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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tangj_0726_3
_database_code_depnum_ccdc_archive 'CCDC 1513110'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 O2'
_chemical_formula_sum            'C13 H8 O2'
_chemical_formula_weight         196.19
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.8942(4)
_cell_length_b                   13.6964(10)
_cell_length_c                   14.1713(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     949.95(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    557
_cell_measurement_temperature    294.44(10)
_cell_measurement_theta_max      19.8040
_cell_measurement_theta_min      4.1340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3701
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.010
_diffrn_reflns_theta_min         4.138
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   36.05   1.9500   12.5000
omega____ theta____ kappa____ phi______ frames
    -       23.1773    0.0000   90.0000 19

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   61.95   1.9500   12.5000
omega____ theta____ kappa____ phi______ frames
    -       23.1773  -99.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   46.85   1.9500   12.5000
omega____ theta____ kappa____ phi______ frames
    -       23.1773  -57.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -56.00   1.9500   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.9586  178.0000  -90.0000 20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0219918000
_diffrn_orient_matrix_UB_12      0.0456426000
_diffrn_orient_matrix_UB_13      -0.0223488000
_diffrn_orient_matrix_UB_21      0.1371853000
_diffrn_orient_matrix_UB_22      -0.0000270000
_diffrn_orient_matrix_UB_23      0.0160808000
_diffrn_orient_matrix_UB_31      0.0409143000
_diffrn_orient_matrix_UB_32      -0.0244767000
_diffrn_orient_matrix_UB_33      -0.0418314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1022
_reflns_number_total             1847
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1038(7) 0.4182(2) 0.2692(2) 0.0888(12) Uani 1 1 d . . . . .
O2 O 0.0198(6) 0.5960(2) 0.0395(2) 0.0607(9) Uani 1 1 d . . . . .
C1 C 0.0868(9) 0.4698(3) 0.1983(3) 0.0587(12) Uani 1 1 d . . . . .
C2 C 0.2471(9) 0.5596(3) 0.1864(3) 0.0528(12) Uani 1 1 d . . . . .
C3 C 0.4476(10) 0.5877(4) 0.2518(3) 0.0723(14) Uani 1 1 d . . . . .
H3 H 0.4830 0.5487 0.3041 0.087 Uiso 1 1 calc R . . . .
C4 C 0.5925(11) 0.6732(5) 0.2388(4) 0.0840(17) Uani 1 1 d . . . . .
H4 H 0.7242 0.6919 0.2825 0.101 Uiso 1 1 calc R . . . .
C5 C 0.5415(11) 0.7310(4) 0.1607(5) 0.0862(18) Uani 1 1 d . . . . .
H5 H 0.6389 0.7886 0.1523 0.103 Uiso 1 1 calc R . . . .
C6 C 0.3511(11) 0.7043(3) 0.0962(4) 0.0712(15) Uani 1 1 d . . . . .
H6 H 0.3176 0.7436 0.0439 0.085 Uiso 1 1 calc R . . . .
C7 C 0.2060(9) 0.6180(3) 0.1087(3) 0.0528(12) Uani 1 1 d . . . . .
C8 C -0.1294(9) 0.5107(3) 0.0460(3) 0.0505(11) Uani 1 1 d . . . . .
C9 C -0.3134(10) 0.4933(4) -0.0268(3) 0.0692(14) Uani 1 1 d . . . . .
H9 H -0.3325 0.5373 -0.0763 0.083 Uiso 1 1 calc R . . . .
C10 C -0.4661(11) 0.4094(4) -0.0235(4) 0.0828(16) Uani 1 1 d . . . . .
H10 H -0.5890 0.3960 -0.0718 0.099 Uiso 1 1 calc R . . . .
C11 C -0.4398(11) 0.3443(4) 0.0508(5) 0.0871(18) Uani 1 1 d . . . . .
H11 H -0.5462 0.2881 0.0523 0.105 Uiso 1 1 calc R . . . .
C12 C -0.2582(10) 0.3625(4) 0.1219(4) 0.0723(15) Uani 1 1 d . . . . .
H12 H -0.2400 0.3180 0.1711 0.087 Uiso 1 1 calc R . . . .
C13 C -0.1000(9) 0.4471(3) 0.1213(3) 0.0515(11) 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
O1 C1 1.230(5) . ?
O2 C7 1.373(5) . ?
O2 C8 1.380(5) . ?
C1 C2 1.469(5) . ?
C1 C13 1.457(6) . ?
C2 C3 1.403(6) . ?
C2 C7 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.355(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(6) . ?
C8 C9 1.389(6) . ?
C8 C13 1.385(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(5) . ?

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
C7 O2 C8 119.3(3) . . ?
O1 C1 C2 122.6(5) . . ?
O1 C1 C13 122.1(5) . . ?
