# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cmpd_5
_database_code_depnum_ccdc_archive 'CCDC 1588548'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_cmpd_5              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.919 Why?
RESPONSE: Data of one domain of a twinned crystal was used
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C76 H70 Fe4 N10 O21, 2(N O3), 2(C2 H3 N)'
_chemical_formula_sum            'C80 H76 Fe4 N14 O27'
_chemical_formula_weight         1888.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9096(6)
_cell_length_b                   12.5269(7)
_cell_length_c                   17.0352(10)
_cell_angle_alpha                83.424(4)
_cell_angle_beta                 81.197(5)
_cell_angle_gamma                69.805(4)
_cell_volume                     2351.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4782
_cell_measurement_theta_min      3.7681
_cell_measurement_theta_max      64.6614

_exptl_crystal_description       block
_exptl_crystal_colour            'black / dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             974
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    5.522
_shelx_estimated_absorpt_T_min   0.124
_shelx_estimated_absorpt_T_max   0.271
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_T_max  0.27
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'BRUKER APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10875
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.631
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_full        67.071
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             7709
_reflns_number_gt                4968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       APEX2
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'PLATON/SQUEEZE (Spek, 2015)'
_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)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7709
_refine_ls_number_parameters     727
_refine_ls_number_restraints     895
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.927
_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
Fe1 Fe 0.12078(6) 0.38655(6) 0.53954(4) 0.0217(2) Uani 1 1 d . . . . .
Fe2 Fe 0.13768(7) 0.41122(6) 0.73360(4) 0.0284(2) Uani 1 1 d . . . . .
O1 O 0.000000 0.500000 0.500000 0.0247(10) Uani 1 2 d S . P . .
N1 N 0.0207(3) 0.2756(3) 0.5338(2) 0.0248(9) Uani 1 1 d . . . . .
C2 C 0.0055(4) 0.2465(4) 0.4648(3) 0.0277(11) Uani 1 1 d . . . . .
C3 C -0.0691(4) 0.1815(4) 0.4613(3) 0.0332(12) Uani 1 1 d . . . . .
H3 H -0.079361 0.160883 0.411571 0.040 Uiso 1 1 calc R U . . .
C4 C -0.1262(5) 0.1488(4) 0.5301(4) 0.0382(13) Uani 1 1 d . . . . .
H4 H -0.174040 0.102271 0.528280 0.046 Uiso 1 1 calc R U . . .
C5 C -0.1160(5) 0.1824(4) 0.6042(3) 0.0360(13) Uani 1 1 d . . . . .
C6 C -0.1770(6) 0.1592(6) 0.6785(4) 0.0495(16) Uani 1 1 d . . . . .
H6 H -0.225299 0.111793 0.682492 0.059 Uiso 1 1 calc R U . . .
C7 C -0.1661(6) 0.2050(5) 0.7440(4) 0.0504(16) Uani 1 1 d . . . . .
H7 H -0.209719 0.190891 0.793261 0.060 Uiso 1 1 calc R U . . .
C8 C -0.0927(5) 0.2728(5) 0.7420(3) 0.0429(14) Uani 1 1 d . . . . .
H01F H -0.090379 0.305667 0.789031 0.052 Uiso 1 1 calc R U . . .
O9 O 0.0490(3) 0.3544(3) 0.6623(2) 0.0293(8) Uani 1 1 d . . . . .
C9 C -0.0244(4) 0.2918(4) 0.6726(3) 0.0294(12) Uani 1 1 d . . . . .
C10 C -0.0387(4) 0.2472(4) 0.6023(3) 0.0284(11) Uani 1 1 d . . . . .
C11 C 0.0642(5) 0.2970(4) 0.3932(3) 0.0311(12) Uani 1 1 d . . . . .
H11A H 0.011120 0.377981 0.384949 0.037 Uiso 1 1 calc R U . . .
O11 O 0.0708(3) 0.2440(3) 0.3243(2) 0.0389(9) Uani 1 1 d . . . . .
H11 H 0.054205 0.293463 0.286261 0.058 Uiso 1 1 calc R U . . .
N22 N 0.2469(3) 0.4582(3) 0.4676(2) 0.0235(9) Uani 1 1 d . . . . .
C23 C 0.2737(4) 0.4530(4) 0.3898(3) 0.0220(10) Uani 1 1 d . . . . .
C24 C 0.3406(5) 0.5149(5) 0.3448(3) 0.0387(13) Uani 1 1 d . . . . .
H24 H 0.357611 0.509999 0.288780 0.046 Uiso 1 1 calc R U . . .
C25 C 0.3819(5) 0.5830(5) 0.3816(3) 0.0385(14) Uani 1 1 d . . . . .
H25 H 0.428992 0.624535 0.351364 0.046 Uiso 1 1 calc R U . . .
C26 C 0.3545(5) 0.5913(4) 0.4646(3) 0.0307(12) Uani 1 1 d . . . . .
C27 C 0.3918(5) 0.6586(4) 0.5091(3) 0.0360(13) Uani 1 1 d . . . . .
H27 H 0.440702 0.701380 0.483343 0.043 Uiso 1 1 calc R U . . .
C28 C 0.3576(5) 0.6623(4) 0.5889(4) 0.0394(14) Uani 1 1 d . . . . .
H28 H 0.381916 0.709264 0.617952 0.047 Uiso 1 1 calc R U . . .
C29 C 0.2866(5) 0.5981(4) 0.6302(3) 0.0341(12) Uani 1 1 d . . . . .
H29 H 0.263766 0.602367 0.685996 0.041 Uiso 1 1 calc R U . . .
C30 C 0.2512(4) 0.5296(4) 0.5887(3) 0.0269(11) Uani 1 1 d . . . . .
O30 O 0.1817(3) 0.4659(3) 0.62048(19) 0.0281(8) Uani 1 1 d . . . . .
C31 C 0.2864(4) 0.5264(4) 0.5061(3) 0.0228(10) Uani 1 1 d . . . . .
C32 C 0.2289(5) 0.3748(4) 0.3517(3) 0.0306(12) Uani 1 1 d . . . . .
H32 H 0.164794 0.421178 0.318010 0.037 Uiso 1 1 calc R U . . .
N33 N 0.1804(3) 0.3004(3) 0.4122(2) 0.0233(9) Uani 1 1 d . . . . .
C34 C 0.2836(4) 0.1880(4) 0.4170(3) 0.0288(11) Uani 1 1 d . . . . .
C35 C 0.3542(5) 0.1853(4) 0.3343(3) 0.0387(13) Uani 1 1 d . . . . .
H35A H 0.441711 0.148850 0.337547 0.046 Uiso 1 1 calc R U . . .
H35B H 0.329256 0.141495 0.299558 0.046 Uiso 1 1 calc R U . . .
O36 O 0.3281(4) 0.3019(3) 0.3029(2) 0.0513(11) Uani 1 1 d . . . . .
C37 C 0.3567(4) 0.1980(4) 0.4808(3) 0.0295(12) Uani 1 1 d . . . . .
H37A H 0.416612 0.122641 0.493037 0.035 Uiso 1 1 calc R U . . .
H37B H 0.400755 0.251610 0.460433 0.035 Uiso 1 1 calc R U . . .
O38 O 0.2781(3) 0.2383(3) 0.55193(19) 0.0289(8) Uani 1 1 d . . . . .
H38 H 0.264381 0.182996 0.579381 0.043 Uiso 1 1 d R U . . .
C39 C 0.2420(5) 0.0851(4) 0.4369(3) 0.0341(13) Uani 1 1 d . . . . .
H39A H 0.192604 0.091426 0.489583 0.041 Uiso 1 1 calc R U . . .
H39B H 0.191968 0.081494 0.396544 0.041 Uiso 1 1 calc R U . . .
O40 O 0.3460(3) -0.0158(3) 0.4379(2) 0.0417(10) Uani 1 1 d . . . . .
H40 H 0.353451 -0.042533 0.485051 0.062 Uiso 1 1 calc R U . . .
C101 C 0.3488(10) 0.3262(9) 0.8158(7) 0.042(3) Uani 0.549(11) 1 d . . P A 1
H10A H 0.313130 0.321724 0.872020 0.050 Uiso 0.549(11) 1 calc R U P A 1
H10B H 0.428361 0.335137 0.815115 0.050 Uiso 0.549(11) 1 calc R U P A 1
O101 O 0.4544(15) 0.1008(11) 0.6698(9) 0.049(3) Uani 0.549(11) 1 d . . P A 1
H101 H 0.518387 0.077145 0.638700 0.074 Uiso 0.549(11) 1 calc R U P A 1
C102 C 0.4528(9) 0.1980(11) 0.7050(8) 0.031(2) Uani 0.549(11) 1 d . . P A 1
H10C H 0.430121 0.265322 0.666693 0.037 Uiso 0.549(11) 1 calc R U P A 1
H10D H 0.534340 0.186942 0.718176 0.037 Uiso 0.549(11) 1 calc R U P A 1
C103 C 0.3946(10) 0.1135(10) 0.8404(7) 0.045(3) Uani 0.549(11) 1 d . . P A 1
H10E H 0.432149 0.041839 0.812914 0.054 Uiso 0.549(11) 1 calc R U P A 1
H10F H 0.450285 0.118809 0.876216 0.054 Uiso 0.549(11) 1 calc R U P A 1
O100 O 0.2713(3) 0.4244(3) 0.7738(2) 0.0381(9) Uani 1 1 d . . . . .
C201 C 0.3732(11) 0.3451(11) 0.7554(10) 0.044(3) Uani 0.451(11) 1 d . . P A 2
H20A H 0.435599 0.354799 0.783458 0.053 Uiso 0.451(11) 1 calc R U P A 2
H20B H 0.398087 0.352892 0.697453 0.053 Uiso 0.451(11) 1 calc R U P A 2
O201 O 0.4620(18) 0.1507(17) 0.6515(11) 0.078(7) Uani 0.451(11) 1 d . . P A 2
H201 H 0.519651 0.100730 0.627520 0.117 Uiso 0.451(11) 1 calc R U P A 2
C202 C 0.4705(14) 0.1339(17) 0.7345(9) 0.056(4) Uani 0.451(11) 1 d . . P A 2
H20C H 0.546242 0.142579 0.745051 0.067 Uiso 0.451(11) 1 calc R U P A 2
H20D H 0.472238 0.055694 0.753459 0.067 Uiso 0.451(11) 1 calc R U P A 2
C203 C 0.3631(12) 0.1930(12) 0.8671(8) 0.046(3) Uani 0.451(11) 1 d . . P A 2
H20E H 0.326434 0.263341 0.896235 0.055 Uiso 0.451(11) 1 calc R U P A 2
H20F H 0.445069 0.152162 0.881979 0.055 Uiso 0.451(11) 1 calc R U P A 2
O309 O 0.0120(3) 0.5587(3) 0.7637(2) 0.0414(10) Uani 1 1 d . . . . .
C311 C 0.1916(5) 0.1703(5) 0.8346(3) 0.0389(13) Uani 1 1 d . . . . .
H311 H 0.156499 0.114143 0.820439 0.047 Uiso 0.578(14) 1 calc R U P B 1
H411 H 0.164636 0.109930 0.817917 0.047 Uiso 0.422(14) 1 calc R U P B 2
N312 N 0.2445(4) 0.2228(4) 0.7617(2) 0.0339(10) Uani 1 1 d . . . . .
H312 H 0.253756 0.177798 0.714879 0.041 Uiso 1 1 calc R U . . .
C313 C 0.3650(5) 0.2188(5) 0.7788(3) 0.0391(12) Uani 1 1 d . . . . .
O315 O 0.2845(4) 0.1171(3) 0.8828(2) 0.0533(11) Uani 1 1 d . . . . .
N301 N 0.0627(17) 0.3711(10) 0.8451(11) 0.031(2) Uani 0.578(14) 1 d D U P B 1
C302 C 0.0924(18) 0.2688(11) 0.8821(10) 0.034(2) Uani 0.578(14) 1 d D U P B 1
C303 C 0.0352(13) 0.2502(10) 0.9588(8) 0.038(2) Uani 0.578(14) 1 d D U P B 1
H303 H 0.056256 0.175682 0.984407 0.046 Uiso 0.578(14) 1 calc R U P B 1
C304 C -0.0498(11) 0.3384(10) 0.9959(7) 0.042(2) Uani 0.578(14) 1 d D U P B 1
H304 H -0.089731 0.325612 1.047014 0.050 Uiso 0.578(14) 1 calc R U P B 1
C305 C -0.0789(10) 0.4498(10) 0.9582(6) 0.037(2) Uani 0.578(14) 1 d D U P B 1
C306 C -0.1637(10) 0.5517(10) 0.9907(6) 0.044(2) Uani 0.578(14) 1 d D U P B 1
H306 H -0.203605 0.548887 1.043222 0.052 Uiso 0.578(14) 1 calc R U P B 1
C307 C -0.1870(11) 0.6528(10) 0.9458(6) 0.044(2) Uani 0.578(14) 1 d D U P B 1
H307 H -0.245797 0.719088 0.967245 0.053 Uiso 0.578(14) 1 calc R U P B 1
C308 C -0.1266(11) 0.6621(10) 0.8689(6) 0.039(2) Uani 0.578(14) 1 d D U P B 1
H308 H -0.143588 0.734181 0.839856 0.047 Uiso 0.578(14) 1 calc R U P B 1
C309 C -0.0430(11) 0.5671(9) 0.8356(7) 0.032(2) Uani 0.578(14) 1 d D U P B 1
C310 C -0.0213(11) 0.4618(9) 0.8810(7) 0.033(2) Uani 0.578(14) 1 d D U P B 1
N401 N 0.057(2) 0.3534(14) 0.8449(14) 0.030(3) Uani 0.422(14) 1 d D U P B 2
C402 C 0.091(2) 0.2484(15) 0.8776(14) 0.034(3) Uani 0.422(14) 1 d D U P B 2
C403 C 0.0314(17) 0.2198(14) 0.9511(11) 0.036(3) Uani 0.422(14) 1 d D U P B 2
H403 H 0.056770 0.144009 0.974411 0.043 Uiso 0.422(14) 1 calc R U P B 2
C404 C -0.0633(15) 0.3023(13) 0.9879(10) 0.039(3) Uani 0.422(14) 1 d D U P B 2
H404 H -0.105459 0.283352 1.036449 0.047 Uiso 0.422(14) 1 calc R U P B 2
C405 C -0.0992(13) 0.4160(12) 0.9544(9) 0.038(2) Uani 0.422(14) 1 d D U P B 2
C406 C -0.1944(14) 0.5132(13) 0.9855(8) 0.042(2) Uani 0.422(14) 1 d D U P B 2
H406 H -0.238151 0.506661 1.036338 0.050 Uiso 0.422(14) 1 calc R U P B 2
C407 C -0.2216(15) 0.6142(13) 0.9420(8) 0.044(3) Uani 0.422(14) 1 d D U P B 2
H407 H -0.286921 0.676289 0.963297 0.053 Uiso 0.422(14) 1 calc R U P B 2
C408 C -0.1606(15) 0.6337(13) 0.8680(8) 0.040(3) Uani 0.422(14) 1 d D U P B 2
H408 H -0.184771 0.706318 0.839739 0.048 Uiso 0.422(14) 1 calc R U P B 2
C409 C -0.0638(15) 0.5443(12) 0.8367(10) 0.032(3) Uani 0.422(14) 1 d D U P B 2
C410 C -0.0369(15) 0.4370(12) 0.8799(9) 0.031(2) Uani 0.422(14) 1 d D U P B 2
N501 N -0.0670(14) 0.0481(11) 0.1013(7) 0.093(4) Uani 0.662(14) 1 d D U P C 1
C502 C -0.0679(16) 0.0792(13) 0.1637(8) 0.082(3) Uani 0.662(14) 1 d D U P C 1
C503 C -0.044(2) 0.0938(15) 0.2419(8) 0.083(4) Uani 0.662(14) 1 d D U P C 1
H50A H -0.058976 0.033638 0.279629 0.125 Uiso 0.662(14) 1 calc R U P C 1
H50B H -0.097042 0.168410 0.259347 0.125 Uiso 0.662(14) 1 calc R U P C 1
H50C H 0.040290 0.089196 0.239502 0.125 Uiso 0.662(14) 1 calc R U P C 1
N601 N 0.035(3) 0.003(2) 0.1015(14) 0.102(5) Uani 0.338(14) 1 d D U P C 2
C602 C -0.001(3) 0.052(3) 0.1604(15) 0.087(4) Uani 0.338(14) 1 d D U P C 2
C603 C -0.057(4) 0.129(3) 0.2239(18) 0.083(6) Uani 0.338(14) 1 d D U P C 2
H60A H -0.116686 0.198251 0.203045 0.124 Uiso 0.338(14) 1 calc R U P C 2
H60B H 0.005056 0.149934 0.243958 0.124 Uiso 0.338(14) 1 calc R U P C 2
H60C H -0.096919 0.091760 0.267310 0.124 Uiso 0.338(14) 1 calc R U P C 2
N900 N 0.3007(5) -0.0268(4) 0.6535(4) 0.0521(14) Uani 1 1 d . . . . .
O901 O 0.2201(4) 0.0689(4) 0.6439(3) 0.0599(12) Uani 1 1 d . . . . .
O902 O 0.3710(4) -0.0732(4) 0.5946(3) 0.0590(12) Uani 1 1 d . . . . .
O903 O 0.3140(5) -0.0690(5) 0.7212(3) 0.0878(17) 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
Fe1 O1 1.7912(7) . ?
Fe1 O30 2.129(3) . ?
Fe1 N1 2.138(4) . ?
Fe1 O38 2.153(3) . ?
Fe1 N22 2.164(4) . ?
Fe1 O9 2.182(3) . ?
Fe1 N33 2.431(4) . ?
Fe2 O100 1.889(4) . ?
Fe2 O309 1.998(4) . ?
Fe2 O30 2.023(3) . ?
Fe2 O9 2.052(3) . ?
Fe2 N301 2.056(14) . ?
Fe2 N401 2.155(18) . ?
Fe2 N312 2.296(4) . ?
N1 C2 1.325(6) . ?
N1 C10 1.348(6) . ?
C2 C3 1.408(7) . ?
C2 C11 1.498(7) . ?
C3 C4 1.357(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(8) . ?
C5 C10 1.416(7) . ?
C6 C7 1.354(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(7) . ?
C8 H01F 0.9500 . ?
O9 C9 1.343(6) . ?
C9 C10 1.435(7) . ?
C11 O11 1.392(6) . ?
C11 N33 1.484(6) . ?
C11 H11A 1.0000 . ?
O11 H11 0.8400 . ?
N22 C23 1.317(6) . ?
N22 C31 1.372(6) . ?
C23 C24 1.389(7) . ?
C23 C32 1.509(7) . ?
C24 C25 1.367(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.408(8) . ?
C25 H25 0.9500 . ?
C26 C31 1.402(7) . ?
C26 C27 1.412(7) . ?
C27 C28 1.360(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.419(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.376(7) . ?
C29 H29 0.9500 . ?
C30 O30 1.355(6) . ?
C30 C31 1.407(7) . ?
C32 O36 1.432(6) . ?
C32 N33 1.495(6) . ?
C32 H32 1.0000 . ?
N33 C34 1.520(6) . ?
C34 C39 1.521(7) . ?
C34 C35 1.524(7) . ?
C34 C37 1.533(7) . ?
C35 O36 1.441(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C37 O38 1.438(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
O38 H38 0.8402 . ?
C39 O40 1.432(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
O40 H40 0.8400 . ?
C101 O100 1.447(11) . ?
C101 C313 1.491(12) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
O101 C102 1.410(18) . ?
O101 H101 0.8400 . ?
C102 C313 1.492(12) . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
C103 O315 1.386(12) . ?
C103 C313 1.562(12) . ?
C103 H10E 0.9900 . ?
C103 H10F 0.9900 . ?
O100 C201 1.296(13) . ?
C201 C313 1.619(15) . ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?
O201 C202 1.42(2) . ?
O201 H201 0.8400 . ?
C202 C313 1.499(15) . ?
C202 H20C 0.9900 . ?
C202 H20D 0.9900 . ?
C203 C313 1.500(14) . ?
C203 O315 1.527(16) . ?
C203 H20E 0.9900 . ?
C203 H20F 0.9900 . ?
O309 C309 1.294(12) . ?
O309 C409 1.453(16) . ?
C311 O315 1.410(7) . ?
C311 C402 1.418(18) . ?
C311 N312 1.494(7) . ?
C311 C302 1.582(14) . ?
C311 H311 1.0000 . ?
C311 H411 1.0000 . ?
N312 C313 1.491(7) . ?
N312 H312 1.0000 . ?
N301 C302 1.317(11) . ?
N301 C310 1.362(10) . ?
C302 C303 1.412(11) . ?
C303 C304 1.356(12) . ?
C303 H303 0.9500 . ?
C304 C305 1.417(12) . ?
C304 H304 0.9500 . ?
C305 C310 1.405(11) . ?
C305 C306 1.434(12) . ?
C306 C307 1.366(13) . ?
C306 H306 0.9500 . ?
C307 C308 1.408(13) . ?
C307 H307 0.9500 . ?
C308 C309 1.376(11) . ?
C308 H308 0.9500 . ?
C309 C310 1.413(11) . ?
N401 C402 1.319(13) . ?
N401 C410 1.355(13) . ?
C402 C403 1.416(14) . ?
C403 C404 1.365(15) . ?
C403 H403 0.9500 . ?
C404 C405 1.415(14) . ?
C404 H404 0.9500 . ?
C405 C410 1.415(13) . ?
C405 C406 1.435(14) . ?
C406 C407 1.354(15) . ?
C406 H406 0.9500 . ?
C407 C408 1.396(15) . ?
C407 H407 0.9500 . ?
C408 C409 1.387(14) . ?
C408 H408 0.9500 . ?
C409 C410 1.414(14) . ?
N501 C502 1.171(14) . ?
C502 C503 1.447(17) . ?
C503 H50A 0.9800 . ?
C503 H50B 0.9800 . ?
C503 H50C 0.9800 . ?
N601 C602 1.181(19) . ?
C602 C603 1.46(2) . ?
C603 H60A 0.9800 . ?
C603 H60B 0.9800 . ?
C603 H60C 0.9800 . ?
N900 O903 1.222(7) . ?
N900 O902 1.259(7) . ?
N900 O901 1.262(6) . ?

