# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_SKM_AP_CoPLY
_database_code_depnum_ccdc_archive 'CCDC 1828004'
loop_
_audit_author_name
_audit_author_address
'Gonela Vijaykumar' IISER-KOLKATA
_audit_update_record             
;
2018-03-07 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C17 H15 Co0.5 O3'
_chemical_formula_sum            'C17 H15 Co0.5 O3'
_chemical_formula_weight         296.77
_chemical_oxdiff_formula         C26H14O4Co1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Co -2.41037 3.56694 12.28410 7.34090 4.00340 2.34880 4.27910 0.27840 13.53590
71.16920 1.01180005074
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.6119(5)
_cell_length_b                   16.0078(7)
_cell_length_c                   12.0749(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.068(6)
_cell_angle_gamma                90
_cell_volume                     1853.22(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.8650
_cell_measurement_theta_min      3.6650
_exptl_absorpt_coefficient_mu    3.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.0636
_exptl_crystal_description       block
_exptl_crystal_F_000             615.0820
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7256
_diffrn_reflns_theta_full        66.3161
_diffrn_reflns_theta_max         66.32
_diffrn_reflns_theta_min         5.38
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9895
_diffrn_measured_fraction_theta_max 0.9895
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   25.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega   75.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   83.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   56.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega   48.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   21.0000   60.0000 149

#__ type_ start__ end____ width___ exp.time_
  7 omega  133.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega  139.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega  101.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430  111.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega  101.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430  111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   89.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6859   77.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega   44.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega   59.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  106.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   58.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6859 -178.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430 -111.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 18 omega   53.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6859  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   53.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   32.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 21 omega   28.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 22 omega   55.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   12.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   -9.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6859   57.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 25 omega   41.00  138.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430   61.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
 26 omega   53.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 27 omega   32.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
 28 omega   31.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       67.3430   77.0000   30.0000 106

