# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_180524b
_database_code_depnum_ccdc_archive 'CCDC 1845186'
loop_
_audit_author_name
_audit_author_address
'Qi Teng'
;Shandong University
China
;
_audit_update_record             
;
2018-05-24 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2170(2)
_cell_length_b                   7.7716(2)
_cell_length_c                   13.2349(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.843(2)
_cell_angle_gamma                90
_cell_volume                     845.08(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5790
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.3940
_cell_measurement_theta_min      5.3600
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7597
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         5.384
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -40.00   1.00    0.10    --  -48.45 -43.00  77.00   34
  2  ω   -115.00 -83.00   1.00    0.10    --  -48.45 -43.00  77.00   32
  3  ω    -49.00   1.00   1.00    0.10    --  -48.45  43.00-131.00   50
  4  ω   -155.00 -73.00   1.00    0.10    --  -86.25 -43.00  77.00   82
  5  ω    -81.00 -56.00   1.00    0.10    --  -86.25  43.00-131.00   25
  6  ω     94.00 125.00   1.00    0.10    --  107.75  43.00-131.00   31
  7  ω     37.00 119.00   1.00    0.10    --  107.75 -43.00  77.00   82
  8  ω    131.00 161.00   1.00    0.10    --  107.75  43.00-131.00   30
  9  ω   -115.00 -89.00   1.00    0.10    --  -48.45-125.00-150.00   26
 10  ω   -120.00 -27.00   1.00    0.10    --  -48.45 -77.00   0.00   93
 11  ω     -8.00  25.00   1.00    0.10    --   48.45 -43.00  77.00   33
 12  ω     41.00  68.00   1.00    0.10    --   48.45  43.00-131.00   27
 13  ω   -145.00-105.00   1.00    0.10    --  -86.25 -77.00  30.00   40
 14  ω    -94.00 -64.00   1.00    0.10    --  -86.25 -77.00  30.00   30
 15  ω   -151.00-106.00   1.00    0.10    --  -86.25 -77.00 -30.00   45
 16  ω    -98.00 -14.00   1.00    0.10    --  -86.25  57.00  60.00   84
 17  ω   -139.00 -64.00   1.00    0.10    --  -86.25 -77.00   0.00   75
 18  ω   -103.00 -64.00   1.00    0.10    --  -86.25 -77.00 -30.00   39
 19  ω   -127.00 -71.00   1.00    0.10    --  -86.25 -69.00 -51.84   56
 20  ω     75.00 109.00   1.00    0.10    --  107.75 -99.00 -90.00   34
 21  ω     39.00  64.00   1.00    0.10    --  107.75 -99.00 -90.00   25
 22  ω     94.00 165.00   1.00    0.10    --  107.75  57.00 -60.00   71
 23  ω     35.00  72.00   1.00    0.10    --  107.75 -37.00-120.00   37
 24  ω     33.00 116.00   1.00    0.10    --  107.75 -19.00-120.00   83
 25  ω    144.00 177.00   1.00    0.10    --  107.75  77.00   0.00   33
 26  ω     85.00 139.00   1.00    0.10    --  107.75  77.00   0.00   54
 27  ω     80.00 105.00   1.00    0.10    --  107.75 -37.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1635935000
_diffrn_orient_matrix_UB_12      0.0954745000
_diffrn_orient_matrix_UB_13      0.0081027000
_diffrn_orient_matrix_UB_21      -0.0083594000
_diffrn_orient_matrix_UB_22      -0.0490688000
_diffrn_orient_matrix_UB_23      0.1125816000
_diffrn_orient_matrix_UB_31      0.0911354000
_diffrn_orient_matrix_UB_32      0.1667225000
_diffrn_orient_matrix_UB_33      0.0284845000
_diffrn_oxdiff_ac3_digest_frames 
