# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_0306_GD-138A
_database_code_depnum_ccdc_archive 'CCDC 1859287'


_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C10 H5 Br O3'
_chemical_formula_weight         253.05
_cell_length_a                   5.5823(6)
_cell_length_b                   8.8647(8)
_cell_length_c                   9.7277(11)
_cell_angle_alpha                107.598(4)
_cell_angle_beta                 104.463(4)
_cell_angle_gamma                98.386(3)
_cell_volume                     431.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P -1'
_exptl_crystal_density_diffrn    1.948
_refine_ls_R_factor_gt           0.0196



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
Br1 Br 0.82236(2) 0.29911(2) 0.99190(2) 0.01845(5) Uani 1 1 d . . . . .
O1 O 0.17824(18) 0.43633(12) 0.59399(11) 0.01914(18) Uani 1 1 d . . . . .
O2 O 0.13900(19) 0.34553(12) 0.30422(11) 0.01910(18) Uani 1 1 d D . . . .
H2 H 0.108(4) 0.399(2) 0.392(2) 0.029 Uiso 1 1 d DR . . . .
O3 O 0.93868(19) 0.14075(14) 0.70223(12) 0.0224(2) Uani 1 1 d . . . . .
C1 C 0.6619(2) 0.29195(15) 0.79524(14) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.4707(2) 0.36512(16) 0.76703(15) 0.0166(2) Uani 1 1 d . . . . .
H2A H 0.412459 0.419557 0.847971 0.020 Uiso 1 1 calc R . . . .
C3 C 0.3493(2) 0.36294(15) 0.61353(14) 0.0143(2) Uani 1 1 d . . . . .
C4 C 0.4339(2) 0.27420(15) 0.48855(14) 0.0139(2) Uani 1 1 d . . . . .
C5 C 0.3227(2) 0.26831(15) 0.33992(14) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.4054(3) 0.18190(16) 0.22133(15) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.328440 0.176530 0.120595 0.022 Uiso 1 1 calc R . . . .
C7 C 0.5995(3) 0.10454(17) 0.25180(16) 0.0194(2) Uani 1 1 d . . . . .
H7 H 0.655285 0.046274 0.171222 0.023 Uiso 1 1 calc R . . . .
C8 C 0.7150(2) 0.11055(16) 0.39904(15) 0.0178(2) Uani 1 1 d . . . . .
H8 H 0.848857 0.057386 0.418492 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6325(2) 0.19472(15) 0.51641(14) 0.0148(2) Uani 1 1 d . . . . .
C10 C 0.7607(2) 0.20279(16) 0.67312(15) 0.0160(2) 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
Br1 C1 1.8761(12) . ?
O1 C3 1.2396(15) . ?
O2 H2 0.920(15) . ?
O2 C5 1.3459(15) . ?
O3 C10 1.2179(15) . ?
C1 C2 1.3411(17) . ?
C1 C10 1.4920(18) . ?
C2 H2A 0.9500 . ?
C2 C3 1.4706(18) . ?
C3 C4 1.4619(17) . ?
C4 C5 1.4054(17) . ?
C4 C9 1.4115(17) . ?
C5 C6 1.4018(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3974(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3854(17) . ?
C9 C10 1.4883(18) . ?

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
C5 O2 H2 107.5(13) . . ?
C2 C1 Br1 121.46(10) . . ?
C2 C1 C10 122.04(11) . . ?
C10 C1 Br1 116.49(9) . . ?
C1 C2 H2A 119.3 . . ?
C1 C2 C3 121.43(12) . . ?
C3 C2 H2A 119.3 . . ?
O1 C3 C2 119.02(11) . . ?
O1 C3 C4 121.98(11) . . ?
C4 C3 C2 119.00(11) . . ?
C5 C4 C3 120.96(11) . . ?
C5 C4 C9 118.94(11) . . ?
C9 C4 C3 120.09(11) . . ?
O2 C5 C4 122.88(11) . . ?
O2 C5 C6 116.94(11) . . ?
C6 C5 C4 120.17(12) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.62(12) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.16(12) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.42(12) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C10 120.49(11) . . ?
C8 C9 C4 120.67(12) . . ?
C8 C9 C10 118.83(11) . . ?
O3 C10 C1 120.81(12) . . ?
O3 C10 C9 122.30(12) . . ?
C9 C10 C1 116.89(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.920(15) 1.814(17) 2.6286(14) 146.2(19) .