#__ type_ start__ end____ width___ exp.time_
 29 omega  -15.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6859   77.0000 -150.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0511824000
_diffrn_orient_matrix_UB_12      0.0875371000
_diffrn_orient_matrix_UB_13      0.0365745000
_diffrn_orient_matrix_UB_21      -0.0499934000
_diffrn_orient_matrix_UB_22      -0.0156793000
_diffrn_orient_matrix_UB_23      0.1167306000
_diffrn_orient_matrix_UB_31      0.1438399000
_diffrn_orient_matrix_UB_32      -0.0366282000
_diffrn_orient_matrix_UB_33      0.0377287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -7
_reflns_number_gt                2514
_reflns_number_total             3218
_reflns_odcompleteness_completeness 97.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.3670
_refine_diff_density_min         -0.2774
_refine_diff_density_rms         0.0621
_refine_ls_d_res_high            0.8418
_refine_ls_d_res_low             8.2252
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9725
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      0.9725
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0944P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1490
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C13(H13a,H13b), C12(H12a,H12b), C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C2(H2), C3(H3), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Co1 Co 0.0 0.0 0.5 0.0430(2) Uani 1.000000 2 S T P
O2 O 0.0677(2) 0.04279(12) 0.35685(16) 0.0505(4) Uani 1.000000 1 . . .
O1 O 0.1026(2) 0.09577(12) 0.57604(15) 0.0529(5) Uani 1.000000 1 . . .
C9A C 0.1950(3) 0.16475(15) 0.4210(2) 0.0432(5) Uani 1.000000 1 . . .
C9 C 0.1436(3) 0.10605(17) 0.3387(2) 0.0458(6) Uani 1.000000 1 . . .
O3 O 0.1873(2) -0.07999(14) 0.5221(2) 0.0671(6) Uani 1.000000 1 . . .
C1 C 0.1699(3) 0.15558(16) 0.5360(2) 0.0475(6) Uani 1.000000 1 . . .
C9B C 0.2749(3) 0.23507(17) 0.3875(3) 0.0489(6) Uani 1.000000 1 . . .
C3A C 0.3258(3) 0.29509(18) 0.4657(3) 0.0575(7) Uani 1.000000 1 . . .
C6A C 0.3047(3) 0.2453(2) 0.2745(3) 0.0593(7) Uani 1.000000 1 . . .
C8 C 0.1812(4) 0.1175(2) 0.2256(3) 0.0642(8) Uani 1.000000 1 . . .
H8 H 0.1516(4) 0.0774(2) 0.1709(3) 0.0771(9) Uiso 1.000000 1 R . .
C7 C 0.2570(4) 0.1837(2) 0.1959(3) 0.0695(9) Uani 1.000000 1 . . .
H7 H 0.2791(4) 0.1893(2) 0.1208(3) 0.0834(10) Uiso 1.000000 1 R . .
C2 C 0.2248(4) 0.2181(2) 0.6126(3) 0.0618(7) Uani 1.000000 1 . . .
H2 H 0.2084(4) 0.2131(2) 0.6890(3) 0.0742(9) Uiso 1.000000 1 R . .
C3 C 0.2989(4) 0.2836(2) 0.5789(3) 0.0686(9) Uani 1.000000 1 . . .
H3 H 0.3343(4) 0.3232(2) 0.6323(3) 0.0823(10) Uiso 1.000000 1 R . .
C4 C 0.4019(4) 0.3640(2) 0.4305(4) 0.0751(10) Uani 1.000000 1 . . .
H4 H 0.4366(4) 0.4041(2) 0.4835(4) 0.0901(12) Uiso 1.000000 1 R . .
C6 C 0.3814(4) 0.3150(2) 0.2441(3) 0.0726(10) Uani 1.000000 1 . . .
H6 H 0.4023(4) 0.3212(2) 0.1688(3) 0.0871(12) Uiso 1.000000 1 R . .
C10 C 0.3175(3) -0.0594(2) 0.4816(4) 0.0750(10) Uani 1.000000 1 . . .
H10a H 0.3073(3) -0.0499(2) 0.4005(4) 0.0899(12) Uiso 1.000000 1 R . .
H10b H 0.3557(3) -0.0080(2) 0.5181(4) 0.0899(12) Uiso 1.000000 1 R . .
C5 C 0.4272(4) 0.3743(2) 0.3196(4) 0.0807(11) Uani 1.000000 1 . . .
H5 H 0.4758(4) 0.4222(2) 0.2963(4) 0.0968(14) Uiso 1.000000 1 R . .
C13 C 0.2021(4) -0.1494(3) 0.5935(4) 0.0855(13) Uani 1.000000 1 . . .
H13a H 0.1783(4) -0.1335(3) 0.6691(4) 0.1026(15) Uiso 1.000000 1 R . .
H13b H 0.1385(4) -0.1947(3) 0.5664(4) 0.1026(15) Uiso 1.000000 1 R . .
C12 C 0.3479(4) -0.1779(3) 0.5960(4) 0.0907(13) Uani 1.000000 1 . . .
H12a H 0.3970(4) -0.1659(3) 0.6692(4) 0.1089(15) Uiso 1.000000 1 R . .
H12b H 0.3519(4) -0.2388(3) 0.5820(4) 0.1089(15) Uiso 1.000000 1 R . .
C11 C 0.4113(4) -0.1317(3) 0.5083(6) 0.1088(19) Uani 1.000000 1 . . .
H11a H 0.4187(4) -0.1674(3) 0.4420(6) 0.131(2) Uiso 1.000000 1 R . .
H11b H 0.5058(4) -0.1122(3) 0.5342(6) 0.131(2) Uiso 1.000000 1 R . .