;
01a97c5b6ba7fcd4e197ed9a279689ed05012769872
;
_diffrn_oxdiff_ac3_digest_hkl    
;
014ae1318d0c73ec81b3d262e2c60dc4c685a2
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2783
_reflns_number_total             2960
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.25(17)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.058
_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)+(0.0704P)²+0.1237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1187
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.08) H1B(0.08) H1C(0.08) H3(0.047) H4(0.051) H6A(0.041)
 H6B(0.041) H7(0.036) H9A(0.045) H9B(0.045) H10(0.04) H14(0.045) H15(0.044)
 H18(0.041) H19(0.051) H20(0.055) H21(0.055) H22(0.047)
 Fixed X: H1A(0.5719) H1B(0.5535) H1C(0.6244) H3(0.4044) H4(0.2098)
 H6A(0.0764) H6B(0.2521) H7(0.2876) H9A(0.1864) H9B(0.1561) H10(-0.0796) H14(-
 0.0264) H15(-0.1469) H18(-0.4432) H19(-0.6901) H20(-0.809) H21(-0.6594) H22(-
 0.3924)
 Fixed Y: H1A(-0.7179) H1B(-0.5175) H1C(-0.6013) H3(-0.4714) H4(-0.2804) H6A(-
 0.5046) H6B(-0.4264) H7(-0.7145) H9A(-0.9475) H9B(-0.7628) H10(-0.899) H14(-
 0.5967) H15(-0.5326) H18(-0.8075) H19(-0.8046) H20(-0.741) H21(-0.608) H22(-
 0.5379)
 Fixed Z: H1A(-0.7895) H1B(-0.7824) H1C(-0.88) H3(-1.0004) H4(-0.9792) H6A(-
 0.7164) H6B(-0.712) H7(-0.7359) H9A(-0.9563) H9B(-1.0024) H10(-0.8576) H14(-
 0.4779) H15(-0.3292) H18(-0.5832) H19(-0.4754) H20(-0.3251) H21(-0.1959) H22(-
 0.2181)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5473(4) -0.6150(6) -0.8268(3) 0.0532(9) Uani 1 1 d . . . . .
H1A H 0.5719 -0.7179 -0.7895 0.080 Uiso 1 1 calc GR . . . .
H1B H 0.5535 -0.5175 -0.7824 0.080 Uiso 1 1 calc GR . . . .
H1C H 0.6244 -0.6013 -0.8800 0.080 Uiso 1 1 calc GR . . . .
C2 C 0.3770(3) -0.6279(4) -0.8719(2) 0.0340(6) Uani 1 1 d . . . . .
C3 C 0.3414(4) -0.4806(5) -0.9428(2) 0.0395(7) Uani 1 1 d . . . . .
H3 H 0.4044 -0.4714 -1.0004 0.047 Uiso 1 1 calc R . . . .
C4 C 0.2269(4) -0.3631(4) -0.9293(2) 0.0421(7) Uani 1 1 d . . . . .
H4 H 0.2098 -0.2804 -0.9792 0.051 Uiso 1 1 calc R . . . .
C5 C 0.1267(4) -0.3583(4) -0.8395(2) 0.0385(7) Uani 1 1 d . . . . .
C6 C 0.1721(4) -0.4810(4) -0.7561(2) 0.0344(7) Uani 1 1 d . . . . .
H6A H 0.0764 -0.5046 -0.7164 0.041 Uiso 1 1 calc R . . . .
H6B H 0.2521 -0.4264 -0.7120 0.041 Uiso 1 1 calc R . . . .
C7 C 0.2418(3) -0.6521(4) -0.79397(19) 0.0299(6) Uani 1 1 d . . . . .
H7 H 0.2876 -0.7145 -0.7359 0.036 Uiso 1 1 calc R . . . .
C8 C 0.1233(3) -0.7696(4) -0.8486(2) 0.0305(6) Uani 1 1 d . . . . .
C9 C 0.2016(4) -0.8252(4) -0.9451(2) 0.0376(7) Uani 1 1 d . . . . .
H9A H 0.1864 -0.9475 -0.9563 0.045 Uiso 1 1 calc R . . . .
H9B H 0.1561 -0.7628 -1.0024 0.045 Uiso 1 1 calc R . . . .
C10 C -0.0200(3) -0.8259(4) -0.8155(2) 0.0330(6) Uani 1 1 d . . . . .
H10 H -0.0796 -0.8990 -0.8576 0.040 Uiso 1 1 calc R . . . .
C11 C -0.0883(3) -0.7825(4) -0.7208(2) 0.0347(6) Uani 1 1 d . . . . .
C12 C -0.1488(3) -0.7512(4) -0.6408(2) 0.0353(6) Uani 1 1 d . . . . .
C13 C -0.2244(3) -0.7110(4) -0.5472(2) 0.0333(6) Uani 1 1 d . . . . .
C14 C -0.1349(3) -0.6257(4) -0.4684(2) 0.0371(6) Uani 1 1 d . . . . .
H14 H -0.0264 -0.5967 -0.4779 0.045 Uiso 1 1 calc R . . . .
C15 C -0.2073(4) -0.5869(4) -0.3799(2) 0.0367(7) Uani 1 1 d . . . . .
