# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_2013_06_26
_audit_creation_date             2013-06-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            2013_06_26
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H18 O2 S'
_chemical_formula_sum            'C20 H18 O2 S'
_chemical_formula_weight         322.40
_chemical_absolute_configuration ad
_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 0.0015 0.0009 '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 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'

_cell_length_a                   8.0288(16)
_cell_length_b                   9.2244(19)
_cell_length_c                   11.460(3)
_cell_angle_alpha                103.126(5)
_cell_angle_beta                 98.144(7)
_cell_angle_gamma                98.902(5)
_cell_volume                     802.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.93
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.7902.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36305
_diffrn_reflns_theta_full        21.95
_diffrn_reflns_theta_max         21.95
_diffrn_reflns_theta_min         1.46
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6054
_reflns_number_total             7505
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(17)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7505
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+1.4036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C24(H24A,H24B), C26(H26A,H26B), C32(H32A,H32B), C37(H37A,
 H37B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19),
 C21(H21), C23(H23), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C35(H35),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.30578(10) -0.70082(10) -0.88771(8) 0.0219(3) Uani 1 1 d . . .
S2 S 0.26395(10) -0.32112(11) -1.13888(8) 0.0211(2) Uani 1 1 d . . .
O1 O 0.2982(4) -0.4643(4) -1.2001(3) 0.0294(8) Uani 1 1 d . . .
O2 O -0.3351(4) -0.5571(4) -0.8231(3) 0.0302(9) Uani 1 1 d . . .
O3 O 0.3700(4) -0.2388(4) -1.0243(3) 0.0301(9) Uani 1 1 d . . .
O4 O -0.4189(4) -0.7807(4) -1.0014(3) 0.0293(8) Uani 1 1 d . . .
C5 C -0.3097(6) -1.0124(6) -0.6286(5) 0.0227(11) Uani 1 1 d . . .
C6 C -0.2985(5) -0.8226(6) -0.7902(4) 0.0209(11) Uani 1 1 d . . .
C7 C 0.2692(6) -0.2045(6) -1.2395(5) 0.0230(11) Uani 1 1 d . . .
C8 C -0.0950(6) -0.6732(6) -0.9160(5) 0.0244(11) Uani 1 1 d . . .
C9 C 0.2747(6) -0.0073(6) -1.3979(5) 0.0230(11) Uani 1 1 d . . .
C10 C -0.2973(6) -1.1102(6) -0.5432(5) 0.0244(11) Uani 1 1 d . . .
C11 C 0.3314(6) -0.0554(6) -1.1971(5) 0.0247(11) Uani 1 1 d . . .
H11 H 0.3709 -0.0136 -1.1121 0.030 Uiso 1 1 calc R . .
C12 C -0.3708(6) -1.0672(6) -0.7490(5) 0.0250(11) Uani 1 1 d . . .
H12 H -0.4069 -1.1736 -0.7823 0.030 Uiso 1 1 calc R . .
C13 C 0.0510(5) -0.3493(6) -1.1144(4) 0.0211(10) Uani 1 1 d . . .
C14 C -0.3821(6) -0.9653(6) -0.8287(5) 0.0259(12) Uani 1 1 d . . .
H14 H -0.4495 -1.0011 -0.9083 0.031 Uiso 1 1 calc R . .
C15 C 0.3394(6) 0.0426(6) -1.2785(5) 0.0256(12) Uani 1 1 d . . .
H15 H 0.3924 0.1463 -1.2463 0.031 Uiso 1 1 calc R . .
C16 C 0.2799(6) 0.0923(7) -1.4831(5) 0.0270(12) Uani 1 1 d . . .
C17 C -0.0071(7) -0.2309(7) -1.0442(6) 0.0344(13) Uani 1 1 d . . .
H17 H 0.0651 -0.1339 -1.0116 0.041 Uiso 1 1 calc R . .
C18 C 0.2497(7) 0.1304(9) -1.6860(6) 0.0439(16) Uani 1 1 d . . .
H18 H 0.2213 0.0892 -1.7717 0.053 Uiso 1 1 calc R . .
C19 C -0.0555(6) -0.4908(6) -1.1643(4) 0.0272(11) Uani 1 1 d . . .
H19 H -0.0145 -0.5698 -1.2140 0.033 Uiso 1 1 calc R . .
C20 C -0.1872(5) -0.7641(5) -0.6656(4) 0.0215(9) Uani 1 1 d . . .
H20A H -0.1763 -0.6528 -0.6379 0.026 Uiso 1 1 calc R . .
H20B H -0.0711 -0.7867 -0.6688 0.026 Uiso 1 1 calc R . .
C21 C 0.0138(6) -0.5360(6) -0.8632(5) 0.0299(12) Uani 1 1 d . . .
H21 H -0.0226 -0.4567 -0.8104 0.036 Uiso 1 1 calc R . .
C22 C 0.2337(7) 0.0318(8) -1.6095(6) 0.0376(14) Uani 1 1 d . . .
C23 C -0.0440(8) -0.7895(7) -0.9937(6) 0.0385(14) Uani 1 1 d . . .
H23 H -0.1212 -0.8832 -1.0302 0.046 Uiso 1 1 calc R . .
