11 1.233(3) . ?
O6 H1W 0.867(10) . ?
O6 H2W 0.869(10) . ?
O7 H3W 0.869(10) . ?
O7 H4W 0.872(10) . ?
C1 C2 1.502(4) . ?
C2 C6 1.382(4) . ?
C2 C3 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(4) . ?
C7 C13 1.370(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.382(4) . ?
C10 C11 1.510(4) . ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.486(4) . ?
C19 C20 1.384(4) . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 O1 88.95(8) 1_565 . ?
O4 Mn1 O7 105.42(9) 1_565 . ?
O1 Mn1 O7 93.23(8) . . ?
O4 Mn1 N3 93.83(9) 1_565 . ?
O1 Mn1 N3 96.83(8) . . ?
O7 Mn1 N3 158.42(8) . . ?
O4 Mn1 O6 85.35(8) 1_565 . ?
O1 Mn1 O6 172.85(8) . . ?
O7 Mn1 O6 84.14(8) . . ?
N3 Mn1 O6 87.88(8) . . ?
O4 Mn1 N2 164.94(9) 1_565 . ?
O1 Mn1 N2 87.67(8) . . ?
O7 Mn1 N2 89.42(9) . . ?
N3 Mn1 N2 72.03(9) . . ?
O6 Mn1 N2 98.93(8) . . ?
C4 N1 C3 117.5(2) . . ?
C23 N2 C19 117.9(3) . . ?
C23 N2 Mn1 124.7(2) . . ?
C19 N2 Mn1 116.9(2) . . ?
C14 N3 C18 117.9(3) . . ?
C14 N3 Mn1 123.5(2) . . ?
C18 N3 Mn1 118.6(2) . . ?
C1 O1 Mn1 143.69(19) . . ?
C5 O3 C7 121.2(2) . . ?
C11 O4 Mn1 131.5(2) . 1_545 ?
Mn1 O6 H1W 94(2) . . ?
Mn1 O6 H2W 109(3) . . ?
H1W O6 H2W 115.7(18) . . ?
Mn1 O7 H3W 123(2) . . ?
Mn1 O7 H4W 107(2) . . ?
H3W O7 H4W 114.7(17) . . ?
O2 C1 O1 124.3(3) . . ?
O2 C1 C2 117.7(2) . . ?
O1 C1 C2 118.0(3) . . ?
C6 C2 C3 118.4(3) . . ?
C6 C2 C1 120.2(2) . . ?
C3 C2 C1 121.4(3) . . ?
N1 C3 C2 123.1(3) . . ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N1 C4 C5 123.2(3) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
O3 C5 C6 126.7(2) . . ?
O3 C5 C4 114.4(3) . . ?
C6 C5 C4 118.7(3) . . ?
C5 C6 C2 119.1(2) . . ?
C5 C6 H6 120.5 . . ?
C2 C6 H6 120.5 . . ?
C8 C7 C13 121.4(3) . . ?
C8 C7 O3 116.8(3) . . ?
C13 C7 O3 121.4(3) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C12 119.1(3) . . ?
C9 C10 C11 119.8(3) . . ?
C12 C10 C11 120.9(3) . . ?
O5 C11 O4 125.2(3) . . ?
O5 C11 C10 119.6(3) . . ?
O4 C11 C10 115.2(3) . . ?
C10 C12 C13 120.4(3) . . ?
C10 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C7 C13 C12 118.9(3) . . ?
C7 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N3 C14 C15 123.7(3) . . ?
N3 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N3 C18 C17 121.4(3) . . ?
N3 C18 C19 116.3(3) . . ?
C17 C18 C19 122.4(3) . . ?
N2 C19 C20 122.0(3) . . ?
N2 C19 C18 115.8(3) . . ?
C20 C19 C18 122.2(3) . . ?
C21 C20 C19 118.8(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 118.3(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
N2 C23 C22 123.0(3) . . ?
N2 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 -101.7(4) . . . . ?
Mn1 O1 C1 C2 80.4(4) . . . . ?
O2 C1 C2 C6 -160.3(3) . . . . ?
O1 C1 C2 C6 17.7(4) . . . . ?
O2 C1 C2 C3 23.2(4) . . . . ?
O1 C1 C2 C3 -158.8(3) . . . . ?
C4 N1 C3 C2 0.5(5) . . . . ?
C6 C2 C3 N1 0.4(4) . . . . ?
C1 C2 C3 N1 177.0(3) . . . . ?
C3 N1 C4 C5 -0.8(5) . . . . ?
C7 O3 C5 C6 14.0(5) . . . . ?
C7 O3 C5 C4 -171.3(3) . . . . ?
N1 C4 C5 O3 -174.9(3) . . . . ?
N1 C4 C5 C6 0.3(5) . . . . ?
O3 C5 C6 C2 175.1(3) . . . . ?
C4 C5 C6 C2 0.7(4) . . . . ?
C3 C2 C6 C5 -0.9(4) . . . . ?
C1 C2 C6 C5 -177.6(3) . . . . ?
C5 O3 C7 C8 -123.2(3) . . . . ?
C5 O3 C7 C13 63.6(4) . . . . ?
C13 C7 C8 C9 1.2(5) . . . . ?
O3 C7 C8 C9 -171.9(3) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C12 -1.0(5) . . . . ?
C8 C9 C10 C11 175.1(3) . . . . ?
Mn1 O4 C11 O5 -24.0(5) 1_545 . . . ?
Mn1 O4 C11 C10 154.0(2) 1_545 . . . ?
C9 C10 C11 O5 9.0(4) . . . . ?
C12 C10 C11 O5 -174.9(3) . . . . ?
C9 C10 C11 O4 -169.2(3) . . . . ?
C12 C10 C11 O4 6.9(4) . . . . ?
C9 C10 C12 C13 -0.1(5) . . . . ?
C11 C10 C12 C13 -176.2(3) . . . . ?
C8 C7 C13 C12 -2.3(5) . . . . ?
O3 C7 C13 C12 170.5(3) . . . . ?
C10 C12 C13 C7 1.7(5) . . . . ?
C18 N3 C14 C15 0.8(4) . . . . ?
Mn1 N3 C14 C15 -178.2(2) . . . . ?
N3 C14 C15 C16 -2.0(5) . . . . ?
C14 C15 C16 C17 1.7(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C14 N3 C18 C17 0.6(4) . . . . ?
Mn1 N3 C18 C17 179.7(2) . . . . ?
C14 N3 C18 C19 -178.0(2) . . . . ?
Mn1 N3 C18 C19 1.1(3) . . . . ?
C16 C17 C18 N3 -0.8(4) . . . . ?
C16 C17 C18 C19 177.8(3) . . . . ?
C23 N2 C19 C20 1.5(4) . . . . ?
Mn1 N2 C19 C20 174.0(2) . . . . ?
C23 N2 C19 C18 -179.3(2) . . . . ?
Mn1 N2 C19 C18 -6.8(3) . . . . ?
N3 C18 C19 N2 3.9(3) . . . . ?
C17 C18 C19 N2 -174.7(3) . . . . ?
N3 C18 C19 C20 -176.9(2) . . . . ?
C17 C18 C19 C20 4.5(4) . . . . ?
N2 C19 C20 C21 -0.5(4) . . . . ?
C18 C19 C20 C21 -179.7(3) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C21 C22 C23 1.3(5) . . . . ?
C19 N2 C23 C22 -1.2(4) . . . . ?
Mn1 N2 C23 C22 -173.0(2) . . . . ?
C21 C22 C23 N2 -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H4W O2 0.872(10) 1.803(10) 2.666(3) 170(3) 1_655
O7 H3W N1 0.869(10) 1.952(11) 2.820(3) 176(3) 2_565
O6 H2W O2 0.869(10) 1.883(17) 2.710(3) 159(4) 1_655
O6 H1W O5 0.867(10) 1.837(11) 2.695(3) 170(3) 1_565

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_289-13Ni
_database_code_depnum_ccdc_archive 'CCDC 1536684'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N3 Ni O7'
_chemical_formula_weight         532.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           ?
_space_group_name_H-M_alt        I2/c
_space_group_name_Hall           ?

_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+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.7135(9)
_cell_length_b                   8.2535(3)
_cell_length_c                   29.2012(19)
_cell_angle_alpha                90
_cell_angle_beta                 108.334(6)
_cell_angle_gamma                90
_cell_volume                     4510.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8522
_cell_measurement_theta_min      3.306
_cell_measurement_theta_max      25.043

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   0.796
_exptl_transmission_factor_max   0.818
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.915
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8522
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.306
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_full        25.043
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3999
_reflns_number_gt                3046
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1000P)²+0.5000P] 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         3999
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Ni1 Ni 0.41092(2) 0.41496(6) 0.38715(2) 0.0327(2) Uani 1 1 d . . . . .
O1 O 0.41994(16) 0.8307(4) 0.39172(9) 0.0507(8) Uani 1 1 d . . . . .
O2 O 0.40602(15) 0.6075(3) 0.43062(9) 0.0372(7) Uani 1 1 d . . . . .
O3 O 0.64994(14) 1.0661(3) 0.50401(10) 0.0437(7) Uani 1 1 d . . . . .
O4 O 0.98097(15) 0.9420(3) 0.59615(10) 0.0466(7) Uani 1 1 d . . . . .
O5 O 0.96181(17) 1.0589(5) 0.65958(11) 0.0672(10) Uani 1 1 d . . . . .
O6 O 0.39527(18) 0.5809(4) 0.32875(10) 0.0413(7) Uani 1 1 d . . . . .
O7 O 0.5000 0.7039(11) 0.2500 0.274(8) Uani 1 2 d S T P . .
H3W H 0.4883 0.6698 0.2223 0.329 Uiso 1 1 d R U . . .
O8 O 0.5000 0.405(2) 0.2500 0.387(11) Uiso 1 2 d S . P . .
H5W H 0.5116 0.4391 0.2774 0.465 Uiso 1 1 d R U . . .
N1 N 0.57055(16) 0.7332(3) 0.55163(10) 0.0326(7) Uani 1 1 d . . . . .
N2 N 0.40482(19) 0.2191(4) 0.34133(11) 0.0406(8) Uani 1 1 d . . . . .
N3 N 0.30141(18) 0.3709(4) 0.36533(11) 0.0381(8) Uani 1 1 d . . . . .
C1 C 0.4367(2) 0.7410(5) 0.42717(13) 0.0361(9) Uani 1 1 d . . . . .
C2 C 0.49988(19) 0.7861(4) 0.46997(12) 0.0298(8) Uani 1 1 d . . . . .
C3 C 0.51415(19) 0.7026(4) 0.51281(12) 0.0302(8) Uani 1 1 d . . . . .
H3 H 0.4829 0.6205 0.5149 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6149(2) 0.8526(4) 0.54806(14) 0.0357(9) Uani 1 1 d . . . . .
H4 H 0.6539 0.8769 0.5749 0.043 Uiso 1 1 calc R U . . .
C5 C 0.60514(19) 0.9405(4) 0.50652(14) 0.0326(9) Uani 1 1 d . . . . .
C6 C 0.5474(2) 0.9083(4) 0.46688(13) 0.0319(9) Uani 1 1 d . . . . .
H6 H 0.5399 0.9666 0.4385 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7218(2) 1.0507(4) 0.53315(14) 0.0364(9) Uani 1 1 d . . . . .
C8 C 0.7677(2) 0.9658(6) 0.51557(16) 0.0541(12) Uani 1 1 d . . . . .
H8 H 0.7510 0.9167 0.4854 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8379(2) 0.9530(6) 0.54229(16) 0.0516(12) Uani 1 1 d . . . . .
H9 H 0.8689 0.8940 0.5304 0.062 Uiso 1 1 calc R U . . .
C10 C 0.86387(19) 1.0278(5) 0.58742(13) 0.0341(9) Uani 1 1 d . . . . .
C11 C 0.9417(2) 1.0097(5) 0.61714(15) 0.0411(10) Uani 1 1 d . . . . .
C12 C 0.8167(2) 1.1116(5) 0.60454(15) 0.0425(10) Uani 1 1 d . . . . .
H12 H 0.8332 1.1609 0.6347 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7450(2) 1.1241(5) 0.57773(16) 0.0452(10) Uani 1 1 d . . . . .
H13 H 0.7134 1.1808 0.5896 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4572(3) 0.1448(6) 0.33077(17) 0.0549(12) Uani 1 1 d . . . . .
H14 H 0.5038 0.1800 0.3454 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4453(4) 0.0153(6) 0.29850(19) 0.0736(16) Uani 1 1 d . . . . .
H15 H 0.4835 -0.0351 0.2921 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3776(4) -0.0365(6) 0.27657(17) 0.0664(16) Uani 1 1 d . . . . .
H16 H 0.3695 -0.1219 0.2547 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3194(3) 0.0374(5) 0.28651(15) 0.0556(13) Uani 1 1 d . . . . .
C18 C 0.3362(2) 0.1676(5) 0.32006(13) 0.0410(10) Uani 1 1 d . . . . .
C19 C 0.2461(4) -0.0059(6) 0.26605(17) 0.0735(18) Uani 1 1 d . . . . .
H19 H 0.2340 -0.0893 0.2435 0.088 Uiso 1 1 calc R U . . .
C20 C 0.1936(3) 0.0700(6) 0.27821(18) 0.0679(17) Uani 1 1 d . . . . .
H20 H 0.1463 0.0386 0.2638 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2098(2) 0.1979(5) 0.31294(16) 0.0520(12) Uani 1 1 d . . . . .
C22 C 0.2813(2) 0.2482(5) 0.33306(13) 0.0396(10) Uani 1 1 d . . . . .
C23 C 0.1588(3) 0.2808(7) 0.3278(2) 0.0713(16) Uani 1 1 d . . . . .
H23 H 0.1109 0.2521 0.3156 0.086 Uiso 1 1 calc R U . . .
C24 C 0.1791(3) 0.4032(7) 0.3601(2) 0.0748(16) Uani 1 1 d . . . . .
H24 H 0.1452 0.4595 0.3700 0.090 Uiso 1 1 calc R U . . .
C25 C 0.2518(3) 0.4442(5) 0.37862(17) 0.0513(11) Uani 1 1 d . . . . .
H25 H 0.2653 0.5270 0.4013 0.062 Uiso 1 1 calc R U . . .
H1W H 0.393(3) 0.661(6) 0.3440(19) 0.072(19) Uiso 1 1 d . . . . .
H2W H 0.439(3) 0.576(5) 0.3241(17) 0.060(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O4 2.043(3) 4_645 ?
Ni1 O2 2.055(3) . ?
Ni1 N2 2.078(3) . ?
Ni1 N3 2.082(3) . ?
Ni1 N1 2.101(3) 5_666 ?
Ni1 O6 2.133(3) . ?
O1 C1 1.230(4) . ?
O2 C1 1.276(4) . ?
O3 C5 1.378(4) . ?
O3 C7 1.410(4) . ?
O4 C11 1.260(5) . ?
O4 Ni1 2.043(3) 4_655 ?
O5 C11 1.245(5) . ?
O6 H1W 0.81(5) . ?
O6 H2W 0.91(5) . ?
O7 H3W 0.8180 . ?
O8 H5W 0.8109 . ?
N1 C3 1.339(4) . ?
N1 C4 1.343(5) . ?
N1 Ni1 2.101(3) 5_666 ?
N2 C14 1.318(5) . ?
N2 C18 1.367(5) . ?
N3 C25 1.308(6) . ?
N3 C22 1.355(5) . ?
C1 C2 1.507(5) . ?
C2 C3 1.378(5) . ?
C2 C6 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(6) . ?
C7 C13 1.377(6) . ?
C8 C9 1.363(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(6) . ?
C9 H9 0.9300 . ?
C10 C12 1.373(6) . ?
C10 C11 1.513(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.395(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.408(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.421(6) . ?
C17 C19 1.425(7) . ?
C18 C22 1.419(6) . ?
C19 C20 1.349(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.429(7) . ?
C20 H20 0.9300 . ?
C21 C23 1.393(7) . ?
C21 C22 1.409(6) . ?
C23 C24 1.354(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.406(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ni1 O2 90.93(11) 4_645 . ?
O4 Ni1 N2 94.79(13) 4_645 . ?
O2 Ni1 N2 174.27(12) . . ?
O4 Ni1 N3 174.54(12) 4_645 . ?
O2 Ni1 N3 94.49(12) . . ?
N2 Ni1 N3 79.78(13) . . ?
O4 Ni1 N1 88.36(11) 4_645 5_666 ?
O2 Ni1 N1 87.37(11) . 5_666 ?
N2 Ni1 N1 93.11(12) . 5_666 ?
N3 Ni1 N1 92.56(12) . 5_666 ?
O4 Ni1 O6 89.91(12) 4_645 . ?
O2 Ni1 O6 88.52(12) . . ?
N2 Ni1 O6 91.17(13) . . ?
N3 Ni1 O6 89.55(12) . . ?
N1 Ni1 O6 175.51(11) 5_666 . ?
C1 O2 Ni1 120.2(2) . . ?
C5 O3 C7 116.0(3) . . ?
C11 O4 Ni1 133.4(3) . 4_655 ?
Ni1 O6 H1W 96(4) . . ?
Ni1 O6 H2W 101(3) . . ?
H1W O6 H2W 110(5) . . ?
C3 N1 C4 117.4(3) . . ?
C3 N1 Ni1 119.1(2) . 5_666 ?
C4 N1 Ni1 123.4(2) . 5_666 ?
C14 N2 C18 119.0(4) . . ?
C14 N2 Ni1 128.4(3) . . ?
C18 N2 Ni1 112.5(3) . . ?
C25 N3 C22 118.0(4) . . ?
C25 N3 Ni1 128.9(3) . . ?
C22 N3 Ni1 113.0(3) . . ?
O1 C1 O2 125.2(3) . . ?
O1 C1 C2 118.8(3) . . ?
O2 C1 C2 115.9(3) . . ?
C3 C2 C6 118.0(3) . . ?
C3 C2 C1 120.6(3) . . ?
C6 C2 C1 121.3(3) . . ?
N1 C3 C2 123.5(3) . . ?
N1 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N1 C4 C5 122.8(3) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 O3 118.5(3) . . ?
C4 C5 O3 122.0(3) . . ?
C5 C6 C2 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C2 C6 H6 120.6 . . ?
C8 C7 C13 121.2(4) . . ?
C8 C7 O3 118.5(4) . . ?
C13 C7 O3 120.2(4) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C12 C10 C9 118.5(4) . . ?
C12 C10 C11 121.4(3) . . ?
C9 C10 C11 120.1(3) . . ?
O5 C11 O4 125.2(4) . . ?
O5 C11 C10 119.2(4) . . ?
O4 C11 C10 115.6(4) . . ?
C10 C12 C13 121.2(4) . . ?
C10 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C7 C13 C12 118.5(4) . . ?
C7 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N2 C14 C15 122.4(5) . . ?
N2 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 116.2(5) . . ?
C16 C17 C19 126.1(5) . . ?
C18 C17 C19 117.6(5) . . ?
N2 C18 C22 117.5(3) . . ?
N2 C18 C17 122.0(4) . . ?
C22 C18 C17 120.5(4) . . ?
C20 C19 C17 122.3(5) . . ?
C20 C19 H19 118.9 . . ?
C17 C19 H19 118.9 . . ?
C19 C20 C21 120.7(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C21 C22 116.8(4) . . ?
C23 C21 C20 124.2(5) . . ?
C22 C21 C20 118.9(5) . . ?
N3 C22 C21 123.0(4) . . ?
N3 C22 C18 117.1(4) . . ?
C21 C22 C18 119.9(4) . . ?
C24 C23 C21 120.0(5) . . ?
C24 C23 H23 120.0 . . ?
C21 C23 H23 120.0 . . ?
C23 C24 C25 119.3(5) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
N3 C25 C24 122.8(4) . . ?
N3 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O2 C1 O1 65.5(5) . . . . ?
Ni1 O2 C1 C2 -112.4(3) . . . . ?
O1 C1 C2 C3 170.5(4) . . . . ?
O2 C1 C2 C3 -11.4(5) . . . . ?
O1 C1 C2 C6 -12.4(6) . . . . ?
O2 C1 C2 C6 165.7(3) . . . . ?
C4 N1 C3 C2 0.3(5) . . . . ?
Ni1 N1 C3 C2 -175.9(3) 5_666 . . . ?
C6 C2 C3 N1 0.7(6) . . . . ?
C1 C2 C3 N1 177.9(3) . . . . ?
C3 N1 C4 C5 -1.1(6) . . . . ?
Ni1 N1 C4 C5 174.8(3) 5_666 . . . ?
N1 C4 C5 C6 1.0(6) . . . . ?
N1 C4 C5 O3 177.9(3) . . . . ?
C7 O3 C5 C6 -151.4(4) . . . . ?
C7 O3 C5 C4 31.8(5) . . . . ?
C4 C5 C6 C2 0.0(6) . . . . ?
O3 C5 C6 C2 -177.0(3) . . . . ?
C3 C2 C6 C5 -0.8(5) . . . . ?
C1 C2 C6 C5 -177.9(3) . . . . ?
C5 O3 C7 C8 85.3(5) . . . . ?
C5 O3 C7 C13 -96.5(4) . . . . ?
C13 C7 C8 C9 -0.2(7) . . . . ?
O3 C7 C8 C9 178.0(4) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 C9 C10 C12 1.2(7) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
Ni1 O4 C11 O5 -12.0(7) 4_655 . . . ?
Ni1 O4 C11 C10 169.1(3) 4_655 . . . ?
C12 C10 C11 O5 6.7(6) . . . . ?
C9 C10 C11 O5 -170.8(4) . . . . ?
C12 C10 C11 O4 -174.3(4) . . . . ?
C9 C10 C11 O4 8.2(6) . . . . ?
C9 C10 C12 C13 -0.7(6) . . . . ?
C11 C10 C12 C13 -178.2(4) . . . . ?
C8 C7 C13 C12 0.7(6) . . . . ?
O3 C7 C13 C12 -177.5(3) . . . . ?
C10 C12 C13 C7 -0.2(6) . . . . ?
C18 N2 C14 C15 0.1(7) . . . . ?
Ni1 N2 C14 C15 -178.9(3) . . . . ?
N2 C14 C15 C16 0.6(8) . . . . ?
C14 C15 C16 C17 -0.9(8) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C15 C16 C17 C19 -179.8(4) . . . . ?
C14 N2 C18 C22 178.7(3) . . . . ?
Ni1 N2 C18 C22 -2.1(4) . . . . ?
C14 N2 C18 C17 -0.6(6) . . . . ?
Ni1 N2 C18 C17 178.5(3) . . . . ?
C16 C17 C18 N2 0.4(6) . . . . ?
C19 C17 C18 N2 -179.4(4) . . . . ?
C16 C17 C18 C22 -178.9(4) . . . . ?
C19 C17 C18 C22 1.2(6) . . . . ?
C16 C17 C19 C20 178.9(5) . . . . ?
C18 C17 C19 C20 -1.3(7) . . . . ?
C17 C19 C20 C21 -0.5(8) . . . . ?
C19 C20 C21 C23 -179.2(5) . . . . ?
C19 C20 C21 C22 2.4(7) . . . . ?
C25 N3 C22 C21 0.8(6) . . . . ?
Ni1 N3 C22 C21 -179.4(3) . . . . ?
C25 N3 C22 C18 -178.4(3) . . . . ?
Ni1 N3 C22 C18 1.4(4) . . . . ?
C23 C21 C22 N3 -0.1(6) . . . . ?
C20 C21 C22 N3 178.4(4) . . . . ?
C23 C21 C22 C18 179.1(4) . . . . ?
C20 C21 C22 C18 -2.4(6) . . . . ?
N2 C18 C22 N3 0.5(5) . . . . ?
C17 C18 C22 N3 179.9(3) . . . . ?
N2 C18 C22 C21 -178.8(3) . . . . ?
C17 C18 C22 C21 0.6(6) . . . . ?
C22 C21 C23 C24 0.0(7) . . . . ?
C20 C21 C23 C24 -178.4(5) . . . . ?
C21 C23 C24 C25 -0.5(8) . . . . ?
C22 N3 C25 C24 -1.4(7) . . . . ?
Ni1 N3 C25 C24 178.9(4) . . . . ?
C23 C24 C25 N3 1.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O8 H5W O7 0.81 2.31 2.47(2) 91.3 .
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645
O7 H3W O5 0.82 1.97 2.779(5) 172.4 3_444
O8 H5W O5 0.81 2.01 2.812(8) 170.9 4_645
C3 H3 O4 0.93 2.44 2.962(5) 115.5 8_465
C4 H4 N3 0.93 2.65 3.146(5) 113.8 5_666
C15 H15 O7 0.93 2.55 3.277(9) 135.1 1_545
O6 H1W O1 0.81(5) 1.93(5) 2.703(4) 161(5) .
O6 H1W O2 0.81(5) 2.50(5) 2.923(4) 114(4) .
O6 H2W O5 0.91(5) 1.87(5) 2.735(5) 158(4) 4_645

