# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_zh-2co
_database_code_depnum_ccdc_archive 'CCDC 1559918'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 Co N6 O8'
_chemical_formula_sum            'C28 H26 Co N6 O8'
_chemical_formula_weight         633.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.286(3)
_cell_length_b                   9.921(2)
_cell_length_c                   19.852(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.46(3)
_cell_angle_gamma                90
_cell_volume                     2855.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.445
_cell_measurement_theta_min      2.321
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4816
_reflns_number_total             6549
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+2.2918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C7(H7A,H7B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N4(H4), C25(H25), C26(H26), C21(H21), C22(H22), C24(H24), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co01 Co 0.48542(2) 0.44847(3) 0.26040(2) 0.02609(11) Uani 1 1 d . . . . .
O5 O 0.41190(12) 0.53404(17) 0.32225(9) 0.0330(4) Uani 1 1 d . . . . .
O1 O 0.55714(12) 0.3602(2) 0.19657(10) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.53604(13) 0.2480(2) 0.09527(11) 0.0502(6) Uani 1 1 d . . . . .
N5 N 0.38258(14) 0.3148(2) 0.19596(10) 0.0287(5) Uani 1 1 d . . . . .
N3 N 0.51858(14) 0.3124(2) 0.34916(11) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.59611(14) 0.5827(2) 0.29771(10) 0.0280(5) Uani 1 1 d . . . . .
O6 O 0.37541(14) 0.5122(2) 0.42173(10) 0.0455(5) Uani 1 1 d . . . . .
O3 O 0.41146(16) 0.1147(2) 0.01111(11) 0.0542(6) Uani 1 1 d . . . . .
H3 H 0.450688 0.164027 0.037361 0.081 Uiso 1 1 calc GR . . . .
N6 N 0.27261(15) 0.1935(2) 0.12394(11) 0.0339(5) Uani 1 1 d . . . . .
H6 H 0.220118 0.154618 0.105778 0.041 Uiso 1 1 calc R . . . .
N1 N 0.44714(15) 0.6049(2) 0.18115(11) 0.0337(5) Uani 1 1 d . . . . .
O7 O 0.3823(2) 0.3240(2) 0.51040(13) 0.0713(8) Uani 1 1 d . . . . .
H7 H 0.376752 0.383762 0.480815 0.107 Uiso 1 1 calc GR . . . .
O4 O 0.26943(17) 0.0525(3) 0.00074(12) 0.0696(7) Uani 1 1 d . . . . .
C2 C 0.41329(17) 0.2636(3) 0.14319(13) 0.0284(5) Uani 1 1 d . . . . .
C5 C 0.29693(17) 0.2700(2) 0.18288(13) 0.0300(6) Uani 1 1 d . . . . .
C9 C 0.41484(17) 0.4738(2) 0.37823(13) 0.0290(6) Uani 1 1 d . . . . .
N4 N 0.52901(19) 0.1504(2) 0.42619(13) 0.0514(7) Uani 1 1 d . . . . .
H4 H 0.544709 0.075500 0.448564 0.062 Uiso 1 1 calc R . . . .
C10 C 0.46785(18) 0.3465(3) 0.39263(13) 0.0296(6) Uani 1 1 d . . . . .
C3 C 0.34506(18) 0.1878(3) 0.09763(13) 0.0323(6) Uani 1 1 d . . . . .
C23 C 0.66782(19) 0.7768(3) 0.26244(14) 0.0348(6) Uani 1 1 d . . . . .
C27 C 0.59484(17) 0.6851(2) 0.25132(13) 0.0289(6) Uani 1 1 d . . . . .
C28 C 0.51602(18) 0.6953(3) 0.18901(13) 0.0306(6) Uani 1 1 d . . . . .
C6 C 0.23502(19) 0.2996(3) 0.22541(15) 0.0389(7) Uani 1 1 d . . . . .
H6A H 0.271632 0.305163 0.275141 0.047 Uiso 1 1 calc R . . . .
H6B H 0.191875 0.225690 0.220218 0.047 Uiso 1 1 calc R . . . .
C25 C 0.74400(19) 0.6595(3) 0.37058(15) 0.0392(7) Uani 1 1 d . . . . .
H25 H 0.793844 0.648127 0.411660 0.047 Uiso 1 1 calc R . . . .
C13 C 0.5551(2) 0.1921(3) 0.37085(15) 0.0405(7) Uani 1 1 d . . . . .