C24 C 0.2164(8) -0.2747(6) -1.3721(4) 0.0427(13) Uani 1 1 d . . .
H24A H 0.1101 -0.3514 -1.3853 0.051 Uiso 1 1 calc R . .
H24B H 0.3064 -0.3290 -1.3999 0.051 Uiso 1 1 calc R . .
C25 C -0.3168(6) -1.2674(6) -0.5857(5) 0.0325(11) Uani 1 1 d . . .
H25 H -0.3352 -1.3121 -0.6709 0.039 Uiso 1 1 calc R . .
C26 C 0.1956(7) -0.2294(6) -1.5789(4) 0.0444(12) Uani 1 1 d . . .
H26A H 0.1132 -0.3270 -1.6108 0.053 Uiso 1 1 calc R . .
H26B H 0.3120 -0.2512 -1.5826 0.053 Uiso 1 1 calc R . .
C27 C 0.1787(7) -0.5168(9) -0.8893(6) 0.0478(18) Uani 1 1 d . . .
H27 H 0.2559 -0.4228 -0.8540 0.057 Uiso 1 1 calc R . .
C28 C -0.2196(6) -0.5165(7) -1.1418(5) 0.0348(13) Uani 1 1 d . . .
H28 H -0.2917 -0.6135 -1.1744 0.042 Uiso 1 1 calc R . .
C29 C -0.2681(6) -0.8403(6) -0.5770(4) 0.0231(10) Uani 1 1 d . . .
H29 H -0.3786 -0.8053 -0.5683 0.028 Uiso 1 1 calc R . .
C30 C -0.2786(7) -0.4000(8) -1.0713(6) 0.0430(16) Uani 1 1 d . . .
H30 H -0.3921 -0.4172 -1.0558 0.052 Uiso 1 1 calc R . .
C31 C 0.2309(8) -0.6301(11) -0.9644(8) 0.062(2) Uani 1 1 d . . .
H31 H 0.3442 -0.6151 -0.9807 0.074 Uiso 1 1 calc R . .
C32 C 0.1607(9) -0.1303(9) -1.6604(6) 0.060(2) Uani 1 1 d . . .
H32A H 0.2058 -0.1659 -1.7356 0.073 Uiso 1 1 calc R . .
H32B H 0.0349 -0.1422 -1.6839 0.073 Uiso 1 1 calc R . .
C33 C -0.2667(6) -1.0462(7) -0.4178(5) 0.0289(12) Uani 1 1 d . . .
C35 C -0.3098(6) -1.3579(6) -0.5060(5) 0.0414(12) Uani 1 1 d . . .
H35 H -0.3229 -1.4645 -0.5364 0.050 Uiso 1 1 calc R . .
C36 C 0.1853(7) -0.1692(7) -1.4503(5) 0.0400(14) Uani 1 1 d . . .
H36 H 0.0612 -0.1648 -1.4527 0.048 Uiso 1 1 calc R . .
C37 C -0.2371(7) -0.8760(6) -0.3654(5) 0.0301(11) Uani 1 1 d . . .
H37A H -0.1615 -0.8476 -0.2843 0.036 Uiso 1 1 calc R . .
H37B H -0.3478 -0.8449 -0.3550 0.036 Uiso 1 1 calc R . .
C38 C -0.2615(7) -1.1409(7) -0.3382(5) 0.0363(13) Uani 1 1 d . . .
H38 H -0.2422 -1.0977 -0.2527 0.044 Uiso 1 1 calc R . .
C39 C -0.1742(8) -0.2581(8) -1.0228(7) 0.0470(17) Uani 1 1 d . . .
H39 H -0.2170 -0.1789 -0.9748 0.056 Uiso 1 1 calc R . .
C40 C 0.1202(10) -0.7675(10) -1.0175(7) 0.060(2) Uani 1 1 d . . .
H40 H 0.1574 -0.8465 -1.0702 0.072 Uiso 1 1 calc R . .
C41 C 0.3295(6) 0.2513(6) -1.4370(6) 0.0349(12) Uani 1 1 d . . .
H41 H 0.3556 0.2944 -1.3514 0.042 Uiso 1 1 calc R . .
C42 C -0.2838(7) -1.2949(7) -0.3820(5) 0.0436(14) Uani 1 1 d . . .
H42 H -0.2815 -1.3583 -0.3272 0.052 Uiso 1 1 calc R . .
C43 C -0.1541(5) -0.7946(5) -0.4510(4) 0.0255(9) Uani 1 1 d . . .
H43A H -0.1369 -0.6835 -0.4175 0.031 Uiso 1 1 calc R . .
H43B H -0.0405 -0.8214 -0.4577 0.031 Uiso 1 1 calc R . .
C1 C 0.3401(6) 0.3447(6) -1.5162(5) 0.0427(13) Uani 1 1 d . . .
H1 H 0.3721 0.4517 -1.4847 0.051 Uiso 1 1 calc R . .
C2 C 0.3040(6) 0.2817(8) -1.6421(6) 0.0460(15) Uani 1 1 d . . .
H2 H 0.3175 0.3448 -1.6964 0.055 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
S1 O2 1.435(4) . ?