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 Fe1 O30 104.08(9) . . ?
O1 Fe1 N1 87.80(10) . . ?
O30 Fe1 N1 142.90(14) . . ?
O1 Fe1 O38 163.52(9) . . ?
O30 Fe1 O38 88.36(13) . . ?
N1 Fe1 O38 88.60(14) . . ?
O1 Fe1 N22 88.85(10) . . ?
O30 Fe1 N22 74.72(14) . . ?
N1 Fe1 N22 141.51(15) . . ?
O38 Fe1 N22 84.00(13) . . ?
O1 Fe1 O9 104.39(9) . . ?
O30 Fe1 O9 68.61(12) . . ?
N1 Fe1 O9 74.44(14) . . ?
O38 Fe1 O9 90.09(12) . . ?
N22 Fe1 O9 143.00(14) . . ?
O1 Fe1 N33 90.98(9) . . ?
O30 Fe1 N33 142.09(13) . . ?
N1 Fe1 N33 70.77(14) . . ?
O38 Fe1 N33 72.67(12) . . ?
N22 Fe1 N33 70.96(14) . . ?
O9 Fe1 N33 141.22(13) . . ?
O100 Fe2 O309 100.30(16) . . ?
O100 Fe2 O30 95.45(15) . . ?
O309 Fe2 O30 95.84(14) . . ?
O100 Fe2 O9 156.94(15) . . ?
O309 Fe2 O9 100.79(15) . . ?
O30 Fe2 O9 73.21(13) . . ?
O100 Fe2 N301 92.4(7) . . ?
O309 Fe2 N301 76.8(3) . . ?
O30 Fe2 N301 170.1(6) . . ?
O9 Fe2 N301 101.4(7) . . ?
O100 Fe2 N401 96.5(10) . . ?
O309 Fe2 N401 80.9(4) . . ?
O30 Fe2 N401 168.0(10) . . ?
O9 Fe2 N401 95.9(10) . . ?
O100 Fe2 N312 79.19(16) . . ?
O309 Fe2 N312 151.63(15) . . ?
O30 Fe2 N312 112.49(14) . . ?
O9 Fe2 N312 86.62(15) . . ?
N301 Fe2 N312 74.9(3) . . ?
N401 Fe2 N312 71.1(4) . . ?
Fe1 O1 Fe1 180.0 2_566 . ?
C2 N1 C10 120.5(4) . . ?
C2 N1 Fe1 121.6(3) . . ?
C10 N1 Fe1 117.4(3) . . ?
N1 C2 C3 121.1(5) . . ?
N1 C2 C11 114.4(5) . . ?
C3 C2 C11 124.2(5) . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 126.0(5) . . ?
C4 C5 C10 115.9(5) . . ?
C6 C5 C10 118.1(5) . . ?
C7 C6 C5 119.4(6) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 122.7(6) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 H01F 119.7 . . ?
C7 C8 H01F 119.7 . . ?
C9 O9 Fe2 136.4(3) . . ?
C9 O9 Fe1 116.0(3) . . ?
Fe2 O9 Fe1 106.72(15) . . ?
O9 C9 C8 126.9(5) . . ?
O9 C9 C10 115.9(4) . . ?
C8 C9 C10 117.0(5) . . ?
N1 C10 C5 122.0(5) . . ?
N1 C10 C9 116.0(4) . . ?
C5 C10 C9 121.9(5) . . ?
O11 C11 N33 115.5(4) . . ?
O11 C11 C2 112.3(4) . . ?
N33 C11 C2 108.5(4) . . ?
O11 C11 H11A 106.7 . . ?
N33 C11 H11A 106.7 . . ?
C2 C11 H11A 106.7 . . ?
C11 O11 H11 109.5 . . ?
C23 N22 C31 119.5(4) . . ?
C23 N22 Fe1 124.6(3) . . ?
C31 N22 Fe1 115.2(3) . . ?
N22 C23 C24 122.2(5) . . ?
N22 C23 C32 116.5(4) . . ?
C24 C23 C32 121.3(4) . . ?
C25 C24 C23 119.7(5) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 119.7(5) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C31 C26 C25 117.4(5) . . ?
C31 C26 C27 117.6(5) . . ?
C25 C26 C27 124.9(5) . . ?
C28 C27 C26 120.0(5) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 122.0(5) . . ?
C27 C28 H28 119.0 . . ?
C29 C28 H28 119.0 . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
O30 C30 C29 125.4(5) . . ?
O30 C30 C31 116.2(4) . . ?
C29 C30 C31 118.4(5) . . ?
C30 O30 Fe2 132.6(3) . . ?
C30 O30 Fe1 117.0(3) . . ?
Fe2 O30 Fe1 109.81(15) . . ?
N22 C31 C26 121.5(4) . . ?
N22 C31 C30 116.0(4) . . ?
C26 C31 C30 122.6(5) . . ?
O36 C32 N33 107.6(4) . . ?
O36 C32 C23 108.4(4) . . ?
N33 C32 C23 112.0(4) . . ?
O36 C32 H32 109.6 . . ?
N33 C32 H32 109.6 . . ?
C23 C32 H32 109.6 . . ?
C11 N33 C32 111.1(4) . . ?
C11 N33 C34 117.4(4) . . ?
C32 N33 C34 104.9(4) . . ?
C11 N33 Fe1 101.9(3) . . ?
C32 N33 Fe1 110.1(3) . . ?
C34 N33 Fe1 111.5(3) . . ?
N33 C34 C39 113.4(4) . . ?
N33 C34 C35 102.9(4) . . ?
C39 C34 C35 111.8(4) . . ?
N33 C34 C37 106.3(4) . . ?
C39 C34 C37 110.8(4) . . ?
C35 C34 C37 111.3(4) . . ?
O36 C35 C34 106.8(4) . . ?
O36 C35 H35A 110.4 . . ?
C34 C35 H35A 110.4 . . ?
O36 C35 H35B 110.4 . . ?
C34 C35 H35B 110.4 . . ?
H35A C35 H35B 108.6 . . ?
C32 O36 C35 109.9(4) . . ?
O38 C37 C34 110.3(4) . . ?
O38 C37 H37A 109.6 . . ?
C34 C37 H37A 109.6 . . ?
O38 C37 H37B 109.6 . . ?
C34 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
C37 O38 Fe1 117.6(3) . . ?
C37 O38 H38 109.3 . . ?
Fe1 O38 H38 114.4 . . ?
O40 C39 C34 108.7(4) . . ?
O40 C39 H39A 110.0 . . ?
C34 C39 H39A 110.0 . . ?
O40 C39 H39B 110.0 . . ?
C34 C39 H39B 110.0 . . ?
H39A C39 H39B 108.3 . . ?
C39 O40 H40 109.5 . . ?
O100 C101 C313 111.3(8) . . ?
O100 C101 H10A 109.4 . . ?
C313 C101 H10A 109.4 . . ?
O100 C101 H10B 109.4 . . ?
C313 C101 H10B 109.4 . . ?
H10A C101 H10B 108.0 . . ?
C102 O101 H101 109.5 . . ?
O101 C102 C313 110.7(10) . . ?
O101 C102 H10C 109.5 . . ?
C313 C102 H10C 109.5 . . ?
O101 C102 H10D 109.5 . . ?
C313 C102 H10D 109.5 . . ?
H10C C102 H10D 108.1 . . ?
O315 C103 C313 105.1(7) . . ?
O315 C103 H10E 110.7 . . ?
C313 C103 H10E 110.7 . . ?
O315 C103 H10F 110.7 . . ?
C313 C103 H10F 110.7 . . ?
H10E C103 H10F 108.8 . . ?
C201 O100 Fe2 115.2(7) . . ?
C101 O100 Fe2 118.9(5) . . ?
O100 C201 C313 112.1(9) . . ?
O100 C201 H20A 109.2 . . ?
C313 C201 H20A 109.2 . . ?
O100 C201 H20B 109.2 . . ?
C313 C201 H20B 109.2 . . ?
H20A C201 H20B 107.9 . . ?
C202 O201 H201 109.5 . . ?
O201 C202 C313 110.3(13) . . ?
O201 C202 H20C 109.6 . . ?
C313 C202 H20C 109.6 . . ?
O201 C202 H20D 109.6 . . ?
C313 C202 H20D 109.6 . . ?
H20C C202 H20D 108.1 . . ?
C313 C203 O315 101.4(9) . . ?
C313 C203 H20E 111.5 . . ?
O315 C203 H20E 111.5 . . ?
C313 C203 H20F 111.5 . . ?
O315 C203 H20F 111.5 . . ?
H20E C203 H20F 109.3 . . ?
C309 O309 Fe2 119.2(5) . . ?
C409 O309 Fe2 111.6(6) . . ?
O315 C311 C402 110.9(13) . . ?
O315 C311 N312 107.4(4) . . ?
C402 C311 N312 114.0(8) . . ?
O315 C311 C302 107.7(9) . . ?
N312 C311 C302 108.4(6) . . ?
O315 C311 H311 111.1 . . ?
N312 C311 H311 111.1 . . ?
C302 C311 H311 111.1 . . ?
O315 C311 H411 108.1 . . ?
C402 C311 H411 108.1 . . ?
N312 C311 H411 108.1 . . ?
C313 N312 C311 105.9(4) . . ?
C313 N312 Fe2 106.5(3) . . ?
C311 N312 Fe2 114.0(3) . . ?
C313 N312 H312 110.1 . . ?
C311 N312 H312 110.1 . . ?
Fe2 N312 H312 110.1 . . ?
N312 C313 C101 107.8(6) . . ?
N312 C313 C102 110.2(6) . . ?
C101 C313 C102 114.3(7) . . ?
N312 C313 C202 115.0(8) . . ?
N312 C313 C203 104.8(7) . . ?
C202 C313 C203 111.3(8) . . ?
N312 C313 C103 100.2(6) . . ?
C101 C313 C103 111.7(7) . . ?
C102 C313 C103 111.6(7) . . ?
N312 C313 C201 106.8(6) . . ?
C202 C313 C201 108.9(10) . . ?
C203 C313 C201 109.9(9) . . ?
C103 O315 C311 109.8(5) . . ?
C311 O315 C203 103.8(6) . . ?
C302 N301 C310 120.6(10) . . ?
C302 N301 Fe2 125.2(8) . . ?
C310 N301 Fe2 114.1(8) . . ?
N301 C302 C303 120.8(10) . . ?
N301 C302 C311 116.1(9) . . ?
C303 C302 C311 123.1(9) . . ?
C304 C303 C302 120.1(10) . . ?
C304 C303 H303 119.9 . . ?
C302 C303 H303 119.9 . . ?
C303 C304 C305 119.7(9) . . ?
C303 C304 H304 120.2 . . ?
C305 C304 H304 120.2 . . ?
C310 C305 C304 117.2(8) . . ?
C310 C305 C306 116.5(8) . . ?
C304 C305 C306 126.2(9) . . ?
C307 C306 C305 119.8(9) . . ?
C307 C306 H306 120.1 . . ?
C305 C306 H306 120.1 . . ?
C306 C307 C308 122.2(9) . . ?
C306 C307 H307 118.9 . . ?
C308 C307 H307 118.9 . . ?
C309 C308 C307 120.2(9) . . ?
C309 C308 H308 119.9 . . ?
C307 C308 H308 119.9 . . ?
O309 C309 C308 128.0(9) . . ?
O309 C309 C310 114.0(8) . . ?
C308 C309 C310 117.7(9) . . ?
N301 C310 C305 121.4(9) . . ?
N301 C310 C309 115.0(9) . . ?
C305 C310 C309 123.5(8) . . ?
C402 N401 C410 121.2(13) . . ?
C402 N401 Fe2 125.7(11) . . ?
C410 N401 Fe2 113.1(10) . . ?
N401 C402 C403 120.9(13) . . ?
N401 C402 C311 115.0(13) . . ?
C403 C402 C311 124.1(13) . . ?
C404 C403 C402 119.2(13) . . ?
C404 C403 H403 120.4 . . ?
C402 C403 H403 120.4 . . ?
C403 C404 C405 120.5(12) . . ?
C403 C404 H404 119.7 . . ?
C405 C404 H404 119.7 . . ?
C410 C405 C404 116.7(10) . . ?
C410 C405 C406 115.2(11) . . ?
C404 C405 C406 128.0(11) . . ?
C407 C406 C405 119.6(11) . . ?
C407 C406 H406 120.2 . . ?
C405 C406 H406 120.2 . . ?
C406 C407 C408 124.7(12) . . ?
C406 C407 H407 117.6 . . ?
C408 C407 H407 117.6 . . ?
C409 C408 C407 118.2(12) . . ?
C409 C408 H408 120.9 . . ?
C407 C408 H408 120.9 . . ?
C408 C409 C410 117.8(12) . . ?
C408 C409 O309 122.3(11) . . ?
C410 C409 O309 119.8(10) . . ?
N401 C410 C409 114.4(11) . . ?
N401 C410 C405 121.3(11) . . ?
C409 C410 C405 124.3(11) . . ?
N501 C502 C503 166.4(19) . . ?
C502 C503 H50A 109.5 . . ?
C502 C503 H50B 109.5 . . ?
H50A C503 H50B 109.5 . . ?
C502 C503 H50C 109.5 . . ?
H50A C503 H50C 109.5 . . ?
H50B C503 H50C 109.5 . . ?
N601 C602 C603 170(4) . . ?
C602 C603 H60A 109.5 . . ?
C602 C603 H60B 109.5 . . ?
H60A C603 H60B 109.5 . . ?
C602 C603 H60C 109.5 . . ?
H60A C603 H60C 109.5 . . ?
H60B C603 H60C 109.5 . . ?
O903 N900 O902 121.0(5) . . ?
O903 N900 O901 118.6(6) . . ?
O902 N900 O901 120.2(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
C10 N1 C2 C3 -2.5(7) . . . . ?
Fe1 N1 C2 C3 -174.4(3) . . . . ?
