# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_huaws0323_3
_audit_creation_date             2013-03-26
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C35 H27 Cl'
_chemical_formula_sum            'C35 H27 Cl'
_chemical_formula_weight         483.02
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.9726(12)
_cell_length_b                   11.8001(9)
_cell_length_c                   12.7945(18)
_cell_angle_alpha                88.880(9)
_cell_angle_beta                 71.972(12)
_cell_angle_gamma                65.771(10)
_cell_volume                     1295.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0010
_cell_measurement_theta_min      3.6110
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8982
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8741
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   16.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000 -180.0000 22

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   20.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000   30.0000 22

#__ type_ start__ end____ width___ exp.time_
  3 omega   72.00   99.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000 -120.0000 18

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   90.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega  -34.00   92.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   48.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -120.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0674461000
_diffrn_orient_matrix_UB_12      -0.0288007000
_diffrn_orient_matrix_UB_13      0.0158465000
_diffrn_orient_matrix_UB_21      -0.0477410000
_diffrn_orient_matrix_UB_22      0.0099328000
_diffrn_orient_matrix_UB_23      0.0561910000
_diffrn_orient_matrix_UB_31      -0.0013834000
_diffrn_orient_matrix_UB_32      -0.0590364000
_diffrn_orient_matrix_UB_33      -0.0064633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3688
_reflns_number_total             5267
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.049
_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/[\s^2^(Fo^2^)+(0.0338P)^2^+0.2323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1141
_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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:
  H12 of C12, H11 of C11, H8 of C8, H7 of C7, H5 of C5, H4 of C4, H3 of C3,
  H1 of C1, H13 of C13, H29 of C29, H31 of C31, H32 of C32, H33 of C33, H34 of
  C34, H35 of C35, H14 of C14, H15 of C15, H17 of C17, H18 of C18, H19 of C19,
  H20 of C20, H21 of C21, H22 of C22, H25 of C25, H26 of C26, H27 of C27, H28
  of C28
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.80318(7) 0.67434(5) 0.47888(6) 0.0689(2) Uani 1 1 d . . .
C1 C 0.9395(2) 0.43772(17) 0.37550(17) 0.0437(5) Uani 1 1 d . . .
H1 H 1.0199 0.4580 0.3348 0.052 Uiso 1 1 calc R . .
C2 C 0.8123(2) 0.52550(18) 0.45556(18) 0.0490(5) Uani 1 1 d . . .
C3 C 0.6912(3) 0.4987(2) 0.5177(2) 0.0631(6) Uani 1 1 d . . .
H3 H 0.6057 0.5585 0.5719 0.076 Uiso 1 1 calc R . .
C4 C 0.6998(2) 0.3817(2) 0.4977(2) 0.0655(6) Uani 1 1 d . . .
H4 H 0.6190 0.3623 0.5390 0.079 Uiso 1 1 calc R . .
C5 C 0.8268(2) 0.29190(19) 0.41715(18) 0.0517(5) Uani 1 1 d . . .
H5 H 0.8303 0.2132 0.4047 0.062 Uiso 1 1 calc R . .
C6 C 0.9489(2) 0.31907(17) 0.35493(16) 0.0399(4) Uani 1 1 d . . .
C7 C 1.0951(2) 0.22246(16) 0.26856(16) 0.0396(4) Uani 1 1 d . . .
H7 H 1.1810 0.1961 0.2986 0.047 Uiso 1 1 calc R . .
C8 C 1.0790(2) 0.10743(17) 0.23661(16) 0.0434(5) Uani 1 1 d . . .
H8 H 1.0136 0.1183 0.1952 0.052 Uiso 1 1 calc R . .
C9 C 1.1483(2) -0.00827(17) 0.26111(15) 0.0395(4) Uani 1 1 d . . .
C10 C 1.1395(2) -0.11658(17) 0.20997(17) 0.0429(5) Uani 1 1 d . . .
C11 C 1.1328(2) -0.21471(18) 0.2694(2) 0.0554(6) Uani 1 1 d . . .