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 2.0101(18) 3_556 ?
Co1 O2 2.0101(18) . ?
Co1 O1 2.0092(19) . ?
Co1 O1 2.0092(19) 3_556 ?
Co1 O3 2.210(2) 3_556 ?
Co1 O3 2.210(2) . ?
O2 C9 1.276(3) . ?
O1 C1 1.271(3) . ?
C9A C9 1.429(4) . ?
C9A C1 1.434(4) . ?
C9A C9B 1.437(4) . ?
C9 C8 1.449(4) . ?
O3 C10 1.415(4) . ?
O3 C13 1.407(4) . ?
C1 C2 1.438(4) . ?
C9B C3A 1.410(4) . ?
C9B C6A 1.424(4) . ?
C3A C3 1.420(5) . ?
C3A C4 1.406(4) . ?
C6A C7 1.422(5) . ?
C6A C6 1.400(5) . ?
C8 C7 1.349(5) . ?
C2 C3 1.347(5) . ?
C4 C5 1.388(6) . ?
C6 C5 1.368(6) . ?
C10 C11 1.488(5) . ?
C13 C12 1.472(5) . ?
C12 C11 1.461(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
O2 Co1 O2 180.0 3_556 . ?
O1 Co1 O2 92.60(7) 3_556 . ?
O1 Co1 O2 87.40(7) . . ?
O1 Co1 O2 92.60(7) . 3_556 ?
O1 Co1 O2 87.40(7) 3_556 3_556 ?
O1 Co1 O1 180.0 3_556 . ?
O3 Co1 O2 90.55(8) 3_556 . ?
O3 Co1 O2 90.55(8) . 3_556 ?
O3 Co1 O2 89.45(8) . . ?
O3 Co1 O2 89.45(8) 3_556 3_556 ?
O3 Co1 O1 88.97(9) 3_556 . ?
O3 Co1 O1 88.97(9) . 3_556 ?
O3 Co1 O1 91.03(9) . . ?
O3 Co1 O1 91.03(9) 3_556 3_556 ?
O3 Co1 O3 180.0 . 3_556 ?
C9 O2 Co1 129.93(18) . . ?
C1 O1 Co1 130.36(18) . . ?
C1 C9A C9 122.1(2) . . ?
C9B C9A C9 119.0(2) . . ?
C9B C9A C1 118.8(3) . . ?
C9A C9 O2 125.2(2) . . ?
C8 C9 O2 116.5(3) . . ?
C8 C9 C9A 118.3(3) . . ?
C10 O3 Co1 123.81(19) . 3_556 ?
C13 O3 Co1 125.3(2) . 3_556 ?
C13 O3 C10 110.0(3) . . ?
C9A C1 O1 124.8(3) . . ?
C2 C1 O1 116.9(3) . . ?
C2 C1 C9A 118.2(2) . . ?
C3A C9B C9A 120.8(3) . . ?
C6A C9B C9A 120.5(3) . . ?
C6A C9B C3A 118.7(3) . . ?
C3 C3A C9B 118.5(3) . . ?
C4 C3A C9B 119.7(3) . . ?
C4 C3A C3 121.8(3) . . ?
C7 C6A C9B 118.9(3) . . ?
C6 C6A C9B 119.3(3) . . ?
C6 C6A C7 121.9(3) . . ?
C7 C8 C9 121.7(3) . . ?
C8 C7 C6A 121.5(3) . . ?
C3 C2 C1 121.6(3) . . ?
C2 C3 C3A 121.9(3) . . ?
C5 C4 C3A 121.0(4) . . ?
C5 C6 C6A 121.9(4) . . ?
C11 C10 O3 106.3(3) . . ?
C6 C5 C4 119.4(3) . . ?
C12 C13 O3 108.2(3) . . ?
C11 C12 C13 105.9(3) . . ?
C12 C11 C10 105.8(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 -0.500 0.000 0.000 319.8 72.0 ?
2 0.000 0.500 0.500 319.8 72.0 ?


_olex2_date_sample_data_collection 2014-05-01
_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_ply_dimer
_database_code_depnum_ccdc_archive 'CCDC 1846773'
loop_
_audit_author_name
_audit_author_address
'Gonela Vijaykumar'
;IISER-KOLKATA
India
;
_audit_update_record             
;
2018-06-01 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H8.65 O2'
_chemical_formula_sum            'C13 H8.64 O2'
_chemical_formula_weight         196.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z'
3 'x+1/2, -y, -z+1/2'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z'
7 '-x-1/2, y, z-1/2'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3790(5)
_cell_length_b                   14.8543(10)
_cell_length_c                   16.8845(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1850.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3670
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      24.9730
_cell_measurement_theta_min      2.7160
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             821
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10323
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -66.00   50.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1399   57.0000  120.0000 116

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00  116.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.5461   77.0000  -30.0000 132