_refine_diff_density_max         0.905
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_289-12Mn1
_database_code_depnum_ccdc_archive 'CCDC 1536683'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H18 Mn N6 O11'
_chemical_formula_weight         765.50

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   15.3257(10)
_cell_length_b                   20.0375(10)
_cell_length_c                   24.9024(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7647.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6625
_cell_measurement_theta_min      3.347
_cell_measurement_theta_max      25.047

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             3112
_exptl_transmission_factor_min   0.902
_exptl_transmission_factor_max   0.921
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.410
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6625
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_point_group_measured_fraction_full 0.801
_reflns_number_total             2714
_reflns_number_gt                1920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.569
_reflns_Friedel_fraction_max     0.596
_reflns_Friedel_fraction_full    0.596

_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.2000P)²+0.3265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     249
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0933
_refine_ls_wR_factor_ref         0.3021
_refine_ls_wR_factor_gt          0.2635
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.081
_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
N1A N 0.3264(8) -0.1252(6) 1.0744(8) 0.101(5) Uani 0.5 1 d . . P A .
Mn1 Mn 0.5000 0.0000 1.01759(10) 0.0616(8) Uani 1 2 d S T P . .
C5B C 0.3264(8) -0.1252(6) 1.0744(8) 0.101(5) Uani 0.5 1 d . . P A .
H5B H 0.3800 -0.1200 1.0940 0.121 Uiso 0.5 1 d R U P . .
N2 N 0.6091(7) 0.0202(5) 0.9546(4) 0.067(3) Uani 1 1 d . . . . .
N3 N 0.4941(6) 0.1088(5) 0.9971(5) 0.065(3) Uani 1 1 d . . . . .
O1 O 0.4032(7) 0.0033(4) 1.0775(4) 0.079(3) Uani 1 1 d . . . . .
O2 O 0.2713(7) 0.0491(5) 1.0769(5) 0.099(3) Uani 1 1 d . . . . .
O3 O 0.3256(15) -0.2423(11) 1.0504(17) 0.149(6) Uani 0.5 1 d . U P A 1
O4 O 0.4843(14) 0.0678(11) 0.1774(12) 0.190(8) Uani 1 1 d . . . . .
O5 O 0.9886(10) 0.9339(9) 0.9836(12) 0.187(10) Uani 1 1 d . . . . .
O6 O 0.8476(19) 0.8722(13) 0.0223(16) 0.281(14) Uani 1 1 d . . . . .
C1 C 0.3210(9) 0.0007(6) 1.0726(6) 0.069(3) Uani 1 1 d . . . . .
C2 C 0.2840(7) -0.0680(7) 1.0597(5) 0.066(3) Uani 1 1 d . . . . .
C3 C 0.2867(12) -0.1838(10) 1.0615(14) 0.150(6) Uani 1 1 d . U . . .
C4 C 0.2047(11) -0.1866(10) 1.0323(13) 0.151(6) Uani 1 1 d . U . . .
C5A C 0.1670(11) -0.1315(8) 1.0196(9) 0.121(5) Uani 0.5 1 d . U P . .
H5A H 0.1102 -0.1284 1.0025 0.146 Uiso 0.5 1 d R U P . .
N1B N 0.1670(11) -0.1315(8) 1.0196(9) 0.121(5) Uani 0.5 1 d . U P . .
C6 C 0.2055(8) -0.0717(8) 1.0340(6) 0.084(4) Uani 1 1 d . . . . .
C7 C 0.6671(8) -0.0219(8) 0.9359(5) 0.074(3) Uani 1 1 d . . . . .
H7 H 0.6630 -0.0664 0.9461 0.089 Uiso 1 1 calc R U . . .
C8 C 0.7328(10) -0.0038(8) 0.9024(7) 0.086(4) Uani 1 1 d . . . . .
H8 H 0.7748 -0.0345 0.8915 0.103 Uiso 1 1 calc R U . . .
C9 C 0.7352(10) 0.0625(10) 0.8851(6) 0.092(5) Uani 1 1 d . . . . .
H9 H 0.7768 0.0754 0.8600 0.111 Uiso 1 1 calc R U . . .
C10 C 0.6790(8) 0.1074(7) 0.9039(4) 0.068(3) Uani 1 1 d . . . . .
C11 C 0.6148(7) 0.0848(6) 0.9392(4) 0.057(3) Uani 1 1 d . . . . .
C12 C 0.6827(10) 0.1746(8) 0.8882(7) 0.089(4) Uani 1 1 d . . . . .
H12 H 0.7257 0.1894 0.8647 0.107 Uiso 1 1 calc R U . . .
C13 C 0.6224(11) 0.2174(8) 0.9079(6) 0.092(5) Uani 1 1 d . . . . .
H13 H 0.6240 0.2615 0.8963 0.110 Uiso 1 1 calc R U . . .
C14 C 0.5560(8) 0.1986(6) 0.9460(5) 0.070(3) Uani 1 1 d . . . . .
C15 C 0.5553(8) 0.1312(6) 0.9599(5) 0.066(3) Uani 1 1 d . . . . .
C16 C 0.4954(11) 0.2412(7) 0.9668(8) 0.084(4) Uani 1 1 d . . . . .
H16 H 0.4950 0.2857 0.9562 0.100 Uiso 1 1 calc R U . . .
C17 C 0.4316(10) 0.2175(6) 1.0055(8) 0.094(5) Uani 1 1 d . . . . .
H17 H 0.3902 0.2452 1.0212 0.113 Uiso 1 1 calc R U . . .
C18 C 0.4378(10) 0.1508(6) 1.0167(7) 0.088(4) Uani 1 1 d . . . . .
H18 H 0.3973 0.1337 1.0409 0.105 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
N1A C3 1.36(2) . ?
N1A C2 1.367(19) . ?
N1A H5B 0.9619 . ?
Mn1 O1 2.105(10) 2_655 ?
Mn1 O1 2.105(10) . ?
Mn1 N3 2.240(10) . ?
Mn1 N3 2.240(10) 2_655 ?
Mn1 N2 2.328(11) 2_655 ?
Mn1 N2 2.328(11) . ?
N2 C7 1.310(17) . ?
N2 C11 1.353(16) . ?
N3 C18 1.301(17) . ?
N3 C15 1.393(17) . ?
O1 C1 1.266(17) . ?
O2 C1 1.238(16) . ?
O3 C3 1.34(3) . ?
O3 C4 1.56(3) 14_545 ?
C1 C2 1.523(18) . ?
C2 C6 1.37(2) . ?
C3 C4 1.45(4) . ?
C4 C5A 1.29(3) . ?
C4 O3 1.56(3) 14_545 ?
C5A C6 1.383(19) . ?
C5A H5A 0.9708 . ?
C7 C8 1.36(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.40(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.33(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(16) . ?
C10 C12 1.40(2) . ?
C11 C15 1.401(17) . ?
C12 C13 1.35(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.44(2) . ?
C13 H13 0.9300 . ?
C14 C16 1.36(2) . ?
C14 C15 1.393(16) . ?
C16 C17 1.45(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(18) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1A C2 116.6(18) . . ?
C3 N1A H5B 126.5 . . ?
C2 N1A H5B 116.8 . . ?
O1 Mn1 O1 89.7(6) 2_655 . ?
O1 Mn1 N3 102.7(3) 2_655 . ?
O1 Mn1 N3 95.9(4) . . ?
O1 Mn1 N3 95.9(4) 2_655 2_655 ?
O1 Mn1 N3 102.7(3) . 2_655 ?
N3 Mn1 N3 153.7(6) . 2_655 ?
O1 Mn1 N2 168.1(3) 2_655 2_655 ?
O1 Mn1 N2 88.7(3) . 2_655 ?
N3 Mn1 N2 89.2(4) . 2_655 ?
N3 Mn1 N2 72.9(4) 2_655 2_655 ?
O1 Mn1 N2 88.7(3) 2_655 . ?
O1 Mn1 N2 168.1(3) . . ?
N3 Mn1 N2 72.9(4) . . ?
N3 Mn1 N2 89.2(4) 2_655 . ?
N2 Mn1 N2 95.2(5) 2_655 . ?
C7 N2 C11 118.1(12) . . ?
C7 N2 Mn1 127.9(10) . . ?
C11 N2 Mn1 113.8(8) . . ?
C18 N3 C15 119.1(11) . . ?
C18 N3 Mn1 124.9(9) . . ?
C15 N3 Mn1 116.0(8) . . ?
C1 O1 Mn1 129.1(10) . . ?
C3 O3 C4 136(2) . 14_545 ?
O2 C1 O1 124.9(12) . . ?
O2 C1 C2 119.8(12) . . ?
O1 C1 C2 115.3(12) . . ?
C6 C2 N1A 119.9(13) . . ?
C6 C2 C1 118.4(13) . . ?
N1A C2 C1 121.6(12) . . ?
O3 C3 N1A 127.1(19) . . ?
O3 C3 C4 104(2) . . ?
N1A C3 C4 123(2) . . ?
C5A C4 C3 118.5(17) . . ?
C5A C4 O3 136.1(16) . 14_545 ?
C3 C4 O3 99(2) . 14_545 ?
C4 C5A C6 119(2) . . ?
C4 C5A H5A 124.5 . . ?
C6 C5A H5A 116.0 . . ?
C2 C6 C5A 122.9(16) . . ?
N2 C7 C8 123.4(15) . . ?
N2 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 117.6(15) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C10 C9 C8 121.2(13) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 117.2(12) . . ?
C9 C10 C12 121.7(13) . . ?
C11 C10 C12 121.1(13) . . ?
N2 C11 C10 122.4(11) . . ?
N2 C11 C15 119.3(10) . . ?
C10 C11 C15 118.4(11) . . ?
C13 C12 C10 118.6(14) . . ?
C13 C12 H12 120.7 . . ?
C10 C12 H12 120.7 . . ?
C12 C13 C14 123.7(13) . . ?
C12 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C16 C14 C15 120.5(13) . . ?
C16 C14 C13 124.5(13) . . ?
C15 C14 C13 115.0(14) . . ?
C11 C15 N3 118.0(10) . . ?
C11 C15 C14 123.2(12) . . ?
N3 C15 C14 118.9(12) . . ?
C14 C16 C17 120.3(12) . . ?
C14 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 114.1(14) . . ?
C18 C17 H17 122.9 . . ?
C16 C17 H17 122.9 . . ?
N3 C18 C17 127.0(15) . . ?
N3 C18 H18 116.5 . . ?
C17 C18 H18 116.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 -104.5(15) . . . . ?
Mn1 O1 C1 C2 74.8(15) . . . . ?
C3 N1A C2 C6 1(2) . . . . ?
C3 N1A C2 C1 179.1(16) . . . . ?
O2 C1 C2 C6 24.3(19) . . . . ?
O1 C1 C2 C6 -155.0(13) . . . . ?
O2 C1 C2 N1A -154.1(14) . . . . ?
O1 C1 C2 N1A 26.5(19) . . . . ?
C4 O3 C3 N1A -176(4) 14_545 . . . ?
C4 O3 C3 C4 -24(5) 14_545 . . . ?
C2 N1A C3 O3 150(3) . . . . ?
C2 N1A C3 C4 2(3) . . . . ?
O3 C3 C4 C5A -156(3) . . . . ?
N1A C3 C4 C5A -2(4) . . . . ?
O3 C3 C4 O3 48(2) . . . 14_545 ?
N1A C3 C4 O3 -158(3) . . . 14_545 ?
C3 C4 C5A C6 0(3) . . . . ?
O3 C4 C5A C6 144(3) 14_545 . . . ?
N1A C2 C6 C5A -3(2) . . . . ?
C1 C2 C6 C5A 178.8(13) . . . . ?
C4 C5A C6 C2 2(3) . . . . ?
C11 N2 C7 C8 0.6(19) . . . . ?
Mn1 N2 C7 C8 -174.3(11) . . . . ?
N2 C7 C8 C9 -3(2) . . . . ?
C7 C8 C9 C10 5(2) . . . . ?
C8 C9 C10 C11 -3(2) . . . . ?
C8 C9 C10 C12 177.7(13) . . . . ?
C7 N2 C11 C10 1.1(16) . . . . ?
Mn1 N2 C11 C10 176.6(8) . . . . ?
C7 N2 C11 C15 -178.0(11) . . . . ?
Mn1 N2 C11 C15 -2.4(12) . . . . ?
C9 C10 C11 N2 0.4(17) . . . . ?
C12 C10 C11 N2 179.2(11) . . . . ?
C9 C10 C11 C15 179.5(11) . . . . ?
C12 C10 C11 C15 -1.7(16) . . . . ?
C9 C10 C12 C13 178.6(13) . . . . ?
C11 C10 C12 C13 -0.1(19) . . . . ?
C10 C12 C13 C14 2(2) . . . . ?
C12 C13 C14 C16 179.2(14) . . . . ?
C12 C13 C14 C15 -2.6(17) . . . . ?
N2 C11 C15 N3 2.1(15) . . . . ?
C10 C11 C15 N3 -177.0(10) . . . . ?
N2 C11 C15 C14 -179.5(10) . . . . ?
C10 C11 C15 C14 1.4(15) . . . . ?
C18 N3 C15 C11 -179.6(11) . . . . ?
Mn1 N3 C15 C11 -0.6(13) . . . . ?
C18 N3 C15 C14 1.9(17) . . . . ?
Mn1 N3 C15 C14 -179.1(8) . . . . ?
C16 C14 C15 C11 178.9(11) . . . . ?
C13 C14 C15 C11 0.6(15) . . . . ?
C16 C14 C15 N3 -2.6(17) . . . . ?
C13 C14 C15 N3 179.0(10) . . . . ?
C15 C14 C16 C17 3(2) . . . . ?
C13 C14 C16 C17 -179.4(12) . . . . ?
C14 C16 C17 C18 -2(2) . . . . ?
C15 N3 C18 C17 -1(2) . . . . ?
Mn1 N3 C18 C17 179.9(12) . . . . ?
C16 C17 C18 N3 1(2) . . . . ?

