# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_C2412
_database_code_depnum_ccdc_archive 'CCDC 1928261'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;


_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2439(15)
_cell_length_b                   11.2793(6)
_cell_length_c                   8.4391(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.062(8)
_cell_angle_gamma                90
_cell_volume                     1451.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1586
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      30.32
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            36332
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_max         34.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5856
_reflns_number_gt                2357
_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_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1043P)²+0.0709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5856
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1882
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2532
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O2 O 0.92246(8) 0.42906(11) 0.37979(17) 0.0490(4) Uani 1 1 d . . . . .
O1 O 0.97996(10) 0.63643(12) 0.28432(19) 0.0572(4) Uani 1 1 d . . . . .
N1 N 0.68045(11) 0.63459(13) 0.6219(2) 0.0488(4) Uani 1 1 d . . . . .
C9 C 0.87628(11) 0.52471(14) 0.4271(2) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.91593(12) 0.63730(16) 0.3699(2) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.80328(12) 0.52383(15) 0.5140(2) 0.0417(4) Uani 1 1 d . . . . .
H10 H 0.7814 0.4515 0.5492 0.050 Uiso 1 1 calc R U . . .
C2 C 0.79881(13) 0.74578(14) 0.5172(2) 0.0414(4) Uani 1 1 d . . . . .
C1 C 0.75675(13) 0.63153(15) 0.5555(2) 0.0410(4) Uani 1 1 d . . . . .
C7 C 0.87453(12) 0.74806(15) 0.4259(2) 0.0412(4) Uani 1 1 d . . . . .
C11 C 0.62994(12) 0.53184(15) 0.6457(3) 0.0451(5) Uani 1 1 d . . . . .
C17 C 0.89135(13) 0.31496(16) 0.4287(3) 0.0496(5) Uani 1 1 d . . . . .
H17A H 0.8811 0.3160 0.5421 0.060 Uiso 1 1 calc R U . . .
H17B H 0.9362 0.2561 0.4072 0.060 Uiso 1 1 calc R U . . .
C16 C 0.60984(14) 0.45338(17) 0.5246(3) 0.0519(5) Uani 1 1 d . . . . .
H16 H 0.6352 0.4632 0.4252 0.062 Uiso 1 1 calc R U . . .
C3 C 0.76198(15) 0.85245(16) 0.5691(3) 0.0522(5) Uani 1 1 d . . . . .
H3 H 0.7115 0.8521 0.6309 0.063 Uiso 1 1 calc R U . . .
C18 C 0.81085(15) 0.28102(17) 0.3481(3) 0.0545(6) Uani 1 1 d . . . . .
C6 C 0.91247(15) 0.85672(16) 0.3838(3) 0.0525(5) Uani 1 1 d . . . . .
H6 H 0.9625 0.8584 0.3210 0.063 Uiso 1 1 calc R U . . .
C12 C 0.59076(14) 0.51603(18) 0.7912(3) 0.0567(6) Uani 1 1 d . . . . .
H12 H 0.6022 0.5693 0.8728 0.068 Uiso 1 1 calc R U . . .
C4 C 0.80136(16) 0.95880(17) 0.5276(3) 0.0608(6) Uani 1 1 d . . . . .
H4 H 0.7772 1.0299 0.5624 0.073 Uiso 1 1 calc R U . . .
C5 C 0.87563(16) 0.96041(17) 0.4356(3) 0.0607(6) Uani 1 1 d . . . . .
H5 H 0.9011 1.0325 0.4083 0.073 Uiso 1 1 calc R U . . .
C15 C 0.55256(15) 0.36092(18) 0.5505(3) 0.0607(6) Uani 1 1 d . . . . .
H15 H 0.5396 0.3087 0.4684 0.073 Uiso 1 1 calc R U . . .
C14 C 0.51457(16) 0.34526(19) 0.6956(3) 0.0639(7) Uani 1 1 d . . . . .
H14 H 0.4754 0.2833 0.7122 0.077 Uiso 1 1 calc R U . . .
C13 C 0.53483(16) 0.4221(2) 0.8171(3) 0.0668(7) Uani 1 1 d . . . . .
H13 H 0.5107 0.4105 0.9170 0.080 Uiso 1 1 calc R U . . .
C19 C 0.74625(19) 0.2500(2) 0.2862(3) 0.0752(8) Uani 1 1 d . . . . .
H19 H 0.6948 0.2253 0.2369 0.090 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
O2 C9 1.3488(19) . ?
O2 C17 1.432(2) . ?
O1 C8 1.215(2) . ?
N1 C1 1.292(2) . ?
N1 C11 1.406(2) . ?
C9 C10 1.333(2) . ?
C9 C8 1.487(2) . ?
C8 C7 1.477(2) . ?
C10 C1 1.450(2) . ?
C10 H10 0.9300 . ?
C2 C7 1.389(3) . ?
C2 C3 1.398(3) . ?
C2 C1 1.475(2) . ?
C7 C6 1.401(2) . ?
C11 C12 1.378(3) . ?
C11 C16 1.386(3) . ?
C17 C18 1.453(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 C15 1.378(3) . ?
C16 H16 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C18 C19 1.168(3) . ?
C6 C5 1.369(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.367(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.377(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C19 H19 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
C9 O2 C17 117.41(14) . . ?
C1 N1 C11 122.24(15) . . ?
C10 C9 O2 126.37(15) . . ?
C10 C9 C8 121.64(16) . . ?
O2 C9 C8 112.00(15) . . ?
O1 C8 C7 122.73(16) . . ?
O1 C8 C9 120.87(16) . . ?
C7 C8 C9 116.39(16) . . ?
C9 C10 C1 122.37(16) . . ?
C9 C10 H10 118.8 . . ?
C1 C10 H10 118.8 . . ?
C7 C2 C3 119.47(17) . . ?
C7 C2 C1 119.95(15) . . ?
C3 C2 C1 120.55(18) . . ?
N1 C1 C10 124.61(16) . . ?
N1 C1 C2 117.60(16) . . ?
C10 C1 C2 117.78(17) . . ?
C2 C7 C6 120.02(17) . . ?
C2 C7 C8 121.16(15) . . ?
C6 C7 C8 118.82(18) . . ?
C12 C11 C16 118.63(19) . . ?
C12 C11 N1 118.18(18) . . ?
C16 C11 N1 122.77(19) . . ?
O2 C17 C18 112.43(17) . . ?
O2 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
O2 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C19 C18 C17 177.6(2) . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.51(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C18 C19 H19 180.0 . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_C2413
_database_code_depnum_ccdc_archive 'CCDC 1928326'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;