C26 C 0.66786(18) 0.5729(3) 0.35529(13) 0.0338(6) Uani 1 1 d . . . . .
H26 H 0.668133 0.504831 0.387588 0.041 Uiso 1 1 calc R . . . .
C20 C 0.5128(2) 0.7972(3) 0.13930(14) 0.0395(7) Uani 1 1 d . . . . .
C11 C 0.4735(2) 0.2464(3) 0.44106(15) 0.0415(7) Uani 1 1 d . . . . .
C1 C 0.50881(18) 0.2922(3) 0.14477(14) 0.0341(6) Uani 1 1 d . . . . .
C21 C 0.5879(2) 0.8902(3) 0.15227(16) 0.0485(8) Uani 1 1 d . . . . .
H21 H 0.585922 0.958146 0.119538 0.058 Uiso 1 1 calc R . . . .
C22 C 0.6613(2) 0.8805(3) 0.21119(16) 0.0462(8) Uani 1 1 d . . . . .
H22 H 0.708977 0.942660 0.218778 0.055 Uiso 1 1 calc R . . . .
C4 C 0.3387(2) 0.1128(3) 0.03190(15) 0.0441(7) Uani 1 1 d . . . . .
C24 C 0.74371(19) 0.7603(3) 0.32438(16) 0.0411(7) Uani 1 1 d . . . . .
H24 H 0.793749 0.818626 0.333636 0.049 Uiso 1 1 calc R . . . .
O8 O 0.4437(3) 0.1225(3) 0.53168(17) 0.1091(13) Uani 1 1 d . . . . .
C17 C 0.3739(2) 0.6160(3) 0.12428(16) 0.0499(8) Uani 1 1 d . . . . .
H17 H 0.325996 0.554829 0.118654 0.060 Uiso 1 1 calc R . . . .
C18 C 0.3642(2) 0.7141(4) 0.07208(17) 0.0600(9) Uani 1 1 d . . . . .
H18 H 0.310706 0.718952 0.033261 0.072 Uiso 1 1 calc R . . . .
C14 C 0.6165(2) 0.1155(3) 0.33991(18) 0.0572(9) Uani 1 1 d . . . . .
H14A H 0.601262 0.139000 0.290088 0.069 Uiso 1 1 calc R . . . .
H14B H 0.604336 0.020029 0.342605 0.069 Uiso 1 1 calc R . . . .
C19 C 0.4345(2) 0.8023(3) 0.07921(16) 0.0538(9) Uani 1 1 d . . . . .
H19 H 0.430490 0.866162 0.044084 0.065 Uiso 1 1 calc R . . . .
C12 C 0.4323(3) 0.2269(3) 0.49795(19) 0.0645(11) Uani 1 1 d . . . . .
C7 C 0.1815(3) 0.4291(4) 0.2041(2) 0.0727(11) Uani 1 1 d . . . . .
H7A H 0.148531 0.426943 0.153570 0.087 Uiso 1 1 calc R . . . .
H7B H 0.224230 0.504277 0.213165 0.087 Uiso 1 1 calc R . . . .
C15 C 0.7176(3) 0.1405(4) 0.3757(3) 0.0904(15) Uani 1 1 d . . . . .
H15A H 0.751577 0.105225 0.345743 0.109 Uiso 1 1 calc R . . . .
H15B H 0.728128 0.236971 0.379924 0.109 Uiso 1 1 calc R . . . .
C8 C 0.1132(3) 0.4507(4) 0.2443(3) 0.0932(15) Uani 1 1 d . . . . .
H8A H 0.064138 0.386220 0.228671 0.140 Uiso 1 1 calc GR . . . .
H8B H 0.088365 0.540201 0.235477 0.140 Uiso 1 1 calc GR . . . .
H8C H 0.144021 0.439371 0.294261 0.140 Uiso 1 1 calc GR . . . .
C16 C 0.7537(4) 0.0809(6) 0.4449(3) 0.130(2) Uani 1 1 d . . . . .
H16A H 0.730868 -0.009562 0.443631 0.195 Uiso 1 1 calc GR . . . .
H16B H 0.734390 0.132977 0.478470 0.195 Uiso 1 1 calc GR . . . .
H16C H 0.819795 0.079407 0.458942 0.195 Uiso 1 1 calc GR . . . .


_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
Co01 O5 2.0894(18) . ?
Co01 O1 2.1104(19) . ?