_refine_diff_density_max         0.684
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_290-13Ni
_database_code_depnum_ccdc_archive 'CCDC 1559267'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N2 Ni O6'
_chemical_formula_weight         412.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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                   7.6886(5)
_cell_length_b                   10.5629(8)
_cell_length_c                   11.5519(7)
_cell_angle_alpha                76.902(6)
_cell_angle_beta                 85.674(5)
_cell_angle_gamma                75.701(6)
_cell_volume                     885.28(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5895
_cell_measurement_theta_min      3.622
_cell_measurement_theta_max      25.050

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   0.735
_exptl_transmission_factor_max   0.762
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.134
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5895
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.622
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3137
_reflns_number_gt                2618
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0323P)²+0.1978P] 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         3137
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Ni1 Ni 0.67727(4) 0.54400(4) 0.80909(3) 0.01949(13) Uani 1 1 d . . . . .
N2 N 0.7875(3) 0.3406(2) 0.8815(2) 0.0230(5) Uani 1 1 d . . . . .
O3 O 0.9952(2) 0.6944(2) 0.39648(16) 0.0316(5) Uani 1 1 d . . . . .
N1 N 0.9010(3) 0.5772(2) 0.71039(19) 0.0208(5) Uani 1 1 d . . . . .
C15 C 0.9892(4) 0.1746(3) 1.0169(3) 0.0347(8) Uani 1 1 d . . . . .
H15 H 1.0705 0.1563 1.0776 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0675(3) 0.5459(3) 0.7521(2) 0.0213(6) Uani 1 1 d . . . . .
H3 H 1.0837 0.5138 0.8334 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8785(3) 0.6300(3) 0.5936(2) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.7632 0.6553 0.5637 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8574(4) 0.8075(3) 0.3585(2) 0.0260(7) Uani 1 1 d . . . . .
C18 C 0.7493(4) 0.2402(3) 0.8436(3) 0.0374(8) Uani 1 1 d . . . . .
H18 H 0.6662 0.2612 0.7837 0.045 Uiso 1 1 calc R U . . .
C5 C 1.0206(3) 0.6479(3) 0.5169(2) 0.0215(6) Uani 1 1 d . . . . .
C16 C 0.9530(3) 0.0706(3) 0.9763(2) 0.0240(7) Uani 1 1 d . . . . .
C14 C 0.9064(4) 0.3044(3) 0.9685(3) 0.0314(7) Uani 1 1 d . . . . .
H14 H 0.9348 0.3716 0.9980 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6407(4) 0.9251(3) 0.2110(3) 0.0337(8) Uani 1 1 d . . . . .
H9 H 0.5814 0.9283 0.1427 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6015(4) 1.0337(3) 0.2641(3) 0.0291(7) Uani 1 1 d . . . . .
C8 C 0.7686(4) 0.8111(3) 0.2596(3) 0.0345(8) Uani 1 1 d . . . . .
H8 H 0.7937 0.7372 0.2247 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6902(4) 1.0276(3) 0.3646(3) 0.0447(9) Uani 1 1 d . . . . .
H12 H 0.6628 1.1005 0.4008 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8258(4) 0.1083(3) 0.8882(3) 0.0406(9) Uani 1 1 d . . . . .
H17 H 0.7921 0.0428 0.8590 0.049 Uiso 1 1 calc R U . . .
C13 C 0.8199(4) 0.9148(3) 0.4131(3) 0.0444(9) Uani 1 1 d . . . . .
H13 H 0.8803 0.9116 0.4809 0.053 Uiso 1 1 calc R U . . .
O4 O 0.3858(3) 1.1576(2) 0.1202(2) 0.0555(7) Uani 1 1 d . . . . .
C11 C 0.4674(4) 1.1598(3) 0.2092(3) 0.0326(8) Uani 1 1 d . . . . .
C2 C 1.2165(3) 0.5592(3) 0.6796(2) 0.0202(6) Uani 1 1 d . . . . .
C6 C 1.1936(3) 0.6090(3) 0.5588(2) 0.0236(7) Uani 1 1 d . . . . .
H6 H 1.2915 0.6160 0.5074 0.028 Uiso 1 1 calc R U . . .
C1 C 1.3985(3) 0.5260(3) 0.7329(3) 0.0225(6) Uani 1 1 d . . . . .
O2 O 1.5361(2) 0.5145(2) 0.66706(16) 0.0258(5) Uani 1 1 d . . . . .
O1 O 1.4088(2) 0.5165(2) 0.84338(16) 0.0290(5) Uani 1 1 d . . . . .
O5 O 0.4498(3) 1.2588(2) 0.25568(18) 0.0317(5) Uani 1 1 d . . . . .
O6 O 0.7491(3) 0.5935(2) 0.9563(2) 0.0255(5) Uani 1 1 d . . . . .
H2W H 0.697(5) 0.682(4) 0.941(3) 0.059(12) Uiso 1 1 d . . . . .
H1W H 0.699(4) 0.561(3) 1.014(3) 0.041(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O6 2.039(2) . ?
Ni1 N1 2.050(2) . ?
Ni1 O5 2.0619(19) 2_676 ?
Ni1 N2 2.104(2) . ?
Ni1 O1 2.1502(18) 1_455 ?
Ni1 O2 2.1529(19) 1_455 ?
Ni1 C1 2.443(3) 1_455 ?
N2 C14 1.336(3) . ?
N2 C18 1.336(4) . ?
O3 C5 1.378(3) . ?
O3 C7 1.396(3) . ?
N1 C3 1.338(3) . ?
N1 C4 1.344(3) . ?
C15 C14 1.369(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C3 C2 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C7 C8 1.364(4) . ?
C7 C13 1.378(4) . ?
C18 C17 1.367(4) . ?
C18 H18 0.9300 . ?
C5 C6 1.381(3) . ?
C16 C17 1.387(4) . ?
C16 C16 1.484(5) 2_757 ?
C14 H14 0.9300 . ?
C9 C10 1.380(4) . ?
C9 C8 1.387(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.371(4) . ?
C10 C11 1.509(4) . ?
C8 H8 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
O4 C11 1.252(4) . ?
C11 O5 1.255(4) . ?
C2 C6 1.384(4) . ?
C2 C1 1.500(3) . ?
C6 H6 0.9300 . ?
C1 O2 1.253(3) . ?
C1 O1 1.264(3) . ?
C1 Ni1 2.443(3) 1_655 ?
O2 Ni1 2.1528(19) 1_655 ?
O1 Ni1 2.1502(18) 1_655 ?
O5 Ni1 2.0620(19) 2_676 ?
O6 H2W 0.91(4) . ?
O6 H1W 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Ni1 N1 94.96(9) . . ?
O6 Ni1 O5 90.12(9) . 2_676 ?
N1 Ni1 O5 88.75(8) . 2_676 ?
O6 Ni1 N2 90.01(9) . . ?
N1 Ni1 N2 95.76(9) . . ?
O5 Ni1 N2 175.46(8) 2_676 . ?
O6 Ni1 O1 106.40(8) . 1_455 ?
N1 Ni1 O1 157.46(8) . 1_455 ?
O5 Ni1 O1 84.19(8) 2_676 1_455 ?
N2 Ni1 O1 91.42(8) . 1_455 ?
O6 Ni1 O2 165.90(7) . 1_455 ?
N1 Ni1 O2 96.54(8) . 1_455 ?
O5 Ni1 O2 82.02(8) 2_676 1_455 ?
N2 Ni1 O2 96.91(8) . 1_455 ?
O1 Ni1 O2 61.33(7) 1_455 1_455 ?
O6 Ni1 C1 135.82(9) . 1_455 ?
N1 Ni1 C1 126.35(9) . 1_455 ?
O5 Ni1 C1 77.34(9) 2_676 1_455 ?
N2 Ni1 C1 99.46(9) . 1_455 ?
O1 Ni1 C1 31.13(8) 1_455 1_455 ?
O2 Ni1 C1 30.83(8) 1_455 1_455 ?
C14 N2 C18 115.6(2) . . ?
C14 N2 Ni1 120.6(2) . . ?
C18 N2 Ni1 123.77(19) . . ?
C5 O3 C7 118.3(2) . . ?
C3 N1 C4 117.8(2) . . ?
C3 N1 Ni1 125.24(18) . . ?
C4 N1 Ni1 116.87(17) . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N1 C3 C2 122.9(2) . . ?
N1 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N1 C4 C5 122.1(2) . . ?
N1 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C8 C7 C13 121.1(3) . . ?
C8 C7 O3 116.8(3) . . ?
C13 C7 O3 122.0(3) . . ?
N2 C18 C17 123.6(3) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C4 C5 O3 120.9(2) . . ?
C4 C5 C6 120.0(2) . . ?
O3 C5 C6 118.8(2) . . ?
C15 C16 C17 115.2(3) . . ?
C15 C16 C16 121.5(3) . 2_757 ?
C17 C16 C16 123.3(3) . 2_757 ?
N2 C14 C15 124.0(3) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C12 C10 C9 119.4(3) . . ?
C12 C10 C11 120.4(3) . . ?
C9 C10 C11 120.1(3) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C12 C13 121.2(3) . . ?
C10 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C7 C13 C12 118.5(3) . . ?
C7 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
O4 C11 O5 125.6(3) . . ?
O4 C11 C10 117.4(3) . . ?
O5 C11 C10 116.9(3) . . ?
C3 C2 C6 119.0(2) . . ?
C3 C2 C1 120.0(2) . . ?
C6 C2 C1 120.8(2) . . ?
C5 C6 C2 117.9(2) . . ?
C5 C6 H6 121.1 . . ?
C2 C6 H6 121.1 . . ?
O2 C1 O1 121.4(2) . . ?
O2 C1 C2 119.8(2) . . ?
O1 C1 C2 118.8(2) . . ?
O2 C1 Ni1 61.70(14) . 1_655 ?
O1 C1 Ni1 61.56(13) . 1_655 ?
C2 C1 Ni1 163.01(19) . 1_655 ?
C1 O2 Ni1 87.47(16) . 1_655 ?
C1 O1 Ni1 87.31(15) . 1_655 ?
C11 O5 Ni1 129.1(2) . 2_676 ?
Ni1 O6 H2W 100(2) . . ?
Ni1 O6 H1W 110(2) . . ?
H2W O6 H1W 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C3 C2 -3.4(4) . . . . ?
Ni1 N1 C3 C2 173.9(2) . . . . ?
C3 N1 C4 C5 2.3(4) . . . . ?
Ni1 N1 C4 C5 -175.2(2) . . . . ?
C5 O3 C7 C8 -144.7(3) . . . . ?
C5 O3 C7 C13 39.6(4) . . . . ?
C14 N2 C18 C17 -0.6(5) . . . . ?
Ni1 N2 C18 C17 177.7(2) . . . . ?
N1 C4 C5 O3 175.9(3) . . . . ?
N1 C4 C5 C6 1.1(4) . . . . ?
C7 O3 C5 C4 48.5(4) . . . . ?
C7 O3 C5 C6 -136.7(3) . . . . ?
C14 C15 C16 C17 -1.9(5) . . . . ?
C14 C15 C16 C16 177.3(3) . . . 2_757 ?
C18 N2 C14 C15 1.0(4) . . . . ?
Ni1 N2 C14 C15 -177.3(2) . . . . ?
C16 C15 C14 N2 0.3(5) . . . . ?
C8 C9 C10 C12 0.1(5) . . . . ?
C8 C9 C10 C11 177.8(3) . . . . ?
C13 C7 C8 C9 1.3(5) . . . . ?
O3 C7 C8 C9 -174.5(3) . . . . ?
C10 C9 C8 C7 -1.1(5) . . . . ?
C9 C10 C12 C13 0.7(5) . . . . ?
C11 C10 C12 C13 -177.0(3) . . . . ?
N2 C18 C17 C16 -1.1(5) . . . . ?
C15 C16 C17 C18 2.3(5) . . . . ?
C16 C16 C17 C18 -176.9(3) 2_757 . . . ?
C8 C7 C13 C12 -0.4(5) . . . . ?
O3 C7 C13 C12 175.1(3) . . . . ?
C10 C12 C13 C7 -0.6(5) . . . . ?
C12 C10 C11 O4 -177.4(3) . . . . ?
C9 C10 C11 O4 5.0(4) . . . . ?
C12 C10 C11 O5 3.9(5) . . . . ?
C9 C10 C11 O5 -173.7(3) . . . . ?
N1 C3 C2 C6 1.1(4) . . . . ?
N1 C3 C2 C1 178.2(2) . . . . ?
C4 C5 C6 C2 -3.4(4) . . . . ?
O3 C5 C6 C2 -178.3(3) . . . . ?
C3 C2 C6 C5 2.4(4) . . . . ?
C1 C2 C6 C5 -174.7(2) . . . . ?
C3 C2 C1 O2 167.0(3) . . . . ?
C6 C2 C1 O2 -15.9(4) . . . . ?
C3 C2 C1 O1 -16.3(4) . . . . ?
C6 C2 C1 O1 160.8(3) . . . . ?
C3 C2 C1 Ni1 -102.7(7) . . . 1_655 ?
C6 C2 C1 Ni1 74.3(8) . . . 1_655 ?
O1 C1 O2 Ni1 -16.0(3) . . . 1_655 ?
C2 C1 O2 Ni1 160.6(2) . . . 1_655 ?
O2 C1 O1 Ni1 16.0(3) . . . 1_655 ?
C2 C1 O1 Ni1 -160.6(2) . . . 1_655 ?
O4 C11 O5 Ni1 -11.8(5) . . . 2_676 ?
C10 C11 O5 Ni1 166.73(19) . . . 2_676 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H1W O1 0.80(3) 1.89(3) 2.689(3) 176(3) 2_767
O6 H2W O4 0.91(4) 1.66(4) 2.552(3) 166(3) 2_676