C10 N1 C2 C11 172.3(4) . . . . ?
Fe1 N1 C2 C11 0.3(5) . . . . ?
N1 C2 C3 C4 0.1(7) . . . . ?
C11 C2 C3 C4 -174.1(5) . . . . ?
C2 C3 C4 C5 2.6(8) . . . . ?
C3 C4 C5 C6 175.9(5) . . . . ?
C3 C4 C5 C10 -2.8(7) . . . . ?
C4 C5 C6 C7 -174.5(6) . . . . ?
C10 C5 C6 C7 4.2(8) . . . . ?
C5 C6 C7 C8 -2.1(10) . . . . ?
C6 C7 C8 C9 -2.5(9) . . . . ?
Fe2 O9 C9 C8 21.4(8) . . . . ?
Fe1 O9 C9 C8 -170.8(4) . . . . ?
Fe2 O9 C9 C10 -163.3(3) . . . . ?
Fe1 O9 C9 C10 4.5(5) . . . . ?
C7 C8 C9 O9 179.9(5) . . . . ?
C7 C8 C9 C10 4.6(8) . . . . ?
C2 N1 C10 C5 2.1(7) . . . . ?
Fe1 N1 C10 C5 174.4(4) . . . . ?
C2 N1 C10 C9 -174.5(4) . . . . ?
Fe1 N1 C10 C9 -2.1(5) . . . . ?
C4 C5 C10 N1 0.5(7) . . . . ?
C6 C5 C10 N1 -178.3(5) . . . . ?
C4 C5 C10 C9 176.9(5) . . . . ?
C6 C5 C10 C9 -2.0(7) . . . . ?
O9 C9 C10 N1 -1.6(6) . . . . ?
C8 C9 C10 N1 174.2(4) . . . . ?
O9 C9 C10 C5 -178.2(4) . . . . ?
C8 C9 C10 C5 -2.4(7) . . . . ?
N1 C2 C11 O11 165.7(4) . . . . ?
C3 C2 C11 O11 -19.7(6) . . . . ?
N1 C2 C11 N33 36.8(5) . . . . ?
C3 C2 C11 N33 -148.7(4) . . . . ?
C31 N22 C23 C24 -0.3(7) . . . . ?
Fe1 N22 C23 C24 169.9(4) . . . . ?
C31 N22 C23 C32 179.1(4) . . . . ?
Fe1 N22 C23 C32 -10.7(6) . . . . ?
N22 C23 C24 C25 0.7(8) . . . . ?
C32 C23 C24 C25 -178.6(5) . . . . ?
C23 C24 C25 C26 -1.1(8) . . . . ?
C24 C25 C26 C31 1.1(8) . . . . ?
C24 C25 C26 C27 -179.9(5) . . . . ?
C31 C26 C27 C28 -2.5(7) . . . . ?
C25 C26 C27 C28 178.5(5) . . . . ?
C26 C27 C28 C29 1.3(8) . . . . ?
C27 C28 C29 C30 0.2(8) . . . . ?
C28 C29 C30 O30 -178.6(4) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C30 O30 Fe2 -17.7(7) . . . . ?
C31 C30 O30 Fe2 164.2(3) . . . . ?
C29 C30 O30 Fe1 171.6(4) . . . . ?
C31 C30 O30 Fe1 -6.6(5) . . . . ?
C23 N22 C31 C26 0.2(6) . . . . ?
Fe1 N22 C31 C26 -170.8(3) . . . . ?
C23 N22 C31 C30 178.3(4) . . . . ?
Fe1 N22 C31 C30 7.3(5) . . . . ?
C25 C26 C31 N22 -0.6(7) . . . . ?
C27 C26 C31 N22 -179.7(4) . . . . ?
C25 C26 C31 C30 -178.6(4) . . . . ?
C27 C26 C31 C30 2.3(7) . . . . ?
O30 C30 C31 N22 -0.6(6) . . . . ?
C29 C30 C31 N22 -178.9(4) . . . . ?
O30 C30 C31 C26 177.5(4) . . . . ?
C29 C30 C31 C26 -0.8(7) . . . . ?
N22 C23 C32 O36 -129.0(4) . . . . ?
C24 C23 C32 O36 50.4(6) . . . . ?
N22 C23 C32 N33 -10.5(6) . . . . ?
C24 C23 C32 N33 168.9(4) . . . . ?
O11 C11 N33 C32 66.8(5) . . . . ?
C2 C11 N33 C32 -166.1(4) . . . . ?
O11 C11 N33 C34 -53.9(6) . . . . ?
C2 C11 N33 C34 73.2(5) . . . . ?
O11 C11 N33 Fe1 -176.0(3) . . . . ?
C2 C11 N33 Fe1 -48.9(4) . . . . ?
O36 C32 N33 C11 -106.1(4) . . . . ?
C23 C32 N33 C11 134.9(4) . . . . ?
O36 C32 N33 C34 21.8(5) . . . . ?
C23 C32 N33 C34 -97.3(4) . . . . ?
O36 C32 N33 Fe1 141.8(3) . . . . ?
C23 C32 N33 Fe1 22.8(5) . . . . ?
C11 N33 C34 C39 -25.0(6) . . . . ?
C32 N33 C34 C39 -148.9(4) . . . . ?
Fe1 N33 C34 C39 92.1(4) . . . . ?
C11 N33 C34 C35 96.1(5) . . . . ?
C32 N33 C34 C35 -27.9(5) . . . . ?
Fe1 N33 C34 C35 -146.9(3) . . . . ?
C11 N33 C34 C37 -146.9(4) . . . . ?
C32 N33 C34 C37 89.2(4) . . . . ?
Fe1 N33 C34 C37 -29.9(4) . . . . ?
N33 C34 C35 O36 24.6(5) . . . . ?
C39 C34 C35 O36 146.7(4) . . . . ?
C37 C34 C35 O36 -88.8(5) . . . . ?
N33 C32 O36 C35 -6.2(6) . . . . ?
C23 C32 O36 C35 115.0(5) . . . . ?
C34 C35 O36 C32 -11.9(6) . . . . ?
N33 C34 C37 O38 49.5(5) . . . . ?
C39 C34 C37 O38 -74.1(5) . . . . ?
C35 C34 C37 O38 160.8(4) . . . . ?
C34 C37 O38 Fe1 -49.2(5) . . . . ?
N33 C34 C39 O40 178.6(4) . . . . ?
C35 C34 C39 O40 62.8(6) . . . . ?
C37 C34 C39 O40 -62.0(5) . . . . ?
C313 C101 O100 Fe2 37.7(10) . . . . ?
O309 Fe2 O100 C201 -172.7(8) . . . . ?
O30 Fe2 O100 C201 -75.7(8) . . . . ?
O9 Fe2 O100 C201 -16.8(9) . . . . ?
N401 Fe2 O100 C201 105.4(9) . . . . ?
N312 Fe2 O100 C201 36.2(8) . . . . ?
O309 Fe2 O100 C101 137.1(6) . . . . ?
O30 Fe2 O100 C101 -125.9(6) . . . . ?
O9 Fe2 O100 C101 -67.0(7) . . . . ?
N301 Fe2 O100 C101 60.1(7) . . . . ?
N312 Fe2 O100 C101 -14.0(6) . . . . ?
Fe2 O100 C201 C313 -53.2(12) . . . . ?
O315 C311 N312 C313 -12.0(5) . . . . ?
C402 C311 N312 C313 111.2(16) . . . . ?
C302 C311 N312 C313 104.1(10) . . . . ?
O315 C311 N312 Fe2 -128.8(4) . . . . ?
C402 C311 N312 Fe2 -5.5(16) . . . . ?
C302 C311 N312 Fe2 -12.7(11) . . . . ?
C311 N312 C313 C101 -90.0(6) . . . . ?
Fe2 N312 C313 C101 31.7(6) . . . . ?
C311 N312 C313 C102 144.7(7) . . . . ?
Fe2 N312 C313 C102 -93.7(6) . . . . ?
C311 N312 C313 C202 108.1(9) . . . . ?
Fe2 N312 C313 C202 -130.2(9) . . . . ?
C311 N312 C313 C203 -14.5(8) . . . . ?
Fe2 N312 C313 C203 107.2(7) . . . . ?
C311 N312 C313 C103 27.0(7) . . . . ?
Fe2 N312 C313 C103 148.7(5) . . . . ?
C311 N312 C313 C201 -131.0(7) . . . . ?
Fe2 N312 C313 C201 -9.3(7) . . . . ?
O100 C101 C313 N312 -44.6(9) . . . . ?
O100 C101 C313 C102 78.2(10) . . . . ?
O100 C101 C313 C103 -153.8(8) . . . . ?
O101 C102 C313 N312 -52.9(13) . . . . ?
O101 C102 C313 C101 -174.5(11) . . . . ?
O101 C102 C313 C103 57.5(13) . . . . ?
O201 C202 C313 N312 53(2) . . . . ?
O201 C202 C313 C203 172.4(18) . . . . ?
O201 C202 C313 C201 -66(2) . . . . ?
O315 C203 C313 N312 33.3(8) . . . . ?
O315 C203 C313 C202 -91.7(12) . . . . ?
O315 C203 C313 C201 147.7(7) . . . . ?
O315 C103 C313 N312 -34.0(9) . . . . ?
O315 C103 C313 C101 79.9(10) . . . . ?
O315 C103 C313 C102 -150.7(8) . . . . ?
O100 C201 C313 N312 38.0(12) . . . . ?
O100 C201 C313 C202 162.7(11) . . . . ?
O100 C201 C313 C203 -75.2(12) . . . . ?
C313 C103 O315 C311 28.5(9) . . . . ?
N312 C311 O315 C103 -11.0(8) . . . . ?
C302 C311 O315 C103 -127.6(9) . . . . ?
C402 C311 O315 C203 -92.1(13) . . . . ?
N312 C311 O315 C203 33.1(7) . . . . ?
C313 C203 O315 C311 -41.3(8) . . . . ?
C310 N301 C302 C303 2(3) . . . . ?
Fe2 N301 C302 C303 -179.9(17) . . . . ?
C310 N301 C302 C311 -179.7(19) . . . . ?
Fe2 N301 C302 C311 -2(3) . . . . ?
O315 C311 C302 N301 125.7(16) . . . . ?
N312 C311 C302 N301 10(2) . . . . ?
O315 C311 C302 C303 -56(2) . . . . ?
N312 C311 C302 C303 -172.0(15) . . . . ?
N301 C302 C303 C304 -1(3) . . . . ?
C311 C302 C303 C304 -179.5(16) . . . . ?
C302 C303 C304 C305 -1(2) . . . . ?
C303 C304 C305 C310 3.3(17) . . . . ?
C303 C304 C305 C306 -178.1(12) . . . . ?
C310 C305 C306 C307 1.8(16) . . . . ?
C304 C305 C306 C307 -176.9(12) . . . . ?
C305 C306 C307 C308 -2.6(18) . . . . ?
C306 C307 C308 C309 1.6(18) . . . . ?
Fe2 O309 C309 C308 176.1(10) . . . . ?
Fe2 O309 C309 C310 -10.7(13) . . . . ?
C307 C308 C309 O309 173.2(12) . . . . ?
C307 C308 C309 C310 0.2(17) . . . . ?
C302 N301 C310 C305 0(3) . . . . ?
Fe2 N301 C310 C305 -178.3(12) . . . . ?
C302 N301 C310 C309 178.7(18) . . . . ?
Fe2 N301 C310 C309 0(2) . . . . ?
C304 C305 C310 N301 -3(2) . . . . ?
C306 C305 C310 N301 178.6(15) . . . . ?
C304 C305 C310 C309 178.7(12) . . . . ?
C306 C305 C310 C309 0.0(18) . . . . ?
O309 C309 C310 N301 6.4(18) . . . . ?
C308 C309 C310 N301 -179.7(15) . . . . ?
O309 C309 C310 C305 -174.9(12) . . . . ?
C308 C309 C310 C305 -1.0(18) . . . . ?
C410 N401 C402 C403 -1(4) . . . . ?
Fe2 N401 C402 C403 -180(2) . . . . ?
C410 N401 C402 C311 -180(3) . . . . ?
Fe2 N401 C402 C311 1(4) . . . . ?
O315 C311 C402 N401 124(2) . . . . ?
N312 C311 C402 N401 3(3) . . . . ?
O315 C311 C402 C403 -55(3) . . . . ?
N312 C311 C402 C403 -176(2) . . . . ?
N401 C402 C403 C404 0(4) . . . . ?
C311 C402 C403 C404 179(2) . . . . ?
C402 C403 C404 C405 -2(3) . . . . ?
C403 C404 C405 C410 3(2) . . . . ?
C403 C404 C405 C406 -178.8(18) . . . . ?
C410 C405 C406 C407 3(2) . . . . ?
C404 C405 C406 C407 -175.1(17) . . . . ?
C405 C406 C407 C408 -2(3) . . . . ?
C406 C407 C408 C409 -1(3) . . . . ?
C407 C408 C409 C410 3(2) . . . . ?
C407 C408 C409 O309 -174.4(16) . . . . ?
Fe2 O309 C409 C408 -177.3(14) . . . . ?
Fe2 O309 C409 C410 4.9(18) . . . . ?
C402 N401 C410 C409 -179(3) . . . . ?
Fe2 N401 C410 C409 0(3) . . . . ?
C402 N401 C410 C405 3(4) . . . . ?
Fe2 N401 C410 C405 -178.3(16) . . . . ?
C408 C409 C410 N401 179(2) . . . . ?
O309 C409 C410 N401 -3(3) . . . . ?
C408 C409 C410 C405 -3(3) . . . . ?
O309 C409 C410 C405 175.1(17) . . . . ?
C404 C405 C410 N401 -4(3) . . . . ?
C406 C405 C410 N401 178(2) . . . . ?
C404 C405 C410 C409 177.7(16) . . . . ?
C406 C405 C410 C409 0(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
_geom_hbond_publ_flag
O11 H11 O309 0.84 1.90 2.692(5) 156.7 2_566 yes
O38 H38 O901 0.84 1.87 2.712(6) 174.8 . yes
O40 H40 O902 0.84 1.89 2.719(6) 168.3 . yes
O101^a H101^a O40 0.84 1.91 2.742(16) 173.6 2_656 yes
O201^b H201^b O40 0.84 1.87 2.694(17) 168.0 2_656 yes
N312 H312 O901 1.00 2.09 3.047(7) 158.4 . yes