S1 O4 1.445(4) . ?
S1 C6 1.757(5) . ?
S1 C8 1.759(5) . ?
S2 O1 1.434(4) . ?
S2 O3 1.434(4) . ?
S2 C7 1.747(5) . ?
S2 C13 1.761(4) . ?
C5 C10 1.478(8) . ?
C5 C12 1.347(7) . ?
C5 C29 1.528(7) . ?
C6 C14 1.325(7) . ?
C6 C20 1.506(6) . ?
C7 C11 1.339(7) . ?
C7 C24 1.481(7) . ?
C8 C21 1.375(8) . ?
C8 C23 1.384(7) . ?
C9 C15 1.339(7) . ?
C9 C16 1.485(8) . ?
C9 C36 1.498(8) . ?
C10 C25 1.397(7) . ?
C10 C33 1.394(8) . ?
C11 H11 0.9500 . ?
C11 C15 1.439(8) . ?
C12 H12 0.9500 . ?
C12 C14 1.455(7) . ?
C13 C17 1.387(7) . ?
C13 C19 1.393(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C22 1.402(8) . ?
C16 C41 1.412(8) . ?
C17 H17 0.9500 . ?
C17 C39 1.393(8) . ?
C18 H18 0.9500 . ?
C18 C22 1.403(8) . ?
C18 C2 1.349(10) . ?
C19 H19 0.9500 . ?
C19 C28 1.373(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C29 1.522(6) . ?
C21 H21 0.9500 . ?
C21 C27 1.392(7) . ?
C22 C32 1.468(10) . ?
C23 H23 0.9500 . ?
C23 C40 1.378(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C36 1.491(7) . ?
C25 H25 0.9500 . ?
C25 C35 1.371(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C32 1.476(9) . ?
C26 C36 1.472(7) . ?
C27 H27 0.9500 . ?
C27 C31 1.356(11) . ?
C28 H28 0.9500 . ?
C28 C30 1.379(9) . ?
C29 H29 1.0000 . ?
C29 C43 1.526(6) . ?
C30 H30 0.9500 . ?
C30 C39 1.387(10) . ?
C31 H31 0.9500 . ?
C31 C40 1.384(12) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C37 1.516(8) . ?
C33 C38 1.400(8) . ?
C35 H35 0.9500 . ?
C35 C42 1.381(8) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C43 1.529(7) . ?
C38 H38 0.9500 . ?
C38 C42 1.370(9) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C41 C1 1.389(7) . ?
C42 H42 0.9500 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C1 H1 0.9500 . ?
C1 C2 1.397(9) . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O4 118.8(2) . . ?
O2 S1 C6 109.6(2) . . ?
O2 S1 C8 107.8(2) . . ?
O4 S1 C6 108.9(2) . . ?
O4 S1 C8 107.9(2) . . ?
C6 S1 C8 102.5(2) . . ?
O1 S2 C7 107.7(2) . . ?
O1 S2 C13 108.5(2) . . ?
O3 S2 O1 119.1(2) . . ?
O3 S2 C7 108.6(2) . . ?
O3 S2 C13 107.0(2) . . ?
C7 S2 C13 105.2(2) . . ?
C10 C5 C29 118.7(5) . . ?
C12 C5 C10 123.1(5) . . ?
C12 C5 C29 118.0(5) . . ?
C14 C6 S1 120.3(4) . . ?
C14 C6 C20 121.0(5) . . ?
C20 C6 S1 118.6(4) . . ?
C11 C7 S2 120.0(4) . . ?
C11 C7 C24 120.9(5) . . ?
C24 C7 S2 119.0(4) . . ?
C21 C8 S1 119.5(4) . . ?
C21 C8 C23 121.5(5) . . ?
C23 C8 S1 118.9(4) . . ?
C15 C9 C16 123.1(5) . . ?
C15 C9 C36 119.9(5) . . ?
C16 C9 C36 116.9(5) . . ?
C25 C10 C5 121.1(5) . . ?
C33 C10 C5 120.1(5) . . ?
C33 C10 C25 118.8(5) . . ?
C7 C11 H11 119.5 . . ?
C7 C11 C15 121.0(5) . . ?
C15 C11 H11 119.5 . . ?
C5 C12 H12 119.7 . . ?
C5 C12 C14 120.7(5) . . ?
C14 C12 H12 119.7 . . ?
C17 C13 S2 119.5(4) . . ?
C17 C13 C19 121.1(4) . . ?
C19 C13 S2 119.5(4) . . ?
C6 C14 C12 120.1(5) . . ?
C6 C14 H14 120.0 . . ?
C12 C14 H14 120.0 . . ?
C9 C15 C11 122.3(5) . . ?
C9 C15 H15 118.8 . . ?
C11 C15 H15 118.8 . . ?
C22 C16 C9 121.2(5) . . ?
C22 C16 C41 118.8(6) . . ?
C41 C16 C9 120.0(5) . . ?
C13 C17 H17 120.9 . . ?
C13 C17 C39 118.2(5) . . ?
C39 C17 H17 120.9 . . ?
C22 C18 H18 118.8 . . ?
C2 C18 H18 118.8 . . ?
C2 C18 C22 122.4(6) . . ?