_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_mo_0309_GD-158E
_database_code_depnum_ccdc_archive 'CCDC 1859290'


_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C11 H8 O5'
_chemical_formula_weight         220.17
_cell_length_a                   6.7736(10)
_cell_length_b                   16.388(3)
_cell_length_c                   8.4836(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.062(5)
_cell_angle_gamma                90
_cell_volume                     905.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P 1 21/n 1'
_exptl_crystal_density_diffrn    1.616
_refine_ls_R_factor_gt           0.0498



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 0.71302(17) 0.38920(6) 0.01816(12) 0.0225(2) Uani 1 1 d D . . . .
H1 H 0.675(3) 0.3422(11) 0.075(2) 0.034 Uiso 1 1 d DR . . . .
O2 O 0.64176(17) 0.29719(6) 0.24143(12) 0.0219(2) Uani 1 1 d . . . . .
O3 O 0.82057(16) 0.64497(6) 0.45403(12) 0.0192(2) Uani 1 1 d D . . . .
H3 H 0.806(3) 0.6221(12) 0.555(2) 0.029 Uiso 1 1 d DR . . . .
O4 O 0.76506(15) 0.54565(6) 0.67007(11) 0.0162(2) Uani 1 1 d . . . . .
O5 O 0.63482(16) 0.26616(6) 0.54036(12) 0.0188(2) Uani 1 1 d . . . . .
C1 C 0.73551(19) 0.45033(8) 0.12866(14) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.72141(18) 0.43707(7) 0.28814(14) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.75112(18) 0.50276(7) 0.40109(14) 0.0123(2) Uani 1 1 d . . . . .
C4 C 0.74147(18) 0.48824(7) 0.56956(14) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.70304(19) 0.40625(7) 0.61881(14) 0.0136(2) Uani 1 1 d . . . . .
H5 H 0.699639 0.396423 0.728384 0.016 Uiso 1 1 calc R . . . .
C6 C 0.67201(19) 0.34369(7) 0.51077(15) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.6758(2) 0.35580(7) 0.33713(15) 0.0145(2) Uani 1 1 d . . . . .
C8 C 0.79070(19) 0.58061(7) 0.35112(15) 0.0137(2) Uani 1 1 d . . . . .
C9 C 0.8023(2) 0.59352(8) 0.18932(15) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.828394 0.646730 0.155397 0.020 Uiso 1 1 calc R . . . .
C10 C 0.7761(2) 0.52971(8) 0.08084(15) 0.0172(3) Uani 1 1 d . . . . .
H10 H 0.785266 0.538999 -0.027431 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6326(2) 0.24615(9) 0.70471(17) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.607962 0.187531 0.712057 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.523100 0.276836 0.733115 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.765353 0.260425 0.781082 0.032 Uiso 1 1 calc GR . . . .


_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 H1 0.980(15) . ?
O1 C1 1.3514(15) . ?
O2 C7 1.2375(15) . ?
O3 H3 0.968(15) . ?
O3 C8 1.3483(15) . ?
O4 C4 1.2500(14) . ?
O5 C6 1.3326(15) . ?
O5 C11 1.4364(16) . ?
C1 C2 1.3995(16) . ?
C1 C10 1.4120(18) . ?
C2 C3 1.4180(16) . ?
C2 C7 1.4537(17) . ?
C3 C4 1.4681(16) . ?
C3 C8 1.3936(16) . ?
C4 C5 1.4518(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3523(17) . ?
C6 C7 1.4936(17) . ?
C8 C9 1.4124(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3718(18) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 H1 103.6(13) . . ?
C8 O3 H3 103.8(12) . . ?
C6 O5 C11 116.99(10) . . ?
O1 C1 C2 122.06(12) . . ?
O1 C1 C10 118.50(11) . . ?
C2 C1 C10 119.44(12) . . ?
C1 C2 C3 120.04(11) . . ?
C1 C2 C7 119.69(11) . . ?
C3 C2 C7 120.27(11) . . ?
C2 C3 C4 119.90(11) . . ?
C8 C3 C2 119.52(11) . . ?
C8 C3 C4 120.58(11) . . ?
O4 C4 C3 120.69(11) . . ?
O4 C4 C5 119.97(11) . . ?
C5 C4 C3 119.34(10) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.88(11) . . ?
C6 C5 H5 119.6 . . ?
O5 C6 C5 126.67(11) . . ?
O5 C6 C7 111.60(10) . . ?
C5 C6 C7 121.73(11) . . ?
O2 C7 C2 122.64(11) . . ?
O2 C7 C6 119.54(11) . . ?
C2 C7 C6 117.82(10) . . ?
O3 C8 C3 121.75(11) . . ?
O3 C8 C9 118.26(11) . . ?
C3 C8 C9 120.00(11) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.40(12) . . ?
C10 C9 H9 119.8 . . ?
C1 C10 H10 119.7 . . ?
C9 C10 C1 120.60(11) . . ?
C9 C10 H10 119.7 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.980(15) 1.662(17) 2.5691(15) 152.0(19) .
O3 H3 O4 0.968(15) 1.656(16) 2.5555(13) 152.8(19) .
C5 H5 O1 0.95 2.44 3.3814(17) 172.2 1_556