C13 C1 C2 115.3(4) . . ?
C3 C2 C1 121.8(4) . . ?
C7 C2 C1 120.0(4) . . ?
C7 C2 C3 118.1(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
O2 C7 C2 122.8(4) . . ?
O2 C7 C6 115.8(4) . . ?
C2 C7 C6 121.4(5) . . ?
O2 C8 C9 116.0(4) . . ?
O2 C8 C13 121.9(4) . . ?
C13 C8 C9 122.1(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.1(5) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(5) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(5) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C1 120.6(4) . . ?
C8 C13 C12 118.0(4) . . ?
C12 C13 C1 121.4(4) . . ?

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
O1 C1 C2 C3 5.6(6) . . . . ?
O1 C1 C2 C7 -175.5(4) . . . . ?
O1 C1 C13 C8 175.0(4) . . . . ?
O1 C1 C13 C12 -3.7(7) . . . . ?
O2 C8 C9 C10 179.9(4) . . . . ?
O2 C8 C13 C1 1.6(6) . . . . ?
O2 C8 C13 C12 -179.7(4) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
C1 C2 C7 O2 -0.5(6) . . . . ?
C1 C2 C7 C6 178.9(4) . . . . ?
C2 C1 C13 C8 -3.5(6) . . . . ?
C2 C1 C13 C12 177.9(4) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C2 C7 O2 178.4(3) . . . . ?
C3 C2 C7 C6 -2.2(6) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C4 C5 C6 C7 -0.1(8) . . . . ?
C5 C6 C7 O2 -179.2(4) . . . . ?
C5 C6 C7 C2 1.4(7) . . . . ?
C7 O2 C8 C9 -179.9(3) . . . . ?
C7 O2 C8 C13 1.0(5) . . . . ?
C7 C2 C3 C4 1.7(6) . . . . ?
C8 O2 C7 C2 -1.6(5) . . . . ?
C8 O2 C7 C6 179.0(4) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
C9 C8 C13 C1 -177.4(4) . . . . ?
C9 C8 C13 C12 1.2(6) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C11 C12 C13 C1 177.5(4) . . . . ?
C11 C12 C13 C8 -1.2(6) . . . . ?
C13 C1 C2 C3 -176.0(4) . . . . ?
C13 C1 C2 C7 2.9(5) . . . . ?
C13 C8 C9 C10 -1.0(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-26
_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_tangj_0727
_database_code_depnum_ccdc_archive 'CCDC 1513109'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_audit_creation_date             2016-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 O'
_chemical_formula_sum            'C13 H8 O'
_chemical_formula_weight         180.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.0871(8)
_cell_length_b                   12.5495(6)
_cell_length_c                   18.6772(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3770.6(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1162
_cell_measurement_temperature    294.44(10)
_cell_measurement_theta_max      22.0690
_cell_measurement_theta_min      3.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10191
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   98.10   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   50.00   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000 -120.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0356690000
_diffrn_orient_matrix_UB_12      0.0266168000
_diffrn_orient_matrix_UB_13      0.0133440000
_diffrn_orient_matrix_UB_21      0.0075060000
_diffrn_orient_matrix_UB_22      -0.0216699000
_diffrn_orient_matrix_UB_23      0.0344867000
_diffrn_orient_matrix_UB_31      0.0247765000
_diffrn_orient_matrix_UB_32      0.0448989000
_diffrn_orient_matrix_UB_33      0.0087329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1810
_reflns_number_total             3702
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.3805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1972
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06369(15) 0.29606(18) 0.36590(13) 0.0875(8) Uani 1 1 d . . . . .
C1 C 0.01128(18) 0.1323(2) 0.34266(17) 0.0595(8) Uani 1 1 d . . . . .
C2 C -0.0030(2) 0.1075(3) 0.27187(18) 0.0758(10) Uani 1 1 d . . . . .
H2 H -0.0364 0.1506 0.2433 0.091 Uiso 1 1 calc R . . . .
C3 C 0.0342(2) 0.0163(3) 0.2445(2) 0.0865(11) Uani 1 1 d . . . . .
H3 H 0.0257 -0.0020 0.1968 0.104 Uiso 1 1 calc R . . . .
C4 C 0.0831(2) -0.0469(3) 0.2869(2) 0.0854(11) Uani 1 1 d . . . . .
H4 H 0.1075 -0.1074 0.2673 0.103 Uiso 1 1 calc R . . . .
C5 C 0.0969(2) -0.0227(2) 0.35839(19) 0.0729(9) Uani 1 1 d . . . . .
H5 H 0.1298 -0.0665 0.3868 0.088 Uiso 1 1 calc R . . . .
C6 C 0.06073(17) 0.0682(2) 0.38636(16) 0.0552(7) Uani 1 1 d . . . . .
