# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1440204'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-01-08 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         'C44 H53 Fe N4 O6'
_chemical_formula_sum            'C44 H53 Fe N4 O6'
_chemical_formula_weight         789.75

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'
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'
Fe Fe 0.3463 0.8444 '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'

_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                   17.1427(14)
_cell_length_b                   14.5854(13)
_cell_length_c                   17.4812(14)
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 100.604(2)
_cell_angle_gamma                90.000(2)
_cell_volume                     4296.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3745
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      20.91

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             1676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33844
_diffrn_reflns_av_unetI/netI     0.1565
_diffrn_reflns_av_R_equivalents  0.1452
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         25.417
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             7677
_reflns_number_gt                3373
_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0927P)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         7677
_refine_ls_number_parameters     533
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1924
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.868
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2451(3) -0.0593(3) 0.2285(2) 0.0390(12) Uani 1 1 d . . . . .
C2 C 0.1630(3) -0.0849(3) 0.2078(3) 0.0422(13) Uani 1 1 d . . . . .
C3 C 0.1376(3) -0.1543(4) 0.2491(3) 0.0480(13) Uani 1 1 d . . . . .
H3 H 0.0846 -0.1713 0.2353 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1841(3) -0.2031(3) 0.3109(3) 0.0449(13) Uani 1 1 d . . . . .
C5 C 0.2604(3) -0.1698(3) 0.3339(2) 0.0438(13) Uani 1 1 d . . . . .
H5 H 0.2927 -0.1963 0.3768 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2907(3) -0.0986(3) 0.2955(2) 0.0366(12) Uani 1 1 d . . . . .
C7 C 0.3688(3) -0.0654(3) 0.3260(2) 0.0410(13) Uani 1 1 d . . . . .
H7 H 0.3934 -0.0878 0.3742 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5204(3) 0.0694(3) 0.2949(2) 0.0347(12) Uani 1 1 d . . . . .
C9 C 0.5972(3) 0.1068(3) 0.3348(2) 0.0359(11) Uani 1 1 d . . . . .
C10 C 0.6287(3) 0.0827(3) 0.4118(3) 0.0474(13) Uani 1 1 d . . . . .
C11 C 0.7019(3) 0.1182(4) 0.4470(3) 0.0622(16) Uani 1 1 d . . . . .
H11 H 0.7239 0.1013 0.4976 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7416(3) 0.1782(4) 0.4071(3) 0.0695(17) Uani 1 1 d . . . . .
H12 H 0.7904 0.2016 0.4314 0.083 Uiso 1 1 calc R U . . .
C13 C 0.7110(3) 0.2040(4) 0.3326(3) 0.0640(16) Uani 1 1 d . . . . .
H13 H 0.7381 0.2450 0.3063 0.077 Uiso 1 1 calc R U . . .
C14 C 0.6391(3) 0.1680(4) 0.2971(3) 0.0515(14) Uani 1 1 d . . . . .
H14 H 0.6180 0.1854 0.2463 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1087(3) -0.0361(4) 0.1405(3) 0.0543(14) Uani 1 1 d . . . . .
C16 C 0.1090(3) 0.0678(4) 0.1544(4) 0.0799(19) Uani 1 1 d . . . . .
H16A H 0.0911 0.0803 0.2023 0.120 Uiso 1 1 calc R U . . .
H16B H 0.1619 0.0911 0.1576 0.120 Uiso 1 1 calc R U . . .
H16C H 0.0743 0.0971 0.1121 0.120 Uiso 1 1 calc R U . . .
C17 C 0.1370(3) -0.0568(4) 0.0648(3) 0.080(2) Uani 1 1 d . . . . .
H17A H 0.1032 -0.0263 0.0225 0.119 Uiso 1 1 calc R U . . .
H17B H 0.1905 -0.0353 0.0683 0.119 Uiso 1 1 calc R U . . .
H17C H 0.1353 -0.1217 0.0558 0.119 Uiso 1 1 calc R U . . .
C18 C 0.0220(3) -0.0680(5) 0.1320(4) 0.093(2) Uani 1 1 d . . . . .
H18A H 0.0031 -0.0554 0.1793 0.139 Uiso 1 1 calc R U . . .
H18B H -0.0101 -0.0356 0.0897 0.139 Uiso 1 1 calc R U . . .
H18C H 0.0189 -0.1326 0.1217 0.139 Uiso 1 1 calc R U . . .
C25 C 0.1508(3) -0.2857(4) 0.3471(3) 0.0588(15) Uani 1 1 d . . . . .
C26 C 0.1129(4) -0.3526(4) 0.2829(3) 0.097(2) Uani 1 1 d . . . . .
H26A H 0.1523 -0.3725 0.2539 0.146 Uiso 1 1 calc R U . . .
H26B H 0.0922 -0.4047 0.3061 0.146 Uiso 1 1 calc R U . . .
H26C H 0.0706 -0.3223 0.2485 0.146 Uiso 1 1 calc R U . . .
C27 C 0.0902(3) -0.2528(5) 0.3939(3) 0.088(2) Uani 1 1 d . . . . .
H27A H 0.0688 -0.3045 0.4171 0.133 Uiso 1 1 calc R U . . .
H27B H 0.1153 -0.2120 0.4341 0.133 Uiso 1 1 calc R U . . .
H27C H 0.0482 -0.2212 0.3603 0.133 Uiso 1 1 calc R U . . .
C28 C 0.2167(3) -0.3387(4) 0.4013(3) 0.0758(19) Uani 1 1 d . . . . .
H28A H 0.2554 -0.3598 0.3720 0.114 Uiso 1 1 calc R U . . .
H28B H 0.2418 -0.2990 0.4423 0.114 Uiso 1 1 calc R U . . .
