# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_a51119b
_database_code_depnum_ccdc_archive 'CCDC 1442356'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 O'
_chemical_formula_weight         284.34

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   13.33(5)
_cell_length_b                   15.13(5)
_cell_length_c                   7.59(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.77(5)
_cell_angle_gamma                90
_cell_volume                     1503(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    535
_cell_measurement_theta_min      3.047
_cell_measurement_theta_max      25.384

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5793
_diffrn_reflns_av_unetI/netI     0.1618
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.555
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2911
_reflns_number_gt                1091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0345P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2911
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   0.692
_refine_ls_restrained_S_all      0.692
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.84669(11) 1.16657(9) 1.0247(2) 0.0632(5) Uani 1 1 d . . . . .
C1 C 0.70941(16) 0.95724(13) 0.4107(3) 0.0453(5) Uani 1 1 d . . . . .
C2 C 0.60856(16) 0.95672(13) 0.3349(3) 0.0529(6) Uani 1 1 d . . . . .
H2 H 0.5638 0.9906 0.3873 0.063 Uiso 1 1 calc R U . . .
C3 C 0.56835(16) 0.90640(14) 0.1785(3) 0.0484(6) Uani 1 1 d . . . . .
C4 C 0.46242(17) 0.90799(14) 0.1061(3) 0.0594(6) Uani 1 1 d . . . . .
H4 H 0.4189 0.9425 0.1600 0.071 Uiso 1 1 calc R U . . .
C5 C 0.42380(18) 0.85913(16) -0.0424(3) 0.0685(7) Uani 1 1 d . . . . .
H5 H 0.3543 0.8605 -0.0903 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4886(2) 0.80781(16) -0.1206(3) 0.0774(8) Uani 1 1 d . . . . .
H6 H 0.4620 0.7741 -0.2210 0.093 Uiso 1 1 calc R U . . .
C7 C 0.59132(18) 0.80524(15) -0.0542(3) 0.0684(7) Uani 1 1 d . . . . .
H7 H 0.6333 0.7703 -0.1106 0.082 Uiso 1 1 calc R U . . .
C8 C 0.63430(16) 0.85463(13) 0.0980(3) 0.0468(6) Uani 1 1 d . . . . .
C9 C 0.74320(16) 0.85539(13) 0.1733(3) 0.0470(6) Uani 1 1 d . . . . .
C10 C 0.81468(17) 0.80812(14) 0.0947(3) 0.0579(6) Uani 1 1 d . . . . .
H10 H 0.7913 0.7728 -0.0048 0.069 Uiso 1 1 calc R U . . .
C11 C 0.91802(18) 0.81257(15) 0.1605(3) 0.0679(7) Uani 1 1 d . . . . .
H11 H 0.9635 0.7812 0.1050 0.082 Uiso 1 1 calc R U . . .
C12 C 0.95383(18) 0.86381(15) 0.3095(3) 0.0630(7) Uani 1 1 d . . . . .
H12 H 1.0236 0.8670 0.3548 0.076 Uiso 1 1 calc R U . . .
C13 C 0.88663(16) 0.90992(13) 0.3903(3) 0.0543(6) Uani 1 1 d . . . . .
H13 H 0.9120 0.9445 0.4901 0.065 Uiso 1 1 calc R U . . .
C14 C 0.77983(15) 0.90687(13) 0.3273(3) 0.0441(5) Uani 1 1 d . . . . .
C15 C 0.74615(14) 1.01096(14) 0.5746(3) 0.0468(6) Uani 1 1 d . . . . .
C16 C 0.79491(15) 0.97181(14) 0.7332(3) 0.0551(6) Uani 1 1 d . . . . .
H16 H 0.8049 0.9110 0.7369 0.066 Uiso 1 1 calc R U . . .
C17 C 0.82899(15) 1.02142(14) 0.8857(3) 0.0556(6) Uani 1 1 d . . . . .
H17 H 0.8614 0.9939 0.9906 0.067 Uiso 1 1 calc R U . . .
C18 C 0.81495(15) 1.11075(14) 0.8821(3) 0.0466(6) Uani 1 1 d . . . . .
C19 C 0.76532(15) 1.15086(14) 0.7260(3) 0.0536(6) Uani 1 1 d . . . . .
H19 H 0.7547 1.2116 0.7234 0.064 Uiso 1 1 calc R U . . .
C20 C 0.73172(15) 1.10142(15) 0.5750(3) 0.0538(6) Uani 1 1 d . . . . .
H20 H 0.6986 1.1293 0.4709 0.065 Uiso 1 1 calc R U . . .
C21 C 0.89765(18) 1.12760(15) 1.1873(3) 0.0811(8) Uani 1 1 d . . . . .
H21A H 0.8544 1.0836 1.2256 0.122 Uiso 1 1 calc R U . . .
H21B H 0.9132 1.1724 1.2780 0.122 Uiso 1 1 calc R U . . .
H21C H 0.9598 1.1004 1.1683 0.122 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
O1 C18 1.375(4) . ?
O1 C21 1.421(4) . ?
C1 C2 1.360(5) . ?
C1 C14 1.444(4) . ?
C1 C15 1.489(5) . ?
C2 C3 1.427(4) . ?
C3 C8 1.400(4) . ?
C3 C4 1.416(5) . ?
C4 C5 1.365(4) . ?
C5 C6 1.376(4) . ?
C6 C7 1.368(5) . ?
C7 C8 1.405(4) . ?
C8 C9 1.457(6) . ?
C9 C10 1.410(4) . ?
C9 C14 1.413(4) . ?
C10 C11 1.376(5) . ?
C11 C12 1.380(4) . ?
C12 C13 1.368(4) . ?
C13 C14 1.415(6) . ?
C15 C20 1.382(5) . ?
C15 C16 1.389(4) . ?
C16 C17 1.383(4) . ?
C17 C18 1.364(5) . ?
C18 C19 1.384(4) . ?
C19 C20 1.371(4) . ?