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00  126.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.5461  178.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00  105.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.5461   57.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
  5 omega  -10.00   15.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       28.5461   57.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0569733000
_diffrn_orient_matrix_UB_12      -0.0080636000
_diffrn_orient_matrix_UB_13      0.0330849000
_diffrn_orient_matrix_UB_21      0.0658070000
_diffrn_orient_matrix_UB_22      -0.0295771000
_diffrn_orient_matrix_UB_23      0.0161076000
_diffrn_orient_matrix_UB_31      0.0405409000
_diffrn_orient_matrix_UB_32      0.0366224000
_diffrn_orient_matrix_UB_33      0.0203419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1372
_reflns_number_total             1635
_reflns_odcompleteness_completeness 86.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+1.0621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1110
_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 O(H) groups
2. Others
 Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C5(H5), C3A(H3A)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.40343(19) 0.15223(8) 0.51136(7) 0.0303(4) Uani 1 d . . .
H2 H 0.4174 0.1789 0.5534 0.045 Uiso 1 calc . . GR
O1 O 0.50027(19) 0.27825(9) 0.60416(7) 0.0318(4) Uani 1 d . . .
C12 C 0.5179(2) 0.29246(12) 0.46508(10) 0.0213(4) Uani 1 d . . .
C8 C 0.5549(2) 0.31422(12) 0.32151(10) 0.0229(4) Uani 1 d . . .
C13 C 0.5666(2) 0.34881(12) 0.39967(9) 0.0208(4) Uani 1 d A . .
C2 C 0.6496(3) 0.40962(12) 0.55560(10) 0.0238(4) Uani 1 d . . .
H2A H 0.7787 0.3977 0.5523 0.029 Uiso 0.823(11) calc A 1 R
H2B H 0.6247 0.4333 0.6080 0.029 Uiso 0.823(11) calc A 1 R
C1 C 0.5494(2) 0.32347(12) 0.54526(10) 0.0225(4) Uani 1 d A . .
C11 C 0.4523(2) 0.20602(12) 0.45140(10) 0.0241(4) Uani 1 d . . .
C6 C 0.6753(3) 0.45351(13) 0.27084(10) 0.0306(5) Uani 1 d . . .
H6 H 0.7160 0.4880 0.2285 0.037 Uiso 1 calc . . R
C7 C 0.6108(3) 0.36844(13) 0.25771(10) 0.0283(5) Uani 1 d . . .
H7 H 0.6038 0.3463 0.2063 0.034 Uiso 1 calc . . R
C9 C 0.4886(3) 0.22457(13) 0.31099(11) 0.0276(5) Uani 1 d . . .
H9 H 0.4795 0.2013 0.2600 0.033 Uiso 1 calc . . R
C4 C 0.6231(3) 0.43890(13) 0.41144(10) 0.0282(5) Uani 1 d . . .
C10 C 0.4386(3) 0.17238(13) 0.37334(11) 0.0279(4) Uani 1 d . . .
H10 H 0.3953 0.1144 0.3646 0.034 Uiso 1 calc . . R
C5 C 0.6805(3) 0.48877(13) 0.34749(11) 0.0312(5) Uani 1 d A . .
H5 H 0.7234 0.5469 0.3554 0.037 Uiso 1 calc . . R
C3 C 0.5989(5) 0.4820(2) 0.49306(12) 0.0199(9) Uani 0.823(11) d . 1 .
H3 H 0.6836 0.5325 0.4978 0.024 Uiso 0.823(11) calc A 1 R
C3A C 0.696(3) 0.4487(10) 0.4969(7) 0.034(5) Uani 0.177(11) d A 2 .
H3A H 0.7879 0.4908 0.5037 0.041 Uiso 0.177(11) calc A 2 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
O2 C11 1.339(2) . ?
O1 C1 1.254(2) . ?
C12 C13 1.432(2) . ?
C12 C1 1.449(2) . ?
C12 C11 1.392(2) . ?
C8 C13 1.419(2) . ?
C8 C7 1.407(3) . ?
C8 C9 1.430(3) . ?
C13 C4 1.416(3) . ?
C2 C1 1.488(3) . ?
C2 C3 1.553(4) . ?
C2 C3A 1.198(12) . ?
C11 C10 1.413(2) . ?
C6 C7 1.369(3) . ?
C6 C5 1.397(2) . ?
C9 C10 1.359(3) . ?
C4 C5 1.376(2) . ?
C4 C3 1.530(3) . ?
C4 C3A 1.547(12) . ?
C3 C3 1.571(8) 5_666 ?

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
C13 C12 C1 119.65(16) . . ?
C11 C12 C13 119.92(15) . . ?
C11 C12 C1 120.28(16) . . ?
C13 C8 C9 118.28(16) . . ?
C7 C8 C13 119.15(17) . . ?
C7 C8 C9 122.57(16) . . ?
C8 C13 C12 119.37(16) . . ?
C4 C13 C12 121.22(15) . . ?
C4 C13 C8 119.40(16) . . ?
C1 C2 C3 113.30(15) . . ?
C3A C2 C1 117.5(6) . . ?
C3A C2 C3 33.9(11) . . ?
O1 C1 C12 121.64(17) . . ?
O1 C1 C2 120.75(15) . . ?
C12 C1 C2 117.56(15) . . ?
O2 C11 C12 121.24(16) . . ?
O2 C11 C10 118.35(17) . . ?
C12 C11 C10 120.40(17) . . ?
C7 C6 C5 120.38(17) . . ?
C6 C7 C8 120.44(16) . . ?
C10 C9 C8 121.88(16) . . ?
C13 C4 C3 119.19(17) . . ?
C13 C4 C3A 108.8(5) . . ?
C5 C4 C13 119.29(16) . . ?
C5 C4 C3 121.15(18) . . ?
C5 C4 C3A 125.1(6) . . ?
C3 C4 C3A 32.9(7) . . ?
C9 C10 C11 120.10(18) . . ?
C4 C5 C6 121.12(18) . . ?
C2 C3 C3 111.0(2) . 5_666 ?
C4 C3 C2 107.1(2) . . ?
C4 C3 C3 112.7(3) . 5_666 ?
C2 C3A C4 128.8(12) . . ?

_olex2_date_sample_data_collection 2018-03-29
_olex2_submission_special_instructions 'No special instructions were received'
