# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522178'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H15 Mn N3 O5, 3(H O0.5)'
_chemical_formula_sum            'C23 H18 Mn N3 O6.50'
_chemical_formula_weight         495.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   27.619(3)
_cell_length_b                   12.3795(15)
_cell_length_c                   13.8652(17)
_cell_angle_alpha                90
_cell_angle_beta                 118.922(2)
_cell_angle_gamma                90
_cell_volume                     4149.4(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1890
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.278
_cell_measurement_theta_min      2.757
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0607 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.8955.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10925
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.685
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             4036
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+1.1204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2W), O3W(H3WA,H3WB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.16793(2) 0.21337(3) 0.77283(3) 0.02512(14) Uani 1 1 d . . . . .
N1 N 0.09832(9) 0.08003(17) 0.70490(19) 0.0304(5) Uani 1 1 d . . . . .
N2 N 0.08148(8) 0.29017(16) 0.70392(17) 0.0214(5) Uani 1 1 d . . . . .
N3 N 0.17563(8) 0.40119(17) 0.80488(17) 0.0247(5) Uani 1 1 d . . . . .
C1 C 0.10931(12) -0.0264(2) 0.7166(3) 0.0401(8) Uani 1 1 d . . . . .
H1 H 0.1461 -0.0484 0.7502 0.048 Uiso 1 1 calc R . . . .
C2 C 0.06873(13) -0.1045(2) 0.6814(3) 0.0432(8) Uani 1 1 d . . . . .
H2 H 0.0779 -0.1774 0.6900 0.052 Uiso 1 1 calc R . . . .
C3 C 0.01444(13) -0.0719(2) 0.6332(3) 0.0423(8) Uani 1 1 d . . . . .
H3 H -0.0138 -0.1228 0.6081 0.051 Uiso 1 1 calc R . . . .
C4 C 0.00234(12) 0.0370(2) 0.6226(2) 0.0341(7) Uani 1 1 d . . . . .
H4 H -0.0342 0.0604 0.5912 0.041 Uiso 1 1 calc R . . . .
C5 C 0.04510(11) 0.1113(2) 0.6590(2) 0.0256(6) Uani 1 1 d . . . . .
C6 C 0.03528(10) 0.2298(2) 0.6510(2) 0.0239(6) Uani 1 1 d . . . . .
C7 C -0.01678(11) 0.2766(2) 0.5946(2) 0.0282(6) Uani 1 1 d . . . . .
H7 H -0.0477 0.2328 0.5569 0.034 Uiso 1 1 calc R . . . .
C8 C -0.02337(10) 0.3882(2) 0.5936(2) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.02493(10) 0.4477(2) 0.6543(2) 0.0250(6) Uani 1 1 d . . . . .
H9 H 0.0227 0.5223 0.6595 0.030 Uiso 1 1 calc R . . . .
C10 C 0.07603(10) 0.3977(2) 0.70688(19) 0.0208(6) Uani 1 1 d . . . . .
C11 C 0.12849(10) 0.4597(2) 0.7671(2) 0.0212(6) Uani 1 1 d . . . . .
C12 C 0.12923(11) 0.5698(2) 0.7816(2) 0.0296(6) Uani 1 1 d . . . . .
H12 H 0.0962 0.6079 0.7554 0.036 Uiso 1 1 calc R . . . .
C13 C 0.17949(12) 0.6236(2) 0.8357(2) 0.0356(7) Uani 1 1 d . . . . .
H13 H 0.1807 0.6979 0.8466 0.043 Uiso 1 1 calc R . . . .
C14 C 0.22732(11) 0.5652(2) 0.8727(2) 0.0341(7) Uani 1 1 d . . . . .
H14 H 0.2616 0.5990 0.9086 0.041 Uiso 1 1 calc R . . . .
C15 C 0.22342(11) 0.4552(2) 0.8555(2) 0.0318(7) Uani 1 1 d . . . . .
H15 H 0.2561 0.4161 0.8807 0.038 Uiso 1 1 calc R . . . .
C16 C -0.07776(10) 0.4436(2) 0.5335(2) 0.0212(6) Uani 1 1 d . . . . .
C17 C -0.12773(10) 0.3870(2) 0.4788(2) 0.0238(6) Uani 1 1 d . . . . .
H17 H -0.1274 0.3119 0.4798 0.029 Uiso 1 1 calc R . . . .
C18 C -0.17812(10) 0.4414(2) 0.4228(2) 0.0210(5) Uani 1 1 d . . . . .
C19 C -0.17891(10) 0.5530(2) 0.4191(2) 0.0235(6) Uani 1 1 d . . . . .
H19 H -0.2124 0.5893 0.3800 0.028 Uiso 1 1 calc R . . . .
C20 C -0.12986(10) 0.6113(2) 0.4738(2) 0.0220(6) Uani 1 1 d . . . . .
C21 C -0.08042(10) 0.5562(2) 0.5300(2) 0.0235(6) Uani 1 1 d . . . . .
H21 H -0.0478 0.5955 0.5669 0.028 Uiso 1 1 calc R . . . .
C22 C -0.23199(10) 0.3807(2) 0.3668(2) 0.0258(6) Uani 1 1 d . . . . .
C23 C -0.13049(11) 0.7329(2) 0.4744(2) 0.0265(6) Uani 1 1 d . . . . .
O1 O -0.23298(8) 0.28005(14) 0.38027(17) 0.0357(5) Uani 1 1 d . . . . .
O1W O 0.16568(8) 0.18102(15) 0.92614(15) 0.0384(5) Uani 1 1 d . . . . .
H1WA H 0.1624 0.1047 0.9335 0.058 Uiso 1 1 d R . . . .
H1WB H 0.1992 0.2068 0.9875 0.058 Uiso 1 1 d R . . . .
O2 O -0.27564(7) 0.43219(15) 0.30733(16) 0.0352(5) Uani 1 1 d . . . . .
O2W O 0.0000 0.6892(2) 0.7500 0.0583(10) Uani 1 2 d S T P . .
H2W H -0.0281 0.7278 0.7098 0.087 Uiso 1 1 d R . . . .
O3 O -0.16413(8) 0.78014(14) 0.38694(15) 0.0332(5) Uani 1 1 d . . . . .
O3W O 0.13289(9) -0.00384(17) 0.99401(19) 0.0542(6) Uani 1 1 d . . . . .
H3WA H 0.1194 -0.0666 0.9731 0.081 Uiso 1 1 d R . . . .
H3WB H 0.1518 -0.0158 1.0628 0.081 Uiso 1 1 d R . . . .
O4 O -0.09799(9) 0.77974(15) 0.56234(17) 0.0472(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N1 2.357(2) . ?
Mn1 N2 2.305(2) . ?
Mn1 N3 2.357(2) . ?
Mn1 O1 2.4026(19) 8_556 ?
Mn1 O1W 2.193(2) . ?
Mn1 O2 2.2769(19) 8_556 ?
Mn1 O3 2.1680(19) 5_566 ?
N1 C1 1.344(3) . ?
N1 C5 1.346(3) . ?
N2 C6 1.349(3) . ?
N2 C10 1.342(3) . ?
N3 C11 1.354(3) . ?
N3 C15 1.336(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 C6 1.486(3) . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(3) . ?
C8 C9 1.395(3) . ?
C8 C16 1.487(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 C11 1.489(3) . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.399(3) . ?
C16 C21 1.395(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.395(3) . ?
C18 C19 1.383(3) . ?
C18 C22 1.504(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C20 C21 1.382(3) . ?
C20 C23 1.506(4) . ?
C21 H21 0.9300 . ?
C22 O1 1.262(3) . ?
C22 O2 1.256(3) . ?
C23 O3 1.259(3) . ?
C23 O4 1.253(3) . ?
O1 Mn1 2.4026(19) 8_455 ?
O1W H1WA 0.9600 . ?
O1W H1WB 0.9600 . ?
O2 Mn1 2.2769(19) 8_455 ?
O2W H2W 0.8499 . ?
O3 Mn1 2.1679(19) 5_566 ?
O3W H3WA 0.8501 . ?
O3W H3WB 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Mn1 O1 137.37(7) . 8_556 ?
N2 Mn1 N1 69.02(7) . . ?
N2 Mn1 N3 69.64(7) . . ?
N2 Mn1 O1 152.15(7) . 8_556 ?
N3 Mn1 N1 138.40(7) . . ?
N3 Mn1 O1 82.99(7) . 8_556 ?
O1W Mn1 N1 81.92(8) . . ?
O1W Mn1 N2 88.15(8) . . ?
O1W Mn1 N3 92.27(7) . . ?
O1W Mn1 O1 87.88(7) . 8_556 ?
O1W Mn1 O2 89.39(7) . 8_556 ?
O2 Mn1 N1 82.69(7) 8_556 . ?
O2 Mn1 N2 151.68(7) 8_556 . ?
O2 Mn1 N3 138.66(7) 8_556 . ?
O2 Mn1 O1 55.79(6) 8_556 8_556 ?
O3 Mn1 N1 89.46(8) 5_566 . ?
O3 Mn1 N2 91.87(7) 5_566 . ?
O3 Mn1 N3 96.40(7) 5_566 . ?