H11 H 1.1328 -0.2128 0.3420 0.067 Uiso 1 1 calc R . .
C12 C 1.1262(3) -0.3161(2) 0.2211(3) 0.0725(7) Uani 1 1 d . . .
H12 H 1.1207 -0.3812 0.2618 0.087 Uiso 1 1 calc R . .
C13 C 1.1275(3) -0.3205(2) 0.1138(3) 0.0787(9) Uani 1 1 d . . .
H13 H 1.1237 -0.3886 0.0816 0.094 Uiso 1 1 calc R . .
C14 C 1.1345(3) -0.2243(3) 0.0541(2) 0.0759(8) Uani 1 1 d . . .
H14 H 1.1350 -0.2271 -0.0186 0.091 Uiso 1 1 calc R . .
C15 C 1.1409(3) -0.1234(2) 0.1013(2) 0.0592(6) Uani 1 1 d . . .
H15 H 1.1463 -0.0588 0.0598 0.071 Uiso 1 1 calc R . .
C16 C 1.2384(2) -0.03580(16) 0.33928(16) 0.0389(4) Uani 1 1 d . . .
C17 C 1.3898(2) -0.12868(18) 0.30824(18) 0.0509(5) Uani 1 1 d . . .
H17 H 1.4351 -0.1739 0.2381 0.061 Uiso 1 1 calc R . .
C18 C 1.4741(3) -0.1546(2) 0.3805(2) 0.0592(6) Uani 1 1 d . . .
H18 H 1.5759 -0.2163 0.3582 0.071 Uiso 1 1 calc R . .
C19 C 1.4083(3) -0.0900(2) 0.48497(19) 0.0554(6) Uani 1 1 d . . .
H19 H 1.4650 -0.1083 0.5335 0.066 Uiso 1 1 calc R . .
C20 C 1.2583(3) 0.00174(19) 0.51735(18) 0.0528(5) Uani 1 1 d . . .
H20 H 1.2134 0.0460 0.5879 0.063 Uiso 1 1 calc R . .
C21 C 1.1741(2) 0.02839(17) 0.44516(17) 0.0456(5) Uani 1 1 d . . .
H21 H 1.0725 0.0905 0.4680 0.055 Uiso 1 1 calc R . .
C22 C 1.1381(2) 0.27943(17) 0.16405(16) 0.0418(5) Uani 1 1 d . . .
H22 H 1.0582 0.3225 0.1357 0.050 Uiso 1 1 calc R . .
C23 C 1.2773(2) 0.27539(16) 0.10746(16) 0.0395(4) Uani 1 1 d . . .
C24 C 1.3027(2) 0.33293(16) 0.00201(16) 0.0394(4) Uani 1 1 d . . .
C25 C 1.4220(2) 0.37062(18) -0.03717(18) 0.0502(5) Uani 1 1 d . . .
H25 H 1.4935 0.3548 0.0000 0.060 Uiso 1 1 calc R . .
C26 C 1.4362(3) 0.4314(2) -0.1308(2) 0.0632(6) Uani 1 1 d . . .
H26 H 1.5159 0.4573 -0.1549 0.076 Uiso 1 1 calc R . .
C27 C 1.3344(3) 0.4540(2) -0.1886(2) 0.0659(7) Uani 1 1 d . . .
H27 H 1.3431 0.4964 -0.2506 0.079 Uiso 1 1 calc R . .
C28 C 1.2196(3) 0.4129(2) -0.15330(19) 0.0639(6) Uani 1 1 d . . .
H28 H 1.1515 0.4255 -0.1928 0.077 Uiso 1 1 calc R . .
C29 C 1.2041(2) 0.3531(2) -0.05987(18) 0.0541(5) Uani 1 1 d . . .
H29 H 1.1257 0.3255 -0.0376 0.065 Uiso 1 1 calc R . .
C30 C 1.4146(2) 0.21163(18) 0.14636(16) 0.0427(5) Uani 1 1 d . . .
