# 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. 
# 
#######################################################################

data_co
_database_code_depnum_ccdc_archive 'CCDC 1583330'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_audit_creation_date             2017-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Co1.5 N3 O7'
_chemical_formula_sum            'C19 H12 Co1.50 N3 O7'
_chemical_formula_weight         482.71
_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 0.0181 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'
Co Co -2.3653 3.6143 '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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   9.3083(2)
_cell_length_b                   10.4819(2)
_cell_length_c                   22.1487(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.098(2)
_cell_angle_gamma                90
_cell_volume                     2148.79(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8950
_cell_measurement_theta_min      4.9750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             974
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10644
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.672
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  30.00   0.50    0.69    --    0.00 -77.00  60.00  134
  2  ω    -33.00  31.00   0.50    0.69    --    0.00 -82.00 -30.00  128
  3  ω    -16.00  10.00   0.50    0.69    --    0.00 -82.00-180.00   52
  4  ω     35.00 118.00   0.50    2.78    --   94.90 -45.00-120.00  166
  5  ω    112.00 158.00   0.50    2.78    --   94.90  15.00  90.00   92
  6  ω    120.00 182.00   0.50    2.78    --   94.90  82.00 150.00  124
  7  ω     96.00 151.00   0.50    2.78    --   94.90  77.00   0.00  110
  8  ω     88.00 184.00   0.50    2.78    --   94.90  30.00 150.00  192
  9  ω     83.00 170.00   0.50    2.78    --   94.90  30.00 120.00  174
 10  ω     86.00 111.00   0.50    2.78    --   94.90  15.00  90.00   50
 11  ω      6.00 113.00   0.50    2.78    --   94.90 -61.00-120.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0637976000
_diffrn_orient_matrix_UB_12      -0.0832773000
_diffrn_orient_matrix_UB_13      -0.0479126000
_diffrn_orient_matrix_UB_21      -0.0523647000
_diffrn_orient_matrix_UB_22      0.0974434000
_diffrn_orient_matrix_UB_23      -0.0495772000
_diffrn_orient_matrix_UB_31      0.1447119000
_diffrn_orient_matrix_UB_32      0.0716978000
_diffrn_orient_matrix_UB_33      0.0117434000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3313
_reflns_number_total             3795
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9f (Rigaku OD, 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         0.590
_refine_diff_density_min         -1.275
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.057
_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)+(0.1160P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C10(H10), C5(H5), C19(H19), C16(H16), C18(H18), C11(H11),
 C14(H14), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
Co1 Co 0.5000 0.5000 0.5000 0.0242(2) Uani 1 2 d S T P . .
Co2 Co 0.26666(6) 0.92517(5) 0.50166(2) 0.0248(2) Uani 1 1 d . . . . .
O6 O 1.0880(3) 0.8444(3) 0.52020(13) 0.0395(7) Uani 1 1 d . . . . .
O3 O 0.4560(3) 0.8908(2) 0.54470(13) 0.0358(6) Uani 1 1 d . . . . .
O4 O 0.7549(3) 0.9061(2) 0.46153(12) 0.0347(6) Uani 1 1 d . . . . .
O2 O 0.2956(3) 0.5081(2) 0.52604(13) 0.0340(6) Uani 1 1 d . . . . .
H2A H 0.2916 0.5649 0.5535 0.051 Uiso 1 1 d GR . . . .
H2B H 0.2729 0.4357 0.5400 0.051 Uiso 1 1 d GR . . . .
O1 O 0.4893(3) 0.7038(2) 0.50223(12) 0.0325(6) Uani 1 1 d . . . . .
O5 O 0.8326(3) 0.7097(2) 0.44926(12) 0.0363(6) Uani 1 1 d . . . . .
O7 O 1.1764(3) 0.6983(3) 0.58752(13) 0.0417(7) Uani 1 1 d . . . . .
N2 N 0.2621(3) 0.9027(3) 0.41033(14) 0.0285(7) Uani 1 1 d . . . . .
N1 N 0.4056(3) 0.5241(3) 0.40411(14) 0.0300(7) Uani 1 1 d . . . . .
N3 N 0.8107(3) 0.7649(3) 0.73975(13) 0.0301(7) Uani 1 1 d . . . . .
C1 C 0.5294(3) 0.7918(3) 0.53770(15) 0.0226(7) Uani 1 1 d . . . . .
C2 C 0.6720(4) 0.7839(3) 0.57570(16) 0.0248(7) Uani 1 1 d . . . . .