H28C H 0.1940 -0.3903 0.4232 0.114 Uiso 1 1 calc R U . . .
C31 C 0.2953(3) 0.2201(3) 0.1232(3) 0.0431(13) Uani 1 1 d . . . . .
C32 C 0.2642(3) 0.3045(3) 0.1453(3) 0.0449(13) Uani 1 1 d . . . . .
C33 C 0.2107(3) 0.3508(4) 0.0907(3) 0.0541(14) Uani 1 1 d . . . . .
H33 H 0.1896 0.4051 0.1062 0.065 Uiso 1 1 calc R U . . .
C34 C 0.1853(3) 0.3223(4) 0.0128(3) 0.0568(15) Uani 1 1 d . . . . .
C35 C 0.2171(3) 0.2428(4) -0.0079(3) 0.0526(14) Uani 1 1 d . . . . .
H35 H 0.2018 0.2213 -0.0585 0.063 Uiso 1 1 calc R U . . .
C36 C 0.2721(3) 0.1922(3) 0.0445(2) 0.0424(13) Uani 1 1 d . . . . .
C37 C 0.3061(3) 0.1125(3) 0.0160(3) 0.0426(13) Uani 1 1 d . . . . .
H37 H 0.2926 0.1007 -0.0371 0.051 Uiso 1 1 calc R U . . .
C38 C 0.4246(3) -0.0782(3) 0.0647(2) 0.0366(12) Uani 1 1 d . . . . .
C39 C 0.4636(3) -0.1527(3) 0.0293(2) 0.0372(12) Uani 1 1 d . . . . .
C40 C 0.4683(3) -0.1572(3) -0.0502(2) 0.0387(12) Uani 1 1 d . . . . .
C41 C 0.5089(3) -0.2283(4) -0.0771(3) 0.0486(14) Uani 1 1 d . . . . .
H41 H 0.5119 -0.2313 -0.1296 0.058 Uiso 1 1 calc R U . . .
C42 C 0.5447(3) -0.2947(4) -0.0270(3) 0.0552(15) Uani 1 1 d . . . . .
H42 H 0.5718 -0.3424 -0.0459 0.066 Uiso 1 1 calc R U . . .
C43 C 0.5409(3) -0.2913(4) 0.0513(3) 0.0547(14) Uani 1 1 d . . . . .
H43 H 0.5658 -0.3359 0.0853 0.066 Uiso 1 1 calc R U . . .
C44 C 0.5000(3) -0.2211(4) 0.0777(3) 0.0487(14) Uani 1 1 d . . . . .
H44 H 0.4965 -0.2195 0.1301 0.058 Uiso 1 1 calc R U . . .
C45 C 0.2904(3) 0.3424(4) 0.2267(3) 0.0565(15) Uani 1 1 d . . . . .
C46 C 0.3804(4) 0.3598(4) 0.2407(3) 0.0777(19) Uani 1 1 d . . . . .
H46A H 0.3975 0.3839 0.2922 0.117 Uiso 1 1 calc R U . . .
H46B H 0.4076 0.3033 0.2354 0.117 Uiso 1 1 calc R U . . .
H46C H 0.3922 0.4032 0.2031 0.117 Uiso 1 1 calc R U . . .
C47 C 0.2709(4) 0.2735(4) 0.2873(3) 0.085(2) Uani 1 1 d . . . . .
H47A H 0.2877 0.2981 0.3387 0.127 Uiso 1 1 calc R U . . .
H47B H 0.2147 0.2626 0.2784 0.127 Uiso 1 1 calc R U . . .
H47C H 0.2982 0.2168 0.2827 0.127 Uiso 1 1 calc R U . . .
C48 C 0.2510(4) 0.4347(4) 0.2393(4) 0.107(3) Uani 1 1 d . . . . .
H48A H 0.2696 0.4554 0.2916 0.160 Uiso 1 1 calc R U . . .
H48B H 0.2643 0.4791 0.2033 0.160 Uiso 1 1 calc R U . . .
H48C H 0.1944 0.4270 0.2308 0.160 Uiso 1 1 calc R U . . .
C55 C 0.1244(4) 0.3779(6) -0.0435(3) 0.087(2) Uani 1 1 d D . . . .
C56A C 0.0999(11) 0.4675(14) -0.0051(9) 0.114(7) Uani 0.542(11) 1 d . U P A 1
H56A H 0.1461 0.4953 0.0255 0.171 Uiso 0.542(11) 1 calc R U P A 1
H56B H 0.0760 0.5094 -0.0449 0.171 Uiso 0.542(11) 1 calc R U P A 1
H56C H 0.0626 0.4529 0.0279 0.171 Uiso 0.542(11) 1 calc R U P A 1
C57A C 0.0705(11) 0.3264(14) -0.0891(11) 0.132(8) Uani 0.542(11) 1 d . U P A 1
H57A H 0.0343 0.3653 -0.1229 0.198 Uiso 0.542(11) 1 calc R U P A 1
H57B H 0.0967 0.2862 -0.1198 0.198 Uiso 0.542(11) 1 calc R U P A 1
H57C H 0.0418 0.2907 -0.0575 0.198 Uiso 0.542(11) 1 calc R U P A 1
C58A C 0.1809(8) 0.4280(8) -0.0998(6) 0.095(5) Uani 0.542(11) 1 d D U P A 1
H58A H 0.2203 0.4655 -0.0682 0.142 Uiso 0.542(11) 1 calc R U P A 1
H58B H 0.2066 0.3818 -0.1254 0.142 Uiso 0.542(11) 1 calc R U P A 1
H58C H 0.1483 0.4655 -0.1380 0.142 Uiso 0.542(11) 1 calc R U P A 1
C56B C 0.1285(13) 0.4682(17) -0.0438(13) 0.122(9) Uani 0.458(11) 1 d . U P A 2
H56D H 0.0863 0.4923 -0.0823 0.183 Uiso 0.458(11) 1 calc R U P A 2
H56E H 0.1237 0.4913 0.0066 0.183 Uiso 0.458(11) 1 calc R U P A 2
H56F H 0.1786 0.4868 -0.0558 0.183 Uiso 0.458(11) 1 calc R U P A 2
C57B C 0.1011(12) 0.3318(16) -0.1287(10) 0.103(7) Uani 0.458(11) 1 d . U P A 2
H57D H 0.0994 0.2664 -0.1235 0.154 Uiso 0.458(11) 1 calc R U P A 2
H57E H 0.0500 0.3538 -0.1538 0.154 Uiso 0.458(11) 1 calc R U P A 2
H57F H 0.1401 0.3480 -0.1594 0.154 Uiso 0.458(11) 1 calc R U P A 2
C58B C 0.0371(8) 0.3584(13) -0.0199(11) 0.115(7) Uani 0.458(11) 1 d D U P A 2
H58D H 0.0283 0.2935 -0.0181 0.173 Uiso 0.458(11) 1 calc R U P A 2
H58E H 0.0358 0.3846 0.0302 0.173 Uiso 0.458(11) 1 calc R U P A 2
H58F H -0.0038 0.3857 -0.0580 0.173 Uiso 0.458(11) 1 calc R U P A 2
N1 N 0.4077(2) -0.0077(3) 0.29269(19) 0.0353(9) Uani 1 1 d . . . . .
N2 N 0.4814(2) 0.0182(3) 0.33584(19) 0.0390(10) Uani 1 1 d . . . . .
N3 N 0.3536(2) 0.0558(3) 0.05703(19) 0.0381(10) Uani 1 1 d . . . . .
N4 N 0.3834(2) -0.0147(3) 0.0187(2) 0.0410(11) Uani 1 1 d . . . . .
O1 O 0.49265(17) 0.0897(2) 0.22200(15) 0.0405(8) Uani 1 1 d . . . . .
O2 O 0.27513(17) 0.0005(2) 0.18539(15) 0.0417(8) Uani 1 1 d . . . . .
O3 O 0.5936(2) 0.0262(3) 0.45498(18) 0.0623(12) Uani 1 1 d . . . . .
O4 O 0.42864(18) -0.0721(2) 0.13680(15) 0.0455(9) Uani 1 1 d . . . . .
O5 O 0.3458(2) 0.1719(2) 0.17309(16) 0.0467(9) Uani 1 1 d . . . . .
O6 O 0.4349(2) -0.0885(2) -0.09898(17) 0.0498(9) Uani 1 1 d D . . . .