C31 C 1.4963(3) 0.0832(2) 0.1277(2) 0.0634(6) Uani 1 1 d . . .
H31 H 1.4631 0.0355 0.0939 0.076 Uiso 1 1 calc R . .
C32 C 1.6279(3) 0.0240(3) 0.1590(2) 0.0820(8) Uani 1 1 d . . .
H32 H 1.6828 -0.0627 0.1450 0.098 Uiso 1 1 calc R . .
C33 C 1.5940(3) 0.2186(3) 0.2327(2) 0.0802(8) Uani 1 1 d . . .
H33 H 1.6252 0.2652 0.2697 0.096 Uiso 1 1 calc R . .
C34 C 1.6768(3) 0.0924(3) 0.2102(2) 0.0796(8) Uani 1 1 d . . .
H34 H 1.7663 0.0528 0.2295 0.096 Uiso 1 1 calc R . .
C35 C 1.4637(3) 0.2785(2) 0.20106(19) 0.0624(6) Uani 1 1 d . . .
H35 H 1.4084 0.3650 0.2169 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0737(4) 0.0457(3) 0.0858(5) -0.0001(3) -0.0412(3) -0.0129(3)
C1 0.0418(11) 0.0458(11) 0.0490(13) 0.0160(9) -0.0216(9) -0.0196(9)
C2 0.0497(12) 0.0442(11) 0.0539(14) 0.0096(10) -0.0282(11) -0.0128(10)
C3 0.0471(13) 0.0630(15) 0.0610(16) 0.0043(12) -0.0116(11) -0.0105(11)
C4 0.0434(13) 0.0704(16) 0.0736(17) 0.0158(13) -0.0092(11) -0.0233(12)
C5 0.0440(12) 0.0514(12) 0.0635(15) 0.0166(11) -0.0195(10) -0.0230(10)
C6 0.0388(10) 0.0397(10) 0.0470(12) 0.0153(9) -0.0229(9) -0.0164(8)
C7 0.0392(10) 0.0386(10) 0.0470(12) 0.0141(9) -0.0210(9) -0.0178(8)
C8 0.0425(11) 0.0485(11) 0.0475(12) 0.0106(9) -0.0203(9) -0.0233(9)
C9 0.0407(10) 0.0406(10) 0.0396(11) 0.0074(8) -0.0128(8) -0.0200(9)
C10 0.0366(10) 0.0428(11) 0.0478(12) 0.0001(9) -0.0110(9) -0.0173(8)
C11 0.0572(13) 0.0462(12) 0.0615(15) 0.0048(10) -0.0121(11) -0.0260(10)
C12 0.0632(16) 0.0510(14) 0.103(2) 0.0029(14) -0.0150(15) -0.0330(12)
C13 0.0568(15) 0.0652(17) 0.112(3) -0.0285(17) -0.0246(15) -0.0247(13)
C14 0.0720(17) 0.0861(19) 0.0715(18) -0.0165(15) -0.0291(14) -0.0304(15)
C15 0.0640(14) 0.0619(14) 0.0579(15) 0.0031(11) -0.0252(12) -0.0287(12)
C16 0.0429(10) 0.0334(10) 0.0443(12) 0.0098(8) -0.0165(9) -0.0188(8)
C17 0.0520(12) 0.0463(12) 0.0494(13) 0.0007(10) -0.0185(10) -0.0145(10)
C18 0.0485(12) 0.0588(14) 0.0660(16) 0.0095(12) -0.0266(11) -0.0132(10)
C19 0.0640(14) 0.0576(13) 0.0591(15) 0.0181(11) -0.0336(12) -0.0306(12)
C20 0.0701(15) 0.0496(12) 0.0429(13) 0.0071(10) -0.0226(11) -0.0267(11)
C21 0.0485(11) 0.0397(11) 0.0456(13) 0.0075(9) -0.0160(9) -0.0157(9)
C22 0.0412(11) 0.0401(10) 0.0477(12) 0.0129(9) -0.0210(9) -0.0164(8)
C23 0.0413(10) 0.0351(10) 0.0444(12) 0.0051(8) -0.0178(9) -0.0158(8)
C24 0.0406(10) 0.0331(10) 0.0404(11) 0.0052(8) -0.0132(8) -0.0119(8)
C25 0.0468(12) 0.0510(12) 0.0513(13) 0.0070(10) -0.0128(10) -0.0218(10)
C26 0.0661(15) 0.0618(14) 0.0575(16) 0.0126(12) -0.0066(12) -0.0336(12)
C27 0.0750(17) 0.0577(14) 0.0509(15) 0.0203(12) -0.0132(13) -0.0209(13)