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.065

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

data_299-14Pb2
_database_code_depnum_ccdc_archive 'CCDC 1536686'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N3 O6 Pb'
_chemical_formula_weight         662.60

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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.7701(3)
_cell_length_b                   16.3976(4)
_cell_length_c                   12.9320(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.766(3)
_cell_angle_gamma                90
_cell_volume                     2243.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7891
_cell_measurement_theta_min      3.436
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   0.203
_exptl_transmission_factor_max   0.204
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    7.568
_shelx_estimated_absorpt_T_min   0.264
_shelx_estimated_absorpt_T_max   0.299
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7891
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.436
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3977
_reflns_number_gt                3316
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0246P)²+3.3155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Pb1 Pb 0.65174(2) 0.47178(2) 0.45513(2) 0.03405(8) Uani 1 1 d . . . . .
N1 N 0.4316(5) 0.3701(3) -0.0205(4) 0.0577(15) Uani 1 1 d . . . . .
N2 N 0.8639(4) 0.4296(3) 0.4080(3) 0.0337(11) Uani 1 1 d . . . . .
N3 N 0.7694(4) 0.5825(3) 0.3560(3) 0.0365(11) Uani 1 1 d . . . . .
O1 O 0.4603(4) 0.5198(2) 0.3002(3) 0.0467(10) Uani 1 1 d . . . . .
O2 O 0.5971(3) 0.4226(2) 0.2838(3) 0.0434(10) Uani 1 1 d . . . . .
O3 O 0.1760(4) 0.5127(3) -0.0726(3) 0.0533(12) Uani 1 1 d . . . . .
O4 O 0.0432(4) 0.8743(2) 0.0409(3) 0.0485(11) Uani 1 1 d . . . . .
O5 O -0.1496(4) 0.8233(2) 0.0020(4) 0.0511(11) Uani 1 1 d . . . . .
C1 C 0.5000(5) 0.4653(3) 0.2484(5) 0.0359(13) Uani 1 1 d . . . . .
C2 C 0.4346(5) 0.4475(3) 0.1377(4) 0.0324(13) Uani 1 1 d . . . . .
C3 C 0.3310(5) 0.4918(3) 0.0903(4) 0.0334(13) Uani 1 1 d . . . . .
H3 H 0.2958 0.5313 0.1277 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2807(5) 0.4765(3) -0.0132(4) 0.0353(13) Uani 1 1 d . . . . .
C5 C 0.3338(6) 0.4148(4) -0.0654(5) 0.0487(16) Uani 1 1 d . . . . .
H5 H 0.2986 0.4046 -0.1355 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4809(6) 0.3873(4) 0.0802(5) 0.0466(16) Uani 1 1 d . . . . .
H6 H 0.5500 0.3571 0.1133 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1308(5) 0.5876(4) -0.0441(4) 0.0379(14) Uani 1 1 d . . . . .
C8 C 0.2079(5) 0.6508(3) -0.0009(5) 0.0406(14) Uani 1 1 d . . . . .
H8 H 0.2952 0.6443 0.0145 0.049 Uiso 1 1 calc R U . . .
C9 C 0.1533(5) 0.7235(4) 0.0188(5) 0.0406(14) Uani 1 1 d . . . . .
H9 H 0.2050 0.7665 0.0470 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0239(5) 0.7346(3) -0.0022(4) 0.0342(13) Uani 1 1 d . . . . .
C11 C -0.0312(5) 0.8160(3) 0.0151(5) 0.0374(13) Uani 1 1 d . . . . .
C12 C -0.0522(5) 0.6698(4) -0.0442(5) 0.0426(15) Uani 1 1 d . . . . .
H12 H -0.1396 0.6759 -0.0587 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0015(6) 0.5966(4) -0.0645(5) 0.0452(15) Uani 1 1 d . . . . .
H13 H -0.0498 0.5532 -0.0920 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9085(5) 0.3547(4) 0.4269(5) 0.0427(15) Uani 1 1 d . . . . .
H14 H 0.8605 0.3178 0.4574 0.051 Uiso 1 1 calc R U . . .
C15 C 1.0231(6) 0.3278(4) 0.4039(5) 0.0569(18) Uani 1 1 d . . . . .
H15 H 1.0488 0.2739 0.4159 0.068 Uiso 1 1 calc R U . . .
C16 C 1.0956(6) 0.3815(5) 0.3639(5) 0.0559(18) Uani 1 1 d . . . . .
H16 H 1.1732 0.3650 0.3494 0.067 Uiso 1 1 calc R U . . .
C17 C 1.0550(5) 0.4629(4) 0.3437(4) 0.0411(15) Uani 1 1 d . . . . .
C18 C 0.9350(5) 0.4838(4) 0.3649(4) 0.0351(13) Uani 1 1 d . . . . .
C19 C 1.1272(6) 0.5229(5) 0.3015(5) 0.0554(19) Uani 1 1 d . . . . .
H19 H 1.2072 0.5092 0.2898 0.066 Uiso 1 1 calc R U . . .
C20 C 1.0832(6) 0.5990(5) 0.2779(5) 0.0552(18) Uani 1 1 d . . . . .
H20 H 1.1327 0.6368 0.2505 0.066 Uiso 1 1 calc R U . . .
O6 O 0.3665(9) 0.6824(6) 0.2539(10) 0.175(4) Uani 1 1 d G . . . .
H2W H 0.3748 0.6337 0.2767 0.262 Uiso 1 1 d G U . . .
H1W H 0.4389 0.7023 0.2519 0.262 Uiso 1 1 d G U . . .
C21 C 0.9601(6) 0.6216(4) 0.2952(4) 0.0448(15) Uani 1 1 d . . . . .
C22 C 0.8867(5) 0.5640(4) 0.3390(4) 0.0356(13) Uani 1 1 d . . . . .
C23 C 0.9060(7) 0.6988(4) 0.2695(5) 0.0560(18) Uani 1 1 d . . . . .
H23 H 0.9508 0.7381 0.2398 0.067 Uiso 1 1 calc R U . . .
C24 C 0.7891(7) 0.7165(4) 0.2879(5) 0.0554(18) Uani 1 1 d . . . . .
H24 H 0.7537 0.7677 0.2719 0.066 Uiso 1 1 calc R U . . .
C25 C 0.7228(6) 0.6563(4) 0.3313(5) 0.0447(15) Uani 1 1 d . . . . .
H25 H 0.6424 0.6685 0.3435 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 O2 2.328(4) . ?
Pb1 O5 2.497(4) 2_545 ?
Pb1 N2 2.567(4) . ?
Pb1 O4 2.647(4) 2_545 ?
Pb1 N3 2.674(5) . ?
Pb1 O1 2.710(4) . ?
N1 C5 1.325(7) . ?
N1 C6 1.342(8) . ?
N2 C14 1.325(7) . ?
N2 C18 1.359(7) . ?
N3 C25 1.326(7) . ?
N3 C22 1.357(7) . ?
O1 C1 1.240(6) . ?
O2 C1 1.271(6) . ?
O3 C4 1.375(6) . ?
O3 C7 1.397(7) . ?
O4 C11 1.251(6) . ?
O4 Pb1 2.647(4) 2 ?
O5 C11 1.260(6) . ?
O5 Pb1 2.497(4) 2 ?
C1 C2 1.501(8) . ?
C2 C3 1.376(7) . ?
C2 C6 1.383(8) . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C13 1.376(7) . ?
C7 C8 1.379(8) . ?
C8 C9 1.374(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(7) . ?
C9 H9 0.9300 . ?
C10 C12 1.388(7) . ?
C10 C11 1.495(7) . ?
C12 C13 1.379(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.394(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.343(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.414(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(8) . ?
C17 C19 1.425(9) . ?
C18 C22 1.431(8) . ?
C19 C20 1.349(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.433(9) . ?
C20 H20 0.9300 . ?
O6 H2W 0.8500 . ?
O6 H1W 0.8499 . ?
C21 C22 1.416(8) . ?
C21 C23 1.408(9) . ?
C23 C24 1.356(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.396(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Pb1 O5 82.08(15) . 2_545 ?
O2 Pb1 N2 76.03(13) . . ?
O5 Pb1 N2 80.54(14) 2_545 . ?
O2 Pb1 O4 75.45(14) . 2_545 ?
O5 Pb1 O4 50.72(12) 2_545 2_545 ?
N2 Pb1 O4 125.89(13) . 2_545 ?
O2 Pb1 N3 80.64(14) . . ?
O5 Pb1 N3 142.47(14) 2_545 . ?
N2 Pb1 N3 63.06(14) . . ?
O4 Pb1 N3 150.21(14) 2_545 . ?
O2 Pb1 O1 51.30(12) . . ?
O5 Pb1 O1 114.19(13) 2_545 . ?
N2 Pb1 O1 119.40(13) . . ?
O4 Pb1 O1 72.12(13) 2_545 . ?
N3 Pb1 O1 79.14(13) . . ?
C5 N1 C6 116.5(5) . . ?
C14 N2 C18 118.0(5) . . ?
C14 N2 Pb1 121.0(4) . . ?
C18 N2 Pb1 121.0(3) . . ?
C25 N3 C22 119.1(5) . . ?
C25 N3 Pb1 122.9(4) . . ?
C22 N3 Pb1 117.7(4) . . ?
C1 O1 Pb1 84.2(3) . . ?
C1 O2 Pb1 101.3(3) . . ?
C4 O3 C7 121.5(4) . . ?
C11 O4 Pb1 89.8(3) . 2 ?
C11 O5 Pb1 96.6(3) . 2 ?
O1 C1 O2 123.1(5) . . ?
O1 C1 C2 120.5(5) . . ?
O2 C1 C2 116.4(5) . . ?
C3 C2 C6 118.7(5) . . ?
C3 C2 C1 121.3(5) . . ?
C6 C2 C1 120.0(5) . . ?
C4 C3 C2 118.6(5) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 O3 126.8(5) . . ?
C3 C4 C5 118.9(5) . . ?
O3 C4 C5 114.2(5) . . ?
N1 C5 C4 123.5(6) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N1 C6 C2 123.7(6) . . ?
N1 C6 H6 118.1 . . ?
C2 C6 H6 118.1 . . ?
C13 C7 C8 120.6(5) . . ?
C13 C7 O3 115.7(5) . . ?
C8 C7 O3 123.7(5) . . ?
C9 C8 C7 118.7(5) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.9(5) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C12 118.4(5) . . ?
C9 C10 C11 120.1(5) . . ?
C12 C10 C11 121.3(5) . . ?
O4 C11 O5 123.0(5) . . ?
O4 C11 C10 118.1(5) . . ?
O5 C11 C10 119.0(5) . . ?
C13 C12 C10 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C10 C12 H12 119.9 . . ?
C7 C13 C12 120.1(5) . . ?
C7 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N2 C14 C15 124.0(6) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C16 C15 C14 118.4(6) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 117.1(6) . . ?
C18 C17 C19 119.5(6) . . ?
C16 C17 C19 123.4(6) . . ?
N2 C18 C17 121.8(5) . . ?
N2 C18 C22 119.3(5) . . ?
C17 C18 C22 118.8(5) . . ?
C20 C19 C17 122.1(6) . . ?
C20 C19 H19 119.0 . . ?
C17 C19 H19 119.0 . . ?
C19 C20 C21 120.0(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
H2W O6 H1W 109.5 . . ?
C22 C21 C23 117.2(6) . . ?
C22 C21 C20 119.5(6) . . ?
C23 C21 C20 123.4(6) . . ?
N3 C22 C21 121.5(6) . . ?
N3 C22 C18 118.4(5) . . ?
C21 C22 C18 120.1(5) . . ?
C24 C23 C21 120.5(6) . . ?
C24 C23 H23 119.7 . . ?
C21 C23 H23 119.7 . . ?
C23 C24 C25 118.8(6) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
N3 C25 C24 122.9(6) . . ?
N3 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pb1 O1 C1 O2 -2.6(5) . . . . ?
Pb1 O1 C1 C2 178.3(5) . . . . ?
Pb1 O2 C1 O1 3.0(6) . . . . ?
Pb1 O2 C1 C2 -177.8(4) . . . . ?
O1 C1 C2 C3 1.2(8) . . . . ?
O2 C1 C2 C3 -178.0(5) . . . . ?
O1 C1 C2 C6 179.2(5) . . . . ?
O2 C1 C2 C6 -0.1(8) . . . . ?
C6 C2 C3 C4 -2.4(8) . . . . ?
C1 C2 C3 C4 175.6(5) . . . . ?
C2 C3 C4 O3 178.1(5) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
C7 O3 C4 C3 20.4(9) . . . . ?
C7 O3 C4 C5 -163.4(5) . . . . ?
C6 N1 C5 C4 -0.8(10) . . . . ?
C3 C4 C5 N1 -0.5(10) . . . . ?
O3 C4 C5 N1 -177.0(6) . . . . ?
C5 N1 C6 C2 0.5(10) . . . . ?
C3 C2 C6 N1 1.1(10) . . . . ?
C1 C2 C6 N1 -176.9(6) . . . . ?
C4 O3 C7 C13 -144.0(6) . . . . ?
C4 O3 C7 C8 37.9(9) . . . . ?
C13 C7 C8 C9 -1.6(9) . . . . ?
O3 C7 C8 C9 176.4(5) . . . . ?
C7 C8 C9 C10 0.8(9) . . . . ?
C8 C9 C10 C12 0.1(9) . . . . ?
C8 C9 C10 C11 -176.7(5) . . . . ?
Pb1 O4 C11 O5 0.4(6) 2 . . . ?
Pb1 O4 C11 C10 179.6(5) 2 . . . ?
Pb1 O5 C11 O4 -0.5(6) 2 . . . ?
Pb1 O5 C11 C10 -179.6(4) 2 . . . ?
C9 C10 C11 O4 5.4(8) . . . . ?
C12 C10 C11 O4 -171.4(6) . . . . ?
C9 C10 C11 O5 -175.4(5) . . . . ?
C12 C10 C11 O5 7.9(9) . . . . ?
C9 C10 C12 C13 -0.2(9) . . . . ?
C11 C10 C12 C13 176.6(5) . . . . ?
C8 C7 C13 C12 1.5(9) . . . . ?
O3 C7 C13 C12 -176.6(5) . . . . ?
C10 C12 C13 C7 -0.6(9) . . . . ?
C18 N2 C14 C15 -1.0(9) . . . . ?
Pb1 N2 C14 C15 -179.7(5) . . . . ?
N2 C14 C15 C16 2.7(10) . . . . ?
C14 C15 C16 C17 -1.4(10) . . . . ?
C15 C16 C17 C18 -1.5(9) . . . . ?
C15 C16 C17 C19 179.9(6) . . . . ?
C14 N2 C18 C17 -2.1(8) . . . . ?
Pb1 N2 C18 C17 176.6(4) . . . . ?
C14 N2 C18 C22 177.1(5) . . . . ?
Pb1 N2 C18 C22 -4.3(6) . . . . ?
C16 C17 C18 N2 3.3(8) . . . . ?
C19 C17 C18 N2 -178.0(5) . . . . ?
C16 C17 C18 C22 -175.9(5) . . . . ?
C19 C17 C18 C22 2.8(8) . . . . ?
C18 C17 C19 C20 -2.1(9) . . . . ?
C16 C17 C19 C20 176.5(6) . . . . ?
C17 C19 C20 C21 0.0(10) . . . . ?
C19 C20 C21 C22 1.3(9) . . . . ?
C19 C20 C21 C23 -177.9(6) . . . . ?
C25 N3 C22 C21 -0.2(8) . . . . ?
Pb1 N3 C22 C21 -174.6(4) . . . . ?
C25 N3 C22 C18 -179.3(5) . . . . ?
Pb1 N3 C22 C18 6.3(6) . . . . ?
C23 C21 C22 N3 -0.3(8) . . . . ?
C20 C21 C22 N3 -179.5(5) . . . . ?
C23 C21 C22 C18 178.8(5) . . . . ?
C20 C21 C22 C18 -0.5(8) . . . . ?
N2 C18 C22 N3 -1.6(8) . . . . ?
C17 C18 C22 N3 177.5(5) . . . . ?
N2 C18 C22 C21 179.2(5) . . . . ?
C17 C18 C22 C21 -1.6(8) . . . . ?
C22 C21 C23 C24 0.8(9) . . . . ?
C20 C21 C23 C24 -180.0(6) . . . . ?
C21 C23 C24 C25 -0.9(10) . . . . ?
C22 N3 C25 C24 0.2(9) . . . . ?
Pb1 N3 C25 C24 174.3(4) . . . . ?
C23 C24 C25 N3 0.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H2W O1 0.85 2.08 2.874(10) 155.5 .
C14 H14 O5 0.93 2.43 3.138(7) 133.2 2_545