Fe1 Fe 0.37805(4) 0.04624(5) 0.18055(3) 0.0388(2) Uani 1 1 d . . . . .
H3O H 0.553(3) 0.010(4) 0.424(3) 0.058 Uiso 1 1 d . U . . .
H6O H 0.447(3) -0.105(3) -0.1424(16) 0.058 Uiso 1 1 d D U . . .
H4N H 0.385(3) -0.018(3) -0.036(3) 0.058 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.317(5) . ?
C1 C6 1.406(6) . ?
C1 C2 1.437(6) . ?
C2 C3 1.361(6) . ?
C2 C15 1.534(6) . ?
C3 C4 1.411(6) . ?
C4 C5 1.384(6) . ?
C4 C25 1.519(7) . ?
C5 C6 1.388(6) . ?
C6 C7 1.431(6) . ?
C7 N1 1.278(5) . ?
C8 N2 1.301(5) . ?
C8 O1 1.310(5) . ?
C8 C9 1.475(6) . ?
C9 C14 1.386(6) . ?
C9 C10 1.400(6) . ?
C10 O3 1.335(5) . ?
C10 C11 1.391(6) . ?
C11 C12 1.375(7) . ?
C12 C13 1.364(7) . ?
C13 C14 1.378(6) . ?
C15 C17 1.520(7) . ?
C15 C16 1.535(7) . ?
C15 C18 1.539(7) . ?
C25 C27 1.514(7) . ?
C25 C26 1.538(7) . ?
C25 C28 1.542(7) . ?
C31 O5 1.314(5) . ?
C31 C36 1.420(6) . ?
C31 C32 1.423(6) . ?
C32 C33 1.373(6) . ?
C32 C45 1.517(6) . ?
C33 C34 1.414(7) . ?
C34 C35 1.359(7) . ?
C34 C55 1.529(7) . ?
C35 C36 1.398(6) . ?
C36 C37 1.429(6) . ?
C37 N3 1.283(5) . ?
C38 O4 1.253(5) . ?
C38 N4 1.339(5) . ?
C38 C39 1.471(6) . ?
C39 C44 1.380(6) . ?
C39 C40 1.409(5) . ?
C40 O6 1.371(5) . ?
C40 C41 1.378(6) . ?
C41 C42 1.372(6) . ?
C42 C43 1.382(6) . ?
C43 C44 1.369(6) . ?
C45 C46 1.537(7) . ?
C45 C47 1.541(7) . ?
C45 C48 1.540(7) . ?
C55 C56B 1.32(2) . ?
C55 C57A 1.335(18) . ?
C55 C56A 1.563(18) . ?
C55 C57B 1.61(2) . ?
C55 C58B 1.650(13) . ?
C55 C58A 1.670(12) . ?
N1 N2 1.399(5) . ?
N1 Fe1 2.087(3) . ?
N3 N4 1.376(5) . ?
N3 Fe1 2.127(3) . ?
O1 Fe1 2.065(3) . ?
O2 Fe1 1.903(3) . ?
O4 Fe1 2.135(3) . ?
O5 Fe1 1.912(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
O2 C1 C6 122.1(4) . . ?
O2 C1 C2 119.7(4) . . ?
C6 C1 C2 118.2(4) . . ?
C3 C2 C1 117.0(4) . . ?
C3 C2 C15 123.0(4) . . ?
C1 C2 C15 120.0(4) . . ?
C2 C3 C4 126.3(5) . . ?
C5 C4 C3 114.6(4) . . ?
C5 C4 C25 124.4(4) . . ?
C3 C4 C25 121.1(5) . . ?
C4 C5 C6 122.7(4) . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 C7 118.8(4) . . ?
C1 C6 C7 120.7(4) . . ?
N1 C7 C6 125.8(4) . . ?
N2 C8 O1 122.2(4) . . ?
N2 C8 C9 117.2(4) . . ?
O1 C8 C9 120.6(4) . . ?
C14 C9 C10 118.4(5) . . ?
C14 C9 C8 120.6(4) . . ?
C10 C9 C8 121.0(4) . . ?
O3 C10 C11 116.3(4) . . ?
O3 C10 C9 124.4(4) . . ?
C11 C10 C9 119.3(4) . . ?
C12 C11 C10 120.2(5) . . ?
C13 C12 C11 121.3(5) . . ?
C12 C13 C14 118.7(5) . . ?
C13 C14 C9 122.0(5) . . ?
C17 C15 C2 109.3(4) . . ?
C17 C15 C16 110.0(5) . . ?
C2 C15 C16 110.6(5) . . ?
C17 C15 C18 108.3(5) . . ?
C2 C15 C18 111.9(4) . . ?
C16 C15 C18 106.7(5) . . ?
C27 C25 C4 108.8(5) . . ?
C27 C25 C26 110.9(5) . . ?
C4 C25 C26 109.9(4) . . ?
C27 C25 C28 108.9(4) . . ?
C4 C25 C28 111.3(4) . . ?
C26 C25 C28 107.1(5) . . ?
O5 C31 C36 121.5(4) . . ?
O5 C31 C32 121.2(4) . . ?
C36 C31 C32 117.3(5) . . ?
C33 C32 C31 118.3(5) . . ?
C33 C32 C45 121.1(5) . . ?
C31 C32 C45 120.6(4) . . ?
C32 C33 C34 124.9(5) . . ?
C35 C34 C33 116.1(5) . . ?
C35 C34 C55 122.7(5) . . ?
C33 C34 C55 121.1(5) . . ?
C34 C35 C36 122.1(5) . . ?
C35 C36 C31 121.2(5) . . ?
C35 C36 C37 118.1(4) . . ?
C31 C36 C37 120.7(4) . . ?
N3 C37 C36 125.9(4) . . ?
O4 C38 N4 118.7(4) . . ?
O4 C38 C39 122.0(4) . . ?
N4 C38 C39 119.3(4) . . ?
C44 C39 C40 118.0(4) . . ?
C44 C39 C38 117.8(4) . . ?
C40 C39 C38 124.2(4) . . ?
O6 C40 C41 121.2(4) . . ?
O6 C40 C39 119.1(4) . . ?
C41 C40 C39 119.7(5) . . ?
C42 C41 C40 120.6(4) . . ?
C41 C42 C43 120.6(5) . . ?
C44 C43 C42 118.7(5) . . ?
C43 C44 C39 122.4(5) . . ?
C32 C45 C46 108.9(4) . . ?
C32 C45 C47 110.1(5) . . ?
C46 C45 C47 109.7(5) . . ?
C32 C45 C48 113.0(5) . . ?
C46 C45 C48 106.7(5) . . ?
C47 C45 C48 108.4(4) . . ?
C56B C55 C34 120.1(11) . . ?
C57A C55 C34 113.7(10) . . ?
C57A C55 C56A 121.1(12) . . ?
C34 C55 C56A 111.8(8) . . ?
C56B C55 C57B 114.6(13) . . ?
C34 C55 C57B 113.4(9) . . ?
C56B C55 C58B 103.0(12) . . ?
C34 C55 C58B 106.9(7) . . ?
C57B C55 C58B 94.4(11) . . ?
C57A C55 C58A 107.9(11) . . ?
C34 C55 C58A 102.2(6) . . ?
C56A C55 C58A 96.8(10) . . ?
C7 N1 N2 115.3(4) . . ?
C7 N1 Fe1 128.2(3) . . ?
N2 N1 Fe1 116.4(2) . . ?
C8 N2 N1 111.3(3) . . ?
C37 N3 N4 117.7(4) . . ?
C37 N3 Fe1 126.6(3) . . ?
N4 N3 Fe1 115.1(3) . . ?
C38 N4 N3 115.3(4) . . ?
C8 O1 Fe1 115.1(3) . . ?
C1 O2 Fe1 136.1(3) . . ?
C38 O4 Fe1 117.8(3) . . ?
C31 O5 Fe1 134.9(3) . . ?
O2 Fe1 O5 94.58(14) . . ?
O2 Fe1 O1 157.27(11) . . ?
O5 Fe1 O1 88.53(13) . . ?
O2 Fe1 N1 83.89(13) . . ?
O5 Fe1 N1 116.30(13) . . ?
O1 Fe1 N1 74.61(13) . . ?
O2 Fe1 N3 93.28(13) . . ?
O5 Fe1 N3 82.38(14) . . ?
O1 Fe1 N3 109.45(12) . . ?
N1 Fe1 N3 161.24(15) . . ?
O2 Fe1 O4 100.01(13) . . ?
O5 Fe1 O4 151.87(12) . . ?
O1 Fe1 O4 87.19(12) . . ?
N1 Fe1 O4 89.25(13) . . ?
N3 Fe1 O4 72.94(13) . . ?

