# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mk_b
_audit_block_doi                 10.5517/ccdc.csd.cc294c61
_database_code_depnum_ccdc_archive 'CCDC 2119352'
loop_
_audit_author_name
_audit_author_address
' Adarsh N Narayanan'
;Solid State and Materials Chemistry Research Group   Mahatma Gandhi University
India
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-06-01 downloaded from the CCDC.
;
_audit_creation_date             2021-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Fe O'
_chemical_formula_sum            'C15 H12 Fe O'
_chemical_formula_weight         264.10
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0806(8)
_cell_length_b                   9.2146(7)
_cell_length_c                   13.0917(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.363(2)
_cell_angle_gamma                90
_cell_volume                     1213.98(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.024
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_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    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41738
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.159
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Microfocal D8 venture Bruker APEX 3'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             2671
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.044
_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)+(0.0330P)²+0.2801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0654
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C14(H14), C15(H15)
2.b :
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.17755(2) 0.13225(2) 0.36651(2) 0.04361(9) Uani 1 1 d . . . . .
O1 O 0.70536(15) 0.44307(19) 0.47850(11) 0.0906(5) Uani 1 1 d . . . . .
C1 C 0.1117(2) 0.1763(2) 0.21916(13) 0.0678(5) Uani 1 1 d . . . . .
H1 H 0.128899 0.121509 0.161733 0.081 Uiso 1 1 calc R U . . .
C2 C 0.18995(17) 0.29186(19) 0.25998(12) 0.0594(4) Uani 1 1 d . . . . .
H2 H 0.267718 0.326869 0.234077 0.071 Uiso 1 1 calc R U . . .
C3 C 0.12968(19) 0.34478(18) 0.34664(14) 0.0610(4) Uani 1 1 d . . . . .
H3 H 0.160647 0.420921 0.388136 0.073 Uiso 1 1 calc R U . . .
C4 C 0.01343(17) 0.2619(2) 0.35979(15) 0.0671(4) Uani 1 1 d . . . . .
H4 H -0.045195 0.273920 0.411399 0.081 Uiso 1 1 calc R U . . .
C5 C 0.00255(19) 0.1585(2) 0.28119(15) 0.0697(5) Uani 1 1 d . . . . .
H5 H -0.064811 0.090053 0.271479 0.084 Uiso 1 1 calc R U . . .
C6 C 0.30511(17) -0.03848(17) 0.36590(12) 0.0563(4) Uani 1 1 d . . . . .
H6 H 0.334869 -0.083734 0.308016 0.068 Uiso 1 1 calc R U . . .
C7 C 0.19095(18) -0.07740(19) 0.41779(14) 0.0651(4) Uani 1 1 d . . . . .
H7 H 0.132988 -0.152965 0.399916 0.078 Uiso 1 1 calc R U . . .
C8 C 0.18013(17) 0.0179(2) 0.50113(12) 0.0621(4) Uani 1 1 d . . . . .
H8 H 0.113938 0.015840 0.547690 0.075 Uiso 1 1 calc R U . . .
C9 C 0.28687(15) 0.11689(18) 0.50181(11) 0.0521(4) Uani 1 1 d . . . . .
H9 H 0.302799 0.191695 0.548618 0.063 Uiso 1 1 calc R U . . .
C10 C 0.36657(14) 0.08245(16) 0.41802(10) 0.0445(3) Uani 1 1 d . . . . .
C11 C 0.48447(13) 0.16198(15) 0.38930(10) 0.0427(3) Uani 1 1 d . . . . .
C12 C 0.53952(15) 0.12126(16) 0.29428(11) 0.0491(3) Uani 1 1 d . . . . .
C13 C 0.58156(18) 0.0879(2) 0.21584(13) 0.0654(4) Uani 1 1 d . . . . .
H13 H 0.614833 0.061513 0.153729 0.078 Uiso 1 1 calc R U . . .
C14 C 0.53959(14) 0.26763(18) 0.44837(11) 0.0517(3) Uani 1 1 d . . . . .
H14 H 0.499113 0.290914 0.508264 0.062 Uiso 1 1 calc R U . . .
C15 C 0.65727(17) 0.3475(2) 0.42533(13) 0.0615(4) Uani 1 1 d . . . . .
H15 H 0.698565 0.323851 0.365865 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 2.0434(16) . ?
Fe1 C2 2.0357(15) . ?
Fe1 C3 2.0301(17) . ?
Fe1 C4 2.0383(18) . ?
Fe1 C5 2.0463(17) . ?