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_328-3Zn
_database_code_depnum_ccdc_archive 'CCDC 1559265'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H30 N6 O10 Zn2'
_chemical_formula_weight         957.50

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9718(3)
_cell_length_b                   12.3725(3)
_cell_length_c                   15.8392(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.280(3)
_cell_angle_gamma                90
_cell_volume                     2074.14(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7320
_cell_measurement_theta_min      3.549
_cell_measurement_theta_max      25.047

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   0.745
_exptl_transmission_factor_max   0.802
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.226
_shelx_estimated_absorpt_T_min   0.725
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7320
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.549
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3660
_reflns_number_gt                2936
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0338P)²+0.8289P] 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         3660
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.040
_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
Zn1 Zn 0.85227(3) 0.60961(3) 0.29983(2) 0.04506(13) Uani 1 1 d . U . . .
N1 N -0.0611(3) 0.2525(2) 0.00205(19) 0.0778(9) Uani 1 1 d . . . . .
N2 N 0.9193(2) 0.71706(17) 0.40149(14) 0.0411(5) Uani 1 1 d . . . . .
N3 N 1.0113(2) 0.52688(17) 0.37225(15) 0.0449(5) Uani 1 1 d . . . . .
O1 O 0.7101(2) 0.50827(19) 0.30109(14) 0.0641(6) Uani 1 1 d . U . . .
O2 O 0.6411(2) 0.67456(19) 0.27122(15) 0.0703(7) Uani 1 1 d . . . . .
O3 O 0.1195(2) 0.4211(2) 0.17348(14) 0.0778(7) Uani 1 1 d . . . . .
O4 O 0.1893(2) 0.47042(19) -0.13269(15) 0.0744(7) Uani 1 1 d . . . . .
O5 O 0.0886(2) 0.33085(17) -0.20368(13) 0.0643(6) Uani 1 1 d . . . . .
C1 C 0.6210(3) 0.5760(3) 0.27787(18) 0.0568(8) Uani 1 1 d . . . . .
C2 C 0.4881(3) 0.5332(2) 0.25465(17) 0.0476(7) Uani 1 1 d . . . . .
C3 C 0.4656(3) 0.4250(3) 0.2386(2) 0.0561(8) Uani 1 1 d . . . . .
H3 H 0.5329 0.3769 0.2465 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3421(3) 0.3876(3) 0.2103(2) 0.0651(9) Uani 1 1 d . . . . .
H4 H 0.3265 0.3145 0.1986 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2439(3) 0.4582(3) 0.19987(18) 0.0574(8) Uani 1 1 d . . . . .
C6 C 0.2642(3) 0.5650(3) 0.2190(2) 0.0668(9) Uani 1 1 d . . . . .
H6 H 0.1965 0.6118 0.2144 0.080 Uiso 1 1 calc R U . . .
C7 C 0.3866(3) 0.6027(3) 0.2452(2) 0.0643(9) Uani 1 1 d . . . . .
H7 H 0.4012 0.6760 0.2567 0.077 Uiso 1 1 calc R U . . .
C8 C 0.0806(3) 0.3765(2) 0.09082(18) 0.0497(7) Uani 1 1 d . . . . .
C9 C 0.1263(3) 0.4063(2) 0.02174(18) 0.0486(7) Uani 1 1 d . . . . .
H9 H 0.1885 0.4591 0.0287 0.058 Uiso 1 1 calc R U . . .
C10 C 0.0789(2) 0.3568(2) -0.05845(17) 0.0405(6) Uani 1 1 d . . . . .
C11 C 0.1241(3) 0.3904(2) -0.13633(18) 0.0451(7) Uani 1 1 d . . . . .
C12 C -0.0122(3) 0.2792(3) -0.0635(2) 0.0623(9) Uani 1 1 d . . . . .
H12 H -0.0418 0.2429 -0.1164 0.075 Uiso 1 1 calc R U . . .
C13 C -0.0145(3) 0.3016(3) 0.0782(2) 0.0609(9) Uani 1 1 d . . . . .
H13 H -0.0478 0.2845 0.1249 0.073 Uiso 1 1 calc R U . . .
C14 C 0.8632(3) 0.8089(2) 0.4148(2) 0.0515(7) Uani 1 1 d . . . . .
H14 H 0.7880 0.8289 0.3750 0.062 Uiso 1 1 calc R U . . .
C15 C 0.9125(3) 0.8747(2) 0.4851(2) 0.0623(9) Uani 1 1 d . . . . .
H15 H 0.8712 0.9380 0.4931 0.075 Uiso 1 1 calc R U . . .
C16 C 1.0238(3) 0.8457(3) 0.5433(2) 0.0646(9) Uani 1 1 d . . . . .
H16 H 1.0591 0.8893 0.5914 0.077 Uiso 1 1 calc R U . . .
C17 C 1.0829(3) 0.7515(2) 0.53012(19) 0.0544(8) Uani 1 1 d . . . . .
H17 H 1.1585 0.7308 0.5691 0.065 Uiso 1 1 calc R U . . .
C18 C 1.0285(2) 0.6880(2) 0.45829(17) 0.0403(6) Uani 1 1 d . . . . .
C19 C 1.0824(3) 0.5837(2) 0.43952(18) 0.0430(6) Uani 1 1 d . . . . .
C20 C 1.1976(3) 0.5445(3) 0.4884(2) 0.0652(9) Uani 1 1 d . . . . .
H20 H 1.2467 0.5846 0.5347 0.078 Uiso 1 1 calc R U . . .
C21 C 1.2383(4) 0.4456(3) 0.4676(3) 0.0790(11) Uani 1 1 d . . . . .
H21 H 1.3157 0.4184 0.4998 0.095 Uiso 1 1 calc R U . . .
C22 C 1.1661(4) 0.3876(3) 0.4003(3) 0.0737(11) Uani 1 1 d . . . . .
H22 H 1.1927 0.3202 0.3862 0.088 Uiso 1 1 calc R U . . .
C23 C 1.0525(3) 0.4303(3) 0.3531(2) 0.0609(9) Uani 1 1 d . . . . .
H23 H 1.0029 0.3909 0.3066 0.073 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
Zn1 O5 1.950(2) 3_665 ?
Zn1 O1 2.006(2) . ?
Zn1 N2 2.068(2) . ?
Zn1 N3 2.086(2) . ?
Zn1 O2 2.380(2) . ?
N1 C13 1.327(4) . ?
N1 C12 1.330(4) . ?
N2 C14 1.335(3) . ?
N2 C18 1.344(3) . ?
N3 C23 1.340(4) . ?
N3 C19 1.341(3) . ?
O1 C1 1.266(4) . ?
O2 C1 1.248(4) . ?
O3 C8 1.381(3) . ?
O3 C5 1.396(3) . ?
O4 C11 1.214(3) . ?
O5 C11 1.270(3) . ?
O5 Zn1 1.950(2) 3_665 ?
C1 C2 1.503(4) . ?
C2 C3 1.373(4) . ?
C2 C7 1.384(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(4) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.369(4) . ?
C8 C13 1.370(4) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.373(4) . ?
C10 C11 1.504(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.482(4) . ?
C19 C20 1.385(4) . ?
C20 C21 1.372(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Zn1 O1 131.58(9) 3_665 . ?
O5 Zn1 N2 104.00(9) 3_665 . ?
O1 Zn1 N2 120.80(9) . . ?
O5 Zn1 N3 102.27(9) 3_665 . ?
O1 Zn1 N3 103.18(9) . . ?
N2 Zn1 N3 79.22(8) . . ?
O5 Zn1 O2 103.37(9) 3_665 . ?
O1 Zn1 O2 59.49(8) . . ?
N2 Zn1 O2 93.42(8) . . ?
N3 Zn1 O2 154.33(9) . . ?
C13 N1 C12 117.3(3) . . ?
C14 N2 C18 119.2(2) . . ?
C14 N2 Zn1 125.88(18) . . ?
C18 N2 Zn1 114.86(17) . . ?
C23 N3 C19 119.1(3) . . ?
C23 N3 Zn1 126.6(2) . . ?
C19 N3 Zn1 114.00(17) . . ?
C1 O1 Zn1 97.25(19) . . ?
C1 O2 Zn1 80.75(19) . . ?
C8 O3 C5 116.7(2) . . ?
C11 O5 Zn1 110.20(18) . 3_665 ?
O2 C1 O1 122.1(3) . . ?
O2 C1 C2 120.4(3) . . ?
O1 C1 C2 117.5(3) . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C1 120.5(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 O3 118.5(3) . . ?
C4 C5 O3 120.3(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 O3 124.3(3) . . ?
C13 C8 O3 116.2(3) . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C12 C10 C9 117.1(3) . . ?
C12 C10 C11 122.5(3) . . ?
C9 C10 C11 120.4(2) . . ?
O4 C11 O5 124.0(3) . . ?
O4 C11 C10 120.2(3) . . ?
O5 C11 C10 115.7(3) . . ?
N1 C12 C10 124.4(3) . . ?
N1 C12 H12 117.8 . . ?
C10 C12 H12 117.8 . . ?
N1 C13 C8 122.5(3) . . ?
N1 C13 H13 118.7 . . ?
C8 C13 H13 118.7 . . ?
N2 C14 C15 122.3(3) . . ?
N2 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
N2 C18 C17 120.9(3) . . ?
N2 C18 C19 115.5(2) . . ?
C17 C18 C19 123.5(2) . . ?
N3 C19 C20 121.0(3) . . ?
N3 C19 C18 115.9(2) . . ?
C20 C19 C18 123.1(3) . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 118.8(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
N3 C23 C22 121.9(3) . . ?
N3 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O2 C1 O1 6.3(3) . . . . ?
Zn1 O2 C1 C2 -171.2(3) . . . . ?
Zn1 O1 C1 O2 -7.5(3) . . . . ?
Zn1 O1 C1 C2 170.1(2) . . . . ?
O2 C1 C2 C3 162.0(3) . . . . ?
O1 C1 C2 C3 -15.6(4) . . . . ?
O2 C1 C2 C7 -14.9(4) . . . . ?
O1 C1 C2 C7 167.5(3) . . . . ?
C7 C2 C3 C4 2.2(5) . . . . ?
C1 C2 C3 C4 -174.8(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C3 C4 C5 O3 -178.5(3) . . . . ?
C8 O3 C5 C6 118.7(3) . . . . ?
C8 O3 C5 C4 -64.6(4) . . . . ?
C4 C5 C6 C7 3.2(5) . . . . ?
O3 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C2 -1.9(5) . . . . ?
C3 C2 C7 C6 -0.8(5) . . . . ?
C1 C2 C7 C6 176.2(3) . . . . ?
C5 O3 C8 C9 -30.3(5) . . . . ?
C5 O3 C8 C13 153.1(3) . . . . ?
C13 C8 C9 C10 -2.6(5) . . . . ?
O3 C8 C9 C10 -179.1(3) . . . . ?
C8 C9 C10 C12 -0.3(4) . . . . ?
C8 C9 C10 C11 178.0(3) . . . . ?
Zn1 O5 C11 O4 -2.4(4) 3_665 . . . ?
Zn1 O5 C11 C10 176.90(18) 3_665 . . . ?
C12 C10 C11 O4 168.2(3) . . . . ?
C9 C10 C11 O4 -9.9(4) . . . . ?
C12 C10 C11 O5 -11.1(4) . . . . ?
C9 C10 C11 O5 170.7(3) . . . . ?
C13 N1 C12 C10 -2.7(6) . . . . ?
C9 C10 C12 N1 3.1(5) . . . . ?
C11 C10 C12 N1 -175.1(3) . . . . ?
C12 N1 C13 C8 -0.5(5) . . . . ?
C9 C8 C13 N1 3.1(5) . . . . ?
O3 C8 C13 N1 179.9(3) . . . . ?
C18 N2 C14 C15 -0.5(4) . . . . ?
Zn1 N2 C14 C15 178.5(2) . . . . ?
N2 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C14 N2 C18 C17 0.3(4) . . . . ?
Zn1 N2 C18 C17 -178.9(2) . . . . ?
C14 N2 C18 C19 178.6(2) . . . . ?
Zn1 N2 C18 C19 -0.6(3) . . . . ?
C16 C17 C18 N2 0.0(4) . . . . ?
C16 C17 C18 C19 -178.2(3) . . . . ?
C23 N3 C19 C20 0.7(4) . . . . ?
Zn1 N3 C19 C20 -173.4(2) . . . . ?
C23 N3 C19 C18 -178.1(2) . . . . ?
Zn1 N3 C19 C18 7.8(3) . . . . ?
N2 C18 C19 N3 -4.9(4) . . . . ?
C17 C18 C19 N3 173.4(3) . . . . ?
N2 C18 C19 C20 176.3(3) . . . . ?
C17 C18 C19 C20 -5.4(4) . . . . ?
N3 C19 C20 C21 -0.5(5) . . . . ?
C18 C19 C20 C21 178.2(3) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C19 N3 C23 C22 -0.3(4) . . . . ?
Zn1 N3 C23 C22 173.1(2) . . . . ?
C21 C22 C23 N3 -0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O2 0.93 2.55 3.439(4) 160.4 2_545
C13 H13 O2 0.93 2.55 3.439(4) 160.4 2_545

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_291-3Ni
_database_code_depnum_ccdc_archive 'CCDC 1536681'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H36 N6 Ni2 O13'
_chemical_formula_weight         998.23

