# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_p160418j-p
_database_code_depnum_ccdc_archive 'CCDC 1544088'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-12-29 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_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         'C11 H6 O2'
_chemical_formula_sum            'C11 H6 O2'
_chemical_formula_weight         170.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     1,3-EBYQS
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7722(3)
_cell_length_b                   8.8640(7)
_cell_length_c                   25.643(2)
_cell_angle_alpha                86.384(7)
_cell_angle_beta                 89.405(7)
_cell_angle_gamma                81.479(7)
_cell_volume                     846.26(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1380
_cell_measurement_temperature    120(10)
_cell_measurement_theta_max      27.4390
_cell_measurement_theta_min      4.0540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5086
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         3.184
_diffrn_ambient_temperature      120(10)
_diffrn_detector_area_resol_mean 16.2116
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   78.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   57.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00    8.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2521  -77.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -85.00   25.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2521  -19.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega   19.00   60.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega  -87.00    0.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2521  -57.0000    0.0000 87
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0412227000
_diffrn_orient_matrix_UB_12      -0.0415218000
_diffrn_orient_matrix_UB_13      -0.0213364000
_diffrn_orient_matrix_UB_21      -0.1685065000
_diffrn_orient_matrix_UB_22      0.0472851000
_diffrn_orient_matrix_UB_23      -0.0028132000
_diffrn_orient_matrix_UB_31      0.0778216000
_diffrn_orient_matrix_UB_32      0.0511126000
_diffrn_orient_matrix_UB_33      -0.0174653000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2171
_reflns_number_total             2978
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+2.0553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C19(H19), C21(H21)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
2.c :
 C20(H20), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4484(8) 0.0588(3) 0.55978(11) 0.0327(8) Uani 1 1 d . . . . .
O2 O 0.6865(10) 0.6737(4) 1.00896(11) 0.0420(9) Uani 1 1 d . . . . .
H2 H 0.6159 0.5978 1.0248 0.063 Uiso 1 1 calc GR . . . .
O3 O 0.7013(9) 0.1730(4) 0.49162(11) 0.0369(8) Uani 1 1 d . . . . .
H3 H 0.6378 0.1014 0.4757 0.055 Uiso 1 1 calc GR . . . .
O4 O 0.5186(9) 0.5648(3) 0.93864(11) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.5936(11) 0.1638(5) 0.54019(16) 0.0281(9) Uani 1 1 d . . . . .
C2 C 0.6359(11) 0.6688(5) 0.95871(16) 0.0295(10) Uani 1 1 d . . . . .
C3 C 0.7639(11) 0.5140(5) 0.62755(15) 0.0255(9) Uani 1 1 d . . . . .
C4 C 0.7010(11) 0.6347(5) 0.70935(15) 0.0260(9) Uani 1 1 d . . . . .
C5 C 0.5960(11) 0.6345(5) 0.76380(17) 0.0285(10) Uani 1 1 d . . . . .
C6 C 0.7129(11) 0.3894(5) 0.59677(15) 0.0275(9) Uani 1 1 d . . . . .
C7 C 0.6634(11) 0.2875(5) 0.57004(15) 0.0282(10) Uani 1 1 d . . . . .
C8 C 1.0894(10) 1.1381(5) 0.78644(16) 0.0269(9) Uani 1 1 d . . . . .
C9 C 0.9532(11) 1.1657(5) 0.89301(16) 0.0302(10) Uani 1 1 d . . . . .
H9 H 0.9096 1.1744 0.9293 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6712(11) 0.5090(5) 0.68029(15) 0.0266(9) Uani 1 1 d . . . . .
H10 H 0.5886 0.4211 0.6963 0.032 Uiso 1 1 calc R . . . .
C11 C 0.8871(11) 0.6424(5) 0.60361(16) 0.0275(9) Uani 1 1 d . . . . .
H11 H 0.9478 0.6453 0.5675 0.033 Uiso 1 1 calc R . . . .
C12 C 0.8252(11) 0.7625(5) 0.68527(16) 0.0289(10) Uani 1 1 d . . . . .