C28 0.0602(14) 0.0729(16) 0.0514(14) 0.0217(12) -0.0252(11) -0.0173(12)
C29 0.0498(12) 0.0651(14) 0.0523(14) 0.0185(11) -0.0218(10) -0.0260(11)
C30 0.0390(10) 0.0487(11) 0.0416(12) 0.0109(9) -0.0142(9) -0.0194(9)
C31 0.0575(14) 0.0528(14) 0.0779(18) 0.0132(12) -0.0304(12) -0.0160(11)
C32 0.0585(16) 0.0695(17) 0.098(2) 0.0291(16) -0.0273(15) -0.0081(13)
C33 0.0654(16) 0.120(3) 0.0719(19) 0.0143(17) -0.0390(14) -0.0440(17)
C34 0.0483(14) 0.123(3) 0.0685(19) 0.0382(18) -0.0298(13) -0.0307(16)
C35 0.0615(14) 0.0716(15) 0.0619(16) 0.0048(12) -0.0285(12) -0.0297(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.748(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(3) . ?
C1 C6 1.389(2) . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.527(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.508(2) . ?
C7 C22 1.507(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.335(2) . ?
C9 C10 1.493(2) . ?
C9 C16 1.489(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.389(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 C21 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.333(2) . ?
C23 C24 1.496(3) . ?
C23 C30 1.500(2) . ?
C24 C25 1.386(3) . ?
C24 C29 1.391(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.370(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(3) . ?
C30 C35 1.380(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.390(3) . ?
C32 H32 0.9300 . ?
C32 C34 1.364(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.358(4) . ?
C33 C35 1.383(3) . ?
C34 H34 0.9300 . ?
C35 H35 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 119.7 . . ?
C2 C1 C6 120.55(18) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 Cl1 119.47(16) . . ?
C1 C2 C3 121.31(19) . . ?
C3 C2 Cl1 119.22(17) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 118.99(16) . . ?
C5 C6 C1 118.28(18) . . ?
C5 C6 C7 122.69(17) . . ?
C6 C7 H7 108.3 . . ?
C8 C7 C6 114.02(14) . . ?
C8 C7 H7 108.3 . . ?
C22 C7 C6 110.44(14) . . ?
C22 C7 H7 108.3 . . ?
C22 C7 C8 107.31(15) . . ?
C7 C8 H8 116.4 . . ?
C9 C8 C7 127.25(17) . . ?
C9 C8 H8 116.4 . . ?
C8 C9 C10 121.01(17) . . ?
C8 C9 C16 122.03(17) . . ?
C16 C9 C10 116.95(16) . . ?
C11 C10 C9 120.59(19) . . ?
C11 C10 C15 118.13(19) . . ?
C15 C10 C9 121.27(18) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C9 120.48(18) . . ?
C17 C16 C21 117.92(18) . . ?
C21 C16 C9 121.59(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.19(19) . . ?
C20 C21 H21 119.4 . . ?
C7 C22 H22 116.2 . . ?
C23 C22 C7 127.68(17) . . ?
C23 C22 H22 116.2 . . ?
C22 C23 C24 121.18(17) . . ?
C22 C23 C30 121.24(17) . . ?
C24 C23 C30 117.57(16) . . ?
C25 C24 C23 122.12(17) . . ?
