# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_flz
_database_code_depnum_ccdc_archive 'CCDC 1062610'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 Cl5 Co N2 O2, C H4 O, C4 H8 O'
_chemical_formula_sum            'C25 H26 Cl5 Co N2 O4'
_chemical_formula_weight         654.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.659(3)
_cell_length_b                   20.200(4)
_cell_length_c                   9.5832(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.056(4)
_cell_angle_gamma                90.00
_cell_volume                     2794.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4439
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.38
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.8436.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15110
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.57
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3722
_reflns_number_total             4932
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1331P)²+5.4705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2243
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C15(H15A,H15B), C16(H16A,H16B), C3(H3A,H3B), C42(H42A,H42B), C43(H43A,H43B),
 C41(H41A,H41B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Co1 Co 0.59440(5) 0.52297(3) 0.54685(7) 0.0308(3) Uani 1 d . . .
Cl2 Cl 0.64631(14) 0.59833(10) 0.99993(16) 0.0644(5) Uani 1 d . . .
Cl3 Cl 0.69526(13) 0.29957(9) 0.6444(2) 0.0674(5) Uani 1 d . . .
Cl4 Cl 0.91481(15) 0.31424(12) 0.2523(3) 0.0888(7) Uani 1 d . . .
Cl5 Cl 0.89875(15) 0.76930(11) 0.8592(3) 0.0875(7) Uani 1 d . . .
O6 O 0.6378(3) 0.43353(18) 0.5517(4) 0.0386(9) Uani 1 d . . .
O8 O 0.6666(3) 0.53285(19) 0.7313(4) 0.0406(9) Uani 1 d . . .
N9 N 0.5573(3) 0.6129(2) 0.5576(4) 0.0335(10) Uani 1 d . . .
C10 C 0.7188(4) 0.5856(3) 0.7604(5) 0.0371(12) Uani 1 d . . .
C11 C 0.5985(4) 0.6559(3) 0.4803(6) 0.0374(12) Uani 1 d . . .
C12 C 0.7784(4) 0.6077(3) 0.6687(6) 0.0403(13) Uani 1 d . . .
N13 N 0.6908(3) 0.5577(2) 0.4464(4) 0.0344(10) Uani 1 d . . .
C14 C 0.8025(4) 0.4148(3) 0.3061(7) 0.0508(15) Uani 1 d . . .
H14 H 0.8266 0.4384 0.2375 0.061 Uiso 1 calc . . R
C15 C 0.7033(4) 0.5120(3) 0.3286(6) 0.0391(13) Uani 1 d . . .
H15A H 0.7475 0.5315 0.2764 0.047 Uiso 1 calc . . R
H15B H 0.6447 0.5081 0.2641 0.047 Uiso 1 calc . . R
C16 C 0.7823(4) 0.5663(3) 0.5423(6) 0.0403(13) Uani 1 d . . .
H16A H 0.8061 0.5230 0.5735 0.048 Uiso 1 calc . . R
H16B H 0.8255 0.5862 0.4887 0.048 Uiso 1 calc . . R
C18 C 0.6999(4) 0.4098(3) 0.4817(6) 0.0379(12) Uani 1 d . . .
C20 C 0.5289(5) 0.7472(3) 0.5770(7) 0.0554(16) Uani 1 d . . .
H20 H 0.5175 0.7924 0.5812 0.066 Uiso 1 calc . . R
C21 C 0.8323(4) 0.6636(3) 0.6999(6) 0.0447(14) Uani 1 d . . .
H21 H 0.8698 0.6782 0.6372 0.054 Uiso 1 calc . . R
C22 C 0.7986(4) 0.3153(3) 0.4427(8) 0.0582(18) Uani 1 d . . .
H22 H 0.8192 0.2724 0.4652 0.070 Uiso 1 calc . . R
C23 C 0.7759(4) 0.6774(3) 0.9173(7) 0.0513(15) Uani 1 d . . .
H23 H 0.7764 0.7003 1.0016 0.062 Uiso 1 calc . . R
C24 C 0.7201(4) 0.6223(3) 0.8848(6) 0.0459(14) Uani 1 d . . .
C25 C 0.7361(4) 0.4438(3) 0.3756(6) 0.0394(12) Uani 1 d . . .
C26 C 0.5042(4) 0.6361(3) 0.6486(6) 0.0421(13) Uani 1 d . . .
H26 H 0.4775 0.6066 0.7042 0.051 Uiso 1 calc . . R
C27 C 0.7339(4) 0.3447(3) 0.5115(7) 0.0471(14) Uani 1 d . . .