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
N4 H4N O6 0.96(4) 1.83(5) 2.615(5) 136(4) .
O3 H3O N2 0.84(5) 1.78(5) 2.565(5) 154(5) .
O6 H6O O1 0.857(19) 1.90(3) 2.674(4) 150(4) 3_655

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.467
_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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1440205'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-01-08 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         'C28 H21 Co N4 O8, C2 H6 O'
_chemical_formula_sum            'C30 H27 Co N4 O9'
_chemical_formula_weight         646.48

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   18.5211(10)
_cell_length_b                   11.1131(6)
_cell_length_c                   12.9945(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3917
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.05

_exptl_crystal_description       cube
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21785
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5032
_reflns_number_gt                3914
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.997

_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+1.8378P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.61(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5032
_refine_ls_number_parameters     417
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8504(3) 0.3784(5) 0.7730(5) 0.0154(13) Uani 1 1 d . . . . .
C2 C 0.9066(3) 0.2932(5) 0.7604(6) 0.0192(14) Uani 1 1 d . . . . .
C3 C 0.9302(3) 0.2224(5) 0.8395(5) 0.0244(15) Uani 1 1 d . . . . .
H3 H 0.9668 0.1642 0.8271 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9015(3) 0.2341(6) 0.9378(6) 0.0236(16) Uani 1 1 d . . . . .
H4 H 0.9178 0.1841 0.9924 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8495(3) 0.3190(6) 0.9547(6) 0.0229(16) Uani 1 1 d . . . . .
H5 H 0.8300 0.3287 1.0218 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8243(3) 0.3925(5) 0.8736(5) 0.0188(14) Uani 1 1 d . . . . .
C7 C 0.7729(3) 0.4835(5) 0.9012(5) 0.0202(14) Uani 1 1 d . . . . .
H7 H 0.7579 0.4890 0.9710 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6676(3) 0.7067(5) 0.7945(6) 0.0198(16) Uani 1 1 d . . . . .
C9 C 0.6155(3) 0.8016(5) 0.8212(6) 0.0183(15) Uani 1 1 d . . . . .
C10 C 0.6121(3) 0.8561(5) 0.9188(6) 0.0199(15) Uani 1 1 d . . . . .
C11 C 0.5651(3) 0.9505(5) 0.9364(6) 0.0274(16) Uani 1 1 d . . . . .
H11 H 0.5639 0.9894 1.0015 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5196(3) 0.9878(6) 0.8579(6) 0.0308(19) Uani 1 1 d . . . . .
H12 H 0.4872 1.0524 0.8701 0.037 Uiso 1 1 calc R U . . .
C13 C 0.5202(3) 0.9341(5) 0.7637(6) 0.0299(17) Uani 1 1 d . . . . .
H13 H 0.4876 0.9596 0.7117 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5685(3) 0.8423(5) 0.7441(6) 0.0240(15) Uani 1 1 d . . . . .
H14 H 0.5699 0.8064 0.6778 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6615(3) 0.3827(5) 0.6009(6) 0.0186(15) Uani 1 1 d . . . . .
C16 C 0.6135(3) 0.2842(5) 0.6130(6) 0.0218(15) Uani 1 1 d . . . . .
C17 C 0.5919(3) 0.2164(5) 0.5296(5) 0.0223(15) Uani 1 1 d . . . . .
H17 H 0.5604 0.1499 0.5399 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6154(3) 0.2439(6) 0.4308(6) 0.0248(15) Uani 1 1 d . . . . .
H18 H 0.6015 0.1953 0.3741 0.030 Uiso 1 1 calc R U . . .
C19 C 0.6587(3) 0.3413(6) 0.4163(6) 0.0241(15) Uani 1 1 d . . . . .
H19 H 0.6732 0.3624 0.3485 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6824(3) 0.4115(5) 0.5004(5) 0.0172(14) Uani 1 1 d . . . . .
C21 C 0.7291(3) 0.5098(6) 0.4794(6) 0.0211(15) Uani 1 1 d . . . . .
H21 H 0.7374 0.5305 0.4094 0.025 Uiso 1 1 calc R U . . .
C22 C 0.8385(3) 0.7141(5) 0.5977(6) 0.0182(15) Uani 1 1 d . . . . .
C23 C 0.8899(3) 0.8126(5) 0.5764(6) 0.0200(15) Uani 1 1 d . . . . .
C24 C 0.8955(3) 0.8625(6) 0.4781(6) 0.0229(15) Uani 1 1 d . . . . .
C25 C 0.9404(3) 0.9608(5) 0.4606(6) 0.0258(17) Uani 1 1 d . . . . .
H25 H 0.9428 0.9964 0.3942 0.031 Uiso 1 1 calc R U . . .
C26 C 0.9811(3) 1.0060(6) 0.5397(7) 0.0300(19) Uani 1 1 d . . . . .
H26 H 1.0119 1.0728 0.5273 0.036 Uiso 1 1 calc R U . . .
C27 C 0.9781(3) 0.9560(6) 0.6376(6) 0.0296(17) Uani 1 1 d . . . . .
H27 H 1.0073 0.9869 0.6916 0.036 Uiso 1 1 calc R U . . .
C28 C 0.9319(3) 0.8609(5) 0.6549(5) 0.0221(15) Uani 1 1 d . . . . .
H28 H 0.9287 0.8275 0.7221 0.027 Uiso 1 1 calc R U . . .
N1 N 0.7468(2) 0.5560(5) 0.8375(5) 0.0130(14) Uani 1 1 d . . . . .
N2 N 0.6995(2) 0.6441(4) 0.8703(4) 0.0181(11) Uani 1 1 d D . . . .
N3 N 0.7612(3) 0.5733(5) 0.5504(5) 0.0164(14) Uani 1 1 d . . . . .
N4 N 0.8070(2) 0.6648(4) 0.5190(4) 0.0207(12) Uani 1 1 d . . . . .
O1 O 0.82819(15) 0.4379(3) 0.6899(5) 0.0176(8) Uani 1 1 d . . . . .
O2 O 0.68140(17) 0.6805(3) 0.7015(4) 0.0208(10) Uani 1 1 d . . . . .
O3 O 0.9362(2) 0.2849(4) 0.6639(3) 0.0307(12) Uani 1 1 d D . . . .
O4 O 0.6575(2) 0.8169(4) 0.9936(4) 0.0275(11) Uani 1 1 d D . . . .
O5 O 0.68095(15) 0.4387(3) 0.6873(4) 0.0181(9) Uani 1 1 d . . . . .
O6 O 0.58616(19) 0.2587(3) 0.7069(4) 0.0272(10) Uani 1 1 d D . . . .
O7 O 0.8579(2) 0.8197(4) 0.3963(4) 0.0283(11) Uani 1 1 d D . . . .
O8 O 0.82644(16) 0.6802(3) 0.6913(4) 0.0206(9) Uani 1 1 d . . . . .