C25 C24 C29 117.14(19) . . ?
C29 C24 C23 120.72(17) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(2) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 120.6 . . ?
C28 C27 C26 118.8(2) . . ?
C28 C27 H27 120.6 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.5(2) . . ?
C29 C28 H28 119.7 . . ?
C24 C29 H29 119.2 . . ?
C28 C29 C24 121.6(2) . . ?
C28 C29 H29 119.2 . . ?
C31 C30 C23 120.47(18) . . ?
C31 C30 C35 117.8(2) . . ?
C35 C30 C23 121.69(18) . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.7(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.8 . . ?
C34 C32 C31 120.3(3) . . ?
C34 C32 H32 119.8 . . ?
C34 C33 H33 119.7 . . ?
C34 C33 C35 120.6(2) . . ?
C35 C33 H33 119.7 . . ?
C32 C34 H34 120.2 . . ?
C33 C34 C32 119.5(2) . . ?
C33 C34 H34 120.2 . . ?
C30 C35 C33 120.9(2) . . ?
C30 C35 H35 119.5 . . ?
C33 C35 H35 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 C3 C4 179.55(17) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 -168.14(16) . . . . ?
C1 C6 C7 C22 -47.2(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -177.57(17) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 177.29(19) . . . . ?
C5 C6 C7 C8 14.3(3) . . . . ?
C5 C6 C7 C22 135.24(19) . . . . ?
C6 C1 C2 Cl1 -179.59(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 C8 C9 -109.8(2) . . . . ?
C6 C7 C22 C23 130.5(2) . . . . ?
C7 C8 C9 C10 -170.99(17) . . . . ?
C7 C8 C9 C16 8.5(3) . . . . ?
C7 C22 C23 C24 177.63(17) . . . . ?
C7 C22 C23 C30 -1.6(3) . . . . ?
C8 C7 C22 C23 -104.7(2) . . . . ?
C8 C9 C10 C11 -145.6(2) . . . . ?
C8 C9 C10 C15 35.8(3) . . . . ?
C8 C9 C16 C17 -127.5(2) . . . . ?
C8 C9 C16 C21 53.4(3) . . . . ?
C9 C10 C11 C12 -179.37(18) . . . . ?
C9 C10 C15 C14 179.3(2) . . . . ?
C9 C16 C17 C18 179.99(18) . . . . ?
C9 C16 C21 C20 179.65(17) . . . . ?
C10 C9 C16 C17 52.0(2) . . . . ?
C10 C9 C16 C21 -127.08(18) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C16 C9 C10 C11 34.9(2) . . . . ?
C16 C9 C10 C15 -143.76(19) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C16 C21 C20 0.6(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C16 -0.2(3) . . . . ?
C21 C16 C17 C18 -0.9(3) . . . . ?
C22 C7 C8 C9 127.6(2) . . . . ?
C22 C23 C24 C25 156.35(19) . . . . ?
C22 C23 C24 C29 -22.3(3) . . . . ?
C22 C23 C30 C31 79.4(3) . . . . ?
C22 C23 C30 C35 -100.9(2) . . . . ?
C23 C24 C25 C26 -175.49(18) . . . . ?
C23 C24 C29 C28 175.92(19) . . . . ?
C23 C30 C31 C32 177.0(2) . . . . ?
C23 C30 C35 C33 -177.5(2) . . . . ?
C24 C23 C30 C31 -99.9(2) . . . . ?
C24 C23 C30 C35 79.8(2) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C25 C24 C29 C28 -2.8(3) . . . . ?
C25 C26 C27 C28 -1.3(4) . . . . ?
C26 C27 C28 C29 1.8(4) . . . . ?
C27 C28 C29 C24 0.4(4) . . . . ?
C29 C24 C25 C26 3.2(3) . . . . ?
C30 C23 C24 C25 -24.4(3) . . . . ?
C30 C23 C24 C29 156.92(18) . . . . ?
C30 C31 C32 C34 0.9(4) . . . . ?