C28 C 0.5849(4) 0.7235(3) 0.4894(7) 0.0483(14) Uani 1 d . . .
H28 H 0.6139 0.7525 0.4358 0.058 Uiso 1 calc . . R
C29 C 0.4889(4) 0.7036(3) 0.6598(7) 0.0513(15) Uani 1 d . . .
H29 H 0.4521 0.7193 0.7225 0.062 Uiso 1 calc . . R
C30 C 0.8306(4) 0.6974(3) 0.8221(7) 0.0516(15) Uani 1 d . . .
C31 C 0.8319(5) 0.3509(4) 0.3400(8) 0.0587(18) Uani 1 d . . .
Cl1 Cl 0.4904(3) 0.4937(2) 0.6256(4) 0.1319(11) Uani 1 d . . .
C3 C 0.6560(4) 0.6227(3) 0.3848(6) 0.0415(13) Uani 1 d . . .
H3A H 0.6188 0.6159 0.2919 0.050 Uiso 1 calc . . R
H3B H 0.7079 0.6508 0.3741 0.050 Uiso 1 calc . . R
O1 O 0.4362(4) 0.8896(3) 0.6938(6) 0.0760(15) Uani 1 d . . .
H1 H 0.4653 0.9221 0.7284 0.114 Uiso 1 calc . . GR
C1 C 0.3824(9) 0.9069(6) 0.5616(13) 0.123(4) Uani 1 d . . .
H1A H 0.4224 0.9225 0.4993 0.185 Uiso 1 calc . . GR
H1B H 0.3394 0.9411 0.5752 0.185 Uiso 1 calc . . GR
H1C H 0.3490 0.8687 0.5206 0.185 Uiso 1 calc . . GR
C42 C 0.9368(9) 0.5628(8) 0.269(2) 0.143(6) Uani 1 d . . .
H42A H 0.9012 0.5225 0.2716 0.171 Uiso 1 calc . . R
H42B H 0.9111 0.5972 0.3216 0.171 Uiso 1 calc . . R
C43 C 1.033(3) 0.6089(15) 0.126(4) 0.277(17) Uani 1 d . . .
H43A H 1.0468 0.6022 0.0316 0.332 Uiso 1 calc . . R
H43B H 1.0381 0.6556 0.1496 0.332 Uiso 1 calc . . R
O3 O 1.026(2) 0.5530(15) 0.320(3) 0.399(19) Uani 1 d . . .
C41 C 0.939(2) 0.5812(16) 0.140(3) 0.254(15) Uani 1 d . . .
H41A H 0.8920 0.6146 0.1118 0.304 Uiso 1 calc . . R
H41B H 0.9251 0.5436 0.0773 0.304 Uiso 1 calc . . R
C40 C 1.0869(18) 0.5722(19) 0.222(3) 0.293(19) Uani 1 d . . .
H40A H 1.1394 0.5975 0.2699 0.352 Uiso 1 calc . . R
H40B H 1.1096 0.5336 0.1782 0.352 Uiso 1 calc . . R


_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 Co1 2.9084(14) 3_666 ?
Co1 O6 1.913(4) . ?
Co1 O8 1.906(4) . ?
Co1 N9 1.905(4) . ?
Co1 N13 1.972(4) . ?
Co1 Cl1 1.909(4) . ?
Co1 Cl1 1.916(4) 3_666 ?
Cl2 C24 1.744(6) . ?
Cl3 C27 1.740(7) . ?
Cl4 C31 1.757(6) . ?
Cl5 C30 1.763(6) . ?
O6 C18 1.312(6) . ?
O8 C10 1.313(7) . ?
N9 C11 1.349(7) . ?
N9 C26 1.350(7) . ?
C10 C12 1.415(8) . ?
C10 C24 1.400(8) . ?
C11 C28 1.385(8) . ?
C11 C3 1.506(8) . ?
C12 C16 1.481(8) . ?
C12 C21 1.380(8) . ?
N13 C15 1.495(7) . ?
N13 C16 1.498(7) . ?
N13 C3 1.492(7) . ?
C14 C25 1.399(8) . ?
C14 C31 1.382(10) . ?
C15 C25 1.501(8) . ?
C18 C25 1.407(8) . ?
C18 C27 1.418(8) . ?
C20 C28 1.361(9) . ?
C20 C29 1.382(9) . ?
C21 C30 1.360(8) . ?
C22 C27 1.381(9) . ?
C22 C31 1.375(10) . ?