C7 C 0.06340(17) 0.1150(2) 0.45899(16) 0.0559(8) Uani 1 1 d . . . . .
C8 C 0.01610(18) 0.2080(2) 0.45910(16) 0.0584(8) Uani 1 1 d . . . . .
C9 C -0.01907(19) 0.2237(2) 0.38623(17) 0.0630(8) Uani 1 1 d . . . . .
C10 C 0.1028(2) 0.0822(3) 0.52035(17) 0.0707(9) Uani 1 1 d . . . . .
H10 H 0.1348 0.0205 0.5207 0.085 Uiso 1 1 calc R . . . .
C11 C 0.0937(2) 0.1428(3) 0.58168(19) 0.0830(11) Uani 1 1 d . . . . .
H11 H 0.1197 0.1210 0.6237 0.100 Uiso 1 1 calc R . . . .
C12 C 0.0472(2) 0.2344(3) 0.5820(2) 0.0830(11) Uani 1 1 d . . . . .
H12 H 0.0421 0.2737 0.6240 0.100 Uiso 1 1 calc R . . . .
C13 C 0.0077(2) 0.2688(3) 0.52044(19) 0.0735(10) Uani 1 1 d . . . . .
H13 H -0.0236 0.3311 0.5203 0.088 Uiso 1 1 calc R . . . .
O2 O 0.08787(16) 0.51902(18) 0.40665(13) 0.0914(8) Uani 1 1 d . . . . .
C14 C 0.17145(18) 0.3656(2) 0.37558(17) 0.0616(8) Uani 1 1 d . . . . .
C15 C 0.1560(2) 0.3437(3) 0.30480(18) 0.0789(10) Uani 1 1 d . . . . .
H15 H 0.1190 0.3854 0.2787 0.095 Uiso 1 1 calc R . . . .
C16 C 0.1964(2) 0.2586(3) 0.2729(2) 0.0891(11) Uani 1 1 d . . . . .
H16 H 0.1866 0.2424 0.2250 0.107 Uiso 1 1 calc R . . . .
C17 C 0.2511(2) 0.1980(3) 0.3121(2) 0.0902(11) Uani 1 1 d . . . . .
H17 H 0.2777 0.1409 0.2901 0.108 Uiso 1 1 calc R . . . .
C18 C 0.2679(2) 0.2196(2) 0.38361(19) 0.0748(9) Uani 1 1 d . . . . .
H18 H 0.3055 0.1784 0.4093 0.090 Uiso 1 1 calc R . . . .
C19 C 0.22692(18) 0.3041(2) 0.41556(17) 0.0586(8) Uani 1 1 d . . . . .
C20 C 0.23123(18) 0.3476(2) 0.48888(16) 0.0589(8) Uani 1 1 d . . . . .
C21 C 0.17782(19) 0.4343(2) 0.49374(16) 0.0602(8) Uani 1 1 d . . . . .
C22 C 0.1373(2) 0.4501(2) 0.42297(18) 0.0665(9) Uani 1 1 d . . . . .
C23 C 0.2769(2) 0.3159(3) 0.54762(18) 0.0729(9) Uani 1 1 d . . . . .
H23 H 0.3124 0.2575 0.5450 0.087 Uiso 1 1 calc R . . . .
C24 C 0.2689(2) 0.3729(3) 0.61043(19) 0.0837(11) Uani 1 1 d . . . . .
H24 H 0.2999 0.3529 0.6503 0.100 Uiso 1 1 calc R . . . .
C25 C 0.2157(2) 0.4588(3) 0.61531(19) 0.0836(10) Uani 1 1 d . . . . .
H25 H 0.2115 0.4960 0.6582 0.100 Uiso 1 1 calc R . . . .
C26 C 0.1685(2) 0.4902(3) 0.55676(18) 0.0741(9) Uani 1 1 d . . . . .
H26 H 0.1317 0.5472 0.5600 0.089 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
O1 C9 1.218(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.394(4) . ?
C1 C9 1.489(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 C7 1.479(4) . ?
C7 C8 1.394(4) . ?
C7 C10 1.373(4) . ?
C8 C9 1.487(4) . ?
C8 C13 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9300 . ?
O2 C22 1.214(3) . ?
C14 C15 1.373(4) . ?
C14 C19 1.396(4) . ?
C14 C22 1.487(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 C20 1.476(4) . ?
C20 C21 1.390(4) . ?
C20 C23 1.379(4) . ?
C21 C22 1.487(4) . ?
C21 C26 1.378(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(5) . ?
C26 H26 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
C2 C1 C6 121.8(3) . . ?
C2 C1 C9 130.1(3) . . ?
C6 C1 C9 108.1(3) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.9(3) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 109.0(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 131.4(3) . . ?
C8 C7 C6 108.5(3) . . ?