_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Br N O2'
_chemical_formula_weight         366.21

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.8522(14)
_cell_length_b                   11.2852(10)
_cell_length_c                   8.2232(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.868(9)
_cell_angle_gamma                90
_cell_volume                     1563.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4165
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      31.41

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    2.639
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.688
_exptl_absorpt_process_details   '(Clark, R. C. & Reid, J. S. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            25444
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         34.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6419
_reflns_number_gt                3051
_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       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6419
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2113
_refine_ls_R_factor_gt           0.1325
_refine_ls_wR_factor_ref         0.4225
_refine_ls_wR_factor_gt          0.3699
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.229
_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
Br1 Br -0.04323(5) -0.21838(8) -0.26348(11) 0.0813(4) Uani 1 1 d . . . . .
O2 O 0.4215(2) -0.0765(3) 0.1202(5) 0.0442(9) Uani 1 1 d . . . . .
O1 O 0.4860(2) 0.1269(4) 0.2026(5) 0.0510(10) Uani 1 1 d . . . . .
C19 C 0.2558(5) -0.2429(8) 0.1974(12) 0.075(2) Uani 1 1 d . . . . .
H19 H 0.2077 -0.2641 0.2412 0.090 Uiso 1 1 calc R U . . .
N1 N 0.2169(3) 0.1434(4) -0.1684(6) 0.0454(10) Uani 1 1 d . . . . .
C9 C 0.3848(3) 0.0219(4) 0.0627(6) 0.0358(9) Uani 1 1 d . . . . .
C10 C 0.3183(3) 0.0248(4) -0.0314(6) 0.0389(10) Uani 1 1 d . . . . .
H10 H 0.2941 -0.0462 -0.0623 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3927(3) 0.2446(4) 0.0566(6) 0.0369(9) Uani 1 1 d . . . . .
C11 C 0.1652(3) 0.0472(5) -0.1907(7) 0.0445(11) Uani 1 1 d . . . . .
C8 C 0.4261(3) 0.1317(4) 0.1164(6) 0.0364(10) Uani 1 1 d . . . . .
C2 C 0.3239(3) 0.2469(4) -0.0432(6) 0.0349(9) Uani 1 1 d . . . . .
C6 C 0.4276(4) 0.3512(5) 0.1069(7) 0.0484(12) Uani 1 1 d . . . . .
H6 H 0.4724 0.3502 0.1760 0.058 Uiso 1 1 calc R U . . .
C1 C 0.2831(3) 0.1352(4) -0.0861(6) 0.0366(9) Uani 1 1 d . . . . .
C12 C 0.1359(3) 0.0189(5) -0.3451(7) 0.0481(12) Uani 1 1 d . . . . .
H12 H 0.1568 0.0561 -0.4352 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3289(4) 0.4602(5) -0.0467(7) 0.0523(14) Uani 1 1 d . . . . .
H4 H 0.3077 0.5323 -0.0817 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2936(4) 0.3550(4) -0.0950(7) 0.0451(11) Uani 1 1 d . . . . .
H3 H 0.2487 0.3567 -0.1636 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0758(4) -0.0640(5) -0.3676(8) 0.0510(13) Uani 1 1 d . . . . .
H13 H 0.0569 -0.0828 -0.4719 0.061 Uiso 1 1 calc R U . . .
C17 C 0.3905(4) -0.1892(5) 0.0684(8) 0.0495(13) Uani 1 1 d . . . . .
H17A H 0.4289 -0.2505 0.0964 0.059 Uiso 1 1 calc R U . . .
H17B H 0.3827 -0.1888 -0.0490 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3147(5) -0.2170(5) 0.1440(8) 0.0536(15) Uani 1 1 d . . . . .
C5 C 0.3965(4) 0.4571(5) 0.0550(7) 0.0533(14) Uani 1 1 d . . . . .
H5 H 0.4207 0.5276 0.0879 0.064 Uiso 1 1 calc R U . . .
C15 C 0.0739(4) -0.0910(6) -0.0839(8) 0.0594(16) Uani 1 1 d . . . . .
H15 H 0.0523 -0.1288 0.0049 0.071 Uiso 1 1 calc R U . . .
C14 C 0.0449(3) -0.1172(6) -0.2370(7) 0.0514(14) Uani 1 1 d . . . . .
C16 C 0.1338(4) -0.0105(5) -0.0578(8) 0.0522(13) Uani 1 1 d . . . . .
H16 H 0.1532 0.0053 0.0471 0.063 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
Br1 C14 1.881(5) . ?
O2 C9 1.350(5) . ?
O2 C17 1.434(6) . ?
O1 C8 1.215(5) . ?
C19 C18 1.136(12) . ?
C19 H19 0.9300 . ?
N1 C1 1.290(6) . ?
N1 C11 1.399(7) . ?
C9 C10 1.341(6) . ?
C9 C8 1.482(6) . ?
C10 C1 1.444(6) . ?
C10 H10 0.9300 . ?
C7 C6 1.396(7) . ?
C7 C2 1.398(7) . ?
C7 C8 1.471(7) . ?
C11 C12 1.385(8) . ?
C11 C16 1.392(8) . ?
C2 C3 1.384(7) . ?
C2 C1 1.473(7) . ?
C6 C5 1.369(9) . ?
C6 H6 0.9300 . ?
C12 C13 1.387(8) . ?
C12 H12 0.9300 . ?
C4 C3 1.381(7) . ?
C4 C5 1.391(9) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C13 C14 1.349(9) . ?
C13 H13 0.9300 . ?
C17 C18 1.474(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C5 H5 0.9300 . ?
C15 C14 1.368(8) . ?
C15 C16 1.370(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
C9 O2 C17 117.8(4) . . ?
C18 C19 H19 180.0 . . ?
C1 N1 C11 122.5(4) . . ?
C10 C9 O2 126.0(4) . . ?
C10 C9 C8 121.8(4) . . ?
O2 C9 C8 112.2(4) . . ?
C9 C10 C1 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
C1 C10 H10 119.1 . . ?
C6 C7 C2 119.4(5) . . ?
C6 C7 C8 119.6(5) . . ?
C2 C7 C8 120.9(4) . . ?
C12 C11 C16 118.6(5) . . ?
C12 C11 N1 120.1(5) . . ?
C16 C11 N1 120.7(5) . . ?
O1 C8 C7 122.4(4) . . ?
O1 C8 C9 120.6(4) . . ?
C7 C8 C9 117.0(4) . . ?
C3 C2 C7 119.2(5) . . ?
C3 C2 C1 121.0(4) . . ?
C7 C2 C1 119.7(4) . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C1 C10 124.3(4) . . ?
N1 C1 C2 117.0(4) . . ?
C10 C1 C2 118.7(4) . . ?
C11 C12 C13 121.0(6) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O2 C17 C18 112.1(5) . . ?
O2 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
O2 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 176.8(8) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C14 C15 C16 121.8(6) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C13 C14 C15 120.1(5) . . ?
C13 C14 Br1 120.1(4) . . ?
C15 C14 Br1 119.6(5) . . ?
C15 C16 C11 119.0(5) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?