C13 C19 H19 119.9 . . ?
C28 C19 C13 120.2(5) . . ?
C28 C19 H19 119.9 . . ?
C6 C20 H20A 109.9 . . ?
C6 C20 H20B 109.9 . . ?
C6 C20 C29 109.0(4) . . ?
H20A C20 H20B 108.3 . . ?
C29 C20 H20A 109.9 . . ?
C29 C20 H20B 109.9 . . ?
C8 C21 H21 120.9 . . ?
C8 C21 C27 118.1(5) . . ?
C27 C21 H21 120.9 . . ?
C16 C22 C18 118.7(6) . . ?
C16 C22 C32 120.5(6) . . ?
C18 C22 C32 120.7(6) . . ?
C8 C23 H23 120.5 . . ?
C40 C23 C8 119.1(6) . . ?
C40 C23 H23 120.5 . . ?
C7 C24 H24A 108.2 . . ?
C7 C24 H24B 108.2 . . ?
C7 C24 C36 116.2(4) . . ?
H24A C24 H24B 107.4 . . ?
C36 C24 H24A 108.2 . . ?
C36 C24 H24B 108.2 . . ?
C10 C25 H25 119.6 . . ?
C35 C25 C10 120.8(5) . . ?
C35 C25 H25 119.6 . . ?
H26A C26 H26B 107.4 . . ?
C32 C26 H26A 108.3 . . ?
C32 C26 H26B 108.3 . . ?
C36 C26 H26A 108.3 . . ?
C36 C26 H26B 108.3 . . ?
C36 C26 C32 115.9(5) . . ?
C21 C27 H27 119.5 . . ?
C31 C27 C21 121.0(6) . . ?
C31 C27 H27 119.5 . . ?
C19 C28 H28 120.3 . . ?
C19 C28 C30 119.4(5) . . ?
C30 C28 H28 120.3 . . ?
C5 C29 H29 107.8 . . ?
C20 C29 C5 110.1(4) . . ?
C20 C29 H29 107.8 . . ?
C20 C29 C43 111.5(4) . . ?
C43 C29 C5 111.6(4) . . ?
C43 C29 H29 107.8 . . ?
C28 C30 H30 119.6 . . ?
C28 C30 C39 120.9(5) . . ?
C39 C30 H30 119.6 . . ?
C27 C31 H31 119.8 . . ?
C27 C31 C40 120.4(6) . . ?
C40 C31 H31 119.8 . . ?
C22 C32 C26 115.6(5) . . ?
C22 C32 H32A 108.4 . . ?
C22 C32 H32B 108.4 . . ?
C26 C32 H32A 108.4 . . ?
C26 C32 H32B 108.4 . . ?
H32A C32 H32B 107.4 . . ?
C10 C33 C37 121.5(5) . . ?
C10 C33 C38 119.4(5) . . ?
C38 C33 C37 119.1(5) . . ?
C25 C35 H35 119.8 . . ?
C25 C35 C42 120.4(5) . . ?
C42 C35 H35 119.8 . . ?
C9 C36 H36 103.7 . . ?
C24 C36 C9 115.7(4) . . ?
C24 C36 H36 103.7 . . ?
C26 C36 C9 113.9(5) . . ?
C26 C36 C24 114.1(5) . . ?
C26 C36 H36 103.7 . . ?
C33 C37 H37A 109.7 . . ?
C33 C37 H37B 109.7 . . ?
C33 C37 C43 109.7(4) . . ?
H37A C37 H37B 108.2 . . ?
C43 C37 H37A 109.7 . . ?
C43 C37 H37B 109.7 . . ?
C33 C38 H38 119.6 . . ?
C42 C38 C33 120.8(6) . . ?
C42 C38 H38 119.6 . . ?
C17 C39 H39 119.8 . . ?
C30 C39 C17 120.4(5) . . ?
C30 C39 H39 119.8 . . ?
C23 C40 C31 119.8(6) . . ?
C23 C40 H40 120.1 . . ?
C31 C40 H40 120.1 . . ?
C16 C41 H41 119.9 . . ?
C1 C41 C16 120.3(6) . . ?
C1 C41 H41 119.9 . . ?
C35 C42 H42 120.1 . . ?
C38 C42 C35 119.7(5) . . ?
C38 C42 H42 120.1 . . ?
C29 C43 C37 110.1(4) . . ?
C29 C43 H43A 109.6 . . ?
C29 C43 H43B 109.6 . . ?
C37 C43 H43A 109.6 . . ?
C37 C43 H43B 109.6 . . ?
H43A C43 H43B 108.2 . . ?
C41 C1 H1 120.0 . . ?
C41 C1 C2 120.1(5) . . ?
C2 C1 H1 120.0 . . ?
C18 C2 C1 119.5(6) . . ?
C18 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?