O3 Mn1 O1 96.31(7) 5_566 8_556 ?
O3 Mn1 O1W 170.76(7) 5_566 . ?
O3 Mn1 O2 86.21(7) 5_566 8_556 ?
C1 N1 Mn1 123.04(19) . . ?
C1 N1 C5 118.1(2) . . ?
C5 N1 Mn1 118.73(17) . . ?
C6 N2 Mn1 120.97(16) . . ?
C10 N2 Mn1 120.36(16) . . ?
C10 N2 C6 118.4(2) . . ?
C11 N3 Mn1 118.20(16) . . ?
C15 N3 Mn1 124.64(17) . . ?
C15 N3 C11 117.1(2) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 116.0(2) . . ?
C4 C5 C6 122.4(2) . . ?
N2 C6 C5 114.6(2) . . ?
N2 C6 C7 121.7(2) . . ?
C7 C6 C5 123.8(2) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 115.8(2) . . ?
C7 C8 C16 123.7(2) . . ?
C9 C8 C16 120.4(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
N2 C10 C9 121.9(2) . . ?
N2 C10 C11 115.8(2) . . ?
C9 C10 C11 122.2(2) . . ?
N3 C11 C10 115.7(2) . . ?
N3 C11 C12 122.0(2) . . ?
C12 C11 C10 122.3(2) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 H14 120.8 . . ?
N3 C15 C14 124.1(3) . . ?
N3 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C17 C16 C8 122.5(2) . . ?
C21 C16 C8 120.2(2) . . ?
C21 C16 C17 117.4(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C22 121.2(2) . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 C22 119.1(2) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C23 120.7(2) . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 C23 120.1(2) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.3(2) . . ?
C20 C21 H21 118.9 . . ?
O1 C22 C18 120.2(2) . . ?
O2 C22 C18 118.7(2) . . ?
O2 C22 O1 121.0(2) . . ?
O3 C23 C20 117.6(2) . . ?
O4 C23 C20 117.6(2) . . ?
O4 C23 O3 124.8(2) . . ?
C22 O1 Mn1 88.54(15) . 8_455 ?
Mn1 O1W H1WA 109.4 . . ?
Mn1 O1W H1WB 109.3 . . ?
H1WA O1W H1WB 109.5 . . ?
C22 O2 Mn1 94.50(15) . 8_455 ?
C23 O3 Mn1 130.53(17) . 5_566 ?
H3WA O3W H3WB 98.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522177'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_method           Olex2
_audit_creation_date             2016-07-27
_chemical_formula_sum            C23
_chemical_formula_weight         486.760
_refine_ls_R_factor_all          0.087
_cell_length_a                   8.6165(14)
_cell_length_b                   10.7021(17)
_cell_length_c                   10.9629(17)
_cell_angle_alpha                78.643(2)
_cell_angle_beta                 87.650(2)
_cell_angle_gamma                79.496(3)
_cell_volume                     974.5(3)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Mn ? 1.200
Cl ? 1.200
O ? 1.200
H ? 1.200
N ? 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
Mn1 Mn 0.2879(1) 0.1811(1) 1.2159(0) 1.000 2 i ? d Uani 0.0234(3)
Cl1 Cl 0.1935(2) 0.0094(1) 1.3417(1) 1.000 2 i ? d Uani 0.0479(4)
O1 O 0.3040(3) 0.3091(3) 0.3308(3) 1.000 2 i ? d Uani 0.0316(7)
O2 O 0.4788(3) 0.4070(4) 0.2137(3) 1.000 2 i ? d Uani 0.0377(8)
O3 O 1.0367(4) 0.3363(4) 0.5959(3) 1.000 2 i ? d Uani 0.0402(8)
O4 O 1.0004(3) 0.3659(4) 0.3911(3) 1.000 2 i ? d Uani 0.0380(8)
H4 H 1.0953 0.3370 0.3897 1.000 2 i ? d Uiso 0.05700
N1 N 0.3743(4) 0.2087(3) 1.0224(3) 1.000 2 i ? d Uani 0.0208(7)
N2 N 0.5490(4) 0.0930(4) 1.2173(3) 1.000 2 i ? d Uani 0.0286(8)
N3 N 0.0801(4) 0.2710(3) 1.0904(3) 1.000 2 i ? d Uani 0.0237(7)
C1 C 0.5259(4) 0.1655(4) 0.9968(3) 1.000 2 i ? d Uani 0.0191(7)
C2 C 0.6202(4) 0.0919(4) 1.1067(3) 1.000 2 i ? d Uani 0.0226(8)
C3 C 0.6298(6) 0.0352(5) 1.3203(4) 1.000 2 i ? d Uani 0.0389(11)
H3 H 0.5802 0.0392 1.3968 1.000 2 i ? calc Uiso 0.04700
C4 C 0.7826(6) -0.0300(5) 1.3195(4) 1.000 2 i ? d Uani 0.0430(12)
H4A H 0.8356 -0.0688 1.3934 1.000 2 i ? calc Uiso 0.05200
C5 C 0.8554(6) -0.0363(5) 1.2052(5) 1.000 2 i ? d Uani 0.0382(11)
H5 H 0.9578 -0.0816 1.2010 1.000 2 i ? calc Uiso 0.04600
C6 C 0.7736(5) 0.0261(5) 1.0969(4) 1.000 2 i ? d Uani 0.0330(9)
H6 H 0.8208 0.0238 1.0193 1.000 2 i ? calc Uiso 0.04000
C7 C 0.5874(4) 0.1935(4) 0.8782(3) 1.000 2 i ? d Uani 0.0240(8)
H7 H 0.6931 0.1630 0.8626 1.000 2 i ? calc Uiso 0.02900
C8 C 0.4898(4) 0.2681(4) 0.7818(3) 1.000 2 i ? d Uani 0.0212(7)
C9 C 0.3326(4) 0.3107(4) 0.8085(3) 1.000 2 i ? d Uani 0.0233(8)
H9 H 0.2647 0.3603 0.7464 1.000 2 i ? calc Uiso 0.02800
C10 C 0.2784(4) 0.2779(4) 0.9294(3) 1.000 2 i ? d Uani 0.0205(7)
C11 C 0.1106(4) 0.3142(4) 0.9686(3) 1.000 2 i ? d Uani 0.0207(7)
C12 C -0.0676(5) 0.2933(4) 1.1317(4) 1.000 2 i ? d Uani 0.0282(9)
H12 H -0.0888 0.2590 1.2141 1.000 2 i ? calc Uiso 0.03400
C13 C -0.1923(5) 0.3657(4) 1.0569(4) 1.000 2 i ? d Uani 0.0286(9)
H13 H -0.2937 0.3834 1.0892 1.000 2 i ? calc Uiso 0.03400
C14 C -0.1597(5) 0.4109(5) 0.9315(4) 1.000 2 i ? d Uani 0.0323(9)
H14 H -0.2395 0.4595 0.8784 1.000 2 i ? calc Uiso 0.03900
C15 C -0.0065(5) 0.3822(4) 0.8875(4) 1.000 2 i ? d Uani 0.0271(8)
H15 H 0.0167 0.4087 0.8038 1.000 2 i ? calc Uiso 0.03200
C16 C 0.5551(4) 0.3038(4) 0.6551(3) 1.000 2 i ? d Uani 0.0205(7)
C17 C 0.4626(4) 0.3180(4) 0.5499(3) 1.000 2 i ? d Uani 0.0197(7)
H17 H 0.3582 0.3063 0.5597 1.000 2 i ? calc Uiso 0.02400
C18 C 0.5245(4) 0.3497(4) 0.4300(3) 1.000 2 i ? d Uani 0.0210(7)
C19 C 0.4297(4) 0.3605(4) 0.3161(4) 1.000 2 i ? d Uani 0.0252(8)
C20 C 0.6817(4) 0.3653(4) 0.4161(3) 1.000 2 i ? d Uani 0.0193(7)
H20 H 0.7225 0.3888 0.3367 1.000 2 i ? calc Uiso 0.02300
C21 C 0.7786(4) 0.3463(4) 0.5191(3) 1.000 2 i ? d Uani 0.0201(7)
C22 C 0.9490(4) 0.3495(4) 0.5080(3) 1.000 2 i ? d Uani 0.0227(8)
C23 C 0.7128(4) 0.3164(4) 0.6388(3) 1.000 2 i ? d Uani 0.0200(7)
H23 H 0.7761 0.3049 0.7083 1.000 2 i ? calc Uiso 0.02400



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
Mn1 Cl1 . . 2.3223(13) no
Mn1 O1 . 1_556 2.061(3) no
Mn1 N1 . . 2.201(3) no
Mn1 N2 . . 2.275(4) no
Mn1 N3 . . 2.253(3) no
O1 Mn1 . 1_554 2.061(3) no
O1 C19 . . 1.292(5) no
O2 C19 . . 1.228(5) no
O3 C22 . . 1.219(5) no
O4 H4 . . 0.8205 no
O4 C22 . . 1.327(5) no
N1 C1 . . 1.341(5) no
N1 C10 . . 1.348(5) no
N2 C2 . . 1.338(5) no
N2 C3 . . 1.332(5) no
N3 C11 . . 1.356(4) no
N3 C12 . . 1.329(5) no
C1 C2 . . 1.485(5) no
C1 C7 . . 1.382(5) no
C2 C6 . . 1.391(6) no
C3 H3 . . 0.9300 no
C3 C4 . . 1.374(7) no
C4 H4A . . 0.9300 no
C4 C5 . . 1.386(7) no
C5 H5 . . 0.9300 no
C5 C6 . . 1.392(6) no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C7 C8 . . 1.399(5) no
C8 C9 . . 1.387(5) no
C8 C16 . . 1.483(5) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.387(5) no
C10 C11 . . 1.495(5) no
C11 C15 . . 1.375(5) no
C12 H12 . . 0.9300 no
C12 C13 . . 1.395(6) no
C13 H13 . . 0.9300 no
C13 C14 . . 1.400(6) no
C14 H14 . . 0.9300 no
C14 C15 . . 1.389(6) no
C15 H15 . . 0.9300 no
C16 C17 . . 1.396(5) no
C16 C23 . . 1.391(5) no
C17 H17 . . 0.9300 no
C17 C18 . . 1.400(5) no
C18 C19 . . 1.494(5) no
C18 C20 . . 1.393(5) no
C20 H20 . . 0.9300 no
C20 C21 . . 1.392(5) no
C21 C22 . . 1.475(5) no