H15 H -0.1469 -0.5326 -0.3292 0.044 Uiso 1 1 calc R . . . .
C16 C -0.3723(3) -0.6268(4) -0.3626(2) 0.0319(6) Uani 1 1 d . . . . .
C17 C -0.4632(3) -0.7112(4) -0.4407(2) 0.0319(6) Uani 1 1 d . . . . .
C18 C -0.3848(3) -0.7518(4) -0.5321(2) 0.0338(6) Uani 1 1 d . . . . .
H18 H -0.4432 -0.8075 -0.5832 0.041 Uiso 1 1 calc R . . . .
C19 C -0.6292(4) -0.7516(5) -0.4244(2) 0.0426(7) Uani 1 1 d . . . . .
H19 H -0.6901 -0.8046 -0.4754 0.051 Uiso 1 1 calc R . . . .
C20 C -0.7002(4) -0.7136(5) -0.3349(2) 0.0457(8) Uani 1 1 d . . . . .
H20 H -0.8090 -0.7410 -0.3251 0.055 Uiso 1 1 calc R . . . .
C21 C -0.6099(4) -0.6328(5) -0.2569(2) 0.0456(8) Uani 1 1 d . . . . .
H21 H -0.6594 -0.6080 -0.1959 0.055 Uiso 1 1 calc R . . . .
C22 C -0.4506(4) -0.5909(4) -0.2703(2) 0.0393(7) Uani 1 1 d . . . . .
H22 H -0.3924 -0.5379 -0.2181 0.047 Uiso 1 1 calc R . . . .
O1 O 0.3709(2) -0.7850(3) -0.93082(15) 0.0404(5) Uani 1 1 d . . . . .
O2 O 0.0150(3) -0.2555(3) -0.83113(18) 0.0541(7) 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
C1 C2 1.517(4) . ?
C2 C3 1.506(4) . ?
C2 C7 1.539(3) . ?
C2 O1 1.449(4) . ?
C3 C4 1.325(5) . ?
C4 C5 1.457(4) . ?
C5 C6 1.502(4) . ?
C5 O2 1.223(4) . ?
C6 C7 1.534(4) . ?
C7 C8 1.512(4) . ?
C8 C9 1.502(4) . ?
C8 C10 1.337(4) . ?
C9 O1 1.435(4) . ?
C10 C11 1.421(4) . ?
C11 C12 1.201(4) . ?
C12 C13 1.429(4) . ?
C13 C14 1.430(4) . ?
C13 C18 1.373(4) . ?
C14 C15 1.356(4) . ?
C15 C16 1.413(4) . ?
C16 C17 1.426(4) . ?
C16 C22 1.417(4) . ?
C17 C18 1.415(4) . ?
C17 C19 1.420(4) . ?
C19 C20 1.360(4) . ?
C20 C21 1.409(5) . ?
C21 C22 1.363(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
C1 C2 C7 114.5(2) . . ?
C3 C2 C1 111.4(3) . . ?
C3 C2 C7 112.0(2) . . ?
O1 C2 C1 107.0(3) . . ?
O1 C2 C3 107.5(2) . . ?
O1 C2 C7 103.8(2) . . ?
C4 C3 C2 124.9(3) . . ?
C3 C4 C5 122.6(3) . . ?
C4 C5 C6 116.5(3) . . ?
O2 C5 C4 121.6(3) . . ?
O2 C5 C6 121.8(3) . . ?
C5 C6 C7 113.6(2) . . ?
C6 C7 C2 112.9(2) . . ?
C8 C7 C2 102.7(2) . . ?
C8 C7 C6 116.1(2) . . ?
C9 C8 C7 107.4(2) . . ?
C10 C8 C7 127.2(2) . . ?
C10 C8 C9 125.1(3) . . ?
O1 C9 C8 104.6(2) . . ?
C8 C10 C11 125.0(3) . . ?
C12 C11 C10 177.7(3) . . ?
C11 C12 C13 178.3(3) . . ?
C12 C13 C14 120.5(2) . . ?
C18 C13 C12 120.4(3) . . ?
C18 C13 C14 119.1(3) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C16 121.7(3) . . ?
C15 C16 C17 118.5(3) . . ?
C15 C16 C22 123.0(3) . . ?
C22 C16 C17 118.4(2) . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 C19 122.1(3) . . ?
C19 C17 C16 119.1(3) . . ?
C13 C18 C17 121.5(3) . . ?
C20 C19 C17 120.6(3) . . ?