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.1392(7)
_cell_length_b                   8.22629(18)
_cell_length_c                   19.7634(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.766(3)
_cell_angle_gamma                90
_cell_volume                     4266.56(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7683
_cell_measurement_theta_min      3.285
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             2056
_exptl_transmission_factor_min   0.787
_exptl_transmission_factor_max   0.818
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.959
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7683
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.285
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3778
_reflns_number_gt                3217
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0217P)²+7.6585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3778
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Ni1 Ni 0.36952(2) 1.14929(4) 0.51393(2) 0.02334(11) Uani 1 1 d . . . . .
N1 N 0.30335(8) 1.0069(2) 0.47855(10) 0.0237(5) Uani 1 1 d . . . . .
N2 N 0.41581(8) 0.9535(3) 0.55202(11) 0.0292(5) Uani 1 1 d . . . . .
N3 N 0.39612(8) 1.0886(3) 0.42812(11) 0.0277(5) Uani 1 1 d . . . . .
O1 O 0.17388(6) 1.1553(2) 0.53288(9) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.13190(7) 0.9316(2) 0.48756(11) 0.0412(5) Uani 1 1 d . . . . .
O3 O 0.25147(7) 0.6767(2) 0.35829(9) 0.0338(5) Uani 1 1 d . . . . .
O4 O 0.41419(8) 0.6886(3) 0.17585(11) 0.0559(7) Uani 1 1 d . . . . .
O5 O 0.34785(7) 0.8080(2) 0.10425(9) 0.0333(5) Uani 1 1 d . . . . .
O6 O 0.43277(6) 1.3116(2) 0.54931(9) 0.0317(4) Uani 1 1 d . . . . .
H1W H 0.4127 1.3918 0.5377 0.038 Uiso 1 1 d R U . . .
H2W H 0.4374 1.3324 0.5937 0.038 Uiso 1 1 d R U . . .
O7 O 0.5000 0.4689(6) 0.7500 0.210(4) Uani 1 2 d S T P . .
H3W H 0.5267 0.4207 0.7731 0.252 Uiso 0.5 1 d R U P . .
H4W H 0.4733 0.4207 0.7269 0.252 Uiso 0.5 1 d R U P . .
C1 C 0.16989(10) 1.0206(3) 0.50048(13) 0.0258(6) Uani 1 1 d . . . . .
C2 C 0.21550(9) 0.9681(3) 0.47527(12) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.26180(9) 1.0459(3) 0.49961(13) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.2641 1.1292 0.5321 0.028 Uiso 1 1 calc R U . . .
C4 C 0.29942(10) 0.8871(3) 0.43137(13) 0.0265(6) Uani 1 1 d . . . . .
H4 H 0.3281 0.8584 0.4164 0.032 Uiso 1 1 calc R U . . .
C5 C 0.25439(10) 0.8051(3) 0.40441(13) 0.0247(6) Uani 1 1 d . . . . .
C6 C 0.21171(10) 0.8451(3) 0.42621(12) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.1810 0.7909 0.4085 0.029 Uiso 1 1 calc R U . . .
C7 C 0.28150(11) 0.6907(3) 0.31016(13) 0.0282(6) Uani 1 1 d . . . . .
C8 C 0.32710(11) 0.6107(3) 0.32153(14) 0.0349(7) Uani 1 1 d . . . . .
H8 H 0.3389 0.5482 0.3616 0.042 Uiso 1 1 calc R U . . .
C9 C 0.35542(11) 0.6243(3) 0.27236(14) 0.0342(7) Uani 1 1 d . . . . .
H9 H 0.3866 0.5711 0.2798 0.041 Uiso 1 1 calc R U . . .
C10 C 0.33784(10) 0.7158(3) 0.21244(13) 0.0283(6) Uani 1 1 d . . . . .
C11 C 0.36919(10) 0.7368(3) 0.16021(13) 0.0300(6) Uani 1 1 d . . . . .
C12 C 0.29125(11) 0.7934(4) 0.20202(15) 0.0422(8) Uani 1 1 d . . . . .
H12 H 0.2788 0.8544 0.1617 0.051 Uiso 1 1 calc R U . . .
C13 C 0.26301(12) 0.7809(4) 0.25106(16) 0.0435(8) Uani 1 1 d . . . . .
H13 H 0.2318 0.8334 0.2439 0.052 Uiso 1 1 calc R U . . .
C14 C 0.42314(11) 0.8894(4) 0.61603(15) 0.0392(7) Uani 1 1 d . . . . .
H14 H 0.4053 0.9328 0.6462 0.047 Uiso 1 1 calc R U . . .
C15 C 0.45602(12) 0.7618(4) 0.63928(18) 0.0494(8) Uani 1 1 d . . . . .
H15 H 0.4601 0.7196 0.6840 0.059 Uiso 1 1 calc R U . . .
C16 C 0.48248(12) 0.6989(4) 0.59497(19) 0.0489(9) Uani 1 1 d . . . . .
H16 H 0.5052 0.6136 0.6096 0.059 Uiso 1 1 calc R U . . .
C17 C 0.47542(11) 0.7624(3) 0.52866(17) 0.0404(7) Uani 1 1 d . . . . .
H17 H 0.4932 0.7207 0.4981 0.049 Uiso 1 1 calc R U . . .
C18 C 0.44127(10) 0.8894(3) 0.50825(15) 0.0302(6) Uani 1 1 d . . . . .
C19 C 0.42902(10) 0.9636(3) 0.43736(14) 0.0299(6) Uani 1 1 d . . . . .
C20 C 0.44840(12) 0.9070(4) 0.38297(17) 0.0429(8) Uani 1 1 d . . . . .
H20 H 0.4715 0.8214 0.3901 0.051 Uiso 1 1 calc R U . . .
C21 C 0.43272(13) 0.9800(5) 0.31863(17) 0.0544(9) Uani 1 1 d . . . . .
H21 H 0.4451 0.9436 0.2815 0.065 Uiso 1 1 calc R U . . .
C22 C 0.39897(14) 1.1062(5) 0.30920(16) 0.0539(9) Uani 1 1 d . . . . .
H22 H 0.3880 1.1563 0.2658 0.065 Uiso 1 1 calc R U . . .
C23 C 0.38139(11) 1.1580(4) 0.36519(15) 0.0391(7) Uani 1 1 d . . . . .
H23 H 0.3585 1.2442 0.3588 0.047 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O5 2.0471(17) 6_576 ?
Ni1 N2 2.063(2) . ?
Ni1 O1 2.0665(17) 7_576 ?
Ni1 N3 2.067(2) . ?
Ni1 N1 2.108(2) . ?
Ni1 O6 2.1462(17) . ?
N1 C3 1.337(3) . ?
N1 C4 1.343(3) . ?
N2 C14 1.338(3) . ?
N2 C18 1.345(3) . ?
N3 C23 1.334(3) . ?
N3 C19 1.343(3) . ?
O1 C1 1.271(3) . ?
O1 Ni1 2.0665(17) 7_576 ?
O2 C1 1.237(3) . ?
O3 C5 1.384(3) . ?
O3 C7 1.406(3) . ?
O4 C11 1.246(3) . ?
O5 C11 1.255(3) . ?
O5 Ni1 2.0471(17) 6_575 ?
O6 H1W 0.8498 . ?
O6 H2W 0.8716 . ?
O7 H3W 0.8500 . ?
O7 H4W 0.8500 . ?
C1 C2 1.510(3) . ?
C2 C3 1.383(3) . ?
C2 C6 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C13 1.366(4) . ?
C7 C8 1.369(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.384(4) . ?
C10 C11 1.506(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.486(4) . ?
C19 C20 1.392(4) . ?
C20 C21 1.372(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Ni1 N2 95.71(8) 6_576 . ?
O5 Ni1 O1 89.95(7) 6_576 7_576 ?
N2 Ni1 O1 174.26(8) . 7_576 ?
O5 Ni1 N3 174.35(8) 6_576 . ?
N2 Ni1 N3 78.66(9) . . ?
O1 Ni1 N3 95.68(8) 7_576 . ?
O5 Ni1 N1 88.56(7) 6_576 . ?
N2 Ni1 N1 94.32(8) . . ?
O1 Ni1 N1 86.75(7) 7_576 . ?
N3 Ni1 N1 92.29(8) . . ?
O5 Ni1 O6 89.59(7) 6_576 . ?
N2 Ni1 O6 90.27(8) . . ?
O1 Ni1 O6 88.82(7) 7_576 . ?
N3 Ni1 O6 89.99(8) . . ?
N1 Ni1 O6 175.20(7) . . ?
C3 N1 C4 117.9(2) . . ?
C3 N1 Ni1 118.57(16) . . ?
C4 N1 Ni1 123.26(17) . . ?
C14 N2 C18 118.5(2) . . ?
C14 N2 Ni1 125.64(19) . . ?
C18 N2 Ni1 115.86(18) . . ?
C23 N3 C19 119.0(2) . . ?
C23 N3 Ni1 125.28(19) . . ?
C19 N3 Ni1 115.61(18) . . ?
C1 O1 Ni1 119.15(16) . 7_576 ?
C5 O3 C7 115.92(19) . . ?
C11 O5 Ni1 132.69(18) . 6_575 ?
Ni1 O6 H1W 89.4 . . ?
Ni1 O6 H2W 110.4 . . ?
H1W O6 H2W 92.1 . . ?
H3W O7 H4W 124.4 . . ?
O2 C1 O1 125.4(2) . . ?
O2 C1 C2 118.2(2) . . ?
O1 C1 C2 116.3(2) . . ?
C3 C2 C6 118.7(2) . . ?
C3 C2 C1 120.1(2) . . ?
C6 C2 C1 121.2(2) . . ?
N1 C3 C2 123.0(2) . . ?
N1 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N1 C4 C5 122.2(2) . . ?
N1 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 O3 118.5(2) . . ?
C4 C5 O3 121.6(2) . . ?
C5 C6 C2 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C2 C6 H6 120.8 . . ?
C13 C7 C8 121.4(3) . . ?
C13 C7 O3 118.2(3) . . ?
C8 C7 O3 120.3(2) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C12 118.8(2) . . ?
C9 C10 C11 121.2(2) . . ?
C12 C10 C11 120.0(2) . . ?
O4 C11 O5 124.8(2) . . ?
O4 C11 C10 118.9(2) . . ?
O5 C11 C10 116.3(2) . . ?
C10 C12 C13 120.6(3) . . ?
C10 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C7 C13 C12 119.4(3) . . ?
C7 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N2 C14 C15 122.9(3) . . ?
N2 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N2 C18 C17 121.5(3) . . ?
N2 C18 C19 114.6(2) . . ?
C17 C18 C19 123.8(3) . . ?
N3 C19 C20 121.3(3) . . ?
N3 C19 C18 115.1(2) . . ?
C20 C19 C18 123.6(3) . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 118.9(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
N3 C23 C22 122.2(3) . . ?
N3 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 O2 -68.2(3) 7_576 . . . ?
Ni1 O1 C1 C2 111.0(2) 7_576 . . . ?
O2 C1 C2 C3 -167.6(2) . . . . ?
O1 C1 C2 C3 13.2(3) . . . . ?
O2 C1 C2 C6 14.3(4) . . . . ?
O1 C1 C2 C6 -165.0(2) . . . . ?
C4 N1 C3 C2 0.3(4) . . . . ?
Ni1 N1 C3 C2 174.99(18) . . . . ?
C6 C2 C3 N1 -0.7(4) . . . . ?
C1 C2 C3 N1 -178.9(2) . . . . ?
C3 N1 C4 C5 0.2(4) . . . . ?
Ni1 N1 C4 C5 -174.18(18) . . . . ?
N1 C4 C5 C6 -0.3(4) . . . . ?
N1 C4 C5 O3 -176.9(2) . . . . ?
C7 O3 C5 C6 147.1(2) . . . . ?
C7 O3 C5 C4 -36.3(3) . . . . ?
C4 C5 C6 C2 -0.1(4) . . . . ?
O3 C5 C6 C2 176.6(2) . . . . ?
C3 C2 C6 C5 0.6(3) . . . . ?
C1 C2 C6 C5 178.8(2) . . . . ?
C5 O3 C7 C13 -81.9(3) . . . . ?
C5 O3 C7 C8 100.4(3) . . . . ?
C13 C7 C8 C9 1.2(4) . . . . ?
O3 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C12 -0.3(4) . . . . ?
C8 C9 C10 C11 177.5(3) . . . . ?
Ni1 O5 C11 O4 8.7(5) 6_575 . . . ?
Ni1 O5 C11 C10 -173.82(17) 6_575 . . . ?
C9 C10 C11 O4 -9.4(4) . . . . ?
C12 C10 C11 O4 168.4(3) . . . . ?
C9 C10 C11 O5 173.0(3) . . . . ?
C12 C10 C11 O5 -9.2(4) . . . . ?
C9 C10 C12 C13 0.7(5) . . . . ?
C11 C10 C12 C13 -177.2(3) . . . . ?
C8 C7 C13 C12 -0.8(5) . . . . ?
O3 C7 C13 C12 -178.4(3) . . . . ?
C10 C12 C13 C7 -0.1(5) . . . . ?
C18 N2 C14 C15 0.7(4) . . . . ?
Ni1 N2 C14 C15 -177.6(2) . . . . ?
N2 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C14 N2 C18 C17 -1.6(4) . . . . ?
Ni1 N2 C18 C17 177.0(2) . . . . ?
C14 N2 C18 C19 177.5(2) . . . . ?
Ni1 N2 C18 C19 -4.0(3) . . . . ?
C16 C17 C18 N2 1.3(4) . . . . ?
C16 C17 C18 C19 -177.7(3) . . . . ?
C23 N3 C19 C20 0.9(4) . . . . ?
Ni1 N3 C19 C20 177.7(2) . . . . ?
C23 N3 C19 C18 -177.2(2) . . . . ?
Ni1 N3 C19 C18 -0.3(3) . . . . ?
N2 C18 C19 N3 2.9(3) . . . . ?
C17 C18 C19 N3 -178.1(2) . . . . ?
N2 C18 C19 C20 -175.2(3) . . . . ?
C17 C18 C19 C20 3.8(4) . . . . ?
N3 C19 C20 C21 -0.9(4) . . . . ?
C18 C19 C20 C21 177.0(3) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C19 N3 C23 C22 -0.3(4) . . . . ?
Ni1 N3 C23 C22 -176.8(2) . . . . ?
C21 C22 C23 N3 -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H1W O2 0.85 1.87 2.725(3) 179.7 7_576
O6 H2W O4 0.87 1.89 2.674(3) 148.3 6_576
O7 H3W O4 0.85 1.89 2.740(3) 179.4 5_666
O7 H4W O4 0.85 1.89 2.740(3) 179.4 6_566

_refine_diff_density_max         0.671
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.057

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

data_326-5Cu
_database_code_depnum_ccdc_archive 'CCDC 1559266'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cu N3 O6'
_chemical_formula_weight         494.93

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1215(5)
_cell_length_b                   17.7404(10)
_cell_length_c                   17.0416(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.330(8)
_cell_angle_gamma                90
_cell_volume                     2130.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7621
_cell_measurement_theta_min      3.334
_cell_measurement_theta_max      25.050