H12 H 0.8449 0.8482 0.7049 0.035 Uiso 1 1 calc R . . . .
C13 C 0.9198(11) 0.7655(5) 0.63297(16) 0.0295(10) Uani 1 1 d . . . . .
H13 H 1.0076 0.8525 0.6171 0.035 Uiso 1 1 calc R . . . .
C14 C 0.9218(11) 1.0285(5) 0.86988(16) 0.0280(9) Uani 1 1 d . . . . .
C15 C 0.9885(11) 1.0153(5) 0.81667(16) 0.0285(10) Uani 1 1 d . . . . .
H15 H 0.9653 0.9228 0.8011 0.034 Uiso 1 1 calc R . . . .
C16 C 0.8186(11) 0.9021(5) 0.90147(16) 0.0291(10) Uani 1 1 d . . . . .
C17 C 1.1740(11) 1.1241(5) 0.73147(17) 0.0294(10) Uani 1 1 d . . . . .
C18 C 0.7361(12) 0.7985(5) 0.92830(16) 0.0312(10) Uani 1 1 d . . . . .
C19 C 1.1176(12) 1.2746(5) 0.81012(16) 0.0309(10) Uani 1 1 d . . . . .
H19 H 1.1856 1.3590 0.7897 0.037 Uiso 1 1 calc R . . . .
C20 C 1.2418(12) 1.1161(5) 0.68657(18) 0.0354(11) Uani 1 1 d . . . . .
H20 H 1.2964 1.1096 0.6505 0.042 Uiso 1 1 calc R . . . .
C21 C 1.0474(12) 1.2871(5) 0.86263(16) 0.0333(10) Uani 1 1 d . . . . .
H21 H 1.0643 1.3805 0.8780 0.040 Uiso 1 1 calc R . . . .
C22 C 0.5096(12) 0.6348(5) 0.80809(18) 0.0358(11) Uani 1 1 d . . . . .
H22 H 0.4400 0.6351 0.8438 0.043 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0452(19) 0.0270(17) 0.0297(16) -0.0101(13) 0.0062(13) -0.0148(14)
O2 0.069(2) 0.0371(19) 0.0261(17) -0.0039(14) 0.0001(15) -0.0288(17)
O3 0.055(2) 0.0344(19) 0.0276(16) -0.0116(13) 0.0086(14) -0.0239(16)
O4 0.057(2) 0.0297(17) 0.0291(16) -0.0069(13) 0.0016(14) -0.0190(15)
C1 0.030(2) 0.028(2) 0.027(2) -0.0066(18) -0.0036(17) -0.0063(18)
C2 0.033(2) 0.027(2) 0.029(2) -0.0030(18) 0.0022(17) -0.0084(19)
C3 0.026(2) 0.021(2) 0.032(2) -0.0094(17) -0.0015(16) -0.0046(17)
C4 0.029(2) 0.021(2) 0.029(2) -0.0075(17) -0.0017(17) -0.0039(17)
C5 0.032(2) 0.021(2) 0.035(3) -0.0073(18) 0.0006(18) -0.0085(18)
C6 0.028(2) 0.028(2) 0.028(2) -0.0050(18) 0.0008(17) -0.0067(18)
C7 0.034(2) 0.026(2) 0.026(2) -0.0052(18) 0.0047(17) -0.0083(19)
C8 0.022(2) 0.024(2) 0.035(2) -0.0030(18) -0.0006(17) -0.0055(17)
C9 0.037(2) 0.028(2) 0.028(2) -0.0100(18) 0.0027(18) -0.0102(19)
C10 0.028(2) 0.024(2) 0.029(2) -0.0045(17) 0.0002(17) -0.0070(17)
C11 0.026(2) 0.028(2) 0.029(2) -0.0031(18) 0.0010(17) -0.0062(18)
C12 0.029(2) 0.025(2) 0.034(2) -0.0084(18) -0.0003(17) -0.0076(18)
C13 0.031(2) 0.021(2) 0.037(2) -0.0038(18) 0.0016(18) -0.0074(18)
C14 0.031(2) 0.025(2) 0.030(2) -0.0020(17) 0.0017(17) -0.0094(18)
C15 0.031(2) 0.023(2) 0.033(2) -0.0030(18) 0.0002(18) -0.0084(18)
C16 0.033(2) 0.028(2) 0.028(2) -0.0075(18) 0.0023(17) -0.0050(19)
C17 0.030(2) 0.026(2) 0.034(3) -0.0030(18) 0.0026(18) -0.0086(18)
C18 0.039(3) 0.030(2) 0.027(2) -0.0052(19) 0.0037(18) -0.014(2)
C19 0.038(2) 0.022(2) 0.034(2) -0.0007(18) -0.0032(19) -0.0101(19)
C20 0.038(3) 0.031(3) 0.038(3) -0.004(2) 0.005(2) -0.009(2)
C21 0.042(3) 0.027(2) 0.035(2) -0.0127(19) 0.0037(19) -0.015(2)
C22 0.045(3) 0.029(2) 0.035(3) -0.010(2) 0.005(2) -0.010(2)

_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 1.227(5) . ?