_database_code_depnum_ccdc_archive 'CCDC 971515'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2260
_audit_creation_date             2014-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H16 Cl N O2'
_chemical_formula_sum            'C20 H16 Cl N O2'
_chemical_formula_weight         337.79
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 N O2 Cl'
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'
Cl Cl 0.1484 0.1585 '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                   11.8439(4)
_cell_length_b                   11.8914(2)
_cell_length_c                   22.4284(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3158.84(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10048
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      30.4500
_cell_measurement_theta_min      1.8200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
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    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.4067
_exptl_crystal_size_mid          0.2282
_exptl_crystal_size_min          0.1761
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.078
_diffrn_reflns_theta_min         1.816
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803   19.0000  120.0000 188

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00   70.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803  -77.0000   30.0000 143

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00  119.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803   57.0000  -90.0000 134

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   37.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.7178 -123.0000   55.8240 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0145428000
_diffrn_orient_matrix_UB_12      -0.0537968000
_diffrn_orient_matrix_UB_13      0.0113045000
_diffrn_orient_matrix_UB_21      0.0083185000
_diffrn_orient_matrix_UB_22      -0.0197581000
_diffrn_orient_matrix_UB_23      -0.0295440000
_diffrn_orient_matrix_UB_31      0.0574303000
_diffrn_orient_matrix_UB_32      0.0164090000
_diffrn_orient_matrix_UB_33      0.0013630000
_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         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                7473
_reflns_number_total             10247
_reflns_odcompleteness_completeness 99.97
_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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 2467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         10247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1417
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(Cl3)=Sof(C4B)=Sof(H4B)=Sof(C3B)=Sof(H3B)=Sof(C6B)=Sof(C5B)=Sof(H5B)=
 Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(Cl1)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C4A)=Sof(H4A)=Sof(C2A)=Sof(H2A)=
 Sof(C3A)=Sof(H3A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C27(H27), C32(H32), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C14(H14A,H14B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C39(H39), C37(H37), C22(H22), C24(H24), C25(H25), C38(H38), C40(H40),
 C23(H23), C29(H29), C30(H30), C9(H9), C18(H18), C20(H20), C10(H10), C17(H17),
 C19(H19), C5A(H5A), C4A(H4A), C2A(H2A), C3A(H3A), C4B(H4B), C3B(H3B), C5B(H5B),
  C2B(H2B)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl2 Cl 0.71705(9) -0.00275(7) 0.71103(4) 0.0351(2) Uani 1 1 d . . . . .
O3 O 1.0129(2) 0.1285(2) 0.51256(13) 0.0397(7) Uani 1 1 d . . . . .
O4 O 0.9367(2) 0.0232(2) 0.58095(14) 0.0378(7) Uani 1 1 d . . . . .
N2 N 0.9493(3) 0.1149(2) 0.55601(15) 0.0310(7) Uani 1 1 d . . . . .
C39 C 0.6579(3) 0.6862(3) 0.72927(17) 0.0334(8) Uani 1 1 d . . . . .
H39 H 0.6297 0.7476 0.7502 0.040 Uiso 1 1 calc R . . . .
C37 C 0.7983(3) 0.6042(3) 0.66626(16) 0.0291(8) Uani 1 1 d . . . . .
H37 H 0.8659 0.6113 0.6455 0.035 Uiso 1 1 calc R . . . .
C21 C 0.6769(3) 0.0043(3) 0.63600(15) 0.0266(7) Uani 1 1 d . . . . .
C22 C 0.6085(3) -0.0817(3) 0.61432(17) 0.0301(8) Uani 1 1 d . . . . .
H22 H 0.5830 -0.1380 0.6398 0.036 Uiso 1 1 calc R . . . .
C24 C 0.6162(3) 0.0024(3) 0.51720(15) 0.0247(7) Uani 1 1 d . . . . .
H24 H 0.5974 0.0011 0.4769 0.030 Uiso 1 1 calc R . . . .
C25 C 0.6817(3) 0.0896(3) 0.53963(16) 0.0244(7) Uani 1 1 d . . . . .
H25 H 0.7040 0.1475 0.5144 0.029 Uiso 1 1 calc R . . . .
C26 C 0.7148(3) 0.0919(2) 0.59968(15) 0.0228(6) Uani 1 1 d . . . . .
C38 C 0.7570(3) 0.6953(3) 0.69721(17) 0.0334(8) Uani 1 1 d . . . . .
H38 H 0.7960 0.7631 0.6965 0.040 Uiso 1 1 calc R . . . .
C27 C 0.7910(3) 0.1868(2) 0.62201(15) 0.0233(6) Uani 1 1 d . . . . .
H27 H 0.8236 0.1639 0.6603 0.028 Uiso 1 1 calc R . . . .
C40 C 0.6009(3) 0.5844(3) 0.72976(17) 0.0303(8) Uani 1 1 d . . . . .
H40 H 0.5350 0.5778 0.7520 0.036 Uiso 1 1 calc R . . . .
C28 C 0.8864(3) 0.2100(3) 0.57916(16) 0.0250(7) Uani 1 1 d . . . . .
C23 C 0.5787(3) -0.0828(3) 0.55466(17) 0.0291(8) Uani 1 1 d . . . . .
H23 H 0.5338 -0.1404 0.5397 0.035 Uiso 1 1 calc R . . . .
C29 C 0.9274(3) 0.3127(3) 0.56933(16) 0.0270(7) Uani 1 1 d . . . . .
H29 H 0.9876 0.3218 0.5432 0.032 Uiso 1 1 calc R . . . .