Co1 Co 0.75462(4) 0.55603(5) 0.69206(11) 0.01651(18) Uani 1 1 d . . . . .
C1S C 0.7300(3) 0.6129(5) 0.1897(7) 0.0344(14) Uani 1 1 d . . . . .
H1S1 H 0.6978 0.6038 0.2500 0.041 Uiso 1 1 calc R U . . .
H1S2 H 0.7497 0.6958 0.1901 0.041 Uiso 1 1 calc R U . . .
O1S O 0.6908(2) 0.5932(4) 0.0986(4) 0.0365(12) Uani 1 1 d . . . . .
C2S C 0.7897(3) 0.5253(5) 0.1964(6) 0.0380(15) Uani 1 1 d . . . . .
H2S1 H 0.7702 0.4434 0.1937 0.057 Uiso 1 1 calc R U . . .
H2S2 H 0.8158 0.5368 0.2613 0.057 Uiso 1 1 calc R U . . .
H2S3 H 0.8229 0.5375 0.1386 0.057 Uiso 1 1 calc R U . . .
H7O H 0.825(3) 0.771(5) 0.421(6) 0.057 Uiso 1 1 d D U . . .
H4O H 0.653(4) 0.856(6) 1.052(3) 0.057 Uiso 1 1 d D U . . .
H3O H 0.9824(17) 0.265(6) 0.670(6) 0.057 Uiso 1 1 d D U . . .
H2N H 0.692(3) 0.666(6) 0.935(3) 0.046 Uiso 1 1 d D U . . .
H6O H 0.605(3) 0.299(6) 0.759(4) 0.057 Uiso 1 1 d D U . . .
H1S H 0.645(4) 0.623(6) 0.108(6) 0.057 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.331(8) . ?
C1 C6 1.403(9) . ?
C1 C2 1.416(7) . ?
C2 C3 1.367(9) . ?
C2 O3 1.371(8) . ?
C3 C4 1.390(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.434(8) . ?
C7 N1 1.253(9) . ?
C7 H7 0.9500 . ?
C8 O2 1.270(9) . ?
C8 N2 1.342(8) . ?
C8 C9 1.471(8) . ?
C9 C14 1.403(9) . ?
C9 C10 1.407(10) . ?
C10 O4 1.357(8) . ?
C10 C11 1.383(8) . ?
C11 C12 1.386(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.362(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O5 1.333(9) . ?
C15 C20 1.399(9) . ?
C15 C16 1.418(8) . ?
C16 O6 1.352(8) . ?
C16 C17 1.379(9) . ?
C17 C18 1.390(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.359(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.419(8) . ?
C21 N3 1.305(9) . ?
C21 H21 0.9500 . ?
C22 O8 1.293(9) . ?
C22 N4 1.299(8) . ?
C22 C23 1.476(8) . ?
C23 C28 1.392(9) . ?
C23 C24 1.396(10) . ?
C24 O7 1.357(8) . ?
C24 C25 1.391(8) . ?
C25 C26 1.370(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(8) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 N2 1.382(6) . ?
N1 Co1 1.895(7) . ?
N2 H2N 0.88(3) . ?
N3 N4 1.386(7) . ?
N3 Co1 1.855(7) . ?
O1 Co1 1.892(3) . ?
O2 Co1 1.941(3) . ?
O3 H3O 0.89(3) . ?
O4 H4O 0.88(3) . ?
O5 Co1 1.888(3) . ?
O6 H6O 0.88(3) . ?
O7 H7O 0.87(3) . ?
O8 Co1 1.916(3) . ?
C1S O1S 1.407(9) . ?
C1S C2S 1.476(6) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
O1S H1S 0.92(7) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 126.4(5) . . ?
O1 C1 C2 117.7(6) . . ?
C6 C1 C2 115.9(6) . . ?
C3 C2 O3 121.4(5) . . ?
C3 C2 C1 122.2(6) . . ?
O3 C2 C1 116.4(6) . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.0(5) . . ?
C1 C6 C7 122.8(6) . . ?
C5 C6 C7 116.2(6) . . ?
N1 C7 C6 122.9(7) . . ?
N1 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
O2 C8 N2 119.4(5) . . ?
O2 C8 C9 121.4(6) . . ?
N2 C8 C9 119.1(7) . . ?
C14 C9 C10 118.5(5) . . ?
C14 C9 C8 118.0(6) . . ?
C10 C9 C8 123.4(6) . . ?
O4 C10 C11 121.0(6) . . ?
O4 C10 C9 118.7(5) . . ?
C11 C10 C9 120.2(6) . . ?
C10 C11 C12 119.2(7) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 121.7(6) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 120.6(7) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O5 C15 C20 127.1(5) . . ?
O5 C15 C16 115.9(6) . . ?
C20 C15 C16 117.0(6) . . ?
O6 C16 C17 119.0(5) . . ?
O6 C16 C15 119.8(6) . . ?
C17 C16 C15 121.1(6) . . ?
C16 C17 C18 120.9(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.3(6) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.0(7) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 120.6(6) . . ?
C15 C20 C21 121.7(6) . . ?
C19 C20 C21 117.7(6) . . ?
N3 C21 C20 123.9(7) . . ?
N3 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
O8 C22 N4 122.7(5) . . ?
O8 C22 C23 120.3(6) . . ?
N4 C22 C23 117.0(6) . . ?
C28 C23 C24 118.4(5) . . ?
C28 C23 C22 120.6(6) . . ?
C24 C23 C22 121.0(6) . . ?
O7 C24 C25 116.9(7) . . ?
O7 C24 C23 122.6(6) . . ?
C25 C24 C23 120.4(6) . . ?
C26 C25 C24 119.6(7) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 121.3(6) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 118.7(6) . . ?
C28 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C27 C28 C23 121.6(7) . . ?
C27 C28 H28 119.2 . . ?
C23 C28 H28 119.2 . . ?
C7 N1 N2 119.8(7) . . ?
C7 N1 Co1 129.1(5) . . ?
N2 N1 Co1 110.9(4) . . ?
C8 N2 N1 114.8(6) . . ?
C8 N2 H2N 119(4) . . ?
N1 N2 H2N 126(4) . . ?
C21 N3 N4 117.9(6) . . ?
C21 N3 Co1 128.0(5) . . ?
N4 N3 Co1 114.1(4) . . ?
C22 N4 N3 110.7(6) . . ?
C1 O1 Co1 123.7(4) . . ?
C8 O2 Co1 111.4(4) . . ?
C2 O3 H3O 108(5) . . ?
C10 O4 H4O 113(5) . . ?
C15 O5 Co1 123.1(4) . . ?
C16 O6 H6O 116(5) . . ?
C24 O7 H7O 106(5) . . ?
C22 O8 Co1 109.6(4) . . ?
N3 Co1 O5 94.9(2) . . ?
N3 Co1 O1 90.6(2) . . ?
O5 Co1 O1 92.34(11) . . ?
N3 Co1 N1 174.03(17) . . ?
O5 Co1 N1 88.7(2) . . ?
O1 Co1 N1 94.0(2) . . ?
N3 Co1 O8 82.8(2) . . ?
O5 Co1 O8 176.8(2) . . ?
O1 Co1 O8 89.97(14) . . ?
N1 Co1 O8 93.3(2) . . ?
N3 Co1 O2 92.0(2) . . ?
O5 Co1 O2 89.38(14) . . ?
O1 Co1 O2 176.8(2) . . ?
N1 Co1 O2 83.3(2) . . ?
O8 Co1 O2 88.42(12) . . ?
O1S C1S C2S 109.5(6) . . ?
O1S C1S H1S1 109.8 . . ?
C2S C1S H1S1 109.8 . . ?
O1S C1S H1S2 109.8 . . ?
C2S C1S H1S2 109.8 . . ?
H1S1 C1S H1S2 108.2 . . ?
C1S O1S H1S 108(5) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?