O2 H2 0.8400 . ?
O2 C2 1.309(5) . ?
O3 H3 0.8400 . ?
O3 C1 1.307(5) . ?
O4 C2 1.223(5) . ?
C1 C7 1.433(6) . ?
C2 C18 1.443(6) . ?
C3 C6 1.433(5) . ?
C3 C10 1.393(6) . ?
C3 C11 1.397(6) . ?
C4 C5 1.448(6) . ?
C4 C10 1.397(5) . ?
C4 C12 1.395(6) . ?
C5 C22 1.178(6) . ?
C6 C7 1.205(6) . ?
C8 C15 1.393(6) . ?
C8 C17 1.451(6) . ?
C8 C19 1.406(6) . ?
C9 H9 0.9500 . ?
C9 C14 1.407(6) . ?
C9 C21 1.376(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C13 1.385(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(6) . ?
C14 C16 1.440(6) . ?
C15 H15 0.9500 . ?
C16 C18 1.189(6) . ?
C17 C20 1.181(6) . ?
C19 H19 0.9500 . ?
C19 C21 1.378(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 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
C2 O2 H2 109.5 . . ?
C1 O3 H3 109.5 . . ?
O1 C1 O3 124.2(4) . . ?
O1 C1 C7 121.5(4) . . ?
O3 C1 C7 114.3(4) . . ?
O2 C2 C18 113.5(4) . . ?
O4 C2 O2 124.2(4) . . ?
O4 C2 C18 122.3(4) . . ?
C10 C3 C6 119.5(4) . . ?
C10 C3 C11 120.8(4) . . ?
C11 C3 C6 119.5(4) . . ?
C10 C4 C5 120.5(4) . . ?
C12 C4 C5 119.9(4) . . ?
C12 C4 C10 119.6(4) . . ?
C22 C5 C4 179.8(5) . . ?
C7 C6 C3 178.2(5) . . ?
C6 C7 C1 177.3(4) . . ?
C15 C8 C17 120.5(4) . . ?
C15 C8 C19 119.2(4) . . ?
C19 C8 C17 120.3(4) . . ?
C14 C9 H9 120.2 . . ?
C21 C9 H9 120.2 . . ?
C21 C9 C14 119.5(4) . . ?
C3 C10 C4 119.3(4) . . ?
C3 C10 H10 120.3 . . ?
C4 C10 H10 120.3 . . ?
C3 C11 H11 120.3 . . ?
C13 C11 C3 119.3(4) . . ?
C13 C11 H11 120.3 . . ?
C4 C12 H12 119.7 . . ?
C13 C12 C4 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C13 H13 119.8 . . ?
C12 C13 C11 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C9 C14 C16 119.6(4) . . ?
C15 C14 C9 120.2(4) . . ?
C15 C14 C16 120.2(4) . . ?
C8 C15 C14 119.8(4) . . ?
C8 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C18 C16 C14 178.8(4) . . ?
C20 C17 C8 178.6(5) . . ?
C16 C18 C2 177.3(4) . . ?
C8 C19 H19 119.7 . . ?
C21 C19 C8 120.5(4) . . ?