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
C17 O2 C9 C10 4.5(8) . . . . ?
C17 O2 C9 C8 -176.0(5) . . . . ?
O2 C9 C10 C1 179.6(5) . . . . ?
C8 C9 C10 C1 0.1(8) . . . . ?
C1 N1 C11 C12 -130.3(6) . . . . ?
C1 N1 C11 C16 58.9(8) . . . . ?
C6 C7 C8 O1 -3.7(8) . . . . ?
C2 C7 C8 O1 179.6(5) . . . . ?
C6 C7 C8 C9 178.1(5) . . . . ?
C2 C7 C8 C9 1.5(7) . . . . ?
C10 C9 C8 O1 179.5(5) . . . . ?
O2 C9 C8 O1 -0.1(7) . . . . ?
C10 C9 C8 C7 -2.3(8) . . . . ?
O2 C9 C8 C7 178.1(4) . . . . ?
C6 C7 C2 C3 2.3(8) . . . . ?
C8 C7 C2 C3 179.0(5) . . . . ?
C6 C7 C2 C1 -175.2(5) . . . . ?
C8 C7 C2 C1 1.5(7) . . . . ?
C2 C7 C6 C5 -2.0(9) . . . . ?
C8 C7 C6 C5 -178.7(5) . . . . ?
C11 N1 C1 C10 10.8(9) . . . . ?
C11 N1 C1 C2 -167.8(5) . . . . ?
C9 C10 C1 N1 -175.6(5) . . . . ?
C9 C10 C1 C2 3.0(8) . . . . ?
C3 C2 C1 N1 -2.5(8) . . . . ?
C7 C2 C1 N1 175.0(5) . . . . ?
C3 C2 C1 C10 178.8(5) . . . . ?
C7 C2 C1 C10 -3.7(7) . . . . ?
C16 C11 C12 C13 0.8(8) . . . . ?
N1 C11 C12 C13 -170.2(5) . . . . ?
C5 C4 C3 C2 0.5(9) . . . . ?
C7 C2 C3 C4 -1.6(8) . . . . ?
C1 C2 C3 C4 175.9(5) . . . . ?
C11 C12 C13 C14 0.5(9) . . . . ?
C9 O2 C17 C18 -72.4(6) . . . . ?
C7 C6 C5 C4 0.9(10) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
C12 C13 C14 C15 -1.2(10) . . . . ?
C12 C13 C14 Br1 173.9(5) . . . . ?
C16 C15 C14 C13 0.5(10) . . . . ?
C16 C15 C14 Br1 -174.7(5) . . . . ?
C14 C15 C16 C11 0.9(10) . . . . ?
C12 C11 C16 C15 -1.5(9) . . . . ?
N1 C11 C16 C15 169.5(6) . . . . ?