C30 C 0.8801(3) 0.4103(3) 0.59851(16) 0.0266(7) Uani 1 1 d . . . . .
H30 H 0.9156 0.4796 0.5941 0.032 Uiso 1 1 calc R . . . .
C31 C 0.7860(3) 0.4035(2) 0.63193(14) 0.0224(6) Uani 1 1 d . . . . .
C32 C 0.7195(3) 0.2945(3) 0.63222(16) 0.0245(7) Uani 1 1 d . . . . .
H32 H 0.6656 0.2990 0.5992 0.029 Uiso 1 1 calc R . . . .
C33 C 0.6500(3) 0.2824(3) 0.6894(2) 0.0367(9) Uani 1 1 d . . . . .
H33A H 0.6039 0.2152 0.6869 0.044 Uiso 1 1 calc R . . . .
H33B H 0.7006 0.2740 0.7232 0.044 Uiso 1 1 calc R . . . .
C34 C 0.5742(4) 0.3841(3) 0.6995(2) 0.0428(10) Uani 1 1 d . . . . .
H34A H 0.5163 0.3859 0.6689 0.051 Uiso 1 1 calc R . . . .
H34B H 0.5370 0.3770 0.7378 0.051 Uiso 1 1 calc R . . . .
C35 C 0.6397(3) 0.4920(3) 0.69788(15) 0.0265(7) Uani 1 1 d . . . . .
C36 C 0.7407(3) 0.5002(3) 0.66524(14) 0.0229(6) Uani 1 1 d . . . . .
O2 O 0.5702(2) 0.8117(2) 0.39069(12) 0.0357(6) Uani 1 1 d . . . . .
O1 O 0.5689(3) 0.8104(2) 0.29326(13) 0.0422(7) Uani 1 1 d . . . . .
N1 N 0.5852(3) 0.7647(2) 0.34175(15) 0.0323(7) Uani 1 1 d . . . . .
C9 C 0.5816(3) 0.5793(3) 0.30131(17) 0.0313(8) Uani 1 1 d . . . . .
H9 H 0.5415 0.6091 0.2694 0.038 Uiso 1 1 calc R . . . .
C14 C 0.8662(3) 0.3347(3) 0.41244(16) 0.0262(7) Uani 1 1 d . . . . .
H14A H 0.9233 0.3553 0.3834 0.031 Uiso 1 1 calc R . . . .
H14B H 0.9037 0.2994 0.4460 0.031 Uiso 1 1 calc R . . . .
C18 C 0.6340(3) 0.0997(3) 0.33307(15) 0.0277(7) Uani 1 1 d . . . . .
H18 H 0.5839 0.0492 0.3158 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6739(3) 0.4162(3) 0.34460(15) 0.0233(7) Uani 1 1 d . . . . .
C16 C 0.6914(3) 0.2932(3) 0.35199(15) 0.0235(7) Uani 1 1 d . . . . .
C20 C 0.8004(3) 0.1366(3) 0.39086(15) 0.0273(7) Uani 1 1 d . . . . .
H20 H 0.8618 0.1099 0.4125 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6220(3) 0.6471(3) 0.34316(16) 0.0262(7) Uani 1 1 d . . . . .
C10 C 0.5999(3) 0.4590(3) 0.30519(16) 0.0274(7) Uani 1 1 d . . . . .
H10 H 0.5600 0.4109 0.2802 0.033 Uiso 1 1 calc R . . . .
C13 C 0.8043(3) 0.4403(3) 0.43349(16) 0.0271(7) Uani 1 1 d . . . . .
H13A H 0.8571 0.4919 0.4520 0.032 Uiso 1 1 calc R . . . .
H13B H 0.7473 0.4204 0.4627 0.032 Uiso 1 1 calc R . . . .
C15 C 0.7844(3) 0.2529(3) 0.38474(14) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.6171(3) 0.2150(3) 0.32681(15) 0.0262(7) Uani 1 1 d . . . . .
H17 H 0.5550 0.2406 0.3054 0.031 Uiso 1 1 calc R . . . .
C19 C 0.7259(3) 0.0607(3) 0.36519(15) 0.0293(8) Uani 1 1 d . . . . .
H19 H 0.7376 -0.0162 0.3695 0.035 Uiso 1 1 calc R . . . .
C12 C 0.7486(3) 0.4963(3) 0.37935(15) 0.0219(6) Uani 1 1 d . . . . .
H12 H 0.804(4) 0.506(4) 0.351(2) 0.052(13) Uiso 1 1 d . . . . .
C1A C 0.7710(3) 0.6939(3) 0.41968(16) 0.0255(7) Uani 1 1 d . . . . .