C31 C30 C35 C33 2.2(3) . . . . ?
C31 C32 C34 C33 1.5(4) . . . . ?
C34 C33 C35 C30 0.2(4) . . . . ?
C35 C30 C31 C32 -2.7(3) . . . . ?
C35 C33 C34 C32 -2.1(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 946280'
#######################################################################
#
#                 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_618
_audit_creation_date             2013-01-08
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H12'
_chemical_formula_sum            'C19 H12'
_chemical_formula_weight         240.29
_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 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
3 '-x, -y, -z'
4 'x, -y-1/2, z'

_cell_length_a                   7.5874(3)
_cell_length_b                   6.8977(4)
_cell_length_c                   12.9328(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.773(4)
_cell_angle_gamma                90.00
_cell_volume                     657.38(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3435
_cell_measurement_temperature    100(7)
_cell_measurement_theta_max      72.4234
_cell_measurement_theta_min      6.1921
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5725
_diffrn_reflns_theta_full        72.57
_diffrn_reflns_theta_max         72.57
_diffrn_reflns_theta_min         6.20
_diffrn_ambient_temperature      100(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9551
_diffrn_measured_fraction_theta_max 0.9456
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -65.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega -129.00 -101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega  -71.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega  -51.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -88.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega  -53.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   73.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  -50.00    7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   25.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega -130.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega -116.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
 19 omega -100.00  -40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 20 omega  -61.00  -31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 21 omega -137.00  -96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 22 omega  -78.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 23 omega   50.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   98.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 25 omega   85.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 26 omega  138.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 27 omega   96.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   63.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 29 omega  110.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   99.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 31 omega  126.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   97.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 33 omega   84.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega  121.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 35 omega   88.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 36 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  168.5096 27

#__ type_ start__ end____ width___ exp.time_
 37 omega  122.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 38 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   49.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 41 omega   44.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 42 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   93.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 44 omega   44.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 45 omega  140.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 46 omega   90.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 47 omega   82.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 48 omega   44.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 49 omega   91.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 50 omega  109.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 51 omega   90.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 52 omega   90.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 53 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega   91.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 56 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 58 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 59 omega  120.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  168.5096 46

#__ type_ start__ end____ width___ exp.time_
 60 omega  124.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   31.0000  121.4345 25

#__ type_ start__ end____ width___ exp.time_
 61 omega  101.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 62 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   31.0000  121.4345 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1993736000
_diffrn_orient_matrix_UB_12      0.0233831000
_diffrn_orient_matrix_UB_13      0.0055960000
_diffrn_orient_matrix_UB_21      -0.0603169000
_diffrn_orient_matrix_UB_22      -0.0143492000
_diffrn_orient_matrix_UB_23      -0.1222341000
_diffrn_orient_matrix_UB_31      -0.0172226000
_diffrn_orient_matrix_UB_32      -0.2216940000
_diffrn_orient_matrix_UB_33      0.0085332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1349
_reflns_number_total             1402
_reflns_odcompleteness_completeness 95.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.201
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   3.220
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0992
_refine_ls_restrained_S_all      3.220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3323
_refine_ls_wR_factor_ref         0.3362
_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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:
  H7 of C7, H9 of C9, H6 of C6, H5 of C5, H4 of C4, H12 of C12, H14 of C14,
  H15 of C15, {H10A,H10B} of C10
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H12(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C6(H6), C4(H4), C5(H5), C15(H15), C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.8435(4) 0.7500 0.8380(2) 0.0266(8) Uani 1 2 d S . .
C2 C 1.0104(4) 0.7500 0.8242(2) 0.0268(8) Uani 1 2 d S . .
C9 C 0.8426(3) 0.7500 0.9543(2) 0.0262(9) Uani 1 2 d S . .
H9 H 0.7416 0.7500 0.9859 0.031 Uiso 1 2 calc SR . .
C7 C 1.1320(4) 0.7500 1.1144(2) 0.0272(9) Uani 1 2 d S . .