_refine_diff_density_max         0.679
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_cmpd_6_0m
_database_code_depnum_ccdc_archive 'CCDC 1832159'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
; 
;
_chemical_name_common            cmpd_6
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 Co3 N16 O8'
_chemical_formula_sum            'C28 H28 Co3 N16 O8'
_chemical_formula_weight         893.45

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4740(4)
_cell_length_b                   17.7982(6)
_cell_length_c                   9.7057(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.4270(10)
_cell_angle_gamma                90
_cell_volume                     1622.85(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8108
_cell_measurement_theta_min      2.2886
_cell_measurement_theta_max      26.3765

_exptl_crystal_description       nugget
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_F_000             906
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.595
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            21623
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3319
_reflns_number_gt                2740
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0398P)²+2.1240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     276
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.63301(4) 0.44962(2) 0.25559(4) 0.01704(11) Uani 1 1 d . . . . .
Co2 Co 0.500000 0.500000 0.500000 0.01905(14) Uani 1 2 d S . P . .
O1 O 0.81081(19) 0.45813(10) 0.37915(19) 0.0205(4) Uani 1 1 d . . . . .
O2 O 0.3670(2) 0.30109(11) 0.0575(2) 0.0306(5) Uani 1 1 d . . . . .
O3 O 0.54669(18) 0.40485(9) 0.40420(18) 0.0179(4) Uani 1 1 d . . . . .
O4 O 0.2948(2) 0.49064(12) 0.3924(2) 0.0273(5) Uani 1 1 d D . . . .
H4A H 0.236(3) 0.5027(18) 0.440(3) 0.033 Uiso 1 1 d D U . . .
N1 N 0.7068(2) 0.49577(13) 0.0976(2) 0.0224(5) Uani 1 1 d D U . . .
N2 N 0.5612(2) 0.54546(12) 0.3150(2) 0.0197(5) Uani 1 1 d . . . . .
N5 N 0.6251(3) 0.60224(13) 0.2954(2) 0.0237(5) Uani 1 1 d . . . . .
N6 N 0.6809(3) 0.65704(15) 0.2739(3) 0.0420(7) Uani 1 1 d . . . . .
N7 N 0.6976(2) 0.35621(12) 0.2121(2) 0.0198(5) Uani 1 1 d . . . . .
N8 N 0.4593(2) 0.41848(13) 0.1372(2) 0.0207(5) Uani 1 1 d . . . . .
H8A H 0.425(3) 0.4534(17) 0.084(3) 0.027(8) Uiso 1 1 d . . . . .
C1 C 0.6213(3) 0.31082(15) 0.1264(3) 0.0238(6) Uani 1 1 d . . . . .
C2 C 0.6702(3) 0.23653(17) 0.1096(3) 0.0326(7) Uani 1 1 d . . . . .
H2 H 0.616996 0.202690 0.047388 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7955(3) 0.21456(17) 0.1847(3) 0.0325(7) Uani 1 1 d . . . . .
H3 H 0.828424 0.164706 0.174344 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8783(3) 0.26416(16) 0.2780(3) 0.0271(6) Uani 1 1 d . . . . .
C5 C 1.0082(3) 0.24908(17) 0.3636(3) 0.0318(7) Uani 1 1 d . . . . .
H5 H 1.053433 0.201634 0.359760 0.038 Uiso 1 1 calc R U . . .
C6 C 1.0672(3) 0.30376(18) 0.4515(3) 0.0310(7) Uani 1 1 d . . . . .
H6 H 1.154426 0.292813 0.507829 0.037 Uiso 1 1 calc R U . . .
C7 C 1.0066(3) 0.37569(16) 0.4638(3) 0.0242(6) Uani 1 1 d . . . . .
H7 H 1.051015 0.411317 0.528302 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8817(3) 0.39310(15) 0.3803(3) 0.0195(5) Uani 1 1 d . . . . .
C9 C 0.8212(3) 0.33623(15) 0.2886(3) 0.0206(6) Uani 1 1 d . . . . .
C10 C 0.4862(3) 0.34873(15) 0.0569(3) 0.0244(6) Uani 1 1 d . . . . .
H10 H 0.498008 0.362439 -0.040849 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3465(3) 0.39483(15) 0.2254(3) 0.0221(6) Uani 1 1 d . . . . .
C12 C 0.2651(3) 0.33668(16) 0.1311(3) 0.0268(6) Uani 1 1 d . . . . .
H12A H 0.219348 0.299444 0.186866 0.032 Uiso 1 1 calc R U . . .
H12B H 0.190368 0.361268 0.065625 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4289(3) 0.35861(15) 0.3543(3) 0.0220(6) Uani 1 1 d . . . . .
H13A H 0.365810 0.352616 0.427297 0.026 Uiso 1 1 calc R U . . .
H13B H 0.462940 0.308223 0.330636 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2498(3) 0.45969(16) 0.2592(3) 0.0246(6) Uani 1 1 d . . . . .
H14A H 0.250516 0.499452 0.187954 0.029 Uiso 1 1 calc R U . . .
H14B H 0.150924 0.441110 0.255900 0.029 Uiso 1 1 calc R U . . .
N3A N 0.8286(3) 0.51971(15) 0.1208(3) 0.0251(7) Uani 0.899(5) 1 d D U P A 1
N4A N 0.9424(3) 0.54363(18) 0.1354(4) 0.0421(9) Uani 0.899(5) 1 d D U P A 1
N3B N 0.815(2) 0.4621(14) 0.072(3) 0.032(5) Uani 0.101(5) 1 d D U P A 2
N4B N 0.919(3) 0.4359(18) 0.044(4) 0.058(8) Uani 0.101(5) 1 d D U P 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
Co1 N7 1.839(2) . ?
Co1 O3 1.9207(18) . ?
Co1 O1 1.9434(17) . ?
Co1 N1 1.947(2) . ?
Co1 N2 1.951(2) . ?
Co1 N8 1.961(2) . ?
Co1 Co2 2.9652(4) . ?
Co2 O3 2.0086(17) . ?
Co2 O3 2.0086(17) 3_666 ?
Co2 O4 2.0913(19) . ?
Co2 O4 2.0913(19) 3_666 ?
Co2 N2 2.117(2) 3_666 ?
Co2 N2 2.117(2) . ?
O1 C8 1.337(3) . ?
O2 C10 1.413(3) . ?
O2 C12 1.422(4) . ?
O3 C13 1.420(3) . ?
O4 C14 1.419(3) . ?
O4 H4A 0.800(18) . ?
N1 N3A 1.223(3) . ?
N1 N3B 1.244(14) . ?
N2 N5 1.206(3) . ?
N5 N6 1.142(3) . ?
N7 C1 1.309(3) . ?
N7 C9 1.351(3) . ?
N8 C10 1.505(4) . ?
N8 C11 1.512(4) . ?
N8 H8A 0.85(3) . ?
C1 C2 1.417(4) . ?
C1 C10 1.524(4) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.401(4) . ?
C4 C5 1.418(4) . ?
C5 C6 1.366(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.524(4) . ?
C11 C13 1.529(4) . ?
C11 C14 1.535(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N3A N4A 1.151(4) . ?
N3B N4B 1.148(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 Co1 O3 89.07(9) . . ?
N7 Co1 O1 85.66(9) . . ?
O3 Co1 O1 89.32(8) . . ?
N7 Co1 N1 92.11(10) . . ?
O3 Co1 N1 175.88(8) . . ?
O1 Co1 N1 94.71(9) . . ?
N7 Co1 N2 175.63(9) . . ?
O3 Co1 N2 86.67(8) . . ?
O1 Co1 N2 93.26(8) . . ?
N1 Co1 N2 92.21(10) . . ?
N7 Co1 N8 83.64(10) . . ?
O3 Co1 N8 85.18(9) . . ?
O1 Co1 N8 168.05(9) . . ?
N1 Co1 N8 91.02(10) . . ?
N2 Co1 N8 97.00(9) . . ?
N7 Co1 Co2 130.18(7) . . ?
O3 Co1 Co2 42.13(5) . . ?
O1 Co1 Co2 84.65(6) . . ?
N1 Co1 Co2 137.33(7) . . ?
N2 Co1 Co2 45.45(7) . . ?
N8 Co1 Co2 98.20(7) . . ?
O3 Co2 O3 180.0 . 3_666 ?
O3 Co2 O4 87.01(7) . . ?
O3 Co2 O4 92.99(7) 3_666 . ?
O3 Co2 O4 92.99(7) . 3_666 ?
O3 Co2 O4 87.01(7) 3_666 3_666 ?
O4 Co2 O4 180.0 . 3_666 ?
O3 Co2 N2 99.85(7) . 3_666 ?
O3 Co2 N2 80.15(7) 3_666 3_666 ?
O4 Co2 N2 93.10(8) . 3_666 ?
O4 Co2 N2 86.90(8) 3_666 3_666 ?
O3 Co2 N2 80.15(7) . . ?
O3 Co2 N2 99.85(7) 3_666 . ?
O4 Co2 N2 86.90(8) . . ?
O4 Co2 N2 93.10(8) 3_666 . ?
N2 Co2 N2 180.0 3_666 . ?
O3 Co2 Co1 140.10(5) . 3_666 ?
O3 Co2 Co1 39.91(5) 3_666 3_666 ?
O4 Co2 Co1 87.69(6) . 3_666 ?
O4 Co2 Co1 92.31(6) 3_666 3_666 ?
N2 Co2 Co1 41.06(6) 3_666 3_666 ?
N2 Co2 Co1 138.94(6) . 3_666 ?
O3 Co2 Co1 39.90(5) . . ?
O3 Co2 Co1 140.09(5) 3_666 . ?
O4 Co2 Co1 92.31(6) . . ?
O4 Co2 Co1 87.69(6) 3_666 . ?
N2 Co2 Co1 138.94(6) 3_666 . ?
N2 Co2 Co1 41.06(6) . . ?
Co1 Co2 Co1 180.0 3_666 . ?
C8 O1 Co1 109.38(15) . . ?
C10 O2 C12 109.3(2) . . ?
C13 O3 Co1 112.11(15) . . ?
C13 O3 Co2 115.85(16) . . ?
Co1 O3 Co2 97.96(7) . . ?
C14 O4 Co2 129.50(17) . . ?
C14 O4 H4A 119(3) . . ?
Co2 O4 H4A 111(3) . . ?
N3A N1 Co1 115.39(19) . . ?
N3B N1 Co1 110.2(12) . . ?
N5 N2 Co1 118.97(19) . . ?
N5 N2 Co2 130.73(18) . . ?
Co1 N2 Co2 93.49(9) . . ?
N6 N5 N2 177.3(3) . . ?
C1 N7 C9 123.8(2) . . ?
C1 N7 Co1 122.07(19) . . ?
C9 N7 Co1 113.73(18) . . ?
C10 N8 C11 104.1(2) . . ?
C10 N8 Co1 110.51(16) . . ?
C11 N8 Co1 110.37(16) . . ?
C10 N8 H8A 112(2) . . ?
C11 N8 H8A 108(2) . . ?
Co1 N8 H8A 112(2) . . ?
N7 C1 C2 119.1(3) . . ?
N7 C1 C10 111.8(2) . . ?
C2 C1 C10 129.1(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C9 C4 C5 116.4(3) . . ?
C9 C4 C3 115.3(3) . . ?
C5 C4 C3 128.3(3) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 124.0(3) . . ?
C5 C6 H6 118.0 . . ?
C7 C6 H6 118.0 . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
O1 C8 C7 126.2(2) . . ?
O1 C8 C9 116.8(2) . . ?
C7 C8 C9 117.0(2) . . ?
N7 C9 C4 121.1(2) . . ?
N7 C9 C8 114.1(2) . . ?
C4 C9 C8 124.8(2) . . ?
O2 C10 N8 107.7(2) . . ?
O2 C10 C1 111.0(2) . . ?
N8 C10 C1 109.0(2) . . ?
O2 C10 H10 109.7 . . ?
N8 C10 H10 109.7 . . ?
C1 C10 H10 109.7 . . ?
N8 C11 C12 100.9(2) . . ?
N8 C11 C13 104.9(2) . . ?
C12 C11 C13 111.7(2) . . ?
N8 C11 C14 113.3(2) . . ?
C12 C11 C14 111.7(2) . . ?
C13 C11 C14 113.5(2) . . ?
O2 C12 C11 106.3(2) . . ?
O2 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
O3 C13 C11 109.3(2) . . ?
O3 C13 H13A 109.8 . . ?
C11 C13 H13A 109.8 . . ?
O3 C13 H13B 109.8 . . ?
C11 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
O4 C14 C11 111.7(2) . . ?
O4 C14 H14A 109.3 . . ?
C11 C14 H14A 109.3 . . ?
O4 C14 H14B 109.3 . . ?
C11 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N4A N3A N1 176.4(3) . . ?
N4B N3B N1 175(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Co1 N7 C1 88.4(2) . . . . ?
O1 Co1 N7 C1 177.8(2) . . . . ?
N1 Co1 N7 C1 -87.7(2) . . . . ?
N8 Co1 N7 C1 3.1(2) . . . . ?
Co2 Co1 N7 C1 98.5(2) . . . . ?
O3 Co1 N7 C9 -84.19(19) . . . . ?
O1 Co1 N7 C9 5.19(19) . . . . ?
N1 Co1 N7 C9 99.76(19) . . . . ?
N8 Co1 N7 C9 -169.4(2) . . . . ?
Co2 Co1 N7 C9 -74.1(2) . . . . ?
C9 N7 C1 C2 -1.0(4) . . . . ?
Co1 N7 C1 C2 -172.9(2) . . . . ?
C9 N7 C1 C10 178.9(2) . . . . ?
Co1 N7 C1 C10 7.1(3) . . . . ?
N7 C1 C2 C3 0.5(5) . . . . ?
C10 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C9 0.9(5) . . . . ?
C2 C3 C4 C5 179.0(3) . . . . ?
C9 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C5 C6 -176.7(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
Co1 O1 C8 C7 -174.6(2) . . . . ?
Co1 O1 C8 C9 4.3(3) . . . . ?
C6 C7 C8 O1 179.9(3) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C1 N7 C9 C4 1.5(4) . . . . ?
Co1 N7 C9 C4 174.0(2) . . . . ?
C1 N7 C9 C8 -176.6(2) . . . . ?
Co1 N7 C9 C8 -4.1(3) . . . . ?
C5 C4 C9 N7 -179.7(3) . . . . ?
C3 C4 C9 N7 -1.4(4) . . . . ?
C5 C4 C9 C8 -1.8(4) . . . . ?
C3 C4 C9 C8 176.5(3) . . . . ?
O1 C8 C9 N7 -0.3(4) . . . . ?
C7 C8 C9 N7 178.6(2) . . . . ?
O1 C8 C9 C4 -178.4(3) . . . . ?
C7 C8 C9 C4 0.6(4) . . . . ?
C12 O2 C10 N8 0.9(3) . . . . ?
C12 O2 C10 C1 120.1(2) . . . . ?
C11 N8 C10 O2 20.3(3) . . . . ?
Co1 N8 C10 O2 138.82(17) . . . . ?
C11 N8 C10 C1 -100.1(2) . . . . ?
Co1 N8 C10 C1 18.3(3) . . . . ?
N7 C1 C10 O2 -134.8(2) . . . . ?
C2 C1 C10 O2 45.1(4) . . . . ?
N7 C1 C10 N8 -16.4(3) . . . . ?
C2 C1 C10 N8 163.5(3) . . . . ?
C10 N8 C11 C12 -31.7(2) . . . . ?
Co1 N8 C11 C12 -150.26(17) . . . . ?
C10 N8 C11 C13 84.5(2) . . . . ?
Co1 N8 C11 C13 -34.1(2) . . . . ?
C10 N8 C11 C14 -151.2(2) . . . . ?
Co1 N8 C11 C14 90.2(2) . . . . ?
C10 O2 C12 C11 -21.9(3) . . . . ?
N8 C11 C12 O2 33.2(3) . . . . ?
C13 C11 C12 O2 -77.8(3) . . . . ?
C14 C11 C12 O2 153.9(2) . . . . ?
Co1 O3 C13 C11 -37.7(2) . . . . ?
Co2 O3 C13 C11 73.6(2) . . . . ?
N8 C11 C13 O3 45.9(3) . . . . ?
C12 C11 C13 O3 154.4(2) . . . . ?
C14 C11 C13 O3 -78.3(3) . . . . ?
Co2 O4 C14 C11 31.7(3) . . . . ?
N8 C11 C14 O4 -97.4(3) . . . . ?
C12 C11 C14 O4 149.4(2) . . . . ?
C13 C11 C14 O4 22.1(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
_geom_hbond_publ_flag
O4 H4A O1 0.800(18) 1.99(2) 2.706(3) 149(3) 3_666 yes
N8 H8A N1 0.85(3) 2.22(3) 3.012(3) 156(3) 3_665 yes