C21 C23 . . 1.409(5) 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
O1 Mn1 Cl1 1_556 . . 105.25(10) no
O1 Mn1 N1 1_556 . . 122.60(13) no
O1 Mn1 N2 1_556 . . 96.56(12) no
O1 Mn1 N3 1_556 . . 106.47(12) no
N1 Mn1 Cl1 . . . 131.8(1) no
N1 Mn1 N2 . . . 71.92(12) no
N1 Mn1 N3 . . . 71.97(11) no
N2 Mn1 Cl1 . . . 98.99(10) no
N3 Mn1 Cl1 . . . 101.54(9) no
N3 Mn1 N2 . . . 143.61(12) no
C19 O1 Mn1 . . 1_554 115.2(2) no
C22 O4 H4 . . . 109.50 no
C1 N1 Mn1 . . . 120.3(2) no
C1 N1 C10 . . . 119.2(3) no
C10 N1 Mn1 . . . 120.2(2) no
C2 N2 Mn1 . . . 116.9(3) no
C3 N2 Mn1 . . . 123.8(3) no
C3 N2 C2 . . . 119.1(4) no
C11 N3 Mn1 . . . 117.5(2) no
C12 N3 Mn1 . . . 123.3(3) no
C12 N3 C11 . . . 118.9(3) no
N1 C1 C2 . . . 114.4(3) no
N1 C1 C7 . . . 121.6(3) no
C7 C1 C2 . . . 124.0(3) no
N2 C2 C1 . . . 115.9(3) no
N2 C2 C6 . . . 121.3(4) no
C6 C2 C1 . . . 122.8(4) no
N2 C3 H3 . . . 118.30 no
N2 C3 C4 . . . 123.4(4) no
C4 C3 H3 . . . 118.30 no
C3 C4 H4A . . . 121.00 no
C3 C4 C5 . . . 117.9(4) no
C5 C4 H4A . . . 121.00 no
C4 C5 H5 . . . 120.40 no
C4 C5 C6 . . . 119.3(4) no
C6 C5 H5 . . . 120.40 no
C2 C6 C5 . . . 118.8(4) no
C2 C6 H6 . . . 120.60 no
C5 C6 H6 . . . 120.60 no
C1 C7 H7 . . . 120.20 no
C1 C7 C8 . . . 119.5(3) no
C8 C7 H7 . . . 120.20 no
C7 C8 C16 . . . 120.4(3) no
C9 C8 C7 . . . 118.5(3) no
C9 C8 C16 . . . 121.1(3) no
C8 C9 H9 . . . 120.60 no
C8 C9 C10 . . . 118.9(3) no
C10 C9 H9 . . . 120.60 no
N1 C10 C9 . . . 122.2(3) no
N1 C10 C11 . . . 114.0(3) no
C9 C10 C11 . . . 123.8(3) no
N3 C11 C10 . . . 115.0(3) no
N3 C11 C15 . . . 121.8(3) no
C15 C11 C10 . . . 123.1(3) no
N3 C12 H12 . . . 118.50 no
N3 C12 C13 . . . 123.0(4) no
C13 C12 H12 . . . 118.50 no
C12 C13 H13 . . . 121.10 no
C12 C13 C14 . . . 117.7(4) no
C14 C13 H13 . . . 121.10 no
C13 C14 H14 . . . 120.50 no
C15 C14 C13 . . . 119.0(4) no
C15 C14 H14 . . . 120.50 no
C11 C15 C14 . . . 119.4(4) no
C11 C15 H15 . . . 120.30 no
C14 C15 H15 . . . 120.30 no
C17 C16 C8 . . . 120.9(3) no
C23 C16 C8 . . . 120.3(3) no
C23 C16 C17 . . . 118.7(3) no
C16 C17 H17 . . . 119.50 no
C16 C17 C18 . . . 121.1(3) no
C18 C17 H17 . . . 119.50 no
C17 C18 C19 . . . 122.0(3) no
C20 C18 C17 . . . 119.1(3) no
C20 C18 C19 . . . 118.8(3) no
O1 C19 C18 . . . 116.8(3) no
O2 C19 O1 . . . 123.0(4) no
O2 C19 C18 . . . 120.0(3) no
C18 C20 H20 . . . 119.50 no
C21 C20 C18 . . . 121.0(3) no
C21 C20 H20 . . . 119.50 no
C20 C21 C22 . . . 122.7(3) no
C20 C21 C23 . . . 118.7(3) no
C23 C21 C22 . . . 118.6(3) no
O3 C22 O4 . . . 122.3(4) no
O3 C22 C21 . . . 124.5(4) no
O4 C22 C21 . . . 113.2(3) no
C16 C23 C21 . . . 121.3(3) no
C16 C23 H23 . . . 119.40 no
C21 C23 H23 . . . 119.40 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
Mn1 O1 C19 O2 1_554 . . . 47.1(5) no
Mn1 O1 C19 C18 1_554 . . . -127.0(3) no
Mn1 N1 C1 C2 . . . . 4.4(4) no
Mn1 N1 C1 C7 . . . . -172.9(3) no
Mn1 N1 C10 C9 . . . . 172.3(3) no
Mn1 N1 C10 C11 . . . . -8.3(4) no
Mn1 N2 C2 C1 . . . . 8.6(4) no
Mn1 N2 C2 C6 . . . . -171.8(3) no
Mn1 N2 C3 C4 . . . . 172.7(4) no
Mn1 N3 C11 C10 . . . . 8.9(4) no
Mn1 N3 C11 C15 . . . . -173.2(3) no
Mn1 N3 C12 C13 . . . . 170.3(3) no
N1 C1 C2 N2 . . . . -8.5(5) no
N1 C1 C2 C6 . . . . 171.9(4) no
N1 C1 C7 C8 . . . . -0.3(6) no
N1 C10 C11 N3 . . . . -0.7(5) no
N1 C10 C11 C15 . . . . -178.5(4) no
N2 C2 C6 C5 . . . . -2.0(7) no
N2 C3 C4 C5 . . . . -0.4(8) no
N3 C11 C15 C14 . . . . 1.8(6) no
N3 C12 C13 C14 . . . . 3.2(7) no
C1 N1 C10 C9 . . . . -2.6(6) no
C1 N1 C10 C11 . . . . 176.8(3) no
C1 C2 C6 C5 . . . . 177.6(4) no
C1 C7 C8 C9 . . . . -0.7(6) no
C1 C7 C8 C16 . . . . 177.5(4) no
C2 N2 C3 C4 . . . . -2.2(7) no
C2 C1 C7 C8 . . . . -177.4(4) no
C3 N2 C2 C1 . . . . -176.2(4) no
C3 N2 C2 C6 . . . . 3.4(6) no
C3 C4 C5 C6 . . . . 1.8(8) no
C4 C5 C6 C2 . . . . -0.6(7) no
C7 C1 C2 N2 . . . . 168.7(4) no
C7 C1 C2 C6 . . . . -10.8(6) no
C7 C8 C9 C10 . . . . 0.1(6) no
C7 C8 C16 C17 . . . . 147.9(4) no
C7 C8 C16 C23 . . . . -28.4(6) no
C8 C9 C10 N1 . . . . 1.5(6) no
C8 C9 C10 C11 . . . . -177.8(4) no
C8 C16 C17 C18 . . . . -179.0(3) no
C8 C16 C23 C21 . . . . 178.0(3) no
C9 C8 C16 C17 . . . . -34.0(6) no
C9 C8 C16 C23 . . . . 149.7(4) no
C9 C10 C11 N3 . . . . 178.7(4) no
C9 C10 C11 C15 . . . . 0.9(6) no
C10 N1 C1 C2 . . . . 179.3(3) no
C10 N1 C1 C7 . . . . 1.9(5) no
C10 C11 C15 C14 . . . . 179.5(4) no
C11 N3 C12 C13 . . . . -3.8(6) no
C12 N3 C11 C10 . . . . -176.6(4) no
C12 N3 C11 C15 . . . . 1.2(6) no
C12 C13 C14 C15 . . . . -0.1(6) no
C13 C14 C15 C11 . . . . -2.3(7) no
C16 C8 C9 C10 . . . . -178.0(4) no
C16 C17 C18 C19 . . . . 177.6(4) no
C16 C17 C18 C20 . . . . 0.9(6) no
C17 C16 C23 C21 . . . . 1.6(6) no
C17 C18 C19 O1 . . . . -16.7(6) no
C17 C18 C19 O2 . . . . 169.0(4) no
C17 C18 C20 C21 . . . . 1.8(6) no
C18 C20 C21 C22 . . . . 173.9(4) no
C18 C20 C21 C23 . . . . -2.8(6) no
C19 C18 C20 C21 . . . . -175.0(4) no
C20 C18 C19 O1 . . . . 160.1(4) no
C20 C18 C19 O2 . . . . -14.2(6) no
C20 C21 C22 O3 . . . . 178.2(4) no
C20 C21 C22 O4 . . . . -3.0(6) no
C20 C21 C23 C16 . . . . 1.0(6) no
C22 C21 C23 C16 . . . . -175.8(3) no
C23 C16 C17 C18 . . . . -2.6(6) no
C23 C21 C22 O3 . . . . -5.1(6) no
C23 C21 C22 O4 . . . . 173.7(4) 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1522179'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 N3 O4 Zn'
_chemical_formula_sum            'C23 H13 N3 O4 Zn'
_chemical_formula_weight         460.73
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   8.613(3)
_cell_length_b                   18.593(6)
_cell_length_c                   38.594(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6181(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.53
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0794 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.8560.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.990
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            7213
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         2.432
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2249
_reflns_number_total             2600
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C11, C9, C10, C8, C8A, C9A, C10A, N1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C9A)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C8A) \\sim Ueq,
Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H11A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(H11)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C8)=Sof(H8)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C11(H11), C11(H11A), C9(H9), C10(H10), C8(H8), C12(H12),
 C8A(H8A), C9A(H9A), C10A(H10A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O -0.5707(4) -0.42226(16) -1.78844(8) 0.0692(9) Uani 1 1 d . . . . .
