# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mo_20170516_madou_ws_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1832662'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-21
_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         'C26 H18 O2'
_chemical_formula_sum            'C26 H18 O2'
_chemical_formula_weight         362.40
_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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.874(3)
_cell_length_b                   4.0616(6)
_cell_length_c                   22.609(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.113(4)
_cell_angle_gamma                90
_cell_volume                     1852.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9639
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.019
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1615
_reflns_number_total             2120
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.022
_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)+(0.0563P)²+0.6230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1130
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O -0.06549(5) 0.6014(3) 0.26087(5) 0.0626(3) Uani 1 1 d . . . . .
C1 C 0.15631(6) 0.0183(3) 0.54643(6) 0.0375(3) Uani 1 1 d . . . . .
C2 C 0.12996(7) -0.0727(4) 0.58833(7) 0.0506(4) Uani 1 1 d . . . . .
H2 H 0.0845 -0.0591 0.5727 0.061 Uiso 1 1 calc R . . . .
C3 C 0.17047(8) -0.1831(4) 0.65285(7) 0.0610(4) Uani 1 1 d . . . . .
H3 H 0.1521 -0.2455 0.6801 0.073 Uiso 1 1 calc R . . . .
C4 C 0.23795(8) -0.2007(4) 0.67670(7) 0.0585(4) Uani 1 1 d . . . . .
H4 H 0.2652 -0.2759 0.7200 0.070 Uiso 1 1 calc R . . . .
C5 C 0.26509(7) -0.1072(4) 0.63662(7) 0.0539(4) Uani 1 1 d . . . . .
H5 H 0.3108 -0.1152 0.6531 0.065 Uiso 1 1 calc R . . . .
C6 C 0.22473(7) -0.0013(4) 0.57189(6) 0.0459(3) Uani 1 1 d . . . . .
H6 H 0.2436 0.0580 0.5449 0.055 Uiso 1 1 calc R . . . .
C7 C 0.11303(6) 0.1305(3) 0.47671(6) 0.0352(3) Uani 1 1 d . . . . .
C8 C 0.05466(6) 0.3045(4) 0.45986(6) 0.0421(3) Uani 1 1 d . . . . .
H8 H 0.0426 0.3501 0.4930 0.051 Uiso 1 1 calc R . . . .
C9 C 0.01445(6) 0.4101(3) 0.39529(6) 0.0421(3) Uani 1 1 d . . . . .
H9 H -0.0244 0.5241 0.3853 0.051 Uiso 1 1 calc R . . . .
C10 C 0.03156(6) 0.3472(3) 0.34471(6) 0.0365(3) Uani 1 1 d . . . . .
C11 C 0.08925(6) 0.1713(3) 0.36058(6) 0.0397(3) Uani 1 1 d . . . . .
H11 H 0.1011 0.1253 0.3273 0.048 Uiso 1 1 calc R . . . .
C12 C 0.12903(6) 0.0644(3) 0.42541(6) 0.0394(3) Uani 1 1 d . . . . .
H12 H 0.1673 -0.0540 0.4351 0.047 Uiso 1 1 calc R . . . .
C13 C -0.01227(6) 0.4714(3) 0.27639(6) 0.0425(3) Uani 1 1 d . . . . .


_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
O1 C13 1.2170(16) . ?
C1 C2 1.3913(18) . ?
C1 C6 1.3921(18) . ?
C1 C7 1.4837(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3806(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.3958(17) . ?
C7 C12 1.3968(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3769(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3956(17) . ?
C10 C11 1.3909(18) . ?
C10 C13 1.4786(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3812(17) . ?
C12 H12 0.9300 . ?
C13 C13 1.540(3) 2 ?

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
C2 C1 C6 117.82(12) . . ?
C2 C1 C7 121.24(12) . . ?
C6 C1 C7 120.94(11) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.95(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.01(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.01(13) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.13(14) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.07(13) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C1 121.26(11) . . ?
C8 C7 C12 117.51(11) . . ?
C12 C7 C1 121.23(11) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.49(11) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.43(12) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C13 118.65(11) . . ?
C11 C10 C9 118.75(11) . . ?
C11 C10 C13 122.59(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(11) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.43(12) . . ?
C11 C12 H12 119.3 . . ?
O1 C13 C10 122.89(12) . . ?
O1 C13 C13 117.20(12) . 2 ?
C10 C13 C13 119.62(13) . 2 ?

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
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C7 C8 C9 179.77(12) . . . . ?
C1 C7 C12 C11 -179.33(12) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C7 C8 32.76(19) . . . . ?
C2 C1 C7 C12 -146.92(13) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C7 C8 -147.66(13) . . . . ?
C6 C1 C7 C12 32.66(19) . . . . ?
C7 C1 C2 C3 178.74(14) . . . . ?
C7 C1 C6 C5 -179.65(13) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C7 C12 C11 0.98(19) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C13 -178.67(12) . . . . ?
C9 C10 C11 C12 -0.67(19) . . . . ?
C9 C10 C13 O1 -6.5(2) . . . . ?
C9 C10 C13 C13 167.05(9) . . . 2 ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C11 C10 C13 O1 173.74(13) . . . . ?
C11 C10 C13 C13 -12.71(16) . . . 2 ?
C12 C7 C8 C9 -0.5(2) . . . . ?
C13 C10 C11 C12 179.09(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