Fe1 C6 2.0321(16) . ?
Fe1 C7 2.0470(17) . ?
Fe1 C8 2.0523(15) . ?
Fe1 C9 2.0355(15) . ?
Fe1 C10 2.0359(14) . ?
O1 C15 1.207(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.412(2) . ?
C1 C5 1.415(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.418(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.416(2) . ?
C6 C10 1.429(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.433(2) . ?
C10 C11 1.464(2) . ?
C11 C12 1.4412(19) . ?
C11 C14 1.343(2) . ?
C12 C13 1.175(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.443(2) . ?
C15 H15 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
C1 Fe1 C5 40.49(8) . . ?
C1 Fe1 C7 120.56(8) . . ?
C1 Fe1 C8 154.11(7) . . ?
C2 Fe1 C1 40.49(7) . . ?
C2 Fe1 C4 68.24(7) . . ?
C2 Fe1 C5 68.05(7) . . ?
C2 Fe1 C7 154.29(8) . . ?
C2 Fe1 C8 163.96(7) . . ?
C2 Fe1 C10 107.21(6) . . ?
C3 Fe1 C1 68.04(8) . . ?
C3 Fe1 C2 40.44(7) . . ?
C3 Fe1 C4 40.79(7) . . ?
C3 Fe1 C5 67.99(8) . . ?
C3 Fe1 C6 153.13(7) . . ?
C3 Fe1 C7 164.37(8) . . ?
C3 Fe1 C8 126.60(8) . . ?
C3 Fe1 C9 106.92(7) . . ?
C3 Fe1 C10 118.08(7) . . ?
C4 Fe1 C1 67.99(8) . . ?
C4 Fe1 C5 40.14(8) . . ?
C4 Fe1 C7 127.22(7) . . ?
C4 Fe1 C8 107.89(7) . . ?
C5 Fe1 C7 109.19(7) . . ?
C5 Fe1 C8 119.77(7) . . ?
C6 Fe1 C1 108.69(8) . . ?
C6 Fe1 C2 119.50(7) . . ?
C6 Fe1 C4 164.94(7) . . ?
C6 Fe1 C5 127.94(8) . . ?
C6 Fe1 C7 40.63(7) . . ?
C6 Fe1 C8 68.27(7) . . ?
C6 Fe1 C9 68.85(7) . . ?
C6 Fe1 C10 41.13(6) . . ?
C7 Fe1 C8 40.23(7) . . ?
C9 Fe1 C1 164.70(7) . . ?
C9 Fe1 C2 126.48(7) . . ?
C9 Fe1 C4 118.35(7) . . ?
C9 Fe1 C5 152.70(8) . . ?
C9 Fe1 C7 68.10(7) . . ?
C9 Fe1 C8 40.36(6) . . ?
C9 Fe1 C10 41.21(6) . . ?
C10 Fe1 C1 127.10(7) . . ?
C10 Fe1 C4 152.61(7) . . ?
C10 Fe1 C5 165.37(8) . . ?
C10 Fe1 C7 68.67(6) . . ?
C10 Fe1 C8 68.61(6) . . ?
Fe1 C1 H1 126.2 . . ?
C2 C1 Fe1 69.46(9) . . ?
C2 C1 H1 126.1 . . ?
C2 C1 C5 107.81(17) . . ?
C5 C1 Fe1 69.86(10) . . ?
C5 C1 H1 126.1 . . ?
Fe1 C2 H2 126.0 . . ?
C1 C2 Fe1 70.05(9) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 Fe1 69.56(9) . . ?
C3 C2 C1 108.01(16) . . ?
C3 C2 H2 126.0 . . ?
Fe1 C3 H3 125.7 . . ?
C2 C3 Fe1 69.99(10) . . ?
C2 C3 H3 126.0 . . ?
C2 C3 C4 108.09(16) . . ?
C4 C3 Fe1 69.92(10) . . ?
C4 C3 H3 126.0 . . ?
Fe1 C4 H4 126.0 . . ?
C3 C4 Fe1 69.29(10) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 Fe1 70.24(11) . . ?
C5 C4 C3 107.86(17) . . ?
C5 C4 H4 126.1 . . ?
Fe1 C5 H5 126.4 . . ?
C1 C5 Fe1 69.65(10) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 Fe1 69.62(10) . . ?
C4 C5 C1 108.22(16) . . ?
C4 C5 H5 125.9 . . ?
Fe1 C6 H6 125.8 . . ?