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
O1 C1 C2 C3 -175.9(5) . . . . ?
C6 C1 C2 C3 4.8(8) . . . . ?
O1 C1 C2 O3 3.8(7) . . . . ?
C6 C1 C2 O3 -175.5(5) . . . . ?
O3 C2 C3 C4 177.9(5) . . . . ?
C1 C2 C3 C4 -2.4(9) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
O1 C1 C6 C5 176.4(5) . . . . ?
C2 C1 C6 C5 -4.4(8) . . . . ?
O1 C1 C6 C7 -5.8(8) . . . . ?
C2 C1 C6 C7 173.4(5) . . . . ?
C4 C5 C6 C1 1.7(9) . . . . ?
C4 C5 C6 C7 -176.3(6) . . . . ?
C1 C6 C7 N1 1.0(9) . . . . ?
C5 C6 C7 N1 179.0(6) . . . . ?
O2 C8 C9 C14 15.4(8) . . . . ?
N2 C8 C9 C14 -162.6(5) . . . . ?
O2 C8 C9 C10 -162.5(6) . . . . ?
N2 C8 C9 C10 19.6(9) . . . . ?
C14 C9 C10 O4 180.0(5) . . . . ?
C8 C9 C10 O4 -2.2(9) . . . . ?
C14 C9 C10 C11 -2.3(9) . . . . ?
C8 C9 C10 C11 175.5(5) . . . . ?
O4 C10 C11 C12 180.0(6) . . . . ?
C9 C10 C11 C12 2.3(9) . . . . ?
C10 C11 C12 C13 -0.2(10) . . . . ?
C11 C12 C13 C14 -1.8(10) . . . . ?
C12 C13 C14 C9 1.8(9) . . . . ?
C10 C9 C14 C13 0.2(9) . . . . ?
C8 C9 C14 C13 -177.7(5) . . . . ?
O5 C15 C16 O6 5.2(7) . . . . ?
C20 C15 C16 O6 -174.0(5) . . . . ?
O5 C15 C16 C17 -177.4(5) . . . . ?
C20 C15 C16 C17 3.4(8) . . . . ?
O6 C16 C17 C18 176.3(5) . . . . ?
C15 C16 C17 C18 -1.2(8) . . . . ?
C16 C17 C18 C19 -1.9(9) . . . . ?
C17 C18 C19 C20 2.7(9) . . . . ?
O5 C15 C20 C19 178.3(5) . . . . ?
C16 C15 C20 C19 -2.6(8) . . . . ?
O5 C15 C20 C21 -0.4(9) . . . . ?
C16 C15 C20 C21 178.7(5) . . . . ?
C18 C19 C20 C15 -0.4(9) . . . . ?
C18 C19 C20 C21 178.3(6) . . . . ?
C15 C20 C21 N3 6.6(9) . . . . ?
C19 C20 C21 N3 -172.1(6) . . . . ?
O8 C22 C23 C28 7.4(8) . . . . ?
N4 C22 C23 C28 -172.7(5) . . . . ?
O8 C22 C23 C24 -170.3(5) . . . . ?
N4 C22 C23 C24 9.7(8) . . . . ?
C28 C23 C24 O7 178.5(5) . . . . ?
C22 C23 C24 O7 -3.8(9) . . . . ?
C28 C23 C24 C25 -2.2(8) . . . . ?
C22 C23 C24 C25 175.5(5) . . . . ?
O7 C24 C25 C26 -178.4(5) . . . . ?
C23 C24 C25 C26 2.3(9) . . . . ?
C24 C25 C26 C27 -0.5(9) . . . . ?
C25 C26 C27 C28 -1.4(9) . . . . ?
C26 C27 C28 C23 1.5(8) . . . . ?
C24 C23 C28 C27 0.3(8) . . . . ?
C22 C23 C28 C27 -177.4(5) . . . . ?
C6 C7 N1 N2 -177.7(5) . . . . ?
C6 C7 N1 Co1 9.4(9) . . . . ?
O2 C8 N2 N1 1.3(7) . . . . ?
C9 C8 N2 N1 179.2(5) . . . . ?
C7 N1 N2 C8 -171.7(5) . . . . ?
Co1 N1 N2 C8 2.4(6) . . . . ?
C20 C21 N3 N4 178.2(5) . . . . ?
C20 C21 N3 Co1 -0.9(9) . . . . ?
O8 C22 N4 N3 -0.7(8) . . . . ?
C23 C22 N4 N3 179.3(4) . . . . ?
C21 N3 N4 C22 -175.6(5) . . . . ?
Co1 N3 N4 C22 3.6(6) . . . . ?
C6 C1 O1 Co1 -0.1(7) . . . . ?
C2 C1 O1 Co1 -179.3(3) . . . . ?
N2 C8 O2 Co1 -4.1(6) . . . . ?
C9 C8 O2 Co1 178.0(4) . . . . ?
C20 C15 O5 Co1 -10.4(7) . . . . ?
C16 C15 O5 Co1 170.5(3) . . . . ?
N4 C22 O8 Co1 -2.3(7) . . . . ?
C23 C22 O8 Co1 177.6(4) . . . . ?
C21 N3 Co1 O5 -7.0(6) . . . . ?
N4 N3 Co1 O5 173.9(4) . . . . ?
C21 N3 Co1 O1 85.4(6) . . . . ?
N4 N3 Co1 O1 -93.7(4) . . . . ?
C21 N3 Co1 O8 175.3(6) . . . . ?
N4 N3 Co1 O8 -3.8(4) . . . . ?
C21 N3 Co1 O2 -96.6(6) . . . . ?
N4 N3 Co1 O2 84.3(4) . . . . ?
C15 O5 Co1 N3 12.0(4) . . . . ?
C15 O5 Co1 O1 -78.7(4) . . . . ?
C15 O5 Co1 N1 -172.7(4) . . . . ?
C15 O5 Co1 O2 104.0(4) . . . . ?
C1 O1 Co1 N3 -177.0(4) . . . . ?
C1 O1 Co1 O5 -82.0(4) . . . . ?
C1 O1 Co1 N1 6.8(4) . . . . ?
C1 O1 Co1 O8 100.2(4) . . . . ?
C7 N1 Co1 O5 80.4(5) . . . . ?
N2 N1 Co1 O5 -93.0(3) . . . . ?
C7 N1 Co1 O1 -11.9(5) . . . . ?
N2 N1 Co1 O1 174.7(3) . . . . ?
C7 N1 Co1 O8 -102.1(5) . . . . ?
N2 N1 Co1 O8 84.5(3) . . . . ?
C7 N1 Co1 O2 169.9(5) . . . . ?
N2 N1 Co1 O2 -3.5(3) . . . . ?