Co01 N5 2.143(2) . ?
Co01 N3 2.149(2) . ?
Co01 N2 2.096(2) . ?
Co01 N1 2.155(2) . ?
O5 C9 1.250(3) . ?
O1 C1 1.256(3) . ?
O2 C1 1.261(3) . ?
N5 C2 1.374(3) . ?
N5 C5 1.328(3) . ?
N3 C10 1.373(3) . ?
N3 C13 1.330(3) . ?
N2 C27 1.367(3) . ?
N2 C26 1.313(3) . ?
O6 C9 1.258(3) . ?
O3 C4 1.304(4) . ?
N6 C5 1.344(3) . ?
N6 C3 1.367(3) . ?
N1 C28 1.354(3) . ?
N1 C17 1.319(3) . ?
O7 C12 1.301(4) . ?
O4 C4 1.202(4) . ?
C2 C3 1.369(4) . ?
C2 C1 1.478(4) . ?
C5 C6 1.484(4) . ?
C9 C10 1.479(3) . ?
N4 C13 1.347(3) . ?
N4 C11 1.368(3) . ?
C10 C11 1.366(4) . ?
C3 C4 1.479(4) . ?
C23 C27 1.402(4) . ?
C23 C22 1.428(4) . ?
C23 C24 1.407(4) . ?
C27 C28 1.431(4) . ?
C28 C20 1.402(4) . ?
C6 C7 1.509(5) . ?
C25 C26 1.401(4) . ?
C25 C24 1.356(4) . ?
C13 C14 1.483(4) . ?
C20 C21 1.432(4) . ?
C20 C19 1.398(4) . ?
C11 C12 1.469(4) . ?
C21 C22 1.343(4) . ?
O8 C12 1.216(4) . ?
C17 C18 1.395(4) . ?
C18 C19 1.358(5) . ?
C14 C15 1.504(6) . ?
C7 C8 1.516(5) . ?
C15 C16 1.436(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Co01 O1 178.82(7) . . ?
O5 Co01 N5 99.96(8) . . ?
O5 Co01 N3 78.72(7) . . ?
O5 Co01 N2 93.34(8) . . ?
O5 Co01 N1 93.68(8) . . ?
O1 Co01 N5 78.88(7) . . ?
O1 Co01 N3 101.49(8) . . ?
O1 Co01 N1 86.16(8) . . ?
N5 Co01 N3 92.22(8) . . ?
N5 Co01 N1 91.81(8) . . ?
N3 Co01 N1 171.92(8) . . ?
N2 Co01 O1 87.77(8) . . ?
N2 Co01 N5 164.12(8) . . ?
N2 Co01 N3 98.91(8) . . ?
N2 Co01 N1 78.61(8) . . ?
C9 O5 Co01 116.99(15) . . ?
C1 O1 Co01 115.58(16) . . ?
C2 N5 Co01 108.71(16) . . ?
C5 N5 Co01 144.62(17) . . ?
C5 N5 C2 106.3(2) . . ?
C10 N3 Co01 109.09(15) . . ?
C13 N3 Co01 142.64(18) . . ?
C13 N3 C10 106.3(2) . . ?
C27 N2 Co01 113.36(16) . . ?
C26 N2 Co01 128.21(18) . . ?
C26 N2 C27 118.1(2) . . ?
C5 N6 C3 108.8(2) . . ?
C28 N1 Co01 111.82(16) . . ?
C17 N1 Co01 130.2(2) . . ?
C17 N1 C28 117.5(2) . . ?
N5 C2 C1 119.1(2) . . ?
C3 C2 N5 109.5(2) . . ?
C3 C2 C1 131.3(2) . . ?
N5 C5 N6 110.1(2) . . ?
N5 C5 C6 126.1(2) . . ?
N6 C5 C6 123.8(2) . . ?
O5 C9 O6 125.1(2) . . ?
O5 C9 C10 116.3(2) . . ?
O6 C9 C10 118.6(2) . . ?
C13 N4 C11 109.0(2) . . ?
N3 C10 C9 118.2(2) . . ?
C11 C10 N3 109.9(2) . . ?
C11 C10 C9 131.8(2) . . ?
N6 C3 C2 105.4(2) . . ?
N6 C3 C4 121.5(2) . . ?
C2 C3 C4 133.1(3) . . ?
C27 C23 C22 118.9(3) . . ?
C27 C23 C24 117.2(2) . . ?