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_cmpd_3_0m
_database_code_depnum_ccdc_archive 'CCDC 1832157'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
; 
;
_chemical_name_common            cmpd_3
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Cl N2 Ni O5'
_chemical_formula_sum            'C15 H19 Cl N2 Ni O5'
_chemical_formula_weight         401.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.0791(5)
_cell_length_b                   8.4696(3)
_cell_length_c                   14.1012(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.0920(10)
_cell_angle_gamma                90
_cell_volume                     1562.05(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.8054
_cell_measurement_theta_max      27.5132

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.443
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            20426
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3590
_reflns_number_gt                3270
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0275P)²+1.6202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.32697(2) 0.59304(2) 0.44415(2) 0.00909(7) Uani 1 1 d . . . . .
Cl1 Cl 0.25830(3) 0.41471(5) 0.32934(3) 0.01651(10) Uani 1 1 d . . . . .
O1 O 0.35886(9) 0.40882(14) 0.54012(9) 0.0139(3) Uani 1 1 d . . . . .
O2 O 0.46376(10) 0.61345(16) 0.37482(9) 0.0155(3) Uani 1 1 d . . . . .
H2 H 0.5158(19) 0.604(3) 0.4046(17) 0.023(6) Uiso 1 1 d . . . . .
O3 O 0.38437(10) 0.75757(15) 0.54347(9) 0.0136(2) Uani 1 1 d . . . . .
H3A H 0.4445(19) 0.783(3) 0.5482(17) 0.026(6) Uiso 1 1 d . . . . .
H3 H 0.2587(17) 0.824(3) 0.3377(17) 0.019(6) Uiso 1 1 d . . . . .
O4 O 0.10932(10) 0.95461(15) 0.43819(11) 0.0230(3) Uani 1 1 d . . . . .
O5 O 0.42382(11) 1.14625(18) 0.44319(13) 0.0290(4) Uani 1 1 d . . . . .
H5A H 0.394(2) 1.210(4) 0.449(2) 0.050(10) Uiso 1 1 d . . . . .
N1 N 0.19714(11) 0.58957(16) 0.51605(10) 0.0103(3) Uani 1 1 d . . . . .
N2 N 0.25191(11) 0.80516(17) 0.39364(10) 0.0103(3) Uani 1 1 d . . . . .
C2 C 0.19115(12) 0.48130(19) 0.58652(11) 0.0101(3) Uani 1 1 d . . . . .
C3 C 0.28009(13) 0.3843(2) 0.59817(12) 0.0117(3) Uani 1 1 d . . . . .
C4 C 0.27583(14) 0.2719(2) 0.66973(12) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.332785 0.204589 0.680417 0.019 Uiso 1 1 calc R U . . .
C5 C 0.18786(14) 0.2566(2) 0.72675(12) 0.0179(4) Uani 1 1 d . . . . .
H5 H 0.186959 0.177365 0.774439 0.021 Uiso 1 1 calc R U . . .
C6 C 0.10333(14) 0.3516(2) 0.71614(13) 0.0176(4) Uani 1 1 d . . . . .
H6 H 0.045605 0.338741 0.756207 0.021 Uiso 1 1 calc R U . . .
C7 C 0.10362(13) 0.4692(2) 0.64446(12) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.02332(13) 0.5786(2) 0.62601(13) 0.0162(4) Uani 1 1 d . . . . .
H8 H -0.037142 0.575877 0.663217 0.019 Uiso 1 1 calc R U . . .
C9 C 0.03284(13) 0.6882(2) 0.55467(13) 0.0155(4) Uani 1 1 d . . . . .
H9 H -0.020177 0.762357 0.542903 0.019 Uiso 1 1 calc R U . . .
C10 C 0.12239(12) 0.6889(2) 0.49923(12) 0.0112(3) Uani 1 1 d . . . . .
C11 C 0.14181(12) 0.7995(2) 0.41593(12) 0.0128(3) Uani 1 1 d . . . . .
H11 H 0.103299 0.760816 0.359195 0.015 Uiso 1 1 calc R U . . .
C12 C 0.19548(14) 1.0536(2) 0.45114(16) 0.0231(4) Uani 1 1 d . . . . .
H12A H 0.192002 1.107257 0.513424 0.028 Uiso 1 1 calc R U . . .
H12B H 0.198210 1.134856 0.400753 0.028 Uiso 1 1 calc R U . . .
C13 C 0.29020(13) 0.9464(2) 0.44630(13) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.32283(14) 0.8967(2) 0.54634(13) 0.0164(4) Uani 1 1 d . . . . .
H14A H 0.361996 0.983435 0.576352 0.020 Uiso 1 1 calc R U . . .
H14B H 0.261316 0.876722 0.585344 0.020 Uiso 1 1 calc R U . . .
C15 C 0.37895(14) 1.0201(2) 0.39140(14) 0.0184(4) Uani 1 1 d . . . . .
H15A H 0.431348 0.938440 0.378748 0.022 Uiso 1 1 calc R U . . .
H15B H 0.353730 1.059939 0.329645 0.022 Uiso 1 1 calc R U . . .
C16 C 0.48023(16) 0.5610(3) 0.27980(14) 0.0290(5) Uani 1 1 d . . . . .
H16A H 0.545438 0.602753 0.256610 0.043 Uiso 1 1 calc R U . . .
H16B H 0.424527 0.598878 0.239185 0.043 Uiso 1 1 calc R U . . .
H16C H 0.482012 0.445336 0.278412 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.9792(14) . ?
Ni1 O2 2.0475(13) . ?
Ni1 O1 2.1066(12) . ?
Ni1 O3 2.1127(12) . ?
Ni1 N2 2.1672(14) . ?
Ni1 Cl1 2.3883(5) . ?
O1 C3 1.333(2) . ?
O2 C16 1.428(2) . ?
O2 H2 0.80(3) . ?
O3 C14 1.428(2) . ?
O3 H3A 0.82(3) . ?
O4 C11 1.416(2) . ?
O4 C12 1.416(2) . ?
O5 C15 1.421(2) . ?
O5 H5A 0.67(3) . ?
N1 C10 1.311(2) . ?
N1 C2 1.355(2) . ?
N2 C11 1.475(2) . ?
N2 C13 1.494(2) . ?
N2 H3 0.81(2) . ?
C2 C7 1.411(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.425(2) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.524(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.538(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.529(3) . ?
C13 C14 1.532(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 O2 175.45(6) . . ?
N1 Ni1 O1 80.16(5) . . ?
O2 Ni1 O1 101.36(5) . . ?
N1 Ni1 O3 88.54(5) . . ?
O2 Ni1 O3 87.19(5) . . ?
O1 Ni1 O3 89.59(5) . . ?
N1 Ni1 N2 78.00(6) . . ?
O2 Ni1 N2 99.72(5) . . ?
O1 Ni1 N2 156.10(5) . . ?
O3 Ni1 N2 80.29(5) . . ?
N1 Ni1 Cl1 90.91(4) . . ?
O2 Ni1 Cl1 93.31(4) . . ?
O1 Ni1 Cl1 92.35(4) . . ?
O3 Ni1 Cl1 177.86(4) . . ?
N2 Ni1 Cl1 97.57(4) . . ?
C3 O1 Ni1 110.92(10) . . ?
C16 O2 Ni1 123.70(12) . . ?
C16 O2 H2 109.2(17) . . ?
Ni1 O2 H2 118.8(17) . . ?
C14 O3 Ni1 111.31(10) . . ?
C14 O3 H3A 109.0(17) . . ?
Ni1 O3 H3A 124.5(17) . . ?
C11 O4 C12 109.80(13) . . ?
C15 O5 H5A 115(3) . . ?
C10 N1 C2 121.54(15) . . ?
C10 N1 Ni1 122.54(12) . . ?
C2 N1 Ni1 115.88(11) . . ?
C11 N2 C13 104.27(13) . . ?
C11 N2 Ni1 110.19(10) . . ?
C13 N2 Ni1 110.43(10) . . ?
C11 N2 H3 108.8(16) . . ?
C13 N2 H3 107.0(16) . . ?
Ni1 N2 H3 115.5(16) . . ?
N1 C2 C7 121.46(15) . . ?
N1 C2 C3 115.09(15) . . ?
C7 C2 C3 123.44(15) . . ?
O1 C3 C4 125.79(16) . . ?
O1 C3 C2 117.94(15) . . ?
C4 C3 C2 116.27(16) . . ?
C3 C4 C5 120.74(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.70(17) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 119.02(17) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 117.81(16) . . ?
C2 C7 C8 116.45(16) . . ?
C6 C7 C8 125.73(16) . . ?
C9 C8 C7 120.36(16) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.04(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N1 C10 C9 121.13(16) . . ?
N1 C10 C11 114.13(14) . . ?
C9 C10 C11 124.74(15) . . ?
O4 C11 N2 108.10(13) . . ?
O4 C11 C10 110.42(14) . . ?
N2 C11 C10 110.36(13) . . ?
O4 C11 H11 109.3 . . ?
N2 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
O4 C12 C13 106.61(14) . . ?
O4 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O4 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
N2 C13 C15 109.22(14) . . ?
N2 C13 C14 109.30(14) . . ?
C15 C13 C14 111.57(15) . . ?
N2 C13 C12 103.02(14) . . ?
C15 C13 C12 113.19(15) . . ?
C14 C13 C12 110.16(15) . . ?
O3 C14 C13 110.91(14) . . ?
O3 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
O5 C15 C13 111.10(16) . . ?
O5 C15 H15A 109.4 . . ?
C13 C15 H15A 109.4 . . ?
O5 C15 H15B 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C10 N1 C2 C7 0.7(2) . . . . ?
Ni1 N1 C2 C7 178.53(12) . . . . ?
C10 N1 C2 C3 -178.11(15) . . . . ?
Ni1 N1 C2 C3 -0.32(18) . . . . ?
Ni1 O1 C3 C4 -179.98(14) . . . . ?
Ni1 O1 C3 C2 0.21(18) . . . . ?
N1 C2 C3 O1 0.1(2) . . . . ?
C7 C2 C3 O1 -178.77(15) . . . . ?
N1 C2 C3 C4 -179.77(15) . . . . ?
C7 C2 C3 C4 1.4(2) . . . . ?
O1 C3 C4 C5 -179.82(16) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
N1 C2 C7 C6 179.48(16) . . . . ?
C3 C2 C7 C6 -1.8(2) . . . . ?
N1 C2 C7 C8 -1.2(2) . . . . ?
C3 C2 C7 C8 177.53(16) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C6 C7 C8 -178.51(17) . . . . ?
C2 C7 C8 C9 0.3(2) . . . . ?
C6 C7 C8 C9 179.56(17) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C2 N1 C10 C9 0.7(2) . . . . ?
Ni1 N1 C10 C9 -176.97(12) . . . . ?
C2 N1 C10 C11 -178.75(14) . . . . ?
Ni1 N1 C10 C11 3.6(2) . . . . ?
C8 C9 C10 N1 -1.5(3) . . . . ?
C8 C9 C10 C11 177.82(16) . . . . ?
C12 O4 C11 N2 -12.3(2) . . . . ?
C12 O4 C11 C10 108.50(17) . . . . ?
C13 N2 C11 O4 25.84(17) . . . . ?
Ni1 N2 C11 O4 144.35(11) . . . . ?
C13 N2 C11 C10 -95.01(15) . . . . ?
Ni1 N2 C11 C10 23.49(16) . . . . ?
N1 C10 C11 O4 -138.10(15) . . . . ?
C9 C10 C11 O4 42.5(2) . . . . ?
N1 C10 C11 N2 -18.6(2) . . . . ?
C9 C10 C11 N2 161.96(16) . . . . ?
C11 O4 C12 C13 -6.1(2) . . . . ?
C11 N2 C13 C15 -148.68(14) . . . . ?
Ni1 N2 C13 C15 92.98(14) . . . . ?
C11 N2 C13 C14 89.00(15) . . . . ?
Ni1 N2 C13 C14 -29.33(16) . . . . ?
C11 N2 C13 C12 -28.11(17) . . . . ?
Ni1 N2 C13 C12 -146.45(12) . . . . ?
O4 C12 C13 N2 21.5(2) . . . . ?
O4 C12 C13 C15 139.33(16) . . . . ?
O4 C12 C13 C14 -94.99(18) . . . . ?
Ni1 O3 C14 C13 -40.97(16) . . . . ?
N2 C13 C14 O3 46.73(19) . . . . ?
C15 C13 C14 O3 -74.17(18) . . . . ?
C12 C13 C14 O3 159.23(14) . . . . ?
N2 C13 C15 O5 -174.67(14) . . . . ?
C14 C13 C15 O5 -53.7(2) . . . . ?
C12 C13 C15 O5 71.2(2) . . . . ?