C1 C -0.6211(6) -0.3697(2) -1.77035(12) 0.0590(12) Uani 1 1 d . . . . .
C2 C -0.6845(5) -0.3070(2) -1.79111(11) 0.0500(10) Uani 1 1 d . . . . .
C4 C -0.6859(5) -0.3067(2) -1.82623(11) 0.0494(10) Uani 1 1 d . . . . .
H4 H -0.6429 -0.3453 -1.8382 0.059 Uiso 1 1 calc R . . . .
C5 C -0.7500 -0.2500 -1.84469(16) 0.0533(15) Uani 1 2 d S T P . .
C6 C -0.7500 -0.2500 -1.88307(16) 0.0499(14) Uani 1 2 d S T P . .
Zn1 Zn -0.7500 -0.2500 -2.00747(2) 0.0490(2) Uani 1 2 d S T P A .
N2 N -0.7500 -0.2500 -1.95409(12) 0.0449(11) Uani 1 2 d S T P . .
O2 O -0.6229(5) -0.36729(18) -1.73937(9) 0.0824(12) Uani 1 1 d . . . . .
C3 C -0.7500 -0.2500 -1.77349(17) 0.0515(14) Uani 1 2 d S T P . .
H3 H -0.7500 -0.2500 -1.7494 0.062 Uiso 1 2 calc RS T P . .
C7 C -0.6273(5) -0.2753(2) -1.93699(11) 0.0511(10) Uani 1 1 d . . . . .
C13 C -0.4996(6) -0.2987(4) -1.95920(16) 0.0827(17) Uani 1 1 d . . . . .
C11 C -0.3590(8) -0.3240(5) -1.9461(2) 0.121(3) Uani 1 1 d . U . . .
H11 H -0.3496 -0.3360 -1.9228 0.145 Uiso 0.53(2) 1 calc R . . A 1
H11A H -0.3234 -0.3155 -1.9237 0.145 Uiso 0.47(2) 1 calc R . . A 2
C9 C -0.2589(19) -0.3185(12) -2.0036(6) 0.112(5) Uani 0.53(2) 1 d . U . A 1
H9 H -0.1801 -0.3255 -2.0197 0.134 Uiso 0.53(2) 1 calc R . . A 1
C10 C -0.2332(18) -0.3310(12) -1.9683(4) 0.099(4) Uani 0.53(2) 1 d . U . A 1
H10 H -0.1355 -0.3436 -1.9601 0.119 Uiso 0.53(2) 1 calc R . . A 1
C8 C -0.4055(17) -0.2953(11) -2.0139(4) 0.094(4) Uani 0.53(2) 1 d . U . A 1
H8 H -0.4177 -0.2807 -2.0368 0.113 Uiso 0.53(2) 1 calc R . . A 1
N1 N -0.5287(5) -0.2927(3) -1.99345(12) 0.0871(16) Uani 1 1 d . U . . .
C12 C -0.6239(5) -0.2756(2) -1.90121(11) 0.0544(11) Uani 1 1 d . . . . .
H12 H -0.5374 -0.2930 -1.8895 0.065 Uiso 1 1 calc R . . . .
C8A C -0.441(2) -0.3373(14) -2.0174(6) 0.110(5) Uani 0.47(2) 1 d . U . A 2
H8A H -0.4745 -0.3437 -2.0401 0.132 Uiso 0.47(2) 1 calc R . . A 2
C9A C -0.310(3) -0.3689(15) -2.0063(7) 0.131(6) Uani 0.47(2) 1 d . U . A 2
H9A H -0.2473 -0.3914 -2.0227 0.157 Uiso 0.47(2) 1 calc R . . A 2
C10A C -0.266(3) -0.3700(17) -1.9749(7) 0.126(6) Uani 0.47(2) 1 d . U . A 2
H10A H -0.1805 -0.3973 -1.9685 0.151 Uiso 0.47(2) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.277(5) . ?
O1 Zn1 1.972(3) 3_545 ?
C1 C2 1.517(6) . ?
C1 O2 1.196(5) . ?
C2 C4 1.356(6) . ?
C2 C3 1.380(5) . ?
C4 C5 1.387(5) . ?
C5 C4 1.387(5) 14_345 ?
C5 C6 1.481(9) . ?
C6 C12 1.377(6) 14_345 ?
C6 C12 1.377(5) . ?
Zn1 O1 1.972(3) 11_444 ?
Zn1 O1 1.972(3) 12_354 ?
Zn1 N2 2.060(5) . ?
Zn1 N1 2.134(5) . ?
Zn1 N1 2.134(5) 14_345 ?
N2 C7 1.332(5) 14_345 ?
N2 C7 1.332(5) . ?
C3 C2 1.380(5) 14_345 ?
C7 C13 1.461(7) . ?
C7 C12 1.381(6) . ?
C13 C11 1.394(8) . ?
C13 N1 1.350(7) . ?
C11 C10 1.388(16) . ?
C11 C10A 1.61(2) . ?
C9 C10 1.40(3) . ?
C9 C8 1.39(2) . ?
C8 N1 1.323(14) . ?
N1 C8A 1.46(2) . ?
C8A C9A 1.34(3) . ?
C9A C10A 1.27(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
C1 O1 Zn1 109.5(3) . 3_545 ?
O1 C1 C2 114.9(4) . . ?
O2 C1 O1 125.4(4) . . ?
O2 C1 C2 119.6(4) . . ?
C4 C2 C1 122.3(4) . . ?
C4 C2 C3 119.1(4) . . ?
C3 C2 C1 118.5(4) . . ?
C2 C4 C5 121.4(4) . . ?
C4 C5 C4 118.2(5) 14_345 . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 C6 120.9(3) 14_345 . ?
C12 C6 C5 120.6(3) . . ?
C12 C6 C5 120.5(3) 14_345 . ?
C12 C6 C12 118.9(6) 14_345 . ?
O1 Zn1 O1 105.39(18) 11_444 12_354 ?
O1 Zn1 N2 127.31(9) 11_444 . ?
O1 Zn1 N2 127.31(9) 12_354 . ?
O1 Zn1 N1 99.0(2) 12_354 14_345 ?
O1 Zn1 N1 98.63(19) 12_354 . ?
O1 Zn1 N1 98.63(19) 11_444 14_345 ?
O1 Zn1 N1 99.0(2) 11_444 . ?
N2 Zn1 N1 75.32(12) . . ?
N2 Zn1 N1 75.32(12) . 14_345 ?
N1 Zn1 N1 150.6(2) . 14_345 ?
C7 N2 Zn1 119.7(3) 14_345 . ?
C7 N2 Zn1 119.7(3) . . ?
C7 N2 C7 120.6(5) 14_345 . ?
C2 C3 C2 121.0(6) 14_345 . ?
N2 C7 C13 114.3(4) . . ?
N2 C7 C12 120.9(4) . . ?
C12 C7 C13 124.7(4) . . ?
C11 C13 C7 122.8(6) . . ?
N1 C13 C7 114.2(4) . . ?