C24 C23 C22 123.9(3) . . ?
N2 C27 C23 122.4(2) . . ?
N2 C27 C28 117.6(2) . . ?
C23 C27 C28 120.0(2) . . ?
N1 C28 C27 117.6(2) . . ?
N1 C28 C20 122.9(2) . . ?
C20 C28 C27 119.4(2) . . ?
C5 C6 C7 113.3(3) . . ?
C24 C25 C26 118.8(3) . . ?
N3 C13 N4 109.7(2) . . ?
N3 C13 C14 125.5(2) . . ?
N4 C13 C14 124.7(3) . . ?
N2 C26 C25 123.4(3) . . ?
C28 C20 C21 119.4(3) . . ?
C19 C20 C28 117.1(3) . . ?
C19 C20 C21 123.5(3) . . ?
N4 C11 C12 121.3(2) . . ?
C10 C11 N4 105.1(2) . . ?
C10 C11 C12 133.6(3) . . ?
O1 C1 O2 124.8(3) . . ?
O1 C1 C2 116.2(2) . . ?
O2 C1 C2 119.0(2) . . ?
C22 C21 C20 120.7(3) . . ?
C21 C22 C23 121.5(3) . . ?
O3 C4 C3 116.6(3) . . ?
O4 C4 O3 123.0(3) . . ?
O4 C4 C3 120.4(3) . . ?
C25 C24 C23 120.1(3) . . ?
N1 C17 C18 123.8(3) . . ?
C19 C18 C17 118.5(3) . . ?
C13 C14 C15 114.2(3) . . ?
C18 C19 C20 120.1(3) . . ?
O7 C12 C11 118.0(3) . . ?
O8 C12 O7 121.1(3) . . ?
O8 C12 C11 121.0(3) . . ?
C6 C7 C8 112.0(3) . . ?
C16 C15 C14 114.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.66 2.480(3) 173.4 .
N6 H6 O6 0.86 1.98 2.807(3) 160.8 2_545
O7 H7 O6 0.82 1.73 2.546(3) 174.9 .
N4 H4 O8 0.86 2.00 2.825(3) 160.5 3_656

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zh-4fe
_database_code_depnum_ccdc_archive 'CCDC 1559920'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 Fe N6 O8'
_chemical_formula_sum            'C28 H26 Fe N6 O8'
_chemical_formula_weight         630.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.276(3)
_cell_length_b                   9.993(2)
_cell_length_c                   19.942(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.46(3)
_cell_angle_gamma                90
_cell_volume                     2887.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.072
_cell_measurement_theta_min      2.305
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            66619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4456
_reflns_number_total             6615
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+2.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1337
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C7(H7A,H7B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N4(H4), C26(H26), C25(H25), C24(H24), C22(H22), C21(H21), C18(H18),
 C19(H19), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.48444(3) 0.55034(4) 0.26059(2) 0.02363(14) Uani 1 1 d . . . . .
O5 O 0.41134(15) 0.4700(2) 0.32374(11) 0.0311(5) Uani 1 1 d . . . . .
O1 O 0.55424(15) 0.6400(2) 0.19631(12) 0.0364(6) Uani 1 1 d . . . . .
O2 O 0.53420(16) 0.7494(3) 0.09498(13) 0.0471(7) Uani 1 1 d . . . . .
N2 N 0.59807(17) 0.4126(2) 0.29696(13) 0.0240(6) Uani 1 1 d . . . . .
N5 N 0.37895(17) 0.6854(3) 0.19388(13) 0.0261(6) Uani 1 1 d . . . . .
N3 N 0.51850(17) 0.6898(3) 0.35096(13) 0.0267(6) Uani 1 1 d . . . . .
O6 O 0.37658(17) 0.4902(2) 0.42392(13) 0.0438(7) Uani 1 1 d . . . . .
N6 N 0.26968(18) 0.8066(3) 0.12171(13) 0.0299(6) Uani 1 1 d . . . . .
H6 H 0.217402 0.845763 0.103450 0.036 Uiso 1 1 calc R . . . .
O3 O 0.41052(19) 0.8832(3) 0.01032(13) 0.0503(7) Uani 1 1 d . . . . .
H3 H 0.448316 0.830820 0.035192 0.075 Uiso 1 1 calc GR . . . .
N1 N 0.44655(18) 0.3885(3) 0.18141(14) 0.0315(6) Uani 1 1 d . . . . .