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
_geom_hbond_publ_flag
O2 H2 O1 0.80(3) 1.82(3) 2.6167(18) 173(2) 3_666 yes
O3 H3A O5 0.82(3) 1.83(3) 2.6440(19) 176(2) 3_676 yes
O5 H5A Cl1 0.67(3) 3.00(3) 3.5246(17) 137(3) 1_565 yes
O5 H5A O1 0.67(3) 2.17(3) 2.746(2) 145(3) 1_565 yes

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.082

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

data_cmpd_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1832156'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
; 
;
_chemical_name_common            cmpd_2
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Cl Co N2 O5'
_chemical_formula_sum            'C15 H19 Cl Co N2 O5'
_chemical_formula_weight         401.70

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'
Cl Cl 0.1484 0.1585 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.1024(5)
_cell_length_b                   8.5218(3)
_cell_length_c                   14.1371(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.3820(10)
_cell_angle_gamma                90
_cell_volume                     1578.46(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.8514
_cell_measurement_theta_max      27.4995

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    1.286
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            16727
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3618
_reflns_number_gt                3151
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'PLATON (Spek, 2003)'
_refine_special_details          
; 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+1.4544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Co1 Co 0.32908(2) 0.58525(3) 0.44186(2) 0.01171(8) Uani 1 1 d . . . . .
Cl1 Cl 0.25776(3) 0.40406(5) 0.32792(3) 0.01856(10) Uani 1 1 d . . . . .
O1 O 0.35751(9) 0.40846(15) 0.54408(9) 0.0166(3) Uani 1 1 d . . . . .
O2 O 0.46559(10) 0.60396(16) 0.37234(9) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.521(2) 0.599(3) 0.4051(19) 0.039(7) Uiso 1 1 d . . . . .
O3 O 0.38971(10) 0.75631(16) 0.54118(9) 0.0177(3) Uani 1 1 d . . . . .
H3A H 0.4465(19) 0.784(3) 0.5443(18) 0.031(7) Uiso 1 1 d . . . . .
H3 H 0.2562(16) 0.819(3) 0.3384(17) 0.022(6) Uiso 1 1 d . . . . .
O4 O 0.10793(10) 0.95010(16) 0.43859(12) 0.0264(3) Uani 1 1 d . . . . .
O5 O 0.41948(12) 1.14390(19) 0.44458(15) 0.0382(4) Uani 1 1 d . . . . .
H5A H 0.388(3) 1.210(5) 0.446(3) 0.089(14) Uiso 1 1 d . . . . .
N1 N 0.19551(10) 0.58548(16) 0.51620(10) 0.0118(3) Uani 1 1 d . . . . .
N2 N 0.25055(11) 0.80221(17) 0.39622(11) 0.0125(3) Uani 1 1 d . . . . .
C2 C 0.18901(12) 0.4792(2) 0.58722(12) 0.0124(3) Uani 1 1 d . . . . .
C3 C 0.27777(13) 0.3829(2) 0.60012(12) 0.0137(3) Uani 1 1 d . . . . .
C4 C 0.27308(14) 0.2711(2) 0.67132(13) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.329834 0.204111 0.682461 0.021 Uiso 1 1 calc R U . . .
C5 C 0.18499(15) 0.2560(2) 0.72734(13) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.183518 0.176748 0.774572 0.025 Uiso 1 1 calc R U . . .
C6 C 0.10118(14) 0.3514(2) 0.71628(13) 0.0203(4) Uani 1 1 d . . . . .
H6 H 0.043570 0.339295 0.756069 0.024 Uiso 1 1 calc R U . . .
C7 C 0.10176(13) 0.4680(2) 0.64476(12) 0.0159(4) Uani 1 1 d . . . . .
C8 C 0.02254(13) 0.5778(2) 0.62615(13) 0.0190(4) Uani 1 1 d . . . . .
H8 H -0.037700 0.575551 0.663154 0.023 Uiso 1 1 calc R U . . .
C9 C 0.03194(13) 0.6868(2) 0.55545(13) 0.0177(4) Uani 1 1 d . . . . .
H9 H -0.020515 0.761551 0.543977 0.021 Uiso 1 1 calc R U . . .
C10 C 0.12127(12) 0.6858(2) 0.50002(12) 0.0131(3) Uani 1 1 d . . . . .
C11 C 0.14046(13) 0.7960(2) 0.41735(13) 0.0150(3) Uani 1 1 d . . . . .
H11 H 0.102521 0.757083 0.360398 0.018 Uiso 1 1 calc R U . . .
C12 C 0.19315(15) 1.0461(2) 0.45784(17) 0.0285(5) Uani 1 1 d . . . . .
H12A H 0.188671 1.090283 0.522439 0.034 Uiso 1 1 calc R U . . .
H12B H 0.196151 1.133850 0.412068 0.034 Uiso 1 1 calc R U . . .
C13 C 0.28868(13) 0.9418(2) 0.44904(13) 0.0172(4) Uani 1 1 d . . . . .
C14 C 0.32528(14) 0.8911(2) 0.54720(13) 0.0201(4) Uani 1 1 d . . . . .
H14A H 0.363304 0.978316 0.577405 0.024 Uiso 1 1 calc R U . . .
H14B H 0.265584 0.866545 0.587133 0.024 Uiso 1 1 calc R U . . .
C15 C 0.37477(14) 1.0181(2) 0.39304(15) 0.0233(4) Uani 1 1 d . . . . .
H15A H 0.427639 0.938601 0.378993 0.028 Uiso 1 1 calc R U . . .
H15B H 0.347465 1.057940 0.332151 0.028 Uiso 1 1 calc R U . . .
C16 C 0.48155(16) 0.5566(3) 0.27672(14) 0.0285(5) Uani 1 1 d . . . . .
H16A H 0.545465 0.602012 0.253724 0.043 Uiso 1 1 calc R U . . .
H16B H 0.424641 0.593360 0.237226 0.043 Uiso 1 1 calc R U . . .
H16C H 0.485510 0.441872 0.273564 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.0474(14) . ?
Co1 O2 2.0528(13) . ?
Co1 O1 2.1189(12) . ?
Co1 O3 2.1708(13) . ?
Co1 N2 2.2100(15) . ?
Co1 Cl1 2.4150(5) . ?
O1 C3 1.333(2) . ?
O2 C16 1.428(2) . ?
O2 H2 0.86(3) . ?
O3 C14 1.428(2) . ?
O3 H3A 0.78(3) . ?
O4 C12 1.409(2) . ?
O4 C11 1.414(2) . ?
O5 C15 1.420(3) . ?
O5 H5A 0.70(4) . ?
N1 C10 1.314(2) . ?
N1 C2 1.356(2) . ?
N2 C11 1.476(2) . ?
N2 C13 1.489(2) . ?
N2 H3 0.83(2) . ?
C2 C7 1.411(2) . ?
C2 C3 1.434(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.410(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.421(3) . ?
C8 C9 1.371(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.521(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.541(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 C15 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 O2 174.99(6) . . ?
N1 Co1 O1 78.32(5) . . ?
O2 Co1 O1 103.41(5) . . ?
N1 Co1 O3 88.72(5) . . ?
O2 Co1 O3 86.63(5) . . ?
O1 Co1 O3 88.54(5) . . ?
N1 Co1 N2 75.59(5) . . ?
O2 Co1 N2 101.58(5) . . ?
O1 Co1 N2 150.85(5) . . ?
O3 Co1 N2 78.15(5) . . ?
N1 Co1 Cl1 90.85(4) . . ?
O2 Co1 Cl1 93.71(4) . . ?
O1 Co1 Cl1 93.77(4) . . ?
O3 Co1 Cl1 177.52(4) . . ?
N2 Co1 Cl1 99.37(4) . . ?
C3 O1 Co1 112.74(10) . . ?
C16 O2 Co1 124.41(11) . . ?
C16 O2 H2 111.3(18) . . ?
Co1 O2 H2 118.5(18) . . ?
C14 O3 Co1 111.39(10) . . ?
C14 O3 H3A 108.5(19) . . ?
Co1 O3 H3A 125.6(19) . . ?
C12 O4 C11 109.91(13) . . ?
C15 O5 H5A 113(3) . . ?
C10 N1 C2 120.91(15) . . ?
C10 N1 Co1 123.07(12) . . ?
C2 N1 Co1 115.96(11) . . ?
C11 N2 C13 104.61(13) . . ?
C11 N2 Co1 111.38(10) . . ?
C13 N2 Co1 111.59(10) . . ?
C11 N2 H3 107.3(15) . . ?
C13 N2 H3 108.6(16) . . ?
Co1 N2 H3 112.9(16) . . ?
N1 C2 C7 121.83(16) . . ?
N1 C2 C3 114.94(15) . . ?
C7 C2 C3 123.22(16) . . ?
O1 C3 C4 125.59(16) . . ?
O1 C3 C2 117.97(15) . . ?
C4 C3 C2 116.43(16) . . ?
C3 C4 C5 120.71(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.58(17) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 119.18(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 117.82(16) . . ?
C2 C7 C8 116.28(16) . . ?
C6 C7 C8 125.89(17) . . ?
C9 C8 C7 120.82(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 118.61(16) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N1 C10 C9 121.51(16) . . ?
N1 C10 C11 114.17(14) . . ?
C9 C10 C11 124.32(15) . . ?
O4 C11 N2 107.82(13) . . ?
O4 C11 C10 111.02(15) . . ?
N2 C11 C10 110.14(13) . . ?
O4 C11 H11 109.3 . . ?
N2 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
O4 C12 C13 107.03(15) . . ?
O4 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O4 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
N2 C13 C14 109.37(15) . . ?
N2 C13 C15 109.06(15) . . ?
C14 C13 C15 111.27(15) . . ?
N2 C13 C12 103.37(14) . . ?
C14 C13 C12 109.88(16) . . ?
C15 C13 C12 113.55(16) . . ?
O3 C14 C13 110.82(14) . . ?
O3 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O5 C15 C13 111.02(17) . . ?
O5 C15 H15A 109.4 . . ?
C13 C15 H15A 109.4 . . ?
O5 C15 H15B 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C10 N1 C2 C7 2.0(2) . . . . ?
Co1 N1 C2 C7 179.22(13) . . . . ?
C10 N1 C2 C3 -176.71(15) . . . . ?
Co1 N1 C2 C3 0.54(19) . . . . ?
Co1 O1 C3 C4 177.93(14) . . . . ?
Co1 O1 C3 C2 -2.74(19) . . . . ?
N1 C2 C3 O1 1.5(2) . . . . ?
C7 C2 C3 O1 -177.12(16) . . . . ?
N1 C2 C3 C4 -179.06(15) . . . . ?
C7 C2 C3 C4 2.3(2) . . . . ?
O1 C3 C4 C5 179.04(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
N1 C2 C7 C6 178.95(16) . . . . ?
C3 C2 C7 C6 -2.5(3) . . . . ?
N1 C2 C7 C8 -2.0(2) . . . . ?
C3 C2 C7 C8 176.56(16) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C6 C7 C8 -178.27(18) . . . . ?
C2 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C9 179.30(18) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C2 N1 C10 C9 -0.2(2) . . . . ?
Co1 N1 C10 C9 -177.23(13) . . . . ?
C2 N1 C10 C11 -179.56(15) . . . . ?
Co1 N1 C10 C11 3.4(2) . . . . ?
C8 C9 C10 N1 -1.5(3) . . . . ?
C8 C9 C10 C11 177.86(16) . . . . ?
C12 O4 C11 N2 -16.0(2) . . . . ?
C12 O4 C11 C10 104.68(18) . . . . ?
C13 N2 C11 O4 26.37(18) . . . . ?
Co1 N2 C11 O4 147.07(11) . . . . ?
C13 N2 C11 C10 -94.90(16) . . . . ?
Co1 N2 C11 C10 25.79(16) . . . . ?
N1 C10 C11 O4 -139.19(15) . . . . ?
C9 C10 C11 O4 41.4(2) . . . . ?
N1 C10 C11 N2 -19.8(2) . . . . ?
C9 C10 C11 N2 160.79(16) . . . . ?
C11 O4 C12 C13 -0.7(2) . . . . ?
C11 N2 C13 C14 91.48(16) . . . . ?
Co1 N2 C13 C14 -29.08(16) . . . . ?
C11 N2 C13 C15 -146.62(14) . . . . ?
Co1 N2 C13 C15 92.82(14) . . . . ?
C11 N2 C13 C12 -25.52(18) . . . . ?
Co1 N2 C13 C12 -146.08(13) . . . . ?
O4 C12 C13 N2 16.7(2) . . . . ?
O4 C12 C13 C14 -99.93(19) . . . . ?
O4 C12 C13 C15 134.72(18) . . . . ?
Co1 O3 C14 C13 -42.81(17) . . . . ?
N2 C13 C14 O3 47.67(19) . . . . ?
C15 C13 C14 O3 -72.9(2) . . . . ?
C12 C13 C14 O3 160.48(15) . . . . ?
N2 C13 C15 O5 -174.96(15) . . . . ?
C14 C13 C15 O5 -54.2(2) . . . . ?
C12 C13 C15 O5 70.4(2) . . . . ?