C10 C7 C6 131.3(3) . . ?
C10 C7 C8 120.1(3) . . ?
C7 C8 C9 108.5(3) . . ?
C13 C8 C7 121.1(3) . . ?
C13 C8 C9 130.4(3) . . ?
O1 C9 C1 126.7(3) . . ?
O1 C9 C8 127.4(3) . . ?
C8 C9 C1 105.9(3) . . ?
C7 C10 H10 120.7 . . ?
C7 C10 C11 118.5(3) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.9 . . ?
C12 C13 C8 118.2(3) . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C19 121.3(3) . . ?
C15 C14 C22 130.5(3) . . ?
C19 C14 C22 108.2(3) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 121.9(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.9 . . ?
C19 C18 C17 118.2(3) . . ?
C19 C18 H18 120.9 . . ?
C14 C19 C20 108.8(3) . . ?
C18 C19 C14 119.8(3) . . ?
C18 C19 C20 131.4(3) . . ?
C21 C20 C19 108.7(3) . . ?
C23 C20 C19 131.0(3) . . ?
C23 C20 C21 120.2(3) . . ?
C20 C21 C22 108.5(3) . . ?
C26 C21 C20 121.4(3) . . ?
C26 C21 C22 130.1(3) . . ?
O2 C22 C14 126.9(3) . . ?
O2 C22 C21 127.2(3) . . ?
C14 C22 C21 105.8(3) . . ?
C20 C23 H23 120.7 . . ?
C20 C23 C24 118.5(3) . . ?
C24 C23 H23 120.7 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 117.9(3) . . ?
C21 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?

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
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 C7 C8 -0.5(3) . . . . ?
C1 C6 C7 C10 179.7(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 C6 C7 -179.5(3) . . . . ?
C2 C1 C9 O1 -0.2(5) . . . . ?
C2 C1 C9 C8 179.7(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 179.9(3) . . . . ?
C5 C6 C7 C10 0.1(5) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C6 C1 C9 O1 179.8(3) . . . . ?
C6 C1 C9 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C13 -179.9(3) . . . . ?
C6 C7 C10 C11 -179.7(3) . . . . ?
C7 C8 C9 O1 179.8(3) . . . . ?
C7 C8 C9 C1 0.0(3) . . . . ?
C7 C8 C13 C12 -0.4(5) . . . . ?
C7 C10 C11 C12 -0.5(5) . . . . ?
C8 C7 C10 C11 0.5(5) . . . . ?
C9 C1 C2 C3 179.6(3) . . . . ?
C9 C1 C6 C5 -179.9(3) . . . . ?
C9 C1 C6 C7 0.5(3) . . . . ?
C9 C8 C13 C12 179.3(3) . . . . ?
C10 C7 C8 C9 -179.9(3) . . . . ?
C10 C7 C8 C13 -0.1(4) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
C13 C8 C9 O1 0.1(5) . . . . ?
C13 C8 C9 C1 -179.8(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C14 C19 C20 C21 0.7(3) . . . . ?
C14 C19 C20 C23 -179.5(3) . . . . ?
C15 C14 C19 C18 0.4(4) . . . . ?
C15 C14 C19 C20 179.2(3) . . . . ?
C15 C14 C22 O2 -0.8(6) . . . . ?
C15 C14 C22 C21 -179.5(3) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C14 -0.8(5) . . . . ?
C17 C18 C19 C20 -179.4(3) . . . . ?
C18 C19 C20 C21 179.4(3) . . . . ?
C18 C19 C20 C23 -0.8(5) . . . . ?
C19 C14 C15 C16 0.2(5) . . . . ?
C19 C14 C22 O2 179.3(3) . . . . ?
C19 C14 C22 C21 0.7(3) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C19 C20 C21 C26 179.3(3) . . . . ?
C19 C20 C23 C24 179.6(3) . . . . ?
C20 C21 C22 O2 -178.8(3) . . . . ?
C20 C21 C22 C14 -0.2(3) . . . . ?
C20 C21 C26 C25 1.5(5) . . . . ?
C20 C23 C24 C25 0.8(5) . . . . ?
C21 C20 C23 C24 -0.7(5) . . . . ?
C22 C14 C15 C16 -179.7(3) . . . . ?
C22 C14 C19 C18 -179.7(3) . . . . ?
C22 C14 C19 C20 -0.8(3) . . . . ?
C22 C21 C26 C25 -179.0(3) . . . . ?
C23 C20 C21 C22 179.9(3) . . . . ?
C23 C20 C21 C26 -0.5(5) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C24 C25 C26 C21 -1.3(5) . . . . ?
C26 C21 C22 O2 1.6(6) . . . . ?
C26 C21 C22 C14 -179.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-27
_olex2_submission_special_instructions 'No special instructions were received'