O4 O 0.2689(2) 0.9474(3) -0.00045(14) 0.0658(9) Uani 1 1 d . . . . .
O7 O 0.3831(2) 0.6778(3) 0.51204(16) 0.0690(10) Uani 1 1 d . . . . .
H7 H 0.380290 0.616400 0.484172 0.104 Uiso 1 1 calc GR . . . .
C2 C 0.4103(2) 0.7355(3) 0.14156(16) 0.0253(7) Uani 1 1 d . . . . .
C27 C 0.5959(2) 0.3111(3) 0.25088(15) 0.0239(7) Uani 1 1 d . . . . .
N4 N 0.5296(2) 0.8504(3) 0.42766(16) 0.0489(9) Uani 1 1 d . . . . .
H4 H 0.545286 0.924968 0.449763 0.059 Uiso 1 1 calc R . . . .
C23 C 0.6690(2) 0.2196(3) 0.26203(17) 0.0300(7) Uani 1 1 d . . . . .
C5 C 0.2932(2) 0.7303(3) 0.18014(17) 0.0283(7) Uani 1 1 d . . . . .
C10 C 0.4684(2) 0.6554(3) 0.39448(16) 0.0266(7) Uani 1 1 d . . . . .
C9 C 0.4155(2) 0.5284(3) 0.38014(17) 0.0277(7) Uani 1 1 d . . . . .
C28 C 0.5167(2) 0.2999(3) 0.18931(16) 0.0266(7) Uani 1 1 d . . . . .
C3 C 0.3430(2) 0.8115(3) 0.09603(16) 0.0294(7) Uani 1 1 d . . . . .
C13 C 0.5556(3) 0.8089(3) 0.37259(18) 0.0374(8) Uani 1 1 d . . . . .
C20 C 0.5134(2) 0.1992(3) 0.13981(17) 0.0360(8) Uani 1 1 d . . . . .
C26 C 0.6701(2) 0.4228(3) 0.35440(16) 0.0299(7) Uani 1 1 d . . . . .
H26 H 0.670792 0.490891 0.386386 0.036 Uiso 1 1 calc R . . . .
C25 C 0.7454(2) 0.3358(4) 0.36936(18) 0.0353(8) Uani 1 1 d . . . . .
H25 H 0.795219 0.346333 0.410358 0.042 Uiso 1 1 calc R . . . .
C11 C 0.4743(3) 0.7551(3) 0.44293(19) 0.0393(9) Uani 1 1 d . . . . .
C24 C 0.7448(2) 0.2359(4) 0.32334(19) 0.0372(8) Uani 1 1 d . . . . .
H24 H 0.794892 0.177949 0.332423 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3373(3) 0.8859(4) 0.03068(18) 0.0395(9) Uani 1 1 d . . . . .
C6 C 0.2308(2) 0.7006(3) 0.22222(19) 0.0381(9) Uani 1 1 d . . . . .
H6A H 0.185483 0.771693 0.214875 0.046 Uiso 1 1 calc R . . . .
H6B H 0.266668 0.699948 0.271987 0.046 Uiso 1 1 calc R . . . .
C1 C 0.5066(2) 0.7070(3) 0.14410(17) 0.0326(8) Uani 1 1 d . . . . .
C22 C 0.6628(3) 0.1170(4) 0.2111(2) 0.0418(9) Uani 1 1 d . . . . .
H22 H 0.710797 0.055902 0.218384 0.050 Uiso 1 1 calc R . . . .
C21 C 0.5887(3) 0.1067(4) 0.1528(2) 0.0446(10) Uani 1 1 d . . . . .
H21 H 0.586345 0.038736 0.120416 0.054 Uiso 1 1 calc R . . . .
C18 C 0.3644(3) 0.2810(4) 0.0729(2) 0.0552(11) Uani 1 1 d . . . . .
H18 H 0.311465 0.276892 0.033730 0.066 Uiso 1 1 calc R . . . .
O8 O 0.4446(3) 0.8783(3) 0.5327(2) 0.1063(16) Uani 1 1 d . . . . .
C19 C 0.4350(3) 0.1928(4) 0.0801(2) 0.0495(10) Uani 1 1 d . . . . .
H19 H 0.431008 0.128746 0.045475 0.059 Uiso 1 1 calc R . . . .
C17 C 0.3729(3) 0.3767(4) 0.12485(19) 0.0462(10) Uani 1 1 d . . . . .