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   0.773
_exptl_transmission_factor_max   0.781
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    1.072
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7621
_diffrn_reflns_av_unetI/netI     0.1285
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3768
_reflns_number_gt                2043
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0204P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3768
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Cu1 Cu 0.40223(10) 0.33702(3) 0.60541(4) 0.0404(2) Uani 1 1 d . . . . .
N1 N 0.8300(7) 0.2828(3) 0.9283(3) 0.0534(14) Uani 1 1 d . . . . .
N2 N 0.3369(6) 0.3471(2) 0.4867(3) 0.0378(12) Uani 1 1 d . . . . .
N3 N 0.3352(6) 0.4461(2) 0.5997(3) 0.0380(12) Uani 1 1 d . . . . .
O1 O 0.5276(5) 0.3425(2) 0.7150(2) 0.0472(11) Uani 1 1 d . . . . .
O2 O 0.7865(6) 0.3833(2) 0.6684(2) 0.0534(11) Uani 1 1 d . . . . .
O3 O 1.2332(6) 0.4030(2) 0.9399(3) 0.0775(16) Uani 1 1 d . . . . .
O4 O 1.7405(6) 0.6730(2) 0.8509(3) 0.0658(14) Uani 1 1 d . . . . .
O5 O 1.5140(5) 0.73421(19) 0.9012(2) 0.0496(11) Uani 1 1 d . . . . .
O6 O 0.1068(6) 0.3089(2) 0.6283(3) 0.0861(18) Uani 1 1 d . . . . .
H1W H 0.0789 0.3322 0.6706 0.129 Uiso 1 1 d R U . . .
H2W H 0.0964 0.2604 0.6360 0.129 Uiso 1 1 d R U . . .
C1 C 0.7030(9) 0.3589(3) 0.7229(4) 0.0373(14) Uani 1 1 d . . . . .
C2 C 0.8103(7) 0.3470(3) 0.8037(3) 0.0344(14) Uani 1 1 d . . . . .
C3 C 0.9762(8) 0.3860(3) 0.8301(4) 0.0422(15) Uani 1 1 d . . . . .
H3 H 1.0270 0.4201 0.7974 0.051 Uiso 1 1 calc R U . . .
C4 C 1.0629(8) 0.3728(3) 0.9061(4) 0.0417(15) Uani 1 1 d . . . . .
C5 C 0.9875(8) 0.3215(3) 0.9539(3) 0.0457(16) Uani 1 1 d . . . . .
H5 H 1.0481 0.3138 1.0054 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7444(8) 0.2968(3) 0.8546(4) 0.0486(16) Uani 1 1 d . . . . .
H6 H 0.6332 0.2707 0.8366 0.058 Uiso 1 1 calc R U . . .
C7 C 1.3022(10) 0.4705(3) 0.9141(4) 0.0527(18) Uani 1 1 d . . . . .
C8 C 1.4804(10) 0.4681(3) 0.8941(4) 0.0597(19) Uani 1 1 d . . . . .
H8 H 1.5416 0.4222 0.8906 0.072 Uiso 1 1 calc R U . . .
C9 C 1.5686(9) 0.5343(3) 0.8792(4) 0.0546(18) Uani 1 1 d . . . . .
H9 H 1.6902 0.5327 0.8654 0.066 Uiso 1 1 calc R U . . .
C10 C 1.4806(9) 0.6031(3) 0.8843(3) 0.0404(15) Uani 1 1 d . . . . .
C11 C 1.5877(9) 0.6748(3) 0.8768(3) 0.0424(15) Uani 1 1 d . . . . .
C12 C 1.2978(9) 0.6038(3) 0.9014(4) 0.0516(17) Uani 1 1 d . . . . .
H12 H 1.2344 0.6494 0.9035 0.062 Uiso 1 1 calc R U . . .
C13 C 1.2069(9) 0.5369(4) 0.9155(4) 0.062(2) Uani 1 1 d . . . . .
H13 H 1.0822 0.5374 0.9258 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3416(8) 0.2928(3) 0.4321(4) 0.0466(16) Uani 1 1 d . . . . .
H14 H 0.3851 0.2452 0.4490 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2857(8) 0.3043(4) 0.3532(4) 0.0508(17) Uani 1 1 d . . . . .
H15 H 0.2869 0.2649 0.3172 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2275(8) 0.3750(4) 0.3279(4) 0.0545(17) Uani 1 1 d . . . . .
H16 H 0.1888 0.3842 0.2743 0.065 Uiso 1 1 calc R U . . .
C17 C 0.2267(8) 0.4320(3) 0.3820(4) 0.0479(16) Uani 1 1 d . . . . .
H17 H 0.1891 0.4803 0.3654 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2820(7) 0.4172(3) 0.4612(4) 0.0325(14) Uani 1 1 d . . . . .
C19 C 0.2820(7) 0.4734(3) 0.5264(4) 0.0323(13) Uani 1 1 d . . . . .
C20 C 0.2309(7) 0.5479(3) 0.5128(4) 0.0456(16) Uani 1 1 d . . . . .
H20 H 0.1961 0.5658 0.4614 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2327(8) 0.5955(3) 0.5778(5) 0.0557(19) Uani 1 1 d . . . . .
H21 H 0.1988 0.6460 0.5707 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2851(8) 0.5669(4) 0.6522(4) 0.0575(18) Uani 1 1 d . . . . .
H22 H 0.2864 0.5977 0.6964 0.069 Uiso 1 1 calc R U . . .
C23 C 0.3363(8) 0.4919(3) 0.6614(4) 0.0480(16) Uani 1 1 d . . . . .
H23 H 0.3725 0.4729 0.7122 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O5 1.927(3) 2_746 ?
Cu1 O1 1.952(4) . ?
Cu1 N3 1.993(4) . ?
Cu1 N2 2.017(4) . ?
Cu1 O6 2.250(4) . ?
N1 C5 1.333(6) . ?
N1 C6 1.338(7) . ?
N2 C14 1.343(6) . ?
N2 C18 1.355(6) . ?
N3 C23 1.328(6) . ?
N3 C19 1.341(6) . ?
O1 C1 1.271(6) . ?
O2 C1 1.249(6) . ?
O3 C4 1.374(6) . ?
O3 C7 1.390(6) . ?
O4 C11 1.233(6) . ?
O5 C11 1.273(6) . ?
O5 Cu1 1.927(3) 2_756 ?
O6 H1W 0.8772 . ?
O6 H2W 0.8748 . ?
C1 C2 1.490(7) . ?
C2 C6 1.373(7) . ?
C2 C3 1.387(7) . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C13 1.361(8) . ?
C7 C8 1.361(8) . ?
C8 C9 1.372(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(7) . ?
C9 H9 0.9300 . ?
C10 C12 1.375(7) . ?
C10 C11 1.499(7) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.361(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.494(7) . ?
C19 C20 1.381(6) . ?
C20 C21 1.392(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O1 90.02(16) 2_746 . ?
O5 Cu1 N3 172.05(18) 2_746 . ?
O1 Cu1 N3 94.12(18) . . ?
O5 Cu1 N2 93.09(17) 2_746 . ?
O1 Cu1 N2 164.16(17) . . ?
N3 Cu1 N2 81.12(19) . . ?
O5 Cu1 O6 96.04(16) 2_746 . ?
O1 Cu1 O6 98.90(17) . . ?
N3 Cu1 O6 90.02(16) . . ?
N2 Cu1 O6 96.21(18) . . ?
C5 N1 C6 117.3(5) . . ?
C14 N2 C18 118.0(5) . . ?
C14 N2 Cu1 127.3(4) . . ?
C18 N2 Cu1 114.7(4) . . ?
C23 N3 C19 119.0(5) . . ?
C23 N3 Cu1 125.5(4) . . ?
C19 N3 Cu1 115.4(4) . . ?
C1 O1 Cu1 114.8(4) . . ?
C4 O3 C7 122.3(5) . . ?
C11 O5 Cu1 128.2(4) . 2_756 ?
Cu1 O6 H1W 111.5 . . ?
Cu1 O6 H2W 110.2 . . ?
H1W O6 H2W 107.7 . . ?
O2 C1 O1 124.5(6) . . ?
O2 C1 C2 120.0(5) . . ?
O1 C1 C2 115.5(5) . . ?
C6 C2 C3 118.2(5) . . ?
C6 C2 C1 119.9(5) . . ?
C3 C2 C1 121.9(5) . . ?
C4 C3 C2 117.8(5) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 O3 125.3(5) . . ?
C3 C4 C5 120.7(6) . . ?
O3 C4 C5 113.9(6) . . ?
N1 C5 C4 121.8(6) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N1 C6 C2 124.2(5) . . ?
N1 C6 H6 117.9 . . ?
C2 C6 H6 117.9 . . ?
C13 C7 C8 121.0(6) . . ?
C13 C7 O3 122.7(7) . . ?
C8 C7 O3 116.0(6) . . ?
C7 C8 C9 119.3(6) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 121.4(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C12 C10 C9 118.3(5) . . ?
C12 C10 C11 121.3(5) . . ?
C9 C10 C11 120.3(6) . . ?
O4 C11 O5 124.5(5) . . ?
O4 C11 C10 119.6(6) . . ?
O5 C11 C10 115.9(5) . . ?
C10 C12 C13 120.5(6) . . ?
C10 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C7 C13 C12 119.4(6) . . ?
C7 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N2 C14 C15 123.0(6) . . ?
N2 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 118.7(6) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 119.6(6) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.4(6) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N2 C18 C17 121.2(5) . . ?
N2 C18 C19 113.9(5) . . ?
C17 C18 C19 124.9(5) . . ?
N3 C19 C20 122.3(5) . . ?
N3 C19 C18 114.9(4) . . ?
C20 C19 C18 122.8(5) . . ?
C19 C20 C21 118.4(6) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C22 C21 C20 118.9(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 119.7(6) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
N3 C23 C22 121.8(6) . . ?
N3 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 12.7(7) . . . . ?
Cu1 O1 C1 C2 -167.2(3) . . . . ?
O2 C1 C2 C6 -156.3(5) . . . . ?
O1 C1 C2 C6 23.5(7) . . . . ?
O2 C1 C2 C3 24.3(8) . . . . ?
O1 C1 C2 C3 -155.8(5) . . . . ?
C6 C2 C3 C4 -0.9(8) . . . . ?
C1 C2 C3 C4 178.4(5) . . . . ?
C2 C3 C4 O3 175.8(5) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C7 O3 C4 C3 25.2(10) . . . . ?
C7 O3 C4 C5 -159.4(6) . . . . ?
C6 N1 C5 C4 -1.5(9) . . . . ?
C3 C4 C5 N1 0.5(9) . . . . ?
O3 C4 C5 N1 -175.1(5) . . . . ?
C5 N1 C6 C2 1.2(9) . . . . ?
C3 C2 C6 N1 0.0(9) . . . . ?
C1 C2 C6 N1 -179.4(5) . . . . ?
C4 O3 C7 C13 60.0(9) . . . . ?
C4 O3 C7 C8 -126.1(6) . . . . ?
C13 C7 C8 C9 3.4(10) . . . . ?
O3 C7 C8 C9 -170.6(6) . . . . ?
C7 C8 C9 C10 0.2(10) . . . . ?
C8 C9 C10 C12 -2.8(9) . . . . ?
C8 C9 C10 C11 173.0(6) . . . . ?
Cu1 O5 C11 O4 7.4(9) 2_756 . . . ?
Cu1 O5 C11 C10 -175.1(4) 2_756 . . . ?
C12 C10 C11 O4 -170.0(6) . . . . ?
C9 C10 C11 O4 14.3(9) . . . . ?
C12 C10 C11 O5 12.4(8) . . . . ?
C9 C10 C11 O5 -163.4(5) . . . . ?
C9 C10 C12 C13 2.0(9) . . . . ?
C11 C10 C12 C13 -173.8(6) . . . . ?
C8 C7 C13 C12 -4.3(10) . . . . ?
O3 C7 C13 C12 169.4(5) . . . . ?
C10 C12 C13 C7 1.5(10) . . . . ?
C18 N2 C14 C15 -3.1(8) . . . . ?
Cu1 N2 C14 C15 176.6(4) . . . . ?
N2 C14 C15 C16 2.1(9) . . . . ?
C14 C15 C16 C17 -0.1(9) . . . . ?
C15 C16 C17 C18 -0.9(9) . . . . ?
C14 N2 C18 C17 2.1(7) . . . . ?
Cu1 N2 C18 C17 -177.7(4) . . . . ?
C14 N2 C18 C19 -179.9(4) . . . . ?
Cu1 N2 C18 C19 0.3(5) . . . . ?
C16 C17 C18 N2 -0.2(8) . . . . ?
C16 C17 C18 C19 -178.0(5) . . . . ?
C23 N3 C19 C20 1.0(8) . . . . ?
Cu1 N3 C19 C20 179.9(4) . . . . ?
C23 N3 C19 C18 -178.9(5) . . . . ?
Cu1 N3 C19 C18 0.0(5) . . . . ?
N2 C18 C19 N3 -0.2(6) . . . . ?
C17 C18 C19 N3 177.7(5) . . . . ?
N2 C18 C19 C20 179.9(5) . . . . ?
C17 C18 C19 C20 -2.2(8) . . . . ?
N3 C19 C20 C21 -0.9(8) . . . . ?
C18 C19 C20 C21 179.0(5) . . . . ?
C19 C20 C21 C22 0.2(8) . . . . ?
C20 C21 C22 C23 0.4(9) . . . . ?
C19 N3 C23 C22 -0.3(8) . . . . ?
Cu1 N3 C23 C22 -179.1(4) . . . . ?
C21 C22 C23 N3 -0.4(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O5 0.93 2.56 3.060(8) 114.2 2_746
O6 H2W O4 0.87 1.93 2.648(5) 138.1 2_746
O6 H1W O2 0.88 2.27 2.804(5) 119.4 1_455
C17 H17 O2 0.93 2.50 3.386(7) 159.4 3_666
C20 H20 O2 0.93 2.41 3.306(7) 161.8 3_666
C23 H23 O1 0.93 2.56 3.058(7) 113.8 .

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_299-13Zn1
_database_code_depnum_ccdc_archive 'CCDC 1536685'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 N3 O5 Zn'
_chemical_formula_weight         502.77

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.1880(7)
_cell_length_b                   12.1197(5)
_cell_length_c                   16.2388(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.082(6)
_cell_angle_gamma                90
_cell_volume                     2144.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7601
_cell_measurement_theta_min      3.362
_cell_measurement_theta_max      25.045

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   0.750
_exptl_transmission_factor_max   0.770
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.190
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7601
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.362
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_full        25.045
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3797
_reflns_number_gt                2004
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0114P)²] 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         3797
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Zn1 Zn 0.65959(6) 0.40696(5) 0.21718(4) 0.0505(2) Uani 1 1 d . . . . .
N1 N 1.5590(5) 0.7636(4) 0.4942(4) 0.0826(18) Uani 1 1 d . . . . .
N2 N 0.6109(4) 0.2963(3) 0.1178(3) 0.0450(12) Uani 1 1 d . . . . .
N3 N 0.5069(4) 0.4878(3) 0.1463(3) 0.0442(11) Uani 1 1 d . . . . .
O1 O 0.8092(3) 0.4927(3) 0.2239(2) 0.0606(11) Uani 1 1 d . . . . .
O2 O 0.8810(3) 0.3240(3) 0.2490(3) 0.0726(13) Uani 1 1 d . . . . .
O3 O 1.3784(4) 0.5966(4) 0.3288(3) 0.0884(14) Uani 1 1 d . . . . .
O4 O 1.4191(4) 0.6682(3) 0.6984(3) 0.0742(13) Uani 1 1 d . . . . .
O5 O 1.3318(4) 0.5234(3) 0.6327(3) 0.1018(18) Uani 1 1 d . . . . .
C1 C 0.8978(5) 0.4234(5) 0.2427(3) 0.0510(15) Uani 1 1 d . . . . .
C2 C 1.0241(5) 0.4719(4) 0.2627(3) 0.0462(14) Uani 1 1 d . . . . .
C3 C 1.0426(5) 0.5824(4) 0.2776(4) 0.0632(17) Uani 1 1 d . . . . .
H3 H 0.9752 0.6291 0.2719 0.076 Uiso 1 1 calc R U . . .
C4 C 1.1603(6) 0.6258(5) 0.3012(4) 0.076(2) Uani 1 1 d . . . . .
H4 H 1.1723 0.7008 0.3122 0.091 Uiso 1 1 calc R U . . .
C5 C 1.2578(6) 0.5562(6) 0.3078(4) 0.0662(18) Uani 1 1 d . . . . .
C6 C 1.2433(5) 0.4460(5) 0.2905(4) 0.074(2) Uani 1 1 d . . . . .
H6 H 1.3108 0.4002 0.2932 0.089 Uiso 1 1 calc R U . . .
C7 C 1.1254(5) 0.4047(4) 0.2688(4) 0.0674(19) Uani 1 1 d . . . . .
H7 H 1.1138 0.3297 0.2579 0.081 Uiso 1 1 calc R U . . .
C8 C 1.4206(5) 0.6379(5) 0.4103(4) 0.0618(17) Uani 1 1 d . . . . .
C9 C 1.5109(5) 0.7170(5) 0.4208(4) 0.0710(19) Uani 1 1 d . . . . .
H9 H 1.5395 0.7387 0.3738 0.085 Uiso 1 1 calc R U . . .
C10 C 1.5177(5) 0.7271(4) 0.5621(4) 0.0651(18) Uani 1 1 d . . . . .
H10 H 1.5496 0.7592 0.6145 0.078 Uiso 1 1 calc R U . . .
C11 C 1.4316(5) 0.6456(4) 0.5571(4) 0.0467(15) Uani 1 1 d . . . . .
C12 C 1.3899(5) 0.6081(5) 0.6344(4) 0.0564(16) Uani 1 1 d . . . . .
C13 C 1.3828(5) 0.5993(4) 0.4794(4) 0.0620(17) Uani 1 1 d . . . . .
H13 H 1.3253 0.5429 0.4739 0.074 Uiso 1 1 calc R U . . .
C14 C 0.6645(5) 0.2024(5) 0.1035(4) 0.0629(18) Uani 1 1 d . . . . .
H14 H 0.7374 0.1816 0.1403 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6146(7) 0.1342(5) 0.0348(5) 0.077(2) Uani 1 1 d . . . . .
H15 H 0.6547 0.0696 0.0259 0.092 Uiso 1 1 calc R U . . .
C16 C 0.5074(7) 0.1626(5) -0.0186(4) 0.076(2) Uani 1 1 d . . . . .
H16 H 0.4738 0.1176 -0.0644 0.092 Uiso 1 1 calc R U . . .
C17 C 0.4475(5) 0.2595(5) -0.0049(4) 0.0549(16) Uani 1 1 d . . . . .
C18 C 0.5033(5) 0.3241(4) 0.0644(4) 0.0439(14) Uani 1 1 d . . . . .
C19 C 0.3349(6) 0.2945(6) -0.0580(4) 0.073(2) Uani 1 1 d . . . . .
H19 H 0.2983 0.2519 -0.1045 0.087 Uiso 1 1 calc R U . . .
C20 C 0.2809(6) 0.3879(6) -0.0420(4) 0.073(2) Uani 1 1 d . . . . .
H20 H 0.2065 0.4083 -0.0771 0.087 Uiso 1 1 calc R U . . .
C21 C 0.3344(5) 0.4567(5) 0.0273(4) 0.0505(15) Uani 1 1 d . . . . .
C22 C 0.4465(4) 0.4258(4) 0.0805(3) 0.0394(13) Uani 1 1 d . . . . .
C23 C 0.2845(6) 0.5566(5) 0.0462(5) 0.071(2) Uani 1 1 d . . . . .
H23 H 0.2092 0.5800 0.0139 0.086 Uiso 1 1 calc R U . . .
C24 C 0.3445(6) 0.6189(5) 0.1105(5) 0.073(2) Uani 1 1 d . . . . .
H24 H 0.3111 0.6858 0.1221 0.087 Uiso 1 1 calc R U . . .
C25 C 0.4575(5) 0.5839(4) 0.1604(4) 0.0591(17) Uani 1 1 d . . . . .
H25 H 0.4986 0.6288 0.2042 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.953(3) . ?
Zn1 O4 2.007(4) 3_766 ?
Zn1 N2 2.074(4) . ?
Zn1 N3 2.077(4) . ?
Zn1 C12 2.599(7) 3_766 ?
N1 C9 1.319(7) . ?
N1 C10 1.361(7) . ?
N2 C14 1.330(6) . ?
N2 C18 1.358(6) . ?
N3 C25 1.331(5) . ?
N3 C22 1.355(6) . ?
O1 C1 1.282(5) . ?
O2 C1 1.227(5) . ?
O3 C8 1.393(7) . ?
O3 C5 1.403(6) . ?
O4 C12 1.251(6) . ?
O4 Zn1 2.007(4) 3_766 ?
O5 C12 1.212(6) . ?
C1 C2 1.497(6) . ?
C2 C3 1.368(6) . ?
C2 C7 1.380(6) . ?
C3 C4 1.389(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(7) . ?
C6 C7 1.379(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.368(7) . ?
C8 C9 1.375(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C13 1.376(7) . ?
C11 C12 1.504(8) . ?
C12 Zn1 2.599(7) 3_766 ?
C13 H13 0.9300 . ?
C14 C15 1.400(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.356(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.398(7) . ?
C17 C19 1.421(7) . ?
C18 C22 1.437(6) . ?
C19 C20 1.336(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.420(7) . ?
C20 H20 0.9300 . ?
C21 C23 1.396(7) . ?
C21 C22 1.404(6) . ?
C23 C24 1.340(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.404(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O4 134.93(18) . 3_766 ?
O1 Zn1 N2 117.31(16) . . ?
O4 Zn1 N2 99.16(17) 3_766 . ?
O1 Zn1 N3 111.54(15) . . ?
O4 Zn1 N3 99.18(17) 3_766 . ?
N2 Zn1 N3 80.57(17) . . ?
O1 Zn1 C12 110.19(18) . 3_766 ?
O4 Zn1 C12 27.92(15) 3_766 3_766 ?
N2 Zn1 C12 127.05(19) . 3_766 ?
N3 Zn1 C12 103.06(17) . 3_766 ?
C9 N1 C10 116.7(5) . . ?
C14 N2 C18 118.1(5) . . ?
C14 N2 Zn1 129.7(4) . . ?
C18 N2 Zn1 112.0(3) . . ?
C25 N3 C22 117.9(5) . . ?
C25 N3 Zn1 129.8(4) . . ?
C22 N3 Zn1 112.1(3) . . ?
C1 O1 Zn1 105.7(3) . . ?
C8 O3 C5 117.2(5) . . ?
C12 O4 Zn1 103.4(4) . 3_766 ?
O2 C1 O1 122.6(5) . . ?
O2 C1 C2 121.4(5) . . ?
O1 C1 C2 115.8(5) . . ?
C3 C2 C7 118.4(5) . . ?
C3 C2 C1 121.3(5) . . ?
C7 C2 C1 120.3(5) . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.2(6) . . ?
C4 C5 O3 120.7(6) . . ?
C6 C5 O3 117.0(6) . . ?
C5 C6 C7 118.0(6) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C2 C7 C6 121.8(5) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C13 C8 C9 119.4(6) . . ?
C13 C8 O3 123.7(5) . . ?
C9 C8 O3 116.8(6) . . ?
N1 C9 C8 123.3(6) . . ?
N1 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N1 C10 C11 123.3(6) . . ?
N1 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C10 C11 C13 118.4(6) . . ?
C10 C11 C12 121.0(6) . . ?
C13 C11 C12 120.6(5) . . ?
O5 C12 O4 123.3(7) . . ?
O5 C12 C11 120.1(6) . . ?
O4 C12 C11 116.5(6) . . ?
O5 C12 Zn1 74.7(4) . 3_766 ?
O4 C12 Zn1 48.7(3) . 3_766 ?
C11 C12 Zn1 165.1(5) . 3_766 ?
C8 C13 C11 118.8(5) . . ?
C8 C13 H13 120.6 . . ?
C11 C13 H13 120.6 . . ?
N2 C14 C15 122.0(6) . . ?
N2 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C16 C15 C14 119.7(6) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.0(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 117.2(6) . . ?
C16 C17 C19 123.2(6) . . ?
C18 C17 C19 119.6(5) . . ?
N2 C18 C17 123.0(5) . . ?
N2 C18 C22 117.5(5) . . ?
C17 C18 C22 119.5(5) . . ?
C20 C19 C17 120.8(6) . . ?
C20 C19 H19 119.6 . . ?
C17 C19 H19 119.6 . . ?
C19 C20 C21 121.6(6) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C23 C21 C22 116.3(6) . . ?
C23 C21 C20 124.5(6) . . ?
C22 C21 C20 119.3(5) . . ?
N3 C22 C21 123.6(5) . . ?
N3 C22 C18 117.2(5) . . ?
C21 C22 C18 119.1(5) . . ?
C24 C23 C21 120.4(6) . . ?
C24 C23 H23 119.8 . . ?
C21 C23 H23 119.8 . . ?
C23 C24 C25 120.4(5) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
N3 C25 C24 121.4(6) . . ?
N3 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 3.6(7) . . . . ?
Zn1 O1 C1 C2 -172.3(4) . . . . ?
O2 C1 C2 C3 -162.5(6) . . . . ?
O1 C1 C2 C3 13.5(8) . . . . ?
O2 C1 C2 C7 15.7(9) . . . . ?
O1 C1 C2 C7 -168.3(5) . . . . ?
C7 C2 C3 C4 -2.2(9) . . . . ?
C1 C2 C3 C4 176.1(6) . . . . ?
C2 C3 C4 C5 1.1(10) . . . . ?
C3 C4 C5 C6 1.3(10) . . . . ?
C3 C4 C5 O3 178.1(5) . . . . ?
C8 O3 C5 C4 67.8(8) . . . . ?
C8 O3 C5 C6 -115.2(6) . . . . ?
C4 C5 C6 C7 -2.5(10) . . . . ?
O3 C5 C6 C7 -179.3(6) . . . . ?
C3 C2 C7 C6 1.0(9) . . . . ?
C1 C2 C7 C6 -177.3(6) . . . . ?
C5 C6 C7 C2 1.3(10) . . . . ?
C5 O3 C8 C13 31.4(9) . . . . ?
C5 O3 C8 C9 -152.9(6) . . . . ?
C10 N1 C9 C8 2.1(10) . . . . ?
C13 C8 C9 N1 -4.3(10) . . . . ?
O3 C8 C9 N1 179.8(6) . . . . ?
C9 N1 C10 C11 0.7(10) . . . . ?
N1 C10 C11 C13 -1.1(9) . . . . ?
N1 C10 C11 C12 179.6(5) . . . . ?
Zn1 O4 C12 O5 -2.9(7) 3_766 . . . ?
Zn1 O4 C12 C11 177.6(4) 3_766 . . . ?
C10 C11 C12 O5 -166.3(6) . . . . ?
C13 C11 C12 O5 14.5(8) . . . . ?
C10 C11 C12 O4 13.2(8) . . . . ?
C13 C11 C12 O4 -166.0(5) . . . . ?
C10 C11 C12 Zn1 20.2(18) . . . 3_766 ?
C13 C11 C12 Zn1 -159.0(13) . . . 3_766 ?
C9 C8 C13 C11 3.7(9) . . . . ?
O3 C8 C13 C11 179.3(5) . . . . ?
C10 C11 C13 C8 -1.2(8) . . . . ?
C12 C11 C13 C8 178.1(5) . . . . ?
C18 N2 C14 C15 1.4(8) . . . . ?
Zn1 N2 C14 C15 176.3(4) . . . . ?
N2 C14 C15 C16 -1.0(10) . . . . ?
C14 C15 C16 C17 0.0(10) . . . . ?
C15 C16 C17 C18 0.6(9) . . . . ?
C15 C16 C17 C19 -179.8(6) . . . . ?
C14 N2 C18 C17 -0.7(8) . . . . ?
Zn1 N2 C18 C17 -176.5(4) . . . . ?
C14 N2 C18 C22 -179.9(4) . . . . ?
Zn1 N2 C18 C22 4.3(6) . . . . ?
C16 C17 C18 N2 -0.2(8) . . . . ?
C19 C17 C18 N2 -179.8(5) . . . . ?
C16 C17 C18 C22 178.9(5) . . . . ?
C19 C17 C18 C22 -0.7(8) . . . . ?
C16 C17 C19 C20 179.7(6) . . . . ?
C18 C17 C19 C20 -0.7(9) . . . . ?
C17 C19 C20 C21 1.1(10) . . . . ?
C19 C20 C21 C23 178.2(6) . . . . ?
C19 C20 C21 C22 -0.2(9) . . . . ?
C25 N3 C22 C21 -0.8(7) . . . . ?
Zn1 N3 C22 C21 174.0(4) . . . . ?
C25 N3 C22 C18 177.9(4) . . . . ?
Zn1 N3 C22 C18 -7.3(5) . . . . ?
C23 C21 C22 N3 -1.0(8) . . . . ?
C20 C21 C22 N3 177.5(5) . . . . ?
C23 C21 C22 C18 -179.7(5) . . . . ?
C20 C21 C22 C18 -1.2(8) . . . . ?
N2 C18 C22 N3 2.0(7) . . . . ?
C17 C18 C22 N3 -177.2(5) . . . . ?
N2 C18 C22 C21 -179.2(5) . . . . ?
C17 C18 C22 C21 1.6(7) . . . . ?
C22 C21 C23 C24 1.8(8) . . . . ?
C20 C21 C23 C24 -176.6(6) . . . . ?
C21 C23 C24 C25 -0.8(10) . . . . ?
C22 N3 C25 C24 1.9(8) . . . . ?
Zn1 N3 C25 C24 -171.9(4) . . . . ?
C23 C24 C25 N3 -1.1(9) . . . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_298-4Mn1
_database_code_depnum_ccdc_archive 'CCDC 1536679'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Mn N O7'
_chemical_formula_weight         348.17