_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_0379_GD-209
_database_code_depnum_ccdc_archive 'CCDC 1859455'

_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C10 H5 Cl O3'
_chemical_formula_weight         208.59
_cell_length_a                   5.9751(4)
_cell_length_b                   8.1685(6)
_cell_length_c                   9.4932(6)
_cell_angle_alpha                106.087(3)
_cell_angle_beta                 105.644(3)
_cell_angle_gamma                96.710(3)
_cell_volume                     419.42(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P -1'
_exptl_crystal_density_diffrn    1.652
_refine_ls_R_factor_gt           0.0254


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
Cl1 Cl 0.19101(5) 0.69862(3) 0.01945(3) 0.01839(11) Uani 1 1 d . . . . .
O1 O 0.06962(15) 0.85658(12) 0.29708(10) 0.0214(2) Uani 1 1 d . . . . .
O2 O 0.87618(15) 0.65705(11) 0.70664(10) 0.01841(19) Uani 1 1 d . . . . .
H2 H 0.916(4) 0.613(3) 0.629(3) 0.047(6) Uiso 1 1 d . . . . .
O3 O 0.83170(14) 0.56903(11) 0.41140(9) 0.01704(18) Uani 1 1 d . . . . .
C1 C 0.3403(2) 0.70454(14) 0.20347(12) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.24277(19) 0.79271(14) 0.32721(13) 0.0150(2) Uani 1 1 d . . . . .
C3 C 0.3708(2) 0.79901(14) 0.48749(12) 0.0137(2) Uani 1 1 d . . . . .
C4 C 0.57179(19) 0.72311(14) 0.51668(12) 0.0133(2) Uani 1 1 d . . . . .
C5 C 0.6873(2) 0.72964(14) 0.66906(13) 0.0147(2) Uani 1 1 d . . . . .
C6 C 0.6032(2) 0.81210(15) 0.78898(13) 0.0177(2) Uani 1 1 d . . . . .
H6 H 0.681481 0.817287 0.891982 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4066(2) 0.88582(15) 0.75747(13) 0.0178(2) Uani 1 1 d . . . . .
H7 H 0.350509 0.941191 0.839354 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2891(2) 0.88014(14) 0.60684(13) 0.0164(2) Uani 1 1 d . . . . .
H8 H 0.154193 0.931484 0.586486 0.020 Uiso 1 1 calc R . . . .
C9 C 0.65808(19) 0.63831(14) 0.39028(12) 0.0131(2) Uani 1 1 d . . . . .
C10 C 0.5329(2) 0.63543(14) 0.23274(13) 0.0155(2) Uani 1 1 d . . . . .
H10 H 0.590116 0.583453 0.150384 0.019 Uiso 1 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
Cl1 C1 1.7183(11) . ?
O1 C2 1.2139(14) . ?
O2 H2 0.84(2) . ?
O2 C5 1.3451(14) . ?
O3 C9 1.2347(14) . ?
C1 C2 1.4957(15) . ?
C1 C10 1.3363(16) . ?
C2 C3 1.4909(15) . ?
C3 C4 1.4118(15) . ?
C3 C8 1.3854(15) . ?
C4 C5 1.4078(16) . ?
C4 C9 1.4635(15) . ?
C5 C6 1.4017(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3809(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3980(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4731(15) . ?
C10 H10 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
C5 O2 H2 110.8(15) . . ?
C2 C1 Cl1 115.89(8) . . ?
C10 C1 Cl1 121.44(9) . . ?
C10 C1 C2 122.66(10) . . ?
O1 C2 C1 121.01(10) . . ?
O1 C2 C3 122.51(10) . . ?
C3 C2 C1 116.47(9) . . ?
C4 C3 C2 120.37(10) . . ?
C8 C3 C2 118.93(10) . . ?
C8 C3 C4 120.70(10) . . ?
C3 C4 C9 120.47(10) . . ?
C5 C4 C3 118.99(10) . . ?
C5 C4 C9 120.53(10) . . ?
O2 C5 C4 122.95(10) . . ?
O2 C5 C6 117.19(10) . . ?
C6 C5 C4 119.85(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.03(11) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.96(10) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 119.46(10) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O3 C9 C4 122.18(10) . . ?
O3 C9 C10 119.06(10) . . ?
C4 C9 C10 118.76(10) . . ?
C1 C10 C9 121.25(10) . . ?
C1 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.84(2) 1.90(2) 2.6230(12) 143(2) . yes
O2 H2 O3 0.84(2) 2.27(2) 2.8938(12) 131.8(19) 2_766 yes