H7 H 1.0654 0.7500 1.1680 0.033 Uiso 1 2 calc SR . .
C8 C 1.0426(3) 0.7500 1.0083(2) 0.0249(8) Uani 1 2 d S . .
C6 C 1.3211(4) 0.7500 1.1421(2) 0.0288(9) Uani 1 2 d S . .
H6 H 1.3837 0.7500 1.2150 0.035 Uiso 1 2 calc SR . .
C3 C 1.1426(4) 0.7500 0.9285(2) 0.0255(8) Uani 1 2 d S . .
C4 C 1.3308(3) 0.7500 0.9562(2) 0.0294(9) Uani 1 2 d S . .
H4 H 1.3979 0.7500 0.9028 0.035 Uiso 1 2 calc SR . .
C5 C 1.4192(4) 0.7500 1.0634(2) 0.0311(9) Uani 1 2 d S . .
H5 H 1.5481 0.7500 1.0835 0.037 Uiso 1 2 calc SR . .
C11 C 0.6949(3) 0.7500 0.64251(19) 0.0287(9) Uani 1 2 d S . .
C10 C 0.6673(3) 0.7500 0.75358(19) 0.0293(9) Uani 1 2 d S . .
H10A H 0.5959 0.6340 0.7632 0.035 Uiso 0.50 1 calc PR . .
H10B H 0.5959 0.8660 0.7632 0.035 Uiso 0.50 1 calc PR . .
C15 C 0.7963(3) 0.6518(4) 0.30318(17) 0.0429(9) Uani 1 1 d . . .
H15 H 0.8138 0.5829 0.2428 0.051 Uiso 1 1 calc R . .
C13 C 0.7450(3) 0.6508(4) 0.47934(17) 0.0395(8) Uani 1 1 d . . .
C14 C 0.7706(7) 0.5516(4) 0.3912(2) 0.0781(13) Uani 1 1 d . . .
H14 H 0.7707 0.4139 0.3911 0.094 Uiso 1 1 calc R . .
C12 C 0.7148(5) 0.5837(5) 0.5833(2) 0.0635(11) Uani 1 1 d . . .
H12 H 0.7098 0.4529 0.6055 0.076 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0290(14) 0.0314(17) 0.0205(13) 0.000 0.0080(10) 0.000
C2 0.0285(14) 0.0308(16) 0.0228(13) 0.000 0.0091(10) 0.000
C9 0.0249(14) 0.0325(16) 0.0245(14) 0.000 0.0125(10) 0.000
C7 0.0318(15) 0.0289(16) 0.0245(15) 0.000 0.0138(10) 0.000
C8 0.0259(14) 0.0254(15) 0.0264(14) 0.000 0.0122(11) 0.000
C6 0.0328(16) 0.0316(16) 0.0244(14) 0.000 0.0116(10) 0.000
C3 0.0268(14) 0.0286(16) 0.0243(14) 0.000 0.0125(11) 0.000
C4 0.0254(14) 0.0370(17) 0.0284(15) 0.000 0.0116(10) 0.000
C5 0.0256(13) 0.0403(19) 0.0289(15) 0.000 0.0098(10) 0.000
C11 0.0202(12) 0.0405(19) 0.0260(15) 0.000 0.0071(9) 0.000
C10 0.0252(14) 0.0394(18) 0.0246(14) 0.000 0.0084(10) 0.000
C15 0.0537(14) 0.0480(17) 0.0320(13) -0.0044(9) 0.0203(9) -0.0051(10)
C13 0.0457(13) 0.0479(16) 0.0271(13) -0.0041(9) 0.0128(9) -0.0141(10)
C14 0.165(4) 0.0404(17) 0.0415(16) -0.0103(11) 0.0498(18) -0.029(2)
C12 0.102(2) 0.063(2) 0.0337(14) -0.0167(11) 0.0318(12) -0.0487(17)

_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 1.320(4) . ?
C1 C9 1.506(3) . ?
C1 C10 1.512(3) . ?