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
_geom_hbond_publ_flag
O2 H2 O1 0.86(3) 1.74(3) 2.5967(18) 172(3) 3_666 yes
O3 H3A O5 0.78(3) 1.87(3) 2.647(2) 178(3) 3_676 yes
O5 H5A Cl1 0.70(4) 2.90(4) 3.4754(19) 142(4) 1_565 yes
O5 H5A O1 0.70(4) 2.22(4) 2.781(2) 138(4) 1_565 yes

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_cmpd_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1832158'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
; 
;
_chemical_name_common            cmpd_4
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl N2 O4 Zn'
_chemical_formula_sum            'C14 H15 Cl N2 O4 Zn'
_chemical_formula_weight         376.10

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   11.0694(5)
_cell_length_b                   9.1258(4)
_cell_length_c                   13.8053(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.676(2)
_cell_angle_gamma                90
_cell_volume                     1393.98(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8865
_cell_measurement_theta_min      2.6759
_cell_measurement_theta_max      27.4926

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    1.974
_shelx_estimated_absorpt_T_min   0.553
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            17433
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3200
_reflns_number_gt                2759
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0234P)²+1.5035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3200
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Zn1 Zn 0.29609(2) 0.57777(2) 0.53784(2) 0.01169(7) Uani 1 1 d . . . . .
Cl1 Cl 0.21275(4) 0.43160(5) 0.64834(3) 0.01693(11) Uani 1 1 d . . . . .
O1 O 0.45255(12) 0.65294(15) 0.60709(10) 0.0139(3) Uani 1 1 d . . . . .
O3 O 0.35830(13) 0.48336(17) 0.41830(10) 0.0174(3) Uani 1 1 d . . . . .
H3A H 0.424(2) 0.438(3) 0.4101(19) 0.029(7) Uiso 1 1 d . . . . .
O4 O 0.11148(13) 0.78149(15) 0.31433(10) 0.0173(3) Uani 1 1 d . . . . .
O5 O 0.01302(14) 0.35295(17) 0.38123(11) 0.0209(3) Uani 1 1 d . . . . .
H5A H -0.047(3) 0.396(4) 0.347(2) 0.060(10) Uiso 1 1 d . . . . .
N1 N 0.27449(14) 0.79819(18) 0.52052(11) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.13394(15) 0.60228(18) 0.43425(12) 0.0130(3) Uani 1 1 d . . . . .
H2A H 0.068(3) 0.556(3) 0.4551(19) 0.033(7) Uiso 1 1 d . . . . .
C2 C 0.35968(17) 0.8798(2) 0.56803(13) 0.0116(4) Uani 1 1 d . . . . .
C3 C 0.45545(17) 0.7986(2) 0.61504(13) 0.0120(4) Uani 1 1 d . . . . .
C4 C 0.54344(18) 0.8789(2) 0.66454(14) 0.0153(4) Uani 1 1 d . . . . .
H4 H 0.607502 0.829461 0.698149 0.018 Uiso 1 1 calc R U . . .
C5 C 0.53912(18) 1.0334(2) 0.66567(14) 0.0169(4) Uani 1 1 d . . . . .
H5 H 0.601255 1.085306 0.699951 0.020 Uiso 1 1 calc R U . . .
C6 C 0.44873(19) 1.1118(2) 0.61924(14) 0.0169(4) Uani 1 1 d . . . . .
H6 H 0.448671 1.215829 0.621090 0.020 Uiso 1 1 calc R U . . .
C7 C 0.35528(18) 1.0344(2) 0.56837(14) 0.0136(4) Uani 1 1 d . . . . .
C8 C 0.25703(19) 1.0993(2) 0.51580(14) 0.0172(4) Uani 1 1 d . . . . .
H8 H 0.248737 1.202959 0.514974 0.021 Uiso 1 1 calc R U . . .
C9 C 0.17374(18) 1.0141(2) 0.46608(14) 0.0161(4) Uani 1 1 d . . . . .
H9 H 0.109163 1.058070 0.429765 0.019 Uiso 1 1 calc R U . . .
C10 C 0.18564(17) 0.8603(2) 0.46979(13) 0.0131(4) Uani 1 1 d . . . . .
C11 C 0.10042(17) 0.7559(2) 0.41593(14) 0.0141(4) Uani 1 1 d . . . . .
H11 H 0.015317 0.773742 0.435281 0.017 Uiso 1 1 calc R U . . .
C12 C 0.10571(18) 0.6410(2) 0.26733(14) 0.0160(4) Uani 1 1 d . . . . .
H12A H 0.149442 0.642671 0.205803 0.019 Uiso 1 1 calc R U . . .
H12B H 0.020817 0.611708 0.253532 0.019 Uiso 1 1 calc R U . . .
C13 C 0.16647(17) 0.5368(2) 0.33993(14) 0.0142(4) Uani 1 1 d . . . . .
C14 C 0.30400(18) 0.5414(2) 0.33130(14) 0.0172(4) Uani 1 1 d . . . . .
H14A H 0.328425 0.482410 0.274942 0.021 Uiso 1 1 calc R U . . .
H14B H 0.331055 0.643570 0.321578 0.021 Uiso 1 1 calc R U . . .
C15 C 0.12259(18) 0.3775(2) 0.33287(15) 0.0176(4) Uani 1 1 d . . . . .
H15A H 0.110785 0.351013 0.263696 0.021 Uiso 1 1 calc R U . . .
H15B H 0.185877 0.312331 0.361094 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 2.0015(14) . ?
Zn1 N1 2.0389(16) . ?
Zn1 O1 2.0706(13) . ?
Zn1 Cl1 2.2449(5) . ?
Zn1 N2 2.2730(16) . ?
O1 C3 1.334(2) . ?
O3 C14 1.429(2) . ?
O3 H3A 0.85(3) . ?
O4 C11 1.431(2) . ?
O4 C12 1.438(2) . ?
O5 C15 1.419(3) . ?
O5 H5A 0.90(3) . ?
N1 C10 1.318(2) . ?
N1 C2 1.356(2) . ?
N2 C11 1.471(2) . ?
N2 C13 1.487(2) . ?
N2 H2A 0.90(3) . ?
C2 C7 1.411(3) . ?
C2 C3 1.433(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.411(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.519(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.531(3) . ?
C13 C15 1.535(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Zn1 N1 111.71(6) . . ?
O3 Zn1 O1 102.71(6) . . ?
N1 Zn1 O1 79.68(6) . . ?
O3 Zn1 Cl1 117.56(5) . . ?
N1 Zn1 Cl1 128.08(5) . . ?
O1 Zn1 Cl1 103.76(4) . . ?
O3 Zn1 N2 78.93(6) . . ?
N1 Zn1 N2 75.01(6) . . ?
O1 Zn1 N2 153.17(6) . . ?
Cl1 Zn1 N2 98.82(5) . . ?
C3 O1 Zn1 112.70(11) . . ?
C14 O3 Zn1 112.78(12) . . ?
C14 O3 H3A 114.2(18) . . ?
Zn1 O3 H3A 129.6(18) . . ?
C11 O4 C12 107.05(14) . . ?
C15 O5 H5A 109(2) . . ?
C10 N1 C2 121.24(17) . . ?
C10 N1 Zn1 124.69(13) . . ?
C2 N1 Zn1 114.06(12) . . ?
C11 N2 C13 107.39(15) . . ?
C11 N2 Zn1 113.12(12) . . ?
C13 N2 Zn1 107.73(11) . . ?
C11 N2 H2A 107.5(18) . . ?
C13 N2 H2A 108.2(17) . . ?
Zn1 N2 H2A 112.7(17) . . ?
N1 C2 C7 121.80(17) . . ?
N1 C2 C3 115.47(17) . . ?
C7 C2 C3 122.71(17) . . ?
O1 C3 C4 125.69(18) . . ?
O1 C3 C2 117.52(17) . . ?
C4 C3 C2 116.79(18) . . ?
C3 C4 C5 120.75(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.67(19) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 118.79(19) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C8 116.23(18) . . ?
C2 C7 C6 118.27(18) . . ?
C8 C7 C6 125.49(19) . . ?
C9 C8 C7 120.76(18) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 118.99(18) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N1 C10 C9 120.94(18) . . ?
N1 C10 C11 115.70(17) . . ?
C9 C10 C11 123.35(17) . . ?
O4 C11 N2 107.20(15) . . ?
O4 C11 C10 107.94(15) . . ?
N2 C11 C10 111.31(15) . . ?
O4 C11 H11 110.1 . . ?
N2 C11 H11 110.1 . . ?
C10 C11 H11 110.1 . . ?
O4 C12 C13 104.28(15) . . ?
O4 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
O4 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
N2 C13 C12 102.24(15) . . ?
N2 C13 C14 108.92(15) . . ?
C12 C13 C14 110.66(16) . . ?
N2 C13 C15 110.60(16) . . ?
C12 C13 C15 114.60(16) . . ?
C14 C13 C15 109.52(16) . . ?
O3 C14 C13 108.62(16) . . ?
O3 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
O5 C15 C13 113.13(17) . . ?
O5 C15 H15A 109.0 . . ?
C13 C15 H15A 109.0 . . ?
O5 C15 H15B 109.0 . . ?
C13 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?

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
C10 N1 C2 C7 2.2(3) . . . . ?
Zn1 N1 C2 C7 -176.60(14) . . . . ?
C10 N1 C2 C3 -176.05(17) . . . . ?
Zn1 N1 C2 C3 5.1(2) . . . . ?
Zn1 O1 C3 C4 174.45(15) . . . . ?
Zn1 O1 C3 C2 -5.8(2) . . . . ?
N1 C2 C3 O1 0.6(2) . . . . ?
C7 C2 C3 O1 -177.67(17) . . . . ?
N1 C2 C3 C4 -179.69(16) . . . . ?
C7 C2 C3 C4 2.1(3) . . . . ?
O1 C3 C4 C5 178.11(18) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
N1 C2 C7 C8 -0.3(3) . . . . ?
C3 C2 C7 C8 177.85(18) . . . . ?
N1 C2 C7 C6 -179.45(17) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C5 C6 C7 C8 -179.00(19) . . . . ?
C2 C7 C8 C9 -1.5(3) . . . . ?
C6 C7 C8 C9 177.59(19) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C2 N1 C10 C9 -2.3(3) . . . . ?
Zn1 N1 C10 C9 176.39(14) . . . . ?
C2 N1 C10 C11 176.88(16) . . . . ?
Zn1 N1 C10 C11 -4.4(2) . . . . ?
C8 C9 C10 N1 0.5(3) . . . . ?
C8 C9 C10 C11 -178.65(18) . . . . ?
C12 O4 C11 N2 21.13(19) . . . . ?
C12 O4 C11 C10 141.14(16) . . . . ?
C13 N2 C11 O4 0.44(19) . . . . ?
Zn1 N2 C11 O4 119.16(13) . . . . ?
C13 N2 C11 C10 -117.40(17) . . . . ?
Zn1 N2 C11 C10 1.33(19) . . . . ?
N1 C10 C11 O4 -115.81(18) . . . . ?
C9 C10 C11 O4 63.3(2) . . . . ?
N1 C10 C11 N2 1.6(2) . . . . ?
C9 C10 C11 N2 -179.28(18) . . . . ?
C11 O4 C12 C13 -33.77(19) . . . . ?
C11 N2 C13 C12 -20.11(19) . . . . ?
Zn1 N2 C13 C12 -142.26(12) . . . . ?
C11 N2 C13 C14 97.02(18) . . . . ?
Zn1 N2 C13 C14 -25.13(18) . . . . ?
C11 N2 C13 C15 -142.57(16) . . . . ?
Zn1 N2 C13 C15 95.29(15) . . . . ?
O4 C12 C13 N2 32.66(19) . . . . ?
O4 C12 C13 C14 -83.21(19) . . . . ?
O4 C12 C13 C15 152.35(16) . . . . ?
Zn1 O3 C14 C13 -51.58(18) . . . . ?
N2 C13 C14 O3 49.3(2) . . . . ?
C12 C13 C14 O3 160.96(16) . . . . ?
C15 C13 C14 O3 -71.8(2) . . . . ?
N2 C13 C15 O5 33.3(2) . . . . ?
C12 C13 C15 O5 -81.6(2) . . . . ?
C14 C13 C15 O5 153.39(16) . . . . ?