C7 C 0.8027(3) 0.7797(3) 0.54980(15) 0.0214(7) Uani 1 1 d . . . . .
C8 C 1.0770(4) 0.7661(3) 0.56294(16) 0.0261(7) Uani 1 1 d . . . . .
C3 C 0.6709(3) 0.7803(3) 0.63824(16) 0.0247(7) Uani 1 1 d . . . . .
H3 H 0.5842 0.7872 0.6553 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7996(4) 0.7664(3) 0.67495(16) 0.0258(7) Uani 1 1 d . . . . .
C17 C 0.2526(4) 0.8936(3) 0.28346(16) 0.0301(8) Uani 1 1 d . . . . .
C15 C 0.1369(4) 0.9162(3) 0.37434(18) 0.0334(9) Uani 1 1 d . . . . .
H15 H 0.0523 0.9277 0.3926 0.040 Uiso 1 1 calc R . . . .
C6 C 0.9319(4) 0.7639(3) 0.58744(16) 0.0235(7) Uani 1 1 d . . . . .
C9 C 0.7992(3) 0.7977(3) 0.48185(16) 0.0246(7) Uani 1 1 d . . . . .
C10 C 0.2676(4) 0.5576(4) 0.38935(19) 0.0365(9) Uani 1 1 d . . . . .
H10 H 0.2117 0.5748 0.4208 0.044 Uiso 1 1 calc R . . . .
C5 C 0.9296(4) 0.7554(3) 0.64987(16) 0.0265(7) Uani 1 1 d . . . . .
H5 H 1.0151 0.7424 0.6749 0.032 Uiso 1 1 calc R . . . .
C19 C 0.3824(4) 0.8814(4) 0.38303(17) 0.0336(8) Uani 1 1 d . . . . .
H19 H 0.4697 0.8701 0.4070 0.040 Uiso 1 1 calc R . . . .
C16 C 0.1283(4) 0.9139(4) 0.31244(19) 0.0363(9) Uani 1 1 d . . . . .
H16 H 0.0396 0.9260 0.2895 0.044 Uiso 1 1 calc R . . . .
C18 C 0.3805(4) 0.8759(4) 0.32103(18) 0.0346(8) Uani 1 1 d . . . . .
H18 H 0.4658 0.8601 0.3039 0.042 Uiso 1 1 calc R . . . .
C11 C 0.2032(5) 0.5684(4) 0.3308(2) 0.0390(9) Uani 1 1 d . . . . .
H11 H 0.1065 0.5919 0.3237 0.047 Uiso 1 1 calc R . . . .
C12 C 0.2833(4) 0.5439(3) 0.28158(17) 0.0314(8) Uani 1 1 d . . . . .
C14 C 0.4826(4) 0.5035(4) 0.35697(19) 0.0391(9) Uani 1 1 d . . . . .
H14 H 0.5794 0.4813 0.3653 0.047 Uiso 1 1 calc R . . . .
C13 C 0.4262(5) 0.5134(4) 0.2973(2) 0.0409(10) Uani 1 1 d . . . . .
H13 H 0.4859 0.4992 0.2668 0.049 Uiso 1 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 O2 2.048(2) 3_666 ?
Co1 O2 2.048(2) . ?
Co1 O1 2.139(2) . ?
Co1 O1 2.139(2) 3_666 ?
Co1 N1 2.225(3) 3_666 ?
Co1 N1 2.225(3) . ?
Co2 O6 1.948(2) 1_455 ?
Co2 O3 1.946(3) . ?
Co2 O4 1.967(3) 3_676 ?
Co2 N2 2.032(3) . ?
O6 Co2 1.948(2) 1_655 ?
O6 C8 1.265(4) . ?
O3 C1 1.261(4) . ?
O4 Co2 1.967(3) 3_676 ?
O4 C9 1.275(4) . ?
O2 H2A 0.8552 . ?
O2 H2B 0.8552 . ?
O1 C1 1.243(4) . ?
O5 C9 1.231(4) . ?
O7 C8 1.245(4) . ?
N2 C15 1.348(5) . ?
N2 C19 1.346(4) . ?
N1 C10 1.339(5) . ?
N1 C14 1.345(5) . ?
N3 N3 1.262(6) 2_656 ?
N3 C4 1.428(4) . ?
C1 C2 1.497(5) . ?
C2 C7 1.399(4) . ?
C2 C3 1.387(5) . ?