_refine_diff_density_max         2.908
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.170

####################################################################### 
# 
# 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_C1814
_database_code_depnum_ccdc_archive 'CCDC 1928361'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;

_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 I N O2'
_chemical_formula_weight         413.20

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1059(8)
_cell_length_b                   11.3027(5)
_cell_length_c                   8.3987(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.703(4)
_cell_angle_gamma                90
_cell_volume                     1623.11(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6786
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      32.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.982
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   '(Clark, R. C. & Reid, J. S. (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            24777
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.988
_diffrn_reflns_theta_max         34.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6500
_reflns_number_gt                4084
_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_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+3.4557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6500
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_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
I1 I 1.04792(2) 0.71424(3) 0.27316(4) 0.06812(14) Uani 1 1 d . . . . .
O2 O 0.57674(14) 0.5770(2) -0.1197(3) 0.0417(5) Uani 1 1 d . . . . .
O1 O 0.51272(15) 0.3747(2) -0.2010(3) 0.0478(6) Uani 1 1 d . . . . .
N1 N 0.77408(16) 0.3559(2) 0.1705(4) 0.0392(6) Uani 1 1 d . . . . .
C9 C 0.61222(18) 0.4787(3) -0.0621(4) 0.0330(6) Uani 1 1 d . . . . .
C1 C 0.71057(18) 0.3646(3) 0.0874(4) 0.0328(6) Uani 1 1 d . . . . .
C12 C 0.8543(2) 0.4768(3) 0.3463(5) 0.0429(8) Uani 1 1 d . . . . .
H12 H 0.8325 0.4400 0.4336 0.052 Uiso 1 1 calc R U . . .
C2 C 0.66979(18) 0.2531(3) 0.0443(4) 0.0315(6) Uani 1 1 d . . . . .
C8 C 0.57077(18) 0.3691(3) -0.1152(4) 0.0343(6) Uani 1 1 d . . . . .
C10 C 0.67711(18) 0.4753(3) 0.0316(4) 0.0341(6) Uani 1 1 d . . . . .
H10 H 0.7012 0.5459 0.0615 0.041 Uiso 1 1 calc R U . . .
C7 C 0.60375(19) 0.2560(3) -0.0569(4) 0.0331(6) Uani 1 1 d . . . . .
C11 C 0.82578(18) 0.4516(3) 0.1942(4) 0.0377(7) Uani 1 1 d . . . . .
C3 C 0.6993(2) 0.1450(3) 0.0958(4) 0.0387(7) Uani 1 1 d . . . . .
H3 H 0.7430 0.1426 0.1644 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6643(2) 0.0410(3) 0.0461(5) 0.0448(8) Uani 1 1 d . . . . .
H4 H 0.6843 -0.0313 0.0812 0.054 Uiso 1 1 calc R U . . .
C18 C 0.6822(3) 0.7169(3) -0.1426(5) 0.0510(9) Uani 1 1 d . . . . .
C13 C 0.9151(2) 0.5563(4) 0.3696(5) 0.0459(8) Uani 1 1 d . . . . .
H13 H 0.9332 0.5743 0.4722 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6079(2) 0.6895(3) -0.0710(5) 0.0468(8) Uani 1 1 d . . . . .
H17A H 0.6150 0.6900 0.0440 0.056 Uiso 1 1 calc R U . . .
H17B H 0.5704 0.7508 -0.0996 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9200(2) 0.5854(4) 0.0892(5) 0.0502(9) Uani 1 1 d . . . . .
H15 H 0.9421 0.6224 0.0025 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5992(2) 0.0438(3) -0.0562(5) 0.0475(9) Uani 1 1 d . . . . .
H5 H 0.5760 -0.0264 -0.0908 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8587(2) 0.5079(4) 0.0654(4) 0.0457(8) Uani 1 1 d . . . . .