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
_geom_hbond_publ_flag
O3 H3A O1 0.85(3) 1.62(3) 2.4693(19) 178(3) 3_666 yes
O5 H5A Cl1 0.90(3) 2.41(4) 3.1967(17) 146(3) 3_566 yes
O5 H5A O4 0.90(3) 2.55(3) 3.065(2) 117(3) 2_545 yes
N2 H2A O5 0.90(3) 2.19(3) 2.729(2) 118(2) . yes
N2 H2A O5 0.90(3) 2.59(3) 3.089(2) 116(2) 3_566 yes

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_cmpd_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1832155'
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
; 
;
_chemical_name_common            cmpd_1
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Cl Mn N2 O5'
_chemical_formula_sum            'C15 H19 Cl Mn N2 O5'
_chemical_formula_weight         397.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.1683(5)
_cell_length_b                   8.5529(3)
_cell_length_c                   14.3906(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.695(2)
_cell_angle_gamma                90
_cell_volume                     1620.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.7707
_cell_measurement_theta_max      27.4977

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.008
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            20227
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3715
_reflns_number_gt                3199
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0262P)²+1.5380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.33123(2) 0.57350(3) 0.43981(2) 0.01325(8) Uani 1 1 d . . . . .
Cl1 Cl 0.25625(3) 0.39629(5) 0.32242(3) 0.02063(11) Uani 1 1 d . . . . .
O1 O 0.34899(9) 0.39304(14) 0.54755(8) 0.0169(3) Uani 1 1 d . . . . .
O2 O 0.47123(10) 0.60339(16) 0.36985(9) 0.0214(3) Uani 1 1 d . . . . .
H2 H 0.531(2) 0.604(3) 0.3994(17) 0.038(7) Uiso 1 1 d . . . . .
O3 O 0.39234(10) 0.75551(15) 0.54169(8) 0.0173(3) Uani 1 1 d . . . . .
H3A H 0.4522(19) 0.790(3) 0.5434(16) 0.033(6) Uiso 1 1 d . . . . .
H3 H 0.2515(15) 0.826(2) 0.3430(15) 0.019(5) Uiso 1 1 d . . . . .
O4 O 0.10581(10) 0.95264(15) 0.44036(11) 0.0268(3) Uani 1 1 d . . . . .
N1 N 0.19215(10) 0.58520(16) 0.51811(9) 0.0130(3) Uani 1 1 d . . . . .
N2 N 0.24598(11) 0.80558(17) 0.39892(10) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.18453(13) 0.48002(19) 0.58820(11) 0.0133(3) Uani 1 1 d . . . . .
C3 C 0.26998(13) 0.3780(2) 0.60277(11) 0.0147(3) Uani 1 1 d . . . . .
C4 C 0.26380(14) 0.2694(2) 0.67400(12) 0.0177(4) Uani 1 1 d . . . . .
H4 H 0.318914 0.199924 0.686184 0.021 Uiso 1 1 calc R U . . .
C5 C 0.17678(14) 0.2607(2) 0.72847(12) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.174194 0.183588 0.775855 0.025 Uiso 1 1 calc R U . . .
C6 C 0.09566(14) 0.3598(2) 0.71545(12) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.038391 0.351929 0.753809 0.025 Uiso 1 1 calc R U . . .
C7 C 0.09817(13) 0.4737(2) 0.64433(12) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.02078(14) 0.5861(2) 0.62437(13) 0.0206(4) Uani 1 1 d . . . . .
H8 H -0.038966 0.586777 0.659786 0.025 Uiso 1 1 calc R U . . .
C9 C 0.03164(13) 0.6932(2) 0.55460(13) 0.0200(4) Uani 1 1 d . . . . .
H9 H -0.019393 0.769528 0.542293 0.024 Uiso 1 1 calc R U . . .
C10 C 0.11976(12) 0.6883(2) 0.50132(12) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.13783(13) 0.7984(2) 0.41992(12) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.098816 0.759708 0.363855 0.020 Uiso 1 1 calc R U . . .
C12 C 0.19112(15) 1.0449(2) 0.46531(16) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.186904 1.080631 0.530512 0.033 Uiso 1 1 calc R U . . .
H12B H 0.194453 1.137860 0.424534 0.033 Uiso 1 1 calc R U . . .
C13 C 0.28594(13) 0.9412(2) 0.45378(13) 0.0178(4) Uani 1 1 d . . . . .
C14 C 0.32513(14) 0.8854(2) 0.54945(12) 0.0202(4) Uani 1 1 d . . . . .
H14A H 0.361185 0.972279 0.581688 0.024 Uiso 1 1 calc R U . . .
H14B H 0.266811 0.854887 0.587357 0.024 Uiso 1 1 calc R U . . .
C15 C 0.37020(14) 1.0204(2) 0.40042(14) 0.0238(4) Uani 1 1 d D . . . .
H15A H 0.420436 0.941335 0.381445 0.029 Uiso 0.873(7) 1 calc R U P A 1
H15B H 0.341076 1.070309 0.343566 0.029 Uiso 0.873(7) 1 calc R U P A 1
H15C H 0.424866 0.940984 0.399664 0.029 Uiso 0.127(7) 1 calc R U P A 2
H15D H 0.342651 1.025465 0.335730 0.029 Uiso 0.127(7) 1 calc R U P A 2
C16 C 0.48329(15) 0.5621(3) 0.27435(13) 0.0287(5) Uani 1 1 d . . . . .
H16A H 0.544003 0.613338 0.250994 0.043 Uiso 1 1 calc R U . . .
H16B H 0.423437 0.596145 0.237654 0.043 Uiso 1 1 calc R U . . .
H16C H 0.490680 0.448419 0.269063 0.043 Uiso 1 1 calc R U . . .
O5 O 0.41959(12) 1.13672(19) 0.4583(2) 0.0229(6) Uani 0.873(7) 1 d D . P A 1
H5A H 0.377356 1.205836 0.472232 0.034 Uiso 0.873(7) 1 calc R U P A 1
O5A O 0.4196(9) 1.1547(13) 0.4116(15) 0.0229(6) Uani 0.127(7) 1 d D . P A 2
H5A1 H 0.377896 1.226652 0.421394 0.034 Uiso 0.127(7) 1 calc R U P 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
Mn1 O2 2.1417(13) . ?
Mn1 N1 2.1808(14) . ?
Mn1 O1 2.1953(12) . ?
Mn1 O3 2.2695(13) . ?
Mn1 N2 2.3468(14) . ?
Mn1 Cl1 2.4551(5) . ?
O1 C3 1.334(2) . ?
O2 C16 1.432(2) . ?
O2 H2 0.88(3) . ?
O3 C14 1.427(2) . ?
O3 H3A 0.84(2) . ?
O4 C12 1.410(2) . ?
O4 C11 1.418(2) . ?
N1 C10 1.316(2) . ?
N1 C2 1.357(2) . ?
N2 C11 1.466(2) . ?
N2 C13 1.491(2) . ?
N2 H3 0.83(2) . ?
C2 C7 1.415(2) . ?
C2 C3 1.434(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.527(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.544(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.526(3) . ?
C13 C14 1.532(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O5A 1.328(11) . ?
C15 O5 1.440(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O5 H5A 0.8400 . ?
O5A H5A1 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
O2 Mn1 N1 170.09(5) . . ?
O2 Mn1 O1 109.92(5) . . ?
N1 Mn1 O1 74.98(5) . . ?
O2 Mn1 O3 85.88(5) . . ?
N1 Mn1 O3 85.52(5) . . ?
O1 Mn1 O3 89.87(5) . . ?
O2 Mn1 N2 101.14(5) . . ?
N1 Mn1 N2 71.82(5) . . ?
O1 Mn1 N2 144.28(5) . . ?
O3 Mn1 N2 74.91(5) . . ?
O2 Mn1 Cl1 94.85(4) . . ?
N1 Mn1 Cl1 93.27(4) . . ?
O1 Mn1 Cl1 94.83(4) . . ?
O3 Mn1 Cl1 174.68(3) . . ?
N2 Mn1 Cl1 99.79(4) . . ?
C3 O1 Mn1 114.82(10) . . ?
C16 O2 Mn1 122.88(11) . . ?
C16 O2 H2 110.1(16) . . ?
Mn1 O2 H2 122.6(16) . . ?
C14 O3 Mn1 112.07(10) . . ?
C14 O3 H3A 107.9(17) . . ?
Mn1 O3 H3A 125.0(16) . . ?
C12 O4 C11 109.48(13) . . ?
C10 N1 C2 120.77(14) . . ?
C10 N1 Mn1 123.42(11) . . ?
C2 N1 Mn1 115.80(11) . . ?
C11 N2 C13 104.66(13) . . ?
C11 N2 Mn1 111.93(10) . . ?
C13 N2 Mn1 111.52(10) . . ?
C11 N2 H3 108.8(14) . . ?
C13 N2 H3 108.2(15) . . ?
Mn1 N2 H3 111.4(15) . . ?
N1 C2 C7 121.84(15) . . ?
N1 C2 C3 115.89(15) . . ?
C7 C2 C3 122.26(15) . . ?
O1 C3 C4 124.62(16) . . ?
O1 C3 C2 118.48(15) . . ?
C4 C3 C2 116.90(16) . . ?
C3 C4 C5 120.82(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.29(17) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 119.32(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 118.39(16) . . ?
C6 C7 C8 125.39(16) . . ?
C2 C7 C8 116.21(16) . . ?
C9 C8 C7 120.64(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 118.97(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N1 C10 C9 121.54(16) . . ?
N1 C10 C11 115.19(14) . . ?
C9 C10 C11 123.26(15) . . ?
O4 C11 N2 107.50(13) . . ?
O4 C11 C10 111.12(14) . . ?
N2 C11 C10 110.99(13) . . ?
O4 C11 H11 109.1 . . ?
N2 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
O4 C12 C13 106.98(14) . . ?
O4 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O4 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
N2 C13 C15 109.22(15) . . ?
N2 C13 C14 109.72(14) . . ?
C15 C13 C14 111.09(15) . . ?
N2 C13 C12 103.30(14) . . ?
C15 C13 C12 113.67(16) . . ?
C14 C13 C12 109.53(15) . . ?
O3 C14 C13 111.45(14) . . ?
O3 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
O3 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O5A C15 C13 133.2(8) . . ?
O5 C15 C13 109.76(19) . . ?
O5 C15 H15A 109.7 . . ?
C13 C15 H15A 109.7 . . ?
O5 C15 H15B 109.7 . . ?
C13 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O5A C15 H15C 103.9 . . ?
C13 C15 H15C 103.9 . . ?
O5A C15 H15D 103.9 . . ?
C13 C15 H15D 103.9 . . ?
H15C C15 H15D 105.4 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 O5 H5A 109.5 . . ?
C15 O5A H5A1 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
C10 N1 C2 C7 1.7(2) . . . . ?
Mn1 N1 C2 C7 -179.61(12) . . . . ?
C10 N1 C2 C3 -177.25(15) . . . . ?
Mn1 N1 C2 C3 1.48(19) . . . . ?
Mn1 O1 C3 C4 178.50(13) . . . . ?
Mn1 O1 C3 C2 -1.19(19) . . . . ?
N1 C2 C3 O1 -0.2(2) . . . . ?
C7 C2 C3 O1 -179.09(15) . . . . ?
N1 C2 C3 C4 -179.90(15) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
O1 C3 C4 C5 -179.38(16) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C6 C7 C8 -178.50(17) . . . . ?
N1 C2 C7 C6 179.44(16) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
N1 C2 C7 C8 -1.3(2) . . . . ?
C3 C2 C7 C8 177.55(16) . . . . ?
C6 C7 C8 C9 178.95(17) . . . . ?
C2 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C2 N1 C10 C9 -0.4(2) . . . . ?
Mn1 N1 C10 C9 -179.06(12) . . . . ?
C2 N1 C10 C11 -179.46(14) . . . . ?
Mn1 N1 C10 C11 1.9(2) . . . . ?
C8 C9 C10 N1 -1.1(3) . . . . ?
C8 C9 C10 C11 177.85(16) . . . . ?
C12 O4 C11 N2 -20.4(2) . . . . ?
C12 O4 C11 C10 101.18(17) . . . . ?
C13 N2 C11 O4 28.94(17) . . . . ?
Mn1 N2 C11 O4 149.88(11) . . . . ?
C13 N2 C11 C10 -92.77(16) . . . . ?
Mn1 N2 C11 C10 28.17(16) . . . . ?
N1 C10 C11 O4 -140.37(15) . . . . ?
C9 C10 C11 O4 40.6(2) . . . . ?
N1 C10 C11 N2 -20.8(2) . . . . ?
C9 C10 C11 N2 160.18(16) . . . . ?
C11 O4 C12 C13 3.6(2) . . . . ?
C11 N2 C13 C15 -146.76(14) . . . . ?
Mn1 N2 C13 C15 92.03(14) . . . . ?
C11 N2 C13 C14 91.25(16) . . . . ?
Mn1 N2 C13 C14 -29.96(16) . . . . ?
C11 N2 C13 C12 -25.47(18) . . . . ?
Mn1 N2 C13 C12 -146.69(12) . . . . ?
O4 C12 C13 N2 14.0(2) . . . . ?
O4 C12 C13 C15 132.19(17) . . . . ?
O4 C12 C13 C14 -102.90(18) . . . . ?
Mn1 O3 C14 C13 -45.23(17) . . . . ?
N2 C13 C14 O3 50.20(19) . . . . ?
C15 C13 C14 O3 -70.67(19) . . . . ?
C12 C13 C14 O3 162.93(15) . . . . ?
N2 C13 C15 O5A 169.1(10) . . . . ?
C14 C13 C15 O5A -69.7(10) . . . . ?
C12 C13 C15 O5A 54.4(10) . . . . ?
N2 C13 C15 O5 -171.53(15) . . . . ?
C14 C13 C15 O5 -50.4(2) . . . . ?
C12 C13 C15 O5 73.7(2) . . . . ?

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
_geom_hbond_publ_flag
O2 H2 O1 0.88(3) 1.74(3) 2.6177(18) 177(2) 3_666 yes
O3 H3A O5^a 0.84(2) 1.80(2) 2.643(2) 178(2) 3_676 yes
O3 H3A O5A^b 0.84(2) 1.85(3) 2.660(12) 161(2) 3_676 yes
O5^a H5A^a O1 0.84 1.98 2.719(2) 147.0 1_565 yes
O5A^b H5A1^b Cl1 0.84 2.56 3.222(15) 136.3 1_565 yes
O5A^b H5A1^b O1 0.84 2.35 2.993(15) 134.1 1_565 yes

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.061