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_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_mo_0349_GD-197A
_database_code_depnum_ccdc_archive 'CCDC 1859454'


_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C12 H10 O4'
_chemical_formula_weight         218.20
_cell_length_a                   3.7933(7)
_cell_length_b                   13.241(2)
_cell_length_c                   19.027(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.330(5)
_cell_angle_gamma                90
_cell_volume                     954.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P 1 21/n 1'
_exptl_crystal_density_diffrn    1.519
_refine_ls_R_factor_gt           0.0473


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 0.7675(3) 0.38711(7) 0.40481(5) 0.0260(2) Uani 1 1 d . . . . .
H1 H 0.806468 0.424087 0.440284 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.7990(3) 0.43002(7) 0.53882(5) 0.0265(2) Uani 1 1 d . . . . .
O3 O 0.3830(3) 0.20948(7) 0.70807(5) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.1418(3) 0.08695(7) 0.59908(5) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.6197(3) 0.29989(9) 0.42447(6) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.5541(3) 0.27760(8) 0.49480(6) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.3983(3) 0.18406(8) 0.51055(6) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.3177(3) 0.16036(9) 0.58413(6) 0.0178(2) Uani 1 1 d . . . . .
C5 C 0.4456(3) 0.23255(9) 0.64027(6) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.5863(3) 0.32320(9) 0.62516(6) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.6511(3) 0.34904(9) 0.55136(6) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.6916(4) 0.39965(10) 0.68045(7) 0.0242(3) Uani 1 1 d . . . . .
H8A H 0.616374 0.376565 0.726171 0.036 Uiso 1 1 calc GR . . . .
H8B H 0.578543 0.464443 0.668482 0.036 Uiso 1 1 calc GR . . . .
H8C H 0.948699 0.407969 0.682883 0.036 Uiso 1 1 calc GR . . . .
C9 C 0.3143(3) 0.11429(9) 0.45812(7) 0.0202(2) Uani 1 1 d . . . . .
H9 H 0.210881 0.051343 0.469182 0.024 Uiso 1 1 calc R . . . .
C10 C 0.3836(4) 0.13770(10) 0.38860(7) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.327873 0.089839 0.352448 0.028 Uiso 1 1 calc R . . . .
C11 C 0.5313(4) 0.22888(10) 0.37158(7) 0.0233(3) Uani 1 1 d . . . . .
H11 H 0.573469 0.243731 0.323946 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5254(4) 0.11466(10) 0.73448(7) 0.0241(3) Uani 1 1 d . . . . .
H12A H 0.368935 0.059367 0.718458 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.543669 0.116202 0.786059 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.760258 0.104133 0.716836 0.036 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C1 1.3462(15) . ?
O2 C7 1.2397(15) . ?
O3 C5 1.3601(14) . ?
O3 C12 1.4454(15) . ?
O4 C4 1.2219(15) . ?
C1 C2 1.4065(17) . ?
C1 C11 1.4036(18) . ?
C2 C3 1.4120(16) . ?
C2 C7 1.4637(16) . ?
C3 C4 1.4837(17) . ?
C3 C9 1.3832(16) . ?
C4 C5 1.4933(17) . ?
C5 C6 1.3511(16) . ?
C6 C7 1.4798(17) . ?
C6 C8 1.4974(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.3983(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3775(18) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 H1 109.5 . . ?
C5 O3 C12 116.26(10) . . ?
O1 C1 C2 122.96(11) . . ?
O1 C1 C11 117.48(11) . . ?
C11 C1 C2 119.56(11) . . ?
C1 C2 C3 119.05(11) . . ?
C1 C2 C7 120.86(11) . . ?
C3 C2 C7 120.08(11) . . ?
C2 C3 C4 119.84(10) . . ?
C9 C3 C2 120.95(11) . . ?
C9 C3 C4 119.20(11) . . ?
O4 C4 C3 122.22(11) . . ?
O4 C4 C5 120.12(11) . . ?
C3 C4 C5 117.60(10) . . ?
O3 C5 C4 117.86(10) . . ?
C6 C5 O3 119.62(11) . . ?
C6 C5 C4 122.16(11) . . ?
C5 C6 C7 119.79(11) . . ?
C5 C6 C8 122.92(11) . . ?
C7 C6 C8 117.27(11) . . ?
O2 C7 C2 120.99(11) . . ?
O2 C7 C6 118.98(11) . . ?
C2 C7 C6 119.98(10) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9 120.5 . . ?
C3 C9 C10 119.09(11) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.20(12) . . ?
C11 C10 H10 119.4 . . ?
C1 C11 H11 119.9 . . ?
C10 C11 C1 120.14(12) . . ?
C10 C11 H11 119.9 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.88 2.6084(14) 144.5 .