H16 H 0.8393 0.4932 -0.0372 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5690(2) 0.1501(3) -0.1062(4) 0.0429(8) Uani 1 1 d . . . . .
H6 H 0.5249 0.1517 -0.1737 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9485(2) 0.6084(4) 0.2414(5) 0.0445(8) Uani 1 1 d . . . . .
C19 C 0.7415(4) 0.7420(5) -0.2004(8) 0.0746(15) Uani 1 1 d . . . . .
H19 H 0.7886 0.7619 -0.2462 0.090 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
I1 C14 2.090(3) . ?
O2 C9 1.349(4) . ?
O2 C17 1.433(4) . ?
O1 C8 1.211(4) . ?
N1 C1 1.277(4) . ?
N1 C11 1.407(4) . ?
C9 C10 1.342(4) . ?
C9 C8 1.489(4) . ?
C1 C10 1.448(4) . ?
C1 C2 1.480(4) . ?
C12 C11 1.384(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C2 C3 1.387(4) . ?
C2 C7 1.394(4) . ?
C8 C7 1.476(5) . ?
C10 H10 0.9300 . ?
C7 C6 1.393(5) . ?
C11 C16 1.388(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9300 . ?
C18 C19 1.173(7) . ?
C18 C17 1.455(6) . ?
C13 C14 1.367(5) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C16 1.376(5) . ?
C15 C14 1.379(5) . ?
C15 H15 0.9300 . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C19 H19 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
C9 O2 C17 117.9(3) . . ?
C1 N1 C11 122.6(3) . . ?
C10 C9 O2 126.1(3) . . ?
C10 C9 C8 122.0(3) . . ?
O2 C9 C8 111.9(3) . . ?
N1 C1 C10 124.4(3) . . ?
N1 C1 C2 117.1(3) . . ?
C10 C1 C2 118.5(3) . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 120.6(3) . . ?
C7 C2 C1 119.8(3) . . ?
O1 C8 C7 122.7(3) . . ?
O1 C8 C9 120.7(3) . . ?
C7 C8 C9 116.6(3) . . ?
C9 C10 C1 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C1 C10 H10 119.1 . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 C8 119.3(3) . . ?
C2 C7 C8 121.1(3) . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 N1 119.5(3) . . ?
C16 C11 N1 120.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C19 C18 C17 178.3(5) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O2 C17 C18 113.1(3) . . ?
O2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
O2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 I1 120.2(3) . . ?
C15 C14 I1 119.4(3) . . ?
C18 C19 H19 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
C17 O2 C9 C10 -3.5(5) . . . . ?
C17 O2 C9 C8 176.7(3) . . . . ?
C11 N1 C1 C10 -11.2(6) . . . . ?
C11 N1 C1 C2 167.8(3) . . . . ?
N1 C1 C2 C3 1.3(5) . . . . ?
C10 C1 C2 C3 -179.6(3) . . . . ?
N1 C1 C2 C7 -174.8(3) . . . . ?
C10 C1 C2 C7 4.3(5) . . . . ?
C10 C9 C8 O1 -179.3(3) . . . . ?
O2 C9 C8 O1 0.5(5) . . . . ?
C10 C9 C8 C7 1.2(5) . . . . ?
O2 C9 C8 C7 -179.0(3) . . . . ?
O2 C9 C10 C1 179.9(3) . . . . ?
C8 C9 C10 C1 -0.3(5) . . . . ?
N1 C1 C10 C9 176.6(3) . . . . ?
C2 C1 C10 C9 -2.4(5) . . . . ?
C3 C2 C7 C6 -0.8(5) . . . . ?
C1 C2 C7 C6 175.4(3) . . . . ?
C3 C2 C7 C8 -179.6(3) . . . . ?
C1 C2 C7 C8 -3.5(5) . . . . ?
O1 C8 C7 C6 2.5(5) . . . . ?
C9 C8 C7 C6 -178.1(3) . . . . ?
O1 C8 C7 C2 -178.7(3) . . . . ?
C9 C8 C7 C2 0.8(5) . . . . ?
C13 C12 C11 C16 -0.4(6) . . . . ?
C13 C12 C11 N1 168.7(3) . . . . ?
C1 N1 C11 C12 132.4(4) . . . . ?
C1 N1 C11 C16 -58.7(5) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 -175.4(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C9 O2 C17 C18 72.1(4) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C12 C11 C16 C15 1.4(6) . . . . ?
N1 C11 C16 C15 -167.5(4) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
C2 C7 C6 C5 0.0(5) . . . . ?
C8 C7 C6 C5 178.9(3) . . . . ?
C12 C13 C14 C15 2.4(6) . . . . ?
C12 C13 C14 I1 -173.4(3) . . . . ?
C16 C15 C14 C13 -1.4(7) . . . . ?
C16 C15 C14 I1 174.5(3) . . . . ?