N1 C13 C11 123.0(5) . . ?
C13 C11 C10A 111.0(12) . . ?
C10 C11 C13 119.1(9) . . ?
C8 C9 C10 118.2(14) . . ?
C11 C10 C9 117.5(13) . . ?
N1 C8 C9 124.7(15) . . ?
C13 N1 Zn1 116.4(3) . . ?
C13 N1 C8A 118.6(10) . . ?
C8 N1 Zn1 125.4(7) . . ?
C8 N1 C13 115.6(8) . . ?
C8A N1 Zn1 121.1(10) . . ?
C6 C12 C7 119.4(4) . . ?
C9A C8A N1 119(2) . . ?
C10A C9A C8A 124(2) . . ?
C9A C10A C11 120.1(19) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522176'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H13 N3 O4 Zn, H2 O'
_chemical_formula_sum            'C23 H15 N3 O5 Zn'
_chemical_formula_weight         478.75
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.2314(17)
_cell_length_b                   10.9907(16)
_cell_length_c                   15.501(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.877(2)
_cell_angle_gamma                90
_cell_volume                     2046.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1238
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.789
_shelx_estimated_absorpt_T_min   0.707
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0623 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.1053
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12369
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         1.951
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2740
_reflns_number_total             4894
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4894
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H5A-O2_$1
 2 with sigma of 0.02
3.a Free rotating group:
 O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C21(H21), C7(H7), C17(H17), C9(H9), C4(H4), C3(H3), C12(H12),
 C2(H2), C1(H1), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.40048(4) 0.18392(5) 0.10630(3) 0.02931(15) Uani 1 1 d . . . . .
O1 O 0.7512(2) 0.3737(3) 0.55713(18) 0.0386(7) Uani 1 1 d . . . . .
C19 C 0.5684(3) 0.3217(4) 0.4292(2) 0.0304(9) Uani 1 1 d . . . . .
H19 H 0.6386 0.3189 0.4144 0.036 Uiso 1 1 calc R . . . .
N2 N 0.0413(2) 0.3319(3) 0.55030(19) 0.0264(7) Uani 1 1 d . . . . .
C21 C 0.3693(3) 0.3048(4) 0.3872(3) 0.0333(10) Uani 1 1 d . . . . .
H21 H 0.3063 0.2911 0.3443 0.040 Uiso 1 1 calc R . . . .
C7 C 0.2230(3) 0.4123(4) 0.5608(2) 0.0293(9) Uani 1 1 d . . . . .
H7 H 0.2770 0.4677 0.5862 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1195(3) 0.4130(3) 0.5837(2) 0.0249(8) Uani 1 1 d . . . . .
C20 C 0.4744(3) 0.3036(4) 0.3645(3) 0.0322(9) Uani 1 1 d . . . . .
C16 C 0.3582(3) 0.3265(4) 0.4738(3) 0.0310(9) Uani 1 1 d . . . . .
C18 C 0.5588(3) 0.3443(4) 0.5168(3) 0.0289(9) Uani 1 1 d . . . . .
C17 C 0.4535(3) 0.3484(4) 0.5376(3) 0.0310(10) Uani 1 1 d . . . . .
H17 H 0.4460 0.3661 0.5949 0.037 Uiso 1 1 calc R . . . .
C8 C 0.2465(3) 0.3283(4) 0.4994(2) 0.0278(9) Uani 1 1 d . . . . .
C10 C 0.0617(3) 0.2479(4) 0.4917(2) 0.0268(9) Uani 1 1 d . . . . .
C9 C 0.1635(3) 0.2456(4) 0.4639(3) 0.0316(9) Uani 1 1 d . . . . .
H9 H 0.1761 0.1894 0.4220 0.038 Uiso 1 1 calc R . . . .
C5 C 0.0836(3) 0.5006(4) 0.6463(2) 0.0274(9) Uani 1 1 d . . . . .
C4 C 0.1492(3) 0.5964(4) 0.6841(3) 0.0379(11) Uani 1 1 d . . . . .
H4 H 0.2201 0.6083 0.6723 0.045 Uiso 1 1 calc R . . . .
C3 C 0.1066(4) 0.6747(4) 0.7404(3) 0.0508(13) Uani 1 1 d . . . . .
H3 H 0.1492 0.7395 0.7666 0.061 Uiso 1 1 calc R . . . .
N1 N -0.0187(3) 0.4809(3) 0.6630(2) 0.0328(8) Uani 1 1 d . . . . .
N3 N -0.1168(3) 0.1718(3) 0.5047(2) 0.0352(8) Uani 1 1 d . . . . .
C11 C -0.0313(3) 0.1628(4) 0.4615(3) 0.0299(9) Uani 1 1 d . . . . .
C12 C -0.0333(4) 0.0794(4) 0.3946(3) 0.0388(11) Uani 1 1 d . . . . .
H12 H 0.0276 0.0723 0.3669 0.047 Uiso 1 1 calc R . . . .
C2 C 0.0019(4) 0.6557(5) 0.7569(3) 0.0544(14) Uani 1 1 d . . . . .
H2 H -0.0279 0.7073 0.7940 0.065 Uiso 1 1 calc R . . . .
C1 C -0.0586(4) 0.5575(5) 0.7169(3) 0.0467(12) Uani 1 1 d . . . . .
H1 H -0.1298 0.5442 0.7278 0.056 Uiso 1 1 calc R . . . .
C22 C 0.4897(4) 0.2808(4) 0.2709(3) 0.0334(10) Uani 1 1 d . . . . .
C13 C -0.1259(4) 0.0064(5) 0.3687(3) 0.0530(13) Uani 1 1 d . . . . .
H13 H -0.1290 -0.0495 0.3232 0.064 Uiso 1 1 calc R . . . .
C14 C -0.2140(4) 0.0192(5) 0.4127(3) 0.0507(13) Uani 1 1 d . . . . .
H14 H -0.2779 -0.0277 0.3968 0.061 Uiso 1 1 calc R . . . .
C15 C -0.2061(3) 0.1016(4) 0.4799(3) 0.0440(12) Uani 1 1 d . . . . .
H15 H -0.2654 0.1089 0.5093 0.053 Uiso 1 1 calc R . . . .
O4 O 0.5838(2) 0.2675(3) 0.25556(19) 0.0497(9) Uani 1 1 d . . . . .
C23 C 0.6610(3) 0.3627(4) 0.5858(3) 0.0309(9) Uani 1 1 d . . . . .
O2 O 0.6515(2) 0.3665(3) 0.6636(2) 0.0526(9) Uani 1 1 d D . . . .
O3 O 0.3989(2) 0.2746(3) 0.21430(18) 0.0414(8) Uani 1 1 d . . . . .
O5 O 0.2139(3) 0.0117(4) 0.3205(2) 0.0678(11) Uani 1 1 d . . . . .
H5A H 0.2145 0.0411 0.2699 0.102 Uiso 1 1 d DG . . . .
H5B H 0.1814 -0.0570 0.3152 0.102 Uiso 1 1 d G . . . .


_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 1.947(3) 4_565 ?
Zn1 N2 2.077(3) 4_665 ?
Zn1 N1 2.169(3) 4_665 ?
Zn1 N3 2.217(3) 4_665 ?
Zn1 O3 1.952(3) . ?
O1 Zn1 1.947(3) 4_666 ?
O1 C23 1.271(4) . ?
C19 C20 1.390(5) . ?
C19 C18 1.408(5) . ?
N2 Zn1 2.077(3) 4_566 ?
N2 C6 1.339(5) . ?
N2 C10 1.351(5) . ?
C21 C20 1.395(5) . ?
C21 C16 1.396(5) . ?
C7 C6 1.377(5) . ?
C7 C8 1.394(5) . ?
C6 C5 1.491(5) . ?
C20 C22 1.520(5) . ?
C16 C17 1.399(5) . ?
C16 C8 1.493(5) . ?
C18 C17 1.386(5) . ?
C18 C23 1.498(5) . ?
C8 C9 1.396(5) . ?
C10 C9 1.393(5) . ?
C10 C11 1.479(5) . ?
C5 C4 1.385(5) . ?
C5 N1 1.342(5) . ?
C4 C3 1.393(6) . ?
C3 C2 1.369(6) . ?
N1 Zn1 2.169(3) 4_566 ?
N1 C1 1.341(5) . ?
N3 Zn1 2.217(3) 4_566 ?
N3 C11 1.347(5) . ?
N3 C15 1.333(5) . ?
C11 C12 1.381(6) . ?
C12 C13 1.385(6) . ?
C2 C1 1.387(6) . ?
C22 O4 1.227(5) . ?
C22 O3 1.281(5) . ?
C13 C14 1.387(6) . ?
C14 C15 1.369(6) . ?
C23 O2 1.233(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N2 126.85(12) 4_565 4_665 ?
O1 Zn1 N1 102.09(13) 4_565 4_665 ?
O1 Zn1 N3 89.86(12) 4_565 4_665 ?
O1 Zn1 O3 109.95(12) 4_565 . ?
N2 Zn1 N1 75.47(12) 4_665 4_665 ?
N2 Zn1 N3 74.83(12) 4_665 4_665 ?