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
C18 O1 C21 117.1(3) . . ?
C2 C1 C14 119.0(3) . . ?
C2 C1 C15 120.1(2) . . ?
C14 C1 C15 121.0(3) . . ?
C1 C2 C3 122.9(2) . . ?
C8 C3 C4 120.1(3) . . ?
C8 C3 C2 119.5(3) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 119.4(3) . . ?
C7 C6 C5 121.5(3) . . ?
C6 C7 C8 120.9(2) . . ?
C3 C8 C7 117.6(3) . . ?
C3 C8 C9 119.0(3) . . ?
C7 C8 C9 123.4(2) . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 C8 122.2(3) . . ?
C14 C9 C8 119.6(2) . . ?
C11 C10 C9 122.1(3) . . ?
C10 C11 C12 119.6(2) . . ?
C13 C12 C11 119.9(3) . . ?
C12 C13 C14 122.3(3) . . ?
C9 C14 C13 117.9(2) . . ?
C9 C14 C1 120.1(3) . . ?
C13 C14 C1 122.0(3) . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 C1 121.2(2) . . ?
C16 C15 C1 121.2(3) . . ?
C17 C16 C15 121.4(3) . . ?
C18 C17 C16 119.9(2) . . ?
C17 C18 O1 124.9(2) . . ?
C17 C18 C19 119.6(2) . . ?
O1 C18 C19 115.5(3) . . ?
C20 C19 C18 120.3(3) . . ?
C19 C20 C15 121.2(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
C14 C1 C2 C3 1.8(3) . . . . ?
C15 C1 C2 C3 -179.69(19) . . . . ?
C1 C2 C3 C8 0.2(3) . . . . ?
C1 C2 C3 C4 179.6(2) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C2 C3 C8 C7 179.2(2) . . . . ?
C4 C3 C8 C9 178.92(18) . . . . ?
C2 C3 C8 C9 -1.7(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C3 C8 C9 C10 -177.09(18) . . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?
C3 C8 C9 C14 1.1(3) . . . . ?
C7 C8 C9 C14 -179.8(2) . . . . ?
C14 C9 C10 C11 -1.7(3) . . . . ?
C8 C9 C10 C11 176.5(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C10 C9 C14 C13 1.9(3) . . . . ?
C8 C9 C14 C13 -176.43(18) . . . . ?
C10 C9 C14 C1 179.20(18) . . . . ?
C8 C9 C14 C1 0.9(3) . . . . ?
C12 C13 C14 C9 -1.3(3) . . . . ?
C12 C13 C14 C1 -178.57(19) . . . . ?
C2 C1 C14 C9 -2.4(3) . . . . ?
C15 C1 C14 C9 179.2(2) . . . . ?
C2 C1 C14 C13 174.86(19) . . . . ?
C15 C1 C14 C13 -3.6(3) . . . . ?
C2 C1 C15 C20 -59.1(3) . . . . ?
C14 C1 C15 C20 119.3(2) . . . . ?
C2 C1 C15 C16 120.0(2) . . . . ?
C14 C1 C15 C16 -61.6(3) . . . . ?
C20 C15 C16 C17 -0.7(3) . . . . ?
C1 C15 C16 C17 -179.9(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 O1 -179.18(19) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C21 O1 C18 C17 -0.1(3) . . . . ?
C21 O1 C18 C19 179.82(19) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
O1 C18 C19 C20 179.12(18) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C1 C15 C20 C19 179.84(19) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2