C7 C6 1.398(5) . ?
C7 C9 1.514(5) . ?
C8 C6 1.509(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 C5 1.389(4) . ?
C17 C17 1.478(7) 2 ?
C17 C16 1.398(5) . ?
C17 C18 1.390(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(6) . ?
C6 C5 1.388(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(6) . ?
C5 H5 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.373(5) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.408(5) . ?
C12 C12 1.469(7) 2 ?
C12 C13 1.376(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.374(6) . ?
C13 H13 0.9300 . ?

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 Co1 O2 180.0 3_666 . ?
O2 Co1 O1 84.55(9) . . ?
O2 Co1 O1 95.45(9) 3_666 . ?
O2 Co1 O1 95.45(9) . 3_666 ?
O2 Co1 O1 84.55(9) 3_666 3_666 ?
O2 Co1 N1 88.83(11) 3_666 3_666 ?
O2 Co1 N1 91.17(11) 3_666 . ?
O2 Co1 N1 91.17(11) . 3_666 ?
O2 Co1 N1 88.84(11) . . ?
O1 Co1 O1 180.0 3_666 . ?
O1 Co1 N1 96.07(10) 3_666 . ?
O1 Co1 N1 83.93(10) . . ?
O1 Co1 N1 96.07(10) . 3_666 ?
O1 Co1 N1 83.93(10) 3_666 3_666 ?
N1 Co1 N1 180.0 3_666 . ?
O6 Co2 O4 100.17(12) 1_455 3_676 ?
O6 Co2 N2 103.38(12) 1_455 . ?
O3 Co2 O6 124.40(12) . 1_455 ?
O3 Co2 O4 95.19(11) . 3_676 ?
O3 Co2 N2 112.84(12) . . ?
O4 Co2 N2 121.64(12) 3_676 . ?
C8 O6 Co2 125.3(2) . 1_655 ?
C1 O3 Co2 124.5(2) . . ?
C9 O4 Co2 134.3(2) . 3_676 ?
Co1 O2 H2A 110.0 . . ?
Co1 O2 H2B 109.7 . . ?
H2A O2 H2B 109.2 . . ?
C1 O1 Co1 138.1(2) . . ?
C15 N2 Co2 120.1(2) . . ?
C19 N2 Co2 122.4(3) . . ?
C19 N2 C15 117.4(3) . . ?
C10 N1 Co1 122.3(3) . . ?
C10 N1 C14 115.4(4) . . ?
C14 N1 Co1 122.3(3) . . ?
N3 N3 C4 112.9(4) 2_656 . ?
O3 C1 C2 115.9(3) . . ?
O1 C1 O3 123.9(3) . . ?
O1 C1 C2 120.2(3) . . ?
C7 C2 C1 121.9(3) . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 C7 120.5(3) . . ?
C2 C7 C9 118.4(3) . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 C9 122.2(3) . . ?
O6 C8 C6 115.2(3) . . ?
O7 C8 O6 125.6(3) . . ?
O7 C8 C6 119.1(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 N3 123.9(3) . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 N3 115.3(3) . . ?
C16 C17 C17 121.3(4) . 2 ?
C18 C17 C17 122.4(4) . 2 ?
C18 C17 C16 116.3(3) . . ?
N2 C15 H15 118.4 . . ?
N2 C15 C16 123.2(3) . . ?
C16 C15 H15 118.4 . . ?
C7 C6 C8 122.0(3) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C8 117.9(3) . . ?
O4 C9 C7 115.7(3) . . ?
O5 C9 O4 123.6(3) . . ?
O5 C9 C7 120.6(3) . . ?
N1 C10 H10 117.9 . . ?
N1 C10 C11 124.3(4) . . ?
C11 C10 H10 117.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
N2 C19 H19 118.9 . . ?
N2 C19 C18 122.2(4) . . ?
C18 C19 H19 118.9 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C12 122.2(4) . 2 ?
C13 C12 C11 115.1(4) . . ?
C13 C12 C12 122.6(4) . 2 ?
N1 C14 H14 118.2 . . ?
N1 C14 C13 123.7(4) . . ?
C13 C14 H14 118.2 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.250 -0.586 0.250 237.3 70.5 ?
2 0.250 -0.564 0.750 237.3 70.7 ?
3 0.000 0.500 0.500 11.4 0.0 ?
4 0.500 0.500 0.000 11.4 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.503
_oxdiff_exptl_absorpt_empirical_full_min 0.199