N1 Zn1 N3 149.37(12) 4_665 4_665 ?
O3 Zn1 N2 122.99(12) . 4_665 ?
O3 Zn1 N1 99.01(13) . 4_665 ?
O3 Zn1 N3 103.25(13) . 4_665 ?
C23 O1 Zn1 130.1(3) . 4_666 ?
C20 C19 C18 120.8(3) . . ?
C6 N2 Zn1 118.9(2) . 4_566 ?
C6 N2 C10 120.4(3) . . ?
C10 N2 Zn1 119.8(3) . 4_566 ?
C20 C21 C16 120.4(4) . . ?
C6 C7 C8 119.8(4) . . ?
N2 C6 C7 121.4(3) . . ?
N2 C6 C5 113.9(3) . . ?
C7 C6 C5 124.7(4) . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 C22 118.6(3) . . ?
C21 C20 C22 121.9(4) . . ?
C21 C16 C17 119.3(3) . . ?
C21 C16 C8 121.2(3) . . ?
C17 C16 C8 119.5(3) . . ?
C19 C18 C23 120.1(3) . . ?
C17 C18 C19 118.7(4) . . ?
C17 C18 C23 121.1(4) . . ?
C18 C17 C16 121.1(4) . . ?
C7 C8 C16 120.4(4) . . ?
C7 C8 C9 118.2(3) . . ?
C9 C8 C16 121.4(3) . . ?
N2 C10 C9 120.6(4) . . ?
N2 C10 C11 114.6(3) . . ?
C9 C10 C11 124.8(4) . . ?
C10 C9 C8 119.5(4) . . ?
C4 C5 C6 123.3(3) . . ?
N1 C5 C6 114.9(3) . . ?
N1 C5 C4 121.8(4) . . ?
C5 C4 C3 118.6(4) . . ?
C2 C3 C4 119.8(4) . . ?
C5 N1 Zn1 115.3(3) . 4_566 ?
C1 N1 Zn1 125.8(3) . 4_566 ?
C1 N1 C5 118.8(4) . . ?
C11 N3 Zn1 115.2(3) . 4_566 ?
C15 N3 Zn1 125.6(3) . 4_566 ?
C15 N3 C11 119.0(4) . . ?
N3 C11 C10 114.8(3) . . ?
N3 C11 C12 121.2(4) . . ?
C12 C11 C10 124.1(4) . . ?
C11 C12 C13 119.9(4) . . ?
C3 C2 C1 118.3(4) . . ?
N1 C1 C2 122.7(4) . . ?
O4 C22 C20 119.6(4) . . ?
O4 C22 O3 125.9(4) . . ?
O3 C22 C20 114.5(3) . . ?
C12 C13 C14 117.8(4) . . ?
C15 C14 C13 119.4(4) . . ?
N3 C15 C14 122.6(4) . . ?
O1 C23 C18 115.2(4) . . ?
O2 C23 O1 125.9(4) . . ?
O2 C23 C18 118.9(3) . . ?
C22 O3 Zn1 117.8(3) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_b-sr
_database_code_depnum_ccdc_archive 'CCDC 1522175'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H49 Mn2 N6 O19'
_chemical_formula_weight         1099.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.367(4)
_cell_length_b                   11.691(4)
_cell_length_c                   20.986(7)
_cell_angle_alpha                80.658(6)
_cell_angle_beta                 74.738(5)
_cell_angle_gamma                73.042(6)
_cell_volume                     2562.4(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6239
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      28.27

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1138
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13810
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             9766
_reflns_number_gt                6287
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1319P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9766
_refine_ls_number_parameters     667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2214
_refine_ls_wR_factor_gt          0.1954
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.22670(6) 0.94514(6) 0.38951(3) 0.0257(2) Uani 1 1 d . . .
Mn2 Mn -0.23707(7) 0.47121(6) 0.91084(3) 0.0309(2) Uani 1 1 d . . .
N1 N -0.1049(4) 0.5988(4) 0.88552(16) 0.0331(9) Uani 1 1 d . . .
N2 N -0.1916(3) 0.5221(3) 0.79959(16) 0.0269(8) Uani 1 1 d . . .
N3 N -0.3398(4) 0.3803(3) 0.85944(16) 0.0306(9) Uani 1 1 d . . .
N4 N 0.2885(3) 1.0368(3) 0.46300(16) 0.0268(8) Uani 1 1 d . . .
N5 N 0.3380(3) 1.0791(3) 0.33227(16) 0.0240(8) Uani 1 1 d . . .
N6 N 0.2162(3) 0.9732(3) 0.27808(16) 0.0265(8) Uani 1 1 d . . .
C1 C -0.0662(5) 0.6390(5) 0.9313(2) 0.0438(13) Uani 1 1 d . . .
H1 H -0.0883 0.6091 0.9754 0.053 Uiso 1 1 calc R . .
C2 C 0.0034(5) 0.7208(5) 0.9164(2) 0.0461(13) Uani 1 1 d . . .
H2 H 0.0278 0.7457 0.9497 0.055 Uiso 1 1 calc R . .
C3 C 0.0371(5) 0.7659(5) 0.8518(2) 0.0432(13) Uani 1 1 d . . .
H3 H 0.0825 0.8236 0.8406 0.052 Uiso 1 1 calc R . .
C4 C 0.0022(5) 0.7238(4) 0.8031(2) 0.0356(11) Uani 1 1 d . . .
H4 H 0.0143 0.7702 0.7702 0.043 Uiso 1 1 d R . .
C5 C -0.0708(4) 0.6420(4) 0.8212(2) 0.0287(10) Uani 1 1 d . . .
C6 C -0.1186(4) 0.5992(4) 0.7730(2) 0.0278(10) Uani 1 1 d . . .
C7 C -0.0901(4) 0.6308(4) 0.70515(19) 0.0251(9) Uani 1 1 d . . .
H7 H -0.0399 0.6838 0.6881 0.030 Uiso 1 1 calc R . .
C8 C -0.1355(4) 0.5842(4) 0.66201(19) 0.0255(9) Uani 1 1 d . . .
C9 C -0.2089(4) 0.5026(4) 0.6913(2) 0.0284(10) Uani 1 1 d . . .
H9 H -0.2385 0.4661 0.6648 0.034 Uiso 1 1 calc R . .
C10 C -0.2366(4) 0.4769(4) 0.75905(19) 0.0245(9) Uani 1 1 d . . .
C11 C -0.3183(4) 0.3955(4) 0.79322(19) 0.0265(9) Uani 1 1 d . . .
C12 C -0.3678(5) 0.3365(4) 0.7579(2) 0.0359(11) Uani 1 1 d . . .
H12 H -0.3490 0.3459 0.7117 0.043 Uiso 1 1 calc R . .
C13 C -0.4451(5) 0.2640(5) 0.7924(2) 0.0418(13) Uani 1 1 d . . .
H13 H -0.4806 0.2256 0.7698 0.050 Uiso 1 1 calc R . .
C14 C -0.4684(5) 0.2495(5) 0.8594(2) 0.0391(12) Uani 1 1 d . . .
H14 H -0.5196 0.2006 0.8834 0.047 Uiso 1 1 calc R . .
C15 C -0.4151(5) 0.3082(5) 0.8916(2) 0.0418(13) Uani 1 1 d . . .
H15 H -0.4317 0.2977 0.9376 0.050 Uiso 1 1 calc R . .
C16 C -0.1071(4) 0.6168(4) 0.58996(19) 0.0242(9) Uani 1 1 d . . .
C17 C -0.0149(4) 0.6759(4) 0.55828(19) 0.0240(9) Uani 1 1 d . . .
H17 H 0.0107 0.7275 0.5700 0.029 Uiso 1 1 d R . .
C18 C 0.0099(4) 0.7072(3) 0.48935(18) 0.0214(8) Uani 1 1 d . . .
C19 C -0.0559(4) 0.6748(4) 0.45137(18) 0.0235(9) Uani 1 1 d . . .
H19 H -0.0385 0.6934 0.4056 0.028 Uiso 1 1 calc R . .
C20 C -0.1481(4) 0.6142(4) 0.48166(19) 0.0244(9) Uani 1 1 d . . .
C21 C -0.1742(4) 0.5867(4) 0.55013(19) 0.0236(9) Uani 1 1 d . . .
H21 H -0.2372 0.5478 0.5700 0.028 Uiso 1 1 calc R . .
C22 C 0.1034(4) 0.7799(4) 0.4562(2) 0.0264(9) Uani 1 1 d . . .
C23 C -0.2202(4) 0.5771(4) 0.4418(2) 0.0308(10) Uani 1 1 d . . .
C24 C 0.2563(4) 1.0182(4) 0.5289(2) 0.0325(11) Uani 1 1 d . . .
H24 H 0.1996 0.9719 0.5476 0.039 Uiso 1 1 calc R . .
C25 C 0.3027(4) 1.0640(4) 0.5713(2) 0.0333(11) Uani 1 1 d . . .
H25 H 0.2778 1.0484 0.6170 0.040 Uiso 1 1 calc R . .
C26 C 0.3862(4) 1.1328(4) 0.5442(2) 0.0304(10) Uani 1 1 d . . .