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
C7 H7 O1S 0.95 2.37 3.221(8) 148.3 1_556
O7 H7O N4 0.87(3) 1.77(5) 2.529(6) 144(7) .
O4 H4O O1 0.88(3) 2.04(3) 2.896(8) 164(6) 3_655
O4 H4O O3 0.88(3) 2.33(6) 2.834(6) 116(5) 3_655
O3 H3O O6 0.89(3) 2.00(3) 2.875(5) 169(7) 4
N2 H2N O4 0.88(3) 1.95(5) 2.619(7) 131(6) .
N2 H2N O1S 0.88(3) 2.27(5) 3.025(7) 143(6) 1_556
O6 H6O O7 0.88(3) 1.93(4) 2.755(7) 156(7) 3_645
O1S H1S O3 0.92(7) 2.46(7) 3.284(6) 150(6) 3_654
C7 H7 O1S 0.95 2.37 3.221(8) 148.3 1_556
O7 H7O N4 0.87(3) 1.77(5) 2.529(6) 144(7) .
O4 H4O O1 0.88(3) 2.04(3) 2.896(8) 164(6) 3_655
O4 H4O O3 0.88(3) 2.33(6) 2.834(6) 116(5) 3_655
O3 H3O O6 0.89(3) 2.00(3) 2.875(5) 169(7) 4
N2 H2N O4 0.88(3) 1.95(5) 2.619(7) 131(6) .
N2 H2N O1S 0.88(3) 2.27(5) 3.025(7) 143(6) 1_556
O6 H6O O7 0.88(3) 1.93(4) 2.755(7) 156(7) 3_645
O1S H1S O3 0.92(7) 2.46(7) 3.284(6) 150(6) 3_654