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.1869(8)
_cell_length_b                   8.2238(13)
_cell_length_c                   26.240(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.688(13)
_cell_angle_gamma                90
_cell_volume                     1334.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4284
_cell_measurement_theta_min      3.359
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   0.774
_exptl_transmission_factor_max   0.798
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.026
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4284
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2369
_reflns_number_gt                1486
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0739P)²] 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         2369
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Mn1 Mn -0.48970(14) 0.87136(12) 0.55293(3) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.2415(7) 0.5345(6) 0.91136(19) 0.0306(12) Uani 1 1 d . . . . .
O1 O -0.3207(6) 0.8823(5) 0.62476(15) 0.0361(11) Uani 1 1 d . . . . .
O2 O -0.0661(7) 0.6974(6) 0.61251(17) 0.0440(12) Uani 1 1 d . . . . .
O3 O 0.1776(7) 0.9110(5) 0.83972(16) 0.0392(11) Uani 1 1 d . . . . .
O4 O 0.8661(7) 0.8569(5) 0.94840(18) 0.0417(12) Uani 1 1 d . . . . .
O5 O 0.8454(6) 0.6026(5) 0.97775(14) 0.0278(10) Uani 1 1 d . . . . .
O6 O -0.6710(10) 0.6524(7) 0.5723(2) 0.0499(15) Uani 1 1 d . . . . .
O7 O -0.2594(7) 0.7084(6) 0.51803(18) 0.0458(12) Uani 1 1 d . . . . .
H3W H -0.3243 0.6465 0.4956 0.069 Uiso 1 1 d R U . . .
H4W H -0.1983 0.6469 0.5411 0.069 Uiso 1 1 d R U . . .
C1 C -0.1570(10) 0.8011(8) 0.6396(2) 0.0304(15) Uani 1 1 d . . . . .
C2 C -0.0718(10) 0.8301(8) 0.6928(2) 0.0313(15) Uani 1 1 d . . . . .
C3 C 0.1174(11) 0.7555(9) 0.7095(3) 0.048(2) Uani 1 1 d . . . . .
H3 H 0.1903 0.6887 0.6871 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2011(11) 0.7766(10) 0.7580(3) 0.051(2) Uani 1 1 d . . . . .
H4 H 0.3284 0.7245 0.7683 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0953(9) 0.8752(8) 0.7909(2) 0.0300(14) Uani 1 1 d . . . . .
C6 C -0.0949(10) 0.9513(9) 0.7760(2) 0.0395(17) Uani 1 1 d . . . . .
H6 H -0.1683 1.0166 0.7986 0.047 Uiso 1 1 calc R U . . .
C7 C -0.1746(10) 0.9286(9) 0.7266(2) 0.0412(17) Uani 1 1 d . . . . .
H7 H -0.3011 0.9816 0.7161 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2770(10) 0.7869(8) 0.8678(2) 0.0315(15) Uani 1 1 d . . . . .
C9 C 0.1629(10) 0.6488(7) 0.8782(2) 0.0318(15) Uani 1 1 d . . . . .
H9 H 0.0286 0.6327 0.8621 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4366(9) 0.5619(8) 0.9324(2) 0.0297(14) Uani 1 1 d . . . . .
H10 H 0.4937 0.4838 0.9546 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5595(9) 0.6978(7) 0.9235(2) 0.0261(14) Uani 1 1 d . . . . .
C12 C 0.7721(9) 0.7249(7) 0.9515(2) 0.0288(14) Uani 1 1 d . . . . .
C13 C 0.4773(10) 0.8146(7) 0.8901(2) 0.0312(15) Uani 1 1 d . . . . .
H13 H 0.5551 0.9083 0.8830 0.037 Uiso 1 1 calc R U . . .
H1W H -0.790(8) 0.675(6) 0.588(2) 0.005(14) Uiso 1 1 d . . . . .
H2W H -0.633(11) 0.564(9) 0.576(3) 0.05(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.130(4) . ?
Mn1 O7 2.177(4) . ?
Mn1 O6 2.189(6) . ?
Mn1 O5 2.204(4) 4_475 ?
Mn1 O5 2.259(4) 2_556 ?
Mn1 N1 2.279(5) 2_456 ?
N1 C10 1.332(7) . ?
N1 C9 1.361(7) . ?
N1 Mn1 2.279(5) 2_446 ?
O1 C1 1.265(7) . ?
O2 C1 1.253(7) . ?
O3 C8 1.392(7) . ?
O3 C5 1.397(7) . ?
O4 C12 1.235(7) . ?
O5 C12 1.293(7) . ?
O5 Mn1 2.205(4) 4_776 ?
O5 Mn1 2.259(4) 2_546 ?
O6 H1W 0.87(5) . ?
O6 H2W 0.77(7) . ?
O7 H3W 0.8673 . ?
O7 H4W 0.8667 . ?
C1 C2 1.497(8) . ?
C2 C7 1.371(9) . ?
C2 C3 1.382(8) . ?
C3 C4 1.370(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(8) . ?
C6 C7 1.385(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.368(8) . ?
C8 C13 1.373(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(8) . ?
C10 H10 0.9300 . ?
C11 C13 1.388(8) . ?
C11 C12 1.504(8) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O7 95.05(18) . . ?
O1 Mn1 O6 94.1(2) . . ?
O7 Mn1 O6 86.4(2) . . ?
O1 Mn1 O5 171.82(16) . 4_475 ?
O7 Mn1 O5 88.55(17) . 4_475 ?
O6 Mn1 O5 93.47(19) . 4_475 ?
O1 Mn1 O5 95.20(16) . 2_556 ?
O7 Mn1 O5 95.63(16) . 2_556 ?
O6 Mn1 O5 170.28(19) . 2_556 ?
O5 Mn1 O5 77.11(15) 4_475 2_556 ?
O1 Mn1 N1 86.27(17) . 2_456 ?
O7 Mn1 N1 177.67(18) . 2_456 ?
O6 Mn1 N1 91.6(2) . 2_456 ?
O5 Mn1 N1 90.39(16) 4_475 2_456 ?
O5 Mn1 N1 86.15(16) 2_556 2_456 ?
C10 N1 C9 116.8(5) . . ?
C10 N1 Mn1 123.5(4) . 2_446 ?
C9 N1 Mn1 115.7(4) . 2_446 ?
C1 O1 Mn1 128.1(4) . . ?
C8 O3 C5 118.4(5) . . ?
C12 O5 Mn1 123.1(4) . 4_776 ?
C12 O5 Mn1 126.9(4) . 2_546 ?
Mn1 O5 Mn1 102.89(15) 4_776 2_546 ?
Mn1 O6 H1W 112(3) . . ?
Mn1 O6 H2W 130(5) . . ?
H1W O6 H2W 114(7) . . ?
Mn1 O7 H3W 110.6 . . ?
Mn1 O7 H4W 110.1 . . ?
H3W O7 H4W 108.4 . . ?
O2 C1 O1 123.6(6) . . ?
O2 C1 C2 119.0(6) . . ?
O1 C1 C2 117.3(6) . . ?
C7 C2 C3 117.5(6) . . ?
C7 C2 C1 122.7(6) . . ?
C3 C2 C1 119.8(6) . . ?
C4 C3 C2 122.1(6) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 O3 122.5(5) . . ?
C6 C5 O3 116.7(5) . . ?
C7 C6 C5 118.8(6) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C2 C7 C6 121.7(6) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C13 121.2(6) . . ?
C9 C8 O3 119.4(5) . . ?
C13 C8 O3 118.9(6) . . ?
N1 C9 C8 121.5(6) . . ?
N1 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
N1 C10 C11 124.5(6) . . ?
N1 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C10 C11 C13 118.4(5) . . ?
C10 C11 C12 121.2(6) . . ?
C13 C11 C12 120.3(5) . . ?
O4 C12 O5 124.1(6) . . ?
O4 C12 C11 120.3(5) . . ?
O5 C12 C11 115.6(5) . . ?
C8 C13 C11 117.6(6) . . ?
C8 C13 H13 121.2 . . ?
C11 C13 H13 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 0.2(9) . . . . ?
Mn1 O1 C1 C2 -178.7(4) . . . . ?
O2 C1 C2 C7 -173.1(6) . . . . ?
O1 C1 C2 C7 5.9(9) . . . . ?
O2 C1 C2 C3 6.7(9) . . . . ?
O1 C1 C2 C3 -174.4(6) . . . . ?
C7 C2 C3 C4 0.4(11) . . . . ?
C1 C2 C3 C4 -179.3(7) . . . . ?
C2 C3 C4 C5 -0.3(12) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C3 C4 C5 O3 -175.8(7) . . . . ?
C8 O3 C5 C4 -40.1(9) . . . . ?
C8 O3 C5 C6 143.2(6) . . . . ?
C4 C5 C6 C7 -1.3(10) . . . . ?
O3 C5 C6 C7 175.5(6) . . . . ?
C3 C2 C7 C6 -1.0(11) . . . . ?
C1 C2 C7 C6 178.8(6) . . . . ?
C5 C6 C7 C2 1.4(11) . . . . ?
C5 O3 C8 C9 -58.3(8) . . . . ?
C5 O3 C8 C13 130.0(6) . . . . ?
C10 N1 C9 C8 -1.5(9) . . . . ?
Mn1 N1 C9 C8 156.9(5) 2_446 . . . ?
C13 C8 C9 N1 0.9(10) . . . . ?
O3 C8 C9 N1 -170.5(5) . . . . ?
C9 N1 C10 C11 1.4(9) . . . . ?
Mn1 N1 C10 C11 -155.1(5) 2_446 . . . ?
N1 C10 C11 C13 -0.7(9) . . . . ?
N1 C10 C11 C12 175.8(5) . . . . ?
Mn1 O5 C12 O4 39.0(8) 4_776 . . . ?
Mn1 O5 C12 O4 -106.5(6) 2_546 . . . ?
Mn1 O5 C12 C11 -141.4(4) 4_776 . . . ?
Mn1 O5 C12 C11 73.1(6) 2_546 . . . ?
C10 C11 C12 O4 -170.1(6) . . . . ?
C13 C11 C12 O4 6.3(9) . . . . ?
C10 C11 C12 O5 10.3(8) . . . . ?
C13 C11 C12 O5 -173.3(5) . . . . ?
C9 C8 C13 C11 -0.2(9) . . . . ?
O3 C8 C13 C11 171.3(5) . . . . ?
C10 C11 C13 C8 0.1(9) . . . . ?
C12 C11 C13 C8 -176.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H2W O4 0.77(7) 2.47(7) 3.134(8) 145(7) 2_546
O6 H1W O2 0.87(5) 1.86(5) 2.716(8) 170(5) 1_455
C13 H13 O2 0.93 2.38 3.196(8) 146.2 2_556
C9 H9 O1 0.93 2.46 3.047(7) 121.4 2_446
O7 H4W O2 0.87 2.06 2.722(7) 132.0 .
O7 H3W O4 0.87 2.25 2.957(7) 138.6 4_475

_refine_diff_density_max         0.800
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.120