C21 C19 H19 119.7 . . ?
C17 C20 H20 180.0 . . ?
C9 C21 C19 120.7(4) . . ?
C9 C21 H21 119.7 . . ?
C19 C21 H21 119.7 . . ?
C5 C22 H22 180.0 . . ?

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
C3 C11 C13 C12 -1.2(6) . . . . ?
C4 C12 C13 C11 1.0(6) . . . . ?
C5 C4 C10 C3 178.1(4) . . . . ?
C5 C4 C12 C13 -178.7(4) . . . . ?
C6 C3 C10 C4 -176.1(4) . . . . ?
C6 C3 C11 C13 176.9(4) . . . . ?
C8 C19 C21 C9 0.9(7) . . . . ?
C9 C14 C15 C8 0.5(6) . . . . ?
C10 C3 C11 C13 0.6(6) . . . . ?
C10 C4 C12 C13 -0.2(6) . . . . ?
C11 C3 C10 C4 0.3(6) . . . . ?
C12 C4 C10 C3 -0.5(6) . . . . ?
C14 C9 C21 C19 -1.2(7) . . . . ?
C15 C8 C19 C21 0.2(6) . . . . ?
C16 C14 C15 C8 -179.8(4) . . . . ?
C17 C8 C15 C14 177.5(4) . . . . ?
C17 C8 C19 C21 -178.2(4) . . . . ?
C19 C8 C15 C14 -0.8(6) . . . . ?
C21 C9 C14 C15 0.5(7) . . . . ?
C21 C9 C14 C16 -179.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p161115c1
_database_code_depnum_ccdc_archive 'CCDC 1544089'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-12-29 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_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         'C11 H5 O2'
_chemical_formula_sum            'C11 H5 O2'
_chemical_formula_weight         169.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     1,4BQS
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   3.8398(8)
_cell_length_b                   6.201(3)
_cell_length_c                   35.222(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.034(17)
_cell_angle_gamma                90
_cell_volume                     838.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    797
_cell_measurement_temperature    120(10)
_cell_measurement_theta_max      26.6590
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            3042
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         3.336
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  27.00   1.00   26.25    --  -19.25  57.00  90.00   61
  2  ω     35.00  87.00   1.00   26.25    --   18.94 178.00-120.00   52
  3  ω    -80.00 -10.00   1.00   26.25    --  -19.25 -77.00-150.00   70
  4  ω     41.00  94.00   1.00   26.25    --   18.94-178.00  30.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321965000
_diffrn_orient_matrix_UB_12      0.0281107000
_diffrn_orient_matrix_UB_13      0.0191731000
_diffrn_orient_matrix_UB_21      0.1719717000
_diffrn_orient_matrix_UB_22      -0.0310447000
_diffrn_orient_matrix_UB_23      0.0051878000
_diffrn_orient_matrix_UB_31      0.0589104000
_diffrn_orient_matrix_UB_32      0.1064303000
_diffrn_orient_matrix_UB_33      -0.0034425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1221
_reflns_number_total             1490
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1490
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0890
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+1.5840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.1961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 O11, C9, O10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
O10 \\sim C9 \\sim O11: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6)
4.b :
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O10 O 0.0342(4) 1.4135(3) 0.46653(4) 0.0404(4) Uani 1 1 d . U . . .
O11 O 0.3266(5) 1.1754(3) 0.50157(4) 0.0407(4) Uani 1 1 d . U . . .
C4 C 0.6965(5) 0.5576(3) 0.32798(5) 0.0195(5) Uani 1 1 d . . . . .
C12 C 0.8079(5) 0.4035(4) 0.30011(5) 0.0204(5) Uani 1 1 d . . . . .
C9 C 0.2125(6) 1.2420(4) 0.46974(6) 0.0290(4) Uani 1 1 d . U . . .
C3 C 0.5544(5) 0.7567(3) 0.31703(5) 0.0211(5) Uani 1 1 d . . . . .
H3 H 0.5326 0.7917 0.2908 0.025 Uiso 1 1 calc R . . . .
C5 C 0.7345(5) 0.5116(4) 0.36660(5) 0.0217(5) Uani 1 1 d . . . . .