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id GD-197A
_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_mo_0348_GD-141A
_database_code_depnum_ccdc_archive 'CCDC 1859288'


_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C11 H8 O3'
_chemical_formula_weight         188.17
_cell_length_a                   13.3129(7)
_cell_length_b                   6.8940(3)
_cell_length_c                   18.8345(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.489(2)
_cell_angle_gamma                90
_cell_volume                     1728.55(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P 1 21/c 1'
_exptl_crystal_density_diffrn    1.446
_refine_ls_R_factor_gt           0.0469


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 0.56608(7) 0.57146(13) 0.07952(4) 0.0405(2) Uani 1 1 d . . . . .
H1 H 0.623084 0.571654 0.098981 0.061 Uiso 1 1 calc GR . . . .
O2 O 0.69378(6) 0.57779(12) 0.18459(4) 0.03391(17) Uani 1 1 d . . . . .
O3 O 0.39820(6) 0.56618(14) 0.37380(5) 0.0405(2) Uani 1 1 d . . . . .
C1 C 0.49484(8) 0.57495(13) 0.12969(5) 0.02917(19) Uani 1 1 d . . . . .
C2 C 0.51858(7) 0.57743(12) 0.20253(5) 0.02196(16) Uani 1 1 d . . . . .
C3 C 0.62318(7) 0.57898(12) 0.22718(5) 0.02236(16) Uani 1 1 d . . . . .
C4 C 0.64434(6) 0.58416(12) 0.30359(5) 0.02266(16) Uani 1 1 d . . . . .
H4 H 0.712401 0.586438 0.319125 0.027 Uiso 1 1 calc R . . . .
C5 C 0.57170(6) 0.58582(12) 0.35267(4) 0.02150(15) Uani 1 1 d . . . . .
C6 C 0.46459(7) 0.57702(12) 0.32967(5) 0.02423(17) Uani 1 1 d . . . . .
C7 C 0.44045(6) 0.57933(12) 0.25230(5) 0.02291(16) Uani 1 1 d . . . . .
C8 C 0.34118(7) 0.58261(14) 0.22990(7) 0.0321(2) Uani 1 1 d . . . . .
H8 H 0.288541 0.585708 0.263618 0.039 Uiso 1 1 calc R . . . .
C9 C 0.31908(9) 0.58133(15) 0.15725(7) 0.0391(3) Uani 1 1 d . . . . .
H9 H 0.250937 0.584246 0.141896 0.047 Uiso 1 1 calc R . . . .
C10 C 0.39398(10) 0.57593(14) 0.10762(6) 0.0375(3) Uani 1 1 d . . . . .
H10 H 0.377509 0.572856 0.058454 0.045 Uiso 1 1 calc R . . . .
C11 C 0.59191(8) 0.59267(14) 0.43076(5) 0.02963(19) Uani 1 1 d . . . . .
H11A H 0.574276 0.467647 0.452046 0.044 Uiso 1 1 calc GR . . . .
H11B H 0.551402 0.695539 0.452187 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.663310 0.619320 0.439268 0.044 Uiso 1 1 calc GR . . . .
O4 O -0.04573(8) 0.88681(13) 0.36678(4) 0.0446(2) Uani 1 1 d . . . . .
H4A H -0.102475 0.877086 0.385612 0.067 Uiso 1 1 calc GR . . . .
O5 O -0.17307(5) 0.81533(11) 0.46518(4) 0.03317(17) Uani 1 1 d . . . . .
O6 O 0.11964(8) 0.59440(15) 0.64310(6) 0.0535(3) Uani 1 1 d . . . . .
C12 C 0.02498(9) 0.82466(13) 0.41239(5) 0.0300(2) Uani 1 1 d . . . . .
C13 C 0.00098(6) 0.76523(11) 0.48155(4) 0.01946(14) Uani 1 1 d . . . . .
C14 C -0.10317(6) 0.76731(11) 0.50543(4) 0.02038(15) Uani 1 1 d . . . . .
C15 C -0.12403(7) 0.71400(13) 0.57885(5) 0.02553(17) Uani 1 1 d . . . . .
H15 H -0.191734 0.715586 0.594374 0.031 Uiso 1 1 calc R . . . .
C16 C -0.05217(8) 0.66304(13) 0.62523(5) 0.02866(19) Uani 1 1 d . . . . .
C17 C 0.05379(8) 0.65001(13) 0.60222(5) 0.02947(19) Uani 1 1 d . . . . .
C18 C 0.07809(6) 0.70645(12) 0.52808(5) 0.02364(16) Uani 1 1 d . . . . .
C19 C 0.17662(7) 0.70322(14) 0.50540(8) 0.0395(3) Uani 1 1 d . . . . .
H19 H 0.228642 0.660807 0.536557 0.047 Uiso 1 1 calc R . . . .