C7 C6 Fe1 70.25(10) . . ?
C7 C6 H6 126.0 . . ?
C7 C6 C10 108.07(14) . . ?
C10 C6 Fe1 69.58(9) . . ?
C10 C6 H6 126.0 . . ?
Fe1 C7 H7 126.6 . . ?
C6 C7 Fe1 69.12(9) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 Fe1 70.08(10) . . ?
C8 C7 C6 108.38(15) . . ?
C8 C7 H7 125.8 . . ?
Fe1 C8 H8 126.9 . . ?
C7 C8 Fe1 69.68(9) . . ?
C7 C8 H8 125.8 . . ?
C7 C8 C9 108.31(15) . . ?
C9 C8 Fe1 69.18(8) . . ?
C9 C8 H8 125.8 . . ?
Fe1 C9 H9 125.8 . . ?
C8 C9 Fe1 70.46(9) . . ?
C8 C9 H9 125.9 . . ?
C8 C9 C10 108.29(14) . . ?
C10 C9 Fe1 69.41(8) . . ?
C10 C9 H9 125.9 . . ?
C6 C10 Fe1 69.29(9) . . ?
C6 C10 C9 106.94(13) . . ?
C6 C10 C11 127.12(13) . . ?
C9 C10 Fe1 69.38(8) . . ?
C9 C10 C11 125.87(13) . . ?
C11 C10 Fe1 124.07(10) . . ?
C12 C11 C10 116.80(13) . . ?
C14 C11 C10 121.98(12) . . ?
C14 C11 C12 121.22(13) . . ?
C13 C12 C11 178.49(18) . . ?
C12 C13 H13 180.0 . . ?
C11 C14 H14 117.7 . . ?
C11 C14 C15 124.52(14) . . ?
C15 C14 H14 117.7 . . ?
O1 C15 C14 124.00(17) . . ?
O1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 C1 C2 C3 -59.43(12) . . . . ?
Fe1 C1 C5 C4 59.13(13) . . . . ?
Fe1 C2 C3 C4 -59.77(12) . . . . ?
Fe1 C3 C4 C5 -59.89(12) . . . . ?
Fe1 C4 C5 C1 -59.14(13) . . . . ?
Fe1 C6 C7 C8 -59.27(12) . . . . ?
Fe1 C6 C10 C9 59.42(10) . . . . ?
Fe1 C6 C10 C11 -117.71(14) . . . . ?
Fe1 C7 C8 C9 -58.55(12) . . . . ?
Fe1 C8 C9 C10 -59.32(11) . . . . ?
Fe1 C9 C10 C6 -59.36(10) . . . . ?
Fe1 C9 C10 C11 117.81(14) . . . . ?
Fe1 C10 C11 C12 -83.83(15) . . . . ?
Fe1 C10 C11 C14 96.40(15) . . . . ?
C1 C2 C3 Fe1 59.73(12) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C1 C5 Fe1 -59.31(12) . . . . ?
C2 C1 C5 C4 -0.2(2) . . . . ?
C2 C3 C4 Fe1 59.82(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 Fe1 59.30(12) . . . . ?
C3 C4 C5 C1 0.2(2) . . . . ?
C5 C1 C2 Fe1 59.57(12) . . . . ?
C5 C1 C2 C3 0.1(2) . . . . ?
C6 C7 C8 Fe1 58.68(11) . . . . ?
C6 C7 C8 C9 0.13(19) . . . . ?
C6 C10 C11 C12 4.8(2) . . . . ?
C6 C10 C11 C14 -174.95(15) . . . . ?
C7 C6 C10 Fe1 -59.95(11) . . . . ?
C7 C6 C10 C9 -0.53(17) . . . . ?
C7 C6 C10 C11 -177.65(14) . . . . ?
C7 C8 C9 Fe1 58.86(12) . . . . ?
C7 C8 C9 C10 -0.46(18) . . . . ?
C8 C9 C10 Fe1 59.97(11) . . . . ?
C8 C9 C10 C6 0.61(17) . . . . ?
C8 C9 C10 C11 177.78(14) . . . . ?
C9 C10 C11 C12 -171.78(14) . . . . ?
C9 C10 C11 C14 8.4(2) . . . . ?
C10 C6 C7 Fe1 59.53(11) . . . . ?
C10 C6 C7 C8 0.26(19) . . . . ?
C10 C11 C14 C15 178.55(15) . . . . ?
C11 C14 C15 O1 179.35(19) . . . . ?
C12 C11 C14 C15 -1.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