H26 H 0.4205 1.1637 0.5711 0.036 Uiso 1 1 calc R . .
C27 C 0.4182(4) 1.1551(4) 0.4758(2) 0.0285(10) Uani 1 1 d . . .
H27 H 0.4732 1.2028 0.4563 0.034 Uiso 1 1 calc R . .
C28 C 0.3683(4) 1.1066(4) 0.43673(19) 0.0227(9) Uani 1 1 d . . .
C29 C 0.3956(4) 1.1306(4) 0.36320(18) 0.0226(9) Uani 1 1 d . . .
C30 C 0.4744(4) 1.2019(4) 0.32882(19) 0.0260(9) Uani 1 1 d . . .
H30 H 0.5180 1.2312 0.3515 0.031 Uiso 1 1 calc R . .
C31 C 0.4889(4) 1.2300(4) 0.2606(2) 0.0251(9) Uani 1 1 d . . .
C32 C 0.4242(4) 1.1793(4) 0.2293(2) 0.0285(10) Uani 1 1 d . . .
H32 H 0.4289 1.1972 0.1841 0.034 Uiso 1 1 calc R . .
C33 C 0.3528(4) 1.1021(4) 0.26589(19) 0.0250(9) Uani 1 1 d . . .
C34 C 0.2832(4) 1.0450(4) 0.23523(19) 0.0255(9) Uani 1 1 d . . .
C35 C 0.2873(5) 1.0603(5) 0.1683(2) 0.0372(12) Uani 1 1 d . . .
H35 H 0.3343 1.1091 0.1400 0.045 Uiso 1 1 calc R . .
C36 C 0.2201(5) 1.0016(4) 0.1435(2) 0.0394(12) Uani 1 1 d . . .
H36 H 0.2237 1.0092 0.0982 0.047 Uiso 1 1 calc R . .
C37 C 0.1496(5) 0.9333(5) 0.1861(2) 0.0386(12) Uani 1 1 d . . .
H37 H 0.1022 0.8957 0.1707 0.046 Uiso 1 1 calc R . .
C38 C 0.1496(4) 0.9207(4) 0.2530(2) 0.0336(11) Uani 1 1 d . . .
H38 H 0.1012 0.8737 0.2819 0.040 Uiso 1 1 calc R . .
C39 C 0.5681(4) 1.3116(4) 0.22260(19) 0.0245(9) Uani 1 1 d . . .
C40 C 0.6088(4) 1.3820(4) 0.25556(19) 0.0282(10) Uani 1 1 d . . .
H40 H 0.5887 1.3757 0.3017 0.034 Uiso 1 1 calc R . .
C41 C 0.6788(4) 1.4614(4) 0.22064(19) 0.0261(9) Uani 1 1 d . . .
C42 C 0.7093(4) 1.4716(4) 0.15246(19) 0.0283(10) Uani 1 1 d . . .
H42 H 0.7554 1.5253 0.1291 0.034 Uiso 1 1 calc R . .
C43 C 0.6707(4) 1.4009(4) 0.11829(19) 0.0263(9) Uani 1 1 d . . .
C44 C 0.6027(4) 1.3208(4) 0.1544(2) 0.0298(10) Uani 1 1 d . . .
H44 H 0.5797 1.2717 0.1316 0.036 Uiso 1 1 calc R . .
C45 C 0.7193(5) 1.5373(4) 0.2575(2) 0.0349(11) Uani 1 1 d . . .
C46 C 0.6990(5) 1.4157(5) 0.0438(2) 0.0350(11) Uani 1 1 d . . .
O1 O 0.1407(3) 0.8344(3) 0.49139(15) 0.0385(8) Uani 1 1 d . . .
O1W O -0.3931(3) 0.6371(3) 0.93002(16) 0.0450(9) Uani 1 1 d . . .
H1WA H -0.3926 0.6693 0.8944 0.067 Uiso 1 1 d R . .
H1WB H -0.4586 0.6334 0.9604 0.067 Uiso 1 1 d R . .
O2 O 0.1396(3) 0.7878(3) 0.39448(14) 0.0389(8) Uani 1 1 d . . .
O2W O -0.0754(3) 0.2985(4) 0.8993(2) 0.0565(10) Uani 1 1 d . . .
H2WA H -0.0420 0.2874 0.8588 0.085 Uiso 1 1 d R . .
H2WB H -0.0114 0.3079 0.9109 0.085 Uiso 1 1 d R . .
O3 O -0.1870(3) 0.6032(3) 0.37814(15) 0.0450(9) Uani 1 1 d . . .
O3W O 0.0367(3) 1.0673(3) 0.40222(17) 0.0437(8) Uani 1 1 d . . .
H3WA H 0.0229 1.1085 0.3664 0.066 Uiso 1 1 d R . .
H3WB H 0.0129 1.0173 0.4284 0.066 Uiso 1 1 d R . .
O4 O -0.3005(3) 0.5220(4) 0.46729(16) 0.0473(10) Uani 1 1 d . . .
O4W O 0.4063(3) 0.8067(3) 0.37690(16) 0.0415(8) Uani 1 1 d . . .
H4WA H 0.4473 0.8069 0.3353 0.062 Uiso 1 1 d R . .
H4WB H 0.3932 0.7356 0.3898 0.062 Uiso 1 1 d R . .
O5 O 0.7031(4) 1.5106(4) 0.32037(16) 0.0617(13) Uani 1 1 d . . .
O5W O 0.8639(4) 0.1314(5) 0.3255(2) 0.0807(15) Uani 1 1 d . . .
H5WA H 0.8875 0.0553 0.3320 0.097 Uiso 1 1 d R . .
H5WB H 0.8276 0.1597 0.2876 0.097 Uiso 1 1 d R . .
O6 O 0.7659(4) 1.6210(3) 0.22759(16) 0.0530(11) Uani 1 1 d . . .
O6W O 0.9558(5) 0.7402(5) 0.2475(3) 0.1011(19) Uani 1 1 d . . .
H6WA H 0.9022 0.7068 0.2423 0.152 Uiso 1 1 d R . .
H6WB H 0.9682 0.8043 0.2246 0.152 Uiso 1 1 d R . .
O7 O 0.7821(3) 1.4679(3) 0.01308(15) 0.0466(9) Uani 1 1 d . . .
O7W O 0.3128(5) 0.7088(4) 0.5874(3) 0.0784(14) Uani 1 1 d G . .
H7WA H 0.2779 0.7682 0.6105 0.118 Uiso 1 1 d G . .
H7WB H 0.2965 0.7272 0.5492 0.118 Uiso 1 1 d G . .
O8 O 0.6391(4) 1.3755(4) 0.01417(15) 0.0534(11) Uani 1 1 d . . .
O8W O 0.4350(5) 0.5636(4) 0.4079(3) 0.0838(16) Uani 1 1 d G . .
H8WA H 0.5001 0.5297 0.3801 0.126 Uiso 1 1 d G . .
H8WB H 0.4460 0.5408 0.4470 0.126 Uiso 1 1 d G . .
O9W O 0.6198(4) 0.8373(4) 0.2902(2) 0.0699(13) Uani 1 1 d . . .
H9WA H 0.5929 0.8730 0.2578 0.105 Uiso 1 1 d R . .
H9WB H 0.6661 0.7791 0.2679 0.105 Uiso 1 1 d R . .
O10W O 0.7959(3) 0.9954(3) 0.2382(2) 0.0563(11) Uani 1 1 d . . .
H10A H 0.7999 0.9422 0.2677 0.084 Uiso 1 1 d R . .
H10B H 0.7991 0.9894 0.1980 0.084 Uiso 1 1 d R . .
O0AA O 0.8187(6) 1.7410(5) 0.0982(2) 0.0892(16) Uani 1 1 d G . .
H0AA H 0.7981 1.8144 0.0835 0.134 Uiso 1 1 d G . .
H0AB H 0.7819 1.7330 0.1390 0.134 Uiso 1 1 d G . .


_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 O4W 2.187(3) . ?
Mn1 O3W 2.190(4) . ?
Mn1 N5 2.289(3) . ?
Mn1 O2 2.307(3) . ?
Mn1 N6 2.338(3) . ?
Mn1 N4 2.359(3) . ?
Mn1 O1 2.438(3) . ?
Mn2 O7 2.206(3) 1_446 ?
Mn2 O1W 2.223(4) . ?
Mn2 N2 2.273(3) . ?
Mn2 O2W 2.296(4) . ?
Mn2 N1 2.322(4) . ?
Mn2 N3 2.327(3) . ?
N1 C1 1.352(6) . ?
N1 C5 1.359(5) . ?
N2 C10 1.341(5) . ?
N2 C6 1.357(5) . ?
N3 C11 1.338(5) . ?
N3 C15 1.353(5) . ?
N4 C24 1.334(5) . ?
N4 C28 1.347(5) . ?
N5 C29 1.340(5) . ?
N5 C33 1.350(5) . ?
N6 C38 1.347(5) . ?
N6 C34 1.364(5) . ?
C1 C2 1.361(7) . ?
C2 C3 1.370(7) . ?
C3 C4 1.389(6) . ?
C4 C5 1.388(6) . ?
C5 C6 1.476(6) . ?
C6 C7 1.387(5) . ?
