# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_renan2
_database_code_depnum_ccdc_archive 'CCDC 1551219'
#Added by publCIF



_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 O3'
_chemical_formula_weight         198.17

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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   8.7768(4)
_cell_length_b                   8.7768(4)
_cell_length_c                   19.3349(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1289.87(13)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9883
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24932
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1972
_reflns_number_gt                1897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTL-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXTL-2014 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL-2014 (Bruker, 2014)'
_computing_publication_material  'SHELXTL-2014 (Bruker, 2014)'

_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

Although the value of the Flack x parameter, 0.5)(2), suggests the presence of
 higher symmetry, the fact that the X-ray source is Mo and the error is very
 high, and the absence of heavy atoms,  indicate that it is not reliable to
 distinguish between space groups P6(5), P6(1) or any higher symmetry space
 group.  Additionally, the molecules are not chiral.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3152P] 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_abs_structure_details 
; 
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.5(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_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 0.3526(2) 0.03157(19) 0.15167(8) 0.0182(3) Uani 1 1 d . . . . .
O2 O -0.17661(18) 0.04799(19) 0.17796(9) 0.0177(3) Uani 1 1 d . . . . .
O3 O 0.37344(19) 0.57761(19) 0.18033(8) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.2779(3) 0.1351(3) 0.16038(10) 0.0143(4) Uani 1 1 d . . . . .
C2 C 0.0954(3) 0.0328(3) 0.16306(10) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.0025(2) 0.1234(3) 0.17276(10) 0.0144(4) Uani 1 1 d . . . . .
C4 C 0.0834(3) 0.3051(3) 0.17866(11) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.2676(3) 0.3986(3) 0.17487(11) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.3695(3) 0.3194(3) 0.16607(10) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.2131(3) -0.1396(3) 0.14826(11) 0.0190(4) Uani 1 1 d . . . . .
H7A H 0.2261 -0.2399 0.1423 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0566(3) -0.1465(3) 0.15448(11) 0.0176(4) Uani 1 1 d . . . . .
H8A H -0.0566 -0.2489 0.1534 0.021 Uiso 1 1 calc R U . . .
C9 C -0.2080(3) 0.1862(3) 0.18664(12) 0.0192(4) Uani 1 1 d . . . . .
H9A H -0.3220 0.1726 0.1911 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0568(3) 0.3435(3) 0.18801(11) 0.0183(4) Uani 1 1 d . . . . .
H10A H -0.0456 0.4561 0.1939 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5441(3) 0.6095(3) 0.17517(13) 0.0227(5) Uani 1 1 d . . . . .
H11A H 0.6456 0.7232 0.1776 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5491(3) 0.4601(3) 0.16632(13) 0.0214(5) Uani 1 1 d . . . . .
H12A H 0.6512 0.4497 0.1612 0.026 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 C1 1.371(2) . ?
O1 C7 1.386(3) . ?
O2 C3 1.371(2) . ?
O2 C9 1.382(3) . ?
O3 C5 1.372(2) . ?
O3 C11 1.383(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.407(3) . ?
C2 C8 1.443(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.402(3) . ?
C4 C10 1.441(3) . ?
C5 C6 1.391(3) . ?
C6 C12 1.436(3) . ?
C7 C8 1.350(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.355(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.345(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?

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 O1 C7 105.58(16) . . ?
C3 O2 C9 105.61(15) . . ?
C5 O3 C11 105.73(17) . . ?
O1 C1 C2 110.73(17) . . ?
O1 C1 C6 125.76(18) . . ?
C2 C1 C6 123.51(19) . . ?
C1 C2 C3 116.43(18) . . ?
C1 C2 C8 105.55(17) . . ?
C3 C2 C8 138.02(18) . . ?
O2 C3 C4 110.63(18) . . ?
O2 C3 C2 125.86(18) . . ?
C4 C3 C2 123.52(17) . . ?
C3 C4 C5 116.45(18) . . ?
C3 C4 C10 105.85(18) . . ?
C5 C4 C10 137.69(19) . . ?
O3 C5 C6 110.18(17) . . ?
O3 C5 C4 126.07(19) . . ?
C6 C5 C4 123.74(18) . . ?
C5 C6 C1 116.35(18) . . ?
C5 C6 C12 105.86(18) . . ?
C1 C6 C12 137.8(2) . . ?
C8 C7 O1 111.83(19) . . ?
C8 C7 H7A 124.1 . . ?
O1 C7 H7A 124.1 . . ?
C7 C8 C2 106.31(18) . . ?
C7 C8 H8A 126.8 . . ?
C2 C8 H8A 126.8 . . ?
C10 C9 O2 111.92(18) . . ?
C10 C9 H9A 124.0 . . ?
O2 C9 H9A 124.0 . . ?
C9 C10 C4 105.98(19) . . ?
C9 C10 H10A 127.0 . . ?
C4 C10 H10A 127.0 . . ?
C12 C11 O3 111.84(19) . . ?
C12 C11 H11A 124.1 . . ?
O3 C11 H11A 124.1 . . ?
C11 C12 C6 106.4(2) . . ?
C11 C12 H12A 126.8 . . ?
C6 C12 H12A 126.8 . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-3