Cl1 Cl 0.70636(10) 0.65425(9) 0.53169(5) 0.0301(3) Uani 0.802(3) 1 d . . P A 1
C5A C 0.8575(4) 0.8089(4) 0.4956(2) 0.0247(9) Uiso 0.802(3) 1 d . . P A 1
H5A H 0.8625 0.8282 0.5357 0.030 Uiso 0.802(3) 1 calc R . P A 1
C6A C 0.7837(4) 0.7236(3) 0.4770(2) 0.0209(9) Uiso 0.802(3) 1 d . . P A 1
C4A C 0.9224(4) 0.8636(4) 0.4539(2) 0.0273(10) Uiso 0.802(3) 1 d . . P A 1
H4A H 0.9705 0.9212 0.4659 0.033 Uiso 0.802(3) 1 calc R . P A 1
C2A C 0.8424(4) 0.7505(4) 0.3771(2) 0.0240(9) Uiso 0.802(3) 1 d . . P A 1
H2A H 0.8383 0.7304 0.3371 0.029 Uiso 0.802(3) 1 calc R . P A 1
C3A C 0.9172(4) 0.8344(4) 0.3945(2) 0.0268(9) Uiso 0.802(3) 1 d . . P A 1
H3A H 0.9629 0.8701 0.3666 0.032 Uiso 0.802(3) 1 calc R . P A 1
Cl3 Cl 0.8502(5) 0.7394(6) 0.3224(2) 0.0495(18) Uani 0.198(3) 1 d . . P A 2
C7 C 0.6876(3) 0.6074(2) 0.39710(15) 0.0223(7) Uani 1 1 d . . . B 2
H7 H 0.6339 0.5907 0.4291 0.027 Uiso 1 1 calc R . . B 2
C4B C 0.9078(15) 0.8455(14) 0.4811(8) 0.020(3) Uiso 0.198(3) 1 d . . P A 2
H4B H 0.9566 0.8977 0.4982 0.024 Uiso 0.198(3) 1 calc R . P A 2
C3B C 0.8317(14) 0.7875(13) 0.5188(8) 0.020(3) Uiso 0.198(3) 1 d . . P A 2
H3B H 0.8304 0.8017 0.5595 0.024 Uiso 0.198(3) 1 calc R . P A 2
C6B C 0.8365(17) 0.7510(16) 0.4010(10) 0.028(4) Uiso 0.198(3) 1 d . . P A 2
C5B C 0.9130(14) 0.8294(13) 0.4231(9) 0.020(3) Uiso 0.198(3) 1 d . . P A 2
H5B H 0.9639 0.8675 0.3988 0.024 Uiso 0.198(3) 1 calc R . P A 2
C2B C 0.7570(16) 0.7067(15) 0.4931(9) 0.024(4) Uiso 0.198(3) 1 d . . P A 2
H2B H 0.7054 0.6652 0.5154 0.028 Uiso 0.198(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C21 1.751(4) . ?
O3 N2 1.243(4) . ?
O4 N2 1.234(4) . ?
N2 C28 1.450(4) . ?
C39 C38 1.381(6) . ?
C39 C40 1.386(5) . ?
C37 C38 1.376(5) . ?
C37 C36 1.413(5) . ?
C21 C22 1.392(5) . ?
C21 C26 1.397(4) . ?
C22 C23 1.384(5) . ?
C24 C25 1.388(4) . ?
C24 C23 1.389(5) . ?
C25 C26 1.403(5) . ?
C26 C27 1.530(4) . ?
C27 C28 1.508(5) . ?
C27 C32 1.552(4) . ?
C40 C35 1.389(5) . ?
C28 C29 1.333(5) . ?
C29 C30 1.445(5) . ?
C30 C31 1.345(5) . ?
C31 C32 1.517(4) . ?
C31 C36 1.473(4) . ?
C32 C33 1.531(5) . ?
C33 C34 1.523(5) . ?
C34 C35 1.501(5) . ?
C35 C36 1.405(5) . ?
O2 N1 1.244(4) . ?
O1 N1 1.231(4) . ?
N1 C8 1.465(4) . ?
C9 C8 1.327(5) . ?
C9 C10 1.450(5) . ?
C14 C13 1.529(5) . ?
C14 C15 1.507(5) . ?
C18 C17 1.393(5) . ?
C18 C19 1.385(5) . ?
C11 C16 1.487(4) . ?
C11 C10 1.345(5) . ?
C11 C12 1.515(4) . ?
C16 C15 1.408(5) . ?
C16 C17 1.399(5) . ?
C20 C15 1.403(4) . ?
C20 C19 1.387(5) . ?
C8 C7 1.513(5) . ?
C13 C12 1.534(5) . ?
C12 C7 1.558(4) . ?
C1A C6A 1.343(5) . ?
C1A C2A 1.442(6) . ?
C1A C7 1.513(4) . ?
C1A C6B 1.11(2) . ?
C1A C2B 1.66(2) . ?
Cl1 C6A 1.738(5) . ?
C5A C6A 1.402(6) . ?
C5A C4A 1.375(7) . ?
C4A C3A 1.379(6) . ?
C2A C3A 1.390(6) . ?
Cl3 C6B 1.78(2) . ?
C4B C3B 1.42(2) . ?
C4B C5B 1.32(2) . ?
C3B C2B 1.43(2) . ?
C6B C5B 1.39(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N2 C28 119.4(3) . . ?
O4 N2 O3 122.9(3) . . ?
O4 N2 C28 117.7(3) . . ?
C38 C39 C40 119.1(3) . . ?
C38 C37 C36 121.7(3) . . ?
C22 C21 Cl2 117.3(3) . . ?
C22 C21 C26 122.1(3) . . ?