C20 C 0.19918(9) 0.76240(16) 0.43673(9) 0.0511(4) Uani 1 1 d . . . . .
H20 H 0.266944 0.760398 0.421348 0.061 Uiso 1 1 calc R . . . .
C21 C 0.12521(11) 0.82349(15) 0.39096(7) 0.0456(3) Uani 1 1 d . . . . .
H21 H 0.142093 0.865188 0.344487 0.055 Uiso 1 1 calc R . . . .
C22 C -0.07295(14) 0.6194(2) 0.70160(6) 0.0534(4) Uani 1 1 d . . . . .
H22A H -0.145000 0.633493 0.710494 0.080 Uiso 1 1 calc GR . . . .
H22B H -0.035336 0.709902 0.731876 0.080 Uiso 1 1 calc GR . . . .
H22C H -0.052100 0.486213 0.712400 0.080 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C1 1.3448(14) . ?
O2 C3 1.2409(11) . ?
O3 C6 1.2207(11) . ?
C1 C2 1.4052(13) . ?
C1 C10 1.4023(15) . ?
C2 C3 1.4641(12) . ?
C2 C7 1.4063(12) . ?
C3 C4 1.4645(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.3435(12) . ?
C5 C6 1.4880(12) . ?
C5 C11 1.4936(12) . ?
C6 C7 1.4897(13) . ?
C7 C8 1.3840(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.3972(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3730(19) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O4 H4A 0.8400 . ?
O4 C12 1.3394(14) . ?
O5 C14 1.2403(10) . ?
O6 C17 1.2234(12) . ?
C12 C13 1.4048(12) . ?
C12 C21 1.3974(17) . ?
C13 C14 1.4614(11) . ?
C13 C18 1.4039(12) . ?
C14 C15 1.4597(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.3370(14) . ?
C16 C17 1.4819(15) . ?
C16 C22 1.4976(14) . ?
C17 C18 1.4877(14) . ?
C18 C19 1.3831(13) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 H1 109.5 . . ?
O1 C1 C2 122.15(9) . . ?
O1 C1 C10 118.10(9) . . ?
C10 C1 C2 119.75(10) . . ?
C1 C2 C3 121.00(9) . . ?
C1 C2 C7 119.30(8) . . ?
C7 C2 C3 119.70(8) . . ?
O2 C3 C2 121.24(8) . . ?
O2 C3 C4 119.67(8) . . ?
C2 C3 C4 119.09(7) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 C3 122.88(8) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 119.53(8) . . ?
C4 C5 C11 123.58(8) . . ?
C6 C5 C11 116.87(8) . . ?
O3 C6 C5 120.13(9) . . ?
O3 C6 C7 121.02(9) . . ?
C5 C6 C7 118.85(8) . . ?
C2 C7 C6 119.83(7) . . ?
C8 C7 C2 120.44(9) . . ?
C8 C7 C6 119.73(9) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.41(11) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.25(9) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 H10 120.1 . . ?
C9 C10 C1 119.83(10) . . ?
C9 C10 H10 120.1 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O4 H4A 109.5 . . ?
O4 C12 C13 121.59(10) . . ?
O4 C12 C21 118.95(10) . . ?
C21 C12 C13 119.44(11) . . ?
C12 C13 C14 120.43(8) . . ?
C18 C13 C12 119.48(9) . . ?
C18 C13 C14 120.08(7) . . ?
O5 C14 C13 121.56(8) . . ?
O5 C14 C15 119.89(8) . . ?
C15 C14 C13 118.54(7) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 C14 122.97(8) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C17 120.16(8) . . ?
C15 C16 C22 122.91(11) . . ?
C17 C16 C22 116.92(11) . . ?
O6 C17 C16 120.91(10) . . ?
O6 C17 C18 120.81(11) . . ?
C16 C17 C18 118.28(8) . . ?
C13 C18 C17 119.85(8) . . ?
C19 C18 C13 120.14(10) . . ?
C19 C18 C17 120.01(9) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.68(11) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.04(10) . . ?
C21 C20 H20 119.5 . . ?
C12 C21 H21 119.9 . . ?
C20 C21 C12 120.20(11) . . ?
C20 C21 H21 119.9 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.86 2.5983(12) 145.8 .
O4 H4A O5 0.84 1.83 2.5701(13) 146.7 .