C19 C20 C21 120.4(3) . . ?
C22 C21 C20 120.5(3) . . ?
C21 C22 C16 120.9(3) . . ?
C9 O1 C2 106.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.909
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_180525a
_database_code_depnum_ccdc_archive 'CCDC 1847564'
loop_
_audit_author_name
_audit_author_address
'Qi Teng'
;Shandong University
China
;
_audit_update_record             
;
2018-06-06 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O2 S'
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8959(3)
_cell_length_b                   10.2141(4)
_cell_length_c                   19.1396(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1348.11(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.1970
_cell_measurement_theta_min      4.3410
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5263
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.908
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -35.00   1.00    0.11    --  -48.45 -77.00-164.00   83
  2  ω   -156.00 -94.00   1.00    0.70    --  -86.25 -53.00 -33.00   62
  3  ω     85.00 130.00   1.00    0.70    --  107.75 -77.00-164.00   45
  4  ω     35.00 106.00   1.00    0.70    --  107.75 -96.00 100.00   71
  5  ω     46.00 120.00   1.00    0.11    --   48.45  19.00  90.00   74
  6  ω     93.00 177.00   1.00    0.70    --  107.75 125.00 -30.00   84
  7  ω     38.00  71.00   1.00    0.70    --  107.75 -19.00-150.00   33
  8  ω     76.00 116.00   1.00    0.70    --  107.75 -19.00-150.00   40
  9  ω     95.00 175.00   1.00    0.70    --  107.75 125.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1825970000
_diffrn_orient_matrix_UB_12      0.0099451000
_diffrn_orient_matrix_UB_13      0.0460786000
_diffrn_orient_matrix_UB_21      0.0673778000
_diffrn_orient_matrix_UB_22      0.1352226000
_diffrn_orient_matrix_UB_23      0.0263045000
_diffrn_orient_matrix_UB_31      -0.1093349000
_diffrn_orient_matrix_UB_32      0.0663071000
_diffrn_orient_matrix_UB_33      -0.0605312000
_diffrn_oxdiff_ac3_digest_frames 
;
01f5cff7a8522e95e54da3877783e526b800572907f
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01df111c561538a5e1023adf1463007ac0e654
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2079
_reflns_number_total             2312
_reflns_odcompleteness_completeness 96.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.102
_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)+(0.1030P)²+0.8530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1821
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.0317(10) 0.1792(6) 0.6066(3) 0.0560(14) Uani 1 1 d . . . . .
H1 H 0.0219 0.1169 0.6418 0.067 Uiso 1 1 calc R . . . .
C2 C 0.0698(10) 0.1491(6) 0.5396(3) 0.0558(14) Uani 1 1 d . . . . .
H2 H 0.0932 0.0635 0.5253 0.067 Uiso 1 1 calc R . . . .
C3 C 0.0722(8) 0.2588(5) 0.4904(3) 0.0445(12) Uani 1 1 d . . . . .
H3 H 0.0902 0.2554 0.4423 0.053 Uiso 1 1 calc R . . . .
C4 C 0.0399(7) 0.3760(5) 0.5341(3) 0.0422(11) Uani 1 1 d . . . . .
C5 C 0.0308(9) 0.5068(5) 0.5097(3) 0.0496(13) Uani 1 1 d . . . . .
C6 C 0.0251(9) 0.6169(5) 0.4886(3) 0.0495(13) Uani 1 1 d . . . . .
C7 C 0.0069(9) 0.7507(5) 0.4674(3) 0.0474(11) Uani 1 1 d . . . . .
H7 H -0.0156 0.8124 0.5022 0.057 Uiso 1 1 calc R . . . .
C8 C 0.0195(7) 0.7939(4) 0.4022(3) 0.0377(10) Uani 1 1 d . . . . .
C9 C -0.0181(8) 0.9356(5) 0.3814(2) 0.0456(11) Uani 1 1 d . . . . .
H9A H -0.1295 0.9704 0.4061 0.055 Uiso 1 1 calc R . . . .
H9B H 0.0939 0.9899 0.3914 0.055 Uiso 1 1 calc R . . . .
C10 C 0.0526(7) 0.7181(4) 0.3351(3) 0.0372(10) Uani 1 1 d . . . . .
H10 H -0.0645 0.6671 0.3250 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2272(7) 0.6253(4) 0.3337(3) 0.0404(11) Uani 1 1 d . . . . .
H11A H 0.2218 0.5698 0.3748 0.048 Uiso 1 1 calc R . . . .