H5 H 0.8351 0.3784 0.3744 0.026 Uiso 1 1 calc R . . . .
C1 C 0.4819(5) 0.8540(3) 0.38232(5) 0.0194(5) Uani 1 1 d . . . . .
C2 C 0.4460(5) 0.9022(3) 0.34390(5) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.3465 1.0358 0.3362 0.025 Uiso 1 1 calc R . . . .
C7 C 0.3731(5) 1.0029(4) 0.41095(5) 0.0223(5) Uani 1 1 d . . . . .
C8 C 0.2894(6) 1.1196(4) 0.43613(5) 0.0261(6) Uani 1 1 d . . . . .
C6 C 0.6288(5) 0.6559(3) 0.39352(5) 0.0220(5) Uani 1 1 d . . . . .
H6 H 0.6547 0.6221 0.4197 0.026 Uiso 1 1 calc R . . . .
C13 C 0.9021(5) 0.2754(4) 0.27780(6) 0.0271(6) Uani 1 1 d . . . . .
H13 H 0.9780 0.1722 0.2598 0.033 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O10 0.0553(9) 0.0323(6) 0.0335(7) -0.0058(6) -0.0032(6) 0.0251(5)
O11 0.0628(10) 0.0341(8) 0.0252(5) -0.0017(5) -0.0008(5) 0.0219(6)
C4 0.0177(9) 0.0155(10) 0.0254(9) -0.0018(8) 0.0049(8) 0.0011(8)
C12 0.0184(9) 0.0194(11) 0.0237(9) 0.0009(8) 0.0043(8) -0.0028(9)
C9 0.0364(10) 0.0242(7) 0.0265(6) -0.0015(7) 0.0025(7) 0.0113(6)
C3 0.0207(9) 0.0224(11) 0.0204(9) 0.0007(9) 0.0031(8) 0.0026(9)
C5 0.0225(10) 0.0174(11) 0.0252(10) 0.0020(9) 0.0011(8) 0.0020(9)
C1 0.0141(8) 0.0198(11) 0.0243(9) -0.0029(9) 0.0019(7) 0.0018(9)
C2 0.0213(9) 0.0152(10) 0.0261(10) 0.0000(9) 0.0027(8) 0.0000(9)
C7 0.0241(10) 0.0200(11) 0.0228(9) 0.0035(9) 0.0021(8) 0.0034(10)
C8 0.0327(11) 0.0236(12) 0.0220(10) 0.0021(9) 0.0046(8) 0.0097(10)
C6 0.0255(10) 0.0212(11) 0.0193(9) 0.0044(9) 0.0025(8) 0.0036(9)
C13 0.0300(11) 0.0247(12) 0.0268(10) -0.0018(10) 0.0043(9) 0.0000(10)

_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
O10 C9 1.269(3) . ?
O11 C9 1.266(3) . ?
C4 C12 1.441(3) . ?
C4 C3 1.401(3) . ?
C4 C5 1.395(3) . ?
C12 C13 1.179(3) . ?
C9 C8 1.441(3) . ?
C3 C2 1.377(3) . ?
C5 C6 1.371(3) . ?
C1 C2 1.390(3) . ?
C1 C7 1.435(3) . ?
C1 C6 1.405(3) . ?
C7 C8 1.193(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 C4 C12 121.06(18) . . ?
C5 C4 C12 120.12(19) . . ?
C5 C4 C3 118.81(18) . . ?
C13 C12 C4 178.8(2) . . ?
O10 C9 C8 119.11(19) . . ?
O11 C9 O10 122.0(2) . . ?
O11 C9 C8 118.9(2) . . ?
C2 C3 C4 120.60(18) . . ?
C6 C5 C4 120.9(2) . . ?
C2 C1 C7 121.39(19) . . ?
C2 C1 C6 119.56(18) . . ?
C6 C1 C7 119.05(17) . . ?
C3 C2 C1 120.16(19) . . ?
C8 C7 C1 176.6(2) . . ?
C7 C8 C9 172.7(2) . . ?
C5 C6 C1 119.93(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.495