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_H2L2
_database_code_depnum_ccdc_archive 'CCDC 1440206'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-01-08 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         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26

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

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

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

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

_cell_length_a                   8.9865(9)
_cell_length_b                   9.5514(7)
_cell_length_c                   14.1428(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.2030(10)
_cell_angle_gamma                90
_cell_volume                     1213.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2941
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.31

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7359
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             2121
_reflns_number_gt                1598
_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+0.0857P] 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         2121
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0558(2) 0.86904(16) 0.15251(12) 0.0203(4) Uani 1 1 d . . . . .
C2 C -0.1283(2) 0.95536(17) 0.21672(11) 0.0204(4) Uani 1 1 d . . . . .
C3 C -0.2389(2) 1.04599(18) 0.18737(12) 0.0235(4) Uani 1 1 d . . . . .
H3 H -0.2868 1.1050 0.2320 0.028 Uiso 1 1 calc R U . . .
C4 C -0.2805(2) 1.05111(17) 0.09223(12) 0.0242(4) Uani 1 1 d . . . . .
H4 H -0.3568 1.1132 0.0720 0.029 Uiso 1 1 calc R U . . .
C5 C -0.2105(2) 0.96585(17) 0.02807(12) 0.0231(4) Uani 1 1 d . . . . .
H5 H -0.2384 0.9700 -0.0367 0.028 Uiso 1 1 calc R U . . .
C6 C -0.0983(2) 0.87262(16) 0.05667(12) 0.0203(4) Uani 1 1 d . . . . .
C7 C -0.0266(2) 0.78340(17) -0.01303(12) 0.0224(4) Uani 1 1 d . . . . .
H7 H -0.0523 0.7914 -0.0780 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2434(2) 0.52164(17) -0.02831(12) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.3152(2) 0.43501(17) -0.10114(12) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.4157(2) 0.32931(17) -0.07210(12) 0.0214(4) Uani 1 1 d . . . . .
C11 C 0.4813(2) 0.24254(18) -0.13865(13) 0.0261(4) Uani 1 1 d . . . . .
H11 H 0.5485 0.1715 -0.1189 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4494(2) 0.25910(19) -0.23319(12) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.4934 0.1982 -0.2782 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3533(2) 0.36430(19) -0.26340(12) 0.0276(4) Uani 1 1 d . . . . .
H13 H 0.3335 0.3763 -0.3289 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2873(2) 0.45058(18) -0.19856(12) 0.0236(4) Uani 1 1 d . . . . .
H14 H 0.2217 0.5221 -0.2197 0.028 Uiso 1 1 calc R U . . .
N1 N 0.07140(17) 0.69385(14) 0.01368(10) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.13857(17) 0.61422(14) -0.05544(10) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.1137 0.6236 -0.1153 0.026 Uiso 1 1 calc R U . . .
O1 O 0.05388(15) 0.78598(13) 0.18744(8) 0.0287(4) Uani 1 1 d . . . . .
H1 H 0.0872 0.7349 0.1440 0.043 Uiso 1 1 calc R U . . .
O2 O 0.27842(15) 0.50957(13) 0.05753(8) 0.0260(3) Uani 1 1 d . . . . .
O3 O -0.08319(15) 0.94365(13) 0.30937(8) 0.0280(3) Uani 1 1 d . . . . .
H3A H -0.1468 0.9809 0.3447 0.042 Uiso 1 1 calc R U . . .
O4 O 0.45096(16) 0.30643(13) 0.02000(8) 0.0298(4) Uani 1 1 d . . . . .
H4A H 0.4075 0.3657 0.0540 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
C1 O1 1.357(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.407(2) . ?
C2 O3 1.375(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(2) . ?
C7 N1 1.284(2) . ?
C7 H7 0.9500 . ?
C8 O2 1.258(2) . ?
C8 N2 1.347(2) . ?
C8 C9 1.472(2) . ?
C9 C14 1.407(2) . ?
C9 C10 1.414(2) . ?
C10 O4 1.357(2) . ?
C10 C11 1.387(3) . ?
C11 C12 1.376(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N1 N2 1.379(2) . ?
N2 H2 0.8800 . ?
O1 H1 0.8400 . ?
O3 H3A 0.8400 . ?
O4 H4A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 116.78(15) . . ?
O1 C1 C6 123.99(16) . . ?
C2 C1 C6 119.23(16) . . ?
O3 C2 C3 123.17(15) . . ?
O3 C2 C1 115.90(15) . . ?
C3 C2 C1 120.93(15) . . ?
C2 C3 C4 120.11(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.62(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.02(16) . . ?
C5 C6 C7 119.69(16) . . ?
C1 C6 C7 121.28(16) . . ?
N1 C7 C6 119.71(16) . . ?
N1 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 N2 120.49(16) . . ?
O2 C8 C9 120.98(16) . . ?
N2 C8 C9 118.54(15) . . ?
C14 C9 C10 118.10(16) . . ?
C14 C9 C8 123.27(16) . . ?
C10 C9 C8 118.63(15) . . ?
O4 C10 C11 117.16(16) . . ?
O4 C10 C9 122.70(16) . . ?
C11 C10 C9 120.13(16) . . ?
C12 C11 C10 120.21(17) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.57(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.92(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 121.05(17) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C7 N1 N2 117.42(14) . . ?
C8 N2 N1 117.88(14) . . ?
C8 N2 H2 121.1 . . ?
N1 N2 H2 121.1 . . ?
C1 O1 H1 109.5 . . ?
C2 O3 H3A 109.5 . . ?
C10 O4 H4A 109.5 . . ?

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
N2 H2 O3 0.88 2.16 2.8117(19) 130.5 4_575
O1 H1 N1 0.84 1.89 2.6155(18) 143.9 .
O3 H3A O2 0.84 1.84 2.6536(18) 161.7 2
O4 H4A O2 0.84 1.80 2.5409(18) 146.3 .

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057

