# 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_141246_0m
_database_code_depnum_ccdc_archive 'CCDC 1062513'
_audit_update_record             
;
2015-04-29 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0914(7)
_cell_length_b                   8.5177(11)
_cell_length_c                   23.947(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.598(7)
_cell_angle_gamma                90
_cell_volume                     1242.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_min      2.9349
_cell_measurement_theta_max      22.1969

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7225
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8860
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.850
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2531
_reflns_number_gt                1579
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.27(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.1269
_refine_ls_wR_factor_ref         0.3920
_refine_ls_wR_factor_gt          0.3426
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_restrained_S_all      1.388
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

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
C1 C 0.4946(8) 0.6899(5) 0.32422(18) 0.0489(12) Uani 1 1 d . . . . .
C2 C 0.6341(10) 0.6736(6) 0.2793(2) 0.0619(14) Uani 1 1 d . . . . .
H2 H 0.7726 0.7195 0.2802 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5650(11) 0.5880(7) 0.2330(2) 0.0714(17) Uani 1 1 d . . . . .
H3 H 0.6584 0.5774 0.2028 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3641(10) 0.5194(7) 0.2310(2) 0.0678(16) Uani 1 1 d . . . . .
H4 H 0.3203 0.4622 0.1998 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2253(10) 0.5353(7) 0.2758(2) 0.0724(17) Uani 1 1 d . . . . .
H5 H 0.0876 0.4882 0.2748 0.087 Uiso 1 1 calc R U . . .
C6 C 0.2902(9) 0.6213(7) 0.3224(2) 0.0605(14) Uani 1 1 d . . . . .
H6 H 0.1955 0.6325 0.3523 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5653(8) 0.7843(5) 0.37473(17) 0.0483(12) Uani 1 1 d . . . . .
H7 H 0.4893 0.8857 0.3741 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5804(8) 0.7754(5) 0.47104(17) 0.0481(12) Uani 1 1 d . . . . .
C9 C 0.7512(8) 0.8750(6) 0.46874(18) 0.0534(13) Uani 1 1 d . . . . .
H9 H 0.7852 0.9377 0.4994 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8836(9) 0.8857(6) 0.41852(18) 0.0545(13) Uani 1 1 d . . . . .
C11 C 0.4600(8) 0.7309(6) 0.52167(18) 0.0500(12) Uani 1 1 d . . . . .
C12 C 0.2561(9) 0.6618(7) 0.5180(2) 0.0633(14) Uani 1 1 d . . . . .
H12 H 0.1965 0.6397 0.4829 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1380(11) 0.6245(8) 0.5650(2) 0.0752(17) Uani 1 1 d . . . . .
H13 H -0.0008 0.5798 0.5618 0.090 Uiso 1 1 calc R U . . .
C14 C 0.2294(12) 0.6548(7) 0.6168(2) 0.0747(17) Uani 1 1 d . . . . .
H14 H 0.1521 0.6292 0.6489 0.090 Uiso 1 1 calc R U . . .
C15 C 0.4333(12) 0.7224(7) 0.6216(2) 0.0721(17) Uani 1 1 d . . . . .
H15 H 0.4922 0.7429 0.6569 0.086 Uiso 1 1 calc R U . . .
C16 C 0.5517(10) 0.7601(7) 0.57483(18) 0.0600(14) Uani 1 1 d . . . . .
H16 H 0.6908 0.8043 0.5783 0.072 Uiso 1 1 calc R U . . .
O1 O 0.5066(6) 0.7014(4) 0.42395(11) 0.0508(10) Uani 1 1 d . . . . .
O2 O 0.7928(6) 0.8103(4) 0.37281(12) 0.0568(11) Uani 1 1 d . . . . .
O3 O 1.0624(6) 0.9401(5) 0.41470(14) 0.0709(13) 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
C1 C6 1.375(7) . ?
C1 C2 1.384(7) . ?
C1 C7 1.511(6) . ?
C2 C3 1.389(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.404(6) . ?
C7 O1 1.423(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.344(7) . ?
C8 O1 1.364(5) . ?
C8 C11 1.473(7) . ?
C9 C10 1.458(7) . ?
C9 H9 0.9300 . ?
C10 O3 1.188(6) . ?
C10 O2 1.380(5) . ?
C11 C12 1.377(8) . ?
C11 C16 1.407(7) . ?
C12 C13 1.380(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(8) . ?
C15 H15 0.9300 . ?
C16 H16 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
C6 C1 C2 119.7(4) . . ?
C6 C1 C7 120.2(4) . . ?
C2 C1 C7 120.2(4) . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.0(5) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O2 C7 O1 111.3(4) . . ?
O2 C7 C1 109.3(4) . . ?
O1 C7 C1 109.1(4) . . ?
O2 C7 H7 109.1 . . ?
O1 C7 H7 109.1 . . ?
C1 C7 H7 109.1 . . ?
C9 C8 O1 120.4(4) . . ?
C9 C8 C11 126.0(4) . . ?
O1 C8 C11 113.5(4) . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O3 C10 O2 118.7(4) . . ?
O3 C10 C9 127.1(4) . . ?
O2 C10 C9 113.9(4) . . ?
C12 C11 C16 118.9(5) . . ?
C12 C11 C8 120.9(4) . . ?
C16 C11 C8 120.2(5) . . ?
C11 C12 C13 121.6(5) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.7(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.3(6) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C8 O1 C7 111.8(3) . . ?
C10 O2 C7 115.8(4) . . ?

_refine_diff_density_max         0.866
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.300

_shelxl_version_number           2014/6