C26 C21 Cl2 120.6(3) . . ?
C23 C22 C21 119.6(3) . . ?
C25 C24 C23 120.2(3) . . ?
C24 C25 C26 121.2(3) . . ?
C21 C26 C25 117.1(3) . . ?
C21 C26 C27 123.3(3) . . ?
C25 C26 C27 119.6(3) . . ?
C37 C38 C39 120.2(3) . . ?
C26 C27 C32 109.5(3) . . ?
C28 C27 C26 111.6(3) . . ?
C28 C27 C32 110.6(3) . . ?
C39 C40 C35 121.7(4) . . ?
N2 C28 C27 118.0(3) . . ?
C29 C28 N2 118.0(3) . . ?
C29 C28 C27 123.0(3) . . ?
C22 C23 C24 119.8(3) . . ?
C28 C29 C30 121.4(3) . . ?
C31 C30 C29 121.6(3) . . ?
C30 C31 C32 119.0(3) . . ?
C30 C31 C36 122.5(3) . . ?
C36 C31 C32 118.4(3) . . ?
C31 C32 C27 114.9(3) . . ?
C31 C32 C33 111.3(3) . . ?
C33 C32 C27 109.9(3) . . ?
C34 C33 C32 111.5(3) . . ?
C35 C34 C33 111.7(3) . . ?
C40 C35 C34 119.5(3) . . ?
C40 C35 C36 119.7(3) . . ?
C36 C35 C34 120.8(3) . . ?
C37 C36 C31 121.0(3) . . ?
C35 C36 C37 117.6(3) . . ?
C35 C36 C31 121.4(3) . . ?
O2 N1 C8 116.8(3) . . ?
O1 N1 O2 124.0(3) . . ?
O1 N1 C8 119.1(3) . . ?
C8 C9 C10 120.2(3) . . ?
C15 C14 C13 110.4(3) . . ?
C19 C18 C17 119.7(3) . . ?
C16 C11 C12 118.7(3) . . ?
C10 C11 C16 122.4(3) . . ?
C10 C11 C12 118.7(3) . . ?
C15 C16 C11 120.1(3) . . ?
C17 C16 C11 121.4(3) . . ?
C17 C16 C15 118.4(3) . . ?
C19 C20 C15 121.0(3) . . ?
N1 C8 C7 117.9(3) . . ?
C9 C8 N1 117.2(3) . . ?
C9 C8 C7 124.1(3) . . ?
C11 C10 C9 120.7(3) . . ?
C14 C13 C12 108.6(3) . . ?
C16 C15 C14 119.9(3) . . ?
C20 C15 C14 120.6(3) . . ?
C20 C15 C16 119.5(3) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C19 C20 119.9(3) . . ?
C11 C12 C13 112.7(3) . . ?
C11 C12 C7 113.2(3) . . ?
C13 C12 C7 111.4(3) . . ?
C6A C1A C2A 116.5(4) . . ?
C7 C1A C2B 109.2(7) . . ?
C6B C1A C7 138.0(12) . . ?
C6B C1A C2B 112.8(13) . . ?
C4A C5A C6A 119.3(4) . . ?
C1A C6A Cl1 119.5(3) . . ?
C1A C6A C5A 123.0(4) . . ?
C5A C6A Cl1 117.6(3) . . ?
C5A C4A C3A 120.9(5) . . ?
C3A C2A C1A 121.6(5) . . ?
C4A C3A C2A 118.7(5) . . ?
C8 C7 C12 107.4(3) . . ?
C1A C7 C8 113.0(3) . . ?
C1A C7 C12 111.1(3) . . ?
C5B C4B C3B 123.3(17) . . ?
C4B C3B C2B 118.9(16) . . ?
C1A C6B Cl3 113.0(15) . . ?
C1A C6B C5B 137(2) . . ?
C5B C6B Cl3 110.3(15) . . ?
C4B C5B C6B 114.8(17) . . ?
C3B C2B C1A 113.5(15) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1009726'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
17 -1 -4 0.0819 16.9881 -0.7895 -4.0810 0.2434 0.2775 0.9571
-16 -3 0 0.0873 -15.9632 -3.1460 -0.1221 -0.0643 -0.0670 -0.9686
14 2 -17 0.0755 13.9396 2.3613 -16.9306 -0.1157 0.5695 0.8162
14 4 17 0.1043 13.9898 3.8942 17.1817 0.1882 -0.4682 0.8908
-2 1 31 0.0821 -1.9459 0.5558 31.0647 0.2930 -0.9449 -0.0603
-16 -3 4 0.0804 -15.9554 -3.2010 3.8794 -0.0160 -0.1841 -0.9636
-12 -10 10 0.0832 -11.8880 -10.2462 9.5247 0.4860 -0.1778 -0.8379
2 15 -11 0.0990 1.8496 15.1818 -11.2581 -0.9171 0.0480 0.3400
-1 0 -32 0.0788 -1.0622 0.4304 -32.0099 -0.4005 0.9284 -0.0976
-12 -9 13 0.0796 -11.8904 -9.2875 12.5758 0.4689 -0.2869 -0.8181

_olex2_submission_special_instructions 'No special instructions were received'