C23 C24 1.384(9) . ?
C23 C30 1.376(9) . ?
C26 C29 1.389(8) . ?
Cl1 Co1 1.916(4) 3_666 ?
O1 C1 1.414(12) . ?
C42 O3 1.32(2) . ?
C42 C41 1.30(3) . ?
C43 C41 1.52(3) . ?
C43 C40 1.33(3) . ?
O3 C40 1.46(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Co1 Co1 90.04(12) . 3_666 ?
O6 Co1 N13 94.86(17) . . ?
O6 Co1 Cl1 91.04(17) . 3_666 ?
O8 Co1 Co1 131.65(12) . 3_666 ?
O8 Co1 O6 87.01(16) . . ?
O8 Co1 N13 94.92(17) . . ?
O8 Co1 Cl1 171.89(16) . 3_666 ?
O8 Co1 Cl1 91.07(16) . . ?
N9 Co1 Co1 93.20(13) . 3_666 ?
N9 Co1 O6 175.15(17) . . ?
N9 Co1 O8 88.14(17) . . ?
N9 Co1 N13 85.53(18) . . ?
N9 Co1 Cl1 93.77(17) . 3_666 ?
N9 Co1 Cl1 91.09(18) . . ?
N13 Co1 Co1 133.39(13) . 3_666 ?
Cl1 Co1 Co1 40.42(12) 3_666 3_666 ?
Cl1 Co1 Co1 40.60(12) . 3_666 ?
Cl1 Co1 O6 89.02(17) . . ?
Cl1 Co1 N13 93.08(17) 3_666 . ?
Cl1 Co1 N13 173.01(17) . . ?
Cl1 Co1 Cl1 81.02(17) . 3_666 ?
C18 O6 Co1 126.2(4) . . ?
C10 O8 Co1 119.4(3) . . ?
C11 N9 Co1 115.1(4) . . ?
C11 N9 C26 119.6(5) . . ?
C26 N9 Co1 124.6(4) . . ?
O8 C10 C12 121.6(5) . . ?
O8 C10 C24 122.1(5) . . ?
C24 C10 C12 116.3(5) . . ?
N9 C11 C28 121.1(5) . . ?
N9 C11 C3 113.5(5) . . ?
C28 C11 C3 125.4(5) . . ?
C10 C12 C16 116.5(5) . . ?
C21 C12 C10 121.0(5) . . ?
C21 C12 C16 122.5(5) . . ?
C15 N13 Co1 109.9(3) . . ?
C15 N13 C16 108.7(4) . . ?
C16 N13 Co1 112.5(3) . . ?
C3 N13 Co1 106.4(3) . . ?
C3 N13 C15 108.9(4) . . ?
C3 N13 C16 110.4(4) . . ?
C31 C14 C25 119.6(6) . . ?
N13 C15 C25 114.6(4) . . ?
C12 C16 N13 114.2(4) . . ?
O6 C18 C25 125.1(5) . . ?
O6 C18 C27 119.2(5) . . ?
C25 C18 C27 115.8(5) . . ?
C28 C20 C29 119.5(6) . . ?
C30 C21 C12 120.1(6) . . ?
C31 C22 C27 118.4(6) . . ?
C30 C23 C24 118.5(6) . . ?
C10 C24 Cl2 118.3(5) . . ?
C23 C24 Cl2 119.2(5) . . ?
C23 C24 C10 122.5(5) . . ?
C14 C25 C15 117.1(5) . . ?
C14 C25 C18 121.4(6) . . ?
C18 C25 C15 121.5(5) . . ?
N9 C26 C29 120.6(6) . . ?
C18 C27 Cl3 119.0(5) . . ?
C22 C27 Cl3 117.6(5) . . ?
C22 C27 C18 123.4(6) . . ?
C20 C28 C11 119.6(6) . . ?
C20 C29 C26 119.4(6) . . ?
C21 C30 Cl5 119.5(5) . . ?
C21 C30 C23 121.6(6) . . ?
C23 C30 Cl5 119.0(5) . . ?
C14 C31 Cl4 119.6(6) . . ?
C22 C31 Cl4 118.9(5) . . ?
C22 C31 C14 121.4(6) . . ?
Co1 Cl1 Co1 98.98(17) . 3_666 ?
N13 C3 C11 109.9(4) . . ?
C41 C42 O3 102(2) . . ?
C40 C43 C41 100(2) . . ?
C42 O3 C40 114(2) . . ?
C42 C41 C43 112(2) . . ?
C43 C40 O3 104(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