C2 C3 1.476(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.512(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C7 C6 1.394(4) . ?
C8 C3 1.419(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(4) . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9500 . ?
C11 C10 1.500(3) . ?
C11 C12 1.407(4) 4_575 ?
C11 C12 1.407(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 C15 1.355(6) 4_575 ?
C15 H15 0.9500 . ?
C15 C14 1.385(4) . ?
C13 C13 1.369(5) 4_575 ?
C13 C14 1.382(4) . ?
C13 C12 1.490(3) . ?
C14 H14 0.9500 . ?
C12 H12 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
C2 C1 C9 111.6(2) . . ?
C2 C1 C10 127.9(2) . . ?
C9 C1 C10 120.5(2) . . ?
C1 C2 C3 110.0(2) . . ?
C1 C9 H9 128.7 . . ?
C1 C9 C8 102.61(19) . . ?
C8 C9 H9 128.7 . . ?
C8 C7 H7 120.4 . . ?
C8 C7 C6 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 131.4(2) . . ?
C7 C8 C3 120.2(2) . . ?
C3 C8 C9 108.4(2) . . ?
C7 C6 H6 119.7 . . ?
C7 C6 C5 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C8 C3 C2 107.4(2) . . ?
C4 C3 C2 132.0(2) . . ?
C4 C3 C8 120.5(2) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C12 C11 C10 125.35(14) 4_575 . ?
C12 C11 C10 125.35(14) . . ?
C12 C11 C12 109.2(3) . 4_575 ?
C1 C10 H10A 109.0 . . ?
C1 C10 H10B 109.0 . . ?
C11 C10 C1 113.0(2) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C15 C15 H15 120.0 4_575 . ?
C15 C15 C14 119.94(17) 4_575 . ?
C14 C15 H15 120.0 . . ?
C13 C13 C14 119.68(16) 4_575 . ?
C13 C13 C12 108.09(18) 4_575 . ?
C14 C13 C12 132.2(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C11 C12 C13 107.3(3) . . ?
C11 C12 H12 126.4 . . ?
C13 C12 H12 126.4 . . ?

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
C1 C2 C3 C8 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(2) . . . . ?
C1 C9 C8 C7 180.000(2) . . . . ?
C1 C9 C8 C3 0.000(1) . . . . ?
C2 C1 C9 C8 0.000(2) . . . . ?
C2 C1 C10 C11 0.000(1) . . . . ?
C2 C3 C4 C5 180.000(2) . . . . ?
C9 C1 C2 C3 0.000(2) . . . . ?
C9 C1 C10 C11 180.000(1) . . . . ?
C9 C8 C3 C2 0.000(1) . . . . ?
C9 C8 C3 C4 180.000(1) . . . . ?
C7 C8 C3 C2 180.000(2) . . . . ?
C7 C8 C3 C4 0.000(2) . . . . ?
C7 C6 C5 C4 0.000(3) . . . . ?
C8 C7 C6 C5 0.000(3) . . . . ?
C8 C3 C4 C5 0.000(2) . . . . ?
C6 C7 C8 C9 180.000(2) . . . . ?
C6 C7 C8 C3 0.000(2) . . . . ?
C3 C4 C5 C6 0.000(2) . . . . ?
C10 C1 C2 C3 180.000(1) . . . . ?
C10 C1 C9 C8 180.000(1) . . . . ?
C10 C11 C12 C13 -178.2(2) . . . . ?
C15 C15 C14 C13 0.0(5) 4_575 . . . ?
C13 C13 C14 C15 0.0(5) 4_575 . . . ?
C13 C13 C12 C11 0.8(3) 4_575 . . . ?
C14 C13 C12 C11 -179.2(3) . . . . ?
C12 C11 C10 C1 88.2(3) . . . . ?
C12 C11 C10 C1 -88.2(3) 4_575 . . . ?
C12 C11 C12 C13 -1.3(4) 4_575 . . . ?
C12 C13 C14 C15 -180.0(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 946281'