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_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_p2c_GD-158A
_database_code_depnum_ccdc_archive 'CCDC 1859289'

_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C11 H8 O4'
_chemical_formula_weight         204.17
_cell_length_a                   8.2501(4)
_cell_length_b                   12.9456(5)
_cell_length_c                   8.2268(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.403(2)
_cell_angle_gamma                90
_cell_volume                     876.05(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P 1 21/c 1'
_exptl_crystal_density_diffrn    1.548
_refine_ls_R_factor_gt           0.0388


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 0.51632(9) 0.41433(5) 0.79319(8) 0.01913(16) Uani 1 1 d D . . . .
H1 H 0.5256(18) 0.3592(10) 0.7169(17) 0.029 Uiso 1 1 d DR . . . .
O2 O 0.59259(9) 0.30888(5) 0.54578(8) 0.01832(16) Uani 1 1 d . . . . .
O3 O 0.93492(9) 0.62528(5) 0.32705(8) 0.01861(16) Uani 1 1 d . . . . .
O4 O 0.89835(8) 0.46031(5) 0.14406(8) 0.01624(15) Uani 1 1 d . . . . .
C1 C 0.60893(11) 0.49045(7) 0.73621(10) 0.01471(17) Uani 1 1 d . . . . .
C2 C 0.68487(10) 0.48025(6) 0.59025(10) 0.01305(16) Uani 1 1 d . . . . .
C3 C 0.77605(10) 0.56370(6) 0.53556(10) 0.01283(16) Uani 1 1 d . . . . .
C4 C 0.79262(11) 0.65431(7) 0.62564(11) 0.01506(17) Uani 1 1 d . . . . .
H4 H 0.855354 0.710004 0.588994 0.018 Uiso 1 1 calc R . . . .
C5 C 0.71604(11) 0.66267(7) 0.77071(11) 0.01716(18) Uani 1 1 d . . . . .
H5 H 0.726638 0.724798 0.832068 0.021 Uiso 1 1 calc R . . . .
C6 C 0.62524(12) 0.58238(7) 0.82665(11) 0.01749(18) Uani 1 1 d . . . . .
H6 H 0.574123 0.589267 0.925689 0.021 Uiso 1 1 calc R . . . .
C7 C 0.85332(10) 0.55557(6) 0.37908(10) 0.01323(16) Uani 1 1 d . . . . .
C8 C 0.82852(10) 0.45688(6) 0.28419(10) 0.01339(17) Uani 1 1 d . . . . .
C9 C 0.74439(11) 0.37668(7) 0.34184(11) 0.01486(17) Uani 1 1 d . . . . .
H9 H 0.734040 0.314551 0.280472 0.018 Uiso 1 1 calc R . . . .
C10 C 0.66975(11) 0.38386(7) 0.49560(11) 0.01409(17) Uani 1 1 d . . . . .
C11 C 0.88094(12) 0.36995(7) 0.04088(11) 0.01811(18) Uani 1 1 d . . . . .
H11A H 0.935413 0.381970 -0.059168 0.027 Uiso 1 1 calc GR . . . .
H11B H 0.765278 0.356368 0.013051 0.027 Uiso 1 1 calc GR . . . .
H11C H 0.930345 0.310273 0.098829 0.027 Uiso 1 1 calc GR . . . .


_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 H1 0.957(12) . ?
O1 C1 1.3526(11) . ?
O2 C10 1.2482(10) . ?
O3 C7 1.2228(10) . ?
O4 C8 1.3285(10) . ?
O4 C11 1.4459(11) . ?
C1 C2 1.4026(12) . ?
C1 C6 1.4045(13) . ?
C2 C3 1.4098(12) . ?
C2 C10 1.4711(12) . ?
C3 C4 1.3886(12) . ?
C3 C7 1.4835(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.3968(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.3807(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.5031(12) . ?
C8 C9 1.3546(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.4517(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 H1 103.9(9) . . ?
C8 O4 C11 116.89(7) . . ?
O1 C1 C2 121.97(8) . . ?
O1 C1 C6 117.87(8) . . ?
C2 C1 C6 120.16(8) . . ?
C1 C2 C3 119.04(8) . . ?
C1 C2 C10 120.51(8) . . ?
C3 C2 C10 120.45(8) . . ?
C2 C3 C7 119.86(8) . . ?
C4 C3 C2 120.67(8) . . ?
C4 C3 C7 119.46(8) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.27(8) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.27(8) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.59(8) . . ?
C5 C6 H6 120.2 . . ?
O3 C7 C3 122.43(8) . . ?
O3 C7 C8 120.14(8) . . ?
C3 C7 C8 117.43(7) . . ?
O4 C8 C7 111.81(7) . . ?
O4 C8 C9 126.69(8) . . ?
C9 C8 C7 121.51(8) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.27(8) . . ?
C10 C9 H9 119.4 . . ?
O2 C10 C2 120.61(8) . . ?
O2 C10 C9 119.98(8) . . ?
C9 C10 C2 119.41(7) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.957(12) 1.682(13) 2.5687(10) 152.3(13) .