_refine_diff_density_max         1.934
_refine_diff_density_min         -2.200
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_C2407
_database_code_depnum_ccdc_archive 'CCDC 1928382'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;


_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.1895(7)
_cell_length_b                   11.6796(19)
_cell_length_c                   32.919(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3308
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      34.6

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR590'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images,thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.237
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3194
_reflns_number_gt                2753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.628
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.959

_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.6154P] 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 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O2 O 0.1943(6) 0.36904(18) 0.67885(6) 0.0463(6) Uani 1 1 d . . . . .
O1 O 0.4743(7) 0.4930(2) 0.73414(7) 0.0628(8) Uani 1 1 d . . . . .
O3 O 0.1950(8) 0.3071(2) 0.42887(7) 0.0692(9) Uani 1 1 d . . . . .
N1 N 0.6249(7) 0.6251(2) 0.57770(7) 0.0429(7) Uani 1 1 d . . . . .
C9 C 0.3612(8) 0.4589(3) 0.66497(9) 0.0374(7) Uani 1 1 d . . . . .
C2 C 0.7309(7) 0.6600(2) 0.64745(9) 0.0360(7) Uani 1 1 d . . . . .
C11 C 0.5018(8) 0.5663(3) 0.54385(9) 0.0380(7) Uani 1 1 d . . . . .
C1 C 0.5867(8) 0.5898(3) 0.61473(9) 0.0356(7) Uani 1 1 d . . . . .
C7 C 0.6852(8) 0.6294(3) 0.68813(9) 0.0395(7) Uani 1 1 d . . . . .
C14 C 0.2718(8) 0.4642(3) 0.47239(9) 0.0373(7) Uani 1 1 d . . . . .
C17 C 0.1447(9) 0.4081(3) 0.43512(9) 0.0437(8) Uani 1 1 d . . . . .
C10 C 0.4009(8) 0.4897(3) 0.62627(9) 0.0377(7) Uani 1 1 d . . . . .
H10 H 0.3066 0.4457 0.6060 0.045 Uiso 1 1 calc R U . . .
C19 C 0.0786(8) 0.2899(3) 0.64877(9) 0.0408(7) Uani 1 1 d . . . . .
H19A H 0.2541 0.2608 0.6326 0.049 Uiso 1 1 calc R U . . .
H19B H -0.0726 0.3274 0.6309 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3192(8) 0.6277(3) 0.51666(9) 0.0419(7) Uani 1 1 d . . . . .
H12 H 0.2722 0.7040 0.5221 0.050 Uiso 1 1 calc R U . . .
C20 C -0.0757(9) 0.1970(3) 0.67071(10) 0.0458(8) Uani 1 1 d . . . . .
C8 C 0.5064(8) 0.5256(3) 0.69913(9) 0.0406(8) Uani 1 1 d . . . . .
C13 C 0.2048(8) 0.5780(3) 0.48148(9) 0.0427(8) Uani 1 1 d . . . . .
H13 H 0.0816 0.6212 0.4637 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4601(9) 0.4030(3) 0.49947(9) 0.0435(8) Uani 1 1 d . . . . .
H15 H 0.5089 0.3269 0.4939 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9087(9) 0.7575(3) 0.63864(10) 0.0457(8) Uani 1 1 d . . . . .
H3 H 0.9451 0.7778 0.6117 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5763(9) 0.4528(3) 0.53447(9) 0.0434(8) Uani 1 1 d . . . . .
H16 H 0.7050 0.4105 0.5519 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8084(9) 0.6984(3) 0.71899(10) 0.0497(9) Uani 1 1 d . . . . .
H6 H 0.7743 0.6787 0.7460 0.060 Uiso 1 1 calc R U . . .
C18 C -0.0400(9) 0.4792(3) 0.40529(10) 0.0535(9) Uani 1 1 d . . . . .
H18A H -0.0561 0.5563 0.4152 0.080 Uiso 1 1 calc R U . . .
H18B H 0.0680 0.4791 0.3796 0.080 Uiso 1 1 calc R U . . .
H18C H -0.2501 0.4477 0.4020 0.080 Uiso 1 1 calc R U . . .
C4 C 1.0312(9) 0.8241(3) 0.66940(11) 0.0551(9) Uani 1 1 d . . . . .
H4 H 1.1494 0.8891 0.6631 0.066 Uiso 1 1 calc R U . . .
C5 C 0.9800(10) 0.7951(3) 0.70964(11) 0.0570(10) Uani 1 1 d . . . . .
H5 H 1.0615 0.8410 0.7303 0.068 Uiso 1 1 calc R U . . .
C21 C -0.1992(11) 0.1235(3) 0.68884(11) 0.0623(10) Uani 1 1 d . . . . .
H21 H -0.2978 0.0650 0.7033 0.075 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
O2 C9 1.341(4) . ?
O2 C19 1.439(4) . ?
O1 C8 1.221(4) . ?
O3 C17 1.216(4) . ?
N1 C1 1.297(4) . ?
N1 C11 1.407(4) . ?
C9 C10 1.334(4) . ?
C9 C8 1.497(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.399(4) . ?
C2 C1 1.482(4) . ?
C11 C12 1.379(4) . ?
C11 C16 1.396(4) . ?
C1 C10 1.455(4) . ?
C7 C6 1.395(4) . ?
C7 C8 1.471(5) . ?
C14 C15 1.389(4) . ?
C14 C13 1.391(4) . ?
C14 C17 1.489(4) . ?
C17 C18 1.501(5) . ?
C10 H10 0.9300 . ?
C19 C20 1.455(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C20 C21 1.166(5) . ?
C13 H13 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
C6 C5 1.374(5) . ?
C6 H6 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C21 H21 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
C9 O2 C19 116.4(2) . . ?
C1 N1 C11 122.9(3) . . ?
C10 C9 O2 126.9(3) . . ?
C10 C9 C8 121.8(3) . . ?
O2 C9 C8 111.3(3) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 121.3(3) . . ?
C7 C2 C1 119.9(3) . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 N1 117.6(3) . . ?
C16 C11 N1 123.8(3) . . ?
N1 C1 C10 124.5(3) . . ?
N1 C1 C2 117.2(3) . . ?
C10 C1 C2 118.2(3) . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 C8 119.0(3) . . ?
C2 C7 C8 121.0(3) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 C17 120.3(3) . . ?
C13 C14 C17 121.7(3) . . ?
O3 C17 C14 120.3(3) . . ?
O3 C17 C18 121.0(3) . . ?
C14 C17 C18 118.7(3) . . ?
C9 C10 C1 122.2(3) . . ?
C9 C10 H10 118.9 . . ?
C1 C10 H10 118.9 . . ?
O2 C19 C20 106.7(2) . . ?
O2 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O2 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C21 C20 C19 179.0(4) . . ?
O1 C8 C7 123.1(3) . . ?
O1 C8 C9 120.1(3) . . ?
C7 C8 C9 116.8(2) . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C20 C21 H21 180.0 . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_C595
_database_code_depnum_ccdc_archive 'CCDC 1928296'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;



_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 F N O2'
_chemical_formula_weight         305.30

