# Electronic Supplementary Material (ESI) for ChemComm.
# 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_no1
_database_code_depnum_ccdc_archive 'CCDC 1045349'
_audit_update_record             
;
2015-01-24 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;
_audit_creation_date             2015-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H18 O'
_chemical_formula_sum            'C25 H18 O'
_chemical_formula_weight         334.39
_chemical_absolute_configuration unk
_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'

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

_cell_length_a                   8.2582(2)
_cell_length_b                   6.2091(2)
_cell_length_c                   17.8371(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1477(14)
_cell_angle_gamma                90.00
_cell_volume                     890.64(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31392
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                3479
_reflns_number_total             4438
_reflns_threshold_expression     >2sigma(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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(14)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.079
_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)+(0.0340P)²+0.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0958
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O -0.98315(13) -0.43300(18) -0.25200(6) 0.0302(3) Uani 1 d . . .
C2 C -0.82171(19) -0.4148(3) -0.11916(10) 0.0312(4) Uani 1 d . . .
H2 H -0.7728 -0.5510 -0.1207 0.037 Uiso 1 calc . . R
C3 C -0.93398(19) -0.3361(3) -0.18060(9) 0.0279(4) Uani 1 d . . .
C4 C -1.09181(19) -0.2887(3) -0.29875(10) 0.0301(4) Uani 1 d . . .
C5 C -0.8591(2) -0.0775(3) -0.05212(10) 0.0347(4) Uani 1 d . . .
C6 C -0.7812(2) -0.2843(3) -0.05272(10) 0.0327(4) Uani 1 d . . .
C7 C -1.38173(18) 0.1117(2) -0.27846(9) 0.0274(3) Uani 1 d . . .
C8 C -1.15316(19) -0.3586(3) -0.37822(10) 0.0320(4) Uani 1 d . . .
C9 C -0.97567(19) -0.0051(3) -0.11761(10) 0.0333(4) Uani 1 d . . .
H9 H -1.0279 0.1292 -0.1172 0.040 Uiso 1 calc . . R
C10 C -1.01252(18) -0.1333(3) -0.18246(9) 0.0280(3) Uani 1 d . . .
C11 C -1.20523(19) 0.0936(3) -0.28924(11) 0.0334(4) Uani 1 d . . .
H11A H -1.2088 0.1047 -0.3444 0.040 Uiso 1 calc . . R
H11B H -1.1418 0.2173 -0.2639 0.040 Uiso 1 calc . . R
C12 C -0.6628(2) -0.3508(3) 0.01433(11) 0.0401(4) Uani 1 d . . .
H12 H -0.6105 -0.4854 0.0148 0.048 Uiso 1 calc . . R
C13 C -1.11225(18) -0.1073(3) -0.25933(10) 0.0295(4) Uani 1 d . . .
C14 C -1.4642(2) 0.3073(3) -0.29340(10) 0.0337(4) Uani 1 d . . .
H14 H -1.4096 0.4250 -0.3099 0.040 Uiso 1 calc . . R
C15 C -0.8151(2) 0.0506(3) 0.01560(11) 0.0455(5) Uani 1 d . . .
H15 H -0.8653 0.1859 0.0171 0.055 Uiso 1 calc . . R
C16 C -1.4654(2) -0.0589(3) -0.25453(10) 0.0341(4) Uani 1 d . . .
H16 H -1.4122 -0.1930 -0.2442 0.041 Uiso 1 calc . . R
C17 C -1.0685(2) -0.5143(3) -0.41054(11) 0.0384(4) Uani 1 d . . .
H17 H -0.9716 -0.5773 -0.3807 0.046 Uiso 1 calc . . R
C18 C -1.6269(2) -0.0340(3) -0.24554(11) 0.0401(4) Uani 1 d . . .
H18 H -1.6820 -0.1513 -0.2292 0.048 Uiso 1 calc . . R
C19 C -1.6250(2) 0.3320(3) -0.28443(11) 0.0387(4) Uani 1 d . . .
H19 H -1.6787 0.4658 -0.2948 0.046 Uiso 1 calc . . R
C20 C -1.7071(2) 0.1612(3) -0.26037(11) 0.0392(4) Uani 1 d . . .
H20 H -1.8165 0.1777 -0.2542 0.047 Uiso 1 calc . . R
C21 C -0.7006(3) -0.0211(4) 0.07856(12) 0.0538(6) Uani 1 d . . .