H11B H 0.2160 0.5691 0.2931 0.048 Uiso 1 1 calc R . . . .
C12 C 0.4197(7) 0.6909(5) 0.3318(3) 0.0427(11) Uani 1 1 d . . . . .
C13 C 0.0696(8) 0.8280(5) 0.2802(2) 0.0401(11) Uani 1 1 d . . . . .
C14 C -0.0053(11) 0.7922(6) 0.2086(3) 0.0611(15) Uani 1 1 d . . . . .
H14A H 0.0189 0.8630 0.1768 0.092 Uiso 1 1 calc GR . . . .
H14B H -0.1423 0.7759 0.2111 0.092 Uiso 1 1 calc GR . . . .
H14C H 0.0597 0.7149 0.1924 0.092 Uiso 1 1 calc GR . . . .
C15 C 0.2714(8) 0.8818(5) 0.2769(3) 0.0414(11) Uani 1 1 d . . . . .
H15 H 0.2879 0.9629 0.2557 0.050 Uiso 1 1 calc R . . . .
C16 C 0.4279(8) 0.8233(5) 0.3016(3) 0.0442(11) Uani 1 1 d . . . . .
H16 H 0.5462 0.8669 0.3000 0.053 Uiso 1 1 calc R . . . .
O1 O -0.0545(5) 0.9303(3) 0.30773(18) 0.0461(9) Uani 1 1 d . . . . .
O2 O 0.5670(6) 0.6355(5) 0.3507(3) 0.0756(15) Uani 1 1 d . . . . .
S1 S 0.0035(3) 0.33956(14) 0.62009(7) 0.0643(5) 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
C1 H1 0.9300 . ?
C1 C2 1.345(9) . ?
C1 S1 1.670(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.463(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.477(7) . ?
C4 C5 1.416(7) . ?
C4 S1 1.706(5) . ?
C5 C6 1.196(7) . ?
C6 C7 1.430(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.328(7) . ?
C8 C9 1.523(6) . ?
C8 C10 1.516(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 O1 1.433(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.533(6) . ?
C10 C13 1.543(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.487(7) . ?
C12 C16 1.471(7) . ?
C12 O2 1.218(7) . ?
C13 C14 1.509(7) . ?
C13 C15 1.497(8) . ?
C13 O1 1.450(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.322(8) . ?
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
C2 C1 H1 123.4 . . ?
C2 C1 S1 113.3(4) . . ?
S1 C1 H1 123.4 . . ?
C1 C2 H2 122.0 . . ?
C1 C2 C3 116.1(5) . . ?
C3 C2 H2 122.0 . . ?
C2 C3 H3 127.6 . . ?
C2 C3 C4 104.8(4) . . ?
C4 C3 H3 127.6 . . ?
C3 C4 S1 113.0(3) . . ?
C5 C4 C3 125.8(5) . . ?
C5 C4 S1 121.1(4) . . ?
C6 C5 C4 179.2(7) . . ?
C5 C6 C7 175.5(6) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 C6 125.3(5) . . ?
C8 C7 H7 117.3 . . ?
C7 C8 C9 123.4(5) . . ?
C7 C8 C10 129.5(4) . . ?
C10 C8 C9 106.9(4) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O1 C9 C8 104.5(4) . . ?
O1 C9 H9A 110.8 . . ?
O1 C9 H9B 110.8 . . ?
C8 C10 H10 108.4 . . ?
C8 C10 C11 116.7(4) . . ?
C8 C10 C13 102.5(3) . . ?
C11 C10 H10 108.4 . . ?
C11 C10 C13 112.2(4) . . ?
C13 C10 H10 108.4 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.0(4) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C16 C12 C11 117.3(4) . . ?
O2 C12 C11 121.9(5) . . ?
O2 C12 C16 120.7(5) . . ?
C14 C13 C10 114.6(4) . . ?
C15 C13 C10 111.5(4) . . ?
C15 C13 C14 111.6(5) . . ?
O1 C13 C10 103.4(4) . . ?
O1 C13 C14 107.6(4) . . ?
O1 C13 C15 107.4(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15 117.3 . . ?
C16 C15 C13 125.3(5) . . ?
C16 C15 H15 117.3 . . ?
C12 C16 H16 119.2 . . ?
C15 C16 C12 121.6(5) . . ?
C15 C16 H16 119.2 . . ?
C9 O1 C13 106.4(3) . . ?
C1 S1 C4 92.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.543
_oxdiff_exptl_absorpt_empirical_full_min 0.737