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_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                   12.4338(17)
_cell_length_b                   7.7886(11)
_cell_length_c                   15.693(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.992(5)
_cell_angle_gamma                90
_cell_volume                     1517.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12429
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR590'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images,thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            20488
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2985
_reflns_number_gt                2254
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL  Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.6886P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2985
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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
O2 O 0.63808(13) 0.1730(2) 0.66748(11) 0.0683(5) Uani 1 1 d . . . . .
N1 N 0.65860(16) 0.7330(2) 0.53741(12) 0.0567(5) Uani 1 1 d . . . . .
O1 O 0.44342(15) 0.2499(3) 0.70834(13) 0.0837(6) Uani 1 1 d . . . . .
F F 1.09479(14) 0.7501(3) 0.49482(13) 0.1279(9) Uani 1 1 d . . . . .
C10 C 0.65544(17) 0.4473(3) 0.59944(13) 0.0497(5) Uani 1 1 d . . . . .
H10 H 0.7247 0.4218 0.5837 0.060 Uiso 1 1 calc R U . . .
C2 C 0.49593(17) 0.6461(3) 0.59806(13) 0.0522(5) Uani 1 1 d . . . . .
C1 C 0.60875(17) 0.6127(3) 0.57582(12) 0.0490(5) Uani 1 1 d . . . . .
C7 C 0.44131(17) 0.5266(3) 0.64537(14) 0.0552(6) Uani 1 1 d . . . . .
C11 C 0.77024(19) 0.7245(3) 0.52664(14) 0.0535(5) Uani 1 1 d . . . . .
C9 C 0.60179(18) 0.3303(3) 0.64323(14) 0.0529(5) Uani 1 1 d . . . . .
C8 C 0.49064(18) 0.3604(3) 0.66940(14) 0.0577(6) Uani 1 1 d . . . . .
C18 C 0.8264(2) 0.2358(3) 0.69524(16) 0.0626(7) Uani 1 1 d . . . . .
C16 C 0.84359(19) 0.7036(3) 0.59553(15) 0.0608(6) Uani 1 1 d . . . . .
H16 H 0.8188 0.6833 0.6495 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8084(2) 0.7567(3) 0.44638(16) 0.0651(6) Uani 1 1 d . . . . .
H12 H 0.7599 0.7737 0.4000 0.078 Uiso 1 1 calc R U . . .
C17 C 0.7467(2) 0.1290(3) 0.64913(17) 0.0692(7) Uani 1 1 d . . . . .
H17A H 0.7553 0.1411 0.5883 0.083 Uiso 1 1 calc R U . . .
H17B H 0.7597 0.0097 0.6641 0.083 Uiso 1 1 calc R U . . .
C19 C 0.8899(2) 0.3247(4) 0.73043(17) 0.0743(7) Uani 1 1 d . . . . .
H19 H 0.9405 0.3955 0.7585 0.089 Uiso 1 1 calc R U . . .
C3 C 0.4463(2) 0.8013(3) 0.57690(17) 0.0708(7) Uani 1 1 d . . . . .
H3 H 0.4825 0.8824 0.5457 0.085 Uiso 1 1 calc R U . . .
C6 C 0.33827(19) 0.5650(4) 0.67173(18) 0.0747(7) Uani 1 1 d . . . . .
H6 H 0.3019 0.4858 0.7040 0.090 Uiso 1 1 calc R U . . .
C15 C 0.9529(2) 0.7125(4) 0.58477(18) 0.0740(7) Uani 1 1 d . . . . .
H15 H 1.0022 0.6991 0.6309 0.089 Uiso 1 1 calc R U . . .
C13 C 0.9173(2) 0.7635(4) 0.43519(18) 0.0806(8) Uani 1 1 d . . . . .
H13 H 0.9431 0.7827 0.3815 0.097 Uiso 1 1 calc R U . . .
C14 C 0.9868(2) 0.7415(4) 0.5049(2) 0.0807(8) Uani 1 1 d . . . . .
C5 C 0.2905(2) 0.7190(5) 0.6502(2) 0.0892(10) Uani 1 1 d . . . . .
H5 H 0.2222 0.7445 0.6682 0.107 Uiso 1 1 calc R U . . .
C4 C 0.3443(2) 0.8357(4) 0.6018(2) 0.0893(9) Uani 1 1 d . . . . .
H4 H 0.3111 0.9387 0.5859 0.107 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
O2 C9 1.353(3) . ?
O2 C17 1.437(3) . ?
N1 C1 1.290(3) . ?
N1 C11 1.409(3) . ?
O1 C8 1.223(3) . ?
F C14 1.362(3) . ?
C10 C9 1.340(3) . ?
C10 C1 1.453(3) . ?
C10 H10 0.9300 . ?
C2 C3 1.389(3) . ?
C2 C7 1.389(3) . ?
C2 C1 1.486(3) . ?
C7 C6 1.399(3) . ?
C7 C8 1.473(3) . ?
C11 C16 1.387(3) . ?
C11 C12 1.392(3) . ?
C9 C8 1.481(3) . ?
C18 C19 1.167(4) . ?
C18 C17 1.457(4) . ?
C16 C15 1.380(3) . ?
C16 H16 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C6 C5 1.373(4) . ?
C6 H6 0.9300 . ?
C15 C14 1.362(4) . ?
C15 H15 0.9300 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C5 C4 1.379(5) . ?
C5 H5 0.9300 . ?
C4 H4 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
C9 O2 C17 117.56(17) . . ?
C1 N1 C11 121.49(18) . . ?
C9 C10 C1 122.1(2) . . ?
C9 C10 H10 119.0 . . ?
C1 C10 H10 119.0 . . ?
C3 C2 C7 119.1(2) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 120.1(2) . . ?
N1 C1 C10 124.6(2) . . ?
N1 C1 C2 117.72(19) . . ?
C10 C1 C2 117.69(19) . . ?
C2 C7 C6 119.7(2) . . ?
C2 C7 C8 121.1(2) . . ?
C6 C7 C8 119.2(2) . . ?
C16 C11 C12 119.0(2) . . ?
C16 C11 N1 121.6(2) . . ?
C12 C11 N1 119.0(2) . . ?
C10 C9 O2 126.3(2) . . ?
C10 C9 C8 122.1(2) . . ?
O2 C9 C8 111.60(19) . . ?
O1 C8 C7 122.8(2) . . ?
O1 C8 C9 120.4(2) . . ?
C7 C8 C9 116.8(2) . . ?
C19 C18 C17 178.2(3) . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O2 C17 C18 112.7(2) . . ?
O2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
O2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C19 H19 180.0 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
F C14 C15 117.9(3) . . ?
F C14 C13 119.1(3) . . ?
C15 C14 C13 122.9(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_C2418
_database_code_depnum_ccdc_archive 'CCDC 1928407'
loop_
_audit_author_name
_audit_author_address
'Carlos Alberto De Simone'
;Instituto de Fisica de Sao Carlos USP
Brazil
;


_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

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

_chemical_name_systematic        
'Ortho-quinones with a ?click? and a pronounced structure -- redox -- biological activity relationship.'


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9084(4)
_cell_length_b                   9.1330(5)
_cell_length_c                   10.9770(4)
_cell_angle_alpha                87.642(4)
_cell_angle_beta                 83.261(4)
_cell_angle_gamma                88.355(4)
_cell_volume                     687.02(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6952
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      33.07