H21 H -0.6728 0.0656 0.1228 0.065 Uiso 1 calc . . R
C22 C -0.6241(2) -0.2226(4) 0.07786(11) 0.0495(5) Uani 1 d . . .
H22 H -0.5454 -0.2694 0.1216 0.059 Uiso 1 calc . . R
C23 C -1.2680(3) -0.4853(4) -0.53134(12) 0.0553(6) Uani 1 d . . .
H23 H -1.3057 -0.5264 -0.5831 0.066 Uiso 1 calc . . R
C24 C -1.2981(2) -0.2718(3) -0.42382(11) 0.0438(5) Uani 1 d . . .
H24 H -1.3590 -0.1698 -0.4027 0.053 Uiso 1 calc . . R
C25 C -1.1262(3) -0.5767(3) -0.48642(12) 0.0492(5) Uani 1 d . . .
H25 H -1.0683 -0.6824 -0.5076 0.059 Uiso 1 calc . . R
C26 C -1.3531(3) -0.3336(4) -0.49958(12) 0.0555(6) Uani 1 d . . .
H26 H -1.4500 -0.2713 -0.5298 0.067 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
O1 C3 1.3833(19) . ?
O1 C4 1.4010(18) . ?
C2 C3 1.355(2) . ?
C2 C6 1.412(2) . ?
C3 C10 1.413(2) . ?
C4 C8 1.459(2) . ?
C4 C13 1.359(2) . ?
C5 C6 1.438(2) . ?
C5 C9 1.408(2) . ?
C5 C15 1.423(2) . ?
C6 C12 1.422(2) . ?
C7 C11 1.517(2) . ?
C7 C14 1.388(2) . ?
C7 C16 1.384(2) . ?
C8 C17 1.393(2) . ?
C8 C24 1.393(2) . ?
C9 C10 1.380(2) . ?
C10 C13 1.439(2) . ?
C11 C13 1.498(2) . ?
C12 C22 1.362(3) . ?
C14 C19 1.382(2) . ?
C15 C21 1.368(3) . ?
C16 C18 1.387(2) . ?
C17 C25 1.384(3) . ?
C18 C20 1.378(3) . ?
C19 C20 1.379(3) . ?
C21 C22 1.403(3) . ?
C23 C25 1.382(3) . ?
C23 C26 1.372(3) . ?
C24 C26 1.379(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
C3 O1 C4 106.51(12) . . ?
C3 C2 C6 117.37(15) . . ?
O1 C3 C10 109.19(13) . . ?
C2 C3 O1 126.24(15) . . ?
C2 C3 C10 124.48(15) . . ?
O1 C4 C8 114.97(14) . . ?
C13 C4 O1 111.11(14) . . ?
C13 C4 C8 133.87(16) . . ?
C9 C5 C6 120.12(16) . . ?
C9 C5 C15 121.36(17) . . ?
C15 C5 C6 118.52(17) . . ?
C2 C6 C5 119.86(15) . . ?
C2 C6 C12 121.72(16) . . ?
C12 C6 C5 118.41(16) . . ?
C14 C7 C11 118.93(14) . . ?
C16 C7 C11 122.94(14) . . ?
C16 C7 C14 118.12(14) . . ?
C17 C8 C4 120.84(15) . . ?
C17 C8 C24 118.19(17) . . ?
C24 C8 C4 120.97(16) . . ?
C10 C9 C5 119.36(15) . . ?
C3 C10 C13 106.41(14) . . ?
C9 C10 C3 118.79(15) . . ?
C9 C10 C13 134.69(15) . . ?
C13 C11 C7 116.48(13) . . ?
C22 C12 C6 121.10(19) . . ?
C4 C13 C10 106.78(14) . . ?
C4 C13 C11 128.32(16) . . ?
C10 C13 C11 124.65(15) . . ?
C19 C14 C7 121.14(16) . . ?
C21 C15 C5 120.68(19) . . ?
C7 C16 C18 120.71(15) . . ?
C25 C17 C8 120.38(18) . . ?
C20 C18 C16 120.58(16) . . ?
C20 C19 C14 120.30(16) . . ?
C18 C20 C19 119.15(15) . . ?
C15 C21 C22 120.8(2) . . ?
C12 C22 C21 120.49(19) . . ?
C26 C23 C25 119.3(2) . . ?
C26 C24 C8 120.82(19) . . ?
C23 C25 C17 120.7(2) . . ?
C23 C26 C24 120.67(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