C7 C8 1.398(6) . ?
C8 C9 1.410(6) . ?
C8 C16 1.471(5) . ?
C9 C10 1.376(5) . ?
C10 C11 1.492(5) . ?
C11 C12 1.397(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.352(6) . ?
C14 C15 1.380(6) . ?
C16 C17 1.388(5) . ?
C16 C21 1.412(5) . ?
C17 C18 1.407(5) . ?
C18 C19 1.384(5) . ?
C18 C22 1.510(5) . ?
C19 C20 1.393(5) . ?
C20 C21 1.392(5) . ?
C20 C23 1.498(6) . ?
C22 O2 1.249(5) . ?
C22 O1 1.267(5) . ?
C23 O4 1.228(5) . ?
C23 O3 1.300(5) . ?
C24 C25 1.385(6) . ?
C25 C26 1.374(6) . ?
C26 C27 1.385(6) . ?
C27 C28 1.379(6) . ?
C28 C29 1.488(5) . ?
C29 C30 1.385(5) . ?
C30 C31 1.392(6) . ?
C31 C32 1.400(5) . ?
C31 C39 1.495(5) . ?
C32 C33 1.391(5) . ?
C33 C34 1.484(5) . ?
C34 C35 1.376(6) . ?
C35 C36 1.400(6) . ?
C36 C37 1.357(6) . ?
C37 C38 1.387(6) . ?
C39 C44 1.377(5) . ?
C39 C40 1.394(6) . ?
C40 C41 1.391(6) . ?
C41 C42 1.374(5) . ?
C41 C45 1.500(5) . ?
C42 C43 1.400(6) . ?
C43 C44 1.390(6) . ?
C43 C46 1.502(5) . ?
C45 O6 1.249(5) . ?
C45 O5 1.281(5) . ?
C46 O7 1.252(5) . ?
C46 O8 1.256(5) . ?
O7 Mn2 2.206(3) 1_664 ?

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
O4W Mn1 O3W 173.42(12) . . ?
O4W Mn1 N5 87.52(13) . . ?
O3W Mn1 N5 98.20(14) . . ?
O4W Mn1 O2 84.58(13) . . ?
O3W Mn1 O2 88.85(13) . . ?
N5 Mn1 O2 151.85(11) . . ?
O4W Mn1 N6 96.19(13) . . ?
O3W Mn1 N6 82.84(13) . . ?
N5 Mn1 N6 69.89(11) . . ?
O2 Mn1 N6 84.15(11) . . ?
O4W Mn1 N4 90.81(13) . . ?
O3W Mn1 N4 94.24(13) . . ?
N5 Mn1 N4 69.36(11) . . ?
O2 Mn1 N4 137.58(11) . . ?
N6 Mn1 N4 138.24(12) . . ?
O4W Mn1 O1 90.69(13) . . ?
O3W Mn1 O1 85.74(13) . . ?
N5 Mn1 O1 152.29(11) . . ?
O2 Mn1 O1 54.98(10) . . ?
N6 Mn1 O1 137.72(10) . . ?
N4 Mn1 O1 83.03(11) . . ?
O7 Mn2 O1W 87.21(14) 1_446 . ?
O7 Mn2 N2 154.05(12) 1_446 . ?
O1W Mn2 N2 93.06(13) . . ?
O7 Mn2 O2W 88.49(15) 1_446 . ?
O1W Mn2 O2W 175.67(13) . . ?
N2 Mn2 O2W 91.01(14) . . ?
O7 Mn2 N1 83.87(12) 1_446 . ?
O1W Mn2 N1 85.24(14) . . ?
N2 Mn2 N1 70.32(12) . . ?
O2W Mn2 N1 94.77(15) . . ?
O7 Mn2 N3 135.58(12) 1_446 . ?
O1W Mn2 N3 96.24(14) . . ?
N2 Mn2 N3 70.22(12) . . ?
O2W Mn2 N3 86.51(14) . . ?
N1 Mn2 N3 140.53(12) . . ?
C1 N1 C5 117.7(4) . . ?
C1 N1 Mn2 124.1(3) . . ?
C5 N1 Mn2 118.1(3) . . ?
C10 N2 C6 118.8(3) . . ?
C10 N2 Mn2 120.7(2) . . ?
C6 N2 Mn2 120.5(3) . . ?
C11 N3 C15 117.4(4) . . ?
C11 N3 Mn2 117.9(3) . . ?
C15 N3 Mn2 124.6(3) . . ?
C24 N4 C28 117.5(3) . . ?
C24 N4 Mn1 124.4(3) . . ?
C28 N4 Mn1 117.9(3) . . ?
C29 N5 C33 118.7(3) . . ?
C29 N5 Mn1 120.8(2) . . ?
C33 N5 Mn1 120.4(3) . . ?
C38 N6 C34 117.5(3) . . ?
C38 N6 Mn1 123.9(3) . . ?
C34 N6 Mn1 118.6(2) . . ?
N1 C1 C2 123.6(4) . . ?
C1 C2 C3 119.1(4) . . ?
C2 C3 C4 118.9(4) . . ?
C5 C4 C3 119.7(4) . . ?
N1 C5 C4 121.0(4) . . ?
N1 C5 C6 116.1(4) . . ?
C4 C5 C6 122.9(4) . . ?
N2 C6 C7 121.1(4) . . ?
N2 C6 C5 114.9(3) . . ?
C7 C6 C5 124.0(4) . . ?
C6 C7 C8 121.1(4) . . ?
C7 C8 C9 116.3(4) . . ?
C7 C8 C16 122.1(4) . . ?
C9 C8 C16 121.6(4) . . ?
C10 C9 C8 120.0(4) . . ?
N2 C10 C9 122.8(4) . . ?
N2 C10 C11 114.6(3) . . ?
C9 C10 C11 122.6(4) . . ?
N3 C11 C12 121.8(4) . . ?
N3 C11 C10 116.4(3) . . ?
C12 C11 C10 121.8(4) . . ?
C13 C12 C11 119.1(4) . . ?
C14 C13 C12 119.3(4) . . ?
C13 C14 C15 119.0(4) . . ?
N3 C15 C14 123.3(4) . . ?
C17 C16 C21 117.4(4) . . ?
C17 C16 C8 122.7(4) . . ?
C21 C16 C8 119.9(4) . . ?
C16 C17 C18 121.8(4) . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 C22 119.2(3) . . ?
C17 C18 C22 121.3(3) . . ?
C18 C19 C20 120.0(3) . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 C23 118.9(4) . . ?
C19 C20 C23 121.2(4) . . ?
C20 C21 C16 121.3(4) . . ?
O2 C22 O1 121.4(4) . . ?
O2 C22 C18 119.2(4) . . ?
O1 C22 C18 119.4(4) . . ?
O4 C23 O3 122.9(4) . . ?
O4 C23 C20 122.4(4) . . ?
O3 C23 C20 114.7(4) . . ?
N4 C24 C25 123.7(4) . . ?
C26 C25 C24 118.5(4) . . ?
C25 C26 C27 118.3(4) . . ?
C28 C27 C26 120.0(4) . . ?
N4 C28 C27 121.9(4) . . ?
N4 C28 C29 115.6(3) . . ?
C27 C28 C29 122.5(4) . . ?
N5 C29 C30 122.0(4) . . ?
N5 C29 C28 115.4(3) . . ?
C30 C29 C28 122.6(4) . . ?
C29 C30 C31 120.5(4) . . ?
C30 C31 C32 116.7(3) . . ?
C30 C31 C39 121.9(3) . . ?
C32 C31 C39 121.4(4) . . ?
C33 C32 C31 120.1(4) . . ?
N5 C33 C32 121.7(4) . . ?
N5 C33 C34 115.8(3) . . ?
C32 C33 C34 122.4(4) . . ?
N6 C34 C35 121.8(4) . . ?
N6 C34 C33 115.1(3) . . ?
C35 C34 C33 123.1(4) . . ?
C34 C35 C36 119.3(4) . . ?
C37 C36 C35 119.3(4) . . ?
C36 C37 C38 118.9(4) . . ?
N6 C38 C37 123.2(4) . . ?
C44 C39 C40 117.8(4) . . ?
C44 C39 C31 121.6(4) . . ?
C40 C39 C31 120.6(3) . . ?
C41 C40 C39 121.1(4) . . ?
C42 C41 C40 120.2(4) . . ?
C42 C41 C45 120.0(4) . . ?
C40 C41 C45 119.9(4) . . ?
C41 C42 C43 119.7(4) . . ?
C44 C43 C42 119.0(4) . . ?
C44 C43 C46 121.1(4) . . ?
C42 C43 C46 119.8(4) . . ?
C39 C44 C43 122.2(4) . . ?
O6 C45 O5 123.3(4) . . ?
O6 C45 C41 120.7(4) . . ?
O5 C45 C41 116.0(4) . . ?
O7 C46 O8 121.9(4) . . ?
O7 C46 C43 118.8(4) . . ?
O8 C46 C43 119.3(4) . . ?
C22 O1 Mn1 87.9(2) . . ?
C22 O2 Mn1 94.4(2) . . ?
C46 O7 Mn2 99.6(3) . 1_664 ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.103