H17 H 0.324206 0.435790 0.119661 0.055 Uiso 1 1 calc R . . . .
C14 C 0.6164(3) 0.8846(4) 0.3416(2) 0.0548(12) Uani 1 1 d . . . . .
H14A H 0.603953 0.979368 0.343948 0.066 Uiso 1 1 calc R . . . .
H14B H 0.601295 0.860660 0.292106 0.066 Uiso 1 1 calc R . . . .
C12 C 0.4330(3) 0.7744(4) 0.4995(2) 0.0640(14) Uani 1 1 d . . . . .
C7 C 0.1812(3) 0.5687(4) 0.2035(3) 0.0672(13) Uani 1 1 d . . . . .
H7A H 0.226172 0.496837 0.213594 0.081 Uiso 1 1 calc R . . . .
H7B H 0.147868 0.567097 0.153250 0.081 Uiso 1 1 calc R . . . .
C15 C 0.7180(4) 0.8608(5) 0.3773(3) 0.0859(18) Uani 1 1 d . . . . .
H15A H 0.728884 0.765088 0.381752 0.103 Uiso 1 1 calc R . . . .
H15B H 0.751711 0.895762 0.347297 0.103 Uiso 1 1 calc R . . . .
C8 C 0.1143(4) 0.5454(5) 0.2443(3) 0.0890(17) Uani 1 1 d . . . . .
H8A H 0.063375 0.606440 0.227986 0.134 Uiso 1 1 calc GR . . . .
H8B H 0.145105 0.559853 0.293721 0.134 Uiso 1 1 calc GR . . . .
H8C H 0.091771 0.455114 0.236930 0.134 Uiso 1 1 calc GR . . . .
C16 C 0.7544(5) 0.9208(7) 0.4464(3) 0.123(3) Uani 1 1 d . . . . .
H16A H 0.732523 1.011184 0.444728 0.184 Uiso 1 1 calc GR . . . .
H16B H 0.820642 0.920843 0.460556 0.184 Uiso 1 1 calc GR . . . .
H16C H 0.734410 0.870374 0.479818 0.184 Uiso 1 1 calc GR . . . .


_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 O5 2.090(2) . ?
Fe1 O1 2.109(2) . ?
Fe1 N2 2.153(2) . ?
Fe1 N5 2.198(3) . ?
Fe1 N3 2.206(3) . ?
Fe1 N1 2.206(3) . ?
O5 C9 1.251(4) . ?
O1 C1 1.258(4) . ?
O2 C1 1.257(4) . ?
N2 C27 1.362(4) . ?
N2 C26 1.317(4) . ?
N5 C2 1.373(4) . ?
N5 C5 1.328(4) . ?
N3 C10 1.370(4) . ?
N3 C13 1.330(4) . ?
O6 C9 1.261(4) . ?
N6 C5 1.342(4) . ?
N6 C3 1.372(4) . ?
O3 C4 1.305(4) . ?
N1 C28 1.361(4) . ?
N1 C17 1.322(4) . ?
O4 C4 1.202(4) . ?
O7 C12 1.302(5) . ?
C2 C3 1.366(4) . ?
C2 C1 1.484(4) . ?
C27 C23 1.405(4) . ?
C27 C28 1.429(4) . ?
N4 C13 1.346(4) . ?
N4 C11 1.369(4) . ?
C23 C24 1.403(5) . ?
C23 C22 1.424(5) . ?
C5 C6 1.486(4) . ?
C10 C9 1.483(4) . ?
C10 C11 1.371(4) . ?
C28 C20 1.399(4) . ?
C3 C4 1.479(5) . ?
C13 C14 1.478(5) . ?
C20 C21 1.434(5) . ?
C20 C19 1.396(5) . ?
C26 C25 1.397(5) . ?
C25 C24 1.354(5) . ?
C11 C12 1.470(5) . ?
C6 C7 1.507(5) . ?
C22 C21 1.346(5) . ?
C18 C19 1.365(6) . ?
C18 C17 1.386(5) . ?
O8 C12 1.214(5) . ?
C14 C15 1.507(7) . ?
C7 C8 1.513(6) . ?
C15 C16 1.443(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Fe1 O1 177.21(9) . . ?
O5 Fe1 N2 94.53(9) . . ?
O5 Fe1 N5 99.88(9) . . ?
O5 Fe1 N3 77.49(9) . . ?
O5 Fe1 N1 94.60(9) . . ?