_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_mo_0307_GD-167A
_database_code_depnum_ccdc_archive 'CCDC 1859453'

_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
'Ruthenium-catalyzed C-H oxygenation of quinones: Practical protocol for functionalization of weakly-coordinating carbonyl compounds and their potential trypanocidal activity.'


_chemical_formula_sum            'C11 H7 Cl O4'
_chemical_formula_weight         238.62
_cell_length_a                   3.7418(4)
_cell_length_b                   14.328(2)
_cell_length_c                   17.615(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     944.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_space_group_name_H-M_alt        'P 21 21 21'
_exptl_crystal_density_diffrn    1.678
_refine_ls_R_factor_gt           0.0387



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
Cl1 Cl 0.91087(15) 0.59684(4) 0.23022(3) 0.01892(13) Uani 1 1 d . . . . .
O1 O 0.7909(5) 0.39934(12) 0.21973(9) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.5719(8) 0.28795(12) 0.34387(11) 0.0322(5) Uani 1 1 d . . . . .
O3 O 0.4229(7) 0.64711(12) 0.51492(10) 0.0256(4) Uani 1 1 d D . . . .
H3 H 0.554(10) 0.669(2) 0.4757(17) 0.038 Uiso 1 1 d DR . . . .
O4 O 0.7196(5) 0.65536(11) 0.38250(10) 0.0212(4) Uani 1 1 d . . . . .
C1 C 0.7402(6) 0.52655(15) 0.30001(12) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.6909(6) 0.43403(15) 0.28699(12) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.5606(7) 0.37294(16) 0.34996(12) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.4332(6) 0.41814(15) 0.42091(11) 0.0153(4) Uani 1 1 d . . . . .
C5 C 0.4845(6) 0.51508(15) 0.43158(12) 0.0157(4) Uani 1 1 d . . . . .
C6 C 0.6533(6) 0.57153(14) 0.37246(12) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.3776(7) 0.55581(16) 0.50045(12) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.2236(7) 0.49979(19) 0.55692(13) 0.0218(5) Uani 1 1 d . . . . .
H8 H 0.153136 0.527120 0.603727 0.026 Uiso 1 1 calc R . . . .
C9 C 0.1732(6) 0.40596(19) 0.54543(13) 0.0221(4) Uani 1 1 d . . . . .
H9 H 0.066557 0.369101 0.584109 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2784(7) 0.36402(17) 0.47682(13) 0.0191(4) Uani 1 1 d . . . . .
H10 H 0.243292 0.299060 0.469000 0.023 Uiso 1 1 calc R . . . .
C11 C 0.6406(7) 0.31382(15) 0.18943(14) 0.0212(4) Uani 1 1 d . . . . .
H11A H 0.758873 0.260077 0.212945 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.677256 0.311929 0.134367 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.384069 0.311660 0.200512 0.032 Uiso 1 1 calc GR . . . .


_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
Cl1 C1 1.713(2) . ?
O1 C2 1.338(3) . ?
O1 C11 1.450(3) . ?
O2 C3 1.223(3) . ?
O3 H3 0.90(2) . ?
O3 C7 1.343(3) . ?
O4 C6 1.239(3) . ?
C1 C2 1.358(3) . ?
C1 C6 1.466(3) . ?
C2 C3 1.495(3) . ?
C3 C4 1.486(3) . ?
C4 C5 1.415(3) . ?
C4 C10 1.381(3) . ?
C5 C6 1.462(3) . ?
C5 C7 1.404(3) . ?
C7 C8 1.402(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 O1 C11 122.08(18) . . ?
C7 O3 H3 105(2) . . ?
C2 C1 Cl1 120.23(17) . . ?
C2 C1 C6 123.09(19) . . ?
C6 C1 Cl1 116.68(16) . . ?
O1 C2 C1 118.3(2) . . ?
O1 C2 C3 122.06(19) . . ?
C1 C2 C3 119.38(19) . . ?
O2 C3 C2 120.4(2) . . ?
O2 C3 C4 121.2(2) . . ?
C4 C3 C2 118.27(19) . . ?
C5 C4 C3 119.74(19) . . ?
C10 C4 C3 119.3(2) . . ?
C10 C4 C5 120.9(2) . . ?
C4 C5 C6 120.48(19) . . ?
C7 C5 C4 119.0(2) . . ?
C7 C5 C6 120.6(2) . . ?
O4 C6 C1 120.4(2) . . ?
O4 C6 C5 121.4(2) . . ?
C5 C6 C1 118.20(18) . . ?
O3 C7 C5 122.2(2) . . ?
O3 C7 C8 118.3(2) . . ?
C8 C7 C5 119.5(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C4 C10 C9 119.4(2) . . ?
C4 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.90(2) 1.76(3) 2.586(3) 150(3) .

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.59(9)
2 0.41(9)