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_reflns_number            22068
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.857
_diffrn_reflns_theta_max         34.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5815
_reflns_number_gt                3551
_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       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.0812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5815
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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
S1 S 0.68227(6) 0.78979(4) 0.77881(3) 0.06022(13) Uani 1 1 d . . . . .
O1 O 0.82895(17) 0.85156(11) 0.24725(8) 0.0597(3) Uani 1 1 d . . . . .
O3 O 0.61427(17) 0.17141(11) 0.94277(10) 0.0645(3) Uani 1 1 d . . . . .
O2 O 0.81791(18) 0.58096(10) 0.35626(9) 0.0649(3) Uani 1 1 d . . . . .
C7 C 0.77233(16) 0.96688(11) 0.43666(10) 0.0376(2) Uani 1 1 d . . . . .
C2 C 0.73449(15) 0.94671(11) 0.56387(10) 0.0371(2) Uani 1 1 d . . . . .
C14 C 0.6448(2) 0.31221(13) 0.90093(10) 0.0480(3) Uani 1 1 d . . . . .
C16 C 0.4967(2) 0.52941(15) 0.82250(11) 0.0503(3) Uani 1 1 d . . . . .
H16 H 0.3877 0.5789 0.7975 0.060 Uiso 1 1 calc R U . . .
C8 C 0.80060(17) 0.83999(12) 0.35747(10) 0.0415(2) Uani 1 1 d . . . . .
C10 C 0.75497(18) 0.67732(12) 0.55156(11) 0.0443(2) Uani 1 1 d . . . . .
H10 H 0.7497 0.5853 0.5911 0.053 Uiso 1 1 calc R U . . .
C1 C 0.72746(17) 0.79707(12) 0.61924(10) 0.0398(2) Uani 1 1 d . . . . .
C9 C 0.79229(18) 0.68718(12) 0.41991(11) 0.0438(2) Uani 1 1 d . . . . .
C15 C 0.4837(2) 0.38581(15) 0.86349(12) 0.0507(3) Uani 1 1 d . . . . .
H15 H 0.3662 0.3380 0.8660 0.061 Uiso 1 1 calc R U . . .
C6 C 0.78294(18) 1.10694(13) 0.38310(12) 0.0458(3) Uani 1 1 d . . . . .
H6 H 0.8081 1.1193 0.2983 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6715(2) 0.60100(14) 0.81814(11) 0.0489(3) Uani 1 1 d . . . . .
C13 C 0.8209(2) 0.38050(16) 0.89355(13) 0.0557(3) Uani 1 1 d . . . . .
H13 H 0.9306 0.3299 0.9162 0.067 Uiso 1 1 calc R U . . .
C3 C 0.70571(19) 1.07034(13) 0.63436(12) 0.0463(3) Uani 1 1 d . . . . .
H3 H 0.6785 1.0595 0.7192 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8329(2) 0.52539(16) 0.85197(13) 0.0559(3) Uani 1 1 d . . . . .
H12 H 0.9515 0.5722 0.8468 0.067 Uiso 1 1 calc R U . . .
C4 C 0.7173(2) 1.20896(13) 0.57940(13) 0.0518(3) Uani 1 1 d . . . . .
H4 H 0.6982 1.2906 0.6277 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7565(2) 1.22800(13) 0.45453(13) 0.0515(3) Uani 1 1 d . . . . .
H5 H 0.7651 1.3218 0.4184 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7676(3) 0.09423(19) 0.99372(17) 0.0782(5) Uani 1 1 d . . . . .
H17A H 0.8752 0.0807 0.9311 0.117 Uiso 1 1 calc R U . . .
H17B H 0.7230 0.0004 1.0263 0.117 Uiso 1 1 calc R U . . .
H17C H 0.8088 0.1492 1.0584 0.117 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
S1 C1 1.7417(11) . ?
S1 C11 1.7617(13) . ?
O1 C8 1.2035(14) . ?
O3 C14 1.3613(15) . ?
O3 C17 1.413(2) . ?
O2 C9 1.2155(14) . ?
C7 C6 1.3859(15) . ?
C7 C2 1.3958(15) . ?
C7 C8 1.4720(15) . ?
C2 C3 1.3914(15) . ?
C2 C1 1.4723(15) . ?
C14 C13 1.375(2) . ?
C14 C15 1.3785(19) . ?
C16 C15 1.3709(18) . ?
C16 C11 1.3848(19) . ?
C16 H16 0.9300 . ?
C8 C9 1.5289(16) . ?
C10 C1 1.3439(16) . ?
C10 C9 1.4374(16) . ?
C10 H10 0.9300 . ?
C15 H15 0.9300 . ?
C6 C5 1.3772(18) . ?
C6 H6 0.9300 . ?
C11 C12 1.375(2) . ?
C13 C12 1.384(2) . ?
C13 H13 0.9300 . ?
C3 C4 1.3801(17) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 S1 C11 104.21(5) . . ?
C14 O3 C17 118.09(13) . . ?
C6 C7 C2 120.37(10) . . ?
C6 C7 C8 119.06(10) . . ?
C2 C7 C8 120.57(9) . . ?
C3 C2 C7 118.26(10) . . ?
C3 C2 C1 122.17(10) . . ?
C7 C2 C1 119.56(9) . . ?
O3 C14 C13 124.51(13) . . ?
O3 C14 C15 115.13(12) . . ?
C13 C14 C15 120.36(12) . . ?
C15 C16 C11 120.20(13) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O1 C8 C7 123.12(11) . . ?
O1 C8 C9 119.27(10) . . ?
C7 C8 C9 117.62(9) . . ?
C1 C10 C9 122.02(10) . . ?
C1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C1 C2 122.40(10) . . ?
C10 C1 S1 123.42(9) . . ?
C2 C1 S1 114.18(8) . . ?
O2 C9 C10 123.53(11) . . ?
O2 C9 C8 118.66(11) . . ?
C10 C9 C8 117.81(10) . . ?
C16 C15 C14 120.07(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C5 C6 C7 120.52(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C12 C11 C16 119.32(12) . . ?
C12 C11 S1 120.49(11) . . ?
C16 C11 S1 120.07(11) . . ?
C14 C13 C12 119.22(13) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C4 C3 C2 120.54(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C11 C12 C13 120.77(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C5 C4 C3 120.89(11) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.41(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.040