O1 Fe1 N2 88.12(9) . . ?
O1 Fe1 N5 77.65(9) . . ?
O1 Fe1 N3 101.21(9) . . ?
O1 Fe1 N1 86.84(10) . . ?
N2 Fe1 N5 162.70(9) . . ?
N2 Fe1 N3 99.91(10) . . ?
N2 Fe1 N1 76.89(10) . . ?
N5 Fe1 N3 92.57(10) . . ?
N5 Fe1 N1 92.35(10) . . ?
N1 Fe1 N3 171.31(10) . . ?
C9 O5 Fe1 118.49(19) . . ?
C1 O1 Fe1 117.2(2) . . ?
C27 N2 Fe1 113.83(19) . . ?
C26 N2 Fe1 127.3(2) . . ?
C26 N2 C27 118.7(3) . . ?
C2 N5 Fe1 108.59(19) . . ?
C5 N5 Fe1 144.9(2) . . ?
C5 N5 C2 106.2(3) . . ?
C10 N3 Fe1 108.95(19) . . ?
C13 N3 Fe1 142.8(2) . . ?
C13 N3 C10 106.5(3) . . ?
C5 N6 C3 108.6(3) . . ?
C28 N1 Fe1 112.07(19) . . ?
C17 N1 Fe1 129.5(2) . . ?
C17 N1 C28 117.8(3) . . ?
N5 C2 C1 119.0(3) . . ?
C3 C2 N5 109.7(3) . . ?
C3 C2 C1 131.2(3) . . ?
N2 C27 C23 122.0(3) . . ?
N2 C27 C28 118.1(3) . . ?
C23 C27 C28 119.9(3) . . ?
C13 N4 C11 109.2(3) . . ?
C27 C23 C22 119.0(3) . . ?
C24 C23 C27 117.3(3) . . ?
C24 C23 C22 123.7(3) . . ?
N5 C5 N6 110.3(3) . . ?
N5 C5 C6 125.7(3) . . ?
N6 C5 C6 124.0(3) . . ?
N3 C10 C9 118.2(3) . . ?
N3 C10 C11 109.8(3) . . ?
C11 C10 C9 131.9(3) . . ?
O5 C9 O6 125.4(3) . . ?
O5 C9 C10 116.3(3) . . ?
O6 C9 C10 118.3(3) . . ?
N1 C28 C27 118.0(3) . . ?
N1 C28 C20 122.3(3) . . ?
C20 C28 C27 119.7(3) . . ?
N6 C3 C4 121.3(3) . . ?
C2 C3 N6 105.3(3) . . ?
C2 C3 C4 133.4(3) . . ?
N3 C13 N4 109.6(3) . . ?
N3 C13 C14 125.6(3) . . ?
N4 C13 C14 124.8(3) . . ?
C28 C20 C21 119.2(3) . . ?
C19 C20 C28 117.6(3) . . ?
C19 C20 C21 123.1(3) . . ?
N2 C26 C25 122.8(3) . . ?
C24 C25 C26 119.1(3) . . ?
N4 C11 C10 104.8(3) . . ?
N4 C11 C12 121.7(3) . . ?
C10 C11 C12 133.5(3) . . ?
C25 C24 C23 120.2(3) . . ?
O3 C4 C3 116.6(3) . . ?
O4 C4 O3 122.7(3) . . ?
O4 C4 C3 120.7(3) . . ?
C5 C6 C7 113.4(3) . . ?
O1 C1 C2 116.0(3) . . ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 118.8(3) . . ?
C21 C22 C23 121.3(3) . . ?
C22 C21 C20 120.9(3) . . ?
C19 C18 C17 118.8(3) . . ?
C18 C19 C20 119.8(3) . . ?
N1 C17 C18 123.6(4) . . ?
C13 C14 C15 114.3(4) . . ?
O7 C12 C11 118.0(3) . . ?
O8 C12 O7 121.5(4) . . ?
O8 C12 C11 120.5(4) . . ?
C6 C7 C8 112.0(4) . . ?
C16 C15 C14 114.4(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6 O6 0.86 1.99 2.811(3) 160.2 2
O3 H3 O2 0.82 1.68 2.488(4) 169.2 .
O7 H7 O6 0.82 1.73 2.550(3) 178.0 .
N4 H4 O8 0.86 1.99 2.816(4) 159.6 3_676

_olex2_submission_special_instructions 'No special instructions were received'
